CN1101914A - 新的甾族化合物及其中间体的制法和用途 - Google Patents
新的甾族化合物及其中间体的制法和用途 Download PDFInfo
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- CN1101914A CN1101914A CN93114775A CN93114775A CN1101914A CN 1101914 A CN1101914 A CN 1101914A CN 93114775 A CN93114775 A CN 93114775A CN 93114775 A CN93114775 A CN 93114775A CN 1101914 A CN1101914 A CN 1101914A
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- Prior art keywords
- alkyl
- cycloalkyl
- aryl
- replacement
- compound
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- 150000002561 ketenes Chemical class 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 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
- 239000000825 pharmaceutical preparation Substances 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
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229940107889 rogaine Drugs 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 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
- 230000028327 secretion Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 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
- 238000010129 solution processing Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 229940095585 testosterone-5-alpha reductase inhibitors for benign prostatic hypertrophy Drugs 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000007738 vacuum evaporation Methods 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)
Applications Claiming Priority (4)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1101914A true CN1101914A (zh) | 1995-04-26 |
Family
ID=26302003
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93121434A Pending CN1101916A (zh) | 1992-11-18 | 1993-11-18 | 17α和17β取代的酰基-3-羧基3，5-二烯甾族化合物 |
| CN93114775A Pending CN1101914A (zh) | 1992-11-18 | 1993-11-18 | 新的甾族化合物及其中间体的制法和用途 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93121434A Pending CN1101916A (zh) | 1992-11-18 | 1993-11-18 | 17α和17β取代的酰基-3-羧基3，5-二烯甾族化合物 |
Country Status (12)
| Country | Link |
|---|---|
| EP (2) | EP0673251A1 (enExample) |
| JP (1) | JPH08503471A (enExample) |
| CN (2) | CN1101916A (enExample) |
| AP (1) | AP9300589A0 (enExample) |
| AU (2) | AU5613394A (enExample) |
| CA (1) | CA2149427A1 (enExample) |
| IL (1) | IL107611A0 (enExample) |
| MA (1) | MA23036A1 (enExample) |
| MX (1) | MX9307203A (enExample) |
| NZ (1) | NZ258723A (enExample) |
| SI (1) | SI9300601A (enExample) |
| WO (2) | WO1994011004A1 (enExample) |
Families Citing this family (10)
| 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 |
| AU3826095A (en) * | 1994-10-05 | 1996-05-02 | Smithkline Beecham Corporation | Process for preparing 17-beta-substituted-androsta-3,5-dien-3-carboxylic acids |
| 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 |
| WO1999024432A1 (fr) | 1997-11-12 | 1999-05-20 | 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)
| 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 |
| 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 |
| 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 |
| CA2045866A1 (en) * | 1990-06-28 | 1991-12-29 | Gary H. Rasmusson | 17-beta-acyl-3-carboxy-androsta-3,5-dienes as testosterone 5 alpha-reductase inhibitors |
| 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 IL IL10761193A patent/IL107611A0/xx unknown
- 1993-11-15 AP APAP/P/1993/000589A patent/AP9300589A0/en unknown
- 1993-11-17 MX MX9307203A patent/MX9307203A/es unknown
- 1993-11-17 MA MA23342A patent/MA23036A1/fr unknown
- 1993-11-18 WO PCT/US1993/011225 patent/WO1994011004A1/en not_active Ceased
- 1993-11-18 CN CN93121434A patent/CN1101916A/zh active Pending
- 1993-11-18 AU AU56133/94A patent/AU5613394A/en not_active Abandoned
- 1993-11-18 CN CN93114775A patent/CN1101914A/zh active Pending
- 1993-11-18 JP JP6512499A patent/JPH08503471A/ja active Pending
- 1993-11-18 AU AU56717/94A patent/AU5671794A/en not_active Abandoned
- 1993-11-18 NZ NZ258723A patent/NZ258723A/en unknown
- 1993-11-18 CA CA002149427A patent/CA2149427A1/en not_active Abandoned
- 1993-11-18 WO PCT/US1993/011241 patent/WO1994011386A1/en not_active Ceased
- 1993-11-18 EP EP94901600A patent/EP0673251A1/en not_active Withdrawn
- 1993-11-18 SI SI9300601A patent/SI9300601A/sl unknown
- 1993-11-18 EP EP94902307A patent/EP0669932A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994011386A1 (en) | 1994-05-26 |
| WO1994011004A1 (en) | 1994-05-26 |
| AU5671794A (en) | 1994-06-08 |
| AP9300589A0 (en) | 1994-01-31 |
| IL107611A0 (en) | 1994-02-27 |
| EP0673251A1 (en) | 1995-09-27 |
| EP0669932A1 (en) | 1995-09-06 |
| EP0673251A4 (enExample) | 1995-10-25 |
| MA23036A1 (fr) | 1994-07-01 |
| JPH08503471A (ja) | 1996-04-16 |
| NZ258723A (en) | 1996-12-20 |
| CA2149427A1 (en) | 1994-05-26 |
| AU5613394A (en) | 1994-06-08 |
| CN1101916A (zh) | 1995-04-26 |
| EP0669932A4 (en) | 1995-10-25 |
| SI9300601A (en) | 1994-06-30 |
| MX9307203A (es) | 1994-07-29 |
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| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
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