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US 5,631,291 AGranted
Cyclopentane- and -pentene-.beta.-amino acids
AssigneeBayer Aktiengesellschaft
InventorsJoachim Mittendorf, Franz Kunisch, Michael Matzke, Hans-Christian Militzer, Rainer Endermann, Karl G. Metzger, Klaus-Dieter Bremm, Manfred Plempel
Life of this patent
Estimating the term…
Abstract
The invention relates to cyclopentane- and -pentene-.beta.-amino acids, processes for their preparation and their use as medicaments.
Claims9
A cyclopentane- or -pentene-.beta.-amino acid compound of the formula (I):
- ##STR124## in which A, B, D, L, M and T are identical or different and, represent hydrogen, halogen, benzyl, hydroxyl or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally monosubstituted or disubstituted by identical or different halogen, hydroxyl, phenyl, benzyloxy, carboxyl, a group of the formula --NR.sup.4 R.sup.5, or by straight-chain or branched alkoxy, acyl or alkoxycarbonyl each having up to 6 carbon atoms;
- in which
- R.sup.4 and R.sup.5 are identical or different and represent hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms;
- E and G together represent a radical of the formula .dbd.CR.sup.6 R.sup.7 ;
- in which
- R.sup.6 and R.sup.7 are identical or different and represent hydrogen, halogen or straight-chain or branched alkyl, alkoxy or oxyacyl each having up to 8 carbon atoms, benzyl or phenyl;
- R.sup.2 represents hydrogen, an amino-protective group, straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally monosubstituted or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, formyl, straight-chain or branched acyl having up to 6 carbon atoms, straight-chain or branched alkyl having up to 6 carbon atoms, or phenyl or benzoyl, each of which is optionally substituted up to 2 times by identical or different substituents selected from the group consisting of halogen, nitro or cyano;
- or R.sup.2 represents straight-chain or branched acyl having up to 8 carbon atoms, benzoyl which is optionally substituted as described above, or a group of the formula --SO.sub.2 R.sup.8, in which
- R.sup.8 represents straight-chain or branched alkyl having up to 8 carbon atoms, or benzyl or phenyl, each of which is optionally substituted up to 3 times by identical or different substituents selected from the group consisting of halogen, hydroxyl, nitro, cyano, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, carboxyl, or --NR.sup.4 R.sup.5 ;
- or R.sup.2 represents phenyl which is optionally substituted up to 3 times by identical or different substituents selected from the group consisting of halogen, hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkyl, acyl, alkoxy or alkoxycarbonyl, each having up to 6 carbon atoms, --NR.sup.4 R.sup.5, or --SO.sub.2 R.sup.8 ;
- or R.sup.2 represents an amino acid radical of the formula --CO--CH(R.sup.9)--NHR.sup.10 ;
- in which
- R.sup.9 represents cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms, hydrogen, or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by a substituent selected from the group consisting of cyano, methylthio, hydroxyl, mercapto, guanidyl, cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms, which is in turn substituted by a substituent selected from the group consisting of hydroxyl, halogen, nitro, alkoxy having up to 8 carbon atoms and a group of the formula --NR.sup.11 R.sup.12, or by a group of the formula --NR.sup.11 R.sup.12 or R.sup.13 --OC--;
- in which
- R.sup.11 and R.sup.12 independently represent hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms or phenyl;
- and
- R.sup.13 represents hydroxyl, benzyloxy, alkoxy having up to 6 carbon atoms or --NR.sup.10 R.sup.11 ;
- and
- R.sup.10 represents hydrogen or an amino-protective group;
- R.sup.3 represents hydrogen or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by phenyl;
- or R.sup.2 and R.sup.3 together represent a radical of the formula .dbd.CHR.sup.14 ;
- in which
- R.sup.14 represents hydrogen or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by a substituent selected from the group consisting of halogen, hydroxyl, phenyl, carboxyl, or straight-chain or branched alkoxy or alkoxycarbonyl each having up to 6 carbon atoms;
- V represents an oxygen or sulphur atom or the --NH group;
- R.sup.1 represents hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted up to 3 times by identical or different substituents selected from the group consisting of hydroxyl, halogen, nitro, cyano, carboxyl, trifluoromethyl, trifluoromethoxy or straight-chain or branched alkoxy, or phenyl, which is optionally substituted up to 3 times by identical or different substituents selected from the group consisting of hydroxyl, halogen, nitro, cyano, carboxyl, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkoxy, alkyl, acyl or alkoxycarbonyl each having up to 6 carbon atoms, --NR.sup.4 R.sup.5 or --SO.sub.2 R.sup.8 ;
- or in the case in which V represents the --NH group, then R.sup.1 may represent --SO.sub.2 R.sup.8 ;
- an isomeric form of said compound, an acid addition salt thereof, or a metal salt complex thereof.
24 more elements
Dependencies are inferred from the claim text.