Patent IL-106147-A (IL)
Title: 4-iminoquinolines, processes for their preparation, and pharmaceutical compositions containing them
IPC: C07D401/06
Filed: 1993-06-25
Abstract: Anti-viral compounds of the formula (R1)nR2 NXR3R4 NY (I) or a tautomeric form thereof, of the formula Ia, Ib or Ic R2NX (R1)nR3 R4NY (Ia) (R1)n R2NXR3 NHY (R1)nNX R2R3 NHY (I b)(I c) in which: n is 0-4, R1 independently of one another are halogen, trifluoromethyl, trifluoromethoxy, hydroxyl, alkyl, cycloalkyl, alkoxy, alkoxy (alkoxy), alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, amino, azido, alkylamino, dialkylamino, piperidino, morpholino, 1-pyrrolidinyl, acyl, acyloxy, acylamino, cyano, carbamoyl, carboxyl, alkyloxycarbonyl, hydroxysulfonyl or sulfamoyl or a phenyl, phenoxy, phenoxycarbonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenoxysulfonyl, phenyl-sulfonyloxy, anilinosulfonyl, phenylsulfonylamino, benzoyl, heteroaroyl, heteroaryl or heteroarylmethyl radical which is optionally substituted by up to five radicals R5 which are independent of one another, in which R5 can be halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, azido, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino, dialkylamino, alkyloxycarbonyl, phenyl, phenoxy or heteroaryl, X is oxygen, sulfur, selenium or substituted nitrogen N-R2 or N-O-R2, in which R2 can have the meanings given below, Y is R6, O-R6, S-R6, N-R6R7, N=C-R6R7 or C-R6R7R8, in which R6, R7 and R8 can have the meanings given below, R2, R6, R7 and R8 can be identical or different and can be, independently of one another hydrogen, an alkyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenyl alkyl or an alkylcarbonyl group each of those groups being optionally substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl or carbamoyl; an alkenylcarbonyl, (cycloalkyl) carbonyl, (cycloalkenyl) carbonyl, (cycloalkyl) - (alkyl) carbonyl, or (cycloalkenyl) - (alkyl) carbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkylthiocarbonyl, alkenylthiocarbonyl, alkylamino- or dialkylaminocarbonyl, alkenylamino- or dialkenylaminocarbonyl, alkenylsulfonyl group all these groups being is optionally substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo or phenyl; an alkylsulfonyl, which is optionally substituted by fluorine, chlorine, hydroxyl, alkoxy, alkythio, oxo or phenyl; an alkyloxycarbonyl, which is optionally substituted by fluorine, cholorine, bromine, hydroxyl, alkoxy, alkylamino, dialkylamino or alkylthio; or aryl, arylcarbonyl, aryl (thiocarbonyl), (arylthio)-carbonyl, (arylthio) thiocarbonyl, aryloxycarbonyl, (arylamino) thiocarbonyl, arylsulfonyl, arylalkyl, aryl-alkenyl, arylalkynyl, arylalkylcarbonyl, arylalkenyl- carbonyl or arylalkoxycarbonyl, which are substituted by up to five radicals R5 which are independent of one another, in which R5 is as defined above; or heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkylcarbonyl or heteroarylalkenylcarbonyl, which are substituted by up to three radicals R5 which are independent of one another, and R3 and R4 are indentical or different and independently are hydrogen, an alkyl, alkenyl, cycloalkyl, or cycloalkenyl group all these groups being optionally substituted by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl or carbamoyl; or an aryl, arylalkyl, heteroaryl or heteroarylalkyl group, which in substituted by up to five radicals R5 or R3 and R4 together can also be a radical =C-Z1Z2 linked via a double bond, in which Z1 and Z2 have the meaning given above for R3 and R4, or an optical isomer thereof, a diastereomer in the pure form or in the form of a mixture of diastereomers, or an addition salt or prodrug thereof, with the exception of the compounds in which, simultaneously, R3 and/or R4 are hydrogen and Y is R6 or CR6R7R8.