GB759014A - Improvements in triazines and their manufacture - Google Patents

Improvements in triazines and their manufacture

Info

Publication number
GB759014A
GB759014A GB496952A GB496952A GB759014A GB 759014 A GB759014 A GB 759014A GB 496952 A GB496952 A GB 496952A GB 496952 A GB496952 A GB 496952A GB 759014 A GB759014 A GB 759014A
Authority
GB
United Kingdom
Prior art keywords
triazine
hydroxy
phenyl
methylthio
action
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
GB496952A
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 GB496952A priority Critical patent/GB759014A/en
Priority to BE517894A priority patent/BE517894A/en
Priority to FR1078476D priority patent/FR1078476A/en
Priority to CH316025D priority patent/CH316025A/en
Priority to DEW10662A priority patent/DE951996C/en
Publication of GB759014A publication Critical patent/GB759014A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises 3 : 5-diamino-6-aryl-1 : 2 : 4-triazines of the general formula: <FORM:0759014/IV(a)/1> in which X and Y may be halogen or hydrogen, and a method for preparing them by the conversion of the corresponding 5-hydroxy-3-alkylmercapto-triazine to the 5-chloro-compound and treating this with ammonia. The triazine may be prepared by the action of an arylglyoxylate ester on thiosemicarbazide and alkylating the mercapto group, or by the action of an arylglyoxylate ester on an S-alkylthiosemicarbazide. In examples, the methods described above are used to prepare 3-mercapto - 5 - hydroxy - 6 - phenyl - 1 : 2 : 4-triazine, the corresponding 3-methylthio, and 3 : 5-diamino derivatives, and similar products in which the 6-phenyl group is substituted by 4-Cl-, 2 : 4-dichlor-, 3 : 4-dichlor- and bromine atoms. The Provisional Specification also gives an alternative method of synthesizing the triazine in which aminoguanidine bicarbonate reacts with a methylphenylglyoxylate to give the 3 - amino - 5 - hydroxy - 6 - phenyl1 : 2 : 4 - triazine direct, and refers to products in which X or Y may also be alkoxy, giving as example the preparation of 3-methylthio-5-hydroxy - 6 - (3 : 4 - dimethoxy - phenyl)-1 : 2 : 4 - triazine; 3 - amino - 5 - hydroxy-6 - phenyl - 1 : 2 : 4 - triazine may be obtained by the action of ammonia on the corresponding 3-methylthio-compound; the 3 : 5-dihydroxy-6-phenyl compound may be obtained by acid hydrolysis of the preceding product.
GB496952A 1952-02-26 1952-02-26 Improvements in triazines and their manufacture Expired GB759014A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB496952A GB759014A (en) 1952-02-26 1952-02-26 Improvements in triazines and their manufacture
BE517894A BE517894A (en) 1952-02-26 1953-02-23 IMPROVEMENTS TO TRIAZINES AND THEIR PREPARATION.
FR1078476D FR1078476A (en) 1952-02-26 1953-02-26 Triazin compounds and their manufacture
CH316025D CH316025A (en) 1952-02-26 1953-02-26 Process for preparing 3,5-diamino-6-aryl-1,2,4-triazines
DEW10662A DE951996C (en) 1952-02-26 1953-02-27 Process for the preparation of 3,5-diamino-6-phenyl-1, 2, 4-triazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB496952A GB759014A (en) 1952-02-26 1952-02-26 Improvements in triazines and their manufacture

Publications (1)

Publication Number Publication Date
GB759014A true GB759014A (en) 1956-10-10

Family

ID=9787296

Family Applications (1)

Application Number Title Priority Date Filing Date
GB496952A Expired GB759014A (en) 1952-02-26 1952-02-26 Improvements in triazines and their manufacture

Country Status (5)

