JPH0481986B2 - - Google Patents
Info
- Publication number
- JPH0481986B2 JPH0481986B2 JP27390884A JP27390884A JPH0481986B2 JP H0481986 B2 JPH0481986 B2 JP H0481986B2 JP 27390884 A JP27390884 A JP 27390884A JP 27390884 A JP27390884 A JP 27390884A JP H0481986 B2 JPH0481986 B2 JP H0481986B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound according
- carbon atoms
- ethylene
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- FGQPVNODELDKQF-UHFFFAOYSA-N 1-chloroisoquinoline-5-sulfonic acid Chemical compound N1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1Cl FGQPVNODELDKQF-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- LAFGPNHTRJDGQR-UHFFFAOYSA-N 1-chloroisoquinoline-5-sulfonyl chloride Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1S(Cl)(=O)=O LAFGPNHTRJDGQR-UHFFFAOYSA-N 0.000 description 7
- -1 1-ethyl-4-(1-chloro-5-isoquinolinesulfonyl)piperazine Chemical compound 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- OMJJWTRJQSZCDF-UHFFFAOYSA-N n-(2-aminoethyl)-1-chloroisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCN)=CC=CC2=C1Cl OMJJWTRJQSZCDF-UHFFFAOYSA-N 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- UHXGSILHEDNFEC-UHFFFAOYSA-N n-(4-aminobutyl)-1-chloroisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCN)=CC=CC2=C1Cl UHXGSILHEDNFEC-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CMDBORFMLULSDI-UHFFFAOYSA-N 1-chloro-5-(1,4-diazepan-1-ylsulfonyl)isoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1S(=O)(=O)N1CCCNCC1 CMDBORFMLULSDI-UHFFFAOYSA-N 0.000 description 4
- NDNIFNMJMOQAJZ-UHFFFAOYSA-N 1-chloro-n-[2-(hexylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCCCCC)=CC=CC2=C1Cl NDNIFNMJMOQAJZ-UHFFFAOYSA-N 0.000 description 4
- PBTMNRARBCMFRB-UHFFFAOYSA-N 2-[4-[(1-chloroisoquinolin-5-yl)sulfonylamino]butyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCNC(=N)N)=CC=CC2=C1Cl PBTMNRARBCMFRB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- ZAVGJDAFCZAWSZ-UHFFFAOYSA-N hydroxyfasudil Chemical compound C1=CC=C2C(O)=NC=CC2=C1S(=O)(=O)N1CCCNCC1 ZAVGJDAFCZAWSZ-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- TWKLKFVBDCXLBO-UHFFFAOYSA-N n-(1-aminopropan-2-yl)-1-chloroisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NC(CN)C)=CC=CC2=C1Cl TWKLKFVBDCXLBO-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MWHDVPBOXQYYNC-UHFFFAOYSA-N 1-chloro-n-[2-(methylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNC)=CC=CC2=C1Cl MWHDVPBOXQYYNC-UHFFFAOYSA-N 0.000 description 3
- BAYNNVRJLJOYGM-UHFFFAOYSA-N 1-chloro-n-[2-[cyclohexyl(methyl)amino]ethyl]isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=C(Cl)N=CC=C2C=1S(=O)(=O)NCCN(C)C1CCCCC1 BAYNNVRJLJOYGM-UHFFFAOYSA-N 0.000 description 3
- YVZWNUVYNWFWIT-UHFFFAOYSA-N 4-(1-chloroisoquinolin-5-yl)sulfonyl-3-methylpiperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)CCN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 YVZWNUVYNWFWIT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000007810 chemical reaction solvent Substances 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
- 230000000052 comparative effect Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- BFIWZEKPARJYJE-UHFFFAOYSA-N isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 BFIWZEKPARJYJE-UHFFFAOYSA-N 0.000 description 3
- OLTMYWPUZCKEKA-UHFFFAOYSA-N n-[2-(butylamino)ethyl]-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCCC)=CC=CC2=C1O OLTMYWPUZCKEKA-UHFFFAOYSA-N 0.000 description 3
- ISWMKKBIFUJCCX-UHFFFAOYSA-N n-[2-(hexylamino)ethyl]-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCCCCC)=CC=CC2=C1O ISWMKKBIFUJCCX-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OUROABALNQZMSL-UHFFFAOYSA-N 1-chloro-5-(2,5-dimethylpiperazin-1-yl)sulfonylisoquinoline Chemical compound CC1CNC(C)CN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 OUROABALNQZMSL-UHFFFAOYSA-N 0.000 description 2
