CA1163993A - Process for the manufacture of an oxo compound and new intermediates required therefor - Google Patents
Process for the manufacture of an oxo compound and new intermediates required thereforInfo
- Publication number
- CA1163993A CA1163993A CA000363450A CA363450A CA1163993A CA 1163993 A CA1163993 A CA 1163993A CA 000363450 A CA000363450 A CA 000363450A CA 363450 A CA363450 A CA 363450A CA 1163993 A CA1163993 A CA 1163993A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- formula
- lysing
- compound
- azepine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 88
- 230000008569 process Effects 0.000 title claims abstract description 82
- 239000000543 intermediate Substances 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- -1 oxo compound Chemical class 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000000802 nitrating effect Effects 0.000 claims abstract description 10
- 230000009467 reduction Effects 0.000 claims abstract description 10
- HENMVDHJHVQKCQ-UHFFFAOYSA-N 5-nitrobenzo[b][1]benzazepine-11-carbonitrile Chemical compound [O-][N+](=O)C1=CC2=CC=CC=C2N(C#N)C2=CC=CC=C12 HENMVDHJHVQKCQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- KMJHZCLHURUEKI-UHFFFAOYSA-N benzo[b][1]benzazepine-11-carbonitrile Chemical compound C1=CC2=CC=CC=C2N(C#N)C2=CC=CC=C21 KMJHZCLHURUEKI-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 209
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 47
- 239000000047 product Substances 0.000 claims description 43
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 36
- 229910015900 BF3 Inorganic materials 0.000 claims description 32
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 15
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 15
- 239000011707 mineral Substances 0.000 claims description 15
- 235000010755 mineral Nutrition 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 claims description 8
- 239000001117 sulphuric acid Substances 0.000 claims description 8
- 235000011149 sulphuric acid Nutrition 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- ZJVRKDNTMMYIKR-UHFFFAOYSA-N 5-nitrobenzo[b][1]benzazepine-11-carboxamide Chemical compound C1=C([N+]([O-])=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 ZJVRKDNTMMYIKR-UHFFFAOYSA-N 0.000 abstract description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 41
- 239000000463 material Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- 238000001816 cooling Methods 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- 235000011167 hydrochloric acid Nutrition 0.000 description 16
- 229960000443 hydrochloric acid Drugs 0.000 description 16
- 230000007935 neutral effect Effects 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 238000002329 infrared spectrum Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- 229960004592 isopropanol Drugs 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- JUGKQCJQHACNBE-UHFFFAOYSA-N 5-oxo-6h-benzo[b][1]benzazepine-11-carbonitrile Chemical compound O=C1CC2=CC=CC=C2N(C#N)C2=CC=CC=C12 JUGKQCJQHACNBE-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000228957 Ferula foetida Species 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- LNMRSKLLRKNZGP-SOFGYWHQSA-N (1e)-1-nitrocyclooctene Chemical compound [O-][N+](=O)C/1=C/CCCCCC\1 LNMRSKLLRKNZGP-SOFGYWHQSA-N 0.000 description 1
- RFLOWQIDXYCARJ-UHFFFAOYSA-N 1-(5-bromobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C1=C(Br)C2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 RFLOWQIDXYCARJ-UHFFFAOYSA-N 0.000 description 1
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 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
-
- 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)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Photoreceptors In Electrophotography (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9703/79-2 | 1979-10-30 | ||
| CH970379 | 1979-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163993A true CA1163993A (en) | 1984-03-20 |
Family
ID=4354732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000363450A Expired CA1163993A (en) | 1979-10-30 | 1980-10-28 | Process for the manufacture of an oxo compound and new intermediates required therefor |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US4452738A (en, 2012) |
| EP (1) | EP0028028B1 (en, 2012) |
| JP (5) | JPS5673067A (en, 2012) |
| KR (1) | KR850000945B1 (en, 2012) |
| AT (1) | ATE13426T1 (en, 2012) |
| AU (1) | AU538069B2 (en, 2012) |
| CA (1) | CA1163993A (en, 2012) |
| CY (1) | CY1418A (en, 2012) |
| DD (1) | DD153835A5 (en, 2012) |
| DE (1) | DE3070675D1 (en, 2012) |
| DK (5) | DK163302C (en, 2012) |
| ES (1) | ES496333A0 (en, 2012) |
| FI (1) | FI75561C (en, 2012) |
| GR (1) | GR71889B (en, 2012) |
| HK (1) | HK50388A (en, 2012) |
| HU (1) | HU181208B (en, 2012) |
| IE (1) | IE50723B1 (en, 2012) |
| IL (1) | IL61360A (en, 2012) |
| KE (1) | KE3791A (en, 2012) |
| LU (1) | LU88347I2 (en, 2012) |
| NL (1) | NL930105I2 (en, 2012) |
| NO (1) | NO154725C (en, 2012) |
| NZ (1) | NZ195395A (en, 2012) |
| PL (1) | PL227523A1 (en, 2012) |
| PT (1) | PT71992B (en, 2012) |
| SG (1) | SG103787G (en, 2012) |
| YU (5) | YU44318B (en, 2012) |
| ZA (1) | ZA806643B (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3874195T2 (de) * | 1987-04-27 | 1993-02-11 | Takeda Chemical Industries Ltd | Reduktion von carbonsaeureestern. |
| US5472714A (en) * | 1993-09-08 | 1995-12-05 | Ciba-Geigy Corporation | Double-layered oxcarbazepine tablets |
| 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 |
| CO4920215A1 (es) * | 1997-02-14 | 2000-05-29 | Novartis Ag | Tabletas de oxacarbazepina recubiertas de una pelicula y metodo para la produccion de estas formulaciones |
| AT408224B (de) * | 1999-03-15 | 2001-09-25 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von oxcarbazepin |
| 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 |
| CA2437402A1 (en) * | 2001-02-12 | 2002-08-22 | Teva Pharmaceutical Industries, Ltd. | New crystal forms of oxcarbazepine and processes for their preparation |
| 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 |
| CA2597740C (en) * | 2006-04-26 | 2012-10-16 | Supernus Pharmaceuticals, Inc. | Modified-release preparations containing oxcarbazepine and derivatives thereof |
| CA2658675A1 (en) * | 2006-07-24 | 2008-01-31 | Jubilant Organosys Limited | Process for producing 10-oxo-10, 11-dihydr0-5h-dibenz [b, f] azepine-5-carboxamide starting from 5-cyanoiminostilbene |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| JP5568013B2 (ja) * | 2007-09-19 | 2014-08-06 | レイブンブリック，エルエルシー | ナノスケールのワイヤグリッドを組み込んだ窓用低放射膜 |
| CN100591672C (zh) * | 2008-07-04 | 2010-02-24 | 浙江工业大学 | 一种奥卡西平的化学合成方法 |
| 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 |
| CN103288736B (zh) * | 2013-02-05 | 2015-08-05 | 南京华威医药科技开发有限公司 | 一种艾司利卡西平中间体的制备方法 |
| EP3459365A1 (en) | 2017-09-22 | 2019-03-27 | Unilever N.V. | Composition comprising vegetable oil and apple cider vinegar |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762796A (en) * | 1956-09-11 | Iminodibenzyl derivative | ||
| BE597793A (fr) * | 1960-12-05 | 1961-06-05 | Geigy Ag J R | Nouveaux dérivés de l'azépine et leur préparation. |
| US3420834A (en) * | 1964-11-13 | 1969-01-07 | Roussel Uclaf | 2,3-dimethoxy-berbines substituted in the 10 position and process |
| FR1532301A (fr) * | 1967-01-18 | 1968-07-12 | Rhone Poulenc Sa | Nouveaux dérivés de la dibenzazépine et leur préparation |
| CH500196A (de) * | 1969-03-10 | 1970-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Azepinderivaten |
| NL144275B (nl) * | 1969-06-24 | 1974-12-16 | Rhone Poulenc Sa | Werkwijze voor de bereiding van fungicide preparaten. |
| US3637661A (en) * | 1970-03-04 | 1972-01-25 | Ciba Geigy Corp | 10-hydroxy-10 11-dihydro-dibenzazepine derivative |
| 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 |
| JPS5681565A (en) * | 1979-10-30 | 1981-07-03 | Ciba Geigy Ag | Manufacture of nnheterocyclic compound |
-
1980
- 1980-09-29 FI FI803078A patent/FI75561C/fi not_active IP Right Cessation
- 1980-10-27 GR GR63227A patent/GR71889B/el unknown
- 1980-10-27 AT AT80106590T patent/ATE13426T1/de active
- 1980-10-27 DE DE8080106590T patent/DE3070675D1/de not_active Expired
- 1980-10-27 CY CY141880A patent/CY1418A/xx unknown
- 1980-10-27 EP EP80106590A patent/EP0028028B1/de not_active Expired
- 1980-10-28 PL PL22752380A patent/PL227523A1/xx unknown
- 1980-10-28 DD DD80224781A patent/DD153835A5/de not_active IP Right Cessation
- 1980-10-28 IL IL61360A patent/IL61360A/xx not_active IP Right Cessation
- 1980-10-28 ES ES496333A patent/ES496333A0/es active Granted
- 1980-10-28 CA CA000363450A patent/CA1163993A/en not_active Expired
- 1980-10-29 NO NO803228A patent/NO154725C/no unknown
- 1980-10-29 NZ NZ195395A patent/NZ195395A/xx unknown
- 1980-10-29 ZA ZA00806643A patent/ZA806643B/xx unknown
- 1980-10-29 IE IE2237/80A patent/IE50723B1/en not_active IP Right Cessation
- 1980-10-29 DK DK457780A patent/DK163302C/da not_active IP Right Cessation
- 1980-10-29 HU HU80802613A patent/HU181208B/hu unknown
- 1980-10-29 AU AU63805/80A patent/AU538069B2/en not_active Expired
- 1980-10-29 PT PT71992A patent/PT71992B/pt unknown
- 1980-10-29 KR KR1019800004136A patent/KR850000945B1/ko not_active Expired
- 1980-10-30 YU YU2778/80A patent/YU44318B/xx unknown
- 1980-10-30 JP JP15152680A patent/JPS5673067A/ja active Granted
-
1983
- 1983-05-26 US US06/498,226 patent/US4452738A/en not_active Expired - Lifetime
- 1983-12-12 US US06/559,861 patent/US4559174A/en not_active Expired - Lifetime
-
1984
- 1984-02-27 US US06/584,056 patent/US4540514A/en not_active Expired - Lifetime
- 1984-02-27 US US06/584,057 patent/US4579683A/en not_active Expired - Lifetime
-
1987
- 1987-11-25 SG SG1037/87A patent/SG103787G/en unknown
- 1987-12-09 KE KE3791A patent/KE3791A/xx unknown
-
1988
- 1988-07-07 HK HK503/88A patent/HK50388A/xx not_active IP Right Cessation
- 1988-07-21 JP JP63180432A patent/JPS6445370A/ja active Granted
- 1988-07-21 JP JP63180431A patent/JPS6445366A/ja active Granted
- 1988-07-21 JP JP63180434A patent/JPS6445368A/ja active Granted
- 1988-07-21 JP JP63180433A patent/JPS6445367A/ja active Granted
-
1989
- 1989-07-10 YU YU1372/89A patent/YU45522B/xx unknown
- 1989-07-10 YU YU1364/89A patent/YU45519B/xx unknown
- 1989-07-10 YU YU1365/89A patent/YU45520B/xx unknown
- 1989-07-10 YU YU1366/89A patent/YU45521B/xx unknown
-
1991
- 1991-05-24 DK DK91992A patent/DK99291D0/da not_active Application Discontinuation
- 1991-05-24 DK DK099391A patent/DK170335B1/da not_active IP Right Cessation
- 1991-05-24 DK DK91990A patent/DK99091D0/da not_active Application Discontinuation
- 1991-05-24 DK DK91991A patent/DK99191D0/da unknown
-
1993
- 1993-06-29 NL NL930105C patent/NL930105I2/nl unknown
- 1993-06-30 LU LU88347C patent/LU88347I2/de unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |