GB1128234A - 5-benzylpyrimidine derivatives and process for the preparation thereof - Google Patents

5-benzylpyrimidine derivatives and process for the preparation thereof

Info

Publication number
GB1128234A
GB1128234A GB737666A GB737666A GB1128234A GB 1128234 A GB1128234 A GB 1128234A GB 737666 A GB737666 A GB 737666A GB 737666 A GB737666 A GB 737666A GB 1128234 A GB1128234 A GB 1128234A
Authority
GB
United Kingdom
Prior art keywords
group
benzyl
hydrogen
halogen
hydrogen atom
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
GB737666A
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 GB737666A priority Critical patent/GB1128234A/en
Priority to GR670133641A priority patent/GR33641B/en
Priority to IL2742467A priority patent/IL27424A/en
Priority to CA983,015A priority patent/CA977754A/en
Priority to NO16687667A priority patent/NO124601B/no
Priority to AT153867A priority patent/AT270653B/en
Priority to AT409368A priority patent/AT275534B/en
Priority to NL6702397A priority patent/NL146811B/en
Priority to DE19671795635 priority patent/DE1795635C3/en
Priority to ES336945A priority patent/ES336945A1/en
Priority to FI48067A priority patent/FI49714C/en
Priority to CH191468A priority patent/CH513179A/en
Priority to CH237967A priority patent/CH511239A/en
Priority to BE694244D priority patent/BE694244A/xx
Priority to DE1967W0043385 priority patent/DE1720012B2/en
Priority to SE227867A priority patent/SE338998B/xx
Priority to DK91167A priority patent/DK120344B/en
Priority to FR95595A priority patent/FR1536204A/en
Priority to SE796270A priority patent/SE390412B/en
Priority to FR106573A priority patent/FR6595M/fr
Priority to FI26868A priority patent/FI55031C/en
Priority to DE19681720031 priority patent/DE1720031A1/en
Priority to FR138498A priority patent/FR94837E/en
Publication of GB1128234A publication Critical patent/GB1128234A/en
Priority to DK59371A priority patent/DK128247B/en
Priority to FI250271A priority patent/FI55032C/en
Priority to NO377771A priority patent/NO133550C/no
Priority to MY7100226A priority patent/MY7100226A/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
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
    • 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
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Abstract

1,128,234. 5-Benzyl-pyrimidine derivatives. WELLCOME FOUNDATION Ltd. (Burroughs Wellcome & Co. (U.S.A.) Inc.). 16 Feb., 1967 [19 Feb., 1966], No. 7376/66. Heading C2C. 5-Benzyl-pyrimidine derivatives of the formula wherein X and Y are the same or different and each is an amino or hydroxyl group, Z is a hydrogen atom, an alkyl group containing not more than 4 carbon atoms, an hydroxyl group, or a substituted or unsubstituted amino group, the said substituted amino group including a cyclic amino group, such as a piperidino or morpholino group, R<SP>1</SP> is a hydrogen atom or a saturated or unsaturated hydrocarbon radical which may be optionally substituted by halogen, and R<SP>2</SP> and R<SP>3</SP> are the same or different and each is a hydrogen atom, a halogen atom, or an alkyl or alkoxy group containing not more than 4 carbon atoms, are prepared by reacting together a pyrimidine derivative and a Mannich base of the respective formulµ wherein NR 2 <SP>4</SP> is a dialkylamino or a cyclicamino group, and optionally reacting the resulting novel 5-benzyl-pyrimidine derivative of the first formula above wherein R<SP>1</SP> is hydrogen with a compound R<SP>1</SP>Q, wherein Q is a reactive atom or group and R<SP>1</SP> is a saturated or unsaturated hydrocarbon radical which may be optionally substituted by halogen, under basic conditions. 2,6 - Dimethoxy - 4 - (N,N - dimethylaminomethyl)-phenol is prepared by reacting together 2,6-dimethoxyphenol, dimethylamine and formaldehyde. Pharmaceutical compositions having antibacterial activity comprise as active ingredient a 5-benzyl-pyrimidine derivative of the first formula above wherein R<SP>1</SP> is hydrogen in admixture with a pharm aceutically acceptable carrier.
GB737666A 1966-02-19 1966-02-19 5-benzylpyrimidine derivatives and process for the preparation thereof Expired GB1128234A (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
GB737666A GB1128234A (en) 1966-02-19 1966-02-19 5-benzylpyrimidine derivatives and process for the preparation thereof
GR670133641A GR33641B (en) 1966-02-19 1967-02-13 CHEMICAL COMPOSITIONS AND METHOD.
IL2742467A IL27424A (en) 1966-02-19 1967-02-13 Method of preparing 5-benzylpyrimidines and novel 5-benzylpyrimidines
CA983,015A CA977754A (en) 1966-02-19 1967-02-15 2-(3',4',5'-trisubstituted-benzyl) pyrimidine compounds
NO16687667A NO124601B (en) 1966-02-19 1967-02-16
AT153867A AT270653B (en) 1966-02-19 1967-02-16 Process for the preparation of new 5-benzylpyrimidines
AT409368A AT275534B (en) 1966-02-19 1967-02-16 Process for the preparation of 5-benzylpyrimidines
BE694244D BE694244A (en) 1966-02-19 1967-02-17
DE19671795635 DE1795635C3 (en) 1966-02-19 1967-02-17 2,4-diamino-5-benzyl pyrimidines
ES336945A ES336945A1 (en) 1966-02-19 1967-02-17 5-benzylpyrimidine derivatives and process for the preparation thereof
FI48067A FI49714C (en) 1966-02-19 1967-02-17 Process for the preparation of 5-benzylpyrimidines.
CH191468A CH513179A (en) 1966-02-19 1967-02-17 Process for the preparation of 5-benzylpyrimidines
CH237967A CH511239A (en) 1966-02-19 1967-02-17 Antibacterial benzylpyrimidines
NL6702397A NL146811B (en) 1966-02-19 1967-02-17 PROCESS FOR THE PREPARATION OF 5-BENZYLPYRIMIDINE DERIVATIVES.
DE1967W0043385 DE1720012B2 (en) 1966-02-19 1967-02-17 Process for the preparation of 2,4-DIAMINO-5- (3,4,5-TRIMETHOXYBENZYL) -PYRIMIDINE
SE796270A SE390412B (en) 1966-02-19 1967-02-20 2,4-DIAMINO-5- (4'-HYDROXYBENZYL) PYRIMIDINES FOR USE, AS A STARTING MATERIAL FOR THE PREPARATION OF 2,4-DIAMINO-5- (3 ', 4', 5'-TRIALICOCIBENSYL) PYRIMIDINES
DK91167A DK120344B (en) 1966-02-19 1967-02-20 Process for the preparation of 5-benzyl-pyrimidines.
FR95595A FR1536204A (en) 1966-02-19 1967-02-20 Process for the preparation of pyrimidine derivatives
SE227867A SE338998B (en) 1966-02-19 1967-02-20
FR106573A FR6595M (en) 1966-02-19 1967-05-16
FR138498A FR94837E (en) 1966-02-19 1968-02-02 Process for the preparation of pyrimidine derivatives.
DE19681720031 DE1720031A1 (en) 1966-02-19 1968-02-02 Biologically active 5-benzylpyrimidine derivatives and processes for their preparation
FI26868A FI55031C (en) 1966-02-19 1968-02-02 FREQUENCY REFRIGERATION OF ANTIBACTERIAL 5-BENZYLPYRIMIDINER
DK59371A DK128247B (en) 1966-02-19 1971-02-10 2,4-Diamino-5- (4'-hydroxybenzyl) -pyrimidines for use as starting materials in the preparation of corresponding compounds in which the hydrogen atom of the hydroxy group is substituted.
FI250271A FI55032C (en) 1966-02-19 1971-09-07 SOM UTGAONGSMATERIAL VID FRAMSTAELLNING AV ANTIBAKTERIELLA 2,4-DIAMINO-5- (3 ', 4', 5'-TRIALKOXIBENYL) -PYRIMIDINER ANVAENDBARA 2,4-DIAMINO-5- (4'-HYDROXIBENYL) -PYRIMIDINER
NO377771A NO133550C (en) 1966-02-19 1971-10-13
MY7100226A MY7100226A (en) 1966-02-19 1971-12-31 5-benzylpyrimidine derivatives and process for the preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB737666A GB1128234A (en) 1966-02-19 1966-02-19 5-benzylpyrimidine derivatives and process for the preparation thereof

Publications (1)

Publication Number Publication Date
GB1128234A true GB1128234A (en) 1968-09-25

Family

ID=9831956

Family Applications (1)

Application Number Title Priority Date Filing Date
GB737666A Expired GB1128234A (en) 1966-02-19 1966-02-19 5-benzylpyrimidine derivatives and process for the preparation thereof

Country Status (16)

Country Link
AT (2) AT275534B (en)
BE (1) BE694244A (en)
CA (1) CA977754A (en)
CH (2) CH511239A (en)
DE (2) DE1795635C3 (en)
DK (2) DK120344B (en)
ES (1) ES336945A1 (en)
FI (1) FI49714C (en)
FR (1) FR6595M (en)
GB (1) GB1128234A (en)
GR (1) GR33641B (en)
IL (1) IL27424A (en)
MY (1) MY7100226A (en)
NL (1) NL146811B (en)
NO (1) NO124601B (en)
SE (2) SE338998B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2249532A1 (en) * 1971-10-12 1973-04-26 Wellcome Found PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES
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
DE2944145A1 (en) 1979-11-02 1981-05-14 Dynamit Nobel Ag, 5210 Troisdorf METHOD FOR PRODUCING 2,4-DIAMINOPYRIMIDINE

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2249532A1 (en) * 1971-10-12 1973-04-26 Wellcome Found PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES
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
DE2944145A1 (en) 1979-11-02 1981-05-14 Dynamit Nobel Ag, 5210 Troisdorf METHOD FOR PRODUCING 2,4-DIAMINOPYRIMIDINE

Also Published As

Publication number Publication date
FI49714B (en) 1975-06-02
DK128247B (en) 1974-03-25
BE694244A (en) 1967-08-17
CH511239A (en) 1971-08-15
DE1795635C3 (en) 1978-05-11
DE1795635A1 (en) 1972-10-19
SE390412B (en) 1976-12-20
NL146811B (en) 1975-08-15
DE1795635B2 (en) 1977-09-22
AT275534B (en) 1969-10-27
CH513179A (en) 1971-09-30
ES336945A1 (en) 1968-01-16
FI49714C (en) 1975-09-10
DE1720012A1 (en) 1972-04-06
GR33641B (en) 1968-01-03
DK120344B (en) 1971-05-17
MY7100226A (en) 1971-12-31
NL6702397A (en) 1967-08-21
AT270653B (en) 1969-05-12
DE1720012B2 (en) 1977-06-08
FR6595M (en) 1969-01-06
CA977754A (en) 1975-11-11
IL27424A (en) 1971-02-25
NO124601B (en) 1972-05-08
SE338998B (en) 1971-09-27

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