Patent NZ-521088-A (NZ)
Title: Substituted 1,2,3,4- tetrahydroquinoline-2-carboxylic acid derivatives their preparation and medicinal uses
Inventor: REISSMULLER ELKE
IPC: A61P13/02
Filed: 2001-01-19
Abstract: Substituted 1,2,3,4-tetrahydroquinoline-2-carboxylic acid derivatives of formula (I) in the form of a racemate; enantiomer, diastereomer, a mixture of enantiomers or diastereomers or of an individual enantiomer or diastereomer; a base or a salt of physiologically tolerated acid that are useful in the treatment of neuropathic or chronic pain or migraine are disclosed, wherein: R1 and R2 together, respectively singly or multiply substituted or unsubstituted form -(CH2)n- with n= 3-10, -CH=CH-CH2-, -CH=CH-CH2-CH2-, -CH2-CH=CH-CH2-, -CH2-CH=CH-CH2-CH2-, -CH2-CH2-CH=CH-CH2-CH2-, -O-CH2-CH2-, -0-CH2-CH2-CH2-, -CH2-O-CH2-, -CH2-CH2-O-CH2-, or substituents having ring structures as described in the specification; R3 is H; branched or unbranched, singly or multiply substituted or unsubstituted C1-C18 alkyl, C2-C18 alkenyl or C2-C18 alkynyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C3-C8 cycloalkyl, or a corresponding heterocycle, in which at least one carbon atom in the ring is replaced by N, S or O, alkyl aryl or alkyl heteroaryl, each singly or multiply substituted or unsubstituted; aryl or heteroaryl; in each case singly or multiply substituted or unsubsti-tuted; R5, R6, R7 and R8, independently of one another, are selected from H, F, CI, Br, I, CN, NO2; respectively branched or unbranched, singly or multiply substituted or unsubstituted C1-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl; OR14, OC(O)R14, OC(S)R14, C(O)R14, C(O)OR14, C(S)R14, C(S)OR14, SR14, S(O)R14 or S(O2)R14, NR15R16, NR15C(O)R16, C(NR15)NR16R17, NR15C(S)R16, C(S)NR15R16 or C(S)NR15NR16R17 or S(O2)NR15R16; R14 is selected from H; respectively branched or unbranched, singly or multiply substituted or unsubstituted C1-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C3-C8 cycloalkyl, or a corresponding heterocycle, in which at least one carbon atom in the ring is replaced by S, O or N; respectively singly or multiply substituted or unsubstituted alkyl aryl or alkyl heteroaryl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; R15, R16 and R17, independently of one another, are selected from H, 0; respectively branched or unbranched, singly or multiply substituted or unsubstituted C1-C18 alkyl, C2-C18 alkenyl or C2-C18 alkynyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C3-C8 cycloalkyl, or a corresponding heterocycle, in which at least one carbon atom in the ring is replaced by S, O or N, respectively singly or multiply substituted or unsubstituted alkyl aryl or alkyl heteroaryl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or R15 and R16 or R16 and R17 together form a saturated or unsaturated, singly or multiply substituted or unsubstituted C3-C8 cycloalkyl, or a corresponding heterocycle in which at least one carbon atom in the ring is replaced by S, O or N; or R5 and R6, R6 and R7 or R7 and R8 jointly form =CR18-CH=CH-CH= or =CH-CR18=CH-CH=; R18 is selected from H, F, CI, Br, I, OH or respectively branched or unbranched, singly or multiply substituted or unsubstituted C1-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl; with the proviso that if R1 and R2 together form -CH=CH-CH2- or a substituent having a ring structure as described in the specification and R3 corresponds to a saturated or unsaturated C3-C8 cycloalkyl, (-)p-menthan-3-ol, menthol or borneol, R7 = CI and R5, R6 and R8 = H do not simultaneously apply; if R1 and R2 together form -CH=CH-CH2- and R3 corresponds to CH3, R7 = H, CI or OCH3 and R5, R6 and R8 = H do not simultaneously apply, if R1 and R2 together form -CH=CH-CH2- and R3 corresponds to H, R7 = OCH or C(O)NH2 and R5, R6 and R8 = H, R5 and R7 = CH3 and R6 and R8 = H or R5 = OCH3 and R6, R7 and R8 = H do not simultaneously apply; if R1 and R2 together form a ring structure as described in the specification or -O-CH2-CH2- and R3 corresponds to C2H5, R7 = H, CI, CH3, OCH3 or NO2 and R5, R6 and R8 = H or R5 = NO2 and R6, R7 and R8 = H do not simultaneously apply.