DD259865A1 - Verfahren zur herstellung neuer stickstoffarylmethoxy-thiophenderivate und deren pharmazeutisch verwendbarer saeureadditionssalze - Google Patents
Verfahren zur herstellung neuer stickstoffarylmethoxy-thiophenderivate und deren pharmazeutisch verwendbarer saeureadditionssalze Download PDFInfo
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- DD259865A1 DD259865A1 DD87299272A DD29927287A DD259865A1 DD 259865 A1 DD259865 A1 DD 259865A1 DD 87299272 A DD87299272 A DD 87299272A DD 29927287 A DD29927287 A DD 29927287A DD 259865 A1 DD259865 A1 DD 259865A1
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- 150000001875 compounds Chemical class 0.000 claims description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- GAGPIMNSNVDGFS-UHFFFAOYSA-N 1-(5-hydroxythiophen-2-yl)hexan-1-one Chemical compound CCCCCC(=O)C1=CC=C(O)S1 GAGPIMNSNVDGFS-UHFFFAOYSA-N 0.000 claims description 5
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002617 leukotrienes Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LXELKVCSBMMSLR-UHFFFAOYSA-N 1-[5-(quinolin-2-ylmethoxy)thiophen-2-yl]hexan-1-one Chemical compound S1C(C(=O)CCCCC)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 LXELKVCSBMMSLR-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- MDVFHLPCTIVLQJ-UHFFFAOYSA-N methyl 4-(quinolin-2-ylmethoxy)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 MDVFHLPCTIVLQJ-UHFFFAOYSA-N 0.000 description 3
- FWHWSIDEKGSJBP-UHFFFAOYSA-N methyl 4-hydroxythiophene-2-carboxylate Chemical compound COC(=O)C1=CC(O)=CS1 FWHWSIDEKGSJBP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RFJBPDCVEYQQRO-UHFFFAOYSA-N 1-[5-(quinolin-2-ylmethoxy)thiophen-2-yl]hexan-1-ol Chemical compound S1C(C(O)CCCCC)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 RFJBPDCVEYQQRO-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 2
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- GIBPHPOCEHSCKO-UHFFFAOYSA-N methyl 5-(quinolin-2-ylmethoxy)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 GIBPHPOCEHSCKO-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
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- 239000002243 precursor Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- OJNQMJIBDOELCS-UHFFFAOYSA-N 1-[4-(quinolin-2-ylmethoxy)thiophen-2-yl]hexan-1-ol Chemical compound S1C(C(O)CCCCC)=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 OJNQMJIBDOELCS-UHFFFAOYSA-N 0.000 description 1
- FRFABKWZEGGDMW-UHFFFAOYSA-N 1-[4-(quinolin-2-ylmethoxy)thiophen-2-yl]hexan-1-one Chemical compound S1C(C(=O)CCCCC)=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 FRFABKWZEGGDMW-UHFFFAOYSA-N 0.000 description 1
- JYBFKXWGXQLINN-UHFFFAOYSA-N 1-[5-(pyridin-2-ylmethoxy)thiophen-2-yl]hexan-1-one Chemical compound S1C(C(=O)CCCCC)=CC=C1OCC1=CC=CC=N1 JYBFKXWGXQLINN-UHFFFAOYSA-N 0.000 description 1
- ALRNRBVFGDCSAK-UHFFFAOYSA-N 1-[5-[(2-methylpropan-2-yl)oxy]thiophen-2-yl]hexan-1-one Chemical compound CCCCCC(=O)C1=CC=C(OC(C)(C)C)S1 ALRNRBVFGDCSAK-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- ODCBXCLIDZAKHW-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]thiophene Chemical compound CC(C)(C)OC1=CC=CS1 ODCBXCLIDZAKHW-UHFFFAOYSA-N 0.000 description 1
- HHZHYQGDABFDTQ-UHFFFAOYSA-N 4-(quinolin-2-ylmethoxy)thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 HHZHYQGDABFDTQ-UHFFFAOYSA-N 0.000 description 1
- FFIUBSLJPHJUCZ-UHFFFAOYSA-N 4-hydroxythiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CS1 FFIUBSLJPHJUCZ-UHFFFAOYSA-N 0.000 description 1
- HIYAVKIYRIFSCZ-CYEMHPAKSA-N 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid Chemical compound O=C([C@@H](C)[C@H]1O[C@@]2([C@@H](C[C@H]1C)C)O[C@@H]([C@@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C1=CC=CN1 HIYAVKIYRIFSCZ-CYEMHPAKSA-N 0.000 description 1
- RDEYORKJEDLLDB-DQVHGTJVSA-N 5-Hydroperoxyeicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(\OO)=C\C=C\C(O)=O RDEYORKJEDLLDB-DQVHGTJVSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
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- 229920000084 Gum arabic Polymers 0.000 description 1
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- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- WKDAHZRKHZOGLQ-UHFFFAOYSA-N [4-(quinolin-2-ylmethoxy)thiophen-2-yl]methanol Chemical compound S1C(CO)=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 WKDAHZRKHZOGLQ-UHFFFAOYSA-N 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 1
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- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
