JPS6125035B2 - - Google Patents
Info
- Publication number
- JPS6125035B2 JPS6125035B2 JP65576A JP65576A JPS6125035B2 JP S6125035 B2 JPS6125035 B2 JP S6125035B2 JP 65576 A JP65576 A JP 65576A JP 65576 A JP65576 A JP 65576A JP S6125035 B2 JPS6125035 B2 JP S6125035B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrrole
- oxathiino
- oxo
- tetrahydro
- group
- 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
Links
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 66
- -1 2 - quinolyl Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 26
- 150000001875 compounds Chemical group 0.000 claims description 24
- HDKFUIKSQDXSSV-UHFFFAOYSA-N 6h-[1,4]oxathiino[2,3-c]pyrrole Chemical class O1C=CSC2=CNC=C12 HDKFUIKSQDXSSV-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000003233 pyrroles Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
- 229940125725 tranquilizer Drugs 0.000 claims description 3
- 239000003204 tranquilizing agent Substances 0.000 claims description 3
- 230000002936 tranquilizing effect Effects 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229940125681 anticonvulsant agent Drugs 0.000 claims 2
- 239000003326 hypnotic agent Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 241000700159 Rattus Species 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- WICNYNXYKZNNSN-UHFFFAOYSA-N hydron;4-methylpiperazine-1-carbonyl chloride;chloride Chemical compound Cl.CN1CCN(C(Cl)=O)CC1 WICNYNXYKZNNSN-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 6
- SAIRAKVVYHJGMH-UHFFFAOYSA-N 2,3-dihydrofuro[3,4-b][1,4]oxathiine-5,7-dione Chemical compound O1CCSC2=C1C(=O)OC2=O SAIRAKVVYHJGMH-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003701 inert diluent 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
- 239000012074 organic phase Substances 0.000 description 4
- HZRXXQDQZKTJTP-UHFFFAOYSA-N 6-(6-methoxypyridazin-3-yl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound N1=NC(OC)=CC=C1N1C(=O)C(SCCO2)=C2C1=O HZRXXQDQZKTJTP-UHFFFAOYSA-N 0.000 description 3
- VAEZXJZPAHMBAL-UHFFFAOYSA-N 6-(7-chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C1=O)C(=O)C2=C1SCCO2 VAEZXJZPAHMBAL-UHFFFAOYSA-N 0.000 description 3
- HRXBYPUUCBEZAS-UHFFFAOYSA-N 7-chloro-1,8-naphthyridin-2-amine Chemical compound C1=CC(Cl)=NC2=NC(N)=CC=C21 HRXBYPUUCBEZAS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001279009 Strychnos toxifera Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 229960005453 strychnine Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CRADWWWVIYEAFR-UHFFFAOYSA-N 1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N)=CC=C21 CRADWWWVIYEAFR-UHFFFAOYSA-N 0.000 description 2
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 2
- JCAIBTLLMPPCQU-UHFFFAOYSA-N 2,3-dihydro-1,4-oxathiine Chemical compound C1CSC=CO1 JCAIBTLLMPPCQU-UHFFFAOYSA-N 0.000 description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 2
- WTGRSQQSHKBXMQ-UHFFFAOYSA-N 6-(1,8-naphthyridin-2-yl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound C1=CC=NC2=NC(N3C(C4=C(SCCO4)C3=O)=O)=CC=C21 WTGRSQQSHKBXMQ-UHFFFAOYSA-N 0.000 description 2
- FKSPTHXBGAZDNB-UHFFFAOYSA-N 6-(3-nitrophenyl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C3=C(OCCS3)C2=O)=O)=C1 FKSPTHXBGAZDNB-UHFFFAOYSA-N 0.000 description 2
- VHEWYKFHHUSGRM-UHFFFAOYSA-N 6-(5-chloropyridin-2-yl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound N1=CC(Cl)=CC=C1N1C(=O)C(SCCO2)=C2C1=O VHEWYKFHHUSGRM-UHFFFAOYSA-N 0.000 description 2
- ZWYUCXSNUSAAFY-UHFFFAOYSA-N 6-(5-nitropyridin-2-yl)-2,3-dihydro-[1,4]oxathiino[2,3-c]pyrrole-5,7-dione Chemical compound N1=CC([N+](=O)[O-])=CC=C1N1C(=O)C(SCCO2)=C2C1=O ZWYUCXSNUSAAFY-UHFFFAOYSA-N 0.000 description 2
- PZPXAFHENKJYSZ-UHFFFAOYSA-N 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=C(OCCS4)C3=O)O)=CC=C21 PZPXAFHENKJYSZ-UHFFFAOYSA-N 0.000 description 2
- SMKXUNVGTZKMSU-UHFFFAOYSA-N 6-(7-chloroquinolin-2-yl)-5-hydroxy-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound C1=CC(Cl)=CC2=NC(N3C(C4=C(OCCS4)C3=O)O)=CC=C21 SMKXUNVGTZKMSU-UHFFFAOYSA-N 0.000 description 2
- YPWBPONDYDVMLX-UHFFFAOYSA-N 6-methoxypyridazin-3-amine Chemical compound COC1=CC=C(N)N=N1 YPWBPONDYDVMLX-UHFFFAOYSA-N 0.000 description 2
- CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical compound C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 description 2
- WLEQWVIWIDRMKX-UHFFFAOYSA-N 7-methoxy-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OC)=CC=C21 WLEQWVIWIDRMKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FDPRJKQGJROHNA-UHFFFAOYSA-N [6-(5-methylpyridin-2-yl)-7-oxo-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-5-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C(SCCO2)=C2C(=O)N1C1=CC=C(C)C=N1 FDPRJKQGJROHNA-UHFFFAOYSA-N 0.000 description 2
- PCALSFUFBRWADQ-UHFFFAOYSA-N [6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-5-yl] phenyl carbonate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=C2SCCO1)=O)C2OC(=O)OC1=CC=CC=C1 PCALSFUFBRWADQ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- GOOCRIHPADOQAS-ZNUXJMJHSA-N (4ar,5as,8ar,13as,15as,15br)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2h-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid Chemical compound OS(O)(=O)=O.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 GOOCRIHPADOQAS-ZNUXJMJHSA-N 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- QUMRLXXCRQWODL-UHFFFAOYSA-N 1-methylpiperazin-1-ium;chloride Chemical compound [Cl-].C[NH+]1CCNCC1 QUMRLXXCRQWODL-UHFFFAOYSA-N 0.000 description 1
- KWVNKWCJDAWNAE-UHFFFAOYSA-N 2,3-dichloroquinoline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=CC2=C1 KWVNKWCJDAWNAE-UHFFFAOYSA-N 0.000 description 1
- ULCKZMCZALOCMB-UHFFFAOYSA-N 2,3-dihydro-1,4-oxathiine-5,6-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)SCCO1 ULCKZMCZALOCMB-UHFFFAOYSA-N 0.000 description 1
- FSWRUYCICUXURT-UHFFFAOYSA-N 2-methyl-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(C)=CC=C21 FSWRUYCICUXURT-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- FRRSLTVSEILNRN-UHFFFAOYSA-N 5-hydroxy-6-(3-nitrophenyl)-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound O=C1C(OCCS2)=C2C(O)N1C1=CC=CC([N+]([O-])=O)=C1 FRRSLTVSEILNRN-UHFFFAOYSA-N 0.000 description 1
- ZBWSPSCYPDMIRA-UHFFFAOYSA-N 5-hydroxy-6-(5-methylpyridin-2-yl)-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound N1=CC(C)=CC=C1N1C(=O)C(OCCS2)=C2C1O ZBWSPSCYPDMIRA-UHFFFAOYSA-N 0.000 description 1
- RFRWSUGQSGFHTN-UHFFFAOYSA-N 5-hydroxy-6-(5-nitropyridin-2-yl)-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound O=C1C(OCCS2)=C2C(O)N1C1=CC=C([N+]([O-])=O)C=N1 RFRWSUGQSGFHTN-UHFFFAOYSA-N 0.000 description 1
- CVGIKNCVJYZCET-UHFFFAOYSA-N 5-hydroxy-6-(7-methyl-1,8-naphthyridin-2-yl)-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound N=1C2=NC(C)=CC=C2C=CC=1N(C1=O)C(O)C2=C1OCCS2 CVGIKNCVJYZCET-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- QHZJHVQGZKBJJN-UHFFFAOYSA-N 6-(5-chloropyridin-2-yl)-5-hydroxy-3,5-dihydro-2h-[1,4]oxathiino[2,3-c]pyrrol-7-one Chemical compound O=C1C(OCCS2)=C2C(O)N1C1=CC=C(Cl)C=N1 QHZJHVQGZKBJJN-UHFFFAOYSA-N 0.000 description 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 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
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008016 pharmaceutical coating Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- AKGSNUOZGBDODP-UHFFFAOYSA-N piperazine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNCC1 AKGSNUOZGBDODP-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960000412 strychnine sulfate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP65576A JPS5283697A (en) | 1976-01-01 | 1976-01-01 | 1*44oxathieno*2*33c*pyrrole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP65576A JPS5283697A (en) | 1976-01-01 | 1976-01-01 | 1*44oxathieno*2*33c*pyrrole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5283697A JPS5283697A (en) | 1977-07-12 |
| JPS6125035B2 true JPS6125035B2 (fr) | 1986-06-13 |
Family
ID=11479724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP65576A Granted JPS5283697A (en) | 1976-01-01 | 1976-01-01 | 1*44oxathieno*2*33c*pyrrole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5283697A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02110934U (fr) * | 1989-02-22 | 1990-09-05 | ||
| JPH03101127U (fr) * | 1990-01-27 | 1991-10-22 |
-
1976
- 1976-01-01 JP JP65576A patent/JPS5283697A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02110934U (fr) * | 1989-02-22 | 1990-09-05 | ||
| JPH03101127U (fr) * | 1990-01-27 | 1991-10-22 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5283697A (en) | 1977-07-12 |
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