FI59093C - Foerfarande foer framstaellning av antikonvulsiviskt verksamma 10- och ev 11-substituerade 5h-dibents(b f)azepin-5-ylkarboxamider - Google Patents
Foerfarande foer framstaellning av antikonvulsiviskt verksamma 10- och ev 11-substituerade 5h-dibents(b f)azepin-5-ylkarboxamider Download PDFInfo
- Publication number
- FI59093C FI59093C FI752579A FI752579A FI59093C FI 59093 C FI59093 C FI 59093C FI 752579 A FI752579 A FI 752579A FI 752579 A FI752579 A FI 752579A FI 59093 C FI59093 C FI 59093C
- Authority
- FI
- Finland
- Prior art keywords
- dibenz
- azepine
- hal
- general formula
- halogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical class NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000001773 anti-convulsant effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- -1 halogen hydrogen Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VBHDDODFOVYLTE-UHFFFAOYSA-N 5-bromo-11h-benzo[b][1]benzazepine Chemical compound BrC1=CC2=CC=CC=C2NC2=CC=CC=C12 VBHDDODFOVYLTE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- FGWUKVYDIGVLTD-UHFFFAOYSA-N 5-bromobenzo[b][1]benzazepine-11-carboxamide Chemical compound C1=C(Br)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FGWUKVYDIGVLTD-UHFFFAOYSA-N 0.000 description 3
- HQXOFJNTUXHWMC-UHFFFAOYSA-N 5-chlorobenzo[b][1]benzazepine-11-carboxamide Chemical compound C1=C(Cl)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 HQXOFJNTUXHWMC-UHFFFAOYSA-N 0.000 description 3
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000001538 azepines Chemical class 0.000 description 3
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OFXBNNVZLVPZKV-UHFFFAOYSA-N 1-(5,6-dibromo-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-2,2,2-trifluoroethanone Chemical compound BrC1C(Br)C2=CC=CC=C2N(C(=O)C(F)(F)F)C2=CC=CC=C21 OFXBNNVZLVPZKV-UHFFFAOYSA-N 0.000 description 2
- PYMQCFJRMGFJMT-UHFFFAOYSA-N 1-(5,6-dichloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound ClC1C(Cl)C2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 PYMQCFJRMGFJMT-UHFFFAOYSA-N 0.000 description 2
- LVOGTSDYPVVLHJ-UHFFFAOYSA-N 1-(5-bromobenzo[b][1]benzazepin-11-yl)-2,2,2-trifluoroethanone Chemical compound C1=C(Br)C2=CC=CC=C2N(C(=O)C(F)(F)F)C2=CC=CC=C21 LVOGTSDYPVVLHJ-UHFFFAOYSA-N 0.000 description 2
- YLJJHYIKVBYASC-UHFFFAOYSA-N 1-benzo[b][1]benzazepin-11-yl-2,2,2-trifluoroethanone Chemical compound C1=CC2=CC=CC=C2N(C(=O)C(F)(F)F)C2=CC=CC=C21 YLJJHYIKVBYASC-UHFFFAOYSA-N 0.000 description 2
- XFSAAPULALSJCQ-UHFFFAOYSA-N 11-benzyl-5-fluorobenzo[b][1]benzazepine Chemical compound C12=CC=CC=C2C(F)=CC2=CC=CC=C2N1CC1=CC=CC=C1 XFSAAPULALSJCQ-UHFFFAOYSA-N 0.000 description 2
- AAWRJHGZUXIYDA-UHFFFAOYSA-N 11-benzylbenzo[b][1]benzazepine Chemical compound C12=CC=CC=C2C=CC2=CC=CC=C2N1CC1=CC=CC=C1 AAWRJHGZUXIYDA-UHFFFAOYSA-N 0.000 description 2
- DJQKHJIGURUVKD-UHFFFAOYSA-N 5,6-dichloro-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide Chemical compound ClC1C(Cl)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 DJQKHJIGURUVKD-UHFFFAOYSA-N 0.000 description 2
- QGKKILZRIPXDQH-UHFFFAOYSA-N 5-chloro-11h-benzo[b][1]benzazepine Chemical compound ClC1=CC2=CC=CC=C2NC2=CC=CC=C12 QGKKILZRIPXDQH-UHFFFAOYSA-N 0.000 description 2
- ROSIDVMJJWXUDC-UHFFFAOYSA-N 5-fluoro-11h-benzo[b][1]benzazepine Chemical compound FC1=CC2=CC=CC=C2NC2=CC=CC=C12 ROSIDVMJJWXUDC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
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- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
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- BMIBQXQBABYZOW-UHFFFAOYSA-N 1-(5-chlorobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C1=C(Cl)C2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 BMIBQXQBABYZOW-UHFFFAOYSA-N 0.000 description 1
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- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001466453 Laminaria Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002635 electroconvulsive therapy Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- BMPDWHIDQYTSHX-UHFFFAOYSA-N licarbazepine Chemical compound C1C(O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 BMPDWHIDQYTSHX-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- PMOBWAXBGUSOPS-UHFFFAOYSA-N selenium tetrafluoride Chemical compound F[Se](F)(F)F PMOBWAXBGUSOPS-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- C07D223/26—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1309574A CH605791A5 (is") | 1974-09-27 | 1974-09-27 | |
| CH1309574 | 1974-09-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752579A7 FI752579A7 (is") | 1976-03-28 |
| FI59093B FI59093B (fi) | 1981-02-27 |
| FI59093C true FI59093C (fi) | 1981-06-10 |
Family
ID=4389259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752579A FI59093C (fi) | 1974-09-27 | 1975-09-16 | Foerfarande foer framstaellning av antikonvulsiviskt verksamma 10- och ev 11-substituerade 5h-dibents(b f)azepin-5-ylkarboxamider |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4076812A (is") |
| JP (1) | JPS5159887A (is") |
| AR (2) | AR207601A1 (is") |
| AT (1) | AT346339B (is") |
| AU (1) | AU504972B2 (is") |
| BE (1) | BE833852A (is") |
| CA (1) | CA1067900A (is") |
| CH (1) | CH605791A5 (is") |
| CS (2) | CS190496B2 (is") |
| DE (1) | DE2542335A1 (is") |
| DK (1) | DK395675A (is") |
| ES (1) | ES441272A1 (is") |
| FI (1) | FI59093C (is") |
| FR (2) | FR2313071A1 (is") |
| GB (2) | GB1495176A (is") |
| HU (1) | HU170395B (is") |
| IE (1) | IE41860B1 (is") |
| IL (1) | IL48182A (is") |
| NL (1) | NL7511313A (is") |
| NO (1) | NO143156C (is") |
| SE (1) | SE413771B (is") |
| ZA (1) | ZA756135B (is") |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011603A1 (de) * | 1978-11-10 | 1980-05-28 | Ciba-Geigy Ag | 10-Cyan-5H-dibenz(b,f)azepin-5-carboxamid, Verfahren zu seiner Herstellung und pharmazeutische Präparate, welche diese Verbindung enthalten |
| US4431641A (en) * | 1980-10-17 | 1984-02-14 | Ciba-Geigy Corporation | Pharmaceutical compositions having antiepileptic and antineuralgic action |
| 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. |
| EP0108715A1 (de) * | 1982-10-15 | 1984-05-16 | Ciba-Geigy Ag | Dibenzazepincarboxamide |
| EP0534436B1 (en) * | 1991-09-24 | 1996-08-14 | Shin-Etsu Chemical Co., Ltd. | Polymer scale preventive agent, polymerization vessel effective in preventing polymer scale deposition, and process of producing polymer using said vessel |
| US5472714A (en) * | 1993-09-08 | 1995-12-05 | Ciba-Geigy Corporation | Double-layered oxcarbazepine tablets |
| DE4421294A1 (de) * | 1994-06-17 | 1995-12-21 | Chemie Linz Deutschland | Verfahren zur Herstellung von 5H-Dibenz-(b,f)-azepin-5-carboxamid |
| 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 |
| US20060252745A1 (en) | 2005-05-06 | 2006-11-09 | Almeida Jose L D | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| CN113395958A (zh) | 2019-02-01 | 2021-09-14 | H.隆德贝克有限公司 | 基本上无10-溴-卡马西平的可注射卡马西平组合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD82719B (is") * | ||||
| US2762796A (en) * | 1956-09-11 | Iminodibenzyl derivative | ||
| BE585357A (fr) * | 1958-12-06 | 1960-06-07 | Geigy Ag J R | Nouvelles dibenzo-azepines et leur préparation. |
| ES262485A1 (es) * | 1959-11-16 | 1961-06-01 | Geigy Ag J R | Procedimiento para la preparaciën de nuevos derivados de la azepina |
-
1974
- 1974-09-27 CH CH1309574A patent/CH605791A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR260598A patent/AR207601A1/es active
- 1975-09-03 DK DK395675A patent/DK395675A/da unknown
- 1975-09-04 SE SE7509844A patent/SE413771B/xx unknown
- 1975-09-16 FI FI752579A patent/FI59093C/fi not_active IP Right Cessation
- 1975-09-19 NO NO753200A patent/NO143156C/no unknown
- 1975-09-22 US US05/615,256 patent/US4076812A/en not_active Expired - Lifetime
- 1975-09-23 DE DE19752542335 patent/DE2542335A1/de not_active Withdrawn
- 1975-09-25 AU AU85173/75A patent/AU504972B2/en not_active Expired
- 1975-09-25 CA CA236,329A patent/CA1067900A/en not_active Expired
- 1975-09-25 GB GB39319/75A patent/GB1495176A/en not_active Expired
- 1975-09-25 ES ES441272A patent/ES441272A1/es not_active Expired
- 1975-09-25 FR FR7529382A patent/FR2313071A1/fr active Granted
- 1975-09-25 GB GB26547/77A patent/GB1495177A/en not_active Expired
- 1975-09-25 IL IL48182A patent/IL48182A/xx unknown
- 1975-09-25 NL NL7511313A patent/NL7511313A/xx not_active Application Discontinuation
- 1975-09-26 JP JP50115723A patent/JPS5159887A/ja active Pending
- 1975-09-26 IE IE2105/75A patent/IE41860B1/en unknown
- 1975-09-26 BE BE160396A patent/BE833852A/xx unknown
- 1975-09-26 AT AT737675A patent/AT346339B/de not_active IP Right Cessation
- 1975-09-26 ZA ZA00756135A patent/ZA756135B/xx unknown
- 1975-09-26 HU HUCI1613A patent/HU170395B/hu unknown
- 1975-09-27 CS CS756548A patent/CS190496B2/cs unknown
- 1975-09-27 CS CS772332A patent/CS190499B2/cs unknown
-
1976
- 1976-06-16 AR AR263640A patent/AR217806A1/es active
- 1976-06-18 FR FR7618603A patent/FR2308370A1/fr active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CIBA-GEIGY AG |