JPS6130677B2 - - Google Patents
Info
- Publication number
- JPS6130677B2 JPS6130677B2 JP55083710A JP8371080A JPS6130677B2 JP S6130677 B2 JPS6130677 B2 JP S6130677B2 JP 55083710 A JP55083710 A JP 55083710A JP 8371080 A JP8371080 A JP 8371080A JP S6130677 B2 JPS6130677 B2 JP S6130677B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- same
- general formula
- carbon atoms
- 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 Sulfonyloxy group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- VLKFUKUDAYVDES-UHFFFAOYSA-N C1=CC2=NSC=CC2=C2C1=NC=N2 Chemical class C1=CC2=NSC=CC2=C2C1=NC=N2 VLKFUKUDAYVDES-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- GGYKIRSLNIYKGV-UHFFFAOYSA-N imidazo[4,5-f][2,1]benzothiazin-2-ylmethanol Chemical class C1=CC2=NSC=CC2=C2C1=NC(CO)=N2 GGYKIRSLNIYKGV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000000101 thioether group Chemical group 0.000 claims description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- IVGGSOCMYLFYSI-UHFFFAOYSA-N imidazo[4,5-f][2,1]benzothiazin-2-ylmethyl 4-methylbenzenesulfonate Chemical class C1=CC(C)=CC=C1S(=O)(=O)OCC1=NC2=C3C=CSN=C3C=CC2=N1 IVGGSOCMYLFYSI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000001816 cooling Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000017531 blood circulation Effects 0.000 description 6
- 210000001105 femoral artery Anatomy 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XGIRELGQSVHYNJ-UHFFFAOYSA-N 2h-[1,3]thiazino[3,2-a]benzimidazole Chemical compound C1=CC=C2N(C=CCS3)C3=NC2=C1 XGIRELGQSVHYNJ-UHFFFAOYSA-N 0.000 description 5
- PJHUFMVAQSHQER-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1SC2=NC3=CC=CC=C3N2CC1 PJHUFMVAQSHQER-UHFFFAOYSA-N 0.000 description 5
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229960001789 papaverine Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 230000000304 vasodilatating effect Effects 0.000 description 3
- NFFPFTGFVSWSTH-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC(C=CC(Cl)=O)=CC(OC)=C1OC NFFPFTGFVSWSTH-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- UOTMYNBWXDUBNX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolin-2-ium;chloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 UOTMYNBWXDUBNX-UHFFFAOYSA-N 0.000 description 1
- KXKGOJGQVRZPHL-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethyl)-1,4-diazepan-1-yl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)N2CCN(CC3SC=4N(C5=CC=CC=C5N=4)CC3)CCC2)=C1 KXKGOJGQVRZPHL-UHFFFAOYSA-N 0.000 description 1
- LVEFUEVTZVDIHF-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethyl)piperazin-1-yl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)N2CCN(CC3SC=4N(C5=CC=CC=C5N=4)CC3)CC2)=C1 LVEFUEVTZVDIHF-UHFFFAOYSA-N 0.000 description 1
- JVDWKJQBWSKJOJ-UHFFFAOYSA-N 1-bromo-3-methylbuta-1,3-diene Chemical compound CC(=C)C=CBr JVDWKJQBWSKJOJ-UHFFFAOYSA-N 0.000 description 1
- CZEOIFUCTVQWHO-UHFFFAOYSA-N 2-(3-methylbuta-1,3-dienoxymethyl)-3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazole Chemical compound C1=CC=C2N3CCC(COC=CC(=C)C)SC3=NC2=C1 CZEOIFUCTVQWHO-UHFFFAOYSA-N 0.000 description 1
- HJMYALXESNFCFD-UHFFFAOYSA-N 2-(benzylsulfanylmethyl)-3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazole Chemical compound C1CN(C2=CC=CC=C2N=2)C=2SC1CSCC1=CC=CC=C1 HJMYALXESNFCFD-UHFFFAOYSA-N 0.000 description 1
- LOEYQALCDYZEQK-UHFFFAOYSA-N 2-[4-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethyl)piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1CN(CC2SC=3N(C4=CC=CC=C4N=3)CC2)CCN1CC(=O)N1CCCC1 LOEYQALCDYZEQK-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- ISONAIWULZXKLB-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethanamine Chemical compound C1=CC=C2N3CCC(CN)SC3=NC2=C1 ISONAIWULZXKLB-UHFFFAOYSA-N 0.000 description 1
- FXRRIXHECVDKRG-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethanol Chemical compound C1=CC=C2N3CCC(CO)SC3=NC2=C1 FXRRIXHECVDKRG-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- CTEBIGXPSGRZJF-UHFFFAOYSA-N imidazo[4,5-c]thiazine Chemical class C1=CSN=C2N=CN=C21 CTEBIGXPSGRZJF-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- HOPLTMSGHBXKJW-UHFFFAOYSA-N n-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-ylmethyl)-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NCC1SC2=NC3=CC=CC=C3N2CC1 HOPLTMSGHBXKJW-UHFFFAOYSA-N 0.000 description 1
- AOZQHGVGIXUVGY-UHFFFAOYSA-N n-benzyl-1-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-2-yl)methanamine Chemical compound C1CN(C2=CC=CC=C2N=2)C=2SC1CNCC1=CC=CC=C1 AOZQHGVGIXUVGY-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229960003207 papaverine hydrochloride Drugs 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 210000002385 vertebral artery Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8371080A JPS579787A (en) | 1980-06-20 | 1980-06-20 | Thiazinobenzimidazole derivative and its preparation |
| US06/240,219 US4369309A (en) | 1980-06-20 | 1981-03-03 | Thiazinobenzimidazole derivatives |
| CA000372278A CA1169424A (en) | 1980-06-20 | 1981-03-04 | Thiazinobenzimidazole derivatives and preparation process thereof |
| US06/417,596 US4450109A (en) | 1980-06-20 | 1982-09-13 | Thiazinobenzimidazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8371080A JPS579787A (en) | 1980-06-20 | 1980-06-20 | Thiazinobenzimidazole derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS579787A JPS579787A (en) | 1982-01-19 |
| JPS6130677B2 true JPS6130677B2 (US06277897-20010821-C00009.png) | 1986-07-15 |
Family
ID=13810048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8371080A Granted JPS579787A (en) | 1980-06-20 | 1980-06-20 | Thiazinobenzimidazole derivative and its preparation |
Country Status (3)
| Country | Link |
|---|---|
| US (2) | US4369309A (US06277897-20010821-C00009.png) |
| JP (1) | JPS579787A (US06277897-20010821-C00009.png) |
| CA (1) | CA1169424A (US06277897-20010821-C00009.png) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS579787A (en) * | 1980-06-20 | 1982-01-19 | Ss Pharmaceut Co Ltd | Thiazinobenzimidazole derivative and its preparation |
| GR81595B (US06277897-20010821-C00009.png) * | 1983-06-18 | 1984-12-11 | Wyeth John & Brother Ltd | |
| JP2519731Y2 (ja) * | 1990-04-18 | 1996-12-11 | トヨタ自動車株式会社 | 識別マーク付き樹脂ハウジング |
| TW200808812A (en) * | 2006-04-12 | 2008-02-16 | Speedel Experimenta Ag | Imidazo compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6021596B2 (ja) * | 1980-06-20 | 1985-05-28 | エスエス製薬株式会社 | チアジノベンズイミダゾール誘導体及びその製造法 |
| JPS579787A (en) * | 1980-06-20 | 1982-01-19 | Ss Pharmaceut Co Ltd | Thiazinobenzimidazole derivative and its preparation |
| US4304908A (en) * | 1980-06-23 | 1981-12-08 | Eastman Kodak Company | Methine colorant materials and the use thereof in electrophoretic migration imaging layers and processes |
-
1980
- 1980-06-20 JP JP8371080A patent/JPS579787A/ja active Granted
-
1981
- 1981-03-03 US US06/240,219 patent/US4369309A/en not_active Expired - Fee Related
- 1981-03-04 CA CA000372278A patent/CA1169424A/en not_active Expired
-
1982
- 1982-09-13 US US06/417,596 patent/US4450109A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4369309A (en) | 1983-01-18 |
| JPS579787A (en) | 1982-01-19 |
| US4450109A (en) | 1984-05-22 |
| CA1169424A (en) | 1984-06-19 |
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