GB767749A - New triazine derivatives - Google Patents

New triazine derivatives

Info

Publication number
GB767749A
GB767749A GB20136/54A GB2013654A GB767749A GB 767749 A GB767749 A GB 767749A GB 20136/54 A GB20136/54 A GB 20136/54A GB 2013654 A GB2013654 A GB 2013654A GB 767749 A GB767749 A GB 767749A
Authority
GB
United Kingdom
Prior art keywords
dimethylaminopropylamino
radical
formula
substituents
trichloromethyl
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
GB20136/54A
Inventor
Stanley Birtwell
Walter Hepworth
Gilbert Joseph Stacey
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 GB20136/54A priority Critical patent/GB767749A/en
Publication of GB767749A publication Critical patent/GB767749A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
    • 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)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention comprises triazine derivatives of the formula <FORM:0767749/IV(b)/1> wherein R stands for an anilino radical the phenyl radical of which may optionally bear substituents or for a phenylguanidino radical, the phenyl radical of which may optionally bear halogeno substituents, A stands for a hydrocarbon linking group and R1 and R2 stand for hydrogen or for alkyl radicals or they are united to form, together with the adjacent nitrogen atom, a heterocyclic ring. Compounds of that formula where R stands for an anilino radical, the phenyl radical of which may optionally bear substituents, are obtained by heating a biguanide of the formula R-C(: NH)-NH-C(: NH)-NHANR1R2 with an acylating derivative of trichloracetic acid. Suitable derivatives are the anhydride, acid chloride or esters. The process may be effected in a solvent or diluent such as trichloracetic acid. Compounds of the above formula where R represents a phenyl guanidino radical, the phenyl radical of which may optionally bear halogen substituents, are obtained by heating a compound of the formula <FORM:0767749/IV(b)/2> wherein R3 stands for a phenyl radical which may optionally bear halogeno substituents with a compound of the formula H2N.A.NR1R2, suitably in the presence of a solvent such as benzene. In Example (1) N1-p-chlorophenyl -N5-g -dimethylaminopropylbiguanide is heated in a mixture of trichloracetic acid and anhydride to form 2-p-chloroanilino-4-g -dimethylaminopropylamino - 6 - trichloromethyl - 1 : 3 : 5 - triazines. Similarly prepared are 6-trichloromethyl-1 : 3 : 5-triazines having as 2- and 4-substituents respectively (2) 3 : 4-dichloroanilino and g -dimethylaminopropylamino, (3) p-chloroanilino and b -dimethylaminoethylamino, (4) p-methoxyanilino and g -dimethylaminopropylamino, (5) anilino and g -dimethylaminopropylamino, (6) p-chloroanilino and b -piperidinoethylamino and (7) p-nitroanilino and g -dimethylaminopropylamino groups. In Example (8) 2 - p - chlorophenylguanidino - 4 : 6 - bis-trichloromethyl - 1 : 3 : 5 - triazine (obtained by reacting 2 : 4 : 6-tristrichloromethyl-1 : 3 : 5-triazine with p-chlorophenylguanidine) is heated with g -dimethylaminopropylamine to form 2 - p - chlorophenylguanidino - 4 - (g - dimethylaminopropylamino) - 6 - trichloromethyl - 1 : 3 : 5-triazine. 2-p-Chlorophenylguanidino-4-(d - diethylamino - a - methylbutylamino) - 6 - trichloromethyl - 1 : 3 : 5 - triazine hydrochloride is similarly prepared.
GB20136/54A 1954-07-09 1954-07-09 New triazine derivatives Expired GB767749A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB20136/54A GB767749A (en) 1954-07-09 1954-07-09 New triazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB20136/54A GB767749A (en) 1954-07-09 1954-07-09 New triazine derivatives

Publications (1)

Publication Number Publication Date
GB767749A true GB767749A (en) 1957-02-06

Family

ID=10140964

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20136/54A Expired GB767749A (en) 1954-07-09 1954-07-09 New triazine derivatives

Country Status (1)

Country Link
GB (1) GB767749A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2966487A (en) * 1958-07-01 1960-12-27 Searle & Co 3-aminoalkylaminobenzotriazine-1-oxides
WO2014159993A1 (en) * 2013-03-13 2014-10-02 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Reed Army Institute Of Research Triazine compounds and compositions thereof and methods for treating malaria and chemoprophylaxis

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2966487A (en) * 1958-07-01 1960-12-27 Searle & Co 3-aminoalkylaminobenzotriazine-1-oxides
WO2014159993A1 (en) * 2013-03-13 2014-10-02 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Reed Army Institute Of Research Triazine compounds and compositions thereof and methods for treating malaria and chemoprophylaxis
US20150210652A1 (en) * 2013-03-13 2015-07-30 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Substituted Triazines for Malaria Treatment and Chemoprophylaxis
US9334246B2 (en) * 2013-03-13 2016-05-10 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Reed Army Institute Of Research Substituted triazines for malaria treatment and chemoprophylaxis
US9700562B2 (en) 2013-03-13 2017-07-11 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Reed Army Institute Of Research Triazine compounds and compositions thereof and methods for treating malaria and chemoprophylaxis
EP3351538A1 (en) * 2013-03-13 2018-07-25 The United States of America, as represented by The Secretary of The Army, on behalf of Walter Reed Army Institute of Research Triazine compounds and compositions thereof and methods for treating malaria and chemoprophylaxis

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