JPH0315637B2 - - Google Patents
Info
- Publication number
- JPH0315637B2 JPH0315637B2 JP56215952A JP21595281A JPH0315637B2 JP H0315637 B2 JPH0315637 B2 JP H0315637B2 JP 56215952 A JP56215952 A JP 56215952A JP 21595281 A JP21595281 A JP 21595281A JP H0315637 B2 JPH0315637 B2 JP H0315637B2
- Authority
- JP
- Japan
- Prior art keywords
- dibenzo
- diazepine
- phthalimido
- propyl
- diphenylamine
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- -1 chloro-5-(dimethylaminoethyl)-11-phenyl-5H-dibenzo[b,e][1,4]diazepine Chemical compound 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000002775 capsule Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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 4
- 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
- 239000001257 hydrogen Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000000969 carrier Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 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
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 2
- CEQDYGZVLYXKTM-UHFFFAOYSA-N 3-[6-(3-fluorophenyl)benzo[b][1,4]benzodiazepin-11-yl]propan-1-amine hydrochloride Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=CC(=CC=C3)F)C=CC=C2 CEQDYGZVLYXKTM-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
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 208000004130 Blepharoptosis Diseases 0.000 description 2
- ANXJKGATPJLQAX-UHFFFAOYSA-N Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)Br)C=CC=C2 Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)Br)C=CC=C2 ANXJKGATPJLQAX-UHFFFAOYSA-N 0.000 description 2
- HLCGWFGCHZZZHX-UHFFFAOYSA-N Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)Cl)C=CC=C2 Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)Cl)C=CC=C2 HLCGWFGCHZZZHX-UHFFFAOYSA-N 0.000 description 2
- DIAZRUKVBBCCCM-UHFFFAOYSA-N Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)F)C=CC=C2 Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=C(C=CC=C3)F)C=CC=C2 DIAZRUKVBBCCCM-UHFFFAOYSA-N 0.000 description 2
- GBOUDJTXTWJDCD-UHFFFAOYSA-N Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=CC(=CC=C3)Br)C=CC=C2 Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=CC(=CC=C3)Br)C=CC=C2 GBOUDJTXTWJDCD-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 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
- 239000013543 active substance Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 150000008533 dibenzodiazepines Chemical class 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004615 ingredient 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
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 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
- 201000003004 ptosis Diseases 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 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
- 239000007858 starting material Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 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 1
- KEZHIFRBZORCGY-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl.ClC(Cl)C(Cl)Cl KEZHIFRBZORCGY-UHFFFAOYSA-N 0.000 description 1
- BLOPFAKSIQBSIG-UHFFFAOYSA-N 11h-benzo[b][1,4]benzodiazepine Chemical compound C1=NC2=CC=CC=C2NC2=CC=CC=C21 BLOPFAKSIQBSIG-UHFFFAOYSA-N 0.000 description 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical class N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 1
- YXGUIKKVTBDGRO-UHFFFAOYSA-N 1h-diazepine;hydrochloride Chemical compound Cl.N1C=CC=CC=N1 YXGUIKKVTBDGRO-UHFFFAOYSA-N 0.000 description 1
- GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 description 1
- VYZYKISVZWEEHW-UHFFFAOYSA-N 3-(6-phenylbenzo[b][1,4]benzodiazepin-11-yl)propan-1-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(CCCN)C2=CC=CC=C2N=C1C1=CC=CC=C1 VYZYKISVZWEEHW-UHFFFAOYSA-N 0.000 description 1
- DBYRDEUNPRAOMS-UHFFFAOYSA-N 3-[6-(2-bromophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC=C1Br DBYRDEUNPRAOMS-UHFFFAOYSA-N 0.000 description 1
- YKVZQFYIHXTSFR-UHFFFAOYSA-N 3-[6-(2-chlorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC=C1Cl YKVZQFYIHXTSFR-UHFFFAOYSA-N 0.000 description 1
- KHYIVTAEWAYRID-UHFFFAOYSA-N 3-[6-(2-fluorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC=C1F KHYIVTAEWAYRID-UHFFFAOYSA-N 0.000 description 1
- AWZDREJIPHJGKY-UHFFFAOYSA-N 3-[6-(3-bromophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC(Br)=C1 AWZDREJIPHJGKY-UHFFFAOYSA-N 0.000 description 1
- RBUYVBXADYQMAW-UHFFFAOYSA-N 3-[6-(3-chlorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC(Cl)=C1 RBUYVBXADYQMAW-UHFFFAOYSA-N 0.000 description 1
- QSYUZNHCOSWJFL-UHFFFAOYSA-N 3-[6-(3-chlorophenyl)benzo[b][1,4]benzodiazepin-11-yl]propan-1-amine hydrochloride Chemical compound Cl.NCCCN1C2=C(N=C(C3=C1C=CC=C3)C3=CC(=CC=C3)Cl)C=CC=C2 QSYUZNHCOSWJFL-UHFFFAOYSA-N 0.000 description 1
- NNDGDNVTFXVDOM-UHFFFAOYSA-N 3-[6-(3-fluorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC(F)=C1 NNDGDNVTFXVDOM-UHFFFAOYSA-N 0.000 description 1
- VCICLOQEZWJSGU-UHFFFAOYSA-N 3-[6-(4-chlorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-N-methylpropan-1-amine hydrochloride Chemical compound Cl.ClC1=CC=C(C=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 VCICLOQEZWJSGU-UHFFFAOYSA-N 0.000 description 1
- TXPONOIBQWEONY-UHFFFAOYSA-N 3-[6-(4-chlorophenyl)benzo[b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=C(Cl)C=C1 TXPONOIBQWEONY-UHFFFAOYSA-N 0.000 description 1
- PBOOZQFGWNZNQE-UHFFFAOYSA-N 3-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=C1 PBOOZQFGWNZNQE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- 229920001817 Agar Polymers 0.000 description 1
- FOSXVJORGZPCCO-UHFFFAOYSA-N Cl.BrC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.BrC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 FOSXVJORGZPCCO-UHFFFAOYSA-N 0.000 description 1
- RIWRLAWJTJIOGE-UHFFFAOYSA-N Cl.BrC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.BrC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 RIWRLAWJTJIOGE-UHFFFAOYSA-N 0.000 description 1
- ADCMTANLMDGJRP-UHFFFAOYSA-N Cl.ClC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.ClC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 ADCMTANLMDGJRP-UHFFFAOYSA-N 0.000 description 1
- UJTCRPMUWJFSRY-UHFFFAOYSA-N Cl.ClC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.ClC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 UJTCRPMUWJFSRY-UHFFFAOYSA-N 0.000 description 1
- RFMVBZISRLYDSX-UHFFFAOYSA-N Cl.FC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.FC1=C(C=CC=C1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 RFMVBZISRLYDSX-UHFFFAOYSA-N 0.000 description 1
- KQLSYKVKQLDVRS-UHFFFAOYSA-N Cl.FC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 Chemical compound Cl.FC=1C=C(C=CC1)C=1C2=C(N(C3=C(N1)C=CC=C3)CCCNC)C=CC=C2 KQLSYKVKQLDVRS-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 235000010489 acacia gum Nutrition 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 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
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004908 diazepines Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 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
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- SYSDAZZVWRRQLU-UHFFFAOYSA-N n,n-dimethyl-3-(6-phenylbenzo[b][1,4]benzodiazepin-11-yl)propan-1-amine Chemical compound C12=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C2N=C1C1=CC=CC=C1 SYSDAZZVWRRQLU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 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
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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, cocaine
-
- 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
Landscapes
- 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)
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30507681A | 1981-09-24 | 1981-09-24 | |
| US305076 | 1981-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5865280A JPS5865280A (ja) | 1983-04-18 |
| JPH0315637B2 true JPH0315637B2 (xx) | 1991-03-01 |
Family
ID=23179221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56215952A Granted JPS5865280A (ja) | 1981-09-24 | 1981-12-29 | ５―（アミノアルキル）―１１―フェニル―５Ｈ―ジベンゾ〔ｂ，ｅ〕〔１，４〕ジアゼピン類 |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS5865280A (xx) |
| KR (1) | KR880001866B1 (xx) |
| AT (1) | AT383121B (xx) |
| AU (2) | AU549806B2 (xx) |
| BE (1) | BE891535A (xx) |
| CA (1) | CA1199325A (xx) |
| CH (2) | CH657126A5 (xx) |
| DE (1) | DE3149923A1 (xx) |
| DK (1) | DK531281A (xx) |
| ES (1) | ES8207157A1 (xx) |
| FI (1) | FI813975L (xx) |
| FR (1) | FR2513249B1 (xx) |
| GB (1) | GB2106894B (xx) |
| GR (1) | GR75123B (xx) |
| HK (1) | HK85785A (xx) |
| HU (1) | HU187394B (xx) |
| IE (1) | IE51880B1 (xx) |
| IL (1) | IL64257A (xx) |
| IN (1) | IN155657B (xx) |
| IT (1) | IT1146729B (xx) |
| LU (1) | LU83798A1 (xx) |
| NL (1) | NL8105892A (xx) |
| NO (1) | NO813838L (xx) |
| NZ (1) | NZ198986A (xx) |
| PH (1) | PH16696A (xx) |
| PL (1) | PL234420A1 (xx) |
| PT (1) | PT74285B (xx) |
| SE (1) | SE448453B (xx) |
| SG (1) | SG65485G (xx) |
| YU (1) | YU43070B (xx) |
| ZA (1) | ZA818481B (xx) |
Family Cites Families (4)
| 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 |
| AT226721B (de) * | 1959-09-22 | 1963-04-10 | Wander Ag Dr A | Verfahren zur Herstellung von neuen, 5-substituierten Diazepinen |
| NL256053A (xx) * | 1959-09-22 |
-
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 NZ NZ198986A patent/NZ198986A/en unknown
- 1981-11-17 GR GR66552A patent/GR75123B/el unknown
- 1981-11-25 IE IE2770/81A patent/IE51880B1/en unknown
- 1981-11-25 PH PH26538A patent/PH16696A/en unknown
- 1981-11-27 LU LU83798A patent/LU83798A1/fr unknown
- 1981-11-27 CH CH65/85A patent/CH657126A5/fr not_active IP Right Cessation
- 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
- 1981-11-30 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 HU HU813778A patent/HU187394B/hu not_active IP Right Cessation
- 1981-12-15 ES ES507970A patent/ES8207157A1/es not_active Expired
- 1981-12-15 AU AU78513/81A patent/AU549806B2/en not_active Ceased
- 1981-12-16 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/en 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
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