JPH0481990B2 - - Google Patents
Info
- Publication number
- JPH0481990B2 JPH0481990B2 JP4628885A JP4628885A JPH0481990B2 JP H0481990 B2 JPH0481990 B2 JP H0481990B2 JP 4628885 A JP4628885 A JP 4628885A JP 4628885 A JP4628885 A JP 4628885A JP H0481990 B2 JPH0481990 B2 JP H0481990B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- phenyl
- oxazolidin
- group
- piperidinopropyl
- 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 26
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 2
- GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229940049906 glutamate Drugs 0.000 description 7
- 229930195712 glutamate Natural products 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- -1 (4RS, 5RS)-4-n-butyl-5-phenyl-3-(3-piperidinopropyl) -1,3-oxazolidin-2-one compound Chemical class 0.000 description 3
- 241000238017 Astacoidea Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010044565 Tremor Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000002964 excitative effect Effects 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000000715 neuromuscular junction Anatomy 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- PBMSFBDTUDFZDV-YADHBBJMSA-N (4r,5s)-4-hexyl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound O([C@H]([C@H]1CCCCCC)C=2C=CC=CC=2)C(=O)N1CCCN1CCCCC1 PBMSFBDTUDFZDV-YADHBBJMSA-N 0.000 description 2
- MHBJZUXIFIWPRT-UHFFFAOYSA-N 1-phenyl-2-(3-piperidin-1-ylpropylamino)octan-1-ol;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(O)C(CCCCCC)NCCCN1CCCCC1 MHBJZUXIFIWPRT-UHFFFAOYSA-N 0.000 description 2
- CBHDABYZJQLLTK-UHFFFAOYSA-N 3-[3-(azepan-1-yl)propyl]-4-hexyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound CCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCCC1 CBHDABYZJQLLTK-UHFFFAOYSA-N 0.000 description 2
- ABZZCQSSDIPILA-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCC(C)(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 ABZZCQSSDIPILA-UHFFFAOYSA-N 0.000 description 2
- OOBBCXZWSAKESQ-UHFFFAOYSA-N 4-(4-methylpentyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OOBBCXZWSAKESQ-UHFFFAOYSA-N 0.000 description 2
- OGJFJARREZDRDX-UHFFFAOYSA-N 4-(5-methylhexyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OGJFJARREZDRDX-UHFFFAOYSA-N 0.000 description 2
- OFBIBBBFSZWAGQ-UHFFFAOYSA-N 4-(6-methylheptyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OFBIBBBFSZWAGQ-UHFFFAOYSA-N 0.000 description 2
- JHTJDDYJMSHYRE-UHFFFAOYSA-N 4-heptan-2-yl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCC(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 JHTJDDYJMSHYRE-UHFFFAOYSA-N 0.000 description 2
- OGAUOMHFUPCPGP-UHFFFAOYSA-N 4-heptyl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OGAUOMHFUPCPGP-UHFFFAOYSA-N 0.000 description 2
- XPRAKDAUULBJFD-UHFFFAOYSA-N 4-hexan-2-yl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCC(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 XPRAKDAUULBJFD-UHFFFAOYSA-N 0.000 description 2
- DCYRXBWGUBWFDZ-UHFFFAOYSA-N 4-hexan-3-yl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCC(CC)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 DCYRXBWGUBWFDZ-UHFFFAOYSA-N 0.000 description 2
- PBMSFBDTUDFZDV-UHFFFAOYSA-N 4-hexyl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 PBMSFBDTUDFZDV-UHFFFAOYSA-N 0.000 description 2
- OSRVBESJHNACJN-UHFFFAOYSA-N 4-hexyl-5-phenyl-3-(3-pyrrolidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCC1 OSRVBESJHNACJN-UHFFFAOYSA-N 0.000 description 2
- MFNKZRGUASOKIC-UHFFFAOYSA-N 4-octan-2-yl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCCC(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 MFNKZRGUASOKIC-UHFFFAOYSA-N 0.000 description 2
- MUFGJIZOGFJGKK-UHFFFAOYSA-N 4-octyl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 MUFGJIZOGFJGKK-UHFFFAOYSA-N 0.000 description 2
- OVTNNOPFEYZNOO-UHFFFAOYSA-N 4-pentan-2-yl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCCC(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OVTNNOPFEYZNOO-UHFFFAOYSA-N 0.000 description 2
- INKOFLHPHGCTFZ-UHFFFAOYSA-N 5-phenyl-3-(3-piperidin-1-ylpropyl)-4-propyl-1,3-oxazolidin-2-one Chemical compound CCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 INKOFLHPHGCTFZ-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- ASNFTDCKZKHJSW-REOHCLBHSA-N Quisqualic acid Chemical compound OC(=O)[C@@H](N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-REOHCLBHSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- IRJCBFDCFXCWGO-SCSAIBSYSA-N (2r)-2-azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC(=O)NO1 IRJCBFDCFXCWGO-SCSAIBSYSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- PBMSFBDTUDFZDV-FGZHOGPDSA-N (4r,5r)-4-hexyl-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound O([C@@H]([C@H]1CCCCCC)C=2C=CC=CC=2)C(=O)N1CCCN1CCCCC1 PBMSFBDTUDFZDV-FGZHOGPDSA-N 0.000 description 1
- HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4628885A JPS61205268A (ja) | 1985-03-08 | 1985-03-08 | 新規な１，３−オキサゾリジン−２−オン誘導体およびその製造法 |
| CN 85104606 CN1011507B (zh) | 1985-03-08 | 1985-06-17 | 制备1，3-唑烷-2-酮衍生物的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4628885A JPS61205268A (ja) | 1985-03-08 | 1985-03-08 | 新規な１，３−オキサゾリジン−２−オン誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205268A JPS61205268A (ja) | 1986-09-11 |
| JPH0481990B2 true JPH0481990B2 (es) | 1992-12-25 |
Family
ID=12743025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4628885A Granted JPS61205268A (ja) | 1985-03-08 | 1985-03-08 | 新規な１，３−オキサゾリジン−２−オン誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205268A (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0314562A (ja) * | 1988-04-11 | 1991-01-23 | Nippon Chemiphar Co Ltd | 新規なアルキレンジアミン誘導体およびグルタミン酸遮断剤 |
-
1985
- 1985-03-08 JP JP4628885A patent/JPS61205268A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61205268A (ja) | 1986-09-11 |
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