C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
167/208, 260/324
C07D 207/26 (2006.01) A61K 31/395 (2006.01) C07D 207/27 (2006.01) C07D 277/02 (2006.01) C07D 277/14 (2006.01) C07D 277/16 (2006.01) C07D 277/20 (2006.01) C07D 277/34 (2006.01) C07D 277/36 (2006.01) C07D 327/04 (2006.01) C07D 417/04 (2006.01) C07D 417/06 (2006.01)
Patent
CA 2013599
i ABSTRACT OF THE DISCLOSURE Provided by the present invention are certain aryl-substituted rhodanine derivatives and pharmaceutically acceptable salts thereof, processes for preparing same, treatment methods and pharmaceutical formulations thereof. The aryl-substituted rhodanine derivatives are of the following generic formula (I): Image wherein: R1 and R2 are each independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy or -C1-C4 Image R3 is hydrogen or C1-C6 alkyl; R4 and R5 are each hydrogen, or when taken together form a bond; R6 and R7 are each hydrogen or when taken together are =S, or when one of R6 or R7 is hydrogen, the other is -OH or -SCH3; X is Image where m is 0, 1 or 2; and Q is -CH2-, -O- or NR8 where R8 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C2-C6 alkenyl, -SO2CH3 or -(CH2)n-Y, where n is an integer from 0 to 3, both ii inclusive, and Y is cyano, OR9, Image , tetrazolyl, -NR11R12, -SH, -S(C1-C4 alkyl) or Image where R9 is hydrogen, C1-C4 alkyl, tosyl or Image alkyl; R10 is C1-C4 alkyl, C1-C4 alkoxy or -NH2; R11 and R12 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -(CH2)qOH, -(CH2)q-N(C1-C4 alkyl)2, -(CH2)q-S(C1-C4 alkyl) or Image where q is an integer from 1 to 6, both inclusive, and n is as defined above; or R11 and R12 taken together form a morpholinyl, piperidinyl, piperazinyl or an N-methyl-piperazinyl ring; with the proviso that when Q is -O- or NR8 (R8 is hydrogen or C1-C4 alkyl), R3 is hydrogen, R4 and R5 are each hydrogen or when taken together form a bond, R4 and R7 are each hydrogen or when taken together are =S and X is iii Image (where m is O), R1 and R2 cannot both be a t-butyl group ; and when Q is NR8 (R8 is hydrogen), R3 i s hydrogen, R6 and R7 taken together are =S and X is -S(O)m - (where m is O), R4 and R5 must both be hydrogen; and when Q is NR8 [R8 is hydrogen or - (CH2) n-Y, where n is O and Y is CO (C1-C4 alkyl), R3 is hydrogen, R4 and R5 taken together form a bond, R6 and R7 are each hydrogen and X is -S (O)m - (where m is O) , R1 and R2 cannot both be an isopropyl group; and when Q is NR8 [R8 is (CH2) n Y, where n is 1 and Y is NR11R12, where one of R11 and R12 is hydrogen and the other is (CH2) n Image where n is 1] , R3 is hydrogen, R4 and R5 taken together forms bond, R6 and R7 taken together are =S, X is -S (O) m- (where m is O) , one of R1 and R2 cannot be hydrogen.
Eli Lilly And Company
Gowling Lafleur Henderson Llp
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