AR055917A1 - Proceso de reduccion catalitica asimetrica para preparar los isomeros (s)-(+) y (r)-(-) del compuesto (10,11-dihidro-10-hidroxi-5-h dibenz [b.f] azepin-5-carboxamida] - Google Patents
Proceso de reduccion catalitica asimetrica para preparar los isomeros (s)-(+) y (r)-(-) del compuesto (10,11-dihidro-10-hidroxi-5-h dibenz [b.f] azepin-5-carboxamida]Info
- Publication number
- AR055917A1 AR055917A1 ARP060101623A ARP060101623A AR055917A1 AR 055917 A1 AR055917 A1 AR 055917A1 AR P060101623 A ARP060101623 A AR P060101623A AR P060101623 A ARP060101623 A AR P060101623A AR 055917 A1 AR055917 A1 AR 055917A1
- Authority
- AR
- Argentina
- Prior art keywords
- dibenz
- azepin
- carboxamide
- aryl
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000010531 catalytic reduction reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 3
- 235000019253 formic acid Nutrition 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000004678 hydrides Chemical class 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 abstract 1
- 229960001816 oxcarbazepine Drugs 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11
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)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Es revelado un proceso para preparar (S)-(+)-10,11-dihidro-10-hidroxi-5H-dibenz/b, f/azepin-5-carboxamida o (R)-(-)-10,11-dihidro-10-hidroxi-5H-dibenz/b, f/azepin-5-carboxamida, mediante la reduccion de oxcarbazepina en la presencia de un catalizador y una fuente de hidruro. El catalizador es preparado a partir de una combinacion de [RuX2(L)]2 en donde X es cloro, bromo o yodo, y L es un ligando arilo o aril-alifático, con un ligando de formula (1) o de formula (2), en donde R1 está elegido a partir de alcoxi C1-6 y alquilo C1-6, n es un numero de 0 a 5, y cuando n es un numero de 2 a 5, R1 puede ser el mismo o diferente, y R2 es alquilo, alquilo sustituido, arilo, arilo sustituido, alcarilo o alcarilo sustituido. La fuente de hidruro es o bien NR3R4R5 y ácido formico, [R3R4R5NH][OOCH] y opcionalmente ácido formico, o [M][OOCH]x y ácido formico, en donde R3, R4 y R5 son alquilo C1-6, M es un metal alcalino o un metal alcalino térreo y x es 1 o 2. un pH de 6,5 a 8 es mantenido durante el proceso.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0515690.6A GB0515690D0 (en) | 2005-07-29 | 2005-07-29 | Asymmetric catalytic reduction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR055917A1 true AR055917A1 (es) | 2007-09-12 |
Family
ID=34983785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060101623A AR055917A1 (es) | 2005-07-29 | 2006-04-24 | Proceso de reduccion catalitica asimetrica para preparar los isomeros (s)-(+) y (r)-(-) del compuesto (10,11-dihidro-10-hidroxi-5-h dibenz [b.f] azepin-5-carboxamida] |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US8288532B2 (es) |
| EP (2) | EP2319836B1 (es) |
| JP (2) | JP5295765B2 (es) |
| KR (1) | KR101362281B1 (es) |
| CN (1) | CN101277937B (es) |
| AR (1) | AR055917A1 (es) |
| AT (1) | ATE520665T1 (es) |
| AU (1) | AU2006273874B2 (es) |
| BR (1) | BRPI0615970A8 (es) |
| CA (1) | CA2616984C (es) |
| CY (1) | CY1111988T1 (es) |
| DK (1) | DK1915346T3 (es) |
| ES (2) | ES2562816T3 (es) |
| GB (1) | GB0515690D0 (es) |
| IL (1) | IL189062A0 (es) |
| MX (1) | MX2008001291A (es) |
| NZ (1) | NZ565462A (es) |
| PL (1) | PL1915346T3 (es) |
| PT (1) | PT103467B (es) |
| RU (1) | RU2439060C2 (es) |
| SI (1) | SI1915346T1 (es) |
| WO (1) | WO2007012793A1 (es) |
| ZA (1) | ZA200800986B (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060252745A1 (en) | 2005-05-06 | 2006-11-09 | Almeida Jose L D | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| GB0515690D0 (en) * | 2005-07-29 | 2005-09-07 | Portela & Ca Sa | Asymmetric catalytic reduction |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| US8372431B2 (en) | 2007-10-26 | 2013-02-12 | Bial-Portela & C.A., S.A. | Pharmaceutical composition comprising licarbazepine acetate |
| EP2414335A4 (en) | 2009-04-02 | 2012-02-08 | Glenmark Generics Ltd | PROCESS FOR PURIFYING ESLICARBAZEPINACETATE |
| EP2459198A1 (en) | 2009-07-27 | 2012-06-06 | Bial-Portela & CA, S.A. | Use of 5h-dibenz / b, f/ azepine-5-carboxamide derivatives for treating fibromyalgia |
| WO2011091131A2 (en) * | 2010-01-23 | 2011-07-28 | Dr. Reddy's Laboratories Ltd. | Eslicarbazepine acetate and its polymorphs |
| EP2383261B1 (en) | 2010-04-23 | 2013-09-04 | Euticals GmbH | Process for the asymmetric hydrogenation of ketones |
| WO2011138795A2 (en) * | 2010-05-03 | 2011-11-10 | Msn Laboratories Limited | Process for preparing (s)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f] azepine-5-carboxamide |
| CN102250005B (zh) * | 2010-05-19 | 2015-04-08 | 浙江九洲药物科技有限公司 | 艾利西平的制备方法 |
| ES2687678T3 (es) | 2011-03-08 | 2018-10-26 | Jubilant Life Sciences Limited | Procedimiento para la preparación de (S)-(+)-10,11-dihidro-10-hidroxi-5H-dibenzo[b,f]azepina-5-carboxamida y ésteres de la misma mediante reducción enantioselectiva de 10,11-dihidro-10-oxo-5H-dibenzo[b,f]azepina-5-carboxamida |
| WO2012142302A2 (en) | 2011-04-13 | 2012-10-18 | Codexis, Inc. | Biocatalytic process for preparing eslicarbazepine and analogs thereof |
| WO2013008194A2 (en) | 2011-07-13 | 2013-01-17 | Ranbaxy Laboratories Limited | Process for the preparation and purification of eslicarbazepine acetate and intermediates thereof |
| US20150232426A1 (en) | 2012-09-26 | 2015-08-20 | Ranbaxy Laboratories Limited | Process for the preparation of oxcarbazepine and its use as intermediate in the preparation of eslicarbazepine acetate |
| EP3042902B1 (en) * | 2013-09-06 | 2018-10-10 | Nippon Soda Co., Ltd. | Method for producing endo-9-azabicyclo[3.3.1]nonan-3-ol derivative |
| EP3064490A1 (en) | 2015-03-06 | 2016-09-07 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of eslicarbazepine and eslicarbazepine acetate |
| WO2018109152A1 (en) | 2016-12-16 | 2018-06-21 | Idorsia Pharmaceuticals Ltd | Pharmaceutical combination comprising a t-type calcium channel blocker |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT101732B (pt) * | 1995-06-30 | 1997-12-31 | Portela & Ca Sa | Novas di-hidrodibenzo<b,f>azepinas substituidas processo para a sua preparacao composicoes farmaceuticas que as contem e utilizacao dos novos compostos na preparacao de composicoes farmaceuticas empregues em doencas do sistema nervoso |
| EP1300381B1 (en) | 1995-12-06 | 2006-03-08 | Japan Science and Technology Agency | Process for preparing optically active alcohols |
| JP2003502296A (ja) | 1999-06-15 | 2003-01-21 | ロディア・シミ | スルホニルアミド及びカルボキサミド並びに不斉触媒作用におけるそれらの使用 |
| GB0111566D0 (en) | 2001-05-11 | 2001-07-04 | Portela & Ca Sa | Method for preparation of (s)-(+)-and (r)-(-)-10,11-dihydro-10-hydroxy-5h-dibenz/b,f/azephine-5-carboxamide |
| GB0112812D0 (en) | 2001-05-25 | 2001-07-18 | Portela & Ca Sa | Mthd for preparation of 10, 11-dihydro-10-hydroxy-5H-dibenz/B,F/azepine-5-c arboxamide and 10,11-dihydro-10-oxo-5H-dibenz/B,F/azepine-5-carb oxamide therefrom |
| JP3504254B2 (ja) | 2001-10-31 | 2004-03-08 | 関東化学株式会社 | 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 |
| US6972275B2 (en) | 2002-06-28 | 2005-12-06 | Exxonmobil Research And Engineering Company | Oil-in-oil emulsion lubricants for enhanced lubrication |
| GB0223224D0 (en) | 2002-10-07 | 2002-11-13 | Novartis Ag | Organic compounds |
| JP4309686B2 (ja) | 2003-01-17 | 2009-08-05 | 関東化学株式会社 | 光学活性化合物の製造方法 |
| GB2401605A (en) | 2003-05-12 | 2004-11-17 | Portela & Ca Sa | Method for racemisation of (S)-(+)- and (R)-(-)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide and optically enriched mixtures thereof |
| CN1328252C (zh) * | 2003-06-12 | 2007-07-25 | 中国科学院成都有机化学研究所 | 新型光学纯水溶性二胺和衍生物及其制备方法和用途 |
| JP4744091B2 (ja) | 2003-09-05 | 2011-08-10 | 関東化学株式会社 | 光学活性ニトロ化合物およびシアノ化合物の製造方法 |
| GB2416167A (en) | 2004-07-13 | 2006-01-18 | Portela & Ca Sa | Chiral inversion and esterification of (S)- and (R)-10-hydroxy-dibenzazepine carboxamides |
| GB2422149A (en) | 2005-01-14 | 2006-07-19 | Portela & Ca Sa | Process for the preparation of 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide |
| GB0515690D0 (en) | 2005-07-29 | 2005-09-07 | Portela & Ca Sa | Asymmetric catalytic reduction |
-
2005
- 2005-07-29 GB GBGB0515690.6A patent/GB0515690D0/en not_active Ceased
-
2006
- 2006-04-21 US US11/997,104 patent/US8288532B2/en active Active
- 2006-04-21 AT AT06726863T patent/ATE520665T1/de active
- 2006-04-21 ES ES11152286.8T patent/ES2562816T3/es active Active
- 2006-04-21 EP EP11152286.8A patent/EP2319836B1/en not_active Not-in-force
- 2006-04-21 ZA ZA200800986A patent/ZA200800986B/xx unknown
- 2006-04-21 CA CA2616984A patent/CA2616984C/en active Active
- 2006-04-21 AU AU2006273874A patent/AU2006273874B2/en not_active Ceased
- 2006-04-21 CN CN2006800364213A patent/CN101277937B/zh not_active Expired - Fee Related
- 2006-04-21 ES ES06726863T patent/ES2371556T3/es active Active
- 2006-04-21 JP JP2008523428A patent/JP5295765B2/ja not_active Expired - Fee Related
- 2006-04-21 KR KR1020087004682A patent/KR101362281B1/ko active Active
- 2006-04-21 MX MX2008001291A patent/MX2008001291A/es active IP Right Grant
- 2006-04-21 WO PCT/GB2006/001473 patent/WO2007012793A1/en not_active Ceased
- 2006-04-21 DK DK06726863.1T patent/DK1915346T3/da active
- 2006-04-21 EP EP06726863A patent/EP1915346B1/en active Active
- 2006-04-21 NZ NZ565462A patent/NZ565462A/en not_active IP Right Cessation
- 2006-04-21 PL PL06726863T patent/PL1915346T3/pl unknown
- 2006-04-21 BR BRPI0615970A patent/BRPI0615970A8/pt not_active Application Discontinuation
- 2006-04-21 SI SI200631160T patent/SI1915346T1/sl unknown
- 2006-04-21 RU RU2008107718/04A patent/RU2439060C2/ru active
- 2006-04-24 PT PT103467A patent/PT103467B/pt active IP Right Grant
- 2006-04-24 AR ARP060101623A patent/AR055917A1/es active IP Right Grant
-
2008
- 2008-01-28 IL IL189062A patent/IL189062A0/en unknown
-
2011
- 2011-11-02 CY CY20111101057T patent/CY1111988T1/el unknown
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2012
- 2012-10-15 US US13/651,844 patent/US9206135B2/en active Active
-
2013
- 2013-04-11 JP JP2013083395A patent/JP2013173764A/ja active Pending
-
2015
- 2015-11-18 US US14/944,546 patent/US9643929B2/en active Active
-
2017
- 2017-03-23 US US15/467,367 patent/US20170190668A1/en not_active Abandoned
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