CA1037042A - Thiazoloisoquinolines, and process for their preparation - Google Patents
Thiazoloisoquinolines, and process for their preparationInfo
- Publication number
- CA1037042A CA1037042A CA201,128A CA201128A CA1037042A CA 1037042 A CA1037042 A CA 1037042A CA 201128 A CA201128 A CA 201128A CA 1037042 A CA1037042 A CA 1037042A
- Authority
- CA
- Canada
- Prior art keywords
- isoquinoline
- tetrahydro
- dimethoxy
- thiazolo
- cyano
- 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
- 238000000034 method Methods 0.000 title claims description 63
- 238000002360 preparation method Methods 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- -1 cyano, carboxy Chemical group 0.000 claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000011593 sulfur Substances 0.000 claims abstract description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- TZEYHTCZIQZAPS-UHFFFAOYSA-N [1,3]thiazolo[4,5-h]isoquinoline Chemical compound C1=CN=CC2=C(SC=N3)C3=CC=C21 TZEYHTCZIQZAPS-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 9
- 125000005518 carboxamido group Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 239000005864 Sulphur Substances 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 150000002537 isoquinolines Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- NKOJJXLZHFCSHK-UHFFFAOYSA-N 3-imino-8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=N)SC(C#N)=C2C2=C1C=C(OC)C(OC)=C2 NKOJJXLZHFCSHK-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
- SHLPPXXKRFINFY-UHFFFAOYSA-N isoquinolin-2-ium;bromide Chemical compound Br.C1=NC=CC2=CC=CC=C21 SHLPPXXKRFINFY-UHFFFAOYSA-N 0.000 claims description 5
- AOYLRXBAWAACHJ-UHFFFAOYSA-N 8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinolin-3-imine Chemical compound C1CN2C(=N)SC=C2C2=C1C=C(OC)C(OC)=C2 AOYLRXBAWAACHJ-UHFFFAOYSA-N 0.000 claims description 4
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012991 xanthate Substances 0.000 claims description 4
- KHZAKBHKVKPSDN-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydro-2h-isoquinolin-1-ylidene)acetonitrile Chemical compound C1CNC(=CC#N)C2=C1C=C(OC)C(OC)=C2 KHZAKBHKVKPSDN-UHFFFAOYSA-N 0.000 claims description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- ISJBQSJDQZLCSF-UHFFFAOYSA-N (4-chlorophenyl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C(Cl)C=C1 ISJBQSJDQZLCSF-UHFFFAOYSA-N 0.000 claims description 2
- WXLYUFVXBYMPNV-UHFFFAOYSA-N 1-(chloromethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.C1CN=C(CCl)C2=C1C=C(OC)C(OC)=C2 WXLYUFVXBYMPNV-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 5
- 239000012458 free base Substances 0.000 claims 4
- DCSXMUZGAXQBMU-UHFFFAOYSA-N 8,9-dimethoxy-3-oxo-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=O)SC(C#N)=C2C2=C1C=C(OC)C(OC)=C2 DCSXMUZGAXQBMU-UHFFFAOYSA-N 0.000 claims 3
- GYPOFOQUZZUVQL-UHFFFAOYSA-N 2h-isoquinolin-3-one Chemical compound C1=CC=C2C=NC(O)=CC2=C1 GYPOFOQUZZUVQL-UHFFFAOYSA-N 0.000 claims 2
- VHKUVZMLWQJUTB-UHFFFAOYSA-N 3-imino-8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carboxylic acid Chemical compound C1CN2C(=N)SC(C(O)=O)=C2C2=C1C=C(OC)C(OC)=C2 VHKUVZMLWQJUTB-UHFFFAOYSA-N 0.000 claims 2
- QRVNEOLWORUKTQ-UHFFFAOYSA-N 8,9-dihydroxy-3-imino-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile hydrochloride Chemical compound Cl.C(#N)C=1SC(N2C1C1=CC(=C(C=C1CC2)O)O)=N QRVNEOLWORUKTQ-UHFFFAOYSA-N 0.000 claims 2
- SFDNVQGVOFEYJY-UHFFFAOYSA-N 8,9-dimethoxy-1-methyl-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinolin-3-imine Chemical compound C1CN2C(=N)SC(C)=C2C2=C1C=C(OC)C(OC)=C2 SFDNVQGVOFEYJY-UHFFFAOYSA-N 0.000 claims 2
- NBVAWHIBAOACTO-UHFFFAOYSA-N 8,9-dimethoxy-1-nitro-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinolin-3-imine Chemical compound C1CN2C(=N)SC([N+]([O-])=O)=C2C2=C1C=C(OC)C(OC)=C2 NBVAWHIBAOACTO-UHFFFAOYSA-N 0.000 claims 2
- GFBJPVOPSPOBDX-UHFFFAOYSA-N 8,9-dimethoxy-1-phenyl-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinolin-3-imine Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(S2)=N)C1=C2C1=CC=CC=C1 GFBJPVOPSPOBDX-UHFFFAOYSA-N 0.000 claims 2
- DNWZEWMQQBOMDQ-UHFFFAOYSA-N 8,9-dimethoxy-3-sulfanylidene-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=S)SC(C#N)=C2C2=C1C=C(OC)C(OC)=C2 DNWZEWMQQBOMDQ-UHFFFAOYSA-N 0.000 claims 2
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims 2
- 150000003840 hydrochlorides Chemical class 0.000 claims 2
- SYNNYKUTSHLGIF-UHFFFAOYSA-N n-(1-cyano-8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinolin-3-ylidene)benzamide Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=C(C#N)SC2=NC(=O)C1=CC=CC=C1 SYNNYKUTSHLGIF-UHFFFAOYSA-N 0.000 claims 2
- 239000001117 sulphuric acid Substances 0.000 claims 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 2
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 claims 1
- PUYGDSCENMSDKC-UHFFFAOYSA-N 3-imino-8,9-dimethoxy-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile;hydrochloride Chemical compound Cl.C1CN2C(=N)SC(C#N)=C2C2=C1C=C(OC)C(OC)=C2 PUYGDSCENMSDKC-UHFFFAOYSA-N 0.000 claims 1
- OWFVBVSNUWCHFU-UHFFFAOYSA-N 8,9-diethoxy-3-imino-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=N)SC(C#N)=C2C2=C1C=C(OCC)C(OCC)=C2 OWFVBVSNUWCHFU-UHFFFAOYSA-N 0.000 claims 1
- VFKKGUXDKHEFAG-UHFFFAOYSA-N 8,9-dihydroxy-3-imino-5,6-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile Chemical compound C1CN2C(=N)SC(C#N)=C2C2=C1C=C(O)C(O)=C2 VFKKGUXDKHEFAG-UHFFFAOYSA-N 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 229940073579 ethanolamine hydrochloride Drugs 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- 238000009740 moulding (composite fabrication) Methods 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 150000003573 thiols Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 239000000376 reactant Substances 0.000 abstract description 6
- 239000007795 chemical reaction product Substances 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 239000002269 analeptic agent Substances 0.000 abstract description 2
- 230000003555 analeptic effect Effects 0.000 abstract description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 2
- 230000000241 respiratory effect Effects 0.000 abstract description 2
- 125000004434 sulfur atom Chemical group 0.000 abstract description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 46
- 239000000203 mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000001953 recrystallisation Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000009835 boiling Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 125000004122 cyclic group Chemical group 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 229940083608 sodium hydroxide Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- KLOIYEQEVSIOOO-UHFFFAOYSA-N carbocromen Chemical compound CC1=C(CCN(CC)CC)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 KLOIYEQEVSIOOO-UHFFFAOYSA-N 0.000 description 6
- 229960005003 carbocromen Drugs 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- JLTCWSBVQSZVLT-CDIPANDDSA-N (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan Chemical compound NCCCC[C@@H](C(=O)NCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1.C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 JLTCWSBVQSZVLT-CDIPANDDSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 102000005320 Posterior Pituitary Hormones Human genes 0.000 description 2
- 108010070873 Posterior Pituitary Hormones Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical compound C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 description 1
- NTASFODDPBHBAM-UHFFFAOYSA-N 1-hydroxyethylazanium;chloride Chemical compound [Cl-].CC([NH3+])O NTASFODDPBHBAM-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- IOYIDSMWPLNHRC-UHFFFAOYSA-N 2h-isoquinoline-1-thione Chemical class C1=CC=C2C(S)=NC=CC2=C1 IOYIDSMWPLNHRC-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- WKEIOLIOXBXISC-UHFFFAOYSA-N 8,9-dihydroxy-3-imino-1,5-dihydro-[1,3]thiazolo[4,3-a]isoquinoline-1-carbonitrile;dihydrate;hydrochloride Chemical compound O.O.Cl.C1N2C(=N)SC(C#N)C2=C2C=C(O)C(O)=CC2=C1 WKEIOLIOXBXISC-UHFFFAOYSA-N 0.000 description 1
- 238000003462 Bender reaction Methods 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 208000001778 Coronary Occlusion Diseases 0.000 description 1
- 206010011086 Coronary artery occlusion Diseases 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- NMEXXONQNKTRCM-UHFFFAOYSA-N [1,2]thiazolo[3,4-h]isoquinoline Chemical compound C1=NC=C2C3=CSN=C3C=CC2=C1 NMEXXONQNKTRCM-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- WNVZCNDFBUPCTL-UHFFFAOYSA-M potassium;ethoxymethanethioate Chemical compound [K+].CCOC([O-])=S WNVZCNDFBUPCTL-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000004088 pulmonary circulation Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1381A HU170680B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-30 | 1973-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037042A true CA1037042A (en) | 1978-08-22 |
Family
ID=10994482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA201,128A Expired CA1037042A (en) | 1973-05-30 | 1974-05-29 | Thiazoloisoquinolines, and process for their preparation |
Country Status (24)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163786A (en) * | 1973-05-30 | 1979-08-07 | Chinoin Pharmaceutical And Chemical Works Ltd. | Thiazoloisoquinolines with coronary and respiratory effects |
| US4062850A (en) * | 1973-05-30 | 1977-12-13 | Chinoin Pharmaceutical And Chemical Works Ltd. | Thiazoloisoquinolines with coronary and respiratory effects |
| NL169076C (nl) * | 1975-08-06 | 1982-06-01 | Rhone Poulenc Ind | Werkwijze voor het bereiden of vervaardigen van farmacologische preparaten met een analgetische en antipyretische werking, alsmede werkwijze voor het bereiden van geneeskrachtige verbindingen, welke geschikt zijn voor gebruik in dergelijke preparaten. |
| US4108999A (en) * | 1977-02-22 | 1978-08-22 | Rhone-Poulenc Industries | Thiazolo[3,4-b]isoquinoline derivatives, pharmaceutical compositions containing them and pharmaceutical methods using them |
| NL7908655A (nl) * | 1978-12-07 | 1980-06-10 | Rhone Poulenc Ind | Nieuwe thienopyridine-derivaten, de bereiding ervan, alsmede farmaceutische preparaten, die de nieuwe derivaten bevatten. |
| HU178454B (en) * | 1979-07-02 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new isoquinoline derivatives containing sulphur |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042671A (en) * | 1959-10-07 | 1962-07-03 | Pfizer & Co C | Benzopyridocolines |
| US3455933A (en) * | 1966-11-15 | 1969-07-15 | American Home Prod | Thiazolo and thiazino isoquinoline derivatives |
| US3665007A (en) * | 1970-05-04 | 1972-05-23 | Squibb & Sons Inc | Thiazolo (3,4-a) benzimidazoles and derivatives thereof |
-
1973
- 1973-05-30 HU HUCI1381A patent/HU170680B/hu unknown
-
1974
- 1974-05-24 IL IL44895A patent/IL44895A/xx unknown
- 1974-05-27 AT AT433674A patent/AT349018B/de not_active IP Right Cessation
- 1974-05-28 CS CS743796A patent/CS227001B2/cs unknown
- 1974-05-28 FR FR7418415A patent/FR2241309B1/fr not_active Expired
- 1974-05-28 SE SE7407049A patent/SE419647B/xx not_active IP Right Cessation
- 1974-05-28 US US05/473,918 patent/US3979397A/en not_active Expired - Lifetime
- 1974-05-28 CS CS746737A patent/CS226901B1/cs unknown
- 1974-05-29 DD DD178843A patent/DD119595A5/xx unknown
- 1974-05-29 CH CH733674A patent/CH622807A5/de not_active IP Right Cessation
- 1974-05-29 AR AR253962A patent/AR213611A1/es active
- 1974-05-29 FI FI1644/74A patent/FI57262C/fi active
- 1974-05-29 SU SU7402033764A patent/SU569291A3/ru active
- 1974-05-29 NO NO741939A patent/NO150281C/no unknown
- 1974-05-29 CA CA201,128A patent/CA1037042A/en not_active Expired
- 1974-05-29 YU YU1480/74A patent/YU37172B/xx unknown
- 1974-05-29 DE DE2426267A patent/DE2426267C2/de not_active Expired
- 1974-05-29 DK DK289774A patent/DK151028C/da not_active IP Right Cessation
- 1974-05-29 BE BE144870A patent/BE815679A/xx not_active IP Right Cessation
- 1974-05-30 ES ES426773A patent/ES426773A1/es not_active Expired
- 1974-05-30 BG BG026826A patent/BG22391A3/xx unknown
- 1974-05-30 JP JP49060321A patent/JPS6014038B2/ja not_active Expired
- 1974-05-30 NL NLAANVRAGE7407280,A patent/NL176944C/xx not_active IP Right Cessation
- 1974-05-30 PL PL1974171518A patent/PL101194B1/pl unknown
- 1974-06-29 EG EG74194A patent/EG11439A/xx active
-
1979
- 1979-02-12 CH CH135379A patent/CH620220A5/de not_active IP Right Cessation
-
1982
- 1982-01-04 JP JP57000010A patent/JPS591714B2/ja not_active Expired
- 1982-01-04 JP JP57000009A patent/JPS5842195B2/ja not_active Expired
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