BRPI0615970A8 - Processo para preparar (s) (+)-10,11-dihidro-10-hidróxi-5h-dibenz/b,f/azepina-5-carboxamida, processo para preparar (s) - (-) -10-acetoxi-10,11 -dihidro-5h-dibenz/b,f/azepina-5-carboxamida e processo para preparar (r) - (+)-10-acetoxi-10,11-dihidro-5h-dibenz/b,f/azepina-5-carboxamida - Google Patents
Processo para preparar (s) (+)-10,11-dihidro-10-hidróxi-5h-dibenz/b,f/azepina-5-carboxamida, processo para preparar (s) - (-) -10-acetoxi-10,11 -dihidro-5h-dibenz/b,f/azepina-5-carboxamida e processo para preparar (r) - (+)-10-acetoxi-10,11-dihidro-5h-dibenz/b,f/azepina-5-carboxamidaInfo
- Publication number
- BRPI0615970A8 BRPI0615970A8 BRPI0615970A BRPI0615970A BRPI0615970A8 BR PI0615970 A8 BRPI0615970 A8 BR PI0615970A8 BR PI0615970 A BRPI0615970 A BR PI0615970A BR PI0615970 A BRPI0615970 A BR PI0615970A BR PI0615970 A8 BRPI0615970 A8 BR PI0615970A8
- Authority
- BR
- Brazil
- Prior art keywords
- carboxamide
- azepine
- preparing
- dibenz
- dihydro
- Prior art date
Links
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 6
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 235000019253 formic acid Nutrition 0.000 abstract 3
- 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
- 238000000034 method Methods 0.000 abstract 2
- 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
- 125000003545 alkoxy 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
- 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)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Abstract
PROCESSO PARA PREPARAR (S) (+) lO,11-DIHIDROlO-HIDROXI-5H-DIBENZ/B, F/AZEPINA-5-CARBOXAMIDA, PROCESSO PARA PREPARAR(S) - (-) -10-ACETOXI-lO,llDIHIDRO5HDIBENZ/B,F/ AZEPINA-5-CARBOXAMIDA E PROCESSO PARA PREPARAR(R) - (+) -10-- ACETOXI-lO, 5H-DIHIDRO-5H~DIBENZ/B,F/AzEPINA-5- CARBOXAMIDA. É divulgado um processo para preparar (S)-(+)-lO,l1- dihidro- 10 -hidroxi-5H-dibeflZ/b, f/azepina-5-carboxamida, ou (R) - (-) -5-carboxamida, por redução de oxcarbazepifla na presença de um catalisador e uma fonte de hidreto. O catalisador é preparado a partir de uma combinação de [RuX~ 2~(L)]~ 2~ sendo que X é cloro, bromo ou iodo, e L é um ligante arila ou aril-alifático, com o ligante de fórmula (A) ou fórmula (B) onde R^ 1^ é selecionado de alcóxi e alquila C~ 1- 6~, n é um número de O a 5, e quando n é um número de 2 a 5, R^1^ poderá ser igual ou diferente, e R^ 2^ é alquila, alquila substituído, arila, arila substituído, alcarila ou alcarila substituído. A fonte de hidreto é ou NR3R4R5 e ácido fórmico, ou [R^ 3^R^ 4^R^ 5^NH] [OOCH] e opcionalmente ácido fórmico, ou [Ml [OOCH]X e ácido fórmico, sendo que R^ 3^, R^ 4^ e R^ 5^ são alquila C~ 1- 6~M é um metal alcalino ou um metal alcalino-terroso e x é 1 ou 2. É mantido um pH de 6,5 a 8 durante o processo.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0515690.6 | 2005-07-29 | ||
| GBGB0515690.6A GB0515690D0 (en) | 2005-07-29 | 2005-07-29 | Asymmetric catalytic reduction |
| PCT/GB2006/001473 WO2007012793A1 (en) | 2005-07-29 | 2006-04-21 | Asymmetric catalytic reduction of oxcarbazepine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0615970A2 BRPI0615970A2 (pt) | 2011-05-31 |
| BRPI0615970A8 true BRPI0615970A8 (pt) | 2017-08-22 |
Family
ID=34983785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0615970A BRPI0615970A8 (pt) | 2005-07-29 | 2006-04-21 | Processo para preparar (s) (+)-10,11-dihidro-10-hidróxi-5h-dibenz/b,f/azepina-5-carboxamida, processo para preparar (s) - (-) -10-acetoxi-10,11 -dihidro-5h-dibenz/b,f/azepina-5-carboxamida e processo para preparar (r) - (+)-10-acetoxi-10,11-dihidro-5h-dibenz/b,f/azepina-5-carboxamida |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US8288532B2 (pt) |
| EP (2) | EP1915346B1 (pt) |
| JP (2) | JP5295765B2 (pt) |
| KR (1) | KR101362281B1 (pt) |
| CN (1) | CN101277937B (pt) |
| AR (1) | AR055917A1 (pt) |
| AT (1) | ATE520665T1 (pt) |
| AU (1) | AU2006273874B2 (pt) |
| BR (1) | BRPI0615970A8 (pt) |
| CA (1) | CA2616984C (pt) |
| CY (1) | CY1111988T1 (pt) |
| DK (1) | DK1915346T3 (pt) |
| ES (2) | ES2371556T3 (pt) |
| GB (1) | GB0515690D0 (pt) |
| IL (1) | IL189062A0 (pt) |
| MX (1) | MX2008001291A (pt) |
| NZ (1) | NZ565462A (pt) |
| PL (1) | PL1915346T3 (pt) |
| PT (1) | PT103467B (pt) |
| RU (1) | RU2439060C2 (pt) |
| SI (1) | SI1915346T1 (pt) |
| WO (1) | WO2007012793A1 (pt) |
| ZA (1) | ZA200800986B (pt) |
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 |
| RU2012106827A (ru) | 2009-07-27 | 2013-09-10 | БИАЛ-ПОРТЕЛА энд КА., С.А. | Применение производных 5н-дибенз/в, f/азепин-5-карбоксамида для лечения фибромиалгии |
| 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 |
| WO2012120356A2 (en) | 2011-03-08 | 2012-09-13 | Jubilant Life Sciences Limited | Process for the preparation of (s)-(+)-or (r)-(-)-10 hydroxy dihydrodibenz[b,f]azepines by enantioselective reduction of 10, 11-dihydro-10-oxo-5h-dibenz[b,f]azepines and polymorphs thereof |
| HUE038800T2 (hu) | 2011-04-13 | 2018-11-28 | Codexis Inc | Biokatalitikus eljárás eszlikarbazepin és ennek analógjai elõállítására |
| US20150065704A1 (en) | 2011-07-13 | 2015-03-05 | Ketan Hirpara | Process for the preparation and purification of eslicarbazepine acetate and intermediates thereof |
| IN2015DN02296A (pt) | 2012-09-26 | 2015-08-21 | Ranbaxy Lab Ltd | |
| 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 |
| MX388586B (es) | 2016-12-16 | 2025-03-20 | Idorsia Pharmaceuticals Ltd | Combinacion farmaceutica que comprende un bloqueador del canal de calcio de tipo t. |
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 |
| WO1997020789A1 (en) | 1995-12-06 | 1997-06-12 | Japan Science And Technology Corporation | Process for preparating optically active compounds |
| 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 AT AT06726863T patent/ATE520665T1/de active
- 2006-04-21 NZ NZ565462A patent/NZ565462A/en not_active IP Right Cessation
- 2006-04-21 BR BRPI0615970A patent/BRPI0615970A8/pt not_active Application Discontinuation
- 2006-04-21 AU AU2006273874A patent/AU2006273874B2/en not_active Ceased
- 2006-04-21 CA CA2616984A patent/CA2616984C/en not_active Expired - Lifetime
- 2006-04-21 PL PL06726863T patent/PL1915346T3/pl unknown
- 2006-04-21 KR KR1020087004682A patent/KR101362281B1/ko not_active Expired - Lifetime
- 2006-04-21 MX MX2008001291A patent/MX2008001291A/es active IP Right Grant
- 2006-04-21 DK DK06726863.1T patent/DK1915346T3/da active
- 2006-04-21 SI SI200631160T patent/SI1915346T1/sl unknown
- 2006-04-21 JP JP2008523428A patent/JP5295765B2/ja not_active Expired - Fee Related
- 2006-04-21 CN CN2006800364213A patent/CN101277937B/zh not_active Expired - Fee Related
- 2006-04-21 US US11/997,104 patent/US8288532B2/en active Active
- 2006-04-21 EP EP06726863A patent/EP1915346B1/en not_active Expired - Lifetime
- 2006-04-21 ES ES06726863T patent/ES2371556T3/es not_active Expired - Lifetime
- 2006-04-21 EP EP11152286.8A patent/EP2319836B1/en not_active Expired - Lifetime
- 2006-04-21 WO PCT/GB2006/001473 patent/WO2007012793A1/en not_active Ceased
- 2006-04-21 ZA ZA200800986A patent/ZA200800986B/xx unknown
- 2006-04-21 ES ES11152286.8T patent/ES2562816T3/es not_active Expired - Lifetime
- 2006-04-21 RU RU2008107718/04A patent/RU2439060C2/ru active
- 2006-04-24 AR ARP060101623A patent/AR055917A1/es active IP Right Grant
- 2006-04-24 PT PT103467A patent/PT103467B/pt active IP Right Grant
-
2008
- 2008-01-28 IL IL189062A patent/IL189062A0/en unknown
-
2011
- 2011-11-02 CY CY20111101057T patent/CY1111988T1/el unknown
-
2012
- 2012-10-15 US US13/651,844 patent/US9206135B2/en not_active Expired - Lifetime
-
2013
- 2013-04-11 JP JP2013083395A patent/JP2013173764A/ja active Pending
-
2015
- 2015-11-18 US US14/944,546 patent/US9643929B2/en not_active Expired - Lifetime
-
2017
- 2017-03-23 US US15/467,367 patent/US20170190668A1/en not_active Abandoned
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