Aminoacid derivatives, a process for their preparation, agents containing these compounds, and the use thereof

A compound of the formula ##STR715## or physiologically tolerated salt thereof, wherein COOR.sub.3 is a) carboxyl,

• b) carboxyl ester and
• R.sub.1 is
• a) alkyl or alkenyl having up to 6 C atoms,
• b) alkyl or alkenyl having up to 6 C atoms substituted by
• 1) (C.sub.5 -C.sub.7)-cycloalkyl,
• 2) (C.sub.5 -C.sub.7)-cycloalkenyl,
• 3) hydroxy,
• 4) (C.sub.1 -C.sub.2)-alkoxy,
• 5) phenoxy,
• 6phenoxy substituted by
• 6.1) halogen,
• 6.2) (C.sub.1 -C.sub.2)-alkyl, or
• 6.3) (C.sub.1 -C.sub.2)-alkoxy,
• 7) naphthyloxy,
• 8) monoalkylamino having up to 7 C atoms,
• 9) monoalkylamino having up to 7 C atoms substituted in the alkyl part by
• 9.1) hydroxy,
• 9.2) carboxy,
• 9.3) carboxamido,
• 9.4) carboethoxy,
• 9.5) amino,
• 9.6) alkylamino,
• 9.7) dialkylamino,
• 9.8) piperidino, or
• 9.9) morpholino,
• 10) dialkylamino having up to 7 C atoms,
• 11) dialkylamino having up to 7 C atoms substituted as defined in b) 9.1-9.9,
• 12) monocycloalkylamino having up to 7 C atoms,
• 13) dicycloalkylamino having up to 7 C atoms,
• 14) alkyloxycarbonylamino,
• 15) phenoxycarbonylamino,
• 16) phenoxycarbonylamino substituted as defined in b) 6.1-6.3,
• 17) naphthyloxycarbonylamino,
• 18) benzyloxycarbonylamino or phenethyloxycarbonylamino,
• 19) benzyloxycarbonylamino or phenethyloxycarbonylamino each substituted in the aryl part by
• 19.1) halogen,
• 19.2) nitro,
• 19.3) (C.sub.1 -C.sub.2)-alkyl, or
• 19.4) (c.sub.1 -C.sub.2)-alkoxy.
• 20) alkylureido,
• 21) phenylureido,
• 22) phenylureido substituted as defined in b) 6.1-6.3,
• 23) naphthylureido,
• 24) benzylureido or phenethylureido,
• 25) benzylureido or phenethylureido each substituted as defined in b) 19.1-19.4,
• 26) formyl,
• 27) alkanoylamino,
• 28) benzoylamino,
• 29) benzoylamino substituted as defined in b) 6.1-6.3,
• 30) naphthoylamino,
• 31) phenylamino or naphthylamino,
• 32) phenylamino or naphthylamino each mono- or di-substituted by
• 32.1) (C.sub.1 -C.sub.2)-alkyl,
• 32.2) (C.sub.1 -C.sub.2)-alkoxy,
• 32.3) methylenedioxy,
• 32.4) amino,
• 32.5) hydroxy,
• 32.6) acetoxy,
• 32.7) carboxy,
• 32.8) carboxamido,
• 32.9) carboethoxy,
• 32.10) halogen, or
• 32.11) nitro,
• 33) benzylamino or phenethylamino,
• 34) benzylamino or phenethyl amino each mono- or di-substituted in the aryl part as defined in b) 32.1-32.11,
• 35) (C.sub.1 -C.sub.7)-alkylmercapto, (C.sub.1 -C.sub.7)-alkylsulfinyl, or (C.sub.1 -C.sub.7)-alkylsulfonyl
• 36) (C.sub.1 -C.sub.7)-alkylmercapto, (C.sub.1 -C.sub.7)-alkylsulfinyl, or (C.sub.1 -C.sub.7)-alkylsulfonyl each substituted by
• 36.1) methoxy,
• 36. 2) ethoxy,
• 36.3) hydroxy,
• 36.4) carboxy,
• 36.5) carboxamido,
• 36.6) carboethoxy,
• 36.7) amino, or
• 36.8) alkylamino,
• 37) phenylmercapto or naphthylmercapto, phenylsulfinyl or naphthylsulfinyl, or phenylsulfonyl or nephthylsulfonyl,
• 38) phenylmercapto or naphthylmercapto, phenylsulfinyl or naphthylsulfinyl, or phenylsulfonyl or naphthylsulfonyl each substituted
• 38.1) as defined in b) 36.1-36.8 or substituted by
• 38.2) halogen,
• 38.3) nitro, or
• 38.4) sulfonamido,
• 39) benzylmercapto, benzylsulfinyl, or benzylsulfonyl,
• 40) benzylmercapto, benzylsulfinyl, or benzylsulfonyl each substituted
• 40.1) in the alkyl part as defined in b) 36.1-36.8 or
• 40. 2) in the aryl part as defined in b) 38.1-38.4,
• 41) carboxy,
• 42) carboethoxy,
• 43) carboxamido,
• 44) alkylaminocarbonyl having up to 6 C atoms,
• 45) cycloalkylaminocarbonyl having up to 6 C atoms,
• 46) cycloalkyleneaminocarbonyl having up to 6 C atoms,
• 47) dialkylaminocarbonyl having up to 6 C atoms,
• 48) phenylaminocarbonyl,
• 49) phenylaminocarbonyl substituted as defined in b) 6.1-6.3,
• 50) naphthylaminocarbonyl,
• 51) benzylaminocarbonyl or phenethylaminocarbonyl,
• 52) benzylaminocarbonyl or phenethylaminocarbonyl each substituted as defined in b) 19.1-19.4,
• 53) guanido,
• 54) phenyl,
• 55) phenyl substituted by
• 55. 1) halogen
• 55.2) hydroxy,
• 55.3) acetoxy,
• 55.4) carboxy,
• 55.5) carboxamido,
• 55.6) sulfonamido,
• 55.7) nitro,
• 55.8) methyl,
• 55.9) ethyl,
• 55.10) methoxy, or
• 55.11) ethoxy,
• 56) naphthyl, dihydronaphthyl, or tetrahydronaphthyl,
• 57) naphthyl, dihydronaphthyl, or tetrahydronaphthyl, each substituted as defined in b) 55.1-55.11,
• 58) imidazol-4-ethyl, or
• 59) indolemethyl,
• c) (C.sub.5 -C.sub.7)-cycloalkyl or (C.sub.5 -C.sub.7)-cycloalkenyl,
• d) phenyl,
• e) naphthyl, dihydronaphthyl, or tetrahydronaphthyl,
• f) imidazol-4-ethyl,
• g) indolemethyl, or
• h) the side-chain of a naturally occurring L-amino acid,
• R.sub.2 is
• a) alkyl or alkenyl having up to 6 C atoms,
• b) alkyl or alkenyl having up to 6 C atoms, substituted by
• 1) (C.sub.5 -C.sub.7)-cycloalkyl,
• 2) (C.sub.5 -C.sub.7)-cycloalkenyl,
• 3) hydroxy,
• 4) (C.sub.1 -C.sub.2)-alkoxy,
• 5) phenoxy,
• 6) phenoxy substituted by
• 6.1) halogen
• 6.2) (C.sub.1 -C.sub.2)-alkyl,
• 6.3) (C.sub.1 -C.sub.2)-alkoxy,
• 6.4) nitro, or
• 7) naphthyloxy,
• 8) benzyloxy,
• 9) benzyloxy substituted in the aryl part by
• 9.1) methoxy,
• 9.2) carboxamido,
• 9.3) amino,
• 9.4) halogen,
• 9.5) nitro, or
• 10) monoalkylamino having up to 7 C atoms,
• 11) monoalkylamino having up to 7 C atoms, substituted in the alkyl part by
• 11.1) hydroxy,
• 11.2) carboxy,
• 11.3) carboxamido,
• 11.4) carboethoxy,
• 11.5) amino,
• 11.6) alkylamino,
• 11.7) dialkylamino,
• 11.8) piperidino, or
• 11.9) morpholino,
• 12) dialkylamino having up to a total of 7 C atoms,
• 13) dialkylamino having up to a total of 7 C atoms substituted as defined in b) 11.1-11.9,
• 14) monocycloalkylamino having up to 7 C atoms,
• 15) dicycloalkylamino having up to 7 C atoms,
• 16) alkoxycarbonylamino,
• 17) phenoxycarbonylamino,
• 18) phenoxycarbonylamino substituted as defined in b) 6.1-6.3,
• 19) nephthyloxycarbonylamino,
• 20) benzyloxycarbonylamino or phenethyloxycarbonylamino,
• 21) benzyloxycarbonylamino or phenethyloxycarbonylamino each substituted in the aryl part by
• 21.1) halogen,
• 21.2) nitro,
• 21.3) (C.sub.1 -C.sub.2)-alkyl, or
• 21.4) (C.sub.1 -C.sub.2)-alkoxy,
• 22) (C.sub.1 -C.sub.10)-alkylureido,
• 23) phenylureido,
• 24) phenylureido substituted as defined in b) 6.1, 6.2, 6.3 or by nitro,
• 25) naphthylureido,
• 26) benzylureido or phenethylureido,
• 27) benzylureido or phenethylureido each substituted as defined in b) 21.1-21.4,
• 28) formyl,
• 29) alkanoylamino,
• 30) benzoylamino,
• 31) benzoylamino mono- to di-substituted by
• 31.1) halogen,
• 31.2) (C.sub.1 -C.sub.2)-alkyl,
• 31.3) (C.sub.1 -C.sub.2)-alkoxy,
• 31. 4) hydroxy,
• 31.5) carboxy,
• 31.6) nitro, or
• 31.7) amino,
• 32) naphthoylamino,
• 33) phenylamino or naphthylamino,
• 34) phenylamino or naphthylamino each mono- or di-substituted by
• 34.1) (C.sub.1 -C.sub.2)-alkyl,
• 34.2) (C.sub.1 -C.sub.2)-alkoxy,
• 34.3) methylenedixoy,
• 34.4) amino,
• 34.5) hydroxy,
• 34.6) acetoxy,
• 34.7) carboxy,
• 34.8) carboxamido,
• 34.9) carboethoxy,
• 34.10) halogen, or
• 34.11) nitro,
• 35) benzylamino or phenethylamino,
• 36) benzylamino or phenethylamino each mono- or di-substituted in the aryl part as defined in b) 34.1-34.11,
• 37) (C.sub.1 -C.sub.7)-alkylmercapto, (C.sub.1 -C.sub.7)-alkylsulfinyl, or (C.sub.1 -C.sub.7)-alkylsulfonyl,
• 38) (C.sub.1 -C.sub.7 )-alkylmercapto, (C.sub.1 -C.sub.7)-alkylsulfinyl, or (C.sub.1 -C.sub.7)-alkylsulfonyl each substituted by
• 38.1) methoxy,
• 38.2) ethoxy,
• 38.3) hydroxy,
• 38.4) carboxy,
• 38.5) carboxamido,
• 38.6) carboethoxy,
• 38.7) amino, or
• 38.8) alkylamino
• 39) phenylmercapto or naphthylmercapto, phenylsulfinyl or naphthylsulfinyl, or phenylsulfonyl or naphthylsulfonyl,
• 40) phenylmercapto or naphthylmercapto, phenylsulfinyl or naphthylsulfinyl, or phenylsulfonyl or naphathylsulfonyl each substituted
• 40.1) as defined in b) 38.1-38.8, or substituted by
• 40.2) halogen,
• 40.3) nitro,
• 40.4) sulfonamido, or
• 41) benzylmercapto, benzylsulfinyl, or benzylsulfonyl,
• 42) benzylmercapto, benzylsulfinyl, or benzylsulfonyl each substituted
• 42.1) in the alkyl part as defined in b) 38.1-38.8 or
• 42.2) in the aryl part as defined in b) 40.1-40.4,
• 43) carboxy,
• 44) alkylaminocarbonyl having up to 6 C atoms,
• 45) cycloalkylaminocarbonyl having up to 6 C atoms,
• 46) cycloalkyleneaminocarbonyl having up to 6 C atoms,
• 47) dialkylaminocarbonyl having up to 6 C atoms,
• 48) phenylaminocarbonyl,
• 49) phenylaminocarbonyl mono- to di-substituted by
• 49.1) halogen,
• 49.2) (C.sub.1 -C.sub.2)-alkyl,
• 49.3) (C.sub.1 -C.sub.2)-alkoxy,
• 49.4) carboxyl,
• 49.5) carboxyamido,
• 49.6) hydroxy, or
• 49.7) nitro,
• 50) naphthylaminocarbonyl,
• 51) benzylaminocarbonyl or phenethylaminocarbonyl,
• 52) benzylaminocarbonyl or phenethylaminocarbonyl each substituted as defined in b) 21.1-21.4,
• 53) guanido,
• 54) naphthyl, dihydronaphthyl, or tetrahydronaphthyl,
• 55) naphthyl, dihydronaphthyl, or tetrahydronaphthyl, each substituted by
• 55.1) halogen,
• 55.2) hydroxy,
• 55.3) acetoxy,
• 55.4) carboxy,
• 55.5) carboxamido,
• 55.6) sulfonamido,
• 55.7) nitro,
• 55.8) methyl,
• 55.9) ethyl,
• 55.10) methoxy, or
• 55.11) ethoxy,
• 56) a 5-membered or 6-membered monocyclic heterocyclic structure, the hetero atoms of which are
• 56. 1) 1 or 2 S atoms or 1 O atom and 0 or 1 N atom or
• 56.2) up to 4N atoms
• 57) a heterocycle as defined in b) 56 substituted by
• 57.1) halogen,
• 51.2) oxo,
• 57.3) S-oxo,
• 57.4) hydroxy,
• 57.5) carboxy,
• 57.6) carboxamido,
• 57.7) sulfonamido,
• 57.8) nitro,
• 57.9) (C.sub.1 -C.sub.9)-alkyl,
• 57.10) benzyl or phenethyl,
• 57.11) methoxy,
• 57.12) ethoxy, or
• 58) a 9-membered or 10-membered bicyclic heterocyclic structure, the hetero atoms of which are 2 O atoms or 1 or 2 N atoms or
• 59) a heterocycle as defined in b) 58 substituted as defined in b) 57.1-57.12,
• 60) phenyl or
• 61) phenyl mono- to di-substituted by
• 61.1) halogen,
• 61.2) hydroxy,
• 61.3) acetoxy,
• 61.4) carboxy,
• 61.5) carboxamido,
• 61.6) sulfonamido,
• 61.7) nitro,
• 61.8) methyl,
• 61.9) ethyl,
• 61.10) methoxy,
• 61.11) ethoxy, or
• c) (C.sub.5 -C.sub.7)-cycloalkyl- or cycloalkenyl,
• d) naphthyl, dihydronaphthyl, or tetrahydronaphthyl,
• e) a 5-membered or 6-membered monocyclic heterocyclic structure, the hetero atoms of which are
• 1) 1 or 2 S atoms or 1O atom and 0 or 1 N atom or
• 2) up to 4 N atoms,
• f) a heterocycle as defined in e) substituted by
• 1) halogen,
• 2) oxo,
• 3) S oxo,
• 4) hydroxy,
• 5) carboxy,
• 6) carboxamido,
• 7) sulfonamido,
• 8) nitro,
• 9) (C.sub.1 -C.sub.9)-alkyl,
• 10) benzyl or phenethyl,
• 11) methoxy, or
• 12) ethoxy,
• g) a 9-membered or 10-membered bicyclic heterocyclic structure, the hetero atoms of which are 2 O atoms or 1 or 2 N atoms or
• h) a heterocycle as defined in g) substituted as defined in f) 1-12,
• i) phenyl.