GB886693A - Heterocyclic compounds - Google Patents

Heterocyclic compounds

Info

Publication number
GB886693A
GB886693A GB7505/59A GB750559A GB886693A GB 886693 A GB886693 A GB 886693A GB 7505/59 A GB7505/59 A GB 7505/59A GB 750559 A GB750559 A GB 750559A GB 886693 A GB886693 A GB 886693A
Authority
GB
United Kingdom
Prior art keywords
group
pyrimidine
substituted
amino
nitro
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
GB7505/59A
Inventor
Richard Clarkson
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB7505/59A priority Critical patent/GB886693A/en
Priority to DEJ17764A priority patent/DE1137441B/en
Priority to FR820320A priority patent/FR1426868A/en
Priority to FR837329A priority patent/FR539M/fr
Publication of GB886693A publication Critical patent/GB886693A/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
    • C07D239/46—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
    • C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

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

Abstract

The nvention comprises sulphanilamido-pyrimidines of the formula <FORM:0886693/IV (b)/1> wherein Y is a hydrogen or halogen atom or an alkyl or nitro group and X stands for the group -OR1 or SR1 wherein R1 is a hydrocarbon radical, e.g. methyl, ethyl, propyl, butyl, phenyl or benzyl, which may optionally be substituted, and it comprises also processes for the preparation of these compounds by (a) reacting a 4 - p - substituted - benzenesulphonamido - 6 - substituted pyrimidine in which the p-substituent is an amino group or a group which is subsequently converted to amino by hydrolysis or reduction (e.g. acylamino, nitro or arylazo) and the 6-substituent is a halogen atom or a trialkyl-ammonium group, with a compound MX wherein M is a metal, preferably an alkali-metal such as sodium; (b) reacting a benzenesulphonyl halide, p-substituted by an amino group or a group which is subsequently converted thereto with the appropriate 4-aminopyrimidine; or (c) heating together a pyrimidine compound substituted in the 6-position with an OR1 or SR1 group and in the 4-position by a halogen atom or an OR1 or SR1 group and sulphanilamide or a salt thereof. The compounds are used as anti-bacterial agents. Specified products include 6-methoxy-, ethoxy-, methylthio-, propoxy-, isopropoxy-, butoxy-, sec. butoxy-, b -methoxyethoxy-, b -hydroxyethoxy-, phenylthio-, benzylthio-, phenoxy- and benzyloxy-, 4-sulphanilamido-pyrimidine and the 5-methyl-, 5-nitro- and 5-chloro-, 6-methoxy-4-sulphanilamido-pyrimidines. Benzenesulphonamido-pyrimidines used as starting materials in process (a) above wherein the benzene ring is p-substituted by a group convertible to an amino group such as a nitro, phenylazo-acetylamino or carbethoxyamino group are prepared by reaction of a substituted benzenesulphonamide with a 4 : 6-dihalopyrimidine and, where the desired starting material is a 6-trialkylammonium compound, reacting the 6-halo-4-benzenesulphonamido-pyrimidine obtained with a trialkylamine. Similarly compounds corresponding to the products of formula I above, but having as a p-substituent a group convertible to an amino group are obtained as intermediates in process (b). 4-Amino-pyrimidines used as starting materials in process (b) such as 6-methoxy-, 6-phenoxy-, and 6-benzyloxy-, 4-amino-pyrimidine are made by reaction of 4-amino-6-chloro-pyrimidine (obtained by reaction of 4 : 6-dichloro-pyrimidine and ammonia) with the appropriate alkali metal alcoholate or phenolate. 4 : 6-Dimethoxy-5-nitro-pyrimidine is made by reaction of 4 : 6-dichloro-5-nitro-pyrimidine with sodium methoxide.
GB7505/59A 1959-03-04 1959-03-04 Heterocyclic compounds Expired GB886693A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB7505/59A GB886693A (en) 1959-03-04 1959-03-04 Heterocyclic compounds
DEJ17764A DE1137441B (en) 1959-03-04 1960-02-29 Process for the preparation of 4-sulfanilamidopyrimidine derivatives
FR820320A FR1426868A (en) 1959-03-04 1960-03-03 Obtaining new pyrimidine derivatives
FR837329A FR539M (en) 1959-03-04 1960-08-31

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7505/59A GB886693A (en) 1959-03-04 1959-03-04 Heterocyclic compounds

Publications (1)

Publication Number Publication Date
GB886693A true GB886693A (en) 1962-01-10

Family

ID=9834406

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7505/59A Expired GB886693A (en) 1959-03-04 1959-03-04 Heterocyclic compounds

Country Status (3)

Country Link
DE (1) DE1137441B (en)
FR (1) FR539M (en)
GB (1) GB886693A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3247193A (en) * 1966-04-19 And the preparatpdn
US3862190A (en) * 1972-09-08 1975-01-21 Pfizer 5-(unsubstituted and substituted phenoxy)-4-amino pyrimidines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1445607A1 (en) * 1962-12-14 1968-12-05 Ciba Geigy New sulfonamides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE926131C (en) * 1951-06-24 1955-04-07 Nordmark Werke Gmbh Process for the preparation of 4- (p-aminobenzenesulfoyl) -amino-2-alkyl-6-alkoxypyrimidines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3247193A (en) * 1966-04-19 And the preparatpdn
US3862190A (en) * 1972-09-08 1975-01-21 Pfizer 5-(unsubstituted and substituted phenoxy)-4-amino pyrimidines

Also Published As

Publication number Publication date
FR539M (en) 1961-05-23
DE1137441B (en) 1962-10-04

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