JPH10510705A - 生物酸化による医薬的に活性なスルホキシドのエナンチオ選択的製造 - Google Patents
生物酸化による医薬的に活性なスルホキシドのエナンチオ選択的製造Info
- Publication number
- JPH10510705A JPH10510705A JP8518669A JP51866996A JPH10510705A JP H10510705 A JPH10510705 A JP H10510705A JP 8518669 A JP8518669 A JP 8518669A JP 51866996 A JP51866996 A JP 51866996A JP H10510705 A JPH10510705 A JP H10510705A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- hydrogen
- biooxidation
- alkyl
- 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
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/185—Heterocyclic compounds containing sulfur atoms as ring hetero atoms in the condensed system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.プロ‐キラルスルフィド対応化合物の立体選択的生物酸化からなる、単一の 鏡像異性体としてのまたは鏡像異性体的に富んだ形態での式(II) 〔式中、 Het1は、 であり、 Het2は、 であり、 Xは、 であり、 ベンズイミダゾール部分におけるNは、場合によってはR6〜R9によ って置換された炭素原子の1個を未置換の窒素原子に換え得ることができること を意味し、 R1、R2およびR3は、同一または異なりそして水素、アルキル、場合によって は弗素により置換されていてもよいアルコキシ、アルキルチオ、アルコキシアル コキシ、ジアルキルアミノ、ピペリジノ、モルホリノ、ハロゲン、フェニルアル キル、フェニルアルコキシから選択されたものであり、 R4およびR4′は、同一または異なりそして水素、アルキル、アルアルキルか ら選択されたものであり、 R5は、水素、ハロゲン、トリフルオロメチル、アルキル、アルコキシであり 、 R6〜R9は、同一または異なりそして水素、アルキル、アルコキシ、ハロゲン 、ハロアルコキシ、アルキルカルボニル、アルコキシカルボニル、オキサゾリル 、トリフルオロアルキルから選択されたものでありまたは隣接基R6〜R9は、それ らが結合している炭素原子と一緒になって場合によっては置換されていてもよい 環構造を完成することができ、 R10は、水素またはアルコキシカルボニルオキシメチルであり、 R11は、水素であるかまたはR3と一緒になってアルキレン鎖を形成し、 R12およびR13は、同一または異なりそして水素、ハロゲンまたはアルキルか ら選択されたものである〕の化合物を製造する方法。 2.Het1が であり、 Het2が であり、 Xが であり、 R1、R2、R3、R6〜R9、R10およびR11が請求項1において定義した通りである 請求項1の方法。 3.式(II)の化合物が、式 である請求項1または2の方法。 4.式(II)の化合物の単一の鏡像異性体を製造する請求項1〜3の何れか1項に 記載の方法。 5.式(IIa)の化合物を製造しそして生物酸化を Penicillium frequentans Brevibacterium paraffinolyticum または Mycobacterium sp. の微生物を使用して実施する請求項3の方法。 6.式(IIb)の化合物を製造しそして生物酸化を Asperigillus niger または Ustilago maydis の微生物を使用して実施する請求項3の方法。 7.式(IId)の化合物を製造しそして生物酸化を Mycobacterium sp. Arthrobacter petroleophagus Brevibacterium paraffinolyticum または Ustilago maydis の微生物を使用して実施する請求項3の方法。 8.式(IIe)の化合物を製造しそして生物酸化を Mycobacterium sp. Penicillium frequentans の微生物を使用して実施する請求項3の方法。 9.実質的に実施例の何れかに記載した請求項1の方法。 10.請求項1〜9の何れか1項に記載の方法によって製造された請求項1の単一 の鏡像異性体としてのまたは鏡像異性体的に富んだ形態での式(II)の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9423970A GB9423970D0 (en) | 1994-11-28 | 1994-11-28 | Oxidation |
GB9423970.4 | 1994-11-28 | ||
PCT/SE1995/001415 WO1996017076A1 (en) | 1994-11-28 | 1995-11-27 | Enantioselective preparation of pharmaceutically active sulfoxides by biooxidation |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10510705A true JPH10510705A (ja) | 1998-10-20 |
JP3684576B2 JP3684576B2 (ja) | 2005-08-17 |
Family
ID=10765078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51866996A Expired - Fee Related JP3684576B2 (ja) | 1994-11-28 | 1995-11-27 | 生物酸化による医薬的に活性なスルホキシドのエナンチオ選択的製造 |
Country Status (11)
Country | Link |
---|---|
US (1) | US5840552A (ja) |
EP (1) | EP0795024B1 (ja) |
JP (1) | JP3684576B2 (ja) |
AT (1) | ATE232907T1 (ja) |
AU (1) | AU699577B2 (ja) |
CA (1) | CA2203999A1 (ja) |
DE (1) | DE69529686T2 (ja) |
DK (1) | DK0795024T3 (ja) |
ES (1) | ES2191066T3 (ja) |
GB (1) | GB9423970D0 (ja) |
WO (1) | WO1996017076A1 (ja) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
GB9423968D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Resolution |
GB9423970D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Oxidation |
SE510650C2 (sv) | 1997-05-30 | 1999-06-14 | Astra Ab | Ny förening |
AU746706B2 (en) | 1997-07-03 | 2002-05-02 | Du Pont Pharmaceuticals Company | Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders |
US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
SE9900274D0 (sv) | 1999-01-28 | 1999-01-28 | Astra Ab | New compound |
