Information
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Patent Application
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20040254182
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Publication Number
20040254182
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Date Filed
December 17, 200221 years ago
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Date Published
December 16, 200419 years ago
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CPC
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US Classifications
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International Classifications
- A61K031/675
- A61K031/541
- A61K031/5377
- A61K031/496
Abstract
This invention relates to compounds which are useful as enhanced propertied pharmaceutical compounds for both human and veterinary application. The pharmaceutical compounds which are suitable for use in this invention are those compounds which can be substituted with a moiety, said moiety comprising a substituent which enhances or changes the properties of the pharmaceutical compound. The chemical modification of drugs into labile derivatives with enhanced physicochemical properties that enable better transport through biological barriers is a useful approach for improving-drug delivery.
Description
[0001] This invention relates to compounds which are useful as enhanced propertied pharmaceutical compounds for both human and veterinary application. The pharmaceutical compounds which are suitable for use in this invention are those compounds which can be substituted with a moiety, said moiety comprising a substituent which enhances or changes the properties of the pharmaceutical compound. The chemical modification of drugs into labile derivatives with enhanced physicochemical properties that enable better transport through biological barriers is a useful approach for improving-drug delivery. This modification can be conveniently practiced on ionizable molecules containing moieties such as a carboxy group, an amino group, a hydroxy group, a mercapto group or a group containing an appropriately substituted phosphorous atom that can be utilized for derivatization in order to modify their ionization at physiological pH and to render desirable partition and solubility properties. A necessary requirement of this approach is that the enhanced propertied drug is non-toxic and, when administered to a warm-blooded animal including a human being, is enzymatically and/or chemically cleaved in such a manner as to release the drug at its target or site of activity, quantitatively and at a desirable rate, while the remaining cleaved moiety remains non-toxic and is metabolized in such a manner that non-toxic metabolic products are produced. It is naturally also desirable that the enhanced propertied drug can be provided without excessive costs in connection with its production, in particular without an appreciable loss of the unmodified drug itself during its production and recovery, since the unmodified drug is usually the more expensive part of the enhanced propertied drug.
[0002] Furthermore, the new substituent on the original pharmaceutical compound may itself optionally comprise a pharmaceutical compound which may be the same as or different from the original pharmaceutical compound. This allows a combination of pharmaceutical compounds to be applied simultaneously as a single compound to the host. The application of such a compound provides many advantages such as a greater spectrum of activity against the disease being treated and an attenuation of the build up of disease resistance since the disease is being controlled with two different modes of action. This type of enhanced propertied pharmaceutical compound will naturally comprise two different pharmaceutical moieties which are compatible with one another and which can be used without an antagonistic interactive effect upon the host. Such combinations should be apparent to one of ordinary skill in the art.
[0003] U.S. Pat. No. 4,760,057, U.S. Pat. No. 4,916,230, U.S. Pat. No. 5,401,868, U.S. Pat. No. 5,459,155, U.S. Pat. No. 5,583,148, U.S. Pat. No. 5,684,018, WO 98/16537, WO 98/43970 and WO 99/61017 describe certain pharmaceutical compounds which are substituted with moieties to alter the properties of pharmaceutical compounds; however, the moieties employed in the compounds of the present invention are neither disclosed nor suggested.
[0004] U.S. Pat. No. 5,284,863, U.S. Pat. No. 4,912,090, U.S. Pat. No. 5,385,880, U.S. Pat. No. 5,391,537, JP 1275565 A2, WO 96/36613, WO 99/35141, WO 00/29378, WO 00/40582, DE 4343831 A1, JP 53-43571 B and JP 54-1771 B disclose certain pesticidal compounds which are substituted with moieties to alter the properties of pesticidal compounds; however, the moieties employed in the compounds of the present invention are neither disclosed nor suggested.
[0005] The pharmaceutical compounds which may be advantageously employed to produce the enhanced propertied human health pharmaceutical compounds of this invention include, but are not limited to, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperezinyl)-3-quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid, accolate, acebutolol, acetaminophen, acetazolamide, acrivistine, acyclovir, adamantamine, adapalene, adenosine phosphate, adrenelone, albendazole, albuterol, albutoin, alendronate sodium, aletamine, aliconazole, alinidine, alisobumal, alizapride, allopurinol, alprazolam, alprenolol, amethopterine, amidephrine, aminorex, amiodarone, amitriptyline, amlodipine, amoxapine, amoxicillin, amphetamine, amrinone, apraclonidine, aprinocid, arthrocine, arthrotec, aspartame, astemizole, atenolol, atorvastatin, atropine, azatadine, azathioprine, azithromycin, aztreonam, baclofen, bamethan, becliconazole, beclomet, benazepril, benzatropine, benzonatate, benzphetamine, benztropine, beperiden, betahistine, bicalutamide, bisacodyl, botalol hydrochloride, brimonidine tartrate, brolaconazole, bromocriptine, bromopheniramine, bucindolol, budesonide, bufenox, bunolol, bupivacaine, buprenorphine, bupropion, buspirone, butaconazole, butopamine, butorphanol, butoxamine, caffeine, cafiminol, cambendazole, captopril, carbamazepam, carbinoxamine, carbuterol, carisoprodal, cartelolol, carvedilol, cefachlor, cefadroxil, cefamandole, cefazolin, cefixime, cefinetazole, cefonicid, cefoperazone, cefotaxime, cefotetan, cefpodoxime, cefprozil, ceftriaxone, celecoxib, centerdrine, cephapirin, cetirizine, chlorambucil, chloramiphene, chlorazepate, chlordiazepoxide, chloroprocaine, chloroquine, chloroxazone, chlorpheniramine, chlorpromazine, chlortermine, chlorthiazide, cimetidine, cinnarizine, ciprofloxacin, cisapride, cisconazole, citalopram, cladribine, clarithromycin, clemastine, clindamycin, clobesol, clofazimine, clomiphene, clonazepam, clonidine, clopidrogrel, clorprenaline, clotrimazole, cloxacillin, clozapine, cocaine, codeine, colchicine, colterol, combivir, cortisine, croconazole, cromolyn sodium, cyclobendazole, cyclobenzaprine, cyclopentolate, cyclophosphamide, cyclopsporin, cyproheptadine, dacarbazine, dactinomycin, dantrolene, deacetylketoconazole, demeclocycline, demethylamitriptyline, demethylimipramine, democonazole, deprenil, desipramine, deterenol, dexpropranolol, diacetolol, diazepam, diazoxide, dibucaine, diclofenac sodium, dicodid, dicyclomine, didanosine, diethylproprion, diflunisal, dihydroergotamine, dilantin, diltiazem, dimenhydrinate, dimethoxyphenethylmine, diphenhydramine, diphenidol, diphenoxylate hydrochloride, dipyridamole, disopyramide, dobutamine, doconazole, donezapil hydrochloride, dopamine, dotycin, doxapram, doxazosin, doxepin, doxylamine, dypyridamole, eberconazole, econazole, EDTA, efavirenz, enalapril, enoxacin, enviroxime, epinephrine, ergotamine, erythromycin, estazolam, ethionamide, etintidine, etodolac, etryptamine, exaprolol, exprenolol, famciclovir, famotidine, felodipine, fenbendazole, fenfluramine, fenmetazole, fenoterol, fentanyl, fenticonazole, fenyripol, fexofenadine, finasteride, flavoxate, fluazepam, flubendazole, fluconazole, fludarabine, fludorex, flufenazin, fluoxetine hydrochloride, fluphenazine, flurazepam, flurbiprofen, fluticasone propionate, fluvastatin, fluvoxamine maleate, folic acid, fosphenyloin, furazolidone, furosemide, gabapentin, ganciclovir, gemfibrozil, genaconazole, gentian violet, glimepiride, glipizide, glyburide, granisetron, guaifenesin, guanethidine, guanfacine hydrochloride, halazepam, haloperidol, homatropine, hydrochlorothiazide, hydrocodone, hydromorphone, hydroxychloroquine, hydroxyitraconazole, hydroxyzine, hyoscyamine, ibuprofen, imipramine hydrochloride, indapamide, indinivar sulfate, indomethacin, iodoquinol, ipratropium bromide, irbesartan, isoconazole, isoniazid, isosornide monnitrate, isotretinoin, itraconazole, ketoconazole, ketoprofen, ketorolac, ketorolac, labetalol, labotolol, lamivudine, lamotrigin, lamotrigine, lansoprazole, levobunolol, levocabastine, levofloxacin, levomethadyl, levorphanol, lidocaine, lincomycin, lisinopril, lomefloxacin, loperidine hydrochloride, loratadine, lorazepam, losartan, lotrisone, lovastatin, loxapine, L-thyroxine, mazindol, mebendazole, mechlorethamine, meclizine hydrochloride, medroxyprogesteron, megestrol, melphalan, meperidine, mepivacaine, mercaptopurine, mesalamine, mesoridazine, metaproterenol, metazoline methadone, methdilazine, methenamine, methimazol, methocarbamol, methochlopramide, methotrexate, methotrimeprazine, methyl dopa, methylphenidate, methysergide, metoclopramide, metolol, metolprolol tartrate, metoprolol, metoprolol succinate, metronidazole, miconazole, midazolam, miloride, minocycline, minoxidil, mitazapine, molindone, mometasone furoate, monopril, monozid, montelukast, morphine, mycophenolate mofetil hydrochloride, N-[3(R)-[2-(piperidin-4-yl)ethyl]-2-piperidon-1-yl]acetyl-3(R)-methyl-beta-alanine, nadolol, nafazodone, naftifine, nalbuphine, nalidixic acid, nalmefene, naloxone, naphazoline, naproxen, natrexone, nedocromil, nefazodone, nelfinavir mesylate, neticonazole, niacin, nicardipine, nicotine, nifedinpine, nifurantin, nimodipine, nitrofurantoin, nitrofurazone, nizatidine, nocodazole, nore phrine, norfloxacina oaan olopatadine hydrochloride, omeprazole, omoconazole, ondansetron, orconazole, orphenadrine, oxaprozin, oxazepam, oxfendazole, obendazole, oxibendazole, oxiconazole, oxmetidine, oxybutynin, oxycodone, oxymetazoline, oxymorphone, oxytetracycline, pamatolol, papaverine, parbendazole, parconazole, paroxetine, pemoline, penbutalol, penicillin VK, pentazocine, pentostatin, pentoxifylline, perphenazine, phenazopyridine, phenobarbitol, phenoxybenzamine, phentermine, phentolamine, phenyloin, physostigmine, pilocarpine, pimozide, pindolol, pipemidic acid, pirbuterol, piroxicam, polymixin, posaconazole, practolol, pramoxine, pravastatin, prazosin, prednisolone, prenalterol, primaquine, primidolol, prizidilol, procainamide, procaine, procaterol, prochlorperazine, promazine, promethazine, propanolol, proparacaine, proparacaine, propoxyphene, propranolol, pyrazinamide, pyrimethamine, pyroxidine, quazepam, quetiapine fumarate, quinapril, quinidine, quinine, quinterenol, raloxifen hydrochloride, ramipril, ranitidine, ranitidine hydrochloride, ravuconazole, retinoic acid, ribavarin, riboflavin, rifabutin, rifampin, rimiterol, risperidone, ritodrine, rocuronium, rosiglitazone, salmeterol, saperconazole, scopolamine, sertaconazole, sertraline, sibutramine, simvastatin, soterenol, sotolol, stavudine, sufentanil, sulconazole, sulfadiazine, sulfamethizole, sulfamethoxazole, sulfasalazine, sulfasoxazole, sulfinolol, sulfonterol, suloctidil, sumatriptan succinate, tacrine, tamoxifen, tamulosin hydrochloride, tazolol, temazepam, tenormin, tentrahydrozoline, terazosin, terbinafine, terbutaline, terconazole, terfenadine, tetracaine, tetracycline, tetrahydrazoline, tetrahydrolipstatin, theophylline, thiabendazole, thiamine, thiethylperazine, thioguanine, thioridazine, thiothixene, tiarnenidine, ticlopidine, timolol, tinazoline, tioconazole, tiotidine, tiprenolol, tipropidil, tocainide, tolamolol, tolazamide, tolazoline, tolmetin, tolteridine, toprimate, tramadol, tramazoline, trazodone, triamcinolone acetonide, triamterene, triazolam, trifluoroperazine, triflupromazine, trihexyphenidyl, trimeprazine, trimethoprin, trimetrexate, trimipramine, triplenamine, troglitazone, troleandomycin, tropicamide, tubocurarine, uracil mustard, valacyclovir hydrochloride, valconazole, valproic acid, valsartan, vecuronium, venlafaxine, verapamil, vidarabine, vinblastine, vincristine, vinorelbine, voriconazole, warfarin, xylometazoline, zinoconazole, zoficonazole and zolmitriptan.
[0006] The preferred pharmaceutical compounds which may be advantageously employed to produce the enhanced propertied human health pharmaceutical compounds of this invention include, but are not limited to, acrivistine, adapalene, aletamine, aliconazole, amiodarone, amitriptyline, amoxapine, amoxicillin, amphetamine, amrinone, arthrocine, astemizole, atorvastatin, atropine, becliconazole, benazepril, benzatropine, benzphetamine, beperiden, betahistine, bicalutamide, bisacodyl, brolaconazole, bromopheniramine, bupivacaine, buprenorphine, bupropion, caffeine, cafiminol, carbamazepam, cefachlor, cefadroxil, centerdrine, chlordiazepoxide, chloroprocaine, chloroquine, ciprofloxacin, citalopram, clemastine, clobesol, clomiphene, clonazepam, clonidine, clotrimazole, cloxacillin, clozapine, colchicine, croconazole, cyclobenzaprine, cyclopentolate, cyproheptadine, demethylimipramine, democonazole, deprenil, desipramine, dicodid, dicyclomine, diethylproprion, diltiazem, diphenidol, diphenoxylate hydrochloride, diphenhydramine doconazole, donezapil hydrochloride, doxapram, doxazosin, doxepin, eberconazole, econazole, enalapril, enoxacin, etintidine, famciclovir, fentanyl, fenfluramine, fenticonazole, flavoxate, fluazepam, fluconazole, fludorex, fluoxetine hydrochloride, flurbiprofen, fluticasone propionate, gabapentin, gemfibrozil, genaconazole, halazepam, haloperidol, hydroxyitraconazole, hydroxyzine, ibuprofen, indomethacin, iodoquinol, isoconazole, ketoprofen, ketorolac, lansoprazole, levomethadyl, lomefloxacin, loperidine hydrochloride, loratadine, lorazepam, lovastatin, mazindol, mechlorethamine, meperidine, mepivacaine, methadone, methimazole, methylphenidate, metronidazole, miconazole, minoxidil, molindone, monopril, monozid, naftifine, naphazoline, naproxen, nefazodone, neticonazole, nifedinpine, nifurantin, norfloxacin, olanzapine, omeprazole, omoconazole, orconazole, orphenadrine, oxaprozin, oxiconazole, oxmetidine, oxybutynin, oxycodone, oxymetazoline, papaverine, parconazole, paroxetine, pentazocine, perphenazine, phenoxybenzamine, phentermine, pilocarpine, pimozide, piroxicam, posaconazole, pramoxine, prazosin, procaine, proparacaine, propoxyphene, pyrazinamide, pyroxidine, quinapril, quinidine, ravuconazole, retinoic acid, risperidone, scopolamine, sertaconazole, sertraline, sibutramine, simvastatin, sufentanil, sulconazole, sulfamethizole, tacrine, tamoxifen, temazepam, terazosin, terbinafine, tetrahydrazoline, thiabendazole, ticlopidine, timolol, tioconazole, tocainide, tolazoline, tolteridine, tramadol, triamterene, trihexyphenidyl, troglitazone, troleandomycin, tropicamide, valconazole, valproic acid, verapamil, voriconazole, warfarin, xylometazoline and zinoconazole.
[0007] The pharmaceutical compounds which may be advantageously employed to produce the enhanced propertied veterinary pharmaceutical compounds of this invention include, but are not limited to, acepromazine, acetaminophen, acetazolamide, acetohydroxamic acid, acetylcysteine, acetylcysteine, acyclovir, aggrastat, albendazole, albuterol, allopurinol, altrenogest, aminocaproic acid, aminopentamide, aminophylline, aminopropazine, amiodarone, amitraz, amitriptyline, amlodipine, amoxicillin, ampicillin, amprolium, amrinone, apomorphine, apramycin, ascorbic acid, aspirin, atenolol, atipamezole, atropine, aurothioglucose, azaperone, azathioprine, benazepril, betamethasone, boldenone, bromocriptine, buprenorphine, buspirone, butorphanol, captopril, carbenicillin, carnitine, carprofen, cefadroxil, cefazolin, cefoperawne, cefotaxime, cefoxitin, ceftiofur, ceftriaxone, cephalexin, cephalothin, cephapirin, chloramphenicol, chlorothiazide, chlorpheniramine, chlorpromazine, chlorpropamide, cilastatin, cimetidine, ciprofloxacin, cisapride, clavulanate, clemastine, clenbuterol, clioquinol, clomipramine, clonazepam, cloprostenol, clorazepate, clorsulon, cloxacillin, codeine, colchicine, cyclophosphamide, cyproheptadine, cytarabine, cythioate, danazol, decoquinate, desoxycorticosterone Piv, detomidine, dexamethasone, dexpanthenol, diazoxide, dichlorphenamide, dicloxacillin, diethylcarbamazine, difloxacin, digitoxin, digoxin, dihydrotachysterol, diltiazem, dimenhydrinate, dimercaprol, dinoprost, diphenhydramine, diphenoxylate, disopyramide, dobutamine, dopamine, doramectin, doxapram, doxepin, doxorubicin, doxylamine, droperidol, edetate calcium, enalapril, enrofloxacin, ephedrine, epinephrine, esmolol, estradiol, ethacrynic acid, ethylisobutrazine, etidronate, etodolac, famotidine, febantel, fenbendazole, fenprostalene, fentanyl, fipronil, florfenicol, fluconazole, flucytosine, fludrocortisone, flumazenil, flumethasone, flunixin, fluprostenol, fomepizole-4-MP, furosemide, glipizide, glycopyrrolate, guaifenesin, hetacillin, hydralazine, hydrochlorothiazide, hydrocodone, hydrocortisone, hydroxyurea, hydroxyzine, imidacloprid, imidocarb, imipenem, imipramine, isopropamide, isoproterenol, isotretinoin, isoxsuprine, itraconazole, ketamine, ketoconazole, ketoprofen, levamisole, levothyroxine, lidocaine, lincomycin, liothyronine, lomustine, lufenuron, mechlorethamine, meclizine, meclofenamic acid, medetomidine, medroxyprogesterone, megestrol, melphalan, meperidine, mephenyloin, mercaptopurine, methenamine, methimazole, methionine, methocarbamol, methotrexate, methylprednisolone, metoclopramide, metoprolol, metronidazole, mexiletine, mibolerone, midazolam, misoprostol, morantel, morphine, naloxone, naltrexone, nandrolone, naproxen, nitrofurantoin, omeprazole, orbifloxacin, ormetoprim, oxacillin, oxazepam, oxfendazole, oxibendazole, oxybutynin, oxymorphone, penicillamine, penicillin G, penicillin V, pentazocine, pentoxifylline, phenoxybenzamine, phenylephrine, phenylpropanolamine, phenyloin, phytonadione, piperazine, pirlimycin, piroxicam, pralidoxime, prazosin, prednisolone, prednisone, primidone, procainamide, promazine, propofol, propranolol, prostaglandin E1, pyrantel, pyrilamine, pyrimethamine, quinacrine, quinidine, ranitidine, selegiline, stanozolol, sulfachlorpyridazine, sulfadiazine, sulfadimethoxine, sulfamethoxazole, sulfasalazine, terbutaline, testosterone, theophylline, thiabendazole, thiamine, thiotepa, tiamulin, ticarcillin, tiletamine, tiopronin, tocainide, tolazoline, triamcinolone, trimeprazine, trimethoprim, tripelennamine, ursodiol, valproic acid, verapamil, vinblastine, vincristine, warfarin, xylazine and yohimbine.
[0008] The preferred pharmaceutical compounds which may be advantageously employed to produce the enhanced propertied veterinary pharmaceutical compounds of this invention include, but are not limited to, acepromazine, albendazole, aminocaproic acid, aminophylline, aminopropazine, amiodarone, amitriptyline, amprolium, atipamezole, atropine, azaperone, benazepril, buspirone, captopril, cephapirin, chlorpheniramine, cisapride, clemastine, clioquinol, clomipramine, cyproheptadine, detomidine, diethylcarbamazine, diltiazem, diphenhydramine, diphenoxylate, disopyramide, doxapram, doxepin, doxylamine, droperidol, enalapril, febantel, fenbendazole, fentanyl, fluconazole, guaifenesin, hetacillin, hydrocodone, hydroxyzine, imidacloprid, itraconazole, ketamine, ketoprofen, levamisole, lidocaine, lincomycin, lomustine, mechlorethamine, meclizine, meclofenamic acid, meperidine, mercaptopurine, methenamine, methotrexate, mexiletine, mibolerone, morantel, naltrexone, omeprazole, ormetoprim, oxazepam, oxybutynin, pentazocine, piroxicam, primidone, procainamide, promazine, prostaglandin E1, pyrantel, quinacrine, quinidine, selegiline, sulfachlorpyridazine, sulfadiazine, sulfamethoxazole, theophylline, thiabendazole, tiamuLin, tiletamine, tocainide, valproic acid, verapamil, vincristine, warfarin and xylazine.
[0009] A first embodiment of this invention relates to a pharmaceutical moiety represented by Z1(X1)m wherein
[0010] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0011] Z1 represents the remainder of said pharmaceutical moiety,
[0012] m is 1, and
[0013] Z1(X1)m—H represents the complete pharmaceutical compound, said pharmaceutical moiety Z1(X1)m being substituted with a second moiety on X1, said second moiety comprising a substituent which enhances or changes the properties of said pharmaceutical compound, said substituent having the formula
1
[0014] wherein
[0015] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0016] G21 is an oxygen atom, a sulfur atom or NR3,
[0017] q is 0,
[0018] t is 0 or 1,
[0019] &Circlesolid;- represents the connection point of said substituent to said pharmaceutical moiety Z1(X1)m,
[0020] Z2(X2)q is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, alkylcarbonylaminoalkenyl, arylcarbonylaminoalkenyl, heteroarylcarbonylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioaLkenyl, haloalkylthioalkynyl, NR3R4, SO2NR3R4, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, dialkoxyphosphorylalkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and alkylNR3R4, aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, alkylcarbonylalkyl, alkenylcarbonylalkyl, alkynylcarbonylalkyl, heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl, or heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0021] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0022] j is 0, 1 or 2,
[0023] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, alkoxy or the anion of a carboxylic acid and j is 0, or 2,
[0024] R1 is
2
[0025] wherein
[0026] G30 is an oxygen atom or a sulfur atom,
[0027] G31 is an oxygen atom, a sulfur atom or NR3,
[0028] d is 0,
[0029] t′ is 0 or 1,
[0030] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkenylcarbonyl, alkenylcarbonylalkyl, alkynylcarbonyl, alkynylcarbonylalkyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylalkylamino, acetylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl, or aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylcarbonylalkyl, heteroaroxycarbonylalkyl, or heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylarylcarbonylalkyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2, Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0031] R2 is a hydrogen atom, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxy, a carboxylate salt, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylaLienyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, carboxy, alkoxycarbonyl, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl or aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl, or arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl or heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl, or heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4,
[0032] R3, R4 and R5 are each independently a hydrogen atom, alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl, alkynyl, or alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl or alkynyl substituted with one or more halo, aryl, aralkyl, aralkenyl, aralkynyl, or aryl, aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo; alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0033] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0034] A second embodiment of this invention relates to a pharmaceutical moiety represented by Z1(X1)m wherein
[0035] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0036] Z1 represents the remainder of said pharmaceutical moiety,
[0037] m is 1, and
[0038] Z1(X1)m—H represents the complete pharmaceutical compound, said pharmaceutical moiety Z1(X1)m being substituted with a second moiety on X1, said second moiety comprising a substituent which enhances or changes the properties of said pharmaceutical compound, said substituent having the formula
3
[0039] wherein
[0040] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0041] G21 is an oxygen atom, a sulfur atom or NR3,
[0042] q is 0 or 1,
[0043] &Circlesolid;- represents the connection point of said substituent to said pharmaceutical moiety Z1(X1)m,
[0044] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0045] t is 0 or 1,
[0046] Z2(X2)q(C(=G20)G21)t is a second pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G2′)t—H represents the second pharmaceutical,
[0047] Z2 represents the remainder of said second pharmaceutical moiety,
[0048] R1 is
4
[0049] wherein
[0050] G30 is an oxygen atom or a sulfur atom,
[0051] G31 is an oxygen atom, a sulfur atom or NR3,
[0052] t′ and d are each independently 0 or 1,
[0053] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0054] Z3(X3)d(G31)t′ is a second alternative pharmaceutical moiety when d is 1 wherein Z3(X3)d(G3′)t—H represents the second alternative pharmaceutical,
[0055] Z3 represents the remainder of said second alternative pharmaceutical moiety,
[0056] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkenylcarbonyl, alkenylcarbonylalkyl, alkynylcarbonyl, alkynylcarbonylalkyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylalkylamino, acetylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkeiiyl, alkoxyalkynyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl, or aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylcarbonylalkyl, heteroaroxycarbonylalkyl, or heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylarylcarbonylalkyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterQcyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0057] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0058] R2 is a hydrogen atom, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxy, a carboxylate salt, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkyl, alkoxy, haloalkoxy, carboxy, alkoxycarbonyl, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl or aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl, or arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl or heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloallcynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl, or heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4,
[0059] R3, R4 and R5 are each independently a hydrogen atom, alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl, alkynyl, or alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl or alkynyl substituted with one or more halo, aryl, aralkyl, aralkenyl, aralkynyl, or aryl, aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, and haloalkoxy, heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring,
[0060] (q+d) is 1, or
[0061] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0062] A third embodiment of this invention relates to a pharmaceutical compound of formula (I)
5
[0063] wherein
[0064] A is
6
[0065] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0066] G21 is an oxygen atom, a sulfur atom or NR3,
[0067] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0068] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0069] m, q and t are each independently 0 or 1,
[0070] n is 1 or 2,
[0071] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m—H represents the pharmaceutical,
[0072] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t—H or Z2(X2)q(C(=G20)G2′)t represents the pharmaceutical,
[0073] Z1(X1)m, when m is 0, is a hydrogen atom, halo, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, hydroxyalkyl, alkylsulfonylalkyl, acetylaminoalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, alkylcarbonylaminoalkenyl, arylcarbonylaminoalkenyl, heteroarylcarbonylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, NR3R4, SO2NR3R4, OR3, S(O)jR3, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, aryl, arylcarbonyl, arylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, or aryl, arylcarbonyl, arylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, aralkylcarbonyl, aralkenylcarbonyl, aralkylcarbonylalkyl, aralkenylcarbonylalkyl, or aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, aralkylcarbonyl, aralkenylcarbonyl, aralkylcarbonylalkyl, aralkenylcarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl, or heteroaryl, heteroarylcarbonyl, heteroaroxycarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, heteroaralkylcarbonyl, heteroaralkylcarbonylalkyl, heteroaralkenylcarbonyl, heteroaralkenylcarbonylalkyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl, heteroaralkylcarbonyl, heteroaralkylcarbonylalkyl, heteroaralkenylcarbonyl, heteroaralkenylcarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0074] Z2(X2)q is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, alkylcarbonylaminoalkenyl, arylcarbonylaminoalkenyl, heteroarylcarbonylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, NR3R4, SO2NR3R4, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, dialkoxyphosphorylalkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and alkylNR3R4, aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, alkylcarbonylalkyl, alkenylcarbonylalkyl, alkynylcarbonylalkyl, heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl, or heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0075] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR37 NR3R4, OSO2NR3R4, OP(—O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0076] j is 0, 1 or 2,
[0077] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0078] R1 is
7
[0079] wherein
[0080] G30 is an oxygen atom or a sulfur atom,
[0081] G31 is an oxygen atom, a sulfur atom or NR3,
[0082] t′ and d are each independently 0 or 1,
[0083] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0084] Z3(X3)d(G31)t, is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t′—H represents the pharmaceutical,
[0085] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkenylcarbonyl, alkenylcarbonylalkyl, alkynylcarbonyl, alkynylcarbonylalkyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylalkylamino, acetylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl, or aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralk-enyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylcarbonylalkyl, heteroarbxycarbonylalkyl, or heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylarylcarbonylalkyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaraLkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0086] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0087] each R2 is independently a hydrogen atom, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxy, a carboxylate salt, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalky nyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, carboxy, alkoxycarbonyl, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl or aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl, or arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl or heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl, or heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4,
[0088] R3, R4 and R5 are each independently a hydrogen atom, alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl, alkynyl, or alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl or alkynyl substituted with one or more halo, aryl, aralkyl, aralkenyl, aralkynyl, or aryl, aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0089] A is
8
[0090] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0091] provided that when both m and q are 0, A is
9
[0092] and
[0093] within the definition of R1
[0094] d is 1,
[0095] G30, G31, Z3, X3 and t′ are as previously defined and
[0096] Z3(X3)d(G31)t′ is a pharmaceutical moiety wherein Z3(X3)d(G3′)t′—H represents the pharmaceutical, or
[0097] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0098] In a preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein t is 1, m is 1, q is 0, (X1) is a nitrogen atom and Z1(X1)m—H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0099] In another preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein t is 1, m is 1, q is 0, (X1)m is a phosphorous, oxygen or sulfur atom and Z1(X1)m—H is a pharmaceutical, or t is 1, m is 0, q is 1, (X2)q is a phosphorous, oxygen or sulfur atom and Z2(X2)q-[(C=G20)-G21]t—H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0100] In another preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein t is 1, m is 0, q is 1, (X2)q is a carbon atom and Z2(X2)q-[(C=G20)-G21]t-H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0101] In another preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein t is 0, m is 1, q is 0, (X1)m is a nitrogen, phosphorous, oxygen or sulfur atom and Z1(X1)m—H is a pharmaceutical, or t is 0, m is 0, q is 1, (X2)q is a nitrogen, phosphorous, oxygen, sulfur or carbon atom and Z2(X2)q-[(C=G20)-G21]t-H is a pharmaceutical or Z2(X2)q-[(C=G20)-G21]t is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0102] In another preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein t is 0 or 1, m is 1, q is 1, (X1)m is a nitrogen, phosphorous, oxygen or sulfur atom, (X2)q is a nitrogen, phosphorous, oxygen, sulfur or carbon atom, Z1(X1)m—H is a pharmaceutical and Z2(X2)q—(C=G20-G21)t-H or Z2(X2)q-(C=G20-G21)t is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0103] In another preferred third embodiment of this invention, the pharmaceutical compound is represented by the compound of formula (I) wherein A is
10
[0104] m and q are 0,
[0105] Z1(X1)m and Z2(X2)q are non-pharmaceutical moieties,
[0106] R1 is
11
[0107] wherein
[0108] G30 is an oxygen atom or a sulfur atom,
[0109] G31 is an oxygen atom, a sulfur atom or NR3,
[0110] d is 1,
[0111] t′ is 0 or 1,
[0112] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G331 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0113] Z3(X3)d(G31)t′ is a pharmaceutical moiety wherein Z3(X3)d(G31)t′-H represents the pharmaceutical, or
[0114] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0115] In another preferred third embodiment of this invention, a pharmaceutical compound is represented by formula (I)
12
[0116] wherein
[0117] A is
13
[0118] R1 is
14
[0119] (d+m+q) is 1 or 2, or
[0120] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0121] In another preferred third embodiment of this invention, a pharmaceutical compound is represented by formula (I)
15
[0122] wherein
[0123] A is
16
[0124] both q and t are 1,
[0125] X2 is a carbon atom, or
[0126] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0127] In another preferred third embodiment of this invention, a pharmaceutical compound is represented by formula (I)
17
[0128] wherein
[0129] A is
18
[0130] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0131] G21 is an oxygen atom, a sulfur atom or NR3,
[0132] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0133] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0134] m, q and t are each independently 0 or 1,
[0135] n is 1 or 2,
[0136] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m—H represents the pharmaceutical,
[0137] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G21)t-H represents the pharmaceutical,
[0138] Z1(X1)m, when m is 0, is a hydrogen atom, halo, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10))alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, OR3, S(O)jR3, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4, and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-Cs)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0139] Z2(X2)q is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkenylcarbonyl, (C1-C20)alkynylcarbonyl, hydroxy(C1-C2-0)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C9)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, di(C1-C10)alkoxyphosphoryl(C1-C10)alkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and (C1-C10)alkylNR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(Ca-CB)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, (C1-C10)alkylcarbonyl(C1-C10)alkyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0140] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0141] j is 0, 1 or 2,
[0142] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M-}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, (C1-C8)alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0143] R1 is
19
[0144] wherein
[0145] G30 is an oxygen atom or a sulfur atom,
[0146] G31 is an oxygen atom, a sulfur atom or NR3,
[0147] t′ and d are each independently 0 or 1,
[0148] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0149] Z3(X3)d(G31)t′ is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t′-H represents the pharmaceutical,
[0150] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclO(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0151] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0152] each R2 is independently a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C1-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C10)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10 alkyl, or a carbon ar C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkWxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0153] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C10)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0154] A is
20
[0155] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0156] provided that when both m and q are 0, A is
21
[0157] and
[0158] within the definition of R1
[0159] d is 1,
[0160] G30, G31, Z3, X3 and t′ are as previously defined and
[0161] Z3(X3)d(G31)t′ is a pharmaceutical moiety wherein Z3(X3)d(G31)t′—H represents the pharmaceutical, or
[0162] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0163] In a fourth embodiment of this invention, a human health pharmaceutical compound is represented by formula (I)
22
[0164] wherein
[0165] A is
23
[0166] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0167] G21 is an oxygen atom, a sulfur atom or NR3,
[0168] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0169] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0170] m is 1,
[0171] q and t are each independently 0 or 1,
[0172] n is 1 or 2,
[0173] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m—H represents the pharmaceutical selected from the group consisting of aletamine, amoxapine, amoxicillin, amphetamine, atorvastatin, benazepril, betahistine, bupropion, carbamazepam, cefachlor, cefadroxil, centerdrine, chlordiazepoxide, chloroquine, ciprofloxacin, clonazepam, clonidine, clozapine, demethylimipramine, deprenil, desipramine, enoxacin, etintidine, fenfluramine, fludorex, fluoxetine hydrochloride, gabapentin, lansoprazole, mepivacalne, metnylpneniclate, moincdone, napnazoline, norfloxacin, olanzapine, omeprazole, oxmetidine, paroxetine, phentermine, pimozide, piroxicam, posaconazole, prazosin, procaine, propanolol, proparacaine, quinapril, sertraline, sulfamethizole, tacrine, temazepam, terazosin, tetrahydrazoline, thiabendazole, timolol, tocainide, tolazoline, tramadol, triamterene, troglitazone and xylometazoline when X1 is a nitrogen atom, or
[0174] the pharmaceutical selected from the group consisting of atorvastatin, atropine, bicalutamide, buprenorphine, cafiminol, clobesol, deprenil, doxazosin, enalapril, famciclovir, fluconazole, fluticasone propionate, genaconazole, haloperidol, hydroxyitraconazole, hydroxyzine, iodoquinol, loperidine hydrochloride, lorazepam, lovastatin, mazindol, metronidazole, oxycodone, quinidine, scopolamine, simvastatin, tramadol and voriconazole when X1 is an oxygen atom, or
[0175] the pharmaceutical methimazole when X1 is a sulfur atom,
[0176] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G21)t—H represents the pharmaceutical,
[0177] Z2(X2)q is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkenylcarbonyl, (C1-C20)alkynylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C2-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10) alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10) alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, di(C1-C10)alkoxyphosphoryl(C1-C10)alkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and (C1-C10)alkylNR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, (C1-C10)alkylcarbonyl(C1-C10)alkyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0178] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0179] j is 0, 1 or 2,
[0180] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, (C1-C8)alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0181] R1 is
24
[0182] wherein
[0183] G30 is an oxygen atom or a sulfur atom,
[0184] G31 is an oxygen atom, a sulfur atom or NR3,
[0185] t′ and d are each independently 0 or 1,
[0186] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0187] Z3(X3)d(G31)t′ is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t′—H represents the pharmaceutical,
[0188] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-CS8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10) alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR1R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein j is 0, 1 or 2,
[0189] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0190] each R2 is independently a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyll cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0191] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halO(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)-alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0192] A is
25
[0193] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0194] provided that when both m and q are 0, A is
26
[0195] and
[0196] within the definition of R1
[0197] d is 1,
[0198] G30, G31, Z3, X3 and t′ are as previously defined and
[0199] Z3(X3)d(G31)t′ is a pharmaceutical moiety wherein Z3(X3)d(G31)t′—H represents the pharmaceutical, or
[0200] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0201] In a fifth embodiment of this invention, a human health pharmaceutical compound is represented by formula (I)
27
[0202] wherein
[0203] A is
28
[0204] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0205] G21 is an oxygen atom, a sulfur atom or NR3,
[0206] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0207] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0208] m and t are each independently 0 or 1,
[0209] q is 1,
[0210] n is 1 or 2,
[0211] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m—H represents the pharmaceutical,
[0212] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G2′)t—H represents the pharmaceutical selected from the group consisting of acrivistine, aliconazole, amiodarone, amitriptyline, amoxapine, amrinone, astemizole, atropine, becliconazole, benzatropine, benzphetamine, beperiden, bisacodyl, brolaconazole, bromopheniramine, bupivacaine, caffeine, chloroprocaine, citalopram, clemastine, clomiphene, clotrimazole, colchicine, croconazole, cyclobenzaprine, cyclopentolate, cyproheptadine, democonazole, dicodid, dicyclomine, diethylproprion, diphenhydramine, diphenidol, diltiazem, diphenoxylate hydrochloride, doconazole, donezapil hydrochloride, doxapram, doxepin, eberconazole, econazole, fentanyl, fenticonazole, flavoxate, fluazepam, fluconazole, halazepam, hydroxyitraconazole, isoconazole, lansoprazole, levomethadyl, loratadine, mechlorethamine, meperidine, mepivacaine, methadone, methimazole, miconazole, minoxidil, naftifine, nefazodone, neticonazole, nifurantin, omoconazole, orconazole, orphenadrine, oxiconazole, oxybutynin, oxymetazoline, papaverine, parconazole, phenoxybenzamine, pilocarpine, pramoxine, propoxyphene, pyrazinamide, pyroxidine, ravuconazole, retinoic acid, risperidone, sertaconazole, sibutramine sufentanil, sulconazole, tamoxifen, terbinafine, ticlopidine, tioconazole, tolteridine, trihexyphenidyl, troleandomycin, tropicamide, valconazole, verapamil and zinoconazole when X2 is a nitrogen atom, or
[0213] the pharmaceutical selected from the group consisting of fluconazole, genaconazole, hydroxyitraconazole, iodoquinol, lovastatin, mazindol, metronidazole, posaconazole, voriconazole and warfarin when X2 is an oxygen atom, or
[0214] the pharmaceutical selected from the group consisting of adapalene, arthrocine, cloxacillin, flurbiprofen, gemfibrozil, hydroxyitraconazole, ibuprofen, indomethacin, ketoprofen, ketorolac, loratadine, monopril, oxaprozin, valproic acid and verapamil when X2 is an carbon atom,
[0215] Z1(X1)m, when m is 0, is a hydrogen atom, halo, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-Cs)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-Cs)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, OR3, S(O)jR3, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4, and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-Cs)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0216] R1 is
29
[0217] wherein
[0218] G30 is an oxygen atom or a sulfur atom,
[0219] G31 is an oxygen atom, a sulfur atom or NR3,
[0220] t′ and d are each independently 0 or 1,
[0221] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0222] Z3(X3)d(G31)t′ is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t′—H represents the pharmaceutical,
[0223] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C10)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein j is 0, 1 or 2,
[0224] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0225] each R2 is independently a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-Cs)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(c3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0226] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0227] A is
30
[0228] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0229] provided that when both m and q are 0, A is
31
[0230] and
[0231] within the definition of R1
[0232] dis 1,
[0233] G30, G31, Z3, X3 and t′ are as previously defined and
[0234] Z3(X3)d(G31)t′ is a pharmaceutical moiety wherein Z3(X3)d(G3′)t′—H represents the pharmaceutical, or
[0235] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0236] In a sixth embodiment of this invention, a veterinary pharmaceutical compound is represented by formula (I)
32
[0237] wherein
[0238] A is
33
[0239] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0240] G21 is an oxygen atom, a sulfur atom or NR3,
[0241] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0242] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0243] m is 1,
[0244] q and t are each independently 0 or 1,
[0245] n is 1 or 2,
[0246] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m-H represents the pharmaceutical selected from the group consisting of albendazole, aminocaproic acid, aminophylline, amprolium, atipamezole, benazepril, cisapride, detomidine, disopyramide, enalapril, febantel, fluconazole, imidacloprid, ketamine, lidocaine, lincomycin, lomustine, mechlorethamine, meclofenamic acid, mercaptopurine, methotrexate, mexiletine, ormetoprim, piroxicam, primidone, procainamide, prostaglandin E1, quinacrine, quinidine, sulfachlorpyridazine, sulfadiazine, sulfamethoxazole, theophylline, thiabendazole, tiletamine, tocainide, vincrist-ine and xylazine when X1 is a nitrogen atom, or
[0247] the pharmaceutical selected from the group consisting of clioquinol, enalapril, guaifenesin, mibolerone, oxazepam, prostaglandin E1 and warfarin when X1 is an oxygen atom,
[0248] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(Y2)q(C(=G20)G21), or Z2(X2)q(C(=G2O)G2′)t—H represents the pharmaceutical,
[0249] Z2(X2)q is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkenylcarbonyl, (C1-C20)alkynylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C8-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, di(C1-C10)alkoxyphosphoryl(C1-C10)alkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, C(═O)OR2, C(═O)SR2, C(—S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and (C1-C10)alkylNR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, (C1-C10)alkylcarbonyl(C1-C10)alkyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0250] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0251] j is 0, 1 or 2,
[0252] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M-}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, (CI-Cg)alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0253] R1 is
34
[0254] wherein
[0255] G30 is an oxygen atom or a sulfur atom,
[0256] G31 is an oxygen atom, a sulfur atom or NR3,
[0257] t′ and d are each independently 0 or 1,
[0258] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0259] Z3(X3)d(G31)t is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t′—H represents the pharmaceutical,
[0260] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-Ca)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-Cs)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-CB)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-Cs)alkyl(C2-C10)alkvnyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)-alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents indepeindently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein j is 0, 1 or 2,
[0261] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0262] each R2 is independently a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-Cg)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alk-enyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarykarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy; nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0263] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(Ca-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-Cs)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkvnyl, (C1-C10)alkloxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0264] A is
35
[0265] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0266] provided that when both m and q are 0, A is
36
[0267] and
[0268] within the definition of R1
[0269] d is 1,
[0270] G30, G31, Z3, X3 and t′ are as previously defined and
[0271] Z3(X3)d(G31)t is a pharmaceutical moiety wherein Z3(X3)d(G3′)t—H represents the pharmaceutical, or
[0272] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0273] In a seventh embodiment of this invention, a veterinary pharmaceutical compound is represented by formula (I)
37
[0274] wherein
[0275] A is
38
[0276] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0277] G21 is an oxygen atom, a sulfur atom or NR3,
[0278] X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1,
[0279] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0280] m and t are each independently 0 or 1,
[0281] q is 1,
[0282] n is 1 or 2,
[0283] Z1(X1)m is a pharmaceutical moiety when m is 1 wherein Z1(X1)m—H represents the pharmaceutical,
[0284] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G21)t—H represents the pharmaceutical selected from the group consisting of acepromazine, albendazole, aminopropazine, amiodarone, amitriptyline, atropine, azaperone, buspirone, captopril, cephapirin, chlorpheniramine, clemastine, clomipramine, cyproheptadine, diethylcarbamazine, diltiazem, diphenhydramine, diphenoxylate, doxapram, doxepin, doxylamine, droperidol, febantel, fenbendazole, fentanyl, hetacillin, hydrocodone, hydroxyzine, itraconazole, levamisole, meclizine, meperidine, methenamine, morantel, naltrexone, omeprazole, oxybutynin, pentazocine, piroxicam, primidone, procainamide, promazine, pyrantel, selegiline, thiabendazole, tiamulin and verapamil when X2 is a nitrogen atom, or
[0285] the pharmaceutical selected from the group consisting of clioquinol, guaifenesin, mibolerone, oxazezam and warfarin when X2 is an oxygen atom, or
[0286] the pharmaceutical selected from the group consisting of ketoprofen and valproic acid when X2 is a carbon atom,
[0287] Z1(X1)m, when m is 0, is a hydrogen atom, halo, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-Ca)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, OR3, S(O)jR3, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4, and NR3R4, ar(C1-C10) alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alken-ylcarbonyl, ar(C2-C10)alkenycarbonyl(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10) alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-Cs)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, hetercar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0288] R1 is
39
[0289] wherein
[0290] G30 is an oxygen atom or a sulfur atom,
[0291] G31 is an oxygen atom, a sulfur atom or NR3,
[0292] t′ and d are each independently 0 or 1,
[0293] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G3′ is an oxygen atom or a sulfur atom,
[0294] Z3(X3)d(G31)t′ is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G31)t—H represents the pharmaceutical,
[0295] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-Cs)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-Cs)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, aryarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arCyclo(C3-Cs)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10))akyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10) alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein i is 0, 1 or 2,
[0296] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0297] each R2 is independently a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-CB)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10) alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alke nyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl; (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10)alkyl, (C2-C10) alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0298] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8) alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alenyl, (C2-C10)alkyriyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0299] A is
40
[0300] wherein each R2, G20, G21, G30 and G31 are as previously defined,
[0301] provided that when both m and q are 0, A is
41
[0302] and
[0303] within the definition of R1
[0304] d is 1,
[0305] G30, G31, Z3, X3 and t′ are as previously defined and
[0306] Z3(X3)d(G3′)t′ is a pharmaceutical moiety wherein Z3(X3)d(G3′)t′—H represents the pharmaceutical, or
[0307] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0308] In an eighth embodiment of this invention, the pharmaceutical compound is represented by formula (I)
42
[0309] wherein
[0310] A is
43
[0311] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0312] G21 is an oxygen atom, a sulfur atom or NR3,
[0313] X1 is a nitrogen atom attached to Z1,
[0314] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0315] m is 1,
[0316] q and t are each independently 0 or 1,
[0317] Z1(X1)m is a pharmaceutical moiety selected from
44
[0318] wherein Z1(X1)m—H represents the respective pharmaceutical selected from
45
[0319] -&Circlesolid; represents the connection point between said pharmaceutical moiety and the moiety represented by
46
[0320] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G21)tH represents the pharmaceutical,
[0321] Z1(X1)m, when m is 0, is a hydrogen atom, halo, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10) alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, R3, S(O)jR3, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4, and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C o)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0322] Z2(X2)q is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkenylcarbonyl, (C1-C20)alkynylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, di(C1-C10)alkoxyphosphoryl(C1-C10)alkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, C(═O)OR2, C(—O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and (C1-C10)alkylNR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydrqxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-Cto)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, (C1-C10)alkylcarbonyl(C1-C10)alkyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10) alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and N—R3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0323] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0324] j is 0, 1 or 2,
[0325] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, (C1-C8)alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0326] R1 is
47
[0327] wherein
[0328] G30 is an oxygen atom or a sulfur atom,
[0329] G31 is an oxygen atom, a sulfur atom or NR3,
[0330] t′ and d are each independently 0 or 1,
[0331] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0332] Z3(X3)d(G31)t′ is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G3′)t—H represents the pharmaceutical,
[0333] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20) alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alkenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10) alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)a kynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C1-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein j is 0, 1 or 2,
[0334] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0335] (d+q)is 0 or 1,
[0336] R2 is a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10) alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynylv (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10) alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0337] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-Cs)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0338] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0339] In a ninth embodiment of this invention, the pharmaceutical-compound is represented by formula (I)
48
[0340] wherein
[0341] A is
49
[0342] G10, G11 and G20 are each independently an oxygen atom or a sulfur atom,
[0343] G21 is an oxygen atom, a sulfur atom or NR3,
[0344] X1 is an oxygen atom attached to Z1,
[0345] X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2,
[0346] m is 1,
[0347] q and t are each independently 0 or 1,
[0348] Z1(X1)m is a pharmaceutical moiety selected from
50
[0349] wherein Z1(X1)m—H represents the respective pharmaceutical selected from
51
[0350] -&Circlesolid; represents the connection point between said pharmaceutical moiety and the moiety represented by
52
[0351] Z2(X2)q(C(=G20)G21)t is a pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G21)t—H represents the pharmaceutical,
[0352] Z1(X1)m, when m is 0, is a hydrogen atom, halo, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C9)cycloalkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, OR3, S(O)jR3, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4, and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C1-C10)alkylcarbonyl(C1-C10)alkyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkenylcarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2,
[0353] Z2(X2)q is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkenylcarbonyl, (C1-C20)alkynylcarbonyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C20)alkenyl, halo(C2-C20)alkenyl, (C1-C10)alkylcarbonylamino(C2-C10)alkenyl, arylcarbonylamino(C2-C10)alkenyl, heteroarylcarbonylamino(C2-C10)alkenyl, (C2-C20)alkynyl, halo(C2-C20)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)Galkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxy(C3-C8)cycloal(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C5)alkoxy(C1-C5)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, SO2NR3R4, NR3R4, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, di(C1-C10)alkoxyphosphoryl(C1-C10)alkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, cyano, hydroxy, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylsulfonyl, thiocyanato, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-Cto)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and (C1-C10)alkylNR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, lieteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, (C1-C10)alkylcarbonyl(C1-C10)alkyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, heterocyclylcarbonyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, arylcarbonyl, arylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, aroxycarbonyl, aroxycarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, heteroarylcarbonyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl, heteroaroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, and C(═N-G22)R2 when q is 0 and t is 1,
[0354] G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4,
[0355] j is 0, 1 or 2,
[0356] Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M− is halo, hydroxy, (C1-C8)alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2,
[0357] R1 is
53
[0358] wherein
[0359] G30 is an oxygen atom or a sulfur atom,
[0360] G31 is an oxygen atom, a sulfur atom or NR3,
[0361] t′ and d are each independently 0 or 1,
[0362] X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G31 is an oxygen atom or a sulfur atom,
[0363] Z3(X3)d(G31)t is a pharmaceutical moiety when d is 1 wherein Z3(X3)d(G3′)t—H represents the pharmaceutical,
[0364] Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, (C1-C20)alkyl, (C1-C10)alkylcarbonyloxy(C1-C10)alkyl, (C1-C20)alkylcarbonyl, (C1-C10)alkylcarbonyl(C1-C10)alkyl, hydroxy(C1-C20)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C1-C10)alkylcarbonylamino(C1-C10)alkyl, arylcarbonylamino(C1-C10)alkyl, heteroarylcarbonylamino(C1-C10)alkyl, acetylamino(C1-C10)alkyl, halo(C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkenylcarbonyl(C1-C10)alkyl, acetylamino(C2-C10)alkenyl, halo(C2-C10)alenyl, (C2-C10)alkynyl, (C2-C10)alkynylcarbonyl(C1-C10)alkyl, halo(C2-C10)alkynyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, carboxycyclo(C3-C8)alkyl, carboxycyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkenyl(C1-C10)alkyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkenyl, carboxycyclo(C3-C8)alkyl(C2-C10)alkynyl, carboxycyclo(C3-C8)alkenyl(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, halo(C1-C10)alkoxy(C1-C10)alkyl, halo(C1-C10)alkoxy(C2-C10)alkenyl, halo(C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, halo(C1-C10)alkylthio(C1-C10)alkyl, halo(C1-C10)alkylthio(C2-C10)alkenyl, halo(C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl, or aryl, arylcarbonyloxy(C1-C10)alkyl, arylcarbonyl(C1-C10)alkyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, (C1-C10)alkyl, (C1-C10)alkylsulfonyl(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl, or ar(C1-C10)alkyl, ar(C1-C10)alkylcarbonyloxy(C1-C10)alkyl, ar(C1-C10)alkylcarbonyl(C1-C10)alkyl, ar(C1-C10)alkoxycarbonyl(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, arcyclo(C3-C8)alkyl, aroxy(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, Cyclo(C3-C8)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxycarbonyl(C1-C10)alkyl, or heteroaryl, heteroarylcarbonyloxy(C1-C10)alkyl, heteroarylcarbonyl(C1-C10)alkyl, heteroaroxyycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl, or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, hetercyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heterocyclyl, heterocyclylcarbonyloxy(C1-C10)alkyl, heterocyclylcarbonyl(C1-C10)alkyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, wherein j is 0, 1 or 2,
[0365] Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2,
[0366] (d+q)is 0 or 1,
[0367] R2 is a hydrogen atom, (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy, a carboxylate salt, carboxy(C1-C20)alkyl, carboxy(C2-C20)alkenyl, carboxy(C2-C20)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-CB)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or (C1-C20)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C1-C10)alkoxy(C2-C10)alkenyl, (C1-C10)alkoxy(C2-C10)alkynyl, (C1-C10)alkylthio(C1-C10)alkyl, (C1-C10)alkylthio(C2-C10)alkenyl, (C1-C10)alkylthio(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C20)alkoxycarbonyl, (C1-C10)alkoxycarbonyl(C1-C10)alkyl, (C1-C10)alkoxycarbonyl(C2-C10)alkenyl, (C1-C10)alkoxycarbonyl(C2-C10)alkynyl, (C1-C20)alkylcarbonyl, (C2-C10)alkenylcarbonyl, (C2-C10)alkynylcarbonyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-Cg)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, SO2NR3R4 and NR3R4, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl, or ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl, or arylcarbonyl, ar(C1-C10)alkylcarbonyl, ar(C2-C10)alkenylcarbonyl, ar(C2-C10)alkynylcarbonyl, aroxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy and NR3R4, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl, or heteroarylcarbonyl, heteroar(C1-C10)alkylcarbonyl, heteroar(C2-C10)alkenylcarbonyl, heteroar(C2-C10)alkynylcarbonyl, heteroaroxycarbonyl(C1-C10)alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl(C1-C10)alkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R1 and R2 taken together with the carbon atom to which they are attached form a 5-7 membered saturated or unsaturated ring,
[0368] R3, R4 and R5 are each independently a hydrogen atom, (C1-C20)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C1-C10)alkyl, cyclo(C3-C8)alkyl, cyclo(C3-C8)alkenyl, cyclo(C3-C8)alkyl(C1-C10)alkyl, cyclo(C3-C8)alkyl(C2-C10)alkenyl, cyclo(C3-C8)alkyl(C2-C10)alkynyl, cyclo(C3-C8)alkenyl(C1-C10)alkyl, cyclo(C3-C8)alkenyl(C2-C10)alkenyl, cyclo(C3-C8)alkenyl(C2-C10)alkynyl, carboxy(C1-C20)alkyl, carboxy(C2-C10)alkenyl, carboxy(C2-C10)alkynyl, (C1-C10)alkoxy(C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl substituted with one or more halo, aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl or aryl, ar(C1-C10)alkyl, ar(C2-C10)alkenyl, ar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl or heteroaryl, heteroar(C1-C10)alkyl, heteroar(C2-C10)alkenyl, heteroar(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy and halo(C1-C10)alkoxy, heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl, or heterocyclyl, heterocyclyl(C1-C10)alkyl, heterocyclyl(C2-C10)alkenyl, heterocyclyl(C2-C10)alkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, halo(C1-C10)alkyl, halo(C2-C10)alkenyl, halo(C2-C10)alkynyl, (C1-C10)alkoxy, halo(C1-C10)alkoxy, SO2NR3R4 and NR3R4, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or
[0369] the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
[0370] Another aspect of this invention relates to pharmaceutical compositions comprising a pharmaceutical compound of this invention and a pharmaceutically acceptable carrier. Preferably, the composition contains from about 0.1% to about 99% by weight of said pharmaceutical compound depending on the host treated, the disease and the particular mode of administration.
[0371] Still another aspect of this invention relates to a method of controlling pain or disease symptoms in a warm-blooded animal exhibiting pain or disease symptoms comprising administering thereto a pharmaceutically effective amount of a compound or a composition comprising a compound of this invention and a pharmaceutically acceptable carrier.
[0372] In all embodiments of this invention, the term “alkyl” includes both branched and straight chain alkyl groups. Typical alkyl groups are methyl, ethyl, it-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl and the like.
[0373] The term “halo” refers to fluoro, chloro, bromo or iodo.
[0374] The term “haloalkyl” refers to an alkyl group substituted with one or more halo groups, for example chloromethyl, 2-bromoethyl, 3-iodopropyl, trifluoromethyl, perfluoropropyl, 8-chlorononyl and the like.
[0375] The term “cycloalkyl” refers to a cyclic aliphatic ring structure, optionally substituted with alkyl, hydroxy and halo, such as cyclopropyl, methylcyclopropyl, cyclobutyl, 2-hydroxycyclopentyl, cyclohexyl, 4-chlorocyclohexyl, cycloheptyl, cyclooctyl and the like.
[0376] The term “alkylcarbonyloxyalkyl” refers to an ester moiety, for example acetoxymethyl, n-butyryloxyethyl and the like.
[0377] The term “alkynylcarbonyl” refers to an alkynylketo functionality, for example propynoyl and the like.
[0378] The term “hydroxyalkyl” refers to an alkyl group substituted with one or more hydroxy groups, for example hydroxymethyl, 2,3-dihydroxybutyl and the like.
[0379] The term “alkylsulfonylalkyl” refers to an alkyl group substituted with an alkylsulfonyl moiety, for example mesylmethyl, isopropylsulfonylethyl and the like.
[0380] The term “alkylsulfonyl” refers to a sulfonyl moiety substituted with an alkyl group, for example mesyl, n-propylsulfonyl and the like.
[0381] The term “acetylaminoalkyl” refers to an alkyl group substituted with an amide moiety, for example acetylaminomethyl and the like.
[0382] The term “acetylaminoalkenyl” refers to an alkenyl group substituted with an amide moiety, for example 2-(acetylamino)vinyl and the like.
[0383] The term “alkenyl” refers to an ethylenicaliy unsaturated hydrocarbon group, straight or branched chain, having 1 or 2 ethlylenic bonds, for example vinyl, allyl, 1-butenyl, 2-butenyl, isopropenyl, 2-pentenyl and the like.
[0384] The term “haloalkenyl” refers to an alkenyl group substituted with one or more halo groups.
[0385] The term “cycloalkenyl” refers to a cyclic aliphatic ring structure, optionally substituted with alkyl, hydroxy and halo, having 1 or 2 ethylenic bonds such as methylcyclopropenyl, trifluoromethylcyclopropenyl, cyclopentenyl, cyclohexenyl, 1,4-cyclohexadienyl and the like.
[0386] The term “alkynyl” refers to an unsaturated hydrocarbon group, straight or branched, having 1 or 2 acetylenic bonds, for example ethynyl, propargyl and the like.
[0387] The term “haloalkynyl” refers to an alkynyl group substituted with one or Smore halo groups.
[0388] The term “alkylcarbonyl” refers to an alkylketo functionality, for example acetyl, n-butyryl and the like.
[0389] The term “alkenylcarbonyl” refers to an alkenylketo functionality, for example, propenoyl and the like.
[0390] The term “aryl” refers to phenyl or naphthyl which may be optionally substituted. Typical aryl substituents include, but are not limited to, phenyl, 4-chlorophenyl, 4-fluorophenyl, 4-bromophenyl, 3-nitrophenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methyphenyl, 4-methylphenyl, 4-ethylphenyl, 2-methyl-3-methoxyphenyl, 2,4-dibromophenyl, 3,5-difluorophenyl, 3,5-dimethylphenyl, 2,4,6-trichlorophenyl, 4-methoxyphenyl, naphthyl, 2-chloronaphthyl, 2,4-dimethoxyphenyl, 4-(trifluoromethyl)phenyl and 2-iodo-4-methylphenyl.
[0391] The term “heteroaryl” refers to a substituted or unsubstituted 5 or 6 membered unsaturated ring containing one, two or three heteroatoms, preferably one or two heteroatoms independently selected from oxygen, nitrogen and sulfur or to a bicyclic unsaturated ring system containing up to 10 atoms including one heteroatom selected from oxygen, nitrogen and sulfur. Examples of heteroaryls include, but is not limited to, 2-, 3- or 4-pyridinyl, pyrazinyl, 2-, 4-, or 5-pyrimidinyl, pyridazinyl, triazolyl, imidazolyl, 2- or 3-thienyl, 2- or 3-furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, quinolyl and isoquinolyl. The heterocyclic ring may be optionally substituted with up to two substituents.
[0392] The term “aralkyl” is used to describe a group wherein the alkyl chain can be branched or straight chain with the aryl portion, as defined hereinbefore, forming a terminal portion of the aralkyl moiety. Examples of aralkyl groups include, but are not limited to, optionally substituted benzyl, phenethyl, phenpropyl and phenbutyl such as 4-chlorobenzyl, 2,4-dibromobenzyl, 2-methylbenzyl, 2-(3-fluorophenyl)ethyl, 2-(4-methylphenyl)ethyl, 2-(4-(trifluoromethyl)phenyl)ethyl, 2-(2-methoxyphenyl)ethyl, 2-(3-nitrophenyl)ethyl, 2-(2,4-dichlorophenyl)ethyl, 2-(3,5-dimethoxyphenyl)ethyl, 3-phenylpropyl, 3-(3-chlorophenyl)propyl, 3-(2-methylphenyl)propyl, 3-(4-methoxyphenyl)propyl, 3-(4-(trifluoromethyl)phenyl)propyl, 3-(2,4-dichlorophenyl)propyl, 4-phenylbutyl, 4-(4-chlorophenyl)butyl, 4-(2-methylphenyl)butyl, 4-(2,4-dichlorophenyl)butyl, 4-(2-methoxphenyl)butyl and 10-phenyldecyl.
[0393] The term “arcycloalkyl” is used to describe a group wherein the aryl group is attached to a cycloalkyl group, for example phenylcyclopentyl and the like.
[0394] The term “aralkenyl” is used to describe a group wherein the alkenyl chain can be branched or straight chain with the aryl portion, as defined hereinbefore, forming a terminal portion of the aralkenyl moiety, for example styryl (2-phenylvinyl), phenpropenyl and the like.
[0395] The term “aralkynyl” is used to describe a group wherein the alkynyl chain can be branched or straight chain with the aryl portion, as defined hereinbefore, forming a terminal portion of the aralkynyl moiety, for example 3-phenyl-1-propynyl and the like.
[0396] The term “aroxy” is used to describe an aryl group attached to a terminal oxygen atom. Typical aroxy groups include phenoxy, 3,4-dichlorophenoxy and the like.
[0397] The term “aroxyalkyl” is used to describe a group wherein an alkyl group is substituted with an aroxy group, for example pentafluorophenoxymethyl and the like.
[0398] The term “heteroaroxy” is used to describe an heteroaryl group attached to a terminal oxygen atom. Typical heteroaroxy groups include 4,6-dimethoxypyrimidin. 2-yloxy and the like.
[0399] The term “heteroaralyl” is used to describe a group wherein the alkyl chain can be branched or straight chain with the heteroaryl portion, as defined hereinbefore, forming a terminal portion of the heteroaralkyl moiety, for example 3-furylmethyl, thenyl, furfuryl and the like.
[0400] The term “heteroaralkenyl” is used to describe a group wherein the alkenyl chain can be branched or straight chain with the heteroaryl portion, as defined hereinbefore, forming a terminal portion of the heteroaralkenyl moiety, for example 3-(4-pyridyl)-1-propenyl.
[0401] The term “heteroaralkynyl” is used to describe a group wherein the alkynyl chain can be branched or straight chain with the heteroaryl portion, as defined hereinbefore, forming a terminal portion of the heteroaralkynyl moiety, for example 4-(2-thienyl)-1-butynyl.
[0402] The term “heterocyclyl” refers to a substituted or unsubstituted 5 or 6 membered saturated ring containing one, two or three heteroatoms, preferably one or two heteroatoms independently selected from oxygen, nitrogen and sulfur or to a bicyclic ring system containing up to 10 atoms including one heteroatom selected from oxygen, nitrogen and sulfur wherein the ring containing the heteroatom is saturated. Examples of heterocyclyls include, but are not limited to, tetrahydrofuryl, pyrrolidinyl, piperidinyl, tetrahydropyranyl, morpholinyl, piperazinyl, dioxolanyl, dioxanyl, indolinyl and 5-methyl-6-chromanyl.
[0403] The term “heterocyclylalkyl” is used to describe a group wherein the alkyl chain can be branched or straight chain with the heterocyclyl portion, as defined hereinabove, forming a terminal portion of the heterocyclylalkyl moiety, for example 3-piperidinylmethyl and the like.
[0404] The term “heterocyclylalkenyl” is used to describe a group wherein the alkenyl chain can be branched or straight chain with the heterocyclyl portion, as defined hereinbefore, forming a terminal portion of the heterocyclylalkenyl moiety, for example 2-morpholinyl-1-propenyl.
[0405] The term “heterocyclylalkynyl” is used to describe a group wherein the alkynyl chain can be branched or straight chain with the heterocyclyl portion, as defined hereinbefore, forming a terminal portion of the heterocyclylalkynyl moiety, for example 2-pyrrolidinyl-1-butynyl.
[0406] The term “carboxyalkyl” includes both branched and straight chain alkyl groups as defined hereinbefore attached to a carboxy (—COOH) group.
[0407] The term “carboxyalkenyl” includes both branched and straight chain alkenyl groups as defined hereinbefore attached to a carboxy group.
[0408] The term “carboxyalkynyl” includes both branched and straight chain alkynyl groups as defined hereinbefore attached to a carboxy group.
[0409] The term “carboxycycloalkyl” refers to a carboxy group attached to a cyclic aliphatic ring structure as defined hereinbefore.
[0410] The term “carboxycycloalkenyl” refers to a carboxy group attached to a cyclic aliphatic ring structure having 1 or 2 ethylenic bonds as defined hereinbefore.
[0411] The term “cycloalkylalkyl” refers to a cycloalkyl group as defined hereinbefore attached to an alkyl group, for example cyclopropylmethyl, cyclohexylethyl and the like.
[0412] The term “cycloalkylalkenyl” refers to a cycloalkyl group as defined hereinbefore attached to an alkenyl group, for example cyclohexylvinyl, cycloheptylallyl and the like.
[0413] The term “cycloalkylalkynyl” refers to a cycloalkyl group as defined hereinbefore attached to an alkynyl group, for example cyclopropylpropargyl, 4-cyclopentyl-2-butynyl and the like.
[0414] The term “cycloalkenylalkyl” refers to a cycloalkenyl group as defined hereinbefore attached to an alkyl group, for example 2-(cyclopenten-1-yl)ethyl and the like.
[0415] The term “cycloalkenylalkenyl” refers to a cycloalkenyl group as defined hereinbefore attached to an alkenyl group, for example 1-(cyclohexen-3-yl)allyl and the like.
[0416] The term “cycloalkenylalkynyl” refers to a cycloalkenyl group as defined hereinbefore attached to an alkynyl group, for example 1-(cyclohexen-3-yl)propargyl and the like.
[0417] The term “carboxycycloalkylalkyl” refers to a carboxy group attached to the cycloalkyl ring portion of a cycloalkylalkyl group as defined hereinbefore.
[0418] The term “carboxycycloalkylalkenyl” refers to a carboxy group attached to the cycloalkyl ring portion of a cycloalkylalkenyl group as defined hereinbefore.
[0419] The term “carboxycycloalkylalkynyl” refers to a carboxy group attached to the cycloalkyl ring portion of a cycloalkylalkynyl group as defined hereinbefore.
[0420] The term “carboxycycloalkenylalkyl” refers to a carboxy group attached to the cycloalkenyl ring portion of a cycloalkenylalkyl group as defined hereinbefore.
[0421] The term “carboxycycloalkenylalkenyl” refers to a carboxy group attached to the cycloalkenyl ring portion of a cycloalkenylalkenyl group as defined hereinbefore.
[0422] The term “carboxycycloalkenylalkynyl” refers to a carboxy group attached to the cycloalkenyl ring portion of a cycloalkenylalkynyl group as defined hereinbefore.
[0423] The term “alkoxy” includes both branched and straight chain alkyl groups attached to a terminal oxygen atom. Typical alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy and the like.
[0424] The term “haloalkoxy” refers to an alkoxy group substituted with one or more halo groups, for example chloromethoxy, trifluoromethoxy, difluoromethoxy, perfluoroisobutoxy and the like.
[0425] The term “alkoxyalkoxyalkyl” refers to an alkyl group substituted with an alkoxy moiety which is in turn substituted with a second alkoxy moiety, for example methoxymethoxymethyl, isopropoxymethoxyethyl and the like.
[0426] The term “alkylthio” includes both branched and straight chain alkyl groups attached to a terminal sulfur atom, for example methylthio.
[0427] The term “haloalkylthio” refers to an alkylthio group substituted with one or more halo groups, for example trifluoromethylthio.
[0428] The term “alkoxyalkyl” refers to an alkyl group substituted with an alkoxy group, for example isopropoxymethyl.
[0429] The term “alkoxyalkenyl” refers to an alkenyl group substituted with an alkoxy group, for example 3-methoxyallyl.
[0430] The term “alkoxyalkynyl” refers to an alkynyl group substituted with an alkoxy group, for example 3-methoxypropargyl.
[0431] The term “alkoxycarbonylalkyl” refers to a straight chain or branched alkyl substituted with an alkoxycarbonyl, for example ethoxycarbonylmethyl, 2-(methoxycarbonyl)propyl and the like.
[0432] The term “alkoxycarbonylalkenyl” refers to a straight chain or branched alkenyl as defined hereinbefore substituted with an alkoxycarbonyl, for example 4-(ethoxycarbonyl)-2-butenyl and the like.
[0433] The term “alkoxycarbonylalkynyl” refers to a straight chain or branched alkynyl as defined hereinbefore substituted with an alkoxycarbonyl, for example 4-(ethoxycarbonyl)-2-butynyl and the like.
[0434] The term “haloalkoxyalkyl” refers to a straight chain or branched alkyl as defined hereinbefore substituted with a haloalkoxy, for example 2-chloroethoxymethyl, trifluoromethoxymethyl and the like.
[0435] The term “haloalkoxyalkenyl” refers to a straight chain or branched alkenyl as defined hereinbefore substituted with a haloalkoxy, for example 4-(chloromethoxy)-2-butenyl and the like.
[0436] The term “haloalkoxyalkynyl” refers to a straight chain or branched alkynyl as defined hereinbefore substituted with a haloalkoxy, for example 4-(2-fluoroethoxy)-2-butynyl and the like.
[0437] The term “alkylthioalkyl” refers to a straight chain or branched alkyl as defined hereinbefore substituted with an alkylthio group, for example methylthiomethyl, 3-(isobutylthio)heptyl and the like.
[0438] The term “alkylthioalkenyl” refers to a straight chain or branched alkenyl as defined hereinbefore substituted with an alkylthio group, for example 4-(methylthio)-2-butenyl and the like.
[0439] The term “alkylthioalkynyl” refers to a straight chain or branched alkynyl as defined hereinbefore substituted with an alkylthio group, for example. 4-(ethylthio)-2-butynyl and the like.
[0440] The term “haloalkylthioalkyl” refers to a straight chain or branched alkyl as defined hereinbefore substituted with an haloalkylthio group, for example 2-chloroethylthiomethyl, trifluoromethylthiomethyl and the like.
[0441] The term “haloalkylthioalkenyl” refers to a straight chain or branched alkenyl as defined hereinbefore substituted with an haloalkylthio group, for example 4-(chloromethylthio)-2-butenyl and the like.
[0442] The term “haloalkylthioalkynyl” refers to a straight chain or branched alkynyl as defined hereinbefore substituted with an haloalkylthio group, for example 4-(2-fluoroethylthio)-2-butynyl and the like.
[0443] The term “dialkoxyphosphorylalkyl” refers to two straight chain or branched alkcoxy groups as defined hereinbefore attached to a pentavalent phosphorous atom, containing an oxo substituent, which is in turn attached to an alkyl, for example diethoxyphosphorylmethyl.
[0444] The term “oligomer” refers to a low-molecular weight polymer, whose number average molecular weight is typically less than about 5000 g/mol, and whose degree of polymerization (average number of monomer units per chain) is greater than one and typically equal to or less than about 50.
[0445] In Schemes 1-20 hereinafter showing how to synthesize compounds of this invention and Tables 1-10 hereinafter listing various representative compounds of this invention, the following abbreviations may be present: Me for methyl, Et for ethyl, iPr or iPr for isopropyl, n-Bu for n-butyl, t-Bu for tert-butyl, Ac for acetyl, Ph for phenyl, 4Cl-Ph or (4Cl)Ph for 4-chlorophenyl, 4Me-Ph or (4Me)Ph for 4-methylphenyl, (p-CH3O)Ph for p-methoxyphenyl, (p-NO2)Ph for p-nitrophenyl, 4Br-Ph or (4Br)Ph for 4-bromophenyl, 2-CF3-Ph or (2CF3)Ph for 2-trifluoromethylphenyl, Bn for benzyl and the like.
[0446] The compounds of Formula I of this invention and the intermediates used in the synthesis of the compounds of this invention can be prepared according to the following methods. Method A can be used when preparing compounds of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t(X3)dZ3] as shown below in Scheme 1:
[0447] Method A:
54
[0448] where Z1(X1)m—H, Z2(X2)q, Z3(X3)d, Z1(X1)m, G10, G11, G20, G21, G30, G31, and R2 are as defined previously for compound of Formula I-A and t=0 or 1, t′=0 or 1, q=C or 1, d=0 or 1, and Y1=halogen such as chlorine.
[0449] In a typical preparation, according to Method A, of a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3], a compound of Formula II is reacted with a compound of Formula III in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula II. The compounds of Formula II are generally commercially available or can be prepared according to known procedures.
[0450] The compounds of Formula III of Scheme 1 are prepared as shown in Scheme 2.
55
[0451] where Z2(X2)q, Z3(X3)d, G10, G11, G20, G21, G30, G31, and R2 are as defined previously for compound of Formula I-A and t=0 or 1, t′=0 or 1, q=0 or 1, d=0 or 1, R12 is an alkyl, aralkyl, or aryl group, and Y1=halogen such as chlorine.
[0452] In a typical preparation of a compound of Formula III, a compound of Formula IV is treated with a suitable halogenating agent in a suitable solvent, where the suitable halogenating agents include chlorine gas, thionyl chloride, and sulfuryl chloride, however, the preferred halogenating agent is sulfuryl chloride. Suitable solvents for use in the above process include, but are not limited to, hexanes, chlorinated solvents such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, and the like, however, the reactions are normally run neat. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired.
[0453] The compounds of Formula IV of Scheme 2 are prepared as shown in Scheme 3:
56
[0454] where Z2(X2)q[(C=G20)-G21]t—H, Z2(X2)q, Z3(X3)d, G10, G11, G20, G21, G30, G31, and R2 are as defined previously for compound of Formula I and t=0 or 1, t′=0 or 1, q=0 or 1, d=0 or 1, R12 is an alkyl, aralkyl, or aryl group, and Y2=halogen such as chlorine.
[0455] In a typical preparation of a compound of Formula IV, a compound of Formula V is reacted with a compound of Formula VI in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula VI. The compounds of Formula VI are generally commercially available or can be prepared according to known procedures.
[0456] The compounds of Formula V of Scheme 3 are prepared as shown in Scheme 4:
57
[0457] where Z3(X3)d, G10, G11, G30, G31, and R2 are as defined previously for compound of Formula I-A and t′=0 or 1, d=0 or 1, R12=alkyl, aralkyl, or aryl, and Y1 and Y2=halogen such as chlorine, bromine, or iodine.
[0458] In a typical preparation of a compound of Formula V, a compound of Formula VII is reacted with a compound of Formula VIII in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran THF), glyme, diethyl ether, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is diethyl ether. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is sodium hydride. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula VIII. The compounds of Formula VIII are generally commercially available or can be prepared according to known procedures. Conversion of Y2 from Cl to Br or Cl to I in compound of Formula V can be prepared according to literature procedures. A general description of the synthesis of halogen exchange (Finkelstein reaction) is described in March, J. Advanced Organic Chemistry, 4th ed.; Wiley and Sons: New York, 1992; pp 430-431.
[0459] The compounds of Formula VII of Scheme 4 are prepared as shown in Scheme 5:
58
[0460] where Z3(X3)d, G10, G11, G30, G31, and R2 are as defined previously for compound of Formula I-A, t′=0 or 1, d=0 or 1, and Y1 and Y2=halogen such as chlorine, bromine, or iodine.
[0461] In a typical preparation of a compound of Formula VII, a compound of Formula IX is reacted with a compound of Formula X (or a suitable precursor of compound of Formula X) in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether, dioxane and the like; aromatic solvents such as benzene and toluene; acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2), carbon tetrachloride (CCl4) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable catalysts for use in the above process include, but are not limited to, pyridine, thioureas and ureas such as tetra-n-butylurea, phosphoramides such as hexamethylphosphotriamide, substituted amides such as dimethylformamide, quaternary ammonium halides such as tetrabutyl or tributylbenzyl ammonium chloride, arylamines such as N,N,-dimethylaminopyridine, N,N-dimethylaniline, tertiary phosphines such as trioctyl phosphine, and alkali metal or alkaline earth metal halides such as cesium or potassium chloride which are used in conjunction with a sequestering agent such as a crown ether (18-crown-6). If desired, mixtures of these catalysts may be used, however, the preferred catalyst is pyridine. Compound of Formula IX may in some cases exist in a polymeric form. If so, the monomeric form can be achieved via, known procedures, one being through thermal depolymerization. Compound of Formula X when G10=O and Y1 and Y2=Cl is phosgene, C(═O)Cl2. However, other forms of phosgene, phosgene equivalents, can be utilized such as trichloromethyl chloroformate (compound of Formula X in which G10=O, Y1=Cl, and Y2=OCCl3) or di(trichloromethyl)carbonate (compound of Formula X in which G10=O and Y1 and Y2=OCCl3). The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 100° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. The catalyst is normally used in lower amounts than that of both compounds of Formula IX and X. The compounds of Formula IX and X are generally commercially available or can be prepared according to known procedures.
[0462] The compounds of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] can be prepared according to Method B as shown in Scheme 6:
[0463] Method B:
59
[0464] where Z1(X1)m, Z2(X2)q, Z3(X3)d, G10, G11, G20, G21, G30, G31, and R2 are as defined previously for compound of Formula I-A and m=0 or 1, t=0 or 1, q=0 or 1, t′=0 or 1, d=0 or 1, and Y2=halogen such as chlorine, bromine, or iodine.
[0465] In a typical preparation, according to Method B, Scheme 6, of a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3], a compound of Formula XI is reacted with a compound of Formula VI in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula VI. The compounds of Formula VI are generally commercially available or can be prepared according to known procedures.
[0466] The compounds of Formula XI of Scheme 6 are prepared as shown in Scheme 7:
60
[0467] where Z1(X1)m—H, Z3(X3)d, Z1(X1)m, G10, G11, G30, G31, and R2 are as defined previously for compound of Formula I-A and m=0 or 1, t′=0 or 1, d=0 or 1, and Y1 and Y2=halogen such as chlorine.
[0468] In a typical preparation of a compound of Formula XI, a compound of Formula II is reacted with a compound of Formula VII in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2CL) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula II. The compounds of Formula II are generally commercially available or can be prepared according to known procedures. Conversion of Y2 from Cl to Br or Cl to I in compound of Formula XI can be prepared according to literature procedures. A general description of the synthesis of halogen exchange (Finkelstein reaction) is described in March, J. Advanced Organiic Chemistry, 4th ed.; Wiley and Sons: New York, 1992; pp 430-431.
[0469] The compounds of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] can be prepared according to Method C as shown in Scheme 8:
[0470] Method C:
61
[0471] where Y2=halogen such of as iodine, bromine, or chlorine, Z1(X1)m, Z3(X3)d, G10, G11, G30, G31, and R2 are as defined previously for compound of Formula I-A and m=0 or 1, t=0, q=0 or 1, t′=0 or 1, and d=0 or 1 where Z2(X2)q═NR3R4, NR3R4R5, or {(NR3R4R5)M} and when q=0, in compound of Formula VI-A, Z2 can be a tertiary amine where in compound of Formula I-A, Z2 is a quaternary amine salt, and when q=1, in compound of Formula VI-A, X2Z2 can be a tertiary amine where in compound of Formula I-A, X2Z2 is a quaternary amine salt.
[0472] In a typical preparation of a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3], according to Method C, a compound of Formula XI is reacted with a compound of Formula VI-A in a suitable solvent. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 200° C. Preferably, the reaction is carried out between 0° C. and about 100° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of compound of Formula XI is used per equivalent of starting material of compound of Formula VI-A. The compounds of Formula VI-A are generally commercially available or can be prepared according to known procedures. The compounds of Formula XI can be prepared by the same process as that of Scheme 7.
[0473] The compounds of Formula I-B, I-C, and I-A [compounds of Formula I where R1 equals C(=G30)-(G31)t′-H, C(=G30)-Y1, and C(=G30)-(G31)t′(X3)dZ3, respectively] can be prepared according to Method D as shown below in Scheme 9:
[0474] Method D:
62
[0475] where Z1(X1)m, Z2(X2)q, Z3(X3)d, G10, G11, G20, G21, G30, G31, and R2 are as defined above for compound of Formula I-A and m 0 or 1, t=0 or 1, t′=0 or 1, q=0 or 1, d=0 or 1, and Y1=halogen such as chlorine.
[0476] In a typical preparation of a compound of Formula I-B [compound of Formula I where R1 equals C(=G30)-(G31)t′-H], a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] is treated with a suitable solvent under suitable reaction conditions which can successfully transform (G31)t′(X3)dZ3 to (G31)t′-H via methods known to one skilled in the art. For example, if d=0, Z3=benzyl (Bn), t′=1, and G30 and G31=oxygen, then typical reaction conditions for the transformation of C(=G30)-G31Z3 (CO2Bn) to C(=G30)-G31H(CO2H) would involve the following: suitable solvents include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; esters such as ethyl acetate; acetonitrile; alcohols such as methanol or ethanol; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is ethyl acetate. Suitable catalysts in the presence of at least one equivalent of hydrogen include, palladium, platinum, nickel, rhodium, iridium and ruthenium. The catalysts are normally adsorbed or admixed on an inert support material which includes carbon, alumina, calcium sulfate, or barium sulfate, however, the preferred catalyst and support is palladium on carbon. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. One skilled in the art would recognize that a hydrogenation reaction to remove a benzyl group as described above would only be utilized when all other functional groups present within compound of Formula I-A are deemed compatible with the reaction conditions. See Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; Wiley and Sons: New York, 1991; pp 227-265 for additional suitable reaction conditions and appropriate C(=G30)-(G31)t′(X3)dZ3 chemical moieties for the transformation of (G31)t′(X3)dZ3 to (G31)t′-H.
[0477] In a typical preparation of a compound of Formula I-C [compound of Formula I where R1 equals C(=G30)-Y1], a compound of Formula I-B [compound of Formula I where R1 equals C(=G30)-(G31)t′-H] is treated with a suitable halo-de-hydroxylation reagent in a suitable solvent, where suitable halo-de-hydroxylation reagents include, but are not limited to, thionyl chloride, oxalyl chloride, oxalyl bromide, triphenyl phosphine in carbon tetrachloride, phosphorus trichloride, and phosphorus pentachloride, however, the preferred halo-de-hydroxylation reagent is thionyl chloride. Suitable solvents for use in the above process include, but are not limited to, hexanes, ethers such as tetrahydrofuran, glyme, and the like; chlorinated solvents such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, and the like, however, the reactions are normally run neat with a catalytic amount of dimethylformamide present. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Compounds of Formula I-C [compound of Formula I where R1 equals C(=G30)-Y1] can also be synthesized directly from compounds of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3]. In a typical preparation of a compound of Formula I-C, a compound of Formula I-A is treated with a suitable solvent in the presence of suitable reaction conditions which can successfully transform C(=G30)-(G31)t′(Y3)dZ3 to C(=G30)-Y1 via methods known to one skilled in the art. For example, if d=0, t′=1, and Z3=trimethylsilyl and G30 and G31=oxygen, then typical reaction conditions for the transformation of C(=G30)-G31Z3 (CO2SiMe3) to C(=G30)-Y1 [C(═O)—Cl] would involve treatment of the compound of Formula I-A in which C(=G30)-G31Z3 is CO2SiMe3 with oxalyl chloride in a suitable solvent such as THF at a temperature ranging from −78° C. and about 100° C. See Larock, R. C. Comprehensive Organic Transformations, 2nd ed, New York, 1999; p 1968 as well as Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; Wiley and Sons: New York, 1991; pp 261-262 for additional suitable reaction conditions for the transformation of C(=G30)-(G31)t′(X3)dZ3 to C(=G30)-Y1. One skilled in the art would recognize that a halogenation reaction to convert a silyl ester to an acid chloride as described above would only be utilized when all other functional groups present within compounds of Formula I-A are deemed compatible with the reaction conditions. Compound of Formula I-C in which Y1 is chlorine can be interconverted to other halo derivatives via reaction conditions listed in Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1950-1951.
[0478] In a typical preparation of a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] from a compound of Formula I-C [compound of Formula I where R1 equals C(=G30)-Y1], a compound of Formula I-C is reacted with Z3(X3)d(G3′)t′-H in a suitable solvent in the presence of a suitable base. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-C. Suitable reaction conditions for the conversion of C(=G30)-Y1 to C(=G30)-(G31)t′(X3)dZ3 can be found in Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1952-1954.
[0479] Additionally, a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] can be prepared via the reaction of a compound of Formula I-B [compound of Formula I where R1 equals C(=G30)-(G31)t′-H] in a suitable solvent with Z3(X3)d—H and a suitable coupling reagent. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried uut at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-B. Suitable coupling reagents for use in the above process include, but are not limited to, lipases, diazo compounds, anhydrides, acid chlorides, carbodiimides, and carbodiimidazoles. Suitable reaction conditions for the conversion of C(=G30)-(G31)t′-H to C(=G30)-(G31)t′(X3)dZ3 can be found in Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1932-1949.
[0480] Alternatively, transformation of a compound of Formula I-B [compound of Formula I where R1 equals C(=G30)-(G3′)t′-H] to a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3] can also be accomplished by reaction of a compound of Formula I-B in a suitable solvent with a suitable base in the presence of a suitable commercially available halide, such as an alkyl halide. Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable halides include, but are not limited to, alkyl halides such as benzyl chloride, benzyl bromide, methyl iodide, and ethyl iodide. The preferred halide is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-B. Suitable reaction conditions for the conversion of C(=G30)-(G31)t′-H to C(=G30)-(G31)t′(X3)dZ3 can be found in Larock, R. C. Comprehensiue Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1938-1940.
[0481] The compounds of Formula I-D of this invention and the intermediates used in the synthesis of the compounds of this invention can be prepared according to the following methods. Method E can be used when preparing compounds of Formula I-D as shown below in Scheme 10:
[0482] Method E:
63
[0483] where Z1(X1)m, Z3(X3)d, G10, G11, G20, G21, G30, G31, and R2 are as defined above for compound of Formula I-A, m=0 or 1, Y1=halogen such as chlorine, and q=0 and Z2=CR13R14G32, where G32 is an oxygen atom, a sulfur atom or NR3, and R13 and R14 are independently defined as for R2.
[0484] In a typical preparation of a compound of Formula I-D, a compound of Formula I-A [compound of Formula I where R1 equals C(=G30)-(G31)t′(X3)dZ3], where the C(=G30)-(G31)t′(X3)dZ3 moiety is reacted intramolecularly with the (X2)qZ2 moiety (where q=0 and Z2=CR13R14G32) in a suitable solvent in the presence of a suitable base to afford cyclic [—C(=G30)-G32-CR13R14C(=G20)G21C(R2)—]. Suitable solvents include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; esters such as ethyl acetate; acetonitrile; alcohols such as methanol or ethanol; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-A.
[0485] A compound of Formula I-D can also be prepared via the reaction of a compound of Formula I-B [compound of Formula I where R1 equals C(=G30)-(G31)t′-H], where C(=G30)-(G31)t′-H is reacted intramolecularly with (X2)qZ2, where Z2═CR13R14G32, in a suitable solvent in the presence of a suitable base along with a suitable coupling reagent. Suitable reaction conditions would involve the following: suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-B. Suitable coupling reagents for use in the above process include, but are not limited to, lipases, diazo compounds, anhydrides, acid chlorides, carbodiimides, and carbodiimidazoles. Suitable reaction conditions for the conversion of H-(G31)t′-(G30=)C—C(R2)-(G21[G20=]C)t(X2)qZ2 where Z2=CR13R14G32, to cyclic [—C(=G30)-G32-CR13R14C(=G20)G21C(R2)—] can be found in Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1932-1949.
[0486] In a typical preparation of a compound of Formula I-D, a compound of Formula I-C [compound of Formula I where R1 equals C(=G30)-Y1] where the C(=G30)Y1 moiety is reacted intramolecularly with the (X2)qZ2 moiety (where Z2=CR13R14G32) in a suitable solvent in the presence of a suitable base. Suitable reaction conditions would involve the following: suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used. The preferred base is dependent upon the substrates employed and is selected according to the properties of the substrates. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula I-C. Suitable reaction conditions for the conversion of Y1-(G30=)C—C(R2)-(G21[G20=]C)t(X2)qZ2, where Z2 CR13R14G32, to cyclic [-C(=G30)-G32CR13R14C(=G20)G20C(R2)—] can be found in Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley and Sons: New York, 1999; pp 1952-1954.
[0487] Application of Method A (Scheme 5) as described previously for the synthesis of compound of Formula VII to the synthesis of compound of Formula XIV is described below in Scheme 11. Compound of Formula XII (compound of Formula IX where G11 and G30=O) is reacted with compound of Formula XIII (compound of Formula X where G10=O) to afford compound of Formula XIV (compound of Formula VII where G10, G11, and G30=O):
64
[0488] where Z3(X3)d, d, t′, G31, and R2 are as defined previously for compound of Formula I-A, Y1 and Y2=halogen such as chlorine, bromine, or iodine.
[0489] Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether, dioxane and the like; acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2), carbon tetrachloride (CCl4) or chloroform (CHCl3). If desired, mixtures of these solvents may be used. The preferred solvent is dependent upon the substrates employed and is selected according to the properties of the substrates. For example, in the reaction of compound of Formula XII, where t′=1, G31=O, d=0, R2=H, and Z3=benzyl (Bn), with compound of Formula XIII, where Y1 and Y2=Cl, to afford compound of Formula XIV where t′=1, G31=O, d=0, R2=H, Z3=benzyl (Bn), and Y1 and Y2=Cl, then the preferred solvent is carbon tetrachloride. However, in the reaction of compound of Formula XII, where t′=1, G31=O, d=0, R2=H, and Z3=ethyl (Et), with compound of Formula XIII, where Y1 and Y2=Cl, to afford compound of Formula XIV, where t′=1, G31=O, d=0, R2=H, Z3=ethyl (Et), and Y1 and Y2=Cl, then the preferred solvent is tetrahydrofuran. Suitable catalysts for use in the above process include, but are not limited to, pyridine, thioureas and ureas such as tetra-n-butylurea, phosphoramides such as hexamethylphosphotriamide, substituted amides such as dimethylformamide, quaternary ammonium halides such as tetrabutyl or tributylbenzyl ammonium chloride, arylamines such as N,N,-dimethylaminopyridine, N,N-dimethylaniline, tertiary phosphines such as trioctyl phosphine, and alkali metal or alkaline earth metal halides such as cesium or potassium chloride which are used in conjunction with a sequestering agent such as a crown ether (18-crown-6). If desired, mixtures of these catalysts may be used, however, the preferred catalyst is pyridine. Compound of Formula XII may in some cases exist in a polymeric form. If so, the monomeric form can be achieved via known procedures, one being through thermal depolymerization. Compound of Formula XIII in which Y1 and Y2=Cl is phosgene, C(═O)Cl2. However, other forms of phosgene, phosgene equivalents, can be utilized such as trichloromethyl chloroformate (compound of Formula XIII in which Y1=Cl, and Y2=OCCl3) or di(trichloromethyl)carbonate (compound of Formula XIII in which Y1 and Y2=OCCl3). The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 100° C. The above process to produce compounds of the present invention is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. The catalyst is normally used in lower amounts than that of both compounds of Formula XII and XIII. The compounds of Formula XII and XIII are generally commercially available or can be prepared according to known procedures.
[0490] Application of Method A (Scheme 4) as described previously for the synthesis of compound of Formula V to the synthesis of compound of Formula XVI is described below in Scheme 12. Compound of Formula XV (compound of Formula VIII where R12=Et and R12S—H is taken together to equal Et-S-L) is reacted with compound of Formula XIV (compound of Formula VII where G10, G11, and G30O) to afford compound of Formula XVI (compound of Formula V where G10, G11, and G30O, and R12=Et):
65
[0491] where Z3(X3)d, d, t′, G31 and R2 are as defined previously for compound of Formula I-A, L=metal cation such as Na or K, and Y1 and Y2=halogen such as chlorine, bromine, or iodine.
[0492] Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is diethyl ether. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is sodium hydride. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. Preparation of the compounds of the present invention by the above process is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XV except when L=Na or K, then no base is required. The compounds of Formula XV are generally commercially available or can be prepared according to known procedures. For example, R12S-L=EtS-Na, is commercially available. Conversion of Y2 from Cl to Br or Cl to I in compound of Formula XVI can be prepared according to literature procedures. A general description of the synthesis of halogen exchange (Finkelstein reaction) is described in March, J. Advanced Organic Chemistry, 4th ed.; Wiley and Sons: New York, 1992; pp 430-431. Also, see synthesis Example 8 for conversion of Y2 from Cl to I in compound of Formula XVI.
[0493] Application of Method A (Scheme 3) as described previously for the synthesis of compound of Formula IV to the synthesis of compound of Formula XVII is described below in Scheme 13. Compound of Formula XVI (compound of Formula V where R12=Et and G10, G11, and G30O) is reacted with compound of Formula VI (where t=1 and q=0 or 1) to afford compound of Formula XVII (compound of Formula IV in which t=1, G10, G11, and G30O, R12=Et, and q=0 or 1):
66
[0494] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula -A, and Y2=halogen such as chlorine, bromine, or iodine
[0495] Suitable solvents for use in the above process include, but are not limited to, ethers such as tetrahydrofuran (THF), glyme, diethyl ether and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) or chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is THF. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or ciisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is diisopropylethylamine. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. Preparation of the compounds of the present invention by the above process is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula VI. The compounds of Formula VI are generally commercially available or can be prepared according to known procedures.
[0496] Application of Method A (Scheme 2) as described previously for the synthesis of compound of Formula III to the synthesis of compound of Formula XVIII is described below in Scheme 14. Compound of Formula XVII (compound of Formula IV where R12=Et, G10, G11, and G30=O, and q=0 or 1) is reacted with a suitable halogenating agent to afford compound of Formula XVIII (compound of Formula III where G10, G11, and G30=O. Y1=Cl, and q=0 or 1):
67
[0497] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A and t=1.
[0498] Suitable halogenating agents include chlorine gas, thionyl chloride, and sulfuryl chloride, however, the preferred halogenating agent is sulfuryl chloride. Suitable solvents for use in the above process include, but are not limited to, hexanes, chlorinated solvents such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride and the like, however, the reactions are normally run neat. The above process may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out between 0° C. and about 50° C. Preparation of the compounds of the present invention by the above process is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired.
[0499] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XX is described below in Scheme 15. Compound of Formula XIX (compound of Formula II where m=1 and Z1(X1)m—H equals fluoxetine hydrochloride) is reacted with compound of Formula XVIII (compound of Formula III where Y1=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XX (compound of Formula I-A where m=1, t=1, q=0 or 1, Z1(X1)m=fluoxetine, and G10, G11, and G30=0):
68
[0500] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A.
[0501] In the reaction of a compound of Formula XVIII with a compound of Formula XIX to afford a compound of Formula XX, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is THF. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is DMAP. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at 22° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, two equivalents of base are used per equivalent of starting material of compound of Formula XIX.
[0502] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XXII is described below in Scheme 16. Compound of Formula XXI (compound of Formula II where m=1 and Z1(X1)m—H equals fluconazole) is reacted with compound of Formula XVIII (compound of Formula III where Y1=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XXII (compound of Formula I-A where m=1, t=1, q=0 or 1, Z1(X1)m=fluconazole, and G10, G11, and G30=O):
69
[0503] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A.
[0504] In the reaction of a compound of Formula XXI with a compound of Formula XVIII to afford a compound of Formula XXII, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is THF. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP), potassium bis(trimethylsilyl)amide (KHMDS) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is KHMDS. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at −78° C. to 0° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XXI.
[0505] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XXIV is described below in Scheme 17. Compound of Formula XXIII (compound of Formula II where m=1 and Z1(X1)m—H equals nifedipine) is reacted with compound of Formula XVIII (compound of Formula III where Y1=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XXIV (compound of Formula I-A where m=1, t=1, q=0 or 1, Z1(X1)m=nifedipine, and G10, G11, and G30=O):
70
[0506] where Z2X2)q, Z3X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A.
[0507] In the reaction of a compound of Formula XXIII with a compound of Formula XVIII to afford a compound of Formula XXIV, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is THF. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine or diisopropylethylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP), potassium bis(trimethylsilyl)amide (KHMDS) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is KHMDS. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at −78° C. to 0° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XXIII.
[0508] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XXVI is described below in Scheme 18. Compound of Formula XXV (compound of Formula II where m=1 and Z1(X1)m—H equals norfloxacin) is reacted with compound of Formula XVIII (compound of Formula III where Y′=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XXVI (compound of Formula I-A where m=1, t
[0509] =1, q=0 or 1, Z1(X1)m=norfloxacin, and G10, G11, and G30O):
71
[0510] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G3′, and R2 are as defined previously for compound of Formula I-A.
[0511] In the reaction of a compound of Formula XXV with a compound of Formula XVIII to afford a compound of Formula XXVI, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3) If desired, mixtures of these solvents may be used, however, the preferred solvent is CH2Cl2. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine, diisopropylethylamine, or trijsopropylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP), potassium bis(trimethylsilyl)amide (KHMDS) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is triisopropylamine. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at 22° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XXV.
[0512] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XXVIII is described below in Scheme 19. Compound of Formula XXVII (compound of Formula II where m=1 and Z1(X1)m—H equals 4-acetamidophenol) is reacted with compound of Formula XVIII (compound of Formula III where Y′=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XXVIII (compound of Formula I-A where m=1, t=1, q=0 or 1, Z1(X1)m=4-acetamidophenol, and G10, G11, and G30=O):
72
[0513] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A.
[0514] In the reaction of a compound of Formula XXVII with a compound of Formula XVIII to afford a compound of Formula XXVIII, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is CH2Cl2. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine, diisopropylethylamine, or triisopropylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP), potassium bis(trimethylsilyl)amide (KHMDS) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is potassium hydroxide. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at 22° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XXVII.
[0515] Application of Method A (Scheme 1) as described previously for the synthesis of compound of Formula I-A to the synthesis of compound of Formula XXX is described below in Scheme 20. Compound of Formula XXIX (compound of Formula II where m=1 and Z1(X1)m—H equals sulfamethoxazole) is reacted with compound of Formula XVIII (compound of Formula III where Y1=Cl, G10, G11, and G30=O, t=1, and q=0 or 1) to afford compound of Formula XXX (compound of Formula I-A where m=1, t=1, q=0 or 1, Z1(X1)m=sulfamethoxazole, and G10, G11, and G30=O):
73
[0516] where Z2(X2)q, Z3(X3)d, d, t′, G20, G21, G31, and R2 are as defined previously for compound of Formula I-A.
[0517] In the reaction of a compound of Formula XXIX with a compound of Formula XVIII to afford a compound of Formula XXX, the following conditions can be used: suitable solvents for use in the above method include ethers such as tetrahydrofuran (THF), glyme, and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; chlorinated solvents such as methylene chloride (CH2Cl2) and chloroform (CHCl3). If desired, mixtures of these solvents may be used, however, the preferred solvent is CH2Cl2. Suitable bases for use in the above process include, but are not limited to, metal hydrides such as sodium or potassium hydride; metal alkoxides such as sodium or potassium alkoxides; alkali metal hydroxides such as sodium or potassium hydroxide; tertiary amines such as triethylamine, diisopropylethylamine, or triisopropylamine; an alkali metal carbonate such as sodium or potassium carbonate; 4-dimethylaminopyridine (DMAP), potassium bis(trimethylsilyl)amide (KHMDS) or pyridine. If desired, mixtures of these bases may be used, however, the preferred base is triisopropylamine. The above method may be carried out at temperatures between about −78° C. and about 100° C. Preferably, the reaction is carried out at 22° C. Preparation of the compounds of the present invention by the above method is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired. Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired. Generally, one equivalent of base is used per equivalent of starting material of compound of Formula XXIX.
[0518] Following the general methods described hereinbefore, the following compounds of Formula VII (where R2=H) as listed in Table 1 were prepared.
1TABLE 1
|
|
|
74
|
Listing of Compounds of Formula VII
Cmpd #Y1G10G11G30Y2G31t′d(X3)dZ3
|
1-1ClOOOClO10benzyl
1-2ClOOOClO10ethyl
1-3ClOOOClO10methyl
1-4ClOOOClO10isopropyl
1-5ClOOOClO10tert-butyl
1-6ClOOOClO10n-butyl
|
[0519] The following Examples are provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 1
[0520] Benzyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-1 of Table 1)
[0521] To a 3-neck round-bottom flask, equipped with nitrogen inlet, a thermometer and a solid addition funnel, was added benzyl glyoxylate (50.9 g, 300 mmol), pyridine (2.5 mL, 31.0 mmol) and 1500 mL of carbon tetrachloride. The solution was cooled with dry ice/acetone to −20° C. and triphosgene (230 g, 770 mmol) was added over 5 minutes, maintaining the temperature between −10° C. and −20° C. The reaction was gradually warmed to room temperature over 2 h, then warmed to 50° C. and was stirred at that temperature for 1 h. The reaction was then cooled and placed in the freezer overnight. The precipitates were filtered by gravity, washing with carbon tetrachloride. The solvent was removed in vacuo, with low heat, to yield 58 g of the desired benzyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate as a clear colorless oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.24 (s, 2H), 6.45 (s, 1H), 7.32 (s, 5H).
EXAMPLE 2
[0522] Ethyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-2 of Table 1)
[0523] Pyridine (0.145 mL, 1.79 mmol) was added to a solution of polymeric ethyl glyoxylate (18.51 g, 181 mmol) and triphosgene (48.5 g, 163 mmol) in dry THF at room temperature in a flask fitted with a reflux condenser and connected to a N2 bubbler. After 10 min the flask was placed in a pre-heated 65° C. oil bath. After 21 h, the reaction was allowed to cool to room temperature, and then the mixture was concentrated under vacuum. Ether was added to the residue, the mixture was filtered through Celite, and the filtrate was concentrated, affording 34.6 g (87% yield) of a yellow oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.36 (t, 3H) 4.36 (q, 2H), 6.48 (s, 1H).
EXAMPLE 3
[0524] Methyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-3 of Table 1)
[0525] The title compound was prepared according to the procedure described in Example 2 above, except methyl glyoxylate was substituted for ethyl glyoxylate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 3.92 (s, 3H), 6.52 (s, 1H).
EXAMPLE 4
[0526] Isopropyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-4 of Table 1)
[0527] The title compound was prepared according to the procedure described in Example 2 above, except isopropyl glyoxylate was substituted for ethyl glyoxylate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.33 (s, 3H), 1.35 (s, 3H), 5.2 (q, 1H), 6.44 (s, 1H).
EXAMPLE 5
[0528] tert-Butyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-5 of Table 1)
[0529] The title compound was prepared according to the procedure described in Example 2 above, except tert-butyl glyoxylate was substituted for ethyl glyoxylate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.53 (s, 9H), 6.35 (s, 1H).
EXAMPLE 6
[0530] n-Butyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (Compound 1-6 of Table 1)
[0531] The title compound was prepared according to the procedure described in Example 2 above, except n-butyl glyoxylate was substituted for ethyl glyoxylate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.94 (t, 3H), 1.40 (q, 2H), 1.68 (m, 2H), 4.28 (m, 2H), 6.49 (s, 1H).
[0532] Following the general methods described hereinbefore, the following compounds of Formula V (where R2=H) as listed in Table 2 were prepared.
2TABLE 2
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75
|
Listing of Compounds of Formula V
Cmpd #R12G10G11G30Y2G31t′d(X3)dZ3
|
2-1EtOOOClO10ethyl
2-2EtOOOIO10ethyl
2-3EtOOOClO10n-butyl
2-4EtOOOIO10n-butyl
2-5EtOOOClO10isopropyl
2-6EtOOOIO10isopropyl
|
[0533] The following Examples are provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 7
[0534] Chloro-ethylsulfanylcarbonyloxy-acetic acid ethyl ester (Compound 2-1 of Table 2)
[0535] A 1000 mL round bottom flask was charged with sodium ethylthiolate (13.3 g, 158 mmol) and 500 mL of dry diethyl ether. The mixture was cooled to −70° C. in an acetone dry ice bath. Ethyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate (32.8 g, 155 mmol) was added as a solution in 20 mL of diethyl ether over 1.5 h at such a rate that the reaction temperature did not exceed −65° C. The reaction was allowed to warm to room temperature and stir for 16 h. The reaction was vacuum filtered, the filtrate dried (MgSO4), gravity filtered, and-concentrated under reduced pressure to yield 33.5 g of a clear liquid. 1H-NMR (300 MHz, CDCl3) δ (Ppm): 1.33 (m, 6H), 2.94 (q, 2H), 4.31 (q, 2H), 6.65 (s, 1H).
EXAMPLE 8
[0536] Iodo-ethylsulfanylcarbonyloxy-acetic acid ethyl ester (Compound 2-2 of Table 2)
[0537] To a stirred solution of chloro-ethylsulfanylcarbonyloxy-acetic acid ethyl ester (33.5 g, 148 mmol) in 160 mL of dry acetone was added NaI (28.8. g, 192 mmol). The mixture was stirred at room temperature for 4 h. The acetone was removed and the remaining slurry was diluted with 100 mL of diethyl ether. The mixture was filtered through Celite and concentrated under reduced pressure to yield a brown liquid. The liquid was redissolved in 50 mL of diethyl ether and gravity filtered to afford 37.1 g of a brown liquid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.33 (m, 6H), 2.95 (q, 2H), 4.30 (q, 2H), 7.21 (s, 1H).
EXAMPLE 9
[0538] Chloro-ethylsulfanylcarbonyloxy-acetic acid butyl ester (Compound 2-3 of Table 2)
[0539] The title compound was prepared according to the procedure described in Example 7 above except for the substitution of n-butyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate for ethyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.95 (t, 3H), 1.33-1.43 (m, 5H), 1.67-1.72 (m, 2H), 2.93 (q, 2H), 4.25-4.30 (m, 2H), 6.65 (s, 1H).
EXAMPLE 10
[0540] Iodo-ethylsulfanylcarbonyloxy-acetic acid butyl ester (Compound 2-4 of Table 2)
[0541] The title compound was prepared according to the procedure described in Example 8 above except for the substitution of chloro-ethylsulfanylcarbonyloxy-acetic acid butyl ester for chloro-ethylsulfanylcarbonyloxy-acetic acid ethyl ester. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.95 (t, 3H), 1.32-1.43 (m, 5H), 1.65-1.70 (m, 2H), 2.92-2.95 (m, 2H), 4.22-4.26 (m, 2H), 7.21 (s, 1H).
EXAMPLE 11
[0542] Chloro-ethylsulfanylcarbonyloxy-acetic acid isopropyl ester (Compound 2-5 of Table 2)
[0543] The title compound was prepared according to the procedure described in Example 7 above except for the substitution of isopropyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate for ethyl 2-chloro-2-[(chlorocarbonyl)oxy]acetate. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.30 (t, 9H), 2.90 (q, 2H), 5.10 (s, 1H), 6.60 (s, 1H).
EXAMPLE 12
[0544] Iodo-ethylsulfanylcarbonyloxy-acetic acid isopropyl ester (Compound 2-6 of Table 2)
[0545] The title compound was prepared according to the procedure described in Example 8 above except for the substitution of chloro-ethylsulfanylcarbonyloxy-acetic acid isopropyl ester for chloro-ethylsulfanylcarbonyloxy-acetic acid ethyl ester. 1H-NMR (300 MHz, CDCl3) 8 (ppm): 1.30 (t, 9H), 2.90 (q, 2H), 5.10 (s, 1H), 7.15 (s, 1H).
[0546] Following the general methods described hereinbefore, the following compounds of Formula IV (where G10, G11, G20, G21, G30, and G31=O, and R2=H) as listed in Table 3 were prepared.
3TABLE 3
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76
|
Listing of Compounds of Formula IV
Cmpd #R12t′d(X3)dZ3tq(X2)qZ2
|
3-1 Et10ethyl102-propyl
3-2 Et10ethyl10t-butyl
3-3 Et10ethyl10ethyl
3-4 Et10ethyl102-ethoxyphenyl
3-5 Et10ethyl10phenyl
3-6 Et10ethyl102,4-dichlorophenoxymethyl
3-7 Et10ethyl103-(2,4-dichlorophenoxy)propyl
3-8 Et10ethyl101-(2,4-dichlorophenoxy)ethyl
3-9 Et10ethyl102,5-dichloro-6-methoxyphenyl
3-10Et10ethyl102,4,6-trimethylphenyl
3-11Et102-propyl10phenyl
3-12Et102-propyl10t-butyl
3-13Et102-propyl101-methyl-1-cyclopropyl
3-14Et102-propyl102-propyl
3-15Et102-propyl10ethyl
3-16Et102-propyl10N-acetyl-N-methyl-aminomethyl
3-17Et10n-butyl10(diethoxyphosphoryl)methyl
3-18Et10n-butyl10t-butyl
3-19Et102-propyl103,7-dichloro-8-quinoline
|
[0547] The following Examples are provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 13
[0548] 2-Methylpropanoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-1 of Table 3)
[0549] To a stirred ice cold solution of iodo-ethylsulfanylcarbonyloxy-acetic acid ethyl ester (5.4 g, 17.0 mmol) in 20 mL of dry THF was added 2-methylpropanoic acid (1.94 g, 22.1 mmol) followed by DIEA (2.85 g, 22.1 mmol). The reaction was allowed to stir at room temperature for 16 h. The reaction was diluted with 100 mL of diethyl ether, gravity filtered, and concentrated under reduced pressure. The liquid was suction filtered through a pad of flash grade silica gel and eluted with 20% methylene chloride/hexanes. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.24 (m, 6H), 1.33 (m, 6H), 2.66 (m, 1H), 2.90 (q, 2H), 4.28 (q, 2H), 5.92 (s, 1H).
EXAMPLE 14
[0550] Pivalic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-2 of Table 3)
[0551] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of pivalic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) 5 (ppm): 1.25 (s, 9H), 1.33 (m, 6H), 2.88 (q, 2H), 4.28 (q, 2H), 6.82 (s, 1H).
EXAMPLE 15
[0552] Propionic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-3 of Table 3)
[0553] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of propionic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.16 (t, 3H), 1.30 (m, 6H), 2.47 (q, 2H), 2.93 (q, 2H), 4.29 (q, 2H), 6.94 (s, 1H).
EXAMPLE 16
[0554] 2-Ethoxybenzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-4 of Table 3)
[0555] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 2-ethoxybenzoic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.23 (m, 6H), 1.44 (t, 3H), 2.92 (q, 2H), 4.12 (q, 2H), 4.31 (q, 2H), 6.96 (m, 2H), 7.15 (s, 1H), 7.43 (t, 1H), 7.92 (d, 1H).
EXAMPLE 17
[0556] Benzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-5 of Table 3)
[0557] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of benzoic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.32 (m, 6H), 2.93 (q, 2H), 4.35 (q, 2H), 7.19 (s, 1H), 7.35 (t, 2H), 7.48 (t, 1H), 8.10 (d, 2H).
EXAMPLE 18
[0558] 2,4-Dichlorophenoxyacetic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-6 of Table 3)
[0559] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 2,4-dichlorophenoxyacetic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.32 (m, 6H), 2.92 (q, 2H), 4.29 (q, 2H), 4.82 (s, 2H), 6.83 (d, 1H), 6.95 (s, 1H), 7.24 (dd, 1H), 7.38 (s, 1H).
EXAMPLE 19
[0560] 4-(2,4-Dichlorophenoxy)butyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-7 of Table 3)
[0561] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 4-(2,4-diclorophenoxy)butyric acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) 8 (ppm): 1.32 (m, 6H), 2.18 (m, 2H), 2.76 (t, 2H), 2.97 (q, 2H), 4.02 (q, 2H), 4.31 (q, 2H), 6.83 (d, 1H), 6.86 (s, 1H), 7.15 (d, 1H), 7.35 (d, 1H).
EXAMPLE 20
[0562] 2′-(2,4-Dichlorophenoxy)propionic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-8 of Table 3)
[0563] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 2′-(2,4-diclorophenoxy)propionic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) 5 (ppm): 1.32 (m, 6H), 1.74 (m, 3H), 2.91 (q, 2H), 4.26 (q, 2H), 4.88 (m, 1H), 6.88 (m, 1H), 6.95 (s, 1H), 7.18 (d, 1H), 7.38 (s, 1H).
EXAMPLE 21
[0564] 2,5-Dichloro-6-methoxybenzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-9 of Table 3)
[0565] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 2,5-dichloro-6-methoxybenzoic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.34 (m, 6H), 2.93(q, 2H), 3.94 (s, 3H), 4.34 (q, 2H), 7.16 (d, 1H), 7.18 (s, 1H), 7.39 (d, 1H).
EXAMPLE 22
[0566] 2,4,6-Trimethylbenzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-10 of Table 3)
[0567] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of 2,4,6-trimethylbenzoic acid for 2-methylpropanoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.33 (m, 6H), 2.27 (s, 3H), 2.34 (s, 6H), 2.90 (q, 2H), 4.31 (q, 2H), 6.86 (s, 2H), 7.16 (s, 1H).
EXAMPLE 23
[0568] Benzoic acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-11 of Table 3)
[0569] To a stirred ice cold solution of iodo-ethylsulfanylcarbonyloxy-acetic acid isopropyl ester (3.1 g, 9.3 mmol) in 40 mL of dry THF was added benzoic acid (1.5 g, 12.0 mmol) followed by DIEA (2.1 mL, 12.0 mmol). The reaction was allowed to stir at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in ether and washed 3 times with a saturated solution of sodium bicarbonate and once with brine. The ether layer was dried over MgSO4 and concentrated to yield 2.0 g (66%) of the desired product, which was used without further purification. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.30 (m, 9H), 2.90 (q, 2H), 5.15 (m, 1H), 7.13 (s, 1H), 7.55 (m, 3H), 8.10 (m, 2H).
EXAMPLE 24
[0570] Pivalic acid isopropoxycarbonyl-ethyl sulfanylcarbonyloxy-methyl ester (Compound 3-12 of Table 3)
[0571] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of pivalic acid for benzoic acid. 1H-NMR (300 MHz, CDCl3) 5 (ppm): 1.30 (m, 18H), 2.90 (q, 2H), 5.10 (m, 1H), 6.85 (s, 1H).
EXAMPLE 25
[0572] 1-Methyl-1-cyclopropanecarboxylic acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-13 of Table 3)
[0573] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of 1-methyl-1-cyclopropanecarboxylic acid for benzoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.75 (d, 2H), 1.35 (m, 14H), 2.90 (m, 2H), 5.10 (m, 1H), 6.85 (s, 1H).
EXAMPLE 26
[0574] Isobutyric acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-14 of Table 3)
[0575] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of isobutyric acid for benzoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.25 (m, 15H), 2.65 (m, 1H), 2.90 (m, 2H), 5.10 (m, 1H), 6.90 (s, 1H).
EXAMPLE 27
[0576] Propionic acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-15 of Table 3)
[0577] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of propionic acid for benzoic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.15 (t, 3H), 1.30 (m, 9H), 2.45 (q, 2H), 2.90 (q, 2H), 5.10 (m, 1H), 6.90 (s, 1H).
EXAMPLE 28
[0578] Acetyl methyl carbamic acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-16 of Table 3)
[0579] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of acetyl methyl carbamic acid for benzoic acid. 1H-NMR (300 MHz; CDCl3) & (ppm): 1.30 (m, 9H), 2.10 (d, 3H), 2.90 (m, 2H), 3.10 (d, 3H), 4.20 (m, 2H), 5.10 (m, 1H), 6.90 (s, 1H).
EXAMPLE 29
[0580] Diethylphosphonoacetic acid butoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-17 of Table 3)
[0581] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of diethylphosphonoacetic acid for 2-methylpropanoic acid and iodoethylsulfanylcarbonyloxy-acetic acid butyl ester for iodoethylsulfanylcarbonyloxy-acetic acid ethyl ester. 1H-NMR (300 MHz, CD3OD) δ (ppm): 1.35 (t, 6H), 2.89 (q, 2H), 3.03 (d, 2H), 4.18 (q, 4H), 5.84 (s, 2H).
EXAMPLE 30
[0582] Pivalic acid butoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-18 of Table 3)
[0583] The title compound was prepared according to the procedure described in Example 13 above except for the substitution of pivalic acid for 2-methylpropanoic acid and iodoethylsulfanylcarbonyloxy-acetic acid butyl ester for iodoethylsulfanylcarbonyloxy-acetic acid ethyl ester. 1H-NMR (300 MHz, CD3OD) δ (ppm): 1.25 (s, 9H), 1.31-1.45 (m, 8H), 1.65 (m 2H), 2.95 (q, 2H), 4.25 (m, 2H), 6.92 (s, 1H).
EXAMPLE 31
[0584] 3,7-Dichloro-8-quinolinecarboxylic acid isopropoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester (Compound 3-19 of Table 3)
[0585] The title compound was prepared according to the procedure described in Example 23 above except for the substitution of 3,7-dichloro-8-quinolinecarboxylic acid for benzoic acid. 1H-NMR (300 MHz, CDCl3) d (ppm): 1.35 (m, 9H), 2.95 (q, 2H), 5.15 (m, 1H), 7.25 (s, 1H), 7.57 (d, 1H), 7.76 (d, 1H), 8.14 (s, 1H) 8.83 (s, 1H).
[0586] Following the general methods described hereinbefore, the following compounds of Formula III (where G10, G11, G20, G21, G30, and G31=O and R2=H) as listed in Table 4 were prepared.
4TABLE 4
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77
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Listing of Compounds of Formula III
Cmpd #Y1t′d(X3)dZ3tq(X2)qZ2
|
4-1 Cl10ethyl102-propyl
4-2 Cl10ethyl10t-butyl
4-3 Cl10ethyl10ethyl
4-4 Cl10ethyl102-ethoxyphenyl
4-5 Cl10ethyl10phenyl
4-6 Cl10ethyl103-(2,4-dichlorophenoxy)propyl
4-7 Cl10ethyl101-(2,4-dichlorophenoxy)ethyl
4-8 Cl10ethyl102,5-dichloro-6-methoxyphenyl
4-9 Cl10ethyl102,4,6-trimethylphenyl
4-10Cl10n-butyl10diethylphosphonomethyl
4-11Cl10n-butyl10t-butyl
4-12Cl102-propyl102-propyl
4-13Cl10n-butyl102-propyl
4-14Cl102-propyl10phenyl
4-15Cl102-propyl10undecanyl
4-16Cl102-propyl111-[4-(2-methylpropyl)phenyl]ethyl
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[0587] The following Examples are provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 32
[0588] 2-Methylpropionic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-1 of Table 4)
[0589] A 100 mL round bottom flask was charged with 2-methylpropionic acid ethoxycarbonyl-ethyl sulfanylcarbonyloxy-methyl ester (4.4 g, 15.8 mmol) and cooled to 5° C. Sulfuryl chloride (2.70 g, 20.0 mmol) was added over 1 min. After 30 min of stirring, the cooling bath was removed and the reaction was allowed to stir for 3 h at room temperature and then placed under vacuum. The material was used without purification. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.26 (m, 9H), 2.58 (m, 1H), 4.32 (q, 2H), 6.83 (s, 1H).
EXAMPLE 33
[0590] Pivalic acid ethoxycarbonyl-chlorocarbonyloxy methyl ester (Compound 4-2 of Table 4)
[0591] The title compound was prepared according to the procedure described in Example 32 above except for the substitution of pivalic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.25 (s, 9H), 1.33 (t, 3H), 4.32 (q, 2H), 6.78 (s, 1H).
EXAMPLE 34
[0592] Propionic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-3 of Table 4)
[0593] The title compound was prepared according to the procedure described in Example 32 above except for the substitution propionic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.4 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.21 (t, 3H), 1.35 (t, 3H), 2.53 (q, 2H), 4.32 (q, 2H), 6.84 (s, 1H).
EXAMPLE 35
[0594] 2-Ethoxybenzoic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-4 of Table 4)
[0595] The title compound was prepared according to the procedure described in Example 32 above except for the substitution 2-ethoxybenzoic acid ethoxycarbonylethylsulfanyl-carbonyloxy methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.4 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.36 (t, 3H), 1.45 (t, 3H), 4.13 (q, 2H), 4.36 (q, 2H), 6.95 (m, 2H), 7.02 (s, 1H), 7.47 (t, 1H), 7.91(d, 1H).
EXAMPLE 36
[0596] Benzoic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-5 of Table 4)
[0597] The title compound was prepared according to the procedure described in Example 32 above except for the substitution benzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.2 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.36 (t, 3H), 4.32 (q, 2H), 7.09 (s, 1H), 7.50 (t, 2H), 7.63 (t, 1H), 8.10 (d, 2H).
EXAMPLE 37
[0598] 2,4-Dichlorophenoxybutyric acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-6 of Table 4)
[0599] The title compound was prepared according to the procedure described in Example 32 above except for the substitution 2,4-dichlorophenoxybutyric acid ethoxycarbonylethyl-sulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl ethylsulfanylcarbonyl-oxy-methyl ester, using 1.45 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCB) δ (ppm): 1.34 (t, 3H), 2.21 (m, 2H), 2.56 (t, 2H), 4.07 (t, 2H), 4.31 (q, 2H), 6.83 (d, 1H), 6.86 (s, 1H), 7.17 (d, 1H), 7.35 (d, 1H).
EXAMPLE 38
[0600] 2′-(2,4-Dichlorophenoxy)propionic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-7 of Table 4)
[0601] The title compound was prepared according to the procedure described in Example 32 above except for the substitution 2′-(2,4-dichlorophenoxy)propionic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.80 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.37 (t, 3H), 1.92 (m, 3H), 4.33 (q, 2H), 4.83 (m, 1H), 6.84 (m, 2H), 7.16 (dd, if), 7.38 (d, 1H).
EXAMPLE 39
[0602] 2,5-Dichloro-6-methoxybenzoic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-8 of Table 4)
[0603] The title compound was prepared according to the procedure described in Example 32 above except for the substitution 2,5-dichloro-6-methoxybenzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.45 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCB) δ (ppm): 1.34 (t, 3H), 3.95 (s, 3H), 4.36 (q, 2H), 7.08 (s, 1H), 7.18 (d, 1H), 7.42 (d, 1H).
EXAMPLE 40
[0604] 2,4,6-Trimethylbenzoic acid ethoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-9 of Table 4)
[0605] The title compound was prepared according to the procedure described in Example 32 above except for the substitution of 2,4,6-trimethylbenzoic acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.45 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) 8 (Ppm): 1.34 (t, 3H), 2.28 (s, 3H), 2.35 (s, 6H), 4.34 (q, 2H), 6.89 (s, 1H), 7.06 (s, 1H), 7.12 (s, 1H).
EXAMPLE 41
[0606] Diethylphosphonoacetic acid butoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-10 of Table 4)
[0607] The title compound was prepared according to the procedure described in Example 32 above except for the substitution diethylphosphonoacetic acid butoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.9 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.96 (t, 3H), 1.37 (t, 6H), 1.72 (m, 2H), 2.01 (m, 2H), 3.15 (d, 2H), 4.27 (m, 6H), 6.85 (s, 1H).
EXAMPLE 42
[0608] Pivalic acid butoxycarbonyl-chlorocarbonyloxy-methyl ester (Compound 4-11 of Table 4)
[0609] The title compound was prepared according to the procedure described in Example 32 above except for the substitution of pivalic acid butoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.9 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3) 8 (ppm): 0.95 (t, 3H), 1.27 (s, 9H), 1.35-1.45 (m, 2H), 1.65-1.75 (m 2H), 4.31 (m, 2H), 6.85 (s, 1H).
EXAMPLE 43
[0610] 2-Methylpropanoic acid (chlorocarbonyloxy)-[(1-methylethoxy)carbonyl]methyl ester (Compound 4-12 of Table 4)
[0611] The title compound was prepared according to the procedure described in Example 32 above except for the substitution of isobutyric acid isobutoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester for isobutyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester, using 1.9 equiv of sulfuryl chloride and starting the reaction at 5° C. 1H-NMR (300 MHz, CDCl3), (ppm): 1.22-1.30 (m, 6H), 1.30-1.40 (m, 6H), 2.70 (heptet, 1H), 5.14 (heptet, 1H), 6.77 (s, 1H).
EXAMPLE 44
[0612] 2-Methylpropanoic acid (chlorocarbonyloxy)(butoxycarbonyl)methyl ester (Compound 4-13 of Table 4)
[0613] Diisopropylethylamine (0.57 g, 4.41 mmole) was added in three portions 2 min apart to a shaken solution of butyl 2-(ethylthiocarbonyloxy)-2-iodoethanoate (1.01 g, 2.92 mmol) and 2-methyl-2-propanoic acid (0.32 g, 3.63 mmole) in 1.11 g anhydrous tetrahydrofuran. One minute later, isobutyric acid (0.13 g, 1.47 mmole) was added to neutralize an accidental amine overcharge. After the mixture stood with occasional shaking for 16 h at room temperature, the slurry was concentrated in vacuo to 2.00 g, and the residue was extracted with three 3.4-5.5 g portions of ca. 2/1 w/w diethylether/hexanes. The supernatants were washed with 41.3 wt. % aqueous potassium carbonate solution and concentrated in vacuo to give 2-methylpropanoic acid (ethylthiocarbonyloxy)-(butoxycarbonyl)methyl ester (0.79 g, 2.58 mmol), as a pale yellow oil. This oil was dissolved in 1.09 g dichloromethane and 97% sulfuryl chloride (0.90 g, 6.67 mmol) was added in three portions 1 min apart at room temperature. After the resulting solution stood for another 68 min, it was concentrated in vacuo to constant weight to give 2-methylpropanoic acid (chlorocarbonyloxy)-(butoxycarbonyl)methyl ester (0.73 g, 2.60 mmole, 89% overall yield) as a yellow oil. 1H-NMR (300 MHz, CDCl3) 8 (ppm): 0.95 (t, 3H), 1.24 (d, 3H), 1.25 (d, 2H), 1.39 (sextet, 2H), 1.68 (p, 4H), 2.71 (septet, 1H), 6.99(s, 1H).
