Pyridyl derivatives and their use as mGlu5 antagonists

US7915424B2 · kind B2 · utility

Assignee

• ELI LILLY AND COMPANY · US

Inventors

• Francisco Javier Agejas-Chicharro · Alcobendas, ES
• Bruce A. Dressman · Indianapolis, US
• Jose Antonio MARTINEZ PEREZ · Madrid, ES
• James Allen Monn · Indianapolis, US
• Mohammad Sadegh Zia-Ebrahimi · Indianapolis, US
• Sonia Maria GUTIERREZ SANFELICIANO · Madrid, ES
• Steven Marc Massey · Indianapolis, US
• Steven S. Henry · New Palestine, US

Key dates

• Filing date: Mar 9, 2005
• Grant date: Mar 29, 2011
• Expiry date: Dec 18, 2026

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D213/85
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention is directed toward pyridyl derivatives of formula (I) as antagonists of the mGlu5 receptor. As such the compounds may be useful for treatment or prevention of disorders remedied by antagonism of the mGlu5 receptor, wherein Ar is phenyl or napthyl each of which may be substituted by one or more C1-C4 alkyl, C1-C4 alkoxy, C1-C5 acyl, halo, amino, nitro, cyano, hydroxy, C1-C5 acylamino, C1-C4 alkylsulfonylamino, mono-, di- or trifluorinated C1-C3 alkyl, substituents which may be the same or different and may bear a CONH2, CONHCH3, CON(CH3)2, CO2H, CO2CH3, OCF3, CH2NHCOCH3, CH2NH2, CH2N(CH3)2, CH2CN, CH2OH, CH2NHSO2CH3, CH2N(CH3)(CH2)2 CN, CH2N(CH3)CH(CH3)2, CH2NHCH(CH3)2, CH2NH(CH2)2CH3, CH2NHCO2R4, CH2NHCH2CH3, CH2NHCH3 NHCOC(CH3)2, or N(S(O)2CH3)2 substituent; R1 is hydrogen, halo, R4, CN, C(NOH)R3, C(NO—R4)R3, (CH)2CO2R4, (CH2)n OR3, COR3, CF3, SR4, S(O)R4, S(O)2R4, COCH2CO2R3, NHSO2R4, NHCOR3, C(NOR3)NH2, CH2OCOR3, (CH2)nNH2, CON(CH3)2 (CH2)nNHCO2R4, CO2R3, CONH2, CSNH2, C(NH)NHOR3, (CH2)nN(CH3)2, or CONHNHCOR3; R2 is 1,2-ethenediyl or 1,2-ethynediyl; R3 is hydrogen or C1-C4 alkyl; R4 is C1-C4 alkyl; and n is 0, 1, 2, 3 or 4; or a pharmaceutically acceptable …