Claims
- 1. A compound of Formula IV
- 2. The compound of claim 1, wherein R13 is selected from the group consisting of
i) hydrogen; ii) C2-C6 alkenylene; iii) halogen or perhaloalkyl; iv) an alkoxy of formula —O—X14, wherein
X14 is selected from the group consisting of hydrogen, lower alkyl, and aryl; and v) a five-membered or six-membered heteroaryl ring or a six-membered aryl or heteroaryl ring, optionally substituted with one or more substituents selected from the group consisting of
A) optionally substituted C1-C4 straight-chain, branched, or cyclic saturated or unsaturated alkyl; B) an alkoxy of formula —O—X14, wherein X14 is hydrogen or lower alkyl; and C) halogen or perhaloalkyl; D) cyano; E) nitro; F) a substituent of formula —(X18)n18—C(O)—X19, wherein
X18 is lower alkylene; X19 is selected from the group consisting of hydrogen, lower alkyl, aryl, heteroaryl, hydroxy, alkoxy, amino, and —NX20X21, wherein X20 and X21 are each independently selected from the group consisting of hydrogen, alkyl, and aryl; and n18 is 0 or 1; and G) a thioether or thiol of formula —S—X23, wherein X23 is selected from the group consisting of hydrogen, lower alkyl, aryl, and heteroaryl; and H) an amide of formula —(X24)n24—NH—C(O)—X25 or —(X26)n26—C(O)—NH—X27 X24 and X26 are each independently lower alkylene; X25 is selected from the group consisting of hydrogen, lower alkyl, aryl, hydroxy, and alkoxy; and X27 is selected from the group consisting of hydrogen, lower alkyl, aryl, and heteroaryl.
- 3. The compound of claim 1, wherein R13 is selected from the group consisting of
i) hydrogen; ii) C2-C6 alkenylene; iii) halogen or perfluoroalkyl; iv) an alkoxy of formula —O—X14, wherein
X14 is selected from the group consisting of hydrogen, methyl, ethyl, and propyl; and v) a six-membered aryl ring, optionally substituted with one or more substituents selected from the group consisting of
A) methyl, ethyl, and propyl; B) hydroxy, methoxy, ethoxy, phenoxy, hydroxymethyl, 2-hydroxyethyl, and 3-hydroxypropyl; and C) halogen or perfluoroalkyl; D) cyano; E) nitro; F) a substituent of formula —C(O)—X19, wherein
X19 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, phenyl, hydroxy, methoxy, ethoxy, propoxy, amino, and —NX20X21, wherein X20 and X21 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, and phenyl; and G) a thioether or thiol of formula —S—X23, wherein X23 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, and phenyl; and H) an amide of formula —(X24)n24—NH—C(O)—X25 or —(X26)n26—C(O)—NH—X27 X24 and X26 are each independently lower alkylene; X25 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, phenyl, hydroxy, methoxy, and phenoxy; and X27 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, and phenyl.
- 4. The compound of claim 1, wherein said five-membered or six-membered heteroaryl ring or said six-membered aryl or heteroaryl ring of R13 is selected from the group consisting of optionally substituted
- 5. The compound of claim 1, wherein said five-membered or six-membered heteroaryl ring or the six-membered aryl or heteroaryl ring of R13 is selected from the group consisting of phenyl, furan, thiophene, pyrrole, pyrroline, pyrrolidine, oxazole, thiazole, imidazole, imidazoline, imidazolidine, pyrazole, pyrazoline, pyrazolidine, isoxazole, isothiazole, triazole, thiadiazole, pyran, pyridine, piperidine, morpholine, thiomorpholine, pyridazine, pyrimidine, pyrazine, piperazine, and triazine.
- 6. The compound of claim 1, wherein R13 is selected from the group consisting of hydrogen, chloro, bromo, hydroxy, —CH═CH—CH2CH2CH2CH3, —CH═CH—C(O)—OH, —CH═CH—C(O)—OCH3, —CH═CH—C(O)—NH2, —CH2CH(NH2)COOH, phenyl, —O—CH2-phenyl, 2-methylphenyl, 3-methylphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-hydroxymethylphenyl, 3-hydroxymethylphenyl, 4-hydroxymethylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-hydroxycarbonylphenyl, 3-hydroxycarbonylphenyl, 4-hydroxycarbonylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-trifluoromethylphenyl, 4-benzyloxyphenyl, 2-phenoxyphenyl, 2,4-dihydroxyphenyl, 3,4-dihydroxyphenyl, 2-hydroxy-4-methoxyphenyl, 4-hydroxy-2-methoxyphenyl, 2,4-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3-fluoro-4-hydroxyphenyl, 3-fluoro-4-methoxyphenyl,
- 7. The compound of claim 1, wherein said R11, R12, R13, and R14 is each independently selected from the group consisting of (i) hydrogen, (ii) hydroxyl, (iii) halogens, (iv) cyano, (v) nitro, (vi) amino, (vii) hydroxycarbonyl, (viii) aminocarbonyl, (ix) aminothiocarbonyl, (x) lower alkoxy, (xi) phenoxy, (xii) (C1-C4)alkylamino, (xiii) arylamino, (xiv) C1-C8 straight-chain, branched, and cyclic saturated and unsaturated alkyl or alkenyl, (xv) optionally substituted aryl and (xvi) optionally substituted hereocycle.
- 8. The compound of claim 1, wherein said R15 is selected from the group consisting of (i) hydrogen, (ii) cyano, (iii) amino, (iv) hydroxycarbonyl, (v) aminocarbonyl, (vi) aminothiocarbonyl, (vii) (C1-C4)alkylamino, (viii) arylamino, (ix) C1-C8 straight-chain, branched, and cyclic saturated and unsaturated alkyl or alkenyl, (x) optionally substituted aryl and (xi) optionally substituted hereocycle.
- 9. The compound of claim 1, wherein said R16 is selected from the group consisting of (i) hydrogen, (ii) amino, (iii) hydroxycarbonyl, (iv) aminocarbonyl, (v) aminothiocarbonyl, (vi) (C1-C4)alkylamino, (vii) arylamino, (vii) C1-C8 straight-chain, branched, and cyclic saturated and unsaturated alkyl or alkenyl, (ix) optionally substituted aryl and (x) optionally substituted hereocycle.
- 10. The compound of claim 1, wherein said R17 is selected from the group consisting of (i) hydrogen, (ii) (C1-C4)alkylamino, (iii) arylamino, (iv) C1-C8 straight-chain, branched, and cyclic saturated and unsaturated alkyl, (v) optionally substituted aryl and (vi) optionally substituted hereocycle.
- 11. The compound of any one of claims 7-10, wherein said heterocycle is selected from the group consisting of furan, thiophene, pyrrole, pyrroline, pyrrolidine, oxazole, thiazole, imidazole, imidazoline, imidazolidine, pyrazole, pyrazoline, pyrazolidine, isoxazole, isothiazole, triazole, thiadiazole, pyran, pyridine, piperidine, morpholine, thiomorpholine, pyridazine, pyrimidine, pyrazine, piperazine, triazine, and benzimidazole.
- 12. A compound selected from the group consisting of 5-bromosalicylaldehyde thiosemicarbazone; 5-bromosalicylaldehyde semicarbazone hydrochloride; 5-phenylsalicylaldehyde thiosemicarbazone; 5-phenylsalicylaldehyde semicarbazone hydrochloride; 5-(3-methoxyphenyl)salicylaldehyde thiosemicarbazone; 5-(3-cyanophenyl)salicylaldehyde thiosemi-carbazone; 5-(3-hydroxymethylphenyl)salicylaldehyde thiosemicarbazone; 5-(3-hydroxymethyl-phenyl)salicylaldehyde semicarbazone hydrochloride; 5-(4-hydroxymethylphenyl)salicyl-aldehyde thiosemicarbazone; 5-(4-nitrophenyl)salicylaldehyde thiosemicarbazone; 5-(3-methoxycarbonylphenyl)salicylaldehyde thiosemicarbazone; 5-(3-methoxycarbonylphenyl)-salicylaldehyde semicarbazone hydrochloride; 5-(3-fluoro-4-methoxyphenyl)salicylaldehyde thiosemicarbazone; 5-(3-fluorophenyl)salicylaldehyde thiosemicarbazone; 5-(4-fluorophenyl)-salicylaldehyde thiosemicarbazone; 5-(3-carboxyphenyl)salicylaldehyde thiosemicarbazone; 5-(3-carboxyphenyl)salicylaldehyde semicarbazone hydrochloride; 5-(4-carboxyphenyl)salicyl-aldehyde thiosemicarbazone; 5-(3-hydroxyphenyl)salicylaldehyde thiosemicarbazone; 5-(4-hydroxyphenyl)salicylaldehyde thiosemicarbazone; 5-(4-hydroxyphenyl)salicylaldehyde semi-carbazone hydrochloride; 5-(3-fluoro-4-hydroxyphenyl)salicylaldehyde thiosemicarbazone; 5-(3-fluoro-4-hydroxyphenyl)salicylaldehyde semicarbazone hydrochloride; 5-(3,4-dihydroxy-phenylsalicylaldehyde thiosemicarbazone; 5-(3,4-dihydroxyphenyl)salicylaldehyde semicarbazone hydrochloride; 5-(2,4-dihydroxyphenyl)salicylaldehyde thiosemicarbazone; 4-hydroxy-5-(4-hydroxyphenyl)salicylaldehyde thiosemicarbazone; 4-hydroxy-5-(4-hydroxy-phenyl)salicylaldehyde semicarbazone hydrochloride; 5-(4-pyridyl)salicylaldehyde thiosemi-carbazone; 5-(3-pyridyl)salicylaldehyde thiosemicarbazone; 5-(5-pyrimidyl)salicylaldehyde thiosemicarbazone; 5-(2-thienyl)salicylaldehyde thiosemicarbazone; 5-(3-thienyl)salicylaldehyde thiosemicarbazone; 5-[2-(5-chloro-thienyl)]salicylaldehyde thiosemicarbazone; 5-(5-indolyl)-salicylaldehyde thiosemicarbazone; methyl (3-formyl-4-hydroxy)cinnamate, thiosemicarbazone; 3-formyl-4-hydroxycinnamic acid, thiosemicarbazone; 3-formyl-4-hydroxycinnamide, thiosemi-carbazone; 3-(3-formyl-4-hydroxyphenyl)propionic acid, thiosemicarbazone; 2-[(2-hydroxy-1-naphthyl)methylidene]hydrazine-1-carbamide hydrochloride; 2-[(2-hydroxy-1-naphthyl)-methylidene]hydrazine-1-carbothioamide; 2-[(2,7-dihydroxy-1-naphthyl)methylidene]hydrazine-1-carbothioamide; 2-[(2,7-dihydroxy-1-naphthyl)methylidene]hydrazine-1-carbothioamide; 2-[(2,6-dihydroxy-1-naphthyl)methylidene]hydrazine-1-carbothioamide; 2-amino-4-[1-(2-hydroxy-naphthyl)]pyrimidine; 3-(2-amino-pyrimidin-4-yl)-biphenyl-4,4′-diol; 2-(2-amino-pyrimidin-4-yl)-4-[2-(2-amino-pyrimidin-4-yl)-vinyl]-phenol.
RELATED APPLICATIONS
[0001] The present application claims priority to the U.S. Provisional Patent Application Serial No. 60/294,792, filed May 30, 2001, by Cao et al., and entitled “INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE,” the disclosure of which is incorporated by reference herein in its entirety.
[0002] The present application is also related to the U.S. patent application Ser. No. 10/______, filed May 28, 2002, by Cao et al., and entitled “INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE,” (Attorney Docket No. LGBIOMD.002DV1) and U.S. patent application Ser. No. 10/______, filed May 28, 2002, by Cao et al., and entitled “INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE,” (Attorney Docket No. LGBIOMD.002DV2), both of whose disclosures are incorporated by reference herein in their entirety.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60294792 |
May 2001 |
US |