Patent EA-004701-B1 (EA)
Title: Anthranilic acid amides and the use thereof as medicaments
Inventor: HUTH ANDREAS
IPC: A61P9/10
Filed: 1999-11-09
Abstract: 1. Compounds of general formula I in which A stands for the group =NR<2>-, W stands for oxygen; Z stands for the group or A, Z and R<1> together form the group m, n and o stand for 0-3, Ra, Rb, Rc, Rd, Re, Rf, independently of one another, stand for hydrogen, methyl, X stands for the group =NR<9>, Y stands for the group -CH2, R<1> stands for phenyl, pyridyl, 5chloro-2,3-dihdyroindenyl, 2,3-dihydroindenyl, thienyl, 6-fluoro-1H-indol-3-yl, naphthyl, 1,2,3,4-tetrahydronaphthyl, benzo-1,2,5-oxadiazole, 6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthyl or substituted in one or more places with halogen, C1-6 alkyl, C1-4alkoxy-, hydroxy-, trifluoromethyl phenyl or pyridyl, or for the group whereby phenyl, substituted phenyl or naphthyl is not right in the =NR<2> group in the meaning of A, R<2> stands for hydrogen or methyl, R<3> stands for optionally substituted in one or more places with halogen; C1-6alkyl, C1-6alkoxy or hydroxy phenyl, pyridyl or pyrimidinyl, or for the group R<4>, R<5>, R<6>, and R<7>, independently of one another, stand for hydrogen, halogen, or C1-6alkoxy, C1-6alkyl or C1-6carboxylalkyl that is unsubstituted or optionally substituted in one or more places with halogen, or R<5> and R<6> together form the group R<8>, R<9>, and R<10>, independently of one another, stand for hydrogen or C1-6alkyl, as well as their isomers and salts, whereby if R<2> stands for hydrogen, R<9> stands for hydrogen, Y stands for the group -CH2-, and R<1> stands for pyridyl, or if R<1> stands for phenyl or phenyl that is substituted in one place by methyl, chlorine or bromine, and Z stands for methyl or ethyl, then R<3> must not stand for pyridyl, phenyl or phenyl that is substituted in one place by methyl, chlorine or bromine. 2. Compounds of general formula I, according to claim 1, in which A stands for the group =NR<2>, W stands for oxygen, Z stands for the group A, Z and R<1> together form the group m, n, and o stand for 0-3, Ra, Rb, Rc, Rd, Re, Rf, independently of one another, stand for hydrogen, methyl, X stands for the group =NR<9>, Y stands for the group -CH2, R<1> stands for phenyl, pyridyl, 5chloro-2,3-dihdyroindenyl, 2,3-dihydroindenyl, thienyl, 6-fluoro-1H-indol-3-yl, naphthyl, 1,2,3,4-tetrahydronaphthyl, benzo-1,2,5-oxadiazole, 6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthyl or substituted in one or more places with halogen, C1-6 alkyl, C1-4alkoxy-, hydroxy-, trifluoromethyl phenyl or pyridyl, or for the group whereby phenyl, substituted phenyl or naphthyl is not right in the =NR<2> group in the meaning of A, R<2> stands for hydrogen or methyl, R<3> stands for pyridyl or optionally substituted in one or more places with halogen methyl or methoxy phenyl or pyridyl, or for the group or R<5> and R<6> independently of one another, stand for hydrogen, halogen, methyl, methoxy group or trifluoromethyl, R<4> and R<7>, independently of one another, stand for hydrogen or halogen, R<9> stands for hydrogen, R<10> stands for hydrogen or methyl, as well as their isomers and salts, whereby if R<2> stands for hydrogen, R<1> stands for phenyl or phenyl that is substituted in one place by methyl, chlorine or bromine, and Z stands for methyl or ethyl, then R<3> must not stand for pyridyl or phenyl that is substituted in one place by methyl, chlorine or bromine. 3. Use of the compounds of formula I according to claim 1or 2 for the production of a pharmaceutical agent as inhibitors of tyrosine kinases KDR and FLT as inhibitors of tyrosine kinases KDR and FLT. 4. Pharmaceutical agent that contains at least one compound according to any one of claims 1 or 2. 5. Pharmaceutical agent according to claim 4 for inhibiting of tyrosine kinases KDR and FLT. 6. Compounds according to any one of claims 1 or 2 and pharmaceutical agents according to claims 4 and 5 with suitable formulations and vehicles for the production of corresponding compositions. 7. Use of the compounds of formula I according to claim 1or 2 as inhibitors of tyrosine kinases KDR and FLT. 8. Use of the compounds of general formula I according to any one of claims 1 or 2 in the form of a pharmaceutical preparation for enteral, parenteral and oral administration.