FR2112710A5 - Thiocolchicoside prepn - from thiocolchicine in high yield in three stages - Google Patents

Thiocolchicoside prepn - from thiocolchicine in high yield in three stages

Info

Publication number
FR2112710A5
FR2112710A5 FR7039971A FR7039971A FR2112710A5 FR 2112710 A5 FR2112710 A5 FR 2112710A5 FR 7039971 A FR7039971 A FR 7039971A FR 7039971 A FR7039971 A FR 7039971A FR 2112710 A5 FR2112710 A5 FR 2112710A5
Authority
FR
France
Prior art keywords
thiocolchicine
demethyl
thiocolchicoside
prepn
stages
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
FR7039971A
Other languages
French (fr)
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7039971A priority Critical patent/FR2112710A5/en
Application granted granted Critical
Publication of FR2112710A5 publication Critical patent/FR2112710A5/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/248—Colchicine radicals, e.g. colchicosides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

3-Glucose-2-yl-3-demethyl-thiocolchicine(thiocolchicoside) and the 2-glucose-2-yl-2-demethyl-deriv. are prepd. by (i) reacting thiocolchicine (T) with BBr3 to give 1,2- and 2,3-bis-demethyl-T (the latter predominating); (ii) reacting with acetobromoglucose in the presence of a tertiary base to give 2- and 3-tetraacetoglucose-2-yl-2,3-bis-demethyl-T and 2-tetraacetoglucose-2-yl-1,2-bis-demethyl-T; (iii) reacting with CH3N2 then a base, and (iv) separating the mixture of the two products obtd. The five named inters. are new.
FR7039971A 1970-11-06 1970-11-06 Thiocolchicoside prepn - from thiocolchicine in high yield in three stages Expired FR2112710A5 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7039971A FR2112710A5 (en) 1970-11-06 1970-11-06 Thiocolchicoside prepn - from thiocolchicine in high yield in three stages

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7039971A FR2112710A5 (en) 1970-11-06 1970-11-06 Thiocolchicoside prepn - from thiocolchicine in high yield in three stages

Publications (1)

Publication Number Publication Date
FR2112710A5 true FR2112710A5 (en) 1972-06-23

Family

ID=9063852

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7039971A Expired FR2112710A5 (en) 1970-11-06 1970-11-06 Thiocolchicoside prepn - from thiocolchicine in high yield in three stages

Country Status (1)

Country Link
FR (1) FR2112710A5 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0789028A2 (en) * 1996-02-08 1997-08-13 INDENA S.p.A. A process for the glycosidation of colchicine derivatives and products obtained

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0789028A2 (en) * 1996-02-08 1997-08-13 INDENA S.p.A. A process for the glycosidation of colchicine derivatives and products obtained
EP0789028A3 (en) * 1996-02-08 1998-01-28 INDENA S.p.A. A process for the glycosidation of colchicine derivatives and products obtained

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