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US 8,008,310 B2Granted
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
Derivatives of pyrido[2,3-d]pyrimidine are provided having formula (I) with Ar1, Ar2 and R1 as defined herein, which are useful for treating cell proliferative conditions, and to the preparation thereof, and to the therapeutic application of the same.
Claims9
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 one or more substituents selected from the group consisting hydroxyl, halogen, and (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 the group consisting of:
- in which X is O or S;
- Y is CH2 or NH;
- R2 is selected from the group consisting of H, (C1-C6) alkyl and (CH2)nNR4R5;
- and R′2 is (CH2)nNR4R5;
- R4 and R5 are each, independently of one another, a substituent selected from the group consisting of H, (C1-C4)alkyl, (C1-C6)alkyl(C3 -C7)cycloalky, (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 the same or different substituents selected from the group consisting of a halogen atom, a (C1-C4)alkyl group, a trifluoromethyl group, and a (C1-C4)alkoxy group;
- n represents 1, 2 or 3;
- or a pharmaceutically acceptable salt thereof.
11 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 the group consisting of:
- R2 is CH3 or (CH2)nNR4R5;
- R′2 is CH2NR4R5, in which R4 and R5 are independently selected from the group consisting of 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 the same or different substituents selected from the group consisting of a halogen atom, a (C1-C4)alkyl group, a trifluoromethyl group and a (C1-C4)alkoxy group;
- n represents 1, 2 or 3;
- or a pharmaceutically acceptable salt thereof.
7 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-ylFN′-(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-ylFN′-(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;
- and
- 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;
- or a pharmaceutically acceptable salt thereof.
9 more elements
Dependencies are inferred from the claim text.