CH542837A - Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten - Google Patents
Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen DerivatenInfo
- Publication number
- CH542837A CH542837A CH1223872A CH1223872A CH542837A CH 542837 A CH542837 A CH 542837A CH 1223872 A CH1223872 A CH 1223872A CH 1223872 A CH1223872 A CH 1223872A CH 542837 A CH542837 A CH 542837A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydro
- dibenzofuran
- acid
- yloxy
- ylthio
- Prior art date
Links
- 125000004104 aryloxy group Chemical group 0.000 title claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- -1 alkaline earth metal salt Chemical class 0.000 claims description 30
- 239000007858 starting material Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- JDMQBSZGCYBGAQ-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)octanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)CCCCCC JDMQBSZGCYBGAQ-UHFFFAOYSA-N 0.000 claims description 3
- HMPKFOIJXCWTOV-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)dodecanoic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)CCCCCCCCCC HMPKFOIJXCWTOV-UHFFFAOYSA-N 0.000 claims description 3
- WAFAZHOCGNGXIK-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)octanoic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)SC(C(=O)O)CCCCCC WAFAZHOCGNGXIK-UHFFFAOYSA-N 0.000 claims description 3
- AOIBRDYGMJIGRN-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)octanoic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC AOIBRDYGMJIGRN-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- AQIRJHCIAYPEPN-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)dodecanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCCCCCC AQIRJHCIAYPEPN-UHFFFAOYSA-N 0.000 claims description 2
- AFOMMDYUQVGYGC-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)dodecanoic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCCCCCC AFOMMDYUQVGYGC-UHFFFAOYSA-N 0.000 claims description 2
- QIJPGKNWNLOTNE-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfanyl)octanoic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)SC(C(=O)O)CCCCCC QIJPGKNWNLOTNE-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- FONXRQRYCNYOMK-UHFFFAOYSA-N 7-octan-2-yloxy-1,2,3,4-tetrahydrodibenzofuran Chemical compound C1=CC(=CC=2OC3=C(C=21)CCCC3)OC(C)CCCCCC FONXRQRYCNYOMK-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 8
- RJPHJNSOVWUNLF-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)octanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC RJPHJNSOVWUNLF-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002632 lipids Chemical class 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract 2
- 206010019842 Hepatomegaly Diseases 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000010828 elution Methods 0.000 description 8
- DLFLWVYSSLYVBK-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzofuran-2-ol Chemical compound C1CCCC2=C1OC1=CC=C(O)C=C12 DLFLWVYSSLYVBK-UHFFFAOYSA-N 0.000 description 7
- IPESETNMSBOYDM-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzofuran-2-thiol Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)S IPESETNMSBOYDM-UHFFFAOYSA-N 0.000 description 7
- NZQLDDRKACJBHY-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzofuran-3-ol Chemical compound C1CCCC2=C1C1=CC=C(O)C=C1O2 NZQLDDRKACJBHY-UHFFFAOYSA-N 0.000 description 7
- SWUWAMMQSPMFKF-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzothiophen-3-ol Chemical compound C1CCCC2=C1C1=CC=C(O)C=C1S2 SWUWAMMQSPMFKF-UHFFFAOYSA-N 0.000 description 7
