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
- 229960000583 acetic acid Drugs 0.000 description 1
- 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
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 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
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 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
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 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
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 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
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan 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) | AT281811B (xx) |
BG (2) | BG15387A3 (xx) |
BR (1) | BR6800997D0 (xx) |
CH (2) | CH484095A (xx) |
CS (2) | CS153467B2 (xx) |
DK (1) | DK121087B (xx) |
FI (2) | FI49415C (xx) |
GT (1) | GT197640170A (xx) |
IE (1) | IE32222B1 (xx) |
IL (1) | IL30442A (xx) |
NO (1) | NO122751B (xx) |
PL (1) | PL69796B1 (xx) |
SE (1) | SE364270B (xx) |
SU (1) | SU393827A3 (xx) |
YU (1) | YU32705B (xx) |
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 FI FI682063A patent/FI49415C/fi active
- 1968-07-19 DK DK351368AA patent/DK121087B/da unknown
- 1968-07-19 NO NO2865/68A patent/NO122751B/no unknown
- 1968-07-19 SE SE09915/68A patent/SE364270B/xx unknown
- 1968-07-19 FI FI682064A patent/FI49416C/fi active
- 1968-07-25 YU YU1783/68A patent/YU32705B/xx unknown
- 1968-07-26 BG BG012203A patent/BG15387A3/bg unknown
- 1968-07-26 PL PL1968128332A patent/PL69796B1/pl unknown
- 1968-07-26 BR BR200997/68A patent/BR6800997D0/pt unknown
- 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 SU SU1415775A patent/SU393827A3/ru active
- 1968-07-26 AT AT729868A patent/AT280272B/de not_active IP Right Cessation
- 1968-07-26 CS CS719771*1A patent/CS153468B2/cs 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 AT AT446869A patent/AT283346B/de not_active IP Right Cessation
- 1968-07-26 IL IL30442A patent/IL30442A/en unknown
-
1976
- 1976-02-13 GT GT197640170A patent/GT197640170A/es unknown
Also Published As
Publication number | Publication date |
---|---|
BG15386A3 (bg) | 1976-03-23 |
SE364270B (xx) | 1974-02-18 |
YU32705B (en) | 1975-06-30 |
IE32222L (en) | 1969-01-28 |
FI49415C (fi) | 1975-06-10 |
PL69796B1 (xx) | 1973-10-31 |
AT281811B (de) | 1970-06-10 |
YU178368A (en) | 1974-12-31 |
IE32222B1 (en) | 1973-05-16 |
IL30442A (en) | 1972-01-27 |
SU393827A3 (xx) | 1973-08-10 |
FI49416C (fi) | 1975-06-10 |
BR6800997D0 (pt) | 1973-01-02 |
FI49415B (xx) | 1975-02-28 |
CS153467B2 (xx) | 1974-02-25 |
CH484094A (de) | 1970-01-15 |
NO122751B (xx) | 1971-08-09 |
AT285595B (de) | 1970-11-10 |
AT283346B (de) | 1970-08-10 |
FI49416B (xx) | 1975-02-28 |
AT280272B (de) | 1970-04-10 |
BG15387A3 (bg) | 1976-05-10 |
GT197640170A (es) | 1977-08-06 |
IL30442A0 (en) | 1968-11-27 |
DK121087B (da) | 1971-09-06 |
CS153468B2 (xx) | 1974-02-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1927393A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsaeuren | |
CH624949A5 (xx) | ||
DE1695677B1 (de) | N-Arylsulfonyl-N'-(3-aza-bicycloalkyl)-harnstoffe,ihre Salze und Verfahren zu ihrer Herstellung | |
DE2021100A1 (de) | Chinolinderivate | |
DE1793047A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsaeuren | |
DE2740836A1 (de) | Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
DE2817661A1 (de) | Neue isoindolinderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen | |
EP0072961B1 (de) | 1-Phenylindazol-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
CH484095A (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren | |
DE1927452A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsaeuren | |
DE1937056A1 (de) | Verfahren zur Herstellung von neuen heterocylischen Carbonsaeuren | |
AT283345B (de) | Verfahren zur herstellung von neuen cumaron-, benzo<b>thiophen- oder indolderivaten und ihren salzen | |
DE2423721A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
AT283344B (de) | Verfahren zur Herstellung von neuen Cumaron-, Benzo[b]thiopen- oder Indolderivaten und ihren Salzen | |
DE1793048A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Aminocarbonsaeuren | |
EP0301245B1 (de) | 3-Sulfonyl-3,7-diazabicyclo-(3,3,1)nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
DE3020895A1 (de) | Ergopeptinderivate, verfahren zu deren herstellung sowie diese ergopeptinderivate enthaltende pharmazeutischen zusammensetzungen | |
DE2045371A1 (de) | Verfahren zur Herstellung von neuen heterocv chschen Carbonsauren | |
CH500966A (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren | |
CH461489A (de) | Verfahren zur Herstellung von neuen Oxazolderivaten | |
DE2055719A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäureestern | |
CH540900A (de) | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren | |
DE1921653A1 (de) | Verfahren zur Herstellung von neuen,substituierten Phenaethylalkoholen und deren Estern | |
DE3545206A1 (de) | Substituierte 4-fluor-isoindoline, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen | |
DE2508251A1 (de) | Neue derivate des indols, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |