GB835753A - Improvements in or relating to heterocyclic sulphonamide compounds - Google Patents

Improvements in or relating to heterocyclic sulphonamide compounds

Info

Publication number
GB835753A
GB835753A GB2162856A GB2162856A GB835753A GB 835753 A GB835753 A GB 835753A GB 2162856 A GB2162856 A GB 2162856A GB 2162856 A GB2162856 A GB 2162856A GB 835753 A GB835753 A GB 835753A
Authority
GB
United Kingdom
Prior art keywords
isothiazole
methyl
amino
sulphanilamido
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2162856A
Inventor
Arthur Adams
Ronald Slack
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB2162856A priority Critical patent/GB835753A/en
Priority to CH4826357A priority patent/CH365077A/en
Publication of GB835753A publication Critical patent/GB835753A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0835753/IV (b)/1> and salts thereof such as the alkali-metal or alkaline-earth metal salts, where R1 is hydrogen or methyl, and of R2 and R3, one is hydrogen and the other is a p-aminobenzenesulphonamido group, with the proviso that when R1 is hydrogen, the sulphanilamido group is in the 4-position, and their o-carboxybenzoyl and b -carboxypropionyl derivatives. The compounds are prepared by the usual methods for N1-heterocyclic sulphanilamides, for example by the reaction of a p-substituted benzenesulphonyl halide wherein the p-substituent is a group convertible into an amino group (e.g. acylamino) with the appropriate 4- or 5-amino-isothiazole followed by conversion of the p-substituent (e.g. by hydrolysis) into an amino group. The reaction is preferably carried out in an organic solvent in the presence of a basic condensing agent. Suitably the condensing agent may also be the solvent, for example pyridine. Examples describe the preparation of (1) 4-sulphanilamido-isothiazole; (2) 5-sulphanilamido-3-methyl-isothiazole and (5) 4-sulphanilamido-3-methyl-isothiazole, by hydrolysis of the intermediate acetyl derivative obtained by the action of p-acetylaminobenzenesulphonyl chloride on the amino-isothiazole; the preparation of the mono-succinoyl and phthaloyl derivatives of (2) is described. 4-Amino-isothiazole is made by oxidizing 5-aminobenz-1 : 2-isothiazole with permanganate, decarboxylating the resulting iso-thiazole-4 : 5-dicarboxylic acid, converting the isothiazole-4-carboxylic acid to its methyl ester, degrading via the carboxyhydrazide and azide to the benzyl urethane and treating with hydrogen bromide in acetic acid. (The ethyl urethane is described in the Provisional Specification.) 5 - Amino - 3 - methyl - isothiazole is made by cyclizing b -iminothiobutyramide. 4-Amino-3-methyl-isothiazole is made by di-azotizing 5-amino-3-methyl-isothiazole, reacting with cuprous bromide, heating the resulting 5-bromo-3-methyl-isothiazole with cuprous cyanide to give 5-cyano-3-methyl-isothiazole, hydrolysing to 3-methyl-isothiazole-5-carboxylic acid, heating to give 3-methyl-isothiazole, nitrating to 3-methyl-4-nitro-isothiazole and reducing with ferrous sulphate.
GB2162856A 1956-07-12 1956-07-12 Improvements in or relating to heterocyclic sulphonamide compounds Expired GB835753A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2162856A GB835753A (en) 1956-07-12 1956-07-12 Improvements in or relating to heterocyclic sulphonamide compounds
CH4826357A CH365077A (en) 1956-07-12 1957-07-11 Process for the preparation of novel isothiazole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2162856A GB835753A (en) 1956-07-12 1956-07-12 Improvements in or relating to heterocyclic sulphonamide compounds

Publications (1)

Publication Number Publication Date
GB835753A true GB835753A (en) 1960-05-25

Family

ID=10166129

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2162856A Expired GB835753A (en) 1956-07-12 1956-07-12 Improvements in or relating to heterocyclic sulphonamide compounds

Country Status (1)

Country Link
GB (1) GB835753A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3186999A (en) * 1961-03-16 1965-06-01 May & Baker Ltd Isothiazole derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3186999A (en) * 1961-03-16 1965-06-01 May & Baker Ltd Isothiazole derivatives

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