4-amino-5-oxy-2,6,6-trimethyl-2-cycloheptene compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai

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514506, 514646, 514579, 514428, 514317, 514212, 5142388, 514255, 514327, 514330, 514278, 514331, 540610, 544173, 544399, 548571, A61K 31135

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058498010

DESCRIPTION:

BRIEF SUMMARY
THE DESCRIPTION

This application is a 35 U.S.C. 371 of PCT/JP96/01023 (Apr. 12, 1996).


TECHNICAL FIELD

The present invention relates to 4-amino-5-oxy-2,6,6-trimethyl-2-cycloheptene compounds which are useful as medicaments, and to their pharmacologically acceptable salts and solvates. More specifically, it relates to a remedy for hypertension, peripheral arterial occlusion or bronchial asthma whose effective components are 4-amino-5-oxy-2,6,6-trimethyl-2-cycloheptene compounds, their pharmacologically acceptable salts and their solvates.


BACKGROUND ART

The present inventors have isolated and identified 4,5-dihydroxy-2,6,6-trimethyl-2-cyclohepten-1-one (hereunder referred to as "Saishin N") from the crude drug Asarum Siebeldi, as a useful antiulcer substance, and have developed a method for its chemical production, filing a patent application therefor (Japanese Unexamined Patent Publication No. Hei-3-275640) as well as a patent application for various Saishin N compounds with antiulcer effects (Japanese Unexamined Patent Publication No. Hei-5-213811).
It was found that the Saishin N compounds are effective for the treatment of ischemic and reperfusion disorders and the improvement of microcirculatory blood flow, and patent applications were filed therefor (Japanese Unexamined Patent Publication Nos. Hei-7-17852, Hei-7-101858).


DISCLOSURE OF THE INVENTION

The present Inventors have diligently researched aminolysis reactions of eucarvone-4,5-oxide for the purpose of synthesizing Saishin N compounds with amino groups, and have completed the present invention based upon the finding that Saishin N compounds with an amino group selectively introduced at position 4 may be obtained by using the method of Marco resulting 4-amino-5-oxy-2,6,6-trimethyl-2-cyclohepten-1-one compounds and their oxime derivatives exhibit an effect against rat peripheral arterial occlusion models, spontaneous hypertensive rats, histamine-induced airway contraction models and passive sensitization models.
According to the present invention there are provided 4-amino-5-oxy-2,6,6-trimethyl-2-cycloheptene compounds represented by the following general formula: ##STR2## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom, an alkyl group, or a phenyl group which may have a hydroxyl group, lower alkoxy group, amino group, nitro group, carboxyl group, lower alkoxycarbonyl group or halogen atom, or R.sup.1, R.sup.2 and the nitrogen atom together represent a saturated nitrogen heterocyclic group; R.sup.3 represents a hydrogen atom, a lower alkyl group or a lower aliphatic acyl group; and W represents an oxo group, oxime group or oxime ether group); and their pharmacologically acceptable salts and their solvates, as well as pharmaceutical composition containing then as an effective ingredient.
The alkyl group is an acyclic or cyclic alkyl group of 1 to 10 carbon atoms, and preferably 1 to 8 carbon atoms, and it may be substituted with a hydroxyl group, lower alkoxy group, amino group, lower alkylamino group, lower dialkylamino group, or a phenyl group which may have a hydroxyl group, lower alkoxy group, amino group, nitro group, carboxyl group, lower alkoxycarbonyl group or halogen atom. Specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, hexyl, isohexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-hydroxyethyl, 2-methoxyethyl, 2-dimethylaminoethyl, benzyl, 4-ethoxycarbonylbenzyl, phenethyl and 4-phenylbutyl groups.
The halogen atom may be fluorine, chlorine, bromine or iodine.
The saturated nitrogen heterocyclic group is pyrrolidine, piperidine, homopiperidine, piperazine, homopiperazine or morpholine which may have a lower alkyl group, hydroxyl group, lower alkoxy group, carboxyl group, lower alkoxycarbonyl group, oxo group or an acetal group thereof on its ring.
The oxime ether is a lower alkyloxime ether or benzyloxime ether.
The term "lower" here refers to an acyclic or cyclic

REFERENCES:
Chini et al., 1990, Metal Salts as New Catalysts . . . Tetrahedron Letters.
Corey et al., 1986, A New Synthetic Route To Prostaglandins, Tetrahedron Letters.
Iwamoto et al., Dec. 1986, Prophylactic Effect Of . . . Japanese Pharmacology & Therapeutics.
Minami et al., 1983, Japanese Journal of Thoracic Diseases.
Ishibashi et al., 1983, Folia Pharmacologica Japonica.
Suzuki et al., Sep. 1987, The Clinical Report vol. 21 No. 13.

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