NO311022B1 - Laktonderivater av 17<beta>-karboksy-karbotio- og amidandrostanderivater, anvendelse og fremstilling derav, samtfarmasoytiske preparater som inneholder dem - Google Patents

Laktonderivater av 17<beta>-karboksy-karbotio- og amidandrostanderivater, anvendelse og fremstilling derav, samtfarmasoytiske preparater som inneholder dem Download PDF

Info

Publication number: NO311022B1
Authority: NO; Norway
Prior art keywords: oxo; formula; hydroxy; difluoro; tetrahydro
Prior art date: 1995-12-29

Application number

NO19983004A

Other languages

English (en)

Norwegian (no)

Other versions

NO983004D0 (no

NO983004L (no

Inventor

Keith Biggadike

Panayiotis Alexandro Procopiou

Original Assignee

Glaxo Group Ltd

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.)

1995-12-29

Filing date

1998-06-26

Publication date

2001-10-01

1995-12-29 Priority claimed from GBGB9526651.6A external-priority patent/GB9526651D0/en

1996-06-21 Priority claimed from GBGB9613121.4A external-priority patent/GB9613121D0/en

1998-06-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1998-06-26 Publication of NO983004D0 publication Critical patent/NO983004D0/no

1998-08-26 Publication of NO983004L publication Critical patent/NO983004L/no

2001-10-01 Publication of NO311022B1 publication Critical patent/NO311022B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 30
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239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 235
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239000002253 acid Substances 0.000 claims description 43
238000000034 method Methods 0.000 claims description 43
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239000001257 hydrogen Substances 0.000 claims description 29
239000012453 solvate Substances 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 21
-1 2-oxo-tetrahydro-furan-3-yl Chemical group 0.000 claims description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 10
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229910052760 oxygen Inorganic materials 0.000 claims description 8
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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238000004458 analytical method Methods 0.000 description 13
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230000003110 anti-inflammatory effect Effects 0.000 description 9
239000002585 base Substances 0.000 description 9
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
LFJJGHGXHXXDFT-UHFFFAOYSA-N 3-bromooxolan-2-one Chemical compound BrC1CCOC1=O LFJJGHGXHXXDFT-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
230000009885 systemic effect Effects 0.000 description 7
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0066—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by a carbon atom forming part of an amide group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19983004A 1995-12-29 1998-06-26 Laktonderivater av 17<beta>-karboksy-karbotio- og amidandrostanderivater, anvendelse og fremstilling derav, samtfarmasoytiske preparater som inneholder dem NO311022B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9526651.6A GB9526651D0 (en)	1995-12-29	1995-12-29	Compounds
GBGB9613121.4A GB9613121D0 (en)	1996-06-21	1996-06-21	Compounds
PCT/GB1996/003140 WO1997024365A1 (en)	1995-12-29	1996-12-19	Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives

Publications (3)

Publication Number	Publication Date
NO983004D0 NO983004D0 (no)	1998-06-26
NO983004L NO983004L (no)	1998-08-26
NO311022B1 true NO311022B1 (no)	2001-10-01

Family

ID=26308402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19983004A NO311022B1 (no)	1995-12-29	1998-06-26	Laktonderivater av 17<beta>-karboksy-karbotio- og amidandrostanderivater, anvendelse og fremstilling derav, samtfarmasoytiske preparater som inneholder dem

Country Status (33)

