RU2007130909A - СПОСОБ ПОЛУЧЕНИЯ 10, 11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b,f/АЗЕПИН-5-КАРБОКСАМИДА - Google Patents
СПОСОБ ПОЛУЧЕНИЯ 10, 11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b,f/АЗЕПИН-5-КАРБОКСАМИДА Download PDFInfo
- Publication number
- RU2007130909A RU2007130909A RU2007130909/04A RU2007130909A RU2007130909A RU 2007130909 A RU2007130909 A RU 2007130909A RU 2007130909/04 A RU2007130909/04 A RU 2007130909/04A RU 2007130909 A RU2007130909 A RU 2007130909A RU 2007130909 A RU2007130909 A RU 2007130909A
- Authority
- RU
- Russia
- Prior art keywords
- dibenz
- carboxamide
- dihydro
- azepine
- hydroxy
- 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 claims 15
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 18
- 238000007142 ring opening reaction Methods 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- JQZDXPWBGFOGCX-UHFFFAOYSA-N 8-oxa-4-azabicyclo[5.1.0]octa-1(7),2,5-triene-6-carboxamide Chemical compound NC(=O)C1=CNC=CC2=C1O2 JQZDXPWBGFOGCX-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (15)
1. Способ получения 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида (1) путем раскрытия кольца 11a,10b-дигидро-6H-дибенз/b,f/оксирено[d]азепин-6-карбоксамида (5), отличающийся тем, что раскрытие кольца осуществляют в условиях повышенного давления.
2. Способ по п.1, где раскрытие кольца осуществляют путем каталитического гидрирования с помощью газообразного водорода при повышенном давлении в присутствии катализатора.
3. Способ по п.1 или 2, где давление составляет от 200 кПа до 4,0 МПа.
4. Способ по п.1 или 2, где давление составляет от 1,0 до 1,5 МПа.
5. Способ по п.1 или 2, где взаимодействие осуществляют при температуре от 40 до 65°C.
6. Способ по п.1 или 2, где взаимодействие осуществляют при температуре от 50 до 60°C.
7. Способ по п.1 или 2, где реакцию раскрытия кольца осуществляют в присутствии металлического катализатора.
8. Способ по п.7, где металлический катализатор, используемый в реакции раскрытия кольца, представляет собой палладий в количестве 0,001-0,01 мол.% в расчете на количество 11a,10b-дигидро-6H-дибенз/b,f/оксирено[d]азепин-6-карбоксамида (5).
9. Способ по п.1 или 2, где реакцию раскрытия кольца осуществляют в присутствии органического основания, которым является триалкиламин.
10. Способ по п.1 или 2, где реакцию раскрытия кольца осуществляют в растворителе, который выбирают из группы, включающей хлорированные углеводороды, спирты с 1-6 атомами углерода и воду, либо смеси указанных соединений.
11. Способ по п.1 или 2, где реакцию раскрытия кольца осуществляют в присутствии метанола, воды и триэтиламина.
12. Способ получения 10,11-дигидро-10-оксо-5H-дибенз/b,f/азепин-5-карбоксамида (2), включающий получение 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида (1) способом по любому из пп.1-11, последующее окисление 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида (1) путем взаимодействия с пероксиуксусной кислотой в присутствии металлического катализатора в практически инертном растворителе.
13. Способ получения соединения формулы (6):
где R1 означает водород, алкил, галогеналкил, аралкил, циклоалкил, циклоалкилалкил, алкокси, арил или пиридил; термин алкил означает линейную или разветвленную углеводородную цепь, содержащую от 1 до 18 атомов углерода; термин галоген означает фтор, хлор, бром или йод; термин циклоалкил означает алициклическую насыщенную группу с 3-6 атомами углерода; и термин арил означает незамещенную фенильную группу или фенил, замещенный алкокси, галогеном или нитрогруппой, включающий получение 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида (1) способом по любому из пп.1-11, последующую обработку 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида (1), приводящую к получению соединения формулы (6).
14. Способ по п.13, где соединение формулы (6) получают ацилированием 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида.
15. Способ получения 10-ацетокси-10,11-дигидро-5H-дибенз/b,f/азепин-5-карбоксамида, включающий получение 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида способом по любому из пп.1-11, затем ацилирование 10,11-дигидро-10-гидрокси-5H-дибенз/b,f/азепин-5-карбоксамида с помощью ацетилхлорида.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0500815A GB2422149A (en) | 2005-01-14 | 2005-01-14 | Process for the preparation of 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide |
| GB0500815.6 | 2005-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007130909A true RU2007130909A (ru) | 2009-02-20 |
| RU2418789C2 RU2418789C2 (ru) | 2011-05-20 |
Family
ID=34224635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007130909/04A RU2418789C2 (ru) | 2005-01-14 | 2006-01-13 | СПОСОБ ПОЛУЧЕНИЯ 10,11-ДИГИДРО-10-ГИДРОКСИ-5Н-ДИБЕНЗ/b, f/АЗЕПИН-5-КАРБОКСАМИДА |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7834177B2 (ru) |
| EP (1) | EP1846376B1 (ru) |
| JP (1) | JP5634660B2 (ru) |
| KR (1) | KR20070107036A (ru) |
| CN (1) | CN101142191B (ru) |
| AR (1) | AR052874A1 (ru) |
| AU (1) | AU2006205280A1 (ru) |
| BR (1) | BRPI0606252B8 (ru) |
| CA (1) | CA2594869C (ru) |
| CY (1) | CY1114858T1 (ru) |
| DK (1) | DK1846376T3 (ru) |
| ES (1) | ES2441794T3 (ru) |
| GB (1) | GB2422149A (ru) |
| MX (1) | MX2007008499A (ru) |
| PL (1) | PL1846376T3 (ru) |
| PT (1) | PT1846376E (ru) |
| RU (1) | RU2418789C2 (ru) |
| SI (1) | SI1846376T1 (ru) |
| WO (1) | WO2006075925A2 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2026815B1 (en) | 2006-04-26 | 2011-01-26 | Supernus Pharmaceuticals, Inc. | Controlled released preparations of oxcarbazepine having sigmoidal release profile |
| US9744137B2 (en) | 2006-08-31 | 2017-08-29 | Supernus Pharmaceuticals, Inc. | Topiramate compositions and methods of enhancing its bioavailability |
| WO2008061226A2 (en) | 2006-11-17 | 2008-05-22 | Supernus Pharmaceuticals Inc. | Sustained-release formulations of topiramate |
| 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 |
| CA2769181C (en) | 2009-07-27 | 2017-11-28 | Bial-Portela & Ca., S.A. | Use of 5h-dibenz / b, f/ azepine-5-carboxamide derivatives for treating fibromyalgia |
| WO2011117885A1 (en) * | 2010-03-23 | 2011-09-29 | Intas Pharmaceuticals Limited | Process for preparation of enantiomers of licarbazepine |
| 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 |
| CN106699661B (zh) * | 2016-11-22 | 2019-04-09 | 大连理工大学 | 一种二苯并[c，e]氮杂-5,7(6H)-二酮化合物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789320A (fr) | 1971-09-30 | 1973-03-27 | Takeda Chemical Industries Ltd | Derives de dibenzoxirenazepine |
| CH633271A5 (en) | 1978-04-18 | 1982-11-30 | Ciba Geigy Ag | Process for the rearrangement of 10,11-epoxy-10,11-dihydro-5H-dibenz[b,f]azepines to give 10-oxo-10,11-dihydro-5H-dibenz(b,f)azepines |
| CH642950A5 (en) | 1979-10-30 | 1984-05-15 | Ciba Geigy Ag | Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide |
| HUT63390A (en) | 1991-12-27 | 1993-08-30 | Alkaloida Vegyeszeti Gyar | Improved process for producing 5-carbamoyl-10-oxo-10,11-dihydro-5h-dibenz/b,f/azepine |
| IT1272897B (it) | 1995-01-13 | 1997-07-01 | I F C Iniziative Finanziaarie | Processo per la produzione di 10-oxo-10,11-diidro-sh- -dibenz(b,f) azepin-5-carbossiammide |
| 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 |
| IT1283594B1 (it) | 1996-04-12 | 1998-04-22 | Trifarma Srl | Derivati della 5h-dibenz- (b,f)-azepin-5-carbossiammide, loro preparazione e uso come sostanze ad azione medicinale |
| AT408224B (de) | 1999-03-15 | 2001-09-25 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von oxcarbazepin |
| 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 |
| 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 |
-
2005
- 2005-01-14 GB GB0500815A patent/GB2422149A/en not_active Withdrawn
-
2006
- 2006-01-13 BR BRPI0606252A patent/BRPI0606252B8/pt not_active IP Right Cessation
- 2006-01-13 PL PL06700407T patent/PL1846376T3/pl unknown
- 2006-01-13 AU AU2006205280A patent/AU2006205280A1/en not_active Abandoned
- 2006-01-13 CA CA2594869A patent/CA2594869C/en active Active
- 2006-01-13 ES ES06700407.7T patent/ES2441794T3/es active Active
- 2006-01-13 SI SI200631719T patent/SI1846376T1/sl unknown
- 2006-01-13 RU RU2007130909/04A patent/RU2418789C2/ru active
- 2006-01-13 WO PCT/PT2006/000002 patent/WO2006075925A2/en active Application Filing
- 2006-01-13 MX MX2007008499A patent/MX2007008499A/es not_active Application Discontinuation
- 2006-01-13 AR ARP060100152A patent/AR052874A1/es unknown
- 2006-01-13 EP EP06700407.7A patent/EP1846376B1/en active Active
- 2006-01-13 KR KR1020077018422A patent/KR20070107036A/ko not_active Application Discontinuation
- 2006-01-13 CN CN200680008363.3A patent/CN101142191B/zh not_active Expired - Fee Related
- 2006-01-13 DK DK06700407.7T patent/DK1846376T3/da active
- 2006-01-13 PT PT67004077T patent/PT1846376E/pt unknown
- 2006-01-13 JP JP2007551215A patent/JP5634660B2/ja not_active Expired - Fee Related
- 2006-01-13 US US11/813,938 patent/US7834177B2/en active Active
-
2014
- 2014-01-07 CY CY20141100011T patent/CY1114858T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2418789C2 (ru) | 2011-05-20 |
| BRPI0606252B1 (pt) | 2020-12-08 |
| AU2006205280A1 (en) | 2006-07-20 |
| WO2006075925A2 (en) | 2006-07-20 |
| DK1846376T3 (da) | 2014-01-20 |
| CN101142191A (zh) | 2008-03-12 |
| AR052874A1 (es) | 2007-04-11 |
| JP2008526960A (ja) | 2008-07-24 |
| CA2594869A1 (en) | 2006-07-20 |
| MX2007008499A (es) | 2007-09-07 |
| EP1846376B1 (en) | 2013-10-09 |
| GB2422149A (en) | 2006-07-19 |
| PT1846376E (pt) | 2014-01-10 |
| CN101142191B (zh) | 2011-07-06 |
| EP1846376A2 (en) | 2007-10-24 |
| CA2594869C (en) | 2014-12-23 |
| US20080139807A1 (en) | 2008-06-12 |
| BRPI0606252A8 (pt) | 2018-03-13 |
| ES2441794T3 (es) | 2014-02-06 |
| SI1846376T1 (sl) | 2014-03-31 |
| JP5634660B2 (ja) | 2014-12-03 |
| US7834177B2 (en) | 2010-11-16 |
| KR20070107036A (ko) | 2007-11-06 |
| PL1846376T3 (pl) | 2014-03-31 |
| GB0500815D0 (en) | 2005-02-23 |
| CY1114858T1 (el) | 2016-12-14 |
| WO2006075925A3 (en) | 2006-08-24 |
| BRPI0606252A2 (pt) | 2009-06-09 |
| BRPI0606252B8 (pt) | 2021-05-25 |
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