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US 9,000,007 B2Granted
5-benzylaminomethyl-6-aminopyrazolo [3, 4 -B] pyridine derivatives as cholesteryl ester-transfer protein (CETP) inhibitors useful for the treatment of atherosclerosis
AssigneeDr. Reddy's Laboratories, Inc.
InventorsAnima Boruah, Shanavas Alikunju
Life of this patent
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Abstract
The present application relates to a series of substituted pyra-zolopyridin-6-amines having the general formula (I), including their stereoisomers and/or their pharmaceutically acceptable salts. Wherein R, R1, R2, Ra, Raa, Rb and n are as defined herein. The present invention further relates to pharmaceutical compositions comprising compounds of formula (I). The compounds of this application are useful as CETP inhibitors for increasing HDL cholesterol and decreasing LDL cholesterol in a patient.
Claims12
A compound having the formula (Ic):
- or a stereoisomer thereof or a pharmaceutically acceptable salt thereof, wherein
- Ra and Raa are independently of each other selected from hydrogen or alkyl;
- and
- Rc is selected from hydrogen, cyano, halogen, alkyl, alkoxy, haloalkoxy, —COORd, —C(═O)—Re, —CONRgRh, —C(═O)—CH═CH—NRiRj, —NHCORt, an optionally substituted group selected from cycloalkyl, aryl, heteroaryl or heterocycle ring, wherein the optional substituent, in each occurrence, is selected independently from hydrogen, halogen, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, alkoxyalkyl or haloalkoxy.
1 more element
A compound, which is selected from the group consisting of:
- N-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)isobutyramide,
- 5-(((3,5-bis(trifluoromethyl)benzyl)(5-cyclopropylpyridin-2-yl)amino)methyl)-1-(tert-butyl) -N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine,
- N-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5 -yl)cyclopropane carboxamide,
- 1-(2-(((6-(bis(cyclopropylmethyl)amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)ethanone,
- 1-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)ethanone,
- (E)-1-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5 -bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)-3-(dimethylamino)prop-2-en-1-one,
- 5(((3,5-bis(trifluoromethyl)benzyl)(5-(isoxazol-3-yl)pyrimidin-2-yl)amino)methyl)-N,N-bis(cyclopropylmethyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-amine,
- 5-(((5-(1H-pyrazol-3-yl)pyrimidin-2-yl)(3,5-bis(trifluoromethyl)benzyl)amino)methyl)- 1-(tert-butyl)-N,N-bis (cyclopropylmethyl)-3-methyl-1H-pyrazolo [3,4-b]pyridin-6-amine,
- 5-(((3,5-bis(trifluoromethyl)benzyl)(5-(1-methyl-1H-pyrazol-3-yl)pyrimidin-2-yl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1 H-pyrazolo [3,4-b]pyridin-6-amine,
- 2-(((6-(bis(cyclopropylmethyl)amino)- 1-(tert-butyl)-3-methyl- 1H-pyrazolo [3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidine-5-carbonitrile,
- 2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo [3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidine-5-carboxamide,
- 2-(((6-(bis(cyclopropylmethyl)amino)- 1-(tert-butyl)-3-methyl- 1H-pyrazolo [3 ,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)-N,N-dimethylpyrimidine -5-carboxamide,
- 3-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)oxazolidin-2-one,
- 5-3,5-bis(trifluoromethyl)benzyl)(5-morpholinopyrimidin-2-yl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo [3,4-b ]pyridin-6-amine,
- 5-(((3,5-bis(trifluoromethyl)benzyl)(5-morpholinopyrimidin-2-yl)amino)methyl)-N,N-bis(cyclopropylmethyl)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-amine,
- 1-(2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidin-5-yl)pyrrolidin-2-one,
- Ethyl-2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)-4-methylpyrimidine-5-carboxylate,
- 2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo [3 ,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)-4-methylpyrimidine -5-carboxylic acid,
- Ethyl-2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidine-5-carboxylate,
- 2-(((6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo [3 ,4-b]pyridin-5-yl)methyl)(3,5-bis(trifluoromethyl)benzyl)amino)pyrimidine-5-carboxylic acid,
- 5-(((3,5-bis(trifluoromethyl)benzyl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine, and
- 5-(((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino) methyl)-1-(tert-butyl) -N,N-bis(cyclopropylmethyl)-3-methyl- 1H-pyrazolo [3,4-b ]pyridin-6-amine;
- or a stereoisomer thereof or a pharmaceutically acceptable salt thereof.
20 more elements
Dependencies are inferred from the claim text.