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US 2010/0144731 A1Published application
Novel Biccyclic Compounds As GATA Modulators
AssigneeDr. Reddy's Laboratories, Inc.
InventorsDibyendu De, Ish Kumar Khanna, Sivaram Pillarisetti
Life of this patent
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Abstract
Novel bicyclic compounds, stereoisomers, and/or pharmaceutically acceptable salts of the novel bicyclic compounds, and/or pharmaceutically acceptable salts of the stereoisomers of the novel bicyclic compounds are provided. Additionally, methods of forming novel bicyclic compounds, stereoisomers, and/or pharmaceutically acceptable salts of the novel bicyclic compounds, and/or pharmaceutically acceptable salts of the stereoisomers of the novel bicyclic compounds are provided.
Claims31
A compound of formula (I),
- stereoisomers thereof and/or pharmaceutically acceptable salts of compounds of formula (I) and/or pharmaceutically acceptable salts of the stereoisomers of compounds of formula (I);
- wherein
- R1 and R2 are each independently selected from —R, —OR, —NRaRb or
- with a proviso that at least one of R1 and R2 is
- R is selected from an optionally substituted group selected from alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl, wherein one or more optional substituents on R are selected from halogen, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, —CO-alkyl, —(CH2)r—OH, —(CH2)r-alkoxy, aryl, heteroaryl, (CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- A is a 3- to 7-member cycloalkyl ring;
- Ra and Rb are each independently selected from hydrogen, —(CH2)r-hydroxy, —(CH2)r-halogen, and an optionally substituted group selected from alkyl, —(CH2)r-cycloalkyl, —(CH2)r-heterocyclyl, —(CH2)r-aryl or —(CH2)r-heteroaryl, wherein one or more optional substituents on Ra and Rb are each independently selected from halogen, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, —CO-alkyl, —(CH2)r—OH, —(CH2)r-alkoxy, aryl, heteroaryl, —(CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- or
- Ra and Rb optionally combine with the nitrogen atom, to which they are attached, to form an optionally substituted 5- to 6-membered heterocyclic ring optionally having 1 to 3 additional hetero atoms or groups selected from nitrogen, oxygen, sulfur, SO2 or CO, wherein one or more optional substituents on the 5- to 6-membered heterocyclic ring are selected from halogen, hydroxy, alkyl, haloalkyl, —CO-alkyl, —(CH2)r—OH or —(CH2)r-alkoxy;
- Rc is selected from hydrogen or alkyl;
- Rd is selected from cyano, —(CH2)r—OH, —(CH2)r-alkoxy, alkyl, aryl, —NH-aryl, heteroaryl, —(CH2)rCO-alkyl, —(CH2)rCOORe, —(CH2)rCONRfRg, —(CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- Re is selected from hydrogen, alkyl, cycloalkyl, aryl, heterocyclyl or heteroaryl;
- Rf and Rg are each independently selected from hydrogen or an optionally substituted group selected from alkyl, cycloalkyl, alkoxy, aryl, heteroaryl or heterocyclyl, wherein one or more optional substituents on Rf and Rg are each independently selected from halogen, hydroxyl or alkyl;
- Rh is selected from alkyl, cycloalkyl, aryl, heterocyclyl or heteroaryl;
- m is an integer from 0 to 2;
- n is an integer from 1 to 3;
- and
- r is an integer from 0 to 3.
15 more elements
A compound comprising one or more of
- 1-[4-(2-Cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(2-Cyclopentylmethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(2-Cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Hydroxy-piperidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Pyrrolidin-1-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(1-Methyl-1H-pyrazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Fluoro-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclopentanecarboxylic acid,
- 1-{4-[2-(4-Acetyl-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(4-tert-Butylamino-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(4-Cyclopentylamino-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(3-Fluoro-phenylamino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Cyclopentylamino-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(Cyclopropylmethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(Bis-cyclopropylmethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Methanesulfonyl-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-p-Tolyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Phenyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(2-Oxo-pyrrolidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid methyl ester,
- 1-{4-[2-(6-Methyl-pyridin-3-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- {1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutyl}-methanol,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- {1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentyl}-methanol,
- 1-[4-(4-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- Sodium 1-[4-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylate,
- 1-{4-[2-(4,4-Difluoro-piperidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid
- 1-[4-(2-Morpholin-4-yl-5,6,7,8-tetrahydro-quinazolin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[4-(3,5-Dimethyl-isoxazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Phenoxy-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid cyclopentylamide,
- 1-(4-{2-[4-(Pyrrolidine-1-sulfonyl)-phenylamino]-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino}-phenyl)-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarbonitrile,
- 1-[4-(4-Phenoxy-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester,
- 1-{4-[4-(Benzyl-ethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- Sodium 1-{4-[ethyl-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-amino]-phenyl}-cyclobutanecarboxylate,
- stereoisomers thereof and/or pharmaceutically acceptable salts of the compounds and/or pharmaceutically acceptable salts of the stereoisomers of the compounds.
33 more elements
A method for the treatment of atherosclerosis and/or diabetes in a subject, which comprises administering to the subject a therapeutically effective amount of a compound comprising:
- stereoisomers thereof and/or pharmaceutically acceptable salts of formula (I) and/or pharmaceutically acceptable salts of the stereoisomers of formula (I);
- wherein
- R1 and R2 are each independently selected from —R, —OR, —NRaRb or
- with a proviso that at least one of R1 and R2 is:
- R is selected from an optionally substituted group selected from alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl, wherein one or more optional substituents on R are selected from halogen, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, —CO-alkyl, —(CH2)r—OH, —(CH2)r-alkoxy, aryl, heteroaryl, —(CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- A is a 3- to 7-member cycloalkyl ring;
- Ra and Rb are each independently selected from hydrogen, —(CH2)r-hydroxy, —(CH2)r-halogen, and an optionally substituted group selected from alkyl, —(CH2)r-cycloalkyl, —(CH2)r-heterocyclyl, —(CH2)r-aryl or —(CH2)r-heteroaryl, wherein one or more optional substituents on Ra and Rb are each independently selected from halogen, hydroxy, cyano, alkyl, haloalkyl, cycloalkyl, —CO-alkyl, —(CH2)r—OH, —(CH2)r-alkoxy, aryl, heteroaryl, —(CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- or
- Ra and Rb optionally combine with the nitrogen atom, to which they are attached, to fowl an optionally substituted 5- to 6-membered heterocyclic ring optionally having 1 to 3 additional hetero atoms or groups selected from nitrogen, oxygen, sulfur, SO2 or CO, wherein one or more optional substituents on the 5- to 6-membered heterocyclic ring are selected from halogen, hydroxy, alkyl, haloalkyl, —CO-alkyl, —(CH2)r—OH or —(CH2)r-alkoxy;
- Rc is selected from hydrogen or alkyl;
- Rd is selected from cyano, —(CH2)r—OH, —(CH2)r-alkoxy, alkyl, aryl, —NH-aryl, heteroaryl, —(CH2)rCO-alkyl, —(CH2)rCOORc, —(CH2)rCONRfRg, —(CH2)rSO2NRfRg or —(CH2)rSO2Rh;
- Re is selected from hydrogen, alkyl, cycloalkyl, aryl, heterocyclyl or heteroaryl;
- Rf and Rg are each independently selected from hydrogen or an optionally substituted group selected from alkyl, cycloalkyl, alkoxy, aryl, heteroaryl or heterocyclyl, wherein one or more optional substituents on Rf and Rg are each independently selected from halogen, hydroxyl or alkyl;
- Rh is selected from alkyl, cycloalkyl, aryl, heterocyclyl or heteroaryl;
- m is an integer from 0 to 2;
- n is an integer from 1 to 3;
- and
- r is an integer from 0 to 3.
15 more elements
A method for the treatment of atherosclerosis and/or diabetes in a subject, which comprises administering to the subject a therapeutically effective amount of at least one compound selected from one or more of:
- 1-[4-(2-Cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(2-Cyclopentylmethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(2-Cyclopentyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Hydroxy-piperidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Pyrrolidin-1-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(1-Methyl-1H-pyrazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Fluoro-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclopentanecarboxylic acid,
- 1-{4-[2-(4-Acetyl-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(4-tert-Butylamino-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- 1-[4-(4-Cyclopentylamino-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(3-Fluoro-phenylamino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Cyclopentylamino-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(Cyclopropylmethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(Bis-cyclopropylmethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-{4-[2-(4-Methanesulfonyl-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-p-Tolyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Phenyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[2-(2-Oxo-pyrrolidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid methyl ester,
- 1-{4-[2-(6-Methyl-pyridin-3-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- {1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutyl}-methanol,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid,
- {1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentyl}-methanol,
- 1-[4-(4-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- Sodium 1-[4-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylate,
- 1-{4-[2-(4,4-Difluoro-piperidin-1-yl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-phenyl}-cyclobutanecarboxylic acid
- 1-[4-(2-Morpholin-4-yl-5,6,7,8-tetrahydro-quinazolin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-{4-[4-(3,5-Dimethyl-isoxazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- 1-[4-(2-Phenoxy-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid cyclopentylamide,
- 1-(4-{2-[4-(Pyrrolidine-1-sulfonyl)-phenylamino]-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino}-phenyl)-cyclobutanecarboxylic acid,
- 1-[4-(2-Morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarbonitrile,
- 1-[4-(4-Phenoxy-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester,
- 1-{4-[4-(Benzyl-ethyl-amino)-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamino]-phenyl}-cyclobutanecarboxylic acid,
- Sodium 1-{4-[ethyl-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-amino]-phenyl}-cyclobutanecarboxylate,
- stereoisomers thereof and/or pharmaceutically acceptable salts of the compounds and/or pharmaceutically acceptable salts of the stereoisomers of the compounds.
33 more elements
Dependencies are inferred from the claim text.