PL402306A1 - Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms - Google Patents

Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms

Info

Publication number
PL402306A1
PL402306A1 PL402306A PL40230612A PL402306A1 PL 402306 A1 PL402306 A1 PL 402306A1 PL 402306 A PL402306 A PL 402306A PL 40230612 A PL40230612 A PL 40230612A PL 402306 A1 PL402306 A1 PL 402306A1
Authority
PL
Poland
Prior art keywords
diisopropylidene
protoescygenin
reaction
precipitate
production method
Prior art date
Application number
PL402306A
Other languages
Polish (pl)
Inventor
Mariusz Gruza
Kamil Jatczak
Marta Łaszcz
Grzegorz Grynkiewicz
Tomasz Giller
Anna Witkowska
Original Assignee
Instytut Farmaceutyczny
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 Instytut Farmaceutyczny filed Critical Instytut Farmaceutyczny
Priority to PL402306A priority Critical patent/PL402306A1/en
Priority to PCT/PL2013/000174 priority patent/WO2014104905A1/en
Priority to EP13828891.5A priority patent/EP2945961A1/en
Publication of PL402306A1 publication Critical patent/PL402306A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals

Landscapes

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

Abstract

Sposób wytwarzania 3,24;16,22-O,O;O,O-diizopropylideno-protoescygeniny obejmuje: a) reakcję acetonidowania monohydratu protoescygeniny w mieszaninie składającej się z 0-100% obj. acetonu i 100-0% obj. 2,2-dimetoksypropanu, w obecności katalitycznej ilości kwasu, prowadzącą do wytrącenia z mieszaniny reakcyjnej osadu 3,24;16,22-O,O;O,O-diizopropylideno-protoescygeniny, b) mieszanie zawiesiny osadu 3,24;16,22-O,O;O,O-diizopropylideno-protoescygeniny z zasadą tworzącą rozpuszczalną w warunkach reakcji sól z użytym w etapie a) kwasem, c) wyodrębnienie osadu 3,24;16,22-O,O;O,O-diizopropylideno-protoescygeniny z mieszaniny reakcyjnej, d) oczyszczanie 3,24;16,22-O,O;O,O-diizopropylideno-protoescygeniny. 3,24; 16,22-O,O;O,O-diizopropylideno-protoescygeninę, mającą potencjalne zastosowanie w syntezie modyfikowanych pochodnych saponinowych, wyodrębnia się z reakcji w postaci krystalicznej A lub B, również stanowiących przedmiot wynalazku.The production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescigene includes: a) the acetonidation reaction of protoescidin monohydrate in a mixture of 0-100 vol.% acetone and 100-0 vol.% 2,2-dimethoxypropane, in the presence of a catalytic amount of acid, resulting in precipitation of a precipitate from the reaction mixture 3.24; 16.22-O, O; O, O-diisopropylidene-proto-censinine, b) stirring the suspension of the precipitate 3.24; 16, 22-O, O; O, O-diisopropylidene-protoescygenin with a base forming a salt soluble under the reaction conditions with the acid used in step a), c) separation of the precipitate 3.24; 16.22-O, O; O, O-O-diisopropylidene - protocidinine from the reaction mixture, d) purification of 3.24; 16.22-O, O; O, O-diisopropylidene-protoescygenin. 3.24; 16,22-O, O; O, O-diisopropylidene-protoescygenin, which has the potential to be used in the synthesis of modified saponin derivatives, is isolated from the reaction in crystalline form A or B, also forming the subject of the invention.

PL402306A 2012-12-30 2012-12-30 Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms PL402306A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PL402306A PL402306A1 (en) 2012-12-30 2012-12-30 Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms
PCT/PL2013/000174 WO2014104905A1 (en) 2012-12-30 2013-12-30 Process for preparation of 3,24;16,22-di-o,o-isopropylideneprotoescigenin and crystalline forms thereof
EP13828891.5A EP2945961A1 (en) 2012-12-30 2013-12-30 Process for preparation of 3,24;16,22-di-o,o-isopropylideneprotoescigenin and crystalline forms thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL402306A PL402306A1 (en) 2012-12-30 2012-12-30 Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms

Publications (1)

Publication Number Publication Date
PL402306A1 true PL402306A1 (en) 2014-07-07

Family

ID=50070653

Family Applications (1)

Application Number Title Priority Date Filing Date
PL402306A PL402306A1 (en) 2012-12-30 2012-12-30 Production method of 3,24; 16,22-O, O; O, O-diisopropylidene-protoescygenin and its crystalline forms

Country Status (3)

Country Link
EP (1) EP2945961A1 (en)
PL (1) PL402306A1 (en)
WO (1) WO2014104905A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3061765B1 (en) 2015-02-27 2018-01-31 Warszawski Uniwersytet Medyczny Protoescigenin derivative, process of its preparation, use of said compound and pharmaceutical composition comprising that compound

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013055244A1 (en) * 2011-10-12 2013-04-18 Instytut Farmaceutyczny Preparation of protoescigenin from escin

Also Published As

Publication number Publication date
EP2945961A1 (en) 2015-11-25
WO2014104905A1 (en) 2014-07-03

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