NO122754B - - Google Patents
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- Publication number
- NO122754B NO122754B NO2126/69A NO212669A NO122754B NO 122754 B NO122754 B NO 122754B NO 2126/69 A NO2126/69 A NO 2126/69A NO 212669 A NO212669 A NO 212669A NO 122754 B NO122754 B NO 122754B
- Authority
- NO
- Norway
- Prior art keywords
- carboxylic acid
- dihydro
- benzofuran
- butyryl
- general formula
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 34
- 239000000243 solution Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- OALGDQAPRDHTMA-UHFFFAOYSA-N 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2CC(C(O)=O)OC2=C1 OALGDQAPRDHTMA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- BOHRSHOOWUCKFK-UHFFFAOYSA-N 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 BOHRSHOOWUCKFK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ANDNWVFDPXBDQS-UHFFFAOYSA-N 5-butanoyl-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C ANDNWVFDPXBDQS-UHFFFAOYSA-N 0.000 description 5
- MXSSAVDQXFOUOF-UHFFFAOYSA-N 6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2CC(C(O)=O)OC2=C1C MXSSAVDQXFOUOF-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 5
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 5
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 229910001023 sodium amalgam Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WEVFUSSJCGAVOH-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)CC2=C1 WEVFUSSJCGAVOH-UHFFFAOYSA-N 0.000 description 4
- LUUIRSXAWQZPKD-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)butanoyl chloride Chemical compound CCC(Br)(CBr)C(Cl)=O LUUIRSXAWQZPKD-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 230000000894 saliuretic effect Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- WEVPVZMJEYAFKM-UHFFFAOYSA-N (6-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound C1=C(Cl)C=C2OC(CO)CC2=C1 WEVPVZMJEYAFKM-UHFFFAOYSA-N 0.000 description 3
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SNWIFVPSGHUJHP-UHFFFAOYSA-N 5-butanoyl-6-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)Cl SNWIFVPSGHUJHP-UHFFFAOYSA-N 0.000 description 3
- QMUWWCFWSDDWNP-UHFFFAOYSA-N 5-butanoyl-7-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C=C(C2=C(CC(O2)C(=O)O)C1)Cl QMUWWCFWSDDWNP-UHFFFAOYSA-N 0.000 description 3
- ADCSXAUMFOOIRE-UHFFFAOYSA-N 6-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C=C2OC(C(=O)O)CC2=C1 ADCSXAUMFOOIRE-UHFFFAOYSA-N 0.000 description 3
- PQRVGXBBBUGWBY-UHFFFAOYSA-N 6-chloro-7-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=C2OC(C(O)=O)CC2=C1 PQRVGXBBBUGWBY-UHFFFAOYSA-N 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- ZBDAMDWKXGTKBT-UHFFFAOYSA-N ethyl 2-cyclohexylacetate Chemical compound CCOC(=O)CC1CCCCC1 ZBDAMDWKXGTKBT-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical class C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- KHRWKDIDZURTCQ-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)butanoyl]-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound BrC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C)(CC)CBr KHRWKDIDZURTCQ-UHFFFAOYSA-N 0.000 description 2
- WPVBSBUSNBWWHS-UHFFFAOYSA-N 5-butanoyl-6-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)OC WPVBSBUSNBWWHS-UHFFFAOYSA-N 0.000 description 2
- CWEMEMQGPCUERS-UHFFFAOYSA-N 5-chloro-2-prop-2-enylphenol Chemical compound OC1=CC(Cl)=CC=C1CC=C CWEMEMQGPCUERS-UHFFFAOYSA-N 0.000 description 2
- LIHRJKHYQHZFSX-UHFFFAOYSA-N 6,7-dimethyl-5-pentanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCCC)(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C LIHRJKHYQHZFSX-UHFFFAOYSA-N 0.000 description 2
- ZYQCKPKFAFHUSJ-UHFFFAOYSA-N 6-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=C2CC(C(O)=O)OC2=C1 ZYQCKPKFAFHUSJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VYLJTMRMHUANLT-UHFFFAOYSA-N (4-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound OCC1OC2=C(C1)C(=CC=C2)Cl VYLJTMRMHUANLT-UHFFFAOYSA-N 0.000 description 1
- HDILUVUJBIHXQV-UHFFFAOYSA-N (7-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol Chemical compound C1=CC(Cl)=C2OC(CO)CC2=C1 HDILUVUJBIHXQV-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- LQZIJTARSXHJOE-UHFFFAOYSA-N 2,3-dibromo-2-methylpropanoyl chloride Chemical compound BrCC(Br)(C)C(Cl)=O LQZIJTARSXHJOE-UHFFFAOYSA-N 0.000 description 1
- ITMGMSZDAOAVNO-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-2-ylmethanol Chemical class C1=CC=C2OC(CO)CC2=C1 ITMGMSZDAOAVNO-UHFFFAOYSA-N 0.000 description 1
- RZWGTXHSYZGXKF-UHFFFAOYSA-N 2-(2-methylphenyl)acetic acid Chemical compound CC1=CC=CC=C1CC(O)=O RZWGTXHSYZGXKF-UHFFFAOYSA-N 0.000 description 1
- RUALOJPMDIKFQU-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)phenol Chemical class OC1=CC=CC=C1CC1OC1 RUALOJPMDIKFQU-UHFFFAOYSA-N 0.000 description 1
- HICFTSKJYUMCHM-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(Br)(CBr)C(Cl)=O HICFTSKJYUMCHM-UHFFFAOYSA-N 0.000 description 1
- ITZMIRCWGDWDCI-UHFFFAOYSA-N 2-chloro-6-(oxiran-2-ylmethyl)phenol Chemical compound OC1=C(Cl)C=CC=C1CC1OC1 ITZMIRCWGDWDCI-UHFFFAOYSA-N 0.000 description 1
- UPEBXJHGPMUFKU-UHFFFAOYSA-N 2-chloro-6-prop-2-enylphenol Chemical compound OC1=C(Cl)C=CC=C1CC=C UPEBXJHGPMUFKU-UHFFFAOYSA-N 0.000 description 1
- IIYDTSAAECYHAE-UHFFFAOYSA-N 2-methylidenebutanoyl chloride Chemical compound CCC(=C)C(Cl)=O IIYDTSAAECYHAE-UHFFFAOYSA-N 0.000 description 1
- WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 1
- YJXFVEWYNFGQAJ-UHFFFAOYSA-N 3-chloro-2-prop-2-enylphenol Chemical compound OC1=CC=CC(Cl)=C1CC=C YJXFVEWYNFGQAJ-UHFFFAOYSA-N 0.000 description 1
- LLIIFMUNEXVLGA-UHFFFAOYSA-N 3-methyl-2-methylidenebutanoyl chloride Chemical compound CC(C)C(=C)C(Cl)=O LLIIFMUNEXVLGA-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- NYKQUPXSAIADCP-UHFFFAOYSA-N 5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C=CC2=C(CC(O2)C(=O)O)C1)CC NYKQUPXSAIADCP-UHFFFAOYSA-N 0.000 description 1
- LXZRWPLSPQYULW-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-2,3-dihydro-1-benzofuran-2-carboxylic acid hydrochloride Chemical compound Cl.CN(C)CC(C(=O)C=1C=CC2=C(CC(O2)C(=O)O)C1)CC LXZRWPLSPQYULW-UHFFFAOYSA-N 0.000 description 1
- TYMFHCSSPRSNCE-UHFFFAOYSA-N 5-butanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C=CC2=C(CC(O2)C(=O)O)C1 TYMFHCSSPRSNCE-UHFFFAOYSA-N 0.000 description 1
- XYZSWFFJRMCPJZ-UHFFFAOYSA-N 5-chloro-2-(oxiran-2-ylmethyl)phenol Chemical compound O1C(CC2=C(C=C(C=C2)Cl)O)C1 XYZSWFFJRMCPJZ-UHFFFAOYSA-N 0.000 description 1
- ZQWOLTVJEJDOFX-UHFFFAOYSA-N 6,7-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1C ZQWOLTVJEJDOFX-UHFFFAOYSA-N 0.000 description 1
- MSMVSVFGSGSXKN-UHFFFAOYSA-N 6,7-dimethyl-5-(2-methylidenepentanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)CCC MSMVSVFGSGSXKN-UHFFFAOYSA-N 0.000 description 1
- CKXVHWNUXVCTCW-UHFFFAOYSA-N 6-chloro-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 CKXVHWNUXVCTCW-UHFFFAOYSA-N 0.000 description 1
- AAOIETLWISYSNR-UHFFFAOYSA-N 6-chloro-7-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(Cl)C=CC2=C1OC(C(O)=O)=C2 AAOIETLWISYSNR-UHFFFAOYSA-N 0.000 description 1
- KQRBOHOKLNORTA-UHFFFAOYSA-N 6-methyl-1-benzothiophene-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)SC2=C1 KQRBOHOKLNORTA-UHFFFAOYSA-N 0.000 description 1
- RJTWHECDADQLII-UHFFFAOYSA-N 6-methyl-5-(2-methylprop-2-enoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C)=CC2=C1OC(C(O)=O)C2 RJTWHECDADQLII-UHFFFAOYSA-N 0.000 description 1
- PGMLRDFXXKSPCQ-UHFFFAOYSA-N 6-methyl-5-(3-methyl-2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C(C)C)=CC2=C1OC(C(O)=O)C2 PGMLRDFXXKSPCQ-UHFFFAOYSA-N 0.000 description 1
- QXBQJXVMLMPNHS-UHFFFAOYSA-N 7,8-dimethylchromen-2-one Chemical compound C1=CC(=O)OC2=C(C)C(C)=CC=C21 QXBQJXVMLMPNHS-UHFFFAOYSA-N 0.000 description 1
- KSSRTMJGUNWSTN-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=CC(Cl)=C2OC(C(=O)O)CC2=C1 KSSRTMJGUNWSTN-UHFFFAOYSA-N 0.000 description 1
- CGWMDCXXZCKHIZ-UHFFFAOYSA-N 7-chloro-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C=C(C2=C(CC(O2)C(=O)O)C1)Cl)CC CGWMDCXXZCKHIZ-UHFFFAOYSA-N 0.000 description 1
- VHOAUUCXGIKDJV-UHFFFAOYSA-N 7-chloro-8-methylchromen-2-one Chemical compound ClC1=CC=C2C=CC(OC2=C1C)=O VHOAUUCXGIKDJV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GXNSYKIULPTNPI-UHFFFAOYSA-N Cl.CN(C)CC(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)CCC Chemical compound Cl.CN(C)CC(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)CCC GXNSYKIULPTNPI-UHFFFAOYSA-N 0.000 description 1
- YBJSXSZNDVBORS-UHFFFAOYSA-N Cl.CN(C)CC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C)CC Chemical compound Cl.CN(C)CC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C)CC YBJSXSZNDVBORS-UHFFFAOYSA-N 0.000 description 1
- SASWQCXPFGPUSP-UHFFFAOYSA-N Cl.CN(C)CC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)Cl)CC Chemical compound Cl.CN(C)CC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)Cl)CC SASWQCXPFGPUSP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- HAJXNVWQYIKNQT-UHFFFAOYSA-N benzene;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.C1=CC=CC=C1 HAJXNVWQYIKNQT-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium 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
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH803268A CH510007A (de) | 1968-05-30 | 1968-05-30 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122754B true NO122754B (xx) | 1971-08-09 |
Family
ID=4334103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2126/69A NO122754B (xx) | 1968-05-30 | 1969-05-23 |
Country Status (19)
| Country | Link |
|---|---|
| AT (3) | AT289783B (xx) |
| BE (1) | BE733769A (xx) |
| BG (3) | BG15576A3 (xx) |
| BR (1) | BR6909330D0 (xx) |
| CH (3) | CH510008A (xx) |
| CS (3) | CS158645B2 (xx) |
| DE (1) | DE1927452C3 (xx) |
| DK (1) | DK122607B (xx) |
| ES (3) | ES367840A1 (xx) |
| FI (1) | FI49417C (xx) |
| FR (1) | FR2009653A1 (xx) |
| GB (1) | GB1266766A (xx) |
| IE (1) | IE33125B1 (xx) |
| IL (1) | IL32311A (xx) |
| NL (1) | NL6907974A (xx) |
| NO (1) | NO122754B (xx) |
| SE (1) | SE360859B (xx) |
| SU (1) | SU402220A3 (xx) |
| YU (1) | YU34041B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756105A (fr) * | 1969-09-15 | 1971-03-15 | Geigy Ag J R | Nouveaux acides carboxyliques heterocycliques et medicaments contenant de tels acides |
| BE759138A (fr) * | 1969-11-20 | 1971-05-19 | Geigy Ag J R | Derives du benzofuranne et du benzothiophene et medicaments contenant de telles substances |
| BE759137R (fr) * | 1969-11-20 | 1971-05-19 | Geigy Ag J R | Acides carboxyliques heterocycliques et medicaments contenant de tels |
| JPS61158976A (ja) * | 1984-12-28 | 1986-07-18 | Shionogi & Co Ltd | ベンゾフランおよびベンゾチオフエン誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE624749A (xx) * | 1961-11-14 |
-
1968
- 1968-05-30 CH CH820371A patent/CH510008A/de not_active IP Right Cessation
- 1968-05-30 CH CH803268A patent/CH510007A/de not_active IP Right Cessation
- 1968-05-30 CH CH820471A patent/CH510009A/de not_active IP Right Cessation
-
1969
- 1969-05-23 FI FI691565A patent/FI49417C/fi active
- 1969-05-23 SE SE07337/69A patent/SE360859B/xx unknown
- 1969-05-23 DK DK283269AA patent/DK122607B/da unknown
- 1969-05-23 NL NL6907974A patent/NL6907974A/xx not_active Application Discontinuation
- 1969-05-23 NO NO2126/69A patent/NO122754B/no unknown
- 1969-05-28 SU SU1334348A patent/SU402220A3/ru active
- 1969-05-29 AT AT142770A patent/AT289783B/de not_active IP Right Cessation
- 1969-05-29 YU YU1335/69A patent/YU34041B/xx unknown
- 1969-05-29 DE DE1927452A patent/DE1927452C3/de not_active Expired
- 1969-05-29 CS CS563772*1A patent/CS158645B2/cs unknown
- 1969-05-29 FR FR6917585A patent/FR2009653A1/fr not_active Withdrawn
- 1969-05-29 BR BR209330/69A patent/BR6909330D0/pt unknown
- 1969-05-29 BG BG012334A patent/BG15576A3/bg unknown
- 1969-05-29 ES ES367840A patent/ES367840A1/es not_active Expired
- 1969-05-29 CS CS383369A patent/CS158643B2/cs unknown
- 1969-05-29 CS CS563672*1A patent/CS158644B2/cs unknown
- 1969-05-29 AT AT511869A patent/AT286285B/de not_active IP Right Cessation
- 1969-05-29 IL IL32311A patent/IL32311A/en unknown
- 1969-05-29 ES ES367838A patent/ES367838A1/es not_active Expired
- 1969-05-29 ES ES367839A patent/ES367839A1/es not_active Expired
- 1969-05-29 AT AT142670A patent/AT289782B/de active
- 1969-05-29 BE BE733769D patent/BE733769A/xx unknown
- 1969-05-29 IE IE732/69A patent/IE33125B1/xx unknown
- 1969-05-29 GB GB1266766D patent/GB1266766A/en not_active Expired
- 1969-10-13 BG BG013176A patent/BG16178A3/bg unknown
- 1969-10-18 BG BG013175A patent/BG15224A3/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK122607B (da) | 1972-03-20 |
| CH510009A (de) | 1971-07-15 |
| CS158644B2 (xx) | 1974-11-25 |
| ES367839A1 (es) | 1971-04-16 |
| YU133569A (en) | 1978-05-15 |
| GB1266766A (xx) | 1972-03-15 |
| YU34041B (en) | 1978-10-31 |
| AT289783B (de) | 1971-05-10 |
| ES367838A1 (es) | 1971-04-16 |
| IE33125L (en) | 1969-11-30 |
| FI49417C (fi) | 1975-06-10 |
| SE360859B (xx) | 1973-10-08 |
| DE1927452A1 (de) | 1969-12-04 |
| CH510008A (de) | 1971-07-15 |
| FI49417B (xx) | 1975-02-28 |
| ES367840A1 (es) | 1971-04-16 |
| IL32311A0 (en) | 1969-07-30 |
| FR2009653A1 (xx) | 1970-02-06 |
| DE1927452B2 (de) | 1978-02-02 |
| BG16178A3 (bg) | 1972-07-20 |
| SU402220A3 (xx) | 1973-10-12 |
| BE733769A (xx) | 1969-12-01 |
| CS158645B2 (xx) | 1974-11-25 |
| CH510007A (de) | 1971-07-15 |
| IL32311A (en) | 1972-09-28 |
| BR6909330D0 (pt) | 1973-02-08 |
| NL6907974A (xx) | 1969-12-02 |
| BG15224A3 (bg) | 1975-11-21 |
| DE1927452C3 (de) | 1978-10-12 |
| AT289782B (de) | 1971-05-10 |
| BG15576A3 (bg) | 1972-05-20 |
| AT286285B (de) | 1970-12-10 |
| IE33125B1 (en) | 1974-03-20 |
| CS158643B2 (xx) | 1974-11-25 |
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