SI9300601A - Pharmaceutical active 17-alpha and 17-beta substituted acyl-3-carboxy-3,5-diene steroidal compounds - Google Patents

Pharmaceutical active 17-alpha and 17-beta substituted acyl-3-carboxy-3,5-diene steroidal compounds Download PDF

Info

Publication number: SI9300601A
Authority: SI; Slovenia
Prior art keywords: substituted; alkyl; aryl; cycloalkyl; hydrogen
Prior art date: 1992-11-18

Application number

SI9300601A

Other languages

English (en)

Slovenian (sl)

Inventor

Alan Dennis Holt

Alan Mark Levy

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

1994-06-30

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

1994-06-30 Publication of SI9300601A publication Critical patent/SI9300601A/sl

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 184
230000003637 steroidlike Effects 0.000 title claims abstract description 6
238000000034 method Methods 0.000 claims abstract description 36
230000008569 process Effects 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims description 181
125000000217 alkyl group Chemical group 0.000 claims description 157
-1 N-acylamino Chemical group 0.000 claims description 147
239000001257 hydrogen Substances 0.000 claims description 96
229910052739 hydrogen Inorganic materials 0.000 claims description 96
125000000753 cycloalkyl group Chemical group 0.000 claims description 82
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 73
229910052736 halogen Inorganic materials 0.000 claims description 68
150000002367 halogens Chemical group 0.000 claims description 68
125000001424 substituent group Chemical group 0.000 claims description 68
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 64
125000004093 cyano group Chemical group *C#N 0.000 claims description 57
125000004423 acyloxy group Chemical group 0.000 claims description 54
125000003545 alkoxy group Chemical group 0.000 claims description 54
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
125000004104 aryloxy group Chemical group 0.000 claims description 52
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 45
125000004043 oxo group Chemical group O=* 0.000 claims description 44
125000005842 heteroatom Chemical group 0.000 claims description 36
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239000012453 solvate Substances 0.000 claims description 27
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150000004795 grignard reagents Chemical class 0.000 claims description 9
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239000008187 granular material Substances 0.000 description 1
230000003779 hair growth Effects 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000012886 linear function Methods 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils 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
210000000056 organ Anatomy 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.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 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-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
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
RGVBYMSUVGONHN-UHFFFAOYSA-N piperazin-2-ylidenemethanone Chemical compound O=C=C1CNCCN1 RGVBYMSUVGONHN-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002953 preparative HPLC Methods 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
125000006239 protecting group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 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
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940100613 topical solution Drugs 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 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
XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
208000019553 vascular disease Diseases 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)

SI9300601A 1992-11-18 1993-11-18 Pharmaceutical active 17-alpha and 17-beta substituted acyl-3-carboxy-3,5-diene steroidal compounds SI9300601A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929224213A GB9224213D0 (en)	1992-11-18	1992-11-18	Compounds
GB939316954A GB9316954D0 (en)	1993-08-14	1993-08-14	Compounds

Publications (1)

Publication Number	Publication Date
SI9300601A true SI9300601A (en)	1994-06-30

Family

ID=26302003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9300601A SI9300601A (en)	1992-11-18	1993-11-18	Pharmaceutical active 17-alpha and 17-beta substituted acyl-3-carboxy-3,5-diene steroidal compounds

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
JPH08503471A (ja)	1996-04-16
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
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
JP2675418B2 (ja)	1997-11-12	芳香族ステロイド５‐α‐レダクターゼ抑制剤
US5595996A (en)	1997-01-21	7-substituted 4-aza cholanic acid derivatives and their use
IE65562B1 (en)	1995-11-01	11-keto or hydroxy 3,5-diene steroids as inhibitors of steroid 5-alpha-reductase
NZ235000A (en)	1992-03-26	7-(keto or hydroxy)-3,5-diene steroids and pharmaceutical compositions
US5527806A (en)	1996-06-18	17α and 17β substituted acyl 4 aza steroids
NZ258723A (en)	1996-12-20	17<beta>-carbonyl-androsta-3,5-diene-3-carboxylic acid derivatives
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.
JPH05194582A (ja)	1993-08-03	テストステロン５α−リダクターゼ抑制剤としての１７β−アシル−３−カルボキシ−アンドロスタ−３，５−ジエン
US5641877A (en)	1997-06-24	17-α and 17-β substituted acyl-3-carboxy-3, 5-dienes and use in inhibiting 5-α-reductase
US5618806A (en)	1997-04-08	17α and 17β-substituted estra-1,3,5(10)-triene-3-carbboxlic acid
JPH0586090A (ja)	1993-04-06	１７β−アシル−３−カルボキシ−アンドロスタ−３，５−ジエンの合成における新規な中間体
JPH0592989A (ja)	1993-04-16	テストステロン５α−還元酵素阻害剤としての１７β−アシル−３−カルボキシ−アンドロスタ−３，５−ジエン類
US5683995A (en)	1997-11-04	17 substituted acyl-3-carboxy 3,5-diene steroidals as α-reductase inhibitors
WO1994000121A1 (fr)	1994-01-06	17-acyl-4-aza-steroide-3-one a titre d'inhibiteurs de 5-alpha-reductase
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
WO1995021185A1 (fr)	1995-08-10	STEROIDES A CYCLE A ACYLE 3-CARBOXY AROMATIQUE UTILISE COMME INHIBITEUR DE 5-α REDUCTASE
WO1995028413A1 (fr)	1995-10-26	STEROIDES 3-CARBOXY A SUBSTITUTION 17β INHIBANT LA 5-α-REDUCTASE