EXAMPLE 45
[0614] Benzoic acid (chlorocarbonyloxy)(isopropoxycarbonyl)methyl ester (Compound 4-14 of Table 4)
[0615] Isopropyl 2-(ethylthiocarbonyloxy)-2-iodoethanoate (1.01 g, 3.04 mmol) was added to a well-mixed solution of benzoic acid (0.56 g, 4.59 mmol) and diisopropylethylamine (0.55 g, 4.25 mmol) in 2.20 g anhydrous tetrahydrofuran. This gave a slight exotherm and slow fading of the red color with precipitation of solid. After the mixture stood with occasional shaking for 4.3 h at room temperature, the slurry was concentrated in vacuo to 2.64 g and the residue was partitioned between 1.32 g deionized water containing 1.09 g 41.3% potassium carbonate solution and three 1.6-2.6 g hexanes extracts. The extracts were concentrated in vacuo to give benzoic acid (ethylthiocarbonyloxy)-(isopropoxycarbonyl)-methyl ester (0.87 g, 2.67 mmole), as a pale yellow oil. This oil was dissolved in 1.32 g dichloromethane and 97% sulfuryl chloride (0.89 g, 6.59 mmol) was added in three portions over 3 min at room temperature. The vigorous foaming soon subsided. After the resulting solution stood for another 2.4 h, it was concentrated in vacuo to constant weight to give benzoic acid (chlorocarbonyloxy)-(isopropoxycarbonyl)methyl ester (0.85 g, 2.83 mmole, 93% overall yield) as a yellow oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.34 (d, 6H), 5.20 (septet, 1H), 7.03 (s, 1H), 7.50 (t, 2H), 7.66 (t, H), 8.11 (d, 2H).
EXAMPLE 46
[0616] Dodecanoic acid (chlorocarbonyloxy)(isopropoxycarbonyl)methyl ester (Compound 4-15 of Table 4)
[0617] Isopropyl 2-(ethylthiocarbonyloxy)-2-iodoethanoate (1.01 g, 3.04 mmol) was added to a well-mixed solution of dodecanoic acid (0.91 g, 4.54 mmol) and diisopropylethylamine (0.56 g, 4.33 mmol) in 2.12 g anhydrous tetrahydrofuran. This gave a slight exotherm and slow fading of the red color with precipitation of solid. After the mixture stood with occasional shaking for 21.7 h at room temperature, the slurry was concentrated in a vacuo to 2.9 g and the residue was extracted with four 2.8-3.9 g portions of hexanes. The extracts were washed with 0.94 g 41.3% potassium carbonate solution and concentrated in vacuo to give dodecanoic acid (ethylthiocarbonyloxy)(isopropoxycarbonyl)methyl ester (0.77 g, 1.90 mmol), as a pale yellow oil. This oil was dissolved in 1.42 g dichloromethane and 97% sulfuryl chloride (0.73 g, 5.41 mmol) was added in three portions over 9 min at room temperature. The vigorous foaming soon subsided. After the resulting solution stood for another 3.6 h, it was concentrated in vacuo to constant weight to give dodecanoic acid (chlorocarbonyloxy)-(isopropoxycarbonyl)methyl ester (0.75 g, 1.98 mmole, 65% overall yield) as a yellow oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.88 (t, 3H), 1.26 (bs, 16H), 1.31 (two equal doublets 1.3 Hz apart, 6H), 1.59 (p, 2H), 5.19 (septet, 1H), 6.78 (s, 1H).
EXAMPLE 47
[0618] 2-[4-(2-Methylpropyl)phenyl]propanoic acid (chlorocarbonyloxy)(isopropoxy-carbonyl)methyl ester (Compound 4-16 of Table 4)
[0619] Five 200 mg ibuprofen (α-methyl-4-(2-methylpropyl)benzeneacetic acid) tablets (total tablet wt. 1.64 g, 4.85 mmol) were stirred for 15 min with 3.56 g dichloromethane containing triisopropylamine (0.63 g, 4.87 mmol). Isopropyl 2-(ethylthiocarbonyloxy)-2-iodoethanoate (1.03 g, 3.10 mmol) was added with a 0.90 g dichloromethane pipet rinse, causing a slight exotherm and fading of a red color. After the mixture stood with occasional shaking for 28 h at room temperature, the slurry was concentrated in vacuo to 3.88 g and the residue was extracted with five 3.3-4.0 g portions of hexanes. The hexanes supernatants were washed with 41.3 wt. % aqueous potassium carbonate solution and concentrated in vacuo to give 2-[4-(2-methylpropyl)phenyl]propanoic acid (ethylthiocarbonyloxy)(isopropoxy-carbonyl)methyl ester (1.05 g, 2.56 mmol), as a pale yellow oil. This oil was dissolved in 1.52 g dichloromethane and 97% sulfuryl chloride (1.05 g, 7.78 mmol) was added in four portions over 5 min at room temperature. After the resulting solution stood for another 120 min, it was concentrated in vacuo to constant weight to give 2-[4-(2-methylpropyl)phenyl]propanoic acid (chloro-carbonyloxy)(isopropoxy-carbonyl)methyl ester (1.00 g, 84% overall yield) as a yellow oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.90 ppm (d, 6H), 1.14-1.20 (two d, total of 3H), 1.27 (d, 3H), 1.55 d (3H), 1.56 (septet, 1H), 1.84 (septet, 1H), 2.45 (dd, 2H), 3.82 and 3.84 (two equal q, total of 1H), 5.04 and 5.11 (two equal septets, total of 1H), 6.74 and 6.76 (two equal s, total of 1H), 7.11 (d, 2H), 7.20 (d, 2H).
[0620] Following Method A described hereinbefore, the following compound of Formula XX as listed in Table 5 was prepared.
5TABLE 5
|
|
|
78
|
Listing of Compound of Formula XX
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
5-1OOOH102-102-
propylpropyl
|
[0621] The following Example is provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 48
[0622] 2-Methylpropionic acid (N-methyl-3-phenyl-3-[(4-trifluoromethyl)phenoxy]propylcarbamoyloxy)-(2-propyloxycarbonyl)methyl ester (Compound 5-1 of Table 5)
[0623] 2-Methylpropanoic acid (chlorocarbonyloxy)-[(1-methylethoxy)carbonyl]methyl ester (Compound 4-12, 28 μL, 0.12 mmol) was added via syringe to a solution of fluoxetine hydrochloride (Sigma Chemical Co., 42.5 mg, 0.123 mmol) and 4-(dimethylamino)pyridine (30.0 mg, 0.246 mmol) in THF (1.9 mL) at room temperature under N2. The reaction was allowed to stir for 16 h. Then saturated aqueous ammonium chloride was added, the product was extracted into ethyl acetate, the extract was dried over Na2SO4, and the volatiles were removed in vacuo. The crude product was purified by flash chromatography on silica gel using a hexanes-ethyl acetate gradient. The title compound was isolated cleanly as a pale yellow oil in 74% yield and consisted of a mixture of diastereomers. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.14-1.28 (m, 12H), 2.10-2.32 (m, 2H), 3.53-3.75 (m, 1H), 2.93-2.95 (m, 3H), 3.51 (t, 2H), 5.05-5.17 (m, 1H), 5.17-5.27 (m, 1H), 6.70-6.75 (four singlets, 1H), 6.89 (d, 2H), 7.22-7.36 (m, 5H), 7.42 (d, 2H).
[0624] Following Method A described hereinbefore, the following compound of Formula XXII as listed in Table 6 was prepared.
6TABLE 6
|
|
|
79
|
Listing of Compound of Formula XXII
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
6-1OOOH102-102-
propylpropyl
|
[0625] The following Example is provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 49
[0626] 2-Methylpropionic acid [(2,4-difluoro-1-phenyl)-bis-(1H-1,2,4-triazol 1-ylmethyl)]methyloxycarbonyloxy-(2-propyloxycarbonyl)methyl ester (Compound 6-1 of Table 6)
[0627] Potassium bis(trimethylsilyl)amide (0.327 mL of a 0.5 M solution in toluene, 0.16 mmol) was added via syringe to a solution of fluconazole (Pfizer, 50.5 mg, 0.165 mmol) in THF (1.5 mL) at −78° C. under N2. The reaction was allowed to stir at −78° C. for 10 min, then at 0° C. for 35 min, at which time 2-methylpropanoic acid (chlorocarbonyloxy)-[(1-methylethoxy)carbonyl]methyl ester (Compound 4-12, 76 μL, 0.16 mmol) was added via syringe. The reaction was allowed to warm slowly to room temperature over 22 h. Then saturated aqueous ammonium chloride was added, the product was extracted into ethyl acetate, the extract was dried over Na2SO4, and the volatiles were removed in vacuo. The crude product was purified by flash chromatography on silica gel using an ethyl acetate-methanol gradient. The title compound was isolated as a pale yellow oil in 40% yield; unreacted fluconazole was also recovered (28%). 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.22-1.25 (m, 6H), 1.28-1.31 (m, 6H), 2.70 (heptet, 1H), 5.06-5.24 (m, 5H), 6.73 (s, 1H), 6.73-6.81 (m, 1H), 6.82-6.96 (m, 2H), 7.85 (s, 1H), 7.86 (s, 1H), 8.08 (s, 1H), 8.12 (s, 1H).
[0628] Following Method A described hereinbefore, the following compound of Formula XXIV as listed in Table 7 was prepared.
7TABLE 7
|
|
|
80
|
Listing of Compound of Formula XXIV
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
7-1OOOH102-102-
propylpropyl
|
[0629] The following Example is provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 50
[0630] 2-Methylpropionic acid [2,6-Dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydropyridin-1-yl]carbonyloxy-(2-propyloxycarbonyl)methyl ester (Compound 7-1 of Table 7)
[0631] Potassium bis(trimethylsilyl)amide (0.296 mL of a 0.5 M solution in toluene, 0.148 mmol) was added via syringe to a solution of nifedipine (Sigma Chemical Co., 51.3 mg, 0.148 mmol) in THF (1.5 mL) at −78° C. under N2. The reaction was allowed to stir at −78° C. for 15 min, then at 0° C. for 35 min, at which time 2-methylpropanoic acid (chlorocarbonyloxy)-[(1-methylethoxy)carbonyl]methyl ester (compound 4-12, 33 uL, 0.15 mmol) was added via syringe. The reaction was allowed to warm slowly to room temperature over 16 h. Then saturated aqueous ammonium chloride was added, the product was extracted into ethyl acetate, the extract was dried over Na2SO4, and the volatiles were removed under reduced pressure. The crude product was purified by flash chromatography on silica gel using a hexanes-ethyl acetate gradient. The title compound was isolated as a pale yellow oil in 12% yield; unreacted nifedipine was also recovered (54%). 1H-NMR (300 MHz, CDCB) δ (ppm): 1.20-1.34 (m, 12H), 2.48 (s, 3H), 2.52 (s, 3H), 2.67 (heptet, 1H), 3.72 (s, 3H), 3.73 (s, 3H), 5.15 (heptet, 1H), 5.73 (s, 1H), 6.86 (s, 1H), 7.24-7.35 (m, 2H), 7.54 (t, 1H), 7.68 (d, 1H).
[0632] Following Method A described hereinbefore, the following compounds of Formula XXVI as listed in Table 8 were prepared.
8TABLE 8
|
|
|
81
|
Listing of Compounds of Formula XXVI
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
8-1OOOH10n-butyl102-propyl
8-2OOOH102-propyl10phenyl
8-3OOOH10n-butyl10undecyl
8-4OOOH102-propyl111-[4-(2-methyl-
propyl)phenyl]ethyl
|
[0633] The following Examples are provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 51
[0634] 7-(4-[(Butoxycarbonyl)(2-methylpropanoyloxy)methoxycarbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Compound 8-1 of Table 8)
[0635] 2-Methylpropanoic acid (chlorocarbonyloxy)(butoxycarbonyl)methyl ester (0.22 g, 0.78 mmol) was added in two portions (0.19 g, 0.03 g) with shaking 2 min apart to a slurry of norfloxacin (0.22 g, 0.69 mmol) and triisopropylamine (0.15 g, 1.05 mmol) in 2.42 g CH2Cl2, causing a moderate exotherm and dissolution of much then almost all of the solid. The mixture stood another 10 min at room temperature before it was concentrated in vacuo to 0.78 g of gum and solid. This residue was repeatedly shaken with small portions of 3-4:1 w:w ethyl acetate:hexanes eluant which were added to the top of a 1.02 g (7.2 cm×0.65 cm ID) silica gel column. Evaporation of the eluate in 3 portions gave a total of 0.34 g of yellow to white solid crystals. The two colored portions of crystals were washed twice with diethyl ether/hexanes to give 0.05 g soluble gum and insoluble off-white crystals. The three portions of crystals were combined to give 7-(4-[(butoxycarbonyl)(2-methylpropanoyloxy)-methoxycarbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylic acid (0.30 g, 77% yield). 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.94 (t, 3H), 1.23 (d, 3H), 1.24 (d, 3H), 1.40 (sextet, 2H), 1.60 (t, 4H, area may include obscured water peak), 1.64 (p, 3H), 2.67 (septet, 1H), 3.31 (t, 4H), 3.77 (s, 4H), 4.24 (t, 2H), 4.33 (q, 2H), 6.85 (s, 1H), 6.86 (d, 1H)., 8.09 (d, 1H), and 8.68 (s, 1H). Mp=151.5-160.0° C. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 563.8 compared with a calculated m/g of 563.23 for the C27H34N3O9F parent ion of the assigned structure.
EXAMPLE 52
[0636] 7-(4-[(Isopropoxycarbonyl)(benzoyloxy)methoxycarbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Compound 8-2 of Table 8)
[0637] The title compound was prepared according to the procedure described in Example 51 above except for the substitution of benzoic acid (chlorocarbonyloxy)-(isopropoxycarbonyl)methyl ester for 2-methylpropanoic acid (chlorocarbonyl-oxy)(butoxycarbonyl)methyl ester. The yield of off-white crystals was 0.30 g (70% after correction for 7 wt. % ethyl acetate). Mp 135-143° C. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 583.7 compared with a calculated m/g of 583.20 for the C29H30N3O9F parent ion of the assigned structure.
EXAMPLE 53
[0638] 7-(4-[(Isopropoxycarbonyl)(dodecanoyloxy)methoxycarbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Compound 8-3 of Table 8)
[0639] The title compound was prepared according to the procedure described in Example 51 above except for the substitution of dodecanoic acid (chlorocarbonyl-oxy)(isopropoxycarbonyl)methyl ester for 2-methylpropanoic acid (chlorocarbonyloxy)(butoxycarbonyl)methyl ester. The yield of off-white crystals was 0.34 g (74%). Mp 105.5-109.2° C. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 661.8 compared with a calculated m/g of 661.34 for the C34H48N3O9F parent ion of the assigned structure.
EXAMPLE 54
[0640] 7-(4-[(2-[4-(2-Methylpropyl)phenyl]propanoyloxy)(isopropoxycarbonyl)methoxy-carbonyl]-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Compound 8-4 of Table 8)
[0641] The title compound was prepared according to the procedure described in Example 51 above except for the substitution of 2-[4-(2-methylpropyl)phenyl]-propanoic acid (chlorocarbonyloxy)(isopropoxycarbonyl)methyl ester for 2-methylpropanoic acid (chlorocarbonyloxy)(butoxycarbonyl)methyl ester. The yield of off-white crystals was 0.41 g (89%). Mp 88.0-96.5° C. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 667.9 compared with a calculated m/g of 667.29 for the C35H42N3O9F parent ion of the assigned structure.
[0642] Following Method A described hereinbefore, the following compound of Formula XXVIII as listed in Table 9 was prepared.
9TABLE 9
|
|
|
82
|
Listing of Compound of Formula XXVIII
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
9-1OOOH102-102-
propylpropyl
|
[0643] The following Example is provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 55
[0644] 2-(2-Methylpropanoyloxy)-2-(4-acetamidophenoxycarbonyloxy)ethanoic acid 1-methylethyl ester (Compound 9-1 of Table 9)
[0645] 4-Acetamidophenol (0.15 g, 0.99 mmol) was stirred for 8 min with 1.06 g absolute ethanol and fragmented 87.11 wt. % potassium hydroxide pellets (0.05 g, 0.78 meq) to form a homogeneous solution. Ethanol (0.96 g) was concentrated in vacuo, toluene (0.50 g) was added, and the mixture was concentrated in vacuo with repeated heating to give an additional 0.04 g weight loss. Dichloromethane (7.87 g) and 2-(chlorocarbonyloxy)-2-(2-methylpropanoyloxy)ethanoic acid 1-methylethyl ester (0.19 g, 0.71 mmol) were added with shaking without dissolving much of the gum. The mixture stood for 17 h at room temperature, causing solid to form in both the solvent and gum layers. The stirring bar was freed by breaking up the solid and the mixture was stirred for 3.3 h, forming a finely dispersed slurry. The slurry was concentrated in vacuo to a tan opaque gum which was extracted with four portions of ethyl acetate to separate crude (0.27 g, ca. 70% by NMR) 2-(2-methylpropanoyloxy)-2-(4-acetamidophenoxycarbonyloxy)ethanoic acid 1-methylethyl ester from insoluble solid. Short column silica gel chromatography using chloroform eluant gave purified 2-(2-methylpropanoyloxy)-2-(4-acetamidophenoxycarbonyloxy)-ethanoic acid 1-methylethyl ester (0.17 g, 63% yield) as a yellowish tan gum. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 381.7 compared with a calculated m/g of 381.14 for the C18H23NO8 parent ion of the assigned structure.
[0646] Following Method A described hereinbefore, the following compound of Formula XXX as listed in Table 10 was prepared.
10TABLE 10
|
|
|
83
|
Listing of Compound of Formula XXX
Cmpd #G20G21G31R2t′d(X3)dZ3tq(X2)qZ2
|
10-1OOOH10n-butyl102-propyl
|
[0647] The following Example is provided for guidance to the practitioner in order to practice the invention.
EXAMPLE 56
[0648] 4-([(Butoxycarbonyl)(2-methylpropanoyloxy)methoxycarbonyl]amino)-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (Compound 10-1 of Table 10)
[0649] 2-Methylpropanoic acid (chlorocarbonyloxy)(butoxycarbonyl)methyl ester (0.21 g, 0.75 mmol) was added in two portions 2 min apart to a shaken slurry of 4-amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide (0.18 g, 0.71 mmol) in 1.51 g CH2Cl2 containing triisopropylamine (0.12 g, 0.84 mmol). This afforded a slightly delayed moderate exotherm and caused most of the solid to dissolve. After 10 min of cooling to room temperature, the mixture was concentrated in vacuo to 0.70 g, 0.67 g diethyl ether was added to induce crystallization, and the mixture was concentrated in vacuo to 0.65 g of partially crystalline gum. The mixture was repeatedly washed with small portions of diethyl ether, then with ethyl acetate/hexanes eluant and the supernatants were passed through a 1.14 g (7.72 cm×0.68 cm ID) silica gel column to give six fractions. Five of these fractions, totaling 0.35 g, appeared by NMR to contain significant amounts of the desired product. Normal phase preparative HPLC of the non-volatiles from the best of these fractions (0.13 g) gave high purity 4-([(butoxycarbonyl)(2-methyl-propanoyloxy)methoxycarbonyl]amino)-N-(5-methyl-3-isoxazolyl)benzene-sulfonamide (0.026 g, 7.3% yield) as a golden gum, along with an equal quantity of less pure material. Reverse phase LC/electrospray MS gave a predominant LC peak with a positively charged P+1 ion at m/g 497.7 compared with a calculated m/g of 497.15 for the C21H27N3O9S parent ion of the assigned structure.
[0650] Table A1 describes additional examples of compounds of Formula I which can be made using the procedures described hereinbefore, where R2 is hydrogen, m=1, q=0, t=0 or 1 and the pharmaceutical which defines the pharmaceutical moiety of these examples is Z1(X1)m—H. The following groups, Z1(X1), —H, X1, G10, G11, R1, G20, G21, t and Z2 are defined within Table A1.
11TABLE A1
|
|
|
84
|
Cmpd #Z1(X1)m—HX1G10G11R1G20G21tZ2
|
A1-1aletamineNOOCO2HOO1methyl
A1-2aletamineNOOCO2HOO1C(CH3)3
A1-3aletamineNOOCO2HOO1Ph
A1-4aletamineNOOCO2HOO14-Me-Ph
A1-5aletamineNOOCO2HOO12-pyridyl
A1-6aletamineNOOCO2HOO14-pyridyl
A1-7aletamineNOOCO2HOO12-furyl
A1-8aletamineNOOCO2HOO12-thienyl
A1-9aletamineNOOCO2H——0Cl
A1-10aletamineNOOCO2H——0{N(Et)3}+Cl−
A1-11aletamineNOOCO2HOO1CF3CH2
A1-12aletamineNOOCO2HOO1cyclopropyl
A1-13aletamineNOOCO2HOO12-OMe-Ph
A1-14aletamineNOOCO2HOO1MeSCH2
A1-15aletamineNOOCO2HOO1MeOCH2
A1-16aletamineNOOCO2HSS1Ph
A1-17aletamineNOOCO2HSS1NMe2
A1-18aletamineNOOCO2HSS1NBn2
A1-19aletamineNOOCO2HOS1Ph
A1-20aletamineNOOCO2HOS1Me
A1-21amphetamineNOOCO2HOO1methyl
A1-22amphetamineNOOCO2HOO1C(CH3)3
A1-23amphetamineNOOCO2HOO1Ph
A1-24amphetamineNOOCO2HOO14-Me-Ph
A1-25amphetamineNOOCO2HOO12-pyridyl
A1-26amphetamineNOOCO2HOO14-pyridyl
A1-27amphetamineNOOCO2HOO12-furyl
A1-28amphetamineNOOCO2HOO12-thienyl
A1-29amphetamineNOOCO2H——0Cl
A1-30amphetamineNOOCO2H——0{N(Et)3)+Cl−
A1-31amphetamineNOOCO2HOO1CF3CH2
A1-32amphetamineNOOCO2HOO1cyclopropyl
A1-33amphetamineNOOCO2HOO12-OMe-Ph
A1-34amphetamineNOOCO2HOO1MeSCH2
A1-35amphetamineNOOCO2HOO1MeOCH2
A1-36amphetamineNOOCO2HSS1Ph
A1-37amphetamineNOOCO2HSS1NMe2
A1-38amphetamineNOOCO2HSS1NBn2
A1-39amphetamineNOOCO2HOS1Ph
A1-40amphetamineNOOCO2HOS1Me
A1-41betahistineNOOCO2HOO1methyl
A1-42betahistineNOOCO2HOO1C(CH3)3
A1-43betahistineNOOCO2HOO1Ph
A1-44betahistineNOOCO2HOO14-Me-Ph
A1-45betahistineNOOCO2HOO12-pyridyl
A1-46betahistineNOOCO2HOO14-pyridyl
A1-47betahistineNOOCO2HOO12-furyl
A1-48betahistineNOOCO2HOO12-thienyl
A1-49betahistineNOOCO2H——0Cl
A1-50betahistineNOOCO2H——0{N(Et)3}+Cl−
A1-51betahistineNOOCO2HOO1CF3CH2
A1-52betahistineNOOCO2HOO1cyclopropyl
A1-53betahistineNOOCO2HOO12-OMe-Ph
A1-54betahistineNOOCO2HOO1MeSCH2
A1-55betahistineNOOCO2HOO1MeOCH2
A1-56betahistineNOOCO2HSS1Ph
A1-57betahistineNOOCO2HSS1NMe2
A1-58betahistineNOOCO2HSS1NBn2
A1-59betahistineNOOCO2HOS1Ph
A1-60betahistineNOOCO2HOS1Me
A1-61clonidineNOOCO2HOO1methyl
A1-62clonidineNOOCO2HOO1C(CH3)3
A1-63clonidineNOOCO2HOO1Ph
A1-64clonidineNOOCO2HOO14-Me-Ph
A1-65clonidineNOOCO2HOO12-pyridyl
A1-66clonidineNOOCO2HOO14-pyridyl
A1-67clonidineNOOCO2HOO12-furyl
A1-68clonidineNOOCO2HOO12-thienyl
A1-69clonidineNOOCO2H——0Cl
A1-70clonidineNOOCO2H——0{N(Et)3}+Cl−
A1-71clonidineNOOCO2HOO1CF3CH2
A1-72clonidineNOOCO2HOO1cyclopropyl
A1-73clonidineNOOCO2HOO12-OMe-Ph
A1-74clonidineNOOCO2HOO1MeSCH2
A1-75clonidineNOOCO2HOO1MeOCH2
A1-76clonidineNOOCO2HSS1Ph
A1-77clonidineNOOCO2HSS1NMe2
A1-78clonidineNOOCO2HSS1NBn2
A1-79clonidineNOOCO2HOS1Ph
A1-80clonidineNOOCO2HOS1Me
A1-81etintidineNOOCO2HOO1methyl
A1-82etintidineNOOCO2HOO1C(CH3)3
A1-83etintidineNOOCO2HOO1Ph
A1-84etintidineNOOCO2HOO14-Me-Ph
A1-85etintidineNOOCO2HOO12-pyridyl
A1-86etintidineNOOCO2HOO14-pyridyl
A1-87etintidineNOOCO2HOO12-furyl
A1-88etintidineNOOCO2HOO12-thienyl
A1-89etintidineNOOCO2H——0Cl
A1-90etintidineNOOCO2H——0{N(Et)3}+Cl−
A1-91etintidineNOOCO2HOO1CF3CH2
A1-92etintidineNOOCO2HOO1cyclopropyl
A1-93etintidineNOOCO2HOO12-OMe-Ph
A1-94etintidineNOOCO2HOO1MeSCH2
A1-95etintidineNOOCO2HOO1MeOCH2
A1-96etintidineNOOCO2HSS1Ph
A1-97etintidineNOOCO2HSS1NMe2
A1-98etintidineNOOCO2HSS1NBn2
A1-99etintidineNOOCO2HOS1Ph
A1-100etintidineNOOCO2HOS1Me
A1-101fenfluramineNOOCO2HOO1methyl
A1-102fenfluramineNOOCO2HOO1C(CH3)3
A1-103fenfluramineNOOCO2HOO1Ph
A1-104fenfluramineNOOCO2HOO14-Me-Ph
A1-105fenfluramineNOOCO2HOO12-pyridyl
A1-106fenfluramineNOOCO2HOO14-pyridyl
A1-107fenfluramineNOOCO2HOO12-furyl
A1-108fenfluramineNOOCO2HOO12-thienyl
A1-109fenfluramineNOOCO2H——0Cl
A1-110fenfluramineNOOCO2H——0{N(Et)3}+Cl−
A1-111fenfluramineNOOCO2HOO1CF3CH2
A1-112fenfluramineNOOCO2HOO1cyclopropyl
A1-113fenfluramineNOOCO2HOO12-OMe-Ph
A1-114fenfluramineNOOCO2HOO1MeSCH2
A1-115fenfluramineNOOCO2HOO1MeOCH2
A1-116fenfluramineNOOCO2HSS1Ph
A1-117fenfluramineNOOCO2HSS1NMe2
A1-118fenfluramineNOOCO2HSS1NBn2
A1-119fenfluramineNOOCO2HOS1Ph
A1-120fenfluramineNOOCO2HOS1Me
A1-121fludorexNOOCO2HOO1methyl
A1-122fludorexNOOCO2HOO1C(CH3)3
A1-123fludorexNOOCO2HOO1Ph
A1-124fludorexNOOCO2HOO14-Me-Ph
A1-125fludorexNOOCO2HOO12-pyridyl
A1-126fludorexNOOCO2HOO14-pyridyl
A1-127fludorexNOOCO2HOO12-furyl
A1-128fludorexNOOCO2HOO12-thienyl
A1-129fludorexNOOCO2H——0Cl
A1-130fludorexNOOCO2H——0{N(Et)3}+Cl−
A1-131fludorexNOOCO2HOO1CF3CH2
A1-132fludorexNOOCO2HOO1cyclopropyl
A1-133fludorexNOOCO2HOO12-OMe-Ph
A1-134fludorexNOOCO2HOO1MeSCH2
A1-135fludorexNOOCO2HOO1MeOCH2
A1-136fludorexNOOCO2HSS1Ph
A1-137fludorexNOOCO2HSS1NMe2
A1-138fludorexNOOCO2HSS1NBn2
A1-139fludorexNOOCO2HOS1Ph
A1-140fludorexNOOCO2HOS1Me
A1-141nifedipineNOOCO2HOO1methyl
A1-142nifedipineNOOCO2HOO1C(CH33)3
A1-143nifedipineNOOCO2HOO1Ph
A1-144nifedipineNOOCO2HOO14-Me-Ph
A1-145nifedipineNOOCO2HOO12-pyridyl
A1-146nifedipineNOOCO2HOO14-pyridyl
A1-147nifedipineNOOCO2HOO12-furyl
A1-148nifedipineNOOCO2HOO12-thienyl
A1-149nifedipineNOOCO2H——0Cl
A1-150nifedipineNOOCO2H——0{N(Et)3}+Cl−
A1-151nifedipineNOOCO2HOO1CF3CH2
A1-152nifedipineNOOCO2HOO1cyclopropyl
A1-153nifedipineNOOCO2HOO12-OMe-Ph
A1-154nifedipineNOOCO2HOO1MeSCH2
A1-155nifedipineNOOCO2HOO1MeOCH2
A1-156nifedipineNOOCO2HSS1Ph
A1-157nifedipineNOOCO2HSS1NMe2
A1-158nifedipineNOOCO2HSS1NBn2
A1-159nifedipineNOOCO2HOS1Ph
A1-160nifedipineNOOCO2HOS1Me
A1-161oxmetidineNOOCO2HOO1methyl
A1-162oxmetidineNOOCO2HOO1C(CH3)3
A1-163oxmetidineNOOCO2HOO1Ph
A1-164oxmetidineNOOCO2HOO14-Me-Ph
A1-165oxmetidineNOOCO2HOO12-pyridyl
A1-166oxmetidineNOOCO2HOO14-pyridyl
A1-167oxmetidineNOOCO2HOO12-furyl
A1-168oxmetidineNOOCO2HOO12-thienyl
A1-169oxmetidineNOOCO2H——0Cl
A1-170oxmetidineNOOCO2H——0{N(Et)3}+Cl−
A1-171oxmetidineNOOCO2HOO1CF3CH2
A1-172oxmetidineNOOCO2HOO1cyclopropyl
A1-173oxmetidineNOOCO2HOO12-OMe-Ph
A1-174oxmetidineNOOCO2HOO1MeSOH2
A1-175oxmetidineNOOCO2HOO1MeOCH2
A1-176oxmetidineNOOCO2HSS1Ph
A1-177oxmetidineNOOCO2HSS1NMe2
A1-178oxmetidineNOOCO2HSS1NBn2
A1-179oxmetidineNOOCO2HOS1Ph
A1-180oxmetidineNOOCO2HOS1Me
A1-181tetrahydrazolineNOOCO2HOO1methyl
A1-182tetrahydrazolineNOOCO2HOO1C(CH3)3
A1-183tetrahydrazolineNOOCO2HOO1Ph
A1-184tetrahydrazolineNOOCO2HOO14-Me-Ph
A1-185tetrahydrazolineNOOCO2HOO12-pyridyl
A1-186tetrahydrazolineNOOCO2HOO14-pyridyl
A1-187tetrahydrazolineNOOCO2HOO12-furyl
A1-188tetrahydrazolineNOOCO2HOO12-thienyl
A1-189tetrahydrazolineNOOCO2H——0Cl
A1-190tetrahydrazolineNOOCO2H——0{N(Et)3}+Cl−
A1-191tetrahydrazolineNOOCO2HOO1CF3CH2
A1-192tetrahydrazolineNOOCO2HOO1cyclopropyl
A1-193tetrahydrazolineNOOCO2HOO12-OMe-Ph
A1-194tetrahydrazolineNOOCO2HOO1MeSCH2
A1-195tetrahydrazolineNOOCO2HOO1MeOCH2
A1-196tetrahydrazolineNOOCO2HSS1Ph
A1-197tetrahydrazolineNOOCO2HSS1NMe2
A1-198tetrahydrazolineNOOCO2HSS1NBn2
A1-199tetrahydrazolineNOOCO2HOS1Ph
A1-200tetrahydrazolineNOOCO2HOS1Me
A1-201procaineNOOCO2HOO1methyl
A1-202procaineNOOCO2HOO1C(CH3)3
A1-203procaineNOOCO2HOO1Ph
A1-204procaineNOOCO2HOO14-Me-Ph
A1-205procaineNOOCO2HOO12-pyridyl
A1-206procaineNOOCO2HOO14-pyridyl
A1-207procaineNOOCO2HOO12-furyl
A1-208procaineNOOCO2HOO12-thienyl
A1-209procaineNOOCO2H——0Cl
A1-210procaineNOOCO2H——0{N(Et)3}+Cl−
A1-211procaineNOOCO2HOO1CF3CH2
A1-212procaineNOOCO2HOO1cyclopropyl
A1-213procaineNOOCO2HOO12-OMe-Ph
A1-214procaineNOOCO2HOO1MeSCH2
A1-215procaineNOOCO2HOO1MeOCH2
A1-216procaineNOOCO2HSS1Ph
A1-217procaineNOOCO2HSS1NMe2
A1-218procaineNOOCO2HSS1NBn2
A1-219procaineNOOCO2HOS1Ph
A1-220procaineNOOCO2HOS1Me
A1-221thiabendazoleNOOCO2HOO1methyl
A1-222thiabendazoleNOOCO2HOO1C(CH3)3
A1-223thiabendazoleNOOCO2HOO1Ph
A1-224thiabendazoleNOOCO2HOO14-Me-Ph
A1-225thiabendazoleNOOCO2HOO12-pyridyl
A1-226thiabendazoleNOOCO2EOO14-pyridyl
A1-227thiabendazoleNOOCO2HOO12-furyl
A1-228thiabendazoleNOOCO2HOO12-thienyl
A1-229thiabendazoleNOOCO2H——0Cl
A1-230thiabendazoleNOOCO2H——0{N(Et)3}+Cl−
A1-231thiabendazoleNOOCO2HOO1CF3CH2
A1-232thiabendazoleNOOCO2HOO1cyclopropyl
A1-233thiabendazoleNOOCO2HOO12-OMe-Ph
A1-234thiabendazoleNOOCO2HOO1MeSCH2
A1-235thiabendazoleNOOCO2HOO1MeOCH2
A1-236thiabendazoleNOOCO2HSS1Ph
A1-237thiabendazoleNOOCO2HSS1NMe2
A1-238thiabendazoleNOOCO2HSS1NBn2
A1-239thiabendazoleNOOCO2HOS1Ph
A1-240thiabendazoleNOOCO2HOS1Me
A1-241tolazolineNOOCO2HOO1methyl
A1-242tolazolineNOOCO2HOO1C(CH3)3
A1-243tolazolineNOOCO2HOO1Ph
A1-244tolazolineNOOCO2HOO14-Me-Ph
A1-245tolazolineNOOCO2HOO12-pyridyl
A1-246tolazolineNOOCO2HOO14-pyridyl
A1-247tolazolineNOOCO2HOO12-furyl
A1-248tolazolineNOOCO2HOO12-thienyl
A1-249tolazolineNOOCO2H——0Cl
A1-250tolazolineNOOCO2H——0{N(Et)3}+Cl−
A1-251tolazolineNOOCO2HOO1CF3CH2
A1-252tolazolineNOOCO2HOO1cyclopropyl
A1-253tolazolineNOOCO2HOO12-OMe-Ph
A1-254tolazolineNOOCO2HOO1MeSCH2
A1-255tolazolineNOOCO2HOO1MeOCH2
A1-256tolazolineNOOCO2HSS1Ph
A1-257tolazolineNOOCO2HSS1NMe2
A1-258tolazolineNOOCO2HSS1NBn2
A1-259tolazolineNOOCO2HOS1Ph
A1-260tolazolineNOOCO2HOS1Me
A1-261proparacaineNOOCO2HOO1methyl
A1-262proparacaineNOOCO2HOO1C(CH3)3
A1-263proparacaineNOOCO2HOO1Ph
A1-264proparacaineNOOCO2HOO14-Me-Ph
A1-265proparacaineNOOCO2HOO12-pyridyl
A1-266proparacaineNOOCO2HOO14-pyridyl
A1-267proparacaineNOOCO2HOO12-furyl
A1-268proparacaineNOOCO2HOO12-thienyl
A1-269proparacaineNOOCO2H——0Cl
A1-270proparacaineNOOCO2H——0{N(Et)3}+Cl−
A1-271proparacaineNOOCO2HOO1CF3CH2
A1-272proparacaineNOOCO2HOO1cyclopropyl
A1-273proparacaineNOOCO2HOO12-OMe-Ph
A1-274proparacaineNOOCO2HOO1MeSCH2
A1-275proparacaineNOOCO2HOO1MeOCH2
A1-276proparacaineNOOCO2HSS1Ph
A1-277proparacaineNOOCO2HSS1NMe2
A1-278proparacaineNOOCO2HSS1NBn2
A1-279proparacaineNOOCO2HOS1Ph
A1-280proparacaineNOOCO2HOS1Me
A1-281tocainideNOOCO2HOO1methyl
A1-282tocainideNOOCO2HOO1C(CH3)3
A1-283tocainideNOOCO2HOO1Ph
A1-284tocainideNOOCO2HOO14-Me-Ph
A1-285tocainideNOOCO2HOO12-pyridyl
A1-286tocainideNOOCO2HOO14-pyridyl
A1-287tocainideNOOCO2HOO12-furyl
A1-288tocainideNOOCO2HOO12-thienyl
A1-289tocainideNOOCO2H——0Cl
A1-290tocainideNOOCO2H——0{N(Et)3}+Cl−
A1-291tocainideNOOCO2HOO1CF3CH2
A1-292tocainideNOOCO2HOO1cyclopropyl
A1-293tocainideNOOCO2HOO12-OMe-Ph
A1-294tocainideNOOCO2HOO1MeSCH2
A1-295tocainideNOOCO2HOO1MeOCH2
A1-296tocainideNOOCO2HSS1Ph
A1-297tocainideNOOCO2HSS1NMe2
A1-298tocainideNOOCO2HSS1NBn2
A1-299tacainideNOOCO2HOS1Ph
A1-300tocainideNOOCO2HOS1Me
A1-301triamtereneNOOCO2HOO1methyl
A1-302triamtereneNOOCO2HOO1C(CH3)3
A1-303triamtereneNOOCO2HOO1Ph
A1-304triamtereneNOOCO2HOO14-Me-Ph
A1-305triamtereneNOOCO2HOO12-pyridyl
A1-306triamtereneNOOCO2HOO14-pyridyl
A1-307triamtereneNOOCO2HOO12-furyl
A1-308triarntereneNOOCO2HOO12-thienyl
A1-309triamtereneNOOCO2H——0Cl
A1-310triamtereneNOOCO2H——0{N(Et)3}+Cl−
A1-311triamtereneNOOCO2HOO1CF3CH2
A1-312triamtereneNOOCO2HOO1cyclopropyl
A1-313triamtereneNOOCO2HOO12-OMe-Ph
A1-314triamtereneNOOCO2HOO1MeSCH2
A1-315triamtereneNOOCO2HOO1MeOCH2
A1-316triamtereneNOOCO2HSS1Ph
A1-317triamtereneNOOCO2HSS1NMe2
A1-318triamtereneNOOCO2HSS1NBn2
A1-319triamtereneNOOCO2HOS1Ph
A1-320triamtereneNOOCO2HOS1Me
A1-321bydroxyitraconazoleOOOCO2HOO1methyl
A1-322hydroxyitraconazoleOOOCO2HOO1C(CH3)3
A1-323hydroxyitraconazoleOOOCO2HOO1Ph
A1-324hydroxyitraconazoleOOOCO2HOO14-Me-Ph
A1-325hydroxyitraconazoleOOOCO2HOO12-pyridyl
A1-326hydroxyitraconazoleOOOCO2HOO14-pyridyl
A1-327hydroxyitraconazoleOOOCO2HOO12-furyl
A1-328hydroxyitraconazoleOOOCO2HOO12-thienyl
A1-329hydroxyitraconazoleOOOCO2H——OCl
A1-330hydroxyitraconazoleOOOCO2H——0{N(Et)3}+Cl−
A1-331hydroxyitraconazoleOOOCO2HOO1CF3CH2
A1-332hydroxyitraconazoleOOOCO2HOO1cyclopropyl
A1-333hydroxyitraconazoleOOOCO2HOO12-OMe-Ph
A1-334hydroxyitraconazoleOOOCO2HOO1MeSCH2
A1-335hydroxyitraconazoleOOOCO2HOO1MeOCH2
A1-336hydroxyitraconazoleOOOCO2HSS1Ph
A1-337hydroxyitraconazoleOOOCO2HSS1NMe2
A1-338hydroxyitraconazoleOOOCO2HSS1NBn2
A1-339hydroxyitraconazoleOOOCO2HOS1Ph
A1-340hydroxyitraconazoleOOOCO2HOS1Me
A1-341posaconazoleOOOCO2HOO1methyl
A1-342posaconazoleOOOCO2HOO1C(CH3)3
A1-343posaconazoleOOOCO2HOO1Ph
A1-344posaconazoleOOOCO2HOO14-Me-Ph
A1-345posaconazoleOOOCO2HOO12-pyridyl
A1-346posaconazoleOOOCO2HOO14-pyridyl
A1-347posaconazoleOOOCO2HOO12-furyl
A1-348posaconazoleOOOCO2HOO12-thienyl
A1-349posaconazoleOOOCO2H——0Cl
A1-350posaconazoleOOOCO2H——0{N(Et)3}+Cl−
A1-351posaconazoleOOOCO2HOO1CF3CH2
A1-352posaconazoleOOOCO2HOO1cyclopropyl
A1-353posaconazoleOOOCO2HOO12-OMe-Ph
A1-354posaconazoleOOOCO2HOO1MeSCH2
A1-355posaconazoleOOOCO2HOO1MeOCH2
A1-356posaconazoleOOOCO2HSS1Ph
A1-357posaconazoleOOOCO2HSS1NMe2
A1-358posaconazoleOOOCO2HSS1NBn2
A1-359posaconazoleOOOCO2HOS1Ph
A1-360posaconazoleOOOCO2HOS1Me
A1-361voriconazoleOOOCO2HOO1methyl
A1-362voriconazoleOOOCO2HOO1C(CH3)3
A1-363voriconazoleOOOCO2HOO1Ph
A1-364voriconazoleOOOCO2HOO14-Me-Ph
A1-365voriconazoleOOOCO2HOO12-pyridyl
A1-366voriconazoleOOOCO2HOO14-pyridyl
A1-367voriconazoleOOOCO2HOO12-furyl
A1-368voriconazoleOOOCO2HOO12-thienyl
A1-369voriconazoleOOOCO2H——0Cl
A1-370voriconazoleOOOCO2H——0{N(Et)3}+Cl−
A1-371voriconazoleOOOCO2HOO1CF3CH2
A1-372voriconazoleOOOCO2HOO1cyclopropyl
A1-373voriconazoleOOOCO2HOO12-OMe-Ph
A1-374voriconazoleOOOCO2HOO1MeSCH2
A1-375voriconazoleOOOCO2HOO1MeOCH2
A1-376voriconazoleOOOCO2HSS1Ph
A1-377voriconazoleOOOCO2HSS1NMe2
A1-378voriconazoleOOOCO2HSS1NBn2
A1-379voriconazoleOOOCO2HOS1Ph
A1-380voriconazoleOOOCO2HOS1Me
A1-381genaconazoleOOOCO2HOO1methyl
A1-382genaconazoleOOOCO2HOO1C(CH3)3
A1-383genaconazoleOOOCO2HOO1Ph
A1-384genaconazoleOOOCO2HOO14-Me-Ph
A1-385genaconazoleOOOCO2HOO12-pyridyl
A1-386genaconazoleOOOCO2HOO14-pyridyl
A1-387genaconazoleOOOCO2HOO12-furyl
A1-388genaconazoleOOOCO2HOO12-thienyl
A1-389genaconazoleOOOCO2H——0Cl
A1-390genaconazoleOOOCO2H——0{N(Et)3}+Cl−
A1-391genaconazoleOOOCO2HOO1CF3CH2
A1-392genaconazoleOOOCO2HOO1cyclopropyl
A1-393genaconazoleOOOCO2HOO12-OMe-Ph
A1-394genaconazoleOOOCO2HOO1MeSCH2
A1-395genaconazoleOOOCO2HOO1MeOCH2
A1-396genaconazoleOOOCO2HSS1Ph
A1-397genaconazoleOOOCO2HSS1NMe2
A1-398genaconazoleOOOCO2HSS1NBn2
A1-399genaconazoleOOOCO2HOS1Ph
A1-400genaconazoleOOOCO2HOS1Me
A1-401fluconazoleOOOCO2HOO1methyl
A1-402fluconazoleOOOCO2HOO1C(CH3)3
A1-403fluconazoleOOOCO2HOO1Ph
A1-404fluconazoleOOOCO2HOO14-Me-Ph
A1-405fluconazoleOOOCO2HOO12-pyridyl
A1-406fluconazoleOOOCO2HOO14-pyridyl
A1-407fluconazoleOOOCO2HOO12-furyl
A1-408fluconazoleOOOCO2HOO12-thienyl
A1-409fluconazoleOOOCO2H——0Cl
A1-410fluconazoleOOOCO2H——0{N(Et)3}+Cl−
A1-411fluconazoleOOOCO2HOO1CF3CH2
A1-412fluconazoleOOOCO2HOO1cyclopropyl
A1-413fluconazoleOOOCO2HOO12-OMe-Ph
A1-414fluconazoleOOOCO2HOO1MeSCH2
A1-415fluconazoleOOOCO2HOO1MeOCH2
A1-416fluconazoleOOOCO2HSS1Ph
A1-417fluconazoleOOOCO2HSS1NMe2
A1.418fluconazoleOOOCO2HSS1NBn2
A1-419fluconazoleOOOCO2HOS1Ph
A1-420fluconazoleOOOCO2HOS1Me
A1-421metronidazoleOOOCO2HOO1methyl
A1-422metronidazoleOOOCO2HOO1C(CH3)3
A1-423metronidazoleOOOCO2HOO1Ph
A1-424metronidazoleOOOCO2HOO14-Me-Ph
A1-425metronidazoleOOOCO2HOO12-pyridyl
A1-426metronidazoleOOOCO2HOO14-pyridyl
A1-427metronidazoleOOOCO2HOO12-furyl
A1-428metronidazoleOOOCO2HOO12-thienyl
A1-429metronidazoleOOOCO2H——0Cl
A1-430metronidazoleOOOCO2H——0{N(Et)3}+Cl−
A1-431metronidazoleOOOCO2HOO1CF3CH2
A1-432metronidazoleOOOCO2HOO1cyclopropyl
A1-433metronidazoleOOOCO2HOO12-OMe-Ph
A1-434metronidazoleOOOCO2HOO1MeSOH2
A1-435metronidazoleOOOCO2HOO1MeOCH2
A1-436metronidazoleOOOCO2HSS1Ph
A1-437metronidazoleOOOCO2HSS1NMe2
A1-438metronidazoleOOOCO2HSS1NBn2
A1-439metronidazoleOOOCO2HOS1Ph
A1-440metronidazoleOOOCO2HOS1Me
A1-441temazepamOOOCO2HOO1methyl
A1-442temazepamOOOCO2HOO1C(CH3)3
A1-443temazepamOOOCO2HOO1Ph
A1-444temazepamOOOCO2HOO14-Me-Ph
A1-445temazepamOOOCO2HOO12-pyridyl
A1-446temazepamOOOCO2HOO14-pyridyl
A1-447temazepamOOOCO2HOO12-furyl
A1-448temazepamOOOCO2HOO12-thienyl
A1-449temazepamOOOCO2H——0Cl
A1-450temazepamOOOCO2H——0{N(Et)3}+Cl−
A1-451temazepamOOOCO2HOO1CF3CH2
A1-452temazepamOOOCO2HOO1cyclopropyl
A1-453temazepamOOOCO2HOO12-OMe-Ph
A1-454temazepamOOOCO2HOO1MeSCH2
A1-455temazepamOOOCO2HOO1MeOCH2
A1-456temazepamOOOCO2HSS1Ph
A1-457temazepamOOOCO2HSS1NMe2
A1-458temazepamOOOCO2HSS1NBn2
A1-459temazepamOOOCO2HOS1Ph
A1-460temazepamOOOCO2HOS1Me
A1-461buprenorphineOOOCO2HOO1methyl
A1-462buprenorphineOOOCO2HOO1C(CH3)3
A1-463buprenorphineOOOCO2HOO1Ph
A1-464buprenorphineOOOCO2HOO14-Me-Ph
A1-465buprenorphineOOOCO2HOO12-pyridyl
A1-466buprenorphineOOOCO2HOO14-pyridyl
A1-467buprenorphineOOOCO2HOO12-furyl
A1-468buprenorphineOOOCO2HOO12-thienyl
A1-469buprenorphineOOOCO2H——0Cl
A1-470buprenorphineOOOCO2H——0{N(Et)3}+Cl−
A1-471buprenorphineOOOCO2HOO1CF3CH2
A1-472buprenorphineOOOCO2HOO1cyclopropyl
A1-473buprenorphineOOOCO2HOO12-OMe-Ph
A1-474buprenorphineOOOCO2HOO1MeSCH2
A1-475buprenorphineOOOCO2HOO1MeOCH2
A1-476buprenorphineOOOCO2HSS1Ph
A1-477buprenorphineOOOCO2HSS1NMe2
A1-478buprenorphineOOOCO2HSS1NBn2
A1-479buprenorphineOOOCO2HOS1Ph
A1-480buprenorphineOOOCO2HOS1Me
A1-481cafiminolOOOCO2HOO1methyl
A1-482cafiminolOOOCO2HOO1C(CH3)3
A1-483cafiminolOOOCO2HOO1Ph
A1-484cafiminolOOOCO2HOO14-Me-Ph
A1-485cafiminolOOOCO2HOO12-pyridyl
A1-486cafiminolOOOCO2HOO14-pyridyl
A1-487cafiminolOOOCO2HOO12-furyl
A1-488cafiminolOOOCO2HOO12-thienyl
A1-489cafiminolOOOCO2H——0Cl
A1-490cafiminolOOOCO2H——0{N(Et)3}+Cl−
A1-491cafiminolOOOCO2HOO1CF3CH2
A1-492cafiminolOOOCO2HOO1cyclopropyl
A1-493cafiminolOOOCO2HOO12-OMe-Ph
A1-494cafiminolOOOCO2HOO1MeSCH2
A1-495cafiminolOOOCO2HOO1MeOCH2
A1-496cafiminolOOOCO2HSS1Ph
A1-497cafiminolOOOCO2HSS1NMe2
A1-498cafiminolOOOCO2HSS1NBn2
A1-499cafiminolOOOCO2HOS1Ph
A1-500cafiminolOOOCO2HOS1Me
A1-501pentazocineOOOCO2HOO1methyl
A1-502pentazocineOOOCO2HOO1C(CH3)3
A1-503pentazocineOOOCO2HOO1Ph
A1-504pentazocineOOOCO2HOO14-Me-Ph
A1-505pentazocineOOOCO2HOO12-pyridyl
A1-506pentazocineOOOCO2HOO14-pyridyl
A1-507pentazocineOOOCO2HOO12-furyl
A1-508pentazocineOOOCO2HOO12-thienyl
A1-509pentazocineOOOCO2H——0Cl
A1-510pentazocineOOOCO2H——0{N(Et)3}+Cl−
A1-511pentazocineOOOCO2HOO1CF3CH2
A1-512pentazocineOOOCO2HOO1cyclopropyl
A1-513pentazocineOOOCO2HOO12-OMe-Ph
A1-514pentazocineOOOCO2HOO1MeSCH2
A1-515pentazocineOOOCO2HOO1MeOCH2
A1-516pentazocineOOOCO2HSS1Ph
A1-517pentazocineOOOCO2HSS1NMe2
A1-518pentazocineOOOCO2HSS1NBn2
A1-519pentazocineOOOCO2HOS1Ph
A1-520pentazocmeOOOCO2HOS1Me
A1-521scopolamineOOOCO2HOO1methyl
A1-522scopolamineOOOCO2HOO1C(CH3)3
A1-523scopolamineOOOCO2HOO1Ph
A1-524scopolamineOOOCO2HOO14-Me-Ph
A1-525scopolamineOOOCO2HOO12-pyridyl
A1-526scopolamineOOOCO2HOO14-pyridyl
A1-527scopolamineOOOCO2HOO12-furyl
A1-528scopolamineOOOCO2HOO12-thienyl
A1-529scopolamineOOOCO2H——0Cl
A1-530scopolamineOOOCO2H——0{N(Et)3}+Cl−
A1-531scopolamineOOOCO2HOO1CF3CH2
A1-532scopolamineOOOCO2HOO1cyclopropyl
A1-533scopolamineOOOCO2HOO12-OMe-Ph
A1-534scopolamineOOOCO2HOO1MeSCH2
A1-535scopolamineOOOCO2HOO1MeOCH2
A1-536scopolamineOOOCO2HSS1Ph
A1-537scopolamineOOOCO2HSS1NMe2
A1-538scopolamineOOOCO2HSS1NBn2
A1-539scopolamineOOOCO2HOS1Ph
A1-540scopolamineOOOCO2HOS1Me
A1-541tramadolOOOCO2HOO1methyl
A1-542tramadolOOOCO2HOO1C(CH3)3
A1-543tramadolOOOCO2HOO1Ph
A1-544tramadolOOOCO2HOO14-Me-Ph
A1-545tramadolOOOCO2HOO12-pyridyl
A1-546tramadolOOOCO2HOO14-pyridyl
A1-547tramadolOOOCO2HOO12-furyl
A1-548tramadolOOOCO2HOO12-thienyl
A1-549tramadolOOOCO2H——0Cl
A1-550tramadolOOOCO2H——0{N(Et)3}+Cl−
A1-551tramadolOOOCO2HOO1CF3CH2
A1-552tramadolOOOCO2HOO1cyclopropyl
A1-553tramadolOOOCO2HOO12-OMe-Ph
A1-554tramadolOOOCO2HOO1MeSCH2
A1-555tramadolOOOCO2HOO1MeOCH2
A1-556tramadolOOOCO2HSS1Ph
A1-557tramadolOOOCO2HSS1NMe2
A1-558tramadolOOOCO2HSS1NBn2
A1-559tramadolOOOCO2HOS1Ph
A1-560tramadolOOOCO2HOS1Me
A1-561quinidineOOOCO2HOO1methyl
A1-562quinidineOOOCO2HOO1C(CH3)3
A1-563quinidineOOOCO2HOO1Ph
A1-564quinidineOOOCO2HOO14-Me-Ph
A1-565quinidineOOOCO2HOO12-pyridyl
A1-566quinidineOOOCO2HOO14-pyridyl
A1-567quinidineOOOCO2HOO12-furyl
A1-568quinidineOOOCO2HOO12-thienyl
A1-569quinidineOOOCO2H——0Cl
A1-570quinidineOOOCO2H——0{N(Et)3}+Cl−
A1-571quinidineOOOCO2HOO1CF3CH2
A1-572quinidineOOOCO2HOO1cyclopropyl
A1-573quinidineOOOCO2HOO12-OMe-Ph
A1-574quinidineOOOCO2HOO1MeSCH2
A1-575quinidineOOOCO2HOO1MeOCH2
A1-576quinidineOOOCO2HSS1Ph
A1-577quinidineOOOCO2HSS1NMe2
A1-578quinidineOOOCO2HSS1NBn2
A1-579quinidineOOOCO2HOS1Ph
A1-580quinidineOOOCO2HOS1Me
A1-581methimazoleSOOCO2HOO1methyl
A1-582methiinazoleSOOCO2HOO1C(CH3)3
A1-583methimazoleSOOCO2HOO1Ph
A1-584methimazoleSOOCO2HOO14-Me-Ph
A1-585methimazoleSOOCO2HOO12-pyridyl
A1-586methimazoleSOOCO2HOO14-pyridyl
A1-587methimazoleSOOCO2HOO12-furyl
A1-588methimazoleSOOCO2HOO12-thienyl
A1-589methimazoleSOOCO2H——0Cl
A1-590methimazoleSOOCO2H——0{N(Et)3}+Cl−
A1-591methimazoleSOOCO2HOO1CF3CH2
A1-592methimazoleSOOCO2HOO1cyclopropyl
A1-593methimazoleSOOCO2HOO12-OMe-Ph
A1-594methimazoleSOOCO2HOO1MeSCH2
A1-595methimazoleSOOCO2HOO1MeOCH2
A1-596methimazoleSOOCO2HSS1Ph
A1-597methimazoleSOOCO2HSS1NMe2
A1-598methimazoleSOOCO2HSS1NBn2
A1-599methimazoleSOOCO2HOS1Ph
A1-600methimazoleSOOCO2HOS1Me
A1-601haloperidolOOOCO2HOO1methyl
A1-602haloperidolOOOCO2HOO1C(CH3)3
A1-603haloperidolOOOCO2HOO1Ph
A1-604haloperidolOOOCO2HOO14-Me-Ph
A1-605haloperidolOOOCO2HOO12-pyridyl
A1-606haloperidolOOOCO2HOO14-pyridyl
A1-607haloperidolOOOCO2HOO12-furyl
A1-608haloperidolOOOCO2HOO12-thienyl
A1-609haloperidolOOOCO2H——0Cl
A1-610haloperidolOOOCO2H——0{N(Et)3}+Cl−
A1-611haloperidolOOOCO2HOO1CF3CH2
A1-612haloperidolOOOCO2HOO1cyclopropyl
A1-613haloperidolOOOCO2HOO12-OMe-Ph
A1-614haloperidolOOOCO2HOO1MeSCH2
A1-615haloperidolOOOCO2HOO1MeOCH2
A1-616haloperidolOOOCO2HSS1Ph
A1-617haloperidolOOOCO2HSS1NMe2
A1-618haloperidolOOOCO2HSS1NBn2
A1-619haloperidolOOOCO2HOS1Ph
A1-620haloperidolOOOCO2HOS1Me
A1-621hydroxyzineOOOCO2HOO1methyl
A1-622hydroxyzineOOOCO2HOO1C(CH3)3
A1-623hydroxyzineOOOCO2HOO1Ph
A1-624hydroxyzineOOOCO2HOO14-Me-Ph
A1-625hydroxyzineOOOCO2HOO12-pyridyl
A1-626hydroxyzineOOOCO2HOO14-pyridyl
A1-627hydroxyzineOOOCO2HOO12-furyl
A1-628hydroxyzineOOOCO2HOO12-thienyl
A1-629hydroxyzineOOOCO2H——0Cl
A1-630hydroxyzineOOOCO2H——0{N(Et)3}+Cl−
A1-631hydroxyzineOOOCO2HOO1CF3CH2
A1-632hydroxyzineOOOCO2HOO1cyclopropyl
A1-633hydroxyzineOOOCO2HOO12-OMe-Ph
A1-634hydroxyzineOOOCO2HOO1MeSCH2
A1-635hydroxyzineOOOCO2HOO1MeOCH2
A1-636hydroxyzineOOOCO2HSS1Ph
A1-637hydroxyzineOOOCO2HSS1NMe2
A1-638hydroxyzineOOOCO2HSS1NBn2
A1-639hydroxyzineOOOCO2HOS1Ph
A1-640hydroxyzineOOOCO2HOS1Me
A1-641lorazepamOOOCO2HOO1methyl
A1-642lorazepamOOOCO2HOO1C(CH3)3
A1-643lorazepamOOOCO2HOO1Ph
A1-644lorazepamOOOCO2HOO14-Me-Ph
A1-645lorazepamOOOCO2HOO12-pyridyl
A1-646lorazepamOOOCO2HOO14-pyridyl
A1-647lorazepamOOOCO2HOO12-furyl
A1-648lorazepamOOOCO2HOO12-thienyl
A1-649lorazepamOOOCO2H——0Cl
A1-650lorazepamOOOCO2H——0{N(Et)3}+Cl−
A1-651lorazepamOOOCO2HOO1CF3CH2
A1-652lorazepamOOOCO2HOO1cyclopropyl
A1-653lorazepamOOOCO2HOO12-OMe-Ph
A1-654lorazepamOOOCO2HOO1MeSCH2
A1-655lorazepamOOOCO2HOO1MeOCH2
A1-656lorazepamOOOCO2HSS1Ph
A1-657lorazepamOOOCO2HSS1NMe2
A1-658lorazepamOOOCO2HSS1NBn2
A1-659lorazepamOOOCO2HOS1Ph
A1-660lorazepamOOOCO2HOS1Me
A1-661iodoquinolOOOCO2HOO1methyl
A1-662iodoquinolOOOCO2HOO1C(CH3)3
A1-663iodoquinolOOOCO2HOO1Ph
A1-664iodoquinolOOOCO2HOO14-Me-Ph
A1-665iodoquinolOOOCO2HOO12-pyridyl
A1-666iodoquinolOOOCO2HOO14-pyridyl
A1-667iodoquinolOOOCO2HOO12-furyl
A1-668iodoquinolOOOCO2HOO12-thienyl
A1-669iodoquinolOOOCO2H——0Cl
A1-670iodoquinolOOOCO2H——0{N(Et)3}+Cl−
A1-671iodoquinolOOOCO2HOO1CF3CH2
A1-672iodoquinolOOOCO2HOO1cyclopropyl
A1-673iodoquinolOOOCO2HOO12-OMe-Ph
A1-674iodoquinolOOOCO2HOO1MeSCH2
A1-675iodoquinolOOOCO2HOO1MeOCH2
A1-676iodoquinolOOOCO2HSS1Ph
A1-677iodoquinolOOOCO2HSS1NMe2
A1-678iodoquinolOOOCO2HSS1NBn2
A1-679iodoquinolOOOCO2HOS1Ph
A1-680iodoquinolOOOCO2HOS1Me
A1-681perphenazineOOOCO2HOO1methyl
A1-682perphenazineOOOCO2HOO1C(CH3)3
A1-683perphenazineOOOCO2HOO1Ph
A1-684perphenazineOOOCO2HOO14-Me-Ph
A1-685perphenazineOOOCO2HOO12-pyridyl
A1-686perphenazineOOOCO2HOO14-pyridyl
A1-687perphenazineOOOCO2HOO12-furyl
A1-688perphenazineOOOCO2HOO12-thienyl
A1-689perphenazineOOOCO2H——0Cl
A1-690perphenazineOOOCO2H——0{N(Et)3}+Cl−
A1-691perphenazineOOOCO2HOO1CF3CH2
A1-692perphenazineOOOCO2HOO1cyclopropyl
A1-693perphenazineOOOCO2HOO12-OMe-Ph
A1-694perphenazineOOOCO2HOO1MeSCH2
A1-695perphenazineOOOCO2HOO1MeOCH2
A1-696perphenazineOOOCO2HSS1Ph
A1-697perphenazineOOOCO2HSS1NMe2
A1-698perphenazineOOOCO2HSS1NBn2
A1-699perphenazineOOOCO2HOS1Ph
A1-700perphenazineOOOCO2HOS1Me
A1-701mazindolOOOCO2HOO1methyl
A1-702mazindolOOOCO2HOO1C(CH3)3
A1-703mazindolOOOCO2HOO1Ph
A1-704mazindolOOOCO2HOO14-Me-Ph
A1-705mazindolOOOCO2HOO12-pyridyl
A1-706mazindolOOOCO2HOO14-pyridyl
A1-707mazindolOOOCO2HOO12-furyl
A1-708mazindolOOOCO2HOO12-thienyl
A1-709mazindolOOOCO2H——OCl
A1-710mazindolOOOCO2H——0{N(Et)3}+Cl−
A1-711mazindolOOOCO2HOO1CF3CH2
A1-712mazindolOOOCO2HOO1cyclopropyl
A1-713mazindolOOOCO2HOO12-OMe-Ph
A1-714mazindolOOOCO2HOO1MeSCH2
A1-715mazindolOOOCO2HOO1MeOCH2
A1-716mazindolOOOCO2HSS1Ph
A1-717mazindolOOOCO2HSS1NMe2
A1-718mazindolOOOCO2HSS1NBn2
A1-719mazindolOOOCO2HOS1Ph
A1-720mazmdolOOOCO2HOS1Me
A1-721astemizoleNOOCO2HOO1methyl
A1-722astemizoleNOOCO2HOO1C(CH3)3
A1-723astemizoleNOOCO2HOO1Ph
A1-724astemizoleNOOCO2HOO14-Me-Ph
A1-725astemizoleNOOCO2HOO12-pyridyl
A1-726astemizoleNOOCO2HOO14-pyridyl
A1-727astemizoleNOOCO2HOO12-furyl
A1-728astemizoleNOOCO2HOO12-thienyl
A1-729astemizoleNOOCO2H——0Cl
A1-730astemizoleNOOCO2H——0{N(Et)3}+Cl−
A1-731astemizoleNOOCO2HOO1CF3CH2
A1-732astemizoleNOOCO2HOO1cyclopropyl
A1-733astemizoleNOOCO2HOO12-OMe-Ph
A1-734astemizoleNOOCO2HOO1MeSCH2
A1-735astemizoleNOOCO2HOO1MeOCH2
A1-736astemizoleNOOCO2HSS1Ph
A1-737astemizoleNOOCO2HSS1NMe2
A1-738astemizoleNOOCO2HSS1NBn2
A1-739astemizoleNOOCO2HOS1Ph
A1-740astemizoleNOOCO2HOS1Me
A1-741amoxapineNOOCO2HOO1methyl
A1-742amoxapineNOOCO2HOO1C(CH3)3
A1-743amoxapineNOOCO2HOO1Ph
A1-744amoxapineNOOCO2HOO14-Me-Ph
A1-745amoxapineNOOCO2HOO12-pyridyl
A1-746amoxapineNOOCO2HOO14-pyridyl
A1-747amoxapineNOOCO2HOO12-furyl
A1-748amoxapineNOOCO2HOO12-thienyl
A1-749amoxapineNOOCO2H——0Cl
A1-750amoxapineNOOCO2H——0{N(Et)3}+Cl−
A1-751amoxapineNOOCO2HOO1CF3CH2
A1-752amoxapineNOOCO2HOO1cyclopropyl
A1-753amoxapineNOOCO2HOO12-OMe-Ph
A1-754amoxapineNOOCO2HOO1MeSCH2
A1-755amoxapineNOOCO2HOO1MeOCH2
A1-756amoxapineNOOCO2HSS1Ph
A1-757amoxapineNOOCO2HSS1NMe2
A1-758amoxapineNOOCO2HSS1NBn2
A1-759amoxapineNOOCO2HOS1Ph
A1-760amoxapineNOOCO2HOS1Me
A1-761ciprofloxacinNOOCO2HOO1methyl
A1-762ciprofloxacinNOOCO2HOO1C(CH3)3
A1-763ciprofloxacinNOOCO2HOO1Ph
A1-764ciprofloxacinNOOCO2HOO14-Me-Ph
A1-765ciprofloxacinNOOCO2HOO12-pyridyl
A1-766ciprofloxacinNOOCO2HOO14-pyridyl
A1-767ciprofloxacinNOOCO2HOO12-furyl
A1-768ciprofloxacinNOOCO2HOO12-thienyl
A1-769ciprofloxacinNOOCO2H——0Cl
A1-770ciprofloxacinNOOCO2H——0{N(Et)3}+Cl−
A1-771ciprofloxacinNOOCO2HOO1CF3CH2
A1-772ciprofloxacinNOOCO2HOO1cyclopropyl
A1-773ciprofloxacinNOOCO2HOO12-OMe-Ph
A1-774ciprofloxacinNOOCO2HOO1MeSCH2
A1-775ciprofloxacinNOOCO2HOO1MeOCH2
A1-776ciprofloxacinNOOCO2HSS1Ph
A1-777ciprofloxacinNOOCO2HSS1NMe2
A1-778ciprofloxacinNOOCO2HSS1NBn2
A1-779ciprofloxacinNOOCO2HOS1Ph
A1-780ciprofloxacinNOOCO2HOS1Me
A1-781chloroquineNOOCO2HOO1methyl
A1-782chloroquineNOOCO2HOO1C(CH3)3
A1-783chloroquineNOOCO2HOO1Ph
A1-784chloroquineNOOCO2HOO14-Me-Ph
A1-785chloroquineNOOCO2HOO12-pyridyl
A1-786chloroquineNOOCO2HOO14-pyridyl
A1-787chloroquineNOOCO2HOO12-furyl
A1-788chloroquineNOOCO2HOO12-thienyl
A1-789chloroquineNOOCO2H——0Cl
A1-790chloroquineNOOCO2H——0{N(Et)3}+Cl−
A1-791chloroquineNOOCO2HOO1CF3CH2
A1-792chloroquineNOOCO2HOO1cyclopropyl
A1-793chloroquineNOOCO2HOO12-OMe-Ph
AI-794chloroquineNOOCO2HOO1MeSCH2
A1-795chloroquineNOOCO2HOO1MeOCH2
A1-796chloroquineNOOCO2HSS1Ph
A1-797chloroquineNOOCO2HSS1NMe2
A1-798chloroquineNOOCO2HSS1NBn2
A1-799chloroquineNOOCO2HOS1Ph
A1-800chloroquineNOOCO2HOS1Me
A1-801chlordiazepoxideNOOCO2HOO1methyl
A1-802chlordiazepoxideNOOCO2HOO1C(CH3)3
A1-503chlordiazepoxideNOOCO2HOO1Ph
A1-804chlordiazepoxideNOOCO2HOO14-Me-Ph
A1-805chlordiazepoxideNOOCO2HOO12-pyridyl
A1-806chlordiazepoxideNOOCO2HOO14-pyridyl
A1-807chlordiazepoxideNOOCO2HOO12-furyl
A1-808chlordiazepoxideNOOCO2HOO12-thienyl
A1-809chlordiazepoxideNOOCO2H——0Cl
A1-810chlordiazepoxideNOOCO2H——0{N(Et)3}+Cl−
A1-811chlordiazepoxideNOOCO2HOO1CF3CH2
A1-812chlordiazepoxideNOOCO2HOO1cyclopropyl
A1-813chlordiazepoxideNOOCO2HOO12-OMe-Ph
A1-814chlordiazepoxideNOOCO2HOO1MeSCH2
A1-815chlordiazepoxideNOOCO2HOO1MeOCH2
A1-816chlordiazepoxideNOOCO2HSS1Ph
A1-817chlordiazepoxideNOOCO2HSS1NMe2
A1-818chlordiazepoxideNOOCO2HSS1NBn2
A1-819chlordiazepoxideNOOCO2HOS1Ph
A1-820chlordiazepoxideNOOCO2HOS1Me
A1-821clozapineNOOCO2HOO1methyl
A1-822clozapineNOOCO2HOO1C(CH3)3
A1-823clozapineNOOCO2HOO1Ph
A1-824clozapineNOOCO2HOO14-Me-Ph
A1-825clozapineNOOCO2HOO12-pyridyl
A1-826clozapineNOOCO2HOO14-pyridyl
A1-827clozapineNOOCO2HOO12-furyl
A1-828clozapineNOOCO2HOO12-thienyl
A1-829clozapineNOOCO2H——0Cl
A1-830clozapineNOOCO2H——0{N(Et)3}+Cl−
A1-831clozapineNOOCO2HOO1CF3CH2
A1-832clozapineNOOCO2HOO1cyclopropyl
A1-833clozapineNOOCO2HOO12-OMe-Ph
A1-834clozapineNOOCO2HOO1MeSCH2
A1-835clozapineNOOCO2HOO1MeOCH2
A1-836clozapineNOOCO2HSS1Ph
A1-837clozapineNOOCO2HSS1NMe2
A1-838clozapineNOOCO2HSS1NBn2
A1-839clozapineNOOCO2HOS1Ph
A1-840clozapineNOOCO2HOS1Me
A1-841desipramineNOOCO2HOO1methyl
A1-842desipramineNOOCO2HOO1C(CH3)3
A1-843desipramineNOOCO2HOO1Ph
A1-844desipramineNOOCO2HOO14-Me-Ph
A1-845desipramineNOOCO2HOO12-pyridyl
A1-846desipramineNOOCO2HOO14-pyridyl
A1-847desipramineNOOCO2HOO12-furyl
A1-848desipramineNOOCO2HOO12-thienyl
A1-849desipramineNOOCO2H——0Cl
A1-850desipramineNOOCO2H——0{N(Et)3}+Cl−
A1-851desipramineNOOCO2HOO1CF3CH2
A1-852desipramineNOOCO2HOO1cyclopropyl
A1-853desipramineNOOCO2HOO12-OMe-Ph
A1-854desipramineNOOCO2HOO1MeSCH2
A1-855desipramineNOOCO2HOO1MeOCH2
A1-856desipramineNOOCO2HSS1Ph
A1-857desipramineNOOCO2HSS1NMe2
A1-858desipramineNOOCO2HSS1NBn2
A1-859desipramineNOOCO2HOS1Ph
A1-860desipramineNOOCO2HOS1Me
A1-861enoxacinNOOCO2HOO1methyl
A1-862enoxacinNOOCO2HOO1C(CH3)3
A1-563enoxacinNOOCO2HOO1Ph
A1-864enoxacinNOOCO2HOO14-Me-Ph
A1-865enoxacinNOOCO2HOO12-pyridyl
A1-866enoxacinNOOCO2HOO14-pyridyl
A1-867enoxacinNOOCO2HOO12-furyl
A1-868enoxacinNOOCO2HOO12-thienyl
A1-869enoxacinNOOCO2H——0Cl
A1-870enoxacinNOOCO2H——0{N(Et)3}+Cl−
A1-871enoxacinNOOCO2HOO1CF3CH2
A1-872enoxacinNOOCO2HOO1cyclopropyl
A1-873enoxacinNOOCO2HOO12-OMe-Ph
A1-874enoxacinNOOCO2HOO1MeSCH2
A1-875enoxacinNOOCO2HOO1MeOCH2
A1-876enoxacinNOOCO2HSS1Ph
A1-877enoxacinNOOCO2HSS1NMe2
A1-878enoxacinNOOCO2HSS1NBn2
A1-879enoxacinNOOCO2HOS1Ph
A1-880enoxacinNOOCO2HOS1Me
A1-881lomefloxacinNOOCO2HOO1methyl
A1-882lomefloxacinNOOCO2HOO1C(CH3)3
A1-883lomefloxacinNOOCO2HOO1Ph
A1-884lomefloxacinNOOCO2HOO14-Me-Ph
A1-885lomefloxacinNOOCO2HOO12-pyridyl
A1-886lomefloxacinNOOCO2HOO14-pyridyl
A1-887lomefloxacinNOOCO2HOO12-furyl
A1-888lomefloxacinNOOCO2HOO12-thienyl
A1-889lomefloxacinNOOCO2H——0Cl
A1-890lomefloxacinNOOCO2H——0{N(Et)3}+Cl−
A1-891lomefloxacinNOOCO2HOO1CF3CH2
A1-892lomefloxacinNOOCO2HOO1cyclopropyl
A1-893lomefloxacinNOOCO2HOO12-OMe-Ph
A1-894lomefloxacinNOOCO2HOO1MeSCH2
A1-895lomefloxacinNOOCO2HOO1MeOCH2
A1-896lomefloxacinNOOCO2HSS1Ph
A1-897lomefloxacinNOOCO2HSS1NMe2
A1-898lomefloxacinNOOCO2HSS1NBn2
A1-899lomefloxacinNOOCO2HOS1Ph
A1-900lomefloxacinNOOCO2HOS1Me
A1-901mepivacaineNOOCO2HOO1methyl
A1-902mepivacaineNOOCO2HOO1C(CH3)3
A1-903mepivacaineNOOCO2HOO1Ph
A1-904mepivacaineNOOCO2HOO14-Me-Ph
A1-905mepivacaineNOOCO2HOO12-pyridyl
A1-906mepivacaineNOOCO2HOO14-pyridyl
A1-907mepivacaineNOOCO2HOO12-furyl
A1-908mepivacaineNOOCO2HOO12-thienyl
A1-909mepivacaineNOOCO2H——0Cl
A1-910mepivacaineNOOCO2H——0{N(Et)3}+Cl−
A1-911mepivacaineNOOCO2HOO1CF3CH2
A1-912mepivacaineNOOCO2HOO1cyclopropyl
A1-913mepivacaineNOOCO2HOO12-OMe-Ph
A1-914mepivacaineNOOCO2HOO1MeSCH2
A1-915mepivacaineNOOCO2HOO1MeOCH2
A1-916mepivacaineNOOCO2HSS1Ph
A1-917mepivacaineNOOCO2HSS1NMe2
A1-918mepivacaineNOOCO2HSS1NBn2
A1-919mepivacaineNOOCO2HOS1Ph
A1-920mepivacaineNOOCO2HOS1Me
A1-921molindoneNOOCO2HOO1methyl
A1-922molindoneNOOCO2HOO1C(CH3)3
A1-923molindoneNOOCO2HOO1Ph
A1-924molindoneNOOCO2HOO14-Me-Ph
A1-925molindoneNOOCO2HOO12-pyridyl
A1-926molindoneNOOCO2HOO14-pyridyl
A1-927molindoneNOOCO2HOO12-furyl
A1-928molindoneNOOCO2HOO12-thienyl
A1-929molindoneNOOCO2H——0Cl
A1-930molindoneNOOCO2H——0{N(Et)3}+Cl−
A1-931molindoneNOOCO2HOO1CF3CH2
A1-932molindoneNOOCO2HOO1cyclopropyl
A1-933molindoneNOOCO2HOO12-OMe-Ph
A1-934molindoneNOOCO2HOO1MeSCH2
A1-935molindoneNOOCO2HOO1MeOCH2
A1-936molindoneNOOCO2HSS1Ph
A1-937molindoneNOOCO2HSS1NMe2
A1-938molindoneNOOCO2HSS1NBn2
A1-939molindoneNOOCO2HOS1Ph
A1-940molindoneNOOCO2HOS1Me
A1-941naphazolineNOOCO2HOO1methyl
A1-942naphazolineNOOCOAlOO1C(CH3)3
A1-943naphazolineNOOCO2HOO1Ph
A1-944naphazolineNOOCO2HOO14-Me-Ph
A1-945naphazolineNOOCO2HOO12-pyridyl
A1-946naphazolineNOOCO2HOO14-pyridyl
A1-947naphazolineNOOCO2HOO12-furyl
A1-948naphazolineNOOCO2HOO12-thienyl
A1-949naphazolineNOOCO2H——0Cl
A1-950naphazolineNOOCO2H——0{N(Et)3}+Cl−
A1-951naphazolineNOOCO2HOO1CF3CH2
A1-952naphazolineNOOCO2HOO1cyclopropyl
A1-953naphazolineNOOCO2HOO12-OMe-Ph
A1-954naphazolineNOOCO2HOO1MeSCH2
A1-955naphazolineNOOCO2HOO1MeOCH2
A1-956naphazolineNOOCO2HSS1Ph
A1-957naphazolineNOOCO2HSS1NMe2
A1-958naphazolineNOOCO2HSS1NBn2
A1-959naphazolineNOOCO2HOS1Ph
A1-960naphazolineNOOCO2HOS1Me
A1-961norfloxacinNOOCO2HOO1methyl
A1-962norfloxacinNOOCO2HOO1C(CH3)3
A1-963norfloxacinNOOCO2HOO1Ph
A1-964norfloxacinNOOCO2HOO14-Me-Ph.
A1-965norfloxacinNOOCO2HOO12-pyridyl
A1-966norfloxacinNOOCO2HOO14-pyridyl
A1-967norfloxacinNOOCO2HOO12-furyl
A1-968norfloxacinNOOCO2HOO12-thienyl
A1-969norfloxacinNOOCO2H——0Cl
A1-970norfloxacinNOOCO2H——0{N(Et)3}+Cl−
A1-971norfloxacinNOOCO2HOO1CF3CH2
A1-972norfloxacinNOOCO2HOO1cyclopropyl
A1-973norfloxacinNOOCO2HOO12-OMe-Ph
A1-974norfloxacinNOOCO2HOO1MeSCH2
A1-975norfloxacinNOOCO2HOO1MeOCH2
A1-976norfloxacinNOOCO2HSS1Ph
A1-977norfloxacinNOOCO2HSS1NMe2
A1-978norfloxacinNOOCO2HSS1NBfl2
A1-979norfloxacinNOOCO2HOS1Ph
A1-980norfloxacinNOOCO2HOS1Me
A1-981pimozideNOOCO2HOO1methyl
A1-982pimozideNOOCO2HOO1O(CH3)3
A1-983pimozideNOOCO2HOO1Ph
A1-984pimozideNOOCO2HOO14-Me-Ph
A1-985pimozideNOOCO2HOO12-pyridyl
A1-986pimozideNOOCO2HOO14-pyridyl
A1-987pimozideNOOCO2HOO12-furyl
A1-988pimozideNOOCO2HOO12-thienyl
A1-989pimozideNOOCO2H——0Cl
A1-990pimozideNOOCO2H——0{N(Et)3}+Cl−
A1-991pimozideNOOCO2HOO1CF3CH2
A1-992pimozideNOOCO2HOO1cyclopropyl
A1-993pimozideNOOCO2HOO12-OMe-Ph
A1-994pimozideNOOCO2HOO1MeSCH2
A1-995pimozideNOOCO2HOO1MeOCH2
A1-996pimozideNOOCO2HSS1Ph
A1-997pimozideNOOCO2HSS1NMe2
A1-998pimozideNOOCO2HSS1NBn2
A1-999pimozideNOOCO2HOS1Ph
A1-1000pimozideNOOCO2HOS1Me
A1-1001prazosinNOOCO2HOO1methyl
A1-1002prazosinNOOCO2HOO1C(CH3)3
A1-1003prazosinNOOCO2HOO1Ph
A1-1004prazosinNOOCO2HOO14-Me-Ph
A1-1005prazosinNOOCO2HOO12-pyridyl
A1-1006prazosinNOOCO2HOO14-pyridyl
A1-1007prazosinNOOCO2HOO12-furyl
A1-1008prazosinNOOCO2HOO12-thienyl
A1-1009prazosinNOOCO2H——0Cl
A1-1010prazosinNOOCO2H——0{N(Et)3}+Cl−
A1-1011prazosinNOOCO2HOO1CF3CH2
A1-1012prazosinNOOCO2HOO1cyclopropyl
A1-1013prazosinNOOCO2HOO12-OMe-Ph
A1-1014prazosinNOOCO2HOO1MeSCH2
A1-1015prazosinNOOCO2HOO1MeOC112
A1-1016prazosinNOOCO2HSS1Ph
A1-1017prazosinNOOCO2HSS1NMe2
A1-1018prazosinNOOCO2HSS1NBn2
A1-1019prazosinNOOCO2HOS1Ph
A1-1020prazosinNOOCO2HOS1Me
A1-1021sulfamethizoleeNOOCO2HOO1methyl
A1-1022sulfamethizoleeNOOCO2HOO1C(CH3)3
A1-1023sulfamethizoleeNOOCO2HOO1Ph
A1-1024sulfamethizoleeNOOCO2HOO14-Me-Ph
A1-1025sulfamethizoleeNOOCO2HOO12-pyridyl
A1-1026sulfamethizoleeNOOCO2HOO14-pyridyl
A1-1027sulfamethizoleeNOOCO2HOO12-furyl
A1-1028sulfamethizoleeNOOCO2HOO12-thienyl
A1-1029sulfamethizoleeNOOCO2H——0Cl
A1-1030sulfamethizoleeNOOCO2H——0{N(Et)3}+Cl−
A1-1031sulfamethizoleeNOOCO2HOO1CF3CH2
A1-1032sulfamethizoleeNOOCO2HOO1cyclopropyl
A1-1033sulfamethizoleeNOOCO2HOO12-OMe-Ph
A1-1034sulfamethizoleeNOOCO2HOO1MeSCH2
A1-1035sulfamethizoleeNOOCO2HOO1MeOCH2
A1-1036sulfamethizoleeNOOCO2HSS1Ph
A1-1037sulfamethizoleeNOOCO2HSS1NMe2
A1-1038sulfamethizoleeNOOCO2HSS1NBn2
A1-1039sulfamethizoleeNOOCO2HOS1Ph
A1-1040sulfamethizoleeNOOCO2HOS1Me
A1-1041tacrineNOOCO2HOO1methyl
A1-1042tacrineNOOCO2HOO1C(CH3)3
A1-1043tacrineNOOCO2HOO1Ph
A1-1044tacrineNOOCO2HOO14-Me-Ph
A1-1045tacrineNOOCO2HOO12-pyridyl
A1-1046tacrineNOOCO2HOO14-pyridyl
A1-1047tacrineNOOCO2HOO12-furyl
A1-1048tacrineNOOCO2HOO12-thienyl
A1-1049tacrineNOOCO2H——0Cl
A1-1050tacrineNOOCO2H——0{N(Et)3}+Cl−
A1-1051tacrineNOOCO2HOO1CF3CH2
A1-1052tacrineNOOCO2HOO1cyclopropyl
A1-1053tacrineNOOCO2HOO12-OMe-Ph
A1-1054tacrineNOOCO2HOO1MeSCH2
A1-1055tacrineNOOCO2HOO1MeOCH2
A1-1056tacrineNOOCO2HSS1Ph
A1-1057tacrineNOOCO2HSS1NMe2
A1-1058tacrineNOOCO2HSS1NBn2
A1-1059tacrineNOOCO2HOS1Ph
A1-1060tacrineNOOCO2HOS1Me
A1-1061terazosinNOOCO2HOO1methyl
A1-1062terazosinNOOCO2HOO1C(CH3)3
A1-1063terazosinNOOCO2HOO1Ph
A1-1064terazosinNOOCO2HOO14-Me-Ph
A1-1065terazosinNOOCO2HOO12-pyridyl
A1-1066terazosinNOOCO2HOO14-pyridyl
A1-1067terazosinNOOCO2HOO12-furyl
A1-1068terazosinNOOCO2HOO12-thienyl
A1-1069terazosinNOOCO2H——0Cl
A1-1070terazosinNOOCO2H——0{N(Et)3}+Cl−
A1-1071terazosinNOOCO2HOO1CF3CH2
A1-1072terazosinNOOCO2HOO1cyclopropyl
A1-1073terazosinNOOCO2HOO12-OMe-Ph
A1-1074terazosinNOOCO2HOO1MeSCH2
A1-1075terazosinNOOCO2HOO1MeOCH2
A1-1076terazosinNOOCO2HSS1Ph
A1-1077terazosinNOOCO2HSS1NMe2
A1-1078terazosinNOOCO2HSS1NBn2
A1-1079terazosinNOOCO2HOS1Ph
A1-1080terazosinNOOCO2HOS1Me
A1-1081timololNOOCO2HOO1methyl
A1-1082timololNOOCO2HOO1O(CH3)3
A1-1083timololNOOCO2HOO1Ph
A1-1084timololNOOCO2HOO14-Me-Ph
A1-1085timololNOOCO2HOO12-pyridyl
A1-1086timololNOOCO2HOO14-pyridyl
A1-1087timololNOOCO2HOO12-furyl
A1-1088timololNOOCO2HOO12-thienyl
A1-1089timololNOOCO2H——0Cl
A1-1090timololNOOCO2H——0{N(Et)3}+Cl−
A1-1091timololNOOCO2HOO1CF3CH2
A1-1092timololNOOCO2HOO1cyclopropyl
A1-1093timololNOOCO2HOO12-OMe-Ph
A1-1094timololNOOCO2HOO1MeSCH2
A1-1095timololNOOCO2HOO1MeOCH2
A1-1096timololNOOCO2HSS1Ph
A1-1097timololNOOCO2HSS1NMe2
A1-1098timololNOOCO2HSS1NBn2
A1-1099timololNOOCO2HOS1Ph
A1-1100timololNOOCO2HOS1Me
A1-1121xylometazolineNOOCO2HOO1methyl
A1-1122xylometazolineNOOCO2HOO1C(CH3)3
A1-1123xylometazolineNOOCO2HOO1Ph
A1-1124xylometazolineNOOCO2HOO14-Me-Ph
A1-1125xylometazolineNOOCO2HOO12-pyridyl
A1-1126xylometazolineNOOCO2HOO14-pyridyl
A1-1127xylometazolineNOOCO2HOO12-furyl
A1-1128xylometazolineNOOCO2HOO12-thienyl
A1-1129xylometazolineNOOCO2H——0Cl
A1-1130xylometazolineNOOCO2H——0{N(Et)3}+Cl−
A1-1131xylometazolineNOOCO2HOO1CF3CH2
A1-1132xylometazolineNOOCO2HOO1cyclopropyl
A1-1133xylometazolineNOOCO2HOO12-OMe-Ph
A1-1134xylometazolineNOOCO2HOO1MeSOH2
A1-1135xylometazolineNOOCO2HOO1MeOCH2
A1-1136xylometazolineNOOCO2HSS1Ph
A1-1137xylometazolineNOOCO2HSS1NMe2
A1-1138xylometazolineNOOCO2HSS1NBn2
A1-1139xylometazolineNOOCO2HOS1Ph
A1-1140xylometazolineNOOCO2HOS1Me
A1-1141lovastatinOOOCO2HOO1methyl
A1-1142lovastatinOOOCO2HOO1C(CH3)3
A1-1143lovastatinOOOCO2HOO1Ph
A1-1144lovastatinOOOCO2HOO14-Me-Ph
A1-1145lovastatinOOOCO2HOO12-pyridyl
A1-1146lovastatinOOOCO2HOO14-pyridyl
A1-1147lovastatinOOOCO2HOO12-furyl
A1-1148lovastatinOOOCO2HOO12-thienyl
A1-1149lovastatinOOOCO2H——0Cl
A1-1150lovastatinOOOCO2H——0{N(Et)3}+Cl−
A1-1151lovastatinOOOCO2HOO1CF3CH2
A1-1152lovastatinOOOCO2HOO1cyclopropyl
A1-1153lovastatinOOOCO2HOO12-OMe-Ph
A1-1154lovastatinOOOCO2HOO1MeSCH2
A1-1155lovastatinOOOCO2HOO1MeOCH2
A1-1156lovastatinOOOCO2HSS1Ph
A1-1157lovastatinOOOCO2HSS1NMe2
A1-1158lovastatinOOOCO2HSS1NBn2
A1-1159lovastatinOOOCO2HOS1Ph
A1-1160lovastatinOOOCO2HOS1Me
A1-1161warfarinOOOCO2HOO1methyl
A1-1162warfarinOOOCO2HOO1C(CH3)3
A1-1163warfarinOOOCO2HOO1Ph
A1-1164warfarinOOOCO2HOO14-Me-Ph
A1-1165warfarinOOOCO2HOO12-pyridyl
A1-1166warfarinOOOCO2HOO14-pyridyl
A1-1167warfarinOOOCO2HOO12-furyl
A1-1168warfarinOOOCO2HOO12-thienyl
A1-1169warfarinOOOCO2H——0Cl
A1-1170warfarinOOOCO2H——0{N(Et)3}+Cl−
A1-1171warfarinOOOCO2HOO1CF3CH2
A1-1172warfarinOOOCO2HOO1cyclopropyl
A1-1173warfarinOOOCO2HOO12-OMePh
A1-1174warfarinOOOCO2HOO1MeSCH2
A1-1175warfarinOOOCO2HOO1MeOCH2
A1-1176warfarinOOOCO2HSS1Ph
A1-1177warfarinOOOCO2HSS1NMe2
A1-1178warfarinOOOCO2HSS1NBn2
A1-1179warfarinOOOCO2HOS1Ph
A1-1180warfarinOOOCO2HOS1Me
A1-1181atorvastatinOOOCO2HOO1methyl
A1-1182atorvastatinOOOCO2HOO1C(CH3)3
A1-1183atorvastatinOOOCO2HOO1Ph
A1-1184atorvastatinOOOCO2HOO14-Me-Ph
A1-1185atarvastatinOOOCO2HOO12-pyridyl
A1-1186atorvastatinOOOCO2HOO14-pyridyl
A1-1187atorvastatinOOOCO2HOO12-furyl
A1-1188atorvastatinOOOCO2HOO12-thienyl
A1-1189atorvastatinOOOCO2H——0Cl
A1-1190atorvastatinOOOCO2H——0{N(Et)3}+Cl−
A1-1191atorvastatinOOOCO2HOO1CF3CH2
A1-1192atorvastatinOOOCO2HOO1cyclopropyl
A1-1193atorvastatinOOOCO2HOO12-OMe-Ph
A1-1194atorvastatinOOOCO2HOO1MeSCH2
A1-1195atorvastatinOOOCO2HOO1MeOCH2
A1-1196atorvastatinOOOCO2HSS1Ph
A1-1197atorvastatinOOOCO2HSS1NMe2
A1-1198atorvastatinOOOCO2HSS1NBn2
A1-1199atorvastatinOOOCO2HOS1Ph
A1-1200atorvastatinOOOCO2HOS1Me
A1-1201atropineOOOCO2HOO1methyl
A1-1202atropineOOOCO2HOO1C(CH3)3
A1-1203atropineOOOCO2HOO1Ph
A1-1204atropineOOOCO2HOO14-Me-Ph
A1-1205atropineOOOCO2HOO12-pyridyl
A1-1206atropineOOOCO2HOO14-pyridyl
A1-1207atropineOOOCO2HOO12-furyl
A1-1208atropineOOOCO2HOO12-thienyl
A1-1209atropineOOOCO2H——0Cl
A1-1210atropineOOOCO2H——0{N(Et)3}+Cl−
A1-1211atropineOOOCO2HOO1CF3CH2
A1-1212atropineOOOCO2HOO1cyclopropyl
A1-1213atropineOOOCO2HOO12-OMe-Ph
A1-1214atropineOOOCO2HOO1MeSCH2
A1-1215atropineOOOCO2HOO1MeOCH2
A1-1216atropineOOOCO2HSS1Ph
A1-1217atropineOOOCO2HSS1NMe2
A1-1218atropineOOOCO2HSS1NBn2
A1-1219atropineOOOCO2HOS1Ph
A1-1220atropineOOOCO2HOS1Me
A1-1221bicalutamideOOOCO2HOO1methyl
A1-1222bicalutamideOOOCO2HOO1C(CH3)3
A1-1223bicalutamideOOOCO2HOO1Ph
A1-1224bicalutamideOOOCO2HOO14-Me-Ph
A1-1225bicalutamideOOOCO2HOO12-pyridyl
A1-1226bicalutamideOOOCO2HOO14-pyridyl
A1-1227bicalutamideOOOCO2HOO12-furyl
A1-1228bicalutamideOOOCO2HOO12-thienyl
A1-1229bicalutamideOOOCO2H——0Cl
A1-1230bicalutamideOOOCO2H——0{N(Et)3}+Cl−
A1-1231bicalutamideOOOCO2HOO1CF3CH2
A1-1232bicalutamideOOOCO2HIOO1cyclopropyl
A1-1233bicalutamideOOOCO2HOO12-OMe-Ph
A1-1234bicalutamideOOOCO2HOO1MeSCH2
AI-1235bicalutamideOOOCO2HOO1MeOCH2
A1-1236bicalutamideOOOCO2H5S1Ph
A1-1237bicalutamideOOOCO2HSS1NMe2
A1-1238bicalutamideOOOCO2HSS1NBn2
A1-1239bicalutamideOOOCO2HOS1Ph
A1-1240bicalutamideOOOCO2HOS1Me
A1-1241clobesolOOOCO2HOO1methyl
A1-1242clobesolOOOCO2HOO1C(CH3)3
A1-1243clobesolOOOCO2HOO1Ph
A1-1244clobesolOOOCO2HOO14-Me-Ph
A1-1245clobesolOOOCO2HOO12-pyridyl
A1-1246clobesolOOOCO2HOO14-pyridyl
A1-1247clobesolOOOCO2HOO12-furyl
A1-1248clobesolOOOCO2HOO12-thienyl
A1-1249clobesolOOOCO2H——0Cl
A1-1250clobesolOOOCO2H——{N(Et)3}+Cl−
A1-1251clobesolOOOCO2HOO1CF3CH2
A1-1252clobesolOOOCO2HOO1cyclopropyl
A1-1253clobesolOOOCO2HOO12-OMe-Ph
A1-1254clobesolOOOCO2HOO1MeSCH2
A1-1255clobesolOOOCO2HOO1MeOCH2
A1-1256clobesolOOOCO2HSS1Ph
A1-1257clobesolOOOCO2HSS1NMe2
A1-1258clobesolOOOCO2HSS1NBn2
A1-1259clobesolOOOCO2HOS1Ph
A1-1260clobesolOOOCO2HOS1Me
A1-1261fluticasoneOOOCO2HOO1methyl
propionate
A1-1262fluticasoneOOOCO2HOO1C(CH3)3
propioriate
A1-1263fluticasoneOOOCO2HOO1Ph
propionate
A1-1264fluticasoneOOOCO2HOO14-Me-Ph
propionate
A1-1265fluticasoneOOOCO2HOO12-pyridyl
propionate
A1-1266fluticasoneOOOCO2HOO14-pyridyl
propionate
A1-1267fluticasoneOOOCO2HOO12-furyl
propionate
A1-1268fluticasoneOOOCO2HOO12-thienyl
propionate
A1-1269fluticasoneOOOCO2H——0Cl
propionate
A1-1270fluticasoneOOOCO2H——0{N(Et)3}+Cl−
propionate
A1-1271fluticasoneOOOCO2HOO1CF3CH2
propionate
A1-1272fluticasoneOOOCO2HOO1cyclopropyl
propionate
A1-1273fluticasoneOOOCO2HOO12-OMe-Ph
propionate
A1-1274fluticasoneOOOCO2HOO1MeSCH2
propionate
A1-1275fluticasoneOOOCO2HOO1MeOCH2
propionate
A1-1276fluticasoneOOOCO2HSS1Ph
propionate
A1-1277fluticasoneOOOCO2HSS1NMe2
propionate
A1-1278fluticasoneOOOCO2HSS1NBn2
propionate
A1-1279fluticasoneOOOCO2HOS1Ph
propionate
A1-1280fluticasoneOOOCO2HOS1Me
propionate
A1-1301loperidine HClOOOCO2HOO1methyl
A1-1302loperidine HClOOOCO2HOO1C(CH3)3
A1-1303loperidine HClOOOCO2HOO1Ph
A1-1304loperidine HClOOOCO2HOO14-Me-Ph
A1-1305loperidine HClOOOCO2HOO12-pyridyl
A1-1306loperidine HClOOOCO2HOO14-pyridyl
AI-1307loperidine HClOOOCO2HOO12-furyl
A1-1308loperidine HClOOOCO2HOO12-thienyl
A1-1309loperidine HClOOOCO2H——0Cl
A1-1310loperidine HClOOOCO2H——0{N(Et)3}+Cl−
A1-1311loperidine HClOOOCO2HOO1CF3CH2
A1-1312loperidine HClOOOCO2HOO1cyclopropyl
A1-1313loperidine HClOOOCO2HOO12-OMe-Ph
A1-1314loperidine HClOOOCO2HOO1MeSCH2
A1-1315loperidine HClOOOCO2HOO1MeOCH2
A1-1316loperidine HClOOOCO2HSS1Ph
A1-1317loperidine HClOOOCO2HSS1NMe2
A1-1318loperidine HClOOOCO2HSS1NBn2
A1-1319loperidine HClOOOCO2HOS1Ph
A1-1320loperidine HClOOOCO2HOS1Me
A1-1321monozidOOOCO2HOO1methyl
A1-1322monozidOOOCO2HOO1C(CH3)3
A1-1323monozidOOOCO2HOO1Ph
A1-1324monozidOOOCO2HOO14-Me-Ph
A1-1325monozidOOOCO2HOO12-pyridyl
A1-1326monozidOOOCO2HOO14-pyridyl
A1-1327monozidOOOCO2H.0O12-furyl
A1-1328monozidOOOCO2HOO12-thienyl
A1-1329monozidOOOCO2H——0Cl
A1-1330monozidOOOCO2H——0{N(Et)3}+Cl−
A1-1331monozidOOOCO2HOO1CF3CH2
A1-1332monozidOOOCO2HOO1cyclopropyl
A1-1333monozidOOOCO2HOO12-OMe-Ph
A1-1334monozidOOOCO2HOO1MeSCH2
A1-1335monozidOOOCO2HOO1MeOCH2
A1-1336monozidOOOCO2HSS1Ph
A1-1337monozidOOOCO2HSS1NMe2
A1-1338monozidOOOCO2HSS1NBn2
A1-1339monozidOOOCO2HOS1Ph
A1-1340monozidOOOCO2HOS1Me
A1-1341oxybutynin HClOOOCO2HOO1methyl
A1-1342oxybutynin HClOOOCO2HOO1C(CH3)3
A1-1343oxybutynin HClOOOCO2HOO1Ph
A1-1344oxybutynin HClOOOCO2HOO14-Me-Ph
A1-1345oxybutynin HClOOOCO2HOO12-pyridyl
A1-1346oxybutynin HClOOOCO2HOO14-pyridyl
AI-1347oxybutynin HClOOOCO2HOO12-furyl
A1-1348oxybutynin HClOOOCO2HOO12-thienyl
A1-1349oxybutynin HClOOOCO2H——0Cl
A1-1350oxybutynin HClOOOCO2H——0{N(Et)3}+Cl−
A1-1351oxybutynin HClOOOCO2HOO1CF3CH2
A1-1352oxybutynin HClOOOCO2HOO1cyclopropyl
A1-1353oxybutynin HClOOOCO2HOO12-OMe-Ph
A1-1354oxybutynin HClOOOCO2HOO1MeSCH2
A1-1355oxybutynin HClOOOCO2HOO1MeOCH2
A1-1356oxybutynin HClOOOCO2HSS1Ph
A1-1357oxybutynin HClOOOCO2HSS1NMe2
A1-1358oxybutynin HClOOOCO2HSS1NBn2
A1-1359oxybutynin HClOOOCO2HOS1Ph
A1-1360oxybutynin HClOOOCO2HOS1Me
A1-1361oxycodoneOOOCO2HOO1methyl
A1-1362oxycodoneOOOCO2HOO1C(CH3)3
A1-1363oxycodoneOOOCO2HOO1Ph
A1-1364oxycodoneOOOCO2HOO14-Me-Ph
A1-1365oxycodoneOOOCO2HOO12-pyridyl
A1-1366oxycodoneOOOCO2HOO14-pyridyl
A1-1367oxycodoneOOOCO2HOO12-furyl
A1-1368oxycodoneOOOCO2HOO12-thienyl
A1-1369oxycodoneOOOCO2H——0Cl
A1-1370oxycodoneOOOCO2H——0{N(Et)3}+Cl−
A1-1371oxycodoneOOOCO2HOO1CF3CH2
A1-1372oxycodoneOOOCO2HOO1cyclopropyl
A1-1373oxycodoneOOOCO2HOO12-OMe-Ph
A1-1374oxycodoneOOOCO2HOO1MeSCH2
A1-1375oxycodoneOOOCO2HOO1MeOCH2
A1-1376oxycodoneOOOCO2HSS1Ph
A1-1377oxycodoneOOOCO2HSS1NMe2
A1-1378oxycodoneOOOCO2HSS1NBn2
A1-1379oxycodoneOOOCO2HOS1Ph
A1-1380oxycodoneOOOCO2HOS1Me
A1-1381piroxicamOOOCO2HOO1methyl
A1-1382piroxicamOOOCO2HOO1C(CH3)3
A1-1383piroxicamOOOCO2HOO1Ph
A1-1384piroxicamOOOCO2HOO14-Me-Ph
A1-1385piroxicamOOOCO2HOO12-pyridyl
A1-1386piroxicamOOOCO2HOO14-pyridyl
A1-1387piroxicamOOOCO2HOO12-furyl
A1-1388piroxicamOOOCO2HOO12-thienyl
A1-1389piroxicamOOOCO2H——0Cl
A1-1390piroxicamOOOCO2H——0{N(Et)3}+Cl−
A1-1391piroxicamOOOCO2HOO1CF3CH2
A1-1392piroxicamOOOCO2HOO1cyclopropyl
A1-1393piroxicamOOOCO2HOO12-OMe-Ph
A1-1394piroxicamOOOCO2HOO1MeSCH2
A1-1395piroxicamOOOCO2HOO1MeOCH2
A1-1396piroxicamOOOCO2HSS1Ph
A1-1397piroxicamOOOCO2HSS1NMe2
A1-1398piroxicamOOOCO2HSS1NBn2
A1-1399piroxicamOOOCO2HOS1Ph
A1-1400piroxicamOOOCO2HOS1Me
A1-1401simvastatinOOOCO2HOO1methyl
AI-1402simvastatinOOOCO2HOO1C(CH3)3
A1-1403simvastatinOOOCO2HOO1Ph
A1-1404simvastatinOOOCO2HOO14-Me-Ph
A1-1405simvastatinOOOCO2HOO12-pyridyl
A1-1406simvastatinOOOCO2HOO14-pyridyl
A1-1407simvastatinOOOCO2HOO12-furyl
A1-1408simvastatinOOOCO2HOO12-thienyl
A1-1409simvastatinOOOCO2H——0Cl
A1-1410simvastatinOOOCO2H——0{N(Et)3}+Cl−
A1-1411simvastatinOOOCO2HOO1CF3OH2
A1-1412simvastatinOOOCO2HOO1cyclopropyl
A1-1413simvastatinOOOCO2HOO12-OMe-Ph
A1-1414simvastatinOOOCO2HOO1MeSCH2
A1-1415simvastatinOOOCO2HOO1MeOOH2
A1-1416simvastatinOOOCO2HSS1Ph
A1-1417simvastatinOOOCO2HSS1NMe2
A1-1418simvastatinOOOCO2HSS1NBn2
A1-1419simvastatinOOOCO2HOS1Ph
A1-1420simvastatinOOOCO2HOS1Me
A1-1421troglitazoneOOOCO2HOO1methyl
A1-1422troglitazoneOOOCO2HOO1C(CH3)a
A1-1423troglitazoneOOOCO2HOO1Ph
A1-1424troglitazoneOOOCO2HOO14-Me-Ph
A1-1425troglitazoneOOOCO2HOO12-pyridyl
A1-1426troglitazoneOOOCO2HOO14-pyridyl
A1-1427troglitazoneOOOCO2HOO12-furyl
A1-1428troglitazoneOOOCO2HOO12-thienyl
A1-1429troglitazoneOOOCO2H——0Cl
A1-1430troglitazoneOOOCO2H——0{N(Et)3}+Cl−
A1-1431troglitazoneOOOCO2HOO1CF3CH2
A1-1432troglitazoneOOOCO2HOO1cyclopropyl
A1-1433troglitazoneOOOCO2HOO12-OMe-Ph
A1-1434troglitazoneOOOCO2HOO1MeSCH2
A1-1435troglitazoneOOOCO2HOO1MeOCH2
A1-1436troglitazoneOOOCO2HSS1Ph
A1-1437troglitazoneOOOCO2HSS1NMe2
A1-1438troglitazoneOOOCO2HSS1NBn2
A1-1439troglitazoneOOOCO2HOS1Ph
A1-1440troglitazoneOOOCO2HOS1Me
A1-1441carbamazepamNOOCO2HOO1methyl
A1-1442carbamazepamNOOCO2HOO1C(CH3)3
A1-1443carbamazepamNOOCO2HOO1Ph
A1-1444carbamazepamNOOCO2HOO14-Me-Ph
A1-1445carbamazepamNOOCO2HOO12-pyridyl
A1-1446carbamazepamNOOCO2HOO14-pyridyl
A1-1447carbamazepamNOOCO2HOO12-furyl
A1-1448carbamazepamNOOCO2HOO12-thienyl
A1-1449carbamazepamNOOCO2H——0Cl
A1-1450carbamazepamNOOCO2H——0{N(Et)3}+Cl−
A1-1451carbamazepamNOOCO2HOO1CF3CH2
A1-1452carbamazepamNOOCO2HOO1cyclopropyl
A1-1453carbamazepamNOOCO2HOO12-OMePh
A1-1454carbamazepamNOOCO2HOO1MeSOH2
A1-1455carbamazepamNOOCO2HOO1MeOCH2
A1-1456carbamazepamNOOCO2HSS1Ph
A1-1457carbamazepamNOOCO2HSS1NMe2
A1-1458carbamazepamNOOCO2HSS1NBn2
A1-1459carbamazepamNOOCO2HOS1Ph
A1-1460carbamazepamNOOCO2HOS1Me
A1-1461amoxicillinNOOCO2HOO1methyl
A1-1462amoxicillinNOOCO2HOO1C(CH3)3
A1-1463amoxicillinNOOCOHOO1Ph
A1-1464amoxicillinNOOCO2HOO14-Me-Ph
A1-1465amoxicillinNOOCO2HOO12-pyridyl
A1-1466amoxicillinNOOCO2HOO14-pyridyl
A1-1467amoxicillinNOOCO2HOO12-furyl
A1-1468amoxicillinNOOCO2HOO12-thienyl
A1-1469amoxicillinNOOCO2H——0Cl
A1-1470amoxicillinNOOCO2H——0{N(Et)3}+Cl−
A1-1471amoxicillinNOOCO2HOO1CF3CH2
A1-1472amoxicillinNOOCO2HOO1cyclopropyl
A1-1473amoxicillinNOOCO2HOO12-OMe-Ph
A1-1474amoxicillinNOOCO2HOO1MeSCH2
A1-1475amoxicillinNOOCO2HOO1MeOCH2
A1-1476amoxicillinNOOCO2HSS1Ph
A1-1477amoxicillinNOOCO2HSS1NMe2
A1-1478amoxicillinNOOCO2HSS1NBn2
A1-1479amoxicihinNOOCO2HOS1Ph
A1-1480amoxicillinNOOCO2HOS1Me
A1-1481benazeprilNOOCO2HOO1methyl
A1-1482benazeprilNOOCO2HOO1C(CH3)3
A1-1483benazeprilNOOCO2HOO1Ph
A1-1484benazeprilNOOCO2HOO14-Me-Ph
A1-1485benazeprilNOOCO2HOO12-pyridyl
A1-1486benazeprilNOOCO2HOO14-pyridyl
A1-1487benazeprilNOOCO2HOO12-furyl
A1-1488benazeprilNOOCO2HOO12-thienyl
A1-1489benazeprilNOOCO2H——0Cl
A1-1490benazeprilNOOCO2H——0{N(Et)3}+Cl−
A1-1491benazeprilNOOCO2HOO1CF3CH2
A1-1492benazeprilNOOCO2HOO1cyclopropyl
A1-1493benazeprilNOOCO2HOO12-OMe-Ph
A1-1494benazeprilNOOCO2HOO1MeSCH2
A1-1495benazeprilNOOCO2HOO1MeOCH2
A1-1496benazeprilNOOCO2HSS1Ph
A1-1497benazeprilNOOCO2HSS1NMe2
A1-1498benazeprilNOOCO2HSS1NBn2
A1-1499benazepnilNOOCO2HOS1Ph
A1-1500benazeprilNOOCO2HOS1Me
A1-1501cefachlorNOOCO2HOO1methyl
A1-1502cefachlorNOOCO2HOO1C(CH3)a
A1-1503cefachlorNOOCO2HOO1Ph
A1-1504cefachlorNOOCO2HOO14-Me-Ph
A1-1505cefachlorNOOCO2HOO12-pyridyl
A1-1506cefachlorNOOCO2HOO14-pynidyl
A1-1507cefachlorNOOCO2HOO12-furyl
A1-1508cefachlorNOOCO2HOO12-thienyl
A1-1509cefachlorNOOCO2H——0Cl
A1-1510cefachlorNOOCO2H——0{N(Et)3}+Cl−
A1-1511cefachlorNOOCO2HOO1CF3CH2
A1-1512cefachlorNOOCO2HOO1cyclopropyl
A1-1513cefachlorNOOCO2HOO12-OMe-Ph
A1-1514cefachlorNOOCO2HOO1MeSCH2
A1-1515cefachlorNOOCO2HOO1MeOCH2
A1-1516cefachlorNOOCO2HSS1Ph
A1-1517cefachlorNOOCO2HSS1NMe2
A1-1518cefachlorNOOCO2HSS1NBn2
A1-1519cefachlorNOOCO2HOS1Ph
A1-1520cefachlorNOOCO2HOS1Me
A1-1521cetirizineNOOCO2HOO1methyl
A1-1522cetirizineNOOCO2HOO1C(CH3)3
A1-1523cetirizineNOOCO2HOO1Ph
A1-1524cetirizineNOOCO2HOO14-Me-Ph
A1-1525cetirizineNOOCO2HOO12-pyridyl
A1-1526cetirizineNOOCO2HOO14-pyridyl
A1-1527cetirizineNOOCO2HOO12-furyl
A1-1528cetirizineNOOCO2HOO12-thienyl
A1-1529cetirizinecNOOCO2H——0Cl
A1-1530cetirizineNOOCO2H——0{N(Et)3}+Cl−
A1-1531cetirizineNOOCO2HOO1CF3CH2
A1-1532cetirizineNOOCO2HOO1cyclopropyl
A1-1533cetirizineNOOCO2HOO12-OMe-Ph
Ai-1534cetirizineNOOCO2HOO1MeSCH2
A1-1535cetirizineNOOCO2HOO1MeOCH2
A1-1536cetirizineNOOCO2HSS1Ph
A1-1537cetirizineNOOCO2HSS1NMe2
A1-1538cetirizineNOOCO2HSS1NBn2
A1-1539cetirizineNOOCO2HOS1Ph
A1-1540cetirizineNOOCO2HOS1Me
A1-1541cefadroxilNOOCO2HOO1methyl
A1-1542cefadroxilNOOCO2HOO1C(CH3)3
A1-1543cefadroxilNOOCO2HOO1Ph
A1-1544cefadroxilNOOCO2HOO14-Me-Ph
A1-1545cefadroxilNOOCO2HOO12-pyridyl
A1-1546cefadroxilNOOCO2HOO14-pyridyl
A1-1547cefadroxilNOOCO2HOO12-furyl
A1-1548cefadroxilNOOCO2HOO12-thienyl
A1-1549cefadroxilNOOCO2H——0Cl
A1-1550cefadroxilNOOCO2H——0{N(Et)3}+Cl−
A1-1551cefadroxilNOOCO2HOO1CF3CH2
A1-1552cefadroxilNOOCO2HOO1cyclopropyl
A1-1553cefadroxilNOOCO2HOO12-OMe-Ph
A1-1554cefadroxilNOOCO2HOO1MeSCH2
A1-1555cefadroxilNOOCO2HOO1MeOCH2
A1-1556cefadroxilNOOCO2HSS1Ph
A1-1557cefadroxilNOOCO2HSS1NMe2
A1-1558cefadroxilNOOCO2HSS1NBn2
A1-1559cefadroxilNOOCO2HOS1Ph
A1-1560cefadroxilNOOCO2HOS1Me
A1-1561clonazepamNOOCO2HOO1methyl
A1-1562clonazepamNOOCO2HOO1C(CH3)3
A1-1563clonazepamNOOCO2HOO1Ph
A1-1564clonazepamNOOCO2HOO14-Me-Ph
AI-1565clonazepamNOOCO2HOO12-pyridyl
A1-1566clonazepamNOOCO2HOO14-pyridyl
A1-1567clonazepamNOOCO2HOO12-furyl
A1-1568clonazepamNOOCO2HOO12-thienyl
A1-1569clonazepamNOOCO2H——0Cl
A1-1570clonazepamNOOCO2H——0{N(Et)3}+Cl−
A1-1571clonazepamNOOCO2HOO1CF3CH2
A1-1572clonazepamNOOCO2HOO1cyclopropyl
A1-1573clonazepamNOOCOYOO12-OMe-Ph
A1-1574clonazepamNOOCO2HOO1MeSCH2
A1-1575clonazepamNOOCO2HOO1MeOCH2
A1-1576clonazepamNOOCO2HSS1Ph
A1-1577clonazepamNOOCO2HSS1NMe2
A1-1578clonazepamNOOCO2HSS1NBn2
A1-1579clonazepamNOOCO2HOS1Ph
A1-1580clonazepainNOOCO2HOS1Me
A1-1581demethylimipramineNOOCO2HOO1methyl
A1-1582demethylimipramineNOOCO2HOO1C(CH3)3
A1-1583demethylimipramineNOOCO2HOO1Ph
A1-1584demethylimipramineNOOCO2HOO14-Me-Ph
A1-1585demethylimipramineNOOCO2HOO12-pyridyl
A1-1586demethylimipramineNOOCO2HOO14-pyridyl
A1-1587demethylimipramineNOOCO2HOO12-furyl
A1-1588demethylimipramineNOOCO2HOO12-thienyl
A1-1589demethylimipramineNOOCO2H——0Cl
A1-1590demethylimipramineNOOCO2H——0{N(Et)3}+Cl−
A1-1591demethylimipramineNOOCO2HOO1CF3CH2
A1-1592demethylimipramineNOOCO2HOO1cyclopropyl
A1-1593demethylimipramineNOOCO2HOO12-OMe-Ph
A1-1594demethylimipramineNOOCO2HOO1MeSCH2
A1-1595demethylimipramineNOOCO2HOO1MeOCH2
A1-1596demethylimipramineNOOCO2HSS1Ph
A1-1597demethylimipramineNOOCO2HS51NMe2
A1-1598demethylimipramineNOOCO2HSS1NBn2
A1-1599demethylimipramineNOOCO2HOS1Ph
A1-1600demethylimipramineNOOCO2HOS1Me
A1-1601deprenilOOOCO2HOO1methyl
A1-1602deprenilOOOCO2HOO1C(CH3)3
A1-1603deprenilOOOCO2HOO1Ph
A1-1604deprenilOOOCO2HOO14-Me-Ph
A1-1605deprenilOOOCO2HOO12-pyridyl
A1-1606deprenilOOOCO2HOO14-pyridyl
A1-1607deprenilOOOCO2HOO12-furyl
A1-1608deprenilOOOCO2HOO12-thienyl
A1-1609deprenilOOOCO2H——0Cl
A1-1610deprenilOOOCO2H——0{N(Et)3}+Cl−
A1-1611deprenilOOOCO2HOO1CF3CH2
A1-1612deprenilOOOCO2HOO1cyclopropyl
A1-1613deprenilOOOCO2HOO12-OMe-Ph
A1-1614deprenilOOOCO2HOO1MeSCH2
A1-1615deprenilOOOCO2HOO1MeOCH2
A1-1616deprenilOOOCO2HSS1Ph
A1-1617deprenilOOOCO2HSS1NMe2
A1-1618deprenilOOOCO2HSS1NBn2
A1-1619deprenilOOOCO2HOS1Ph
A1-1620deprenilOOOCO2HOS1Me
A1-1621doxazosinOOOCO2HOO1methyl
A1-1622doxazosinOOOCO2HOO1C(CH3)3
A1-1623doxazosinOOOCO2HOO1Ph
A1-1624doxazosinOOOCO2HOO14-Me-Ph
A1-1625doxazosinOOOCO2HOO12-pyridyl
A1-1626doxazosinOOOCO2HOO14-pyridyl
A1-1627doxazosinOOOCO2HOO12-furyl
A1-1628doxazosinOOOCO2HOO12-thienyl
A1-1629doxazosinOOOCO2H——0Cl
A1-1630doxazosinOOOCO2H——0{N(Et)3}+Cl−
A1-1631doxazosinOOOCO2HOO1CF3CH2
A1-1632doxazosinOOOCO2HOO1cyclopropyl
A1-1633doxazosinOOOCO2HOO12-OMe-Ph
A1-1634doxazosinOOOCO2HOO1MeSCH2
A1-1635doxazosinOOOCO2HOO1MeOCH2
A1-1636doxazosinOOOCO2HSS1Ph
A1-1637doxazosinOOOCO2HSS1NMe2
A1-1638doxazosinOOOCO2HSS1NBn2
A1-1639doxazosinOOOCO2HOS1Ph
A1-1640doxazosinOOOCO2HOS1Me
A1-1641enalaprilOOOCO2HOO1methyl
A1-1642enalaprilOOOCO2HOO1C(CH3)3
A1-1643enalaprilOOOCO2HOO1Ph
A1-1644enalaprilOOOCO2HOO14-Me-Ph
A1-1645enalaprilOOOCO2HOO12-pyridyl
A1-1646enalaprilOOOCO2HOO14-pyridyl
A1-1647enalaprilOOOCO2HOO12-furyl
A1-1648enalaprilOOOCO2HOO12-thienyl
A1-1649enalaprilOOOCO2H——0Cl
A1-1650enalaprilOOOCO2H——0{N(Et)3}+Cl−
A1-1651enalaprilOOOCO2HOO1CF3CH2
A1-1652enalaprilOOOCO2HOO1cyclopropyl
A1-1653enalaprilOOOCO2HOO12-OMe-Ph
A1-1654enalaprilOOOCO2HOO1MeSCH2
A1-1655enalaprilOOOCO2HOO1MeOCH2
A1-1656enalaprilOOOCO2HSS1Ph
A1-1657enalaprilOOOCO2HSS1NMe2
A1-1658enalaprilOOOCO2HSS1NBn2
A1-1659enalaprilOOOCO2HOS1Ph
A1-1660enalaprilOOOCO2HOS1Me
A1-1661famciclovirOOOCO2HOO1methyl
A1-1662famciclovirOOOCO2HOO1C(CH3)3
A1-1663famciclovirOOOCO2HOO1Ph
A1-1664famciclovirOOOCO2HOO14-Me-Ph
A1-1665famciclovirOOOCO2HOO12-pyridyl
A1-1666famciclovirOOOCO2HOO14-pyridyl
A1-1667famciclovirOOOCO2HOO12-furyl
A1-1668famciclovirOOOCO2HOO12-thienyl
A1-1669famciclovirOOOCO2H——0Cl
A1-1670famciclovirOOOCO2H——0{N(Et)3}+Cl−
A1-1671famciclovirOOOCO2HOO1CF3CH2
A1-1672famciclovirOOOCO2HOO1cyclopropyl
A1-1673famciclovirOOOCO2HOO12-OMe-Ph
A1-1674famciclovirOOOCO2HOO1MeSCH2
A1-1675famciclovirOOOCO2HOO1MeOCH2
A1-1676famciclovirOOOCO2HSS1Ph
AI-1677famciclovirOOOCO2HSS1NMe2
A1-1678famciclovirOOOCO2HSS1NBn2
A1-1679famciclovirOOOCO2HOS1Ph
A1-1680famciclovirOOOCO2HOS1Me
AI-1681fluoxetine HClNOOCO2HOO1methyl
A1-1682fluoxetine HClNOOCO2HOO1C(CH3)3
A1-1683fluoxetine HClNOOCO2HOO1Ph
A1-1684fluoxetine HClNOOCO2HOO14-Me-Ph
A1-1685fluoxetine HClNOOCO2HOO12-pyridyl
A1-1686fluoxetine HClNOOCO2HOO14-pyridyl
A1-1687fluoxetine HClNOOCO2HOO12-furyl
A1-1688fluoxetine HClNOOCO2HOO12-thienyl
A1-1689fluoxetine HClNOOCO2H——0Cl
A1-1690fluoxetine HClNOOCO2H——0{N(Et)3}+Cl−
A1-1691fluoxetine HClNOOCO2HOO1CF3CH2
A1-1692fluoxetine HClNOOCO2HOO1cyclopropyl
A1-1693fluoxetine HClNOOCO2HOO12-OMe-Ph
A1-1694fluoxetine HClNOOCO2HOO1MeSCH2
A1-1695fluoxetine HClNOOCO2HOO1MeOCH2
A1-1696fluoxetine HClNOOCO2HSS1Ph
A1-1697fluoxetine HClNOOCO2HSS1NMe2
A1-1698fluoxetine HClNOOCO2HSS1NBn2
A1-1699fluoxetine HClNOOCO2HOS1Ph
A1-1700fluoxetine HClNOOCO2HOS1Me
A1-1701gabapentinNOOCO2HOO1methyl
A1-1702gabapentinNOOCO2HOO1C(CH3)a
A1-1703gabapentinNOOCO2HOO1Ph
A1-1704gabapentinNOOCO2HOO14-Me-Ph
A1-1705gabapentinNOOCO2HOO12-pyridyl
A1-1706gabapentinNOOCO2HOO14-pyridyl
A1-1707gabapentinNOOCO2HOO12-furyl
AJ-1708gabapentinNOOCO2HOO12-thienyl
A1-1709gabapentinNOOCO2H——0Cl
A1-1710gabapentinNOOCO2H——0{N(Et)3}+Cl−
A1-1711gabapentinNOOCO2HOO1CF3CH2
A1-1712gabapentinNOOCO2HOO1cyclopropyl
A1-1713gabapentinNOOCO2HOO12-OMe-Ph
A1-1714gabapentinNOOCO2HOO1MeSCH2
A1-1715gabapentinNOOCO2HOO1MeOCH2
A1-1716gabapentinNOOCO2HSS1Ph
A1-1717gabapentinNOOCO2HSS1NMe2
A1-1718gabapentinNOOCO2HSS1NBn2
A1-1719gabapentinNOOCO2HOS1Ph
A1-1720gabapentinNOOCO2HOS1Me
A1-1721methylphenidateNOOCO2HOO1methyl
A1-1722methylphenidateNOOCO2HOO1C(CH3)3
A1-1723methylphenidateNOOCO2HOO1Ph
A1-1724methylphenidateNOOCO2HOO14-Me-Ph
A1-1725methylphenidateNOOCO2HOO12-pyridyl
A1-1726methylphenidateNOOCO2HOO14-pyridyl
A1-1727methylphenidateNOOCO2HOO12-furyl
A1-1728methylphenidateNOOCO2HOO12-thienyl
A1-1729methylphenidateNOOCO2H——0Cl
A1-1730methylphenidateNOOCO2H——0{N(Et)3}+Cl−
A1-1731methylphenidateNOOCO2HOO1CF3CH2
A1-1732methylphenidateNOOCO2HOO1cyclopropyl
A1-1733methylphenidateNOOCO2HOO12-OMe-Ph
A1-1734methylphenidateNOOCO2HOO1MeSCH2
A1-1735methylphenidateNOOCO2HOO1MeOCH2
A1-1736methylphenidateNOOCO2HSS1Ph
A1-1737methylphenidateNOOCO2HSS1NMe2
A1-1738methylphenidateNOOCO2HSS1NBn2
A1-1739methylphenidateNOOCO2HOS1Ph
A1-1740methylphenidateNOOCO2HOS1Me
A1-1741olanzapineNOOCO2HOO1methyl
A1-1742olanzapineNOOCO2HOO1C(CH3)3
A1-1743olanzapineNOOCO2HOO1Ph
A1-1744olanzapineNOOCO2HOO14-Me-Ph
A1-1745olanzapineNOOCO2HOO12-pyridyl
A1-1746olanzapineNOOCO2HOO14-pyridyl
A1-1747olanzapineNOOCO2HOO12-furyl
A1-1748olanzapineNOOCO2HOO12-thienyl
A1-1749alanzapineNOOCO2H——0Cl
A1-1750olanzapineNOOCO2H——0{N(Et)3}+Cl−
A1-1751olanzapineNOOCO2HOO1CF3CH2
A1-1752olanzapineNOOCO2HOO1cyclopropyl
A1-1753olanzapineNOOCO2HOO12-OMe-Ph
A1-1754olanzapineNOOCO2HOO1MeSCH2
A1-1755olanzapineNOOCO2HOO1MeOCH2
A1-1756olanzapineNOOCO2HSS1Ph
A1-1757olanzapineNOOCO2HSS1NMe2
A1-1758olanzapineNOOCO2HSS1NBn2
A1-1759olanzapineNOOCO2HOS1Ph
A1-1760olanzapineNOOCO2HOS1Me
A1-1761lansoprazoleNOOCO2HOO1methyl
A1-1762lansoprazoleNOOCO2HOO1C(CH3)3
A1-1763lansoprazoleNOOCO2HOO1Ph
A1-1764lansoprazoleNOOCO2HOO14-Me-Ph
A1-l765lansoprazoleNOOCO2HOO12-pyridyl
A1-1766lansoprazoleNOOCO2HOO14-pyridyl
A1-1767lansoprazoleNOOCO2HOO12-furyl
A1-1768lansoprazoleNOOCO2HOO12-thienyl
A1-1769lansoprazoleNOOCO2H——0Cl
A1-1770lansoprazoleNOOCO2H——0{N(Et)3}+Cl−
A1-1771lansoprazoleNOOCO2HOO1CF3CH2
A1-1772lansoprazoleNOOCO2HOO1cyclopropyl
A1-1773lansoprazoleNOOCO2HOO12-OMe-Ph
A1-1774lansoprazoleNOOCO2HOO1MeSCH2
A1-1775lansoprazoleNOOCO2HOO1MeOCH2
A1-1776lansoprazoleNOOCO2HSS1Ph
A1-1777lansoprazoleNOOCO2HSS1NMe2
A1-1778lansoprazoleNOOCO2HSS1NBn2
A1-1779lansoprazoleNOOCO2HOS1Ph
A1-1780lansoprazoleNOOCO2HOS1Me
A1-1781omeprazoleNOOCO2HOO1methyl
A1-1782omeprazoleNOOCO2HOO1C(CH3)3
A1-1783omeprazoleNOOCO2HOO1Ph
A1-1784omeprazoleNOOCO2HOO14-Me-Ph
A1-1785omeprazoleNOOCO2HOO12-pyridyl
A1-1786omeprazoleNOOCO2HOO14-pyridyl
A1-1787omeprazoleNOOCO2HOO12-furyl
A1-1788omeprazoleNOOCO2HOO12-thienyl
A1-1789omeprazoleNOOCO2H——0Cl
A1-1790omeprazoleNOOCO2H——0{N(Et)3}+Cl−
A1-1791omeprazoleNOOCO2HOO1CF3CH2
A1-1792omeprazoleNOOCO2HOO1cyclopropyl
A1-1793omeprazoleNOOCO2HOO12-OMe-Ph
A1-1794omeprazoleNOOCO2HOO1MeSCH2
A1-1795omeprazoleNOOCO2HOO1MeOCH2
A1-1796omeprazoleNOOCO2HSS1Ph
A1-1797omeprazoleNOOCO2HSS1NMe2
A1-1798omeprazoleNOOCO2HSS1NBn2
A1-1799omeprazoleNOOCO2HOS1Ph
A1-1800omeprazoleNOOCO2HOS1Me
A1-1801omeprazoleOOOCO2HOO1methyl
A1-1802omeprazoleOOOCO2HOO1C(CH3)3
A1-1803omeprazoleOOOCO2HOO1Ph
A1-1804omeprazoleOOOCO2HOO14-Me-Ph
A1-1805omeprazoleOOOCO2HOO12-pyridyl
A1-1806omeprazoleOOOCO2HOO14-pyridyl
A1-1807omeprazoleOOOCO2HOO12-furyl
A1-1808omeprazoleOOOCO2HOO12-thienyl
A1-1809omeprazoleOOOCO2H——0Cl
A1-1810omeprazoleOOOCO2H——0{N(Et)3}+Cl−
A1-1811omeprazoleOOOCO2HOO1CF3CH2
A1-1812omeprazoleOOOCO2HOO1cyclopropyl
A1-1813omeprazoleOOOCO2HOO12-OMe-Ph
A1-1814omeprazoleOOOCO2HOO1MeSOH2
A1-1815omeprazoleOOOCO2HOO1MeOCH2
A1-1816omeprazoleOOOCO2HSS1Ph
A1-1817omeprazoleOOOCO2HSS1NMe2
A1-1818omeprazoleOOOCO2HSS1NBn2
A1-1819omeprazoleOOOCO2HOS1Ph
A1-1820omeprazoleOOOCO2HOS1Me
A1-1821phentermineOOOCO2HOO1methyl
A1-1822phentermineOOOCO2HOO1C(CH3)3
A1-1823phentermineOOOCO2HOO1Ph
A1-1824phentermineOOOCO2HOO14-Me-Ph
A1-1825phentermineOOOCO2HOO12-pyridyl
A1-1826phentermineOOOCO2HOO14-pyridyl
A1-1827phentermineOOOCO2HOO12-furyl
A1-1828phentermineOOOCO2HOO12-thienyl
A1-1829phentermineOOOCO2H——0Cl
A1-1830phentermineOOOCO2H——0{N(Et)3}+Cl−
A1-1831phentermineOOOCO2HOO1CF3CH2
A1-1832phentermineOOOCO2HOO1cyclopropyl
A1-1833phentermineOOOCO2HOO12-OMe-Ph
A1-1834phentermineOOOCO2HOO1MeSCH2
A1-1835phentermineOOOCO2HOO1MeOCH2
A1-1836phentermineOOOCO2HSS1Ph
A1-1837phentermineOOOCO2HSS1NMe2
A1-1838phentermineOOOCO2HSS1NBn2
A1-1839phentermineOOOCO2HOS1Ph
A1-1840phentermineOOOCO2HOS1Me
A1-1841paroxetineNOOCO2HOO1methyl
A1-1842paroxetineNOOCO2HOO1C(CH3)a
A1-1843paroxetineNOOCO2HOO1Ph
A1-1844paroxetineNOOCO2HOO14-Me-Ph
A1-1845paroxetineNOOCO2HOO12-pyridyl
A1-1846paroxetineNOOCO2HOO14-pyridyl
A1-1847paroxetineNOOCO2HOO12-furyl
A1-1848paroxetineNOOCO2HOO12-thienyl
A1-1849paroxetineNOOCO2H——0Cl
A1-1850paroxetineNOOCO2H——0{N(Et)3}+Cl−
A1-1851paroxetineNOOCO2HOO1CF3CH2
A1-1852paroxetineNOOCO2HOO1cyclopropyl
A1-1853paroxetineNOOCO2HOO12-OMe-Ph
A1-1854paroxetineNOOCO2HOO1MeSCH2
A1-1855paroxetineNOOCO2HOO1MeOCH2
A1-1856paroxetineNOOCO2HSS1Ph
A1-1857paroxetineNOOCO2HSS1NMe2
A1-1858paroxetineNOOCO2HSS1NBn2
A1-1859paroxetineNOOCO2HOS1Ph
A1-1860paroxetineNOOCO2HOS1Me
A1-1861quinaprilNOOCO2HOO1methyl
A1-1862quinaprilNOOCO2HOO1C(CH3)3
A1-1863quinaprilNOOCO2HOO1Ph
A1-1864quinaprilNOOCO2HOO14-Me-Ph
A1-1865quinaprilNOOCO2HOO12-pyridyl
A1-1866quinaprilNOOCO2HOO14-pyridyl
A1-1867quinaprilNOOCO2HOO12-furyl
A1-1868quinaprilNOOCO2HOO12-thienyl
A1-1869quinaprilNOOCO2H——0Cl
A1-1870quinaprilNOOCO2H——0{N(Et)3}+Cl−
A1-1871quinaprilNOOCO2HOO1CF3CH2
A1-1872quinaprilNOOCO2HOO1cyclopropyl
A1-1873quinaprilNOOCO2HOO12-OMe-Ph
A1-1874quinaprilNOOCO2HOO1MeSCH2
A1-1875quinaprilNOOCO2HOO1MeOCH2
A1-1876quinaprilNOOCO2HSS1Ph
A1-1877quinaprilNOOCO2HSS1NMe2
A1-1878quinaprilNOOCO2HSS1NBn2
A1-1879quinaprilNOOCO2HOS1Ph
A1-1880quinaprilNOOCO2HOS1Me
A1-1881sertralineNOOCO2HOO1methyl
A1-1882sertralineNOOCO2HOO1C(CH3)a
A1-1883sertralineNOOCO2HOO1Ph
A1-1884sertralineNOOCO2HOO14-Me-Ph
A1-1885sertralineNOOCO2HOO12-pyridyl
A1-1886sertralineNOOCO2HOO14-pyridyl
A1-1887sertralineNOOCO2HOO12-furyl
A1-1888sertralineNOOCO2HOO12-thienyl
A1-1889sertralineNOOCO2H——0Cl
A1-1890sertralineNOOCO2H——0{N(Et)3}+Cl−
A1-1891sertralineNOOCO2HOO1CF3CH2
A1-1892sertralineNOOCO2HOO1cyclopropyl
A1-1893sertralineNOOCO2HOO12-OMe-Pli
A1-1894sertralineNOOCO2HOO1MeSCH2
A1-1895sertralineNOOCO2HOO1MeOCH2
A1-1896sertralineNOOCO2HSS1Ph
A1-1897sertralineNOOCO2HSS1NMe2
A1-1898sertralineNOOCO2HSS1NBn2
A1-1899sertralineNOOCO2HOS1Ph
A1-1900sertralineNOOCO2HOS1Me
A1-1901bupropionNOOCO2HOO1methyl
A1-1902bupropionNOOCO2HOO1C(CH3)a
A1-1903bupropionNOOCO2HOO1Ph
A1-l904bupropionNOOCO2HOO14-Me-Ph
A1-l905bupropionNOOCO2HOO12-pyridyl
A1-1906bupropionNOOCO2HOO14-pyridyl
A1-1907bupropionNOOCO2HOO12-furyl
A1-1908bupropionNOOCO2HOO12-thienyl
A1-1909bupropionNOOCO2H——0Cl
A1-1910bupropionNOOCO2H——0{N(Et)3}+Cl−
A1-1911bupropionNOOCO2HOO1CF3CH2
A1-1912bupropionNOOCO2HOO1cyclopropyl
A1-1913bupropionNOOCO2HOO12-OMe-Ph
A1-1914bupropionNOOCO2HOO1MeSCH2
A1-1915bupropionNOOCO2HOO1MeOCH2
A1-1916bupropionNOOCO2HSS1Ph
A1-1917bupropionNOOCO2HSS1NMe2
A1-1918bupropionNOOCO2HSS1NBn2
A1-1919bupropionNOOCO2HOS1Ph
A1-1920bupropionNOOCO2HOS1Me
|
[0651] Table A2: Compounds (A2-1)-(A2-1920) are compounds of Formula I where X1, Z(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2Me.
[0652] Table A3: Compounds (A3-1)-(A3-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2Et.
[0653] Table A4: Compounds (A4-1)-(A4-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2n-Pr.
[0654] Table A5: Compounds (A5-1)-(A5-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2t-Bu.
[0655] Table A6: Compounds (A6-1)-(A6-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2cyclopropyl.
[0656] Table A7: Compounds (A7-1)-(A7-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2Bn.
[0657] Table A8: Compounds (A8-1)-(A8-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2CH2CH2Ph.
[0658] Table A9: Compounds (A9-1)-(A9-1920) are compounds of Formula I where X1, Z1(X1)-H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2CH2CF3.
[0659] Table A10: Compounds (A10-1)-(A10-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2CH2OMe.
[0660] Table A11: Compounds (A11-1)-(A11-1920) are compounds of Formula I where X1, Z1(X1), —H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2allyl.
[0661] Table A12: Compounds (A12-1)-(A12-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2Ph.
[0662] Table A13: Compounds (A13-1)-(A13-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2-2(OMe)Ph.
[0663] Table A14: Compounds (A14-1)-(A14-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2-3-(OMe)Ph.
[0664] Table A15: Compounds (A15-1)-(A15-1920) are compounds of Formula I where X1, Z1(X1), —H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2-4-(OMe)-Ph.
[0665] Table A16: Compounds (A16-1)-(A16-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2-2(Me)Ph.
[0666] Table A17: Compounds (A17-1)-(A17-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2-3(Me)Ph.
[0667] Table A18: Compounds (A18-1)-(A18-1920) are compounds of Formula I where X1, Z1(X)m-H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2-4(Me)Ph.
[0668] Table A19: Compounds (A19-1)-(A19-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2-4(NO2)Ph.
[0669] Table A20: Compounds (A20-1)-(A20-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals Co2SiMe3.
[0670] Table A21: Compounds (A21-1)-(A21-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)Me.
[0671] Table A22: Compounds (A22-1)-(A22-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)NMe2.
[0672] Table A23: Compounds (A23-1)-(A23-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)NBn2.
[0673] Table A24: Compounds (A24-1)-(A24-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(Me)Bn.
[0674] Table A25: Compounds (A25-1)-(A25-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(Me)Ph.
[0675] Table A26: Compounds (A26-1)-(A26-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)Ph.
[0676] Table A27: Compounds (A27-1)-(A27-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)NMe2.
[0677] Table A28: Compounds (A28-1)-(A28-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals CO2n-octyl.
[0678] Table A29: Compounds (A29-1)-(A29-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)n-Bu.
[0679] Table A30: Compounds (A30-1)-(A30-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)N(H)CO2Et.
[0680] Table A31: Compounds (A31-1)-(A31-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)N(H)Co2t-Bu.
[0681] Table A32: Compounds (A32-1)-(A32-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)N═CHMe.
[0682] Table A33: Compounds (A33-1)-(A33-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)N═CMe2.
[0683] Table A34: Compounds (A34-1)-(A34-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table AI except for R1 which equals C(═O)N(H)N═CHPh.
[0684] Table A35: Compounds (A35-1)-(A35-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)SPh.
[0685] Table A36: Compounds (A36-1)-(A36-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G2′, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)SEt.
[0686] Table A37: Compounds (A37-1)-(A37-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G2′, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)Sn-Bu.
[0687] Table A38: Compounds (A38-1)-(A38-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)OMe.
[0688] Table A39: Compounds (A39-1)-(A39-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)OBn.
[0689] Table A40: Compounds (A40-1)-(A40-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)NH2.
[0690] Table A41: Compounds (A41-1)-(A41-1920) are compounds of Formula I where X1, Z1(X1)m—H, G10, G11, R2, G20, G21, m, t, q and Z2 are identical to those in Table A1 except for R1 which equals C(═O)N(H)OH.
[0691] Table B1 describes additional examples of compounds of Formula I which can be made using the procedures described hereinbefore, where R2 is hydrogen, m=0, q=1, t=0 or 1 and the pharmaceutical which defines the pharmaceutical moiety of these examples is Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2). The following groups, Z1, G10, G11, R1, G20, G21, t, X2 and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are defined within Table B1.
12TABLE B1
|
|
85
|
Z2(X2)q—[(C═G20)—
G21]t-H or when t = 0,
Cmpd#Z1G10G11R1G20G21tX2Z2(X2)q or Z2(X2)q—H
|
B1-1MeOOCO2H——0Nbisacodyl
B1-2cyclohexylOOCO2H——0Nbisacodyl
B1-3t-BuOOCO2H——0Nbisacodyl
B1-4CF3CH2OOCO2H——0Nbisacodyl
B1-5allylOOCO2H——0Nbisacodyl
B1-64-(NO2)PhOOCO2H——0Nbisacodyl
B1-7PhSOOCO2H——0Nbisacodyl
B1-8N(Me)PhOOCO2H——0Nbisacodyl
B1-9N(H)OMeOOCO2H——0Nbisacodyl
B1-10N(H)CO2EtOOCO2H——0Nbisacodyl
B1-11MeOOCO2H——0Nbupivacaine
B1-12cyclohexylOOCO2H——0Nbupivacaine
B1-13t-BuOOCO2H——0Nbupivacaine
B1-14CF3CH2OOCO2H——0Nbupivacaine
B1-15allylOOCO2H——0Nbupivacaine
B1-164-(NO2)PhOOCO2H——0Nbupivacaine
B1-17PhSOOCO2H——0Nbupivacaine
B1-18N(Me)PhOOCO2H——0Nbupivacaine
B1-19N(H)OMeOOCO2H——0Nbupivacaine
B1-20N(H)CO2EtOOCO2H——0Nbupivacaine
B1-21MeOOCO2H——0Nchloroprocaine
B1-22cyclohexylOOCO2H——0Nchloroprocaine
B1-23t-BuOOCO2H——0Nchloroprocaine
B1-24CF3CH2OOCO2H——0Nchloroprocaine
B1-25allylOOCO2H——0Nchloroprocaine
B1-264-(NO2)PhOOCO2H——0Nchloroprocaine
B1-27PhSOOCO2H——0Nchloroprocaine
B1-28N(Me)PhOOCO2H——0Nchloroprocaine
B1-29N(H)OMeOOCO2H——0Nchloroprocaine
B1-30N(H)CO2EtOOCO2H——0Nchloroprocaine
B1-31MeOOCO2H——0Ntetracaine
B1-32cyclohexylOOCO2H——0Ntetracaine
B1-33t-BuOOCO2H——0Ntetracaine
B1-34CF3CH2OOCO2H——0Ntetracaine
B1-35allylOOCO2H——0Ntetracaine
B1-364-(NO2)PhOOCO2H——0Ntetracaine
B1-37PhSOOCO2H——0Ntetracaine
B1-38N(Me)PhOOCO2H——0Ntetracaine
B1-39N(H)OMeOOCO2H——0Ntetracaine
B1-40N(H)CO2EtOOCO2H——0Ntetracaine
B1-41MeOOCO2H——0Nacrivistine
B1-42cyclohexylOOCO2H——0Nacrivistine
B1-43t-BuOOCO2H——0Nacrivistine
B1-44CF3CH2OOCO2H——0Nacrivistine
B1-45allylOOCO2H——0Nacrivistine
B1-464-(NO2)PhOOCO2H——0Nacrivistine
B1-47PhSOOCO2H——0Nacrivistine
B1-48N(Me)PhOOCO2H——0Nacrivistine
B1-49N(H)OMeOOCO2H——0Nacrivistine
B1-50N(H)CO2EtOOCO2H——0Nacrivistine
B1-51MeOOCO2H——0Namiodarone
B1-52cyclohexylOOCO2H——0Namiodarone
B1-53t-BuOOCO2H——0Namiodarone
B1-54CF3CH2OOCO2H——0Namiodarone
B1-55allylOOCO2H——0Namiodarone
B1-564-(NO2)PhOOCO2H——0Namiodarone
B1-57PhSOOCO2H——0Namiodarone
B1-58N(Me)PhOOCO2H——0Namiodarone
B1-59N(H)OMeOOGO2H——0Namiodarone
B1-60N(H)CO2EtOOCO2H——0Namiodarone
B1-61MeOOCO2H——0Namitriptyline
B1-62cyclohexylOOCO2H——0Namitriptyline
B1-63t-BuOOCO2H——0Namitriptyline
B1-64CF3CH2OOCO2H——0Namitriptyline
B1-65allylOOCO2H——0Namitriptylme
B1-664-(NO2)PhOOCO2H——0Namitriptyline
B1-67PhSOOCO2H——0Namitriptyline
B1-68N(Me)PhOOCO2H——0Namitriptyline
B1-69N(H)OMeOOCO2H——0Namitriptyline
B1-70N(H)CO2EtOOCO2H——0Namitriptyline
B1-71MeOOCO2H——0Namrinone
B1-72cyclohexylOOCO2H——0Namrinone
B1-73t-BuOOCO2H——0Namrinone
B1-74CF3CH2OOCO2H——0Namrinone
B1-75allylOOCO2H——0Namrinone
B1-764-(NO2)PhOOCO2H——0Namrinone
B1-77PhSOOCO2H——0Namrinone
B1-78N(Me)PhOOCO2H——0Namrinone
B1-79N(H)OMeOOCO2H——0Namrinone
B1-80N(H)CO2EtOOCO2H——0Namrinone
B1-81MeOOCO2H——0Natropine
B1-82cyclohexylOOCO2H——0Natropine
B1-83t-BuOOCO2H——0Natropine
B1-84CF3CH2OOCO2H——0Natropine
B1-85allylOOCO2H——0Natropine
B1-864-(NO2)PhOOCO2H——0Natropine
B1-87PhSOOCO2H——0Natropine
BL-88N(Me)PhOOCO2H——0Natropine
B1-89N(H)OMeOOCO2H——0Natropine
B1-90N(H)CO2EtOOCO2H——0Natropine
B1-91MeOOCO2H——0Nbenzphetamine
B1-92cyclohexylOO00211——0Nbenzphetamine
B1-93t-BuOOCO2H——0Nbenzphetamine
B1-94CF3CH2OOCO2H——0Nbenzphetamine
B1-95allylOOCO2H——0Nbenzphetamine
B1-964-(NO2)PhOOCO2H——0Nbenzphetamine
B1-97PhSOOCO2H——0Nbenzphetamine
B1-98N(Me)PhOOCO2H——0Nbenzphetamine
B1-99N(H)OMeOOCO2H——0Nbenzphetamine
B1-100N(H)CO2EtOOCO2H——0Nbenzphetamine
B1-101MeOOCO2H——0Nbeperiden
B1-102cyclohexylOOCO2H——0Nbeperiden
B1-103t-BuOOCO2H——0Nbeperiden
B1-104CF3CH2OOCO2H——0Nbeperiden
B1-105allylOOCO2H——0Nbeperiden
B1-1064-(NO2)PhOOCO2H——0Nbeperiden
B1-107PhSOOCO2H——0Nbeperiden
B1-108N(Me)PhOOCO2H——0Nbeperiden
B1-109N(H)OMeOOCO2H——0Nbeperiden
B1-110N(H)CO2EtOOCO2H——0Nbeperiden
B1-111MeOOCO2H——0Nbromopheniramine
B1-112cyclohexylOOCO2H——0Nbromopheniramine
B1-113t-BuOOCO2H——0Nbromopheniramine
B1-114CF3CH2OOCO2H——0Nbromopheniramine
B1-115allylOOCO2H——0Nbromopheniramine
B1-1164-(NO2)PhOOCO2H——0Nbromopheniramine
B1-117PhSOOCO2H——0Nbromopheniramine
B1-118N(Me)PhOOCO2H——0Nbromopheniramine
B1-119N(H)OMeOOCO2H——0Nbromopheniramine
B1-120N(H)CO2EtOOCO2H——0Nbromopheniramine
B1-121MeOOCO2H——0Nclemastine
B1-122cyclohexylOOCO2H——0Nclemastine
B1-123t-BuOOCO2H——0Nclemastine
B1-124CF3CH2OOCO2H——0Nclemastine
B1-125allylOOCO2H——0Nclemastine
B1-1264-(NO2)PhOOCO2H——0Nclemastine
B1-127PhSOOCO2H——0Nclemastine
B1-128N(Me)Ph00CO2H——0Nclemastine
B1-129N(H)OMeOOCO2H——0Nclemastine
B1-130N(H)CO2EtOOCO2H——0Nclemastine
B1-131MeOOCO2H——0Nclomiphene
B1-132cyclohexylOOCO2H——0Nclomiphene
B1-133t-BuOOCO2H——0Nclomiphene
B1-134CF3CH2OOCO2H——0Nclomiphene
B1-135allylOOCO2H——0Nclomiphene
B1-1364-(NO2)PhOOCO2H——0Nclomiphene
B1-137PhSOOCO2H——0Nclomiphene
B1-138N(Me)PhOOCO2H——0Nclomiphene
B1-139N(H)OMeOOCO2H——0Nclomiphene
B1-140N(H)CO2EtOOCO2H——0Nclomiphene
B1-141MeOOCO2H——0Ncyclobenzaprine
B1-142cyclohexylOOCO2H——0Ncyclobenzaprine
B1-143t-BuOOCO2H——0Ncyclobenzaprine
B1-144CF3CH2OOCO2H——0Ncyclobenzaprine
B1-145allylOOCO2H——0Ncyclobenzaprine
B1-1464-(NO2)PhOOCO2H——0Ncyclobenzaprine
B1-147PhSOOCO2H——0Ncyclobenzaprine
B1-148N(Me)PhOOCO2H——0Ncyclobenzaprine
B1-149N(H)OMeOOCO2H——0Ncyclobenzaprine
B1-150N(H)CO2EtOOCO2H——0Ncyclobenzaprine
B1-151MeOOCO2H——0Ncyclopentolate
B1-152cyclohexylOOCO2H——0Ncyclopentolate
B1-153t-BuOOCO2H——0Ncyclopentolate
B1-154CF3CH2OOCO2H——0Ncyclopentolate
B1-155allylOOCO2H——0Ncyclopentolate
B1-1564-(NO2)PhOOCO2H——0Ncyclopentolate
B1-157PhSOOCO2H——0Ncyclopentolate
B1-158N(Me)PhOOCO2H——0Ncyclopentolate
B1-159N(H)OMeOOCO2H——0Ncyclopentolate
B1-160N(H)CO2EtOOCO2H——0Ncyclopentolate
B1-161MeOOCO2H——0Ndicyclomine
B1-162cyclohexylOOCO2H——0Ndicyclomine
B1-163t-BuOOCO2H——0Ndicyclomine
B1-164CF3CH2OOCO2H——0Ndicyclomine
B1-165allylOOCO2H——0Ndicyclomine
B1-1664-(NO2)PhOOCO2H——0Ndicyclomine
B1-167PhSOOCO2H——0Ndicyclomine
B1-168N(Me)PhOOCO2H——0Ndicyclomine
B1-169N(H)OMeOOCO2H——0Ndicyclomine
B1-170N(H)CO2EtOOCO2H——0Ndicyclomine
B1-171MeOOCO2H——0Ndiethylproprion
B1-172cyclohexylOOCO2H——0Ndiethylproprion
B1-173t-BuOOCO2H——0Ndiethylproprion
B1-174CF3CH2OOCO2H——0Ndiethylproprion
B1-175allylOOCO2H——0Ndiethylproprion
B1-1764-(NO2)PhOOCO2H——0Ndiethylproprion
B1-177PhSOOCO2H——0Ndiethylproprion
B1-178N(Me)PhOOCO2H——0Ndiethylproprion
B1-179N(H)OMeOOCO2H——0Ndiethylproprion
B1-180N(H)CO2EtOOCO2H——0Ndiethylproprion
B1-181MeOOCO2H——0Ndiltiazem
B1-182cyclohexylOOCO2H——0Ndiltiazem
B1-183t-BuOOCO2H——0Ndiltiazem
B1-184CF3CH2OOCO2H——0Ndiltiazem
B1-185allylOOCO2H——0Ndiltiazem
B1-1864-(NO2)PhOOCO2H——0Ndiltiazem
B1-187PhSOOCO2H——0Ndiltiazem
B1-188N(Me)PhOOCO2H——0Ndiltiazem
B1-189N(H)OMeOOCO2H——0Ndiltiazem
B1-190N(H)CO2EtOOCO2H——0Ndiltiazem
B1-191MeOOCO2H——0Ndiphenhydramine
B1-192cyclohexylOOCO2H——0Ndiphenhydramine
B1-193t-BuOOCO2H——0Ndiphenhydramine
B1-194CF3CH2OOCO2H——0Ndiphenhydramine
B1-195allylOOCO2H——0Ndiphenhydramine
B1-1964-(NO2)PhOOCO2H——0Ndiphenhydramine
B1-197PhSOOCO2H——0Ndiphenhydramine
B1-198N(Me)PhOOCO2H——0Ndiphenhydramine
B1-199N(H)OMeOOCO2H——0Ndiphenhydramine
B1-200N(H)CO2EtOOCO2H——0Ndiphenhydramine
B1-201MeOOCO2H——0Ndiphenidol
B1-202cyclohexylOOCO2H——0Ndiphenidol
B1-203t-BuOOCO2H——0Ndiphenidol
B1-204CF3CH2OOCO2H——0Ndiphenidol
B1-205allylOOCO2H——0Ndiphenidol
B1-2064-(NO2)PhOOCO2H——0Ndiphenidol
B1-207PhSOOCO2H——0Ndiphenidol
B1-208N(Me)PhOOCO2H——0Ndiphenidol
B1-209N(H)OMeOOCO2H——0Ndiphenidol
B1-210N(H)CO2EtOOCO2H——0Ndiphenidol
B1-211MeOOCO2H——0Ndiphenoxylate
B1-212cyclohexylOOCO2H——0Ndiphenoxylate
B1-213t-BuOOCO2H——0Ndiphenoxylate
B1-214CF3CH2OOCO2H——0Ndiphenoxylate
B1-215allylOOCO2H——0Ndiphenoxylate
B1-2164-(NO2)PhOOCO2H——0Ndiphenoxylate
B1-217PhSOOCO2H——0Ndiphenoxylate
B1-218N(Me)PhOOCO2H——0Ndiphenoxylate
B1-219N(H)OMeOOCO2H——0Ndiphenoxylate
B1-220N(H)CO2EtOOCO2H——0Ndiphenoxylate
B1-221MeOOCO2H——0Ndoxapram
B1-222cyclohexylOOCO2H——0Ndoxapram
B1-223t-BuOOCO2H——0Ndoxapram
B1-224CF3CH2OOCO2H——0Ndoxapram
B1-225allylOOCO2H——0Ndoxapram
B1-2264-(NO2)PhOOCO2H——0Ndoxapram
B1-227PhSOOCO2H——0Ndoxapram
B1-228N(Me)PhOOCO2H——0Ndoxapram
B1-229N(H)OMeOOCO2H——0Ndoxapram
B1-230N(H)CO2EtOOCO2H——0Ndoxapram
B1-231MeOOCO2H——0Ndoxepin
B1-232cyclohexylOOCO2H——0Ndoxepin
B1-233t-BuOOCO2H——0Ndoxepin
B1-234CF3CH2OOCO2H——0Ndoxepin
B1-235allylOOCO2H——0Ndoxepin
B1-2364-(NO2)PhOOCO2H——0Ndoxepin
B1-237PhSOOCO2H——0Ndoxepin
B1-238N(Me)PhOOCO2H——0Ndoxepin
B1-239N(H)OMeOOCO2H——0Ndoxepin
B1-240N(H)CO2EtOOCO2H——0Ndoxepin
B1-241MeOOCO2H——0Nfentanyl
B1-242cyclohexylOOCO2H——0Nfentanyl
B1-243t-BuOOCO2H——0Nfentanyl
B1-244CF3CH2OOCO2H——0Nfentanyl
B1-245allylOOCO2H——0Nfentanyl
B1-2464-(NO2)PhOOCO2H——0Nfentanyl
B1-247PhSOOCO2H——0Nfentanyl
B1-248N(Me)PhOOCO2H——0Nfentanyl
B1-249N(H)OMeOOCO2H——0Nfentanyl
B1-250N(H)CO2EtOOCO2H——0Nfentanyl
B1-251MeOOCO2H——0Nflavoxate
B1-252cyclohexylOOCO2H——0Nflavoxate
B1-253t-BuOOCO2H——0Nflavoxate
B1-254CF3CH2OOCO2H——0Nflavoxate
B1-255allylOOCO2H——0Nflavoxate
B1-2564-(NO2)PhOOCO2H——0Nflavoxate
B1-257PhSOOCO2H——0Nflavoxate
B1-258N(Me)PhOOCO2H——0Nflavoxate
B1-259N(H)OMeOOCO2H——0Nflavoxate
B1-260N(H)CO2EtOOCO2H——0Nflavoxate
B1-261MeOOCO2H——0Nflurazepam
B1-262cyclohexylOOCO2H——0Nflurazepam
B1-263t-BuOOCO2H——0Nflurazepam
B1-264CF3CH2OOCO2H——0Nflurazepam
B1-265allylOOCO2H——0Nflurazepam
B1-2664-(NO2)PhOOCO2H——0Nflurazepam
B1-267PhSOOCO2H——0Nflurazepam
B1-268N(Me)PhOOCO2H——0Nflurazepam
B1-269N(H)OMeOOCO2H——0Nflurazepam
B1-270N(H)CO2EtOOCO2H——0Nflurazepam
B1-271MeOOCO2H——0Nlevomethadyl
B1-272cyclohexylOOCO2H——0Nlevomethadyl
B1-273t-BuOOCO2H——0Nlevomethadyl
B1-274CF3CH2OOCO2H——0Nlevomethadyl
B1-275allylOOCO2H——0Nlevomethadyl
B1-2764-(NO2)PhOOCO2H——0Nlevomethadyl
B1-277PhSOOCO2H——0Nlevomethadyl
B1-278N(Me)PhOOCO2H——0Nlevomethadyl
B1-279N(H)OMeOOCO2H——0Nlevomethadyl
B1-280N(H)CO2EtOOCO2H——0Nlevomethadyl
B1-281MeOOCO2H——0Nloratadine
B1-282cyclohexylOOCO2H——0Nloratadine
B1-283t-BuOOCO2H——0Nloratadine
B1-284CF3CH2OOCO2H——0Nloratadine
B1-285allylOOCO2H——0Nloratadine
B1-2864-(NO2)PhOOCO2H——0Nloratadine
B1-287PhSOOCO2H——0Nloratadine
B1-288N(Me)PhOOCO2H——0Nloratadine
B1-289N(H~OMeOOCO2H——0Nloratadine
B1-290N(H)CO2EtOOCOdI——0Nloratadine
B1-291MeOOCO2H——0Nmechlorethamine
B1-292cyclohexylOOCO2H——0Nmechlorethamine
B1-293t-BuOOCO2H——0Nmechlorethamine
B1-294CF3CH2OOCO2H——0Nmechlorethamine
B1-295allylOOCO2H——0Nmechlorethamine
B1-2964-(NO2)PhOOCO2H——0Nmechlorethamine
B1-297PhSOOCO2H——0Nmechlorethamine
B1-298N(Me)PhOOCO2H——0Nmechlorethamine
B1-299N(H)OMeOOCO2H——0Nmechlorethamine
B1-300N(H)CO2EtOOCO2H——0Nmechlorethamine
B1-301MeOOCO2H——0Nmeperidine
B1-302cyclohexylOOCO2H——0Nmeperidine
B1-303t-BuOOCO2H——0Nmeperidine
B1-304CF3CH2OOCOdI——0Nmeperidine
B1-305allylOOCO2H——0Nmeperidine
B1-3064-(NO2)PhOOCO2H——0Nmeperidine
B1-307PhSOOCO2H——0Nmeperidine
B1-308N(Me)PhOOCO2H——0Nmeperidine
B1-309N(H)OMeOOCO2H——0Nmeperidine
B1-310N(H)CO2EtOOCO2H——0Nmeperidine
B1-311MeOOCO2H——0Nmepivacaine
B1-312cyclohexylOOCO2H——0Nmepivacaine
B1-313t-BuOOCO2H——0Nmepivacaine
B1-314CF3CH2OOCO2H——0Nmepivacaine
B1-315allylOOCO2H——0Nmepivacaine
B1-3164-(NO2)PhOOCO2H——0Nmepivacaine
B1-317PhSOOCO2H——0Nmepivacaine
B1-318N(Me)PhOOCO2H——0Nmepivacaine
B1-319N(H)OMeOOCO2H——0Nmepivacaine
B1-320N(H)CO2EtOOCO2H——0Nmepivacaine
B1-321MeOOCO2H——0Nmethadone
B1-322cyclohexylOOCO2H——0Nmethadone
B1-323t-BuOOCO2H——0Nmethadone
B1-324CF3CH2OOCO2H——0Nmethadone
B1-325allylOOCO2H——0Nmethadone
B1-3264-(NO2)PhOOCO2H——0Nmethadone
B1-327PhSOOCO2H——0Nmethadone
B1-328N(Me)PhOOCO2H——0Nmethadone
B1-329N(H)OMeOOCO2H——0Nmethadone
B1-330N(H)CO2EtOOCO2H——0Nmethadone
B1-331MeOOCO2H——0Nminoxidil
B1-332cyclohexylOOCO2H——0Nminoxidil
B1-333t-BuOOCO2H——0Nminoxidil
B1-334CF3CH2OOCO2H——0Nminoxidil
B1-335allylOOCO2H——0Nminoxidil
B1-3364-(NO2)PhOOCO2H——0Nminoxidil
B1-337PhSOOCO2H——0Nminoxidil
B1-338N(Me)PhOOCO2H——0Nminoxidil
B1-339N(H)OMeOOCO2H——0Nminoxidil
B1-340N(H)CO2EtOOCO2H——0Nminoxidil
B1-341MeOOCO2H——0Nnaftifine
B1-342cyclohexylOOCO2H——0Nnaftifine
B1-343t-BuOOCO2H——0Nnaftifine
B1-344CF3CH2OOCO2H——0Nnaftifine
B1-345allylOOCO2H——0Nnaftifine
B1-3464-(NO2)PhOOCO2H——0Nnaftifine
B1-347PhSOOCO2H——0Nnaftifine
B1-348N(Me)PhOOCO2H——0Nnaftifine
B1-349N(H)OMeOOCO2H——0Nnaftifine
B1-350N(H)CO2EtOOCO2H——0Nnaftifine
B1-351MeOOCO2H——0Norphenadrine
B1-352cyclohexylOOCO2H——0Norphenadrine
B1-353t-BuOOCO2H——0Norphenadrine
B1-354CF3CH2OOCO2H——0Norphenadrine
B1-355ally1OOCO2H——0Norphenadrine
B1-3564-(NO2)PhOOCO2H——0Norphenadrine
B1-357PhSOOCO2H——0Norphenadrine
B1-358N(Me)PhOOCO2H——0Norphenadrine
B1-359N(H)OMeOOCO2H——0Norphenadrine
B1-360N(H)CO2EtOOCO2H——0Norphenadrine
B1-361MeOOCO2H——0Noxybutynin
B1-362cyclohexylOOCO2H——0Noxybutynin
B1-363t-BuOOCO2H——0Noxybutynin
B1-364CF3CH2OOCO2H——0Noxybutynin
B1-365allylOOCO2H——0Noxybutynin
B1-3664-(NO2)PhOOCO2H——0Noxybutynin
B1-367PhSOOCO2H——0Noxybutynin
B1-368N(Me)PhOOCO2H——0Noxybutynin
B1-369N(H)OMeOOCO2H——0Noxybutynin
B1-370N(H)CO2EtOOCO2H——0Noxybutynin
B1-371MeOOCO2H——0Noxymetazoline
B1-372cyclohexylOOCO2H——0Noxymetazohne
B1-373t-BuOOCQ2H——0Noxymetazoline
B1-374CF3CH2OOCO2H——0Noxymetazoline
B1-375allylOOCO2H——0Noxymetazoline
B1-3764-(NO2)PhOOCO2H——0Noxymetazoline
B1-377PhSOOCO2H——0Noxymetazoline
B1-378N(Me)PhOOCO2H——0Noxymetazoline
B1-379N(H)OMeOOCO2H——0Noxymetazoline
B1-380N(H)CO2EtOOCO2H——0Noxymetazoline
B1-381MeOOCO2H——0Nphenoxybenzamine
B1-382cyclohexylOOCO2H——0Nphenoxybenzamine
B1-383t-BuOOCO2H——0Nphenoxybenzamine
B1-384CF3CH2OOCO2H——0Nphenoxybenzamine
B1-385allylOOCO2H——0Nphenoxybenzamine
B1-3864-(NO2)PhOOCO2H——0Nphenoxybenzamine
B1-387PhSOOCO2H——0Nphenoxybenzamine
B1-388N(Me)PhOOCO2H——0Nphenoxybenzamine
B1-389N(H)OMeOOCO2H——0Nphenoxybenzamine
B1-390N(H)CO2EtOOCO2H——0Nphenoxybenzamine
B1-391MeOOCO2H——0Npilocarpine
B1-392cyclohexylOOCO2H——0Npilocarpine
B1-393t-BuOOCO2H——0Npilocarpine
B1-394CF3CH2OOCO2H——0Npilocarpine
B1-395allylOOCO2H——0Npilocarpine
B1-3964-(NO2)PhOOCO2H——0Npilocarpine
B1-397PhSOOCO2H——0Npilocarpine
B1-398N(Me)PhOOCO2H——0Npilocarpine
B1-399N(H)OMeOOCO2H——0Npilocarpine
B1-400N(H)CO2EtOOCO2H——0Npilocarpine
B1-401MeOOCO2H——0Npyrazinamide
B1-402cyclohexylOOCO2H——0Npyrazinamide
B1-403t-BuOOCO2H——0Npyrazinamide
B1-404CF3CH2OOCO2H——0Npyrazinamide
B1-405allylOOCO2H——0Npyrazinamide
B1-4064-(NO2)PhOOCO2H——0Npyrazinamide
B1-407PhSOOCO2H——0Npyrazinamide
B1-408N(Me)PhOOCO2H——0Npyrazinamide
B1-409N(H)OMeOOCO2H——0Npyrazinamide
B1-410N(H)CO2EtOOCO2H——0Npyrazinamide
B1-411MeOOCO2H——0Npyroxidine
B1-412cyclohexylOOCO2H——0Npyroxidine
BL-413t-BuOOCO2H——0Npyroxidine
B1-414CF3CH2OOCO2H——0Npyroxidine
B1-415allylOOCO2H——0Npyroxidine
B1-4164-(NO2)PhOOCO2H——0Npyroxidine
B1-417PhSOOCO2H——0Npyroxidine
B1-418N(Me)PhOOCO2H——0Npyroxidine
B1-419N(H)OMeOOCO2H——0Npyroxidine
B1-420N(H)CO2EtOOCO2H——0Npyroxidine
BL-421MeOOCO2H——0Nrisperidone
B1-422cyclohexylOOCO2H——0Nrisperidone
B1-423t-BuOOCO2H——0Nrisperidone
B1-424CF3CH2OOCO2H——0Nrisperidone
B1-425allylOOCO2H——0Nrisperidone
B1-4264-(NO2)PhOOCO2H——0Nrisperidone
B1-427PhSOOCO2H——0Nrisperidone
B1-428N(Me)PhOOCO2H——0Nrisperidone
B1-429N(H)OMeOOCO2H——0Nrisperidone
B1-430N(H)CO2EtOOCO2H——0Nrisperidone
BL-431MeOOCO2H——0Nsufentanil
B1-432cyclohexylOOCO2H——0Nsufentanil
B1-433t-BuOOCO2H——0Nsufentanil
B1-434CF3CH2OOCO2H——0Nsufentanil
B1-435allylOOCO2H——0Nsufentanil
B1-4364-(NO2)PhOOCO2H——0Nsufentanil
B1-437PhSOOCO2H——0Nsufentanil
B1-438N(Me)PhOOCO2H——0Nsufentanil
B1-439N(H)OMeOOCO2H——0Nsufentanil
B1-440N(H)CO2EtOOCO2H——0Nsufentanil
B1-441MeOOCO2H——0Ntamoxifen
B1-442cyclohexylOOCO2H——0Ntamoxifen
B1-443t-BuOOCO2H——0Ntamoxifen
B1-444CF3CH2OOCO2H——0Ntamoxifen
B1-445allylOOCO2H——0Ntamoxifen
B1-4464-(NO2)PhOOCO2H——0Ntamoxifen
B1-447PhSOOCO2H——0Ntamoxifen
B1-448N(Me)PhOOCO2H——0Ntamoxifen
B1-449N(H)OMeOOCO2H——0Ntamoxifen
B1-450N(H)CO2EtOOCO2H——0Ntamoxifen
B1-451MeOOCO2H——0Nterbinafine
B1-452cyclohexylOOCO2H——0Nterbinafine
B1-453t-BuOOCO2H——0Nterbinafine
B1-454CF3CH2OOCO2H——0Nterbinafine
B1-455allylOOCO2H——0Nterbinafine
B1-4564-(NO2)PhOOCO2H——0Nterbinafine
B1-457PhSOOCO2H——0Nterbinafine
B1-458N(Me)PhOOCO2H——0Nterbinafine
B1-459N(H)OMeOOCO2H——0Nterbinafine
B1-460N(H)CO2EtOOCO2H——0Nterbinafine
B1-461MeOOCO2H——0Ntrihexyphenidyl
B1-462cyclohexylOOCO2H——0Ntrihexyphenidyl
B1-463t-BuOOCO2H——0Ntrihexyphenidyl
B1-464CF3CH2OOCO2H——0Ntrihexyphenidyl
B1-465allylOOCO2H——0Ntrihexyphenidyl
B1-4664-(NO2)PhOOCO2H——0Ntrihexyphenidyl
B1-467PhSOOCO2H——0Ntrihexyphenidyl
B1-468N(Me)PhOOCO2H——0Ntrihexyphenidyl
B1-469N(H)OMeOOCO2H——0Ntrihexyphenidyl
B1-470N(H)CO2EtOOCO2H——0Ntrihexyphenidyl
B1-471Me OOCO2H——0Ntroleandomycin
B1-472cyclohexylOOCO2H——0Ntroleandomycin
B1-473t-BuOOCO2H——0Ntroleandomycin
B1-474CF3CH2OOCO2H——0Ntroleandomycin
B1-475allylOOCO2H——0Ntroleandomycin
B1-4764-(NO2)PhOOCO2H——0Ntroleandomycin
B1-477PhSOOCO2H——0Ntroleandomycin
B1-478N(Me)PhOOCO2H——0Ntroleandomycin
B1-479N(H)OMeOOCO2H——0Ntroleandomycin
B1-480N(H)CO2EtOOCO2H——0Ntroleandomycin
B1-481MeOOCO2H——0Nverapamil
B1-482cyclohexylOOCO2H——0Nverapamil
B1-483t-BuOOCO2H——0Nverapamil
B1-484CF3CH2OOCO2H——0Nverapamil
B1-485allylOOCO2H——0Nverapamil
B1-4864-(NO2)PhOOCO2H——0Nverapamil
B1-487PhSOOCO2H——0Nverapamil
B1-488N(Me)PhOOCO2H——0Nverapamil
B1-489N(H)OMeOOCO2H——0Nverapamil
B1-490N(H)CO2EtOOCO2H——0Nverapamil
B1-491MeOOCO2H——0Ncaffeine
B1-492cyclohexylOOCO2H——0Ncaffeine
B1-493t-BuOOCO2H——0Ncaffeine
B1-494CF3CH2OOCO2H——0Ncaffeine
B1-495allylOOCO2H——0Ncaffeine
B1-4964-(NO2)PhOOCO2H——0Ncaffeine
B1-497PhSOOCO2H——0Ncaffeine
B1-498N(Me)PhOOCO2H——0Ncaffeine
B1-499N(H)OMeOOCO2H——0Ncaffeine
B1-500N(H)CO2EtOOCO2H——0Ncaffeine
B1-501MeOOCO2H——0Ncyproheptadine
B1-502cyclohexylOOCO2H——0Ncyproheptadine
B1-503t-BuOOCO2H——0Ncyproheptadine
B1-504CF3CH2OOCO2H——0Ncyproheptadine
B1-505allylOOCO2H——0Ncyproheptadine
B1-5064-(NO2)PhOOCO2H——0Ncyproheptadine
B1-507PhSOOCO2H——0Ncyproheptadine
B1-508N(Me)PhOOCO2H——0Ncyproheptadine
B1-509N(H)OMeOOCO2H——0Ncyproheptadine
B1-510N(H)CO2EtOOCO2H——0Ncyproheptadine
B1-511MeOOCO2H——0Npramoxine
B1-512cyclohexylOOCO2H——0Npramoxine
B1-513t-BuOOCO2H——0Npramoxine
B1-514CF3CH2OOCO2H——0Npramoxine
B1-515allylOOCO2H——0Npramoxine
B1-5164-(NO2)PhOOCO2H——0Npramoxine
B1-517PhSOOCO2H——0Npraniioxine
B1-518N(Me)PhOOCO2H——0Npramoxine
B1-519N(H)OMeOOCO2H——0Npramoxine
B1-520N(H)CO2EtOOCO2H——0Npramoxine
B1-521MeOOCO2H——0Oiodoquinol
B1-522cyclohexylOOCO2H——0Oiodoquinol
B1-523t-BuOOCO2H——0Oiodoquinol
B1-524CF3CH2OOCO2H——0Oiodoquinol
B1-525allylOOCO2H——0Oiodoquinol
B1-5264-(NO2)PhOOCO2H——0Oiodoquinol
B1-527PhSOOCO2H——0Oiodoquinol
B1-528N(Me)PhOOCO2H——0Oiodoquinol
B1-529N(H)OMeOOCO2H——0Oiodoquinol
B1-530N(H)CO2EtOOCO2H——0Oiodoquinol
B1-531MeOOCO2H——0Ometronidazole
B1-532cyclohexylOOCO2H——0Ometronidazole
B1-533t-BuOOCO2H——0Ometronidazole
B1-534CF3CH2OOCO2H——0Ometronidazole
B1-535allylOOCO2H——0Ometronidazole
B1-5364-(NO2)PhOOCO2H——0Ometronidazole
B1-537PhSOOCO2H——0Ometronidazole
B1-538N(Me)PhOOCO2H——0Ometronidazole
B1-539N(H)OMeOOCO2H——0Ometronidazole
B1-540N(H)CO2EtOOCO2H——0Ometronidazole
B1-541MeOOCO2H——0Npapaverine
B1-542cyclohexylOOCO2H——0Npapaverine
B1-543t-BuOOCO2H——0Npapaverine
B1-544CF3CH2OOCO2H——0Npapaverine
B1-545allylOOCO2H——0Npapaverine
B1-5464-(NO2)PhOOCO2H——0Npapaverine
B1-547PhSOOCO2H——0Npapaverine
B1-548N(Me)PhOOCO2H——0Npapaverine
B1-549N(H)OMeOOCO2H——0Npapaverine
B1-550N(H)CO2EtOOCO2H——0Npapaverine
B1-551MeOOCO2H——0Ntropicamide
B1-552cyclohexylOOCO2H——0Ntropicamide
B1-553t-BuOOCO2H——0Ntropicamide
B1-554CF3CH2OOCO2H——0Ntropicamide
B1-555allyLOOCO2H——0Ntropicamide
B1-5564-(NO2)PhOOCO2H——0Ntropicamide
B1-557PhSOOCO2H——0Ntropicamide
B1-558N(Me)PhOOCO2H——0Ntropicamide
B1-559N(H)OMeOOCO2H——0Ntropicamide
B1-560N(H)CO2EtOOCO2H——0Ntropicamide
B1-561MeOOCO2H——0Nhalazepam
B1-562cyclohexylOOCO2H——0Nhalazepam
B1-563t-BuOOCO2H——0Nhalazepam
B1-564CF3CH2OOCO2H——0Nhalazepam
B1-565allylOOCO2H——0Nhalazepam
B1-5664-(NO2)PhOOCO2H——0Nhalazepam
B1-567PhSOOCO2H——0Nhalazepam
B1-568N(Me)PhOOCO2H——0Nhalazepam
B1-569N(H)OMeOOCO2H——0Nhalazepam
B1-570N(H)CO2EtOOCO2H——0Nhalazepam
B1-571MeOOCO2H——0Omazindol
B1-572cyclohexylOOCO2H——0Omazindol
B1-573t-BuOOCO2H——0Omazindol
B1-574CF3CH2OOCO2H——0Omazindol
B1-575allylOOCO2H——0Omazindol
B1-5764-(NO2)PhOOCO2H——0Omazindol
B1-577PhSOOCO2H——0Omazindol
B1-578N(Me)PhOOCO2H——0Omazindol
B1-579N(H)OMeOOCO2H——0Omazindol
B1-580N(H)CO2EtOOCO2H——0Omazindol
B1-581MeOOCO2H——0Ohydroxyitraconazole
B1-582cyclohexylOOCO2H——0Ohydroxyitraconazole
B1-583t-BuOOCO2H——0Ohydroxyitraconazole
B1-584CF3CH2OOCO2H——0Ohydroxyitraconazole
B1-585allylOOCO2H——0Ohydroxyitraconazole
B1-5864-(NO2)PhOOCO2H——0Ohydroxyitraconazole
B1-587PhSOOCO2H——0Ohydroxyitraconazole
B1-588N(Me)PhOOCO2H——0Ohydroxyitraconazole
B1-589N(H)OMeOOCO2H——0Ohydroxyitraconazole
B1-590N(H)CO2EtOOCO2H——0Ohydroxyitraconazole
B1-591MeOOCO2H——0Oposaconazole
B1-593t-BuOOCO2H——0Oposaconazole
B1-594CF3CH2OOCOdI——0Oposaconazole
B1-595allylOOCO2H——0Oposaconazole
B1-5964-(NO2)PhOOCO2H——0Oposaconazole
B1-597PhSOOCO2H——0Oposaconazole
B1-598N(Me)PhOOCO2H——0Oposaconazole
B1-599N(H)OMeOOCO2H——0Oposaconazole
B1-600N(H)CO2EtOOCO2H——0Oposaconazole
B1-601MeOOCO2H——0Ovoriconazole
B1-602cyclohexylOOCO2H——0Ovoriconazole
B1-603t-BuOOCO2H——0Ovoriconazole
B1-604CF3CH2OOCO2H——0Ovoriconazole
B1-605allylOOCO2H——0Ovoriconazole
B1-6064-(NO2)PhOOCO2H——0Ovoriconazole
B1-607PhSOOCO2H——0Ovoriconazole
B1-608N(Me)PhOOCO2H——0Ovoriconazole
B1-609N(H)OMeOOCO2H——0Ovoriconazole
B1-610N(H)CO2EtOOCO2H——0Ovoriconazole
B1-611MeOOCO2H——0Ofluconazole
B1-612cyclohexylOOCO2H——0Ofluconazole
B1-613t-BuOOCO2H——0Ofluconazole
B1-614CF3CH2OOCO2H——0Ofluconazole
B1-615allylOOCO2H——0Ofluconazole
B1-6164-(NO2)PhOOCO2H——0Ofluconazole
B1-617PhSOOCO2H——0Ofluconazole
B1-618N(Me)PhOOCO2H——0Ofluconazole
B1-619N(H)OMeOOCO2H——0Ofluconazole
B1-620N(H)CO2EtOOCO2H——0Ofluconazole
B1-621MeOOCO2H——0Ogenaconazole
B1-622cyclohexylOOCO2H——0Ogenaconazole
B1-623t-BuOOCO2H——0Ogenaconazole
B1-624CF3CH2OOCO2H——0Ogenaconazole
B1-625allylOOCO2H——0Ogenaconazole
B1-6264-(NO2)PhOOCO2H——0Ogenaconazole
B1-627PhSOOCO2H——0Ogenaconazole
B1-628N(Me)PhOOCO2H——0Ogenaconazole
B1-629N(H)OMeOOCO2H——0Ogenaconazole
B1-630N(H)CO2EtOOCO2H——0Ogenaconazole
B1-631MeOOCO2H——0Naliconazole
B1-632cyclohexylOOCO2H——0Naliconazole
B1-633t-BuOOCO2H——0Naliconazole
B1-634CF3CH2OOCO2H——0Naliconazole
B1-635allylOOCO2H——0Naliconazole
B1-6364-(NO2)PhOOCO2H——0Naliconazole
B1-637PhSOOCO2H——0Naliconazole
B1-638N(Me)PhOOCO2H——0Naliconazole
B1-639N(H)OMeOOCO2H——0Naliconazole
B1-640N(H)CO2EtOOCO2H——0Naliconazole
B1-641MeOOCO2H——0Nbecliconazole
B1-642cyclohexylOOCO2H——0Nbeciconazole
B1-643t-BuOOCO2H——0Nbeciconazole
B1-644CF3CH2OOCO2H——0Nbeciconazole
B1-645allylOOCO2H——0Nbecliconazole
B1-6464-(NO2)PhOOCO2H——0Nbecliconazole
B1-647PhSOOCO2H——0Nbeciconazole
B1-648N(Me)PhOOCO2H——0Nbecliconazole
B1-649N(H)OMeOOCO2H——0Nbecliconazole
B1-650N(H)CO2EtOOCO2H——0Nbeciconazole
B1-651MeOOCO2H——0Nbrolaconazole
B1-652cyclohexylOOCO2H——0Nbrolaconazole
B1-653t-BuOOCO2H——0Nbrolaconazole
B1-654CF3CH2OOCO2H——0Nbrolaconazole
B1-655aIlylOOCO2H——0Nbrolaconazole
B1-6564-(NO2)PhOOCO2H——0Nbrolaconazole
B1-657PhSOOCO2H——0Nbrolaconazole
B1-658N(Me)PhOOCO2H——0Nbrolaconazole
B1-659N(H)OMeOOCO2H——0Nbrolaconazole
B1-660N(H)CO2EtOOCO2H——0Nbrolaconazole
B1-661MeOOCO2H——0Nbutaconazole
B1-662cyclohexylOOCO2H——0Nbutaconazole
B1-663t-BuOOCO2H——0Nbutaconazole
B1-664CF3CH2OOCO2H——0Nbutaconazole
B1-665allylOOCO2H——0Nbutaconazole
B1-6664-(NO2)PhOOCO2H——0Nbutaconazole
B1-667PhSOOCO2H——0Nbutaconazole
B1-668N(Me)PhOOCO2H——0Nbutaconazole
B1-669N(H)OMeOOCO2H——0Nbutaconazole
B1-670N(H)CO2EtOOCO2H——0Nbutaconazole
B1-671MeOOCO2H——0Nclotrimazole
B1-672cyclohexylOOCO2H——0Nclotriinazole
B1-673t-BuOOCO2H——0Nclotrimazole
B1-674CF3CH2OOCO2H——0Nclotrimazole
B1-675allylOOCO2H——0Nclotrimazole
B1-6764-(NO2)PhOOCO2H——0Nclotrimazole
B1-677PhSOOCO2H——0Nclotrimazole
B1-678N(Me)PhOOCO2H——0Nclotrimazole
B1-679N(H)OMeOOCO2H——0Nclotrimazole
B1-680N(H)CO2EtOOCO2H——0Nclotrimazole
B1-681MeOOCO2H——0Ncroconazole
B1-682cyclohexylOOCO2H——0Ncroconazole
B1-683t-BuOOCO2H——0Ncroconazole
B1-684CF3CH2OOCO2H——0Ncroconazole
B1-685allylOOCO2H——0Ncroconazole
B1-6864-(NO2)PhOOCO2H——0Ncroconazole
B1-687PhSOOCO2H——0Ncroconazole
B1-688N(Me)PhOOCO2H——0Ncroconazole
B1-689N(H)OMeOOCO2H——0Ncroconazole
B1-690N(H)CO2EtOOCO2H——0Ncroconazole
B1-691MeOOCO2H——0Neconazole
B1-692cyclohexylOOCO2H——0Neconazole
B1-693t-BuOOCO2H——0Neconazole
B1-694CF3CH2OOCO2H——0Neconazole
B1-695allylOOCO2H——0Neconazole
B1-6964-(NO2)PhOOCO2H——0Neconazole
B1-697PhSOOCO2H——0Neconazole
B1-698N(Me)PhOOCO2H——0Neconazole
B1-699N(H)OMeOOCO2H——0Neconazole
B1-700N(H)CO2EtOOCO2H——0Neconazole
B1-701MeOOCO2H——0Ndemoconazole
B1-702cyclohexylOOCO2H——0Ndemoconazole
B1-703t-BuOOCO2H——0Ndemoconazole
B1-704CF3CH2OOCO2H——0Ndemoconazole
B1-705aHylOOCO2H——0Ndemoconazole
B1-7064-(NO2)PhOOCO2H——0Ndemoconazole
B1-707PhSOOCO2H——0Ndemoconazole
B1-708N(Me)PhOOCO2H——0Ndemoconazole
B1-709N(H)OMeOOCO2H——0Ndemoconazole
B1-710N(H)CO2EtOOCO2H——0Ndemoconazole
B1-711MeOOCO2H——0Ndoconazole
B1-712cyclohexylOOCO2H——0Ndoconazole
B1-713t-BuOOCO2H——0Ndoconazole
B1-714CF3CH2OOCO2H——0Ndoconazole
B1-715allylOOCO2H——0Ndoconazole
B1-7164-(NO2)PhOOCO2H——0Ndoconazole
B1-717PhSOOCO2H——0Ndoconazole
B1-718N(Me)PhOOCO2H——0Ndoconazole
B1-719N(H)OMeOOCO2H——0Ndoconazale
B1-720N(H)CO2EtOOCO2H——0Ndoconazole
B1-721MeOOCO2H——0Nfenticonazole
B1-722cyclohexylOOCO2H——0Nfenticonazole
B1-723t-BuOOCO2H——0Nfenticonazole
B1-724CF3CH2OOCO2H——0Nfenticonazole
B1-725allylOOCO2H——0Nfenticonazole
B1-7264-(NO2)PhOOCO2H——0Nfenticonazo1e
B1-727PhSOOCO2H——0Nfenticonazole
B1-728N(Me)PhOOCO2H——0Nfenticonazole
B1-729N(H)OMeOOCO2H——0Nfenticonazole
B1-730N(H)CO2EtOOCO2H——0Nfenticonazole
B1-731MeOOCO2H——0Neberconazole
B1-732cyclohexylOOCO2H——0Neberconazole
B1-733t-BuOOCO2H——0Neberconazole
B1-734CF3CH2OOCO2H——0Neberconazole
B1-735allylOOCO2H——0Neberconazole
B1-7364-(NO2)PhOOCO2H——0Neberconazole
B1-737PhSOOCO2H——0Neberconazole
B1-738N(Me)PhOOCO2H——0Neberconazole
B1-739N(H)OMeOOCO2H——0Neberconazole
B1-740N(H)CO2EtOOCO2H——0Neberconazole
B1-741MeOOCO2H——0Nisoconazole
B1-742cyclohexylOOCO2H——0Nisoconazole
B1-743t-BuOOCO2H——0Nisoconazole
B1-744CF3CH2OOCO2H——0Nisoconazole
B1-745allylOOCO2H——0Nisoconazole
B1-7464-(NO2)PhOOCO2H——0Nisoconazole
B1-747PhSOOCO2H——0Nisoconazole
B1-748N(Me)PhOOCO2H——0Nisoconazole
B1-749N(H)OMeOOCO2H——0Nisoconazole
B1-750N(H)CO2EtOOCO2H——0Nisoconazole
B1-751MeOOCO2H——0Nmiconazole
B1-752cyclohexylOOCO2H——0Nmiconazole
B1-753t-BuOOCO2H——0Nmiconazole
B1-754CF3CH2OO0021-I——0Nmiconazole
B1-755allylOOCO2H——0Nmiconazole
B1-7564-(NO2)PhOOCO2H——0Nmiconazole
B1-757PhSOOCO2H——0Nmiconazole
B1-758N(Me)PhOOCO2H——0Nmiconazole
B1-759N(H)OMeOOCO2H——0Nmiconazole
B1-760N(H)CO2EtOOCO2H——0Nmiconazole
B1-761MeOOCO2H——0Nneticonazole
B1-762cyclohexylOOCO2H——0Nneticonazole
B1-763t-BuOOCO2H——0Nneticonazole
B1-764CF3CH2OOCO2H——0Nneticonazole
B1-765allylOOCO2H——0Nneticonazole
B1-7664-(NO2)PhOOCO2H——0Nneticonazole
B1-767PhSOOCO2H——0Nneticonazole
B1-768N(Me)PhOOCO2H——0Nneticonazole
B1-769N(H)OMeOOCO2H——0Nneticonazole
B1-770N(H)CO2EtOOCO2H——0Nneticonazole
B1-771MeOOCO2H——0Nomoconazole
B1-772cyclohexylOOCO2H——0Nomoconazole
B1-773t-BuOOCO2H——0Nomoconazole
B1-774CF3CH2OOCO2H——0Nomoconazole
B1-775allylOOCO2H——0Nomoconazole
B1-7764-(NO2)PhOOCO2H——0Nomoconazole
B1-777PhS0OCO2H——0Nomoconazole
B1-778N(Me)PhOOCO2H——0Nomoconazole
B1-779N(H)OMeOOCO2H——0Nomoconazole
B1-780N(H)CO2EtOOCO2H——0Nomoconazole
B1-781MeOOCO2H——0Norconazole
B1-782cyclohexylOOCO2H——0Norconazole
B1-783t-BuOOCO2H——0Norconazole
B1-784CF3CH2OOCO2H——0Norconazole
B1-785allylOOCO2H——0Norconazole
B1-7864-(NO2)PhOOCO2H——0Norconazole
B1-787PhSOOCO2H——0Norconazole
B1-788N(Me)PhOOCO2H——0Norconazole
B1-789N(H)OMeOOCO2H——0Norconazole
B1-790N(H)CO2EtOOCO2H——0Norconazole
B1-791MeOOCO2H——0Noxiconazole
B1-792cyclohexylOOCO2H——0Noxiconazole
B1-793t-BuOOCO2H——0Noxiconazole
B1-794CF3CH2OOCO2H——0Noxiconazole
B1-795allylOOCO2H——0Noxiconazole
B1-7964-(NO2)PhOOCO2H——0Noxiconazole
B1-797PhSOOCO2H——0Noxiconazole
B1-798N(Me)PhOOCO2H——0Noxiconazole
B1-799N(H)OMeOOCO2H——0Noxiconazole
B1-800N(H)CO2EtOOCO2H——0Noxiconazole
B1-801MeOOCO2H——0Nparconazole
B1-802cyclohexylOOCO2H——0Nparconazole
B1-803t-BuOOCO2H——0Nparconazole
B1-804CF3CH2OOCO2H——0Nparconazole
B1-805allylOOCO2H——0Nparconazole
B1-8064-(NO2)PhOOCO2H——0Nparconazole
B1-807PhSOOCO2H——0Nparconazole
B1-808N(Me)PhOOCO2H——0Nparconazole
B1-809N(H)OMeOOCO2H——0Nparconazole
B1-810N(H)CO2EtOOCO2H——0Nparconazole
B1-811MeOOCO2H——0Nravuconazole
B1-812cyclohexylOOCO2H——0Nravuconazole
B1-813t-BuOOCO2H——0Nravuconazole
B1-814CF3CH2OOCO2H——0Nravuconazole
B1-815allylOOCO2H——0Nravuconazole
B1-8164-(NO2)PhOOCO2H——0Nravuconazole
B1-817PhSOOCO2H——0Nravuconazole
B1-818N(Me)PhOOCO2H——0Nravuconazole
B1-819N(H)OMeOOCO2H——0Nravuconazole
B1-820N(H)CO2EtOOCO2H——0Nravuconazole
B1-821MeOOCO2H——0Nsertaconazole
B1-822cyclohexylOOCO2H——0Nsertaconazole
B1-823t-BuOOCO2H——0Nsertaconazole
B1-824CF3CH2OOCO2H——0Nsertaconazole
B1-825allylOOCO2H——0Nsertaconazole
B1-8264-(NO2)PhOOCO2H——0Nsertaconazole
B1-827PhSOOCO2H——0Nsertaconazole
B1-828N(Me)PhOOCO2H——0Nsertaconazole
B1-829N(H)OMeOOCO2H——0Nsertaconazole
B1-830N(H)CO2EtOOCO2H——0Nsertaconazole
B1-831MeOOCO2H——0Nsulconazole
B1-832cyclohexylOOCO2H——0Nsulconazole
B1-833t-BuOOCO2H——0Nsulconazole
B1-834CF3CH2OOCO2H——0Nsulconazole
B1-835allylOOCO2H——0Nsulconazole
B1-8364-(NO2)PhOOCO2H——0Nsulconazole
B1-837PhSOOCO2H——0Nsulconazole
B1-838N(Me)PhOOCO2H——0Nsulconazole
B1-839N(H)OMeOOCO2H——0Nsulconazole
B1-840N(H)CO2EtOOCO2H——0Nsulconazole
B1-841MeOOCO2H——0Ntioconazole
B1-842cyclohexylOOCO2H——0Ntioconazole
B1-843t-BuOOCO2H——0Ntioconazole
B1-844CF3CH2OOCO2H——0Ntioconazole
B1-845allylOOCO2H——0Ntioconazole
B1-8464-(NO2)PhOOCO2H——0Ntioconazole
B1-847PhSOOCO2H——0Ntioconazole
B1-848N(Me)PhOOCO2H——0Ntioconazole
B1-849N(H)OMeOOCO2H——0Ntioconazole
B1-850N(H)CO2EtOOCO2H——0Ntioconazole
B1-851MeOOCO2H——0Nvalconazole
B1-852cyclohexylOOCO2H——0Nvalconazole
B1-853t-BuOOCO2H——0Nvalconazole
B1-854CF3CH2OOCO2H——0Nvakonazole
B1-855allylOOCO2H——0Nvalconazole
B1-8564-(NO2)PhOOCO2H——0Nvalconazole
B1-857PhSOOCO2H——0Nvalconazale
B1-858N(Me)PhOOCO2H——0Nvalconazole
B1-859N(H)OMeOOCO2H——0Nvalconazole
B1-860N(H)CO2EtOOCO2H——0Nvalconazole
B1-861MeOOCO2H——0Nzinoconazole
B1-862cyclohexylOOCO2H——0Nzinoconazole
B1-863t-BuOOCO2H——0Nzinoconazole
B1-864CF3CH2OOCO2H——0Nzinoconazole
B1-865allylOOCO2H——0Nzinoconazole
B1-8664-(NO2)PhOOCO2H——0Nzinoconazole
B1-867PhSOOCO2H——0Nzinoconazole
B1-868N(Me)PhOOCO2H——0Nzinoconazole
B1-869N(H)OMeOOCO2H——0Nzinoconazole
B1-870N(H)CO2EtOOCO2H——0Nzinoconazole
B1-871MeOOCO2HOO1Ccloxacillin
B1-872cyclohexylOOCO2HOO1Ccloxacillin
B1-873t-BuOOCO2HOO1Ccloxacillin
B1-874CF3CH2OOCO2HOO1Ccloxacillin
B1-875alLylOOCO2HOO1Ccloxacillin
B1-8764-(NO2)PhOOCO2HOO1Ccloxacillin
B1-877PhSOOCO2HOO1Ccloxacillin
B1-878N(Me)PhOOCO2HOO1Ccloxacillin
B1-879N(H)OMeOOCO2HOO1Ccloxacillin
B1-880N(H)CO2EtOOCO2HOO1Ccloxacillin
B1-881MeOOCO2HOO1Cvalproic acid
B1-882cyclohexylOOCO2HOO1Cvalproic acid
B1-883t-BuOOCO2HOO1Cvalproic acid
B1-884CF3CH2OOCO2HOO1Cvalproic acid
B1-885allylOOCO2HOO1Cvalproic acid
B1-8864-(NO2)PhOOCO2HOO1Cvalproic acid
B1-887PhSOOCO2HOO1Cvalproic acid
B1-888N(Me)PhOOCO2HOO1Cvalproic acid
B1-889N(H)OMeOOCO2HOO1Cvalproic acid
B1-890N(H)CO2EtOOCO2HOO1Cvalproic acid
B1-891MeOOCO2HOO1Cretinoic acid
B1-892cyclohexylOOCO2HOO1Cretinoic acid
B1-893t-BuOOCO2HOO1Cretinoic acid
B1-894CF3CH2OOCO2HOO1Cretinoic acid
B1-895allylOOCO2HOO1Cretinoic acid
B1-8964-(NO2)PhOOCO2HOO1Cretinoic acid
B1-897PhSOOCO2HOO1Cretinoic acid
B1-898N(Me)PhOOCO2HOO1Cretinoic acid
B1-899N(H)OMeOOCO2HOO1Cretinoic acid
B1-900N(H)CO2EtOOCO2HOO1Cretinoic acid
B1-901MeOOCO2HOO1Coxaprozin
B1-902cyclohexylOOCO2HOO1Coxaprozin
B1-903t-BuOOCO2HOO1Coxaprozin
B1-904CF3CH2OOCO2HOO1Coxaprozrn
B1-905allylOOCO2HOO1Coxaprozin
B1-9064-(NO2)PhOOCO2HOO1Coxaprozin
B1-907PhSOOCO2HOO1Coxaprozin
B1-908N(Me)PhOOCO2HOO1Coxaprozin
B1-909N(H)OMeOOCO2HOO1Coxaprozin
B1-910N(H)CO2EtOOCO2HOO1Coxaprozin
B1-911MeOOCO2HOO1Cnaproxen
B1-912cyclohexylOOCO2HOO1Cnaproxen
B1-913t-BuOOCO2HOO1Cnaproxen
B1-914CF3CH2OOCO2HOO1Cnaproxen
B1-915allylOOCO2HOO1Cnaproxen
B1-9164-(NO2)PhOOCO2HOO1Cnaproxen
B1-917PhSOOCO2HOO1Cnaproxen
B1-918N(Me)PhOOCO2HOO1Cnaproxen
B1-919N(H)OMeOOCO2HOO1Cnaproxen
B1-920N(H)CO2EtOOCO2HOO1Cnaproxen
B1-921MeOOCO2HOO1Cmonopril
B1-922cyclohexylOOCO2HOO1Cmonopril
B1-923t-BuOOCO2HOO1Cmonopril
B1-924CF3CH2OOCO2HOO1Cmonopril
B1-925allylOOCO2HOO1Cmonopril
B1-9264-(NO2)PhOOCO2HOO1Cmonopril
B1-927PhSOOCO2HOO1Cmonopril
B1-928N(Me)PhOOCO2HOO1Cmonopril
B1-929N(H)OMeOOCO2HOO1Cmonopril
B1-930N(H)CO2EtOOCO2HOO1Cmonopril
B1-931MeOOCO2HOO1Cketorolac
B1-932cyclohexylOOCO2HOO1Cketorolac
B1-933t-BuOOCO2HOO1Cketorolac
B1-934CF3CH2OOCO2HOO1Cketorolac
B1-935allylOOCO2HOO1Cketorolac
B1-9364-(NO2)PhOOCO2HOO1Cketorolac
B1-937PhSOOCO2HOO1Cketorolac
B1-938N(Me)PhOOCO2HOO1Cketorolac
B1-939N(H)OMeOOCO2HOO1Cketorolac
B1-940N(H)CO2EtOOCO2HOO1Cketorolac
B1-941MeOOCO2HOO1Cketoprofen
B1-942cyclohexylOOCO2HOO1Cketoprofen
B1-943t-BuOOCO2HOO1Cketoprofen
B1-944CF3CH2OOCO2HOO1Cketoprofen
B1-945allylOOCO2HOO1Cketoprofen
B1-9464-(NO2)PhOOCO2HOO1Cketoprofen
B1-947PhSOOCO2HOO1Cketoprofen
B1-948N(Me)PhOOCO2HOO1Cketoprofen
B1-949N(H)OMeOOCO2HOO1Cketoprofen
B1-950N(H)CO2EtOOCO2HOO1Cketoprofen
B1-951MeOOCO2HOO1Cindomethacin
B1-952cyclohexylOOCO2HOO1Cindomethacin
B1-953t-BuOOCO2HOO1Cindomethacin
B1-954CF3CH2OOCO2HOO1Cindomethacin
B1-955allylOOCO2HOO1Cindomethacin
B1-9564-(NO2)PhOOCO2HOO1Cindomethacin
B1-957PhSOOCO2HOO1Cindomethacin
B1-958N(Me)PhOOCO2HOO1Cindomethacin
B1-959N(H)OMeOOCO2HOO1Cindomethacin
B1-960N(H)CO2EtOOCO2HOO1Cindomethacin
B1-961MeOOCO2HOO1Cibuprofen
B1-962cyclohexylOOCO2HOO1Cibuprofen
B1-963t-BuOOCO2HOO1Cibuprofen
B1-964CF3CH2OOCO2HOO1Cibuprofen
B1-965allylOOCO2HOO1Cibuprofen
B1-9664-(NO2)PhOOCO2HOO1Cibuprofen
B1-967PhSOOCO2HOO1Cibuprofen
B1-968N(Me)PhOOCO2HOO1Cibuprofen
B1-969N(H)OMeOOCO2HOO1Cibuprofen
B1-970N(H)CO2EtOOCO2HOO1Cibuprofen
B1-971MeOOCO2HOO1Cgemfibrozil
B1-972cyclohexylOOCO2HOO1Cgemfibrozil
B1-973t-BuOOCO2HOO1Cgemfibrozil
B1-974CF3CH2OOCO2HOO1Cgemfibrozil
B1-975allylOOCO2HOO1Cgemfibrozil
B1-9764-(NO2)PhOOCO2HOO1Cgemfibrozil
B1-977PhSOOCO2HOO1Cgemfibrozil
B1-978N(Me)PhOOCO2HOO1Cgemfibrozil
B1-979N(H)OMeOOCO2HOO1Cgemfibrozil
B1-980N(H)CO2EtOOCO2HOO1Cgemfibrozil
B1-981MeOOCO2HOO1Cflubiprofen
B1-982cyclohexylOOCO2HOO1Cflurbiprofen
B1-983t-BuOOCO2HOO1Cflurbiprofen
B1-984CF3CH2OOCO2HOO1Cflurbiprofen
B1-985allylOOCO2HOO1Cflurbiprofen
B1-9864-(NO2)PhOOCO2HOO1Cflurbiprofen
B1-987PhSOOCO2HOO1Cflurbiprofen
B1-988N(Me)PhOOCO2HOO1Cflurbiprofen
B1-989N(H)OMeOOCO2HOO1Cflurbiprofen
B1-990N(H)CO2EtOOCO2HOO1Cflurbiprofen
B1-991MeOOCO2HOO1Carthrocine
B1-992cyclohexylOOCO2HOO1Carthrocine
B1-993t-BuOOCO2HOO1Carthrocine
B1-994CF3CH2OOCO2HOO1Carthrocine
B1-995allylOOCO2HOO1Carthrocine
B1-9964-(NO2)PhOOCO2HOO1Carthrocine
B1-997PhSOOCO2HOO1Carthrocine
B1-998N(Me)PhOOCO2HOO1Carthrocine
B1-999N(H)OMeOOCO2HOO1Carthrocine
B1-1000N(H)CO2EtOOCO2HOO1Carthrocine
B1-1001MeOOCO2HOO1Cadapalene
B1-1002cyclohexylOOCO2HOO1Cadapalene
B1-1003t-BuOOCO2HOO1Cadapalene
B1-1004CF3CH2OOCO2HOO1Cadapalene
B1-1005allylOOCO2HOO1Cadapalene
B1-10064-(NO2)PhOOCO2HOO1Cadapalene
B1-1007PhSOOCO2HOO1Cadapalene
B1-1008N(Me)PhOOCO2HOO1Cadapalene
B1-1009N(H)OMeOOCO2HOO1Cadapalene
B1-1010N(H)CO2EtOOCO2HOO1Cadapalene
B1-1011MeOOCO2HOO1Clansoprazole
B1-1012cyclohexylOOCO2HOO1Clansoprazole
B1-1013t-BuOOCO2HOO1Clansoprazole
B1-1014CF3CH2OOCO2HOO1Clansoprazole
B1-1015allylOOCO2HOO1Clansoprazole
B1-10164-(NO2)PhOOCO2HOO1Clansoprazole
B1-1017PhSOOCO2HOO1Clansoprazole
B1-1018N(Me)PhOOCO2HOO1Clansoprazole
B1-1019N(H)OMeOOCO2HOO1Clansoprazole
B1-1020N(H)CO2EtOOCO2HOO1Clansoprazole
B1-1021MeOOCO2HOO1Clovastatin
B1-1022cyclohexylOOCO2HOO1Clovastatin
B1-1023t-BuOOCO2HOO1Clovastatin
B1-1024CF3CH2OOCO2HOO1Clovastatin
B1-1025allyLOOCO2HOO1Clovastatin
B1-10264-(NO2)PhOOCO2HOO1Clovastatin
B1-1027PhSOOCO2HOO1Clovastatin
B1-1028N(Me)PhOOCO2HOO1Clovastatin
B1-1029N(H)OMeOOCO2HOO1Clovastatiin
B1-1030N(H)CO2EtOOCO2HOO1Clovastatin
H1-1031MeOOCO2HOO1Cwarfarin
B1-1032cyclohexylOOCO2HOO1Cwarfarin
B1-1033t-BuOOCO2HOO1Cwarfarin
B1-1034CF3CH2OOCO2HOO1Cwarfarin
B1-1035allylOOCO2HOO1Cwarfarin
B1-10364-(NO2)PhOOCOAlOO1Cwarfarin
B1-1037PhSOOCO2HOO1Cwarfarin
B1-1038N(Me)PhOOCO2HOO1Cwarfarin
B1-1039N(H)OMeOOCO2HOO1Cwarfarin
B1-1040N(H)CO2EtOOCO2HOO1Cwarfarin
B1-1041MeOOCO2H——0Ntolteridine
B1-1042cycbohexylOOCO2H——0Ntolteridine
B1-1043t-BuOOCO2H——0Ntolteridine
B1-1044CF3CH2OOCO2H——0Ntolteridine
B1-1045allylOOCO2H——0Ntolteridine
B1-10464-(NO2)PhOOCO2H——0Ntolteridine
B1-1047PhSOOCO2H——0Ntolteridine
B1-1048N(Me)PhOOCO2H——0Ntolteridine
B1-1049N(H)OMeOOCO2H——0Ntolteridine
B1-1050N(H)CO2EtOOCO2H——0Ntolteridine
B1-1051MeOOCO2H——0Nticlopidine
B1-1052cyclohexylOOCO2H——0Nticlopidine
B1-1053t-BuOOCO2H——0Nticlopidine
B1-1054CF3CH2OOCO2H——0Nticlopidine
B1-1055allylOOCO2H——0Nticiopidine
B1-10564-(NO2)PhOOCO2H——0Nticlopidine
B1-1057PhSOOCO2H——0Nticlopidine
B1-1058N(Me)PhOOCO2H——0Nticlopidine
B1-1059N(H)OMeOOCO2H——0Nticlopidine
B1-1060N(H)CO2EtOOCO2H——0Nticlopidine
B1-1061MeOOCO2H——0Nsibutramine
B1-1062cyclohexylOOCO2H——0Nsibutramine
B1-1063t-BuOOCO2H——0Nsibutramine
B1-1064CF3CH2OOCO2H——0Nsibutramine
B1-1065allylOOCO2H——0Nsibutramine
B1-10664-(NO2)PhOOCO2H——0Nsibutramine
B1-1067PhSOOCO2H——0Nsibutramine
B1-1068N(Me)PhOOCO2H——0Nsibutramine
B1-1069N(H)OMeOOCO2H——0Nsibutramine
B1-1070N(H)CO2EtOOCO2H——0Nsibutramine
B1-1071MeOOCO2H——0Npropoxyphene
B1-1072cyclohexylOOCO2H——0Npropoxyphene
B1-1073t-BuOOCO2H——0Npropoxyphene
B1-1074CF3CH2OOCO2H——0Npropoxyphene
B1-1075allylOOCO2H——0Npropoxyphene
B1-10764-(NO2)PhOOCO2H——0Npropoxyphene
B1-1077PhSOOCO2H——0Npropoxyphene
B1-1078N(Me)PhOOCO2H——0Npropoxyphene
B1-1079N(H)OMeOOCO2H——0Npropoxyphene
B1-1080N(H)CO2EtOOCO2H——0Npropoxyphene
B1-1081MeOOCO2H——0Nnifurantin
B1-1082cyclohexylOOCO2H——0Nnifurantin
B1-1083t-BuOOCO2H——0Nnifurantin
B1-1084CF3CH2OOCO2H——0Nnifurantin
B1-1085allylOOCO2H——0Nnifurantin
B1-10864-(NO2)PhOOCO2H——0Nnifurantin
B1-1087PhSOOCO2H——0Nnifurantin
B1-1088N(Me)PhOOCO2H——0Nnifurantin
B1-1089N(H)OMeOOCO2H——0Nnifurantin
B1-1090N(H)CO2EtOOCO2H——0Nnifurantin
B1-1091MeOOCO2H——0Nnefazodone
B1-1092cyclohexylOOCO2H——0Nnefazodone
B1-1093t-BuOOCO2H——0Nnefazodone
B1-1094CF3CH2OOCO2H——0Nnefazodone
B1-1095allylOOCO2H——0Nnefazodone
B1-10964-(NO2)PhOOCO2H——0Nnefazodone
B1-1097PhSOOCO2H——0Nnefazodone
B1-1098N(Me)PhOOCO2H——0Nnefazodone
B1-1099N(H)OMeOOCO2H——0Nnefazodone
B1-1100N(H)CO2EtOOCO2H——0Nnefazodone
B1-1101MeOOCO2H——0Ndonezapil
B1-1102cyclohexylOOCO2H——0Ndonezapil
B1-1103t-BuOOCO2H——0Ndonezapil
B1-1104CF3CH2OOCO2H——0Ndonezapil
B1-1105allylOOCO2H——0Ndonezapil
B1-11064-(NO2)PhOOCO2H——0Ndonezapil
B1-1107PhSOOCO2H——0Ndonezapil
B1-1108N(Me)PHOOCO2H——0Ndonezapil
B1-1109N(H)OMeOOCO2H——0Ndonezapil
B1-1110N(H)CO2EtOOCO2H——0Ndonezapil
B1-1111MeOOCO2H——0Ndicodid
B1-1112cyclohexylOOCO2H——0Ndicodid
B1-1113t-BuOOCO2H——0Ndicodid
B1-1114CF3CH2OOCO2H——0Ndicodid
B1-1115allylOOCO2H——0Ndicodid
B1-11164-(NO2)PhOOCO2H——0Ndicodid
B1-1117PhSOOCO2H——0Ndicodid
B1-1118N(Me)PhOOCO2H——0Ndicodid
B1-1119N(H)OMeOOCO2H——0Ndicodid
B1-1120N(H)CO2EtOOCO2H——0Ndicodid
B1-1121MeOOCO2H——0Ncolchicine
B1-1122cyclohexylOOCO2H——0Ncolchicine
B1-1123t-BuOOCO2H——0Ncolchicine
B1-1124CF3CH2OOCO2H——0Ncolchicine
B1-1125allylOOCO2H——0Ncolchicine
B1-11264-(NO2)PhOOCO2H——0Ncolchicine
B1-1127PhSOOCO2H——0Ncolchicine
B1-1128N(Me)PhOOCO2H——0Ncolchicine
B1-1129N(H)OMeOOCO2H——0Ncolchicine
B1-1130N(H)CO2EtOOCO2H——0Ncolchicine
B1-1131MeOOCO2H——0Ncitalopram
B1-1132cyclohexylOOCO2H——0Ncitalopram
B1-1133t-BuOOCO2H——0Ncitalopram
B1-1134CF3CH2OOCO2H——0Ncitalopram
B1-1135allylOOCO2H——0Ncitalopram
B1-11364-(NO2)PhOOCO2H——0Ncitalopram
B1-1137PhSOOCO2H——0Ncitalopram
B1-1138N(Me)PhOOCO2H——0Ncitalopram
B1-1139N(H)OMeOOCO2H——0Ncitalopram
B1-1140N(H)CO2EtOOCO2H——0Ncitalopram
B1-1141MeOOCO2H——0Nbenzatropine
B1-1142cyclohexylOOCO2H——0Nbenzatropine
B1-1143t-BuOOCO2H——0Nbenzatropine
B1-1144CF3CH2OOCO2H——0Nbenzatropine
B1-1145allylOOCO2H——0Nbenzatropine
B1-11464-(NO2)PhOOCO2H——0Nbenzatropine
B1-1147PhSOOCO2H——0Nbenzatropine
B1-1148N(Me)PhOOCO2H——0Nbenzatropine
B1-1149N(H)OMeOOCO2H——0Nbenzatropine
B1-1150N(H)CO2EtOOCO2H——0Nbenzatropine
B1-1151EtSOOCO2H——0Nbisacodyl
B1-1152EtOOOCO2H——0Nbisacodyl
B1-1153t-BuOOOCO2H——0Nbisacodyl
B1-1154cyclohexylOOOCO2H——0Nbisacodyl
B1-1155iPrOOOCO2H——0Nbisacodyl
B1-1156PhOOOCO2H——0Nbisacodyl
B1-1157(HOCH2—OOCO2H——0Nbisacodyl
CH2)2N
B1-1158N(H)NMe2OOCO2H——0Nbisacodyl
B1-11594-(OH)PhOOCO2H——0Nbisacodyl
B1-11604-(NH2)PhOOCO2H——0Nbisacodyl
B1-1161EtSOOCO2H——0Nbupivacaine
B1-1162EtOOOCO2H——0Nbupivacaine
B1-1163t-BuOOOCO2H——0Nbupivacaine
B1-1164cyclohexylOOOCO2H——0Nbupivacaine
B1-1165iPrOOOCO2H——0Nbupivacaine
B1-1166PhOOOCO2H——0Nbupivacaine
B1-1167(HOCH2—OOCO2H——0Nbupivacaine
CH2)2N
B1-1168N(H)NMe2OOCO2H——0Nbupivacaine
B1-11694-(OH)PhOOCO2H——0Nbupivacaine
B1-11704-(NH2)PhOOCO2H——0Nbupivacaine
B1-1171EtSOOCO2H——0Nchloroprocaine
B1-1172EtOOOCO2H——0Nchloroprocaine
B1-1173t-BuOOOCO2H——0Nchloroprocaine
B1-1174cyclohexylOOOCO2H——0Nchloroprocaine
B1-1175iPrOOOCO2H——0Nchloroprocaine
B1-1176PhOOOCO2H——0Nchloroprocaine
B1-1177(HOCH2—OOCO2H——0Nchloroprocaine
CH2)2N
B1-1178N(H)NMe2OOCO2H——0Nchloroprocaine
B1-11794-(OH)PhOOCO2H——0Nchloroprocaine
B1-11804-(NH2)PhOOCO2H——0Nchloroprocaine
B1-1181EtSOOCO2H——0Ntetracaine
B1-1182EtOOOCO2H——0Ntetracaine
B1-1183t-BuOOOCO2H——0Ntetracaine
B1-1184cyclohexylOOOCO2H——0Ntetracaine
B1-1185iPrOOOCO2H——0Ntetracaine
B1-1186PhOOOCO2H——0Ntetracaine
B1-1187(HOCH2—OOCO2H——0Ntetracaine
CH2)2N
B1-1188N(H)NMe2OOCO2H——0Ntetracaine
B1-11894-(OH)PhOOCO2H——0Ntetracaine
B1-11904-(NH2)PhOOCO2H——0Ntetracaine
B1-1191EtSOOCO2H——0Nacrivistine
B1-1192EtOOOCO2H——0Nacrivistine
B1-1193t-BuOOOCO2H——0Nacrivistine
B1-1194cyclohexylOOOCO2H——0Nacrivistine
B1-1195iPrOOOCO2H——0Nacrivistine
B1-1196PhOOOCO2H——0Nacrivistine
B1-1197(HOCH2—OOCO2H——0Nacrivistine
CH2)2N
B1-1198N(H)NMe2OOCO2H——0Nacrivistine
B1-11994-(OH)PhOOCO2H——0Nacrivistine
B1-12004-(NH2)PhOOCO2H——0Nacrivistine
B1-1201EtSOOCO2H——0Namiodarone
B1-1202EtOOOCO2H——0Namiodarone
B1-1203t-BuOOOCO2H——0Namiodarone
B1-1204cyclohexylOOOCO2H——0Namiodarone
B1-1205iPrOOOCO2H——0Namiodarone
B1-1206PhOOOCO2H——0Namiodarone
B1-1207(HOCH2—OOCO2H——0Namiodarone
CH2)2N
B1-1208N(H)NMe2OOCO2H——0Namiodarone
B1-12094-(OH)PhOOCO2H——0Namiodarone
B1-12104-(NH2)PhOOCO2H——0Namiodarone
B1-1211EtSOOCO2H——0Namitriptyline
B1-1212EtOOOCO2H——0Namitriptyline
B1-1213t-BuOOOCO2H——0Namitriptyline
B1-1214cyclohexylOOOCO2H——0Namitriptyline
B1-1215iPrOOOCO2H——0Namitriptyline
B1-1216PhOOOCO2H——0Namitriptyline
B1-1217(HOCH2—OOCO2H——0Namitriptyline
CH2)2N
B1-1218N(H)NMe2OOCO2H——0Namitriptyhine
B1-12194-(OH)PhOOCO2H——0Namitriptyline
B1-12204-(NH2)PhOOCO2H——0Namitriptyline
B1-1221EtSOOCO2H——0Namrinone
B1-1222EtOOOCO2H——0Namrinone
B1-1223t-BuOOOCO2H——0Namrinone
B1-1224cyclohexylOOOCO2H——0Namrinone
B1-1225iPrOOOCO2H——0Namrinone
B1-1226PhOOOCO2H——0Namrinone
B1-1227(HOCH2—OOCO2H——0Namrinone
CH2)2N
B1-1228N(H)NMe2OOCO2H——0Namrinone
B1-12294-(OH)PhOOCO2H——0Namrinone
B1-12304-(NH2)PhOOCO2H——0Namrinone
B1-1231EtSOOCO2H——0Natropine
B1-1232EtOOOCO2H——0Natropine
B1-1233t-BuOOOCO2H——0Natropine
B1-1234cyclohexylOOOCO2H——0Natropine
B1-1235iPrOOOCO2H——0Natropine
B1-1236PhOOOCO2H——0Natropine
B1-1237(HOCH2—OOCO2H——0Natropine
CH2)2N
B1-1238N(H)NMe2OOCO2H——0Natropine
B1-12394-(OH)PhOOCO2H——0Natropine
B1-12404-(NH2)PhOOCO2H——0Natropine
B1-1241EtSOOCO2H——0Nbenzphetamine
B1-1242EtOOOCO2H——0Nbenzphetamine
B1-1243t-BuOOOCO2H——0Nbenzphetamine
B1-1244cyclohexylOOOCO2H——0Nbenzphetamine
B1-1245iPrOOOCO2H——0Nbenzphetamine
B1-1246PhOOOCO2H——0Nbenzphetamine
B1-1247(HOCH2—OOCO2H——0Nbenzphetamine
CH2)2N
B1-1248N(H)NMe2OOCO2H——0Nbenzphetamine
B1-12494-(OH)PhOOCO2H——0Nbenzphetamine
B1-12504-(NH2)PhOOCO2H——0Nbenzphetamine
B1-1251EtSOOCO2H——0Nbeperiden
B1-1252EtOOOCO2H——0Nbeperiden
B1-1253t-Bu0OOCO2H——0Nbeperiden
B1-1254cyclohexylOOOCO2H——0Nbeperiden
B1-1255iPrOOOCO2H——0Nbeperiden
B1-1256PhOOOCO2H——0Nbeperiden
B1-1257(HOCH2—OOCO2H——0Nbeperiden
CH2)2N
B1-1258N(H)NMe2OOCO2H——0Nbeperiden
B1-12594-(OH)PhOOCO2H——0Nbeperiden
B1-12604-(NH2)PhOOCO2H——0Nbeperiden
B1-1261EtSOOCO2H——0Nbromopheniramine
B1-1262EtOOOCO2H——0Nbromopheniramine
B1-1263t-BuOOOCO2H——0Nbromopheniramine
B1-1264cyclohexylOOOCO2H——0Nbromopheniramine
B1-1265iPrOOOCO2H——0Nbromopheniramine
B1-1266PhOOOCO2H——0Nbromopheniramine
B1-1267(HOCH2—OOCO2H——0Nbromopheniramine
CH2)2N
B1-1268N(H)NMe2OOCO2H——0Nbromopheniramine
B1-12694-(OH)PhOOCO2H——0Nbromopheniramine
B1-12704-(NH2)PhOOCO2H——0Nbromopheniramine
B1-1271EtSOOCO2H——0Nclemastine
B1-1272EtOOOCO2H——0Nclemastine
B1-1273t-BuOOOCO2H——0Nclemastine
B1-l274cyclohexylOO0CO2H——0Nclemastine
B1-1275iPrOOOCO2H——0Nclemastine
B1-1276PhOOOC021i——0Nclemastine
B1-1277(HOCH2—OOCO2H——0Nclemastine
CH2)2N
B1-1278N(H)NMe2OOCO2H——0Nclemastine
B1-12794-(OH)PhOOCO2H——0Nclemastine
B1-12804-(NH2)PhOOCO2H——0Nclemastine
B1-1281EtSOOCO2H——0Nclomiphene
B1-1282EtOOOCO2H——0Nclomiphene
B1-1283t-BuOOOCO2H——0Nclomiphene
B1-1284cyclohexylOOOCO2H——0Nclomiphene
B1-1285iPrOOOCO2H——0Nclomiphene
B1-1286PhOOOCO2H——0Nclomiphene
B1-1287(HOCH2—OOCO2H——0Nclomiphene
CH2)2N
B1-1288N(H)NMe2OOCO2H——0Nclomiphene
B1-12894-(OH)PhOOCO2H——0Nclomiphene
B1-12904-(NH2)PhOOCO2H——0Nclomiphene
B1-1291EtSOOCO2H——0Ncyclobenzaprine
B1-1292EtOOOCO2H——0Ncyclobenzaprine
B1-1293t-BuOOOCO2H——0Ncyclobenzaprine
B1-1294cyclohexylOOOCO2H——0Ncyclobenzaprine
B1-1295iPrOOOCO2H——0Ncyclobenzaprine
B1-1296PhOOOCO2H——0Ncyclobenzaprine
B1-1297(HOCH2—OOCO2H——0Ncyclobenzaprine
CH2)2N
B1-1298N(H)NMe2OOCO2H——0Ncyclobenzaprine
B1-12994-(OH)PhOOCO2H——0Ncyclobenzaprine
B1-13004-(NH2)PhOOCO2H——0Ncyclobenzaprine
B1-1301EtSOOCO2H——0Ncyclopentolate
B1-1302EtOOOCO2H——0Ncyclopentolate
B1-1303t-BuOOOCO2H——0Ncyclopentolate
B1-1304cyclohexylOOOCO2H——0Ncyclopentolate
B1-1305iPrOOOCO2H——0Ncyclopentolate
B1-1306PhOOOCO2H——0Ncyclopentolate
B1-1307(HOCH2—OOCO2H——0Ncyclopentolate
CH2)2N
B1-1308N(H)NMe2OOCO2H——0Ncyclopentolate
B1-13094-(OH)PhOOCO2H——0Ncyclopentolate
B1-13104-(NH2)PhOOCO2H——0Ncyclopentolate
B1-1311EtSOOCO2H——0Ndicyclomine
B1-1312EtOOOCO2H1——0Ndicyclomine
B1-1313t-Bu0OOCO2H——0Ndicyclomine
B1-1314cyclohexylOOOCO2H——0Ndicyclomine
B1-1315iPrOOOCO2H——0Ndicyclomine
B1-1316PhOOOCO2H——0Ndicyclomine
B1-1317(HOCH2—OOCO2H——0Ndicyclomine
CH2)2N
B1-1318N(H)NMe2OOCO2H——0Ndicyclomine
B1-13194-(OH)PhOOCO2H——0Ndicyclomine
B1-13204-(NH2)PhOOCO2H——0Ndicyclomine
B1-1321EtSOOCO2H——0Ndiethylproprion
B1-1322EtOOOCO2H——0Ndiethylproprion
B1-1323t-BuOOOCO2H——0Ndiethylproprion
B1-1324cyclohexylOOOCO2H——0Ndiethylproprion
B1-1325iPrOOOCO2H——0Ndiethylproprion
B1-1326Ph0OOCO2H——0Ndiethylproprion
B1-1327(HOCH2—OOCO2H——0Ndiethylproprion
CH2)2N
B1-1328N(H)NMe2OOCO2H——0Ndiethylproprion
B1-13294-(OH)PhOOCO2H——0Ndiethylproprion
B1-13304-(NH2)PhOOCO2H——0Ndiethylproprion
B1-1331EtSOOCO2H——0Ndiltiazem
B1-1332EtOOOCO2H——0Ndiltiazem
B1-1333t-BuOOOCO2H——0Ndiltiazem
B1-1334cyclohexylOOOCO2H——0Ndiltiazem
B1-1335iPrOOOCO2H——0Ndiltiazem
B1-1336PhOOOCO2H——0Ndiltiazem
B1-1337(HOCH2—OOCO2H——0Ndiltiazem
CH2)2N
B1-1338N(H)NMe2OOCO2H——0Ndiltiazem
B1-13394-(OH)PhOOCO2H——0Ndiltiazem
B1-13404-(NH2)PhOOCO2H——0Ndiltiazem
B1-1341EtSOOCO2H——0Ndiphenhydramine
B1-1342EtOOOCO2H——0Ndiphenhydramine
B1-1343t-BuOOOCO2H——0Ndiphenhydramine
B1-1344cyclohexylOOOCO2H——0Ndiphenhydramine
B1-1345iPrOOOCO2H——0Ndiphenhydramine
B1-1346PhOOOCO2H——0Ndiphenhydramine
B1-1347(HOCH2—OOCO2H——0Ndiphenhydramine
CH2)2N
B1-1348N(H)NMe2OOCO2H——0Ndiphenhydramine
B1-13494-(OH)PhOOCO2H——0Ndiphenhydramine
B1-13504-(NH2)PhOOCO2H——0Ndiphenhydramine
B1-1351EtSOOCO2H——0Ndiphenidol
B1-1352EtOOOCO2H——0Ndiphenidol
B1-1353t-BuOOOCO2H——0Ndiphenidol
B1-1354cyclohexylOOOGO2H——0Ndiphenidol
B1-1355iPr0OOCO2H——0Ndiphenidol
B1-1356PhOOOCO2H——0Ndiphenidol
B1-1357(HOCH2—OOCO2H——0Ndiphenidol
CH2)2N
B1-1358N(H)NMe2OOCO2H——0Ndiphenidol
B1-13594-(OH)PhOOCO2H——0Ndiphenidol
B1-13604-(NH2)PhOOCO2H——0Ndiphenidol
B1-1361EtSOOCO2H——0Ndiphenoxylate
B1-1362Et0OOCO2H——0Ndiphenoxylate
B1-1363t-BuOOOCO2H——0Ndiphenoxylate
B1-1364cyclohexylOOOCO2H——0Ndiphenoxylate
B1-1365iPrOOOCO2H——0Ndiphenoxylate
B1-1366PhOOOCO2H——0Ndiphenoxylate
B1-1367(HOCH2—OOCO2H——0Ndiphenoxylate
CH2)2N
B1-1368N(H)NMe2OOCO2H——0Ndiphenoxylate
B1-13694-(OH)PhOOCO2H——0Ndiphenoxylate
B1-13704-(NH2)PhOOCO2H——0Ndiphenoxylate
B1-1371EtSOOCO2H——0Ndoxapram
B1-1372EtOOOCO2H——0Ndoxapram
B1-1373t-BuOOOCO2H——0Ndoxapram
B1-1374cyclohexylOOOCO2H——0Ndoxapram
B1-1375iPrOOOCO2H——0Ndoxapram
B1-1376PhOOOCO2H——0Ndoxapram
B1-1377(HOCH2—OOCO2H——0Ndoxapram
CH2)2N
B1-1378N(H)NMe2OOCO2H——0Ndoxapram
B1-13794-(OH)PhOOCO2H——0Ndoxapram
B1-13804-(NH2)PhOOCO2H——0Ndoxapram
B1-1381EtSOOCO2H——0Ndoxepin
B1-1382EtOOOCO2H——0Ndoxepin
B1-1383t-BuOOOCO2H——0Ndoxepin
B1-1384cyclohexylOOOCO2H——0Ndoxepin
B1-1385iPrOOOCO2H——0Ndoxepm
B1-1386PhOOOCO2H——0Ndoxepin
B1-1387(HOCH2—OOCO2H——0Ndoxepin
CH2)2N
B1-1388N(H)NMe2OOCO2H——0Ndoxepin
B1-13894-(OH)PhOOCO2H——0Ndoxepin
B1-13904-(NH2)PhOOCO2H——0Ndoxepin
B1-1391EtSOOCO2H——0Nfentanyl
B1-1392EtOOOCO2H——0Nfentanyl
B1-1393t-BuOOOCO2H——0Nfentanyl
B1-1394cyclohexylOOOCO2H——0Nfentanyl
B1-1395iPrOOOCO2H——0Nfentanyl
B1-1396PhOOOCO2H——0Nfentanyl
B1-1397(HOCH2—OOCO2H——0Nfentanyl
CH2)2N
B1-1398N(H)NMe2OOCO2H——0Nfentanyl
B1-13994-(OH)PhOOCO2H——0Nfentanyl
B1-14004-(NH2)PhOOCO2H——0Nfentanyl
B1-1401EtSOOCO2H——0Nflavoxate
B1-1402Et0OOCO2H——0Nflavoxate
B1-1403t-BuOOOCO2H——0Nflavoxate
B1-1404cyclohexylOOOCO2H——0Nflavoxate
B1-1405iPrOOOCO2H——0Nflavoxate
B1-1406PhOOOCO2H——0Nflavoxate
B1-1407(HOCH2—OOCO2H——0Nflavoxate
CH2)2N
B1-1408N(H)NMe2OOCO2H——0Nflavoxate
B1-14094-(OH)PhOOOCO2H——0Nflavoxate
B1-14104-(NH2)PhOOCO2H——0Nflavoxate
B1-1411EtSOOCO2H——0Nflurazepam
B1-1412EtOOOCO2H——0Nflurazepam
B1-1413t-BuOOOCO2H——0Nflurazepam
B1-1414cyclohexylOOOCO2H——0Nflurazepam
B1-1415iPrOOOCO2H——0Nflurazepam
B1-1416PhOOOCO2H——0Nflurazepam
B1-1417(HOCH2—OOCO2H——0Nflurazepam
CH2)2N
B1-1418N(H)NMe2OOCO2H——0Nflurazepam
B1-14194-(OH)PhOOCO2H——0Nflurazepam
B1-14204-(NH2)PhOOCO2H——0Nflurazepam
B1-1421EtSOOCO2H——0Nlevomethadyl
B1-1422EtOOOCO2H——0Nlevomethadyl
B1-1423t-BuOOOCO2H——0Nlevomethadyl
B1-1424cyclohexylOOOCO2H——0Nlevornethadyl
B1-1425iPrOOOCO2H——0Nlevomethadyl
B1-1426PhOOOCO2H——0Nlevomethadyl
B1-1427(HOCH2—OOCO2H——0Nlevomethadyl
CH2)2N
B1-1428N(H)NMe2OOCO2H——0Nlevomethadyl
B1-14294-(OH)PhOOCO2H——0Nlevomethadyl
B1-14304-(NH2)PhOOCO2H——0Nlevomethadyl
B1-1431EtSOOCO2H——0Nloratadine
B1-1432EtOOOCO2H——0Nloratadine
B1-1433t-BuOOOCO2H——0Nloratadine
B1-1434cyclohexylOOOCO2H——0Nloratadine
B1-1435iPrOOOCO2H——0Nloratadine
B1-1436PhOOOCO2H——0Nloratadine
B1-1437(HOCH2—OOCO2H——0Nloratadine
CH2)2N
B1-1438N(H)NMe2OOCO2H——0Nloratadine
B1-14394-(OH)PhOOCO2H——0Nloratadine
B1-14404-(NH2)PhOOCO2H——0Nloratadine
B1-1441EtSOOCO2H——0Nmechlorethamine
B1-1442EtOOOCO2H——0Nmechlorethamine
B1-1443t-BuOOOCO2H——0Nmechlorethamine
B1-1444cyclohexylOOOCO2H——0Nmechlorethamine
B1-1445iPrOOOCO2H——0Nmechlorethamirie
B1-1446PhOOOCO2H——0Nmechlorethamine
B1-1447(HOCH2—OOCO2H——0Nmechlorethamine
CH2)2N
B1-1448N(H)NMe2OOCO2H——0Nmechlorethamine
B1-14494-(OH)PhOOCO2H——0Nmechlorethainine
B1-14504-(NH2)PhOOCO2H——0Nmechlorethamine
B1-1451EtSOOCO2H——0Nmeperidine
B1-1452EtOOOCO2H——0Nmeperidine
B1-1453t-BuOOOCO2H——0Nmeperidine
B1-1454cyclohexylOOOCO2H——0Nmeperidine
B1-1455iPrOOOCO2H——0Nmeperidine
B1-1456PhOOOCO2H——0Nmeperidine
B1-1457(HOCH2—OOCO2H——0Nmeperidine
CH2)2N
B1-1458N(H)NMe2OOCO2H——0Nmeperidine
B1-14594-(OH)PhOOCO2H——0Nmeperidine
B1-14604-(NH2)PhOOCO2H——0Nmeperidine
B1-1461EtSOOCO2H——0Nmepivacaine
B1-1462EtOOOCO2H——0Nmepivacaine
B1-1463t-BuOOOCO2H——0Nmepivacaine
B1-1464cyclohexylOOOCO2H——0Nmepivacaine
B1-1465iPrOOOCO2H——0Nmepivacame
B1-1466PhOOOCO2H——0Nmepivacaine
B1-1467(HOCH2—OOCO2H——0Nmepivacaine
CH2)2N
B1-1468N(H)NMe2OOCO2H——0Nmepivacaine
B1-14694-(OH)PhOOCO2H——0Nmepivacaine
B1-14704-(NH2)PhOOCO2H——0Nmepivacaine
B1-1471EtSOOCO2H——0Nmethadone
B1-1472EtOOOCO2H——0Nmethadone
B1-1473t-BuOOOCO2H——0Nmethadone
B1-1474cyclohexylOOOCO2H——0Nmethadone
B1-1475iPrOOOCO2H——0Nmethadone
B1- 1476PhOOOCO2H——0Nmethadone
B1-1477(HOCH2—OOCOdI——0Nmethadone
CH2)2N
B1-1478N(H)NMe2OOCO2H——0Nmethadone
B1-14794-(OH)PhOOCO2H——0Nmethadone
B1-14804-(NH2)PhOOCO2H——0Nmethadone
B1-1481EtSOOCO2H——0Nminoxidil
B1-1482EtOOOCO2H——0Nminoxidil
B1-1483t-BuOOOCO2H——0Nminoxidil
B1-1484cyclohexylOOOCO2H——0Nminoxidil
B1-1485iPrOOOCO2H——0Nminoxidil
B1-1486PhOOOCO2H——0Nminoxidil
B1-1487(HOCH2—OOCO2H——0Nminoxidil
CH2)2N
B1-1488N(H)NMe2OOCO2H——0Nmininoxidil
B1-14894-(OH)PhOOCO2H——0Nminoxidil
B1-14904-(NH2)PhOOCO2H——0Nminoxidil
B1-1491EtSOOCO2H——0Nnaftifine
B1-1492EtOOOCO2H——0Nnaftifine
B1-1493t-BuOOOCO2H——0Nnaftffine
B1-1494cyclohexylOOOCO2H——0Nnaftifine
B1-1495iPrOOOCO2H——0Nnaftifine
B1-1496PhOOOCO2H——0Nnaftifine
B1-1497(HOCH2—OOCO2H——0Nnaftifine
CH2)2N
B1-1498N(H)NMe2OOCO2H——0Nnaftifine
B1-14994-(OH)PhOOCO2H——0Nnaftifine
B1-15004-(NH2)PhOOCO2H——0Nnaftifine
B1-1501EtSOOCO2H——0Norphenadrine
B1-1502EtOOOCO2H——0Norphenadrine
B1-1503t-BuOOOCO2H——0Norphenadrine
B1-1504cyclohexylOOOCO2H——0Norphenadrine
B1-1505iPrOOOCO2H——0Norphenadrine
B1-1506PhOOOCO2H——0Norphenadrine
B1-1507(HOCH2—OOCO2H——0Norphenadrine
CH2)2N
B1-1508N(H)NMe2OOCO2H——0Norphenadrine
B1-15094-(OH)PhOOCO2H——0Norphenadrine
B1-15104-(NH2)PhOOCO2H——0Norphenadrine
B1-1511EtSOOCO2H——0Noxybutynin
B1-1512EtOOOCO2H——0Noxybutynin
B1-1513t-BuOOOCO2H——0Noxybutynin
B1-1514cyclohexylOOOCO2H——0Noxybutynin
B1-1515iPrOOOCO2H——0Noxybutynin
B1-1516PhOOOCO2H——0Noxybutynin
B1-1517(HOCH2—OOCO2H——0Noxybutynin
CH2)2N
B1-1518N(H)NMe2OOCO2H——0Noxybutynin
B1-15194-(OH)PhOOCO2H——0Noxybutynin
B1-15204-(NH2)PhOOCO2H——0Noxybutynin
B1-1521EtSOOCO2H——0Noxymetazoline
B1-1522EtOOOCO2H——0Noxymetazoline
B1-1523t-BuOOOCO2H——0Noxymetazoline
B1-1524cyclohexylOOOCO2H——0Noxymetazoline
B1-1525iPrOOOCO2H——0Noxymetazoline
B1-1526PhOOOCO2H——0Noxymetazoline
B1-1527(HOCH2—OOCO2H——0Noxymetazoline
CH2)2N
B1-1528N(H)NMe2OOCO2H——0Noxymetazoline
B1-15294-(OH)PhOOCO2H——0Noxymetazoline
B1-15304-(NH2)PhOOCO2H——0Noxymetazoline
B1-1531EtSOOCO2H——0Nphenoxybenzamine
B1-1532EtOOOCO2H——0Nphenoxybenzamine
B1-1533t-BuOOOCO2H——0Nphenoxybenzamine
B1-1534cyclohexylOOOCO2H——0Nphenoxybenzamine
B1-1535iPrOOOCO2H——0Nphenoxybenzamine
B1-1536PhOOOCO2H——0Nphenoxybenzamine
B1-1537(HOCH2—OOCOAl——0Nphenoxybenzamine
CH2)2N
B1-1538N(H)NMe2OOCO2H——0Nphenoxybenzamine
B1-15394-(OH)PhOOCO2H——0Nphenoxybenzamine
B1-15404-(NH2)PhOOCO2H——0Nphenoxybenzamine
B1-1541EtSOOCO2H——0Npilocarpine
B1-1542EtOOOCO2H——0Npilocarpine
B1-1543t-BuOOOCO2H——0Npilocarpine
B1-1544cyclohexylOOOCO2H——0Npilocarpine
B1-1545iPrOOOCO2H——0Npilocarpine
B1-1546PhOOOCO2H——0Npilocarpine
B1-1547(HOCH2—OOCO2H——0Npilocarpine
CH2)2N
B1-1548N(H)NMe2OOCO2H——0Npilocarpine
B1-15494-(OH)PhOOCO2H——0Npilocarpine
B1-15504-(NH2)PhOOCO2H——0Npilocarpine
B1-1551EtSOOCO2H——0Npyrazinamide
B1-1552EtOOOCO2H——0Npyrazinamide
B1-1553t-BuOOOCO2H——0Npyrazinamide
B1-1554cyclohexylOOOCO2H——0Npyrazinamide
B1-1555iPrOOOCO2H——0Npyrazinamide
B1-1556PhOOOCO2H——0Npyrazinamide
B1-1557(HOCH2—OOCO2H——0Npyrazinamide
CH2)2N
B1-1558N(H)NMe2OOCO2H——0Npyrazinamide
B1-15594-(OH)PhOOCO2H——0Npyrazinamide
B1-15604-(NH2)PhOOCO2H——0Npyrazinamide
B1-1561EtSOOCO2H——0Npyroxidine
B1-1562EtOOOCO2H——0Npyroxidine
B1-1563t-BuOOOCO2H——0Npyroxidine
B1-1564cyclohexylOOOCO2H——0Npyroxidine
B1-1565iPrOOOCO2H——0Npyroxidine
B1-1566PhOOOCO2H——0Npyroxidine
B1-1567(HOCH2—OOCO2H——0Npyroxidine
CH2)2N
B1-1568N(H)NMe2OOCO2H——0Npyroxidine
B1-15694-(OH)PhOOCO2H——0Npyroxidine
B1-15704-(NH2)PhOOCO2H——0Npyroxidine
B1-1571EtSOOCO2H——0Nrisperidone
B1-1572EtOOOCO2H——0Nrisperidone
B1-1573t-BuOOOCO2H——0Nrisperidone
B1-1574cyclohexylOOOCO2H——0Nrisperidone
B1-1575iPrOOOCO2H——0Nrisperidone
B1-1576Ph0OOCO2H——0Nrisperidone
B1-1577(HOCH2—OOCO2H——0Nrisperidone
CH2)2N
B1-1578N(H)NMe2OOCO2H——0Nrisperidone
B1-15794-(OH)PhOOCO2H——0Nrisperidone
B1-15804-(NH2)PhOOCO2H——0Nrisperidone
B1-1581EtSOOCO2H——0Nsufentanil
B1-1582EtOOOCO2H——0Nsufentanil
B1-1583t-BuOOOCO2H——0Nsufentanil
B1-1584cyclohexylOOOCO2H——0Nsufentanil
B1-1585iPrOOOCO2H——0Nsufentanil
B1-1586PhOOOCO2H——0Nsufentanil
B1-1587(HOCH2—OOCO2H——0Nsufentanil
CH2)2N
B1-1588N(H)NMe2OOCO2H——0Nsufentanil
B1-15894-(OH)PhOOCO2H——0Nsufentanil
B1-15904-(NH2)PhOOCO2H——0Nsufentanil
B1-1591EtSOOCO2H——0Ntamoxifen
B1-1592EtOOOCO2H——0Ntamoxifen
B1-1593t-BuOOOCO2H——0Ntamoxifen
B1-1594cyclohexylOOOCO2H——0Ntamoxifen
B1-1595iPrOOOCO2H——0Ntamoxifen
B1-1596PhOOOCO2H——0Ntamoxifen
B1-1597(HOCH2—OOCO2H——0Ntamoxifen
CH2)2N
B1-1598N(H)NMe2OOCO2H——0Ntamoxifen
B1-15994-(OH)PhOOCO2H——0Ntamoxifen
B1-16004-(NH2)PhOOCO2H——0Ntamoxifen
B1-1601EtSOOCO2H——0Nterbinafine
B1-1602EtOOOCO2H——0Nterbinafine
B1-1603t-BuOOOCO2H——0Nterbinafine
B1-1604cyclohexylOOOCO2H——0Nterbinafine
B1-1605iPrOOOCO2H——0Nterbinafine
B1-1606PhOOOCO2H——0Nterbinafine
B1-1607(HOCH2—OOCO2H——0Nterbinafine
CH2)2N
B1-1608N(H)NMe2OOCO2H——0Nterbinafine
B1-16094-(OH)PhOOCO2H——0Nterbinafine
B1-16104-(NH2)PhOOCO2H——0Nterbinafine
B1-1611EtSOOCO2H——0Ntrihexyphenidyl
B1-1612EtOOOCO2H——0Ntrihexyphenidyl
B1-1613t-BuOOOCO2H——0Ntrihexyphenidyl
B1-1614cyclohexylOOOCO2H——0Ntrihexyphenidyl
B1-1615iPrOOOCO2H——0Ntrihexyphenidyl
B1-1616PhOOOCO2H——0Ntrihexyphenidyl
B1-1617(HOCH2—OOCO2H——0Ntrihexyphenidyl
CH2)2N
B1-1618N(H)NMe2OOCO2H——0Ntrihexyphenidyl
B1-16194-(OH)PhOOCO2H——0Ntrihexyphenidyl
B1-16204-(NH2)PhOOCO2H——0Ntrihexyphenidyl
B1-1621EtSOOCO2H——0Ntroleandomycin
B1-1622EtOOOCO2H——0Ntroleandomycin
B1-1623t-BuOOOCO2H——0Ntroleandomycin
Bl-1624cyclohexylOOOCO2H——0Ntroleandomycin
B1-1625iPr0OOCO2H——0Ntroleandomycin
B1-1626PhOOOCO2H——0Ntroleandomycin
B1-1627(HOCH2—OOCO2H——0Ntroleandomycin
CH2)2N
B1-1628N(H)NMe2OOCO2H——0Ntroleandomycin
B1-16294-(OH)PhOOCO2H——0Ntroleandomycin
B1-16304-(NH2)PhOOCO2H——0Ntroleandomycin
B1-1631EtSOOCO2H——0Nverapamil
B1-1632EtOOOCO2H——0Nverapamil
B1-1633t-BuOOOCO2H——0Nverapamil
B1-1634cyclohexylOOOCO2H——0Nverapamil
B1-1635iPrOOOCO2H——0Nverapamil
B1-1636PhOOOCO2H——0Nverapamil
B1-1637(HOCH2—OOCO2H——0Nverapamil
CH2)2N
B1-1638N(H)NMe2OOCO2H——0Nverapamil
B1-16394-(OH)PhOOCO2H——0Nverapamil
B1-16404-(NH2)PhOOCO2H——0Nverapamil
B1-1641EtSOOCO2H——0Ncaffeine
B1-1642EtOOOCO2H——0Ncaffeine
B1-1643t-BuOOOCO2H——0Ncaffeine
B1-1644cyclohexylOOOCO2H——0Ncaffeine
B1-1645iPrOOOCO2H——0Ncaffeine
B1-1646PhOOOCO2H——0Ncaffeine
B1-1647(HOCH2—OOCO2H——0Ncaffeine
CH2)2N
B1-1648N(H)NMe2OOCO2H——0Ncaffeine
B1-16494-(OH)PhOOCO2H——0Ncaffeine
B1-16504-(NH2)PhOOCO2H——0Ncaffeine
B1-1651EtSOOCO2H——0Ncyproheptadine
B1-1652EtOOOCO2H——0Ncyproheptadine
B1-1653t-BuOOOCO2H——0Ncyproheptadine
B1-1654cyclohexylOOOCO2H——0Ncyproheptadine
B1-1655iPrOOOCO2H——0Ncyproheptadine
B1-1656PhOOOCO2H——0Ncyproheptadine
B1-1657(HOCH2—OOCO2H——0Ncyproheptadine
CH2)2N
B1-1658N(H)NMe2OOCO2H——0Ncyproheptadine
B1-16594-(OH)PhOOCO2H——0Ncyproheptadine
B1-16604-(NH2)PhOOCO2H——0Ncyproheptadine
B1-1661EtSOOCO2H——0Npramoxine
B1-1662EtOOOCO2H——0Npramoxine
B1-1663t-BuOOOCO2H——0Npramoxine
B1-1664cyclohexylOOOCO2H——0Npramoxine
B1-1665iPrOO0CO2H——0Npramoxine
B1-1666PhOOOCO2H——0Npramoxine
B1-1667(HOCH2—OOCO2H——0Npramoxine
CH2)2N
B1-1668N(H)NMe2OOCO2H——0Npramoxine
B1-16694-(OH)PhOOCO2H——0Npramoxine
B1-16704-(NH2)PhOOCO2H——0Npramoxine
B1-1671EtSOOCO2H——0Oiodoquinol
B1-1672EtOOOCO2H——0Oiodoquinol
B1-1673t-BuOOOCO2H——0Oiodoquinol
B1-1674cyclohexylOOOCO2H——0Oiodoquinol
B1-1675iPrOOOCO2H——0Oiodoquinol
B1-1676PhOOOCO2H——0Oiodoquinol
B1-1677(HOCH2—OOCO2H——0Oiodoquinol
CH2)2N
B1-1678N(H)NMe2OOCO2H——0Oiodoquinol
B1-16794-(OH)PhOOCO2H——0Oiodoquinol
B1-16804-(NH2)PhOOCO2H——0Oiodoquinol
B1-1681EtSOOCO2H——0Ometronidazole
B1-1682EtOOOCO2H——0Ometronidazole
B1-1683t-BuOOOCO2H——0Ometronidazole
B1-1684cyclohexylOOOCO2H——0Ometronidazole
B1-1685iPrOOOCO2H——0Ometronidazole
B1-1686PhOOOCO2H——0Ometronidazole
B1-1687(HOCH2—OOCO2H——0Ometronidazole
CH2)2N
B1-1688N(H)NMe2OOCO2H——0Ometronidazole
B1-16894-(OH)PhOOCO2H——0Ometronidazole
B1-16904-(NH2)PhOOCO2H——0Ometronidazole
B1-1691EtSOOCO2H——0Npapaverine
B1-1692EtOOOCO2H——0Npapaverine
B1-1693t-BuOOOCO2H——0Npapaverine
B1-1694cyclohexylOOOCO2H——0Npapaverine
B1-1695iPrOOOCO2H——0Npapaverme
B1-1696PhOOOCO2H——0Npapaverine
B1-1697(HOCH2—OOCO2H——0Npapaverine
CH2)2N
B1-1698N(H)NMe2OOCO2H——0Npapaverine
B1-16994-(OH)PhOOCO2H——0Npapaverine
B1-17004-(NH2)PhOOCO2H——0Npapaverine
B1-1701EtSOOCO2H——0Ntropicamide
B1-1702EtOOOCO2H——0Ntropicamide
B1-1703t-BuOOOCO2H——0Ntropicamide
B1-1704cyclohexylOOOCO2H——0Ntropicamide
B1-1705iPrOOOCO2H——0Ntropicamide
B1-1706PhOOOCO2H——0Ntropicamide
B1-1707(HOCH2—OOCO2H——0Ntropicamide
CH2)2N
B1-1708N(H)NMe2OOCO2H——0Ntropicamide
B1-17094-(OH)PhOOCO2H——0Ntropicamide
B1-17104-(NH2)PhOOCO2H——0Ntropicamide
B1-1711EtSOOCO2H——0Nhalazepam
B1-1712EtOOOCO2H——0Nhalazep am
B1-1713t-BuOOOCO2H——0Nhalazepam
B1-1714cyclohexylOOOCO2H——0Nhalazepam
B1-1715iPrOOOCO2H——0Nhalazepam
B1-1716PhOOOCO2H——0Nhalazepam
B1-1717(HOCH2—OOCO2H——0Nhalazepam
CH2)2N
B1-1718N(H)NMe2OOCO2H——0Nhalazepam
B1-17194-(OH)PhOOCO2H——0Nhalazepam
B1-17204-(NH2)PhOOCO2H——0Nhalazepam
B1-1721EtSOOCO2H——0Omazindol
B1-1722EtOOOCO2H——0Omazindol
B1-1723t-BuOOOCO2H——0Omazindol
B1-1724cyclohexylOOOCO2H——0Omazindol
B1-1725iPrOOOCO2H——0Omazindol
B1-1726PhOOOCO2H——0Omazindol
B1-1727(HOCH2—OOCO2H——0Omazindol
CH2)2N
B1-1728N(H)NMe2OOCO2H——0Omazindol
B1-17294-(OH)PhOOCO2H——0Omazindol
B1-17304-(NH2)PhOOCO2H——0Omazindol
B1-1731EtSOOCO2H——0Ohydroxyitraconazole
B1-1732EtOOOCO2H——0Ohydroxyitraconazole
B1-1733t-BuOOOCO2H——0Ohydroxyitraconazole
B1-1734cyclohexylOOOCO2H——0Ohydroxyitraconazole
B1-1735iPrOOOCO2H——0Ohydroxyitraconazole
B1-1736PhOOOCO2H——0Ohydroxyitraconazole
B1-1737(HOCH2—OOCO2H——0Ohydroxyitraconazole
CH2)2N
B1-1738N(H)NMe2OOCO2H——0Ohydroxyitraconazole
B1-17394-(OH)PhOOCO2H——0Ohydroxyitraconazole
B1-17404-(NH2)PhOOCO2H——0Ohydroxyitraconazole
B1-1741EtSOOCO2H——0Oposaconazole
B1-1742EtOOOCO2H——0Oposaconazole
B1-1743t-BuOOOCO2H——0Oposaconazole
B1-1744cyclohexylOOOCO2H——0Oposaconazole
B1-1745iPrOOOCO2H——0Oposaconazole
B1-1746PhOOOCO2H——0Oposaconazole
B1-1747(HOCH2—OOCO2H——0Oposaconazole
CH2)2N
B1-1748N(H)NMe2OOCO2H——0Oposaconazole
B1-17494-(OH)PhOOCO2H——0Oposaconazole
B1-17504-(NH2)PhOOCO2H——0Oposaconazole
B1-1751EtSOOCO2H——0Ovoriconazole
B1-1752EtOOOCO2H——0Ovoriconazole
B1-1753t-BuOOOCO2H——0Ovoriconazole
B1-1754cyclohexylOOOCO2H——0Ovoriconazole
B1-1755iPrOOOCO2H——0Ovoriconazole
B1-1756PhOOOCO2H——0Ovoriconazole
B1-1757(HOCH2—OOCO2H——0Ovoriconazole
CH2)2N
B1-1758N(H)NMe2OOCO2H——0Ovoriconazole
B1-17594-(OH)PhOOCO2H——0Ovoriconazole
B1-17604-(NH2)PhOOCO2H——0Ovoriconazole
B1-1761EtSOOCO2H——0Ofluconazole
B1-1762EtOOOCO2H——0Ofluconazole
B1-1763t-BuOOOCO2H——0Ofluconazole
B1-1764cyclohexylOOOCO2H——0Ofluconazole
B1-1765iPrOOOCO2H——0Ofluconazole
B1-1766PhOOOCO2H——0Ofluconazole
B1-1767(HOCH2—OOCO2H——0Ofluconazole
CH2)2N
B1-1768N(H)NMe2OOCO2H——0Ofluconazole
B1-17694-(OH)PhOOCO2H——0Ofluconazole
B1-17704-(NH2)PhOOCO2H——0Ofluconazole
B1-1771EtSOOCO2H——0Ogenaconazole
B1-1772EtOOOCO2H——0Ogenaconazole
B1-1773t-BuOOOCO2H——0Ogenaconazole
B1-1774cyclohexylOOOCO2H——0Ogenaconazole
B1-1775iPrOOOCO2H——0Ogenaconazole
B1-1776PhOOOCO2H——0Ogenaconazole
B1-1777(HOCH2—OOCO2H——0Ogenaconazole
CH2)2N
B1-1778N(H)NMe2OOCO2H——0Ogenaconazole
B1-17794-(OH)PhOOCO2H——0Ogenaconazole
B1-17804-(NH2)PhOOCO2H——0Ogenaconazole
B1-1781EtSOOCO2H——0Naliconazole
B1-1782EtOOOCO2H——0Naliconazole
B1-1783t-BuOOOCO2H——0Naliconazole
B1-1784cyclohexylOOOCO2H——0Naliconazole
B1-1785iPrOOOCO2H——0Naliconazole
B1-1786PhOOOCO2H——0Naliconazole
B1-1787(HOCH2—OOCO2H——0Naliconazole
CH2)2N
B1-1788N(H)NMe2OOCO2H——0Naliconazole
B1-17894-(OH)PhOOCO2H——0Naliconazole
B1-17904-(NH2)PhOOCO2H——0Naliconazole
B1-1791EtSOOCO2H——0Nbeciconazole
B1-1792EtOOOCO2H——0Nbecliconazole
B1-1793t-BuOOOCO2H——0Nbeciconazole
B1-1794cyclohexylOOOCO2H——0Nbecliconazole
B1-1795iPrOOOCO2H——0Nbecliconazole
B1-1796PhOOOCO2H——0Nbeciconazole
B1-1797(HOCH2—OOCO2H——0Nbeciconazole
CH2)2N
B1-1798N(H)NMe2OOCO2H——0Nbeciconazole
B1-17994-(OH)PhOOCO2H——0Nbecliconazole
B1-18004-(NH2)PhOOCO2H——0Nbecliconazole
B1-1801EtSOOCO2H——0Nbrolaconazole
B1-1802EtOOOCO2H——0Nbrolaconazole
B1-1803t-BuOOOCO2H——0Nbrolaconazole
B1-1804cyclohexylOOOCO2H——0Nbrolaconazole
B1-1805iPrOOOCO2H——0Nbrolaconazole
B1-1806PhOOOCO2H——0Nbrolaconazole
B1-1807(HOCH2—OOCO2H——0Nbrolaconazole
CH2)2N
B1-1808N(H)NMe2OOCO2H——0Nbrolaconazole
B1-18094-(OH)PhOOCO2H——0Nbrolaconazole
B1-18104-(NH2)PhOOCO2H——0Nbrolaconazole
B1-1811EtSOOCO2H——0Nbutaconazole
B1-1812EtOOOCO2H——0Nbutaconazole
B1-1813t-BuOOOCO2H——0Nbutaconazole
B1-1814cyclohexylOOOCO2H——0Nbutaconazole
B1-1815iPrOOOCO2H——0Nbutaconazole
B1-1816PhOOOCO2H——0Nbutaconazole
B1-1817(HOCH2—OOCO2H——0Nbutaconazole
CH2)2N
B1-1818N(H)NMe2OOCO2H——0Nbutaconazole
B1-18194-(OH)PhOOCO2H——0Nbutaconazole
B1-18204-(NH2)PhOOCO2H——0Nbutaconazole
B1-1821EtSOOCO2H——0Nclotrimazole
B1-1822EtOOOCO2H——0Nclotrimazole
B1-1823t-BuOOOCO2H——0Nclotrimazole
B1-1824cyclohexylOOOCO2H——0Nclotrimazole
B1-1825iPrOOOCO2H——0Nclotrimazole
B1-1826PhOOOCO2H——0Nclotrimazole
B1-1827(HOCH2—OOCO2H——0Nclotrimazole
CH2)2N
B1-1828N(H)NMe2OOCO2H——0Nclotrimazole
B1-18294-(OH)PhOOCO2H——0Nclotrimazole
B1-18304-(NH2)PhOOCO2H——0Nclotrimazole
B1-1831EtSOOCO2H——0Ncroconazole
B1-1832EtOOOCO2H——0Ncroconazole
B1-1833t-BuOOOCO2H——0Ncroconazole
B1-1834cyclohexylOOOCO2H——0Ncroconazole
B1-1835iPrOOOCO2H——0Ncroconazole
B1-1836PhOOOCO2H——0Ncroconazole
B1-1837(HOCH2—OOCO2H——0Ncroconazole
CH2)2N
B1-1838N(H)NMe2OOCO2H——0Ncroconazole
B1-18394-(OH)PhOOCO2H——0Ncroconazole
B1-18404-(NH2)PhOOCO2H——0Ncroconazole
B1-1841EtSOOCO2H——0Neconazole
B1-1842EtOOOCO2H——0Neconazole
B1-1843t-BuOOOCO2H——0Neconazole
B1-1844cyclohexylOOOCO2H——0Neconazole
B1-1845iPrOOOCO2H——0Neconazole
B1-1846PhOOOCOdI——0Neconazole
B1-1847(HOCH2—OOCO2H——0Neconazole
CH2)2N
B1-1848N(H)NMe2OOCO2H——0Neconazole
B1-18494-(OH)PhOOCO2H——0Neconazole
B1-18504-(NH2)PhOOCO2H——0Neconazole
B1-1851EtSOOCO2H——0Ndemoconazole
B1-1852EtOOOCO2H——0Ndemoconazole
B1-1853t-BuOOOCO2H——0Ndemoconazole
B1-1854cyclohexylOOOCO2H——0Ndemoconazole
B1-1855iPrOOOCO2H——0Ndemoconazole
B1-1856PhOOOCO2H——0Ndemoconazole
B1-1857(HOCH2—OOCO2H——0Ndemoconazole
CH2)2N
B1-1858N(H)NMe2OOCO2H——0Ndemoconazole
B1-18594-(OH)PhOOCO2H——0Ndemoconazole
B1-18604-(NH2)PhOOCO2H——0Ndemoconazole
B1-1861EtSOOCO2H——0Ndoconazole
B1-1862EtOOOCO2H——0Ndoconazole
B1-1863t-BuOOOCO2H——0Ndoconazole
B1-1864cyclohexylOOOCO2H——0Ndoconazole
B1-1865iPrOOOCO2H——0Ndoconazole
B1-1866PhOOOCO2H——0Ndoconazole
B1-1867(HOCH2—OOCO2H——0Ndoconazole
CH2)2N
B1-1868N(H)NMe2OOCO2H——0Ndoconazole
B1-18694-(OH)PhOOCO2H——0Ndoconazole
B1-18704-(NH2)PhOOCO2H——0Ndoconazole
B1-1871EtSOOCO2H——0Nfenticonazole
B1-1872EtOOOCO2H——0Nfenticonazole
B1-1873t-BuOOOCO2H——0Nfenticonazole
B1-1874cyclohexylOOOCO2H——0Nfenticonazole
B1- 1875iPrOOOCO2H——0Nfenticonazole
B1-1876PhOOOCO2H——0Nfenticonazole
B1-1877(HOCH2—OOCO2H——0Nfenticonazole
CH2)2N
B1-1878N(H)NMe2OOCO2H——0Nfenticonazole
B1-18794-(OH)PhOOCO2H——0Nfenticonazole
B1-18804-(NH2)PhOOCO2H——0Nfenticonazole
B1-1881EtSOOCO2H——0Neberconazole
B1-1882EtOOOCO2H——0Neberconazole
B1-1883t-BuOOOCO2H——0Neberconazole
B1-1884cyclohexylOOOCO2H——0Neberconazole
B1-1885iPrOOOCO2H——0Neberconazole
B1-1886PhOOOCO2H——0Neberconazole
B1-1887(HOCH2—OOCO2H——0Neberconazole
CH2)2N
B1-1888N(H)NMe2OOCO2H——0Neberconazole
B1-18894-(OH)PhOOCO2H——0Neberconazole
B1-18904-(NH2)PhOOCO2H——0Neberconazole
B1-1891EtSOOCO2H——0Nisoconazole
B1-1892EtOO0CO2H——0Nisoconazole
B1-1893t-BuOOOCO2H——0Nisoconazole
B1-1894cyclohexylOOOCO2H——0Nisoconazole
B1-1895iPrOOOCO2H——0Nisoconazole
B1-1896PhOOOCO2H——0Nisoconazole
B1-1897(HOCH2—OOCO2H——0Nisoconazole
CH2)2N
B1-1898N(H)NMe2OOCO2H——0Nisoconazole
B1-18994-(OH)PhOOCO2H——0Nisoconazole
B1-19004-(NH2)PhOOCO2H——0Nisoconazole
B1-1901EtSOOCO2H——0Nmiconazole
B1-1902EtOOOCO2H——0Nmiconazole
B1-1903t-BuOOOCO2H——0Nmiconazole
B1-1904cyclohexylOOOCO2H——0Nmiconazole
B1-1905iPrOOOCO2H——0Nmiconazole
B1-1906PhOOOCO2H——0Nmiconazole
B1-1907(HOCH2—OOCO2H——0Nmiconazole
CH2)2N
B1-1908N(H)NMe2OOCO2H——0Nmiconazole
B1-19094-(OH)PhOOCO2H——0Nmiconazole
B1-19104-(NH2)PhOOCO2H——0Nmiconazole
B1-1911EtSOOCO2H——0Nneticonazole
B1-1912EtOOOCO2H——0Nneticonazole
B1-1913t-BuOOOCO2H——0Nneticonazok
B1-1914cyclohexylOOOCO2H——0Nneticonazole
B1-1915iPrOOOCO2H——0Nneticonazole
B1-1916PhOOOCO2H——0Nneticonazole
B1-1917(HOCH2—OOCO2H——0Nneticonazole
CH2)2N
B1-1918N(H)NMe2OOCO2H——0Nneticonazole
B1-19194-(OH)PhOOCO2H——0Nneticonazole
B1-19204-(NH2)PhOOCO2H——0Nneticonazole
B1-1921EtSOOCO2H——0Nomoconazole
B1-1922EtOOOCO2H——0Nomoconazole
B1-1923t-BuOOOCO2H——0Nomoconazole
B1-1924cyclohexylOOOCO2H——0Nomoconazole
B1-1925iPrOOOCO2H——0Nomoconazole
