GB886693A - Heterocyclic compounds - Google Patents
Heterocyclic compoundsInfo
- 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
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.
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1445607A1 (en) * | 1962-12-14 | 1968-12-05 | Ciba Geigy | New sulfonamides |
Family Cites Families (1)
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 |
-
1959
- 1959-03-04 GB GB7505/59A patent/GB886693A/en not_active Expired
-
1960
- 1960-02-29 DE DEJ17764A patent/DE1137441B/en active Pending
- 1960-08-31 FR FR837329A patent/FR539M/fr active Active
Cited By (2)
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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