JP2003529564A5 - - Google Patents
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- Publication number
- JP2003529564A5 JP2003529564A5 JP2001561731A JP2001561731A JP2003529564A5 JP 2003529564 A5 JP2003529564 A5 JP 2003529564A5 JP 2001561731 A JP2001561731 A JP 2001561731A JP 2001561731 A JP2001561731 A JP 2001561731A JP 2003529564 A5 JP2003529564 A5 JP 2003529564A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- acid group
- reaction
- salt
- 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
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
- -1 alkoxide salt Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/513,399 | 2000-02-25 | ||
| US09/513,399 US20020133032A1 (en) | 2000-02-25 | 2000-02-25 | Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods |
| PCT/US2001/006055 WO2001062722A2 (en) | 2000-02-25 | 2001-02-23 | Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003529564A JP2003529564A (ja) | 2003-10-07 |
| JP2003529564A5 true JP2003529564A5 (enExample) | 2007-04-05 |
| JP3986313B2 JP3986313B2 (ja) | 2007-10-03 |
Family
ID=24043095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001561731A Expired - Fee Related JP3986313B2 (ja) | 2000-02-25 | 2001-02-23 | カルボチオ酸の新規な合成方法及び新規な精製方法を使用するフルチカゾン及び近縁の１７β−カルボチオ酸エステルの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20020133032A1 (enExample) |
| EP (1) | EP1257531B1 (enExample) |
| JP (1) | JP3986313B2 (enExample) |
| AT (1) | ATE276235T1 (enExample) |
| CA (1) | CA2400919C (enExample) |
| DE (1) | DE60105555T2 (enExample) |
| DK (1) | DK1257531T3 (enExample) |
| ES (1) | ES2228832T3 (enExample) |
| MX (1) | MXPA02008275A (enExample) |
| PT (1) | PT1257531E (enExample) |
| WO (1) | WO2001062722A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0017988D0 (en) * | 2000-07-21 | 2000-09-13 | Glaxo Group Ltd | Novel process |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| SI1305329T2 (sl) | 2000-08-05 | 2015-07-31 | Glaxo Group Limited | S-fluorometil ester 6alfa,9alfa-difluoro-17alfa-(2-furanilkarboksil)oksi-11beta-hidroksi- 16alfa-metil-3-okso-androst-1,4-dien-17-karbotiojske kisline kot protivnetno sredstvo |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6777400B2 (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 |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| 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 (en) | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| AU2002321884A1 (en) * | 2001-08-03 | 2003-02-24 | Smithkline Beecham Corporation | A method for preparing fluticasone derivatives |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| AU2003263575A1 (en) | 2002-06-20 | 2004-01-06 | Sun Pharmaceutical Industries Limited | Convenient synthesis of s-fluoromethyl 6alpha, 9alpha-difluoro-11beta-hydroxy-16alpha- methyl-17alpha-propionyloxy-3-oxoandrosta-1, 4-diene-17beta-carbothioate |
| IL153462A0 (en) * | 2002-12-16 | 2003-07-06 | Chemagis Ltd | Thiocarboxylic acid organic salts and processes utilizing the same |
| EP1466920A1 (en) * | 2003-04-04 | 2004-10-13 | Alpharma APS | Process for the preparation of steroidal 17 beta-carbothioates |
| CA2530680A1 (en) * | 2003-04-04 | 2004-10-14 | Alpharma Aps | Process for the preparation of steroidal carbothioic acid derivatives and intermediates |
| EP1526139A1 (en) * | 2003-10-24 | 2005-04-27 | S.N.I.F.F. Italia S.P.A. | A process for preparing highly pure androstane 17-beta-carboxylic acids and androstane 17-beta-carbothioic acid fluoromethyl esters |
| PT103202B (pt) | 2004-10-19 | 2011-01-27 | Hovione Farmaciencia S A | Processo para a esterificação de um ácido carbotiótico |
| CN100560598C (zh) * | 2005-07-26 | 2009-11-18 | 上海奥锐特国际贸易有限公司 | 氟替卡松丙酸酯的合成方法 |
| EP2402361B1 (en) * | 2006-06-14 | 2020-04-15 | Generics [UK] Limited | Process for the preparation of s-fluoromethyl-6,9-difluoro-11-hydroxy-16-methyl-17-propionyloxy-3-oxo-androsta-1,4-diene-17-carbothioate and intermediates |
| US7265247B1 (en) | 2006-07-28 | 2007-09-04 | Im&T Research, Inc. | Substituted phenylsulfur trifluoride and other like fluorinating agents |
| US8399720B2 (en) * | 2007-03-23 | 2013-03-19 | Ube Industries, Ltd. | Methods for producing fluorinated phenylsulfur pentafluorides |
| RU2472779C2 (ru) * | 2007-03-23 | 2013-01-20 | УБЭ Индастриз, Лтд. | Способ получения пентафторидов арилсеры |
| US8030516B2 (en) * | 2007-10-19 | 2011-10-04 | Ube Industries, Ltd. | Methods for producing perfluoroalkanedi(sulfonyl chloride) |
| JP2011518765A (ja) * | 2007-12-11 | 2011-06-30 | 宇部興産株式会社 | ジフルオロメチレン−及びトリフルオロメチル−含有化合物を製造するための方法及び組成物 |
| TW201006787A (en) * | 2008-03-07 | 2010-02-16 | Im & T Res Inc | Fluorination processes with arylsulfur halotetrafluorides |
| WO2010022001A1 (en) * | 2008-08-18 | 2010-02-25 | Im&T Research, Inc. | Methods for preparing fluoroalkyl arylsulfinyl compounds and fluorinated compounds thereto |
| KR101676054B1 (ko) * | 2008-09-22 | 2016-11-14 | 우베 고산 가부시키가이샤 | 폴리(펜타플루오로설파닐)방향족 화합물을 제조하기 위한 공정 |
| US20100174096A1 (en) * | 2009-01-05 | 2010-07-08 | Im&T Research, Inc. | Methods for Production of Optically Active Fluoropyrrolidine Derivatives |
| WO2010081014A1 (en) | 2009-01-09 | 2010-07-15 | Im&T Research, Inc. | Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds and their preparative methods |
| EP2611821A2 (en) | 2010-09-01 | 2013-07-10 | Cadila Healthcare Limited | Process for preparing fluticasone propionate/furoate |
| CN102558273B (zh) * | 2010-12-14 | 2014-07-02 | 浙江省天台县奥锐特药业有限公司 | 氟替卡松糠酸酯的制备方法 |
| US9303060B1 (en) | 2014-10-03 | 2016-04-05 | Amphaster Pharmaceuticals, Inc. | Methods of preparing intermediate of fluticasone propionate |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4188385A (en) * | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| US4198403A (en) * | 1978-04-05 | 1980-04-15 | Syntex (U.S.A.) Inc. | 17 Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes |
| US4263289A (en) * | 1978-04-05 | 1981-04-21 | 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 |
| CY1291A (en) | 1980-02-15 | 1985-10-18 | Glaxo Group Ltd | Androstane 17 beta carbothioates |
| CA1201114A (en) * | 1980-02-15 | 1986-02-25 | Gordon H. Phillipps | Androstane carbothioates |
| US4578221A (en) * | 1980-04-23 | 1986-03-25 | Glaxo Group Limited | Androstane carbothioic acids |
| IL109656A (en) | 1994-05-15 | 1998-02-22 | Chemagis Ltd | Process for the manufacture of androstane - 17 - carbothioates and androstane - 17 - carbothioates prepared thereby |
| GB9622173D0 (en) * | 1996-10-24 | 1996-12-18 | Glaxo Group Ltd | Particulate Products |
| US6858593B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative 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 |
-
2000
- 2000-02-25 US US09/513,399 patent/US20020133032A1/en not_active Abandoned
-
2001
- 2001-02-23 WO PCT/US2001/006055 patent/WO2001062722A2/en not_active Ceased
- 2001-02-23 CA CA002400919A patent/CA2400919C/en not_active Expired - Fee Related
- 2001-02-23 DK DK01916231T patent/DK1257531T3/da active
- 2001-02-23 EP EP01916231A patent/EP1257531B1/en not_active Expired - Lifetime
- 2001-02-23 MX MXPA02008275A patent/MXPA02008275A/es active IP Right Grant
- 2001-02-23 PT PT01916231T patent/PT1257531E/pt unknown
- 2001-02-23 AT AT01916231T patent/ATE276235T1/de active
- 2001-02-23 JP JP2001561731A patent/JP3986313B2/ja not_active Expired - Fee Related
- 2001-02-23 ES ES01916231T patent/ES2228832T3/es not_active Expired - Lifetime
- 2001-02-23 DE DE60105555T patent/DE60105555T2/de not_active Expired - Lifetime
-
2004
- 2004-05-18 US US10/847,846 patent/US7214807B2/en not_active Expired - Fee Related
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