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 thereof

Info

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
Application number
GB3187/51A
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Publication of GB691020A publication Critical patent/GB691020A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48Two nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50Three nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56One 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.
GB3187/51A 1950-02-15 1951-02-09 Improvements in or relating to pyrimidine derivatives of therapeutic value and to the manufacture thereof Expired GB691020A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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