RU2168502C2 - Замещенные дигидродибенз/b, f/азепины, способ их получения, фармацевтическая композиция, обладающая антиэпилептической активностью - Google Patents
Замещенные дигидродибенз/b, f/азепины, способ их получения, фармацевтическая композиция, обладающая антиэпилептической активностью Download PDFInfo
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- RU2168502C2 RU2168502C2 RU98101463/04A RU98101463A RU2168502C2 RU 2168502 C2 RU2168502 C2 RU 2168502C2 RU 98101463/04 A RU98101463/04 A RU 98101463/04A RU 98101463 A RU98101463 A RU 98101463A RU 2168502 C2 RU2168502 C2 RU 2168502C2
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- Russia
- Prior art keywords
- dibenz
- dihydro
- carboxamide
- azepine
- group
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Images
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT101732 | 1995-06-30 | ||
| PT101732A PT101732B (pt) | 1995-06-30 | 1995-06-30 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98101463A RU98101463A (ru) | 2000-02-10 |
| RU2168502C2 true RU2168502C2 (ru) | 2001-06-10 |
Family
ID=20085522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98101463/04A RU2168502C2 (ru) | 1995-06-30 | 1996-06-27 | Замещенные дигидродибенз/b, f/азепины, способ их получения, фармацевтическая композиция, обладающая антиэпилептической активностью |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5753646A (en:Method) |
| EP (1) | EP0751129B3 (en:Method) |
| JP (2) | JP3852984B2 (en:Method) |
| KR (1) | KR100376603B1 (en:Method) |
| CN (1) | CN1070853C (en:Method) |
| AR (1) | AR003962A1 (en:Method) |
| AT (1) | ATE173468T3 (en:Method) |
| AU (1) | AU705388B2 (en:Method) |
| BR (1) | BRPI9602933B8 (en:Method) |
| CA (1) | CA2180301C (en:Method) |
| DE (2) | DE69600985T3 (en:Method) |
| DK (1) | DK0751129T6 (en:Method) |
| ES (1) | ES2124612T7 (en:Method) |
| FR (1) | FR09C0040I2 (en:Method) |
| HU (1) | HU221382B1 (en:Method) |
| NL (1) | NL300406I1 (en:Method) |
| PL (1) | PL185476B1 (en:Method) |
| PT (1) | PT101732B (en:Method) |
| RU (1) | RU2168502C2 (en:Method) |
| SI (1) | SI0751129T1 (en:Method) |
| TR (1) | TR199701734T1 (en:Method) |
| WO (1) | WO1997002250A1 (en:Method) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2189225C1 (ru) * | 2001-09-14 | 2002-09-20 | Нестерук Владимир Викторович | Лекарственное средство на основе карбамазепина |
| RU2345986C2 (ru) * | 2003-05-12 | 2009-02-10 | Портела Энд К.А., С.А. | СПОСОБ РАЦЕМИЗАЦИИ (S)-(+) И (R)-(-)-10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ(b, f)АЗЕПИН-5-КАРБОКСАМИДА И ИХ ОПТИЧЕСКИ ОБОГАЩЕННЫХ СМЕСЕЙ |
| RU2351338C2 (ru) * | 2003-04-01 | 2009-04-10 | Новартис Аг | Применение производных карбамазепина для лечения возбуждения у пациентов, страдающих деменцией |
| RU2382772C2 (ru) * | 2004-07-13 | 2010-02-27 | Биал-Портела Энд Ка. С.А. | СПОСОБ ОБРАЩЕНИЯ (S)-(+)- И (R)-(-)-10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b, f/АЗЕПИН-5-КАРБОКСАМИДА И ИХ ОПТИЧЕСКИ ОБОГАЩЕННЫХ СМЕСЕЙ |
| RU2418789C2 (ru) * | 2005-01-14 | 2011-05-20 | Биал-Портела Энд К.А., С.А. | СПОСОБ ПОЛУЧЕНИЯ 10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b, f/АЗЕПИН-5-КАРБОКСАМИДА |
| RU2439060C2 (ru) * | 2005-07-29 | 2012-01-10 | Биал-Портела Энд Ка, С.А. | Асимметрическое каталитическое восстановление окскарбазепина |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9930058D0 (en) | 1999-12-20 | 2000-02-09 | Novartis Ag | Organic compounds |
| 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 |
| PT1446383E (pt) * | 2001-11-12 | 2008-12-29 | Novartis Ag | Mono-hidroxicarbamazepina para uso na preparação de um medicamento para o tratamento de perturbações do foro afectivo e perturbações da atenção e dores neuropáticas |
| EP1528927A1 (en) | 2002-08-06 | 2005-05-11 | Novartis AG | Use of carboxamides for the treatment of tinnitus |
| GB0223224D0 (en) * | 2002-10-07 | 2002-11-13 | Novartis Ag | Organic compounds |
| GB0303613D0 (en) * | 2003-02-17 | 2003-03-19 | Novartis Ag | Use of organic compounds |
| BRPI0407569A (pt) * | 2003-02-17 | 2006-02-14 | Novartis Ag | uso de s-10-hidróxi-10, 11-diidro-carbamazepina para o tratamento de ansiendade e distúrbios bipolares |
| TW200502222A (en) | 2003-04-02 | 2005-01-16 | Novartis Ag | Use of 10-hydroxy-10,11-dihydrocarbamazepine derivatives for the treatment of affective disorders |
| ITMI20042230A1 (it) * | 2004-11-19 | 2005-02-19 | Farchemia Srl | Procedimento per la preparazione della 10,11-diidro-10 idrossi-5h-dibenz-b,f-azepin-5carbossiammide |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| JP2008540405A (ja) * | 2005-05-06 | 2008-11-20 | ポルテラ・アンド・シーエー・エスエー | 酢酸エスリカルバゼピン及び使用方法 |
| RU2417085C2 (ru) * | 2005-05-06 | 2011-04-27 | Биал-Портела Энд Ка, С.А. | Эсликарбазепина ацетат и способы его применения |
| US20060252745A1 (en) | 2005-05-06 | 2006-11-09 | Almeida Jose L D | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| WO2006120501A1 (en) * | 2005-05-06 | 2006-11-16 | Portela & C.A., S.A. | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| GB0517740D0 (en) * | 2005-08-31 | 2005-10-12 | Novartis Ag | Organic compounds |
| GB0603008D0 (en) * | 2006-02-14 | 2006-03-29 | Portela & Ca Sa | Method |
| GB2437078A (en) * | 2006-04-11 | 2007-10-17 | Portela & Ca Sa | 10-Acyloxy-5H-dibenzo[b,f]azepine-5-carboxamides & their asymmetric hydrogenation to the chiral 10,11-dihydro derivatives |
| 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 |
| US20120022047A1 (en) | 2009-04-02 | 2012-01-26 | Glenmark Generics Ltd | Process for the purification of eslicarbazepine acetate |
| UA106384C2 (ru) * | 2009-07-27 | 2014-08-26 | БИАЛ-ПОРТЕЛА энд КА., С.А. | ПРИМЕНЕНИЕ ПРОИЗВОДНЫХ 5H-ДИБЕНЗ/б,ф/АЗЕПИН-5-КАРБОКСАМИДА ДЛЯ ЛЕЧЕНИЯ ФИБРОМИАЛГИИ |
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| MX350531B (es) | 2010-12-31 | 2017-09-08 | BIAL PORTELA & Cª S A | Granulados que comprenden acetato de eslicarbazepina. |
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| 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 |
| US9102963B2 (en) | 2011-04-13 | 2015-08-11 | 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 |
| US9750747B2 (en) | 2011-08-26 | 2017-09-05 | Bail-Portela & Ca, S.A. | Treatments involving eslicarbazepine acetate or eslicarbazepine |
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| WO2014049550A1 (en) | 2012-09-26 | 2014-04-03 | Ranbaxy Laboratories Limited | Process for the preparation of oxcarbazepine and its use as intermediate in the preparation of eslicarbazepine acetate |
| EP3240779B1 (en) * | 2014-09-26 | 2020-10-28 | Cellixbio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| CN105384689B (zh) * | 2014-12-24 | 2017-10-31 | 开封制药(集团)有限公司 | 一种改进的醋酸艾司利卡西平的合成方法 |
| 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 |
| CN105130899A (zh) * | 2015-08-25 | 2015-12-09 | 安徽省新星药物开发有限责任公司 | 一种醋酸艾司利卡西平的合成方法 |
| ES2903037T3 (es) | 2015-12-18 | 2022-03-30 | Jubilant Generics Ltd | Formas de dosificación orales sólidas de eslicarbazepina |
| CN106588773B (zh) * | 2016-11-10 | 2019-09-27 | 北京现代药物代谢研究院 | 一种脑靶向艾司利卡西平酯类前药及其应用 |
| BR112021005955A2 (pt) | 2018-09-28 | 2021-07-27 | Griffith University | agentes e métodos para modular atividade de patógeno |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310120A (en) * | 1969-03-31 | 1973-03-14 | Ciba Geigy Ag | Azepine derivative its preparation and composition containing it |
| SU1650008A3 (ru) * | 1988-07-12 | 1991-05-15 | Циба-Гейги Аг (Фирма) | Способ получени 1,5-дибенз[ @ , @ ]-азепин-5-карбоксамида |
| US5466683A (en) * | 1994-08-25 | 1995-11-14 | Teva Pharmaceutical Industries Ltd. | Water-soluble analogs of carbamazepine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH500196A (de) * | 1969-03-10 | 1970-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Azepinderivaten |
| FI75561C (fi) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av 5- karbamoyl-10-oxo-10,11-dihydro-5h-dibens/b,f/azepin och daertill noedvaendiga mellanprodukter. |
| CH649080A5 (de) * | 1981-04-16 | 1985-04-30 | Ciba Geigy Ag | 5h-dibenz(b,f)azepin-5-carboxamide als mittel zur prophylaxe und behandlung von zerebraler leistungsinsuffizienz. |
| DD218889B3 (de) * | 1983-11-09 | 1992-11-05 | Dresden Arzneimittel | Verfahren zur herstellung neuer 5-carbamoyl-10,11-dihydro-5h-dibenz|b,f¨azepine |
-
1995
- 1995-06-30 PT PT101732A patent/PT101732B/pt not_active IP Right Cessation
-
1996
- 1996-06-27 AU AU63106/96A patent/AU705388B2/en not_active Expired
- 1996-06-27 RU RU98101463/04A patent/RU2168502C2/ru active Protection Beyond IP Right Term
- 1996-06-27 US US08/673,819 patent/US5753646A/en not_active Expired - Lifetime
- 1996-06-27 AR ARP960103352A patent/AR003962A1/es active IP Right Grant
- 1996-06-27 PL PL96324313A patent/PL185476B1/pl unknown
- 1996-06-27 TR TR97/01734T patent/TR199701734T1/xx unknown
- 1996-06-27 KR KR1019970709780A patent/KR100376603B1/ko not_active Expired - Lifetime
- 1996-06-27 CN CN96196397A patent/CN1070853C/zh not_active Expired - Lifetime
- 1996-06-27 WO PCT/GB1996/001565 patent/WO1997002250A1/en active IP Right Grant
- 1996-06-27 HU HU9900172A patent/HU221382B1/hu active Protection Beyond IP Right Term
- 1996-06-28 AT AT96110490T patent/ATE173468T3/de unknown
- 1996-06-28 DK DK96110490.8T patent/DK0751129T6/da active
- 1996-06-28 EP EP96110490.8A patent/EP0751129B3/en not_active Expired - Lifetime
- 1996-06-28 BR BRPI9602933A patent/BRPI9602933B8/pt not_active IP Right Cessation
- 1996-06-28 DE DE69600985.4T patent/DE69600985T3/de not_active Expired - Lifetime
- 1996-06-28 DE DE122009000049C patent/DE122009000049I2/de active Active
- 1996-06-28 ES ES96110490T patent/ES2124612T7/es active Active
- 1996-06-28 SI SI9630030T patent/SI0751129T1/xx unknown
- 1996-07-01 JP JP17146096A patent/JP3852984B2/ja not_active Expired - Lifetime
- 1996-07-02 CA CA002180301A patent/CA2180301C/en not_active Expired - Lifetime
-
2003
- 2003-12-25 JP JP2003428815A patent/JP2004256516A/ja active Pending
-
2009
- 2009-08-26 FR FR09C0040C patent/FR09C0040I2/fr active Active
- 2009-08-26 NL NL300406C patent/NL300406I1/nl unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310120A (en) * | 1969-03-31 | 1973-03-14 | Ciba Geigy Ag | Azepine derivative its preparation and composition containing it |
| SU1650008A3 (ru) * | 1988-07-12 | 1991-05-15 | Циба-Гейги Аг (Фирма) | Способ получени 1,5-дибенз[ @ , @ ]-азепин-5-карбоксамида |
| US5466683A (en) * | 1994-08-25 | 1995-11-14 | Teva Pharmaceutical Industries Ltd. | Water-soluble analogs of carbamazepine |
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| RU2189225C1 (ru) * | 2001-09-14 | 2002-09-20 | Нестерук Владимир Викторович | Лекарственное средство на основе карбамазепина |
| RU2351338C2 (ru) * | 2003-04-01 | 2009-04-10 | Новартис Аг | Применение производных карбамазепина для лечения возбуждения у пациентов, страдающих деменцией |
| RU2345986C2 (ru) * | 2003-05-12 | 2009-02-10 | Портела Энд К.А., С.А. | СПОСОБ РАЦЕМИЗАЦИИ (S)-(+) И (R)-(-)-10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ(b, f)АЗЕПИН-5-КАРБОКСАМИДА И ИХ ОПТИЧЕСКИ ОБОГАЩЕННЫХ СМЕСЕЙ |
| RU2382772C2 (ru) * | 2004-07-13 | 2010-02-27 | Биал-Портела Энд Ка. С.А. | СПОСОБ ОБРАЩЕНИЯ (S)-(+)- И (R)-(-)-10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b, f/АЗЕПИН-5-КАРБОКСАМИДА И ИХ ОПТИЧЕСКИ ОБОГАЩЕННЫХ СМЕСЕЙ |
| RU2418789C2 (ru) * | 2005-01-14 | 2011-05-20 | Биал-Портела Энд К.А., С.А. | СПОСОБ ПОЛУЧЕНИЯ 10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b, f/АЗЕПИН-5-КАРБОКСАМИДА |
| RU2439060C2 (ru) * | 2005-07-29 | 2012-01-10 | Биал-Портела Энд Ка, С.А. | Асимметрическое каталитическое восстановление окскарбазепина |
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