Country	Link
US (1)	US6197761B1 (cs)
EP (1)	EP0876392B1 (cs)
JP (1)	JP2947944B2 (cs)
KR (1)	KR19990076859A (cs)
CN (1)	CN1133643C (cs)
AP (1)	AP9801274A0 (cs)
AT (1)	ATE194356T1 (cs)
AU (1)	AU721865B2 (cs)
BG (1)	BG102625A (cs)
BR (1)	BR9612309A (cs)
CA (1)	CA2241728A1 (cs)
CZ (1)	CZ207498A3 (cs)
DE (1)	DE69609199T2 (cs)
DK (1)	DK0876392T3 (cs)
EA (1)	EA001401B1 (cs)
EE (1)	EE9800227A (cs)
ES (1)	ES2150150T3 (cs)
GR (1)	GR3034564T3 (cs)
HU (1)	HUP9903707A3 (cs)
IL (1)	IL124938A0 (cs)
IS (1)	IS4781A (cs)
MX (1)	MX9805181A (cs)
NO (1)	NO311022B1 (cs)
NZ (1)	NZ324373A (cs)
OA (1)	OA10701A (cs)
PE (1)	PE87598A1 (cs)
PL (1)	PL327629A1 (cs)
PT (1)	PT876392E (cs)
SI (1)	SI0876392T1 (cs)
SK (1)	SK89198A3 (cs)
TR (1)	TR199801247T2 (cs)
TW (1)	TW498072B (cs)
WO (1)	WO1997024365A1 (cs)

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GB9909229D0 (en) *	1999-04-23	1999-06-16	Glaxo Group Ltd	Enantiomers of mercapto lactones and processes for their synthesis
GB0017988D0 (en) *	2000-07-21	2000-09-13	Glaxo Group Ltd	Novel process
US6858596B2 (en) *	2000-08-05	2005-02-22	Smithkline Beecham Corporation	Formulation containing anti-inflammatory androstane derivative
US6777399B2 (en) *	2000-08-05	2004-08-17	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6759398B2 (en)	2000-08-05	2004-07-06	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative
US6777400B2 (en)	2000-08-05	2004-08-17	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
GB0019172D0 (en) *	2000-08-05	2000-09-27	Glaxo Group Ltd	Novel compounds
EP2067784A3 (en) *	2000-08-05	2012-08-22	Glaxo Group Limited	17.beta.-carbothioate 17.alpha.-arylcarbonyloxyloxy androstane derivatives as anti-inflammatory agents
US6750210B2 (en)	2000-08-05	2004-06-15	Smithkline Beecham Corporation	Formulation containing novel anti-inflammatory androstane derivative
US6858593B2 (en)	2000-08-05	2005-02-22	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6787532B2 (en)	2000-08-05	2004-09-07	Smithkline Beecham Corporation	Formulation containing anti-inflammatory androstane derivatives
UA77656C2 (en)	2001-04-07	2007-01-15	Glaxo Group Ltd	S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent
WO2002088167A1 (en) *	2001-04-30	2002-11-07	Glaxo Group Limited	Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha
ATE399174T1 (de) *	2001-06-12	2008-07-15	Glaxo Group Ltd	Neue anti inflammatorische 17.alpha.- heterozyklische ester von 17.beta.-carbothioat androstan derivativen
WO2003018575A1 (en) *	2001-08-24	2003-03-06	Wyeth Holdings Corporation	5-substituted-3(2h)-furanones useful for inhibition of farnesyl-protein transferase
GB0125259D0 (en) *	2001-10-20	2001-12-12	Glaxo Group Ltd	Novel compounds
WO2003042229A1 (en) *	2001-11-12	2003-05-22	Glaxo Group Limited	Non-aromatic heterocyclic esters of furan-2-one-esters of 17.beta.-carboxyl or 17.beta.-carbothio glucocorticoids
GB0127160D0 (en) *	2001-11-12	2002-01-02	Glaxo Group Ltd	Novel compounds
US20050175545A1 (en) *	2002-02-04	2005-08-11	Keith Biggadike	Formulation for inhalation comprising a glucocorticoid and a beta 2-adrenoreceptor agonist
GB0202635D0 (en) *	2002-02-05	2002-03-20	Glaxo Wellcome Mfg Pte Ltd	Formulation containing novel anti-inflammatory androstane derivative
GB2389530B (en) *	2002-06-14	2007-01-10	Cipla Ltd	Pharmaceutical compositions
CA2530680A1 (en) *	2003-04-04	2004-10-14	Alpharma Aps	Process for the preparation of steroidal carbothioic acid derivatives and intermediates
EP1466920A1 (en) *	2003-04-04	2004-10-13	Alpharma APS	Process for the preparation of steroidal 17 beta-carbothioates
CN100558362C (zh) *	2004-04-01	2009-11-11	霍夫曼-拉罗奇有限公司	三氧嘧啶治疗和预防支气管炎症疾病的应用
PT103202B (pt)	2004-10-19	2011-01-27	Hovione Farmaciencia S A	Processo para a esterificação de um ácido carbotiótico
GB0507165D0 (en) *	2005-04-08	2005-05-18	Glaxo Group Ltd	Novel crystalline pharmaceutical product
AR059216A1 (es) *	2006-01-27	2008-03-19	Sun Pharmaceutical Ind Ltd	11b-hidroxiandrosta-4-eno-3-onas
GB0615108D0 (en) *	2006-07-28	2006-09-06	Glaxo Group Ltd	Novel formulations
CN103087137A (zh) *	2011-11-07	2013-05-08	天津金耀集团有限公司	一种21位为硫代烃基的糖皮质激素
US20250296918A1 (en)	2022-04-28	2025-09-25	Resonac Corporation	Method for producing mercapto heterocyclic compound and method for testing the same
EP4635969A1 (en) *	2022-12-16	2025-10-22	Tianjin Pharmaceutical Biotechnology Co., Ltd.	Novel glucocorticoid, method for preparing same, and use thereof
WO2025256615A1 (zh) *	2024-06-14	2025-12-18	津药药业股份有限公司	新型糖皮质激素的晶型

