Nitro compounds, process for preparation thereof and use thereof

A process for preparing a compound of the following formula or its salt:

• ##STR16## which comprises reacting a compound of the following formula or its salt ##STR17## with dinitrogen trioxide, or in the presence of an acid, a nitrite, wherein
• in the above formulas, R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR18## is cyclized to form ##STR19## X is --O--, --S-- or --NH--, m is an integer 0 or 1, and
• R.sup.3 is carbamoyl, lower alkylcarbamoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula:
• --(Y).sub.n --R.sup.4
• wherein Y is --CO, --SO.sub.2 --, --COCH.sub.2 -- or ##STR20## n is an integer of 0 or 1, and R.sup.4 is a 3-pyridyl or 4-pyridyl group which is optionally substituted with one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl.

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and, as an effective ingredient, a compound of the formula:

• ##STR21## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)alkyl, or ##STR22## is cyclized to form ##STR23## X is --O--, --S-- or --NH--, m is an integer 0 or 1, and
• R.sup.3 is carbamoyl, lower alkylcarbamoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula:
• --(Y).sub.n --R.sup.4
• wherein Y is --CO, --SO.sub.2 --, --COCH.sub.2 -- or ##STR24## n is an integer of 0 or 1, and R.sup.4 is a 3-pyridyl or 4-pyridyl group which is optionally substituted with one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, or pharmaceutically acceptable salt thereof.

A compound selected from the group consisting of 4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl 3-pyridinecarboxylate, 4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl carbamate, 4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl ethylcarbamate, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-phthalimide, 1-acetylamino-4-ethyl-2-hydroxyimino-5-nitro-3-hexene, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexane-yl)-3-pyridinecarboxamide, N,N-dimethyl-N'-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)sulfamide, N-cyano-N'-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridinecarboxi midamide, 6-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-thiopurine, 1-phenyl-5-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)thiotetrazole, 1-methyl-2-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)thioimidazole, 1-methyl-5-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)thiotetrazole, 5-methyl-2-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)thio-1,3,4-thiadia zole, 2-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)thiobenzothiazole, 2-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-thiopyrimidine, N-(4-ethyl-2-hydroxyimino-6-methyl-5-nitro-3-hepten-1-yl)-3-pyridinecarbox amide, 1-acetylamino-4-ethyl-2-hydroxyimino-6-methyl-5-nitro-3-heptene, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-3-pyridinecarboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hexen-1-yl)-3-pyridinecarboxamide, N-(2-hydroxyimino-4-isopropyl-5-nitro-3-hexen-1-yl)-3-pyridinecarboxamide, N-(2-hydroxyimino-3-(2-nitrocyclohexylidene)propyl)-3-pyridinecarboxamide, N-(2-hydroxyimino-6-methoxy-4-methyl-5-nitro-3-hexen-1-yl)-4-pyridinecarbo xamide, 1-acetylamino-2-hydroxyimino-4-methyl-5-nitro-3-heptene, 1-acetylamino-4-ethyl-2-hydroxyimino-5-nitro-3-heptene, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hepten-1-yl)-3-pyridinecarboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridinecarboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)urea, 3-(N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-carbamoyl)-4-pyridineca rboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-4-pyridinecarboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-methyl-3-pyridinecarboxa mide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-methylthio-3-pyridinecar boxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-chloro-3-pyridinecarboxa mide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-hydroxy-3-pyridinecarbox amide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-quinolinecarboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-6-methyl-3-pyridinecarboxa mide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-pyrazinecarboxamide, N-( 4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-methanesulfonamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-propionamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridinesulfonamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-oxamate, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-4-pyrimidinecarboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridylacetamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2,4-dimethylthiazole-5-car boxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3,5-dimethylisoxazole-4-ca rboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-5-methyl-4-imidazolecarbox amide, 5-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-thiotetrazole-1-acetamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-5-methylimidazole-4-carb oxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-3-methylpyrazole-5-carbo xamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-8-oxo-7H-pyrido(2,3-d)py ridazin-5-acetamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-6-amino-3-pyridinecarbox amide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-6-amino-3-pyridinecarboxam ide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-6-oxo-1,4,5,6-tetrahydro pyridazine-3-carboxamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-6-methansulfonamido-3-pyri dinecarboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-1H-1,2,4-triazole-3-carb oxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-4-imidazolecarboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-3-pyridylacetamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-2-oxoindoline-5-carboxam ide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-2-fluoro-3-pyridinecarbo xamide, N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-2-methoxy-3-pyridinecarbox amide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-4-hydroxy-7-methyl-1,8-n aphthyridine-3-carboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-2-ethyl-4-imidazolecarbo xamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-3-aminopyrazine-2-carbox amide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-3-amino-2-pyrazinecarbox amide, N-(2-hydroxyimino-4-methyl-5-nitro-3-hepten-1-yl)-2,5-dimethylimidazole-4- carboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-octen-1-yl)-3-pyridinecarboxamide, N-(2-hydroxyimino-4-methyl-5-nitro-3-octen-1-yl)-3-pyridylacetamide.