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US 2024/0400575 A1Published application
Polycyclic compounds as soluble epoxide hydrolase inhibitors
AssigneeUniversitat De Barcelona
InventorsSandra Codony Gisbert, Carlos Galdeano Cantador, Rosana Leiva Martínez, Andreea Larisa Turcu, Elena Valverde Murillo, Santiago Vázquez Cruz
Life of this patent
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Abstract
The present invention relates to soluble epoxide hydrolase (sEH) inhibitors of formula (1) to processes for their obtention and to their therapeutic indications.
Claims18
A compound of formula (I)
- or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein:
- G1 represents an oxygen atom or a methylene group or a single bond;
- G2 represents an oxygen atom or a sulphur atom;
- G3 represents a radical selected from the group consisting of —NH—(CH2)m—, —O—(CH2)m- and —(CH2)n—;
- m is an integer from 0 to 6;
- n is an integer from 1 to 7
- R1 is a radical selected from the group consisting of:
- a) C6-C10 aryl which may be optionally substituted by 1 to 4 substituents selected from the group consisting of halogen atoms, C1-C6 acyl, nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SF5), sulfonyl (SO3H), fluorosulfonyl (SO2F), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxycarbonylmethyl and methylaminocarbonylpyridyloxy;
- b) heteroaryl having from 2 to 11 carbon atoms and 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S and which may be optionally substituted by 1 to 4 substituents selected from the group consisting of halogen atoms, C1-C6 acyl, nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SF5), sulfonyl (SO3H), fluorosulfonyl (SO2F), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl and C1-C6 alkoxycarbonylmethyl;
- c) saturated or partially unsaturated, monocyclic or bicyclic heterocyclyl having from 5 to 11 carbon atoms and 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S and which may be optionally substituted by 1 to 4 substituents selected from the group consisting of halogen atoms, C1-C6 acyl, C3-C6 cycloalkyl-C(═O), nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethylcarbonyl (CF3CO), pentafluorosulfanyl (SF5), sulfonyl (SO3H), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxycarbonylmethyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfonyl, benzyl, heteroarylmethyl, pyridincarbonyl, phenylcarbonyl, tetrahydropyrancarbonyl, C6-C10 arylsulfonyl which may be optionally substituted by 1 to 2 substituents selected from the group consisting of halogen atoms, nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SF5), sulfonyl (SO3H), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxycarbonylmethyl and phenyl which may be optionally substituted by 1 to 4 substituents selected from the group consisting of halogen atoms, C1-C6 acyl, nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SF5), sulfonyl (SO3H), fluorosulfonyl (SO2F), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl, C3-C6 cycloalkyl and C1-C6 alkoxycarbonylmethyl;
- d) C6-C10 cycloalkyl which may be optionally substituted by 1 to 4 substituents selected from the group consisting of halogen atoms, C1-C6 acyl, nitro (NO2), cyano (C≡N), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SF5), sulfonyl (SO3H), carboxylic group (COOH), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxycarbonylmethyl, pyridinyloxy which may be unsubstituted or substituted by a group selected from COOH and CONHCH3, and phenoxy which may be unsubstituted or substituted by COOH, COOR5, CONH2, CN or OH;
- R2 is a radical selected from the group consisting of hydrogen or deuterium atoms, halogen atoms, methyl, hydroxy and C1-C6 alkoxy;
- R3 and R4 are radicals which may be identical or different and which are independently selected from the group consisting of hydrogen atoms, halogen atoms, C1-C6 acyl, nitro (NO2), cyano (C≡N), carboxylic group (COOH), hydroxy (OH), trifluoromethyl (CF3), trifluoromethoxy (OCF3), pentafluorosulfanyl (SFs), sulfonyl (SO3H), fluorosulfonyl (SO2F), amino (NH2), mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxy, C1-C6 alkyl and C1-C6 alkoxycarbonylmethyl;
- or R3 and R4 may form together a radical —O—(CH2)p-O—, wherein p is an integer from 1 to 3;
- R5 is a radical selected from C1-C6 alkyl and C3-C6 cycloalkyl.
12 more elements
Dependencies are inferred from the claim text.