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Details for Patent: 4,575,503

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Details for Patent: 4,575,503

Title: 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
Abstract:Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin -2-ones and functional derivatives are angiotensin converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.
Inventor(s): Watthey; Jeffrey W. H. (Chappaqua, NY)
Assignee: Ciba-Geigy Corporation (Ardsley, NY)
Filing Date:Feb 09, 1984
Application Number:06/578,456
Claims:1. A compound of the formula ##STR25## wherein the carbocyclic ring may also be hexahydro; R.sub.1 is indolyl(lower)alkyl, carboxy(lower)alkyl, lower alkoxycarbonyl(lower)alkyl, hydroxy(lower)alkyl, lower alkylthio(lower)alkyl, aryloxy(lower)alkyl or arylthio(lower)alkyl wherein aryl represents phenyl unsubstituted or mono- or di-substituted by lower alkyl, hydroxy, lower alkoxy, lower alkylenedioxy, lower alkanoyloxy, halogen or trifluoromethyl; R.sub.2 and R.sub.5 are hydrogen or lower alkyl; R.sub.3 and R.sub.4 are hydrogen, lower alkoxy, lower alkyl, halogen or trifluoromethyl; or R.sub.3 and R.sub.4 taken together on adjacent carbons represent alkylenedioxy; X represents oxo, one hydroxy or acylated hydroxy and one hydrogen, or 2 hydrogens; R.sub.6 and R.sub.7 independently represent hydroxy, amino, lower alkoxy, phenyl(lower)alkoxy, lower alkoxycarbonyl(lower)alkoxy; and wherein within the above definitions acylated hydroxy represents lower alkanoyloxy, nicotinoyloxy, benzoyloxy or benzoyloxy substituted on the phenyl ring by lower alkyl, halogen or lower alkoxy; or a pharmaceutically acceptable salt thereof.

2. A compound of the formula ##STR26## wherein the carbocyclic ring may also be hexahydro; R.sub.1 is acylamino(lower)alkyl in which acylamino represents lower alkanoylamino; lower alkoxycarbonylamino; aryl(lower)alkanoylamino; aryl(lower)alkoxycarbonylamino; or aroylamino in which aroyl represents benzoyl or benzoyl substituted by lower alkyl, lower alkoxy or halogen, or nicotinoyl; or R.sub.1 is mono- or di(lower)alkylamino(lower)alkyl, aryl-N-(lower alkyl)-amino(lower)alkyl or arylamino(lower)alkyl wherein aryl represents phenyl unsubstituted or mono- or di substituted by lower alkyl, hydroxy, lower alkoxy, lower alkylenedioxy, lower alkanoyloxy, halogen or trifluoromethyl; R.sub.2 and R.sub.5 are hydrogen or lower alkyl; R.sub.3 and R.sub.4 are hydrogen, lower alkoxy, lower alkyl, halogen or trifluoromethyl; or R.sub.3 and R.sub.4 taken together represent alkylenedioxy; X represents oxo, one hydroxy or acylated hydroxy and one hydrogen, or 2 hydrogens; R.sub.6 and R.sub.7 independently represent hydroxy, amino, lower alkoxy, phenyl(lower)alkoxy, lower alkoxycarbonyl(lower)alkoxy; wherein the above definitions acylated hydroxy represents lower alkanoyloxy, nicotinoyloxy, benzoyloxy or benzoyloxy or benzoyloxy substituted on the phenyl ring by lower alkyl, halogen or lower alkoxy; or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 being 1-carboxymethyl-3-[1-ethoxycarbonyl-2-(benzylthio)ethylamino]-2,3,4,5-tetr ahydro-1H-[1]-benzazepin-2-one, a stereoisomer or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 1 being 1-carboxymethyl-3[1-ethoxycarbonyl-2-(3-indolyl)-ethylamino]-2,3,4,5-tetra hydro-1H[1]-benzazepin-2-one, a stereoisomer or a pharmaceutically acceptable salt thereof.

5. 1-Carboxymethyl-3-[1-e thoxycarbonyl-(1S)-butyl-amino]-2,3,4,5-tetrahydro-1H-[1]-(3S)-benzazepin-2 one or a pharmaceutically acceptable salt thereof.

6. A compound according to claim 1 being 1-carboxymethyl-3-[1-ethoxycarbonyl-3-methylthiopropylamino]-2,3,4,5-tetra hydro-1H-[1]-benzazepin-2-one, a stereoisomer or a pharmaceutically acceptable salt thereof.

7. A compound according to claim 1 being 1-carboxymethyl-3-[1-ethoxycarbonyl-2-benzyloxyethylamino]-2,3,4,5-tetrahy dro-1H-[1]-benzazepin-2 one, a stereoisomer or a pharmaceutically acceptable salt thereof.

8. A compound according to claim 2 being 1-carboxymethyl-3-[1-ethoxycarbonyl-5-(benzoylamino)-pentylamino]-2,3,4,5- tetrahydro-1H-[1]-benzazepin-2-one, a stereoisomer or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition suitable for oral or parenteral administration to mammals for the treatment or prevention of diseases responsive to inhibition of angiotensin-converting enzyme comprising an effective amount of a compound of claim 1 in combination with one or more pharmaceutically acceptable carriers.

10. A method of treating hypertensive or cardiac conditions in mammals which comprises administering to a mammal in need thereof an effective amount of a composition of claim 9.

11. A method of inhibiting angiotensin-converting enzyme which comprises administering to a mammal in need thereof an effective amount of a composition of claim 9.
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