CYCLOALKANECARBOXYLIC ACID DERIVATIVES AS CXCR3 RECEPTOR ANTAGONISTS Russian patent published in 2017 - IPC C07D207/40 C07D209/48 C07D209/52 C07D209/94 C07D211/88 C07D221/20 C07D233/74 C07D239/54 C07D263/44 C07D277/34 C07D405/12 C07D413/12 C07D417/12 A61K31/4015 A61K31/403 A61K31/4035 A61K31/4166 A61K31/421 A61K31/426 A61K31/427 A61K31/438 A61K31/45 A61K31/506 A61K31/513 A61K31/53 A61P37/08 

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula 1 where R is hydrogen or a C_1-4-alkyl group; R¹ means a group selected from the group consisting of structures represented by formulas (Ia), where R² means hydrogen or a C_1-4-alkyl group; R³ means hydrogen, a halogen, CF₃, CN or C_1-4-alkyl and R⁴ means hydrogen, a halogen or a C_1-4-alkyl; a=0, 1, or 2; b=0, 1, 2 or 3; C=1, 2 or 3, and R^a, R^b, R^c and R^d represent, independently of one another, H or a C_1-4-alkyl; X means a C₂ aliphatic hydrocarbon bridge optionally containing a double bond or a triple bond or a hetero-atom selected from O and S, or CH(CH₂)CH-; Y means hydrogen, a halogen, a C_1-4-alkyl, C_1-4-alcoxy or C_1-4-hydroxyalkyl; Z means a C_1-4-aliphatic hydrocarbon bridge optionally containing one double bond and/or one hetero-atom selected from O, S, N and N(CH₃), or means a C_2-4-aliphatic hydrocarbon bridge fused with a C_3-6-cycloalkyl, optionally containing one or more double bonds or with a phenyl ring, or means a C_1-4-aliphatic hydrocarbon bridge substituted with a spiro-C_3-6-cycloalkyl, optionally containing one or more double bonds; or its pharmaceutically acceptable salt, or a stereoisomer, or a pharmaceutically acceptable salt of the stereoisomer. The compounds according to the invention are obtained due to reductive amination of the benzaldehyde of formula 4 by means of a primary amine R¹-NH₂, the introduction in the interaction of the obtained secondary amine of formula 2 with ether formyl - or oxocyclohexanecarboxylic acid of formula 3, where X, Y, Z, R¹, R, R^a, R^b, R^c, R^d, b and c have the meanings as specified for formula 1, and R' means -CHO or =O, and, optionally, the hydrolysis of the obtained ester of formula 1. The invention also relates to an intermediate compound of formula 2 or a salt thereof. The compound of formula 1 according to the invention is intended for use in the preventive and / or therapeutic treatment of a disease or disorder mediated by CXCR3 receptor as a medicament or as part of a pharmaceutical composition.

EFFECT: cycloalkanecarboxylic acid derivatives as CXCR3 receptor antagonists.

20 cl, 6 tbl, 160 ex