GB598472A - Manufacture of para-aminobenzene sulphonacylamides - Google Patents

Manufacture of para-aminobenzene sulphonacylamides

Info

Publication number
GB598472A
GB598472A GB21582/44A GB2158244A GB598472A GB 598472 A GB598472 A GB 598472A GB 21582/44 A GB21582/44 A GB 21582/44A GB 2158244 A GB2158244 A GB 2158244A GB 598472 A GB598472 A GB 598472A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
aminobenzene
dimethyl
para
sulphon
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
GB21582/44A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB598472A publication Critical patent/GB598472A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/14—Nitrogen atoms
    • C07D261/16—Benzene-sulfonamido isoxazoles

Landscapes

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

Abstract

Para-aminobenzene sulphonacylamides of the general formula <FORM:0598472/IV/1> where R1 is a heterocyclic residue containing as substituents halogen, an alkyl residue, and/or an alkoxy alkylthio-residue, R2 represents hydrogen, alkyl or aralkyl and R3 represents hydrogen or alkyl are made by treating a sulphonamide of the benzene series, containing in the para position an amino group or a group which may be converted into an amino group by hydrolysis or reduction, with a carboxylic acid of the formula R1-COOH or with a functional derivative of such an acid. In a modified process, a benzene sulpho-halide substituted in the para position with a group containing nitrogen and which is convertible by reduction or hydrolysis to an amino group, is reacted with a salt of an acid amide of the general formula R1-CO.NH2, where R1 has the meaning previously ascribed to it, giving the desired type of product. Suitable sulphonamides are those mentioned in the parent Specification and also the ureides, urethanes and amino alkylene sulphonic acids. Specified heterocyclic carboxylic acids are 2 : 5-dimethylpyrrole-3-carboxylic acid, 2 : 5-dimethylfurane-3-carboxylic acid, 5-tertiary-butyl-furane-2-carboxylic acid, 2 - methylfurane - 5 - carboxylic acid, 2 : 4 - dimethylfurane - 3 - carboxylic acid, 3-methyl-pyrazole-5-carboxylic acid, 5-methyl-isoxazole-3-carboxylic acid, 3-methylisoxazole-5-carboxylic acid, 3 : 5 - dimethylisoxazole-4-carboxylic acid, 4-methyl-thiazole-5-carboxylic acid, 2 - chloro - 4 - methylthiazole - 5 - carboxylic acid, 2 : 4 - dimethylthiazole - 5 - carboxylic acid, 6 - chloro - pyridine - 3 - carboxylic acid, 2 : 4 - dimethylpyridine-3-carboxylic acid, 6-methoxypyridine-3-carboxylic acid, 6-methylmercaptopyridine-3-carboxylic acid, 1 - ethyl - pyridone-(6)-3-carboxylic acid, 1-isobutylpyridone-(6)-3-carboxylic acid, 6 - methoxy - 2 : 4 - dimethylpyridine - 3 - carboxylic acid, 6-ethyl mercapto-2 : 4 - dimethyl - pyridine - 3 - carboxylic acid, 5 - methyl - pyrimidine - 4 - carboxylic acid, 5 - methylthiodiazole-(1 : 2 : 3)-4-carboxylic acid, 4 : 6 - dimethyl - pyrimidine - 2 - carboxylic acid, 3 : 6 - dimethyl - pyridazine - 4 - carboxylic acid, 3-methyl-oxdiazole-(1 : 2 : 4)-5-carboxylic acid, 2 - ethyl - pyrimidine - 4 - carboxylic acid, 5 : 6-dimethylpyrazine-3-carboxylic acid, 1-methylpyrrolidine-2-carboxylic acid, 2-methyl-benzthiazole - 7 - carboxylic acid, 5 - ethylthiodiazole-(1 : 3 : 4)-2-carboxylic acid, 2-methylpyridine-3-carboxylic acid, 2-methylpyridine-3-acetic acid, 2 : 6-dimethyl-4-chlorpyridine-3-carboxylic acid and 4 : 5 - dimethylpyridine - 3 - carboxylic acid. These are made as described in the literature. In examples: (I) para-aminobenzene-sulphon-3 : 5-dimethylisoxazole-4-carboxylic acid is prepared by the reaction of sodium para-nitrobenzene sulphonamide with 3 : 5-dimethylisoxazole-4-carboxylic acid chloride followed by reduction of the nitro group in an analogous manner; (II) 4-aminobenzene-sulphon-21 : 61-dimethyl-41-chloropyridine-31-carboxylic acid amide is prepared from 2 : 6-dimethyl-4-chloropyridine-3-carboxylic acid chloride and 4-acetylaminobenzene sulphonamide. 4-Ureido-aminobenzene - sulphon - 21 : 61 - dimethyl - 41 - chloropyridine-31-carboxylic acid amide and sodium benzene - sulphon - 21 : 61 - dimethyl - 41 - chlorpyridine-31-carboxylic acid amide 4-aminomethane sulphonate can be obtained in a similar manner; (III) 4-aminobenzene-sulphon-11-ethylpyridone-(61) -carboxylic acid amide is prepared from para-acetylaminobenzene sulphonamide and 1-ethylpyridone-(6)-3-carboxylic acid; (IV) 4 - aminobenzene - sulphon - 21 : 41 - dimethylcoumalic acid amide is prepared from 4-carbethoxy-aminobenzene sulphonamide and 2 : 4-dimethyl coumalic acid chloride; (V) 4-aminobenzene - sulphon - 51 - methylpyrimidine - (41)-carboxylic acid amide is prepared from para-nitrobenzene-sulphochloride and 5-methylpyrimidine-(4)-carboxylic acid amide; (VI) 4-aminobenzene-sulphon-21-61-dimethyl-41 -ethoxypyridine-31-carboxylic acid amide is prepared from 2 : 6-dimethyl-4-ethoxypyridine-3-carboxylic acid chloride and para nitrobenzene sulphonamide; (VII) 4-aminobenzene-sulphon-51 - tertiary - butylfurane - 21 - carboxylic acid is prepared from 5-tertiary-butylfurance-2-carboxylic acid chloride and para-nitrobenzene sulphonamide. Specification 578,564 is referred to.
GB21582/44A 1943-11-05 1944-11-03 Manufacture of para-aminobenzene sulphonacylamides Expired GB598472A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH598472X 1943-11-05

Publications (1)

Publication Number Publication Date
GB598472A true GB598472A (en) 1948-02-19

Family

ID=4522596

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21582/44A Expired GB598472A (en) 1943-11-05 1944-11-03 Manufacture of para-aminobenzene sulphonacylamides

Country Status (1)

Country Link
GB (1) GB598472A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065225A (en) * 1960-02-05 1962-11-20 Hoffmann La Roche N', n4-di-isoxazolylcarbonyl-sulfanilamide derivatives
WO2008147797A3 (en) * 2007-05-25 2009-07-09 Vertex Pharma Ion channel modulators and methods of use

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065225A (en) * 1960-02-05 1962-11-20 Hoffmann La Roche N', n4-di-isoxazolylcarbonyl-sulfanilamide derivatives
WO2008147797A3 (en) * 2007-05-25 2009-07-09 Vertex Pharma Ion channel modulators and methods of use
US8193194B2 (en) 2007-05-25 2012-06-05 Vertex Pharmaceuticals Incorporated Ion channel modulators and methods of use

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