SK89198A3 - Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives - Google Patents
Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives Download PDFInfo
- Publication number
- SK89198A3 SK89198A3 SK891-98A SK89198A SK89198A3 SK 89198 A3 SK89198 A3 SK 89198A3 SK 89198 A SK89198 A SK 89198A SK 89198 A3 SK89198 A3 SK 89198A3
- Authority
- SK
- Slovakia
- Prior art keywords
- oxo
- hydroxy
- formula
- difluoro
- tetrahydrofuran
- Prior art date
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- -1 amide androstane derivatives Chemical class 0.000 title claims description 87
- 150000002596 lactones Chemical class 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 216
- 239000012453 solvate Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 150000001441 androstanes Chemical class 0.000 claims abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 62
- 150000002148 esters Chemical class 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000686 lactone group Chemical group 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
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- 238000000926 separation method Methods 0.000 description 1
- 239000011492 sheep wool Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000007751 thermal spraying Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| SK89198A3 true SK89198A3 (en) | 1999-03-12 |
Family
ID=26308402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK891-98A SK89198A3 (en) | 1995-12-29 | 1996-12-19 | Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6197761B1 (bg) |
| EP (1) | EP0876392B1 (bg) |
| JP (1) | JP2947944B2 (bg) |
| KR (1) | KR19990076859A (bg) |
| CN (1) | CN1133643C (bg) |
| AP (1) | AP9801274A0 (bg) |
| AT (1) | ATE194356T1 (bg) |
| AU (1) | AU721865B2 (bg) |
| BG (1) | BG102625A (bg) |
| BR (1) | BR9612309A (bg) |
| CA (1) | CA2241728A1 (bg) |
| CZ (1) | CZ207498A3 (bg) |
| DE (1) | DE69609199T2 (bg) |
| DK (1) | DK0876392T3 (bg) |
| EA (1) | EA001401B1 (bg) |
| EE (1) | EE9800227A (bg) |
| ES (1) | ES2150150T3 (bg) |
| GR (1) | GR3034564T3 (bg) |
| HK (1) | HK1012193A1 (bg) |
| HU (1) | HUP9903707A3 (bg) |
| IL (1) | IL124938A0 (bg) |
| IS (1) | IS4781A (bg) |
| MX (1) | MX9805181A (bg) |
| NO (1) | NO311022B1 (bg) |
| NZ (1) | NZ324373A (bg) |
| OA (1) | OA10701A (bg) |
| PE (1) | PE87598A1 (bg) |
| PL (1) | PL327629A1 (bg) |
| PT (1) | PT876392E (bg) |
| SI (1) | SI0876392T1 (bg) |
| SK (1) | SK89198A3 (bg) |
| TR (1) | TR199801247T2 (bg) |
| TW (1) | TW498072B (bg) |
| WO (1) | WO1997024365A1 (bg) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2215310T3 (es) * | 1997-06-30 | 2004-10-01 | Glaxo Group Limited | Procedimiento para identificar compuestos que tienen una actividad sistemica reducida. |
| 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 |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6777399B2 (en) * | 2000-08-05 | 2004-08-17 | 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 |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6759398B2 (en) * | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| GB0019172D0 (en) * | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| IL154175A0 (en) * | 2000-08-05 | 2003-07-31 | Glaxo Group Ltd | 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 |
| 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 |
| AU2002253342B2 (en) * | 2001-04-30 | 2007-01-04 | Glaxo Group Limited | Novel anti-inflammatory androstane derivatives |
| 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 |
| GB0127160D0 (en) * | 2001-11-12 | 2002-01-02 | 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 |
| 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 |
| EP1466920A1 (en) * | 2003-04-04 | 2004-10-13 | Alpharma APS | Process for the preparation of steroidal 17 beta-carbothioates |
| WO2004087731A1 (en) * | 2003-04-04 | 2004-10-14 | Alpharma Aps | Process for the preparation of steroidal carbothioic acid derivatives and intermediates |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093721A (en) * | 1974-08-30 | 1978-06-06 | Glaxo Laboratories Limited | Pharmaceutical compositions of 6α,9α-difluoro-androst-4-ene-17β-carboxylates and derivatives thereof |
| US4188385A (en) | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| 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 PT PT96942493T patent/PT876392E/pt unknown
- 1996-12-19 EP EP96942493A patent/EP0876392B1/en not_active Expired - Lifetime
- 1996-12-19 KR KR1019980704986A patent/KR19990076859A/ko not_active Application Discontinuation
- 1996-12-19 CN CNB961801077A patent/CN1133643C/zh not_active Expired - Lifetime
- 1996-12-19 CZ CZ982074A patent/CZ207498A3/cs unknown
- 1996-12-19 US US09/091,748 patent/US6197761B1/en not_active Expired - Fee Related
- 1996-12-19 EE EE9800227A patent/EE9800227A/xx unknown
- 1996-12-19 JP JP9524095A patent/JP2947944B2/ja not_active Expired - Fee Related
- 1996-12-19 DE DE69609199T patent/DE69609199T2/de not_active Expired - Fee Related
- 1996-12-19 ES ES96942493T patent/ES2150150T3/es not_active Expired - Lifetime
- 1996-12-19 EA EA199800484A patent/EA001401B1/ru not_active IP Right Cessation
- 1996-12-19 HU HU9903707A patent/HUP9903707A3/hu unknown
- 1996-12-19 AU AU11409/97A patent/AU721865B2/en not_active Ceased
- 1996-12-19 IL IL12493896A patent/IL124938A0/xx unknown
- 1996-12-19 SI SI9630232T patent/SI0876392T1/xx unknown
- 1996-12-19 DK DK96942493T patent/DK0876392T3/da active
- 1996-12-19 CA CA002241728A patent/CA2241728A1/en not_active Abandoned
- 1996-12-19 PL PL96327629A patent/PL327629A1/xx unknown
- 1996-12-19 TR TR1998/01247T patent/TR199801247T2/xx unknown
- 1996-12-19 AT AT96942493T patent/ATE194356T1/de not_active IP Right Cessation
- 1996-12-19 NZ NZ324373A patent/NZ324373A/en unknown
- 1996-12-19 AP APAP/P/1998/001274A patent/AP9801274A0/en unknown
- 1996-12-19 BR BR9612309A patent/BR9612309A/pt not_active Application Discontinuation
- 1996-12-19 SK SK891-98A patent/SK89198A3/sk unknown
- 1996-12-19 WO PCT/GB1996/003140 patent/WO1997024365A1/en 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/bg unknown
- 1998-12-16 HK HK98113683A patent/HK1012193A1/xx not_active IP Right Cessation
-
2000
- 2000-10-04 GR GR20000402254T patent/GR3034564T3/el not_active IP Right Cessation
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