(1h-imidazol-1-ylmethyl) substituted benzimidazole derivatives

Details (1h-imidazol-1-ylmethyl) substituted benzimidazole derivatives (1h-imidazol-1-ylmethyl) substituted benzimidazole derivatives

C - Chemistry, Metallurgy

07

D

167/207, 260/280

C07D 401/14 (2006.01) C07D 403/00 (2006.01) C07D 417/14 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1323366

0991f JAB 522 ABSTRACT NOVEL (1H-IMIDAZOL-1-YLMETHYL) SUBSTITUTED BENZIMIDAZOLE DERIVATIVES Novel (1H-imidazol-1-ylmethyl) substituted benzimidazole derivatives, compositions containing the same, and methods of treating androgen dependent disorders in mammals. The present invention therefore is concerned with imidazole derivatives of formula Image (I), the pharmaceutically acceptable acid addition, metal or amine substitution salts and the stereochemically isomeric forms thereof, wherein R is hydrogen; C1-10alkyl; C3-7cycloalkyl; Ar1 or Ar1-C1-6alkyl; R1 is hydrogen; C3-7cycloalkyl; Ar1; C1-10alkyl; C1-6alkyl substituted wlth Arl or C3-7cycloalkyl; hydroxy; C1-10alkyloxy; C1-6alkyloxy substi- tuted with Ar1 or C3-7cycloalkyl; C3-6alkenyloxy optionally substituted with Ar2; C3-6alkynyloxy optionally substituted with Ar2; or Ar1-oxy; A is a bivalent radical having the formula -CR2=N- (a) or Image (b), wherein the carbon atom in the bivalent radical (a) or (b) is connected to -NR1; said R2 being hydrogen; halo; C1-4alkyl substituted with up to 4 halo atoms; C3-7cycloalkyl; Ar1; quinolinyl; indolinyl; C1-10alkyl; C1-6alkyl substituted with Ar1, C3-7cycloalkyl. quinolinyl, indolinyl or hydroxy; C1-10alkyloxy; C1-6alkyloxy substituted with Ar1 or C3-7cycloalkyl: C3-6alkenyl optionally substituted with Ar1; Ar2-oxy; C1-6alkyloxycarbonyl; carboxyl; C1-6alkylcarbonyl; Ar1-carbonyl or Ar1-(CHOH)-; said X being O or S; said R3 being hydrogen. C1-6alkyl or Ar2-C1-6alkyl: Ar1 is phenyl, substituted phenyl, pyridinyl, aminopyridinyl, imidazolyl, thienyl, halothienyl, furanyl, halofuranyl or thiazolyl; Ar2 is phenyl or substituted phenyl; in Ar1 and Ar2 said substituted phenyl being phenyl substituted with 1, 2 or 3 substltuents each independently selected from halo, hydroxy, trifluoromethyl, C1-6alkyl, C1-6alkyloxy, cyano, amino, mono- and di(C1-6alkyl)amino. nitro. carboxyl. formyl and C1-6alkyl- oxycarbonyl.

546763

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