FR2421912A1 - Derives d'acide thio-etianique, leur procede de production et medicament les contenant - Google Patents
Derives d'acide thio-etianique, leur procede de production et medicament les contenantInfo
- Publication number
- FR2421912A1 FR2421912A1 FR7907823A FR7907823A FR2421912A1 FR 2421912 A1 FR2421912 A1 FR 2421912A1 FR 7907823 A FR7907823 A FR 7907823A FR 7907823 A FR7907823 A FR 7907823A FR 2421912 A1 FR2421912 A1 FR 2421912A1
- Authority
- FR
- France
- Prior art keywords
- radical
- alpha
- beta
- chloro
- thio
- Prior art date
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 bromo radical Chemical class 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- 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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention a trait au domaine de la chimie médicale. Elle concerne certains esters d'acides 3-oxoandrost-4-ène et 3-oxoandrosta-1,4-diène- 17 beta -thiocarboxyliques. Ces composés sont éventuellement substitués en position 6 alpha avec un radical fluoro ou chloro; en position 9 alpha avec un radical fluoro, chloro ou bromo; en position 11 avec un radical céto, un radical beta -hydroxy ou un radical beta -chloro (ce dernier seulement lorsqu'il y a un radical chloro en position 9 alpha ; en positions 16 alpha et 17 alpha avec un radical isopropylidènedioxy; et en position 16 alpha (ou 16 beta ) avec un radical méthyle ou un atome d'hydrogène lorsqu'il y a un groupe hydroxy ou un ester en position 17 alpha . Les composés de l'invention sont des stéroïdes anti-inflammatoires.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/893,388 US4188385A (en) | 1978-04-05 | 1978-04-05 | Thioetianic acid derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2421912A1 true FR2421912A1 (fr) | 1979-11-02 |
FR2421912B1 FR2421912B1 (fr) | 1981-03-20 |
Family
ID=25401484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7907823A Granted FR2421912A1 (fr) | 1978-04-05 | 1979-03-28 | Derives d'acide thio-etianique, leur procede de production et medicament les contenant |
Country Status (28)
Country | Link |
---|---|
US (1) | US4188385A (fr) |
EP (1) | EP0004741B1 (fr) |
JP (2) | JPS54141758A (fr) |
AR (1) | AR226035A1 (fr) |
AT (1) | AT368168B (fr) |
AU (1) | AU526025B2 (fr) |
CA (1) | CA1134345A (fr) |
CS (1) | CS203956B2 (fr) |
DE (2) | DE2960096D1 (fr) |
DK (1) | DK147735C (fr) |
ES (1) | ES479271A1 (fr) |
FI (1) | FI66393C (fr) |
FR (1) | FR2421912A1 (fr) |
GB (1) | GB2018256B (fr) |
GR (1) | GR67275B (fr) |
HK (1) | HK41284A (fr) |
HU (1) | HU179314B (fr) |
IL (1) | IL56972A0 (fr) |
IT (1) | IT1120954B (fr) |
MY (1) | MY8500575A (fr) |
NO (1) | NO152935C (fr) |
NZ (1) | NZ190076A (fr) |
PL (1) | PL121469B1 (fr) |
PT (1) | PT69409A (fr) |
SG (1) | SG6786G (fr) |
SU (1) | SU1052161A3 (fr) |
YU (1) | YU40929B (fr) |
ZA (1) | ZA791635B (fr) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4261984A (en) * | 1978-04-05 | 1981-04-14 | Syntex (U.S.A.) Inc. | 17β-thiocarboxylic acid esters of 3-oxo-4-halo-16β-methylandrost-4-enes |
US4263289A (en) * | 1978-04-05 | 1981-04-21 | Syntex (U.S.A.) Inc. | Thio etianic acid derivatives |
US4310466A (en) * | 1979-08-31 | 1982-01-12 | Syntex (U.S.A.) Inc. | Thio etianic acid derivatives |
GB2137206B (en) * | 1980-02-15 | 1985-04-03 | Glaxo Group Ltd | Androstane 17-carbothioc acid derivatives |
CA1201114A (fr) * | 1980-02-15 | 1986-02-25 | Gordon H. Phillipps | Carbothioates d'androstane |
NL191792C (nl) * | 1980-02-15 | 1996-08-02 | Glaxo Group Ltd | Esters van een androstaan-17beta-carbothiozuur, werkwijze ter bereiding van deze esters, en farmaceutische preparaten, die deze esters bevatten. |
US4578221A (en) * | 1980-04-23 | 1986-03-25 | Glaxo Group Limited | Androstane carbothioic acids |
SE449106B (sv) * | 1980-07-10 | 1987-04-06 | Otsuka Pharma Co Ltd | Steroid med anti-inflammatorisk verkan samt komposition innehallande denna |
IL78144A0 (en) * | 1985-04-04 | 1986-07-31 | Draco Ab | Novel androstane-17beta-carboxylic acid esters |
GB9225923D0 (en) * | 1992-12-11 | 1993-02-03 | Rhone Poulenc Rorer Ltd | New compositions of matter |
CZ159195A3 (en) * | 1992-12-24 | 1996-03-13 | Rhone Poulenc Rorer Ltd | Novel steroids, process of their preparation and pharmaceutical compositions containing thereof |
BR9612309A (pt) * | 1995-12-29 | 1999-07-13 | Glaxo Group Ltd | Composto uso de um composto composição farmacêutica formulação farmacêutica de aerossol combinação e processos para o tratamento de um indivíduo humano ou animal com uma condição anti-inflamatória e/ou alérgica e para a preparação de um composto |
US5981517A (en) * | 1996-05-09 | 1999-11-09 | Soft Drugs, Inc. | Androstene derivatives |
US20020133032A1 (en) * | 2000-02-25 | 2002-09-19 | Jufang Barkalow | Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods |
GB0017988D0 (en) * | 2000-07-21 | 2000-09-13 | Glaxo Group Ltd | Novel process |
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 |
US6750210B2 (en) * | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
AR032471A1 (es) * | 2000-08-05 | 2003-11-12 | Glaxo Group Ltd | Derivado de androstano y solvatos del mismo, su uso para la fabricacion de medicamentos, composiciones farmaceuticas que los comprenden, procesos para preparar tales derivados, intermediarios utiles en la preparacion de tales derivados, procesos para preparar tales intermediarios, y compuestos inter |
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 |
US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
US6858593B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
US6858596B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing 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 |
CA2445839A1 (fr) * | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Derives anti-inflammatoires d'androstane 17.beta.-carbothioate ester avec un groupe cyclique en position 17.alpha |
US20040248867A1 (en) * | 2001-06-12 | 2004-12-09 | Keith Biggadike | Novel anti-inflammatory 17.alpha.-heterocyclic-esters of 17.beta.carbothioate androstane derivatives |
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 |
IL150654A (en) | 2002-07-09 | 2006-12-10 | Ori Lerman | Method for acid isolation 6α, 9α - difluoro - ß, 17α11 - dihydroxy - 16α - methylfargana - 3 - oxo - 1, 4 - diene - 17ß - carboxylate |
WO2004087731A1 (fr) * | 2003-04-04 | 2004-10-14 | Alpharma Aps | Methode de preparation de derives et d'intermediaires d'acides carbothioiques steroides |
GB0507165D0 (en) * | 2005-04-08 | 2005-05-18 | Glaxo Group Ltd | Novel crystalline pharmaceutical product |
TWI374147B (en) * | 2006-01-27 | 2012-10-11 | Sun Pharma Advance Res Company Ltd | Novel 11β-hydroxyandrosta-4-ene-3-ones |
GB0615108D0 (en) * | 2006-07-28 | 2006-09-06 | Glaxo Group Ltd | Novel formulations |
WO2009085879A2 (fr) * | 2007-12-21 | 2009-07-09 | Schering Corporation | Agonistes du récepteur de glucocorticoïde substitués en c20-c21 |
JP2012530140A (ja) | 2009-06-16 | 2012-11-29 | メルク・シャープ・アンド・ドーム・コーポレーション | グルココルチコイド受容体アゴニストとしての新規[3,2−c]ヘテロアリールステロイド、組成物およびこの使用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2509171A (en) * | 1946-02-06 | 1950-05-23 | Ciba Ltd | Primary alcohols from thiocarboxylic acids and esters |
US3636010A (en) * | 1968-12-23 | 1972-01-18 | Ciba Geigy Corp | Esters of steroid-17-carboxylic acids |
US3989686A (en) * | 1972-06-15 | 1976-11-02 | Glaxo Laboratories Limited | Anaesthetic steroids of the androstane series and process for preparing same |
GB1438940A (en) * | 1972-07-19 | 1976-06-09 | Glaxo Lab Ltd | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
CH628355A5 (de) * | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze. |
-
1978
- 1978-04-05 US US05/893,388 patent/US4188385A/en not_active Expired - Lifetime
-
1979
- 1979-03-28 DE DE7979300500T patent/DE2960096D1/de not_active Expired
- 1979-03-28 FR FR7907823A patent/FR2421912A1/fr active Granted
- 1979-03-28 DE DE19792912331 patent/DE2912331A1/de not_active Ceased
- 1979-03-28 IT IT67652/79A patent/IT1120954B/it active
- 1979-03-28 EP EP79300500A patent/EP0004741B1/fr not_active Expired
- 1979-03-28 GB GB7910862A patent/GB2018256B/en not_active Expired
- 1979-03-29 CS CS792107A patent/CS203956B2/cs unknown
- 1979-03-29 IL IL56972A patent/IL56972A0/xx not_active IP Right Cessation
- 1979-03-29 AU AU45583/79A patent/AU526025B2/en not_active Ceased
- 1979-03-30 PT PT69409A patent/PT69409A/pt unknown
- 1979-03-30 AR AR276014A patent/AR226035A1/es active
- 1979-03-30 CA CA000324557A patent/CA1134345A/fr not_active Expired
- 1979-03-31 GR GR58748A patent/GR67275B/el unknown
- 1979-04-02 NZ NZ190076A patent/NZ190076A/en unknown
- 1979-04-02 FI FI791081A patent/FI66393C/fi not_active IP Right Cessation
- 1979-04-03 DK DK136579A patent/DK147735C/da not_active IP Right Cessation
- 1979-04-03 HU HU79SI1682A patent/HU179314B/hu not_active IP Right Cessation
- 1979-04-04 NO NO791140A patent/NO152935C/no unknown
- 1979-04-04 PL PL1979214676A patent/PL121469B1/pl unknown
- 1979-04-04 AT AT0251979A patent/AT368168B/de not_active IP Right Cessation
- 1979-04-04 SU SU792787402A patent/SU1052161A3/ru active
- 1979-04-04 YU YU803/79A patent/YU40929B/xx unknown
- 1979-04-04 ES ES479271A patent/ES479271A1/es not_active Expired
- 1979-04-05 ZA ZA791635A patent/ZA791635B/xx unknown
- 1979-04-05 JP JP4041479A patent/JPS54141758A/ja active Granted
-
1984
- 1984-05-10 HK HK412/80A patent/HK41284A/xx unknown
- 1984-07-27 JP JP59155726A patent/JPS6069019A/ja active Granted
-
1985
- 1985-12-30 MY MY575/85A patent/MY8500575A/xx unknown
-
1986
- 1986-01-22 SG SG67/86A patent/SG6786G/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |