GB914929A - Novel sulphonamides and a process for the manufacture thereof - Google Patents

Novel sulphonamides and a process for the manufacture thereof

Info

Publication number
GB914929A
GB914929A GB23391/61A GB2339161A GB914929A GB 914929 A GB914929 A GB 914929A GB 23391/61 A GB23391/61 A GB 23391/61A GB 2339161 A GB2339161 A GB 2339161A GB 914929 A GB914929 A GB 914929A
Authority
GB
United Kingdom
Prior art keywords
pyrimidine
lower alkoxy
condensing
methoxy
sulphanilamido
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
GB23391/61A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB914929A publication Critical patent/GB914929A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D239/34—One oxygen atom
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or 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
    • C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)

Abstract

The invention comprises 4-sulphanilamido-5-(lower alkoxy)-pyrimidines (wherein "lower alkoxy" indicates a group fo 1-6 carbon atoms) and salts thereof, and their preparation by (a) condensing a 4-halogeno-5-(lower alkoxy)-pyrimidine with an alkali-metal salt of sulphanilamide or an N4-acyl derivative thereof; (b) reacting a 4-halogeno-5-(lower alkoxy)-pyrimidine with a tri(lower alkyl)amine, e.g. trimethylamine, and condensing the resulting 4-trialkylammonium-5-(lower alkoxy)-pyrimidine halide with an alkali-metal salt of sulphanilamide or an N4-acyl sulphanilamide or (c) reacting the 4-halogeno-5-(lower alkoxy)-pyrimidine with ammonia and condensing the resulting 4-amino-5-(lower alkoxy)-pyrimidine with a benzenesulphonyl halide containing in the para position a substituent convertible to amino by hydrolysis or reduction (e.g. an acylamino such as acetylamino or alkoxycarbonylamino, benzyloxycarbonylamino, nitro, nitroso, azo or hydrazo group); and where necessary converting the para-substituent in the products of the above processes into an amino group, by reduction or hydrolysis. The preferred product is 4-sulphanilamido-5-methoxy-pyrimidine. 4-Halo-5-(lower alkoxy)-pyrimidines, e.g. 4-chloro-5-methoxy-pyrimidine used as starting materials are made by treating a 4-hydroxy-5-(lower alkoxy)-pyrimidine with an oxyhalide such as phosphorus oxychloride. 4-Hydroxy-5-methoxy-pyrimidine is made by reacting methyl methoxyacetate, ethylformate and sodium to give the sodium salt of methyl formyl-methoxyacetate, condensing with thiourea in the presence of sodium methoxide to form 4-hydroxy-5-methoxy-2-mercapto-pyrimidine and removing the mercapto group by treating with Raney nickel in aqueous ammonia. Pharmaceutical preparations having antibacterial activity comprise the 4-sulphanilamido-5-alkoxy pyrimidines of the invention or salts thereof in admixture with a pharmaceutical, organic or inorganic, solid or liquid carrier suitable for enteral (e.g. oral) or parenteral administration, suitably in the form of tablets, dragees, suppositories, capsules, solutions, suspensions or emulsions, which may contain, in addition to conventional excipients, stabilizing, preserving, wetting or emulsifying agents, salts for varying osmotic pressure or buffers.
GB23391/61A 1960-07-01 1961-06-28 Novel sulphonamides and a process for the manufacture thereof Expired GB914929A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH750760A CH393334A (en) 1960-07-01 1960-07-01 Process for the preparation of new sulfonamides of the pyrimidine series

Publications (1)

Publication Number Publication Date
GB914929A true GB914929A (en) 1963-01-09

Family

ID=4326203

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23391/61A Expired GB914929A (en) 1960-07-01 1961-06-28 Novel sulphonamides and a process for the manufacture thereof

Country Status (4)

Country Link
CH (1) CH393334A (en)
FR (1) FR1282M (en)
GB (1) GB914929A (en)
NL (1) NL266593A (en)

Also Published As

Publication number Publication date
CH393334A (en) 1965-06-15
FR1282M (en) 1962-05-02
NL266593A (en)

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