4-substituted amino-ethylene-phenol compounds

C - Chemistry – Metallurgy – 07 – D

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C07D 215/22 (2006.01) C07C 43/174 (2006.01) C07C 43/23 (2006.01) C07C 45/51 (2006.01) C07C 65/24 (2006.01) C07C 275/28 (2006.01) C07C 323/25 (2006.01) C07D 215/227 (2006.01) C07D 215/26 (2006.01) C07D 263/14 (2006.01) C07D 319/08 (2006.01)

Patent

CA 1258459

-1- Abstract There are Provided compounds of formula I Image in which R1 represents NR11R21, CH2R12, or fluorine, when R1 represents CH2R12 or fluorine, R2 and R3, which may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, alkyl C1 to 6, nitro, nitrile, (CH2)pRg or SR9, when R1 represents NR11R21, R11 represents hydrogen, CHO, COR13, COOR13, CONH2, SO2R13, CH2R14 or alky. C1 to 6 and R21 represents hydrogen and R2 and R3 are as defined above, or R11 and R2 together form the chain =CR23-CH=CH- in which the carbon bearing R23 is adjacent to the nitrogen, R23 represents hydrogen or hydroxy, R3 is as defined above and R21 has no meaning, or R11 and R2 together form the chain -COCH2- in which -CO- is adjacent to the nitrogen, R3 is as defined above and R21 represents hydrogen, or R11 and R2 together represent 1,2-phenylene, R3 -2- is as defined above, and R21 represents hydrogen, R12 represents hydrogen, OH, SO2R13 or alkyl C1 to 6, R13 represents alkyl C1 to 6, R14 represents phenyl or alkoxy C1 to 6 phenyl, W represents a single bond, a 1,2-, 1,3- or 1,4-phenylene; a -CH=CH-group or a 1,4-cyclohexanediyl group; X represents NH, O, S, SO2, CO, CH2, CONH or -COO; Y represents (CH2)q, CO, CS, SO2 and R20 represents hydrogen, or Y represents CR15R16CR17R18, wherein the carbon atom bearing R15 and R16 is adjacent to X and in which R17 and R18, together with the carbon atom to which they are attached form a carbonyl group, and R15, R16 and R20 each represent hydrogen, or R15 and R20 together form a chain -CH2-, and R16, R17 and R18 each represent hydrogen, or R15, R16, R17 and R18 each independently represent hydrogen or alkyl C1 to 6 and R20 represents hydrogen; Z represents a single bond, NR19, CH2, O, CO, S or SO2, in which R19 represents hydrogen or alkyl C1 to 6; -3- n, and m each independently represent an integer from 1 to 4 inclusive; q represents an integer from 1 to 3 inclusive; p represents 0 or an integer from 1 to 3 inclusive; R9 represents phenyl or phenyl substituted by hydroxy, and R10 represents hydrogen or chlorine, provided that i) when X represents SO2, CO, COO or CONH, then Y does not represent CO, CS or SO2; ii) when Y represents CO, CS or SO2, then Z does not represent CO or SO2, and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

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