Patent ID: 6114349
Filing Date: 2000-09-05
Classification: A61K,A61P,C07D

Abstract:
A compound of the formula I ##STR117## or a tautomeric form thereof, of the formula Ia ##STR118## in which: I) n is zero, one, two, three, or four,the individual substituents R.sup.1 independently of one another are fluorine, chlorine, bromine, iodine, 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, sulfamoyl, ora phenyl, phenoxy, phenoxycarbonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenoxysulfonyl, phenylsulfonyloxy, anilinosulfonyl, phenylsulfonylamino, benzoyl, heteroaroyl, heteroaryl or heteroarylmethyl radical, each of which is unsubstituted or substituted by up to five radicals R.sup.6 which are independent of one another,where R.sup.6 isfluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, azido, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkyloxycarbonyl, phenyl, phenoxy or heteroaryl,X is oxygen, sulfur, selenium or substituted nitrogen N--R.sup.2, N--O--R.sup.2, in which R.sup.2 has the meanings given below,and R.sup.2 is hydrogen,alkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkenyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkynyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;cycloalkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;(cycloalkenyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;(cycloalkyl)-(alkyl), which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;(cycloalkenyl)-(alkyl), which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkylcarbonyl, which is unsubstituted or substituted by fluorine, chlorine , bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkenylcarbonyl, which is unsubstituted or substituted by fluorine, chlorine or hydroxyl, alkoxy, oxo, phenyl;(cycloalkyl) carbonyl, which is unsubstituted or substituted by fluorine, chlorine or hydroxyl, alkoxy, oxo, phenyl;(cycloalkenyl)carbonyl, which is unsubstituted or substituted by fluorine, chlorine or hydroxyl, alkoxy, oxo, phenyl;(cycloalkyl)-(alkyl)carbonyl, which is unsubstituted or substituted by fluorine, chlorine or hydroxyl, alkoxy, oxo, phenyl;(cycloalkenyl)-(alkyl)carbonyl, which is unsubstituted or substituted by fluorine, chlorine or hydroxyl, alkoxy, oxo, phenyl;alkyloxycarbonyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, hydroxyl, alkoxy, alkylamino, dialkylamino, alkylthio;alkenyloxycarbonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkynyloxycarbonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkylthiocarbonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkenylthiocarbonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkylamino- or dialkylaminocarbonyl, each of which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkenylamino- or dialkenylaminocarbonyl, each of which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;alkylsulfonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, alkylthio, oxo, phenyl;alkenylsulfonyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, alkoxy, oxo, phenyl;or aryl, arylcarbonyl, aryl(thiocarbonyl), (arylthio)carbonyl, (arylthio)thiocarbonyl, aryloxycarbonyl, (arylamino)thiocarbonyl, arylsulfonyl, arylalkyl, arylalkenyl, aralkynyl, arylalkylcarbonyl, arylalkenylcarbonyl, arylalkoxycarbonyl, each of which is unsubstituted or substituted by up to five radicals R.sup.6 which are independent of one another, where R.sup.6 is as defined above;or heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkylcarbonyl or heteroarylalkenylcarbonyl, each of which is substituted by up to three radicals R.sup.6 which are independent of one another, where R.sup.6 is as defined above, andR.sup.3 is hydrogen,alkyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl, carbamoyl;alkenyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl, carbamoyl;cycloalkyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl, carbamoyl;cycloalkenyl, which is unsubstituted or substituted by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl, carbamoyl;or aryl, arylalkyl, heteroaryl or heteroarylalkyl, each of which is unsubstituted or substituted by up to five radicals R.sup.6 which are independent of one another, where R.sup.6 is as defined above,and R.sup.4 is oxygen, sulfur, NOR.sup.2, NOH, where R.sup.2 is as defined above,or R.sup.4 is an alkyl radical bonded via a double bond, which is unsubstituted or substitute by fluorine, chlorine, hydroxyl, amino, mercapto, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, alkylsulfinyl, carboxyl, carbamoyl,or R.sup.4 is two hydrogen atoms residing on the linking carbon atom, where in this case R.sup.5 additionally to the definitions indicated below for R.sup.5 this radical can also be hydrogen or alkylcarbonyl,and in whichm is 1,and R.sup.5 isalkyl, which is substituted by at least one fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkenyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;alkynyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;cycloalkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;cycloalkenyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;(cycloalkyl)-(alkyl), which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;(cycloalkenyl)-(alkyl), which is unsubstituted or substituted by fluorine, chlorine, bromine, iodine, cyano, amino, mercapto, hydroxyl, acyloxy, benzoyloxy, benzyloxy, phenoxy, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, phenylsulfonyl, oxo, thioxo, carboxyl, carbamoyl;or arylalkyl, arylalkenyl, arylalkynyl, each of which is unsubstituted or substituted by up to five radicals R.sup.6 which are independent of one another, where R.sup.6 is as defined above;or aryl which is substituted by up to five radicals R.sup.6 which are independent of one another, where R.sup.6 is defined above,or heteroaryl, heteroarylalkyl, heteroarylalkenyl, which is unsubstituted or substituted by up to three radicals R.sup.6 which are independent of one another, where R.sup.6 is as defined above,or an optical isomer, a diastereomer in pure form, or a mixture of diastereomers in pure form, or an addition salt thereof,with the exception of a compound of the formula I in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and m simultaneously have the following meanings:R.sup.2 is hydrogen,R.sup.3 is phenyl, which is unsubstituted or substituted as indicated above,X is oxygen,R.sup.4 is oxygen,m is 1 andR.sup.5 is C.sub.1 -C.sub.6 -alkylfurthermore with the exception of a compound of the formula I in whichR.sup.1 and R.sup.2 are hydrogen,R.sup.3 is hydrogen, methyl or ethyl,R.sup.4 is oxygen andR.sup.5 is methyl,furthermore with the exception of a compound of the formula I in whichR.sup.1 is hydrogen,R.sup.2 is C.sub.1 -C.sub.4 -alkyl,R.sup.3 is phenyl, which is unsubstituted or substituted as indicated above,R.sup.4 is 0,m is 1,X is 0 andR.sup.5 is methyl, ethyl,furthermore with the exception of a compound of the formula I in whichR.sup.1 and R.sup.2 are hydrogen,R.sup.3 is ethenyl,R.sup.4 is 0,m is 1,X is 0 andR.sup.5 is methyl, ethyl, andfurthermore with the exception of a compound of the formula Ia in whichR.sup.1 and R.sup.2 are hydrogen,R.sup.3 is ethyl,R.sup.4 is 0,m is 1,X is 0 andR.sup.5 is methyl.