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- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
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- ZHZKXNQCVRXTBL-UHFFFAOYSA-N methyl 4-(pyridin-2-ylmethoxy)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(OCC=2N=CC=CC=2)=C1 ZHZKXNQCVRXTBL-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
- PRFXRIUZNKLRHM-OSJNIVAESA-N prostaglandin b2 Chemical compound CCCCC[C@H](O)\C=C\C1=C(C\C=C\CCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-OSJNIVAESA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT10786 | 1986-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD259865A1 true DD259865A1 (de) | 1988-09-07 |
Family
ID=3481700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87299272A DD259865A1 (de) | 1986-01-17 | 1987-01-15 | Verfahren zur herstellung neuer stickstoffarylmethoxy-thiophenderivate und deren pharmazeutisch verwendbarer saeureadditionssalze |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4778803A (cs) |
| EP (1) | EP0229660B1 (cs) |
| JP (1) | JPH0784465B2 (cs) |
| KR (1) | KR950009826B1 (cs) |
| AT (1) | ATE56971T1 (cs) |
| AU (1) | AU588960B2 (cs) |
| CA (1) | CA1297109C (cs) |
| CS (2) | CS264287B2 (cs) |
| DD (1) | DD259865A1 (cs) |
| DE (1) | DE3765124D1 (cs) |
| DK (1) | DK21787A (cs) |
| ES (1) | ES2031833T3 (cs) |
| FI (1) | FI86063C (cs) |
| GR (1) | GR3002512T3 (cs) |
| HU (1) | HU200604B (cs) |
| NO (1) | NO165677C (cs) |
| NZ (1) | NZ218892A (cs) |
| SG (1) | SG39992G (cs) |
| YU (2) | YU45815B (cs) |
| ZA (1) | ZA87311B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT391316B (de) * | 1988-09-15 | 1990-09-25 | Ebewe Arzneimittel | Neue thienyloxy-alkylamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| AT394045B (de) * | 1989-07-05 | 1992-01-27 | Chem Pharm Forsch Gmbh | Neue sulfamoyl-thiophene, verfahren zu ihrer herstellung und ihre verwendung |
| DE10234527A1 (de) * | 2002-07-25 | 2004-02-05 | Infineon Technologies Ag | Polymerisierbare Zusammensetzung, Resist und Verfahren zur Elektronenstrahllithographie |
| TWI675033B (zh) * | 2015-01-05 | 2019-10-21 | 日商綜研化學股份有限公司 | 含有雜環的化合物、使用該化合物的聚合物及其用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5734275B2 (cs) * | 1973-07-30 | 1982-07-22 | ||
| CA1134828A (en) * | 1978-12-28 | 1982-11-02 | Tadao Tanouchi | Pyridine derivatives |
| DE2950064A1 (de) * | 1979-12-13 | 1981-06-19 | Basf Ag, 6700 Ludwigshafen | Piperidinderivate von 3-hydroxythiophen-2-carbonsaeure und -estern, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| GB2065121A (en) * | 1979-12-13 | 1981-06-24 | Pfizer Ltd | Isoquinoline Derivatives |
| GB2068950A (en) * | 1980-02-06 | 1981-08-19 | Pfizer Ltd | Pyridine Derivatives |
| GR75101B (cs) * | 1980-10-23 | 1984-07-13 | Pfizer | |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| US4631287A (en) * | 1985-04-16 | 1986-12-23 | Usv Pharmaceutical Corp. | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
-
1986
- 1986-12-23 CA CA000526227A patent/CA1297109C/en not_active Expired - Fee Related
- 1986-12-24 US US06/947,418 patent/US4778803A/en not_active Expired - Fee Related
-
1987
- 1987-01-07 FI FI870045A patent/FI86063C/fi not_active IP Right Cessation
- 1987-01-12 YU YU3487A patent/YU45815B/sh unknown
- 1987-01-13 EP EP87100347A patent/EP0229660B1/de not_active Expired - Lifetime
- 1987-01-13 ES ES198787100347T patent/ES2031833T3/es not_active Expired - Lifetime
- 1987-01-13 DE DE8787100347T patent/DE3765124D1/de not_active Expired - Fee Related
- 1987-01-13 AT AT87100347T patent/ATE56971T1/de not_active IP Right Cessation
- 1987-01-15 CS CS87280A patent/CS264287B2/cs unknown
- 1987-01-15 DD DD87299272A patent/DD259865A1/de unknown
- 1987-01-15 NO NO870162A patent/NO165677C/no unknown
- 1987-01-16 JP JP62006291A patent/JPH0784465B2/ja not_active Expired - Lifetime
- 1987-01-16 ZA ZA87311A patent/ZA87311B/xx unknown
- 1987-01-16 KR KR1019870000296A patent/KR950009826B1/ko not_active Expired - Fee Related
- 1987-01-16 HU HU87133A patent/HU200604B/hu not_active IP Right Cessation
- 1987-01-16 AU AU67638/87A patent/AU588960B2/en not_active Ceased
- 1987-01-16 DK DK021787A patent/DK21787A/da not_active Application Discontinuation
- 1987-06-12 NZ NZ218892A patent/NZ218892A/xx unknown
- 1987-10-17 CS CS877505A patent/CS264298B2/cs unknown
- 1987-12-22 YU YU2356/87A patent/YU45479B/xx unknown
-
1990
- 1990-10-30 GR GR90400478T patent/GR3002512T3/el unknown
-
1992
- 1992-04-11 SG SG399/92A patent/SG39992G/en unknown
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