GB875562A - Improvements in and relating to pyrimidine derivatives and the preparation thereof - Google Patents

Improvements in and relating to pyrimidine derivatives and the preparation thereof

Info

Publication number
GB875562A
GB875562A GB5871/57A GB587157A GB875562A GB 875562 A GB875562 A GB 875562A GB 5871/57 A GB5871/57 A GB 5871/57A GB 587157 A GB587157 A GB 587157A GB 875562 A GB875562 A GB 875562A
Authority
GB
United Kingdom
Prior art keywords
dimethoxy
ethyl
pyrimidine
formula
trimethoxyhydrocinnamate
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
GB5871/57A
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
Priority to GB5871/57A priority Critical patent/GB875562A/en
Priority to CH5610458A priority patent/CH366835A/en
Publication of GB875562A publication Critical patent/GB875562A/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
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0875562/IV (b)/1> (wherein R1, R2, R3 are alkyl groups with one to four carbon atoms and may be the same or different); the preparation thereof by formylating a hydrocinnamic ester of the formula: <FORM:0875562/IV (b)/2> condensing the formyl derivative with guanidine, and chlorinating and subsequently aminating the intermediate 2 - amino - 4 - hydroxy - 5 - benzylpyrimidine; and pharmaceutical preparations containing the products (see Group VI). In Example (1), ethyl-3,4,5-trimethoxyhydrocinnamate is reacted with ethyl formate and the formyl derivative condensed with guanidine to give 2-amino-4-hydroxy-5-(3,4,5-trimethoxybenzyl)-pyrimidine, which on treatment with phosphoryl chloride followed by ethanolic ammonia gives 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine. Similarly made is 2,4-diamino - 5 - (3,5-dimethoxy-4-n-butoxybenzyl)-pyrimidine. Ethyl 3,4,5-trimethoxyhydrocinnamate is made by hydrogenating in the presence of Raney nickel ethyl 3,4,5-trimethoxycinnamate, itself made by reacting 3,4,5-trimethoxycinnamic acid with absolute ethanol in the presence of conc. H2SO4. Ethyl 3,5 - dimethoxy-4-n-butoxyhydrocinnamate is similarly made from 3,5-dimethoxy-4-n-butoxy cinnamic acid, itself made from malonic acid and 3,5 - dimethoxy-4-n-butoxybenzaldehyde, which is made from n-butyl iodide and 3,5-dimethoxy-4-hydroxybenzaldehyde. Specifications 687,032 and 734,801 are referred to.ALSO:Antibacterial and antiprotozoal pharmaceutical preparations comprise a compound of the general formula <FORM:0875562/VI/1> (wherein R1, R2 and R3 represent identical or different C1-4 alkyl groups), together with a carrier therefor. They may take the form of tablets, capsules or suspensions in liquids, and may additionally contain chemotherapeutic sulphonamides (e.g. sulphaguanidine). Specifications 687,032 and 734,801 are referred to.
GB5871/57A 1957-02-21 1957-02-21 Improvements in and relating to pyrimidine derivatives and the preparation thereof Expired GB875562A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5871/57A GB875562A (en) 1957-02-21 1957-02-21 Improvements in and relating to pyrimidine derivatives and the preparation thereof
CH5610458A CH366835A (en) 1957-02-21 1958-02-20 Process for the production of new, therapeutically effective pyrimidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5871/57A GB875562A (en) 1957-02-21 1957-02-21 Improvements in and relating to pyrimidine derivatives and the preparation thereof

Publications (1)

Publication Number Publication Date
GB875562A true GB875562A (en) 1961-08-23

Family

ID=9804169

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5871/57A Expired GB875562A (en) 1957-02-21 1957-02-21 Improvements in and relating to pyrimidine derivatives and the preparation thereof

Country Status (2)

Country Link
CH (1) CH366835A (en)
GB (1) GB875562A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006987A1 (en) * 1978-05-24 1980-01-23 The Wellcome Foundation Limited 2,4-Diamino-5-benzylpyrimidines, especially for the treatment of microbial infections, pharmaceutical compositions containing these compounds and processes for preparing these compounds
US4992430A (en) * 1984-05-22 1991-02-12 Dr. Karl Thomae Gmbh Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase
WO2002010157A1 (en) * 2000-07-29 2002-02-07 Arpida Ag Benzofuran derivatives and their use as antibacterial agents
WO2005005418A1 (en) 2003-07-11 2005-01-20 Arpida Ag Benzofuran derivatives and their use in the treatment of microbial infections
US7524855B2 (en) 2005-01-07 2009-04-28 Arpida Ag Selected benzofuran derivatives

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006987A1 (en) * 1978-05-24 1980-01-23 The Wellcome Foundation Limited 2,4-Diamino-5-benzylpyrimidines, especially for the treatment of microbial infections, pharmaceutical compositions containing these compounds and processes for preparing these compounds
US4992430A (en) * 1984-05-22 1991-02-12 Dr. Karl Thomae Gmbh Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase
US5084449A (en) * 1984-05-22 1992-01-28 Dr. Karl Thomae Gmbh Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase
WO2002010157A1 (en) * 2000-07-29 2002-02-07 Arpida Ag Benzofuran derivatives and their use as antibacterial agents
WO2002010156A1 (en) * 2000-07-29 2002-02-07 Arpida Ag Benzofuran derivatives and their use as antibacterial agents
US7030130B2 (en) 2000-07-29 2006-04-18 Arpida Ag Benzofuran derivatives and their use as antibacterial agents
CN1317277C (en) * 2000-07-29 2007-05-23 阿皮德公开股份有限公司 Benzofuran derivatives and their use as antibacterial agents
WO2005005418A1 (en) 2003-07-11 2005-01-20 Arpida Ag Benzofuran derivatives and their use in the treatment of microbial infections
US7524855B2 (en) 2005-01-07 2009-04-28 Arpida Ag Selected benzofuran derivatives

Also Published As

Publication number Publication date
CH366835A (en) 1963-01-31

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