GB685866A - Improvements in or relating to nitroso substituted pteridines and preparation thereof - Google Patents

Improvements in or relating to nitroso substituted pteridines and preparation thereof

Info

Publication number
GB685866A
GB685866A GB14601/50A GB1460150A GB685866A GB 685866 A GB685866 A GB 685866A GB 14601/50 A GB14601/50 A GB 14601/50A GB 1460150 A GB1460150 A GB 1460150A GB 685866 A GB685866 A GB 685866A
Authority
GB
United Kingdom
Prior art keywords
acid
nitroso
carbon atoms
hydrogen atom
alkyl group
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
GB14601/50A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB685866A publication Critical patent/GB685866A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
    • C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Catalysts (AREA)

Abstract

The invention comprises 10-nitroso substituted pteridines of the general formula <FORM:0685866/IV (b)/1> wherein R1 is a hydrogen atom or an alkyl group having one to four carbon atoms, R2 is a hydrogen atom or an alkyl group having one to four carbon atoms, X is a hydroxyl group or a group having the general formula -NR3R4 in which R3 is a hydrogen atom or an alkyl group having one to four carbon atoms, R4 is a hydrogen atom or an alkyl group having one to four carbon atoms or R3 and R4 together represent a polymethylene group connected at both ends to the nitrogen atom, R5 is a hydrogen atom or an alkyl group having one to four carbon atoms and -NHR6 is a carboxylic amino acid group, and a process for preparing the above compounds by treating a pteridine of the general formula <FORM:0685866/IV (b)/2> wherein R1, R2, R5, R6 and X have th above significance, with nitrous acid in an aqueous solvent. The nitrous acid may be formed in situ from a mineral acid and a nitrite, e.g. an alkali metal, alkaline earth metal or ammonium nitrite. The preferred reaction temperature is in the range of - 10 DEG to +10 DEG C. or - 5 DEG to +5 DEG C. The amide grouping may be derived from glutamic acid, glutamylglutamic acid, diglutamylglutamic acid, amino acids having a plurality of peptide linkages such as serylglutamic acid, glycine, aspartic acid, leucine, serine, sarcosine, phenylalanine, alanine, isovaline or cystine. In the examples, the following compounds are prepared: N10-nitrosopteroylglutamic acid, N10-nitrosopteroyltriglutamic acid, N10-nitrosopteroylglutamylglutamic acid, N10 - nitroso - 4 - (2,4 - diamino - 6 - pteridylmethyl) aminobenzoylglutamic acid, N10 - nitroso - 2 - dimethylamino - 4 - aminopteroylglutamic acid, N10 - nitroso - 2 - dimethylaminopteroylglutamic acid, N10-nitroso-4-(1-piperidyl) pteroylglutamic acid and 9-methyl - N10 - nitrosopteroylglutamic acid. Specification 685,860 is referred to.
GB14601/50A 1949-07-02 1950-06-12 Improvements in or relating to nitroso substituted pteridines and preparation thereof Expired GB685866A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US685866XA 1949-07-02 1949-07-02

Publications (1)

Publication Number Publication Date
GB685866A true GB685866A (en) 1953-01-14

Family

ID=22083480

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14601/50A Expired GB685866A (en) 1949-07-02 1950-06-12 Improvements in or relating to nitroso substituted pteridines and preparation thereof

Country Status (1)

Country Link
GB (1) GB685866A (en)

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