Benzoazepinyl compounds as oxytocin and vasopressin antagonists

Details Benzoazepinyl compounds as oxytocin and vasopressin antagonists Benzoazepinyl compounds as oxytocin and vasopressin antagonists

1994-04-20

1996-03-12

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540593, C07D22316, A61K 3155

Patent

active

054986095

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
The invention relates to novel benzoheterocyclic compounds which are useful as medicines.
2. Background Art
Various benzoheterocyclic compounds analogous to the compounds of the present invention have been known to have anti-vasopressin activities in European Patent Publication 0382185 (published on Aug. 16, 1990), WO 91/05549 (published on May 2, 1991), and EP-A-0470514 (published on Feb. 12, 1992). These known compounds are similar to the compounds of the present invention in the benzoheterocyclic nucleus of the chemical structure but are different from the compounds of the present invention in the substituent at 1-position and in the anti-vasopressin activities to some extent.


DISCLOSURE OF THE INVENTION

An object of the present invention is to provide benzoheterocyclic compounds of the formula (1): ##STR2## wherein R.sup.1 is hydrogen atom or a halogen atom, group, a lower alkoxy group, a lower alkenyloxy group, a hydroxy-substituted lower alkoxy group, a lower alkoxycarbonyl-substituted lower alkoxy group, a carboxy-substituted lower alkoxy group, a lower alkylsulfonyloxy-substituted lower alkoxy group, a phthalimide-substituted lower alkoxy group, a hydroxy-substituted lower alkyl group, a group of the formula: --O--D--(CO).sub.I NR.sup.4 R.sup.5 (wherein D is a lower alkylene group, I is 0 or 1, R.sup.4 and R.sup.5 are the same or different and are hydrogen atom, a lower alkyl group, a lower alkanoyl group, a cycloalkyl group, or an amino-substituted lower alkyl group which may optionally have a lower alkyl substituent, or R.sup.4 and R.sup.5 may combine together with the nitrogen atom to which they bond to form a 5- or 6-membered saturated heterocyclic group which may be intervened or not with a nitrogen atom, an oxygen atom or a sulfur atom, wherein said heterocyclic group may optionally be substituted by a lower alkyl group or a lower alkanoyl group), a group of the formula: --E--(CO).sub.I NR.sup.6 R.sup.7 (wherein I is the same as defined above, E is a lower alkylene group, R.sup.6 and R.sup.7 are the same or different and are hydrogen atom, a lower alkyl group, an amino-substituted lower alkyl group which may optionally have a lower alkyl substituent, or a lower alkanoyl group, or R.sup.6 and R.sup.7 may combine together with the nitrogen atom to which they bond to form a 5- or 6-membered saturated heterocyclic group which may be intervened or not with a nitrogen atom, an oxygen atom or a sulfur atom, wherein said heterocyclic group may optionally be substituted by a lower alkyl group, a lower alkanoyl group or a lower alkoxycarbonyl group), a lower alkanoyloxy-substituted lower alkyl group, a lower alkoxycarbonyl-substituted lower alkyl group, an amino which may optionally be substituted by a lower alkyl group or a cycloalkyl group, a carboxy-substituted lower alkyl group, a lower alkylsulfonyloxy-substituted lower alkyl group, a phthalimide-substituted lower alkyl group, an imidazolyl-substituted lower alkyl group, a 1,2,4-triazolyl-substituted lower alkyl group, an amino-substituted lower alkanoyloxy group which may optionally have a lower alkyl substituent, or an imidazolyl-substituted lower alkoxy group, lower alkyl group, --NR.sup.8 -- (wherein R.sup.8 is hydrogen atom or a lower alkyl group), heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom, and ##STR3## wherein R.sup.A is a group of the formula: ##STR4## [wherein m is an integer of 1 to 3, R.sup.18 is hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, nitro group, a lower alkoxycarbonyl group, carboxy group, a lower alkoxycarbonyl-substituted lower alkoxy group, a hydroxy-substituted lower alkoxy group, a carboxy-substituted lower alkoxy group, a lower alkylsulfonyloxy-substituted lower alkoxy group, a phthalimide-substituted lower alkoxy group, or a group of the formula: --O--E--(CO).sub.I NR.sup.19 R.sup.20 (wherein E and I are the same as defined above, R.sup.19 and R.sup.20 are the same or different and are hydrogen atom or a lower alkyl group, or

REFERENCES:
Boyer, S. et al. "The Synthesis of 1,3-Dihydro-1-[1-[(4-methyl-4H,6H-pyrrolo[1,2-a [4,1]benzoxazepin-4-yl)methyl]-4-piperidinyl]-2H-benzimidazol-2-one (1:1) Maleate (CG59443B, Potent Calmodulin Inhibitor)." J. Hetereocyclic Chem. 25, 1003-1005 (1988).
Roe E. T. et al. "Fatty Acid Amides. I. Preparation of Amides of Oleic and the 9,10-Dihydroxystearic Acids." J. Am. Chem. Soc. 71, 2215-2218 (1949).

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