GB606195A - Improvements in and relating to thiophene compounds and processes of preparing the same - Google Patents

Improvements in and relating to thiophene compounds and processes of preparing the same

Info

Publication number
GB606195A
GB606195A GB22788/45A GB2278845A GB606195A GB 606195 A GB606195 A GB 606195A GB 22788/45 A GB22788/45 A GB 22788/45A GB 2278845 A GB2278845 A GB 2278845A GB 606195 A GB606195 A GB 606195A
Authority
GB
United Kingdom
Prior art keywords
tetrahydrothiophene
benzamido
carboxybutyl
acetamido
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
GB22788/45A
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 GB606195A publication Critical patent/GB606195A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

2-(41-Carboxybutyl)-3 : 4-diamino-tetrahydrothiophene and mineral acid salts thereof are obtained by the hydrolysis of a compound of the formula <FORM:0606195/IV(b)/1> wherein R and R1 are different acyl groups and R11 is an alkyl, aryl or aralkyl group, preferably by means of aqueous alkali, followed by acidification of the hydrolysis mixture with a mineral acid. The corresponding free base is obtained by treating the mineral acid salt with alkali. Among the compounds which may be used as starting materials are 2-(41-carboethoxybutyl)-, 2-(41-carbomethoxybutyl)-2-(41-carbopropoxybutyl)-, 2 - (41 - carbobenzoxybutyl)-, 2 - (41 - carbophenoxybutyl) - 3 - acetamido - 4 - benzamido or 3-benzamido-4-acetamido-tetrahydrothiophene and the corresponding 3-propamido-4-benzamido compounds. In examples: (1) dl-cis-2-(41-carbomethoxybutyl)-3-acetamido - 4 - benzamido - tetrahydrothiophene is hydrolysed with barium hydroxide, the reaction mixture being acidified with sulphuric acid to produce the acid sulphate of dl-cis-2-(41-carboxybutyl)-3 : 4-diamino-tetrahydrothiophene; (2) dl-trans-epiallo-2-(41-carboxybutyl)-3 : 4-diamino-tetrahydrothiophene acid sulphate is produced as in (1) using the corresponding dl-trans-epiallo-compound as starting material; (3) as in (1), but using hydrochloric and hydrobromic acids instead of sulphuric; (4) as in (1) using the p dl-trans-allo-compound as starting material. Specifications 606,194 and 606,196 are referred to.
GB22788/45A 1944-09-16 1945-09-04 Improvements in and relating to thiophene compounds and processes of preparing the same Expired GB606195A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US606195XA 1944-09-16 1944-09-16

Publications (1)

Publication Number Publication Date
GB606195A true GB606195A (en) 1948-08-10

Family

ID=22030667

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22788/45A Expired GB606195A (en) 1944-09-16 1945-09-04 Improvements in and relating to thiophene compounds and processes of preparing the same

Country Status (1)

Country Link
GB (1) GB606195A (en)

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