NO813838L - Fremgangsmaate ved fremstilling av 5-(aminoalkyl)-11-fenyl-5h-dibenzo(b,e)(1,4)diazepiner. - Google Patents

Fremgangsmaate ved fremstilling av 5-(aminoalkyl)-11-fenyl-5h-dibenzo(b,e)(1,4)diazepiner.

Info

Publication number: NO813838L
Authority: NO; Norway
Prior art keywords: dibenzo; phthalimido; diazepine; phenyl; formula
Prior art date: 1981-09-24

Application number

NO813838A

Other languages

English (en)

Norwegian (no)

Inventor

Chandler Roy Taylor Jr

Original Assignee

Robins Co Inc A H

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.)

1981-09-24

Filing date

1981-11-12

Publication date

1983-03-25

1981-11-12 Application filed by Robins Co Inc A H filed Critical Robins Co Inc A H

1983-03-25 Publication of NO813838L publication Critical patent/NO813838L/no

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title description 4
150000004908 diazepines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 34
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 22
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 claims 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims 1
GGFSSROLWJCQEW-UHFFFAOYSA-N 3-(1H-diazepin-5-yl)propan-1-amine Chemical compound N1N=CC=C(C=C1)CCCN GGFSSROLWJCQEW-UHFFFAOYSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 54
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 15
YXGUIKKVTBDGRO-UHFFFAOYSA-N 1h-diazepine;hydrochloride Chemical compound Cl.N1C=CC=CC=N1 YXGUIKKVTBDGRO-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
-1 5-(3-dimethylaminopropyl)-11-phenyl-5H-dibenzodiazepine Chemical compound 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
MMNVGURNVQTZHT-UHFFFAOYSA-N Cl.N1N=CC=C(C=C1)CCCN Chemical compound Cl.N1N=CC=C(C=C1)CCCN MMNVGURNVQTZHT-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000012458 free base Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000002775 capsule Substances 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 2
PBOOZQFGWNZNQE-UHFFFAOYSA-N 3-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=C1 PBOOZQFGWNZNQE-UHFFFAOYSA-N 0.000 description 2
WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 2
SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
NZDVQIKGLZNHOC-UHFFFAOYSA-N 5h-benzo[d][1,2]benzodiazepine Chemical compound N1N=CC2=CC=CC=C2C2=CC=CC=C12 NZDVQIKGLZNHOC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229960005333 tetrabenazine Drugs 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
206010015995 Eyelid ptosis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
229930006000 Sucrose Natural products 0.000 description 1
241000906446 Theraps Species 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
229940124575 antispasmodic agent Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000001506 calcium phosphate Substances 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
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
150000008533 dibenzodiazepines Chemical class 0.000 description 1
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
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239000008273 gelatin Substances 0.000 description 1
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
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230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000001126 phototherapy Methods 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
239000006187 pill Substances 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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230000001528 ptotic effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
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239000000932 sedative agent Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, ***e
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Psychiatry (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO813838A 1981-09-24 1981-11-12 Fremgangsmaate ved fremstilling av 5-(aminoalkyl)-11-fenyl-5h-dibenzo(b,e)(1,4)diazepiner. NO813838L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US30507681A	1981-09-24	1981-09-24

Publications (1)

Publication Number	Publication Date
NO813838L true NO813838L (no)	1983-03-25

Family

ID=23179221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO813838A NO813838L (no)	1981-09-24	1981-11-12	Fremgangsmaate ved fremstilling av 5-(aminoalkyl)-11-fenyl-5h-dibenzo(b,e)(1,4)diazepiner.

Country Status (31)

Country	Link
JP (1)	JPS5865280A (fr)
KR (1)	KR880001866B1 (fr)
AT (1)	AT383121B (fr)
AU (2)	AU549806B2 (fr)
BE (1)	BE891535A (fr)
CA (1)	CA1199325A (fr)
CH (2)	CH651028A5 (fr)
DE (1)	DE3149923A1 (fr)
DK (1)	DK531281A (fr)
ES (1)	ES8207157A1 (fr)
FI (1)	FI813975L (fr)
FR (1)	FR2513249B1 (fr)
GB (1)	GB2106894B (fr)
GR (1)	GR75123B (fr)
HK (1)	HK85785A (fr)
HU (1)	HU187394B (fr)
IE (1)	IE51880B1 (fr)
IL (1)	IL64257A (fr)
IN (1)	IN155657B (fr)
IT (1)	IT1146729B (fr)
LU (1)	LU83798A1 (fr)
NL (1)	NL8105892A (fr)
NO (1)	NO813838L (fr)
NZ (1)	NZ198986A (fr)
PH (1)	PH16696A (fr)
PL (1)	PL234420A1 (fr)
PT (1)	PT74285B (fr)
SE (1)	SE448453B (fr)
SG (1)	SG65485G (fr)
YU (1)	YU43070B (fr)
ZA (1)	ZA818481B (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT228215B (de) *	1959-01-23	1963-07-10	Wander Ag Dr A	Verfahren zur Herstellung von neuen Diazepin-Derivaten
GB907646A (en) *	1959-01-23	1962-10-10	Wander S A A	Method of production of new derivatives of diazepin
NL120551C (fr) *	1959-09-22
AT226721B (de) *	1959-09-22	1963-04-10	Wander Ag Dr A	Verfahren zur Herstellung von neuen, 5-substituierten Diazepinen

1981
- 1981-11-06 SE SE8106594A patent/SE448453B/sv not_active IP Right Cessation
- 1981-11-10 IL IL64257A patent/IL64257A/xx unknown
- 1981-11-12 NO NO813838A patent/NO813838L/no unknown
- 1981-11-13 IN IN1260/CAL/81A patent/IN155657B/en unknown
- 1981-11-16 GB GB08134501A patent/GB2106894B/en not_active Expired
- 1981-11-17 GR GR66552A patent/GR75123B/el unknown
- 1981-11-17 NZ NZ198986A patent/NZ198986A/en unknown
- 1981-11-25 IE IE2770/81A patent/IE51880B1/en unknown
- 1981-11-25 PH PH26538A patent/PH16696A/en unknown
- 1981-11-27 FR FR8122288A patent/FR2513249B1/fr not_active Expired
- 1981-11-27 CH CH7633/81A patent/CH651028A5/fr not_active IP Right Cessation
- 1981-11-27 CH CH65/85A patent/CH657126A5/fr not_active IP Right Cessation
- 1981-11-27 LU LU83798A patent/LU83798A1/fr unknown
- 1981-11-30 DK DK531281A patent/DK531281A/da not_active Application Discontinuation
- 1981-12-07 ZA ZA818481A patent/ZA818481B/xx unknown
- 1981-12-09 AT AT0526981A patent/AT383121B/de not_active IP Right Cessation
- 1981-12-10 FI FI813975A patent/FI813975L/fi not_active Application Discontinuation
- 1981-12-10 IT IT68607/81A patent/IT1146729B/it active
- 1981-12-15 ES ES507970A patent/ES8207157A1/es not_active Expired
- 1981-12-15 AU AU78513/81A patent/AU549806B2/en not_active Ceased
- 1981-12-15 HU HU813778A patent/HU187394B/hu not_active IP Right Cessation
- 1981-12-16 DE DE19813149923 patent/DE3149923A1/de not_active Ceased
- 1981-12-18 BE BE0/206880A patent/BE891535A/fr not_active IP Right Cessation
- 1981-12-23 PL PL23442081A patent/PL234420A1/xx unknown
- 1981-12-29 JP JP56215952A patent/JPS5865280A/ja active Granted
- 1981-12-29 NL NL8105892A patent/NL8105892A/nl not_active Application Discontinuation
1982
- 1982-01-14 CA CA000394124A patent/CA1199325A/fr not_active Expired
- 1982-01-15 PT PT74285A patent/PT74285B/pt unknown
- 1982-02-02 KR KR8200419A patent/KR880001866B1/ko active
- 1982-03-23 YU YU624/82A patent/YU43070B/xx unknown
1985
- 1985-09-09 SG SG654/85A patent/SG65485G/en unknown
- 1985-10-18 AU AU48905/85A patent/AU576010B2/en not_active Ceased
- 1985-10-31 HK HK857/85A patent/HK85785A/xx unknown

Also Published As

Publication number	Publication date
CH657126A5 (fr)	1986-08-15
AU549806B2 (en)	1986-02-13
YU62482A (en)	1984-12-31
DE3149923A1 (de)	1983-04-14
IE51880B1 (en)	1987-04-15
ATA526981A (de)	1986-10-15
CH651028A5 (fr)	1985-08-30
IT8168607A0 (it)	1981-12-10
PT74285B (en)	1983-06-27
ES507970A0 (es)	1982-09-01
CA1199325A (fr)	1986-01-14
IT1146729B (it)	1986-11-19
PT74285A (en)	1982-02-01
SE448453B (sv)	1987-02-23
FR2513249A1 (fr)	1983-03-25
GR75123B (fr)	1984-07-13
NL8105892A (nl)	1983-04-18
PH16696A (en)	1984-01-06
IN155657B (fr)	1985-02-16
FR2513249B1 (fr)	1986-07-11
FI813975L (fi)	1983-03-25
AU7851381A (en)	1983-03-31
PL234420A1 (en)	1983-05-09
GB2106894A (en)	1983-04-20
IE812770L (en)	1983-03-24
JPH0315637B2 (fr)	1991-03-01
JPS5865280A (ja)	1983-04-18
DK531281A (da)	1983-03-25
IL64257A0 (en)	1982-02-28
GB2106894B (en)	1985-05-30
HK85785A (en)	1985-11-08
SE8106594L (sv)	1983-03-25
SG65485G (en)	1986-05-02
AT383121B (de)	1987-05-25
HU187394B (en)	1985-12-28
IL64257A (en)	1985-10-31
LU83798A1 (fr)	1983-09-01
AU4890585A (en)	1986-04-10
BE891535A (fr)	1982-04-16
ZA818481B (en)	1982-10-27
ES8207157A1 (es)	1982-09-01
KR880001866B1 (ko)	1988-09-23
YU43070B (en)	1989-02-28
KR830009057A (ko)	1983-12-17
AU576010B2 (en)	1988-08-11
NZ198986A (en)	1986-02-21

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EP3319959B1 (fr)	2021-09-01	Inhibiteurs hétéro-halogéno d'histone désacétylase
JPS6254792B2 (fr)	1987-11-17
JPH0413347B2 (fr)	1992-03-09
US4351770A (en)	1982-09-28	Preparation of N(2-pyrrolidinylmethyl)2-methoxy-5-benzenesulfonamidobenzamides
NO166940B (no)	1991-06-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4 (5)-substituerte imidazol-derivater, og mellomprodukttil bruk ved fremstillingen.
US3513239A (en)	1970-05-19	Pharmaceutical compositions containing 2-aminoalkyl coumaran derivatives and methods of treating depression therewith
KR900005278B1 (ko)	1990-07-27	치환된 디벤조디아제피논의 제조방법
US3732212A (en)	1973-05-08	1,2,3,10,11,11a-hexahydro-5h-pyrrolo(2,1-c)(1,4)benzodiazepine-5,11-diones
US3860600A (en)	1975-01-14	Octahydropyrrido{8 2,1-c{9 {8 1,4{9 benzodiazepines
NO813838L (no)	1983-03-25	Fremgangsmaate ved fremstilling av 5-(aminoalkyl)-11-fenyl-5h-dibenzo(b,e)(1,4)diazepiner.
TW452574B (en)	2001-09-01	Sulfonamide-substituted fused 7-membered ring compounds, their use as a medicament, and pharmaceutical preparations comprising them
US4447361A (en)	1984-05-08	Aryl substituted pyrido[1,4]benzodiazepines
US4694003A (en)	1987-09-15	Method of treating depression with 5-(aminoalkyl)-11-phenyl-5H-dibenzo(b,e)(1,4) diazepines
CA1184493A (fr)	1985-03-26	Antidepresseur
CA1126729A (fr)	1982-06-29	[1,2]cond.-7-phenyl-1,4-benzodiazepines, compositions pharmaceutiques qui en renferment et methodes pour les preparer
NZ199610A (en)	1985-05-31	Tricyclic pyrrole derivatives
JPH04312585A (ja)	1992-11-04	ピロリジン誘導体
US3457271A (en)	1969-07-22	11-lower alkyl-hexahydro-1-benzazepino (3,2,1-h,i)pyrido(4,3-b)indole
KR830001838B1 (ko)	1983-09-14	페닐-퀴놀리지딘의 제조방법
IE54331B1 (en)	1989-08-30	(2-((nitropyridinyl)amino)phenyl)arylmethanones and salts, their use in medicine, pharmaceutical compositions containing them and their use in the preparation of (2-((aminopyridinyl)amino)phenyl)arylmethanones and pyrido (1,4)benzodiazepines
NO158062B (no)	1988-03-28	Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrido (1,4)benzodiazepiner.
HU179948B (en)	1983-01-28	Process for preparing new piperazino- and hexahydroazepino/1,2-a/-pyrrolo/2,1-c/1,4-benzodiazepine derivatives and pharmaceutical compositions containing such compounds
EP0076017B1 (fr)	1990-08-16	Pyrido(1,4)benzodiazépines substituées par un phényl et intermédiaires
JPS6254114B2 (fr)	1987-11-13
US3407258A (en)	1968-10-22	Methods of treating arteriosclerotic vertigo and depression