ES269656A1 - Novel sulphonamides and a process for their manufacture - Google Patents

Novel sulphonamides and a process for their manufacture

Info

Publication number
ES269656A1
ES269656A1 ES0269656A ES269656A ES269656A1 ES 269656 A1 ES269656 A1 ES 269656A1 ES 0269656 A ES0269656 A ES 0269656A ES 269656 A ES269656 A ES 269656A ES 269656 A1 ES269656 A1 ES 269656A1
Authority
ES
Spain
Prior art keywords
pyrimidine
lower alkoxy
amino
sulphanilamido
pyrimidines
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
ES0269656A
Other languages
Spanish (es)
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 ES269656A1 publication Critical patent/ES269656A1/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
    • C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

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

Abstract

The invention comprises 5-sulphanilamido-6-(lower alkoxy, i.e C1-5 alkoxy)-pyrimidines and pharmaceutically acceptable salts thereof, 5 - (N4-acyl-sulphanilamido)-6-(lower alkoxy)-pyrimidines, and the process for the preparation of the sulphanilamides by condensing a 5-amino-6-(lower alkoxy)-pyrimidine with a benzenesulphonyl halide containing in the para-position a substituent convertible to the amino group by reduction or hydrolysis, e.g. a nitro, alkoxycarbonylamino, benzyloxycarbonylamino or acylamino (such as acetylamino) group, converting the para substituent in the resulting para-substituted-(e.g. p-acylamino-)benzenesulphonamido - pyrimidine to the amino group and, if desired, converting the product into a pharmaceutically acceptable salt, such as an alkali-metal, alkaline-earth metal or organic base (e.g. diethanolamine) salt. Preferred products comprise 5-sulphanilamido-6-methoxy-pyrimidine and its N -acetyl derivative. 5-Amino-6-(lower alkoxy)-pyrimidines such as 5-amino-6-methoxy-pyrimidine are made by reacting 4,6-dichloro-5-nitro-pyrimidine with an alkali-metal alcoholate, reducing the resulting 4-chloro-5-nitro-6-(lower alkoxy)-pyrimidine to 4-chloro-5-amino-6-(lower alkoxy)-pyrimidine and removing the 4-chloroatom by catalytic hydrogenation. Pharmaceutical preparations, having antibacterial activity, comprise the sulphanilamido-pyrimidines of the invention, or salts thereof, in admixture with a solid or liquid, organic or inorganic carrier suitable for enteral (e.g. oral) or parenteral administration. The preparations suitably take the form of tablets, dragees, suppositories, capsules, solutions, emulsions or suspensions and may contain, in addition to usual excipients, preserving, stabilizing, wetting or emulsifying agents, salts for varying osmotic pressure or buffers.
ES0269656A 1960-08-09 1961-08-08 Novel sulphonamides and a process for their manufacture Expired ES269656A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH899560 1960-08-09

Publications (1)

Publication Number Publication Date
ES269656A1 true ES269656A1 (en) 1962-03-16

Family

ID=4347166

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0269656A Expired ES269656A1 (en) 1960-08-09 1961-08-08 Novel sulphonamides and a process for their manufacture

Country Status (5)

Country Link
BE (1) BE606495A (en)
ES (1) ES269656A1 (en)
FR (1) FR1440M (en)
GB (1) GB914417A (en)
NL (1) NL267524A (en)

Also Published As

Publication number Publication date
GB914417A (en) 1963-01-02
NL267524A (en)
BE606495A (en) 1962-01-25
FR1440M (en) 1962-08-13

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