CH484095A - Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren - Google Patents
Verfahren zur Herstellung von neuen heterocyclischen CarbonsäurenInfo
- Publication number
- CH484095A CH484095A CH1807069A CH1807069A CH484095A CH 484095 A CH484095 A CH 484095A CH 1807069 A CH1807069 A CH 1807069A CH 1807069 A CH1807069 A CH 1807069A CH 484095 A CH484095 A CH 484095A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- formula
- group
- benzofuran
- halogen
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- IHZAGSISYYKXQJ-UHFFFAOYSA-N 1,4-dimethylindole-2-carboxylic acid Chemical compound CC1=CC=CC2=C1C=C(C(O)=O)N2C IHZAGSISYYKXQJ-UHFFFAOYSA-N 0.000 description 3
- IIYDTSAAECYHAE-UHFFFAOYSA-N 2-methylidenebutanoyl chloride Chemical compound CCC(=C)C(Cl)=O IIYDTSAAECYHAE-UHFFFAOYSA-N 0.000 description 3
- FDOKRIDWESVKTM-UHFFFAOYSA-N 4-chloro-5-(2-methylidenebutanoyl)-1H-indole-2-carboxylic acid Chemical compound ClC1=C2C=C(NC2=CC=C1C(C(CC)=C)=O)C(=O)O FDOKRIDWESVKTM-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 2
- VXZHQADIRFFCMJ-UHFFFAOYSA-N 4-chloro-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1Cl VXZHQADIRFFCMJ-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical compound CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- UWWHJLKVWYOXKR-UHFFFAOYSA-N 5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1)CC UWWHJLKVWYOXKR-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IKMJGHPYOYVETB-UHFFFAOYSA-N 1,4-dioxane;ethyl acetate Chemical compound CCOC(C)=O.C1COCCO1 IKMJGHPYOYVETB-UHFFFAOYSA-N 0.000 description 1
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- MAHAMBLNIDMREX-UHFFFAOYSA-N 1-methylindole-2-carboxylic acid Chemical compound C1=CC=C2N(C)C(C(O)=O)=CC2=C1 MAHAMBLNIDMREX-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- CYTFMBZVPUBGMY-UHFFFAOYSA-N 3,6-dimethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(OC2=C1C=C(C(=C2)C)C(C(CC)=C)=O)C(=O)O CYTFMBZVPUBGMY-UHFFFAOYSA-N 0.000 description 1
- RYPIRYIQTPHBCI-UHFFFAOYSA-N 4,6-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC(C)=C2C=C(C(O)=O)OC2=C1 RYPIRYIQTPHBCI-UHFFFAOYSA-N 0.000 description 1
- YVEZTZZKJXJOEF-UHFFFAOYSA-N 4,6-dimethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C(=CC2=C1C=C(O2)C(=O)O)C)C(C(CC)=C)=O YVEZTZZKJXJOEF-UHFFFAOYSA-N 0.000 description 1
- UPUYXAOCRSQHJL-UHFFFAOYSA-N 4-chloro-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound ClC1=C(C=CC2=C1C=C(O2)C(=O)O)C(C(CC)=C)=O UPUYXAOCRSQHJL-UHFFFAOYSA-N 0.000 description 1
- QMSCXKCJGFIXDF-UHFFFAOYSA-N 4-methyl-1h-indole-2-carboxylic acid Chemical compound CC1=CC=CC2=C1C=C(C(O)=O)N2 QMSCXKCJGFIXDF-UHFFFAOYSA-N 0.000 description 1
- IPBNJWPJVRBOCK-UHFFFAOYSA-N 4-methyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=CC2=C1C=C(O2)C(=O)O)C(C(CC)=C)=O IPBNJWPJVRBOCK-UHFFFAOYSA-N 0.000 description 1
- FTWKTEYMZJWOSZ-UHFFFAOYSA-N 6-chloro-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)Cl)CC FTWKTEYMZJWOSZ-UHFFFAOYSA-N 0.000 description 1
- FRPJVIKXPDPKEW-UHFFFAOYSA-N 6-ethoxy-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C(C)OC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CC)=C)=O FRPJVIKXPDPKEW-UHFFFAOYSA-N 0.000 description 1
- PSBUPVYEUWGKHS-UHFFFAOYSA-N 6-methoxy-5-(2-methylprop-2-enoyl)-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(C)=C)=O PSBUPVYEUWGKHS-UHFFFAOYSA-N 0.000 description 1
- VMQDSECUDLRTDK-UHFFFAOYSA-N 6-methyl-5-(3-methyl-2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(C(C)C)=C)=O VMQDSECUDLRTDK-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GJVQPEVJKAYSFZ-UHFFFAOYSA-N CCC(C(C(C=CC1=C2C(Cl)=C(C(O)=O)O1)=C2Cl)=O)=C Chemical compound CCC(C(C(C=CC1=C2C(Cl)=C(C(O)=O)O1)=C2Cl)=O)=C GJVQPEVJKAYSFZ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001466453 Laminaria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 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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- DLTWLXUYSLIIQN-UHFFFAOYSA-N furacrinic acid Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)=C2 DLTWLXUYSLIIQN-UHFFFAOYSA-N 0.000 description 1
