Patent EP-0046953-A2 (EP)
Inventor: GEIGER ROLF PROF DR
IPC: C07D209/42
Filed: 1981-08-22
Abstract: 1. Claims for the Contracting States : BE, DE, GB, FR, IT, LU, LI, CH, NL, SE A compound of the formula I'  see diagramm : EP0046953,P38,F1  in which R1 and R2 are identical or different and denote a) alkyl or alkenyl having up to 6 C atoms, each of which may be substituted by one or more identical or different substituents from the series comprising 1. (C5 -C7 )-cycloalkyl, 2. (C5 -C7 )-cycloalkenyl, 3. fluorine, 4. mercapto, 5. hydroxyl, 6. (C1 -C2 ) -alkoxy which may be substituted in the alkyl moiety by 6.1 methoxy, 6.2 ethoxy, 6.3 carboxyl, 6.4 carbamoyl, 6.5 amino or 6.6 (C1 -C6 )-alkylamino, 7. aryloxy which may be substituted by the radicals stated under a) 6.1 - 6.6 or by 7.1 halogen and/or 7.2 nitro, 8. aralkyloxy having 1 or 2 C atoms in the alkyl moiety, which may be substituted in the alkyl moiety as described under a) 6.1 - 6.6 and which may be substituted in the aryl moiety as described above for the alkyl moiety or as described under a) 7.1 or 7.2, 9. amino, 10. monoalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical by 10.1 hydroxyl, 10.2 carboxyl, 10.3 carbamoyl, 10.4 ethoxycarbonyl, 10.5 amino, 10.6 (C1 -C6 )-alkylamino, 10.7 di-(C1 -C6 )-alkylamino, 10.8 piperidino or 10.9 morpholino, 11. dialkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 12. cycloalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 13. dicycloalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 14. (C1 -C6 )-alkoxycarbonylamino, 15. aryloxycarbonylamino which may be monosubstituted or disubstituted in the aryl moiety by 15.1 (C1 -C2 )-alkyl, 15.2 (C1 -C2 )-alkoxy, 15.3 methylenedioxy, 15.4 amino, 15.5 hydroxyl, 15.6 acetoxy, 15.7 carboxyl, 15.8 carbamoyl, 15.9 ethoxycarbonyl, 15.10 halogen or 15.11 nitro, 16. aralkyloxycarbonylamin which may be substituted in the aryl moiety as described under a) 15.1 - 15.11, 17. (C1 -C6 )-alkylureido, 18. arylureido which may be monosubstituted or disubstituted in the aryl moiety by identical or different radicals as described under a) 15.1 - 15.11, 19. aralkylureido which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 20. formyl, 21. alkanoylamino having up to 10 C atoms, 22. aroylamino having up to 10 C atoms, which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 23. aralkanoylamino having up to 10 C atoms, which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 24. arylamino which may be monosubstituted or disubstituted in the aryl moiety by identical or different radicals as described under a) 15.1 - 15.11, 25. aralkylamino which may be substituted in the aryl moiety as described under a) 15.1 - 15.11, 26. alkylmercapto, alkylsulfinyl or alkylsulfonyl having up to 7 C atoms, each of which may be substituted in the alkyl moiety by 26.1 methoxy, 26.2 ethoxy, 26.3 hydroxyl, 26.4 carboxyl, 26.5 carbamoyl, 26.6 ethoxycarbonyl, 26.7 amino or 26.8 (C1 -C6 )-alkylamino, 27. phenylmercapto, phenylsulfinyl or phenylsulfonyl, which may be substituted in the aryl moiety as described under a) 26.1 - 26.8 or by 27.1 halogen, 27.2 nitro or 27.3 sulfamoyl, 28. benzylmercapto, benzylsulfinyl or benzylsulfonyl, which may be substituted in the alkyl moiety as described under a) 26.1 - 26.8 and which may be substituted in the aryl moiety as for the above alkyl moiety or as described under a) 27.1 - 27.3, 29. carboxyl, 30. ethoxycarbonyl, 31. carbamoyl, 32. alkylaminocarbonyl having up to 6 C atoms, 33. cycloalkylcarbamoyl having up to 6 C atoms, 34. cycloalkyleneaminocarbonyl having up to 6 C atoms, 35. dialkylcarbamoyl having up to 6 C atoms, 36. arylcarbamoyl which may be substituted in the aryl moiety by 36.1 halogen, 36.2 (C1 -C6 )alkyl or 36.3 (C1 -C6 )-alkoxy, 37. aralkylcarbamoyl, 38. guanidino, 39. phenyl, naphthyl, dihydronaphthyl or tetrahydronaphthyl, each of which may be monosubstituted or disubstituted by 39.1 halogen, 39.2 hydroxyl, 39.3 acetoxy, 39.4 carboxyl, 39.5 carbamoyl, 39.6 sulfamoyl, 39.7 nitro, 39.8 methyl, 39.9 ethyl, 39.10 methoxy and/or 39.11 ethoxy, 40. a 5-membered to 7 membered monocyclic or 9 membered or 10-membered bicyclic heterocyclic radical which may contain 1 or 2 S or O atoms and/or up to 4 N atoms per ring and which may be substituted by 40.1 halogen, 40.2 oxygen, 40.3 hydroxyl, 40.4 carboxyl, 40.5 carbamoyl, 40.6 sulfamoyl, 40.7 nitro, 40.8 alkyl having up to 9 C atoms, 40.9 aralkyl having up to 9 C atoms, 40.10 methoxy and/or 40.11 ethoxy ; b) denote cycloalkyl or cycloalkenyl, each having 5 - 7 C atoms ; c) denote aryl or partially hydrogenated aryl ; or d) denote a monocyclic or bicyclic heterocyclic radical having 5 - 7 or 8 - 10 members, including 1 or 2 -S- or -O- and/or up to 4 N atoms, which radical may be substituted as described under a) 40.1 - 40.11, and R3 denotes hydrogen, alkyl having 1 to 6 C atoms, alkenyl having 2 to 6 C atoms, aralkyl having 7 to 14 C atoms, including p-nitrobenzyl, and, unless specifically defined otherwise, aryl has 6 to 10 C atoms and may be substituted by halogen, (C1 -C6 ) -alkyl or (C1 -C6 )-alkoxy, and denotes aralkyl, benzyl or phenethyl and may be substituted by halogen, (C1 -C6 )-alkyl or (C1 -C6 )-alkoxy in the phenyl nucleus, or their physiologically tolerated salts. 1. Claims for the Contracting State : AT A process for the preparation of a compound of the formula I'  see diagramm : EP0046953,P42,F3  in which R1 and R2 are identical or different and denote a) alkyl or alkenyl having up to 6 C atoms, each of which may be substituted by one or more identical or different substituents from the series comprising 1. (C5 -C7 )-cycloalkyl, 2. (C5 -C7 )-cycloalkenyl, 3. fluorine, 4. mercapto, 5. hydroxyl, 6. (C1 -C2 )-alkoxy which may be substituted in the alkyl moiety by 6.1 methoxy, 6.2 ethoxy, 6.3 carboxyl, 6.4 carbamoyl, 6.5 amino or 6.6 (C1 -C6 )-alkylamino, 7. aryloxy which may be substituted by the radicals stated under a) 6.1 - 6.6 or by 7.1 halogen and/or 7.2 nitro, 8. aralkyloxy having 1 or 2 C atoms in the alkyl moiety, which may be substituted in the alkyl moiety as described under a) 6.1 - 6.6 and which may be substituted in the aryl moiety as described above for the alkyl moiety or as described under a) 7.1 or 7.2, 9. amino, 10. monoalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical by 10.1 hydroxyl, 10.2 carboxyl, 10.3 carbamoyl, 10.4 ethoxycarbonyl, 10.5 amino, 10.6 (C1 -C6 )-alkylamino, 10.7 di-(C1 -C6 )-alkylamino, 10.8 piperidino or 10.9 morpholino, 11. dialkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 12. cycloalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 13. dicycloalkylamino having up to 7 C atoms, which may be substituted in the alkyl radical as described under a) 10.1 - 10.9, 14. (C1 -C6 )-alkoxycarbonylamino, 15. aryloxycarbonylamino which may be monosubstituted or disubstituted in the aryl moiety by 15.1 (C1 -C2 )-alkyl, 15.2 (C1 -C2 )-alkoxy, 15.3 methylenedioxy, 15.4 amino, 15.5 hydroxyl, 15.6 acetoxy, 15.7 carboxyl, 15.8 carbamoyl, 15.9 ethoxycarbonyl, 15.10 halogen or 15.11 nitro, 16. aralkyloxycarbonylamin which may be substituted in the aryl moiety as described under a) 15.1 - 15.11, 17. (C1 -C6 )-alkylureido, 18. arylureido which may be monosubstituted or disubstituted in the aryl moiety by identical or different radical as described under a) 15.1 - 15.11, 19. aralkylureido which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 20. formyl, 21. alkanoylamino having up to 10 C atoms, 22. aroylamino having up to 10 C atoms, which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 23. aralkanoylamino having up to 10 C atoms, which may be monosubstituted or disubstituted in the aryl moiety as described under a) 15.1 - 15.11, 24. arylamino which may be monosubstituted or disubstituted in the aryl moiety by identical or different radicals as described under a) 15.1 - 15.11, 25. aralkylamino which may be substituted in the aryl moiety as described under a) 15.1 - 15.11, 26. alkylmercapto, alkylsulfinyl or alkylsulfonyl having up to 7 C atoms, each of which may be substituted in the alkyl moiety by 26.1 methoxy, 26.2 ethoxy, 26.3 hydroxyl, 26.4 carboxyl, 26.5 carbamoyl, 26.6 ethoxycarbonyl, 26.7 amino or 26.8 (C1 -C6 )-alkylamino, 27. phenylmercapto, phenylsulfinyl or phenylsulfonyl, which may be substituted in the aryl moiety as described under a) 26.1 - 26.8 or by 27.1 halogen, 27.2 nitro or 27.3 sulfamoyl, 28. benzylmercapto, benzylsulfinyl or benzylsulfonyl, which may be substituted in the alkyl moiety as described under a) 26.1 - 26.8 and which may be substituted in the aryl moiety as for the above alkyl moiety or as described under a) 27.1 - 27.3, 29. carboxyl, 30. ethoxycarbonyl, 31. carbamoyl, 32. alkylaminocarbonyl having up to 6 C atoms, 33. cycloalkylcarbamoyl having up to 6 C atoms, 34. cycloalkyleneaminocarbonyl having up to 6 C atoms, 35. dialkylcarbamoyl having up to 6 C atoms, 36. arylcarbamoyl which may be substituted in the aryl moiety by 36.1 halogen, 36.2 (C1 -C6 )-alkyl or 36.3 (C1 -C6 )-alkoxy, 37. aralkylcarbamoyl, 38. guanidino, 39. phenyl, naphthyl, dihydronaphthyl or tetrahydronaphthyl, each of which may be monosubstituted or disubstituted by 39.1 halogen, 39.2 hydroxyl, 39.3 acetoxy, 39.4 carboxyl, 39.5 carbamoyl, 39.6 sulfamoyl, 39.7 nitro, 39.8 methyl, 39.9 ethyl, 39.10 methoxy and/or 39.11 ethoxy, 40. a 5-membered to 7 membered monocyclic or 9 membered or 10-membered bicyclic heterocyclic radical which may contain 1 or 2 S or O atoms and/