DE964859T1 - Neues verfahren - Google Patents
Neues verfahrenInfo
- Publication number
- DE964859T1 DE964859T1 DE0964859T DE98953132T DE964859T1 DE 964859 T1 DE964859 T1 DE 964859T1 DE 0964859 T DE0964859 T DE 0964859T DE 98953132 T DE98953132 T DE 98953132T DE 964859 T1 DE964859 T1 DE 964859T1
- Authority
- DE
- Germany
- Prior art keywords
- process according
- omeprazole
- prepared
- methoxy
- titanium
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims 13
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 5
- 229960000381 omeprazole Drugs 0.000 claims 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 4
- 229910052719 titanium Inorganic materials 0.000 claims 4
- 239000010936 titanium Substances 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 2
- -1 titanium (IV) compound Chemical class 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 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
Claims (13)
1. Verfahren zur Herstellung von Omeprazol, bei dem man 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)
methyl]thio]-lH-benzimidazol in einem organischen
Lösungsmittel mit einem Oxidationsmittel und gegebenenfalls in Gegenwart einer Base oxidiert, dadurch gekennzeichnet,
daß man die Oxidation in Gegenwart eines Titankomplexes durchführt.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Oxidation in Gegenwart einer Base
durchführt.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man den Titankomplex aus einer
Titan(IV)-Verbindung und einem Enantiomerengemisch chiraler Liganden herstellt.
4. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man als Enantiomerengemisch ein
racemisches Gemisch einsetzt.
5. Verfahren nach Anspruch 1, dadurch gekennzeichnet,
daß man den Titankomplex aus einer Titan(IV)-Verbindung und einem achiralen Liganden herstellt.
6. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man aus der Reaktionsmischung Omeprazol
ausfällt.
7. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man keinen Extraktionsschritt durchführt.
8. Verfahren nach einem der Ansprüche 1-7, dadurch gekennzeichnet, daß man den Titankomplex in Gegenwart
von 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]thio]-lH-benzimidazol
herstellt.
9. Verfahren nach einem der Ansprüche 1-8, dadurch gekennzeichnet, daß man als Oxidationsmittel Cumolhydroperoxid
oder tert.-Butylhydroperoxid einsetzt.
10. Verfahren nach einem der Ansprüche 1-9, dadurch gekennzeichnet, daß man als organisches Lösungsmittel
Toluol einsetzt.
11. Verfahren nach einem der Ansprüche 1-10, dadurch gekennzeichnet, daß man als Base Triethylamin
oder &Ngr;,&Ngr;-Diisopropylethylamin einsetzt.
12. Pharmazeutische Zusammensetzung, enthaltend Omeprazol und einen pharmazeutisch unbedenklichen
Träger oder ein pharmazeutisch unbedenkliches Verdünnungsmittel, dadurch gekennzeichnet, daß das Omeprazol
nach einem der Ansprüche 1-11 hergestellt wird.
13. Nach einem Verfahren gemäß einem der Ansprüche 1-11 hergestelltes Omeprazol.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9704183A SE9704183D0 (sv) | 1997-11-14 | 1997-11-14 | New process |
PCT/SE1998/001984 WO1999025711A1 (en) | 1997-11-14 | 1998-11-03 | New process |
Publications (1)
Publication Number | Publication Date |
---|---|
DE964859T1 true DE964859T1 (de) | 2000-05-04 |
Family
ID=20408989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE0964859T Pending DE964859T1 (de) | 1997-11-14 | 1998-11-03 | Neues verfahren |
Country Status (35)
Country | Link |
---|---|
US (1) | US6303788B1 (de) |
EP (1) | EP0964859A1 (de) |
JP (1) | JP2001508466A (de) |
KR (1) | KR20000070069A (de) |
CN (1) | CN1145624C (de) |
AR (1) | AR013740A1 (de) |
AU (1) | AU750743B2 (de) |
BR (1) | BR9806871A (de) |
CA (1) | CA2276753A1 (de) |
DE (1) | DE964859T1 (de) |
DZ (1) | DZ2641A1 (de) |
EE (1) | EE04154B1 (de) |
ES (1) | ES2138950T1 (de) |
GR (1) | GR990300046T1 (de) |
HR (1) | HRP990218A2 (de) |
HU (1) | HUP0003737A3 (de) |
ID (1) | ID21999A (de) |
IL (1) | IL130647A0 (de) |
IN (1) | IN190801B (de) |
IS (1) | IS5106A (de) |
MA (1) | MA26564A1 (de) |
MY (1) | MY118199A (de) |
NO (1) | NO318197B1 (de) |
NZ (1) | NZ336447A (de) |
PL (1) | PL334701A1 (de) |
RU (1) | RU2211218C2 (de) |
SE (1) | SE9704183D0 (de) |
SK (1) | SK87299A3 (de) |
TN (1) | TNSN98202A1 (de) |
TR (1) | TR199901643T1 (de) |
TW (1) | TW588046B (de) |
UA (1) | UA68342C2 (de) |
WO (1) | WO1999025711A1 (de) |
YU (1) | YU31199A (de) |
ZA (1) | ZA989999B (de) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
IL142703A (en) | 1998-11-10 | 2006-04-10 | Astrazeneca Ab | Crystalline form of omeprazole |
UA72748C2 (en) | 1998-11-10 | 2005-04-15 | Astrazeneca Ab | A novel crystalline form of omeprazole |
JP2004524303A (ja) * | 2001-02-02 | 2004-08-12 | テバ ファーマシューティカル インダストリーズ リミティド | 置換された2−(2−ピリジルメチル)スルフィニル−1h−ベンゾイミダゾール類の製造方法 |
SE0203092D0 (en) * | 2002-10-18 | 2002-10-18 | Astrazeneca Ab | Method for the synthesis of a benzimidazole compound |
US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
DE602005016705D1 (de) * | 2004-10-11 | 2009-10-29 | Ranbaxy Lab Ltd | Verfahren zur herstellung substituierter sulfoxide |
EP1801110A1 (de) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Argininsalz des Esomeprazols |
CN1810803B (zh) * | 2006-02-17 | 2010-11-17 | 中国科学院上海有机化学研究所 | 高对映体选择性制备(s)-奥美拉唑的方法 |
CN101538264A (zh) * | 2008-03-19 | 2009-09-23 | 中国科学院成都有机化学有限公司 | 手性亚砜类化合物的制备新方法 |
CN102603621B (zh) * | 2012-02-07 | 2013-09-04 | 成都苑东药业有限公司 | 一种新型手性亚砜化合物和以该化合物制备埃索美拉唑钠的方法 |
CN106083819A (zh) * | 2016-06-08 | 2016-11-09 | 扬子江药业集团有限公司 | 一种奥美拉唑的制备方法 |
ES2948511A1 (es) * | 2021-09-08 | 2023-09-13 | Fundacion Para La Investigacion Biomedica Del Hospital Univ De La Princesa | Derivados de n-sulfonilureas y su uso terapeutico |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
SE9002043D0 (sv) | 1990-06-07 | 1990-06-07 | Astra Ab | Improved method for synthesis |
NZ244301A (en) | 1991-09-20 | 1994-08-26 | Merck & Co Inc | Preparation of 2-pyridylmethylsulphinylbenzimidazole and pyridoimidazole derivatives from the corresponding sulphenyl compounds |
SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
-
1997
- 1997-11-14 SE SE9704183A patent/SE9704183D0/xx unknown
-
1998
- 1998-03-11 UA UA99073870A patent/UA68342C2/uk unknown
- 1998-11-02 AR ARP980105504A patent/AR013740A1/es unknown
- 1998-11-02 IN IN3213DE1998 patent/IN190801B/en unknown
- 1998-11-02 MY MYPI98004977A patent/MY118199A/en unknown
- 1998-11-02 TW TW087118172A patent/TW588046B/zh not_active IP Right Cessation
- 1998-11-02 ZA ZA989999A patent/ZA989999B/xx unknown
- 1998-11-03 CN CNB988017970A patent/CN1145624C/zh not_active Expired - Fee Related
- 1998-11-03 SK SK872-99A patent/SK87299A3/sk unknown
- 1998-11-03 BR BR9806871-7A patent/BR9806871A/pt not_active Application Discontinuation
- 1998-11-03 EP EP98953132A patent/EP0964859A1/de not_active Ceased
- 1998-11-03 ES ES98953132T patent/ES2138950T1/es active Pending
- 1998-11-03 AU AU10582/99A patent/AU750743B2/en not_active Ceased
- 1998-11-03 WO PCT/SE1998/001984 patent/WO1999025711A1/en not_active Application Discontinuation
- 1998-11-03 HU HU0003737A patent/HUP0003737A3/hu unknown
- 1998-11-03 EE EEP199900391A patent/EE04154B1/xx not_active IP Right Cessation
- 1998-11-03 PL PL98334701A patent/PL334701A1/xx unknown
- 1998-11-03 US US09/194,647 patent/US6303788B1/en not_active Expired - Fee Related
- 1998-11-03 RU RU99117541/04A patent/RU2211218C2/ru not_active IP Right Cessation
- 1998-11-03 IL IL13064798A patent/IL130647A0/xx not_active IP Right Cessation
- 1998-11-03 YU YU31199A patent/YU31199A/sh unknown
- 1998-11-03 DZ DZ980251A patent/DZ2641A1/xx active
- 1998-11-03 JP JP52827799A patent/JP2001508466A/ja not_active Ceased
- 1998-11-03 ID IDW990692A patent/ID21999A/id unknown
- 1998-11-03 DE DE0964859T patent/DE964859T1/de active Pending
- 1998-11-03 TR TR1999/01643T patent/TR199901643T1/xx unknown
- 1998-11-03 CA CA002276753A patent/CA2276753A1/en not_active Abandoned
- 1998-11-03 NZ NZ336447A patent/NZ336447A/en unknown
- 1998-11-03 KR KR1019997006290A patent/KR20000070069A/ko active IP Right Grant
- 1998-11-05 MA MA25335A patent/MA26564A1/fr unknown
- 1998-11-09 TN TNTNSN98202A patent/TNSN98202A1/fr unknown
-
1999
- 1999-07-02 NO NO19993298A patent/NO318197B1/no unknown
- 1999-07-02 IS IS5106A patent/IS5106A/is unknown
- 1999-07-13 HR HR990218A patent/HRP990218A2/hr not_active Application Discontinuation
-
2000
- 2000-07-31 GR GR990300046T patent/GR990300046T1/el unknown
Also Published As
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