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SE8306370D0 (sv)	1983-11-18	1983-11-18	Draco Ab	Novel androstane-17beta-carboxylic acid esters, a process and intermediates for their preparation, compositions and method for the treatment of inflammatory conditions
IL78144A0 (en)	1985-04-04	1986-07-31	Draco Ab	Novel androstane-17beta-carboxylic acid esters
US5767113A (en) *	1995-05-10	1998-06-16	The Salk Institute For Biological Studies	Compounds useful for concurrently activating glucocorticoid-induced response and reducing multidrug resistance

1996
- 1996-12-19 SK SK891-98A patent/SK89198A3/sk unknown
- 1996-12-19 DK DK96942493T patent/DK0876392T3/da active
- 1996-12-19 CA CA002241728A patent/CA2241728A1/en not_active Abandoned
- 1996-12-19 EP EP96942493A patent/EP0876392B1/en not_active Expired - Lifetime
- 1996-12-19 AP APAP/P/1998/001274A patent/AP9801274A0/en unknown
- 1996-12-19 PT PT96942493T patent/PT876392E/pt unknown
- 1996-12-19 US US09/091,748 patent/US6197761B1/en not_active Expired - Fee Related
- 1996-12-19 NZ NZ324373A patent/NZ324373A/en unknown
- 1996-12-19 ES ES96942493T patent/ES2150150T3/es not_active Expired - Lifetime
- 1996-12-19 PL PL96327629A patent/PL327629A1/xx unknown
- 1996-12-19 HU HU9903707A patent/HUP9903707A3/hu unknown
- 1996-12-19 WO PCT/GB1996/003140 patent/WO1997024365A1/en not_active Ceased
- 1996-12-19 EA EA199800484A patent/EA001401B1/ru not_active IP Right Cessation
- 1996-12-19 CN CNB961801077A patent/CN1133643C/zh not_active Expired - Lifetime
- 1996-12-19 AU AU11409/97A patent/AU721865B2/en not_active Ceased
- 1996-12-19 AT AT96942493T patent/ATE194356T1/de not_active IP Right Cessation
- 1996-12-19 JP JP9524095A patent/JP2947944B2/ja not_active Expired - Fee Related
- 1996-12-19 SI SI9630232T patent/SI0876392T1/xx unknown
- 1996-12-19 CZ CZ982074A patent/CZ207498A3/cs unknown
- 1996-12-19 EE EE9800227A patent/EE9800227A/xx unknown
- 1996-12-19 IL IL12493896A patent/IL124938A0/xx unknown
- 1996-12-19 DE DE69609199T patent/DE69609199T2/de not_active Expired - Fee Related
- 1996-12-19 TR TR1998/01247T patent/TR199801247T2/xx unknown
- 1996-12-19 KR KR1019980704986A patent/KR19990076859A/ko not_active Withdrawn
- 1996-12-19 BR BR9612309A patent/BR9612309A/pt not_active Application Discontinuation
1997
- 1997-06-26 TW TW086108975A patent/TW498072B/zh active
- 1997-06-27 PE PE1997000549A patent/PE87598A1/es not_active Application Discontinuation
1998
- 1998-06-19 OA OA9800089A patent/OA10701A/en unknown
- 1998-06-23 IS IS4781A patent/IS4781A/is unknown
- 1998-06-25 MX MX9805181A patent/MX9805181A/es unknown
- 1998-06-26 NO NO19983004A patent/NO311022B1/no not_active IP Right Cessation
- 1998-07-13 BG BG102625A patent/BG102625A/xx unknown
2000
- 2000-10-04 GR GR20000402254T patent/GR3034564T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA2241728A1 (en)	1997-07-10
CN1133643C (zh)	2004-01-07
IL124938A0 (en)	1999-01-26
JP2947944B2 (ja)	1999-09-13
BG102625A (en)	1999-04-30
NZ324373A (en)	1999-10-28
NO983004D0 (no)	1998-06-26
DE69609199T2 (de)	2001-03-01
DE69609199D1 (de)	2000-08-10
ATE194356T1 (de)	2000-07-15
ES2150150T3 (es)	2000-11-16
PT876392E (pt)	2000-12-29
TR199801247T2 (xx)	1998-11-23
AU721865B2 (en)	2000-07-13
HUP9903707A3 (en)	2000-04-28
WO1997024365A1 (en)	1997-07-10
JPH11501675A (ja)	1999-02-09
SI0876392T1 (en)	2000-12-31
EP0876392B1 (en)	2000-07-05
BR9612309A (pt)	1999-07-13
CZ207498A3 (cs)	1998-11-11
OA10701A (en)	2002-05-21
TW498072B (en)	2002-08-11
GR3034564T3 (en)	2001-01-31
AU1140997A (en)	1997-07-28
EA001401B1 (ru)	2001-02-26
EA199800484A1 (ru)	1999-02-25
SK89198A3 (en)	1999-03-12
KR19990076859A (ko)	1999-10-25
AP9801274A0 (en)	1998-06-30
IS4781A (is)	1998-06-23
EP0876392A1 (en)	1998-11-11
MX9805181A (es)	1998-10-31
PE87598A1 (es)	1999-01-15
PL327629A1 (en)	1998-12-21
DK0876392T3 (da)	2000-11-06
EE9800227A (et)	1998-12-15
CN1209135A (zh)	1999-02-24
US6197761B1 (en)	2001-03-06
HUP9903707A2 (hu)	2000-03-28
HK1012193A1 (en)	1999-07-30
NO983004L (no)	1998-08-26

Legal Events

Date	Code	Title	Description
2005-09-12	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP0876392B1 (en)	2000-07-05	Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives
US7405206B2 (en)	2008-07-29	Anti-inflammatory androstane derivatives
EP0998484B1 (en)	2004-03-03	Method of identifying compounds having reduced systemic effects
WO2003048181A1 (en)	2003-06-12	17.alpha. -cyclic esters of 16-methylpregnan-3,20-dione as anti-inflammatory agents
EP0876393B1 (en)	2000-07-05	21-(2-oxo-tetrahydrofuran)-thio pregnane derivatives, a process for their production and pharmaceutical compositions containing them
US20020019378A1 (en)	2002-02-14	Compounds
US6114318A (en)	2000-09-05	17β-(2-oxo-tetrahydrofuranyl)-thio- substituted androstane derivatives
HK1012193B (en)	2001-01-23	Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives