GB876601A - Pyrimidine derivatives - Google Patents

Pyrimidine derivatives

Info

Publication number
GB876601A
GB876601A GB22904/59A GB2290459A GB876601A GB 876601 A GB876601 A GB 876601A GB 22904/59 A GB22904/59 A GB 22904/59A GB 2290459 A GB2290459 A GB 2290459A GB 876601 A GB876601 A GB 876601A
Authority
GB
United Kingdom
Prior art keywords
radical
formula
alkyl
phenylazo
prepared
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
GB22904/59A
Inventor
Alan Hodgson Laird
Justus Kenneth Landquist
Bernard William Langley
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 GB22904/59A priority Critical patent/GB876601A/en
Priority to CH747860A priority patent/CH410962A/en
Priority to FR837072A priority patent/FR377M/en
Publication of GB876601A publication Critical patent/GB876601A/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
    • 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
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Landscapes

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

Abstract

The invention comprises compounds of the general formula: <FORM:0876601/IV (b)/1> and salts thereof wherein R1 represents an hydroxy or amino radical, R2 a hydrogen atom or an alkyl radical R3 represents a substituted phenylazo or phenylhydrazo radical of the formula: <FORM:0876601/IV (b)/2> wherein R4, R5, R6 and R7 which may be the same or different each represent a hydrogen or a halogen atom, or an alkyl or an alkenyl radical, and the preparation of the phenylazopyrimidines by reacting a hydrazinopyrimidine of the formula <FORM:0876601/IV (b)/3> with a benzoquinone of the formula: <FORM:0876601/IV (b)/4> and of the phenylhydrazopyrimidines by reducing the corresponding azo compound (The phenylazo radical of the general formula: <FORM:0876601/IV (b)/5> may be represented by the tautomeric formula: <FORM:0876601/IV (b)/6> 4-Hydrazino -2,6- dihydroxypyrimidine is prepared from 4-chloro-2,6-dihydroxypyrimidine and hydrazine hydrate. Similarly prepared is 4-hydrazino-2,6-dihydroxy-5-methylpyrimidine. 4-Chloro-2,6-dihydroxy-5- methylpyrimidine is prepared by acid hydrolysis of the dimethyl ether. 2-Amino-4-hydrazino-6- hydroxypyrimidine is prepared from 2-amino-4-chloro-6-hydroxypyrimidine and hydrazine hydrate.ALSO:Azo compounds of the general formula:- <FORM:0876601/IV(c)/1> wherein R1 is a hydroxy or amino radical, R2 a hydrogen atom or an alkyl radical and R4, R5, R6 and R7 are the same or different and are hydrogen or halogen atoms or alkyl or alkenyl radicals, are prepared by reacting a compound of the formula:- <FORM:0876601/IV(c)/2> with a quinone of the general formula:- <FORM:0876601/IV(c)/3> The reaction may be carried out in an inert diluent or solvent and in the presence of an acid catalyst. Alternatively the reaction may be carried out in acetic or formic acid.ALSO:Pharmaceutical and veterinary compositions comprise at least one phenylazo or phenylhydrazo-pyrimidine of the general formula <FORM:0876601/VI/1> or a salt thereof in admixture with a non-toxic pharmaceutically-acceptable diluent or carrier. In the above formula R1 represents a hydroxy or amino radical, R2 a hydrogen atom or an alkyl group, and R3 a substituted phenylazo or phenylhydrazo radical of the formula <FORM:0876601/VI/2> wherein R4, R5, R6 and R7 which may be the same or different represent hydrogen or halogen atoms or alkyl or alkenyl radicals. The compositions may be for oral, parenteral or topical administration and may be in the form of tablets, aqueous or oily solutions or suspensions which may also be sterile, ointments or creams. A cream useful for intramamnary injection contains 2,6 - dihydroxy - 4 - (4 - hydroxy - phenylazo) pyridine and polyethylene glycols.
GB22904/59A 1959-07-03 1959-07-03 Pyrimidine derivatives Expired GB876601A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB22904/59A GB876601A (en) 1959-07-03 1959-07-03 Pyrimidine derivatives
CH747860A CH410962A (en) 1959-07-03 1960-07-01 Process for the preparation of phenylazopyrimidines
FR837072A FR377M (en) 1959-07-03 1960-08-29 Antibacterial drug based on 2: 6-dihydroxy-4- (4'-hydroxyphenylazo) pyrimidine, or its salts.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22904/59A GB876601A (en) 1959-07-03 1959-07-03 Pyrimidine derivatives

Publications (1)

Publication Number Publication Date
GB876601A true GB876601A (en) 1961-09-06

Family

ID=10186945

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22904/59A Expired GB876601A (en) 1959-07-03 1959-07-03 Pyrimidine derivatives

Country Status (3)

Country Link
CH (1) CH410962A (en)
FR (1) FR377M (en)
GB (1) GB876601A (en)

Also Published As

Publication number Publication date
FR377M (en) 1961-04-04
CH410962A (en) 1966-04-15

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