IL36447A - 6,7,8,9-tetrahydrodibenzofuran and 6,7,8,9-tetrahydrodibenzothiophene derivatives,their production and pharmaceuticalcompositions containing them - Google Patents
6,7,8,9-tetrahydrodibenzofuran and 6,7,8,9-tetrahydrodibenzothiophene derivatives,their production and pharmaceuticalcompositions containing themInfo
- Publication number
- IL36447A IL36447A IL36447A IL3644771A IL36447A IL 36447 A IL36447 A IL 36447A IL 36447 A IL36447 A IL 36447A IL 3644771 A IL3644771 A IL 3644771A IL 36447 A IL36447 A IL 36447A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- mmol
- yloxy
- tetrahydrodibenzofuran
- general formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- LREHXNMBUBVFHA-UHFFFAOYSA-N 1,2,3,4-tetrahydrodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1CCCC2 LREHXNMBUBVFHA-UHFFFAOYSA-N 0.000 title description 4
- JCLPOPNXITXHOR-UHFFFAOYSA-N 1,2,3,4-tetrahydrodibenzothiophene Chemical class S1C2=CC=CC=C2C2=C1CCCC2 JCLPOPNXITXHOR-UHFFFAOYSA-N 0.000 title description 3
- -1 alkali metal salt Chemical class 0.000 claims description 171
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 151
- 239000002253 acid Substances 0.000 claims description 126
- 238000000034 method Methods 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052783 alkali metal Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 30
- 150000007513 acids Chemical class 0.000 claims description 25
- 150000002825 nitriles Chemical class 0.000 claims description 24
- 150000001735 carboxylic acids Chemical class 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 150000001340 alkali metals Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001447 alkali salts Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical group CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 345
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 247
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 204
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 179
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 177
- 239000000243 solution Substances 0.000 description 156
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 100
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 70
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 70
- 239000011541 reaction mixture Substances 0.000 description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
- 238000001704 evaporation Methods 0.000 description 50
- 239000003921 oil Substances 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- 230000008020 evaporation Effects 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
- 238000003756 stirring Methods 0.000 description 42
- 238000001816 cooling Methods 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000007858 starting material Substances 0.000 description 38
- 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 37
- 125000004494 ethyl ester group Chemical group 0.000 description 37
- 238000001035 drying Methods 0.000 description 36
- 238000010992 reflux Methods 0.000 description 36
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- 235000019341 magnesium sulphate Nutrition 0.000 description 35
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 239000002904 solvent Substances 0.000 description 33
- 230000007935 neutral effect Effects 0.000 description 32
- 229960000583 acetic acid Drugs 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- 238000010828 elution Methods 0.000 description 27
- 239000012071 phase Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 239000012362 glacial acetic acid Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 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 24
- 238000004440 column chromatography Methods 0.000 description 23
- 239000011734 sodium Substances 0.000 description 23
- 229910052708 sodium Inorganic materials 0.000 description 23
- 239000012043 crude product Substances 0.000 description 22
- 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 description 21
- 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 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 229960003424 phenylacetic acid Drugs 0.000 description 16
- 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 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 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 13
- 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 13
- 238000001953 recrystallisation Methods 0.000 description 13
- 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 12
- 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 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- JHBMPQFJFJKMFS-UHFFFAOYSA-N 6,7,8,9-tetrahydrodibenzothiophene-3-thiol Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)S JHBMPQFJFJKMFS-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000001117 sulphuric acid Substances 0.000 description 11
- 235000011149 sulphuric acid Nutrition 0.000 description 11
- 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 10
- 239000013078 crystal Substances 0.000 description 10
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 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 9
- 239000013543 active substance Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 8
- 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 8
- GTGTXZRPJHDASG-UHFFFAOYSA-N 2-bromooctanoic acid Chemical compound CCCCCCC(Br)C(O)=O GTGTXZRPJHDASG-UHFFFAOYSA-N 0.000 description 8
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000012259 ether extract Substances 0.000 description 8
- JIQJOKSCSVMZAN-UHFFFAOYSA-N ethyl 2-bromooctanoate Chemical compound CCCCCCC(Br)C(=O)OCC JIQJOKSCSVMZAN-UHFFFAOYSA-N 0.000 description 8
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 8
- 235000010755 mineral Nutrition 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 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 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 230000001376 precipitating effect Effects 0.000 description 7
- 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 description 6
- 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 6
- FFOILHLQMLNURQ-UHFFFAOYSA-N 2-chlorooctanamide Chemical compound CCCCCCC(Cl)C(N)=O FFOILHLQMLNURQ-UHFFFAOYSA-N 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 6
- 150000001342 alkaline earth metals Chemical group 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 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 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
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- VGYZSIMAKGWWOP-UHFFFAOYSA-N ethyl 2-bromododecanoate Chemical compound CCCCCCCCCCC(Br)C(=O)OCC VGYZSIMAKGWWOP-UHFFFAOYSA-N 0.000 description 6
- FZNMMDGZAGNHMH-UHFFFAOYSA-N ethyl 2-bromohexadecanoate Chemical compound CCCCCCCCCCCCCCC(Br)C(=O)OCC FZNMMDGZAGNHMH-UHFFFAOYSA-N 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 235000012222 talc Nutrition 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- GZHNWRYYMJCHBM-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)heptanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCC GZHNWRYYMJCHBM-UHFFFAOYSA-N 0.000 description 5
- USBMICJKYWSDCF-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)octanamide Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)N)CCCCCC USBMICJKYWSDCF-UHFFFAOYSA-N 0.000 description 5
- KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 235000019759 Maize starch Nutrition 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- VPWIQUHAZFGHIN-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)octanoate Chemical compound C(C)OC(C(CCCCCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O VPWIQUHAZFGHIN-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- BRTORKIVDSBTDG-UHFFFAOYSA-N 2-(4-methoxyphenoxy)cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1OC1C(=O)CCCC1 BRTORKIVDSBTDG-UHFFFAOYSA-N 0.000 description 4
- DJRHWPULZPJTPW-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)dodecanamide Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)OC(C(=O)N)CCCCCCCCCC DJRHWPULZPJTPW-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 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 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
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- LVWKRTDDUIYWBR-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)acetic acid Chemical compound C1CCCC2=C1OC1=CC=C(OCC(=O)O)C=C12 LVWKRTDDUIYWBR-UHFFFAOYSA-N 0.000 description 3
- GJLPBGDDRRJKPD-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)acetic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)SCC(=O)O GJLPBGDDRRJKPD-UHFFFAOYSA-N 0.000 description 3
- STCQQQKMTXZMLU-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)heptanamide Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)SC(C(=O)N)CCCCC STCQQQKMTXZMLU-UHFFFAOYSA-N 0.000 description 3
- JLPBZLRUPIBVQI-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)heptanoic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)SC(C(=O)O)CCCCC JLPBZLRUPIBVQI-UHFFFAOYSA-N 0.000 description 3
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 3
- HXKXBCBZXXQPPD-UHFFFAOYSA-N 2-bromododecanoic acid Chemical compound CCCCCCCCCCC(Br)C(O)=O HXKXBCBZXXQPPD-UHFFFAOYSA-N 0.000 description 3
- NQRFAUVGDLHPGH-UHFFFAOYSA-N 2-bromoheptanoic acid Chemical compound CCCCCC(Br)C(O)=O NQRFAUVGDLHPGH-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
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- CSLQAXTUGPUBCW-UHFFFAOYSA-N diethyl 2-bromo-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(Br)C(=O)OCC CSLQAXTUGPUBCW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- HEJXPENXHAIYNJ-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)butanoate Chemical compound C(C)OC(C(CC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O HEJXPENXHAIYNJ-UHFFFAOYSA-N 0.000 description 3
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- 238000006460 hydrolysis reaction Methods 0.000 description 3
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- 229920001592 potato starch Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- RAJQWFNCAGFSMN-UHFFFAOYSA-N 2-(3-methoxyphenyl)sulfanylcyclohexan-1-one Chemical compound COC1=CC=CC(SC2C(CCCC2)=O)=C1 RAJQWFNCAGFSMN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OZXRXMBHKBSCFO-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)heptanamide Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)N)CCCCC OZXRXMBHKBSCFO-UHFFFAOYSA-N 0.000 description 2
- LPKGWOMIRYYFQU-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)hexadecanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCCCCCCCCCC LPKGWOMIRYYFQU-UHFFFAOYSA-N 0.000 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 description 2
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- IARPNSGOWKGBSG-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)acetic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SCC(=O)O IARPNSGOWKGBSG-UHFFFAOYSA-N 0.000 description 2
- IHZHFTMOGOROKQ-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)octanamide Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)N)CCCCCC IHZHFTMOGOROKQ-UHFFFAOYSA-N 0.000 description 2
- RVPIVYQDONUXFZ-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)acetic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)OCC(=O)O RVPIVYQDONUXFZ-UHFFFAOYSA-N 0.000 description 2
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- YRHIKQMIBZMSQV-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)acetic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OCC(=O)O YRHIKQMIBZMSQV-UHFFFAOYSA-N 0.000 description 2
- RVHWPWHODQYSOD-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)octanamide Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OC(C(=O)N)CCCCCC RVHWPWHODQYSOD-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
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- AQQAHBQCIBGFLA-UHFFFAOYSA-N 2-chloroheptanamide Chemical compound CCCCCC(Cl)C(N)=O AQQAHBQCIBGFLA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- BUWVWTCJFZEYNY-UHFFFAOYSA-N 2-methyl-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)C BUWVWTCJFZEYNY-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
