AR075496A1 - Proceso para la preparacion de compuestos opticamente activos usando hidrogenacion de transferencia y uso de los mismos - Google Patents
Proceso para la preparacion de compuestos opticamente activos usando hidrogenacion de transferencia y uso de los mismosInfo
- Publication number
- AR075496A1 AR075496A1 ARP090105061A ARP090105061A AR075496A1 AR 075496 A1 AR075496 A1 AR 075496A1 AR P090105061 A ARP090105061 A AR P090105061A AR P090105061 A ARP090105061 A AR P090105061A AR 075496 A1 AR075496 A1 AR 075496A1
- Authority
- AR
- Argentina
- Prior art keywords
- preparation
- catalytic reduction
- asymmetric catalytic
- optically active
- active compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 title 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 abstract 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 abstract 2
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229960004136 rivastigmine Drugs 0.000 abstract 2
- 238000009901 transfer hydrogenation reaction Methods 0.000 abstract 2
- GQZXRLWUYONVCP-QMMMGPOBSA-N 3-[(1s)-1-(dimethylamino)ethyl]phenol Chemical compound CN(C)[C@@H](C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-QMMMGPOBSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000008186 active pharmaceutical agent Substances 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940088679 drug related substance Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hospice & Palliative Care (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Abstract
Un proceso catalítico para la preparacion de compuestos opticamente activo y su conversion posteriormente hasta las sustancias de fármaco deseadas. En particular, el proceso se refiere a la preparacion del (S)-3-(1-dimetil-amino-etil)-fenol utilizando reduccion catalítica asimétrica e hidrogenacion de transferencia, proporcionando de esta manera una mejor ruta para la formacion de sustancias de fármaco, tales como rivastigmina y tartrato ácido de rivastigmina. Reivindicacion 1: Un proceso para la preparacion de un compuesto de acuerdo con la formula general (1) en donde: R1 = alquilo C1-20, alquenilo C2-20, alquinilo C2-20, haluro orgánico de 2 a 20 átomos de carbono, un arilo, un grupo amina o amida; y n =1 a 5; comprendiendo este proceso: (a) llevar a cabo una reduccion catalítica asimétrica sobre una hidroxifenona de acuerdo con la siguiente formula general (2) en donde: R1 = alquilo C1-20, alquenilo C2-20, alquinilo C2-20, haluro orgánico de 2 a 20 átomos de carbono, un arilo, un grupo que contiene amina o amida; n = 1 a 5; y en donde esta reduccion catalítica asimétrica se lleva a cabo utilizando hidrogenacion de transferencia, y en donde esta reduccion catalítica asimétrica se lleva a cabo utilizando un catalizador de metal quiral. Reivindicacion 33: El uso de un alcohol quiral preparado de acuerdo con cualquiera de las reivindicaciones 1 a 20, en la preparacion de un material de partida de un ingrediente farmacéutico activo para la produccion de composiciones farmacéuticas.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0823554.1A GB0823554D0 (en) | 2008-12-24 | 2008-12-24 | Process for the preparation of optically active compounds using transfer hydrogenation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR075496A1 true AR075496A1 (es) | 2011-04-06 |
Family
ID=40344210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090105061A AR075496A1 (es) | 2008-12-24 | 2009-12-22 | Proceso para la preparacion de compuestos opticamente activos usando hidrogenacion de transferencia y uso de los mismos |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8415508B2 (es) |
| EP (1) | EP2382172A1 (es) |
| JP (1) | JP2012513966A (es) |
| KR (1) | KR20110098964A (es) |
| CN (1) | CN102264672A (es) |
| AR (1) | AR075496A1 (es) |
| AU (1) | AU2009331493B2 (es) |
| BR (1) | BRPI0923394A2 (es) |
| CA (1) | CA2748349A1 (es) |
| CL (1) | CL2011001563A1 (es) |
| CO (1) | CO6382153A2 (es) |
| EC (1) | ECSP11011221A (es) |
| GB (1) | GB0823554D0 (es) |
| IL (1) | IL213520A0 (es) |
| MA (1) | MA32983B1 (es) |
| MX (1) | MX2011006918A (es) |
| MY (1) | MY151103A (es) |
| NZ (1) | NZ593493A (es) |
| SG (1) | SG172052A1 (es) |
| TN (1) | TN2011000290A1 (es) |
| TW (1) | TW201035028A (es) |
| WO (1) | WO2010072798A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193600B (zh) * | 2012-01-07 | 2016-04-06 | 浙江九洲药物科技有限公司 | 卡巴拉汀中间体的制备方法 |
| US20160130193A1 (en) * | 2013-06-14 | 2016-05-12 | Nissan Chemical Industries, Ltd. | Production method for optically active alcohol compound |
| CN103980270A (zh) * | 2014-05-19 | 2014-08-13 | 埃斯特维华义制药有限公司 | 一种（r）-3-奎宁醇的制备方法 |
| CN108752322A (zh) * | 2018-09-12 | 2018-11-06 | 广州新民培林医药科技有限公司 | 一种新型Tepotinib衍生物和制备方法及其在抗肿瘤药物中的应用 |
| CN109809967B (zh) * | 2019-03-04 | 2022-03-18 | 陕西师范大学 | 一种合成手性醇的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU201906B (en) | 1987-03-04 | 1991-01-28 | Sandoz Ag | Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them |
| US4996235A (en) * | 1987-11-25 | 1991-02-26 | Eli Lilly And Company | 3,4-diphenylbutanamines |
| JPH0899940A (ja) * | 1994-09-30 | 1996-04-16 | Kanegafuchi Chem Ind Co Ltd | 光学活性な１−（３，４−ジメトキシフェニル）−２−アミノプロパンの製造法 |
| GB9706321D0 (en) | 1997-03-26 | 1997-05-14 | Zeneca Ltd | Catalytic hydrogenation |
| JP3938651B2 (ja) * | 2000-04-13 | 2007-06-27 | セントラル硝子株式会社 | 光学活性α−メチル−ビス−３、５−（トリフルオロメチル）ベンジルアミンの製造方法 |
| JPWO2002051781A1 (ja) | 2000-12-25 | 2004-04-22 | 味の素株式会社 | 光学活性ハロヒドリン化合物の製造方法 |
| DE602004017747D1 (de) * | 2003-07-08 | 2008-12-24 | Unilever Nv | Verfahren zur herstellung einer kosmetisch aktiven verbindung |
| GB0329284D0 (en) | 2003-12-18 | 2004-01-21 | Avecia Ltd | Process |
| WO2005092825A1 (ja) * | 2004-03-29 | 2005-10-06 | Nagoya Industrial Science Research Institute | 光学活性アルコールの製法 |
| US6939981B1 (en) * | 2004-06-25 | 2005-09-06 | Eastman Chemical Company | Ruthenium complexes of phosphine-aminophosphine ligands |
| RU2393148C2 (ru) * | 2004-11-08 | 2010-06-27 | Эмкюр Фармасьютикалз Лимитед | Способ получения (s)-3-[(1-диметиламино)этил]-фенил-n-этил-n-метил-карбамата |
| WO2006137167A1 (ja) * | 2005-06-20 | 2006-12-28 | Kanto Kagaku Kabushiki Kaisha | スルホナート触媒及びそれを利用したアルコール化合物の製法 |
| TWI389709B (zh) | 2005-12-01 | 2013-03-21 | Novartis Ag | 經皮治療系統 |
| WO2007147897A1 (de) | 2006-06-23 | 2007-12-27 | Basf Se | Verfahren zur herstellung von optisch aktiven 2-halogen-1-phenylethanol-derivaten und folgeprodukten davon |
| US20110105693A1 (en) | 2008-05-01 | 2011-05-05 | Kanata Chemical Technologies Inc. | Cationic transition-metal arene catalysts |
-
2008
- 2008-12-24 GB GBGB0823554.1A patent/GB0823554D0/en not_active Ceased
-
2009
- 2009-12-17 US US12/653,748 patent/US8415508B2/en not_active Expired - Fee Related
- 2009-12-22 AR ARP090105061A patent/AR075496A1/es not_active Application Discontinuation
- 2009-12-23 NZ NZ593493A patent/NZ593493A/xx not_active IP Right Cessation
- 2009-12-23 BR BRPI0923394A patent/BRPI0923394A2/pt not_active IP Right Cessation
- 2009-12-23 KR KR1020117017258A patent/KR20110098964A/ko not_active Application Discontinuation
- 2009-12-23 MX MX2011006918A patent/MX2011006918A/es not_active Application Discontinuation
- 2009-12-23 SG SG2011042108A patent/SG172052A1/en unknown
- 2009-12-23 CA CA2748349A patent/CA2748349A1/en not_active Abandoned
- 2009-12-23 EP EP09799106A patent/EP2382172A1/en not_active Withdrawn
- 2009-12-23 CN CN2009801523437A patent/CN102264672A/zh active Pending
- 2009-12-23 TW TW098144595A patent/TW201035028A/zh unknown
- 2009-12-23 WO PCT/EP2009/067821 patent/WO2010072798A1/en active Application Filing
- 2009-12-23 AU AU2009331493A patent/AU2009331493B2/en not_active Ceased
- 2009-12-23 MY MYPI20112891 patent/MY151103A/en unknown
- 2009-12-23 MA MA34036A patent/MA32983B1/fr unknown
- 2009-12-23 JP JP2011542822A patent/JP2012513966A/ja active Pending
-
2011
- 2011-06-09 TN TN2011000290A patent/TN2011000290A1/fr unknown
- 2011-06-13 IL IL213520A patent/IL213520A0/en unknown
- 2011-06-23 CL CL2011001563A patent/CL2011001563A1/es unknown
- 2011-06-29 CO CO11081447A patent/CO6382153A2/es active IP Right Grant
- 2011-07-22 EC EC2011011221A patent/ECSP11011221A/es unknown
-
2012
- 2012-12-05 US US13/705,884 patent/US8637713B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CL2011001563A1 (es) | 2012-01-13 |
| KR20110098964A (ko) | 2011-09-02 |
| ECSP11011221A (es) | 2011-08-31 |
| AU2009331493B2 (en) | 2013-03-07 |
| CN102264672A (zh) | 2011-11-30 |
| MX2011006918A (es) | 2011-07-29 |
| TW201035028A (en) | 2010-10-01 |
| EP2382172A1 (en) | 2011-11-02 |
| CO6382153A2 (es) | 2012-02-15 |
| MA32983B1 (fr) | 2012-01-02 |
| AU2009331493A1 (en) | 2011-07-07 |
| IL213520A0 (en) | 2011-07-31 |
| MY151103A (en) | 2014-04-15 |
| NZ593493A (en) | 2013-03-28 |
| CA2748349A1 (en) | 2010-07-01 |
| US20100168229A1 (en) | 2010-07-01 |
| TN2011000290A1 (en) | 2012-12-17 |
| BRPI0923394A2 (pt) | 2016-01-12 |
| JP2012513966A (ja) | 2012-06-21 |
| US20130096337A1 (en) | 2013-04-18 |
| US8415508B2 (en) | 2013-04-09 |
| GB0823554D0 (en) | 2009-01-28 |
| US8637713B2 (en) | 2014-01-28 |
| WO2010072798A1 (en) | 2010-07-01 |
| SG172052A1 (en) | 2011-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |