CH677731A5 - Use of isoquinoline derivs. - Google Patents
Use of isoquinoline derivs. Download PDFInfo
- Publication number
- CH677731A5 CH677731A5 CH2174/88A CH217488A CH677731A5 CH 677731 A5 CH677731 A5 CH 677731A5 CH 2174/88 A CH2174/88 A CH 2174/88A CH 217488 A CH217488 A CH 217488A CH 677731 A5 CH677731 A5 CH 677731A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- group
- methoxy
- tritoqualine
- phthalidyl
- Prior art date
Links
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title abstract 4
- 208000019423 liver disease Diseases 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- IRGJVQIJENCTQF-UHFFFAOYSA-N tritoqualine Chemical group CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 IRGJVQIJENCTQF-UHFFFAOYSA-N 0.000 claims description 57
- 229960002634 tritoqualine Drugs 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 28
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 15
- 239000002775 capsule Substances 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- KMUSOPLYTZFTHI-UHFFFAOYSA-N 7-amino-4,5,6-triethoxy-3-(6-ethyl-4-methoxy-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3h-2-benzofuran-1-one Chemical compound CCN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 KMUSOPLYTZFTHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- JCNRNGDSYYXAKC-UHFFFAOYSA-N 4,5,6-triethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-7-nitro-3h-2-benzofuran-1-one Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C([N+]([O-])=O)=C2C(=O)O1 JCNRNGDSYYXAKC-UHFFFAOYSA-N 0.000 claims description 3
- AKNNEGZIBPJZJG-UHFFFAOYSA-N 6,7-dimethoxy-3-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- FOUSOWYPAPRWMA-UHFFFAOYSA-N 7-amino-3-(6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl)-4,5,6-triethoxy-3h-2-benzofuran-1-one Chemical compound CN1CCC2=CC(OC)=C(OC)C=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 FOUSOWYPAPRWMA-UHFFFAOYSA-N 0.000 claims 2
- BXRBUOIPVXWSGG-UHFFFAOYSA-N 7-amino-4,5,6-triethoxy-3-(4-methoxy-8-methyl-7,9-dihydro-6h-[1,3]dioxolo[4,5-h]isoquinolin-9-yl)-3h-2-benzofuran-1-one Chemical compound CN1CCC2=CC(OC)=C3OCOC3=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 BXRBUOIPVXWSGG-UHFFFAOYSA-N 0.000 claims 2
- 239000008247 solid mixture Substances 0.000 claims 2
- -1 lipid peroxides Chemical class 0.000 abstract description 19
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 238000001727 in vivo Methods 0.000 abstract description 2
- 241001262617 Japonica Species 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 238000012261 overproduction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000008187 granular material Substances 0.000 description 25
- 235000012054 meals Nutrition 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000546 pharmaceutical excipient Substances 0.000 description 11
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- 239000007864 aqueous solution Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 238000005469 granulation Methods 0.000 description 10
- 230000003179 granulation Effects 0.000 description 10
- 239000000454 talc Substances 0.000 description 10
- 229910052623 talc Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- 235000010980 cellulose Nutrition 0.000 description 8
- 239000008120 corn starch Substances 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 6
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 6
- 229920001592 potato starch Polymers 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 6
- 206010008909 Chronic Hepatitis Diseases 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 239000007884 disintegrant Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 208000006454 hepatitis Diseases 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- REPOQDYGCLEMFC-UHFFFAOYSA-N 4-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline Chemical compound C1CN=CC2=C1C=C1OCOC1=C2OC REPOQDYGCLEMFC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008116 calcium stearate Substances 0.000 description 4
- 235000013539 calcium stearate Nutrition 0.000 description 4
- 210000000170 cell membrane Anatomy 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000002440 hepatic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 230000003908 liver function Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 101710098398 Probable alanine aminotransferase, mitochondrial Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 238000006482 condensation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
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- 238000005303 weighing Methods 0.000 description 3
- FTLVJOVZLDLKLZ-UHFFFAOYSA-N 4,5,6-triethoxy-7-nitro-3h-2-benzofuran-1-one Chemical compound CCOC1=C(OCC)C(OCC)=C2COC(=O)C2=C1[N+]([O-])=O FTLVJOVZLDLKLZ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PAPMYQLKLNRZIR-UHFFFAOYSA-N Cotarnine Chemical compound C1CN(C)C(O)C2=C1C=C1OCOC1=C2OC PAPMYQLKLNRZIR-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