Country Link
BE (1) BE517894A (en)
CH (1) CH316025A (en)
DE (1) DE951996C (en)
FR (1) FR1078476A (en)
GB (1) GB759014A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3077473A (en) * 1959-05-28 1963-02-12 Hoffmann La Roche Hydrazino-1, 2, 4-triazines
EP0024351A1 (en) * 1979-08-16 1981-03-04 The Wellcome Foundation Limited Solid pharmaceutical formulation containing substitued phenyl-triazines
EP0021121B1 (en) * 1979-06-01 1983-05-11 The Wellcome Foundation Limited 1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them
EP0142306A2 (en) * 1983-10-27 1985-05-22 The Wellcome Foundation Limited Triazine compounds having cardiovascular activity
US4560687A (en) * 1979-06-01 1985-12-24 Baxter Martin G Substituted aromatic compounds
US6586593B1 (en) 2001-12-24 2003-07-01 Brantford Chemicals Inc. Efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines
GB2440242A (en) * 2006-07-13 2008-01-23 Univ Greenwich 1,2,4-Triazine derivatives as sodium channel blockers, antifolates and antimalarials
WO2009090431A1 (en) * 2008-01-16 2009-07-23 University Of Greenwich Cyclic triazo and diazo sodium channel blockers

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3357976A (en) * 1960-06-30 1967-12-12 Squibb & Sons Inc Mercury derivatives of certain as-triazine-5 (2h)-ones
DE1670912C3 (en) * 1967-08-18 1981-06-11 Bayer Ag, 5090 Leverkusen Herbicidal agents based on 1,2,4-triazin-5-ones

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3077473A (en) * 1959-05-28 1963-02-12 Hoffmann La Roche Hydrazino-1, 2, 4-triazines
EP0021121B1 (en) * 1979-06-01 1983-05-11 The Wellcome Foundation Limited 1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them
US4486354A (en) * 1979-06-01 1984-12-04 Baxter Martin G Substituted aromatic compounds
US4560687A (en) * 1979-06-01 1985-12-24 Baxter Martin G Substituted aromatic compounds
US4602017A (en) * 1979-06-01 1986-07-22 Sawyer David A Substituted aromatic compounds
EP0024351A1 (en) * 1979-08-16 1981-03-04 The Wellcome Foundation Limited Solid pharmaceutical formulation containing substitued phenyl-triazines
EP0086502A2 (en) * 1979-08-16 1983-08-24 The Wellcome Foundation Limited Substituted aromatic triazines
EP0086502A3 (en) * 1979-08-16 1984-02-01 The Wellcome Foundation Limited Substituted aromatic triazines
EP0142306A2 (en) * 1983-10-27 1985-05-22 The Wellcome Foundation Limited Triazine compounds having cardiovascular activity
EP0142306A3 (en) * 1983-10-27 1986-11-20 The Wellcome Foundation Limited Triazine compounds having cardiovascular activity
US4649139A (en) * 1983-10-27 1987-03-10 Burroughs Wellcome Co. 1,2,4-triazines
US6586593B1 (en) 2001-12-24 2003-07-01 Brantford Chemicals Inc. Efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines
GB2440242A (en) * 2006-07-13 2008-01-23 Univ Greenwich 1,2,4-Triazine derivatives as sodium channel blockers, antifolates and antimalarials
WO2008007149A3 (en) * 2006-07-13 2008-03-13 Univ Greenwich New medical use of triazine derivatives
GB2440242B (en) * 2006-07-13 2009-10-07 Univ Greenwich New medical use of triazine derivatives
AU2007274038B2 (en) * 2006-07-13 2011-08-04 University Of Greenwich New medical use of triazine derivatives
US8268823B2 (en) 2006-07-13 2012-09-18 University Of Greenwich Medical use of triazine derivatives
KR101482049B1 (en) * 2006-07-13 2015-01-13 유니버시티 오브 그리니치 New medical use of triazine derivatives
WO2009090431A1 (en) * 2008-01-16 2009-07-23 University Of Greenwich Cyclic triazo and diazo sodium channel blockers
US8691818B2 (en) 2008-01-16 2014-04-08 University Of Greenwich Cyclic triazo and diazo sodium channel blockers
AU2009205396B2 (en) * 2008-01-16 2014-10-02 University Of Greenwich Cyclic triazo and diazo sodium channel blockers
EP3002280A1 (en) * 2008-01-16 2016-04-06 University of Greenwich Cyclic triazo and diazo sodium channel blockers
US9422253B2 (en) 2008-01-16 2016-08-23 University Of Greenwich Cyclic triazo and diazo sodium channel blockers
US9862691B2 (en) 2008-01-16 2018-01-09 University Of Greenwich Cyclic triazo and diazo sodium channel blockers

Also Published As

Publication number Publication date
FR1078476A (en) 1954-11-18
CH316025A (en) 1956-09-15
BE517894A (en) 1955-01-21
DE951996C (en) 1956-11-08

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