MX2009008158A - Sintesis enantioselectiva de 6-amino-7-hidroxi-4,5,6,7-tetrahidro- imidazo[4,5,1-jk][1]-benzazepin-2[1h]-ona y zilpaterol. - Google Patents
Sintesis enantioselectiva de 6-amino-7-hidroxi-4,5,6,7-tetrahidro- imidazo[4,5,1-jk][1]-benzazepin-2[1h]-ona y zilpaterol.Info
- Publication number
- MX2009008158A MX2009008158A MX2009008158A MX2009008158A MX2009008158A MX 2009008158 A MX2009008158 A MX 2009008158A MX 2009008158 A MX2009008158 A MX 2009008158A MX 2009008158 A MX2009008158 A MX 2009008158A MX 2009008158 A MX2009008158 A MX 2009008158A
- Authority
- MX
- Mexico
- Prior art keywords
- benzazepin
- imidazo
- tetrahydro
- hydroxy
- amino
- Prior art date
Links
- JJFWDSAUXLLXOO-UHFFFAOYSA-N 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,l-j-k][1]-benzazepin-2(1h)-one Chemical compound OC1C(N)CCN2C(=O)NC3=CC=CC1=C32 JJFWDSAUXLLXOO-UHFFFAOYSA-N 0.000 title abstract 3
- ZSTCZWJCLIRCOJ-DGCLKSJQSA-N Zilpaterol Chemical compound O[C@H]1[C@H](NC(C)C)CCN2C(=O)NC3=CC=CC1=C32 ZSTCZWJCLIRCOJ-DGCLKSJQSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229960000960 zilpaterol Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 5
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 241001465754 Metazoa Species 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fodder In General (AREA)
Abstract
La invención se refiere a un proceso para la hidrogenación de una cetooxima para selectivamente formar un estereoisómero de aminoalcohol, y, en particular, a un proceso para la hidrogenación de 4,5-dihidro-imidazo[4,5,1-jkl[1]benzazepin-2,6,7[ 1H]-triona-6-oxima o una sal del mismo para selectivamente formar un estereoisómero de 6-amino-7-hidroxi-4,5,6,7-tetrahidro-imidazo[ 4,5,1-jk][1]-benzazepin-2[1H]-ona o una sal del mismo. Esta invención también se refiere al uso de un producto de hidrogenación de 6-amino-7-hidroxi-4,5,6,7-tetrahidro-imidazo[4,5, 1-jk][1]-benzazepin-2[1H]-ona o una sal del mismo para selectivamente hacer un estereoisómero de zilpaterol o una sal del mismo, así como el uso de un estereoisómero de zilpaterol o sal en métodos de tratamiento y medicamentos para animales.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89933607P | 2007-02-01 | 2007-02-01 | |
| PCT/EP2008/051206 WO2008092924A1 (en) | 2007-02-01 | 2008-01-31 | Enantioselective synthesis of 6-amino-7-hydroxy-4, 5, 6, 7-tetrahydro-imidazo [4, 5, 1-jk] [1] -benzazepin-2 [1h] -one and zilpaterol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2009008158A true MX2009008158A (es) | 2009-09-23 |
Family
ID=39430962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2009008158A MX2009008158A (es) | 2007-02-01 | 2008-01-31 | Sintesis enantioselectiva de 6-amino-7-hidroxi-4,5,6,7-tetrahidro- imidazo[4,5,1-jk][1]-benzazepin-2[1h]-ona y zilpaterol. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8629134B2 (es) |
| EP (1) | EP2109614B1 (es) |
| JP (1) | JP5126626B2 (es) |
| KR (1) | KR101150634B1 (es) |
| CN (1) | CN101600719B (es) |
| AU (1) | AU2008209743B2 (es) |
| BR (1) | BRPI0807865A2 (es) |
| CA (1) | CA2675651C (es) |
| IL (1) | IL199772A (es) |
| MX (1) | MX2009008158A (es) |
| RU (1) | RU2433131C2 (es) |
| SI (1) | SI2109614T1 (es) |
| WO (1) | WO2008092924A1 (es) |
| ZA (1) | ZA200905103B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008012343A2 (en) * | 2006-07-28 | 2008-01-31 | Intervet International B.V. | Macrolide synthesis process |
| CA2675651C (en) | 2007-02-01 | 2012-10-02 | Intervet International B.V. | Enantioselective synthesis of 6-amino-7-hydroxy-4, 5, 6, 7-tetrahydro-imidazo [4, 5, 1-jk] [1] -benzazepin-2 [1h] -one and zilpaterol |
| MX2009010499A (es) * | 2007-03-31 | 2009-10-19 | Intervet Int Bv | Procesos para elaborar zilpaterol y sales del mismo. |
| TW201033217A (en) | 2008-12-17 | 2010-09-16 | Intervet Int Bv | Process for making a crystalline zilpaterol salt |
| WO2012059807A1 (en) * | 2010-11-02 | 2012-05-10 | United Phosphorus Limited | Chiral intermediates useful for the preparation of hydroxyphosphine ligands |
| WO2013171330A1 (en) | 2012-05-18 | 2013-11-21 | Intervet International B.V. | A method of enhancing performance in broiler chickens |
| KR102214967B1 (ko) * | 2012-12-18 | 2021-02-10 | 인터벳 인터내셔널 비.브이. | 개선된 질파테롤 제조 공정 |
| CN103554113B (zh) * | 2013-09-25 | 2016-04-27 | 湖北美天生物科技有限公司 | 一种盐酸齐帕特罗的合成方法 |
| WO2015174812A1 (es) * | 2014-05-15 | 2015-11-19 | Interquim, S.A. De C.V. | Proceso mejorado para la preparación de zilpaterol |
| CN112662599B (zh) * | 2021-01-27 | 2022-06-14 | 吉林省农业科学院 | 一株禽源贝莱斯芽孢杆菌cl-4及其应用 |
| CN116675707A (zh) * | 2023-04-25 | 2023-09-01 | 宜宾学院 | 一种合成齐帕特罗顺式光学异构体的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US514869A (en) * | 1894-02-13 | Smokeless boiler | ||
| FR2534257A1 (fr) * | 1982-10-12 | 1984-04-13 | Roussel Uclaf | Nouveaux derives de la 6-amino 7-hydroxy 4,5,6,7-tetrahydro-imidazo/4,5,1-j-k/ /1/ benzazepin-2(1h)-one, leurs sels, application a titre de medicaments, compositions les renfermant et un intermediaire |
| IT1185550B (it) | 1985-04-12 | 1987-11-12 | Dox Al Italia Spa | Miscele non polverose di sfarinati o farine con principi attivi per mangimistica |
| HU203667B (en) * | 1986-12-11 | 1991-09-30 | Roussel Uclaf | Process for producing synergetic zootechnical compositions containing three components |
| JP2915161B2 (ja) | 1991-04-18 | 1999-07-05 | 三井化学株式会社 | 光学活性アミノアルコールおよびその中間体の製造方法 |
| FR2735474B1 (fr) | 1995-06-13 | 1997-08-08 | Roussel Uclaf | Chlorhydrate de zilpaterol sous une forme cristallisee particuliere, son procede de preparation et les produits intermediaires mis en oeuvre |
| EP0965574B1 (de) | 1998-06-19 | 2004-10-13 | Degussa AG | Verfahren zur enantioselektiven Hydrierung |
| JP4618607B2 (ja) * | 1999-07-30 | 2011-01-26 | 日本曹達株式会社 | 光学活性イミノアルコール類及びアミノアルコール類の製造法 |
| MXPA05011392A (es) | 2003-05-09 | 2005-12-12 | Umicore Ag & Co Kg | Ferrocenildifosfinas sustituidas, como ligaduras para catalizadores de hidrogenacion homogeneos. |
| WO2008006828A1 (en) | 2006-07-10 | 2008-01-17 | Intervet International B.V. | Zilpaterol enantiomer compositions and methods of making and using such compositions |
| EP2079747B1 (en) | 2006-10-13 | 2011-03-09 | Pfizer Limited | Heterocyclic compounds useful as anabolic agents for livestock animals |
| WO2008050207A1 (en) | 2006-10-25 | 2008-05-02 | Pfizer Limited | Heterocyclic compounds useful as anabolic agents for livestock animals |
| CA2675651C (en) | 2007-02-01 | 2012-10-02 | Intervet International B.V. | Enantioselective synthesis of 6-amino-7-hydroxy-4, 5, 6, 7-tetrahydro-imidazo [4, 5, 1-jk] [1] -benzazepin-2 [1h] -one and zilpaterol |
-
2008
- 2008-01-31 CA CA2675651A patent/CA2675651C/en active Active
- 2008-01-31 MX MX2009008158A patent/MX2009008158A/es active IP Right Grant
- 2008-01-31 CN CN2008800038779A patent/CN101600719B/zh not_active Expired - Fee Related
- 2008-01-31 BR BRPI0807865-3A2A patent/BRPI0807865A2/pt not_active IP Right Cessation
- 2008-01-31 RU RU2009132658/04A patent/RU2433131C2/ru not_active IP Right Cessation
- 2008-01-31 US US12/525,222 patent/US8629134B2/en active Active
- 2008-01-31 AU AU2008209743A patent/AU2008209743B2/en not_active Ceased
- 2008-01-31 EP EP08708517.1A patent/EP2109614B1/en not_active Not-in-force
- 2008-01-31 JP JP2009547692A patent/JP5126626B2/ja not_active Expired - Fee Related
- 2008-01-31 KR KR1020097017618A patent/KR101150634B1/ko not_active Expired - Fee Related
- 2008-01-31 WO PCT/EP2008/051206 patent/WO2008092924A1/en not_active Ceased
- 2008-01-31 SI SI200831309T patent/SI2109614T1/sl unknown
-
2009
- 2009-07-09 IL IL199772A patent/IL199772A/en not_active IP Right Cessation
- 2009-07-21 ZA ZA200905103A patent/ZA200905103B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL199772A (en) | 2013-08-29 |
| KR20090108720A (ko) | 2009-10-16 |
| IL199772A0 (en) | 2010-04-15 |
| KR101150634B1 (ko) | 2012-07-04 |
| ZA200905103B (en) | 2010-05-26 |
| SI2109614T1 (sl) | 2014-12-31 |
| US20100173892A1 (en) | 2010-07-08 |
| CN101600719B (zh) | 2013-06-12 |
| RU2009132658A (ru) | 2011-03-10 |
| CA2675651C (en) | 2012-10-02 |
| AU2008209743A1 (en) | 2008-08-07 |
| JP5126626B2 (ja) | 2013-01-23 |
| EP2109614B1 (en) | 2014-08-06 |
| AU2008209743B2 (en) | 2011-03-24 |
| WO2008092924A1 (en) | 2008-08-07 |
| BRPI0807865A2 (pt) | 2014-06-17 |
| CA2675651A1 (en) | 2008-08-07 |
| US8629134B2 (en) | 2014-01-14 |
| CN101600719A (zh) | 2009-12-09 |
| RU2433131C2 (ru) | 2011-11-10 |
| EP2109614A1 (en) | 2009-10-21 |
| JP2010517968A (ja) | 2010-05-27 |
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Legal Events
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