AU2004274248B2 - Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation - Google Patents

Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation Download PDF

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Publication number
AU2004274248B2
AU2004274248B2 AU2004274248A AU2004274248A AU2004274248B2 AU 2004274248 B2 AU2004274248 B2 AU 2004274248B2 AU 2004274248 A AU2004274248 A AU 2004274248A AU 2004274248 A AU2004274248 A AU 2004274248A AU 2004274248 B2 AU2004274248 B2 AU 2004274248B2
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AU
Australia
Prior art keywords
formula
sulphide
chiral ligand
sulphoxide
ligand complex
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Expired
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AU2004274248A
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English (en)
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AU2004274248A1 (en
Inventor
Gerard Duret
Laurence Prat
Francois Rebiere
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Cephalon France SAS
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Cephalon France SAS
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Publication of AU2004274248B2 publication Critical patent/AU2004274248B2/en
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Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
AU2004274248A 2003-09-19 2004-09-17 Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation Expired AU2004274248B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP03292312.0 2003-09-19
EP03292312A EP1516869A1 (en) 2003-09-19 2003-09-19 Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation
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 (2)

Publication Number Publication Date
AU2004274248A1 AU2004274248A1 (en) 2005-03-31
AU2004274248B2 true AU2004274248B2 (en) 2010-08-26

Family

ID=34178643

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2004274248A Expired AU2004274248B2 (en) 2003-09-19 2004-09-17 Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7368591B2 (en) 2003-09-19 2008-05-06 Cephalon France Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation
EP1516869A1 (en) * 2003-09-19 2005-03-23 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
EP1986994A2 (en) * 2006-02-21 2008-11-05 Teva Pharmaceutical Industries Ltd Novel crystalline forms of armodafinil and preparation thereof
CA2634133A1 (en) 2006-03-01 2007-09-13 Teva Pharmaceutical Industries Ltd. An improved process for the preparation of armodafinil
US20080214862A1 (en) * 2006-12-06 2008-09-04 Ben-Zion Dolitzky Processes for preparing armodafinil intermediate
CA2688430A1 (en) * 2007-06-04 2008-12-11 Generics [Uk] Limited Novel process
WO2009024863A2 (en) * 2007-06-26 2009-02-26 Actavis Group Ptc Ehf Process for the preparation of modafinil enantiomers
WO2009025791A2 (en) * 2007-08-16 2009-02-26 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
US20110224196A1 (en) * 2010-01-07 2011-09-15 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
EP2985279B1 (en) 2014-08-13 2017-08-02 Red Bull GmbH Heterocyclic compounds with working memory enhancing 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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4177290A (en) * 1977-03-31 1979-12-04 Laboratoire L. Lafon Acetamide derivatives
EP0233106B1 (fr) * 1986-01-31 1989-05-31 Laboratoire L. Lafon (-)-Benzhydrylsulfinylacétamide, procédé de préparation et utilisation en thérapeutique
WO2002010125A1 (en) * 2000-07-27 2002-02-07 Teva Pharmaceutical Industries Ltd. Crystalline and pure modafinil, and process of preparing the same
EP1260501A1 (en) * 2001-05-13 2002-11-27 Chemagis Ltd. Process for the preparation of diphenylmethylthioacetamide

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4127722A (en) * 1975-10-02 1978-11-28 Laboratoire L. Lafon Benzhydrylsulphinyl derivatives
FR2528038B2 (fr) * 1982-06-04 1985-08-09 Lafon Labor Derives de benzhydrylsulfinylacetamide et leur utilisation en therapeutique
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

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4177290A (en) * 1977-03-31 1979-12-04 Laboratoire L. Lafon Acetamide derivatives
EP0233106B1 (fr) * 1986-01-31 1989-05-31 Laboratoire L. Lafon (-)-Benzhydrylsulfinylacétamide, procédé de préparation et utilisation en thérapeutique
US4927855A (en) * 1986-01-31 1990-05-22 Laboratoire L. Lafon Levorotatory isomer of benzhydrylsulfinyl derivatives
WO2002010125A1 (en) * 2000-07-27 2002-02-07 Teva Pharmaceutical Industries Ltd. Crystalline and pure modafinil, and process of preparing the same
US20020043207A1 (en) * 2000-07-27 2002-04-18 Claude Singer Oxidation method for preparing highly pure modafinil, crystalline forms of modafinil, and methods of preparing the crystalline forms
EP1260501A1 (en) * 2001-05-13 2002-11-27 Chemagis Ltd. Process for the preparation of diphenylmethylthioacetamide

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Cotton, H et al: Tetrahedron Assym., 2000, 11, 3819-3825. *
Kagan et al: J. Am Chem Soc, 1984, 106, 8188-8193. *
Kagan et al: Org. Synthesis, Coll. 1993, 8, 464. *
Kagan et al: Tetrahedron, 1987, 43(21), 5135-5144. *
Madesclaire, M: Tetrahedron, 1986, 42(20), 5459-5495. *

Also Published As

Publication number Publication date
ATE365711T1 (de) 2007-07-15
SI1663963T1 (sl) 2007-12-31
CA2538697A1 (en) 2005-03-31
US20080171896A1 (en) 2008-07-17
EP1663963A1 (en) 2006-06-07
UA85196C2 (ru) 2009-01-12
US20050080256A1 (en) 2005-04-14
MXPA06002935A (es) 2006-06-14
CN1867544A (zh) 2006-11-22
EP1663963B1 (en) 2007-06-27
CA2538697C (en) 2012-11-13
NZ545739A (en) 2010-01-29
BRPI0414298B1 (pt) 2021-06-08
BRPI0414298A (pt) 2006-11-14
US7812193B2 (en) 2010-10-12
KR101136703B1 (ko) 2012-05-24
EA200600593A1 (ru) 2006-08-25
EP1516869A1 (en) 2005-03-23
DE602004007278T2 (de) 2008-02-28
JP4713480B2 (ja) 2011-06-29
DE602004007278D1 (de) 2007-08-09
PT1663963E (pt) 2007-10-19
ZA200601962B (en) 2007-06-27
CN100404502C (zh) 2008-07-23
DK1663963T3 (da) 2007-10-29
KR20070009968A (ko) 2007-01-19
JP2007505891A (ja) 2007-03-15
WO2005028428A1 (en) 2005-03-31
EA009385B1 (ru) 2007-12-28
PL1663963T3 (pl) 2007-11-30
ES2289556T3 (es) 2008-02-01
US7317126B2 (en) 2008-01-08
AU2004274248A1 (en) 2005-03-31

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MK14 Patent ceased section 143(a) (annual fees not paid) or expired