Claims
- 1. A glycoside derivative of an aglycon selected from aliphatic, alicyclic, aliphatic-aromatic and aromatic aglycon compounds having a functional group selected from the group consisting of --OH, --SH, and --COOH, said glycoside derivative being selected from the group consisting of mono- and disaccharides having a 2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside moiety of the formulas A, B, C, D, E and F: ##STR21## where Acyl is a lower aliphatic acyl group or an aromatic acyl group, and X is selected from --O--, --S--, and --OCO--, provided that said aglycon is not cholesterol; and further provided that said aglycon is not acetaminophen.
- 2. The glycoside derivative according to claim 1, wherein said pyranoside moiety comprises a 4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside moiety.
- 3. The glycoside derivative according to claim 1, wherein said pyranoside moiety comprises a 4,6-di-hydroxy-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside moiety.
- 4. The glycoside derivative according to claim 2, wherein the aglycon compound is selected from bile salts, steroid hormones, and vitamin D compounds.
- 5. The glycoside derivative according to claim 3, wherein the aglycon compound is selected from bile salts, steroid hormones, and vitamin D compounds.
- 6. The glycoside derivative according to claim 2, wherein the aglycon compound is selected from 25-hydroxy-calciferol, pregnenolone, 17.alpha.-hydroxy-progesterone, 17.alpha.-hydroxy-pregnenolone, 11-desoxy-corticosterone, 11-desoxycortisol, corticosterone, cortisol, cortisone, dolichol, androsterone, testosterone, estrone, 17.beta.-estradiol, 3,16.alpha.,17.beta.-estratriol, tetrahydrocorticosterone, urocortisol, and allocortolone.
- 7. The glycoside derivative according to claim 3, wherein the aglycon compound is selected from 25-hydroxy-calciferol, pregnenolone, 17.alpha.-hydroxy-progesterone, 17.alpha.-hydroxy-pregnenolone, 11-desoxy-corticosterone, 11-desoxycortisol, corticosterone, cortisol, cortisone, dolichol, androsterone, testosterone, estrone, 17.beta.-estradiol, 3,16.alpha.,17.beta.-estratriol, tetrahydrocorticosterone, urocortisol, and allocortolone.
- 8. The glycoside derivative according to claim 2, wherein the aglycon compound is selected from clavulanic acid, amoxicillin, daunorubicin, lovastatin, mevastatin, simvastatin, mephenesin, and capsaicin.
- 9. The glycoside derivative according to claim 3, wherein the aglycon compound is selected from clavulanic acid, amoxicillin, daunorubicin, lovastatin, mevastatin, simvastatin, mephenesin, and capsaicin.
- 10. The glycoside derivative of cholic acid according to claim 1, wherein the aglycon compound is selected from cholic acid 3,7-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), cholic acid 3,12-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), cholic acid 3,7,12-tri-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), chenodeoxycholic acid 3,7-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), and deoxycholic acid 3,12-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside).
- 11. The glycoside derivative of cholic acid according to claim 3, wherein the aglycon compound is selected from cholic acid 3,7-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), cholic acid 3,12-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), cholic acid 3,7,12-tri-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), chenodeoxycholic acid 3,7-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside), and deoxycholic acid 3,12-di-(4,6-di-O-acyl-2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside).
- 12. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from p-hydroxyphenylethanolamine, norfenefrine, synephrine, etilefrin, phenylephrine, octapamine, isoprenaline, dichloroisoproterenol, metaproterenol, terbutaline, and buphenine.
- 13. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from atropine, homatropine, scopolamine and its methobromide and butyl bromide quaternary compounds, podine methyl sulfate, and tropine benzilate.
- 14. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from acetophenazine, fluphenazine, dixyrazine, perphenazine, hydroxyzine, pericyazine, haloperidol, trifluperidol, and moperone.
- 15. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from estrogen, ethinylestradiol, mestranol, and quinestrol.
- 16. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from amoxicillin, chloramphenicol, thiamphenicol, tetracycline, chlortetracycline, and oxytetracycline.
- 17. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from chlophendianol, clobutinol, and zipeprol.
- 18. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from ergonovine and prostaglandin F.sub.2.alpha..
- 19. The glycoside derivative according to claim 1, wherein the aglycon compound is cycloheximide.
- 20. The glycoside derivative according to claim 1, wherein the aglycon compound is oxyphenbutazone.
- 21. The glycoside derivative according to claim 1, wherein the aglycon compound is hymecromone.
- 22. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from methyldopa, levodopa, carbidopa, and droxidopa.
- 23. The glycoside derivative according to claim 1, wherein the aglycon compound is ephedrine.
- 24. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from phenprobamate and guaiacol glycerol ether.
- 25. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from dexamethasone and beclomethasone.
- 26. The glycoside derivative according to claim 1, wherein the aglycon compound is selected from provitamin D, xanthophyll, vitamin A, vitamin E, thiamine and ascorbic acid.
PRIOR APPLICATIONS
This is a continuation of allowed U.S. application Ser. No. 08/251,869, filed Jun. 1, 1994, issued Dec. 2, 1997 as U.S. Pat. No. 5,693,767 which is a continuation-in-part of U.S. application Ser. No. 08/006,447, filed Jan. 21, 1993, which is a continuation-in-part of U.S. application Ser. No. 07/815,691 filed Jan. 24, 1992, now abandoned, which is a continuation-in-part of U.S. application Ser. No. 07/733,915 filed Jul. 22, 1991, now abandoned, which is a continuation-in-part of U.S. application Ser. No. 07/644,002 filed Jan. 22, 1991, issued Jan. 11, 1994 as U.S. Pat. No. 5,278,296.
US Referenced Citations (8)
Foreign Referenced Citations (2)
Number |
Date |
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3127933 A1 |
Aug 1982 |
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3127933 |
Aug 1982 |
DEX |
Non-Patent Literature Citations (9)
Entry |
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Ferrier, J. Chem. Soc. (1962), "The Reaction Between 3,4,6-Tri-O-Acetyl-D-Glucal and p-Nitrophenol," 3667-3670. |
Ferrier, "Unsaturated Sugars," Adv. Carbohydrate Chemistry, 20, pp. 90-91 (1965). |
Ferrier, J. Chem. Soc., (1969) "Unsaturated Carbohydrates," 570-575. |
Honda, Carbohydrate Research, 29 (1973), Preparation of O-(2-deoxy-.alpha.-D-arabino-hexopyranosyl) (1-6)-D-glucose by oxyiodination-hydrogenation method, pp. 488-491. |
Garegg, Carbohydrate Research, 92 (1981), Novel Glycosylation Reagents: synthesis of disaccharides containing 2-deoxy-2-iodo-.alpha.-D-talopyranosyl groups, pp. 157-159. |
Thiem, Liebigs Ann. Chem. 1985, "Untersuchungen aur Darstellung von Desoxyzuker-Steroidglysosiden", pp. 2135-2150. |
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Continuations (1)
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251869 |
Jun 1994 |
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Continuation in Parts (4)
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006447 |
Jan 1993 |
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815691 |
Jan 1992 |
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733915 |
Jul 1991 |
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644002 |
Jan 1991 |
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