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GB687760A - Improvements relating to the preparation of heterocyclic sulphonamides - Google Patents

Improvements relating to the preparation of heterocyclic sulphonamides

Info

Publication number
GB687760A
GB687760A GB6980/51A GB698051A GB687760A GB 687760 A GB687760 A GB 687760A GB 6980/51 A GB6980/51 A GB 6980/51A GB 698051 A GB698051 A GB 698051A GB 687760 A GB687760 A GB 687760A
Authority
GB
United Kingdom
Prior art keywords
sulphonamide
thiadiazole
acetylamino
dimethyl
triazole
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
GB6980/51A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB687760A publication Critical patent/GB687760A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/76—Sulfur atoms attached to a second hetero atom
    • C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Heterocyclic sulphonamides of the general formula <FORM:0687760/IV (b)/1> in which R and R1 are hydrogen, alkyl, aralkyl, alkaryl or thiazolyl radicals, Y is sulphur nitrogen or carbon, and Z is a 2- or 3-membered radical necessary to form a 5- or 6-membered heterocyclic ring, which may contain carbon and/or nitrogen or may be a portion of a carbocyclic ring or nitrogen-containing heterocyclic ring, are prepared by reacting a mercapto compound of the formula <FORM:0687760/IV (b)/2> with an excess of chlorine in an aqueous acid solution and subsequently reacting the sulphonyl chloride thus obtained with ammonia or a primary or secondary amine containing the radicals R and R1. The temperature during chlorination is maintained between - 10 DEG and 25 DEG C. and during the reaction of the sulphonyl chloride with ammonia or amine not above 60 DEG C. The acid used during the chlorination may be aqueous hydrochloric or acetic acid. The invention also includes specifically the compound 2 - acetylamino - 1,3,4 - thiadiazole - 5 - sulphonamide. Examples are given of the preparation of 1,2,4-triazole-3-sulphonamide, 3 - hydroxy - 4 - phenyl - 4,1,2 - triazole - 5 - sulphonamide, 4 - phenyl - 4,1,2 - triazole - 3,5 - disulphonamide, 2 - acetylamino - 1,3,4 - thiadiazole - 5 - sulphonamide, 2 - amino - 1,3,4 - thiadiazole - 5 - sulphonamide, 1,3,4 - thiadiazole - 2,5 - disulphonamide, 2 - acetylamino - 1,3,4 - thiadiazole - 5 - sulphon - n - propylamide, 2 - acetylamino - 1,3,4 - thiadiazole - 5 - sulphondi - n - butylamide, 2 - acetylamino - 1,3,4 - thiadiazole - 5 - sulphonbenzylamide, 2-acetylamino - 1,3,4 - thiadiazole - 5 - sulphon - p - toluidide, 1 - methyl - 5 - tetrazolesulphonamide, 1 - phenyl - 5 - tetrazolesulphonamide, pyrido - [2,1 - c] - s - triazole - 3 - sulphonamide, pyrido - [2,1 - c] - s - triazole - 3 - sulphon-p - toluidide, 2 - imidazolesulphonamide, 1 - methyl - 2 - imidazolesulphonamide, 1 - phenyl - 2 - imidazolesulphonamide, 2 - benzimidazole sulphonamide, 2 - imidazolesulphon - di - n - butylamide, 2 - imidazolesulphon - p - toluidide, 2 - benzolthiazolesulphonamide, 2 - benzothiazolesulphon - n - propylamide, 2 - benzothiaxolesulphon - di - n - butylamide, N - (21 - thiazolyl) benzothiazole - 2 - sulphonamide, 2 - pyrimidinesulphonamide, 5 - chloro - 2 - pyrimidinesulphonamide, 4,6 - dimethyl - 2 - pyrimidinesulphonamide, 4,6 - dimethyl - 2 - pyrimidinesulphon - n - propylamide, 4,6 - dimethyl - 2 - pyrimidinesulphon - di - n - butylamide, 4,6 - dimethyl - 2 - pyrimidinesulphon - p - toluidide, 4,6 - dimethyl - 2 - pyrimidinesulphonbenzylamide, N - (21 - thiazolyl) - 4,6 - dimethyl-2-pyrimidinesulphonamide and 2-pyrazinesulphonamide.
GB6980/51A 1950-04-04 1951-03-22 Improvements relating to the preparation of heterocyclic sulphonamides Expired GB687760A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US687760XA 1950-04-04 1950-04-04

Publications (1)

Publication Number Publication Date
GB687760A true GB687760A (en) 1953-02-18

Family

ID=22084635

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6980/51A Expired GB687760A (en) 1950-04-04 1951-03-22 Improvements relating to the preparation of heterocyclic sulphonamides

Country Status (5)

Country Link
BE (1) BE502319A (en)
DE (1) DE915809C (en)
FR (2) FR1034958A (en)
GB (1) GB687760A (en)
NL (1) NL77246C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2597478A1 (en) * 1986-04-21 1987-10-23 Esteve Labor Dr BENZIMIDAZOLES AND IMIDAZOPYRIDINES SULFONAMIDES, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS.

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2744907A (en) * 1954-01-27 1956-05-08 American Cyanamid Co Production of heterocyclic sulfonyl chlorides
US2868800A (en) * 1954-10-13 1959-01-13 Upjohn Co 6-ethoxybenzothiazole-2-sulfonamide
DE1024973B (en) * 1955-07-15 1958-02-27 Schering Ag Process for the preparation of 2-acylamino-1, 3, 4-thiodiazole-5-sulfonacylamides
DE1103341B (en) * 1957-04-04 1961-03-30 Omikron Gagliardi Societa Di F Process for the preparation of heterocyclic sulfohalides
IT1176613B (en) * 1984-08-14 1987-08-18 Ravizza Spa PHARMACOLOGICALLY ACTIVE PIPERAZINIC DERIVATIVES AND PROCESS FOR THEIR PREPARATION

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2597478A1 (en) * 1986-04-21 1987-10-23 Esteve Labor Dr BENZIMIDAZOLES AND IMIDAZOPYRIDINES SULFONAMIDES, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS.
EP0246126A1 (en) * 1986-04-21 1987-11-19 Laboratorios Del Dr. Esteve, S.A. Benzimidazoles and imidazopyridine sulfone amides, process for their preparation and their use as medicaments
US4933338A (en) * 1986-04-21 1990-06-12 Laboratorios Del Dr. Esteve, S.A. Benzimidazolesulfonamides and their application as drugs

Also Published As

Publication number Publication date
FR72707E (en) 1960-04-28
NL77246C (en)
BE502319A (en)
FR1034958A (en) 1953-08-10
DE915809C (en) 1954-07-29

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