WO2008092939A3 - Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation - Google Patents

Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation Download PDF

Info

Publication number
WO2008092939A3
WO2008092939A3 PCT/EP2008/051230 EP2008051230W WO2008092939A3 WO 2008092939 A3 WO2008092939 A3 WO 2008092939A3 EP 2008051230 W EP2008051230 W EP 2008051230W WO 2008092939 A3 WO2008092939 A3 WO 2008092939A3
Authority
WO
WIPO (PCT)
Prior art keywords
optically pure
preparation
entiomer
treatment
converting enzyme
Prior art date
Application number
PCT/EP2008/051230
Other languages
French (fr)
Other versions
WO2008092939A2 (en
Inventor
Igor Plaper
Anica Pecavar
Berta Kotar-Jordan
Natalija Zajc
Miha Vrbinc
Anton Kocevar
Mitja Pelko
Miroslav Veverka
Eva Veverkova
Janez Smodis
Rok Zupet
Original Assignee
Krka Tovarna Zdravil D D Novo
Igor Plaper
Anica Pecavar
Berta Kotar-Jordan
Natalija Zajc
Miha Vrbinc
Anton Kocevar
Mitja Pelko
Miroslav Veverka
Eva Veverkova
Janez Smodis
Rok Zupet
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from SI200700024A external-priority patent/SI22447A/en
Priority claimed from SI200700078A external-priority patent/SI22490A/en
Priority claimed from EP07019823A external-priority patent/EP2048144A1/en
Application filed by Krka Tovarna Zdravil D D Novo, Igor Plaper, Anica Pecavar, Berta Kotar-Jordan, Natalija Zajc, Miha Vrbinc, Anton Kocevar, Mitja Pelko, Miroslav Veverka, Eva Veverkova, Janez Smodis, Rok Zupet filed Critical Krka Tovarna Zdravil D D Novo
Priority to EP08708540A priority Critical patent/EP2114919A2/en
Priority to EA200900985A priority patent/EA200900985A1/en
Publication of WO2008092939A2 publication Critical patent/WO2008092939A2/en
Publication of WO2008092939A3 publication Critical patent/WO2008092939A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to a process for the preparation of substantially optically pure omeprazole, or a pharmaceutically acceptable salt or solvate thereof. The invention also relates to a process for preparing a pharmaceutical composition comprising the substantially optically pure omeprazole or the pharmaceutically acceptable salt or solvate thereof and to intermediates useful for the preparation of optically pure omeprazole.
PCT/EP2008/051230 2007-01-31 2008-01-31 Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation WO2008092939A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP08708540A EP2114919A2 (en) 2007-01-31 2008-01-31 Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic seperation
EA200900985A EA200900985A1 (en) 2007-01-31 2008-01-31 METHOD OF OBTAINING OPTICAL PURE OMEPRAZOL

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
SIP-200700024 2007-01-31
SI200700024A SI22447A (en) 2007-01-31 2007-01-31 New procedure for preparation of enantiomerically enriched omeprazole
SI200700078A SI22490A (en) 2007-03-28 2007-03-28 New procedure for preparation of enantiomerically enriched omeprazole
SIP-200700078 2007-03-28
EP07019823.9 2007-10-10
EP07019823A EP2048144A1 (en) 2007-10-10 2007-10-10 Process for the preparation of optically pure omeprazole via salt formation with a chiral amine

Publications (2)

Publication Number Publication Date
WO2008092939A2 WO2008092939A2 (en) 2008-08-07
WO2008092939A3 true WO2008092939A3 (en) 2009-01-29

Family

ID=39638287

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/051230 WO2008092939A2 (en) 2007-01-31 2008-01-31 Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation

Country Status (3)

Country Link
EP (1) EP2114919A2 (en)
EA (1) EA200900985A1 (en)
WO (1) WO2008092939A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010058409A2 (en) * 2008-11-18 2010-05-27 Hetero Research Foundation Optical purification of esomeprazole
EP2486032A4 (en) 2009-10-09 2013-03-27 Hetero Research Foundation Optical resolution of substituted 2-(2- pyridinylmethylsulphinyl)-1h-benzimidazoles
EP2499125B1 (en) 2009-11-12 2016-01-27 Hetero Research Foundation Process for the resolution of omeprazole
WO2013088272A1 (en) * 2011-12-14 2013-06-20 Wockhardt Limited Pharmaceutical composition comprising esomeprazole magnesium dihydrate
CN102775418B (en) * 2012-06-11 2014-12-24 中国人民解放军第四军医大学 Synthesis and application of novel chiral quaternary ammonium salt phase-transfer catalyst
CN106632248A (en) * 2016-09-30 2017-05-10 青岛云天生物技术有限公司 Preparation process of (S)-pantoprazole sodium
CN112666304B (en) * 2019-10-15 2022-12-09 扬子江药业集团有限公司 Method for detecting enantiomer in esomeprazole sodium medicine
CN115791995A (en) * 2022-09-09 2023-03-14 宜昌东阳光长江药业股份有限公司 Detection method of esomeprazole sodium isomer for injection

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994027988A1 (en) * 1993-05-28 1994-12-08 Astra Aktiebolag Optically pure salts of pyridinylmethyl sulfinyl-ih-benzimidazole compounds
WO1997046557A1 (en) * 1996-06-05 1997-12-11 Wolfgang Lindner Cinchonan based chiral selectors for separation of stereoisomers
WO1998054171A1 (en) * 1997-05-30 1998-12-03 Astra Aktiebolag Novel form of s-omeprazole
EP1018340A1 (en) * 1999-01-06 2000-07-12 Tecnimede-Sociedade Tecnico-Medicinal, S.A. Inclusion aminoacid salts compounds of benzimidazole derivatives with cyclodextrins, their preparation and pharmaceutical formulations containing them
WO2004099182A1 (en) * 2003-05-05 2004-11-18 Ranbaxy Laboratories Limited Zinc salt of (s)-omeprazole
ES2281292A1 (en) * 2006-03-08 2007-09-16 Quimica Sintetica S.A. Novel esomeprazole salts are L-lysine esomeprazole and choline esomeprazole, where salts are stable

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE7804231L (en) 1978-04-14 1979-10-15 Haessle Ab Gastric acid secretion
SE8204879D0 (en) 1982-08-26 1982-08-26 Haessle Ab NOVEL CHEMICAL INTERMEDIATES
DK171989B1 (en) 1987-08-04 1997-09-08 Takeda Chemical Industries Ltd Process for the preparation of 2- (2-pyridylmethylsulfinyl) benzimidazoles
AT391693B (en) 1988-11-15 1990-11-12 Cl Pharma METHOD FOR PRODUCING 3-5-DIMETHYL-4METHOXYPYRIDINE DERIVATIVES AND NEW INTERMEDIATE PRODUCT THEREFOR
SE9002043D0 (en) 1990-06-07 1990-06-07 Astra Ab IMPROVED METHOD FOR SYNTHESIS
ES2026761A6 (en) 1990-10-31 1992-05-01 Genesis Para La Investigacion A process for the preparation of omeprazol.
NZ244301A (en) 1991-09-20 1994-08-26 Merck & Co Inc Preparation of 2-pyridylmethylsulphinylbenzimidazole and pyridoimidazole derivatives from the corresponding sulphenyl compounds
UA72748C2 (en) 1998-11-10 2005-04-15 Astrazeneca Ab A novel crystalline form of omeprazole
SI20875A (en) 2001-04-25 2002-10-31 LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. Crystal form of omeprazole
SE0104295D0 (en) 2001-12-18 2001-12-18 Astrazeneca Ab New process
EP1487818B1 (en) 2002-03-05 2007-05-30 AstraZeneca AB Alkylammonium salts of omeprazole and esomeprazole
EA200500673A1 (en) 2002-10-22 2005-12-29 Рэнбакси Лабораториз Лимитед AMORPHIC FORM OF SALT EZOMEPRAZOL, METHOD FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION ON ITS BASIS
WO2004099181A1 (en) 2003-05-05 2004-11-18 Ranbaxy Laboratories Limited Barium salt of benzimidazole derivative
SE0302381D0 (en) 2003-09-04 2003-09-04 Astrazeneca Ab New salts I
SE0302382D0 (en) 2003-09-04 2003-09-04 Astrazeneca Ab New salts II
EP1726305A1 (en) 2005-05-25 2006-11-29 Ratiopharm GmbH Zinc salt of omeprazole and its enantiomers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994027988A1 (en) * 1993-05-28 1994-12-08 Astra Aktiebolag Optically pure salts of pyridinylmethyl sulfinyl-ih-benzimidazole compounds
WO1997046557A1 (en) * 1996-06-05 1997-12-11 Wolfgang Lindner Cinchonan based chiral selectors for separation of stereoisomers
WO1998054171A1 (en) * 1997-05-30 1998-12-03 Astra Aktiebolag Novel form of s-omeprazole
EP1018340A1 (en) * 1999-01-06 2000-07-12 Tecnimede-Sociedade Tecnico-Medicinal, S.A. Inclusion aminoacid salts compounds of benzimidazole derivatives with cyclodextrins, their preparation and pharmaceutical formulations containing them
WO2004099182A1 (en) * 2003-05-05 2004-11-18 Ranbaxy Laboratories Limited Zinc salt of (s)-omeprazole
ES2281292A1 (en) * 2006-03-08 2007-09-16 Quimica Sintetica S.A. Novel esomeprazole salts are L-lysine esomeprazole and choline esomeprazole, where salts are stable

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ABELO, ANGELA ET AL: "Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes", DRUG METABOLISM AND DISPOSITION , 28(8), 966-972 CODEN: DMDSAI; ISSN: 0090-9556, 2000, XP009109537 *
ANON.: "Process for preparing 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2- pyridyl)methyl]sulfinyl]-1H-benzimidazole by optical resolution", IP.COM JOURNAL , 5(8A), 9 (NO. IPCOM000126473D), 20 JUL 2005 CODEN: IJPOBX; ISSN: 1533-0001, 2005, XP009103605 *
KANAZAWA, HIDEKO ET AL: "Stereospecific analysis of omeprazole in human plasma as a probe for CYP2C19 phenotype", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS , 30(6), 1817-1824 CODEN: JPBADA; ISSN: 0731-7085, 2003, XP009103015 *
LI, XUE-QING ET AL: "Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities", DRUG METABOLISM AND DISPOSITION , 32(8), 821-827 CODEN: DMDSAI; ISSN: 0090-9556, 2004, XP009109474 *
LI, XUE-QING ET AL: "Enantiomer/enantiomer interactions between the S- and R-isomers of omeprazole in human cytochrome P450 enzymes: Major role of CYP2C19 and CYP3A4", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS , 315(2), 777-787 CODEN: JPETAB; ISSN: 0022-3565, 2005, XP009109551 *
URAY, G. ET AL: "Diphenylethanediamine derivatives as chiral selectors. VIII. Influence of the second amido function on the high-performance liquid chromatographic enantioseparation characteristics of (N-3,5-dinitrobenzoyl)- diphenylethanediamine based chiral stationary phases", JOURNAL OF CHROMATOGRAPHY, A , 799(1 + 2), 67-81 CODEN: JCRAEY; ISSN: 0021-9673, 1998, XP004111373 *
ZARBL, ELFRIEDE ET AL: "Strong versus weak chiral cation exchangers: comparative evaluation for enantiomer separation of chiral bases by non-aqueous CEC", JOURNAL OF SEPARATION SCIENCE , 25(15-17), 1269-1283 CODEN: JSSCCJ; ISSN: 1615-9306, 2002, XP009102961 *

Also Published As

Publication number Publication date
WO2008092939A2 (en) 2008-08-07
EP2114919A2 (en) 2009-11-11
EA200900985A1 (en) 2009-12-30

Similar Documents

Publication Publication Date Title
WO2008092939A3 (en) Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation
WO2007141283A3 (en) Salts and crystalline salt forms of an 2-indolinone derivative
TW200621776A (en) Process for the preparation of chiral 8-(3-aminopiperidin-1-yl)-xanthines
WO2008130678A3 (en) Rosuvastatin intermediates and process for the preparation of rosuvastatin
EP2518039B8 (en) Method for the preparation of therapeutically valuable triphenylbutene derivatives
WO2009066326A3 (en) Improved process for the preparation of prasugrel and its pharmaceutically acceptable salts
WO2010060624A3 (en) Dry processing and novel forms of lacosamide
WO2010140765A3 (en) Novel method for preparing rosuvastatin, intermediate compounds useful for preparing same, and method for preparing same
WO2007081890A8 (en) Production of dolasetron
WO2007132354A3 (en) Process for preparing voriconazole, new polymorphic form of intermediate thereof, and uses thereof
WO2010049449A3 (en) Novel salts of sunitinib
WO2009005647A3 (en) Compounds and process to prepare chiral intermediates for synthesis of paroxetine
WO2006075139A3 (en) Novel process for the preparation of substituted indoles
WO2009053446A3 (en) Pregabalin intermediates and process for preparing them and pregabalin
WO2008117305A3 (en) A novel process for preparing pregabalin and its acid addition salts
WO2008137134A3 (en) Amorphous eletriptan hydrobromide and process for preparing it and other forms of eletriptan hydrobromide
WO2010012459A3 (en) A process for the preparation of solifenacin salts and their inclusion into pharmaceutical dosage forms
WO2007098273A3 (en) Novel crystalline forms of armodafinil and preparation thereof
WO2010079045A3 (en) Crystalline salt forms of flibanserine
WO2011067236A3 (en) Raltegravir polymorphs
EP2181989B8 (en) Process for the preparation of olopatadine
WO2008049922A3 (en) A new process for the preparation of montelukast
WO2010119450A3 (en) An improved process for the preparation of desmopressin or its pharmaceutically acceptable salts
WO2009062659A3 (en) Polymorphs of enantiopure erdosteine
WO2009047634A3 (en) Aqueous formulations of acetaminophen for injection

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2008708540

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 200900985

Country of ref document: EA

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08708540

Country of ref document: EP

Kind code of ref document: A2