CA1112241A - Rearrangement de la 10,11-epoxy-10,11-dihydro-5h- dibenz¬b,f|azepine-5-carboxamides en 10-oxo-10,11- dibenz¬b,f|azepine-5-carboxamides - Google Patents

Rearrangement de la 10,11-epoxy-10,11-dihydro-5h- dibenz¬b,f|azepine-5-carboxamides en 10-oxo-10,11- dibenz¬b,f|azepine-5-carboxamides

Info

Publication number: CA1112241A
Authority: CA; Canada
Prior art keywords: process according; dihydro; carboxamide; dibenz; azepine
Prior art date: 1978-04-18
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

Application number

CA325,802A

Other languages

English (en)

Inventor

Roland Heckendorn

Janos Zergenyi

Enrico Menard

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date 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 date listed.)

1978-04-18

Filing date

1979-04-12

Publication date

1981-11-10

1979-04-12 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-11-10 Application granted granted Critical

1981-11-10 Publication of CA1112241A publication Critical patent/CA1112241A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 27
230000008707 rearrangement Effects 0.000 title claims abstract description 14
ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 title description 10
239000002904 solvent Substances 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 9
239000011777 magnesium Substances 0.000 claims abstract description 9
239000000126 substance Substances 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052749 magnesium Inorganic materials 0.000 claims abstract description 8
150000004677 hydrates Chemical class 0.000 claims abstract description 5
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
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
239000011575 calcium Substances 0.000 claims abstract description 3
229910052791 calcium Inorganic materials 0.000 claims abstract description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052744 lithium Inorganic materials 0.000 claims abstract description 3
ZRWWEEVEIOGMMT-UHFFFAOYSA-N carbamazepine-10,11-epoxide Chemical compound NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12 ZRWWEEVEIOGMMT-UHFFFAOYSA-N 0.000 claims abstract 3
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
WUSJALRVWRGZMI-UHFFFAOYSA-L calcium;diiodide;tetrahydrate Chemical compound O.O.O.O.[Ca+2].[I-].[I-] WUSJALRVWRGZMI-UHFFFAOYSA-L 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 10
229910001641 magnesium iodide Inorganic materials 0.000 description 8
239000000725 suspension Substances 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
-1 aliphatic epoxides Chemical class 0.000 description 5
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910001623 magnesium bromide Inorganic materials 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910001640 calcium iodide Inorganic materials 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
229910001486 lithium perchlorate Inorganic materials 0.000 description 3
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
239000000047 product Substances 0.000 description 3
LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
229910001622 calcium bromide Inorganic materials 0.000 description 2
WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 2
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
150000001983 dialkylethers Chemical class 0.000 description 2
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
238000007157 ring contraction reaction Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
WNEUNPWLVWPBGB-UHFFFAOYSA-N 1,6-dimethyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2(C)OC21C WNEUNPWLVWPBGB-UHFFFAOYSA-N 0.000 description 1
KNSPBSQWRKKAPI-UHFFFAOYSA-N 2,2-dimethylcyclohexan-1-one Chemical compound CC1(C)CCCCC1=O KNSPBSQWRKKAPI-UHFFFAOYSA-N 0.000 description 1
MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
MIOWCLFTUUSRGK-UHFFFAOYSA-N bicyclo[4.1.0]heptane-7-carbaldehyde Chemical compound C1CCCC2C(C=O)C21 MIOWCLFTUUSRGK-UHFFFAOYSA-N 0.000 description 1
DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000001384 succinic acid 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Epoxy Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA325,802A 1978-04-18 1979-04-12 Rearrangement de la 10,11-epoxy-10,11-dihydro-5h- dibenz¬b,f|azepine-5-carboxamides en 10-oxo-10,11- dibenz¬b,f|azepine-5-carboxamides Expired CA1112241A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH413478A CH633271A5 (en)	1978-04-18	1978-04-18	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
CH4134/78-1		1978-04-18

Publications (1)

Publication Number	Publication Date
CA1112241A true CA1112241A (fr)	1981-11-10

Family

ID=4270467

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA325,802A Expired CA1112241A (fr)	1978-04-18	1979-04-12	Rearrangement de la 10,11-epoxy-10,11-dihydro-5h- dibenz¬b,f\|azepine-5-carboxamides en 10-oxo-10,11- dibenz¬b,f\|azepine-5-carboxamides

Country Status (17)

Country	Link
JP (1)	JPS54138588A (fr)
AR (1)	AR222329A1 (fr)
AT (1)	AT373877B (fr)
BG (1)	BG29282A3 (fr)
CA (1)	CA1112241A (fr)
CH (1)	CH633271A5 (fr)
DK (1)	DK157779A (fr)
ES (1)	ES479600A1 (fr)
FI (1)	FI70010C (fr)
GR (1)	GR72260B (fr)
HU (1)	HU182477B (fr)
NL (1)	NL7902811A (fr)
NO (1)	NO149776C (fr)
PL (1)	PL214954A1 (fr)
PT (1)	PT69495A (fr)
SE (1)	SE7903328L (fr)
YU (1)	YU91779A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7125987B2 (en)	2004-06-18	2006-10-24	Apotex Pharmachem Inc.	Process for the preparation of oxcarbazepine and related intermediates

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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

1978
- 1978-04-18 CH CH413478A patent/CH633271A5/de not_active IP Right Cessation
1979
- 1979-04-07 GR GR58835A patent/GR72260B/el unknown
- 1979-04-10 NL NL7902811A patent/NL7902811A/xx not_active Application Discontinuation
- 1979-04-12 CA CA325,802A patent/CA1112241A/fr not_active Expired
- 1979-04-16 BG BG043253A patent/BG29282A3/xx unknown
- 1979-04-16 ES ES479600A patent/ES479600A1/es not_active Expired
- 1979-04-16 AR AR276195A patent/AR222329A1/es active
- 1979-04-17 AT AT0288379A patent/AT373877B/de not_active IP Right Cessation
- 1979-04-17 SE SE7903328A patent/SE7903328L/xx not_active Application Discontinuation
- 1979-04-17 YU YU00917/79A patent/YU91779A/xx unknown
- 1979-04-17 NO NO791274A patent/NO149776C/no unknown
- 1979-04-17 PT PT69495A patent/PT69495A/pt unknown
- 1979-04-17 FI FI791233A patent/FI70010C/fi not_active IP Right Cessation
- 1979-04-17 DK DK157779A patent/DK157779A/da not_active IP Right Cessation
- 1979-04-17 PL PL21495479A patent/PL214954A1/xx unknown
- 1979-04-17 HU HU79CI1926A patent/HU182477B/hu unknown
- 1979-04-18 JP JP4680279A patent/JPS54138588A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7125987B2 (en)	2004-06-18	2006-10-24	Apotex Pharmachem Inc.	Process for the preparation of oxcarbazepine and related intermediates

Also Published As

Publication number	Publication date
HU182477B (en)	1984-01-30
ES479600A1 (es)	1979-07-16
FI70010C (fi)	1986-09-12
CH633271A5 (en)	1982-11-30
NO149776C (no)	1984-06-20
NO791274L (no)	1979-10-19
AT373877B (de)	1984-02-27
BG29282A3 (bg)	1980-10-15
ATA288379A (de)	1983-07-15
YU91779A (en)	1983-01-21
DK157779A (da)	1979-10-19
JPS54138588A (en)	1979-10-27
SE7903328L (sv)	1979-10-19
NO149776B (no)	1984-03-12
FI791233A7 (fi)	1979-10-19
NL7902811A (nl)	1979-10-22
PL214954A1 (fr)	1980-07-01
GR72260B (fr)	1983-10-10
AR222329A1 (es)	1981-05-15
PT69495A (en)	1979-05-01
FI70010B (fi)	1986-01-31

Legal Events

Date	Code	Title	Description
1998-11-10	MKEX	Expiry

Publication	Publication Date	Title
Martin et al.	1968	Synthesis of 1, 4-substituted imidazoles
US4146643A (en)	1979-03-27	Increasing vigilance or treating cerebral insufficiency with substituted vincamines
CN112679420A (zh)	2021-04-20	一种2,5-二溴吡啶的制备方法
CA1051899A (fr)	1979-04-03	Composes de la vincamine
Zinnes et al.	1965	1, 2-Benzothiazines. II. The Preparation and Sodium Borohydride Reduction of 3-Acyl-2H-1, 2-benzothiazin-4 (3H)-one 1, 1-Dioxides1
JPS6337793B2 (fr)	1988-07-27
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CA1112241A - Rearrangement de la 10,11-epoxy-10,11-dihydro-5h- dibenz¬b,f|azepine-5-carboxamides en 10-oxo-10,11- dibenz¬b,f|azepine-5-carboxamides - Google Patents

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