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GB813560A - Substituted-1:2-dihydro-1:3:5-triazines - Google Patents

Substituted-1:2-dihydro-1:3:5-triazines

Info

Publication number
GB813560A
GB813560A GB6718/57A GB671857A GB813560A GB 813560 A GB813560 A GB 813560A GB 6718/57 A GB6718/57 A GB 6718/57A GB 671857 A GB671857 A GB 671857A GB 813560 A GB813560 A GB 813560A
Authority
GB
United Kingdom
Prior art keywords
methylmercaptophenyl
biguanide
dihydro
ethylmercaptophenyl
diamino
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
GB6718/57A
Inventor
Royal Anzly Cutler
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Priority to GB6718/57A priority Critical patent/GB813560A/en
Publication of GB813560A publication Critical patent/GB813560A/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
    • C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • 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
    • 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
    • C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
    • 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
    • C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
    • 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
    • C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • 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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0813560/IV (b)/1> and the manufacture therefor by reacting a 1 - (41 - lower alkylmercaptophenyl)biguanide of of the formula <FORM:0813560/IV (b)/2> with a lower aliphatic carbonyl compound of the formula <FORM:0813560/IV (b)/3> wherein R1 and R2 are lower alkyl groups and R is an hydrogen atom or a lower alkyl group. Lower alkyl groups contain not more than four carbon atoms. In two examples, 4-(methylmercapto)aniline or 4-(ethylmercapto)aniline are reacted with acetone and dicyanodiamide in the presence of concentrated hydrochloric acid to form the biguanide derivatives (not isolated) and finally 4 : 6-diamino-1-(41-methylmercaptophenyl - 1 : 2 - dihydro - 2,2 - dimethyl - 1 : 3 : 5 - triazine and 4 : 6 - diamino - 1 - (41 - ethylmercaptophenyl) - 1 : 2 - dihydro - 2 : 2 - dimethyl - 1 : 3 : 5 - triazine respectively. On addition of aqueous sodium hydroxide solution the respective bases are liberated, that of the (41-methylmercaptophenyl)-derivative is isolated as its monohydrate. In two further examples 4-(methylmercapto)- and 4-(ethylmercapto)-anilines are reacted with dicyanodiamide in the presence of concentrated hydrochloric acid to form 1-(41-methylmercaptophenyl)- and 1-(41-ethylmercaptophenyl)biguanide hydrochlorides which are isolated and may be converted into their respective bases as above. By interacting the 1 - (41 - methylmercaptophenyl) - biguanide with n-butyraldehyde and the 1-(41-ethylmercaptophenyl)biguanide with methyl propyl ketone in the presence of concentrated hydrochloric acid, 4 : 6-diamino - 1 - (41 - methylmercaptophenyl) - 1 : 2 - dihydro - 2 - (n - propyl) - 1 : 3 : 5 - triazine hydrochloride and 4 : 6 - diamino - 1 - (41 - ethylmercaptophenyl) - 1 : 2 - dihydro - 2 - methyl - 2 - n - propyl - 1 : 3 : 5 - triazine hydrochloride are formed respectively, the corresponding bases being prepared as above.
GB6718/57A 1957-02-28 1957-02-28 Substituted-1:2-dihydro-1:3:5-triazines Expired GB813560A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB6718/57A GB813560A (en) 1957-02-28 1957-02-28 Substituted-1:2-dihydro-1:3:5-triazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6718/57A GB813560A (en) 1957-02-28 1957-02-28 Substituted-1:2-dihydro-1:3:5-triazines

Publications (1)

Publication Number Publication Date
GB813560A true GB813560A (en) 1959-05-21

Family

ID=9819518

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6718/57A Expired GB813560A (en) 1957-02-28 1957-02-28 Substituted-1:2-dihydro-1:3:5-triazines

Country Status (1)

Country Link
GB (1) GB813560A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3074947A (en) * 1963-01-22 Certificate of correction
US3215600A (en) * 1962-06-29 1965-11-02 Parke Davis & Co Antimalarial composition containing an acylated sulfonylaniline with triazine or pyrimidine salt, and method of use
US3223705A (en) * 1965-12-14 Salts of x,g-dlamino-i,z-dh-llydro-z-lower alkyl-i-aryl-s-triazenes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3074947A (en) * 1963-01-22 Certificate of correction
US3223705A (en) * 1965-12-14 Salts of x,g-dlamino-i,z-dh-llydro-z-lower alkyl-i-aryl-s-triazenes
US3215600A (en) * 1962-06-29 1965-11-02 Parke Davis & Co Antimalarial composition containing an acylated sulfonylaniline with triazine or pyrimidine salt, and method of use

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