NO122751B - - Google Patents
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- Publication number
- NO122751B NO122751B NO2865/68A NO286568A NO122751B NO 122751 B NO122751 B NO 122751B NO 2865/68 A NO2865/68 A NO 2865/68A NO 286568 A NO286568 A NO 286568A NO 122751 B NO122751 B NO 122751B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- carboxylic acid
- benzofuran
- compound
- butyryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 heterocyclic carboxylic acids Chemical class 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000029142 excretion Effects 0.000 description 7
- 230000000894 saliuretic effect Effects 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- JYVZRRLDAFCFJH-UHFFFAOYSA-N 6-ethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C(C)C1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CC)=C)=O JYVZRRLDAFCFJH-UHFFFAOYSA-N 0.000 description 3
- STGSJLZWQHRTGE-UHFFFAOYSA-N 6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1 STGSJLZWQHRTGE-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 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 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- DXASAURXULABHM-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)butanoyl]-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound BrC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)(CC)CBr DXASAURXULABHM-UHFFFAOYSA-N 0.000 description 2
- ISHJFUWRRWBXGC-UHFFFAOYSA-N 5-butanoyl-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(CCC)=O ISHJFUWRRWBXGC-UHFFFAOYSA-N 0.000 description 2
- OJBJSQSBMJPVBA-UHFFFAOYSA-N 7-ethylchromen-2-one Chemical compound C1=CC(=O)OC2=CC(CC)=CC=C21 OJBJSQSBMJPVBA-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000001477 organic nitrogen group Chemical group 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LUUIRSXAWQZPKD-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)butanoyl chloride Chemical compound CCC(Br)(CBr)C(Cl)=O LUUIRSXAWQZPKD-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
- 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
- ZNCWIQRZAFXNOO-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-6-methyl-1-benzofuran-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C)C(C(=O)C(CN(C)C)CC)=CC2=C1OC(C(O)=O)=C2 ZNCWIQRZAFXNOO-UHFFFAOYSA-N 0.000 description 1
- OKXNBEIPOLGRLI-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)butanoyl]-4-chloro-1-benzofuran-2-carboxylic acid Chemical compound ClC1=C(C=CC2=C1C=C(O2)C(=O)O)C(C(CC)(CBr)Br)=O OKXNBEIPOLGRLI-UHFFFAOYSA-N 0.000 description 1
- WJIPEVRFWFDPCT-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)butanoyl]-6-ethoxy-1-benzofuran-2-carboxylic acid Chemical compound BrC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)OCC)(CC)CBr WJIPEVRFWFDPCT-UHFFFAOYSA-N 0.000 description 1
- CGEVYEGCZHDLSZ-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)pentanoyl]-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound BrC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)(CCC)CBr CGEVYEGCZHDLSZ-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
- FECWAUVNWRDABN-UHFFFAOYSA-N 6-ethyl-1-benzofuran-2-carboxylic acid Chemical compound CCC1=CC=C2C=C(C(O)=O)OC2=C1 FECWAUVNWRDABN-UHFFFAOYSA-N 0.000 description 1
- UKNLZJGUUXBXPU-UHFFFAOYSA-N 6-methyl-5-(2-methylidenepentanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CCC)=C)=O UKNLZJGUUXBXPU-UHFFFAOYSA-N 0.000 description 1
- DLCASBFCJDKEJT-UHFFFAOYSA-N 6-methyl-5-(2-methylprop-2-enoyl)-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C)=CC2=C1OC(C(O)=O)=C2 DLCASBFCJDKEJT-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RHNXDVDQPSDYRO-UHFFFAOYSA-N BrC(C(=O)C=1C(=CC2=C(C(=C(O2)C(=O)O)C)C1)C)(CC)CBr Chemical compound BrC(C(=O)C=1C(=CC2=C(C(=C(O2)C(=O)O)C)C1)C)(CC)CBr RHNXDVDQPSDYRO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CCHZULQXRDHKMJ-UHFFFAOYSA-N ClC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)CC)(CC)CCl Chemical compound ClC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)CC)(CC)CCl CCHZULQXRDHKMJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- VTUOVBVMHPBQLX-UHFFFAOYSA-N benzene heptane Chemical compound CCCCCCC.C1=CC=CC=C1.C1=CC=CC=C1 VTUOVBVMHPBQLX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1076467A CH484092A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122751B true NO122751B (es) | 1971-08-09 |
Family
ID=4366590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2865/68A NO122751B (es) | 1967-07-28 | 1968-07-19 |
Country Status (15)
| Country | Link |
|---|---|
| AT (4) | AT281811B (es) |
| BG (2) | BG15387A3 (es) |
| BR (1) | BR6800997D0 (es) |
| CH (2) | CH484095A (es) |
| CS (2) | CS153467B2 (es) |
| DK (1) | DK121087B (es) |
| FI (2) | FI49415C (es) |
| GT (1) | GT197640170A (es) |
| IE (1) | IE32222B1 (es) |
| IL (1) | IL30442A (es) |
| NO (1) | NO122751B (es) |
| PL (1) | PL69796B1 (es) |
| SE (1) | SE364270B (es) |
| SU (1) | SU393827A3 (es) |
| YU (1) | YU32705B (es) |
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 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
- 1968-07-19 DK DK351368AA patent/DK121087B/da unknown
- 1968-07-25 YU YU1783/68A patent/YU32705B/xx 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 PL PL1968128332A patent/PL69796B1/pl unknown
- 1968-07-26 CS CS719771*1A patent/CS153468B2/cs unknown
- 1968-07-26 BG BG012203A patent/BG15387A3/bg unknown
- 1968-07-26 BG BG012202A patent/BG15386A3/bg unknown
- 1968-07-26 AT AT729868A patent/AT280272B/de not_active IP Right Cessation
- 1968-07-26 IL IL30442A patent/IL30442A/en unknown
- 1968-07-26 BR BR200997/68A patent/BR6800997D0/pt unknown
- 1968-07-26 SU SU1415775A patent/SU393827A3/ru active
- 1968-07-26 IE IE904/68A patent/IE32222B1/xx unknown
- 1968-07-26 AT AT446869A patent/AT283346B/de not_active IP Right Cessation
- 1968-07-26 AT AT06940/69A patent/AT285595B/de not_active IP Right Cessation
-
1976
- 1976-02-13 GT GT197640170A patent/GT197640170A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI49416B (es) | 1975-02-28 |
| YU178368A (en) | 1974-12-31 |
| YU32705B (en) | 1975-06-30 |
| PL69796B1 (es) | 1973-10-31 |
| CS153467B2 (es) | 1974-02-25 |
| FI49416C (fi) | 1975-06-10 |
| BR6800997D0 (pt) | 1973-01-02 |
| BG15387A3 (bg) | 1976-05-10 |
| AT285595B (de) | 1970-11-10 |
| BG15386A3 (bg) | 1976-03-23 |
| CH484095A (de) | 1970-01-15 |
| AT281811B (de) | 1970-06-10 |
| SE364270B (es) | 1974-02-18 |
| FI49415B (es) | 1975-02-28 |
| IL30442A (en) | 1972-01-27 |
| FI49415C (fi) | 1975-06-10 |
| IE32222L (en) | 1969-01-28 |
| IL30442A0 (en) | 1968-11-27 |
| DK121087B (da) | 1971-09-06 |
| AT280272B (de) | 1970-04-10 |
| AT283346B (de) | 1970-08-10 |
| GT197640170A (es) | 1977-08-06 |
| SU393827A3 (es) | 1973-08-10 |
| IE32222B1 (en) | 1973-05-16 |
| CH484094A (de) | 1970-01-15 |
| CS153468B2 (es) | 1974-02-25 |
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