GB759981A - Process for the manufacture of xanthine derivatives - Google Patents

Process for the manufacture of xanthine derivatives

Info

Publication number
GB759981A
GB759981A GB26138/54A GB2613854A GB759981A GB 759981 A GB759981 A GB 759981A GB 26138/54 A GB26138/54 A GB 26138/54A GB 2613854 A GB2613854 A GB 2613854A GB 759981 A GB759981 A GB 759981A
Authority
GB
United Kingdom
Prior art keywords
group
acetonyl
refluxing
propargyl
prepared
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
GB26138/54A
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB759981A publication Critical patent/GB759981A/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
    • 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
    • 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
    • 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:0759981/IV(a)/1> (wherein R1 and R2 are alkyl groups each containing from 1 to 5 carbon atoms and R3 is an acetonyl or propargyl group) are prepared by reacting the appropriate 1,3-dialkyl-xanthine unsubstituted in the 7-position in the presence of a tertiary base (preferably triethylamine) with a compound R3-halogen or, when R3 is an acetonyl group, a ketal thereof. When R3 is the propargyl group this may be subsequently transformed into the acetonyl group by the addition of 1 molecule of water to the triple bond. Examples illustrate the use of theophylline and, respectively, chloroacetone and propargyl bromide in the process of the invention, which is performed by refluxing the reactants with triethylamine in ethanol. 7-Acetonyltheophylline is also prepared from 7-propargyltheophylline by refluxing the latter with sulphuric acid and mercury oxide. Specification 750,588 is referred to.
GB26138/54A 1953-09-09 1954-09-09 Process for the manufacture of xanthine derivatives Expired GB759981A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH759981X 1953-09-09

Publications (1)

Publication Number Publication Date
GB759981A true GB759981A (en) 1956-10-24

Family

ID=4534597

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26138/54A Expired GB759981A (en) 1953-09-09 1954-09-09 Process for the manufacture of xanthine derivatives

Country Status (1)

Country Link
GB (1) GB759981A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422107A (en) * 1964-09-05 1969-01-14 Albert Ag Chem Werke Certain oxoalkyldimethylxanthines and a process for the preparation thereof
JPS50101386A (en) * 1974-01-22 1975-08-11
EP0018135B1 (en) * 1979-04-05 1983-09-28 BEECHAM - WUELFING GmbH &amp; Co. KG Xanthine derivatives, a process for their preparation and their use in pharmaceutical compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422107A (en) * 1964-09-05 1969-01-14 Albert Ag Chem Werke Certain oxoalkyldimethylxanthines and a process for the preparation thereof
JPS50101386A (en) * 1974-01-22 1975-08-11
JPS5912677B2 (en) * 1974-01-22 1984-03-24 ヨハン ア ウイルフイング Production method of xanthine derivatives
EP0018135B1 (en) * 1979-04-05 1983-09-28 BEECHAM - WUELFING GmbH &amp; Co. KG Xanthine derivatives, a process for their preparation and their use in pharmaceutical compositions

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