PL376791A1 - Stereospecyficzna redukcja sapogen-3-onów - Google Patents

Stereospecyficzna redukcja sapogen-3-onów

Info

Publication number: PL376791A1
Authority: PL; Poland
Prior art keywords: derivative; steroidal; steroidal sapogenin; sapogenin; reducing
Prior art date: 2002-10-28

Application number

PL376791A

Other languages

English (en)

Other versions

PL210114B1 (pl

Inventor

Philip James Gunning

Peter David Tiffin

Original Assignee

Phytopharm Plc

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.)

2002-10-28

Filing date

2003-04-28

Publication date

2006-01-09

2002-10-28 Priority claimed from GB0225106A external-priority patent/GB0225106D0/en

2003-01-22 Priority claimed from GB0301505A external-priority patent/GB0301505D0/en

2003-04-28 Application filed by Phytopharm Plc filed Critical Phytopharm Plc

2006-01-09 Publication of PL376791A1 publication Critical patent/PL376791A1/pl

2011-12-30 Publication of PL210114B1 publication Critical patent/PL210114B1/pl

Links

230000000707 stereoselective effect Effects 0.000 title 1
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 abstract 7
230000003637 steroidlike Effects 0.000 abstract 7
NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 abstract 6
RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 abstract 4
GMBQZIIUCVWOCD-UQHLGXRBSA-N (25R)-5beta-spirostan-3beta-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-UQHLGXRBSA-N 0.000 abstract 2
GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 abstract 2
229910000091 aluminium hydride Inorganic materials 0.000 abstract 2
125000002370 organoaluminium group Chemical group 0.000 abstract 2
INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 abstract 1
GMBQZIIUCVWOCD-RHHRBMONSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16R,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-RHHRBMONSA-N 0.000 abstract 1
AZXZUBZBLNFUPF-UHFFFAOYSA-N Tamogenone Natural products CC1C(C2(CCC3C4(C)CCC(=O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 AZXZUBZBLNFUPF-UHFFFAOYSA-N 0.000 abstract 1
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 abstract 1
AZXZUBZBLNFUPF-CLGLNXEMSA-N chembl1915879 Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCC(=O)C=C4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 AZXZUBZBLNFUPF-CLGLNXEMSA-N 0.000 abstract 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
239000003638 chemical reducing agent Substances 0.000 abstract 1
WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 abstract 1
GMBQZIIUCVWOCD-SGKIHABASA-N epismilagenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-SGKIHABASA-N 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
229950002323 smilagenin Drugs 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

PL376791A 2002-10-28 2003-04-28 Sposób stereospecyficznego wytwarzania 3β-hydroksy-5β-H-steroidowych sapogenin PL210114B1 (pl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB0225106A GB0225106D0 (en)	2002-10-28	2002-10-28	Synthesis of 3 hydroxy-5 -steroids
GB0301505A GB0301505D0 (en)	2003-01-22	2003-01-22	Stereospecific synthesis of sapogenins

Publications (2)

Publication Number	Publication Date
PL376791A1 true PL376791A1 (pl)	2006-01-09
PL210114B1 PL210114B1 (pl)	2011-12-30

Family

ID=32178884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL376791A PL210114B1 (pl)	2002-10-28	2003-04-28	Sposób stereospecyficznego wytwarzania 3β-hydroksy-5β-H-steroidowych sapogenin

Country Status (17)

Country	Link
US (1)	US7718792B2 (pl)
EP (1)	EP1558627B1 (pl)
JP (1)	JP4607758B2 (pl)
KR (1)	KR101092150B1 (pl)
AT (1)	ATE459636T1 (pl)
AU (1)	AU2003224308A1 (pl)
BR (1)	BR0315746A (pl)
CA (1)	CA2503899C (pl)
DE (1)	DE60331572D1 (pl)
ES (1)	ES2342274T3 (pl)
MX (1)	MXPA05004494A (pl)
PL (1)	PL210114B1 (pl)
PT (1)	PT1558627E (pl)
RU (1)	RU2326890C2 (pl)
SG (1)	SG148860A1 (pl)
TW (1)	TWI334781B (pl)
WO (1)	WO2004037845A1 (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0000228D0 (en) *	2000-01-06	2000-03-01	Phytopharm Plc	Fluoro substituted sapogenins and their use
KR101130212B1 (ko) *	2002-03-27	2012-04-13	파이토팜 피엘씨	사포게닌 및 그 유도체의 치료 방법 및 사용법
GB0409567D0 (en)	2004-04-28	2004-06-02	Phytopharm Plc	Chemical compounds
CA2722798A1 (en) *	2008-04-30	2009-11-05	Institute Of Radiation Medicine, Acadaemy Of Military Medical Scientces	Synthesis of timosaponin bii
CN106810592A (zh) *	2016-11-29	2017-06-09	杭州裕美生物科技有限公司	一种4‑烯‑3,6‑二酮甾体的合成工艺
CN115595353B (zh) *	2022-10-29	2024-08-23	西北农林科技大学	一种利用微生物转化制备薯蓣皂苷酮的方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB736818A (en)	1951-12-28	1955-09-14	Glidden Co	Improvements in or relating to preparation of 3-keto steroids having cis junction of rings a and b
GB763301A (en)	1953-09-05	1956-12-12	Farmaceutici Italia	Process for the reduction of í¸-3-keto-steroids to 5-ª -dihydro-steroids
DE2257132C3 (de) *	1972-11-18	1982-05-13	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Verfahren zur Reduktion von 3-Ketosteroiden
BR9306619A (pt) *	1992-06-26	1998-12-08	Pfizer	Glicosídeos esteroidais para o tratamento da hipercolesterolemia
CA2180148A1 (en) *	1993-12-28	1995-07-06	Michael Paul Deninno	Hypocholesterolemic agents
US5807834A (en) *	1994-09-20	1998-09-15	Pfizer Inc.	Combination of a cholesterol absorption inhibitor and a cholesterol synthesis inhibitor
WO1996038466A1 (en)	1995-05-29	1996-12-05	Pfizer Inc.	Steroidal glycosides
GB9923076D0 (en)	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
ATE337788T1 (de) *	1998-03-26	2006-09-15	Phytopharm Plc	Steroidale saponine zur behandlung der alzheimerischen krankheit
GB0000228D0 (en) *	2000-01-06	2000-03-01	Phytopharm Plc	Fluoro substituted sapogenins and their use
GB0107822D0 (en) *	2001-03-28	2001-05-23	Phytopharm Plc	Sapogenin derivatives their synthesis and use methods based upon their use

2003
- 2003-04-28 PL PL376791A patent/PL210114B1/pl not_active IP Right Cessation
- 2003-04-28 US US10/531,086 patent/US7718792B2/en not_active Expired - Fee Related
- 2003-04-28 PT PT03720733T patent/PT1558627E/pt unknown
- 2003-04-28 AU AU2003224308A patent/AU2003224308A1/en not_active Abandoned
- 2003-04-28 ES ES03720733T patent/ES2342274T3/es not_active Expired - Lifetime
- 2003-04-28 BR BR0315746-6A patent/BR0315746A/pt not_active IP Right Cessation
- 2003-04-28 RU RU2005111593/04A patent/RU2326890C2/ru not_active IP Right Cessation
- 2003-04-28 MX MXPA05004494A patent/MXPA05004494A/es active IP Right Grant
- 2003-04-28 TW TW092109883A patent/TWI334781B/zh not_active IP Right Cessation
- 2003-04-28 AT AT03720733T patent/ATE459636T1/de active
- 2003-04-28 JP JP2005501542A patent/JP4607758B2/ja not_active Expired - Fee Related
- 2003-04-28 SG SG200703083-6A patent/SG148860A1/en unknown
- 2003-04-28 KR KR1020057007429A patent/KR101092150B1/ko not_active Expired - Fee Related
- 2003-04-28 EP EP03720733A patent/EP1558627B1/en not_active Expired - Lifetime
- 2003-04-28 DE DE60331572T patent/DE60331572D1/de not_active Expired - Lifetime
- 2003-04-28 CA CA2503899A patent/CA2503899C/en not_active Expired - Fee Related
- 2003-04-28 WO PCT/GB2003/001780 patent/WO2004037845A1/en not_active Ceased

Also Published As

Publication number	Publication date
MXPA05004494A (es)	2005-07-26
PT1558627E (pt)	2010-05-06
JP4607758B2 (ja)	2011-01-05
DE60331572D1 (de)	2010-04-15
KR20050090379A (ko)	2005-09-13
TWI334781B (en)	2010-12-21
EP1558627A1 (en)	2005-08-03
RU2326890C2 (ru)	2008-06-20
CA2503899C (en)	2011-12-20
ES2342274T3 (es)	2010-07-05
TW200406215A (en)	2004-05-01
US20060041119A1 (en)	2006-02-23
US7718792B2 (en)	2010-05-18
AU2003224308A1 (en)	2004-05-13
RU2005111593A (ru)	2006-05-10
BR0315746A (pt)	2005-09-06
KR101092150B1 (ko)	2011-12-12
WO2004037845A1 (en)	2004-05-06
EP1558627B1 (en)	2010-03-03
PL210114B1 (pl)	2011-12-30
CA2503899A1 (en)	2004-05-06
JP2006507360A (ja)	2006-03-02
ATE459636T1 (de)	2010-03-15
SG148860A1 (en)	2009-01-29

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Legal Events

Date	Code	Title	Description
2013-07-31	RECP	Rectifications of patent specification
2014-05-30	LAPS	Decisions on the lapse of the protection rights	Effective date: 20130428