Nitro compounds, process for preparation thereof and use thereof

Details Nitro compounds, process for preparation thereof and use thereof Nitro compounds, process for preparation thereof and use thereof

1994-05-03

1996-02-27

Bernhardt, Emily

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544224, 544236, 544242, 544265, 544315, 544406, 546 22, 546122, 546169, 546318, 546323, 546329, 546335, 548136, 548169, 548200, 548248, 548251, 5482668, 5483335, 5483751, 548472, 548477, 5483261, 548473, 552 10, 558170, 558458, 560165, 564 59, 564 79, 564 95, 564191, 564193, 564197, 564258, 564268, C07D21381, C07D21371, C07D21382, A61K 3144

Patent

active

054950236

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP92/01414 filed Nov. 2, 1992.


TECHNICAL FIELD

This invention relates to new nitro compounds. More particularly, this invention relates to new nitro compounds and their pharmaceutically acceptable salts, which are useful for vasodilator, to processes for preparation thereof, to a pharmaceutical composition comprising the same and to a method of use thereof.


BACKGROUND ART

EP-A-0113106 discloses nitro compounds which are useful for vasodilator, but an increase of durability of pharmacological effect of these compounds is desired.
This invention is to provide new nitro compounds which are useful for vasodilator and have increased durability of pharmacological effect.


DISCLOSURE OF INVENTION

The objective new nitro compounds are represented by the following formula (I): ##STR5## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR6## is cyclized to form ##STR7## X is --O--, --S-- or --NH--, m is an integer 0 or 1, and alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4 ##STR8## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl.
Preferred examples and illustrations of various definitions in the description hereinabove and hereinbelow, which the present invention includes within the scope thereof are explained in detail as follows.
The term "lower" is intended to mean 1 to 6 carbon atoms, unless otherwise indicated.
Preferred example of "lower alkyl" may include a residue of straight and branched alkane having 1 to 6 carbon atom(s) such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl and the like.
Preferred examples of "lower alkylcarbamoyl" may include methylcarbamoyl, N,N-dimethylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl, isobutylcarbamoyl, tert-butylcarbamoyl and the like.
Preferred examples of "lower alkanoyl" may include formyl, acetyl, propionyl, butyl, isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl, 3,3-dimethylbutyryl and the like.
Preferred examples of "di-lower alkylaminosulfonyl" may include di-methylaminosulfonyl, di-ethylaminosulfonyl and the like.
Preferred examples of "halogen" is fluorine, chlorine, bromine and iodine.
Preferred examples of "lower alkoxy" may include a straight or branched one such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy or the like, in which the preferable one is C.sub.1 -C.sub.4 alkoxy and the most preferable one is methoxy or ethoxy.
Preferred examples of "lower alkylsulfonylamino" may include methylsulfonylamino, ethylsulfonylamino and the like.
Preferred examples of "lower alkoxy(lower)alkyl" may include methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl and the like.
Preferred examples of "lower alkylthio" may include methylthio, ethylthio, propylthio, isopropylthio, butylthio and the like.
Preferred examples of "lower alkylsulfonyl" may include mesyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl and the like.
Preferred examples of "heterocyclic group" may include a unsaturated 3- to 8-membered monocyclic heterocyclic group containing 1 to 4 nitrogen atoms such as pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl and its N-oxide, dihydropyridyl, pyrimidinyl, pyrazinyl, 6-oxo-1,4,5,6-tetrahydropyridazinyl, pyridazinyl, triazolyl (e.g. 4H-1,2,4-triazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, 1H-1,2,4-triazolyl, etc.), tetrazolyl (e.g. 1H-tetrazolyl, 2H-tetrazolyl, etc.), and the like, a 3- to 8- membered monocyclic heterocyclic group containing at least one sulfur atom and at least one nitrogen atom such as thiazolyl, isothiazolyl, thiadiazolyl and the like, 3- to 8- membered monocyclic heterocyclic group containing at least one oxygen atom and at least on

REFERENCES:
patent: 4863926 (1989-09-01), Okamoto et al.

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