Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1995-08-14
1996-05-28
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
514605, 546234, 564 99, C07C31108, C07D295873
Patent
active
055213111
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/00228 filed Feb. 16, 1994.
TECHNICAL FIELD
The present invention relates to 5-aminoacetylaminosulfonanilide compounds having anti-inflammatory, antipyretic, analgesic and anti-allergic actions.
BACKGROUND ART
Although various sulfonanilide compounds, in particular 2-phenoxysulfonanilide compounds in the specification of U.S. Pat. No. 3,856,857, have been known, 5-aminoacetylaminosulfonanilide compounds of the present invention have not been known.
However, the above-mentioned known sulfonanilide compounds have been insufficient in drug effect.
An object of the present invention is to provide compounds having excellent anti-inflammatory, antipyretic, analgesic and anti-allergic actions.
DISCLOSURE OF THE INVENTION
As a result of extensive researches for the purpose of solving the above-mentioned problem, the present inventors have found that the purpose could be achieved by the following 5-aminoacetylaminosulfonanilide compounds, and have accomplished the present invention.
The present invention relates to the compounds represented by Formula (I): ##STR2## (wherein R.sup.1 is a phenyl group, a halophenyl group or a cycloalkyl group having 3 to 8 carbon atoms, R.sup.2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R.sup.3 is a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or a benzyl group, or R.sup.2 and R.sup.3 are bonded together to form a 5- to 7-membered heterocycle) and salts thereof.
The halophenyl group for R.sup.1 refers to a phenyl group substituted by one or two of the same or different atoms selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom, and the cycloalkyl group having 3 to 8 carbon atoms refers to a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.
The alkyl group having 1 to 5 carbon atoms for R.sup.2 refers to a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-pentyl group.
The alkyl group having 1 to 7 carbon atoms for R.sup.3 refers to a straight or branched chain alkyl group such as, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an n-hexyl group or an n-heptyl group; the cycloalkyl group having 3 to 8 carbon atoms refers to a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group; and examples of the alkenyl group having 3 to 5 carbon atoms are an allyl group, a 2-butenyl group, a 3-butenyl group and a 3-methyl-2-butenyl group.
Examples of the 5- to 7-membered heterocycle formed by bonding R.sup.2 and R.sup.3 together are a pyrrolidino group, a piperidino group, a hexamethyleneimino group, a morpholino group, a thiomorpholino group, a piperazino group and a 4-methylpiperazino group.
The salt refers to salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid or phosphoric acid, or organic acids such as acetic acid, propionic acid, succinic acid, fumaric acid, maleic acid, benzoic acid, phthalic acid, cinnamic acid, glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, methanesufonic acid or p-toluenesulfonic acid.
Methods for preparing the compounds of the present invention are as follows:
(1) The compounds of Formula (I) of the present invention can be prepared, for example, according to a preparation method shown by the following Reaction Route (i) using 2-fluoro-5-nitroaniline as a starting material. ##STR3## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, X is a chlorine atom, a bromine atom or an iodine atom).
(a) First, the amino group of 2-fluoro-5-nitroaniline is sulfonylated by using methanesulfonyl chloride to give N-(2-fluoro-5-nitrophenyl)methanesulfonamide.
This reaction is preferably carried out in the presence of a base such as, for example, an in
REFERENCES:
patent: 3856857 (1974-12-01), Beregi et al.
Hatayama Katsuo
Kashiwa Mariko
Saito Shiuji
Shimazaki Yohichi
Yoshikawa Kensei
Ramsuer Robert W.
Taisho Pharmaceutical Co. Ltd.
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