GB845552A - Pyrimidine derivatives - Google Patents

Pyrimidine derivatives

Info

Publication number
GB845552A
GB845552A GB32563/56A GB3256356A GB845552A GB 845552 A GB845552 A GB 845552A GB 32563/56 A GB32563/56 A GB 32563/56A GB 3256356 A GB3256356 A GB 3256356A GB 845552 A GB845552 A GB 845552A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydroxypyrimidine
triazolo
hydroxy
pyrimidine
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
GB32563/56A
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB845552A publication Critical patent/GB845552A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients

Abstract

The invention comprises (a) 5-hydroxy-7-methyl-s-triazolo (3,4-a) pyrimidines of the general formula: <FORM:0845552/IV(b)/1> where R represents an unsubstituted or carboxylsubstituted alkyl or aryl group; (b) the preparation of compounds (a), and of the compound of formula I in which R represents hydrogen, by thermal cyclization of 2-acylhydrazino-4-methyl-6-hydroxypyrimidines of the general formula: <FORM:0845552/IV(b)/2> (c) the combination of (b) with the preparation of the compounds of formula II by acylation of 2-hydrazino-4-methyl-6-hydroxypyrimidine by the following methods: (i) when R is hydrogen, heating with concentrated formic acid, (ii) when R is other than hydrogen, heating with the appropriate acid chloride or anhydride in the presence of pyridine; (d) therapeutic compositions containing the compounds (a) or the products of (b) or (c) (see Group VI). Cyclisation is accomplished by heating to 220-280 DEG under reduced pressure in an inert atmosphere or, when R = -CH3 or -CH2CH2COOH, by refluxing in glacial acetic acid for some hours. when R = -C6H4.COOH, cyclisation occurs directly during the preparation of the acyl intermediate. The preparation of the following is described in the examples: 5-hydroxy-7-methyl-s-triazolo (3,4-a) pyrimidine, 5-hydroxy-3,7-dimethyl-s-triazolo (3,4-a) pyrimidine, [5-hydroxy-7-methyl -s-triazolo (3,4-a) pyrimidine]-3-b -propionic acid, 3-phenyl-5-hydroxy-7-methyl-s-triazolo (3,4-a) pyrimidine and [5-hydroxy-7-methyl-s-triazolo (3,4-a) pyrimidine] - 3 - o - benzoic acidtogether with the following intermediates:2-formyl, hydrazino-4-methyl-6-hydroxypyrimidine, acetylhydrazino-4-methyl-6-hydroxypyrimidine, 2-succinylhydrazino-4-methyl-6-hydroxypyrimidine and 2-benzoylhydrazino-4-methyl-6-hydroxypyrimidine. 2-Hydrazino-4-methyl-6-hydroxypyrimidine is prepared by condensing 2-methylthio-4-methyl-6-hydroxypyrimidine with hydrazine hydrate in ethanol, and is characterised by refluxing with acetone to form 2-isopropylidene-hydrazine-4-methyl-6-hydroxypyrimidine.ALSO:Therapeutic compositions comprise, in admixture with a therapeutically acceptable carrier, at least one 5-hydroxy-7-methyl-s-triazolo (3,4-a) pyrimidine of the general formula <FORM:0845552/VI/1> wherein R represents a hydrogen atom or an unsubstituted or carboxyl-substituted alkyl or aryl group. The said compound, which possesses antitumoral activity, may be made up in solution or suspension in liquids, including oil bases, for injection, in tablets or capsules for oral administration, or in bases suitable for topical administration.
GB32563/56A 1955-10-26 1956-10-25 Pyrimidine derivatives Expired GB845552A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT845552X 1955-10-26

Publications (1)

Publication Number Publication Date
GB845552A true GB845552A (en) 1960-08-24

Family

ID=11325143

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32563/56A Expired GB845552A (en) 1955-10-26 1956-10-25 Pyrimidine derivatives

Country Status (1)

Country Link
GB (1) GB845552A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2549834A1 (en) * 1983-07-25 1985-02-01 Sanofi Sa TRIAZOLO-PYRIMIDINE DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC APPLICATION AS TONICARDIACS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2549834A1 (en) * 1983-07-25 1985-02-01 Sanofi Sa TRIAZOLO-PYRIMIDINE DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC APPLICATION AS TONICARDIACS
EP0136198A1 (en) * 1983-07-25 1985-04-03 Sanofi Triazolo pyrimidine derivatives, process for their preparation and their therapeutical use as cardiotonics

Similar Documents

Publication Publication Date Title
US3843681A (en) 1-carboxamido pyrano(thiopyrano)(3,4-6)indole derivatives
SE7614539L (en) PROCEDURE FOR THE PREPARATION OF CARBOSTYRIL DERIVATIVES WITH THERAPEUTIC EFFECT
GB1055055A (en) Improvements in or relating to 4-[1-lower alkyl piperidylidene-(4)]-9,10-dihydro-4h-benzo[4,5]-cyclohepta[1,2-b]thiophene derivatives
JPH03503889A (en) 1H/3H-[4-(N,N-dicycloalkyl/branched alkylcarboxamide)-benzyl]imidazo[4,5-c]pyridines as PAF antagonists
US3825558A (en) Substituted aminopropoxy-2-indolinones
GB753919A (en) Improvements relating to derivatives of 2-aryl indoles and of 2-aryl indolines, and their use
US4818772A (en) Derivatives of 4-aminoethoxy-5-isopropyl-2-methylbenzenes: methods of synthesis and utilization as medicines
GB1023220A (en) Production of carboxylic acid amides
US3150143A (en) Therapeutically active nu-substituted azaspiranes
GB1254332A (en) Amino acids and their derivatives and processes for preparing them
US3646046A (en) 1 6-dimethyl-10alpha-ergoline derivatives
GB845552A (en) Pyrimidine derivatives
KR880011122A (en) 4-thioquinazolin derivatives, preparation method thereof and pharmaceutical composition
US4176184A (en) Imidazoisoquinoline-diones and salts thereof
NO139130B (en) PROCEDURE FOR PREPARING 2-ALKYLAMINO-DIHYDROPYRIDINES
US4757070A (en) 3-oxadiazolyl-5-aminoalkyl-beta-carboline derivatives compositions and use
US3819634A (en) 4-phenyl-3-thioacrylaminoquinolines
CA1245228A (en) Allylic amines
US3882143A (en) 4-(2-hydroxy-3-aminopropoxy)oxindole derivatives
GB1109690A (en) 5-oxo-3,4,5,6-tetrahydro-1h-azepino[4,3,2-cd]indoles and the manufacture thereof
ES355312A1 (en) Pyrimidine derivatives
US3775421A (en) 5a,6,7,8,9,9a-hexahydro-9a-hydroxypyrido(2,1-b)benzothiazolium halides
US3518269A (en) 1-oxime substituted quinolizines
GB721171A (en) Derivatives of ª‰- and ª†- carbolines
US3823153A (en) 2-substituted-3a,4,5,6,7,7a-hexahydro-3a-hydroxybenzothiazolium halides