- 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
- 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 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XMAQIACJUAOTJC-UHFFFAOYSA-N C(C)OC(C(C(C)C)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O Chemical compound C(C)OC(C(C(C)C)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O XMAQIACJUAOTJC-UHFFFAOYSA-N 0.000 description 2
- QRGHGTZMIRKVKJ-UHFFFAOYSA-N C1=C(C=CC=2SC3=C(C=21)CCCC3)OC(C(=O)O)(C)C Chemical compound C1=C(C=CC=2SC3=C(C=21)CCCC3)OC(C(=O)O)(C)C QRGHGTZMIRKVKJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 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
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RQMWFQLFLCRKIZ-UHFFFAOYSA-N diethyl 2-decyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCC)SC=1C=CC2=C(OC3=C2CCCC3)C1)=O RQMWFQLFLCRKIZ-UHFFFAOYSA-N 0.000 description 2
- PHMKLNKGJIMGLO-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O PHMKLNKGJIMGLO-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- GFHOIZOFHCYOMR-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)octanoate Chemical compound C(C)OC(C(CCCCCC)SC=1C=CC2=C(OC3=C2CCCC3)C1)=O GFHOIZOFHCYOMR-UHFFFAOYSA-N 0.000 description 2
- HWOINWCLQKIPLO-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)propanoate Chemical compound C(C)OC(C(C)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O HWOINWCLQKIPLO-UHFFFAOYSA-N 0.000 description 2
- RJTBLJNHBFLWFN-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)hexadecanoate Chemical compound C(C)OC(C(CCCCCCCCCCCCCC)OC=1C=CC2=C(SC3=C2CCCC3)C1)=O RJTBLJNHBFLWFN-UHFFFAOYSA-N 0.000 description 2
- ASAVSTVCQPMIFA-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)propanoate Chemical compound C(C)OC(C(C)OC=1C=CC2=C(SC3=C2CCCC3)C1)=O ASAVSTVCQPMIFA-UHFFFAOYSA-N 0.000 description 2
- SXZHDULBCLKRAE-UHFFFAOYSA-N ethyl 2-bromo-5-methylhexanoate Chemical compound CCOC(=O)C(Br)CCC(C)C SXZHDULBCLKRAE-UHFFFAOYSA-N 0.000 description 2
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 2
- ICHJBBQVLWQXPZ-UHFFFAOYSA-N ethyl 2-cyano-2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)octanoate Chemical compound C(C)OC(C(CCCCCC)(OC1=CC2=C(OC3=C2CCCC3)C=C1)C#N)=O ICHJBBQVLWQXPZ-UHFFFAOYSA-N 0.000 description 2
- NQAGGKSIUUFXIZ-UHFFFAOYSA-N ethyl 2-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)propanoate Chemical compound C(C)OC(C(C)(C)SC1=CC2=C(OC3=C2CCCC3)C=C1)=O NQAGGKSIUUFXIZ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
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- 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 1
- AZCWNVXXHATZBK-UHFFFAOYSA-N diethyl 2-bromo-2-propylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCC)Br)=O AZCWNVXXHATZBK-UHFFFAOYSA-N 0.000 description 1
- QQWUOQUOEVWDMJ-UHFFFAOYSA-N diethyl 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCC)SC=1C=CC2=C(OC3=C2CCCC3)C1)=O QQWUOQUOEVWDMJ-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
- 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
- QFZMAYOYNUTWLQ-UHFFFAOYSA-N diethyl 2-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(C)OC=1C=CC2=C(OC3=C2CCCC3)C1)=O QFZMAYOYNUTWLQ-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
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UZHSPLZWMUFOKV-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)dodecanoate Chemical compound C(C)OC(C(CCCCCCCCCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O UZHSPLZWMUFOKV-UHFFFAOYSA-N 0.000 description 1
- WODQEQQCVCRNQP-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)hexadecanoate Chemical compound C(C)OC(C(CCCCCCCCCCCCCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O WODQEQQCVCRNQP-UHFFFAOYSA-N 0.000 description 1
- HCXBWQQLOZGEOX-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)pentanoate Chemical compound C(C)OC(C(CCC)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O HCXBWQQLOZGEOX-UHFFFAOYSA-N 0.000 description 1
- WULFSZBGUFZJKJ-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanoate Chemical compound C(C)OC(C(C)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O WULFSZBGUFZJKJ-UHFFFAOYSA-N 0.000 description 1
- PVXGSCIZBRFHSD-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)octanoate Chemical compound C(C)OC(C(CCCCCC)OC=1C=CC2=C(OC3=C2CCCC3)C1)=O PVXGSCIZBRFHSD-UHFFFAOYSA-N 0.000 description 1
- QASIXEKMBVCHDN-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)propanoate Chemical compound C(C)OC(C(C)OC=1C=CC2=C(OC3=C2CCCC3)C1)=O QASIXEKMBVCHDN-UHFFFAOYSA-N 0.000 description 1
- BXVUAMAKEJEWJT-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanoate Chemical compound C(C)OC(C(C)SC=1C=CC2=C(OC3=C2CCCC3)C1)=O BXVUAMAKEJEWJT-UHFFFAOYSA-N 0.000 description 1
- IBGNXGIYRSMROJ-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)dodecanoate Chemical compound C(C)OC(C(CCCCCCCCCC)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O IBGNXGIYRSMROJ-UHFFFAOYSA-N 0.000 description 1
- MHNXBAJGPLEKMR-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)octanoate Chemical compound C(C)OC(C(CCCCCC)OC1=CC2=C(SC3=C2CCCC3)C=C1)=O MHNXBAJGPLEKMR-UHFFFAOYSA-N 0.000 description 1
- AQWQKRCAOBMHHT-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)dodecanoate Chemical compound C(C)OC(C(CCCCCCCCCC)SC1=CC2=C(SC3=C2CCCC3)C=C1)=O AQWQKRCAOBMHHT-UHFFFAOYSA-N 0.000 description 1
- DEAOATHDUVSHFK-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)hexadecanoate Chemical compound C(C)OC(C(CCCCCCCCCCCCCC)SC1=CC2=C(SC3=C2CCCC3)C=C1)=O DEAOATHDUVSHFK-UHFFFAOYSA-N 0.000 description 1
- WRTKVWCAFJFJQW-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-2-ylsulfanyl)octanoate Chemical compound C(C)OC(C(CCCCCC)SC1=CC2=C(SC3=C2CCCC3)C=C1)=O WRTKVWCAFJFJQW-UHFFFAOYSA-N 0.000 description 1
- MEKBELFFLGWWFF-UHFFFAOYSA-N ethyl 2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfanyl)dodecanoate Chemical compound C(C)OC(C(CCCCCCCCCC)SC=1C=CC2=C(SC3=C2CCCC3)C1)=O MEKBELFFLGWWFF-UHFFFAOYSA-N 0.000 description 1
- LBUGMEORJQXPEE-UHFFFAOYSA-N ethyl 2-[2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)cyclopentyl]acetate Chemical compound C(C)OC(CC1C(CCC1)OC1=CC2=C(OC3=C2CCCC3)C=C1)=O LBUGMEORJQXPEE-UHFFFAOYSA-N 0.000 description 1
- AZRBWVKLYGQVTI-UHFFFAOYSA-N ethyl 2-bromo-2-cyanoheptanoate Chemical compound C(C)OC(C(C#N)(CCCCC)Br)=O AZRBWVKLYGQVTI-UHFFFAOYSA-N 0.000 description 1
- WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-UHFFFAOYSA-N 0.000 description 1
- IOOXHTJCOQWOJW-UHFFFAOYSA-N ethyl 2-bromodecanoate Chemical compound CCCCCCCCC(Br)C(=O)OCC IOOXHTJCOQWOJW-UHFFFAOYSA-N 0.000 description 1
- GNCLPIAYAPQPOU-UHFFFAOYSA-N ethyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OCC GNCLPIAYAPQPOU-UHFFFAOYSA-N 0.000 description 1
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
- JQQZIRFEGUUJBP-UHFFFAOYSA-N ethyl 2-bromotetradecanoate Chemical compound CCCCCCCCCCCCC(Br)C(=O)OCC JQQZIRFEGUUJBP-UHFFFAOYSA-N 0.000 description 1
- WJGFHJCJABTNPO-UHFFFAOYSA-N ethyl 2-cyano-2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)heptanoate Chemical compound C(C)OC(C(CCCCC)(OC=1C=CC2=C(SC3=C2CCCC3)C1)C#N)=O WJGFHJCJABTNPO-UHFFFAOYSA-N 0.000 description 1
- CLUHOXPLTPHBTE-UHFFFAOYSA-N ethyl 2-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-yloxy)propanoate Chemical compound C(C)OC(C(C)(C)OC=1C=CC2=C(OC3=C2CCCC3)C1)=O CLUHOXPLTPHBTE-UHFFFAOYSA-N 0.000 description 1
- BEDWZGWVHQRKFB-UHFFFAOYSA-N ethyl 5-methyl-2-(6,7,8,9-tetrahydrodibenzofuran-2-ylsulfanyl)hexanoate Chemical compound C(C)OC(C(CCC(C)C)SC1=CC2=C(OC3=C2CCCC3)C=C1)=O BEDWZGWVHQRKFB-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000007902 hard capsule Substances 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
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000002035 hexane extract Substances 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
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine 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
- 239000004922 lacquer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- XEENYBWXUFATQF-UHFFFAOYSA-N methyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OC XEENYBWXUFATQF-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 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
- 125000001400 nonyl 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])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- LYFBUEDPAUEDSU-UHFFFAOYSA-N propyl 2-bromoheptanoate Chemical compound C(CC)OC(C(CCCCC)Br)=O LYFBUEDPAUEDSU-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
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- HLVQCKKRDJBZSS-UHFFFAOYSA-M sodium 6,7,8,9-tetrahydrodibenzofuran-3-olate Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)[O-].[Na+] HLVQCKKRDJBZSS-UHFFFAOYSA-M 0.000 description 1
- ZXAVSKJGMIZPCH-UHFFFAOYSA-M sodium 6,7,8,9-tetrahydrodibenzofuran-3-thiolate Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)[S-].[Na+] ZXAVSKJGMIZPCH-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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)
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36447A0 IL36447A0 (en) | 1971-05-26 |
| IL36447A true IL36447A (en) | 1974-10-22 |
Family
ID=4272721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36447A IL36447A (en) | 1970-03-20 | 1971-03-19 | 6,7,8,9-tetrahydrodibenzofuran and 6,7,8,9-tetrahydrodibenzothiophene derivatives,their production and pharmaceuticalcompositions containing them |
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 |
| US4185108A (en) * | 1977-05-10 | 1980-01-22 | Westwood Pharmaceuticals Inc. | Antiosteoporotic agents |
| US4101668A (en) * | 1977-05-10 | 1978-07-18 | Bristol-Myers Company | Antiosteoporotic agents |
| US4436748A (en) | 1980-10-20 | 1984-03-13 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4528399A (en) * | 1981-04-22 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes intermediates |
| US4537976A (en) * | 1981-04-22 | 1985-08-27 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| EP1100792B1 (en) * | 1998-07-30 | 2004-03-17 | Warner-Lambert Company LLC | 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 CH1224172A patent/CH531502A/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 CH1223672A patent/CH542835A/de not_active IP Right Cessation
- 1970-03-20 CH CH425670A patent/CH531501A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223872A patent/CH542837A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223772A patent/CH542836A/de not_active IP Right Cessation
-
1971
- 1971-03-12 SE SE7103195A patent/SE378106B/xx unknown
- 1971-03-12 DK DK118371AA patent/DK128003B/da unknown
- 1971-03-12 NO NO956/71A patent/NO134655C/no unknown
- 1971-03-12 NL NL7103358A patent/NL7103358A/xx unknown
- 1971-03-18 ES ES389360A patent/ES389360A1/es not_active Expired
- 1971-03-18 OA OA54203A patent/OA03697A/xx unknown
- 1971-03-18 US US00125823A patent/US3784602A/en not_active Expired - Lifetime
- 1971-03-19 SU SU1688520A patent/SU419022A3/ru active
- 1971-03-19 AT AT964771A patent/AT307404B/de not_active IP Right Cessation
- 1971-03-19 AT AT964971A patent/AT307406B/de not_active IP Right Cessation
- 1971-03-19 SU SU711631737D patent/SU404258A3/ru active
- 1971-03-19 IE IE348/71A patent/IE35027B1/xx unknown
- 1971-03-19 AT AT964571A patent/AT307402B/de not_active IP Right Cessation
- 1971-03-19 FR FR7109724A patent/FR2085725B1/fr not_active Expired
- 1971-03-19 ZA ZA711800A patent/ZA711800B/xx unknown
- 1971-03-19 AT AT964671A patent/AT307403B/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 SU SU1705729A patent/SU390716A3/ru active
- 1971-03-19 AT AT965271A patent/AT307409B/de not_active IP Right Cessation
- 1971-03-19 AT AT964871A patent/AT307405B/de not_active IP Right Cessation
- 1971-03-19 SU SU1701191A patent/SU391776A3/ru active
- 1971-03-19 AT AT239671A patent/AT302288B/de active
- 1971-03-19 DE DE19712113455 patent/DE2113455A1/de active Pending
- 1971-03-19 AT AT965171A patent/AT307408B/de not_active IP Right Cessation
- 1971-03-19 CA CA108,184A patent/CA948209A/en not_active Expired
- 1971-03-19 IL IL36447A patent/IL36447A/en unknown
- 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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