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PKJAPNISIINOOB-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzothiophen-2-ol Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)O PKJAPNISIINOOB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- VCNVCTNYSFIDOO-UHFFFAOYSA-N diethyl 2-bromo-2-hexylpropanedioate Chemical compound CCCCCCC(Br)(C(=O)OCC)C(=O)OCC VCNVCTNYSFIDOO-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 description 5
- LWSQNKUPPZYRGH-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzothiophene-2-thiol Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)S LWSQNKUPPZYRGH-UHFFFAOYSA-N 0.000 description 5
- JHBMPQFJFJKMFS-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzothiophene-3-thiol Chemical class C1=CC(=CC=2SC3=C(C21)CCCC3)S JHBMPQFJFJKMFS-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JCLPOPNXITXHOR-UHFFFAOYSA-N 1,2,3,4-tetrahydrodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1CCCC2 JCLPOPNXITXHOR-UHFFFAOYSA-N 0.000 description 3
- ULBHLXGSAOUDPE-UHFFFAOYSA-N 2-(3-methoxyphenoxy)cyclohexan-1-one Chemical compound COC1=CC=CC(OC2C(CCCC2)=O)=C1 ULBHLXGSAOUDPE-UHFFFAOYSA-N 0.000 description 3
- BRTORKIVDSBTDG-UHFFFAOYSA-N 2-(4-methoxyphenoxy)cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1OC1C(=O)CCCC1 BRTORKIVDSBTDG-UHFFFAOYSA-N 0.000 description 3
- ZNLGDZWIVKXSBA-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)octanoic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC ZNLGDZWIVKXSBA-UHFFFAOYSA-N 0.000 description 3
- LOKNQAJRNAVSBM-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanedioic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC LOKNQAJRNAVSBM-UHFFFAOYSA-N 0.000 description 3
- QANXKDIOWPLAHH-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzofuran-3-thiol Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)S QANXKDIOWPLAHH-UHFFFAOYSA-N 0.000 description 3
- IYLJKXUILQMUON-UHFFFAOYSA-N 8-methoxy-1,2,3,4-tetrahydrodibenzofuran Chemical compound C1CCCC2=C1OC1=CC=C(OC)C=C12 IYLJKXUILQMUON-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- LREHXNMBUBVFHA-UHFFFAOYSA-N 1,2,3,4-tetrahydrodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1CCCC2 LREHXNMBUBVFHA-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NESNJGILYGANHV-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanylcyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1SC1C(=O)CCCC1 NESNJGILYGANHV-UHFFFAOYSA-N 0.000 description 2
- QPWMVKSUTLRMHE-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)octanoic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC QPWMVKSUTLRMHE-UHFFFAOYSA-N 0.000 description 2
- KQXVBULMXCKYDK-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)octanoic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)CCCCCC KQXVBULMXCKYDK-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CCHNWURRBFGQCD-UHFFFAOYSA-N 2-chlorocyclohexan-1-one Chemical compound ClC1CCCCC1=O CCHNWURRBFGQCD-UHFFFAOYSA-N 0.000 description 2
- VDAIHBXECIYFNB-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)propanedioic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCC VDAIHBXECIYFNB-UHFFFAOYSA-N 0.000 description 2
- NGBLPWCHHQTFLD-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)propanedioic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC NGBLPWCHHQTFLD-UHFFFAOYSA-N 0.000 description 2
- GLLSZVCKUJMZJS-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCC GLLSZVCKUJMZJS-UHFFFAOYSA-N 0.000 description 2
- RXRLHXRLEXHXPJ-UHFFFAOYSA-N 2-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanedioic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)C RXRLHXRLEXHXPJ-UHFFFAOYSA-N 0.000 description 2
- QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 2
- MTBGXMWOHXOKSK-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydrodibenzofuran Chemical compound C1CCCC2=C1C1=CC=C(OC)C=C1O2 MTBGXMWOHXOKSK-UHFFFAOYSA-N 0.000 description 2
- VJBQKDWOHBMPTI-UHFFFAOYSA-N 8-methoxy-1,2,3,4-tetrahydrodibenzothiophene Chemical compound COC1=CC2=C(SC3=C2CCCC3)C=C1 VJBQKDWOHBMPTI-UHFFFAOYSA-N 0.000 description 2
- KMTXVBVKFHGJLL-UHFFFAOYSA-N 9-methoxy-1,2,3,4-tetrahydrodibenzofuran Chemical compound COC1=CC=CC=2OC3=C(C21)CCCC3 KMTXVBVKFHGJLL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PYQIJFIYVUNARD-UHFFFAOYSA-N C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCCCCCCCCCC Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCCCCCCCCCC PYQIJFIYVUNARD-UHFFFAOYSA-N 0.000 description 2
- IYUUHGFTXOMTIX-UHFFFAOYSA-N C1=CC(=CC=2OC3=C(C21)CCCC3)OC(N(C)C)=S Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)OC(N(C)C)=S IYUUHGFTXOMTIX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NHDARYNQTXLNRO-UHFFFAOYSA-N S-(6,7,8,9-tetrahydrodibenzofuran-2-yl) N,N-dimethylcarbamothioate Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)SC(N(C)C)=O NHDARYNQTXLNRO-UHFFFAOYSA-N 0.000 description 2
- KFXZJDLLAFQFEF-UHFFFAOYSA-N S-(6,7,8,9-tetrahydrodibenzofuran-3-yl) N,N-dimethylcarbamothioate Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(N(C)C)=O KFXZJDLLAFQFEF-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- KBASHUUJJGWTIH-UHFFFAOYSA-N diethyl 2-bromo-2-decylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCC)Br)=O KBASHUUJJGWTIH-UHFFFAOYSA-N 0.000 description 2
- GUSSIIXBELKDGF-UHFFFAOYSA-N diethyl 2-bromo-2-tetradecylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)Br)=O GUSSIIXBELKDGF-UHFFFAOYSA-N 0.000 description 2
- KTQLAOXRRWFQRS-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O KTQLAOXRRWFQRS-UHFFFAOYSA-N 0.000 description 2
- HSHMTDVEKPAEGS-UHFFFAOYSA-N diethyl 2-hexylpropanedioate Chemical compound CCCCCCC(C(=O)OCC)C(=O)OCC HSHMTDVEKPAEGS-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000000055 hyoplipidemic effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RAJQWFNCAGFSMN-UHFFFAOYSA-N 2-(3-methoxyphenyl)sulfanylcyclohexan-1-one Chemical compound COC1=CC=CC(SC2C(CCCC2)=O)=C1 RAJQWFNCAGFSMN-UHFFFAOYSA-N 0.000 description 1
- FTHYCAZEMLBXOJ-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)C FTHYCAZEMLBXOJ-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- QHTRBQBPXGFDDO-UHFFFAOYSA-N 2-bromo-2-methylpropanedioic acid Chemical compound OC(=O)C(Br)(C)C(O)=O QHTRBQBPXGFDDO-UHFFFAOYSA-N 0.000 description 1
- VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical class OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 1
- VHCPLBNNFPYAFS-UHFFFAOYSA-N 2-decyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCCCCCC VHCPLBNNFPYAFS-UHFFFAOYSA-N 0.000 description 1
- AGHKGTALSVPVFI-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)propanedioic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC AGHKGTALSVPVFI-UHFFFAOYSA-N 0.000 description 1
- NRJVMJLEFIUTIG-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)propanedioic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC NRJVMJLEFIUTIG-UHFFFAOYSA-N 0.000 description 1
- QCCWABJHNDRSNX-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCC QCCWABJHNDRSNX-UHFFFAOYSA-N 0.000 description 1
- HGIDRHWWNZRUEP-UHFFFAOYSA-N 2-hydroxydibenzofuran Chemical compound C1=CC=C2C3=CC(O)=CC=C3OC2=C1 HGIDRHWWNZRUEP-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CIRSWPZIDFTMED-UHFFFAOYSA-N 5a-morpholin-4-yl-7,8,9,9a-tetrahydro-6h-dibenzofuran-2-ol Chemical compound C1CCCC2C3=CC(O)=CC=C3OC21N1CCOCC1 CIRSWPZIDFTMED-UHFFFAOYSA-N 0.000 description 1
- SPVSRSKMSMLTEP-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzofuran-1-ol Chemical compound C1CCCC2=C1OC1=C2C(O)=CC=C1 SPVSRSKMSMLTEP-UHFFFAOYSA-N 0.000 description 1
- BFWZHKLATBONKY-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydrodibenzothiophene Chemical compound C1CCCC2=C1C1=CC=C(OC)C=C1S2 BFWZHKLATBONKY-UHFFFAOYSA-N 0.000 description 1
- GKKRSLDEKUNJFW-UHFFFAOYSA-N CCC(CC)(CCC(C(O)=O)C(O)=O)Br Chemical compound CCC(CC)(CCC(C(O)=O)C(O)=O)Br GKKRSLDEKUNJFW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical group CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- YIZFMRWRTQJUKE-UHFFFAOYSA-N S-(6,7,8,9-tetrahydrodibenzothiophen-2-yl) N,N-dimethylcarbamothioate Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)SC(N(C)C)=O YIZFMRWRTQJUKE-UHFFFAOYSA-N 0.000 description 1
- PWLMXNILCSULLF-UHFFFAOYSA-N SC1=C2C(OC3=C2CCCC3)=CC=C1 Chemical compound SC1=C2C(OC3=C2CCCC3)=CC=C1 PWLMXNILCSULLF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- CSLQAXTUGPUBCW-UHFFFAOYSA-N diethyl 2-bromo-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(Br)C(=O)OCC CSLQAXTUGPUBCW-UHFFFAOYSA-N 0.000 description 1
- KUWPEIMJRNJBII-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)SC1=CC2=C(OC3=C2CCCC3)C=C1)=O KUWPEIMJRNJBII-UHFFFAOYSA-N 0.000 description 1
- XVZLYLJJEXZTQE-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)OC=1C=CC2=C(OC3=C2CCCC3)C1)=O XVZLYLJJEXZTQE-UHFFFAOYSA-N 0.000 description 1
- CVYHCDDNYIZWQA-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)SC1=CC2=C(SC3=C2CCCC3)C=C1)=O CVYHCDDNYIZWQA-UHFFFAOYSA-N 0.000 description 1
- GHYAZTGZUDNEJQ-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)OC=1C=CC2=C(SC3=C2CCCC3)C1)=O GHYAZTGZUDNEJQ-UHFFFAOYSA-N 0.000 description 1
- NXAVOIHNEHIXBG-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfanyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)SC=1C=CC2=C(SC3=C2CCCC3)C1)=O NXAVOIHNEHIXBG-UHFFFAOYSA-N 0.000 description 1
- DSGUYHWHKYWRDG-UHFFFAOYSA-N diethyl 2-tetradecyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O DSGUYHWHKYWRDG-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- 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
-
- 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
- C07D333/76—Dibenzothiophenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/02—Bonding areas ; Manufacturing methods related thereto
- H01L24/04—Structure, shape, material or disposition of the bonding areas prior to the connecting process
- H01L24/05—Structure, shape, material or disposition of the bonding areas prior to the connecting process of an individual bonding area
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1223872A CH542837A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH425670A CH531501A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
| CH1223872A CH542837A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH542837A true CH542837A (de) | 1973-10-15 |
Family
ID=4272721
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1223872A CH542837A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
| CH425670A CH531501A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
| CH1223972A CH530388A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäureamiden |
| CH1224072A CH530389A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäureamiden |
| CH1223772A CH542836A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren und ihren Salzen |
| CH1223672A CH542835A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren und ihren Salzen |
| CH1224172A CH531502A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäurealkylestern |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH425670A CH531501A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
| CH1223972A CH530388A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäureamiden |
| CH1224072A CH530389A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäureamiden |
| CH1223772A CH542836A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren und ihren Salzen |
| CH1223672A CH542835A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren und ihren Salzen |
| CH1224172A CH531502A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäurealkylestern |
Country Status (19)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789072A (fr) * | 1971-09-23 | 1973-03-21 | Astra Laekemedel Ab | Composes abaissant le taux de lipides du serum et leur obtention |
| US3953601A (en) * | 1973-03-16 | 1976-04-27 | Aktiebolaget Astra | Dibenzothiophene derivatives as serum lipid lowering agents |
| US4101668A (en) * | 1977-05-10 | 1978-07-18 | Bristol-Myers Company | Antiosteoporotic agents |
| US4185108A (en) * | 1977-05-10 | 1980-01-22 | Westwood Pharmaceuticals Inc. | Antiosteoporotic agents |
| US4436748A (en) | 1980-10-20 | 1984-03-13 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4537976A (en) * | 1981-04-22 | 1985-08-27 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4528399A (en) * | 1981-04-22 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes intermediates |
| HRP20010078A2 (en) * | 1998-07-30 | 2002-02-28 | Warner Lambert Co | Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1997744A (en) * | 1932-10-05 | 1935-04-16 | Gen Aniline Works Inc | Hydroxydiphenylene compound |
-
1970
- 1970-03-20 CH CH1223872A patent/CH542837A/de not_active IP Right Cessation
- 1970-03-20 CH CH425670A patent/CH531501A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223972A patent/CH530388A/de not_active IP Right Cessation
- 1970-03-20 CH CH1224072A patent/CH530389A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223772A patent/CH542836A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223672A patent/CH542835A/de not_active IP Right Cessation
- 1970-03-20 CH CH1224172A patent/CH531502A/de not_active IP Right Cessation
-
1971
- 1971-03-12 NL NL7103358A patent/NL7103358A/xx unknown
- 1971-03-12 SE SE7103195A patent/SE378106B/xx unknown
- 1971-03-12 NO NO956/71A patent/NO134655C/no unknown
- 1971-03-12 DK DK118371AA patent/DK128003B/da unknown
- 1971-03-18 ES ES389360A patent/ES389360A1/es not_active Expired
- 1971-03-18 US US00125823A patent/US3784602A/en not_active Expired - Lifetime
- 1971-03-18 OA OA54203A patent/OA03697A/xx unknown
- 1971-03-19 SU SU1705729A patent/SU390716A3/ru active
- 1971-03-19 SU SU1701191A patent/SU391776A3/ru active
- 1971-03-19 AT AT965171A patent/AT307408B/de not_active IP Right Cessation
- 1971-03-19 DE DE19712113455 patent/DE2113455A1/de active Pending
- 1971-03-19 IE IE348/71A patent/IE35027B1/xx unknown
- 1971-03-19 CA CA108,184A patent/CA948209A/en not_active Expired
- 1971-03-19 AT AT239671A patent/AT302288B/de active
- 1971-03-19 AT AT965271A patent/AT307409B/de not_active IP Right Cessation
- 1971-03-19 AT AT965071A patent/AT307407B/de not_active IP Right Cessation
- 1971-03-19 BE BE764536A patent/BE764536A/xx unknown
- 1971-03-19 AT AT964671A patent/AT307403B/de not_active IP Right Cessation
- 1971-03-19 AT AT964571A patent/AT307402B/de not_active IP Right Cessation
- 1971-03-19 AT AT964971A patent/AT307406B/de not_active IP Right Cessation
- 1971-03-19 AT AT964871A patent/AT307405B/de not_active IP Right Cessation
- 1971-03-19 ZA ZA711800A patent/ZA711800B/xx unknown
- 1971-03-19 FR FR7109724A patent/FR2085725B1/fr not_active Expired
- 1971-03-19 IL IL36447A patent/IL36447A/en unknown
- 1971-03-19 AT AT964771A patent/AT307404B/de not_active IP Right Cessation
- 1971-03-19 SU SU711631737D patent/SU404258A3/ru active
- 1971-03-19 SU SU1688520A patent/SU419022A3/ru active
- 1971-04-19 GB GB2467171*#A patent/GB1331839A/en not_active Expired
-
1972
- 1972-02-01 AR AR240319A patent/AR195372A1/es active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |