ATE195931T1 - Enantioselektive herstellung von optisch reinem albuterol - Google Patents
Enantioselektive herstellung von optisch reinem albuterolInfo
- Publication number
- ATE195931T1 ATE195931T1 AT95919913T AT95919913T ATE195931T1 AT E195931 T1 ATE195931 T1 AT E195931T1 AT 95919913 T AT95919913 T AT 95919913T AT 95919913 T AT95919913 T AT 95919913T AT E195931 T1 ATE195931 T1 AT E195931T1
- Authority
- AT
- Austria
- Prior art keywords
- optically pure
- albuterol
- enantioselective production
- pure albuterol
- acid
- Prior art date
Links
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229960002052 salbutamol Drugs 0.000 title abstract 2
- ICDQPCBDGAHBGG-SFHVURJKSA-N (1r)-2-(tert-butylamino)-1-[3-(hydroxymethyl)-4-phenylmethoxyphenyl]ethanol Chemical compound OCC1=CC([C@@H](O)CNC(C)(C)C)=CC=C1OCC1=CC=CC=C1 ICDQPCBDGAHBGG-SFHVURJKSA-N 0.000 abstract 1
- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 abstract 1
- WMJNKBXKYHXOHC-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylbenzoyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=CC=C1C WMJNKBXKYHXOHC-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- XKKHEBAZHSBZQI-UHFFFAOYSA-N methyl 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC(C(O)CNC(C)(C)C)=CC=C1OCC1=CC=CC=C1 XKKHEBAZHSBZQI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/247,302 US5399765A (en) | 1994-05-23 | 1994-05-23 | Enantioselective preparation of optically pure albuterol |
| US08/376,072 US5545745A (en) | 1994-05-23 | 1995-01-20 | Enantioselective preparation of optically pure albuterol |
| PCT/US1995/006539 WO1995032178A1 (en) | 1994-05-23 | 1995-05-23 | Enantioselective preparation of optically pure albuterol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE195931T1 true ATE195931T1 (de) | 2000-09-15 |
Family
ID=26938588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT95919913T ATE195931T1 (de) | 1994-05-23 | 1995-05-23 | Enantioselektive herstellung von optisch reinem albuterol |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5545745A (de) |
| EP (1) | EP0763010B1 (de) |
| JP (1) | JP3826208B2 (de) |
| AT (1) | ATE195931T1 (de) |
| AU (1) | AU686386B2 (de) |
| DE (1) | DE69518646T2 (de) |
| DK (1) | DK0763010T3 (de) |
| ES (1) | ES2151065T3 (de) |
| GR (1) | GR3034982T3 (de) |
| PT (1) | PT763010E (de) |
| WO (1) | WO1995032178A1 (de) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6136327A (en) | 1997-12-01 | 2000-10-24 | Alza Corporation | Stereospecific delivery of a drug using electrotransport |
| WO1999042460A1 (en) * | 1998-02-20 | 1999-08-26 | Fine Chemicals Corporation (Proprietary) Limited | Process for the production of optically enriched (r)- or (s)-albuterol |
| ZA994264B (en) | 1998-07-01 | 2000-01-25 | Warner Lambert Co | Stereoisomers with high affinity for adrenergic receptors. |
| US7232837B2 (en) * | 1999-06-29 | 2007-06-19 | Mcneil-Ppc, Inc. | Stereoisomers with high affinity for adrenergic receptors |
| US6451289B2 (en) * | 2000-03-24 | 2002-09-17 | Sepracor Inc. | Albuterol formulations |
| GB0030171D0 (en) * | 2000-12-11 | 2001-01-24 | Cipla Ltd | Process for preparing isomers of salbutamol |
| US6596686B2 (en) | 2001-03-12 | 2003-07-22 | International Flavors & Fragrances Inc. | Use of dihydropyrans as fragrance Material |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| DE60336089D1 (de) * | 2002-12-10 | 2011-03-31 | Sunovion Pharmaceuticals Inc | Aerosolformulierung umfassend Levalbuterol L-Tartratsalz |
| WO2004101592A1 (ja) * | 2003-05-19 | 2004-11-25 | Taisho Pharmaceutical Co., Ltd. | エリスロマイシンａ誘導体の製造方法 |
| US20050020692A1 (en) * | 2003-07-24 | 2005-01-27 | Ciofalo Vincent B. | Treatment of heaves |
| NZ547178A (en) * | 2003-11-20 | 2008-06-30 | Alteragon Pty Ltd | Method of decreasing fat deposits and body weight in mammals and birdsusing the R-isomer of Salbutamol |
| US7488758B2 (en) * | 2004-05-20 | 2009-02-10 | Teva Pharmaceutical Fine Chemicals, S.R.L. | Levalbuterol hydrochloride polymorph B |
| DE102004054054A1 (de) * | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| US7579505B2 (en) * | 2004-12-17 | 2009-08-25 | Cipla Limited | Crystalline levosalbutamol sulphate and polymorphic forms thereof |
| EP2311793A1 (de) | 2004-12-17 | 2011-04-20 | Cipla Ltd. | Kristallines Levosalbutamol-sulphate (Form II) |
| EP1832572A1 (de) * | 2006-03-08 | 2007-09-12 | Stirling Products Limited | Verfahren zur Enantiomerenanreicherung von Salbutamol und von Salbutamolvorläufern |
| EP1852108A1 (de) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | Zusammensetzungen von DPP-IV-Inhibitoren |
| EP2540725A1 (de) | 2006-05-04 | 2013-01-02 | Boehringer Ingelheim International GmbH | Polymorphe von 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| WO2008015689A1 (en) | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
| EP1935872A1 (de) * | 2006-12-11 | 2008-06-25 | Stirling Products Limited | Verfahren zur Gewinnung des R-Enantiomers von Salbutamol |
| WO2009073051A1 (en) * | 2007-12-03 | 2009-06-11 | Bridge Pharma, Inc. | Use of rr/sr-ractopamine |
| PE20091730A1 (es) | 2008-04-03 | 2009-12-10 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| WO2010047717A1 (en) * | 2008-10-24 | 2010-04-29 | Biolink Life Sciences, Inc. | Stable, water-insoluble r-(+)-alpha-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities |
| CN102256976A (zh) | 2008-12-23 | 2011-11-23 | 贝林格尔.英格海姆国际有限公司 | 有机化合物的盐形式 |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| KR20240090632A (ko) | 2009-11-27 | 2024-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 ｄｐｐ－ｉｖ 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
| CN102946875A (zh) | 2010-05-05 | 2013-02-27 | 贝林格尔.英格海姆国际有限公司 | 组合疗法 |
| WO2011161161A1 (en) | 2010-06-24 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Diabetes therapy |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| US8883800B2 (en) | 2011-07-15 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| JP6224084B2 (ja) | 2012-05-14 | 2017-11-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| JP6218811B2 (ja) | 2012-05-14 | 2017-10-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｉｒｓ及び／又は敗血症の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| CA2921385C (en) * | 2013-08-15 | 2021-10-19 | Allergan, Inc. | (-)-(2r,3s)-2-amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one (l)-(+) tartrate salt, its method of production and use |
| EP3110449B1 (de) | 2014-02-28 | 2023-06-28 | Boehringer Ingelheim International GmbH | Medizinische verwendung eines dpp-4-inhibitors |
| EP3042892A1 (de) | 2015-01-09 | 2016-07-13 | Deva Holding Anonim Sirketi | Amorphisierung von Levosalbutamoltartrat |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
| KR102789259B1 (ko) * | 2021-11-30 | 2025-04-02 | 주식회사 브이에스팜텍 | 고순도의 1-(1-(2-벤질페녹시)프로판-2-일)-2-메틸피페리딘 단일 이성질체의 제조방법 |
| CN115286521B (zh) * | 2022-07-11 | 2023-11-03 | 上海医药集团(本溪)北方药业有限公司 | 一种盐酸左沙丁胺醇的合成方法 |
| CN116693406B (zh) * | 2023-06-02 | 2024-04-19 | 山东锐顺药业有限公司 | 一种硫酸沙丁胺醇的制备方法 |
| CN116836069B (zh) * | 2023-06-02 | 2024-01-30 | 山东锐顺药业有限公司 | 一种盐酸左沙丁胺醇的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU648114B2 (en) * | 1990-09-11 | 1994-04-14 | Schering Corporation | Process for preparing albuterol, acetal, hemi-acetal, and hydrates of arylglyoxal intermediates thereof |
-
1995
- 1995-01-20 US US08/376,072 patent/US5545745A/en not_active Expired - Lifetime
- 1995-05-23 DE DE69518646T patent/DE69518646T2/de not_active Expired - Lifetime
- 1995-05-23 AT AT95919913T patent/ATE195931T1/de active
- 1995-05-23 ES ES95919913T patent/ES2151065T3/es not_active Expired - Lifetime
- 1995-05-23 JP JP53051395A patent/JP3826208B2/ja not_active Expired - Lifetime
- 1995-05-23 AU AU25559/95A patent/AU686386B2/en not_active Expired
- 1995-05-23 DK DK95919913T patent/DK0763010T3/da active
- 1995-05-23 EP EP95919913A patent/EP0763010B1/de not_active Expired - Lifetime
- 1995-05-23 WO PCT/US1995/006539 patent/WO1995032178A1/en not_active Ceased
- 1995-05-23 PT PT95919913T patent/PT763010E/pt unknown
-
2000
- 2000-11-24 GR GR20000402605T patent/GR3034982T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5545745A (en) | 1996-08-13 |
| AU2555995A (en) | 1995-12-18 |
| DE69518646T2 (de) | 2001-04-19 |
| AU686386B2 (en) | 1998-02-05 |
| PT763010E (pt) | 2000-12-29 |
| EP0763010B1 (de) | 2000-08-30 |
| EP0763010A4 (de) | 1997-07-16 |
| JPH10500954A (ja) | 1998-01-27 |
| JP3826208B2 (ja) | 2006-09-27 |
| DK0763010T3 (da) | 2001-01-08 |
| DE69518646D1 (de) | 2000-10-05 |
| ES2151065T3 (es) | 2000-12-16 |
| WO1995032178A1 (en) | 1995-11-30 |
| EP0763010A1 (de) | 1997-03-19 |
| GR3034982T3 (en) | 2001-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification |