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US 2008/0176874 A1Published application
Derivatives of Pyrido[2,3-d]pyrimidine, the Preparation Thereof, and the Therapeutic Application of the Same
AssigneeSanofi-Aventis
InventorsBernard BOURRIE, Pierre CASELLAS, Samir JEGHAM, Claude MUNEAUX, Pierre PERREAUT
Life of this patent
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Abstract
The invention relates to derivatives of pyrido[2,3-d]pyrimidine, to the preparation thereof, and to the therapeutic application of the same.
Claims21
A compound according to formula (I):
- in which:
- R1 is selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkyl(C3-C7)cycloalkyl, CH2COR3, phenyl, and phenyl substituted with hydroxyl and/or halogen and/or (C1-C6)alkyl;
- R3 is a hydroxyl, (C1-C4)alkoxy, amino, (C1-C4)alkylamino or di(C1-C4)alkylamino group;
- Ar1 is a radical selected from:
- in which X is O or S, Y is CH2 or NH, and R2 is selected from the group consisting of H, (C1-C6)alkyl and (CH2)nNR4R5, and R12 is (CH2)nNR4R5;
- R4 and R5 are each, independently of one another, a substituent selected from H, (C1-C4)alkyl, (C1-C6)alkyl(C3-C7)cycloalkyl, (C3-C7)cycloalkyl, C(═NH)NH2 and SO2(C1-C6)alkyl, R5 can also be a CO—(C1-C4)alkyl, CO—(C3-C7)cycloalkyl, CO-aryl, SO2-aryl, tert-butoxycarbonyl or benzyloxycarbonyl group;
- or R4 and R5, together with the nitrogen atom to which they are attached, constitute an azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl or morpholinyl radical, said radical being unsubstituted or substituted one or more times with a (C1-C6)alkyl, (C1-C4)alkyl-OH or COO(C1-C6)alkyl group;
- Ar2 is a phenyl group which is unsubstituted or substituted from 1 to 5 times with similar or different substituents selected from a halogen atom, a (C1-C4)alkyl group, a trifluoromethyl group or a (C1-C4)alkoxy group;
- n represents 1, 2 or 3;
- or a pharmaceutically acceptable salt, hydrate or solvate thereof.
7 more elements
A compound according to formula (I):
- in which:
- R1 is selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkyl(C3-C7)cycloalkyl, CH2COR3, phenyl, and phenyl substituted with hydroxyl and/or halogen and/or (C1-C6)alkyl;
- R3 is a hydroxyl, (C1-C4)alkoxy, amino, (C1-C4)alkylamino or di(C1-C4)alkylamino group;
- Ar1 is a radical selected from:
- R2 is CH3 or (CH2)nNR4R5, and R12 is CH2NR4R5, in which R4 and R5 are independently selected from H and (C1-C6)alkyl, and Y is CH2 or NH;
- Ar2 is a phenyl group which is unsubstituted or substituted from 1 to 5 times with similar or different substituents selected from a halogen atom, a (C1-C4)alkyl group, a trifluoromethyl group or a (C1-C4)alkoxy group;
- n represents 1, 2 or 3;
- or a pharmaceutically acceptable salt, hydrate or solvate thereof.
5 more elements
A compound selected from the group consisting of:
- N-[2-(2,1,3-benzothiadiazol-4-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[6-(2,6-dichlorophenyl)-2-[(1,3-dihydro-2,2-dioxido-2,1-benzisothiazol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[6-(2,6-dichlorophenyl)-2-[(2-methyl-6-benzoxazolyl)amino]pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[6-(2,6-dichlorophenyl)-2-[[2-[(diethylamino)methyl]-5-benzofuranyl]amino]pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- 1,1-dimethylethyl [[5-[[6-(2,6-dichlorophenyl)-7-[[[(1,1-dimethylethyl)-amino]carbonyl]amino]pyrido[2,3-d]pyrimidin-2-yl]amino]-2-benzoxazolyl]methyl]carbamate;
- N-[2-[[2-(aminomethyl)-5-benzoxazolyl]amino]-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[6-(2,6-dichlorophenyl)-2-(imidazo[1,2-a]pyridin-6-ylamino)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[6-(2,6-dichlorophenyl)-2-([1,2,4]triazolo[1,5-a]pyridin-6-ylamino)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzoxadiazol-5-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(1,3-dihydro-2,2-dioxido-2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2-bromo-6-chlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-ethylurea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dibromophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dibromophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-ethylurea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-phenylurea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dimethylphenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-difluorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1,1-dimethylethyl)urea;
- and
- N-[2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-N′-(1-methylethyl)urea;
- or a pharmaceutically acceptable salt, hydrate or solvate thereof.
19 more elements
Dependencies are inferred from the claim text.