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- DWEJZKONIFQYPG-UHFFFAOYSA-N methyl 1,4-dimethylindole-2-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)OC)=CC2=C1C DWEJZKONIFQYPG-UHFFFAOYSA-N 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
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- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup 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
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1807069A CH484095A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1807069A CH484095A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
| CH1076467A CH484092A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH484095A true CH484095A (de) | 1970-01-15 |
Family
ID=4366590
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1807069A CH484095A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
| CH1806969A CH484094A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1806969A CH484094A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen |
Country Status (15)
| Country | Link |
|---|---|
| AT (4) | AT280272B (fi) |
| BG (2) | BG15386A3 (fi) |
| BR (1) | BR6800997D0 (fi) |
| CH (2) | CH484095A (fi) |
| CS (2) | CS153467B2 (fi) |
| DK (1) | DK121087B (fi) |
| FI (2) | FI49415C (fi) |
| GT (1) | GT197640170A (fi) |
| IE (1) | IE32222B1 (fi) |
| IL (1) | IL30442A (fi) |
| NO (1) | NO122751B (fi) |
| PL (1) | PL69796B1 (fi) |
| SE (1) | SE364270B (fi) |
| SU (1) | SU393827A3 (fi) |
| YU (1) | YU32705B (fi) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2467004C2 (ru) * | 2010-10-07 | 2012-11-20 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | СПОСОБ ПОЛУЧЕНИЯ МЕТИЛОВОГО ЭФИРА 2-БЕНЗО[b]ФУРАНКАРБОНОВОЙ КИСЛОТЫ |
-
1967
- 1967-07-28 CH CH1807069A patent/CH484095A/de not_active IP Right Cessation
- 1967-07-28 CH CH1806969A patent/CH484094A/de not_active IP Right Cessation
-
1968
- 1968-07-19 DK DK351368AA patent/DK121087B/da unknown
- 1968-07-19 FI FI682063A patent/FI49415C/fi active
- 1968-07-19 SE SE09915/68A patent/SE364270B/xx unknown
- 1968-07-19 NO NO2865/68A patent/NO122751B/no unknown
- 1968-07-19 FI FI682064A patent/FI49416C/fi active
- 1968-07-25 YU YU1783/68A patent/YU32705B/xx unknown
- 1968-07-26 AT AT729868A patent/AT280272B/de not_active IP Right Cessation
- 1968-07-26 CS CS547268A patent/CS153467B2/cs unknown
- 1968-07-26 AT AT07301/68A patent/AT281811B/de not_active IP Right Cessation
- 1968-07-26 BG BG012202A patent/BG15386A3/bg unknown
- 1968-07-26 BG BG012203A patent/BG15387A3/bg unknown
- 1968-07-26 IL IL30442A patent/IL30442A/en unknown
- 1968-07-26 IE IE904/68A patent/IE32222B1/xx unknown
- 1968-07-26 AT AT06940/69A patent/AT285595B/de not_active IP Right Cessation
- 1968-07-26 PL PL1968128332A patent/PL69796B1/pl unknown
- 1968-07-26 SU SU1415775A patent/SU393827A3/ru active
- 1968-07-26 CS CS719771*1A patent/CS153468B2/cs unknown
- 1968-07-26 BR BR200997/68A patent/BR6800997D0/pt unknown
- 1968-07-26 AT AT446869A patent/AT283346B/de not_active IP Right Cessation
-
1976
- 1976-02-13 GT GT197640170A patent/GT197640170A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG15387A3 (bg) | 1976-05-10 |
| YU32705B (en) | 1975-06-30 |
| PL69796B1 (fi) | 1973-10-31 |
| SE364270B (fi) | 1974-02-18 |
| BR6800997D0 (pt) | 1973-01-02 |
| YU178368A (en) | 1974-12-31 |
| IE32222B1 (en) | 1973-05-16 |
| NO122751B (fi) | 1971-08-09 |
| FI49415B (fi) | 1975-02-28 |
| IE32222L (en) | 1969-01-28 |
| AT281811B (de) | 1970-06-10 |
| FI49416B (fi) | 1975-02-28 |
| DK121087B (da) | 1971-09-06 |
| AT280272B (de) | 1970-04-10 |
| FI49416C (fi) | 1975-06-10 |
| AT283346B (de) | 1970-08-10 |
| SU393827A3 (fi) | 1973-08-10 |
| CS153467B2 (fi) | 1974-02-25 |
| BG15386A3 (bg) | 1976-03-23 |
| CH484094A (de) | 1970-01-15 |
| FI49415C (fi) | 1975-06-10 |
| AT285595B (de) | 1970-11-10 |
| IL30442A (en) | 1972-01-27 |
| GT197640170A (es) | 1977-08-06 |
| CS153468B2 (fi) | 1974-02-25 |
| IL30442A0 (en) | 1968-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |