JPH0429665B2 - - Google Patents
Info
- Publication number
- JPH0429665B2 JPH0429665B2 JP7634883A JP7634883A JPH0429665B2 JP H0429665 B2 JPH0429665 B2 JP H0429665B2 JP 7634883 A JP7634883 A JP 7634883A JP 7634883 A JP7634883 A JP 7634883A JP H0429665 B2 JPH0429665 B2 JP H0429665B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- atom
- alkyl
- acid
- 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
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- -1 1,2-ethylene group Chemical group 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000003248 quinolines Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 230000008485 antagonism Effects 0.000 claims description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- SCROVKIJQJPORT-UHFFFAOYSA-N 2-(4-methoxy-3-phenylquinolin-2-yl)sulfanyl-n,n-dimethylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 SCROVKIJQJPORT-UHFFFAOYSA-N 0.000 claims description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- PFRNEUIQJBZPGH-UHFFFAOYSA-N n,n,2-trimethyl-1-(4-methyl-3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)(C)CSC1=NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 PFRNEUIQJBZPGH-UHFFFAOYSA-N 0.000 claims description 2
- BFMRUJHBZJHKSB-UHFFFAOYSA-N n,n,2-trimethyl-1-(4-methyl-3-propan-2-ylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound C1=CC=CC2=C(C)C(C(C)C)=C(SCC(C)(C)N(C)C)N=C21 BFMRUJHBZJHKSB-UHFFFAOYSA-N 0.000 claims description 2
- FSTDVTGZMIKTPI-UHFFFAOYSA-N n,n-dimethyl-1-(4-methyl-3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)CSC1=NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 FSTDVTGZMIKTPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000007792 addition Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000002024 ethyl acetate extract Substances 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 5
- 229960001582 fenfluramine Drugs 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- LDCYZAJDBXYCGN-UHFFFAOYSA-N 5-hydroxytryptophan Chemical compound C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 4
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 3
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003420 antiserotonin agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KXZSVYHFYHTNBI-UHFFFAOYSA-N 1h-quinoline-2-thione Chemical class C1=CC=CC2=NC(S)=CC=C21 KXZSVYHFYHTNBI-UHFFFAOYSA-N 0.000 description 2
- OPOZKNSOYMQBJG-UHFFFAOYSA-N 2,4-dichloro-3-(2-methylphenyl)quinoline Chemical compound CC1=CC=CC=C1C1=C(Cl)N=C(C=CC=C2)C2=C1Cl OPOZKNSOYMQBJG-UHFFFAOYSA-N 0.000 description 2
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 2
- DYSUHDOSVZCJEW-UHFFFAOYSA-N 2-chloro-4-methyl-3-phenylquinoline Chemical compound ClC1=NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 DYSUHDOSVZCJEW-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- SHVIRSKRYBVTNK-UHFFFAOYSA-N 4-methoxy-3-(2-methylphenyl)-1h-quinoline-2-thione Chemical group S=C1NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1C SHVIRSKRYBVTNK-UHFFFAOYSA-N 0.000 description 2
- XFZBPNJCSZJCMB-UHFFFAOYSA-N 4-methoxy-3-phenyl-1h-quinoline-2-thione Chemical compound S=C1NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 XFZBPNJCSZJCMB-UHFFFAOYSA-N 0.000 description 2
- YESOXEMDYDGUKE-UHFFFAOYSA-N 4-methyl-3-phenyl-1h-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 YESOXEMDYDGUKE-UHFFFAOYSA-N 0.000 description 2
- RWSUWKVNULWQKJ-UHFFFAOYSA-N 4-methyl-3-phenyl-1h-quinoline-2-thione Chemical compound S=C1NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 RWSUWKVNULWQKJ-UHFFFAOYSA-N 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010020843 Hyperthermia Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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 compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000005056 cell body Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000036031 hyperthermia Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940102398 methyl anthranilate Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000000715 neuromuscular junction Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- DYCQAGMQFDFGOO-LVEZLNDCSA-N (e)-but-2-enedioic acid;n,n,2-trimethyl-1-(4-methyl-3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.CN(C)C(C)(C)CSC1=NC2=CC=CC=C2C(C)=C1C1=CC=CC=C1 DYCQAGMQFDFGOO-LVEZLNDCSA-N 0.000 description 1
- MWYSPSBQVHZIQJ-UHFFFAOYSA-N 1-[3-(2-methoxyphenyl)-4-methylquinolin-2-yl]sulfanyl-n,n,2-trimethylpropan-2-amine Chemical compound COC1=CC=CC=C1C1=C(C)C2=CC=CC=C2N=C1SCC(C)(C)N(C)C MWYSPSBQVHZIQJ-UHFFFAOYSA-N 0.000 description 1
- XNGJEHMQLGWOBI-UHFFFAOYSA-N 1-chloro-n,n,2-trimethylpropan-2-amine;hydrochloride Chemical compound Cl.CN(C)C(C)(C)CCl XNGJEHMQLGWOBI-UHFFFAOYSA-N 0.000 description 1
- SJFHLJHMEGDQLP-UHFFFAOYSA-N 2,4-dimethoxy-3-(2-methylphenyl)quinoline Chemical compound COC1=NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1C SJFHLJHMEGDQLP-UHFFFAOYSA-N 0.000 description 1
- RZWGTXHSYZGXKF-UHFFFAOYSA-N 2-(2-methylphenyl)acetic acid Chemical compound CC1=CC=CC=C1CC(O)=O RZWGTXHSYZGXKF-UHFFFAOYSA-N 0.000 description 1
- QWBUGHDPXASAKQ-UHFFFAOYSA-N 2-(4-methoxy-3-phenylquinolin-2-yl)sulfanyl-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CN(C)CCSC1=NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 QWBUGHDPXASAKQ-UHFFFAOYSA-N 0.000 description 1
- KOGGVCFTLJOEPU-UHFFFAOYSA-N 2-acetyl-3-methyl-n-phenylbutanamide Chemical compound CC(C)C(C(C)=O)C(=O)NC1=CC=CC=C1 KOGGVCFTLJOEPU-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- ZADAUMPQRWXRQI-UHFFFAOYSA-N 4-hydroxy-3-(2-methylphenyl)-1h-quinolin-2-one Chemical compound CC1=CC=CC=C1C1=C(O)C2=CC=CC=C2NC1=O ZADAUMPQRWXRQI-UHFFFAOYSA-N 0.000 description 1
- NIOAVQYSSKOCQP-UHFFFAOYSA-N 4-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(O)=C21 NIOAVQYSSKOCQP-UHFFFAOYSA-N 0.000 description 1
- YILDYWWFKZJGDW-UHFFFAOYSA-N 4-methoxy-3-(2-methylphenyl)-1h-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1C YILDYWWFKZJGDW-UHFFFAOYSA-N 0.000 description 1
- ZWBJEJQWJDYUHV-UHFFFAOYSA-N 4-methoxy-3-phenyl-1h-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 ZWBJEJQWJDYUHV-UHFFFAOYSA-N 0.000 description 1
- OZAHUQLAJKQMFB-UHFFFAOYSA-N 4-methyl-3-propan-2-yl-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(C(C)C)=C(C)C2=C1 OZAHUQLAJKQMFB-UHFFFAOYSA-N 0.000 description 1
- HNIJVVONOCUTMM-UHFFFAOYSA-N 4-methyl-3-propan-2-yl-1h-quinoline-2-thione Chemical compound C1=CC=C2NC(=S)C(C(C)C)=C(C)C2=C1 HNIJVVONOCUTMM-UHFFFAOYSA-N 0.000 description 1
- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
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- 239000005457 ice water Substances 0.000 description 1
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- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- XFHLMFXJJWZYGP-UHFFFAOYSA-N methyl 2-[[2-(2-methylphenyl)acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC1=CC=CC=C1C XFHLMFXJJWZYGP-UHFFFAOYSA-N 0.000 description 1
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- 239000003279 phenylacetic acid Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- 229960003329 sulfinpyrazone Drugs 0.000 description 1
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- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8212787 | 1982-05-04 | ||
| GB8212787 | 1982-05-04 | ||
| GB8302236 | 1983-01-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58213761A JPS58213761A (ja) | 1983-12-12 |
| JPH0429665B2 true JPH0429665B2 (en]) | 1992-05-19 |
Family
ID=10530143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7634883A Granted JPS58213761A (ja) | 1982-05-04 | 1983-05-02 | キノリン誘導体、その製造法及び該化合物を含有する、５−ヒドロキシトリプタミン拮抗作用を有する医薬品 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58213761A (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62135423A (ja) * | 1985-12-09 | 1987-06-18 | Otsuka Pharmaceut Co Ltd | 低酸素症改善剤 |
-
1983
- 1983-05-02 JP JP7634883A patent/JPS58213761A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58213761A (ja) | 1983-12-12 |
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