GB691020A - Improvements in or relating to pyrimidine derivatives of therapeutic value and to the manufacture thereof - Google Patents
Improvements in or relating to pyrimidine derivatives of therapeutic value and to the manufacture thereofInfo
- Publication number
- GB691020A GB691020A GB3187/51A GB318751A GB691020A GB 691020 A GB691020 A GB 691020A GB 3187/51 A GB3187/51 A GB 3187/51A GB 318751 A GB318751 A GB 318751A GB 691020 A GB691020 A GB 691020A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- give
- diamino
- phenylpyrimidine
- hydroxy
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen 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
- C07D239/48—Two nitrogen 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
- C07D239/50—Three nitrogen 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
- C07D239/56—One oxygen atom and one sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 5-phenylpyrimidines of the general formula <FORM:0691020/IV (b)/1> wherein X is hydrogen, halogen, nitro, amino or acidylamine and Y is halogen or hydrogen and their acid addition salts. They are prepared by (a) condensing an a -formylphenylacetic acid ester with guanidine to give a 2-amino-4-hydroxy-5-phenylpyrimidine which is chlorinated and aminated to give the 2 : 4-diamino compound; (b) introducing a nitro group into the phenyl nucleus of 2 : 4-diamino-5-phenyl pyrimidine to give 2 : 4-diamino-5-p-nitro phenyl pyrimidine which may be reduced and acetylated to give the p-amino and p-acetylamino compounds; (c) reacting a 5-phenylpyrimidine containing 2 : 4-dihydroxy, 2-mercapto-4-hydroxy, 2-ethylmercapto-4-hydroxy or 2 - amino - 4 - hydroxy substituents with phosphorus pentasulphide to give the 2 : 4-dimercapto derivative which is converted to the 2 : 4-diamino compound by reaction with ammonium or by the methods of Specifications 663,567, 671,927 and 684,759; or (d) condensing an a -formylphenylacetonitrile or its enol ether with guanidine. In examples: (1)-(6) 2-amino-4-hydroxy-5-phenylpyrimidines are chlorinated and aminated to give the corresponding 2 : 4-diaminopyrimidines substituted in the 5-position by phenyl, p-chlorophenyl, p-bromophenyl, 3 : 4 - dichlorophenyl, m - chlorophenyl or m-bromophenyl groups; (7) 2 : 4-diamino-5-phenylpyrimidine is nitrated to give 2 : 4-diamino - 5 - p - nitrophenyl pyrimidine; (8) the product of (7) is reduced to give the p-amino compound; (9) the p-amino compound from (8) is acetylated to 2 : 4-diamino-5-p-acetamidophenylpyrimidine; (10) 2 : 4-dithiol-5-phenylpyrimidine is aminated to 4-amino-5-phenyl-2-thiol pyrimidine which is reacted with chloracetic acid to give 4-amino-2-carboxymethylthio-5-phenylpyrimidine which is further aminated to 2 : 4 - diamino - 5 - phenylpyrimidine; and (11) phenylformylacetonitrile methyl ether is treated with guanidine to give 2 : 4-diamino-5-phenylpyrimidine. 2 - Amino - 4 - hydroxy - 5 - phenylpyrimidines. The 5-phenyl-, 5-p-chlorophenyl-, 5-p-bromophenyl-, 5-(31 : 41-dichlorophenyl)- and 5-m-chlorophenyl-, 2-amino-4-hydroxypyrimidines are prepared from the corresponding ethyl phenylacetate, ethyl formate and guanidine. Specification 687,032 also is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US691020XA | 1950-02-15 | 1950-02-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB691020A true GB691020A (en) | 1953-05-06 |
Family
ID=22086773
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3187/51A Expired GB691020A (en) | 1950-02-15 | 1951-02-09 | Improvements in or relating to pyrimidine derivatives of therapeutic value and to the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB691020A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
-
1951
- 1951-02-09 GB GB3187/51A patent/GB691020A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
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