B1-1926PhOOOCO2H——0Nomoconazole
B1-1927(HOCH2—OOCO2H——0Nomoconazole
CH2)2N
B1-1928N(H)NMe2OOCO2H——0Nomoconazole
B1-19294-(OH)PhOOCO2H——0Nomoconazole
B1-19304-(NH2)PhOOCO2H——0Nomoconazole
B1-1931EtSOOCO2H——0Norconazole
B1-1932EtOOOCO2H——0Norconazole
B1-1933t-BuOOOCO2H——0Norconazole
B1-1934cyclohexylOOOCO2H——0Norconazole
B1-1935iPrOOOCO2H——0Norconazole
B1-1936PhOOOCO2H——0Norconazole
B1-1937(HOCH2—OOCO2H——0Norconazole
CH2)2N
B1-1938N(H)NMe2OOCO2H——0Norconazole
B1-19394-(OH)PhOOCO2H——0Norconazole
B1-19404-(NH2)PhOOCO2H——0Norconazole
B1-1941EtSOOCO2H——0Noxiconazole
B1-1942EtOOOCO2H——0Noxiconazole
B1-1943tBuOO0CO2H——0Noxiconazole
B1-1944cyclohexylOOOCO2H——0Noxiconazole
B1-1945iPrOOOCO2H——0Noxiconazole
B1-1946PhOOOCO2H——0Noxiconazole
B1-1947(HOCH2—OOCO2H——0Noxiconazole
CH2)2N
B1-1948N(H)NMe2OOCO2H——0Noxiconazole
B1-19494-(OH)PhOOCO2H——0Noxiconazole
B1-19504-(NH2)PhOOCO2H——0Noxiconazole
B1-1951EtSOOCO2H——0Nparconazole
B1-1952EtOOOCO2H——0Nparconazole
B1-1953t-BuOOOCO2H——0Nparconazole
B1-1954cyclohexylOOOCO2H——0Nparconazole
B1-1955iPrOOOCO2H——0Nparconazole
B1-1956PhOO0CO2H——0Nparconazole
B1-1957(HOCH2—OOCO2H——0Nparconazole
CH2)2N
B1-1958N(H)NMe2OOCO2H——0Nparconazole
B1-19594-(OH)PhOOCO2H——0Nparconazole
B1-19604-(NH2)PhOOCO2H——0Nparconazole
B1-1961EtSOOCO2H——0Nravuconazole
B1-1962EtOOOCO2H——0Nravuconazole
B1-1963t-BuOOOCO2H——0Nravuconazole
B1-1964cyclohexylOOOCO2H——0Nravuconazole
B1-1965iPrOOOCO2H——0Nravuconazole
B1-1966PhOOOCO2H——0Nravuconazole
B1-1967(HOCH2—OOCO2H——0Nravuconazole
CH2)2N
B1-1968N(H)NMe2OOCO2H——0Nravuconazole
B1-19694-(OH)PhOOCO2H——0Nravuconazole
B1-19704-(NH2)PhOOCO2H——0Nravuconazole
B1-1971EtSOOCO2H——0Nsertaconazole
B1-1972EtOOOCO2H——0Nsertaconazole
B1-1973t-BuOOOCO2H——0Nsertaconazole
B1-1974cyclohexylOOOCO2H——0Nsertaconazole
B1-1975iPrOOOCO2H——0Nsertaconazole
B1-1976PhOOOCO2H——0Nsertaconazole
B1-1977(HOCH2—OOCO2H——0Nsertaconazole
CH2)2N
B1-1978N(H)NMe2OOCO2H——0Nsertaconazole
B1-19794-(OH)PhOOCO2H——0Nsertaconazole
B1-19804-(NH2)PhOOCO2H——0Nsertaconazole
B1-1981EtSOOCO2H——0Nsulconazole
B1-1982EtOOOCO2H——0Nsulconazole
B1-1983t-BuOOOCO2H——0Nsulconazole
B1-1984cyclohexylOOOCO2H——0Nsulconazole
B1-1985iPrOOOCO2H——0Nsulconazole
B1-1986PhOOOCO2H——0Nsulconazole
B1-1987(HOCH2—OOCO2H——0Nsulconazole
CH2)2N
B1-1988N(H)NMe2OOCO2H——0Nsulconazole
B1-19894-(OH)PhOOCO2H——0Nsulconazole
B1-19904-(NH2)PhOOCO2H——0Nsulconazole
B1-1991EtSOOCO2H——0Ntioconazole
B1-1992EtOOOCO2H——0Ntioconazole
B1-1993t-BuOOOCO2H——0Ntioconazole
B1-1994cyclohexylOOOCO2H——0Ntioconazole
B1-1995iPrOOOCO2H——0Ntioconazole
B1-1996Ph0OOCO2H——0Ntioconazole
B1-1997(HOCH2—OOCO2H——0Ntioconazole
CH2)2N
B1-1998N(H)NMe2OOCO2H——0Ntioconazole
B1-19994-(OH)PhOOCO2H——0Ntioconazole
B1-20004-(NH2)PhOOCO2H——0Ntioconazole
B1-2001EtSOOCO2H——0Nvalconazole
B1-2002EtOOOCO2H——0Nvalconazole
B1-2003t-BuOOOCO2H——0Nvalconazole
B1-2004cyclohexylOOOCO2H——0Nvalconazole
B1-2005iPrOOOCO2H——0Nvalconazole
B1-2006PhOOOCO2H——0Nvalconazole
B1-2007(HOCH2—OOCO2H——0Nvalconazole
CH2)2N
B1-2008N(H)NMe2OOCO2H——0Nvalconazole
B1-20094-(OH)PhOOCO2H——0Nvalconazole
B1-20104-(NH2)PhOOCO2H——0Nvalconazole
B1-2011EtSOOCO2H——0Nzinoconazole
B1-2012EtOOOCO2H——0Nzinoconazole
B1-2013t-BuOOOCO2H——0Nzinoconazole
B1-2014cyclohexylOOOCO2H——0Nzinoconazole
B1-2015iPrOOOCO2H——0Nzinoconazole
B1-2016PhOOOCO2H——0Nzinoconazole
B1-2017(HOCH2—OOCO2H——0Nzinoconazole
CH2)2N
B1-2018N(H)NMe2OOCO2H——0Nzinoconazole
B1-20194-(OH)PhOOCO2H——0Nzinoconazole
B1-20204-(NH2)PhOOCO2H——0Nzinoconazole
B1-2021EtSOOCO2HOO1Ccloxacillin
B1-2022EtOOOCO2HOO1Ccloxacillin
B1-2023t-BuOOOCO2HOO1Ccloxacillin
B1-2024cyclohexylOOOCO2HOO1Ccloxacillin
B1-2025iPrOOOCO2HOO1Ccloxacillin
B1-2026PhOOOCO2HOO1Ccloxacillin
B1-2027(HOCH2—OOCO2HOO1Ccloxacillin
CH2)2N
B1-2028N(H)NMe2OOCO2HOO1Ccloxacillin
B1-20294-(OH)PhOOCO2HOO1Ccloxacillin
B1-20304-(NH2)PhOOCO2HOO1Ccloxacillin
B1-2031EtSOOCO2HOO1Cvalproic acid
B1-2032EtOOOCO2HOO1Cvalproic acid
B1-2033t-BuOOOCO2HOO1Cvalproic acid
B1-2034cyclohexylOOOCO2HOO1Cvalproic acid
B1-2035iPrOOOCO2HOO1Cvalproic acid
B1-2036PhOOOCO2HOO1Cvalproic acid
B1-2037(HOCH2—OOCO2HOO1Cvalproic acid
CH2)2N
B1-2038N(H)NMe2OOCO2HOO1Cvalproic acid
B1-20394-(OH)PhOOCO2HOO1Cvalproic acid
B1-20404-(NH2)PhOOCO2HOO1Cvalproic acid
B1-2041EtSOOCO2HOO1Cretinoic acid
B1-2042EtOOOCO2HOO1Cretinoic acid
B1-2043t-BuOOOCO2HOO1Cretinoic acid
B1-2044cyclohexylOOOCO2HOO1Cretinoic acid
B1-2045iPrOOOCO2HOO1Cretinoic acid
B1-2046PhOOOCO2HOO1Cretinoic acid
B1-2047(HOCH2—OOCO2HOO1Cretinoic acid
CH2)2N
B1-2048N(H)NMe2OOCO2HOO1Cretinoic acid
B1-20494-(OH)PhOOCO2HOO1Cretinoic acid
B1-20504-(NH2)PhOOCO2HOO1Cretinoic acid
B1-2051EtSOOCO2HOO1Coxaprozin
B1-2052EtOOOCO2HOO1Coxaprozin
B1-2053t-BuOOOCO2HOO1Coxaprozin
B1-2054cyclohexylOOOCO2HOO1Coxaprozin
B1-2055iPrOOOCO2HOO1Coxaprozin
B1-2056PhOOOCO2HOO1Coxaprozin
B1-2057(HOCH2—OOCO2HOO1Coxaprozin
CH2)2N
B1-2058N(H)NMe2OOCO2HOO1Coxaprozin
B1-20594-(OH)PhOOCO2HOO1Coxaprozin
B1-20604-(NH2)PhOOCO2HOO1Coxaprozin
B1-2061EtSOOCO2HOO1Cnaproxen
B1-2062EtOOOCO2HOO1Cnaproxen
B1-2063t-BuOOOCO2HOO1Cnaproxen
B1-2064cyclohexylOOOCO2HOO1Cnaproxen
B1-2065iPrOOOCO2HOO1Cnaproxen
B1-2066PhOOOCO2HOO1Cnaproxen
B1-2067(HOCH2—OOCO2HOO1Cnaproxen
CH2)2N
B1-2068N(H)NMe2OOCO2HOO1Cnaproxen
B1-20694-(OH)PhOOCO2HOO1Cnaproxen
B1-20704-(NH2)PhOOCO2HOO1Cnaproxen
B1-2071EtSOOCO2HOO1Cmonopril
B1-2072EtOOOCO2HOO1Cmonopril
B1-2073t-BuOOOCO2HOO1Cmonopril
B1-2074cyclohexylOOOCO2HOO1Cmonopril
B1-2075iPrOOOCO2HOO1Cmonopril
B1-2076PhOOOCO2HOO1Cmonopril
B1-2077(HOCH2—OOCO2HOO1Cmonopril
CH2)2N
B1-2078N(H)NMe2OOCO2HOO1Cmonopril
B1-20794-(OH)PhOOCO2HOO1Cmonopril
B1-20804-(NH2)PhOOCO2HOO1Cmonopril
B1-2081EtSOOCO2HOO1Cketorolac
B1-2082EtOOOCO2HOO1Cketorolac
B1-2083t-BuOOOCO2HOO1Cketorolac
B1-2084cyclohexylOOOCO2HOO1Cketorolac
B1-2085iPrOOOCO2HOO1Cketorolac
B1-2086PhOOOCO2HOO1Cketorolac
B1-2087(HOCH2—OOCO2HOO1Cketorolac
CH2)2N
B1-2088N(H)NMe2OOCO2HOO1Cketorolac
B1-20894-(OH)PhOOCO2HOO1Cketorolac
B1-20904-(NH2)PhOOCO2HOO1Cketorolac
B1-2091EtSOOCO2HOO1Cketoprofen
B1-2092EtOOOCO2HOO1Cketoprofen
B1-2093t-BuOOOCO2HOO1Cketoprofen
B1-2094cyclohexylOOOCO2HOO1Cketoprofen
B1-2095iPrOOOCO2HOO1Cketoprofen
B1-2096Ph0OOCO2HOO1Cketoprofen
B1-2097(HOCH2—OOCO2HOO1Cketoprofen
CH2)2N
B1-2098N(H)NMe2OOCO2HOO1Cketoprofen
B1-20994-(OH)PhOOCO2HOO1Cketoprofen
B1-21004-(NH2)PhOOCO2HOO1Cketoprofen
B1-2101EtSOOCO2HOO1Cindomethacin
B1-2102EtOOOCO2HOO1Cindomethacin
B1-2103t-BuOOOCO2HOO1Cindomethacin
B1-2104cyclohexylOOOCO2HOO1Cindomethacin
B1-2105iPrOOOCO2HOO1Cindomethacin
B1-2106PhOOOCO2HOO1Cindomethacin
B1-2107(HOCH2—OOCO2HOO1Cindomethacin
CH2)2N
B1-2108N(H)NMe2OOCO2HOO1Cindomethacin
B1-21094-(OH)PhOOCO2HOO1Cindomethacin
B1-21104-(NH2)PhOOCO2HOO1Cindomethacin
B1-2111EtSOOCO2HOO1Cibuprofen
B1-2112EtOOOCO2HOO1Cibuprofen
B1-2113i-BuOOOCO2HOO1Cibuprofen
B1-2114cyclohexylOOOCO2HOO1Cibuprofen
B1-2115iPrOOOCO2HOO1Cibuprofen
B1-2116PhOOOCO2HOO1Cibuprofen
B1-2117(HOCH2—OOCO2HOO1Cibuprofen
CH2)2N
B1-2118N(H)NMe2OOCO2HOO1Cibuprofen
B1-21194-(OH)PhOOCO2HOO1Cibuprofen
B1-21204-(NH2)PhOOCO2HOO1Cibuprofen
B1-2121EtSOOCO2HOO1Cgemfibrozil
B1-2122EtOOOCO2HOO1Cgemfibrozil
B1-2123t-BuOOOCO2HOO1Cgemfibrozil
B1-2124cyclohexylOOOCO2HOO1Cgemfibrozil
B1-2125iPrOOOCO2HOO1Cgemfibrozil
B1-2126PhOOOCO2HOO1Cgemfibrozil
B1-2127(HOCH2—OOCO2HOO1Cgemfibrozil
CH2)2N
B1-2128N(H)NMe2OOCO2HOO1Cgemfibrozil
B1-21294-(OH)PhOOCO2HOO1Cgemfibrozil
B1-21304-(NH2)PhOOCO2HOO1Cgemfibrozil
B1-2131EtSOOCO2HOO1Cflurbiprofen
B1-2132EtOOOCO2HOO1Cflurbiprofen
B1-2133t-BuOOOCO2HOO1Cflurbiprofen
B1-2134cyclohexylOOOCO2HOO1Cflurbiprofen
B1-2135iPrOOOCO2HOO1Cflurbiprofen
B1-2136PhOOOCO2HOO1Cflurbiprofen
B1-2137(HOCH2—OOCO2HOO1Cflurbiprofen
CH2)2N
B1-2138N(H)NMe2OOCO2HOO1Cflurbiprofen
B1-21394-(OH)PhOOCO2HOO1Cflurbiprofen
B1-21404-(NH2)PhOOCO2HOO1Cflurbiprofen
B1-2141EtSOOCO2HOO1Carthrocine
B1-2142EtOOOCO2HOO1Carthrocine
B1-2143t-BuOOOCO2HOO1Carthrocine
B1-2144cyclohexylOOOCO2HOO1Carthrocine
B1-2145iPrOOOCO2HOO1Carthrocine
B1-2146PhOOOCO2HOO1Carthrocine
B1-2147(HOCH2—OOCO2HOO1Carthrocine
CH2)2N
B1-2148N(H)NMe2OOCO2HOO1Carthrocine
B1-21494-(OH)PhOOCO2HOO1Carthrocine
B1-21504-(NH2)PhOOCO2HOO1Carthrocine
B1-2151EtSOOCO2HOO1Cadapalene
B1-2152EtOOOCO2HOO1Cadapalene
B1-2153t-BuOOOCO2HOO1Cadapalene
B1-2154cyclohexylOOOCO2HOO1Cadapalene
B1-2155iPrOOOCO2HOO1Cadapalene
B1-2156PhOOOCO2HOO1Cadapalene
B1-2157(HOCH2—OOCO2HOO1Cadapalene
CH2)2N
B1-2158N(H)NMe2OOCO2HOO1Cadapalene
B1-21594-(OH)PhOOCO2HOO1Cadapalene
B1-21604-(NH2)PhOOCO2HOO1Cadapalene
B1-2161EtSOOCO2HOO1Clansoprazole
B1-2162EtOOOCO2HOO1Clansoprazole
B1-2163t-BuOOOCO2HOO1Clansoprazole
B1-2164cyclohexylOOOCO2HOO1Clansoprazole
B1-2165iPrOOOCO2HOO1Clansoprazole
B1-2166PhOOOCO2HOO1Clansoprazole
B1-2167(HOCH2—OOCO2HOO1Clansoprazole
CH2)2N
B1-2168N(H)NMe2OOCO2HOO1Clansoprazole
B1-21694-(OH)PhOOCO2HOO1Clansoprazole
B1-21704-(NH2)PhOOCO2HOO1Clansoprazole
B1-2171EtSOOCO2HOO1Clovastatin
B1-2172EtOOOCO2HOO1Clovastatin
B1-2173t-Bu0OOCO2HOO1Clovastatin
B1-2174cyclohexylOOOCO2HOO1Clovastatin
B1-2175iPrOOOCO2HOO1Clovastatin
B1-2176PhOOOCO2HOO1Clovastatin
B1-2177(HOCH2—OOCO2HOO1Clovastatin
CH2)2N
B1-2178N(H)NMe2OOCO2HOO1Clovastatin
B1-21794-(OH)PhOOCO2HOO1Clovastatin
B1-21804-(NH2)PhOOCO2HOO1Clovastatin
B1-2181EtSOOCO2HOO1Cwarfarin
B1-2182EtOOOCO2HOO1Cwarfarin
B1-2183t-Bu0OOCO2HOO1Cwarfarin
B1-2184cyclohexylOOOCO2HOO1Cwarfarin
B1-2185iPrOOOCO2HOO1Cwarfarin
B1-2186PhOOOCO2HOO1Cwarfarin
B1-2187(HOCH2—OOCO2HOO1Cwarfarin
CH2)2N
B1-2188N(H)NMe2OOCO2HOO1Cwarfarin
B1-21894-(OH)PhOOCO2HOO1Cwarfarin
B1-21904-(NH2)PhOOCO2HOO1Cwarfarin
B1-2191EtSOOCO2H——0Ntolteridine
B1-2192EtOOOCO2H——0Ntolteridine
B1-2193t-BuOOOCO2H——0Ntolteridine
B1-2194cyclohexylOOOCO2H——0Ntolteridine
B1-2195iPrOOOCO2H——0Ntolteridine
B1-2196PhOOOCO2H——0Ntolteridine
B1-2197(HOCH2—OOCO2H——0Ntolteridine
CH2)2N
B1-2198N(H)NMe2OOCO2H——0Ntolteridine
B1-21994-(OH)PhOOCO2H——0Ntolteridine
B1-22004-(NH2)PhOOCO2H——0Ntolteridine
B1-2201EtSOOCO2H——0Nticlopidine
B1-2202EtOOOCO2H——0Nticlopidine
B1-2203t-BuOOOCO2H——0Nticlopidine
B1-2204cyclohexylOOOCO2H——0Nticlopidine
B1-2205iPrOOOCO2H——0Nticlopidine
B1-2206PhOOOCO2H——0Nticlopidine
B1-2207(HOCH2—OOCO2H——0Nticlopidine
CH2)2N
B1-2208N(H)NMe2OOCO2H——0Nticlopidine
B1-22094-(OH)PhOOCO2H——0Nticlopidine
B1-22104-(NH2)PhOOCO2H——0Nticlopidine
B1-2211EtSOOCO2H——0Nsibutramine
B1-2212EtOOOCO2H——0Nsibutramine
B1-2213t-BuOOOCO2H——0Nsibutramine
B1-2214cyclohexylOOOCO2H——0Nsibutramine
B1-2215iPrOOOCO2H——0Nsibutramine
B1-2216PhOOOCO2H——0Nsibutramine
B1-2217(HOCH2—OOCO2H——0Nsibutramine
CH2)2N
B1-2218N(H)NMe2OOCO2H——0Nsibutramine
B1-22194-(OH)PhOOCO2H——0Nsibutramine
B1-22204-(NH2)PhOOCO2H——0Nsibutramine
B1-2221EtSOOCO2H——0Npropoxyphene
B1-2222EtOOOCO2H——0Npropoxyphene
B1-2223t-BuOOOCO2H——0Npropoxyphene
B1-2224cyclohexylOOOCO2H——0Npropoxyphene
B1-2225iPrOOOCO2H——0Npropoxyphene
B1-2226PhOOOCO2H——0Npropoxyphene
B1-2227(HOCH2—OOCO2H——0Npropoxyphene
CH2)2N
B1-2228N(H)NMe2OO—CO2H——0Npropoxyphene
B1-22294-(OH)PhOOCO2H——0Npropoxyphene
B1-22304-(NH2)PhOOCO2H——0Npropoxyphene
B1-2231EtSOOCO2H——0Nnifurantin
B1-2232EtOO0CO2H——0Nnifurantin
B1-2233t-BuOOOCO2H——0Nnifurantin
B1-2234cyclohexylOOOCO2H——0Nnifurantin
B1-2235iPrOOOCO2H——0Nnifurantin
B1-2236PhOOOCO2H——0Nnifurantin
B1-2237(HOCH2—OOCO2H——0Nnifurantin
CH2)2N
B1-2238N(H)NMe2OOCO2H——0Nnifurantin
B1-22394-(OH)PhOOCO2H——0Nnifurantin
B1-22404-(NH2)PhOOCO2H——0Nnifurantin
B1-2241EtSOOCO2H——0Nnefazodone
B1-2242EtOOOCO2H——0Nnefazodone
B1-2243t-BuOOOCO2H——0Nnefazodone
B1-2244cyclohexylOOOCO2H——0Nnefazodone
B1-2245iPrOOOCO2H——0Nnefazodone
B1-2246PhOOOCO2H——0Nnefazodone
B1-2247(HOCH2—OOCO2H——0Nnefazodone
CH2)2N
B1-2248N(H)NMe2OOCO2H——0Nnefazodone
B1-22494-(OH)PhOOCO2H——0Nnefazodone
B1-22504-(NH2)PhOOCO2H——0Nnefazodone
B1-2251EtSOOCO2H——0Ndonezapil
B1-2252EtOOOCO2H——0Ndonezapil
B1-2253t-BuOOOCO2H——0Ndonezapil
B1-2254cyclohexylOOOCO2H——0Ndonezapil
B1-2255iPrOOOCO2H——0Ndonezapil
B1-2256PhOOOCO2H——0Ndonezapil
B1-2257(HOCH2—OOCO2H——0Ndonezapil
CH2)2N
B1-2258N(H)NMe2OOCO2H——0Ndonezapil
B1-22594-(OH)PhOOCO2H——0Ndonezapil
B1-22604-(NH2)PhOOCO2H——0Ndonezapil
B1-2261EtSOOCO2H——0Ndicodid
B1-2262EtOOOCO2H——0Ndicodid
B1-2263t-BuOOOCO2H——0Ndicodid
B1-2264cyclohexylOOOCO2H——0Ndicodid
B1-2265iPrOOOCO2H——0Ndicodid
B1-2266PhOOOCO2H——0Ndicodid
B1-2267(HOCH2—OOCO2H——0Ndicodid
CH2)2N
B1-2268N(H)NMe2OOCO2H——0Ndicodid
B1-22694-(OH)PhOOCO2H——0Ndicodid
B1-22704-(NH2)PhOOCO2H——0Ndicodid
B1-2271EtSOOCO2H——0Ncoichicine
B1-2272EtOOOCO2H——0Ncoichicine
B1-2273t-BuOOOCO2H——0Ncoichicine
B1-2274cyclohexylOOOCO2H——0Ncoichicine
B1-2275iPrOOOCO2H——0Ncoichicine
B1-2276Ph0OOCO2H——0Ncoichicine
B1-2277(HOCH2—OOCO2H——0Ncoichicine
CH2)2N
B1-2278N(H)NMe2OOCO2H——0Ncoichicine
B1-22794-(OH)PhOOCO2H——0Ncoichicine
B1-22804-(NH2)PhOOCO2H——0Ncoichicine
B1-2281EtSOOCO2H——0Ncitalopram
B1-2282EtOOOCO2H——0Ncitalopram
B1-2283t-BuOOOCO2H——0Ncitalopram
B1-2284cyclohexylOOOCO2H——0Ncitalopram
B1-2285iPrOOOGCO2H——0Ncitalopram
B1-2286Ph0OOCO2H——0Ncitalopram
B1-2287(HOCH2—OOCO2H——0Ncitalopram
CH2)2N
B1-2288N(H)NMe2OOCO2H——0Ncitalopram
B1-22894-(OH)PhOOCO2H——0Ncitalopram
B1-22904-(NH2)PhOOCO2H——0Ncitalopram
B1-2291EtSOOCO2H——0Nbenzatropine
B1-2292EtOOOCO2H——0Nbenzatropine
B1-2293t-BuOOOCO2H——0Nbenzatropine
B1-2294cyclohexylOOOCO2H——0Nbenzatropine
B1-2295iPrOOOCO2H——0Nbenzatropine
B1-2296PhOOOCO2H——0Nbenzatropine
B1-2297(HOCH2—OOCO2H——0Nbenzatropine
CH2)2N
B1-2298N(H)NMe2OOCO2H——0Nbenzatropine
B1-22994-(OH)PhOOCO2H——0Nbenzatropine
B1-23004-(NH2)PhOOCO2H——0Nbenzatropine
|
[0692] Table B2: Compounds (B2-1)-(B2-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21′ m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2Me.
[0693] Table B3: Compounds (B3-1)-(B3-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2Et.
[0694] Table B4: Compounds (B4-1)-(B4-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B 1 except for R1 which equals CO21t-Pr. Table B5: Compounds (B5-1)-(B5-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2t-Bu.
[0695] Table B6: Compounds (B6-1)-(B6-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2cyclopropyl.
[0696] Table B7: Compounds (B7-1)-(B7-2300) are compounds of Formula I where X2, Z11, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2Bn.
[0697] Table B8: Compounds (B8-1)-(B8-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2CH2CH2Ph.
[0698] Table B9: Compounds (B9-1)-(B9-2300) are compounds of Formula I where X2, Z1, G10, G1, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2CH2CF3.
[0699] Table B10: Compounds (B10-1)-(B10-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2CH2OMe.
[0700] Table B11: Compounds (B11-1)-(B11-2300) are compounds of Formula I where X2, Z1, G10, G10, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2) are identical to those in Table B1 except for R1 which equals Co2allyl.
[0701] Table B12: Compounds (B12-1)-(B12-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2Ph.
[0702] Table B13: Compounds (B13-1)-(B13-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-2(OMe)Ph.
[0703] Table B14: Compounds (B14-1)-(B14-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-3-(OMe)Ph.
[0704] Table B15: Compounds (B15-1)-(B15-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-4-(OMe)-Ph.
[0705] Table B16: Compounds (B16-1)-(B16-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2-2(Me)Ph.
[0706] Table B17: Compounds (B17-1)-(B17-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G2, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals Co2-3(Me)Ph.
[0707] Table-B18: Compounds (B18-1)-(B18-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-4(Me)Ph.
[0708] Table B19: Compounds (B19-1)-(B19-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-4(NO2)Ph.
[0709] Table B20: Compounds (B20-1)-(B20-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2SiMe3.
[0710] Table B21: Compounds (B21-1)-(B21-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)Me.
[0711] Table B22: Compounds B22-1)-(B22-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(—O)NMe2.
[0712] Table B23: Compounds (B23-1)-(B23-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)NBn2. Table B24: Compounds (B24-1)-(B24-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(Me)Bn.
[0713] Table B25: Compounds (B25-1)-(B25-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(Me)Ph.
[0714] Table B26: Compounds B26-1)-(B26-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(E)Ph.
[0715] Table B27: Compounds (B27-1)-(B27-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)G21]-H, Z2(X2)q—H or Z2(X1) are identical to those in Table B1 except for R1 which equals C(═O)N(H)NMe2.
[0716] Table B28: Compounds (B28-1)-(B28-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals CO2-octyl.
[0717] Table B29: Compounds (B29-1)-(B29-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)n-Bu.
[0718] Table B30: Compounds (B30-1)-(B30-2300) are compounds of Formula I where X2, Z11, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2), are identical to those in Table B1 except for R1 which equals C(═O)N(H)N(H)Co2Et.
[0719] Table B31: Compounds (B31-1)-(B31-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B13 except for R1 which equals C(═O)N(H)N(H)Co2t-Bu.
[0720] Table B32: Compounds (B32-1)-(B32-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B13 except for R1 which equals C(═O)N(H)N═CHMe.
[0721] Table B33: Compounds (B33-1)-(B33-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)N═CMe2.
[0722] Table B34: Compounds (B34-1)-(B34-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)N═CHPh.
[0723] Table B35: Compounds (B35-1)-(B3-52300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)SPh.
[0724] Table B36: Compounds (B36-1)-(B36-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)SEt.
[0725] Table B37: Compounds (B37-1)-(B37-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)Sn-Bu.
[0726] Table B38: Compounds (B38-1)-(B38-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G2]-H, Z2(X2)qH or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)OMe.
[0727] Table B39: Compounds (B39-1)-(B39-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20; G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)OBn.
[0728] Table B40: Compounds (B40-1)-(B40-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)NH2.
[0729] Table B41: Compounds (B41-1)-(B41-2300) are compounds of Formula I where X2, Z1, G10, G11, R2, G20, G21, m, t, q and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are identical to those in Table B1 except for R1 which equals C(═O)N(H)OH.
[0730] Table C describes additional examples of compounds of Formula I which can be made using the procedures described hereinbefore, where R2 is hydrogen, m=1, q=0, t=0 or 1 and the pharmaceutical (a veterinary drug) which defines the pharmaceutical moiety of these examples is Z1(X1)m—H. The following groups, Z1(X1)m—H, X1, G10, G11, R1, G20, G21, t and Z2 are defined within Table C.
13TABLE C
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86
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Cmpd #Z1(X1)m-HX1G10G11R1G20G21tZ2
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C-1albendazoleNOOCO2HOO1methyl
C-2clioquinolOOOCO2HOO1C(CH3)3
C-3febantelNOOCO2HOO1Ph
C-4fenbendazoleNOOCO2HOO14Me(Ph)
C-5guaifenesinOOOCO2H——0Cl
C-6miboleroneOOOCO2H——0{N(Et)3}+Cl−
C-7omeprazoleNOOCO2H——0{N(Me)2Ph}+Cl−
C-8oxazepamOOOCO2MeOO1methyl
C-9piroxicamNOOCO2MeOO1C(CH3)3
C-10primidoneNOOCO2MeOO1Ph
C-11procainamideNOOCO2MeOO14Me(Ph)
C-12thiabendazoleNOOCO2Me——0Cl
C-13warfarinOOOCO2Me——0{N(Et)3}+Cl−
C-14albendazoleNOOCO2Me——0{N(Me)2Ph}+Cl−
C-15clioquinolOOOCO2EtOO1methyl
C-16febantelNOOCO2Et——0Cl
C-17fenbendazoleNOSCO2n-PrOO1methyl
C-18guaifenesinOOSCO2n-Pr——0Cl
C-19miboleroneOOOCO2n-BuOO1methyl
C-20omeprazoleNOOCO2n-BuOO1C(CH3)3
C-21oxazepamOOOCO2n-BuOO1Ph
C-22piroxicamNOSCO2n-BuOO14Me(Ph)
C-23primidoneNOSCO2n-BuOO1CF3CH2
C-24procainamideNOOCO2n-Bu——0Cl
C-25thiabendazoleNOOCO2n-Bu——0{N(Et)3}+Cl−
C-26warfarinOOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-27albendazoleNOOCO2n-Bu——0O—C(CH3)3
C-28clioquinolOOOCO2—BnOO1methyl
C-29febantelNOOCO2—BnOO1C(CH3)3
C-30fenbendazoleNOOCO2—BnOO1Ph
C-31guaifenesinOOSCO2—BnOO14Me(Ph)
C-32miboleroneOOSCO2—BnOO1CF3CH2
C-33omeprazoleNOOCO2—Bn——0Cl
C-34oxazepamOOOCO2—Bn——0{N(Et)3}+Cl−
C-35piroxicamNOOCO2—Bn——0{N(Me)2Ph}+Cl−
C-36primidoneNOOCO2—BnOO0O—C(CH3)3
C-37procainamideNOOCOSMeOO1methyl
C-38thiabendazoleNOSCOSMeOO1C(CH3)3
C-39warfarinOOOCOSMe——0Cl
C-40albendazoleNOOCOSMeOO0{N(Et)3}+Cl−
C-41clioquinolOOSCOSEtOO1methyl
C-42febantelNOOCOSEt——0Cl
C-43fenbendazoleNOOCOSn-BuOO1methyl
C-44guaifenesinOOSCOSn-Bu——0Cl
C-45miboleroneOOOCOSBnOO1methyl
C-46omeprazoleNOOCOSBn——0Cl
C-47oxazepamOOOCONHMeOO1methyl
C-48piroxicamNOOCONHMeOO1C(CH3)3
C-49primidoneNOOCONHEtOO1methyl
C-50procainamideNOOCONHn-PrOO1methyl
C-51thiabendazoleNOOCONHn-BuOO1methyl
C-52warfarinOOOCONHn-BuOO1C(CH3)3
C-53albendazoleNOOCONHn-BuOO1Ph
C-54clioquinolOOOCONHn-BuOO14Me(Ph)
C-55febantelNOOCONHn-BuOO1CF3CH2
C-56fenbendazoleNOOCONHn-Bu——0Cl
C-57guaifenesinOOOCONHn-BuOOO{N(Et)3}+Cl−
C-58miboleroneOOOCONH—BnOO1methyl
C-59omeprazoleNOOCONH—BnOO1C(CH3)3
C-60oxazepamOOOCONH—Bn——0{N(Et)3}+Cl−
C-61piroxicamNOOCONNH2OO1methyl
C-62primidoneNOOCONHNHMeOO1methyl
C-63procainamideNOOCONHNHEtOO1methyl
C-64thiabendazoleNOOCONHNHPrOO1methyl
C-65warfarinOOOCONHNHt-BuOO1C(CH3)3
C-66albendazoleNOOCONHNHCO2MeOO1C(CH3)3
C-67clioquinolOOOCONHNHCO2EtOO1C(CH3)3
C-68febantelNOOCONHNHCO2t-BuOO1C(CH3)3
C-69fenbendazoleNOOCONHNHCO2BnOO1C(CH3)3
C-70guaifenesinOOOCONHN═CHMeOO1methyl
C-71miboleroneOOOCONHN═CHMe——0{N(Et)3}+Cl−
C-72omeprazoleNOOCONHN═CHPhOO1methyl
C-73oxazepamOOOCONHN═CHPhOO1C(CH3)3
C-74disopyramideNOOCO2HOO1methyl
C-75disopyramideNOOCO2HOO1C(CH3)3
C-76disopyramideNOOCO2HOO1Ph
C-77disopyramideNOOCO2HOO14Me(Ph)
C-78disopyramideNOOCO2H——0Cl
C-79disopyramideNOOCO2H——0{N(Et)3}+Cl−
C-80disopyramideNOOCO2H——0{N(Me)2Ph}+Cl−
C-81disopyramideNOOCO2MeOO1methyl
C-82disopyramideNOOCO2MeOO1C(CH3)3
C-83disopyramideNOOCO2MeOO1Ph
C-84disopyramideNOOCO2MeOO14Me(Ph)
C-85disopyramideNOOCO2Me——0Cl
C-86aminocaproic acidNOOCO2Me——0{N(Et)3}+Cl−
C-87aminocaproic acidNOOCO2Me——0{N(Me)2Ph}+Cl−
C-88aminocaproic acidNOOCO2EtOO1methyl
C-89aminocaproic acidNOOCO2Et——0Cl
C-90aminophyllineNOSCO2n-PrOO1methyl
C-91aminophyllineNOSCO2n-Pr——0Cl
C-92aminophyllineNOOCO2n-BuOO1methyl
C-93aminophyllineNOOCO2n-BuOO1C(CH3)3
C-94aminophyllineNOOCO2n-BuOO1Ph
C-95aminophyllineNOSCO2n-BuOO14Me(Ph)
C-96aminophyllineNOSCO2n-BuOO1CF3CH2
C-97aminophyllineNOOCO2n-Bu——0Cl
C-98aminophyllineNOOCO2n-Bu——0{N(Et)3}+Cl−
C-99aminophyllineNOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-100aminophyllineNOOCO2n-Bu——0O—C(CH3)3
C-101amproliumNOOCO2-BnOO1methyl
C-102amproliumNOOCO2-BnOO1O(CH3)3
C-103amproliumNOOCO2-BnOO1Ph
C-104amproliumNOSCO2-BnOO14Me(Ph)
C-105amproliumNOSCO2-BnOO1CF3CH2
C-106atipamezoleNOOCO2-Bn——0Cl
C-107atipamezoleNOOCO2-Bn——0{N(Et)3}+Cl−
C-108atipamezoleNOOCO2-Bn——0{N(Me)2Ph}+Cl−
C-109atipamezoleNOOCO2-Bn——0OC(CH3)3
C-110atipamezoleNOOCOSMeOO1methyl
C-111atipamezoleNOSCOSMeOO1C(CH3)3
C-112atipamezoleNOOCOSMe——0Cl
C-113atipamezoleNOOCOSMe——0{N(Et)3}+Cl−
C-114benazeprilNOSCOSEtOO1methyl
C-115benazeprilNOOCOSEt——0Cl
C-116benazeprilNOOCOSn-BuOO1methyl
C-117benazeprilNOSCOSn-Bu——0Cl
C-118benazeprilNOOCOSBnOO1methyl
C-119benazeprilNOOCOSBn——0Cl
C-120benazeprilNOOCONHMeOO1methyl
C-121benazeprilNOOCONHMeOO1C(CH3)3
C-122benazeprilNOOCONHEtOO1methyl
C-123cisaprideNOOCONHn-PrOO1methyl
C-124detomidineNOOCONHn-BuOO1methyl
C-125enalaprilOOOCONHn-BuOO1C(CH3)3
C-126enalaprilOOOCONHn-BuOO1Ph
C-127enalaprilOOOCONHn-BuOO14Me(Ph)
C-128enalaprilOOOCONHn-BuOO1CF3CH2
C-129enalaprilOOOCONHn-Bu——0Cl
C-130enalaprilOOOCONHn-Bu——0{N(Et)}+Cl−
C-131enalaprilNOOCONH—BnOO1methyl
C-132enalaprilNOOCONH—BnOO1C(CH3)3
C-133enalaprilNOOCONH—Bn——0{N(Et)3}+Cl−
C-134enalaprilNOOCONNH2OO1methyl
C-135enalaprilNOOCONHNHMeOO1methyl
C-136enalaprilNOOCONHNHEtOO1methyl
C-137enalaprilNOOCONHNHPrOO1methyl
C-138enalaprilNOOCONHNHt-BuOO1C(CH3)3
C-139enalaprilNOOCONHNHCO2MeOO1C(CH3)3
C-140enalaprilNOOCONHNHCO2EtOO1C(CH3)3
C-141enalaprilNOOCONHNHCO2t-BuOO1C(CH3)3
C-142enalaprilNOOCONHNHCO2BnOO1C(CH3)3
C-143enalaprilNOOCONHN═CHMeOO1methyl
C-144enalaprilNOOCONHN═CHMe——0{N(Et)3}+Cl−
C-145enalaprilNOOCONHN═CHPhOO1methyl
C-146enalaprilNOOCONHN═CHPhOO1C(CH3)3
C-147enalaprilNOOCO2HOO1methyl
C-148enalaprilNOOCO2HOO1C(CH3)3
C-149enalaprilNOOCO2HOO1Ph
C-150enalaprilNOOCO2HOO14Me(Ph)
C-151enalaprilNOOCO2H——0Cl
C-152enalaprilNOOCO2H——0{N(Et)3}+Cl−
C-153enalaprilNOOCO2H——0{N(Me)2Ph}+Cl−
C-154enalaprilNOOCO2MeOO1methyl
C-155enalaprilNOOCO2MeOO1C(CH3)3
C-156enalaprilNOOCO2MeOO1Ph
C-157fluconazoleNOOCO2HOO1methyl
C-158fluconazoleNOOCO2HOO1C(CH3)3
C-159fluconazoleNOOCO2MeOO1Ph
C-160fluconazoleNOOCO2MeOO14Me(Ph)
C-161fluconazoleNOOCO2Me——0Cl
C-162fluconazoleNOOCO2Me——0{N(Et)3}+Cl−
C-163fluconazoleNOOCO2Me——0{N(Me)2Ph}+Cl−
C-164fluconazoleNOOCO2MeOO1methyl
C-165fluconazoleNOOCO2MeOO1C(CH3)3
C-166fluconazoleNOOCO2EtOO1Ph
C-167fluconazoleNOOCO2n-PrOO14Me(Ph)
C-168fluconazoleNOOCO2n-Bu——0Cl
C-169fluconazoleNOOCO2—Bn——0{N(Et)3}+Cl−
C-170fluconazoleNOOCOSMe——0{N(Me)2Ph}+Cl−
C-171fluconazoleNOOCOSEtOO1methyl
C-172fluconazoleNOOCOSn-BuOO1C(CH3)3
C-173fluconazoleNOOCONHMeOO1Ph
C-174fluconazoleNOOCONHEtOO14Me(Ph)
C-175fluconazoleNOOCONHn-Bu——0Cl
C-176fluconazoleNOOCONH—Bn——0{N(Et)3}+Cl−
C-177fluconazoleNOOCONNH2——0{N(Me)2Ph}+Cl−
C-178fluconazoleNOOCONHNHMeOO1methyl
C-179fluconazoleNOOCONHNHEtOO1C(CH3)3
C-180fluconazoleNOOCONHNHPrOO1Ph
C-181fluconazoleNOOCONHNHt-BuOO14Me(Ph)
C-182fluconazoleNOOCONHNHCO2Me——0Cl
C-183fluconazoleNOOCONHNHCO2Et——0{N(Et)3}+Cl−
C-184fluconazoleNOOCONHNHCO2t-Bu——0{N(Me)2Ph}+Cl−
C-185fluconazoleNOOCONHNHCO2BnOO1methyl
C-186fluconazoleNOOCONHN═CHMeOO1C(CH3)3
C-187fluconazoleNOOCONHN═CHMeOO14Me(Ph)
C-188fluconazoleNOOCONHN═CHPh——0Cl
C-189fluconazoleNOOCONHN═CHPh——0{N(Et)3}+Cl−
C-190hetacillinNOOCO2MeOO14Me(Ph)
C-191imidaclopridNOOCO2Me——0Cl
C-192imidaclopridNOOCO2Me——0{N(Et)3}+Cl−
C-193imidaclopridNOOCO2Me——0{N(Me)2Ph}+Cl−
C-194imidaclopridNOOCO2EtOO1methyl
C-195imidaclopridNOOCO2Et——0Cl
C-196imidaclopridNOSCO2n-PrOO1methyl
C-197imidaclopridNOSCO2n-Pr——0Cl
C-198imidaclopridNOOCO2n-BuOO1methyl
C-199imidaclopridNOOCO2n-BuOO1C(CH3)3
C-200imidaclopridNOOCO2n-BuOO1Ph
C-201imidaclopridNOSCO2n-BuOO14Me(Ph)
C-202imidaclopridNOSCO2n-BuOO1CF3CH2
C-203imidaclopridNOOCO2n-Bu——0Cl
C-204imidaclopridNOOCO2n-Bu——0{N(Et)3}+Cl−
C-205imidaclopridNOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-206imidaclopridNOOCO2n-Bu——0OC(CH3)3
C-207imidaclopridNOOCO2—BnOO1methyl
C-208imidaclopridNOOCO2—BnOO1C(CH3)3
C-209imidaclopridNOOCO2—BnOO1Ph
C-210imidaclopridNOSCO2—BnOO14Me(Ph)
C-211imidaclopridNOSCO2—BnOO1CF3CH2
C-212imidaclopridNOOCO2—Bn——0Cl
C-213imidaclopridNOOCO2—Bn——0{N(Et)3}+Cl−
C-214imidaclopridNOOCO2—Bn——0{N(Me)2Ph}+Cl−
C-215imidaclopridNOOCO2—Bn——0OC(CH3)3
C-216imidaclopridNOOCOSMeOO1methyl
C-217imidaclopridNOSCOSMeOO1C(CH3)3
C-218imidaclopridNOOCOSMe——0Cl
C-219imidaclopridNOOCOSMe——0{N(Et)3}+Cl−
C-220imidaclopridNOSCOSEtOO1methyl
C-221imidaclopridNOOCOSEt——0Cl
C-222imidaclopridNOOCOSn-BuOO1methyl
C-223imidaclopridNOSCOSn-Bu——0Cl
C-224imidaclopridNOOCOSBnOO1methyl
C-225imidaclopridNOOCOSBn——0Cl
C-226imidaclopridNOOCONHMeOO1methyl
C-227imidaclopridNOOCONHMeOO1C(CH3)3
C-228imidaclopridNOOCONHEtOO1methyl
C-229imidaclopridNOOCONHn-PrOO1methyl
C-230imidaclopridNOOCONHn-BuOO1methyl
C-231imidaclopridNOOCONHn-BuOO1C(CH3)3
C-232imidaclopridNOOCONHn-BuOO1Ph
C-233imidaclopridNOOCONHn-BuOO14Me(Ph)
C-234imidaclopridNOOCONHn-BuOO1CF3CH2
C-235imidaclopridNOOCONHn-Bu——0Cl
C-236imidaclopridNOOCONHn-Bu——0{N(Et)3}+Cl−
C-237imidaclopridNOOCONH—BnOO1methyl
C-238imidaclopridNOOCONH—BnOO1C(CH3)3
C-239imidaclopridNOOCONH—Bn——0{N(Et)3}+Cl−
C-240imidaclopridNOOCONNH2OO1methyl
C-241ketamineNOOCONHNHMeOO1methyl
C-242ketamineNOOCONHNHEtOO1methyl
C-243ketamineNOOCONHNHPrOO1methyl
C-244ketamineNOOCONHNHt-BuOO1C(CH3)3
C-245ketamineNOOCONHNHCO2MeOO1C(CH3)3
C-246ketamineNOOCONHNHCO2EtOO1C(CH3)3
C-247ketamineNOOCONHNHCO2t-BuOO1C(CH3)3
C-248ketamineNOOCONHNHCO2BnOO1C(CH3)3
C-249ketamineNOOCONHN═CHMeOO1methyl
C-250ketamineNOOCONHN═CHMe——0{N(Et)3}+Cl−
C-251ketamineNOOCONHN═CHPhOO1methyl
C-252ketamineNOOCONHN═CHPhOO1C(CH3)3
C-253lidocaineNOOCO2HOO1methyl
C-254lincomycinNOOCO2HOO1C(CH3)3
C-255lomustineNOOCO2HOO1Ph
C-256lomustineNOOCO2HOO14Me(Ph)
C-257lomustineNOOCO2H——0Cl
C-258lomustineNOOCO2H——0{N(Et)3}+Cl−
C-259lomustineNOOCO2H——0{N(Me)2Ph}+Cl−
C-260lomustineNOOCO2MeOO1methyl
C-261lomustineNOOCO2MeOO1C(CH3)3
C-262lomustineNOOCO2MeOO1Ph
C-263lomustineNOOCO2MeOO14Me(Ph)
C-264lomustineNOOCO2Me——0Cl
C-265lomustineNOOCO2Me——0{N(Et)3}+Cl−
C-266lomustineNOOCO2Me——0{N(Me)2Ph}+Cl−
C-267lomustineNOOCO2EtOO1methyl
C-268lomustineNOOCO2Et——0Cl
C-269lomustineNOSCO2n-PrOO1methyl
C-270lomustineNOSCO2n-Pr——0Cl
C-271lomustineNOOCO2n-BuOO1methyl
C-272lomustineNOOCO2n-BuOO1C(CH3)3
C-273mechlorethamineNOOCO2n-BuOO1Ph
C-274mechlorethamineNOSCO2n-BuOO14Me(Ph)
C-275mechlorethamineNOSCO2n-BuOO1CF3CH2
C-276mechlorethamineNOOCO2n-Bu——0Cl
C-277mechlorethamineNOOCO2n-Bu——0{N(Et)3}+Cl−
C-278mechlorethamineNOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-279mechlorethamineNOOCO2n-Bu——0O—C(CH3)3
C-280meclofenamic acidNOOCO2—BnOO1methyl
C-281mercaptopurineNOOCO2—BnOO1C(CH3)3
C-282methotrexateNOOCO2—BnOO1Ph
C-283mexiletineNOSCO2—BnOO14Me(Ph)
C-284mexiletineNOSCO2—BnOO1CF3CH2
C-285mexiletineNOOCO2—Bn——0Cl
C-286mexiletineNOOCO2—Bn——0{N(Et)3}+Cl−
C-287mexiletineNOOCO2—Bn——0{N(Me)2Ph}+Cl−
C-288mexiletineNOOCO2—Bn——0OC(CH3)3
C-289mexiletineNOOCOSMeOO1methyl
C-290mexiletineNOSCOSMeOO1C(CH3)3
C-291mexiletineNOOCOSMe——0Cl
C-292mexiletineNOOCOSMe——0{N(Et)3}+Cl−
C-293mexiletineNOSCOSEtOO1methyl
C-294mexiletineNOOCOSEt——0Cl
C-295mexiletineNOOCOSn-BuOO1methyl
C-296mexiletineNOSCOSn-Bu——0Cl
C-297mexiletineNOOCOSBnOO1methyl
C-298mexiletineNOOCOSBn——0Cl
C-299mexiletineNOOCONHMeOO1methyl
C-300mexiletineNOOCONHMeOO1C(CH3)3
C-301mexiletineNOOCONHEtOO1methyl
C-302mexiletineNOOCONHn-PrOO1methyl
C-303mexiletineNOOCONHn-BuOO1methyl
C-304mexiletineNOOCONHn-BuOO1C(CH3)3
C-305mexiletineNOOCONHn-BuOO1Ph
C-306mexiletineNOOCONHn-BuOO14Me(Ph)
C-307mexiletineNOOCONHn-BuOO1CF3CH2
C-308mexiletineNOOCONHn-Bu——0Cl
C-309mexiletineNOOCONHn-Bu——0{N(Et)3}+Cl−
C-310ormetoprimNOOCONH—BnOO1methyl
C-311prostaglandin E1OOOCONH—BnOO1C(CH3)3
C-312quinacrineNOOCONH—Bn——0{N(Et)3}+Cl−
C-313quinacrineNOOCONNH2OO1methyl
C-314quinacrineNOOCONHNHMeOO1methyl
C-315quinacrineNOOCONHNHEtOO1methyl
C-316quinacrineNOOCONHNHPrOO1methyl
C-317quinacrineNOOCONHNHt-BuOO1C(CH3)3
C-318quinacrineNOOCONHNHCO2MeOO1C(CH3)3
C-319quinacrineNOOCONHNHCO2EtOO1C(CH3)3
C-320quinacrineNOOCONHNHCO2t-BuOO1C(CH3)3
C-321quinacrineNOOCONHNHCO2BnOO1C(CH3)3
C-322quinacrineNOOCONHN═CHMeOO1methyl
C-323quinacrineNOOCONHN═CHMe——0{N(Et)3}+Cl−
C-324quinacrineNOOCONHN═CHPhOO1methyl
C-325quinacrineNOOCONHN═CHPhOO1C(CH3)3
C-326quinidineNOOCO2HOO1methyl
C-327quinidineNOOCO2HOO1C(CH3)3
C-328quinidineNOOCO2HOO1Ph
C-329quinidineNOOCO2HOO14Me(Ph)
C-330quinidineNOOCO2H——0Cl
C-331quinidineNOOCO2H——0{N(Et)3}+Cl−
C-332quinidineNOOCO2HOO0{N(Me)2Ph}+Cl−
C-333quinidineNOOCO2Me——1methyl
C-334quinidineNOOCO2MeOO1C(CH3)3
C-335quinidineNOOCO2MeOO1Ph
C-336quinidineNOOCO2MeOO14Me(Ph)
C-337quinidineNOOCO2Me——0Cl
C-338quinidineNOOCO2Me——0{N(Et)3}+Cl−
C-339quinidineNOOCO2Me——0{N(Me)2Ph}+Cl−
C-340quinidineNOOCO2EtOO1methyl
C-341quinidineNOOCO2EtOO0Cl
C-342quinidineNOSCO2n-PrOO1methyl
C-343quinidineNOSCO2n-Pr——0Cl
C-344quinidineNOOCO2n-BuOO1methyl
C-345sulfachlor-NOOCO2n-BuOO1C(CH3)3
pyridazine
C-346sulfadiazineNOOCO2n-BuOO1Ph
C-347sulfamethoxazoleNOSCO2n-BuOO14Me(Ph)
C-348theophyllineNOSCO2n-BuOO1CF3CH2
C-349theophyllineNOOCO2n-Bu——0Cl
C-350theophyllineNOOCO2n-Bu——0{N(Et)3}+Cl−
C-351theophyllineNOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-352theophyllineNOOCO2n-Bu——0OC(CH3)3
C-353theophyllineNOOCO2—BnOO1methyl
C-354theophyllineNOOCO2—BnOO1C(CH3)3
C-355theophyllineNOOCO2—BnOO1Ph
C-356theophyllineNOSCO2—BnOO14Me(Ph)
C-357theophyllineNOSCO2—BnOO1CF3CH2
C-358theophyllineNOOCO2—Bn——0Cl
C-359theophyllineNOOCO2—Bn——0{N(Et)3}+Cl−
C-360theophyllineNOOCO2—Bn——0{N(Me)2Ph}+Cl−
C-361theophyllineNOOCO2—BnOO0OC(CH3)3
C-362theophyllineNOOCOSMeOO1methyl
C-363theophyllineNOSCOSMeOO1C(CH3)3
C-364theophyllineNOOCOSMe——0Cl
C-365theophyllineNOOCOSMe——0{N(Et)3}+Cl−
C-366theophyllineNOSCOSEtOO1methyl
C-367theophyllineNOOCOSEt——0Cl
C-368theophyllineNOOCOSn-BuOO1methyl
C-369theophyllineNOSCOSn-Bu——0Cl
C-370theophyllineNOOCOSBnOO1methyl
C-371theophyllineNOOCOSBn——0Cl
C-372theophyllineNOOCONHMeOO1methyl
C-373theophyllineNOOCONHMeOO1C(CH3)3
C-374theophyllineNOOCONHEtOO1methyl
C-375theophyllineNOOCONHn-PrOO1methyl
C-376theophyllineNOOCONHn-BuOO1methyl
C-377tiletamineNOOCONHn-BuOO1C(CH3)3
C-378tiletamineNOOCONHn-BuOO1Ph
C-379tiletamineNOOCONHn-BuOO14Me(Ph)
C-380tiletamineNOOCONHn-BuOO1CF3CH2
C-381tiletamineNOOCONHn-Bu——0Cl
C-382tiletamineNOOCONHn-Bu——0{N(Et)3}+Cl−
C-383tiletamineNOOCONH—BnOO1methyl
C-384tiletamineNOOCONH—BnOO1C(CH3)3
C-385tiletamineNOOCONH—Bn——0{N(Et)3}+Cl−
C-386tiletamineNOOCONNH2OO1methyl
C-387tiletamineNOOCONHNHMeOO1methyl
C-388tiletamineNOOCONHNHEtOO1methyl
C-389tiletamineNOOCONHNHPrOO1methyl
C-390tiletamineNOOCONHNHt-BuOO1C(CH3)3
C-391tiletamineNOOCONHNHCO2MeOO1C(CH3)3
C-392tiletamineNOOCONHNHCO2EtOO1C(CH3)3
C-393tiletamineNOOCONHNHCO2t-BuOO1C(CH3)3
C-394tiletamineNOOCONHNHCO2BnOO1C(CH3)3
C-395tiletamineNOOCONHN═CHMeOO1methyl
C-396tiletamineNOOCONHN═CHMe——0{N(Et)3}+Cl−
C-397tiletamineNOOCONHN═CHPhOO1methyl
C-398tiletamineNOOCONHN═CHPhOO1C(CH3)3
C-399tacainideNOOCO2HOO1methyl
C-400tocainideNOOCO2HOO1C(CH3)3
C-401tocainideNOOCO2HOO1Ph
C-402tocainideNOOCO2HOO14Me(Ph)
C-403tocainideNOOCO2H——0Cl
C-404tocainideNOOCO2H——0{N(Et)3}+Cl−
C-405tocainideNOOCO2H——0{N(Me)2Ph}+Cl−
C-406tocainideNOOCO2MeOO1methyl
C-407tocainideNOOCO2MeOO1C(CH3)3
C-408tocainideNOOCO2MeOO1Ph
C-409tocainideNOOCO2MeOO14Me(Ph)
C-410tocainideNOOCO2Me——0Cl
C-411tocainideNOOCO2Me——0{N(Et)3}+Cl−
C-412tocainideNOOCO2Me——0{N(Me)2Ph}+Cl−
C-413tocainideNOOCO2EtOO1methyl
C-414tocainideNOOCO2Et——0Cl
C-415tocainideNOSCO2n-PrOO1methyl
C-416tocainideNOSCO2n-Pr——0Cl
C-417tocainideNOOCO2n-BuOO1methyl
C-418tocainideNOOCO2n-BuOO1C(CH3)3
C-419tocainideNOOCO2n-BuOO1Ph
C-420tocainideNOSCO2n-BuOO14Me(Ph)
C-421tocainideNOSCO2n-BuOO1CF3CH2
C-422tocainideNOOCO2n-Bu——0Cl
C-423tocainideNOOCO2n-Bu——0{N(Et)3}+Cl−
C-424tocainideNOOCO2n-Bu——0{N(Me)2Ph}+Cl−
C-425tocainideNOOCO2n-Bu——0OC(CH3)3
C-426vincristineNOOCO2—BnOO1methyl
C-427xylazineNOOCO2—BnOO1C(CH3)3
C-428xylazineNOOCO2—BnOO1Ph
C-429xylazineNOSCO2—BnOO14Me(Ph)
C-430xylazineNOSCO2—BnOO1CF3CH2
C-431xylazineNOOCO2—Bn——0Cl
C-432xylazineNOOCO2—Bn——0{N(Et)3}+Cl−
C-433xylazineNOOCO2—Bn——0{N(Me)2Ph}+Cl−
C-434xylazineNOOCO2—Bn——0OC(CH3)3
C-435xylazineNOOCOSMeOO1methyl
C-436xylazineNOSCOSMeOO1C(CH3)3
C-437xylazineNOOCOSMe——0Cl
C-438xylazineNOOCOSMe——0{N(Et)3}+Cl−
C-439xylazineNOSCOSEtOO1methyl
C-440xylazineNOOCOSEt——0Cl
C-441xylazineNOOCOSn-BuOO1methyl
C-442xylazineNOSCOSn-Bu——0Cl
C-443xylazineNOOCOSBnOO1methyl
C-444xylazineNOOCOSBn——0Cl
C-445xylazineNOOCONHMeOO1methyl
C-446xylazineNOOCONHMeOO1C(CH3)3
C-447xylazineNOOCONHEtOO1methyl
C-448xylazineNOOCONHn-PrOO1methyl
C-449xylazineNOOCONHn-BuOO1methyl
C-450xylazineNOOCONHn-BuOO1C(CH3)3
C-451xylazineNOOCONHn-BuOO1Ph
C-452xylazineNOOCONHn-BuOO14Me(Ph)
C-453xylazineNOOCONHn-BuOO1CF3CH2
C-454xylazineNOOCONHn-Bu——0Cl
C-455xylazineNOOCONHn-Bu——0{N(Et)3}+Cl−
C-456xylazineNOOCONH—BnOO1methyl
C-457xylazineNOOCONH—BnOO1C(CH3)3
C-458xylazineNOOCONH—Bn——0{N(Et)3}+Cl−
C-459xylazineNOOCONNH2OO1methyl
C-460xylazineNOOCONHNHMeOO1methyl
C-461xylazineNOOCONHNHEtOO1methyl
C-462xylazineNOOCONHNHPrOO1methyl
C-463xylazineNOOCONHNHt-BuOO1C(CH3)3
C-464xylazineNOOCONHNHCO2MeOO1C(CH3)3
C-465xylazineNOOCONHNHCO2EtOO1C(CH3)3
C-466xylazineNOOCONHNHCO2t-BuOO1C(CH3)3
C-467xylazineNOOCONHNHCO2BnOO1C(CH3)3
C-468xylazineNOOCONHN═CHMeOO1methyl
C-469xylazineNOOCONHN═CHMe——0{N(Et)3}+Cl−
C-470xylazineNOOCONHN═CHPhOO1methyl
C-471xylazineNOOCONHN═CHPhOO1C(CH3)3
|
[0731] Table D describes additional examples of compounds of Formula I which can be made using the procedures described hereinbefore, where R2 is hydrogen, m=0, q=1, t=0 or 1 and the pharmaceutical (a veterinary drug) which defines the 5 pharmaceutical moiety of these examples is Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2).). The following groups, Z1, G10, G11, R1, G20, G21, t, X2 and Z2(X2)—[(C=G20)-G21]-H, Z2(X2)q—H or Z2(X2) are defined within Table D.
