GB755036A - Improvements in or relating to cyclic nitrogen compounds - Google Patents

Improvements in or relating to cyclic nitrogen compounds

Info

Publication number
GB755036A
GB755036A GB4104/54A GB410454A GB755036A GB 755036 A GB755036 A GB 755036A GB 4104/54 A GB4104/54 A GB 4104/54A GB 410454 A GB410454 A GB 410454A GB 755036 A GB755036 A GB 755036A
Authority
GB
United Kingdom
Prior art keywords
amino
glyoxal
methyl
triazine
substituted
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
GB4104/54A
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB755036A publication Critical patent/GB755036A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises 3-amino-as-triazines having the formula <FORM:0755036/IV(a)/1> in which R and R1 may be separate or joined to complete a second ring, each of R and R1, when separate, representing a hydrogen atom or a hydroxy or alkyl group, and R and R1 when joined, representing a polymethylene or substituted polymethylene radical. Such compounds are obtained by reacting aminoguanidine or a salt thereof with a 1 : 2-carbonyl compound of the formula R.CO.CO.R1. Suitable 1,2-dicarbonyl compounds are glyoxal and monoalkyl glyoxals such as methyl glyoxal (pyruvic aldehyde) and ethyl-, propyl, isopropyl-, butyl-, isobutyl-, tertiary butyl, amyl and hexy.-glyoxal, 1,2-diketones such as 2,3-butanedione (diacetyl), 2,3-pentanedione, 2,3- or 3,4-hexanedione, 3,4-heptanedione, 2,3-, 3,4- or 4,5-octanedione, 5,6-decanedione, 2,5-dimethyl-3,4-hexanedione, 5 - methyl - 3,4 - hexanedione and cyclohexanedione, and a -oxocarboxylic and a -dicarboxylic acids such as pyruvic acid, glyoxylic acid and oxalic acid. When an unsymmetrical, e.g. an alkyl glyoxal, is reacted is it not known whether the product is 5- or 6-substituted or a mixture of both, and this is indicated by describing the products as 3-amino - 5(6) - substituted - as-triazines. In Example (1) 3-amino-as-triazine is prepared by reacting glyoxal and aminoguanidine in alkaline medium. Similarly obtained are (2) 3-amino-5(6) - methyl - as - triazine, (3) 3 - amino - 5,6 - dimethyl-as-triazine and (4) 3-amino-5,6,7,8-tetrahydro-1,2,4-benzotriazine. A list is given of further derivatives containing 5- and/or 6-substituents selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, hexyl and hydroxy radicals. The products are useful as intermediates. By reaction with p-nitrophenylisocyanate there are obtained 1-(4-nitrophenyl)-3-(3-as-triazinyl) urea, the corresponding compounds substituted in the triazine nucleus by methyl radicals, and 1 - (4 - nitrophenyl) - 3 - [3 - (5,6,7,8 - tetrahydro-1,2,4-benzotriazinyl)] urea, which are effective against coccidiosis in poultry.
GB4104/54A 1953-03-11 1954-02-11 Improvements in or relating to cyclic nitrogen compounds Expired GB755036A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US755036XA 1953-03-11 1953-03-11

Publications (1)

Publication Number Publication Date
GB755036A true GB755036A (en) 1956-08-15

Family

ID=22126189

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4104/54A Expired GB755036A (en) 1953-03-11 1954-02-11 Improvements in or relating to cyclic nitrogen compounds

Country Status (1)

Country Link
GB (1) GB755036A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1232155B (en) * 1962-11-16 1967-01-12 Abic Chemical Lab Ltd Process for the preparation of asymmetric aminotriazine derivatives
US3412083A (en) * 1967-04-17 1968-11-19 Squibb & Sons Inc Azauridine derivatives
DE10109204A1 (en) * 2001-02-26 2002-09-19 4Sc Ag Use of new and known diphenylurea compounds for the preparation of a medicament for the inhibition of intracellular protein-degradation pathway
US6949567B2 (en) 2001-02-26 2005-09-27 4Sc Ag Compounds for the treatment of protozoal diseases
FR2986794A1 (en) * 2012-02-09 2013-08-16 Oreal Cosmetic composition, used as care, cleansing and/or makeup product for body skin, and to treat keratin materials and to condition, shape and protect hair by chemical or mechanical treatments, comprises new or known aldehyde compound

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1232155B (en) * 1962-11-16 1967-01-12 Abic Chemical Lab Ltd Process for the preparation of asymmetric aminotriazine derivatives
US3349086A (en) * 1962-11-16 1967-10-24 Haber Ralph Raphael George Process for the preparation of asymmetric amino triazine derivatives
US3412083A (en) * 1967-04-17 1968-11-19 Squibb & Sons Inc Azauridine derivatives
DE10109204A1 (en) * 2001-02-26 2002-09-19 4Sc Ag Use of new and known diphenylurea compounds for the preparation of a medicament for the inhibition of intracellular protein-degradation pathway
US6949567B2 (en) 2001-02-26 2005-09-27 4Sc Ag Compounds for the treatment of protozoal diseases
FR2986794A1 (en) * 2012-02-09 2013-08-16 Oreal Cosmetic composition, used as care, cleansing and/or makeup product for body skin, and to treat keratin materials and to condition, shape and protect hair by chemical or mechanical treatments, comprises new or known aldehyde compound

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