JPH0144188B2 - - Google Patents
Info
- Publication number
- JPH0144188B2 JPH0144188B2 JP57002229A JP222982A JPH0144188B2 JP H0144188 B2 JPH0144188 B2 JP H0144188B2 JP 57002229 A JP57002229 A JP 57002229A JP 222982 A JP222982 A JP 222982A JP H0144188 B2 JPH0144188 B2 JP H0144188B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound according
- carbon atoms
- isoquinolinesulfonamide
- methyl
- 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
- -1 group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- GZZCYMXZJQCAJU-UHFFFAOYSA-N isoquinoline-1-sulfonamide Chemical class C1=CC=C2C(S(=O)(=O)N)=NC=CC2=C1 GZZCYMXZJQCAJU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 230000017531 blood circulation Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- LGYZKSZRHKGWKF-UHFFFAOYSA-N n-(2-amino-2-phenylethyl)isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCC(N)C1=CC=CC=C1 LGYZKSZRHKGWKF-UHFFFAOYSA-N 0.000 description 6
- FHRRATMJUOJBHY-UHFFFAOYSA-N n-(4-aminobutyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCN)=CC=CC2=C1 FHRRATMJUOJBHY-UHFFFAOYSA-N 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 230000002040 relaxant effect Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 210000001105 femoral artery Anatomy 0.000 description 5
- WHIDHHUCCTYJKA-UHFFFAOYSA-N isoquinoline-5-sulfonyl chloride Chemical compound N1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 WHIDHHUCCTYJKA-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- AQRJIQVLRKQGRE-UHFFFAOYSA-N n-[2-[benzyl(propan-2-yl)amino]ethyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCN(C(C)C)CC1=CC=CC=C1 AQRJIQVLRKQGRE-UHFFFAOYSA-N 0.000 description 5
- 210000002385 vertebral artery Anatomy 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 210000004204 blood vessel Anatomy 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- DCVZSHVZGVWQKV-UHFFFAOYSA-N n-(2-aminoethyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCN)=CC=CC2=C1 DCVZSHVZGVWQKV-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 210000001363 mesenteric artery superior Anatomy 0.000 description 3
- CYFIUPHXLRDBFV-UHFFFAOYSA-N n-(1-aminohexan-2-yl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NC(CN)CCCC)=CC=CC2=C1 CYFIUPHXLRDBFV-UHFFFAOYSA-N 0.000 description 3
- DRDPMBPWBDJGNY-UHFFFAOYSA-N n-(2-amino-1-phenylethyl)isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NC(CN)C1=CC=CC=C1 DRDPMBPWBDJGNY-UHFFFAOYSA-N 0.000 description 3
- IUTUTTFXRMHOKO-UHFFFAOYSA-N n-(2-amino-3-methylbutyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(N)C(C)C)=CC=CC2=C1 IUTUTTFXRMHOKO-UHFFFAOYSA-N 0.000 description 3
- GONCPDOKLGIBMC-UHFFFAOYSA-N n-(3-piperidin-1-ylpropyl)isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCCN1CCCCC1 GONCPDOKLGIBMC-UHFFFAOYSA-N 0.000 description 3
- YWLUTHLGXGOMKN-UHFFFAOYSA-N n-(6-aminohexyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCCCN)=CC=CC2=C1 YWLUTHLGXGOMKN-UHFFFAOYSA-N 0.000 description 3
- XZJJRUHJVYIWST-UHFFFAOYSA-N n-[2-[benzyl(methyl)amino]ethyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCN(C)CC1=CC=CC=C1 XZJJRUHJVYIWST-UHFFFAOYSA-N 0.000 description 3
- HIXWYUARBOQXCH-UHFFFAOYSA-N n-[3-(dibutylamino)propyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN(CCCC)CCCC)=CC=CC2=C1 HIXWYUARBOQXCH-UHFFFAOYSA-N 0.000 description 3
