NO865203L - Sulfinyl- og sulfonylsubstituerte 3-benzazepiner. - Google Patents
Sulfinyl- og sulfonylsubstituerte 3-benzazepiner.Info
- Publication number
- NO865203L NO865203L NO865203A NO865203A NO865203L NO 865203 L NO865203 L NO 865203L NO 865203 A NO865203 A NO 865203A NO 865203 A NO865203 A NO 865203A NO 865203 L NO865203 L NO 865203L
- Authority
- NO
- Norway
- Prior art keywords
- benzazepine
- tetrahydro
- formula
- hydrogen
- methoxy
- Prior art date
Links
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 title 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims abstract 2
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 8
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical group N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- HZQZSHLPFAEMLD-UHFFFAOYSA-N 7-methylsulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound C1CNCCC2=C1C=C(S(=O)(=O)C)C(O)=C2 HZQZSHLPFAEMLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- LSIWGVDWJZZPPD-UHFFFAOYSA-N 7-methylsulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)C)=CC=C21 LSIWGVDWJZZPPD-UHFFFAOYSA-N 0.000 claims description 2
- XMYRUQMDLCYTGP-UHFFFAOYSA-N 8-hydroxy-n-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine-7-sulfonamide Chemical compound C1CNCCC2=C1C=C(S(=O)(=O)NC)C(O)=C2 XMYRUQMDLCYTGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- YRSZNBKHBNNZHJ-UHFFFAOYSA-N 7-propylsulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound C1CNCCC2=C1C=C(S(=O)(=O)CCC)C(O)=C2 YRSZNBKHBNNZHJ-UHFFFAOYSA-N 0.000 claims 1
- VWYGGPYUGQNJTC-UHFFFAOYSA-N 8-hydroxy-n,n-dimethyl-2,3,4,5-tetrahydro-1h-3-benzazepine-7-sulfonamide Chemical compound C1CNCCC2=C1C=C(S(=O)(=O)N(C)C)C(O)=C2 VWYGGPYUGQNJTC-UHFFFAOYSA-N 0.000 claims 1
- 101100203601 Caenorhabditis elegans sor-3 gene Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 208000017228 Gastrointestinal motility disease Diseases 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 12
- 210000000111 lower esophageal sphincter Anatomy 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- YRCIUWJOZUZNKX-UHFFFAOYSA-N 3-acetyl-8-methoxy-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(S(Cl)(=O)=O)=C2 YRCIUWJOZUZNKX-UHFFFAOYSA-N 0.000 description 5
- FCXHDGPCFOITRR-UHFFFAOYSA-N 7-methylsulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol;hydrobromide Chemical compound Br.C1CNCCC2=C1C=C(S(=O)(=O)C)C(O)=C2 FCXHDGPCFOITRR-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002024 ethyl acetate extract Substances 0.000 description 5
- -1 sulfonyl-substituted benzazepine compounds Chemical class 0.000 description 5
- GPANJUYZJQNVCT-UHFFFAOYSA-N 1-(8-methoxy-7-methylsulfanyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(SC)=C2 GPANJUYZJQNVCT-UHFFFAOYSA-N 0.000 description 4
- MRLXAVIZYIIFHK-UHFFFAOYSA-N 1-(8-methoxy-7-methylsulfonyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(S(C)(=O)=O)=C2 MRLXAVIZYIIFHK-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000008991 intestinal motility Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000030136 gastric emptying Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GGQGEUNWYGXQDS-UHFFFAOYSA-N 1,2-bis(bromomethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CBr)=C1CBr GGQGEUNWYGXQDS-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
- ZWVLCYBGEDEMPS-UHFFFAOYSA-N 1-(7-bromo-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(Br)=C2 ZWVLCYBGEDEMPS-UHFFFAOYSA-N 0.000 description 2
- WXXFGGLJXIASEO-UHFFFAOYSA-N 1-(7-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=CC(OC)=CC=C21 WXXFGGLJXIASEO-UHFFFAOYSA-N 0.000 description 2
- YYIRQGYTESVBPN-UHFFFAOYSA-N 1-(8-bromo-7-methoxy-6-methylsulfonyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=C(S(C)(=O)=O)C(OC)=C(Br)C=C21 YYIRQGYTESVBPN-UHFFFAOYSA-N 0.000 description 2
- LEFRHAFHLMOJIG-UHFFFAOYSA-N 1-(8-methoxy-7-methylsulfinyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(S(C)=O)=C2 LEFRHAFHLMOJIG-UHFFFAOYSA-N 0.000 description 2
- DIBHLLCULXPKSO-UHFFFAOYSA-N 1-[8-methoxy-7-(trichloromethylsulfanyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(SC(Cl)(Cl)Cl)=C2 DIBHLLCULXPKSO-UHFFFAOYSA-N 0.000 description 2