AU6727700A (en) * | 1999-08-25 | 2001-03-19 | Takeda Chemical Industries Ltd. | Process for the preparation of optically active sulfoxide derivatives |
US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
KR100775802B1 (ko) * | 2000-04-28 | 2007-11-12 | 다케다 야쿠힌 고교 가부시키가이샤 | 광학 활성 술폭시드 유도체의 제조 방법 |
DE10254167A1 (de) | 2002-11-20 | 2004-06-09 | Icon Genetics Ag | Verfahren zur Kontrolle von zellulären Prozessen in Pflanzen |
US7301030B2 (en) | 2002-12-06 | 2007-11-27 | Nycomed Gmbh | Process for preparing (S)-pantoprazole |
BRPI0310118B1 (pt) | 2002-12-06 | 2015-10-20 | Altana Pharma Ag | processo para a preparação de inibidores de bomba de próton (ppi) opticamente puro possuindo uma estrutura de sulfinila |
EP1801110A1 (en) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Esomeprazole arginine salt |
BRPI0621832A2 (pt) | 2006-07-05 | 2013-03-19 | Lupin Ltd | processo para a preparaÇço de enantiâmeros oticamente puros ou oticamente enriquecidos de compostos de sulfàxido |
SG181535A1 (en) | 2009-12-08 | 2012-07-30 | Codexis Inc | Synthesis of prazole compounds |
CZ302612B6 (cs) * | 2010-11-01 | 2011-08-03 | Zentiva, K.S. | Kmen mikroorganismu Bacillus sp. B71 CCM 7718 |
US9267159B2 (en) | 2010-12-08 | 2016-02-23 | Codexis, Inc. | Biocatalysts and methods for the synthesis of armodafinil |
CN108239618A (zh) * | 2016-12-23 | 2018-07-03 | 浙江京新药业股份有限公司 | 共表达环己酮单加氧酶和异丙醇脱氢酶的基因工程菌及其应用 |
CN108251466B (zh) * | 2016-12-28 | 2021-07-02 | 浙江京新药业股份有限公司 | 一种酶法合成埃索美拉唑的方法 |
CN107418923B (zh) | 2017-09-20 | 2018-03-23 | 华东理工大学 | 伯克霍尔德菌及其应用 |
CN113461663B (zh) * | 2020-03-30 | 2023-11-28 | 江苏奥赛康药业有限公司 | 一种质子泵抑制剂艾司奥美拉唑钠的膜分离纯化方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
US5049674A (en) * | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
CA2083606C (en) * | 1990-06-20 | 2001-08-21 | Arne Elof Brandstrom | Dialkoxy-pyridinyl-benzimidazole derivatives, process for their preparation and their pharmaceutical use |
DE4035455A1 (de) * | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
TNSN95062A1 (fr) * | 1994-05-27 | 1996-02-06 | Astra Ab | Nouveaux derives dialkoxy-pyridinyle-benzimidazole |
TNSN95063A1 (fr) * | 1994-05-27 | 1996-02-06 | Astra Ab | Nouveaux benzimidazoles substitues |
GB9423970D0 (en) * | 1994-11-28 | 1995-01-11 | Astra Ab | Oxidation |
-
1994
- 1994-11-28 GB GB9423970A patent/GB9423970D0/en active Pending
-
1995
- 1995-11-27 US US08/569,114 patent/US5840552A/en not_active Expired - Lifetime
- 1995-11-27 WO PCT/SE1995/001415 patent/WO1996017076A1/en active IP Right Grant
- 1995-11-27 EP EP95939460A patent/EP0795024B1/en not_active Expired - Lifetime
- 1995-11-27 AU AU41269/96A patent/AU699577B2/en not_active Ceased
- 1995-11-27 JP JP51866996A patent/JP3684576B2/ja not_active Expired - Fee Related
- 1995-11-27 DE DE69529686T patent/DE69529686T2/de not_active Expired - Fee Related
- 1995-11-27 DK DK95939460T patent/DK0795024T3/da active
- 1995-11-27 ES ES95939460T patent/ES2191066T3/es not_active Expired - Lifetime
- 1995-11-27 AT AT95939460T patent/ATE232907T1/de not_active IP Right Cessation
- 1995-11-27 CA CA002203999A patent/CA2203999A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP0795024B1 (en) | 2003-02-19 |
DE69529686D1 (de) | 2003-03-27 |
ES2191066T3 (es) | 2003-09-01 |
JP3684576B2 (ja) | 2005-08-17 |
DE69529686T2 (de) | 2004-01-15 |
AU699577B2 (en) | 1998-12-10 |
CA2203999A1 (en) | 1996-06-06 |
EP0795024A1 (en) | 1997-09-17 |
DK0795024T3 (da) | 2003-04-22 |
WO1996017076A1 (en) | 1996-06-06 |
GB9423970D0 (en) | 1995-01-11 |
ATE232907T1 (de) | 2003-03-15 |
US5840552A (en) | 1998-11-24 |
AU4126996A (en) | 1996-06-19 |
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