JPH0555509B2 - - Google Patents
Info
- Publication number
- JPH0555509B2 JPH0555509B2 JP8848464A JP4846488A JPH0555509B2 JP H0555509 B2 JPH0555509 B2 JP H0555509B2 JP 8848464 A JP8848464 A JP 8848464A JP 4846488 A JP4846488 A JP 4846488A JP H0555509 B2 JPH0555509 B2 JP H0555509B2
- Authority
- JP
- Japan
- Prior art keywords
- benzothiepino
- pyridazin
- tetrahydro
- chlorophenyl
- dihydro
- 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
- -1 hydroxy, amino Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- 150000001875 compounds Chemical class 0.000 description 61
- 238000002844 melting Methods 0.000 description 51
- 230000008018 melting Effects 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 238000000034 method Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 230000000949 anxiolytic effect Effects 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 210000000265 leukocyte Anatomy 0.000 description 7
- FQHCPFMTXFJZJS-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine;hydrochloride Chemical compound Cl.COC1=CC=C(NN)C=C1 FQHCPFMTXFJZJS-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002249 anxiolytic agent Substances 0.000 description 6
- GLFHMYMOGBMFKJ-UHFFFAOYSA-N 10-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=C(CCSC=2C3=CC(Cl)=CC=2)C3=N1 GLFHMYMOGBMFKJ-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 5
- 229960003529 diazepam Drugs 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- 239000008267 milk Substances 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- LEJAYRGELPEHFV-UHFFFAOYSA-N 10-chloro-2-(4-chlorophenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CC(CCSC=2C3=CC(Cl)=CC=2)C3=N1 LEJAYRGELPEHFV-UHFFFAOYSA-N 0.000 description 4
- IIDYJQBIULBPTJ-UHFFFAOYSA-N 2-(4-bromophenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)CC(CCSC=2C3=CC=CC=2)C3=N1 IIDYJQBIULBPTJ-UHFFFAOYSA-N 0.000 description 4
- 102000004300 GABA-A Receptors Human genes 0.000 description 4
- 108090000839 GABA-A Receptors Proteins 0.000 description 4
- 206010057249 Phagocytosis Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001557 benzodiazepines Chemical class 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000010438 heat treatment Methods 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
- 230000008782 phagocytosis Effects 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 230000028527 righting reflex Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QKMNPUHPWJFRFL-UHFFFAOYSA-N 10-fluoro-2-(4-fluorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C=C(CCSC=2C3=CC(F)=CC=2)C3=N1 QKMNPUHPWJFRFL-UHFFFAOYSA-N 0.000 description 3
- DSKPZHRMHYDUHZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CC(CCSC=2C3=CC=CC=2)C3=N1 DSKPZHRMHYDUHZ-UHFFFAOYSA-N 0.000 description 3
- YIEYSFIVIUQNBF-UHFFFAOYSA-N 2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=C(CCSC=2C3=CC=CC=2)C3=N1 YIEYSFIVIUQNBF-UHFFFAOYSA-N 0.000 description 3
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229940005530 anxiolytics Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 210000002540 macrophage Anatomy 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OQTSXIJQJPCVIU-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-10-fluoro-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound N1=C2C3=CC(F)=CC=C3SCCC2=CC(=O)N1C1=CC=C(Cl)C(Cl)=C1 OQTSXIJQJPCVIU-UHFFFAOYSA-N 0.000 description 2
- PTHZTNTXODWBHO-UHFFFAOYSA-N 2-(4-bromophenyl)-7-oxo-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C=C(CCS(=O)C=2C3=CC=CC=2)C3=N1 PTHZTNTXODWBHO-UHFFFAOYSA-N 0.000 description 2
- CDXGDOAOYZJBAQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-10-fluoro-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound N1=C2C3=CC(F)=CC=C3SCCC2=CC(=O)N1C1=CC=C(Cl)C=C1 CDXGDOAOYZJBAQ-UHFFFAOYSA-N 0.000 description 2
- NGTOQMBNKLHRJA-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C=C(CCSC=2C3=CC=CC=2)C3=N1 NGTOQMBNKLHRJA-UHFFFAOYSA-N 0.000 description 2
- HYICCTJUXYNMNK-UHFFFAOYSA-N 4,4a,5,6-tetrahydro-2h-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1CSC2=CC=CC=C2C2=NNC(=O)CC21 HYICCTJUXYNMNK-UHFFFAOYSA-N 0.000 description 2
- VSDILCSZFNGZRF-UHFFFAOYSA-N 8-chloro-2-(4-chlorophenyl)-7-oxo-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=C(CCS(=O)C=2C3=CC=CC=2Cl)C3=N1 VSDILCSZFNGZRF-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 239000002253 acid Substances 0.000 description 2
- 208000007502 anemia Diseases 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 2
- 229960002456 hexobarbital Drugs 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- FRAKPAVZKUGWSR-UHFFFAOYSA-M sodium;bromite;trihydrate Chemical compound O.O.O.[Na+].[O-]Br=O FRAKPAVZKUGWSR-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000003568 synaptosome Anatomy 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 1
- RGGOWBBBHWTTRE-UHFFFAOYSA-N (4-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Br)C=C1 RGGOWBBBHWTTRE-UHFFFAOYSA-N 0.000 description 1
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 1
- HMHWNJGOHUYVMD-UHFFFAOYSA-N (4-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=C(NN)C=C1 HMHWNJGOHUYVMD-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- YZQAOIUQEJUTCP-UHFFFAOYSA-N 10-chloro-2-(4-chlorophenyl)-7-oxo-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=C(CCS(=O)C=2C3=CC(Cl)=CC=2)C3=N1 YZQAOIUQEJUTCP-UHFFFAOYSA-N 0.000 description 1
- QTUADMKLXGUNBO-UHFFFAOYSA-N 10-fluoro-2-(4-fluorophenyl)-7-oxo-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C=C(CCS(=O)C=2C3=CC(F)=CC=2)C3=N1 QTUADMKLXGUNBO-UHFFFAOYSA-N 0.000 description 1
- IILBZRVUJYTNNV-UHFFFAOYSA-N 10-fluoro-7-oxo-2-[3-(trifluoromethyl)phenyl]-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C=1C(F)=CC=C(S(CCC2=CC3=O)=O)C=1C2=NN3C1=CC=CC(C(F)(F)F)=C1 IILBZRVUJYTNNV-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- AYJPYHRSFOISQA-UHFFFAOYSA-N 2-(2-chlorophenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound ClC1=CC=CC=C1N1C(=O)CC(CCSC=2C3=CC=CC=2)C3=N1 AYJPYHRSFOISQA-UHFFFAOYSA-N 0.000 description 1
- NAVGADCTWBNCPQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound ClC1=CC=CC(N2C(CC3C(C4=CC=CC=C4SCC3)=N2)=O)=C1 NAVGADCTWBNCPQ-UHFFFAOYSA-N 0.000 description 1
- TYANXHYCUFWXFG-UHFFFAOYSA-N 2-(4-bromophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C1=CC(Br)=CC=C1N1C(=O)C=C(CCSC=2C3=CC=CC=2)C3=N1 TYANXHYCUFWXFG-UHFFFAOYSA-N 0.000 description 1
- WXVRWFDYIKCQMT-UHFFFAOYSA-N 2-(4-chlorophenyl)-10-fluoro-7-oxo-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one Chemical compound C=1C(F)=CC=C(S(CCC2=CC3=O)=O)C=1C2=NN3C1=CC=C(Cl)C=C1 WXVRWFDYIKCQMT-UHFFFAOYSA-N 0.000 description 1
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|---|---|---|---|
| JP63048464A JPH01250383A (ja) | 1987-03-02 | 1988-03-01 | ベンゾチエピノ〔５，４−ｃ〕ピリダジン化合物 |
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| JP4849787 | 1987-03-02 | ||
| JP62-48497 | 1987-03-02 | ||
| JP62-172469 | 1987-07-09 | ||
| JP62-306227 | 1987-12-02 | ||
| JP63048464A JPH01250383A (ja) | 1987-03-02 | 1988-03-01 | ベンゾチエピノ〔５，４−ｃ〕ピリダジン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01250383A JPH01250383A (ja) | 1989-10-05 |
| JPH0555509B2 true JPH0555509B2 (pt) | 1993-08-17 |
Family
ID=26388741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63048464A Granted JPH01250383A (ja) | 1987-03-02 | 1988-03-01 | ベンゾチエピノ〔５，４−ｃ〕ピリダジン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01250383A (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5597918A (en) * | 1991-08-27 | 1997-01-28 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused pyridazine compound |
| CA2116448A1 (en) * | 1991-08-27 | 1993-03-04 | Tohru Nakao | Fused pyridazine compound and pharmaceutical use thereof |
-
1988
- 1988-03-01 JP JP63048464A patent/JPH01250383A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01250383A (ja) | 1989-10-05 |
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