JP2007505891A5 - - Google Patents
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- Publication number
- JP2007505891A5 JP2007505891A5 JP2006526728A JP2006526728A JP2007505891A5 JP 2007505891 A5 JP2007505891 A5 JP 2007505891A5 JP 2006526728 A JP2006526728 A JP 2006526728A JP 2006526728 A JP2006526728 A JP 2006526728A JP 2007505891 A5 JP2007505891 A5 JP 2007505891A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chiral ligand
- ligand complex
- compound
- metal
- 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
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- 238000000034 method Methods 0.000 claims 52
- 239000003446 ligand Substances 0.000 claims 16
- 229910052751 metal Inorganic materials 0.000 claims 14
- 239000002184 metal Substances 0.000 claims 14
- -1 sulfoxide compound Chemical class 0.000 claims 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 6
- 239000007800 oxidant agent Substances 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 4
- 150000003462 sulfoxides Chemical class 0.000 claims 4
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims 3
- 150000002736 metal compounds Chemical class 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 238000007112 amidation reaction Methods 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- QARQPIWTMBRJFX-UHFFFAOYSA-N modafinil acid Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)O)C1=CC=CC=C1 QARQPIWTMBRJFX-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 2
- 125000000101 thioether group Chemical group 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- AIABEETXTKSDLE-UHFFFAOYSA-J 2,3-dihydroxybutanedioate;titanium(4+) Chemical compound [Ti+4].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O AIABEETXTKSDLE-UHFFFAOYSA-J 0.000 claims 1
- CKIWWDLKOCDKHX-UHFFFAOYSA-N 2-benzhydrylsulfinylacetonitrile Chemical compound C=1C=CC=CC=1C(S(CC#N)=O)C1=CC=CC=C1 CKIWWDLKOCDKHX-UHFFFAOYSA-N 0.000 claims 1
- MGZFHNIXTKWXDI-UHFFFAOYSA-N 2-methyl-3,3-diphenylpropanethioic s-acid Chemical compound C=1C=CC=CC=1C(C(C)C(S)=O)C1=CC=CC=C1 MGZFHNIXTKWXDI-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960001165 modafinil Drugs 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03292312A EP1516869A1 (en) | 2003-09-19 | 2003-09-19 | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| EP03292312.0 | 2003-09-19 | ||
| US50708903P | 2003-10-01 | 2003-10-01 | |
| US60/507,089 | 2003-10-01 | ||
| PCT/IB2004/003026 WO2005028428A1 (en) | 2003-09-19 | 2004-09-17 | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007505891A JP2007505891A (ja) | 2007-03-15 |
| JP2007505891A5 true JP2007505891A5 (enExample) | 2007-11-22 |
| JP4713480B2 JP4713480B2 (ja) | 2011-06-29 |
Family
ID=34178643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006526728A Expired - Fee Related JP4713480B2 (ja) | 2003-09-19 | 2004-09-17 | 不斉酸化によるモダフィニルの単一エナンチオマーのエナンチオ選択的合成方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7317126B2 (enExample) |
| EP (2) | EP1516869A1 (enExample) |
| JP (1) | JP4713480B2 (enExample) |
| KR (1) | KR101136703B1 (enExample) |
| CN (1) | CN100404502C (enExample) |
| AT (1) | ATE365711T1 (enExample) |
| AU (1) | AU2004274248B2 (enExample) |
| BR (1) | BRPI0414298B1 (enExample) |
| CA (1) | CA2538697C (enExample) |
| DE (1) | DE602004007278T2 (enExample) |
| DK (1) | DK1663963T3 (enExample) |
| EA (1) | EA009385B1 (enExample) |
| ES (1) | ES2289556T3 (enExample) |
| MX (1) | MXPA06002935A (enExample) |
| NZ (1) | NZ545739A (enExample) |
| PL (1) | PL1663963T3 (enExample) |
| PT (1) | PT1663963E (enExample) |
| SI (1) | SI1663963T1 (enExample) |
| UA (1) | UA85196C2 (enExample) |
| WO (1) | WO2005028428A1 (enExample) |
| ZA (1) | ZA200601962B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| EP1702915A1 (en) * | 2005-03-14 | 2006-09-20 | Cephalon France | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
| CN1321978C (zh) * | 2005-04-29 | 2007-06-20 | 浙江工业大学 | 一种2－（二苯基甲基亚硫酰基）乙酰胺的合成方法 |
| WO2007027328A2 (en) * | 2005-07-28 | 2007-03-08 | University Of Iowa Research Foundation | Microbial sulfoxidation and amidation of benzhdrylsulfanyl carboxylic acids and uses thereof |
| US20070293702A1 (en) * | 2006-02-21 | 2007-12-20 | Viviana Braude | Novel crystalline forms of armodafinil and preparation thereof |
| WO2007103221A2 (en) | 2006-03-01 | 2007-09-13 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of armodafinil |
| WO2008070143A1 (en) * | 2006-12-06 | 2008-06-12 | Teva Pharmaceutical Industries Ltd. | Processes for preparing armodafinil intermediate |
| EP2155664A2 (en) * | 2007-06-04 | 2010-02-24 | Generics Ýuk¨Limited | Novel process |
| WO2009024863A2 (en) * | 2007-06-26 | 2009-02-26 | Actavis Group Ptc Ehf | Process for the preparation of modafinil enantiomers |
| US7960586B2 (en) * | 2007-08-16 | 2011-06-14 | Teva Pharmaceutical Industries Ltd. | Purification of armodafinil |
| CN102471290B (zh) * | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| AU2011203970A1 (en) * | 2010-01-07 | 2012-07-12 | Vivus, Inc. | Treatment of obstructive sleep apnea syndrome with a combination of a carbonic anhydrase inhibitor and an additional active agent |
| RU2448954C1 (ru) * | 2010-10-18 | 2012-04-27 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Способ получения сульфоксидов |
| EP2649187B1 (en) | 2010-12-08 | 2017-11-22 | Codexis, Inc. | Biocatalysts and methods for the synthesis of armodafinil |
| FR2970711B1 (fr) * | 2011-01-20 | 2016-03-04 | Hopitaux Paris Assist Publique | La lauflumide et ses enantiomeres, preparation et utilisations therapeutiques |
| RU2477316C1 (ru) * | 2011-12-29 | 2013-03-10 | Учреждение Российской академии наук Институт экологии и генетики микроорганизмов Уральского отделения РАН | Биокаталитический способ получения (r)-фенилметилового сульфоксида |
| CN104447440B (zh) * | 2013-09-12 | 2016-05-18 | 中国科学院大连化学物理研究所 | 一种催化不对称氧化硫醚的方法 |
| CN104045588A (zh) * | 2014-06-11 | 2014-09-17 | 江苏斯威森生物医药工程研究中心有限公司 | 一种2-(4,4’-二卤-二苯基甲基亚磺酰)乙酰胺的合成方法 |
| HUE035104T2 (en) | 2014-08-13 | 2018-05-02 | Red Bull Gmbh | Heterocyclic compounds with activity memory stimulating activity |
| CA2989243C (en) | 2014-08-13 | 2023-03-14 | Red Bull Gmbh | Heterocyclic compounds with working memory enhancing activity |
| US9616068B2 (en) | 2014-10-27 | 2017-04-11 | Pohela LLC | Animal training using cognitive enhancement |
| CN110698482A (zh) * | 2019-10-29 | 2020-01-17 | 株洲千金药业股份有限公司 | 一种s型手性亚砜类化合物的制备方法 |
| CN110746428A (zh) * | 2019-10-29 | 2020-02-04 | 株洲千金药业股份有限公司 | 一种r型手性亚砜类化合物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127722A (en) * | 1975-10-02 | 1978-11-28 | Laboratoire L. Lafon | Benzhydrylsulphinyl derivatives |
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2528038B2 (fr) * | 1982-06-04 | 1985-08-09 | Lafon Labor | Derives de benzhydrylsulfinylacetamide et leur utilisation en therapeutique |
| FR2593809B1 (fr) * | 1986-01-31 | 1988-07-22 | Lafon Labor | Benzhydrylsulfinylacetamide, procede de preparation et utilisation en therapeutique |
| CA2634702C (en) * | 2000-07-27 | 2011-07-19 | Teva Pharmaceutical Industries Ltd. | Crystalline and pure modafinil, and process of preparing the same |
| IL143106A (en) * | 2001-05-13 | 2005-11-20 | Chemagis Ltd | Process for the preparation of diphenylmethylthioacetamide |
| US20040048931A1 (en) | 2002-07-12 | 2004-03-11 | Craig Heacock | Modafinil pharmaceutical compositions |
| FR2849029B1 (fr) | 2002-12-20 | 2005-03-18 | Lafon Labor | Procede de preparation et formes cristallines des enantiomeres optiques du modafinil. |
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
-
2003
- 2003-09-19 EP EP03292312A patent/EP1516869A1/en not_active Withdrawn
-
2004
- 2004-09-17 WO PCT/IB2004/003026 patent/WO2005028428A1/en not_active Ceased
- 2004-09-17 CN CNB2004800298265A patent/CN100404502C/zh not_active Expired - Fee Related
- 2004-09-17 DE DE602004007278T patent/DE602004007278T2/de not_active Expired - Lifetime
- 2004-09-17 ES ES04769402T patent/ES2289556T3/es not_active Expired - Lifetime
- 2004-09-17 EP EP04769402A patent/EP1663963B1/en not_active Expired - Lifetime
- 2004-09-17 PL PL04769402T patent/PL1663963T3/pl unknown
- 2004-09-17 EA EA200600593A patent/EA009385B1/ru not_active IP Right Cessation
- 2004-09-17 UA UAA200604415A patent/UA85196C2/ru unknown
- 2004-09-17 MX MXPA06002935A patent/MXPA06002935A/es active IP Right Grant
- 2004-09-17 CA CA2538697A patent/CA2538697C/en not_active Expired - Fee Related
- 2004-09-17 AU AU2004274248A patent/AU2004274248B2/en not_active Expired
- 2004-09-17 AT AT04769402T patent/ATE365711T1/de active
- 2004-09-17 SI SI200430411T patent/SI1663963T1/sl unknown
- 2004-09-17 JP JP2006526728A patent/JP4713480B2/ja not_active Expired - Fee Related
- 2004-09-17 PT PT04769402T patent/PT1663963E/pt unknown
- 2004-09-17 US US10/943,360 patent/US7317126B2/en not_active Expired - Fee Related
- 2004-09-17 KR KR1020067007002A patent/KR101136703B1/ko not_active Expired - Fee Related
- 2004-09-17 NZ NZ545739A patent/NZ545739A/en not_active IP Right Cessation
- 2004-09-17 DK DK04769402T patent/DK1663963T3/da active
- 2004-09-17 BR BRPI0414298-5A patent/BRPI0414298B1/pt not_active IP Right Cessation
-
2006
- 2006-03-08 ZA ZA200601962A patent/ZA200601962B/en unknown
-
2007
- 2007-10-30 US US11/929,030 patent/US7812193B2/en not_active Expired - Fee Related
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