Patent RU-2600928-C2 (RU)
Inventor: CHZHAN KHeshen
IPC: C07D405/12
Filed: 2011-06-08
Granted: 2016-10-27
Abstract: FIELD: chemistry. 
     SUBSTANCE: invention relates to novel cyanoquinoline derivatives of general formula I, as well as to stereoisomers, cis-trans-isomers or pharmaceutically acceptable salts thereof, where R 1  is selected from a group consisting of 4-bromobut-2-enamide, 4-(dimethylamino)but-2-enamide, acrylamido, but-2-enamide, 3-methylbut-2-enamide, 2-(1-tert-butoxycarbonylpiperidin-4-ylidene) acetamide, 2-(piperidin-4-ylidene)acetamide, 2-(1-methylpiperidin-4-ylidene) acetamide, 2-(1-ethylpiperidin-4-ylidene) acetamide, 2-(1-benzylpiperidin-4-ylidene) acetamide, 2-(1-(2-methoxyethyl) piperidin-4-ylidene)acetamide, 2-(1-(2-methoxycarbonylmethylene)piperidin-4-ylidene)acetamide, 2-(1-isopropylpiperidin-4-ylidene) acetamide, 2-(1-(2-hydroxyethyl)piperidine-4-ylidene)acetamide, 2-(pyrrolidin-3-ylidene)-acetamide, N-(N-(2-(2-(dimethylamino)ethoxy)ethyl)amino)fumaramide, 2-(1-(2-(2-(2-hydroxyethoxy)ethylamino)acetyl) piperidin-4-ylidene)acetamide, 2-((1-methylsulphonyl)piperidin-4-ylidene) acetamide, 4-(piperidin-1-yl)but-2-enamide, 4-(morpholin-4-yl)but-2-enamide, 4-(tert-butylamino)but-2-enamide, 4-(benzylamino)but-2-enamide, 4-(6-hydroxyhexylamino)but-2-enamide, 4-(N-methylbenzylamino)but-2-enamide, 4-(diethylamino)but-2-enamide, 4-(2-methoxyethylamino)but-2-enamide, 4-(diethanolamino)but-2-enamide, 4-(N-methylmethoxyethylamino) but-2-enamide, 4-(N-methyl-ethanolamino)but-2-enamide, 4-(dimethoxyethylamino)but-2-enamide, 4-(N-methyl-6-amino-1-hexanolyl)but-2-enamide and propylamide; one of R 2  and R 3  is H, while other is selected from unsubstituted C 6 -aryl-C 1-2 -alkyl, substituted with 1-2 substitutes or unsubstituted C 6 -aryl and substituted with 1 substitute or unsubstituted 6-9-member heteroaryl, where, when R 2  or R 3  is selected from a substituted C 6 -aryl, substitute is selected from C 2 -C 6 -alkynyl, halogen, C 6 -aryl-C 1 -alkyloxy (where said C 6 -aryl can be substituted with 1 substitute selected from halogen, cyano, C 1 -C 6  alkyl, C 1 -C- 6  alkoxy), and 6-member heteroaryl-C- 1 -alkyloxy, and when R 2  or R 3  are selected from a substituted heteroaryl, substitute is selected from a group comprising C 6 -aryl-C 1 -alkyl (where said C 6 -aryl is optionally substituted with 1 substitute selected from halogen and cyano, methoxy group), C 6 -arylamido (where the said C 6 -aryl can be unsubstituted or substituted with 1 dimethylamino group), C 6 -arylsulphonylamino, C 5 -heteroarylamido, C 6 -cycloalkylamido, C 6 -arylaminocarbonyl (where said C 6 -aryl is substituted with 1 methoxy group), C 6 -aryl-C 1 -alkyloxy and C 6 -aryloxy; or R 2  and R 3 , together with a nitrogen atom to which they are bonded, form a substituted or unsubstituted 9-10-member heterocyclyl, where heterocycyl substitutes are selected from halogen, C 1 -C- 6  alkyl, CF 3 , C 6 -aryl-C 1 -alkoxy, -COOMe, -CH 2 OH and pyrrolyl; and R 4  is substituted with 1 methyl or unsubstituted 5-6-member heterocyclyl or unsubstituted 6-member heteroaryl. Invention also relates to specific compounds, pharmaceutical composition based on compound of formula I and use of formula I. 
     EFFECT: technical result is obtaining novel cyanoquinoline derivatives which are useful in treating tumours. 
     33 cl, 20 tbl, 228 ex