PL81003B1 - - Google Patents
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- Publication number
- PL81003B1 PL81003B1 PL1970143170A PL41317070A PL81003B1 PL 81003 B1 PL81003 B1 PL 81003B1 PL 1970143170 A PL1970143170 A PL 1970143170A PL 41317070 A PL41317070 A PL 41317070A PL 81003 B1 PL81003 B1 PL 81003B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- dihydro
- general formula
- methyl
- mixture
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 150000007529 inorganic bases Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 16
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910001023 sodium amalgam Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- YHGXUBDJYPGDLL-UHFFFAOYSA-N 5-formyl-6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C YHGXUBDJYPGDLL-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JBGVCHAJHGUTBQ-UHFFFAOYSA-N 5-formyl-6-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)OC JBGVCHAJHGUTBQ-UHFFFAOYSA-N 0.000 description 3
- DQVIZIDHNMMJLT-UHFFFAOYSA-N 6-chloro-5-formyl-2,3-dihydro-1-benzothiophene-2-carboxylic acid Chemical compound C(=O)C1=CC2=C(SC(C2)C(=O)O)C=C1Cl DQVIZIDHNMMJLT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- VZTPRAHUNORRBF-UHFFFAOYSA-N 5-formyl-3,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1C(OC2=C1C=C(C(=C2)C)C=O)C(=O)O VZTPRAHUNORRBF-UHFFFAOYSA-N 0.000 description 2
- MBQUUOLHNUKYPQ-UHFFFAOYSA-N 5-formyl-4-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=CC2=C1CC(O2)C(=O)O)C=O MBQUUOLHNUKYPQ-UHFFFAOYSA-N 0.000 description 2
- RIXAVCVRWLBYIH-UHFFFAOYSA-N C(C)(=O)C(=CC1=CC2=C(SC(C2)C(=O)O)C=C1Cl)C(C)=O Chemical compound C(C)(=O)C(=CC1=CC2=C(SC(C2)C(=O)O)C=C1Cl)C(C)=O RIXAVCVRWLBYIH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JZGZKRJVTIRPOK-UHFFFAOYSA-N ethyl thiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=CS1 JZGZKRJVTIRPOK-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000155 melt Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 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
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4 dichlorobenzoic acid Natural products OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- MTVMBYHIKUWTPS-UHFFFAOYSA-N 2-methyl-3h-1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C)(C(O)=O)CC2=C1 MTVMBYHIKUWTPS-UHFFFAOYSA-N 0.000 description 1
- OTOOLZPZIKKFLE-UHFFFAOYSA-N 3,4-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound C1=CC(C)=C2C(C)=C(C(O)=O)OC2=C1 OTOOLZPZIKKFLE-UHFFFAOYSA-N 0.000 description 1
- ZUKWIQSZWLJEMT-UHFFFAOYSA-N 3,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C(C)C(C(O)=O)OC2=C1 ZUKWIQSZWLJEMT-UHFFFAOYSA-N 0.000 description 1
- LQWJCKLAJRCTRP-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-sulfanylprop-2-enoic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C=C(C(=O)O)S LQWJCKLAJRCTRP-UHFFFAOYSA-N 0.000 description 1
- IPAXPERGAMNMIJ-UHFFFAOYSA-N 4-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1Cl IPAXPERGAMNMIJ-UHFFFAOYSA-N 0.000 description 1
- DEXIXUHOXHEGAO-UHFFFAOYSA-N 4-chloro-2,3-dihydro-1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C(Cl)C2=C1SC(C(=O)O)C2 DEXIXUHOXHEGAO-UHFFFAOYSA-N 0.000 description 1
- SNKGYZVEYQQMFY-UHFFFAOYSA-N 4-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=CC2=C1C=C(C(O)=O)O2 SNKGYZVEYQQMFY-UHFFFAOYSA-N 0.000 description 1
- VFMMQNOMLYYGOW-UHFFFAOYSA-N 5-(2-acetyl-3-oxobut-1-enyl)-3,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=C(C(C)=O)C(C)=O)C=C2C(C)C(C(O)=O)OC2=C1 VFMMQNOMLYYGOW-UHFFFAOYSA-N 0.000 description 1
- ODJORMXGVXXWEE-UHFFFAOYSA-N 5-(2-acetyl-3-oxobut-1-enyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C)C(C=C(C(=O)C)C(C)=O)=CC2=C1OC(C(O)=O)C2 ODJORMXGVXXWEE-UHFFFAOYSA-N 0.000 description 1
- AWTXBSRTTWQTCT-UHFFFAOYSA-N 5-(2-acetyl-3-oxobut-1-enyl)-6-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C=C(C(C)=O)C(C)=O)C(OC)=CC2=C1CC(C(O)=O)O2 AWTXBSRTTWQTCT-UHFFFAOYSA-N 0.000 description 1
- SOTTZVOPFKOHCR-UHFFFAOYSA-N 5-(2-acetyl-3-oxobut-1-enyl)-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C=C(C(=O)C)C(C)=O)=CC2=C1OC(C(O)=O)C2 SOTTZVOPFKOHCR-UHFFFAOYSA-N 0.000 description 1
- PZCBAVDZUVWUFY-UHFFFAOYSA-N 5-(2-acetyl-3-oxopent-1-enyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C)C(C=C(C(=O)CC)C(C)=O)=CC2=C1OC(C(O)=O)C2 PZCBAVDZUVWUFY-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
- AVAGKGZNBMZOLD-UHFFFAOYSA-N 6-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(C(=O)O)=CC2=C1 AVAGKGZNBMZOLD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 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
- 206010030113 Oedema Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution 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
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 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
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1395269 | 1969-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81003B1 true PL81003B1 (enrdf_load_stackoverflow) | 1975-08-30 |
Family
ID=4396729
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970143170A PL81003B1 (enrdf_load_stackoverflow) | 1969-09-15 | 1970-09-14 | |
| PL1970143204A PL72916B1 (enrdf_load_stackoverflow) | 1969-09-15 | 1970-09-15 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970143204A PL72916B1 (enrdf_load_stackoverflow) | 1969-09-15 | 1970-09-15 |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH521963A (enrdf_load_stackoverflow) |
| ES (2) | ES383634A1 (enrdf_load_stackoverflow) |
| IE (1) | IE34661B1 (enrdf_load_stackoverflow) |
| IL (1) | IL35288A (enrdf_load_stackoverflow) |
| NO (1) | NO129740B (enrdf_load_stackoverflow) |
| PL (2) | PL81003B1 (enrdf_load_stackoverflow) |
-
1969
- 1969-09-15 CH CH437172A patent/CH521963A/de not_active IP Right Cessation
-
1970
- 1970-09-08 NO NO03422/70A patent/NO129740B/no unknown
- 1970-09-14 IE IE1183/70A patent/IE34661B1/xx unknown
- 1970-09-14 PL PL1970143170A patent/PL81003B1/pl unknown
- 1970-09-14 ES ES383634A patent/ES383634A1/es not_active Expired
- 1970-09-14 IL IL35288A patent/IL35288A/xx unknown
- 1970-09-14 ES ES383633A patent/ES383633A1/es not_active Expired
- 1970-09-15 PL PL1970143204A patent/PL72916B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE34661B1 (en) | 1975-07-09 |
| IL35288A0 (en) | 1970-11-30 |
| ES383634A1 (es) | 1973-03-01 |
| IL35288A (en) | 1973-06-29 |
| CH521963A (de) | 1972-04-30 |
| IE34661L (en) | 1971-03-15 |
| ES383633A1 (es) | 1973-02-16 |
| NO129740B (enrdf_load_stackoverflow) | 1974-05-20 |
| PL72916B1 (enrdf_load_stackoverflow) | 1974-08-30 |
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