GB982079A - Process for the production of xanthine derivatives - Google Patents

Process for the production of xanthine derivatives

Info

Publication number
GB982079A
GB982079A GB1669862A GB1669862A GB982079A GB 982079 A GB982079 A GB 982079A GB 1669862 A GB1669862 A GB 1669862A GB 1669862 A GB1669862 A GB 1669862A GB 982079 A GB982079 A GB 982079A
Authority
GB
United Kingdom
Prior art keywords
uracil
general formula
amino
heating
dehydration
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
GB1669862A
Inventor
Herbert Goldner
Guenther Dietz
Ernst Carstens
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.)
AWD Pharma GmbH and Co KG
Original Assignee
Arzneimittelwerk Dresden GmbH
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 Arzneimittelwerk Dresden GmbH filed Critical Arzneimittelwerk Dresden GmbH
Priority to GB1669862A priority Critical patent/GB982079A/en
Publication of GB982079A publication Critical patent/GB982079A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Landscapes

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

Abstract

Xanthine derivatives of the general formula <FORM:0982079/C2/1> wherein R1 and R2 represent hydrogen atoms or alkyl radicals and R3 represents a hydrogen atom or an alkyl, aryl, aralkyl, carbalkoxy, hydroxyalkyl or di-alkylaminoalkyl radical, are prepared by dehydrating 4-amino-5-nitrosouracils of the general formula <FORM:0982079/C2/2> The dehydration may be performed by dry heating, usually at 50 DEG to 200 DEG C., the uracil or by heating a solution thereof in an organic solvent, e.g. dimethylformamide, benzene, toluene, xylenes and alcohols. The uracil starting materials may be prepared by: (1) reacting the corresponding 4-chloro-uracils with amine of the general formula H2NCH2R3 and nitrosating the product; or (2) transamination of the corresponding 4-amino-uracils with amine hydrochlorides of the general formula H2NCH2R3.HCl and subsequent nitrosation. When the methylene group a to the 4-amino group in the uracil intermediate of (1) above is activated by the presence of another group in the substituent R3, partial or complete dehydration to xanthines of formula I may occur during the nitrosation step. If the ring closure is incomplete the dehydration may be completed by heating the nitrosation mixture or by isolating the nitrosouracil thereform and heating said uracil alone or in solution. In another embodiment 1-R1-3-R2-4-amino-5-nitroso-uracil are simultaneously transaminated with amine hydrochlorides of the formula given in (2) above and dehydrated to the corresponding xanthine derivatives.
GB1669862A 1962-05-01 1962-05-01 Process for the production of xanthine derivatives Expired GB982079A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1669862A GB982079A (en) 1962-05-01 1962-05-01 Process for the production of xanthine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1669862A GB982079A (en) 1962-05-01 1962-05-01 Process for the production of xanthine derivatives

Publications (1)

Publication Number Publication Date
GB982079A true GB982079A (en) 1965-02-03

Family

ID=10082033

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1669862A Expired GB982079A (en) 1962-05-01 1962-05-01 Process for the production of xanthine derivatives

Country Status (1)

Country Link
GB (1) GB982079A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0039780A1 (en) * 1980-05-02 1981-11-18 Societe Des Produits Nestle S.A. Di- or trisubstituted xanthines with neuroleptic activity, process for their preparation and pharmaceutical preparations containing them
US4452788A (en) * 1982-04-21 1984-06-05 Warner-Lambert Company Substituted 8-phenylxanthines
FR2541281A1 (en) * 1983-02-18 1984-08-24 Univ Johns Hopkins SUBSTITUTED 8-PHENYLXANTHINES AND COMPOSITIONS THEREOF FOR BLOCKING ADENOSINE RECEPTORS
US4548818A (en) * 1978-10-20 1985-10-22 Kjellin Per G Composition and methods for the treatment of chronic obstructive airway disease and cardiac disease using 3-alkylxanthines
WO1987004435A2 (en) * 1986-01-21 1987-07-30 Beecham Group P.L.C. Xanthine compounds
US4769377A (en) * 1983-02-18 1988-09-06 The Johns Hopkins University Adenosine receptor antagonists

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4548818A (en) * 1978-10-20 1985-10-22 Kjellin Per G Composition and methods for the treatment of chronic obstructive airway disease and cardiac disease using 3-alkylxanthines
US4644001A (en) * 1978-10-20 1987-02-17 Aktiebolaget Draco 3-Alkylxanthines, composition and methods for the treatment of chronic obstructive-airway disease and cardiac disease
EP0039780A1 (en) * 1980-05-02 1981-11-18 Societe Des Produits Nestle S.A. Di- or trisubstituted xanthines with neuroleptic activity, process for their preparation and pharmaceutical preparations containing them
US4452788A (en) * 1982-04-21 1984-06-05 Warner-Lambert Company Substituted 8-phenylxanthines
FR2541281A1 (en) * 1983-02-18 1984-08-24 Univ Johns Hopkins SUBSTITUTED 8-PHENYLXANTHINES AND COMPOSITIONS THEREOF FOR BLOCKING ADENOSINE RECEPTORS
GB2135311A (en) * 1983-02-18 1984-08-30 Univ Johns Hopkins Novel xanthine-type adenosine receptor antagonists
DE3406275A1 (en) * 1983-02-18 1984-09-27 The Johns Hopkins University, Baltimore, Md. NEW ADENOSINE RECEPTOR ANTAGONISTS
US4593095A (en) * 1983-02-18 1986-06-03 The Johns Hopkins University Xanthine derivatives
US4769377A (en) * 1983-02-18 1988-09-06 The Johns Hopkins University Adenosine receptor antagonists
WO1987004435A2 (en) * 1986-01-21 1987-07-30 Beecham Group P.L.C. Xanthine compounds
WO1987004435A3 (en) * 1986-01-21 1988-03-24 Beecham Group Plc Xanthine compounds

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