- GGBYVYWMIIUGKL-UHFFFAOYSA-N n-[3-(diethylamino)propyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN(CC)CC)=CC=CC2=C1 GGBYVYWMIIUGKL-UHFFFAOYSA-N 0.000 description 3
- OMQGGBZLIOJPMN-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN(C)C)=CC=CC2=C1 OMQGGBZLIOJPMN-UHFFFAOYSA-N 0.000 description 3
- GFOFQQQFZVJBOE-UHFFFAOYSA-N n-[3-[benzyl(methyl)amino]propyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCCN(C)CC1=CC=CC=C1 GFOFQQQFZVJBOE-UHFFFAOYSA-N 0.000 description 3
- NZVLOUAFBBSRJZ-UHFFFAOYSA-N n-[3-[cyclohexyl(methyl)amino]propyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCCN(C)C1CCCCC1 NZVLOUAFBBSRJZ-UHFFFAOYSA-N 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PJWUXKNZVMEPPH-UHFFFAOYSA-N N-[2-(methylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNC)=CC=CC2=C1 PJWUXKNZVMEPPH-UHFFFAOYSA-N 0.000 description 2
- KLZGKIDSEJWEDW-UHFFFAOYSA-N N-acetylputrescine Chemical compound CC(=O)NCCCCN KLZGKIDSEJWEDW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- KTHVYEOXWAKQIF-UHFFFAOYSA-N benzyl n-[2-(isoquinolin-5-ylsulfonylamino)propyl]carbamate Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NC(C)CNC(=O)OCC1=CC=CC=C1 KTHVYEOXWAKQIF-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- MIGRFORREVIOBF-UHFFFAOYSA-N isoquinoline-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=NC=CC2=C1 MIGRFORREVIOBF-UHFFFAOYSA-N 0.000 description 2
- BFIWZEKPARJYJE-UHFFFAOYSA-N isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 BFIWZEKPARJYJE-UHFFFAOYSA-N 0.000 description 2
- YFMJTLUPSMCTOQ-UHFFFAOYSA-N isoquinoline-5-sulfonic acid Chemical compound N1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 YFMJTLUPSMCTOQ-UHFFFAOYSA-N 0.000 description 2
- GZQNTWHQJJVIAK-UHFFFAOYSA-N isoquinoline-5-sulfonyl chloride;hydrochloride Chemical compound Cl.N1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 GZQNTWHQJJVIAK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- CMMJQXIVCKIUMN-UHFFFAOYSA-N n'-benzyl-n'-ethylethane-1,2-diamine Chemical compound NCCN(CC)CC1=CC=CC=C1 CMMJQXIVCKIUMN-UHFFFAOYSA-N 0.000 description 2
- LIUGRXFEJOSPIA-UHFFFAOYSA-N n'-benzyl-n'-methylethane-1,2-diamine Chemical compound NCCN(C)CC1=CC=CC=C1 LIUGRXFEJOSPIA-UHFFFAOYSA-N 0.000 description 2
- QMKKHAZKAINWEW-UHFFFAOYSA-N n-(1-aminobutan-2-yl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NC(CN)CC)=CC=CC2=C1 QMKKHAZKAINWEW-UHFFFAOYSA-N 0.000 description 2
- MFAMIGGDMFDDBW-UHFFFAOYSA-N n-(1-aminopropan-2-yl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NC(CN)C)=CC=CC2=C1 MFAMIGGDMFDDBW-UHFFFAOYSA-N 0.000 description 2
- KALVCSANYRICMX-UHFFFAOYSA-N n-(2-aminobutyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(N)CC)=CC=CC2=C1 KALVCSANYRICMX-UHFFFAOYSA-N 0.000 description 2
- ZGUQVKFXDFFLBL-UHFFFAOYSA-N n-(2-aminopropyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(N)C)=CC=CC2=C1 ZGUQVKFXDFFLBL-UHFFFAOYSA-N 0.000 description 2
- PCNFFWMDJLKJNC-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCCN1CCOCC1 PCNFFWMDJLKJNC-UHFFFAOYSA-N 0.000 description 2
- NDJQUUNXWKRXTH-UHFFFAOYSA-N n-[2-(butylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCCC)=CC=CC2=C1 NDJQUUNXWKRXTH-UHFFFAOYSA-N 0.000 description 2
- XVYVGPWWUBVYDU-UHFFFAOYSA-N n-[2-(ethylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCC)=CC=CC2=C1 XVYVGPWWUBVYDU-UHFFFAOYSA-N 0.000 description 2
- ANIVFUPAJTZEFM-UHFFFAOYSA-N n-[2-(propan-2-ylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNC(C)C)=CC=CC2=C1 ANIVFUPAJTZEFM-UHFFFAOYSA-N 0.000 description 2
- VOWSLOLBEBKWBB-UHFFFAOYSA-N n-[3-(n-methylanilino)propyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCCN(C)C1=CC=CC=C1 VOWSLOLBEBKWBB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- YUOFWVVIGKNIEG-UHFFFAOYSA-N 1-[2-(methylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound C1=CC=C2C(CCNC)=NC=CC2=C1S(N)(=O)=O YUOFWVVIGKNIEG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 1
- VPBWZBGZWHDNKL-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCC1 VPBWZBGZWHDNKL-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- 241000283977 Oryctolagus Species 0.000 description 1
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- 208000007536 Thrombosis Diseases 0.000 description 1
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- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- GGFHGJCSVCTZJU-UHFFFAOYSA-N benzyl n-(1-aminopropan-2-yl)carbamate Chemical compound NCC(C)NC(=O)OCC1=CC=CC=C1 GGFHGJCSVCTZJU-UHFFFAOYSA-N 0.000 description 1
- PRGWXRXVMOOPKN-UHFFFAOYSA-N benzyl n-(2-amino-2-phenylethyl)carbamate Chemical compound C=1C=CC=CC=1C(N)CNC(=O)OCC1=CC=CC=C1 PRGWXRXVMOOPKN-UHFFFAOYSA-N 0.000 description 1
- AIGKIQKESHOKBW-UHFFFAOYSA-N benzyl n-(2-aminobutyl)carbamate Chemical compound CCC(N)CNC(=O)OCC1=CC=CC=C1 AIGKIQKESHOKBW-UHFFFAOYSA-N 0.000 description 1
- HVQKTRVTQIMUEL-UHFFFAOYSA-N benzyl n-(2-aminopropyl)carbamate Chemical compound CC(N)CNC(=O)OCC1=CC=CC=C1 HVQKTRVTQIMUEL-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QPGRDTXELAFGRG-UHFFFAOYSA-N n',n'-di(propan-2-yl)propane-1,3-diamine Chemical compound CC(C)N(C(C)C)CCCN QPGRDTXELAFGRG-UHFFFAOYSA-N 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- GZUCMODGDIGMBI-UHFFFAOYSA-N n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CCCN GZUCMODGDIGMBI-UHFFFAOYSA-N 0.000 description 1
- LZQYISZOMMPPIP-UHFFFAOYSA-N n'-benzyl-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CC1=CC=CC=C1 LZQYISZOMMPPIP-UHFFFAOYSA-N 0.000 description 1
- JHXBPQUKAFQZCE-UHFFFAOYSA-N n'-benzyl-n'-propan-2-ylethane-1,2-diamine Chemical compound NCCN(C(C)C)CC1=CC=CC=C1 JHXBPQUKAFQZCE-UHFFFAOYSA-N 0.000 description 1
- GOODZUIQBJNDNO-UHFFFAOYSA-N n'-cyclohexyl-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)C1CCCCC1 GOODZUIQBJNDNO-UHFFFAOYSA-N 0.000 description 1
- WGHBKYWUOOANEX-UHFFFAOYSA-N n'-methyl-n'-phenylpropane-1,3-diamine Chemical compound NCCCN(C)C1=CC=CC=C1 WGHBKYWUOOANEX-UHFFFAOYSA-N 0.000 description 1
- IBWNCINMTUAPHO-UHFFFAOYSA-N n-(1-amino-3-methylbutan-2-yl)acetamide Chemical compound CC(C)C(CN)NC(C)=O IBWNCINMTUAPHO-UHFFFAOYSA-N 0.000 description 1
- IGIJDAVPCAUGCU-UHFFFAOYSA-N n-(1-aminopropan-2-yl)acetamide Chemical compound NCC(C)NC(C)=O IGIJDAVPCAUGCU-UHFFFAOYSA-N 0.000 description 1
- IYQFMEUXLIHZDF-UHFFFAOYSA-N n-(10-aminodecyl)acetamide Chemical compound CC(=O)NCCCCCCCCCCN IYQFMEUXLIHZDF-UHFFFAOYSA-N 0.000 description 1
- WZAXYDAXUMOZJX-UHFFFAOYSA-N n-(10-aminodecyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCCCCCCCN)=CC=CC2=C1 WZAXYDAXUMOZJX-UHFFFAOYSA-N 0.000 description 1
- RVZKQKRNVVWQMQ-UHFFFAOYSA-N n-(2-amino-1-phenylethyl)acetamide Chemical compound CC(=O)NC(CN)C1=CC=CC=C1 RVZKQKRNVVWQMQ-UHFFFAOYSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- YFZBPSXRYCOKCW-UHFFFAOYSA-N n-(3-aminopropyl)acetamide Chemical compound CC(=O)NCCCN YFZBPSXRYCOKCW-UHFFFAOYSA-N 0.000 description 1
- TWCBRFPELLHNLG-UHFFFAOYSA-N n-(3-aminopropyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN)=CC=CC2=C1 TWCBRFPELLHNLG-UHFFFAOYSA-N 0.000 description 1
- JAEJQOUXXMFTJU-UHFFFAOYSA-N n-(4-aminobutyl)formamide Chemical compound NCCCCNC=O JAEJQOUXXMFTJU-UHFFFAOYSA-N 0.000 description 1
- WRJPJZTWQTUPQK-UHFFFAOYSA-N n-(6-aminohexyl)acetamide Chemical compound CC(=O)NCCCCCCN WRJPJZTWQTUPQK-UHFFFAOYSA-N 0.000 description 1
- GWPUBAZPNRZCKG-UHFFFAOYSA-N n-(8-aminooctyl)acetamide Chemical compound CC(=O)NCCCCCCCCN GWPUBAZPNRZCKG-UHFFFAOYSA-N 0.000 description 1
- DCINBVIJDUHDET-UHFFFAOYSA-N n-[1-(isoquinolin-5-ylsulfonylamino)propan-2-yl]acetamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(C)NC(C)=O)=CC=CC2=C1 DCINBVIJDUHDET-UHFFFAOYSA-N 0.000 description 1
- OUWQOGOLAMDDLY-UHFFFAOYSA-N n-[2-[benzyl(ethyl)amino]ethyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)NCCN(CC)CC1=CC=CC=C1 OUWQOGOLAMDDLY-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
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57002229A JPS58121278A (ja) | 1982-01-12 | 1982-01-12 | イソキノリンスルホン酸アミド誘導体 |
| US06/357,770 US4456757A (en) | 1981-03-20 | 1982-03-12 | Isoquinolinesulfonyl derivatives and process for the preparation thereof |
| DE8282102291T DE3261029D1 (en) | 1981-03-20 | 1982-03-19 | Isoquinolinesulfonyl derivatives and process for the preparation thereof |
| EP82102291A EP0061673B1 (en) | 1981-03-20 | 1982-03-19 | Isoquinolinesulfonyl derivatives and process for the preparation thereof |
| US06/572,419 US4560755A (en) | 1981-03-20 | 1984-01-20 | Isoquinolinesulfonyl derivatives which possess a relaxatory action |
| US06/572,418 US4525589A (en) | 1981-03-20 | 1984-01-20 | Isoquinolinesulfonyl derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57002229A JPS58121278A (ja) | 1982-01-12 | 1982-01-12 | イソキノリンスルホン酸アミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58121278A JPS58121278A (ja) | 1983-07-19 |
| JPH0144188B2 true JPH0144188B2 (en, 2012) | 1989-09-26 |
Family
ID=11523520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57002229A Granted JPS58121278A (ja) | 1981-03-20 | 1982-01-12 | イソキノリンスルホン酸アミド誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58121278A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2020027C (en) * | 1990-03-08 | 1996-10-15 | Akiro Kajihara | Isoquinoline- or quinoline-sulfonamide derivative and a pharmaceutical composition comprising the same |
| CA2080128A1 (en) * | 1991-02-13 | 1992-08-14 | Akiro Kajihara | Substituted sulfonamide derivative and a pharmaceutical composition comprising the same |
| AU738620B2 (en) | 1996-08-12 | 2001-09-20 | Mitsubishi Pharma Corporation | Pharmaceutical agent containing Rho kinase inhibitor |
-
1982
- 1982-01-12 JP JP57002229A patent/JPS58121278A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58121278A (ja) | 1983-07-19 |
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