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
CN102727501A (zh) *	2002-03-27	2012-10-17	菲特法姆股份有限公司	皂角苷配基及其衍生物的用途
GB0409567D0 (en) *	2004-04-28	2004-06-02	Phytopharm Plc	Chemical compounds
KR20110018886A (ko) *	2008-04-30	2011-02-24	인스티튜트 오브 레디에이션 메디신, 아카데미 오브 밀리터리 메디칼 사이언티시즈 오브 더 피엘에이	티모사포닌 ｂｉｉ의 합성
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
US5629295A (en) *	1992-06-26	1997-05-13	Pfizer Inc.	Steroidal glycosides for treating hypercholesterolemia
EP0737202A1 (en) *	1993-12-28	1996-10-16	Pfizer Inc.	Hypocholesterolemic agents
AU2453295A (en) *	1994-09-20	1996-04-19	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
PL195897B1 (pl)	1998-03-26	2007-11-30	Phytopharm Plc	Zastosowanie smilageniny
GB9923076D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
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 SG SG200703083-6A patent/SG148860A1/en unknown
- 2003-04-28 JP JP2005501542A patent/JP4607758B2/ja not_active Expired - Fee Related
- 2003-04-28 AU AU2003224308A patent/AU2003224308A1/en not_active Abandoned
- 2003-04-28 BR BR0315746-6A patent/BR0315746A/pt not_active IP Right Cessation
- 2003-04-28 WO PCT/GB2003/001780 patent/WO2004037845A1/en not_active Ceased
- 2003-04-28 KR KR1020057007429A patent/KR101092150B1/ko not_active Expired - Fee Related
- 2003-04-28 MX MXPA05004494A patent/MXPA05004494A/es active IP Right Grant
- 2003-04-28 AT AT03720733T patent/ATE459636T1/de active
- 2003-04-28 ES ES03720733T patent/ES2342274T3/es not_active Expired - Lifetime
- 2003-04-28 RU RU2005111593/04A patent/RU2326890C2/ru not_active IP Right Cessation
- 2003-04-28 TW TW092109883A patent/TWI334781B/zh not_active IP Right Cessation
- 2003-04-28 PT PT03720733T patent/PT1558627E/pt unknown
- 2003-04-28 CA CA2503899A patent/CA2503899C/en not_active Expired - Fee Related
- 2003-04-28 DE DE60331572T patent/DE60331572D1/de not_active Expired - Lifetime
- 2003-04-28 EP EP03720733A patent/EP1558627B1/en not_active Expired - Lifetime

Also Published As

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

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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