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GB957797A - Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor - Google Patents

Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor

Info

Publication number
GB957797A
GB957797A GB30102/59A GB3010259A GB957797A GB 957797 A GB957797 A GB 957797A GB 30102/59 A GB30102/59 A GB 30102/59A GB 3010259 A GB3010259 A GB 3010259A GB 957797 A GB957797 A GB 957797A
Authority
GB
United Kingdom
Prior art keywords
group
alkoxy
diamino
electrophilic
nitriles
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
GB30102/59A
Inventor
Harold Malcolm Hood
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27258299&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB957797(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to DENDAT1303727D priority Critical patent/DE1303727B/en
Priority to GB30102/59A priority patent/GB957797A/en
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to IT13817/60A priority patent/IT1061608B/en
Priority to ES0260242A priority patent/ES260242A1/en
Priority to DE1445176A priority patent/DE1445176C3/en
Priority to DE19601795586 priority patent/DE1795586C3/en
Priority to AT656060A priority patent/AT230379B/en
Priority to CH996260A priority patent/CH418338A/en
Priority to SE836660A priority patent/SE219368C1/sv
Priority to FI1465/60A priority patent/FI42960B/fi
Publication of GB957797A publication Critical patent/GB957797A/en
Priority to MY196661A priority patent/MY6600061A/en
Priority to FI68670A priority patent/FI49156C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises compounds of the general formula: Ar1.CH:C(CN).CH2Z1 wherein Ar1 has 6 to 15 carbon atoms and is a phenyl group optionally substituted by an alkoxy group and/or a halogen atom or by the residue CH:CH.CH:CH- and Z1 is an alkoxy group; the preparation of a substance consisting of one or more nitriles of the formulae: <FORM:0957797/C2/1> <FORM:0957797/C2/2> wherein Ar is a phenyl group optionally substituted by an alkoxy, alkyl, amino, dialkylamino, group and/or a halogen atom or with a -CH:CH.CH:CH. residue and Z is an electrophilic group, by condensing an aldehyde Ar.CHO in the presence of a strong base with a b -substituted propionitrile Y.CH2CH2CN where Y is an electrophilic group, the group Z being the group Y or an alkoxy group derived from a solvent alcohol; and the preparation of a 2,4-diamino-5-arylmethylpyrimidine of the formula: <FORM:0957797/C2/3> by reacting a substance consisting of one or more nitriles Ia and Ib, prepared by the process above, with guanidine. Suitable electrophilic groups (Y) are ether, thioether and tertiary amino groups. The reaction to prepare the pyrimidines may be carried through in one stage. The b -alkoxypropionitrile may be prepared in situ from acrylonitrile and the solvent alcohol. Specifications 687,032, 734,801, 875,562, 920,412, U.S.A. Specifications 2,579,259, 2,624,732, 2,658,897, 2,823,160 and 2,909,522 are referred to.
GB30102/59A 1959-09-03 1959-09-03 Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor Expired GB957797A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DENDAT1303727D DE1303727B (en) 1959-09-03 Alpha-arylidene-substituted propioni-iriles
GB30102/59A GB957797A (en) 1959-09-03 1959-09-03 Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor
IT13817/60A IT1061608B (en) 1959-09-03 1960-08-06 METHOD FOR THE PREPARATION OF 2.4 DIAMOND 5 ARYLMETHYLPYRIMIDINE AND COMPOUNDS SO OBTAINED
ES0260242A ES260242A1 (en) 1959-09-03 1960-08-08 A method for making 2,4-diamino-5-arilmetil-pyridines (Machine-translation by Google Translate, not legally binding)
DE1445176A DE1445176C3 (en) 1959-09-03 1960-08-12 Process for the preparation of 2,4-diamino-5-benzyl-pyrimidines
DE19601795586 DE1795586C3 (en) 1959-09-03 1960-08-12 Process for the preparation of 2,4-diamino-5-benzyl-pyrimidines
AT656060A AT230379B (en) 1959-09-03 1960-08-29 Process for the preparation of 2,4-diamino-5-arylmethylpyrimidines
CH996260A CH418338A (en) 1959-09-03 1960-09-02 Process for the preparation of 2,4-diamino-5-arylmethylpyrimidines
SE836660A SE219368C1 (en) 1959-09-03 1960-09-02
FI1465/60A FI42960B (en) 1959-09-03 1960-09-03
MY196661A MY6600061A (en) 1959-09-03 1966-12-31 Method for making 2, 4-diamino-5-arylmethyl pyrimidines and intermediates therefor
FI68670A FI49156C (en) 1959-09-03 1970-03-13 Novel propionitrile derivatives which are intermediates in the preparation of pharmaceutically valuable 2,4-diamino-5-benzylpyrimidines and processes for their preparation.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB30102/59A GB957797A (en) 1959-09-03 1959-09-03 Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor
GB3956059 1959-11-20
GB2410160 1960-07-11

Publications (1)

Publication Number Publication Date
GB957797A true GB957797A (en) 1964-05-13

Family

ID=27258299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30102/59A Expired GB957797A (en) 1959-09-03 1959-09-03 Method for making 2,4-diamino-5-arylmethylpyrimidines and intermediates therefor

Country Status (8)

Country Link
AT (1) AT230379B (en)
CH (1) CH418338A (en)
DE (2) DE1445176C3 (en)
FI (1) FI42960B (en)
GB (1) GB957797A (en)
IT (1) IT1061608B (en)
MY (1) MY6600061A (en)
SE (1) SE219368C1 (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3461206A (en) * 1964-11-12 1969-08-12 Hoffmann La Roche Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine
DE2010166A1 (en) * 1969-03-06 1970-09-17 The Wellcome Foundation Ltd., London Stabilized alpha-benzylaeryl nitriles, process for their preparation and their use
DE2065367A1 (en) * 1969-03-06 1973-05-24 Wellcome Found Beta-amino-alpha-aryloxymethylacrylonitrile - and 2,4-diamino-5-benzylpyrimidine derivs. useful as antibacterial agents
US3852276A (en) * 1969-03-06 1974-12-03 Burroughs Wellcome Co 5-benzyl pyrimidines intermediate therefore, and method
US3855265A (en) * 1969-03-06 1974-12-17 Burroughs Wellcome Co 5-benzyl pyrimidines intermediates therefore, and method
US3950378A (en) * 1969-03-06 1976-04-13 Burroughs Wellcome Co. Preparation of β-anilino-α-benzylacrylonitriles
US3991050A (en) * 1969-03-06 1976-11-09 Burroughs Wellcome Co. Preparation of β-Amino-α-benzylacrylonitriles
US3998814A (en) 1969-03-06 1976-12-21 Burroughs Wellcome Co. Process for preparing β-amino-α-benzylacrylonitriles
US4052553A (en) * 1969-03-06 1977-10-04 Burroughs Wellcome Co. 5-benzyl pyrimidines intermediates therefore, and method
US4116958A (en) * 1971-10-12 1978-09-26 Burroughs Wellcome Co. Organic synthetic methods benzylpyrimidine derivatives
US4137411A (en) * 1977-02-04 1979-01-30 Hoffmann-La Roche Inc. Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines
US4180578A (en) 1977-05-09 1979-12-25 Ludwig Heumann, & Co. GmbH 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use
US4251454A (en) 1974-12-24 1981-02-17 Hoffmann-La Roche Inc. Benzylpyrimidines
EP0051879A3 (en) * 1980-11-11 1982-08-04 The Wellcome Foundation Limited Substituted pyrimidines, their synthesis and compositions containing them, their use in medicine and intermediates for making them
EP0096214A1 (en) * 1982-05-01 1983-12-21 The Wellcome Foundation Limited Antibacterial pyrimidine compounds
US4587341A (en) * 1982-05-07 1986-05-06 Burroughs Wellcome Co. 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials
AT384023B (en) * 1980-11-11 1987-09-25 Wellcome Found METHOD FOR PRODUCING NEW 2,4-DIAMINO-5- (SUBST.) PYRIMIDINES AND THEIR SALTS, N-OXIDES AND N-ACYL DERIVATIVES
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

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2051871A1 (en) * 1969-05-16 1971-11-18 The Wellcome Foundation Ltd., London Beta-amino-alpha-aryloxymethylacrylonitrile - and 2,4-diamino-5-benzylpyrimidine derivs. useful as antibacterial agents
BR6915082D0 (en) 1969-05-16 1973-03-08 Wellcome Found PROCESS OF PREPARATION OF BENZYL-PYRIMIDINES
BE792096A (en) * 1971-12-01 1973-05-30 Hoffmann La Roche NEW BENZYLPYRIMIDINES
EP0046856A3 (en) * 1980-08-29 1982-07-28 Hüls Troisdorf Aktiengesellschaft Process for preparing 4-amino-2-mercapto-pyrimidines
HU186413B (en) * 1981-06-26 1985-07-29 Egyt Gyogyszervegyeszeti Gyar Process for producing 2,4-diamino-5-bracket-3-comma above,4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine
HU187370B (en) * 1981-06-26 1985-12-28 Egyt Gyogyszervegyeszeti Gyar Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine
DE3603577A1 (en) * 1986-02-06 1987-08-13 Joachim K Prof Dr Seydel NEW SUBSTITUTED 2,4-DIAMINO-5-BENZYLPYRIMIDINE, THEIR PRODUCTION AND USE THEREOF AS A MEDICINE WITH ANTIBACTERIAL EFFECTIVENESS

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3461206A (en) * 1964-11-12 1969-08-12 Hoffmann La Roche Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine
DE2010166A1 (en) * 1969-03-06 1970-09-17 The Wellcome Foundation Ltd., London Stabilized alpha-benzylaeryl nitriles, process for their preparation and their use
US3697512A (en) * 1969-03-06 1972-10-10 Burroughs Wellcome Co 5-benzyl pyrimidines intermediates
DE2065367A1 (en) * 1969-03-06 1973-05-24 Wellcome Found Beta-amino-alpha-aryloxymethylacrylonitrile - and 2,4-diamino-5-benzylpyrimidine derivs. useful as antibacterial agents
US3852276A (en) * 1969-03-06 1974-12-03 Burroughs Wellcome Co 5-benzyl pyrimidines intermediate therefore, and method
US3855265A (en) * 1969-03-06 1974-12-17 Burroughs Wellcome Co 5-benzyl pyrimidines intermediates therefore, and method
US3950378A (en) * 1969-03-06 1976-04-13 Burroughs Wellcome Co. Preparation of β-anilino-α-benzylacrylonitriles
US3991050A (en) * 1969-03-06 1976-11-09 Burroughs Wellcome Co. Preparation of β-Amino-α-benzylacrylonitriles
US3998814A (en) 1969-03-06 1976-12-21 Burroughs Wellcome Co. Process for preparing β-amino-α-benzylacrylonitriles
US4052553A (en) * 1969-03-06 1977-10-04 Burroughs Wellcome Co. 5-benzyl pyrimidines intermediates therefore, and method
US4116958A (en) * 1971-10-12 1978-09-26 Burroughs Wellcome Co. Organic synthetic methods benzylpyrimidine derivatives
US4251454A (en) 1974-12-24 1981-02-17 Hoffmann-La Roche Inc. Benzylpyrimidines
US4137411A (en) * 1977-02-04 1979-01-30 Hoffmann-La Roche Inc. Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines
US4180578A (en) 1977-05-09 1979-12-25 Ludwig Heumann, & Co. GmbH 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use
EP0051879A3 (en) * 1980-11-11 1982-08-04 The Wellcome Foundation Limited Substituted pyrimidines, their synthesis and compositions containing them, their use in medicine and intermediates for making them
US4438267A (en) 1980-11-11 1984-03-20 Daluge Susan M Monoheteroring compounds and their use
AT384023B (en) * 1980-11-11 1987-09-25 Wellcome Found METHOD FOR PRODUCING NEW 2,4-DIAMINO-5- (SUBST.) PYRIMIDINES AND THEIR SALTS, N-OXIDES AND N-ACYL DERIVATIVES
US4761475A (en) * 1980-11-11 1988-08-02 Daluge Susan M 2,4-diaminopyrimidines substituted with heterobicyclomethyl radicals at the 5 position useful as antibacterials
EP0096214A1 (en) * 1982-05-01 1983-12-21 The Wellcome Foundation Limited Antibacterial pyrimidine compounds
AU569468B2 (en) * 1982-05-01 1988-02-04 Wellcome Foundation Limited, The 2,4 - diamino -s- (substituted) pyrimidines
US4587341A (en) * 1982-05-07 1986-05-06 Burroughs Wellcome Co. 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials
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
US5712276A (en) * 1988-12-07 1998-01-27 Glaxo Wellcome Inc. 2-(n-alkylpiperazino or morpholino)-4-amino-5-aryl-pyrimidines

Also Published As

Publication number Publication date
FI42960B (en) 1970-09-02
DE1303727B (en) 1976-02-05
SE219368C1 (en) 1968-03-12
MY6600061A (en) 1966-12-31
DE1445176B2 (en) 1973-09-06
AT230379B (en) 1963-12-10
IT1061608B (en) 1983-04-30
DE1445176A1 (en) 1968-10-17
DE1445176C3 (en) 1974-04-25
CH418338A (en) 1966-08-15

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