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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- 230000001154 acute effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
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- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical class C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
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- HHYNQHYHCMNEET-UHFFFAOYSA-N 3-(2-hydroxy-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-1-yl)-6,7-dimethoxy-3H-2-benzofuran-1-one Chemical compound ON1C(C2=CC(=C(C=C2CC1)OC)OC)C1OC(=O)C2=C(C(=CC=C12)OC)OC HHYNQHYHCMNEET-UHFFFAOYSA-N 0.000 description 1
- SLMOCWCRMFJOKH-UHFFFAOYSA-N 3-(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)-6,7-dimethoxy-4-nitro-3H-2-benzofuran-1-one Chemical compound CN1C(C2=CC(=C(C=C2CC1)OC)OC)C1OC(=O)C2=C(C(=CC(=C12)[N+](=O)[O-])OC)OC SLMOCWCRMFJOKH-UHFFFAOYSA-N 0.000 description 1
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- ARDQVQOWCIYLER-UHFFFAOYSA-N 4-amino-3-(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)-6,7-dimethoxy-3H-2-benzofuran-1-one Chemical compound CN1C(C2=CC(=C(C=C2CC1)OC)OC)C1OC(=O)C2=C(C(=CC(=C12)N)OC)OC ARDQVQOWCIYLER-UHFFFAOYSA-N 0.000 description 1
- LMUQVJGWTVHGDX-UHFFFAOYSA-N 4-bromo-3-(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)-6,7-dimethoxy-3H-2-benzofuran-1-one Chemical compound CN1C(C2=CC(=C(C=C2CC1)OC)OC)C1OC(=O)C2=C(C(=CC(=C12)Br)OC)OC LMUQVJGWTVHGDX-UHFFFAOYSA-N 0.000 description 1
- XXANNZJIZQTCBP-UHFFFAOYSA-N 4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline Chemical compound C1CN(C)CC2=C1C=C1OCOC1=C2OC XXANNZJIZQTCBP-UHFFFAOYSA-N 0.000 description 1
- OIUUEDTVPIUEGI-UHFFFAOYSA-N 6,7-dimethoxy-3-(2-methyl-6-methylsulfanyl-3,4-dihydro-1H-isoquinolin-1-yl)-3H-2-benzofuran-1-one Chemical compound CN1C(C2=CC=C(C=C2CC1)SC)C1OC(=O)C2=C(C(=CC=C12)OC)OC OIUUEDTVPIUEGI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69230985A | 1985-01-17 | 1985-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH677731A5 true CH677731A5 (en) | 1991-06-28 |
Family
ID=24780061
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2174/88A CH677731A5 (en) | 1985-01-17 | 1986-01-17 | Use of isoquinoline derivs. |
| CH167/86A CH670642A5 (enExample) | 1985-01-17 | 1986-01-17 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH167/86A CH670642A5 (enExample) | 1985-01-17 | 1986-01-17 |
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| Country | Link |
|---|---|
| EP (1) | EP0201359A3 (enExample) |
| JP (2) | JPS61165326A (enExample) |
| BE (1) | BE904059A (enExample) |
| CH (2) | CH677731A5 (enExample) |
| FR (1) | FR2578164B1 (enExample) |
| IT (1) | IT1213024B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63270678A (ja) * | 1987-04-30 | 1988-11-08 | Mitsui Petrochem Ind Ltd | 新規含窒素化合物 |
| US20050049278A1 (en) * | 2003-08-27 | 2005-03-03 | Youssef Bennani | Benzo[1,3]dioxole compounds, pharmaceutical compositions thereof, and processes of making and using the same |
| CN101735229A (zh) * | 2009-12-24 | 2010-06-16 | 沈阳药科大学 | 四氢异喹啉类化合物及其制备方法和用途 |
| FR3111071B1 (fr) * | 2020-06-04 | 2023-01-13 | H4 Orphan Pharma | Utilisation de ligands multifonctionnels pour traiter les syndromes de détresse respiratoire et le choc cytokinique liés aux infections virales à coronavirus. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1206909B (de) * | 1959-08-14 | 1965-12-16 | Maurice Jeanson | Verfahren zur Herstellung von Inhibitoren der Histidindecarboxylase |
| FR2424271A1 (fr) * | 1978-04-28 | 1979-11-23 | Laire Chimie Sa De | Derives de phtalidyl-isoquinoleines, leur preparation et leur application comme medicaments |
| EP0028279B1 (fr) * | 1979-10-22 | 1983-02-16 | Calaire Chimie S.A. | Dérivés de phtalidyl-isoquinoléines, leur préparation et leur application comme médicaments |
-
1986
- 1986-01-14 JP JP61006118A patent/JPS61165326A/ja active Pending
- 1986-01-14 JP JP61006117A patent/JPS61165327A/ja active Pending
- 1986-01-17 EP EP86400095A patent/EP0201359A3/en not_active Withdrawn
- 1986-01-17 CH CH2174/88A patent/CH677731A5/fr not_active IP Right Cessation
- 1986-01-17 IT IT8619100A patent/IT1213024B/it active
- 1986-01-17 BE BE0/216148A patent/BE904059A/fr not_active IP Right Cessation
- 1986-01-17 CH CH167/86A patent/CH670642A5/fr not_active IP Right Cessation
- 1986-01-17 FR FR868600651A patent/FR2578164B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0201359A3 (en) | 1989-07-19 |
| FR2578164A1 (fr) | 1986-09-05 |
| JPS61165326A (ja) | 1986-07-26 |
| JPS61165327A (ja) | 1986-07-26 |
| CH670642A5 (enExample) | 1989-06-30 |
| FR2578164B1 (fr) | 1990-08-10 |
| IT1213024B (it) | 1989-12-07 |
| EP0201359A2 (en) | 1986-11-12 |
| IT8619100A0 (it) | 1986-01-17 |
| BE904059A (fr) | 1986-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |