NO130314B - - Google Patents
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- Publication number
- NO130314B NO130314B NO00756/70*[A NO75670A NO130314B NO 130314 B NO130314 B NO 130314B NO 75670 A NO75670 A NO 75670A NO 130314 B NO130314 B NO 130314B
- Authority
- NO
- Norway
- Prior art keywords
- azepine
- dibenz
- carboxamide
- pentetrazole
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010043994 Tonic convulsion Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PIZOFBKQWNPKDK-UHFFFAOYSA-N 5-methoxybenzo[b][1]benzazepine-11-carboxamide Chemical compound COC1=CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C12 PIZOFBKQWNPKDK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010053398 Clonic convulsion Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000004279 orbit Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 1
- ANRYPESGCUZAHS-UHFFFAOYSA-N 5-methoxybenzo[b][1]benzazepine-11-carbonyl chloride Chemical compound COC1=CC2=CC=CC=C2N(C(Cl)=O)C2=CC=CC=C12 ANRYPESGCUZAHS-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- KNAHARQHSZJURB-UHFFFAOYSA-N Propylthiouracile Chemical compound CCCC1=CC(=O)NC(=S)N1 KNAHARQHSZJURB-UHFFFAOYSA-N 0.000 description 1
- 208000012545 Psychophysiologic disease Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002635 electroconvulsive therapy Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940090016 tegretol Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH358369A CH500196A (de) | 1969-03-10 | 1969-03-10 | Verfahren zur Herstellung von neuen Azepinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130314B true NO130314B (sv) | 1974-08-12 |
Family
ID=4259115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00756/70*[A NO130314B (sv) | 1969-03-10 | 1970-03-03 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US3642775A (sv) |
| AT (1) | AT298492B (sv) |
| BE (1) | BE747085A (sv) |
| BG (1) | BG17576A3 (sv) |
| BR (1) | BR7017332D0 (sv) |
| CA (1) | CA920586A (sv) |
| CH (1) | CH500196A (sv) |
| CS (1) | CS154294B2 (sv) |
| DE (1) | DE2011087C3 (sv) |
| DK (1) | DK125649B (sv) |
| ES (1) | ES377279A1 (sv) |
| FI (1) | FI50523C (sv) |
| FR (1) | FR2034781B1 (sv) |
| GB (1) | GB1310571A (sv) |
| HK (1) | HK51976A (sv) |
| IE (1) | IE34046B1 (sv) |
| IL (1) | IL34026A (sv) |
| KE (1) | KE2635A (sv) |
| MY (1) | MY7600194A (sv) |
| NL (1) | NL162904C (sv) |
| NO (1) | NO130314B (sv) |
| PL (1) | PL80549B1 (sv) |
| SE (1) | SE349301B (sv) |
| YU (1) | YU33862B (sv) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI75561C (sv) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Förfarande för framställning av 5-karbamoyl-10-oxo-10,11-dihydro-5H-di bens/b,f/azepin och därtill nödvändiga mellanprodukter. |
| EP0108715A1 (de) * | 1982-10-15 | 1984-05-16 | Ciba-Geigy Ag | Dibenzazepincarboxamide |
| FR2700117B1 (fr) * | 1993-01-07 | 1995-02-03 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement de la maladie de Parkinson et des syndromes parkinsoniens. |
| US5472714A (en) * | 1993-09-08 | 1995-12-05 | Ciba-Geigy Corporation | Double-layered oxcarbazepine tablets |
| 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 |
| PT101876B (pt) * | 1996-05-27 | 1999-09-30 | Portela & Ca Sa | Novos derivados de 10,11-di-hidro-10-oxo-5h-dibenzo(b,f)azepina-5-carboxamida |
| US20020022056A1 (en) * | 1997-02-14 | 2002-02-21 | Burkhard Schlutermann | Oxacarbazepine film-coated tablets |
| DE59902734D1 (de) | 1998-11-25 | 2002-10-24 | Dsm Fine Chem Austria Gmbh | Verfahren zur Oxidation von Methyl-, Methylen- oder Methingruppen enthaltenden Substraten |
| AT406957B (de) * | 1998-11-25 | 2000-11-27 | Dsm Fine Chem Austria Gmbh | Verfahren zur oxidation von methyl-, methylen- oder methingruppen enthaltenden substraten |
| GB9930058D0 (en) | 1999-12-20 | 2000-02-09 | Novartis Ag | Organic compounds |
| IT1317854B1 (it) * | 2000-02-25 | 2003-07-15 | Farchemia Srl | 5-ciano-10-idrossi-10,11-diidro-5h-dibenz(b,f)azepina e procedimentiper la sua preparazione e per la sua conversione in |
| WO2002064557A2 (en) * | 2001-02-12 | 2002-08-22 | Teva Pharmaceutical Industries Ltd. | New crystal forms of oxcarbazepine and processes for their preparation |
| TW200501962A (en) * | 2003-04-01 | 2005-01-16 | Novartis Ag | Use of carbamazepine derivatives for the treatment of agitation in dementia patients |
| SG146631A1 (en) | 2003-09-03 | 2008-10-30 | Novartis Ag | Use of oxcarbazepine for the treatment of diabetic neuropathic pain and the improvement of sleep |
| WO2005066133A2 (en) * | 2003-10-20 | 2005-07-21 | Amoli Organics Ltd. | NOVEL PROCESS FOR PREPARATION OF 10-OXO-10, 11-DIHYDRO-5H-DIBENZ [b,f]AZEPINE-5-CARBOXAMIDE (OXCARBAZEPINE) VIA INTERMEDIATE, 10-METHOXY-5H-DIBENZ[b,f] AZEPINE-5-CARBONYLCHLORIDE |
| ITMI20040452A1 (it) * | 2004-03-09 | 2004-06-09 | Clariant Lsm Italia Spa | Processo per la preparazione di oxcarbazepina |
| US7459553B2 (en) * | 2004-03-11 | 2008-12-02 | Glenmark Generics Ltd. | Process for the preparation of carboxamide compounds |
| WO2005096709A2 (en) * | 2004-03-11 | 2005-10-20 | Sun Pharmaceutical Industries Limited | A process for the preparation of 10,11-dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide |
| EP1600443A1 (en) * | 2004-05-26 | 2005-11-30 | Alberto Milanese | Process for the preparation of oxcarbazepine |
| CA2471666C (en) * | 2004-06-18 | 2009-10-13 | Apotex Pharmachem Inc. | An improved process for the preparation of oxcarbazepine and related intermediates |
| US20060252745A1 (en) | 2005-05-06 | 2006-11-09 | Almeida Jose L D | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| ATE496623T1 (de) | 2006-04-26 | 2011-02-15 | Supernus Pharmaceuticals Inc | Oxcarbazepin-zubereitungen für kontrollierte freisetzung mit sigmoidalem freisetzungsprofil |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| US20090082335A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched oxcarbazepine |
| WO2009073154A1 (en) | 2007-11-28 | 2009-06-11 | Nektar Therapeutics Al, Corporation | Oligomer-tricyclic conjugates |
| US8530647B2 (en) * | 2008-05-08 | 2013-09-10 | Mylan Laboratories Limited | Process for the preparation of oxcarbazepine |
| WO2011091050A1 (en) | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| 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 |
| AU2016381366A1 (en) | 2015-12-30 | 2018-06-28 | Adamas Pharmaceuticals, Inc. | Methods and compositions for the treatment of seizure-related disorders |
| PT3554490T (pt) | 2016-12-16 | 2022-03-17 | Idorsia Pharmaceuticals Ltd | Combinação farmacêutica compreendendo um bloqueador de canais de cálcio de tipo t |
| US10639313B2 (en) | 2017-09-01 | 2020-05-05 | Ndsu Research Foundation | Compound for inhibition of delta-5-desaturase (D5D) and treatment of cancer and inflammation |
| MX2021003730A (es) | 2018-09-28 | 2021-06-18 | Univ Griffith | Agentes y métodos para modular la actividad patógena. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH403767A (de) * | 1961-06-09 | 1965-12-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen |
-
1969
- 1969-03-10 CH CH358369A patent/CH500196A/de not_active IP Right Cessation
-
1970
- 1970-03-03 NO NO00756/70*[A patent/NO130314B/no unknown
- 1970-03-03 DK DK104570AA patent/DK125649B/da not_active IP Right Cessation
- 1970-03-03 FI FI700559A patent/FI50523C/sv active
- 1970-03-03 SE SE02770/70A patent/SE349301B/xx unknown
- 1970-03-03 NL NL7003022.A patent/NL162904C/xx not_active IP Right Cessation
- 1970-03-04 US US16552A patent/US3642775A/en not_active Expired - Lifetime
- 1970-03-05 YU YU536/70A patent/YU33862B/xx unknown
- 1970-03-09 CS CS155670A patent/CS154294B2/cs unknown
- 1970-03-09 BE BE747085D patent/BE747085A/xx not_active IP Right Cessation
- 1970-03-09 BR BR217332/70A patent/BR7017332D0/pt unknown
- 1970-03-09 AT AT218770A patent/AT298492B/de not_active IP Right Cessation
- 1970-03-09 FR FR707008344A patent/FR2034781B1/fr not_active Expired
- 1970-03-09 IE IE302/70A patent/IE34046B1/xx unknown
- 1970-03-09 ES ES377279A patent/ES377279A1/es not_active Expired
- 1970-03-09 CA CA076787A patent/CA920586A/en not_active Expired
- 1970-03-09 PL PL1970139290A patent/PL80549B1/pl unknown
- 1970-03-09 GB GB1111070A patent/GB1310571A/en not_active Expired
- 1970-03-09 DE DE2011087A patent/DE2011087C3/de not_active Expired
- 1970-03-09 BG BG014133A patent/BG17576A3/xx unknown
- 1970-03-09 IL IL34026A patent/IL34026A/en unknown
-
1971
- 1971-09-20 US US00182213A patent/US3716640A/en not_active Expired - Lifetime
-
1976
- 1976-05-31 KE KE2635*UA patent/KE2635A/xx unknown
- 1976-08-19 HK HK519/76*UA patent/HK51976A/xx unknown
- 1976-12-30 MY MY194/76A patent/MY7600194A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE747085A (fr) | 1970-09-09 |
| HK51976A (en) | 1976-08-27 |
| NL162904B (nl) | 1980-02-15 |
| BR7017332D0 (pt) | 1973-01-04 |
| DK125649B (da) | 1973-03-19 |
| FI50523B (sv) | 1975-12-31 |
| PL80549B1 (sv) | 1975-08-30 |
| CS154294B2 (sv) | 1974-03-29 |
| IL34026A (en) | 1972-12-29 |
| KE2635A (en) | 1976-06-11 |
| SE349301B (sv) | 1972-09-25 |
| US3716640A (en) | 1973-02-13 |
| CA920586A (en) | 1973-02-06 |
| FR2034781B1 (sv) | 1973-04-06 |
| BG17576A3 (bg) | 1973-11-10 |
| MY7600194A (en) | 1976-12-31 |
| NL7003022A (sv) | 1970-09-14 |
| GB1310571A (en) | 1973-03-21 |
| YU33862B (en) | 1978-06-30 |
| IE34046L (en) | 1970-09-10 |
| ES377279A1 (es) | 1972-12-16 |
| DE2011087C3 (de) | 1979-08-30 |
| IE34046B1 (en) | 1975-01-08 |
| IL34026A0 (en) | 1970-05-21 |
| FI50523C (sv) | 1976-04-12 |
| AT298492B (de) | 1972-05-10 |
| YU53670A (en) | 1977-12-31 |
| DE2011087A1 (de) | 1970-09-24 |
| NL162904C (nl) | 1980-07-15 |
| FR2034781A1 (sv) | 1970-12-18 |
| CH500196A (de) | 1970-12-15 |
| US3642775A (en) | 1972-02-15 |
| DE2011087B2 (de) | 1978-12-21 |
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