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Details for Patent: 5,158,959

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Details for Patent: 5,158,959

Title: Decahydroisoquinoline carboxylic acids
Abstract:What are disclosed are aminoacid compounds of the formula ##STR1## wherein n is 0 or 1, and salts thereof, said compounds and salts having hypotensive properties; methods for making the compounds; pharmaceutical compositions containing the compounds or salts; and use of the compounds and salts for treating hypertension.
Inventor(s): Geiger; Rolf (Frankfurt am Main, DE), Teetz; Volker (Hofheim am Taunus, DE), Urbach; Hansjorg (Kronberg/Taunus, DE), Scholkens; Bernward (Kelkheim(Taunus), DE), Henning; Rainer (Giessen, DE)
Assignee: Hoechst Aktiengesellschaft (Frankfurt am Main, DE)
Filing Date:Dec 27, 1983
Application Number:06/565,900
Claims:1. A compound of the formula

or a physiologically tolerated salt thereof,

wherein R.sub.1 and R.sub.2, which are the same or different, each represent

a) alkyl or alkenyl having up to 6 C-atoms,

b) alkyl or aklenyl 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) fluoro,

4) mercapto,

5) hydroxy,

6) (C.sub.1 -C.sub.3)-alkoxy optionally substituted by N,N-dimethylamino,

7) phenoxy,

8) phenoxy substituted by

8.1 halogen

8.2 (C.sub.1 -C.sub.6)-alkyl,

8.3 (C.sub.1 -C.sub.6)-alkoxy,

8.4 nitro, and/or

8.5 carbethoxy,

9) naphthyloxy,

10) benzyloxy,

11) benzyloxy substituted in the aryl part by

11.1 methoxy,

11.2 carboxamido,

11.3 amino,

11.4 halogen,

11.5 nitro, or

11.6 methyl,

12) amino,

13) monoalkylamino having up to 7 C-atoms,

14) monoalkylamino having up to 7 C-atoms substituted in the alkyl part by

14.1 hydroxy,

14.2 carboxy,

14.3 carboxamido,

14.4 carbethoxy,

14.5 amino,

14.6 (C.sub.1 -C.sub.6)-alkylamino,

14.7 di-(C.sub.1 -C.sub.6)-alkylamino,

14.8 piperidino, or

14.9 morpholino,

15) dialkylamino having up to 7 C-atoms,

16) dialkylamino having up to a total of 7 C-atoms substituted in the alkyl part by

16.1 hydroxy,

16.2 carboxy,

16.3 carboxamido,

16.4 carbethoxy,

16.5 amino,

16. 6 (C.sub.1 -C.sub.6)-alkylamino,

16.7 di-(C.sub.1 -C.sub.6)-alkylamino,

16.8 piperidino, or

16.9 morpholino,

17) monocycloalkylamino having up to 7 C-atoms,

18) dicycloalkylamino having up to 7 C-atoms,

19) (C.sub.1 -C.sub.6)-alkoxycarbonylamino,

20) phenoxycarbonylamino,

21) phenoxycarbonylamino substituted by

21.1 halogen,

21.2 (C.sub.1 -C.sub.6)-alkyl,

21.3 C.sub.1 -C.sub.6)-alkoxy,

21.4 nitro, and/or

21.5 carbethoxy,

22) naphthyloxycarbonylamino,

23) benzyloxycarbonylamino or phenethyloxycarbonylamino,

24) benzyloxycarbonylamino or phenethyloxycarbonylamino each substituted in the aryl part by

