FI87557C - Foerfarande foer framstaellning av farmakologiskt vaerdefullt naftalenderivat - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefullt naftalenderivat Download PDFInfo
- Publication number
- FI87557C FI87557C FI860089A FI860089A FI87557C FI 87557 C FI87557 C FI 87557C FI 860089 A FI860089 A FI 860089A FI 860089 A FI860089 A FI 860089A FI 87557 C FI87557 C FI 87557C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- ring
- lower alkoxy
- compound
- hydroxy
- Prior art date
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- 230000000144 pharmacologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 23
- 150000002790 naphthalenes Chemical class 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 aldehyde compound Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 26
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- DTCYXOLBEPGOHV-UHFFFAOYSA-N dimethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C2C=1C1=CC=C(OC)C(OC)=C1 DTCYXOLBEPGOHV-UHFFFAOYSA-N 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 5
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- KIRMKSWFOVIEPB-UHFFFAOYSA-N 2-bromo-1-(dimethoxymethyl)-3,4,5-trimethoxybenzene Chemical compound COC(OC)C1=CC(OC)=C(OC)C(OC)=C1Br KIRMKSWFOVIEPB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 description 5
- XLVKBGZAHXFDRM-UHFFFAOYSA-N diethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound CCOC(=O)C=1C(C(=O)OCC)=C(O)C2=CC(OC)=C(OC)C(OC)=C2C=1C1=CC=C(OC)C(OC)=C1 XLVKBGZAHXFDRM-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SWTCCCJQNPGXLQ-UHFFFAOYSA-N 1-(1-butoxyethoxy)butane Chemical compound CCCCOC(C)OCCCC SWTCCCJQNPGXLQ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- IOKYUTCABAXWAK-UHFFFAOYSA-N 3,4-dipropoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C=C1OCCC IOKYUTCABAXWAK-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010023302 HDL Cholesterol Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
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- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- UDLBGIABCAYPEG-UHFFFAOYSA-N methyl 5-(3,4-diethoxyphenyl)-8-hydroxybenzo[f][1,3]benzodioxole-6-carboxylate Chemical compound C1=C(OCC)C(OCC)=CC=C1C(C1=C2)=C(C(=O)OC)C=C(O)C1=CC1=C2OCO1 UDLBGIABCAYPEG-UHFFFAOYSA-N 0.000 description 2
- DPQLKYMWTKSNFS-UHFFFAOYSA-N methyl 5-hydroxybenzo[f][1,3]benzodioxole-8-carboxylate Chemical compound C1=C2C(C(=O)OC)=CC=C(O)C2=CC2=C1OCO2 DPQLKYMWTKSNFS-UHFFFAOYSA-N 0.000 description 2
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 2
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- MISTZQJSHHTDCF-UHFFFAOYSA-N 1-(1-propoxyethoxy)propane Chemical compound CCCOC(C)OCCC MISTZQJSHHTDCF-UHFFFAOYSA-N 0.000 description 1
- SYGGHUGFNOMYNG-UHFFFAOYSA-N 1-(3,4-diethoxyphenyl)-4-hydroxy-3-(hydroxymethyl)-6,7,8-trimethoxynaphthalene-2-carboxylic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1C1=C(C(O)=O)C(CO)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 SYGGHUGFNOMYNG-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- NGJCECHSFLMJIE-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)-hydroxymethyl]-3,4,5-trimethoxybenzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C(O)C1=C(C=O)C=C(OC)C(OC)=C1OC NGJCECHSFLMJIE-UHFFFAOYSA-N 0.000 description 1
- WCHRPSHIMRQFRS-UHFFFAOYSA-N 2-bromo-5,6-dihydro-4h-thieno[2,3-c]pyridin-7-one Chemical compound C1CNC(=O)C2=C1C=C(Br)S2 WCHRPSHIMRQFRS-UHFFFAOYSA-N 0.000 description 1
- QFBCKNMDZNOWNO-UHFFFAOYSA-N 2-o-ethyl 3-o-methyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OCC)=C(O)C2=CC(OC)=C(OC)C(OC)=C2C=1C1=CC=C(OC)C(OC)=C1 QFBCKNMDZNOWNO-UHFFFAOYSA-N 0.000 description 1
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 1
- MDWHWNRETVPUMN-UHFFFAOYSA-N 3,4-di(propan-2-yloxy)benzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1OC(C)C MDWHWNRETVPUMN-UHFFFAOYSA-N 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- SSTRYEXQYQGGAS-UHFFFAOYSA-N 3,4-diethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OCC SSTRYEXQYQGGAS-UHFFFAOYSA-N 0.000 description 1
- VAMZHXWLGRQSJS-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OC VAMZHXWLGRQSJS-UHFFFAOYSA-N 0.000 description 1
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- PXHRXDBHCHYICT-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)-hydroxymethyl]-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C(O)C1=C(OCO2)C2=CC=C1C=O PXHRXDBHCHYICT-UHFFFAOYSA-N 0.000 description 1
- OXFJWKUPPOELCX-UHFFFAOYSA-N 4-hydroxy-3h-benzo[f][2]benzofuran-1-one Chemical compound C1=CC=C2C(O)=C(COC3=O)C3=CC2=C1 OXFJWKUPPOELCX-UHFFFAOYSA-N 0.000 description 1
- OJZGSVIMJSKINR-UHFFFAOYSA-N 5-(3,4-diethoxyphenyl)-8-hydroxybenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1C(C1=C2)=C(C(O)=O)C=C(O)C1=CC1=C2OCO1 OJZGSVIMJSKINR-UHFFFAOYSA-N 0.000 description 1
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- UUWYMYFARXLEDO-UHFFFAOYSA-N dimethyl 1-(3,4-dimethoxyphenyl)-4-hydroxy-6-methoxy-7-phenylmethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C2C(C=3C=C(OC)C(OC)=CC=3)=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C1OCC1=CC=CC=C1 UUWYMYFARXLEDO-UHFFFAOYSA-N 0.000 description 1
- DQOCYKDRQPFAIG-UHFFFAOYSA-N dimethyl 4-(3,4-diethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C(OCC)C(OCC)=CC=C1C1=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 DQOCYKDRQPFAIG-UHFFFAOYSA-N 0.000 description 1
- RSHYRACMZOBDGB-UHFFFAOYSA-N dimethyl 4-(3,4-dipropoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C(OCCC)C(OCCC)=CC=C1C1=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 RSHYRACMZOBDGB-UHFFFAOYSA-N 0.000 description 1
- QYIHMCQTQJMMNW-UHFFFAOYSA-N dimethyl 4-(3-ethoxy-4-methoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C(OC)C(OCC)=CC(C=2C3=C(OC)C(OC)=C(OC)C=C3C(O)=C(C(=O)OC)C=2C(=O)OC)=C1 QYIHMCQTQJMMNW-UHFFFAOYSA-N 0.000 description 1
- SABMKICAAHGWHD-UHFFFAOYSA-N dimethyl 5,6-dichloro-4-(3,4-dimethoxyphenyl)-1-hydroxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=C(Cl)C(Cl)=C2C=1C1=CC=C(OC)C(OC)=C1 SABMKICAAHGWHD-UHFFFAOYSA-N 0.000 description 1
- WHGUGJFBBKVAFK-UHFFFAOYSA-N dimethyl 8-(3,4-diethoxyphenyl)-5-hydroxybenzo[f][1,3]benzodioxole-6,7-dicarboxylate Chemical compound C1=C(OCC)C(OCC)=CC=C1C(C1=C2)=C(C(=O)OC)C(C(=O)OC)=C(O)C1=CC1=C2OCO1 WHGUGJFBBKVAFK-UHFFFAOYSA-N 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000005976 liver dysfunction Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VHUUJNPEPCKPGF-UHFFFAOYSA-N methyl 5,8-dihydroxybenzo[f][1,3]benzodioxole-6-carboxylate Chemical compound COC(=O)C1=C(C2=CC3=C(C=C2C(=C1)O)OCO3)O VHUUJNPEPCKPGF-UHFFFAOYSA-N 0.000 description 1
- SBENHWZAAXMTNK-UHFFFAOYSA-N n-cyclohexyl-1-(3,4-dichlorophenyl)methanimine Chemical compound C1=C(Cl)C(Cl)=CC=C1C=NC1CCCCC1 SBENHWZAAXMTNK-UHFFFAOYSA-N 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP309085 | 1985-01-10 | ||
| JP309085 | 1985-01-10 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI860089A0 FI860089A0 (fi) | 1986-01-09 |
| FI860089L FI860089L (fi) | 1986-07-11 |
| FI87557B FI87557B (fi) | 1992-10-15 |
| FI87557C true FI87557C (fi) | 1993-01-25 |
Family
ID=11547645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI860089A FI87557C (fi) | 1985-01-10 | 1986-01-09 | Foerfarande foer framstaellning av farmakologiskt vaerdefullt naftalenderivat |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4771072A (OSRAM) |
| EP (1) | EP0188248B1 (OSRAM) |
| JP (3) | JPS61267541A (OSRAM) |
| KR (1) | KR890001884B1 (OSRAM) |
| CN (1) | CN1006464B (OSRAM) |
| AT (1) | ATE54441T1 (OSRAM) |
| AU (1) | AU584153B2 (OSRAM) |
| BG (2) | BG45383A3 (OSRAM) |
| DD (1) | DD270529A5 (OSRAM) |
| DE (1) | DE3672501D1 (OSRAM) |
| ES (2) | ES8705837A1 (OSRAM) |
| FI (1) | FI87557C (OSRAM) |
| HU (1) | HU196737B (OSRAM) |
| IL (1) | IL91117A0 (OSRAM) |
| MY (1) | MY101268A (OSRAM) |
| NO (1) | NO170760C (OSRAM) |
| PH (1) | PH22105A (OSRAM) |
| PT (1) | PT81814B (OSRAM) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4644072A (en) * | 1985-04-12 | 1987-02-17 | Bristol-Myers Company | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
| US5011948A (en) * | 1985-04-12 | 1991-04-30 | Bristol-Myers Company | Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof |
| JPS6310746A (ja) * | 1986-07-01 | 1988-01-18 | Tanabe Seiyaku Co Ltd | ナフタレン誘導体 |
| AT388372B (de) * | 1987-10-08 | 1989-06-12 | Tanabe Seiyaku Co | Neue naphthalinderivate und sie enthaltende pharmazeutika |
| JPH01135766A (ja) * | 1987-11-20 | 1989-05-29 | Tanabe Seiyaku Co Ltd | ビフェニル誘導体 |
| PH26342A (en) * | 1988-11-29 | 1992-04-29 | Univ Texas | Microbial cellulose modified during synthesis |
| MY105057A (en) * | 1989-01-27 | 1994-07-30 | Tanabe Seiyaku Co | A process for preparing naphthalene derivatives |
| US5003087A (en) * | 1989-02-03 | 1991-03-26 | Tanabe Seiyaku Co., Ltd. | Process for preparing a naphthalene derivative and a synthetic intermediate thereof |
| US5281720A (en) * | 1991-02-28 | 1994-01-25 | Merck Frosst Canada, Inc. | Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis |
| EP0501579A1 (en) * | 1991-02-28 | 1992-09-02 | Merck Frosst Canada Inc. | Naphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5227399A (en) * | 1991-02-28 | 1993-07-13 | Merck Frosst Canada, Inc. | Pyranylphenyl naphthalene lactones as inhibitors of leukotriene biosynthesis |
| EP0501578A1 (en) * | 1991-02-28 | 1992-09-02 | Merck Frosst Canada Inc. | Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis |
| DE69228262D1 (de) * | 1991-10-17 | 1999-03-04 | Shionogi & Co | Verfahren zum Herstellen von Lignin-Analoga und Ausgangsprodukte dafür |
| US5308852A (en) * | 1992-06-29 | 1994-05-03 | Merck Frosst Canada, Inc. | Heteroarylnaphthalenes as inhibitors of leukotriene biosynthesis |
| US5426109A (en) * | 1992-08-27 | 1995-06-20 | Merck Frosst Canada, Inc. | Phenylnaphthalene hydroxy acids |
| US5350744A (en) * | 1992-08-27 | 1994-09-27 | Merck Frosst Canada, Inc. | Phenylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5428060A (en) * | 1992-08-27 | 1995-06-27 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5252599A (en) * | 1992-08-27 | 1993-10-12 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene hydroxy acids as inhibitors of leukotriene biosynthesis |
| CA2121060C (en) * | 1993-04-16 | 2004-04-06 | Sachio Mori | Preparation of lignan analogues |
| ID18046A (id) * | 1996-08-20 | 1998-02-19 | Takeda Chemical Industries Ltd | Senyawa siklik campuran, pembuatan dan penngunaannya. |
| CA2341540A1 (en) | 1998-08-25 | 2000-03-02 | Yale University | Inhibition and treatment of hepatitis b virus and flavivirus by helioxanthin and its analogs |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| MXPA01012494A (es) | 1999-06-01 | 2002-07-02 | Univ Texas Southwestern Med Ct | Metodo para tratar perdida capilar con el uso de compuestos sulfonil tiromimeticos. |
| JP2003500432A (ja) | 1999-06-01 | 2003-01-07 | ザ・ユニバーシティ・オブ・テキサス・サウスウエスタン・メディカル・センター | ジフェニルエーテル誘導体を用いて脱毛症を処置する方法 |
| SE0102168D0 (sv) | 2001-06-19 | 2001-06-19 | Karolinska Innovations Ab | New use and new compounds |
| BR0212254A (pt) * | 2001-08-28 | 2004-10-19 | Sankyo Co | Composição farmaceutica |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| MX382960B (es) | 2011-10-28 | 2025-03-13 | Shire Human Genetic Therapies | Inhibidores de la recirculación de ácidos biliares para el tratamiento de hipercolemia y enfermedad hepática colestásica. |
| EA030839B1 (ru) | 2011-10-28 | 2018-10-31 | ЛУМЕНА ФАРМАСЬЮТИКАЛС ЭлЭлСи | Ингибиторы рециклинга желчных кислот при лечении холестатических заболеваний печени у детей |
| CA2907214A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of barrett's esophagus and gastroesophageal reflux disease |
| KR20230152818A (ko) | 2013-03-15 | 2023-11-03 | 샤이어 휴먼 지네틱 테라피즈 인크. | 원발성 담관염 및 염증성 장 질환 치료용 담즙산 재순환 억제제 |
| WO2015153653A1 (en) * | 2014-03-31 | 2015-10-08 | Ohio State Innovation Foundation | Arylnaphthalene lactone derivatives and methods of making and using thereof |
| WO2017147624A1 (en) | 2016-02-26 | 2017-08-31 | Ohio State Innovation Foundation | Antitumor arylnaphthalene ligand glycosides |
| AU2020221834B2 (en) | 2019-02-12 | 2025-10-23 | Mirum Pharmaceuticals, Inc. | Genotype and dose-dependent response to an ASBTI in patients with bile salt export pump deficiency |
-
1985
- 1985-12-30 US US06/814,805 patent/US4771072A/en not_active Expired - Fee Related
- 1985-12-30 NO NO855355A patent/NO170760C/no unknown
- 1985-12-30 ES ES550578A patent/ES8705837A1/es not_active Expired
- 1985-12-31 AU AU51751/85A patent/AU584153B2/en not_active Ceased
-
1986
- 1986-01-08 PH PH33266A patent/PH22105A/en unknown
- 1986-01-08 JP JP61002624A patent/JPS61267541A/ja active Pending
- 1986-01-09 BG BG073061A patent/BG45383A3/xx unknown
- 1986-01-09 FI FI860089A patent/FI87557C/fi not_active IP Right Cessation
- 1986-01-09 KR KR1019860000074A patent/KR890001884B1/ko not_active Expired
- 1986-01-09 PT PT81814A patent/PT81814B/pt not_active IP Right Cessation
- 1986-01-09 BG BG082397A patent/BG45385A3/xx unknown
- 1986-01-09 HU HU8690A patent/HU196737B/hu not_active IP Right Cessation
- 1986-01-10 AT AT86100282T patent/ATE54441T1/de not_active IP Right Cessation
- 1986-01-10 CN CN86100090A patent/CN1006464B/zh not_active Expired
- 1986-01-10 DE DE8686100282T patent/DE3672501D1/de not_active Expired - Lifetime
- 1986-01-10 EP EP86100282A patent/EP0188248B1/en not_active Expired - Lifetime
- 1986-09-03 ES ES557052A patent/ES8801239A1/es not_active Expired
-
1987
- 1987-07-15 MY MYPI87001017A patent/MY101268A/en unknown
-
1988
- 1988-01-15 DD DD88312249A patent/DD270529A5/de not_active IP Right Cessation
- 1988-12-08 JP JP63310353A patent/JPH0272136A/ja active Pending
- 1988-12-08 JP JP63310354A patent/JPH0272170A/ja active Granted
-
1989
- 1989-07-26 IL IL91117A patent/IL91117A0/xx unknown
-
1990
- 1990-01-02 US US07/459,859 patent/US5070103A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: TANABE SEIYAKU CO., . LTD. |