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US 9,758,474 B2Granted
Immunomodulator and anti-inflammatory compounds
AssigneesIncozen Therapeutics Pvt. Ltd., Rhizen Pharmaceuticals SA
InventorsMeyyappan Muthuppalaniappan, Prashant K. Bhavar, Srikant Viswanadha, Swaroop K. Vakkalanka, Gayatri S. Merikapudi
Life of this patent
Estimating the term…
Abstract
The present invention provides dihydroorotate dehydrogenase inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of diseases or disorders wherein the inhibition of Dihydroorotate dehydrogenase is known to show beneficial effect.
Claims8
A compound of formula (I)
- or a tautomer, stereoisomer, pharmaceutically acceptable salt, pharmaceutically acceptable ester, or N-oxide thereof, wherein
- Ring A including substituent R1 is
- Ring B, including X1, X2 and X3 is selected from
- wherein Ring A and Ring B may each independently be optionally substituted by one or more R4 and C* is attached to —NR—;
- R is hydrogen;
- L1 and L2 are absent;
- Cy is selected from the group consisting of
- each occurrence of R4 is independently selected from the group consisting of hydrogen, hydroxy, halogen, cyano, —ORa, —S(═O)q—Ra, —NRaRb, —C(═Y)—Ra, —C(═Y)—ORa, —C(═Y)—NRaRb, —S(═O)q—NRaRb, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylakyl, and substituted or unsubstituted cycloalkenyl;
- each occurrence of Ra and Rb may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and —ORc (wherein Rc is substituted or unsubstituted (C1-6)alkyl);
- each occurrence of Y is independently selected from the group consisting of O, S and NRa;
- and
- each occurrence of q independently represents 0, 1 or 2
- wherein the term substituted refers to substitution with any one or any combination of the following substituents which may be the same or different and are selected from hydroxy, halogen, carboxyl, cyano, nitro, oxo (═O), thio (═S), unsubstituted alkyl, unsubstituted alkoxy, halo-substituted alkoxy, unsubstituted alkenyl, unsubstituted (alkynyl, unsubstituted cycloalkyl, unsubstituted cycloalkenyl, unsubstituted cycloalkylalkyl, unsubstituted cycloalkenylalkyl, unsubstituted heterocyclic ring, unsubstituted heterocycicylalkyl, unsubstituted aryl, unsubstituted arylalkyl, unsubstituted heteroaryl, unsubstituted heteroarylalkyl, unsubstituted guanidine, —COORx, —C(O)Rx, —C(S)Rx, —C(O)NRxRy, —C(O)ONRxRy, —NRyRz, —NRxCORyRz, —N(Rx)SORy, —N(Rx)SO2Ry, —(═N—N(Rx)Ry), —NRxC(O)ORy, —NRxC(O)Ry—, —NRxC(S)Ry, —NRxC(S)NRyRz, —SONRxRy, —SO2NRxRy—, —ORx, —ORxC(O)NRyRz, —ORxC(O)ORy, —OC(O)Rx, —OC(0)NRxRy, —RxNRyC(O)Rz, —RxORy, —RxC(O)ORy, —RxC(O)NRyRz, —RxC(O)Rx, —RxOC(O)Ry, —SRx, —SORx, —SO2Rx, —ONO2, wherein Rx, Ry and Rz in each of the above groups can be hydrogen, unsubstituted alkyl, unsubstituted alkoxy, unsubstituted alkenyl, unsubstituted alkynyl, unsubstituted cycloalkyl, unsubstituted cycloalkenyl, unsubstituted cycloalkylalkyl, unsubstituted cycloalkenylalkyl, unsubstituted heterocyclic ring, heterocycicylalkyl, unsubstituted aryl, unsubstituted arylalkyl, unsubstituted heteroaryl, unsubstituted heteroarylalkyl.
10 more elements
A compound selected from
- 2-(6-(3-Methoxyphenyl)pyridin-3-ylcarbamoyl)benzoic acid
- 2-(3′-Ethoxy-3-fluorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-[3-Fluoro-3′-(trifluoromethoxy)biphenyl-4-ylcarbamoyl]benzoic acid
- 2-[2′-Fluoro-3-(trifluoromethoxy)biphenyl-4-ylcarbamoyl]benzoic acid
- 2-(3-fluoro-3′-methoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-ethoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-[3′-(ethylthio)-2,3,5,6-tetrafluorobiphenyl-4-ylcarbamoyl]benzoic acid
- 2-(2′-chloro-2-fluoro-5′-methoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3-fluoro-3′-propoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-propoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-[3′-(ethylthio)-2-fluorobiphenyl-4-ylcarbamoyl]benzoic acid
- 2-(2′-chlorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-methoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-[3′-(trifluoromethoxy)biphenyl-4-ylcarbamoyl]benzoic acid
- 2-(3′-ethylbiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-butoxy-2,3,5,6-tetrafluorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-butoxy-3-fluorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-cyclopropoxy-3-fluorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-cyclopropoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-butoxybiphenyl-4-ylcarbamoyl)benzoic acid
- 2-(3′-butoxy-2-fluorobiphenyl-4-ylcarbamoyl)benzoic acid
- 2-[2,6-Difluoro-4-(3-propyl-1H-indol-5-yl)phenylcarbamoyl]benzoic acid
- 2-[2-Chloro-4-(3-ethyl-1H-indol-5-yl)-6-fluorophenylcarbamoyl]benzoic acid
- and pharmaceutically acceptable salts thereof.
21 more elements
Dependencies are inferred from the claim text.