24.1 halogen,

24.2 nitro,

24.3 (C.sub.1 -C.sub.6)-alkyl, or

24.4 (C.sub.1 -C.sub.6)-alkoxy,

25) phenylcarbamoyloxy,

26) (C.sub.1 -C.sub.6)-alkylureido,

27) cyclohexylureido,

28) phenylureido,

29) phenylureido substituted by

29.1 halogen,

29. 2 (C.sub.1 -C.sub.6)-alkyl,

29.3 (C.sub.1 -C.sub.6)-alkoxy, and/or

29.4 nitro,

30) naphthylureido,

31) benzylureido or phenethylureido,

32) benzylureido or phenethylureido each substituted by

32.1 halogen,

32.2 nitro,

32.3 (C.sub.1 -C.sub.6)-alkyl, or

32.4 (C.sub.1 -C.sub.6)-alkoxy,

33) formyl,

34) (C.sub.1 -C.sub.6)-alkanoylamino,

35) benzoylamino,

36) benzoylamino mono- to tri-substituted by

36.1 halogen,

36.2 (C.sub.1 -C.sub.6)-alkyl,

36.3 (C.sub.1 -C.sub.6)-alkoxy,

36.4 hydroxy,

36.5 carboxy,

36.6 nitro, or

36.7 amino,

37) naphthoylamino,

38) benzylcarbonylamino or phenethylcarbonylamino,

39) benzylcarbonylamino or phenethylcarbonylamino each substituted by

39.1 halogen,

39.2 nitro,

39.3 (C.sub.1 -C.sub.6)-alkyl, or

39.4 (C.sub.1 -C.sub.6)-alkoxy,

40) phenylamino or naphthylamino,

41) phenylamino or naphthylamino each mono- or di-substituted by

41.1 (C.sub.1 -C.sub.2)-alkyl,

41.2 (C.sub.1 -C.sub.2)-alkoxy,

41.3 methylenedioxy,

41.4 amino,

41.5 hydroxy,

41.6 acetoxy,

41.7 carboxy,

41.8 carboxamido,

41.9 carbethoxy,

41.10 halogen, and/or

41.11 nitro,

42) 4,6-dimethyl-pyrimidyl-amino,

43) benzylamino or phenethylamino,

44) benzylamino or phenethylamino each mono- or di-substituted in the aryl part by

44.1 (C.sub.1 -C.sub.2)-alkyl,

44.2 (C.sub.1 -C.sub.2)-alkoxy,

44.3 methylenedioxy,

44.4 amino,

44.5 hydroxy,

44.6 acetoxy,

44.7 carboxy,

44.8 carboxamido,

44.9 carbethoxy,

44.10 halogen, and/or

44.11 nitro,

45) (C.sub.1 -C.sub.6)-alkylmercapto, (C.sub.1 -C.sub.6)-alkylsulfinyl, or (C.sub.1 -C.sub.6)-alkylsulfonyl,

46) (C.sub.1 -C.sub.6)-alkylmercapto, (C.sub.1 -C.sub.6)-alkylsulfinyl, or (C.sub.1 -C.sub.6)-alkylsulfonyl each substituted by

46.1 methoxy,

46.2 ethoxy,

46.3 hydroxy,

46.4 carboxy,

46.5 carboxamido,

46.6 carbethoxy,

46.7 amino,

46.8 (C.sub.1 -C.sub.6)-alkylamino, or

46.9 dimethylamino,

47) phenylmercapto, naphthylmercapto, phenylsulfinyl, naphthylsulfinyl, phenylsulfonyl, or naphthylsulfonyl,

48) phenylmercapto, naphthylmercapto, phenylsulfinyl, naphthylsulfinyl, phenylsulfonyl, or naphthylsulfonyl each substituted by

48.1 methoxy,

48.2 ethoxy,

48.3 hydroxy,

48.4 carboxy,

48.5 carboxamido,

48.6 carbethoxy,

48.7 amino,

48.8 (C.sub.1 -C.sub.6)-alkylamino,

48.9 halogen,

48.10 nitro,

48. 11 sulfonamido, or

48.12 methyl,

49) benzylmercapto, benzylsulfinyl, or benzylsulfonyl,

50) benzylmercapto, benzylsulfinyl, or benzylsulfonyl each substituted in the alkyl part by

50.1 methoxy,

50.2 ethoxy,

50.3 hydroxy,

50.4 carboxy,

50.5 carboxamido,

50.6 carbethoxy,

50.7 amino,

50.8 (C.sub.1 -C.sub.6)-alkylamino, or substituted in the aryl part by

50.9 methoxy,

50.10 ethoxy,

50.11 hydroxy, or

50.12 carboxy,

51) carboxy,

52) carboalkoxy with alkyl having up to 3 C-atoms,

53) carbobenzyloxy,

54) carbamoyl,

55) alkylaminocarbonyl having up to 6 C-atoms,

56) cycloalkylaminocarbonyl having up to 6 C-atoms,

57) cycloalkenylaminocarbonyl having up to 6 C-atoms,

58) dialkylaminocarbonyl having up to 6 C-atoms,

59) phenylaminocarbonyl,

60) phenylaminocarbonyl mono- to tri-substituted by

60.1 halogen,

60.2 (C.sub.1 -C.sub.6)-alkyl,

60.3 (C.sub.1 -C.sub.6)-alkoxy,

60.4 carboxy,

60.5 carboxamido,

60.6 carbethoxy,

60.7 hydroxy, and/or

60.8 nitro,

61) naphthylaminocarbonyl,

62) benzylaminocarbonyl or phenethylaminocarbonyl,

63) benzylaminocarbonyl or phenethylaminocarbonyl each substituted by

63.1 halogen,

63.2 nitro,

63.3 (C.sub.1 -C.sub.6)-alkyl, or

63.4 (C.sub.1 -C.sub.6)-alkoxy,

64) guanido,

65) phenyl, naphthyl, dihydronaphthyl, or tetrahydronaphthyl,

66) phenyl, naphthyl, dihydronaphthyl, or tetrahydronaphthyl, each mono- to tri-substituted by

66.1 halogen,

66.2 hydroxy,

66.3 acetoxy,

66.4 carboxy,

66. 5 carboxamido,

66.6 sulfonamido,

66.7 nitro,

66.8 methyl,

66.9 ethyl,

66.10 methoxy,

66.11 ethoxy, and/or

66.12 amino,

67) a 5-membered to 7-membered monocyclic heterocyclic structure, the hetero atoms of which are one or two S- or O-atoms and/or up to four N-atoms,

68) a 5-membered to 7-membered monocyclic heterocyclic structure, the hetero atoms of which are one or two S- or O-atoms and up to four N-atoms, which heterocyclic structure is substituted by

68.1 halogen,

68.2 oxo,

68.3 S-oxo,

68.4 hydroxy,

68.5 carboxy,

68.6 carboxamido,

68.7 sulfonamido,

68.8 nitro,

68.9 (C.sub.1 -C.sub.6)-alkyl,

68.10 benzyl or phenethyl,

68.11 methoxy,

68.12 ethoxy, or

68.13 amino,

69) a 9-membered or 10-membered bicyclic heterocyclic structure, the hetero atoms of which are one or two S- or O-atoms and/or up to four N-atoms per ring, or

70) a 9-membered or 10-membered bicyclic heterocyclic structure, the hetero atoms of which are one or two S- or O-atoms per ring, which heterocyclic structure is substituted by

70.1 halogen,

70.2 oxo,

70.3 S-oxo,

70.4 hydroxy,

70.5 carboxy,

70.6 carboxamido,

70.7 sulfonamido,

70.8 nitro,

70.9 (C.sub.1 -C.sub.6)-alkyl,

70.10 benzyl or phenethyl,

70.11 methoxy, or

70.12 ethoxy,

c) (C.sub.5 -C.sub.7)-cycloalkyl- or cycloalkenyl,

d) (C.sub.7 -C.sub.12)-cycloalkylalkyl,

e) phenyl, naphthyl, dihydronaphthyl, or tetrahydronaphthyl,

f) phenyl, naphthyl, dehydronaphthyl, or tetrahydronaphthyl, each substituted by

1) halogen,

2) (C.sub.1 -C.sub.6)-alkyl, or

3) (C.sub.1 -C.sub.6)-alkoxy,

g) a 6-membered monocyclic heterocycle, the hetero atoms of which are one or two S-atoms; or

wherein R.sub.1 is hydrogen and R.sub.2 is defined as above in a)-g); and

wherein R.sub.3 is hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 10 carbon atoms, or aralkyl having 7 to 14 carbon atoms.

2. A compound as in claim 1 in which is N-(1-carboethoxy-3-phenyl-propyl)-L-alanyl-L-decahydroisoquinoline-3-carbo xylic acid.

3. A compound as in claim 1 which is N-[1-S-carboethoxy-3-(3-indolyl)-propyl]-S-alanyldecahydroisoquinoline-3-S -carboxylic acid.

4. A compound as in claim 1 which is N-[1-S-carboethoxy-2-(3-indolyl)-ethyl]-S-alanyldecahydroisoquinoline-3-S- carboxylic acid.

5. A pharmaceutical preparation for the treatment of hypertension, said preparation comprising a hypotensively effective amount of a compound or salt as in claim 1 and a pharmaceutically acceptable carrier therefor.

6. A method for treating hypertension in a patient suffering therefrom, which method comprises orally, intravenously, or subcutaneously administering to said patient a hypotensively effective amount of a compound as in claim 1.
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