JPH08503471A - ５−アルファ−レダクターゼ阻害剤としての１７置換アシル−３−カルボキシ３，５−ジエンステロイド類 - Google Patents

５−アルファ−レダクターゼ阻害剤としての１７置換アシル−３−カルボキシ３，５−ジエンステロイド類

Info

Publication number: JPH08503471A
Authority: JP; Japan
Prior art keywords: substituted; formula; compound; pharmaceutically acceptable; compound according
Prior art date: 1992-11-18
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.): Pending

Application number

JP6512499A

Other languages

English (en)

Japanese (ja)

Inventor

ホルト，デニス・アラン

レヴィ，マーク・アラン

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.)

SmithKline Beecham Corp

Original Assignee

SmithKline Beecham Corp

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.)

1992-11-18

Filing date

1993-11-18

Publication date

1996-04-16

1992-11-18 Priority claimed from GB929224213A external-priority patent/GB9224213D0/en

1993-08-14 Priority claimed from GB939316954A external-priority patent/GB9316954D0/en

1993-11-18 Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp

1996-04-16 Publication of JPH08503471A publication Critical patent/JPH08503471A/ja

Status Pending legal-status Critical Current

Links

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239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
229950006238 nadide Drugs 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
QEKXARSPUFVXIX-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dibromide Chemical compound [Ni+2].[Br-].[Br-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QEKXARSPUFVXIX-UHFFFAOYSA-L 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000010466 nut oil Substances 0.000 description 1
235000019488 nut oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
SJPOVWGOESAUHV-YBYOAESISA-N s-pyridin-2-yl (8s,9s,10r,13s,14s,17s)-3-cyano-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene-17-carbothioate Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(CCC(=CC4=CC3)C#N)C)CC[C@@]21C)SC1=CC=CC=N1 SJPOVWGOESAUHV-YBYOAESISA-N 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
235000012046 side dish Nutrition 0.000 description 1
238000007873 sieving Methods 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 0.000 description 1
MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
229940100613 topical solution Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
YNIRKEZIDLCCMC-UHFFFAOYSA-K trisodium;phosphate;hydrate Chemical compound [OH-].[Na+].[Na+].[Na+].OP([O-])([O-])=O YNIRKEZIDLCCMC-UHFFFAOYSA-K 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0014—Androstane derivatives substituted in position 17 alfa, not substituted in position 17 beta
- 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
- 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
- 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
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Chemical Kinetics & Catalysis (AREA)
Toxicology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP6512499A 1992-11-18 1993-11-18 ５−アルファ−レダクターゼ阻害剤としての１７置換アシル−３−カルボキシ３，５−ジエンステロイド類 Pending JPH08503471A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB929224213A GB9224213D0 (en)	1992-11-18	1992-11-18	Compounds
GB9224213.0		1992-11-18
GB9316954.8		1993-08-14
GB939316954A GB9316954D0 (en)	1993-08-14	1993-08-14	Compounds
PCT/US1993/011225 WO1994011004A1 (fr)	1992-11-18	1993-11-18	Steroides 17 substitutes acyle-3-carboxy 3,5-diene en tant qu'inhibiteurs de 5-alpha-reductase

Publications (1)

Publication Number	Publication Date
JPH08503471A true JPH08503471A (ja)	1996-04-16

Family

ID=26302003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6512499A Pending JPH08503471A (ja)	1992-11-18	1993-11-18	５−アルファ−レダクターゼ阻害剤としての１７置換アシル−３−カルボキシ３，５−ジエンステロイド類

Country Status (12)

Country	Link
EP (2)	EP0673251A1 (fr)
JP (1)	JPH08503471A (fr)
CN (2)	CN1101914A (fr)
AP (1)	AP9300589A0 (fr)
AU (2)	AU5613394A (fr)
CA (1)	CA2149427A1 (fr)
IL (1)	IL107611A0 (fr)
MA (1)	MA23036A1 (fr)
MX (1)	MX9307203A (fr)
NZ (1)	NZ258723A (fr)
SI (1)	SI9300601A (fr)
WO (2)	WO1994011004A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW369521B (en) *	1993-09-17	1999-09-11	Smithkline Beecham Corp	Androstenone derivative
GB9415183D0 (en) *	1994-07-28	1994-09-21	Erba Carlo Spa	3-carboxysteroids with a fluorinated side-chain
GB9415178D0 (en) *	1994-07-28	1994-09-21	Erba Carlo Spa	4-azasteroids with side-chain fluoroketones
JPH10507176A (ja) *	1994-10-05	1998-07-14	スミスクライン・ビーチャム・コーポレイション	１７−ベータ−置換アンドロスタ−３，５−ジエン−３−カルボン酸の製法
US5541322A (en) *	1994-10-14	1996-07-30	Glaxo Wellcome Inc.	Synthesis of 6-azaandrostenones
US5543417A (en) *	1994-10-21	1996-08-06	Merck & Co., Inc.	Combination method of treating acne using 4-AZA-5α-cholestan-ones and 4-AZA-5α-androstan-ones as selective 5α-reductase inhibitors with anti-bacterial, keratolytic, or anti-inflammatory agents
CA2309350C (fr)	1997-11-12	2007-04-03	Mitsubishi Chemical Corporation	Derives de purine et medicament les renfermant en tant qu'ingredient actif
CN1160355C (zh)	1999-05-11	2004-08-04	三菱化学株式会社	嘌呤衍生物二水合物、含有该化合物作为有效成分的药物及其制备中间体
FR2817257B1 (fr)	2000-11-30	2009-03-20	Sanofi Synthelabo	Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant
GB201102913D0 (en)	2011-02-18	2011-04-06	Univ Birmingham	Novel therapeutic

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5041433A (en) *	1987-04-29	1991-08-20	Smithkline Beecham Corporation	11-keto or hydroxy 3,5-diene steroids as inhibitors of steriod 5-α-reductase
US4910226A (en) *	1987-04-29	1990-03-20	Smithkline Beckman Corporation	Steroid 5-alpha-reductase inhibitors
US4954446A (en) *	1988-05-25	1990-09-04	Smithkline Beecham Corporation	Aromatic steroid 5-α-reductase inhibitors
US5032586A (en) *	1989-08-24	1991-07-16	Smithkline Beecham Corporation	7-keto or hydroxy 3,5-diene steroids as inhibitors of steroid 5-alpha reductase
US5137882A (en) *	1990-06-11	1992-08-11	Holt Dennis A	Steroidal 3-acetic acid derivatives as 5-alpha-reductase inhibitors
US5091380A (en) *	1990-06-28	1992-02-25	Merck & Co., Inc.	N-monosubstituted adamantyl/norbornanyl 17β-carbamides of 3-carboxy-androst-3,5-dienes as testosterone 5α-reductase inhibitors
EP0465123A3 (en) *	1990-06-28	1992-05-06	Merck & Co. Inc.	New intermediates in the synthesis of 17beta-acyl-3-carboxy-androsta-3,5-dienes
CA2045866A1 (fr) *	1990-06-28	1991-12-29	Gary H. Rasmusson	17-beta-acyl-3-carboxyandrosta-3,5-dienes comme inhibiteurs de la testosterone-5-alpha-reductase
US5196411A (en) *	1991-08-16	1993-03-23	Merck & Co., Inc.	17β-acyl-3-carboxy-androsta-3,5-dienes as testosterone 5α-reductase inhibitors

1993
- 1993-11-15 AP APAP/P/1993/000589A patent/AP9300589A0/en unknown
- 1993-11-15 IL IL10761193A patent/IL107611A0/xx unknown
- 1993-11-17 MX MX9307203A patent/MX9307203A/es unknown
- 1993-11-17 MA MA23342A patent/MA23036A1/fr unknown
- 1993-11-18 NZ NZ258723A patent/NZ258723A/en unknown
- 1993-11-18 CN CN93114775A patent/CN1101914A/zh active Pending
- 1993-11-18 EP EP94901600A patent/EP0673251A1/fr not_active Withdrawn
- 1993-11-18 AU AU56133/94A patent/AU5613394A/en not_active Abandoned
- 1993-11-18 SI SI9300601A patent/SI9300601A/sl unknown
- 1993-11-18 WO PCT/US1993/011225 patent/WO1994011004A1/fr not_active Ceased
- 1993-11-18 EP EP94902307A patent/EP0669932A4/fr not_active Withdrawn
- 1993-11-18 JP JP6512499A patent/JPH08503471A/ja active Pending
- 1993-11-18 WO PCT/US1993/011241 patent/WO1994011386A1/fr not_active Ceased
- 1993-11-18 CN CN93121434A patent/CN1101916A/zh active Pending
- 1993-11-18 CA CA002149427A patent/CA2149427A1/fr not_active Abandoned
- 1993-11-18 AU AU56717/94A patent/AU5671794A/en not_active Abandoned

Also Published As

Publication number	Publication date
WO1994011004A1 (fr)	1994-05-26
CN1101914A (zh)	1995-04-26
AU5671794A (en)	1994-06-08
NZ258723A (en)	1996-12-20
MX9307203A (es)	1994-07-29
AP9300589A0 (en)	1994-01-31
IL107611A0 (en)	1994-02-27
MA23036A1 (fr)	1994-07-01
CA2149427A1 (fr)	1994-05-26
EP0669932A4 (fr)	1995-10-25
EP0673251A4 (fr)	1995-10-25
SI9300601A (en)	1994-06-30
EP0669932A1 (fr)	1995-09-06
WO1994011386A1 (fr)	1994-05-26
CN1101916A (zh)	1995-04-26
AU5613394A (en)	1994-06-08
EP0673251A1 (fr)	1995-09-27

Publication	Publication Date	Title
EP0375345B1 (fr)	1994-11-30	Stéroides aromatiques substituées par l'acide phosphonique comme inhibiteurs de 5-alpha-réductase
EP0375344B1 (fr)	1995-02-15	Stéroides aromatiques, substitués par l'acide phosphonique, comme inhibiteurs de 5-alpha réductase
EP0375347B1 (fr)	1994-12-21	Stéroides aromatiques substitués par l'acide sulfonique, comme inhibiteurs de 5alpha-réductase
JP2675418B2 (ja)	1997-11-12	芳香族ステロイド５‐α‐レダクターゼ抑制剤
US5032586A (en)	1991-07-16	7-keto or hydroxy 3,5-diene steroids as inhibitors of steroid 5-alpha reductase
JPH03169890A (ja)	1991-07-23	ステロイド５―α―レダクターゼの抑制剤としての１１―ケトまたはヒドロキシ３，５―ジエンステロイド類
US4954446A (en)	1990-09-04	Aromatic steroid 5-α-reductase inhibitors
US5527806A (en)	1996-06-18	17α and 17β substituted acyl 4 aza steroids
WO1994011004A1 (fr)	1994-05-26	Steroides 17 substitutes acyle-3-carboxy 3,5-diene en tant qu'inhibiteurs de 5-alpha-reductase
US5137882A (en)	1992-08-11	Steroidal 3-acetic acid derivatives as 5-alpha-reductase inhibitors
AP412A (en)	1995-09-29	17a and 17B-Alkylketone-3-carboxyaromatic a ring steroidal compounds and pharmaceutical compositions containing these compounds.
US5641877A (en)	1997-06-24	17-α and 17-β substituted acyl-3-carboxy-3, 5-dienes and use in inhibiting 5-α-reductase
US5683995A (en)	1997-11-04	17 substituted acyl-3-carboxy 3,5-diene steroidals as α-reductase inhibitors
US5618806A (en)	1997-04-08	17α and 17β-substituted estra-1,3,5(10)-triene-3-carbboxlic acid
JPH08503474A (ja)	1996-04-16	１７‐アルファおよび１７‐ベータ置換アシル−３−カルボキシ−３，５−ジエンおよび５−アルファ−リダクターゼの阻害における使用
EP0650358A1 (fr)	1995-05-03	17-acyl-4-aza-steroide-3-one a titre d'inhibiteurs de 5-alpha-reductase
WO1995021185A1 (fr)	1995-08-10	STEROIDES A CYCLE A ACYLE 3-CARBOXY AROMATIQUE UTILISE COMME INHIBITEUR DE 5-α REDUCTASE