WO1997021720B1 - Procedes de preparation de steroides 7.alpha.-carboxylyl9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doubles - Google Patents
Procedes de preparation de steroides 7.alpha.-carboxylyl9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doublesInfo
- Publication number
- WO1997021720B1 WO1997021720B1 PCT/US1996/020780 US9620780W WO9721720B1 WO 1997021720 B1 WO1997021720 B1 WO 1997021720B1 US 9620780 W US9620780 W US 9620780W WO 9721720 B1 WO9721720 B1 WO 9721720B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- chr
- compound
- hydrogen
- hydroxycarbonyl
- 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.)
- Ceased
Links
Abstract
L'invention concerne de multiples procédés de réaction nouveaux, de nouvelles phase de procédés et de nouveaux intermédiaires pour la synthèse de l'époxymexrénone et d'autres composés de formule (I). Dans cette formule (I), -A-A- représente le groupe -CHR4-CHR5- ou -CR?4=CR5-; R3, R4 et R5¿ sont choisis séparément dans le groupe constitué d'hydrogène, d'halo, d'hydroxy, d'alkyle inférieur, d'alcoxy inférieur, d'hydroxyalkyle, d'alcoxyalkyle, d'hydroxycarbonyle, de cyano et d'aryloxy; R1 représente un radical alcoxycarbonyle ou hydroxycarbonyle à orientation alpha, -B-B- représente le groupe -CHR6-CHR7- ou un groupe à orientation alpha ou bêta de formule (III), dans lequel R6 et R7 sont choisis séparément dans le groupe constitué d'hydrogène, d'halo, d'alcoxy inférieur, d'acyle, d'hydroxyalkyle, d'alcoxyalkyle, d'hydroxycarbonyle, d'alkyle, d'alcoxycarbonyle, d'acyloxyalkyle, de cyano, d'aryloxy et R8 et R9 sont choisis séparément dans le groupe constitué d'hydrogène, d'halo, d'alcoxy inférieur, d'acyle, d'hydroxyalkyle, d'alcoxyalkyle, d'hydroxycarbonyle, d'alkyle, d'alcoxycarbonyle, d'acyloxyalkyle, de cyano, d'aryloxy, ou R8 et R9 comprennent conjointement avec R6 ou R7 une structure cyclique carbocyclique ou hétérocyclique fusionnée au cycle D pentacyclique.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002347345A CA2347345C (fr) | 1995-12-11 | 1996-12-11 | Procedes de preparation de steroides 7 alpha-carboxylyl9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doubles |
| EA199800449A EA009176B1 (ru) | 1995-12-11 | 1996-12-11 | Способ получения 7-альфа-карбоксил-9,11-эпоксистероидов и промежуточных продуктов, используемых для их получения, и общий способ эпоксидирования по олефиновым двойным связям |
| EP96945103A EP0973791B1 (fr) | 1995-12-11 | 1996-12-11 | Procede pour la preparation d'un composé époxy |
| DK96945103T DK0973791T3 (da) | 1995-12-11 | 1996-12-11 | Fremgangsmåde til fremstilling af en epoxyforbindelse |
| CA002347346A CA2347346C (fr) | 1995-12-11 | 1996-12-11 | Procedes de preparation de steroides 7 alpha-carboxylyl 9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doubles |
| DE69637140T DE69637140T2 (de) | 1995-12-11 | 1996-12-11 | Verfahren zur herstellung einer epoxy-verbindung |
| AU13551/97A AU719260B2 (en) | 1995-12-11 | 1996-12-11 | Process for preparation of 7 alpha-carboxyl 9, 11-epoxy steroids and intermediates useful therein |
| HU9900493A HU222453B1 (hu) | 1995-12-11 | 1996-12-11 | Általános eljárás olefines kettős kötés epoxidálására |
| IL12463196A IL124631A (en) | 1995-12-11 | 1996-12-11 | Processes for preparations of steroids and intermediates useful therein |
| IL158857A IL158857A (en) | 1995-12-11 | 1996-12-11 | Processes for preparation of steroids and intermediates useful therein |
| JP52230497A JP4146897B2 (ja) | 1995-12-11 | 1996-12-11 | 7―アルファ―カルボキシル―9,11―エポキシステロイド化合物の製造方法およびこの方法に有用な中間体ならびにオレフィン二重結合の一般的エポキシ化方法 |
| CA 2240388 CA2240388A1 (fr) | 1995-12-11 | 1996-12-11 | Procedes de preparation de steroides 7.alpha.-carboxylyl9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doubles |
| KR10-2004-7011499A KR100523146B1 (ko) | 1995-12-11 | 1996-12-11 | 7α-카르복실 9,11-에폭시 스테로이드의 제조방법 및 여기에 유용한 중간체 및 올레핀계 이중결합의 에폭시화를 위한 일반방법 |
| IL175299A IL175299A0 (en) | 1995-12-11 | 2006-04-27 | Steroids, processes for their preparation and intermediates useful therein |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US845595P | 1995-12-11 | 1995-12-11 | |
| US60/008,455 | 1995-12-11 | ||
| US08/763,910 US5981744A (en) | 1995-12-11 | 1996-12-11 | Processes for preparation of 9,11-epoxy steroids and intermediates useful therein |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1997021720A2 WO1997021720A2 (fr) | 1997-06-19 |
| WO1997021720A3 WO1997021720A3 (fr) | 1997-10-30 |
| WO1997021720B1 true WO1997021720B1 (fr) | 1997-12-31 |
Family
ID=26678218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/020780 Ceased WO1997021720A2 (fr) | 1995-12-11 | 1996-12-11 | Procedes de preparation de steroides 7.alpha.-carboxylyl9,11-epoxy et intermediaires utiles dans ces procedes et procede general d'epoxydation de liaisons olefiniques doubles |
Country Status (12)
| Country | Link |
|---|---|
| US (13) | US5981744A (fr) |
| EP (1) | EP0973791B1 (fr) |
| JP (2) | JP4146897B2 (fr) |
| CN (1) | CN100384866C (fr) |
| AT (1) | ATE365171T1 (fr) |
| DE (1) | DE69637140T2 (fr) |
| DK (1) | DK0973791T3 (fr) |
| EA (1) | EA009176B1 (fr) |
| ES (1) | ES2287943T3 (fr) |
| IL (2) | IL124631A (fr) |
| PT (1) | PT973791E (fr) |
| WO (1) | WO1997021720A2 (fr) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050267302A1 (en) * | 1995-12-11 | 2005-12-01 | G.D. Searle & Co. | Eplerenone crystalline form exhibiting enhanced dissolution rate |
| US20020038021A1 (en) * | 1995-12-11 | 2002-03-28 | Barton Kathleen P. | Eplerenone crystalline form exhibiting enhanced dissolution rate |
| DE69637140T2 (de) | 1995-12-11 | 2008-04-10 | G.D. Searle Llc, Chicago | Verfahren zur herstellung einer epoxy-verbindung |
| US20020045746A1 (en) * | 1995-12-11 | 2002-04-18 | Barton Kathleen P. | Eplerenone crystalline form |
| EP1148061B1 (fr) * | 1996-12-11 | 2007-10-17 | G.D. Searle LLC. | Procédé d'époxydation |
| US6887991B1 (en) | 1996-12-11 | 2005-05-03 | G. D. Searle & Company | Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein |
| KR100523409B1 (ko) * | 1996-12-11 | 2005-10-24 | 지.디. 썰 엘엘씨 | 9,11-에폭시 스테로이드의 제조방법 및 이 제조방법에유용한 중간체 |
| DK1955700T3 (da) | 1999-09-30 | 2011-05-23 | Harbor Biosciences Inc | Terapeutisk behandling af androgenreceptor-betingede lidelser |
| KR100584104B1 (ko) * | 1999-12-08 | 2006-05-30 | 파마시아 코포레이션 | 결정형 에플레레논 |
| US20030083493A1 (en) * | 1999-12-08 | 2003-05-01 | Barton Kathleen P. | Eplerenone drug substance having high phase purity |
| US6716829B2 (en) | 2000-07-27 | 2004-04-06 | Pharmacia Corporation | Aldosterone antagonist and cyclooxygenase-2 inhibitor combination therapy to prevent or treat inflammation-related cardiovascular disorders |
| DK1487859T3 (da) * | 2002-03-22 | 2008-10-06 | Pharmacia & Upjohn Co Llc | Fremstillingsmetoder til at fremstille Eplerenon |
| US7235655B2 (en) | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| US20070066579A1 (en) * | 2002-08-16 | 2007-03-22 | White Michael J | 5-androsten-3beta-ol steroid intermediates and processs for their preparation |
| EP1534732B1 (fr) * | 2002-08-16 | 2006-09-13 | Pharmacia & Upjohn Company LLC | Intermediaires de 5 androstene-3-ol steroides et leurs procedes de preparation |
| US7196208B2 (en) * | 2002-11-06 | 2007-03-27 | Peter Guillaume Marie Wuts | Processes for preparing 7-carboxy substituted steroids |
| CA2500580A1 (fr) * | 2002-11-07 | 2004-05-27 | Pharmacia & Upjohn Company Llc | Procedes de preparation de 5-androstenes substitues en c-7 |
| CL2004000574A1 (es) * | 2003-03-21 | 2005-02-11 | Pharmacia Corp Sa Organizada B | Proceso para preparar un compuesto 17-espirolactona o la sal de lactona abierta por carbonilacion del correspondiente 17-alquenil o alquinil derivado, los intermediarios que se usan y su proceso de obtencion. |
| US20040265948A1 (en) * | 2003-06-27 | 2004-12-30 | White Michael Jon | Microbial method for hydrolysis and oxidation of androst-5-ene and pregn-5-ene steroid esters |
| WO2005016912A1 (fr) * | 2003-08-19 | 2005-02-24 | Pfizer Inc. | Preparation microbienne efficace de metabolites de capravirine m4 et m5 |
| CA2560389A1 (fr) * | 2004-03-22 | 2005-10-06 | Pharmacia & Upjohn Company Llc | Procede ameliore de preparation de 9,11 epoxy steroides |
| CN1321128C (zh) * | 2005-07-15 | 2007-06-13 | 浙江医药股份有限公司新昌制药厂 | 孕甾-4-烯-7,21-二甲酸,9,11-环氧-17-羟基-3-氧代,γ-内酯,甲酯,(7α,11α,17α)-的制备方法 |
| WO2007025780A2 (fr) * | 2005-09-02 | 2007-03-08 | Recordati Ireland Limited | Antagonistes des recepteurs de l'aldosterone |
| US20080176269A1 (en) * | 2006-10-06 | 2008-07-24 | Mohler James L | Method for determination of DHT levels in tissue samples |
| US20080242856A1 (en) * | 2007-04-02 | 2008-10-02 | Funci Biotechnology Co., Ltd. | Extracts of taiwanofungus camphoratus with a capacity for inhibiting the activity of matrix metalloproteinases and method for preparing the same |
| HU227304B1 (en) * | 2007-07-04 | 2011-02-28 | Richter Gedeon Nyrt | Process for producing 9alpha-hydroxy-steroids |
| EP2367808A4 (fr) * | 2008-11-25 | 2012-05-09 | Evestra Inc | g-LACTONES D'ACIDE 3-(6,6-ÉTHYLÈNE-17b-HYDROXY-3-OXO-17a-PRÉGNA-4-ÈNE-17a-YL) PROPIONIQUE PROGESTATIVES |
| JP6148175B2 (ja) | 2010-05-10 | 2017-06-14 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 網膜中および/または網膜下における液体貯留の処置のための方法および組成物 |
| EP2582365B1 (fr) | 2010-06-16 | 2019-03-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Compositions pour stimuler la réépithélialisation durant la cicatrisation d'une blessure |
| CN104262450A (zh) * | 2014-09-19 | 2015-01-07 | 江苏嘉逸医药有限公司 | 依普利酮的制备及精制方法 |
| ES2699923T3 (es) | 2014-10-17 | 2019-02-13 | Ind Chimica Srl | Proceso para la preparación de 7alfa-(metoxicarbonil)-3-oxo-17alfa-pregn-4,9(11)-dien-21,17-carbolactona, un intermedio útil para la síntesis de moléculas con actividad farmacológica |
| WO2016063269A1 (fr) | 2014-10-20 | 2016-04-28 | Prendergast Patrick T | Utilisation d'antagonistes au récepteur stéroïdien nucléaire, seuls ou en association, comme agents antiviraux directs pour inhiber des alphavirus, togavirus, filovirus, arénavirus, bunyavirus, flavivirus et rhabdovirus |
| WO2017055248A1 (fr) | 2015-09-28 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Méthodes et compositions pharmaceutiques pour le traitement d'une insuffisance cardiaque |
| EP3362095B1 (fr) | 2015-10-13 | 2020-11-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Méthodes et préparations pharmaceutiques pour le traitement de la neovascularisation choroidienne |
| CN105753930A (zh) * | 2016-03-30 | 2016-07-13 | 北京万全德众医药生物技术有限公司 | 依普利酮的一种合成方法 |
| US20190262363A1 (en) | 2016-07-26 | 2019-08-29 | INSERM (Institut National de la Santé et de la Recherche Médicale | Antagonist of mineralocorticoid receptor for the treatment of osteoarthritis |
| CN106501388A (zh) * | 2016-09-22 | 2017-03-15 | 北京万全德众医药生物技术有限公司 | 一种用气相色谱法分离测定依普利酮中三氯乙酰胺的方法 |
| CN108085359B (zh) * | 2016-11-22 | 2020-07-24 | 保定九孚生化有限公司 | 一种11α-羟基-4-烯-3,17-雄甾二酮的生产方法 |
| CN110698529A (zh) * | 2019-11-19 | 2020-01-17 | 湖南新合新生物医药有限公司 | 一种依普利酮中间体△9,11烯酯的制备方法 |
| US20240366632A1 (en) | 2021-08-31 | 2024-11-07 | Institut National de la Santé et de la Recherche Médicale | Methods for the treatment of ocular rosacea |
| CN114235976B (zh) * | 2021-11-09 | 2023-11-03 | 暨南大学 | 一种含氮杂环有机化合物中间产物的合成和分析方法 |
| US12060148B2 (en) | 2022-08-16 | 2024-08-13 | Honeywell International Inc. | Ground resonance detection and warning system and method |
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|---|---|---|---|---|
| US2602769A (en) | 1952-02-23 | 1952-07-08 | Upjohn Co | Oxygenation of steroids by mucorales fungi |
| US2691030A (en) * | 1952-03-28 | 1954-10-05 | Upjohn Co | 11 alpha-hydroxy-6-dehydroprogesterone and esters thereof |
| US3053856A (en) * | 1958-10-29 | 1962-09-11 | Shell Oil Co | Epoxidation of ethylenic compounds with peroxycarboximidic acids |
| US3095412A (en) * | 1961-12-19 | 1963-06-25 | Searle & Co | 9alpha, 11alpha-epoxy and 11beta-chloro-9alpha-hydroxy 17alpha-(2-carboxyethyl)-17beta-hydroxyandrost-4-en-3-one gamma-lactones and delta1 and delta6 analogs |
| US3120515A (en) * | 1962-05-31 | 1964-02-04 | Sterling Drug Inc | 5-cyano steroids, their preparation, and derivatives thereof |
| US3200113A (en) * | 1963-01-09 | 1965-08-10 | Sterling Drug Inc | 7-cyano steroids and derivatives thereof |
| US3300489A (en) * | 1964-07-24 | 1967-01-24 | Smith Kline French Lab | Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof |
| US3413288A (en) * | 1965-07-07 | 1968-11-26 | Parke Davis & Co | Process for the production of steroidal c-17 spirolactones |
| US3741990A (en) * | 1969-07-28 | 1973-06-26 | Upjohn Co | Organic compounds and processes |
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| FR2216273B1 (fr) * | 1973-02-06 | 1977-07-22 | Roussel Uclaf | |
| GB1455220A (fr) * | 1973-09-14 | 1976-11-10 | Searle & Co | |
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| US3972871A (en) * | 1975-09-22 | 1976-08-03 | G. D. Searle & Co. | 6β,17-Dihydroxy-7α-(lower alkoxy)carbonyl-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactones and congeners |
| CH631462A5 (de) * | 1976-03-05 | 1982-08-13 | Schering Ag | Verfahren zur herstellung von neuen steroiden der androstan- oder oestranreihe. |
| US4069219A (en) | 1976-12-27 | 1978-01-17 | G. D. Searle & Co. | 7ξ-(Alkoxycarbonyl)-6ξ-alkyl/halo-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactones and corresponding 21-carboxylic acids, their salts, and esters |
| YU41412B (en) * | 1978-08-15 | 1987-04-30 | Gist Brocades Nv | Process for obtaining 17 beta-hydroxy -3-dxo-17 alpha-pregn-4-en-21-carboxylic acid |
| US4270994A (en) | 1980-02-20 | 1981-06-02 | G. D. Searle & Co. | Electrochemical dehydrogenation of steroidal Δ3,5 enol ethers under basic conditions to provide steroidal Δ4,6 dienones |
| JPS56120697A (en) * | 1980-02-28 | 1981-09-22 | Mitsubishi Chem Ind Ltd | Preparation of 4,6-diene-3-oxosteroid |
| JPS58179498A (ja) * | 1982-04-13 | 1983-10-20 | Dainippon Ink & Chem Inc | 微生物による11α−ヒドロキシル化アンドロスタン系化合物の製造方法 |
| FI77669C (fi) * | 1983-04-13 | 1989-04-10 | Ciba Geigy Ag | 20-spiroxaner och analoger, som innehaoller en oeppen ring e, foerfarande foer deras framstaellning samt dessa innehaollande farmaceutiska preparat. |
| EP0123734A1 (fr) * | 1983-04-29 | 1984-11-07 | Gist-Brocades N.V. | 17-(Isocyano-sulfonylméthylène)-stéroides, 17-(formamido-sulfonylméthylène)-stéroides et leur préparation |
| US4670551A (en) * | 1984-06-21 | 1987-06-02 | Ciba-Geigy Corporation | Epoxy steroids |
| US5352809A (en) | 1986-10-10 | 1994-10-04 | Gist-Brocades N.V. | 9-alpha-hydroxy steroids, process for their preparation, process for the preparation of the corresponding 9(11)-dehydro derivatives and pharmaceutical preparations containing such steroids |
| US5502222A (en) * | 1994-06-01 | 1996-03-26 | Schering Corporation | Process for preparing delta 9,11 and 21-chloro corticosteroids |
| US5565558A (en) * | 1994-12-30 | 1996-10-15 | Mccully; Kilmer S. | Thioretinaco ozonide and enhanced biological activity of thioretinaco ozonide in combination with interferon |
| DE69637140T2 (de) | 1995-12-11 | 2008-04-10 | G.D. Searle Llc, Chicago | Verfahren zur herstellung einer epoxy-verbindung |
-
1996
- 1996-12-11 DE DE69637140T patent/DE69637140T2/de not_active Expired - Fee Related
- 1996-12-11 IL IL12463196A patent/IL124631A/en not_active IP Right Cessation
- 1996-12-11 DK DK96945103T patent/DK0973791T3/da active
- 1996-12-11 ES ES96945103T patent/ES2287943T3/es not_active Expired - Lifetime
- 1996-12-11 WO PCT/US1996/020780 patent/WO1997021720A2/fr not_active Ceased
- 1996-12-11 PT PT96945103T patent/PT973791E/pt unknown
- 1996-12-11 AT AT96945103T patent/ATE365171T1/de not_active IP Right Cessation
- 1996-12-11 EP EP96945103A patent/EP0973791B1/fr not_active Expired - Lifetime
- 1996-12-11 US US08/763,910 patent/US5981744A/en not_active Expired - Fee Related
- 1996-12-11 JP JP52230497A patent/JP4146897B2/ja not_active Expired - Fee Related
- 1996-12-11 EA EA199800449A patent/EA009176B1/ru not_active IP Right Cessation
- 1996-12-11 CN CNB961999616A patent/CN100384866C/zh not_active Expired - Fee Related
-
1999
- 1999-02-08 US US09/246,204 patent/US6331622B1/en not_active Expired - Fee Related
- 1999-02-09 US US09/246,908 patent/US6180780B1/en not_active Expired - Fee Related
-
2000
- 2000-05-30 US US09/583,158 patent/US6335441B1/en not_active Expired - Fee Related
- 2000-05-30 US US09/583,137 patent/US6258946B1/en not_active Expired - Fee Related
-
2001
- 2001-04-03 US US09/826,406 patent/US20020016455A1/en not_active Abandoned
- 2001-04-04 US US09/826,434 patent/US20020019522A1/en not_active Abandoned
- 2001-08-07 US US09/923,977 patent/US6630587B2/en not_active Expired - Fee Related
- 2001-08-31 US US09/943,117 patent/US6586591B2/en not_active Expired - Fee Related
-
2003
- 2003-06-27 US US10/608,101 patent/US7038040B2/en not_active Expired - Fee Related
- 2003-09-26 US US10/672,680 patent/US6953851B2/en not_active Expired - Fee Related
-
2005
- 2005-06-20 US US11/156,418 patent/US7129345B2/en not_active Expired - Fee Related
-
2006
- 2006-04-27 IL IL175299A patent/IL175299A0/en unknown
- 2006-07-21 US US11/459,040 patent/US20070060746A1/en not_active Abandoned
-
2007
- 2007-10-12 JP JP2007265977A patent/JP2008100996A/ja not_active Withdrawn
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