Novel androgens

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 209/40 (2006.01) A61K 31/40 (2006.01) A61P 5/26 (2006.01) A61P 15/16 (2006.01) C07D 401/04 (2006.01) C07D 401/12 (2006.01) C07D 403/04 (2006.01) C07D 405/04 (2006.01) C07D 413/04 (2006.01)

Patent

CA 2562571

The compounds of the subject invention have a structure according to formula I: wherein X is S or SO2; R1 is (1C-6C)alkyl, (3C-6C)alkenyl, or (3C- 6C)alkynyl, each optionally subst ituted with (3C-6C)cycloalkyl, OH, OC(O)(1C- 4C)alkyl, (1C- 4C)alkoxy, halogen, cyano, formyl, C(O)(1C-4C)alkyl, CO2H, CO2(1C- 4C)alkyl, C(O)NR5R6, S(O)(1C-4C)alkyl or S(O)2(1C-4C)alkyl; R2 is hydrogen, (1C-4C)alkyl or C(O)(1C-4C)alkyl; R3 is a phenyl group optionally substituted with (1C-4C)alkyl, (1C-4C)fluoroalkyl, (1C-4C)alkoxy, (1C- 4C)fluoroalkoxy, halogen, cyano or nitro; or R3 is a 5- or 6-membered aromatic heterocyclic ring structure optionally substituted with (1C-4C)alkyl, (1C- 4C)fluoroalkyl, (1C-4C)alkoxy, halogen or cyano; R4 is a phenyl group or an aromatic 6-membered heterocycle, substituted at the ortho position with 1- hydroxy(1C-4C)alkyl, (1C-4C)alkoxy, C(O)(1C- 4C)alkyl, CO2(1C-4C)alkyl, C(O)NH2, cyano, nitro, or CH=NOR7, and optionally further substituted with (1C- 2C)alkyl, (1C-2C)fluoroalkyl or halogen; R5 is 2-pyridyl optionally substituted with (1C-2C)alkyl, (1C- 2C)fluoroalkyl or halogen; or R5 and R6 are independently hydrogen or (1C-4C)alkyl; R7 is hydrogen or C(O)(1C- 4C)alkyl; R8 , R9 , R10 are independently hydrogen, (1C-2C)alkyl, fluoro or chloro; or a salt or hydrate form thereof.

L'invention concerne des composés possédant une structure de formule (I): dans laquelle X désigne S ou SO¿2?; R?1¿ représente (1C-6C)alkyle, (3C-6C)alcényle ou (3C-6C)alkynyle, éventuellement substitués individuellement par (3C-6C)cycloalkyle, OH, OC(O)(1C-4C)alkyle, (1C- 4C)alcoxy, halogène, cyano, formyle, C(O)(1C-4C)alkyle, CO¿2?H, CO¿2?(1C- 4C)alkyle, C(O)NR?5¿R?6¿, S(O)(1C-4C)alkyle ou S(O)¿2?(1C-4C)alkyle; R?2¿ désigne hydrogène, (1C-4C)alkyle ou C(O)(1C-4C)alkyle; R?3¿ représente un groupe phényle éventuellement substitué par (1C-4C)alkyle, (1C-4C)fluoroalkyle, (1C-4C)alcoxy, (1C-4C)fluoroalcoxy, halogène, cyano ou nitro; ou R?3¿ désigne une structure de noyau hétérocyclique aromatique à 5 ou 6 chaînons éventuellement substituée par (1C-4C)alkyle, (1C-4C)fluoroalkyle, (1C-4C)alcoxy, halogène ou cyano; R?4¿ représente un groupe phényle ou un hétérocycle aromatique à 6 chaînons, substitué à la position ortho par 1-hydroxy(1C-4C)alkyle, (1C-4C)alcoxy, C(O)(1C- 4C)alkyle, CO¿2?(1C-4C)alkyle, C(O)NH¿2?, cyano, nitro, ou CH=NOR?7¿, et éventuellement encore substitué par (1C-2C)alkyle, (1C-2C)fluoroalkyle ou halogène; ou R?4¿ représente 2-pyridyle éventuellement substitué par (1C-2C)alkyle, (1C- 2C)fluoroalkyle ou halogène; R?5¿ et R?6 ¿représentent de manière indépendante hydrogène ou (1C-4C)alkyle; R?7¿ désigne hydrogène ou C(O)(1C-4C)alkyle; et R?8¿, R?9¿, R?10¿ représentent individuellement hydrogène, (1C-2C)alkyle, fluoro ou chloro; ou une forme de sel ou d'hydrate de ceux-ci.

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