US 2002/0165259 A1 · Carbon substituted aminothiazole inhibitors of cyclin dependent kinases

Abstract

Compounds of the formula 1 and pharmaceutically acceptable salts thereof. As used in formula I, and throughout the specification, the symbols have the following meanings: R1═R2, COR3, CONH2, CONR2R3, COOR2, or SO2R2; R2=alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl; R3═H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl; 2 , where n=0,1,2; m=1,2 but both n and m cannot be 2, or , where i, j=0 or 1 but cannot both be 1, and Y=optionally substituted alkene, alkyne, or any 2 adjacent carbon atoms of a cycloalkyl or cycloheteroalkyl ring of 3-7 atoms; R4=alkyl with two or more carbon atoms, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, or R9 with the proviso that when R1 is acetyl or propionyl and Y=alkene, then R4 cannot be nitrofuryl or 2-quinolinyl; R5, R6, R7, R8=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, halo, or hydroxy, alkoxy, amino, NR12R13, thio, or alkylthio with the proviso that only one such heteroatom group is bonded to any one carbon atom; R9= 3 where Z═O, NR14, S; R10, R11=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, halo, hydroxy, alkoxy, alkylcarbonyloxy, carboxy, alkyloxycarbonyl, amino, NR15R16, carbamoyl, ureido, thio, or alkylthio; R12, R13, R14, R15, R16=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl. The compounds of formula I are protein kinase inhibitors and are useful in the treatment of proliferative diseases, for example, cancer, inflammation and arthritis. They may also be useful in the treatment of Alzheimer's disease, and cardiovascular disease.

Claims35

Dependent claims

A compound of the formula:

206
and pharmaceutically acceptable salts thereof wherein:
R1═R2, COR3, CONH2, CONR2R3, COOR2, or SO2R2;
R2=alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl;
R3═H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl;
207
, where n=0,1,2;
m=1,2 but both n and m cannot be 2, or
, where i, j=0 or 1 but cannot both be 1, and Y=optionally substituted alkene, alkyne, or any 2 adjacent carbon atoms of a cycloalkyl or cycloheteroalkyl ring of 3-7 atoms;
R4=alkyl with two or more carbon atoms, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, or R9 with the proviso that when R1 is acetyl or propionyl and Y=alkene, then R4 cannot be nitrofuryl or 2-quinolinyl;
R5, R6, R7, R8=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, halo, or
hydroxy, alkoxy, amino, NR12R13, thio, or alkylthio with the proviso that only one such heteroatom group is bonded to any one carbon atom;
208
where Z═O, NR14, S;
R10, R11=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, halo, hydroxy, alkoxy, alkylcarbonyloxy, carboxy, alkyloxycarbonyl, amino, NR15R16, carbamoyl, ureido, thio, or alkylthio;
R12, R13, R14, R15, R16=independently H, alkyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl.

13 more elements

A compound selected from the group consisting of:

Ethyl 3-((E)-2-acetamido-thiazol-5-yl)-acrylate;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
N-[5-(2-(5-t-Butyl-oxazol-2-yl)-ethyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenylacetamide;
N-[5-(2-(5-t-Butyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-aminopyridine;
Ethyl 3-(2-acetamido-thiazol-5-yl)-propionate;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
[(E)-5-(2-(5-Isopropyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-carbamic acid t-butyl ester;
N-[(E)-5-(2-(5-Isopropyl-oxazol -2-yl)-vinyl)-thiazol-2-yl]-2-pyridin-3-yl-acetamide;
N-[(E)-5-(2-(5-Isopropyl-oxazol -2-yl)-vinyl)-thiazol-2-yl]-acetamide;
1-(2,6-Difluorophenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2,6-Difluorophenyl)-3-[(Z)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-pyridin-3-yl-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-pyridin-3-yl-acetamide;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-naphthalen-2-yl-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-naphthalen-2-yl-acetamide;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenylacetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenylacetamide;
N-[5-(2-(2-Isopropyl-tetrazol-5-yl)-ethyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(3-Methylphenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-Phenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(4-t-Butyl-phenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(3-Chlorophenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-Bromo-2-(5-isopropyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
N-[5-(2-(5-Isopropyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-acetamide;
N-[5-(2-Phenyl)-ethyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(3-Isopropylphenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[5-(2-(3-Isopropylphenyl)-ethyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(3-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[5-(2-(2-t-Butyl-tetrazol-5-yl)-ethyl)-thiazol-2-yl]-acetamide;
N-[(Z)-5-(2-Phenyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(Z)-5-(2-(3-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
1-(2,6-Difluorophenyl)-3-[(E)-5-(2-(5-isobutyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-isobutyramide;
Ethyl 3-((Z)-2-acetamido-thiazol-5-yl)-acrylate;
N-[5-(2-(5-t-Butyl-oxazol-2-yl)-ethyl)-thiazol-2-yl]-2-pyridin-3-yl-acetamide;
N-[(E)-5-(2-(4-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(2-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(Z)-5-(2-(4-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(Z)-5-(2-(2-Pyridinyl)-vinyl)-thiazol-2-yl]-acetamide;
4-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylcarbamoylmethyl]-piperazine-1-carboxylic acid t-butyl ester;
1-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylcarbamoylmethyl]-4-methylpiperazine;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-morpholin-4-yl-acetamide;
N-[5-(3-(5-t-Butyl-oxazol-2-yl)-propyl)-thiazol-2-yl]-acetamide;
N-[5-(3-(5-t-Butyl-oxazol-2-yl)-propynyl)-thiazol-2-yl]-acetamide;
N-[(Z)-5-(2-Fluoro-2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(3H-imidazol-4-yl)-acetamide;
)-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-piperazin-1-yl-acetamide;
Methyl 4-N-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-carbamoylmethoxy-benzoate;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(1-methyl-piperidin-4-yloxy)-acetamide;
N-[5-(5-Phenyl-3H-imidazol-4-yl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(5-phenyloxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
Isobutyl-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenethylamine;
1-Cyclohexyl-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(4-Carbamoylphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(4-Piperidinylphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(Benzo[1,3]dioxol-5-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2-Hydroxyphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2,6-Dichloro-4-methoxyphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2-Pyridinyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(3-Hydroxyphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(3-Carbamoylphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(4-Hydroxyphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(3-Carbamoyl-4-methylphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
2-Dimethylamino-ethyl 4-{3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-ureido}-benzoate;
1-[4-(N,N-Dimethylcarbamoyl)phenyl]-3-[(E)-5-(2-(5-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-urea;
1-(2-Morpholinylpyridin-5-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-urea;
Methyl 5-{3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-ureido}-2-N-morpholino-benzoate;
1-(3-Pyridinyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2-Methylcyclohexyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
4-Hydroxy-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-amide;
2-(2-Hydroxyethyl)-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide;
2-Methyl-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-amide;
1-Cyclohexyl-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-methyl-urea;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-methyl-1-(1-methyl-piperidin-4-yl)-urea;
3-Hydroxy-pyrrolidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol -2-yl]-amide;
4-Methyl-piperazine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide
4-Hydroxymethyl-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide;
4-(2-Hydroxyethyl)-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl )-thiazol-2-yl]-amide;
1-[4-carboxyphenyl]-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
Piperidine-1,4-dicarboxylic acid 4-amide 1-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide;
1-(4-Pyridinyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
4-N-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-carbamoylmethoxy-benzoic acid;
6-{3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-ureido}-1,1-dioxo-1,2,3a,7a-tetrahydro-1λ6-benzo[d]isothiazol-3-one;
3-Hydroxymethyl-piperidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide;
1-(2-Chloro-4-hydroxyphenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-[4-(4-Methyl-piperazin-1-yl)phenyl]-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-methyl-1-phenyl-urea;
1-(2,6-Dihydroxy-pyrimidin-4-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3-(2,3-dihydro-phthalazine-1,4-dion-6-yl)-urea;
1-[(1S,2S)-2-Hydroxycyclohexyl]-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
(1R,2S)-2-{3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-ureido}-cyclohexanecarboxylic acid ethyl ester;
(1R,2S)-2-{3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-ureido}-cyclohexanecarboxylic acid;
1-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-2-fluoro-vinyl)-thiazol-2-yl]carbamoyl-piperidine-4-carboxylic acid;
1-(2,6-Difluorophenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-2-fluoro-vinyl)-thiazol-2-yl]-urea;
2-Piperidin-4-yl-N-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-acetamide;
1-(4-cyanophenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2-Chloro-pyridin-5-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
[5-(2-(5-t-Butyl-oxazol-2-yl)-ethyl)-thiazol-2-yl]-carbamic acid t-butyl ester;
N-[5-((S)-2-(5-t-Butyl-oxazol-2-yl)-cyclopropyl)-thiazol-2-yl]-acetamide;
N-[5-(2-(5-t-Butyl-oxazol-2-yl)-2-hydroxyethyl)-thiazol-2-yl]-acetamide;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-pyridin-3-ylmethyl-amine;
1-(2,6-Difluorophenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-2-fluoro-ethyl)-thiazol-2-yl]-urea;
1-(5-Carboxy-pyridin-2-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(5-Carbamoyl-pyridin-2-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
N-[5-((R)-2-(5-t-Butyl-oxazol-2-yl)-cyclopropyl)-thiazol-2-yl]-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(3-hydroxy)-propionamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(N-methylpiperidin-4-yl)-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-((4-(2-diethylamino)ethoxy)phenyl)-acetamide;
N-[(E)-5-(2-(5-Isopropyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-phenyl-acetamide;
1-(3,5-Dichloro-pyridin-4-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2,6-Difluorophenyl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-urea;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino)-acetic acid;
2-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-acetamide;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-propan-1-ol;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(2,2,2-trifluoroethyl)-amine;
N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-formamide;
(3R,4R)-3,4-Dihydroxy-pyrrolidine-1-carboxylic acid [(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amide;
1-(4-methylpiperizin-1-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
1-(2,6-Dimethylpiperidin-1-yl)-3-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-urea;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-acetic acid, t-butyl ester;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-acetic acid, methyl ester;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(cyanomethyl)-amine;
N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(imidazol-1-yl)-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-aniline;
N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(1-methyl-imidazol-4-yl)-acetamide;
N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3[(imidazol-4-yl)]-2-(N′-acetylamino)-propionamide;
N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-[3-(1-methyl-benzimidazol-2-yl)]-propionamide;
(S)-N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3[(1-methyl-imidazol-4-yl)]-2-(N-t-butoxyacetylamino)-propionamide;
(S)-N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3[(1-methyl-imidazol-4-yl)]-2-(N-t-butoxyacetylamino)-propionamide;
(S)-N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3-(imidazol-4-yl)-2-amino-propionamide;
(S)-N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3-(1-methyl-imidazol-5-yl)-2-amino-propionamide;
(S)-N-[(E)-5-(3-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3-(1-methyl-imidazol-4-yl)-2-amino-propionamide;
2-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-ethanol;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(4-hydroxy-butyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(3-methoxypropyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(3-hydroxy-3-methyl-butyl)-amine;
(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(3-hydroxy-propyl)-amine;
N′-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-N,N-dimethyl-pentane-1,5-diamine;
6-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-ylamino]-4-propoxy-[1,3,5]triazin-2-ol;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-carbamic acid t-butyl ester;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(2,6-dimethylphenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(2-methylphenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(4-chlorophenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(4-methoxyphenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(pyridyl-3-yl)-amine;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-(1-methyl-piperidin-4-yl)-urea;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(pyrazine-2-yl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(pyridyl-4-yl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(3-chloro-phenyl)-amine;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(2-methylpyridin-3-yl)-acetamide;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(imidazol-1-yl)-acetamide;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenylacetamide;
N-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-isobutyramide;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(pyrimidin-2-yl)-amine;
1-[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-3-(2,6-difluorophenyl)-urea;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(1-oxy-pyridin-3-yl)-acetamide;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(2-methoxyphenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(3-methoxyphenyl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(isoquinolin-3-yl)-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl-(pyrimidin-4-yl)-amine;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine;
(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(1-oxy-pyridin-2-yl)-amine;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-benzene-1,3-diamine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(1-oxy-pyridin-4-yl)-amine;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-(4-(N-pyrrolidin-1-ylethyl-carbamoyl)phenyl)-urea;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(pyridin-3-yl)-propionamide;
3-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-1-[4-(pyrrolidin-1-ylethoxy)-phenyl]-urea;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-[4-(pyrrolidin-1 -ylethoxy)-phenyl]-acetamide;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-pyridazin-3-yl-amine;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(2-methyl-pyridin-3-yl)-propionamide;
N-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-pyridine-2,6-diamine;
Cyclopropyl-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-amine;
3-(N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-carbamoyl-methyl)-1-methyl-pyridinium iodide;
N-[5-(5-t-Butyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-isobutyramide;
[5-(5-t-Butyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-2-phenylacetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-imidazol-1-yl-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-pyrazol-1-yl-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(4,5-dichloro-imidazol-1-yl)-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(4,5-dicyano-imidazol-1-yl)-acetamide;
N-[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-2-(2-methyl-imidazol-1-yl)-acetamide;
[5-(5-t-Butyl-oxazol-2-yl)-ethynyl)-thiazol-2-yl]-(pyridin-2-yl)-amine;
[(Z)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(pyridin-2-yl)-amine;
(5-Benzyl-thiazol-2-yl)-pyridin-2-yl-amine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(6-methoxy-pyrimidin-4-yl)-amine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(3-hydroxymethyl-phenyl)-amine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(4-methyl-pyridin-2-yl)-amine;
[(E)-5-(2-(5-t-Butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-(6-methyl-pyridin-2-yl)-amine.

188 more elements

Dependencies are inferred from the claim text.

Carbon substituted aminothiazole inhibitors of cyclin dependent kinases

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Carbon substituted aminothiazole inhibitors of cyclin dependent kinases

Life of this patent

Abstract

Claims35