14TABLE D
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|
|
87
|
Z2(X2)q-[(C═G20)-G21]t-H
or when t = 0, Z2(X2)q or
Cmpd #Z1G10G11R1G20G21tX2Z2(X2)q-H
|
D-1methylOOCO2H——0Nalbendazole
D-2methylOOCO2H——0Oclioquinol
D-3n-propylOOCO2H——0Nfebantel
D-4n-propylOOCO2H——0Nfenbendazole
D-5C(CH3)3OOCO2H——0Oguaifenesin
D-6C(CH3)3OOCO2H——0Omibolerone
D-7PhOOCO2H——0Nomeprazole
D-8PhOOCO2Me——0Ooxazepam
D-94Cl(Ph)OOCO2Me——0Npiroxicam
D-104Cl(Ph)OOCO2Me——0Nprimidone
D-11methylOOCO2Me——0Nprocainamide
D-12methylOOCO2Me——0Nthiabendazole
D-13n-propylOOCO2Me——0Owarfarin
D-14n-propylOOCO2Me——0Nalbendazole
D-15PhOOCO2Et——0Oclioquinol
D-16PhOOCO2Et——0Nfebantel
D-17methylOSCO2n-Pr——0Nfenbendazole
D-18n-propylOSCO2n-Pr——0Oguaifenesin
D-19C(CH3)3OOCO2n-Bu——0Omibolerone
D-20PhOOCO2n-Bu——0Nomeprazole
D-21PhOOOCO2n-Bu——0Ooxazepam
D-22PhNHOSCO2n-Bu——0Npiroxicam
D-234Cl(Ph)OSCO2n-Bu——0Nprimidone
D-244Cl(Ph)OOOCO2n-Bu——0Nprocainamide
D-254Cl(Ph)NHOOCO2n-Bu——0Nthiabendazole
D-26pyrid-2-ylOOCO2n-Bu——0Owarfarin
D-27pyrid-4-ylOOCO2n-Bu——0Nalbendazole
D-28methylOOCO2—Bn——0Oclioquinol
D-29n-propylOOCO2—Bn——0Nfebantel
D-30C(CH3)3OOCO2—Bn——0Nfenbendazole
D-31PhOSCO2—Bn——0Oguaifenesin
D-32PhOOSCO2—Bn——0Omibolerone
D-33PhNHOOCO2—Bn——0Nomeprazole
D-344Cl(Ph)OOCO2—Bn——0Ooxazepam
D-354Cl(Ph)OOOCO2—Bn——0Npiroxicam
D-364Cl(Ph)NHOOCO2—Bn——0Nprimidone
D-37pyrid-2-ylOOCOSMe——0Nprocainamide
D-38pyrid-4-ylOSCOSMe——0Nthiabendazole
D-39methylOOCOSMe——0Owarfarin
D-40n-propylOOCOSMe——0Nalbendazole
D-41C(CH3)3OSCOSEt——0Oclioquinol
D-42PhOOCOSEt——0Nfebantel
D-43PhOOOCOSn-Bu——0Nfenbendazole
D-44Ph—NHOSCOSn-Bu——0Oguaifenesin
D-454Cl(Ph)OOCOSBn——0Omibolerone
D-464Cl(Ph)OOOCOSBn——0Nomeprazole
D-474Cl(Ph)NHOOCONHMe——0Ooxazepam
D-48pyrid-2-ylOOCONHMe——0Npiroxicam
D-49pyrid-4-ylOOCONHEt——0Nprimidone
D-50methylOOCONHn-Pr——0Nprocainamide
D-51n-propylOOCONHn-Bu——0Nthiabendazole
D-52C(CH3)3OOCONHn-Bu——0Owarfarin
D-53PhOOCONHn-Bu——0Nalbendazole
D-54PhOOOCONHn-Bu——0Oclioquinol
D-55Ph—NHOOCONHn-Bu——0Nfebantel
D-564C1(Ph)OOCONHn-Bu——0Nfenbendazole
D-574Cl(Ph)OOOCONHn-Bu——0Oguaifenesin
D-584Cl(Ph)NHOOCONH—Bn——0Omibolerone
D-59pyrid-2-ylOOCONH—Bn——0Nomeprazole
D-60pyrid-4-ylOOCONH—Bn——0Ooxazepam
D-61methylOOCONNH2——0Npiroxicam
D-62n-propylOOCONHNHMe——0Nprimidone
D-63C(CH3)3OOCONHNHEt——0Nprocainamide
D-64PhOOCONHNHPr——0Nthiabendazole
D-65PhOOOCONHNHt-Bu——0Owarfarin
D-66Ph—NHOOCONHNHCO2Me——0Nalbendazole
D-674Cl(Ph)OOCONHNHCO2Et——0Oclioquinol
D-684Cl(Ph)OOOCONHNHCO2t-Bu——0Nfebantel
D-694Cl(Ph)NHOOCONHNHCO2Bn——0Nfenbendazole
D-70pyrid-2-ylOOCONHN═CHMe——0Oguaifenesin
D-71pyrid-4-ylOOCONHN═CHMe——0Omibolerone
D-72methylOOCONHN═CHPh——0Nomeprazole
D-73n-propylOOCONHN═CHPh——0Ooxazepam
D-74methylOOCO2HOO1Ccaptopril
D-75ethylOOCO2HOO1Ccaptopril
D-76n-propylOOCO2HOO1Ccaptopril
D-77C(CH3)3OOCO2HOO1Ccaptopril
D-78MeOOOCO2HOO1Ccaptopril
D-79EtOOOCO2HOO1Ccaptopril
D-80n-PrOOOCO2HOO1Ccaptopril
D-81MeNHOOCO2MeOO1Ccaptopril
D-82EtNHOOCO2MeOO1Ccaptopril
D-83n-PrNHOOCO2MeOO1Ccaptopril
D-84n-PrOOOCO2MeOO1Ccaptopril
D-85PhOOOCO2MeOO1Ccaptopril
D-86Ph—NHOOCO2MeOO1Ccaptopril
D-874Cl(Ph)OOCO2MeOO1Ccaptopril
D-884Cl(Ph)OOOCO2EtOO1Ccaptopril
D-894Cl(Ph)NHOOCO2EtOO1Ccaptopril
D-90MeOOSCO2n-PrOO1Ccaptopril
D-91EtOOSCO2n-PrOO1Ccaptopril
D-92n-PrOOOCO2n-BuOO1Ccaptopril
D-93MeNHOOCO2n-BuOO1Ccaptopril
D-94EtNHOOCO2n-BuOO1Ccaptopril
D-95n-PrNHOSCO2n-BuOO1Ccaptopril
D-96n-PrOOSCO2n-BuOO1Ccaptopril
D-97PhOOOCO2n-BuOO1Ccaptopril
D-98Ph—NHOOCO2n-BuOO1Ccaptopril
D-994Cl(Ph)OOCO2n-BuOO1Ccaptopril
D-1004Cl(Ph)OOOCO2n-BuOO1Ccaptopril
D-101MeOOOCO2—BnOO1Ccephapirin
D-102EtOOOCO2—BnOO1Ccephapirin
D-103n-PrOOOCO2—BnOO1Ccephapirin
D-104MeNHOSCO2—BnOO1Ccephapirin
D-105EtNHOSCO2—BnOO1Ccephapirin
D-106n-PrNHOOCO2—BnOO1Ccephapirin
D-108PhOOOCO2—BnOO1Ccephapirin
D-109Ph—NHOOCO2—BnOO1Ccephapirin
D-1104Cl(Ph)OOCOSMeOO1Ccephapirin
D-1114Cl(Ph)OOSCOSMeOO1Ccephapirin
D-1124Cl(Ph)NHOOCOSMeOO1Ccephapirin
D-113MeOOOCOSMeOO1Ccephapirin
D-114EtOOSCOSEtOO1Ccephapirin
D-115n-PrOOOCOSEtOO1Ccephapirin
D-116MeNHOOCOSn-BuOO1Ccephapirin
D-117EtNHOSCOSn-BuOO1Ccephapirin
D-118n-PrNHOOCOSBnOO1Ccephapirin
D-119n-PrOOOCOSBnOO1Ccephapirin
D-120PhOOOCONHMeOO1Ccephapirin
D-121PhNHOOCONHMeOO1Ccephapirin
D-1224Cl(Ph)OOCONHEtOO1Ccephapirin
D-1234Cl(Ph)OOOCONHn-PrOO1Ccephapirin
D-1244Cl(Ph)NHOOCONHn-BuOO1Ccephapirin
D-125MeOOOCONHn-BuOO1Ccephapirin
D-126EtOOOCONHn-BuOO1Ccephapirin
D-127n-PrOOOCONHn-BuOO1Ccephapirin
D-128MeNHOOCONHn-BuOO1Ccephapirin
D-129EtNHOOCONHn-BuOO1Ccephapirin
D-130n-PrNHOOCONHn-BuOO1Ccephapirin
D-131n-PrOOOCONH—BnOO1Ccephapirin
D-132PhOOOCONH—BnOO1Ccephapirin
D-133Ph—NHOOCONH—BnOO1Ccephapirin
D-1344Cl(Ph)OOCONNH2OO1Ccephapirin
D-1354Cl(Ph)OOOCONHNHMeOO1Ccephapirin
D-1364Cl(Ph)NHOOCONHNHEtOO1Ccephapirin
D-137MeOOOCONHNHPrOO1Ccephapirin
D-138EtOOOCONHNHt-BuOO1Ccephapirin
D-139n-PrOOOCONHNHCO2MeOO1Ccephapirin
D-140MeNHOOCONHNHCO2EtOO1Ccephapirin
D-141EtNHOOCONHNHCO2t-BuOO1Ccephapirin
D-142n-PrNHOOCONHNHCO2BnOO1Ccephapirin
D-143n-PrOOOCONHN═CHMeOO1Ccephapirin
D-144PhOOOCONHN═CHMeOO1Ccephapirin
D-145Ph—NHOOCONHN═CHPhOO1Ccephapirin
D-1464Cl(Ph)NHOOCONHN═CHPhOO1Ccephapirin
D-147methylOOCO2H——0Ncephapirin
D-148ethylOOCO2H——0Ncephapirin
D-149n-propylOOCO2H——0Ncephapirin
D-150C(CH3)3OOCO2H——0Ncephapirin
D-151MeOOOCO2H——0Ncephapirin
D-152EtOOOCO2H——0Ncephapirin
D-153n-PrOOOCO2H——0Ncephapirin
D-154MeNHOOCO2Me——0Ncephapirin
D-155EtNHOOCO2Me——0Ncephapirin
D-156n-PrNHOOCO2Me——0Ncephapirin
D-157n-PrOOOCO2Me——0Ncephapirin
D-158PhOOOCO2Me——0Ncephapirin
D-159PhNHOOCO2Me——0Ncephapirin
D-1604Cl(Ph)OOCO2Me——0Ncephapirin
D-1614Cl(Ph)OOOCO2Et——0Ncephapiirin
D-1624Cl(Ph)NHOOCO2Et——0Ncephapirin
D-163Ph—NHOSCO2n-Pr——0Ncephapirin
D-1644Cl(Ph)OSCO2n-Pr——0Ncephapirin
D-1654Cl(Ph)OOOCO2n-Bu——0Ncephapirin
D-1664Cl(Ph)NHOOCO2n-Bu——0Ncephapirin
D-167pyrid-2-ylOOCO2n-Bu——0Ncephapirin
D-168pyrid-4-ylOSCO2n-Bu——0Ncephapirin
D-169MeOOSCO2n-Bu——0Ncephapirin
D-170EtOOOCO2n-Bu——0Ncephapirin
D-171n-PrOOOCO2n-Bu——0Ncephapirin
D-172PhOOOCO2n-Bu——0Ncephapirin
D-173MeOOOCO2n-BuOO1Cketoprofen
D-174EtOOOCO2—BnOO1Cketoprofen
D-175n-PrOOOCO2—BnOO1Cketoprofen
D-176(CH3)3COOOCO2—BnOO1Cketoprofen
D-177MeNHOSCO2—BnOO1Cketoprofen
D-178EtNHOSCO2—BnOO1Cketoprofen
D-179n-PrNHOOCO2—BnOO1Cketoprofen
D-180(CH3)3CNHOOCO2—BnOO1Cketoprofen
D-181PhOOOCO2—BnOO1Cketoprofen
D-182PhNHOOCO2—BnOO1Cketoprofen
D-1834Cl(Ph)OOCOSMeOO1Cketaprofen
D-1844Cl(Ph)OOSCOSMeOO1Cketoprofen
D-1854Cl(Ph)NHOOCOSMeOO1Cketoprofen
D-186MeOOOCOSMeOO1Cketoprofen
D-187EtOOSCOSEtOO1Cketoprofen
D-188n-PrOOOCOSEtOO1Cketoprofen
D-189(CH3)3COOOCOSn-BuOO1Cketoprofen
D-190MeNHOSCOSn-BuOO1Cketoprofen
D-191EtNHOOCOSBnOO1Cketoprofen
D-192n-PrNHOOCOSBnOO1Cketoprofen
D-193(CH3)3CNHOOCONHMeOO1Cketoprofen
D-194PhOOOCONHMeOO1Cketoprofen
D-195Ph—NHOOCONHEtOO1Cketoprofen
D-1964Cl(Ph)OOCONHn-PrOO1Cketoprofen
D-1974Cl(Ph)OOOCONHn-BuOO1Cketoprofen
D-1984Cl(Ph)NHOOCONHn-BuOO1Cketoprofen
D-199MeOOOCONHn-BuOO1Cketoprofen
D-200EtOOOCONHn-BuOO1Cketoprofen
D-201n-PrOOOCONHn-BuOO1Cketoprofen
D-202(CH3)3COOOCONHn-BuOO1Cketoprofen
D-203MeNHOOCONHn-BuOO1Cketoprofen
D-204EtNHOOCONH—BnOO1Cketoprofen
D-205n-PrNHOOCONH—BnOO1Cketoprofen
D-206(CH3)3CNHOOCONH—BnOO1Cketoprofen
D-207PhOOOCONNH2OO1Cketoprofen
D-208Ph—NHOOCONHNHMeOO1Cketoprofen
D-2094Cl(Ph)OOCONHNHEtOO1Cketoprofen
D-2104Cl(Ph)OOOCONHNHPrOO1Cketoprofen
D-2114CH3O(Ph)OOOCONHNHt-BuOO1Cketoprofen
D-2124NO2(Ph)OOOCONHNHCO2MeOO1Cketoprofen
D-2134Cl(Ph)NHOOCONHNHCO2EtOO1Cketoprofen
D-2144MeO(Ph)NHOOCONHNHCO2t-BuOO1Cketoprofen
D-215MeOOOCONHNHCO2BnOO1Cketoprofen
D-216EtOOOCONHN═CHMeOO1Cketoprofen
D-217n-PrOOOCONHN═CHMeOO1Cketoprofen
D-218(CH3)3COOOCONHN═CHPhOO1Cketoprofen
D-219MeNHOOCONHN═CHPhOO1Cketoprofen
D-220EtNHOOCO2HOO1Cketoprofen
D-221n-PrNHOOCO2HOO1Cketoprofen
D-222(CH3)3CNHOOCO2HOO1Cketoprofen
D-223PhOOOCO2HOO1Cketoprofen
D-224PhNHOOCO2HOO1Cketoprofen
D-2254Cl(Ph)OOCO2HOO1Cketoprofen
D-2264Cl(Ph)OOOCO2HOO1Cketoprofen
D-2274CH3O(Ph)OOOCO2MeOO1Cketoprofen
D-2284NO2(Ph)OOOCO2MeOO1Cketoprofen
D-2294Cl(Ph)NHOOCO2MeOO1Cketoprofen
D-2304MeO(Ph)NHOOCO2MeOO1Cketoprofen
D-231PhNHOOCO2MeOO1Cketoprofen
D-2344Cl(Ph)NHOOCO2EtOO1Cketoprofen
D-2354MeO(Ph)NHOOCO2EtOO1Cketoprofen
D-236PhOOSCO2n-PrOO1Cketoprofen
D-237PhNHOSCO2n-PrOO1Cketoprofen
D-238methylOOCO2n-BuOO1Cketoprofen
D-239ethylOOCO2n-BuOO1Cketoprofen
D-240n-propylOOCO2n-BuOO1Cketoprofen
D-241C(CH3)3OSCO2n-BuOO1Cketoprofen
D-242MeOOSCO2n-BuOO1Cketoprofen
D-243EtOOOCO2n-BuOO1Cketoprofen
D-244n-PrOOOCO2n-BuOO1Cketoprofen
D-245MeNHOOCO2n-BuOO1Cketoprofen
D-246EtNHOOCO2n-BuOO1Cketoprofen
D-247n-PrNHOOCO2—BnOO1Cvalproic acid
D-248n-PrOOOCO2—BnOO1Cvalproic acid
D-249PhOOOCO2—BnOO1Cvalproic acid
D-250Ph—NHOSCO2—BnOO1Cvalproic acid
D-2514Cl(Ph)OSCO2—BnOO1Cvalproic acid
D-2524Cl(Ph)OOOCO2—BnOO1Cvalproic acid
D-2534CH3O(Ph)OOOCO2—BnOO1Cvalproic acid
D-2544NO2(Ph)OOOCO2—BnOO1Cvalproic acid
D-2554Cl(Ph)NHOOCO2—BnOO1Cvalproic acid
D-2564F(Ph)NHOOCOSMeOO1Cvalproic acid
D-2574MeO(Ph)NHOSCOSMeOO1Cvalproic acid
D-258pyrid-2-ylOOCOSMeOO1Cvalproic acid
D-259pyrid-4-ylOOCOSMeOO1Cvalproic acid
D-260MeOOSCOSEtOO1Cvalproic acid
D-261EtOOOCOSEtOO1Cvalproic acid
D-262n-PrOOOCOSn-BuOO1Cvalproic acid
D-263PhOOSCOSn-BuOO1Cvalproic acid
D-264MeNHOOCOSBnOO1Cvalproic acid
D-265PhNHOOCOSBnOO1Cvalproic acid
D-266MeOOOCONHMeOO1Cvalproic acid
D-267EtOOOCONHMeOO1Cvalproic acid
D-268n-PrOOOCONHEtOO1Cvalproic acid
D-269(CH3)3COOOCONHn-PrOO1Cvalproic acid
D-270MeNHOOCONHn-BuOO1Cvalproic acid
D-271EtNHOOCONHn-BuOO1Cvalproic acid
D-272n-PrNHOOCONHn-BuOO1Cvalproic acid
D-273(CH3)3CNHOOCONHn-BuOO1Cvalproic acid
D-274PhOOOCONHn-BuOO1Cvalproic acid
D-275PhNHOOCONHn-BuOO1Cvalproic acid
D-2764Cl(Ph)OOCONHn-BuOO1Cvalproic acid
D-2774Cl(Ph)OOOCONH—BnOO1Cvalproic acid
D-2784Cl(Ph)NHOOCONH—BnOO1Cvalproic acid
D-279MeOOOCONH—BnOO1Cvalproic acid
D-280EtOOOCONNH2OO1Cvalproic acid
D-281n-PrOOOCONHNHMeOO1Cvalproic acid
D-282(CH3)3COOOCONHNHEtOO1Cvalproic acid
D-283MeNHOOCONHNHPrOO1Cvalproic acid
D-284EtNHOOCONHNHt-BuOO1Cvalproic acid
D-285n-PrNHOOCONHNHCO2MeOO1Cvalproic acid
D-286(CH3)3CNHOOCONHNHCO2EtOO1Cvalproic acid
D-287PhOOOCONHNHCO2t-BuOO1Cvalproic acid
D-288PhNHOOCONHNHCO2BnOO1Cvalproic acid
D-2894Cl(Ph)OOCONHN═CHMeOO1Cvalproic acid
D-2904Cl(Ph)OOOCONHN═CHMeOO1Cvalproic acid
D-2914Cl(Ph)NHOOCONHN═CHPhOO1Cvalproic acid
D-292MeOOOCONHN═CHPhOO1Cvalproic acid
D-293EtOOOCO2HOO1Cvalproic acid
D-294n-PrOOOCO2HOO1Cvalproic acid
D-295(CH3)3COOOCO2HOO1Cvalproic acid
D-296MeNHOOCO2HOO1Cvalproic acid
D-297EtNHOOCO2HOO1Cvalproic acid
D-298n-PrNHOOCO2HOO1Cvalproic acid
D-299(CH3)3CNHOOCO2HOO1Cvalproic acid
D-300PhOOOCO2MeOO1Cvalproic acid
D-301PhNHOOCO2MeOO1Cvalproic acid
D-3024Cl(Ph)OOCO2MeOO1Cvalproic acid
D-3034Cl(Ph)OOOCO2MeOO1Cvalproic acid
D-3044CH3O(Ph)OOOCO2MeOO1Cvalproic acid
D-3054NO2(Ph)OOOCO2MeOO1Cvalproic acid
D-3064Cl(Ph)NHOOCO2MeOO1Cvalproic acid
D-3074F(Ph)NHOOCO2EtOO1Cvalproic acid
D-3084MeO(Ph)NHOOCO2EtOO1Cvalproic acid
D-309MeOOSCO2n-PrOO1Cvalproic acid
D-310EtOOSCO2n-PrOO1Cvalproic acid
D-311n-PrOOOCO2n-BuOO1Cvalproic acid
D-312(CH3)3COOOCO2n-BuOO1Cvalproic acid
D-313MeNHOOCO2n-BuOO1Cvalproic acid
D-314EtNHOSCO2n-BuOO1Cvalproic acid
D-315n-PrNHOSCO2n-BuOO1Cvalproic acid
D-316(CH3)3CNHOOCO2n-BuOO1Cvalproic acid
D-317PhOOOCO2n-BuOO1Cvalproic acid
D-318PhNHOOCO2n-BuOO1Cvalproic acid
D-3194Cl(Ph)OOCO2n-BuOO1Cvalproic acid
D-320methylOOCO2—Bn——0Nacepromazine
D-321ethylOOCO2—Bn——0Naminopropazine
D-322n-propylOOCO2—Bn——0Namiodarone
D-323C(CH3)3OSCO2—Bn——0Namitriptyline
D-324MeOOSCO2—Bn——0Natropine
D-325EtOOOCO2—Bn——0Natropine
D-326n-PrOOOCO2—Bn——0Oatropine
D-327MeNHOOCO2—Bn——0Oatropine
D-328EtNHOOCO2—Bn——0Nazaperone
D-329n-PrNHOOCOSMe——0Nbuspirone
D-330n-PrOOSCOSMe——0Nchlorpheniramine
D-331PhOOOCOSMe——0Nclemastine
D-332Ph—NHOOCOSMe——0Nclomipramine
D-3334Cl(Ph)OSCOSEt——0Ncyproheptadine
D-3344Cl(Ph)OOOCOSEt——0Ndiethylcarbamazine
D-3354CH3O(Ph)OOOCOSn-Bu——0Ndiltiazem
D-3364NO2(Ph)OOSCOSn-Bu——0Ndiphenhydramine
D-3374Cl(Ph)NHOOCOSBn——0Ndiphenoxylate
D-3384F(Ph)NHOOCOSBn——0Ndoxapram
D-3394MeO(Ph)NHOOCONHMe——0Ndoxepin
D-340pyrid-2-ylOOCONHMe——0Ndoxylamine
D-341pyrid-4-ylOOCONHEt——0Ndroperidol
D-342MeOOOCONHn-Pr——0Nfentanyl
D-343EtOOOCONHn-Bu——0Nfentanyl
D-344n-PrOOOCONHn-Bu——0Nfluconazole
D-345PhOOOCONHn-Bu——0Nfluconazole
D-346MeNHOOCONHn-Bu——0Nfluconazole
D-347Ph—NHOOCONHn-Bu——0Nfluconazole
D-348EtNHOOCONHn-Bu——0Nfluconazole
D-349n-PrNHOOCONHn-Bu——0Nfluconazole
D-350(CH3)3CNHOOCONH—Bn——0Nfluconazole
D-351PhOOOCONH—Bn——0Nfluconazole
D-352Ph—NHOOCONH—Bn——0Nfluconazole
D-3534Cl(Ph)OOCONNH2——0Nfluconazole
D-354methylOOCONHNHMe——0Nfluconazole
D-355ethylOOCONHNHEt——0Nfluconazole
D-356n-propylOOCONHNHPr——0Nfluconazole
D-357C(CH3)3OOCONHNHt-Bu——0Nfluconazole
D-358MeOOOCONHNHCO2Me——0Nfluconazole
D-359EtOOOCONHNHCO2Et——0Nfluconazole
D-360n-PrOOOCONHNHCO2t-Bu——0Nfluconazole
D-361MeNHOOCONHNHCO2Bn——0Nfluconazole
D-362EtNHOOCONHN═CHMe——0Nfluconazole
D-363n-PrNHOOCONHN═CHMe——0Nfluconazole
D-364(CH3)3CNHOOCONHN═CHPh——0Nfluconazole
D-365PhOOOCONHN═CHPh——0Nfluconazole
D-366methylOOCO2H——0Nfluconazole
D-367ethylOOCO2H——0Nfluconazole
D-368n-propylOOCO2H——0Nfluconazole
D-369C(CH3)3OOCO2H——0Nfluconazole
D-370MeOOOCO2H——0Nfluconazole
D-371EtOOOCO2H——0Nfluconazole
D-372n-PrOOOCO2H——0Nfluconazole
D-373MeNHOOCO2Me——0Nfluconazole
D-374EtNHOOCO2Me——0Nfluconazole
D-375n-PrNHOOCO2Me——0Nfluconazole
D-376n-PrOOOCO2Me——0Nfluconazole
D-377PhOOOCO2Me——0Nflucanazole
D-378Ph—NHOOCO2Me——0Nfluconazole
D-3794Cl(Ph)OOCO2Me——0Nfluconazole
D-3804Cl(Ph)OOOCO2Et——0Nfluconazole
D-3814Cl(Ph)NHOOCO2Et——0Nfluconazole
D-382MeOOSCO2n-Pr——0Nfluconazole
D-383EtOOSCO2n-Pr——0Nfluconazole
D-384n-PrOOOCO2n-Bu——0Nfluconazole
D-385MeNHOOCO2n-Bu——0Nfluconazole
D-386EtNHOOCO2n-Bu——0Nfluconazole
D-387n-PrNHOSCO2n-Bu——0Nfluconazole
D-388n-PrOOSCO2n-Bu——0Ofluconazole
D-389PhOOOCO2n-Bu——0Ofluconazole
D-390PhNHOOCO2n-Bu——0Ofluconazole
D-3914Cl(Ph)OOCO2n-Bu——0Ofluconazole
D-3924Cl(Ph)OOOCO2n-Bu——0Ofluconazole
D-393MeOOOCO2—Bn——0Ofluconazole
D-394EtOOOCO2—Bn——0Ofluconazole
D-395n-PrOOOCO2—Bn——0Ofluconazole
D-396(CH3)3COOSCO2—Bn——0Ofluconazole
D-397MeNHOSCO2—Bn——0Ofluconazole
D-398EtNHOOCO2—Bn——0Ofluconazole
D-399n-PrNHOOCO2—Bn——0Ofluconazole
D-400(CH3)3CNHOOCO2—Bn——0Ofluconazole
D-401PhOOOCO2—Bn——0Ofluconazole
D-402Ph—NHOOCOSMe——0Ofluconazole
D-4034Cl(Ph)OSCOSMe——0Ofluconazole
D-404methylOOCOSMe——0Ofluconazole
D-405ethylOOCOSMe——0Ofluconazole
D-406n-propylOSCOSEt——0Ofluconazole
D-407C(CH3)3OOCOSEt——0Ofluconazole
D-408MeOOOCOSn-Bu——0Ofluconazole
D-409EtOOSCOSn-Bu——0Ofluconazole
D-410n-PrOOOCOSBn——0Ofluconazole
D-411MeNHOOCOSBn——0Ofluconazole
D-412EtNHOOCONHMe——0Ofluconazole
D-413n-PrNHOOCONHMe——0Ofluconazole
D-414n-PrOOOCONHEt——0Ofluconazole
D-415PhOOOCONHn-Pr——0Nhydrocodone
D-416Ph—NHOOCONHn-Bu——0Ohydrocodone
D-417methylOOCONHn-Bu——0Nhydroxyzine
D-418ethylOOCONHn-Bu——0Nitraconazole
D-419n-propylOOCONHn-Bu——0Nlevamisole
D-420C(CH3)3OOCONHn-Bu——0Nmeclizine
D-421MeOOOCONHn-Bu——0Nmeclizine
D-422EtOOOCONHn-Bu——0Nmeclizine
D-423n-PrOOOCONH—Bn——0Nmeclizine
D-424MeNHOOCONH—Bn——0Nmeclizine
D-425EtNHOOCONH—Bn——0Nmeclizine
D-426n-PrNHOOCONNH2——0Nmeclizine
D-427n-PrOOOCONHNHMe——0Nmeclizine
D-428PhOOOCONHNHEt——0Nmeclizine
D-429Ph—NHOOCONHNHPr——0Nmeclizine
D-4304Cl(Ph)OOCONHNHt-Bu——0Nmeclizine
D-4314Cl(Ph)OOOCONHNHCO2Me——0Nmeclizine
D-4324Cl(Ph)NHOOCONHNHCO2Et——0Nmeclizine
D-433MeOOOCONHNHCO2t-Bu——0Nmecizine
D-434EtOOOCONHNHCO2Bn——0Nmeclizine
D-435n-PrOOOCONHN═CHMe——0Nmeclizine
D-436MeNHOOC0NHN═CHMe——0Nmeclizine
D-437EtNHOOCONHN═CHPh——0Nmeclizine
D-438n-PrNHOOCONHN═CHPh——0Nmeclizine
D-439methylOOCO2H——0Nmeperidine
D-440ethylOOCO2H——0Nmeperidine
D-441n-propylOOCO2H——0Nmeperidine
D-442C(CH3)3OOCO2H——0Nmeperidine
D-443MeOOOCO2H——0Nmeperidine
D-444EtOOOCO2H——0Nmeperidine
D-445n-PrOOOCO2H——0Nmeperidine
D-446MeNHOOCO2Me——0Nmeperidine
D-447EtNHOOCO2Me——0Nmeperidine
D-448n-PrNHOOCO2Me——0Nmeperidine
D-449n-PrOOOCO2Me——0Nmeperidine
D-450PhOOOCO2Me——0Nmeperidine
D-451Ph—NHOOCO2Me——0Nmeperidine
D-4524Cl(Ph)OOCO2Me——0Nmeperidine
D-4534Cl(Ph)OOOCO2Et——0Omeperidine
D-4544Cl(Ph)NHOOCO2Et——0Omeperidine
D-455methylOOCO2n-Pr——0Omeperidine
D-456ethylOOCO2n-Pr——0Omeperidine
D-457n-propylOOCO2n-Bu——0Nmeperidine
D-458C(CH3)3OOCO2n-Bu——0Nmeperidine
D-459MeOOOCO2n-Bu——0Nmeperidine
D-460EtOOSCO2n-Bu——0Nmeperidine
D-461n-PrOOSCO2n-Bu——0Nmeperidine
D-462MeNHOOCO2n-Bu——0Nmeperidine
D-463EtNHOOCO2n-Bu——0Nmeperidine
D-464n-PrNHOOCO2n-Bu——0Nmeperidine
D-465n-PrOOOCO2n-Bu——0Nmeperidine
D-466PhOOOCO2—Bn——0Nmeperidine
D-467Ph—NHOOCO2—Bn——0Nmeperidine
D-4684Cl(Ph)OOCO2—Bn——0Nmeperidine
D-4694Cl(Ph)OOSCO2—Bn——0Nmeperidine
D-4704MeO(Ph)OOSCO2—Bn——0Nmeperidine
D-4714NO2(Ph)OOOCO2—Bn——0Nmeperidine
D-4724Cl(Ph)NHOOCO2—Bn——0Nmeperidine
D-4734F(Ph)NHOOCO2—Bn——0Nmeperidine
D-4744MeO(Ph)NHOOCO2—Bn——0Nmeperidine
D-475pyrid-2-ylOOCOSMe——0Nmeperidine
D-476pyrid-4-ylOSCOSMe——0Nmeperidine
D-477methylOOCOSMe——0Nmeperidine
D-478ethylOOCOSMe——0Nmeperidine
D-479methylOSCOSEt——0Nmeperidine
D-480ethylOOCOSEt——0Nmeperidine
D-481n-propylOOCOSn-Bu——0Nmeperidine
D-482C(CH3)3OSCOSn-Bu——0Nmeperidine
D-483MeOOOCOSBn——0Nmeperidine
D-484EtOOOCOSBn——0Nmeperidine
D-485n-PrOOOCONHMe——0Nmeperidine
D-486MeNHOOCONEMe——0Nmeperidine
D-487EtNHOOCONHEt——0Nmeperidine
D-488n-PrNHOOCONHn-Pr——0Nmeperidine
D-489n-PrOOOCONHn-Bu——0Nmeperidine
D-490PhOOOCONHn-Bu——0Nmeperidine
D-491Ph—NHOOCONHn-Bu——0Nmeperidine
D-4924Cl(Ph)OOCONHn-Bu——0Nmeperidine
D-4934Cl(Ph)OOOCONHn-Bu——0Nmeperidine
D-4944CH3O(Ph)OOOCONHn-Bu——0Nmeperidine
D-4954NO2(Ph)OOOCONHn-Bu——0Nmeperidine
D-4964Cl(Ph)NHOOCONH—Bn——0Nmethenamine
D-4974F(Ph)NHOOCONH—Bn——0Nmethenamine
D-4984MeO(Ph)NHOOCONH—Bn——0Nmethenamine
D-499pyrid-2-ylOOCONNH2——0Nmethenamine
D-500pyrid-4-ylOOCONHNHMe——0Nmethenamine
D-501methylOOCONHNHEt——0Nmethenamine
D-502ethylOOCONHNHPr——0Nmethenamine
D-503n-propylOOCONHNHt-Bu——0Nmethenamine
D-504C(CH3)3OOCONHNHCO2Me——0Nmethenamine
D-505MeOOOCONHNHCO2Et——0Nmethenamine
D-506EtOOOCONHNHCO2t-Bu——0Nmethenamine
D-507n-PrOOOCONHNHCO2Bn——0Nmethenamine
D-508MeNHOOCONHN═CHMe——0Nmethenamine
D-509EtNHOOCONHN═CHMe——0Nmethenamine
D-510n-PrNHOOCONHN═CHPh——0Nmethenamine
D-511n-PrOOOCONHN═CHPh——0Nmethenamine
D-512PhOOOCO2H——0Nmethenamine
D-513Ph—NHOOCO2H——0Nmorantel
D-5144Cl(Ph)OOCO2H——0Nmorantel
D-5154Cl(Ph)OOOCO2H——0Nmorantel
D-5164CH3O(Ph)OOOCO2H——0Nmorantel
D-5174NO2(Ph)OOOCO2H——0Nmorantel
D-5184Cl(Ph)NHOOCO2H——0Nmorantel
D-5194F(Ph)NHOOCO2Me——0Nmorantel
D-5204MeO(Ph)NHOOCO2Me——0Nmorantel
D-521pyrid-2-ylOOCO2Me——0Nmorantel
D-522pyrid-4-ylOOCO2Me——0Nmorantel
D-523methylOOCO2Me——0Nmorantel
D-524ethylOOCO2Me——0Nmorantel
D-525n-propylOOCO2Me——0Nmorantel
D-526C(CH3)3OOCO2Et——0Nmorantel
D-527MeOOOCO2Et——0Nmorantel
D-528EtOOOCO2n-Pr——0Nmorantel
D-529n-PrOOOCO2n-Pr——0Nmorantel
D-530MeNHOOCO2n-Bu——0Nmorantel
D-531EtNHOOCO2n-Bu——0Nmorantel
D-532n-PrNHOOCO2n-Bu——0Nmorantel
D-533n-PrOOOCO2n-Bu——0Nnaltrexone
D-534PhOOOCO2n-Bu——0Nnaltrexone
D-535Ph—NHOSCO2n-Bu——0Nnaltrexone
D-5364Cl(Ph)OSCO2n-Bu——0Nnaltrexone
D-5374Cl(Ph)OOSCO2n-Bu——0Nnaltrexone
D-5384CH3O(Ph)OOOCO2n-Bu——0Nnaltrexone
D-5394NO2(Ph)OOOCO2—Bn——0Nnaltrexone
D-5404Cl(Ph)NHOOCO2—Bn——0Nnaltrexone
D-5414F(Ph)NHOOCO2—Bn——0Nnaltrexone
D-5424MeO(Ph)NHOOCO2—Bn——0Nnaltrexone
D-543pyrid-2-ylOOCO2—Bn——0Nnaltrexone
D-544pyrid-4-ylOOCO2—Bn——0Nnaltrexone
D-545methylOOCO2—Bn——0Noxybutynin
D-546ethylOOCO2—Bn——0Noxybutynin
D-547n-propylOOCO2—Bn——0Noxybutynin
D-548C(CH3)3OOCOSMe——0Noxybutynin
D-549MeOOOCOSMe——0Noxybutynin
D-550EtOOOCOSMe——0Noxybutynin
D-551n-PrOOOCOSMe——0Noxybutynin
D-552MeNHOOCOSEt——0Noxybutynin
D-553EtNHOOCOSEt——0Npentazocine
D-554n-PrNHOOCOSn-Bu——0Npentazocine
D-555n-PrOOOCOSn-Bu——0Npentazocine
D-556PhOOOCOSBn——0Npentazocine
D-557Ph—NHOOCOSBn——0Npentazocine
D-5584Cl(Ph)OOCONHMe——0Npentazocine
D-5594Cl(Ph)OOOCONHMe——0Npentazocine
D-5604MeO(Ph)OOOCONHEt——0Npentazocine
D-561methylOOCONHn-Pr——0Npentazocine
D-562ethylOOCONHn-Bu——0Npentazocine
D-563n-propylOOCONHn-Bu——0Npentazocine
D-564C(CH3)3OOCONHn-Bu——0Npentazocine
D-565MeOOOCONHn-Bu——0Npentazocine
D-566EtOOOCONHn-Bu——0Npentazocine
D-567n-PrOOOCONHn-Bu——0Npentazocine
D-568MeNHOOCONHn-Bu——0Npentazocine
D-569EtNHOOCONH—Bn——0Npentazocine
D-570n-PrNHOOCONH—Bn——0Npentazocine
D-571n-PrOOOCONH—Bn——0Npentazocine
D-572PhOOOCONNH2——0Npentazocine
D-573Ph—NHOOCONHNHMe——0Npentazocine
D-5744Cl(Ph)OOCONHNHEt——0Npentazocine
D-5754Cl(Ph)OOOCONHNHPr——0Npentazocine
D-5764CH3O(Ph)OOOCONHNHt-Bu——0Npentazocine
D-5774NO2(Ph)OOSCONHNHCO2Me——0Npentazocine
D-5784Cl(Ph)NHOSCONHNHCO2Et——0Npentazocine
D-5794F(Ph)NHOSCONHNHCO2t-Bu——0Npentazocine
D-5804MeO(Ph)NHOOCONHNHCO2Bn——0Npentazocine
D-581pyrid-2-ylOOCONHN═CHMe——0Npentazocine
D-582pyrid-4-ylOOCONHN═CHMe——0Npentazocine
D-583methylOOCO2H——0Npentazocine
D-584ethylOOCO2H——0Npromazine
D-585n-propylOOCO2H——0Npyrantel
D-586C(CH3)3OOCO2H——0Nselegiline
D-587MeOOOCO2H——0Ntiamulin
D-588EtOOOCO2H——0Nverapamil
D-589n-PrOOOCO2H——0Nverapamil
D-590MeNHOOCO2Me——0Nverapamil
D-591EtNHOOCO2Me——0Nverapamil
D-592n-PrNHOOCO2Me——0Nverapamil
D-593n-PrOOOCO2Me——0Nverapamil
D-594PhOOOCO2Me——0Nverapamil
D-595Ph—NHOOCO2Me——0Nverapamil
D-5964Cl(Ph)OOCO2Me——0Nverapamil
D-5974Cl(Ph)OOOCO2Et——0Nverapamil
D-5984CH3O(Ph)OOOCO2Et——0Nverapamil
D-5994NO2(Ph)OOOCO2n-Pr——0Nverapamil
D-6004Cl(Ph)NHOOCO2n-Pr——0Nverapamil
D-6014F(Ph)NHOOCO2n-Bu——0Nverapamil
D-6024MeO(Ph)NHOOCO2n-Bu——0Nverapamil
D-603pyrid-2-ylOOCO2n-Bu——0Nverapamil
D-604pyrid-4-ylOOCO2n-Bu——0Nverapamil
D-6054NO2(Ph)OOOCO2n-Bu——0Nverapamil
D-6064Cl(Ph)NHOOCO2n-Bu——0Nverapamil
D-610pyrid-4-ylOOCO2—Bn——0Nverapamil
D-611methylOOCO2—Bn——0Nverapamil
D-612ethylOOCO2—Bn——0Nverapamil
D-613n-propylOOCO2—Bn——0Nverapamil
D-614C(CH3)3OOCO2—Bn——0Nverapamil
D-615MeOOSCO2—Bn——0Nverapamil
D-616EtOOSCO2—Bn——0Nverapamil
D-617n-PrOOSCO2—Bn——0Nverapamil
D-618MeNHOOCO2—Bn——0Nverapamil
D-619EtNHOOCOSMe——0Nverapamil
D-620n-PrNHOOCOSMe——0Nverapamil
D-621n-PrOOOCOSMe——0Nverapamil
D-622PhOOOCOSMe——0Nverapamil
D-623Ph—NHOOCOSEt——0Nverapamil
D-6244Cl(Ph)OOCOSEt——0Nverapamil
D-6254Cl(Ph)OOOCOSn-Bu——0Nverapamil
D-6264CH3O(Ph)OOOCOSn-Bu——0Nverapamil
D-6274NO2(Ph)OOOCOSBn——0Nverapamil
D-6284Cl(Ph)NHOOCOSBn——0Nverapamil
D-6294F(Ph)NHOOCONHMe——0Nverapamil
D-6304MeO(Ph)NHOOCONHMe——0Nverapamil
D-631pyrid-2-ylOOCONHEt——0Nverapamil
D-632pyrid-4-ylOOCONHn-Pr——0Nverapamil
|
Escherichia coli
8739 and Staphylococcus aureus 6538 Minimum Inhibitory Concentration (MIC) Test Methods and Results
[0732] Several compounds of this invention were tested for biological activity in vitro against Escherichia coli 8739 and Staphylococcus aureus 6538 described below. The following test procedures were employed.
[0733] MIC Determination: The lowest concentration of test compound required to inhibit Escherichia coli 8739 and Staphylococcus aureus 6538 was determined by a high resolution minimum inhibitory concentration (HRMIC) test. Varying amounts of the test compounds were added to minimal salts glucose medium (Maniatis, T., Fritsch, E. F., Sambrook, J. 1982 Molecular Cloning, page 68) supplemented with 0.1% yeast extract (M9GY) in a 96-well microtiter plate. Ten-fold serial dilutions were performed on a Biomek 2000 Workstation to obtain a range of closely spaced concentrations of test compound as shown in FIG. 1. A cell suspension of inoculum, adjusted to provide 106 CFU/mL in each well, was added to the microtiter plate. Microtiter plates were incubated at 30° C. for 24 h and then were checked for the presence or absence of microbial growth in each well. The concentration of compound in the first microtiter well demonstrating no growth was the minimum inhibitory concentration (MIC) for the test compound.
15TABLE 11
|
|
MIC (ppm AI*) of Kathon CG Biocide, Norfloxacin and compound
8-1 vs S. aureus 6538 and E. coli 8739:
S. aureus 6538E. coli 8739
CompoundGram-positiveGram-negative
|
Kathon CG Biocide0.40.75
Norfloxacin0.90.2
8-10.062.5
|
[0734]
16
TABLE 12
|
|
|
MIC (ppm AI*) of compounds 8-2, 8-3 and 8-4 vs S. aureus 6538 and
|
E. coli
8739:
|
S. aureus
6538
E. coli
8739
|
Compound
Gram-positive
Gram-negative
|
|
8-2
0.45
3
|
8-3
4.5
40
|
8-4
0.7
>1000
|
|
Claims
- 1. A pharmaceutical moiety represented by Z1(X1), wherein
X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1, Z1 represents the remainder of said pharmaceutical moiety, m is 1, and Z1(X1)m—H represents the complete pharmaceutical compound, said pharmaceutical moiety Z1(X1)m being substituted with a second moiety on X1, said second moiety comprising a substituent which enhances or changes the properties of said pharmaceutical compound, said substituent having the formula 88wherein G10, G11 and G20 are each independently an oxygen atom or a sulfur atom, G21 is an oxygen atom, a sulfur atom or NR3, q is 0, t is 0 or 1, &Circlesolid;- represents the connection point of said substituent to said pharmaceutical moiety Z1(X1)m, Z2(X2)q is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, alkylcarbonylaminoalkenyl, arylcarbonylaminoalkenyl, heteroarylcarbonylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkyltlioaalkenyl, haloalkylthioalkynyl, NR3R4, SO2NR3R4, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, dialkoxyphosphorylalkyl, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, C(═O)OR2, C(═O)SR2, C(═S)OR2, C(═S)SR2, C(═O)NR3R4, C(═S)NR3R4, C(═O)R2, C(═S)R2, C(═N—R3)R2, C(═N—OR3)R2, C(═N—NR3R4)R2, OP(═O)(OR2)2, SO2NR3R4, NR3R4 and alkylNR3R4, aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, alkylcarbonylalkyl, alkenylcarbonylalkyl, alkynylcarbonylalkyl, beterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl, or heterocyclylcarbonyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonyl, heterocyclyloxycarbonylalkyl, arylcarbonyl, arylcarbonylalkyl, aralkylcarbonyl, aralkylcarbonylalkyl, aroxycarbonyl, aroxycarbonylalkyl, aralkoxycarbonyl, aralkoxycarbonylalkyl, heteroarylcarbonyl, heteroarylcarbonylalkyl, heteroaroxycarbonyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, and C(—N-G22)R2 when q is 0 and t is 1, G22 is OR3, OCOR3, S(O)jR3, OS(O)jR3, NR3R4, OSO2NR3R4, OP(═O)OR3NR3R4, OP(═O)(OR3)2 or N═CR3R4, j is 0, 1 or 2, Z2(X2)q is halo, NR3R4, {(NR3R4R5)+M−}, OR3, S(O)jR3 or SO2NR3R4 when both q and t are 0 wherein M is halo, hydroxy, alkoxy or the anion of a carboxylic acid and j is 0, 1 or 2, R1 is 89wherein G30 is an oxygen atom or a sulfur atom, G31 is an oxygen atom, a sulfur atom or NR3, d is 0, t′ is 0 or 1, Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkenylcarbonyl, alkenylcarbonylalkyl, alkynylcarbonyl, alkynylcarbonylalkyl, hydroxyalkyl, alkylsulfonylalkyl, alkylcarbonylaminoalkyl, arylcarbonylaminoalkyl, heteroarylcarbonylalkylamino, acetylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloaLkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, NR3R4, OR3, S(O)jR3, aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl, or aryl, arylcarbonyloxyalkyl, arylcarbonylalkyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkylcarbonyloxyalkyl, aralkylcarbonylalkyl, aralkoxycarbonylalkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylcarbonylalkyl, heteroaroxycarbonylalkyl, or heteroaryl, heteroarylcarbonyloxyalkyl, heteroarylarylcarbonylalkyl, heteroaroxycarbonylalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylcarbonyloxyalkyl, heterocyclylcarbonylalkyl, heterocyclyloxycarbonylalkyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aLkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2, Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2, R2 is a hydrogen atom, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxy, a carboxylate salt, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyciylalkynyl, or alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, carboxy, alkoxycarbonyl, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl or aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl, or arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl or heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl, or heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, R3, R4 and R5 are each independently a hydrogen atom, alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl, alkynyl, or alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl or alkynyl substituted with one or more halo, aryl, aralkyl, aralkenyl, aralkynyl, or aryl, aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 2. A pharmaceutical moiety represented by Z1(X1)m wherein
X1 is an oxygen atom, a sulfur atom, a phosphorous atom or a nitrogen atom attached to Z1, Z1 represents the remainder of said pharmaceutical moiety, m is 1, and Z1(X1)m—H represents the complete pharmaceutical compound, said pharmaceutical moiety Z1(X1)m being substituted with a second moiety on X1, said second moiety comprising a substituent which enhances or changes the properties of said pharmaceutical compound, said substituent having the formula 90wherein G10, G11 and G20 are each independently an oxygen atom or a sulfur atom, G21 is an oxygen atom, a sulfur atom or NR3, q is 0 or 1, &Circlesolid;- represents the connection point of said substituent to said pharmaceutical moiety Z1(X1)m, X2 is an oxygen atom, a sulfur atom, a phosphorous atom, a nitrogen atom or a carbon atom attached to Z2, t is 0 or 1, Z2(X2)q(C(=G20)G21)t is a second pharmaceutical moiety when q is 1 wherein Z2(X2)q(C(=G20)G21)t or Z2(X2)q(C(=G20)G2′)t—H represents the second pharmaceutical, Z2 represents the remainder of said second pharmaceutical moiety, R1 is 91wherein G30 is an oxygen atom or a sulfur atom, G31 is an oxygen atom, a sulfur atom or NR3, t′ and d are each independently 0 or 1, X3 is an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorous atom or a carbon atom attached to Z3 when t′ is 0, a nitrogen atom attached to Z3 when t′ is 1 and G31 is NR3, or a carbon atom attached to Z3 when t′ is 1 and G3′ is an oxygen atom or a sulfur atom, Z3(X3)d(G31)t′ is a second alternative pharmaceutical moiety when d is 1 wherein Z3(X3)d(G3′)t—H represents the second alternative pharmaceutical, Z3 represents the remainder of said second alternative pharmaceutical moiety, Z3(X3)d, when d is 0 and t′ is 1, is a hydrogen atom, alkyl, alkylcarbonyloxyalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, hydroxyalkyl, alkylsulfonylalkyl, acetylaminoalkyl, haloalkyl, alkenyl, acetylaminoalkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, carboxycycloalkyl, carboxycycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, carboxycycloalkylalkyl, carboxycycloalkylalkenyl, carboxycycloalkenylalkyl, carboxycycloalkenylalkenyl, carboxycycloalkylalkynyl, carboxycycloalkenylalkynyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, haloalkylthioalkyl, haloalkylthioalkenyl, haloalkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, NR3R4, OR3, S(O)jR3, aryl, aryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, thiocyanato, alkyl, alkylsulfonylalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl, or aralkyl, aralkenyl, aralkynyl, arcycloalkyl, aroxyalkyl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl, heteroaryl substituted with one or more substituents independently selected from halo, nitro, hydroxy, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4 wherein j is 0, 1 or 2, Z3(X3)d is halo, NR3R4, OR3, N(R3)—N═CR3R4, S(O)jR3 or SO2NR3R4 when both d and t′ are 0 and j is 0, 1 or 2, R2 is a hydrogen atom, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxy, a carboxylate salt, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkylthioalkyl, alkylthioalkenyl, alkylthioalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkylalkynyl, cycloalkenylalkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, SO2NR3R4 and NR3R4, aryl or aryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, carboxy, alkoxycarbonyl, SO2NR3R4 and NR3R4, aralkyl, aralkenyl, aralkynyl or aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl, or arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl, aralkynylcarbonyl, aroxycarbonylalkyl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaryl or heteroaryl substituted with one or more substituents independently selected from halo, hydroxy, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroaralkyl, heteroaralkenyl, heteroaralkynyl or heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxyearbonylalkyl, heterocyclylcarboryl, heterocyclyloxycarbonylalkyl, or heteroarylcarbonyl, heteroaralkylcarbonyl, heteroaralkenylcarbonyl, heteroaralkynylcarbonyl, heteroaroxycarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxycarbonylalkyl substituted with one or more substituents independently selected from halo, cyano, hydroxy, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, SO2NR3R4 and NR3R4, R3, R4 and R5 are each independently a hydrogen atom, alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl, alkynyl, or alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenylalkyl, cycloalkenylalkenyl, cycloalkenylalkynyl, carboxyalkyl, carboxyalkenyl, carboxyalkynyl, alkoxyalkyl, alkenyl or alkynyl substituted with one or more halo, aryl, aralkyl, aralkenyl, aralkynyl, or aryl, aralkyl, aralkenyl, aralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl, or heteroaryl, heteroaralkyl, heteroaralkenyl, heteroaralkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl, or heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl substituted with one or more substituents independently selected from halo, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy and haloalkoxy, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or unsaturated heterocyclic ring, (q+d) is 1, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 3. A pharmaceutical compound of the formula
- 4. The pharmaceutical compound of claim 3 wherein t is 1, m is 1, q is 0, (X1)m is a nitrogen atom and Z1(X1)m—H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 5. The pharmaceutical compound of claim 3 wherein t is 1, m is 1, q is 0, (X1)m is a phosphorous, oxygen or sulfur atom and Z1(X1), —H is a pharmaceutical, or t is 1, m is 0, q is 1, (X2)q is a phosphorous, oxygen or sulfur atom and Z2(X2)q-[(C=G20)-G21]t-H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 6. The pharmaceutical compound of claim 3 wherein t is 1, m is 0, q is 1, (2)q is a carbon atom and Z2(X2)q—[(C=G20)-G21]t—H is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 7. The pharmaceutical compound of claim 3 wherein t is 0, m is 1, q is 0, (X1)m is a nitrogen, phosphorous, oxygen or sulfur atom and Z1(X1)m—H is a pharmaceutical, or t is 0, m is 0, q is 1, (X2)q is a nitrogen, phosphorous, oxygen, sulfur or carbon atom and Z2(X2)q-[(C=G20)-G21]t—H is a pharmaceutical or
Z2(X2)q—[(C=G20)-G21]t is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 8. The pharmaceutical compound of claim 3 wherein t is 0 or 1, m is 1, q is 1, (X1)m is a nitrogen, phosphorous, oxygen or sulfur atom, (X2)q is a nitrogen, phosphorous, oxygen, sulfur or carbon atom, Z1(X1)m—H is a pharmaceutical and Z2(X2)q—(C=G20-G2′)t—H or Z2(X2)q—(C=G20-G21)t is a pharmaceutical, or the pharmaceutically acceptable salts, isomers, tautomers, enantiomers and mixtures thereof.
- 9. The pharmaceutical compound of claim 3 wherein A is
- 10. The pharmaceutical compound of claim 3
- 11. The pharmaceutical compound of claim 3
- 12. The pharmaceutical compound of claim 3
- 13. A human health pharmaceutical compound of the formula
- 14. A human health pharmaceutical compound of the formula
- 15. A veterinary pharmaceutical compound of the formula
- 16. A veterinary pharmaceutical compound of the formula
- 17. A pharmaceutical compound of the formula
- 18. A pharmaceutical compound of the formula
- 19. The pharmaceutical composition of any one of claims 3-18 comprising a pharmaceutical compound of this invention and a pharmaceutically acceptable carrier.
- 20. The composition of claim 19 containing from about 0.1% to about 99% by weight of said pharmaceutical compound.
- 21. A method of controlling pain or disease symptoms in a warm-blooded animal exhibiting pain or disease symptoms comprising administering thereto a pharmaceutically effective amount of a compound of any one of claims 3-18.
- 22. A method of controlling pain or disease symptoms in a warm-blooded animal exhibiting pain or disease symptoms comprising administering thereto a pharmaceutically effective amount of the composition of claim 19.
- 23. A method of controlling pain or disease symptoms in a warm-blooded animal exhibiting pain or disease symptoms comprising administering thereto a pharmaceutically effective amount of the composition of claim 20.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US01/00653 |
1/26/2001 |
WO |
|
Provisional Applications (1)
|
Number |
Date |
Country |
|
60178878 |
Jan 2000 |
US |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
09493865 |
Jan 2000 |
US |
Child |
10182076 |
Dec 2002 |
US |