DE2238904A1 - Verfahren zur herstellung von 5-acyl-iminostilben-derivaten - Google Patents
Verfahren zur herstellung von 5-acyl-iminostilben-derivatenInfo
- Publication number
- DE2238904A1 DE2238904A1 DE19722238904 DE2238904A DE2238904A1 DE 2238904 A1 DE2238904 A1 DE 2238904A1 DE 19722238904 DE19722238904 DE 19722238904 DE 2238904 A DE2238904 A DE 2238904A DE 2238904 A1 DE2238904 A1 DE 2238904A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- bromine
- iminodibenzyl
- formula iii
- 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.)
- Pending
Links
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 25
- 238000010438 heat treatment Methods 0.000 title claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims description 55
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims description 43
- 238000000034 method Methods 0.000 claims abstract description 38
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 238000005893 bromination reaction Methods 0.000 claims abstract description 7
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 238000002955 isolation Methods 0.000 claims abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000008096 xylene Substances 0.000 claims abstract description 5
- 239000005662 Paraffin oil Substances 0.000 claims abstract description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 74
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 32
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- -1 carbon tetrachloride Chemical class 0.000 claims description 18
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 claims description 10
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 7
- 229940117389 dichlorobenzene Drugs 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 claims description 6
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- 230000009435 amidation Effects 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 2
- 206010059516 Skin toxicity Diseases 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 231100000438 skin toxicity Toxicity 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- FYFJMRRHHBAMEH-UHFFFAOYSA-N 4-imino-3-(2-phenylethenyl)cyclohexa-1,5-diene-1-carbonyl chloride Chemical compound N=C1C=CC(C(=O)Cl)=CC1C=CC1=CC=CC=C1 FYFJMRRHHBAMEH-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 5
- 238000007269 dehydrobromination reaction Methods 0.000 description 5
- JNUDAWGGNBKWNN-UHFFFAOYSA-N 4-imino-3-(2-phenylethenyl)cyclohexa-1,5-diene-1-carbonyl bromide Chemical compound BrC(=O)C=1C=CC(C(C=1)C=CC1=CC=CC=C1)=N JNUDAWGGNBKWNN-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000007256 debromination reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- WXGBMVAPOXRLDB-UHFFFAOYSA-N 6-(2-phenylethenyl)cyclohexa-2,4-dien-1-imine Chemical class N=C1C=CC=CC1C=CC1=CC=CC=C1 WXGBMVAPOXRLDB-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QBSUAHGUFKVVTM-UHFFFAOYSA-N 1-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 QBSUAHGUFKVVTM-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- XKBPLVWTTZDLBP-UHFFFAOYSA-N 4-imino-3-(2-phenylethenyl)cyclohexa-1,5-diene-1-carboxamide Chemical compound C(N)(=O)C=1C=CC(C(C=1)C=CC1=CC=CC=C1)=N XKBPLVWTTZDLBP-UHFFFAOYSA-N 0.000 description 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- LVEUAKZNZPHTDU-UHFFFAOYSA-N BrC(=O)N=C1CC=CC(=C1)C=CC1=CC=CC=C1 Chemical compound BrC(=O)N=C1CC=CC(=C1)C=CC1=CC=CC=C1 LVEUAKZNZPHTDU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AMERLHBNRWKVQY-UHFFFAOYSA-N [3-(2-phenylethenyl)cyclohexa-2,4-dien-1-ylidene]urea Chemical compound C(N)(=O)N=C1CC=CC(=C1)C=CC1=CC=CC=C1 AMERLHBNRWKVQY-UHFFFAOYSA-N 0.000 description 1
- RNSXYRQCNALSEZ-UHFFFAOYSA-N [C].C1CCOC1 Chemical compound [C].C1CCOC1 RNSXYRQCNALSEZ-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical group OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 108010084652 homeobox protein PITX1 Proteins 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD15718871A DD100948A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-13 | 1971-08-13 | |
| DD16111172A DD101671A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-25 | 1972-02-25 | |
| DD16111272A DD102150A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-25 | 1972-02-25 | |
| DD16374472A DD108535A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-16 | 1972-06-16 | |
| DD16374372A DD102151A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-16 | 1972-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2238904A1 true DE2238904A1 (de) | 1973-02-15 |
Family
ID=27509727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722238904 Pending DE2238904A1 (de) | 1971-08-13 | 1972-08-07 | Verfahren zur herstellung von 5-acyl-iminostilben-derivaten |
Country Status (7)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423679A2 (de) | 1989-10-16 | 1991-04-24 | Alkaloida Vegyeszeti Gyar | Verfahren zur Herstellung von 5-(Carbamoyl)-5H-dibenz[b,f]azepin |
| CN116626209A (zh) * | 2023-07-26 | 2023-08-22 | 北京四环制药有限公司 | 一种高灵敏度的奥卡西平起始物料含量检测方法及其应用 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106946780A (zh) * | 2017-02-09 | 2017-07-14 | 上海现代哈森（商丘）药业有限公司 | 一种奥卡西平的合成方法 |
-
1972
- 1972-08-07 DE DE19722238904 patent/DE2238904A1/de active Pending
- 1972-08-09 CH CH1177672A patent/CH588468A5/xx not_active IP Right Cessation
- 1972-08-09 AT AT687372A patent/AT327910B/de not_active IP Right Cessation
- 1972-08-10 YU YU205772A patent/YU205772A/xx unknown
- 1972-08-11 SE SE1049172A patent/SE393611B/xx unknown
- 1972-08-11 NL NL7211002A patent/NL7211002A/xx not_active Application Discontinuation
- 1972-08-11 HU HUAE000364 patent/HU166535B/hu unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423679A2 (de) | 1989-10-16 | 1991-04-24 | Alkaloida Vegyeszeti Gyar | Verfahren zur Herstellung von 5-(Carbamoyl)-5H-dibenz[b,f]azepin |
| CN116626209A (zh) * | 2023-07-26 | 2023-08-22 | 北京四环制药有限公司 | 一种高灵敏度的奥卡西平起始物料含量检测方法及其应用 |
| CN116626209B (zh) * | 2023-07-26 | 2023-10-31 | 北京四环制药有限公司 | 一种高灵敏度的奥卡西平起始物料含量检测方法及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU166535B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-28 |
| CH588468A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-15 |
| ATA687372A (de) | 1975-05-15 |
| NL7211002A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-15 |
| YU205772A (en) | 1980-06-30 |
| AT327910B (de) | 1976-02-25 |
| SE393611B (sv) | 1977-05-16 |
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