- YXTOORLTEBRSAL-UHFFFAOYSA-N 1-[8-methoxy-7-(trifluoromethylsulfanyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1CN(C(C)=O)CCC2=C1C=C(OC)C(SC(F)(F)F)=C2 YXTOORLTEBRSAL-UHFFFAOYSA-N 0.000 description 2
- AOEVRCZZWJWKPG-UHFFFAOYSA-N 1-bromo-3-methoxy-5-methylbenzene Chemical compound COC1=CC(C)=CC(Br)=C1 AOEVRCZZWJWKPG-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- KOAWADFHROEGLV-UHFFFAOYSA-N 2-(3-bromo-5-methoxyphenyl)acetic acid Chemical compound COC1=CC(Br)=CC(CC(O)=O)=C1 KOAWADFHROEGLV-UHFFFAOYSA-N 0.000 description 2
- IVKIDNUBLJFKNF-UHFFFAOYSA-N 2-(3-bromo-5-methoxyphenyl)acetonitrile Chemical compound COC1=CC(Br)=CC(CC#N)=C1 IVKIDNUBLJFKNF-UHFFFAOYSA-N 0.000 description 2
- CDZQOJQRDZMMCP-UHFFFAOYSA-N 2-[2-(cyanomethyl)-3-methoxyphenyl]acetonitrile Chemical compound COC1=CC=CC(CC#N)=C1CC#N CDZQOJQRDZMMCP-UHFFFAOYSA-N 0.000 description 2
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- HDYXOGXOWXWJHV-UHFFFAOYSA-N 3-acetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride Chemical compound C1CN(C(=O)C)CCC2=CC=C(S(Cl)(=O)=O)C=C21 HDYXOGXOWXWJHV-UHFFFAOYSA-N 0.000 description 2
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- XLOJPRJMBDTXTC-UHFFFAOYSA-N 6-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=C1C=CC=C2OC XLOJPRJMBDTXTC-UHFFFAOYSA-N 0.000 description 2
- WUNQZFYRIABBKP-UHFFFAOYSA-N 7-methoxy-1,2,3,5-tetrahydro-3-benzazepin-4-one Chemical compound C1CNC(=O)CC2=CC(OC)=CC=C21 WUNQZFYRIABBKP-UHFFFAOYSA-N 0.000 description 2
- QTFBRRKMULNOSW-UHFFFAOYSA-N 7-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine;hydrochloride Chemical compound Cl.C1CNCCC2=CC(OC)=CC=C21 QTFBRRKMULNOSW-UHFFFAOYSA-N 0.000 description 2
- SGIXUEKEYWFKAR-UHFFFAOYSA-N 8-bromo-6-methoxy-3-methyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1CN(C)CCC2=C1C=C(Br)C=C2OC SGIXUEKEYWFKAR-UHFFFAOYSA-N 0.000 description 2
- OQNNFDKEVAURGV-UHFFFAOYSA-N 8-methoxy-1,3-dihydro-3-benzazepin-2-one Chemical compound C1=CNC(=O)CC2=CC(OC)=CC=C21 OQNNFDKEVAURGV-UHFFFAOYSA-N 0.000 description 2
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- 239000000908 ammonium hydroxide Substances 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000012267 brine Substances 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
- 210000004534 cecum Anatomy 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007256 debromination reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000030135 gastric motility Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 230000005176 gastrointestinal motility Effects 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
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- XTVQIYBOITXGSU-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)-2-(3-methoxyphenyl)acetamide Chemical compound COC(OC)CNC(=O)CC1=CC=CC(OC)=C1 XTVQIYBOITXGSU-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 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
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000004203 pyloric antrum Anatomy 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000018556 stomach disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/16—Radicals substituted by nitrogen atoms
-
- 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
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/811,789 US4659706A (en) | 1985-12-20 | 1985-12-20 | Sulfinyl and sulfonyl substituted 3-benzazepines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO865203D0 NO865203D0 (no) | 1986-12-19 |
| NO865203L true NO865203L (no) | 1987-06-22 |
Family
ID=25207582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO865203A NO865203L (no) | 1985-12-20 | 1986-12-19 | Sulfinyl- og sulfonylsubstituerte 3-benzazepiner. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4659706A (xx) |
| EP (1) | EP0229510B1 (xx) |
| JP (1) | JPS62158255A (xx) |
| KR (1) | KR870006007A (xx) |
| CN (1) | CN86108627A (xx) |
| AT (1) | ATE53385T1 (xx) |
| AU (1) | AU589240B2 (xx) |
| CA (1) | CA1263384A (xx) |
| DE (1) | DE3671746D1 (xx) |
| DK (1) | DK610686A (xx) |
| FI (1) | FI865220A (xx) |
| HU (1) | HUT43826A (xx) |
| IL (1) | IL81006A0 (xx) |
| NO (1) | NO865203L (xx) |
| PH (1) | PH22358A (xx) |
| PT (1) | PT83929B (xx) |
| ZA (1) | ZA869501B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0285287A3 (en) * | 1987-03-23 | 1990-08-16 | Smithkline Beecham Corporation | 3-benzazepine compounds for use in treating gastrointestinal motility disorders |
| AU1927992A (en) * | 1991-06-21 | 1993-01-25 | Smithkline Beecham Plc | Medicaments |
| JP2002526443A (ja) | 1998-09-18 | 2002-08-20 | アルコン ラボラトリーズ， インコーポレーテッド | 緑内障治療用セロトニン作動性５ｈｔ２作用物質 |
| CA2347095A1 (en) * | 1998-10-16 | 2000-04-27 | Takeda Chemical Industries, Ltd. | Nitrogen-containing condensed heterocyclic derivatives, their production and agent |
| KR100480782B1 (ko) * | 2002-10-26 | 2005-04-07 | 삼성에스디아이 주식회사 | 연료전지 단위체, 그 제조방법 및 상기 연료전지 단위체를채용한 연료전지 |
| US20060073172A1 (en) * | 2004-10-01 | 2006-04-06 | Schneider L W | Stabilized ophthalmic solution for the treatment of glaucoma and lowering intraocular pressure |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3483185A (en) * | 1966-08-16 | 1969-12-09 | American Home Prod | N-substituted 2,3,4,5-tetrahydro-1h-3-benzazepines |
| CA974989A (en) * | 1968-03-11 | 1975-09-23 | Wallace And Tiernan Inc. | Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby |
| DE1921737A1 (de) * | 1969-04-29 | 1970-11-12 | Bayer Ag | Heterocyclische Acylreste enthaltende Sulfonylharnstoffe und Sulfonylsemicarbazide mit antidiabetischer Wirkung |
| US3671519A (en) * | 1969-07-14 | 1972-06-20 | American Home Prod | N-substituted 2,3,4,5,-tetrahydro-1h-3-benzazepines |
| US3725388A (en) * | 1970-06-25 | 1973-04-03 | Boehringer Sohn Ingelheim | N-acyl-7-(n{41 -cycloalkyl-ureido-n{40 -sulfonyl)-isoquinolines and -benzazepines and alkali metal salts thereof |
| CH593263A5 (xx) * | 1974-02-22 | 1977-11-30 | Hoffmann La Roche | |
| US4206210A (en) * | 1977-01-19 | 1980-06-03 | Smithkline Corporation | Alkylthio-7,8-dihdroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines having dopaminergic activity |
| US4265890A (en) * | 1978-07-07 | 1981-05-05 | Smithkline Corporation | 6-Phenyl thio- and 6-cyclohexyl thio-2,3,4,5-tetrahydro-1H-3-benzazepines |
| US4469634A (en) * | 1982-07-29 | 1984-09-04 | Smithkline Beckman Corporation | Allyloxy- and allylthio-2,3,4,5-tetrahydro-1H-3-benzazepines |
-
1985
- 1985-12-20 US US06/811,789 patent/US4659706A/en not_active Expired - Fee Related
-
1986
- 1986-12-15 PT PT83929A patent/PT83929B/pt not_active IP Right Cessation
- 1986-12-15 PH PH34597A patent/PH22358A/en unknown
- 1986-12-17 EP EP86309846A patent/EP0229510B1/en not_active Expired - Lifetime
- 1986-12-17 DE DE8686309846T patent/DE3671746D1/de not_active Expired - Fee Related
- 1986-12-17 DK DK610686A patent/DK610686A/da not_active Application Discontinuation
- 1986-12-17 AT AT86309846T patent/ATE53385T1/de active
- 1986-12-17 IL IL81006A patent/IL81006A0/xx unknown
- 1986-12-18 ZA ZA869501A patent/ZA869501B/xx unknown
- 1986-12-19 KR KR860010916A patent/KR870006007A/ko not_active Application Discontinuation
- 1986-12-19 AU AU66779/86A patent/AU589240B2/en not_active Ceased
- 1986-12-19 FI FI865220A patent/FI865220A/fi not_active Application Discontinuation
- 1986-12-19 CN CN198686108627A patent/CN86108627A/zh active Pending
- 1986-12-19 CA CA000525851A patent/CA1263384A/en not_active Expired
- 1986-12-19 HU HU865351A patent/HUT43826A/hu unknown
- 1986-12-19 NO NO865203A patent/NO865203L/no unknown
- 1986-12-20 JP JP61305158A patent/JPS62158255A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62158255A (ja) | 1987-07-14 |
| DE3671746D1 (de) | 1990-07-12 |
| CA1263384A (en) | 1989-11-28 |
| FI865220A0 (fi) | 1986-12-19 |
| EP0229510A1 (en) | 1987-07-22 |
| PH22358A (en) | 1988-08-12 |
| AU589240B2 (en) | 1989-10-05 |
| PT83929B (pt) | 1989-05-12 |
| EP0229510B1 (en) | 1990-06-06 |
| PT83929A (en) | 1987-01-01 |
| US4659706A (en) | 1987-04-21 |
| FI865220A (fi) | 1987-06-21 |
| ATE53385T1 (de) | 1990-06-15 |
| DK610686D0 (da) | 1986-12-17 |
| DK610686A (da) | 1987-06-21 |
| KR870006007A (ko) | 1987-07-08 |
| NO865203D0 (no) | 1986-12-19 |
| CN86108627A (zh) | 1987-07-22 |
| IL81006A0 (en) | 1987-03-31 |
| ZA869501B (en) | 1987-08-26 |
| AU6677986A (en) | 1987-06-25 |
| HUT43826A (en) | 1987-12-28 |
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