5-aminosulfonanilide compounds

Details 5-aminosulfonanilide compounds 5-aminosulfonanilide compounds

1994-02-03

1994-12-20

Dees, Jose G.

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

Organic compounds

Carboxylic acid esters

564 99, C07C31102

Patent

active

053747640

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND ART

The present inventors have already disclosed useful sulfonanilide compounds having anti-inflammatory, antipyretic, analgesic and anti-allergic actions as described in the specification of U.S. Pat. No. 4,885,369.


DISCLOSURE OF THE INVENTION

For the purpose of providing compounds which have higher anti-inflammatory, antipyretic, analgesic and anti-allergic actions, the present inventors have synthesized various 5-aminosulfonanilide compounds, and have studied the pharmacological actions thereof. As a result, it has been found that 5-aminosulfonanilide compounds represented by Formula (I): ##STR2## (wherein R is a hydrogen atom, a formyl group, an acetyl group, a propionyl group, an n-butyryl group, an n-valeryl group, an ethoxyoxalyl group, an n-propoxyoxalyl group, a methoxycarbonylacetyl group or a 3-ethoxycarbonylpropionyl group) have potent anti-inflammatory, antipyretic, analgesic and anti-allergic actions, and thus the present invention has been accomplished. That is, the present invention is the compounds of Formula (I) useful as anti-inflammatory, antipyretic, analgesic and anti-allergic agents.
The compounds of Formula (I) of the present invention can be prepared, for example, by a method as shown below. can be prepared from 2-fluoro-5-nitroaniline as a starting material as follows: ##STR3## (wherein R.sup.1 is R other than a hydrogen 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 may be preferably carried out in the presence of a base such as, for example, an inorganic base (e.g. lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate), or an organic base (e.g. triethylamine, tri-n-butylamine, 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, 4-methylmorpholine, 1-methylpiperidine, pyridine or N,N-dimethylaminopyridine).
Furthermore, this reaction is usually carried out in a solvent such as, for example, dichloromethane, chloroform, ethyl acetate, dioxane, tetrahydrofuran, ethyl ether, benzene, toluene, xylene, acetone, acetonitrile, water, pyridine, N,N-dimethylformamide or dimethyl sulfoxide. subjected to etherification in the presence of a base to give N-(2-cyclohexyloxy-5-nitrophenyl)methanesulfonamide.
Examples of the base in the reaction include alkali metal hydroxides (e.g. lithium hydroxide, sodium hydroxide and potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate and potassium carbonate), alkali metal bicarbonates (sodium bicarbonate and potassium bicarbonate), alkali metal hydrides (e.g. sodium hydride and potassium hydride), inorganic bases (e.g. sodium and sodium amide) and organic bases (e.g. triethylamine, tri-n-butylamine, 1,5-diazabicyclo[4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine and N,N-dimethylaminopyridine).
This reaction may be carried out in the absence or presence of a solvent which is arbitrarily chosen, for example, dioxane, tetrahydrofuran, ethyl ether, petroleum ether, n-hexane, cyclohexane, benzene, toluene, xylene, chlorobenzene, pyridine, N,N-dimethylformamide, dimethyl sulfoxide, dichloromethane or chloroform. Furthermore, the reaction can be accelerated by adding sodium iodide, tris[2-(2-methoxyethoxy)ethyl]amine, a quaternary ammonium salt (e.g. tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide and tricaprylylmethylammonium chloride) or a crown ether (e.g. 18-crown-6 ether). N-(2-cyclohexyloxy-5-nitrophenyl)methanesulfonamide is reduced to give N-(5-amino-2-cyclohexyloxyphenyl)methanesulfonamide.
This reaction may be an ordinary reduction by which a nitro group leads to an amino group, for example, a catalytic reduction using palladium-carbon, Raney nickel or platinum as a catalyst, a reduction using iron or tin, a reduction using sodium sulfideammonium chloride or a reduction using sodium borohydride or

REFERENCES:
patent: 3840597 (1974-10-01), Moore et al.
patent: 3906024 (1975-09-01), Moore et al.
patent: 4866091 (1989-09-01), Matsuo
patent: 4885367 (1989-12-01), Yoshikawa et al.
Chemical Abstract 114: 192589; JP 02300122 1990.

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