- NCNGJXOENPCGBX-UHFFFAOYSA-N 1-chloro-5-(3-methylpiperazin-1-yl)sulfonylisoquinoline Chemical compound C1CNC(C)CN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 NCNGJXOENPCGBX-UHFFFAOYSA-N 0.000 description 2
- SOTRBWDIONKYJY-UHFFFAOYSA-N 1-chloro-5-[3-(2-methylpropyl)piperazin-1-yl]sulfonylisoquinoline Chemical compound C1CNC(CC(C)C)CN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 SOTRBWDIONKYJY-UHFFFAOYSA-N 0.000 description 2
- YRLLHVOVPATUBK-UHFFFAOYSA-N 1-chloro-5-piperazin-1-ylsulfonylisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1S(=O)(=O)N1CCNCC1 YRLLHVOVPATUBK-UHFFFAOYSA-N 0.000 description 2
- VYVLGXZHVXKVRB-UHFFFAOYSA-N 1-chloro-n-[2-(ethylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCC)=CC=CC2=C1Cl VYVLGXZHVXKVRB-UHFFFAOYSA-N 0.000 description 2
- FKZLQYKLHIXCDW-UHFFFAOYSA-N 1-chloro-n-[2-(propylamino)ethyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCC)=CC=CC2=C1Cl FKZLQYKLHIXCDW-UHFFFAOYSA-N 0.000 description 2
- MSWDJEZDSOTJRZ-UHFFFAOYSA-N 1-chloro-n-[3-(dibutylamino)propyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN(CCCC)CCCC)=CC=CC2=C1Cl MSWDJEZDSOTJRZ-UHFFFAOYSA-N 0.000 description 2
- MHPOJONPKVWVLQ-UHFFFAOYSA-N 1-oxo-n-[2-(propylamino)ethyl]-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNCCC)=CC=CC2=C1O MHPOJONPKVWVLQ-UHFFFAOYSA-N 0.000 description 2
- RZOZMHIUXLDVLN-UHFFFAOYSA-N 2,5-dimethyl-4-[(1-oxo-2h-isoquinolin-5-yl)sulfonyl]piperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)C(C)CN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 RZOZMHIUXLDVLN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HTUSMQLEADLWJA-UHFFFAOYSA-N 2-[(1-chloroisoquinolin-5-yl)sulfonylamino]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCNS(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 HTUSMQLEADLWJA-UHFFFAOYSA-N 0.000 description 2
- BLUGBQQQKDRJOB-UHFFFAOYSA-N 2-[1-[(1-chloroisoquinolin-5-yl)sulfonylamino]-3-methylbutan-2-yl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCC(C(C)C)NC(N)=N)=CC=CC2=C1Cl BLUGBQQQKDRJOB-UHFFFAOYSA-N 0.000 description 2
- SMZRZURMYMDLCM-UHFFFAOYSA-N 2-[2-[(1-chloroisoquinolin-5-yl)sulfonylamino]propyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NC(CNC(N)=N)C)=CC=CC2=C1Cl SMZRZURMYMDLCM-UHFFFAOYSA-N 0.000 description 2
- MWORFUXVBBINOC-UHFFFAOYSA-N 2-[2-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]ethyl]guanidine Chemical compound C1=CNC(=O)C2=C1C(S(=O)(=O)NCCN=C(N)N)=CC=C2 MWORFUXVBBINOC-UHFFFAOYSA-N 0.000 description 2
- ZMUDNNGOVQCXAK-UHFFFAOYSA-N 2-[2-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]hexyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NC(CNC(N)=N)CCCC)=CC=CC2=C1O ZMUDNNGOVQCXAK-UHFFFAOYSA-N 0.000 description 2
- NZJOOMHMWFRUKT-UHFFFAOYSA-N 2-[2-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]propyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NC(CNC(N)=N)C)=CC=CC2=C1O NZJOOMHMWFRUKT-UHFFFAOYSA-N 0.000 description 2
- WYHNENMAMZDMGO-UHFFFAOYSA-N 2-[2-methyl-3-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]propyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCC(CNC(N)=N)C)=CC=CC2=C1O WYHNENMAMZDMGO-UHFFFAOYSA-N 0.000 description 2
- ZZJJWVFOSDHSLW-UHFFFAOYSA-N 2-[3-[(1-chloroisoquinolin-5-yl)sulfonylamino]-2-methylpropyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCC(CNC(N)=N)C)=CC=CC2=C1Cl ZZJJWVFOSDHSLW-UHFFFAOYSA-N 0.000 description 2
- KYFNVYRUPFOLAX-UHFFFAOYSA-N 2-[3-methyl-1-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]butan-2-yl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCC(C(C)C)NC(N)=N)=CC=CC2=C1O KYFNVYRUPFOLAX-UHFFFAOYSA-N 0.000 description 2
- HLSSVGIHBLCMOK-UHFFFAOYSA-N 2-[4-[(1-chloroisoquinolin-5-yl)sulfonylamino]-2-methylbutyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCCC(C)CNC(N)=N)=CC=CC2=C1Cl HLSSVGIHBLCMOK-UHFFFAOYSA-N 0.000 description 2
- YLECXZWIWZPRFE-UHFFFAOYSA-N 2-[4-[(1-oxo-2h-isoquinolin-5-yl)sulfonylamino]butyl]guanidine Chemical compound N1=CC=C2C(S(=O)(=O)NCCCCNC(=N)N)=CC=CC2=C1O YLECXZWIWZPRFE-UHFFFAOYSA-N 0.000 description 2
- IXYWTDKPXSIYLG-UHFFFAOYSA-N 3-methyl-4-[(1-oxo-2h-isoquinolin-5-yl)sulfonyl]piperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)CCN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 IXYWTDKPXSIYLG-UHFFFAOYSA-N 0.000 description 2
- PEKWCRDMZSCPBR-UHFFFAOYSA-N 4-(1-chloroisoquinolin-5-yl)sulfonyl-1,4-diazepane-1-carboximidamide Chemical compound C1CN(C(=N)N)CCCN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 PEKWCRDMZSCPBR-UHFFFAOYSA-N 0.000 description 2
- UEGOTHGVASLLJI-UHFFFAOYSA-N 4-(1-chloroisoquinolin-5-yl)sulfonyl-2,5-dimethylpiperazine-1-carboximidamide Chemical compound CC1CN(C(N)=N)C(C)CN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 UEGOTHGVASLLJI-UHFFFAOYSA-N 0.000 description 2
- FTKDGPSJSKTNNI-UHFFFAOYSA-N 4-(1-chloroisoquinolin-5-yl)sulfonylpiperazine-1-carboximidamide Chemical compound C1CN(C(=N)N)CCN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 FTKDGPSJSKTNNI-UHFFFAOYSA-N 0.000 description 2
- QYVSFVAMNCARIE-UHFFFAOYSA-N 4-[(1-oxo-2h-isoquinolin-5-yl)sulfonyl]piperazine-1-carboximidamide Chemical compound C1CN(C(=N)N)CCN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 QYVSFVAMNCARIE-UHFFFAOYSA-N 0.000 description 2
- GIADEZXEPFCAJY-UHFFFAOYSA-N 5-(2,5-dimethylpiperazin-1-yl)sulfonyl-2h-isoquinolin-1-one Chemical compound CC1CNC(C)CN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 GIADEZXEPFCAJY-UHFFFAOYSA-N 0.000 description 2
- WQHSWQPTFGTARW-UHFFFAOYSA-N 5-(3-ethylpiperazin-1-yl)sulfonyl-2h-isoquinolin-1-one Chemical compound C1CNC(CC)CN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 WQHSWQPTFGTARW-UHFFFAOYSA-N 0.000 description 2
- QQXWWAPBBSYFBA-UHFFFAOYSA-N 5-(3-methylpiperazin-1-yl)sulfonyl-2h-isoquinolin-1-one Chemical compound C1CNC(C)CN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 QQXWWAPBBSYFBA-UHFFFAOYSA-N 0.000 description 2
- PRLBSYVUDMVRQG-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)sulfonyl-2h-isoquinolin-1-one Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 PRLBSYVUDMVRQG-UHFFFAOYSA-N 0.000 description 2
- QAZBOXNKUGJKGF-UHFFFAOYSA-N 5-[3-(2-methylpropyl)piperazin-1-yl]sulfonyl-2h-isoquinolin-1-one Chemical compound C1CNC(CC(C)C)CN1S(=O)(=O)C1=CC=CC2=C(O)N=CC=C12 QAZBOXNKUGJKGF-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000283977 Oryctolagus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
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- MNBCKNPSBQGEOL-UHFFFAOYSA-N n-(3-amino-2-methylbutyl)-1-chloroisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(C)C(N)C)=CC=CC2=C1Cl MNBCKNPSBQGEOL-UHFFFAOYSA-N 0.000 description 2
- ALCFGPGJCADNGY-UHFFFAOYSA-N n-(3-amino-2-methylbutyl)-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC(C)C(N)C)=CC=CC2=C1O ALCFGPGJCADNGY-UHFFFAOYSA-N 0.000 description 2
- VKESMKSGPXOCME-UHFFFAOYSA-N n-(3-aminooctan-2-yl)-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NC(C)C(N)CCCCC)=CC=CC2=C1O VKESMKSGPXOCME-UHFFFAOYSA-N 0.000 description 2
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- AWZVOOPFMFOCFS-UHFFFAOYSA-N n-[2-(methylamino)ethyl]-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCNC)=CC=CC2=C1O AWZVOOPFMFOCFS-UHFFFAOYSA-N 0.000 description 2
- HUJCGCODFKPWIP-UHFFFAOYSA-N n-[2-[cyclohexyl(methyl)amino]ethyl]-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound C=1C=CC2=C(O)N=CC=C2C=1S(=O)(=O)NCCN(C)C1CCCCC1 HUJCGCODFKPWIP-UHFFFAOYSA-N 0.000 description 2
- VFFUTDLEEDRUDU-UHFFFAOYSA-N n-[3-(dibutylamino)propyl]-1-oxo-2h-isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCCN(CCCC)CCCC)=CC=CC2=C1O VFFUTDLEEDRUDU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- MUDVUWOLBJRUGF-UHFFFAOYSA-N (c-methoxycarbonimidoyl)azanium;chloride Chemical compound Cl.COC(N)=N MUDVUWOLBJRUGF-UHFFFAOYSA-N 0.000 description 1
- YQSJLQCFWPSKKI-UHFFFAOYSA-N 1-chloro-5-(3-ethylpiperazin-1-yl)sulfonylisoquinoline Chemical compound C1CNC(CC)CN1S(=O)(=O)C1=CC=CC2=C(Cl)N=CC=C12 YQSJLQCFWPSKKI-UHFFFAOYSA-N 0.000 description 1
- KGACEAILWGQILV-UHFFFAOYSA-N 1-chloro-n-(2-hydroxyethyl)isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCCO)=CC=CC2=C1Cl KGACEAILWGQILV-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- SADHVOSOZBAAGL-UHFFFAOYSA-N 3-(trifluoromethoxy)aniline Chemical compound NC1=CC=CC(OC(F)(F)F)=C1 SADHVOSOZBAAGL-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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- STDZGCHUVZWDNY-UHFFFAOYSA-N 5-piperazin-1-ylsulfonyl-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(O)=NC=CC2=C1S(=O)(=O)N1CCNCC1 STDZGCHUVZWDNY-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- GZZCYMXZJQCAJU-UHFFFAOYSA-N isoquinoline-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=NC=CC2=C1 GZZCYMXZJQCAJU-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 239000007788 liquid Substances 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
- 238000005259 measurement Methods 0.000 description 1
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27390884A JPS61152658A (ja) | 1984-12-27 | 1984-12-27 | 置換されたイソキノリンスルホンアミド誘導体 |
| AT85116520T ATE64598T1 (de) | 1984-12-27 | 1985-12-23 | Substituierte isochinolinsulfonyl-verbindungen. |
| DE8585116520T DE3583287D1 (de) | 1984-12-27 | 1985-12-23 | Substituierte isochinolinsulfonyl-verbindungen. |
| EP19850116520 EP0187371B1 (en) | 1984-12-27 | 1985-12-23 | Substituted isoquinolinesulfonyl compounds |
| US06813973 US4678783B1 (en) | 1983-11-04 | 1985-12-27 | Substituted isoquinolinesulfonyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27390884A JPS61152658A (ja) | 1984-12-27 | 1984-12-27 | 置換されたイソキノリンスルホンアミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61152658A JPS61152658A (ja) | 1986-07-11 |
| JPH0481986B2 true JPH0481986B2 (cs) | 1992-12-25 |
Family
ID=17534244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27390884A Granted JPS61152658A (ja) | 1983-11-04 | 1984-12-27 | 置換されたイソキノリンスルホンアミド誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61152658A (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0667926B2 (ja) * | 1985-11-12 | 1994-08-31 | 旭化成工業株式会社 | 環状のイソキノリンスルホンアミド誘導体 |
| JP2720348B2 (ja) * | 1989-03-30 | 1998-03-04 | 旭化成工業株式会社 | 脳細胞機能障害改善剤 |
| DE69606721T2 (de) * | 1995-07-03 | 2000-06-21 | Asahi Chemical Ind | 1-(5-isochinolinsulfonyl)homopiperazin hydrochlorid |
| AU1557497A (en) * | 1996-02-02 | 1997-08-22 | Nippon Shinyaku Co. Ltd. | Isoquinoline derivatives and drugs |
| DK0956865T4 (da) | 1996-08-12 | 2010-11-22 | Mitsubishi Tanabe Pharma Corp | Medikamenter omfattende Rho-kinaseinhibitor |
| WO1999054306A1 (fr) * | 1997-03-10 | 1999-10-28 | Hiroyoshi Hidaka | Derives isoquinolinesulfonamide et medicaments integrant ces derives comme principe actif |
| JP5042419B2 (ja) * | 2001-08-15 | 2012-10-03 | 旭化成ファーマ株式会社 | 骨形成促進剤および骨形成促進組成物 |
| JP4854070B2 (ja) * | 2004-01-29 | 2012-01-11 | 旭化成ファーマ株式会社 | バイパス術に伴う血管攣縮治療剤 |
-
1984
- 1984-12-27 JP JP27390884A patent/JPS61152658A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61152658A (ja) | 1986-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |