JPS62228045A - 新規アミノケトン誘導体 - Google Patents
新規アミノケトン誘導体Info
- Publication number
- JPS62228045A JPS62228045A JP61082180A JP8218086A JPS62228045A JP S62228045 A JPS62228045 A JP S62228045A JP 61082180 A JP61082180 A JP 61082180A JP 8218086 A JP8218086 A JP 8218086A JP S62228045 A JPS62228045 A JP S62228045A
- Authority
- JP
- Japan
- Prior art keywords
- propanone
- formula
- tables
- formulas
- phenyl
- 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.)
- Granted
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 89
- 150000001412 amines Chemical class 0.000 abstract description 9
- 239000003158 myorelaxant agent Substances 0.000 abstract description 5
- 239000012442 inert solvent Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000003113 alkalizing effect Effects 0.000 abstract description 2
- 206010008129 cerebral palsy Diseases 0.000 abstract description 2
- 208000026106 cerebrovascular disease Diseases 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 189
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 105
- 238000006243 chemical reaction Methods 0.000 description 104
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 239000010410 layer Substances 0.000 description 68
- 239000000203 mixture Substances 0.000 description 47
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- 239000002274 desiccant Substances 0.000 description 41
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 23
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy Chemical group 0.000 description 22
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
- 229920002866 paraformaldehyde Polymers 0.000 description 15
- 229930040373 Paraformaldehyde Natural products 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000001294 propane Substances 0.000 description 10
- 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 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 241000220317 Rosa Species 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 5
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 4
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 4
- BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000002040 relaxant effect Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 3
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 3
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 206010041415 Spastic paralysis Diseases 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 210000002747 omentum Anatomy 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 2
- CQLXSFDDEBUZQZ-UHFFFAOYSA-N 1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C)C(=O)C1=CC=CC=C1 CQLXSFDDEBUZQZ-UHFFFAOYSA-N 0.000 description 2
- KTJWVFYKGHSIAS-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C)=C1C KTJWVFYKGHSIAS-UHFFFAOYSA-N 0.000 description 2
- DKVCHMQHUMLKPO-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(OC)=CC=C1OC DKVCHMQHUMLKPO-UHFFFAOYSA-N 0.000 description 2
- OLNPULMJEIPMJE-UHFFFAOYSA-N 1-(2-methoxy-3,5-dimethylphenyl)but-2-en-1-one Chemical compound COC1=C(C)C=C(C)C=C1C(=O)C=CC OLNPULMJEIPMJE-UHFFFAOYSA-N 0.000 description 2
- PELVKTMDDXVZAT-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C=C1OC PELVKTMDDXVZAT-UHFFFAOYSA-N 0.000 description 2
- LXNFHTDXRXVSMN-UHFFFAOYSA-N 1-[4-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]propan-1-one Chemical compound C1CCCC2=C1C(N(C)C)=CC=C2C(=O)CC LXNFHTDXRXVSMN-UHFFFAOYSA-N 0.000 description 2
- HVRUGFJYCAFAAN-UHFFFAOYSA-N 1-bromo-2-ethylbenzene Chemical compound CCC1=CC=CC=C1Br HVRUGFJYCAFAAN-UHFFFAOYSA-N 0.000 description 2
- UJCFZCTTZWHRNL-UHFFFAOYSA-N 2,4-Dimethylanisole Chemical compound COC1=CC=C(C)C=C1C UJCFZCTTZWHRNL-UHFFFAOYSA-N 0.000 description 2
- FQKYTBQZPFRTDH-UHFFFAOYSA-N 2-hydroxy-1-phenylbutan-1-one Chemical compound CCC(O)C(=O)C1=CC=CC=C1 FQKYTBQZPFRTDH-UHFFFAOYSA-N 0.000 description 2
- SJZAUIVYZWPNAS-UHFFFAOYSA-N 2-methoxy-1,4-dimethylbenzene Chemical compound COC1=CC(C)=CC=C1C SJZAUIVYZWPNAS-UHFFFAOYSA-N 0.000 description 2
- OEHXPXTWKPIZMD-UHFFFAOYSA-N 2-methoxy-1-phenylbutan-1-one Chemical compound CCC(OC)C(=O)C1=CC=CC=C1 OEHXPXTWKPIZMD-UHFFFAOYSA-N 0.000 description 2
- FSKFPVLPFLJRQB-UHFFFAOYSA-N 2-methyl-1-(4-methylphenyl)-3-(1-piperidinyl)-1-propanone Chemical compound C=1C=C(C)C=CC=1C(=O)C(C)CN1CCCCC1 FSKFPVLPFLJRQB-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 2
- 229920002160 Celluloid Polymers 0.000 description 2
- 241000283074 Equus asinus Species 0.000 description 2
- 206010020852 Hypertonia Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 108091027881 NEAT1 Proteins 0.000 description 2
- 208000007502 anemia Diseases 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000003287 bathing Methods 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229960005334 tolperisone Drugs 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 210000001364 upper extremity Anatomy 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 2
- XLLPLDFNCXWUOT-UHFFFAOYSA-N (2-methylphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC=C1C XLLPLDFNCXWUOT-UHFFFAOYSA-N 0.000 description 1
- GTCXLDAXYLNXFJ-UHFFFAOYSA-N (3,5-dimethylphenyl) propanoate Chemical compound CCC(=O)OC1=CC(C)=CC(C)=C1 GTCXLDAXYLNXFJ-UHFFFAOYSA-N 0.000 description 1
- XGELLKLPQUNEAN-UHFFFAOYSA-N 1-(2,3,4-trimethoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C(OC)=C1OC XGELLKLPQUNEAN-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- SXTXIWHKFWESDQ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(C)C=C1C SXTXIWHKFWESDQ-UHFFFAOYSA-N 0.000 description 1
- KZMGRXHQECJOEN-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=C(C)C=CC=C1Cl KZMGRXHQECJOEN-UHFFFAOYSA-N 0.000 description 1
- POPZXZAQZJPTJK-UHFFFAOYSA-N 1-(2-fluoro-4-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1F POPZXZAQZJPTJK-UHFFFAOYSA-N 0.000 description 1
- VJAWQHFZOOLASY-UHFFFAOYSA-N 1-(2-hydroxy-3-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C)=C1O VJAWQHFZOOLASY-UHFFFAOYSA-N 0.000 description 1
- BHKDPAPVRAFUKH-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=C(C)C=C(C)C=C1O BHKDPAPVRAFUKH-UHFFFAOYSA-N 0.000 description 1
- MNYKYNWYHKXAEO-UHFFFAOYSA-N 1-(2-methoxy-4,5-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(C)=C(C)C=C1OC MNYKYNWYHKXAEO-UHFFFAOYSA-N 0.000 description 1
- HXJFDGOJFTWPIR-UHFFFAOYSA-N 1-(2-methoxy-5-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(C)=CC=C1OC HXJFDGOJFTWPIR-UHFFFAOYSA-N 0.000 description 1
- NCSYADOGPPUQKI-UHFFFAOYSA-N 1-(2-phenylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1C1=CC=CC=C1 NCSYADOGPPUQKI-UHFFFAOYSA-N 0.000 description 1
- UWYYJEBJXVVOOX-UHFFFAOYSA-N 1-(2-propan-2-ylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1C(C)C UWYYJEBJXVVOOX-UHFFFAOYSA-N 0.000 description 1
- QSHLXVTVXQTHBS-UHFFFAOYSA-N 1-(3-bromophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(Br)=C1 QSHLXVTVXQTHBS-UHFFFAOYSA-N 0.000 description 1
- BHGMMWSZUKCAOT-UHFFFAOYSA-N 1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=C(O)C=C(C)C(Cl)=C1C BHGMMWSZUKCAOT-UHFFFAOYSA-N 0.000 description 1
- WWFQBFYTKIGFFH-UHFFFAOYSA-N 1-(3-chloro-6-methoxy-2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=C(C)C(Cl)=C(C)C=C1OC WWFQBFYTKIGFFH-UHFFFAOYSA-N 0.000 description 1
- SQXQCZIODUUTAD-UHFFFAOYSA-N 1-(3-fluoro-4-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C(F)=C1 SQXQCZIODUUTAD-UHFFFAOYSA-N 0.000 description 1
- QHVNQIJBHWOZRJ-UHFFFAOYSA-N 1-(3-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C)=C1 QHVNQIJBHWOZRJ-UHFFFAOYSA-N 0.000 description 1
- UWSZEAAIPZTRHC-UHFFFAOYSA-N 1-(3-phenylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 UWSZEAAIPZTRHC-UHFFFAOYSA-N 0.000 description 1
- VPQAAPQIOHXFHX-UHFFFAOYSA-N 1-(4-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)propan-1-one Chemical compound C1CCCC2=C1C(O)=CC=C2C(=O)CC VPQAAPQIOHXFHX-UHFFFAOYSA-N 0.000 description 1
- IDTDBDJLMMIARX-UHFFFAOYSA-N 1-(4-methoxy-2,5-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(C)=C(OC)C=C1C IDTDBDJLMMIARX-UHFFFAOYSA-N 0.000 description 1
- UOYQXLFNCLUVBD-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C=C1C UOYQXLFNCLUVBD-UHFFFAOYSA-N 0.000 description 1
- GCPDOMUOJMJEEP-UHFFFAOYSA-N 1-(4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl)-2-(pyrrolidin-1-ylmethyl)butan-1-one Chemical compound C=1C=C(OC)C=2CCCCC=2C=1C(=O)C(CC)CN1CCCC1 GCPDOMUOJMJEEP-UHFFFAOYSA-N 0.000 description 1
- RRWUTJXRXYJZKO-UHFFFAOYSA-N 1-(4-methoxynaphthalen-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(=O)CC)=CC=C(OC)C2=C1 RRWUTJXRXYJZKO-UHFFFAOYSA-N 0.000 description 1
- JLCDSZXBELPBRD-UHFFFAOYSA-N 1-(4-methoxyphenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(OC)C=C1 JLCDSZXBELPBRD-UHFFFAOYSA-N 0.000 description 1
- GHHKIYATZAGODA-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-1-yl)propan-1-one Chemical compound C1CCCC2=C1C=CC=C2C(=O)CC GHHKIYATZAGODA-UHFFFAOYSA-N 0.000 description 1
- BTKVIVVFZPBRNC-UHFFFAOYSA-N 1-(5-chloro-4-methoxy-2-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(Cl)=C(OC)C=C1C BTKVIVVFZPBRNC-UHFFFAOYSA-N 0.000 description 1
- NTLBDKBUIZZRKC-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(F)=CC=C1OC NTLBDKBUIZZRKC-UHFFFAOYSA-N 0.000 description 1
- YZBNCNJACOIPLW-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(F)=CC=C1C YZBNCNJACOIPLW-UHFFFAOYSA-N 0.000 description 1
- SFPLEZVLRMSLCX-UHFFFAOYSA-N 1-chloro-2-methoxy-3-methylbenzene Chemical compound COC1=C(C)C=CC=C1Cl SFPLEZVLRMSLCX-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VIPWUFMFHBIKQI-UHFFFAOYSA-N 1-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(F)C=C1 VIPWUFMFHBIKQI-UHFFFAOYSA-N 0.000 description 1
- WRSWNYCNECGVNL-UHFFFAOYSA-N 1-phenyl-3-pyrrolidin-1-ylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)CCN1CCCC1 WRSWNYCNECGVNL-UHFFFAOYSA-N 0.000 description 1
- MTJVUMGKHCIMJL-UHFFFAOYSA-N 1-piperidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCCC1 MTJVUMGKHCIMJL-UHFFFAOYSA-N 0.000 description 1
- YEJJUJNTWYKFLS-UHFFFAOYSA-N 1-pyrrolidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCC1 YEJJUJNTWYKFLS-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- MPJOJCZVGBOVOV-UHFFFAOYSA-N 2-phenylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C1=CC=CC=C1 MPJOJCZVGBOVOV-UHFFFAOYSA-N 0.000 description 1
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 1
- HGZXQCCQZLSOPP-UHFFFAOYSA-N 3-amino-1-phenylpropan-1-one Chemical class NCCC(=O)C1=CC=CC=C1 HGZXQCCQZLSOPP-UHFFFAOYSA-N 0.000 description 1
- SUDOFTVBCPEFQK-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropanal Chemical compound O=CCCN1CCCC1 SUDOFTVBCPEFQK-UHFFFAOYSA-N 0.000 description 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
- WDNLCUAIHSXPBR-UHFFFAOYSA-N 5-bromo-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=C1C=CC=C2Br WDNLCUAIHSXPBR-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- SOCPHAQYFATGGB-UHFFFAOYSA-N CC[Cd] Chemical compound CC[Cd] SOCPHAQYFATGGB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QHJYQWRLIBPDHL-UHFFFAOYSA-N Cl.CC(C(=O)C1=CC=CC=C1)C Chemical compound Cl.CC(C(=O)C1=CC=CC=C1)C QHJYQWRLIBPDHL-UHFFFAOYSA-N 0.000 description 1
- HVKVTGRFLCLDLK-UHFFFAOYSA-N ClCC(C(=O)C1=CC=CC=C1)OC Chemical compound ClCC(C(=O)C1=CC=CC=C1)OC HVKVTGRFLCLDLK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 206010041591 Spinal osteoarthritis Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N but-2-enal Chemical compound CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000003194 forelimb Anatomy 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000022084 motor paralysis Diseases 0.000 description 1
- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SZZGNBSCRNJZCQ-UHFFFAOYSA-N nitric acid;pyrrolidine Chemical compound O[N+]([O-])=O.C1CCNC1 SZZGNBSCRNJZCQ-UHFFFAOYSA-N 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000009153 reflex inhibition Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 208000005801 spondylosis Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002972 tibial nerve Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-75379 | 1985-04-11 | ||
| JP7537985 | 1985-04-11 | ||
| JP60-113103 | 1985-05-28 | ||
| JP60-131629 | 1985-06-19 | ||
| JP60-271381 | 1985-12-04 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62232080A Division JPS63119424A (ja) | 1985-04-11 | 1987-09-18 | 筋弛緩剤 |
| JP62232081A Division JPH0623140B2 (ja) | 1985-04-11 | 1987-09-18 | 新規アミノケトン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62228045A true JPS62228045A (ja) | 1987-10-06 |
| JPH0335318B2 JPH0335318B2 (ko) | 1991-05-27 |
Family
ID=13574503
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61082180A Granted JPS62228045A (ja) | 1985-04-11 | 1986-04-11 | 新規アミノケトン誘導体 |
| JP62232080A Granted JPS63119424A (ja) | 1985-04-11 | 1987-09-18 | 筋弛緩剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62232080A Granted JPS63119424A (ja) | 1985-04-11 | 1987-09-18 | 筋弛緩剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS62228045A (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003835A1 (fr) * | 1997-07-18 | 1999-01-28 | Nippon Kayaku Kabushiki Kaisha | Derives cetoniques aromatiques et leurs utilisations |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1301863A (fr) * | 1961-06-29 | 1962-08-24 | Science Union & Cie | Aminocétones substituées et leurs procédés de préparation |
| JPS5716845A (en) * | 1980-05-22 | 1982-01-28 | Bayer Ag | Novel aminopropiophenone derivative, manufacture,bactericidal composition and pasteurization |
-
1986
- 1986-04-11 JP JP61082180A patent/JPS62228045A/ja active Granted
-
1987
- 1987-09-18 JP JP62232080A patent/JPS63119424A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1301863A (fr) * | 1961-06-29 | 1962-08-24 | Science Union & Cie | Aminocétones substituées et leurs procédés de préparation |
| JPS5716845A (en) * | 1980-05-22 | 1982-01-28 | Bayer Ag | Novel aminopropiophenone derivative, manufacture,bactericidal composition and pasteurization |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003835A1 (fr) * | 1997-07-18 | 1999-01-28 | Nippon Kayaku Kabushiki Kaisha | Derives cetoniques aromatiques et leurs utilisations |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH034525B2 (ko) | 1991-01-23 |
| JPS63119424A (ja) | 1988-05-24 |
| JPH0335318B2 (ko) | 1991-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0099148B1 (en) | Piperazine derivatives, processes for their preparation and pharmaceutical preparations containing them | |
| DE60006113T2 (de) | Benzolderivate, ein verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese enthalten | |
| JPS6277357A (ja) | フエノキシ酢酸誘導体、その製法及び該化合物を含有する肥満症治療用医薬組成物 | |
| JPS6158472B2 (ko) | ||
| CA2495903A1 (en) | Novel biphenyl and biphenyl-like cannabinoids | |
| JPH02138238A (ja) | ベンジリデン−およびシンナミリデン−マロンニトリル誘導体およびその製法 | |
| TW200530200A (en) | 1,2-Di(cyclic)substituted benzene compounds | |
| DE60122484T2 (de) | Verbindungen für die modulation der proliferation von zellen | |
| WO2000043016A1 (fr) | DERIVE DE DICARBA-closo-DODECABORANE | |
| DE68909253T2 (de) | 1-Aminomethyl-1,2,3,4-tetrahydronaphthaline und -indane. | |
| JPH0623140B2 (ja) | 新規アミノケトン誘導体 | |
| EP0061907A1 (en) | Secondary amines, their preparation, pharmaceutical compositions containing them and their use | |
| KR20000048601A (ko) | 니트론 유도체 | |
| DE60023898T2 (de) | Antipsychotische n-aralkyl cyclische amine | |
| JPS62228045A (ja) | 新規アミノケトン誘導体 | |
| CN106278857A (zh) | α,β‑不饱和羰基四氢萘酮衍生物及其应用 | |
| EP0646110A1 (de) | N-substituierte 3-azabicyclo 3.2.0]heptan-derivate als neuroleptika usw. | |
| JPH05320103A (ja) | プロパンアミンおよびその治療用とくに止瀉用医薬組成物 | |
| DE2332707A1 (de) | Tricyclische tetrahydronaphthalinderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| JPS6069089A (ja) | ジヒドロピリジン−５−ホスホネ−ト誘導体およびその製造法 | |
| US4333930A (en) | Orthoarylideneaminophenethylamines and pharmaceutical compositions | |
| JPS6165869A (ja) | キノリン−ｎ−オキシド誘導体 | |
| DE69828087T2 (de) | Aminderivate | |
| EP0099017A2 (de) | Neue Phenylessigsäure-Derivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2341507A1 (de) | Neue biphenylderivate und verfahren zur herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |