FI58629C - Foerfarande foer framstaellning av en hypokolesterolemiskt och hypotriglyseridemiskt aktiv foerening - Google Patents
Foerfarande foer framstaellning av en hypokolesterolemiskt och hypotriglyseridemiskt aktiv foerening Download PDFInfo
- Publication number
- FI58629C FI58629C FI2675/73A FI267573A FI58629C FI 58629 C FI58629 C FI 58629C FI 2675/73 A FI2675/73 A FI 2675/73A FI 267573 A FI267573 A FI 267573A FI 58629 C FI58629 C FI 58629C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- phenoxy
- methylpropionate
- compound
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 70
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 34
- 239000000460 chlorine Chemical group 0.000 claims description 31
- 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 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052801 chlorine Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 10
- 239000008280 blood Substances 0.000 claims description 9
- 210000004369 blood Anatomy 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- JCHIUDLMOJNKRT-UHFFFAOYSA-N 4-(2,2-dichlorocyclopropyl)phenol Chemical compound C1=CC(O)=CC=C1C1C(Cl)(Cl)C1 JCHIUDLMOJNKRT-UHFFFAOYSA-N 0.000 claims description 6
- KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229950005228 bromoform Drugs 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 230000000871 hypocholesterolemic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 52
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- -1 bromoisobutyric acid ester Chemical class 0.000 description 23
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 229960001214 clofibrate Drugs 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XCTSGGVBLWBSIJ-UHFFFAOYSA-N 1-methoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=CC=C(C(C)=C)C=C1 XCTSGGVBLWBSIJ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- DTFRUPMUXJEBNK-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(1-phenylethenyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=C)C1=CC=CC=C1 DTFRUPMUXJEBNK-UHFFFAOYSA-N 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- PKYFPAVMKXQOCO-UHFFFAOYSA-N 4-(2,2-dichloro-1-methylcyclopropyl)phenol Chemical compound C=1C=C(O)C=CC=1C1(C)CC1(Cl)Cl PKYFPAVMKXQOCO-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- HNLHEYFTSQKTMX-UHFFFAOYSA-N ethyl 2-(2-chloro-4-ethenylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C=C)C=C1Cl HNLHEYFTSQKTMX-UHFFFAOYSA-N 0.000 description 4
- BYZWKIOOOBNGRO-UHFFFAOYSA-N ethyl 2-(4-ethenylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C=C)C=C1 BYZWKIOOOBNGRO-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- COQONOOFSJESDI-UHFFFAOYSA-N methyl 2-(4-but-2-en-2-ylphenoxy)-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC1=CC=C(C(C)=CC)C=C1 COQONOOFSJESDI-UHFFFAOYSA-N 0.000 description 4
- IXLWIDFWUUTFDT-UHFFFAOYSA-N methyl 2-methyl-2-(4-propanoylphenoxy)propanoate Chemical compound CCC(=O)C1=CC=C(OC(C)(C)C(=O)OC)C=C1 IXLWIDFWUUTFDT-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HPEKGLFCNUERTK-UHFFFAOYSA-N 1-(2,2-dichloro-1,3-dimethylcyclopropyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1(C)C(Cl)(Cl)C1C HPEKGLFCNUERTK-UHFFFAOYSA-N 0.000 description 3
- NDCBKNOIEQBTMX-UHFFFAOYSA-N 1-(2,2-dichloro-1-methylcyclopropyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1(C)C(Cl)(Cl)C1 NDCBKNOIEQBTMX-UHFFFAOYSA-N 0.000 description 3
- JLRGWZLYZHGEHM-UHFFFAOYSA-N 1-(2,2-dichlorocyclopropyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1C1C(Cl)(Cl)C1 JLRGWZLYZHGEHM-UHFFFAOYSA-N 0.000 description 3
- KNZWRFVSBJPWCE-UHFFFAOYSA-N 1-(2,2-difluoro-1-methylcyclopropyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1(C)C(F)(F)C1 KNZWRFVSBJPWCE-UHFFFAOYSA-N 0.000 description 3
- YETNAKJGOPZJBO-UHFFFAOYSA-N 1-(2,2-difluorocyclopropyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1C(F)(F)C1 YETNAKJGOPZJBO-UHFFFAOYSA-N 0.000 description 3
- YZNSKTOWHDRUQB-UHFFFAOYSA-N 1-but-2-en-2-yl-4-methoxybenzene Chemical compound COC1=CC=C(C(C)=CC)C=C1 YZNSKTOWHDRUQB-UHFFFAOYSA-N 0.000 description 3
- CDUYSGJRDZEJPK-UHFFFAOYSA-N 2-(4-acetylphenoxy)-2-methylpropanoic acid Chemical compound CC(=O)C1=CC=C(OC(C)(C)C(O)=O)C=C1 CDUYSGJRDZEJPK-UHFFFAOYSA-N 0.000 description 3
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 3
- SJBMBBSHOITKOV-UHFFFAOYSA-N 4-(2,2-dibromo-1-methylcyclopropyl)phenol Chemical compound C=1C=C(O)C=CC=1C1(C)CC1(Br)Br SJBMBBSHOITKOV-UHFFFAOYSA-N 0.000 description 3
- GPEGRFLERNEJIP-UHFFFAOYSA-N 4-(2,2-dichloro-1,3-dimethylcyclopropyl)phenol Chemical compound CC1C(Cl)(Cl)C1(C)C1=CC=C(O)C=C1 GPEGRFLERNEJIP-UHFFFAOYSA-N 0.000 description 3
- QSBXMKGMCIDJCG-UHFFFAOYSA-N 4-[(2,2-dichlorocyclopropyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1C(Cl)(Cl)C1 QSBXMKGMCIDJCG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- RGANFHLXCJSHAV-UHFFFAOYSA-N [bromo(dichloro)methyl]-phenylmercury Chemical compound ClC(Cl)(Br)[Hg]C1=CC=CC=C1 RGANFHLXCJSHAV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- GMGNIZODWQUHHL-UHFFFAOYSA-N ethyl 2-(3-acetylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C(C)=O)=C1 GMGNIZODWQUHHL-UHFFFAOYSA-N 0.000 description 3
- TYWBCJQKHPKZIC-UHFFFAOYSA-N ethyl 2-(3-ethenylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C=C)=C1 TYWBCJQKHPKZIC-UHFFFAOYSA-N 0.000 description 3
- ZNVQWEKDWFYMMZ-UHFFFAOYSA-N ethyl 2-(4-acetyl-2-chlorophenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C(C)=O)C=C1Cl ZNVQWEKDWFYMMZ-UHFFFAOYSA-N 0.000 description 3
- CISUSLQTNJUNKV-UHFFFAOYSA-N ethyl 2-[2-chloro-4-(1-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C(C)O)C=C1Cl CISUSLQTNJUNKV-UHFFFAOYSA-N 0.000 description 3
- ADHZBPSBMDNJMF-UHFFFAOYSA-N ethyl 2-[4-(2,2-dichloro-3-phenylcyclopropyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1C(Cl)(Cl)C1C1=CC=CC=C1 ADHZBPSBMDNJMF-UHFFFAOYSA-N 0.000 description 3
- AGBBPJPJZCHECM-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(2-phenylethenyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C=CC1=CC=CC=C1 AGBBPJPJZCHECM-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- BOPUUZSQLQYFOL-UHFFFAOYSA-N methyl 2-(4-but-1-en-2-ylphenoxy)-2-methylpropanoate Chemical compound CCC(=C)C1=CC=C(OC(C)(C)C(=O)OC)C=C1 BOPUUZSQLQYFOL-UHFFFAOYSA-N 0.000 description 3
- YFDNNKGQVQSPHR-UHFFFAOYSA-N methyl 2-methyl-2-(4-prop-1-enylphenoxy)propanoate Chemical compound COC(=O)C(C)(C)OC1=CC=C(C=CC)C=C1 YFDNNKGQVQSPHR-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NWFRTSLXRDGBHY-UHFFFAOYSA-N 1-(2,2-dibromo-1-methylcyclopropyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1(C)C(Br)(Br)C1 NWFRTSLXRDGBHY-UHFFFAOYSA-N 0.000 description 2
- ZTQCYPYTWDMMHA-UHFFFAOYSA-N 1-[(2,2-dichlorocyclopropyl)methyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CC1C(Cl)(Cl)C1 ZTQCYPYTWDMMHA-UHFFFAOYSA-N 0.000 description 2
- ZCZFPBCRZGDTEB-UHFFFAOYSA-N 2-(2,2-dichlorocyclopropyl)phenol Chemical compound OC1=CC=CC=C1C1C(Cl)(Cl)C1 ZCZFPBCRZGDTEB-UHFFFAOYSA-N 0.000 description 2
- DVPAMMZKRSYREL-UHFFFAOYSA-N 2-(4-acetyl-2-chlorophenoxy)-2-methylpropanoic acid Chemical compound CC(=O)C1=CC=C(OC(C)(C)C(O)=O)C(Cl)=C1 DVPAMMZKRSYREL-UHFFFAOYSA-N 0.000 description 2
- APKUMQIYSDQVPT-UHFFFAOYSA-N 2-[4-(2,2-dibromo-1-phenylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1(C=2C=CC=CC=2)C(Br)(Br)C1 APKUMQIYSDQVPT-UHFFFAOYSA-N 0.000 description 2
- YSXUEFRQDYBFOK-UHFFFAOYSA-N 2-[4-(2,2-dibromocyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Br)(Br)C1 YSXUEFRQDYBFOK-UHFFFAOYSA-N 0.000 description 2
- HKLPKOXQVPABDC-UHFFFAOYSA-N 2-[4-(2,2-dichloro-1-methylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1(C)C(Cl)(Cl)C1 HKLPKOXQVPABDC-UHFFFAOYSA-N 0.000 description 2
- WFCIHASSJSTHMG-UHFFFAOYSA-N 2-[4-(2,2-difluoro-1-methylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1(C)C(F)(F)C1 WFCIHASSJSTHMG-UHFFFAOYSA-N 0.000 description 2
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 2
- DECOEVQNIFPJIC-UHFFFAOYSA-N 2-methyl-2-(4-propanoylphenoxy)propanoic acid Chemical compound CCC(=O)C1=CC=C(OC(C)(C)C(O)=O)C=C1 DECOEVQNIFPJIC-UHFFFAOYSA-N 0.000 description 2
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- CWWRAMLRPASOKP-UHFFFAOYSA-N ethyl 2-[4-[(2,2-dichlorocyclopropyl)methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CC1C(Cl)(Cl)C1 CWWRAMLRPASOKP-UHFFFAOYSA-N 0.000 description 1
- AESMBAOYBVZEOY-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(2-phenylethyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CCC1=CC=CC=C1 AESMBAOYBVZEOY-UHFFFAOYSA-N 0.000 description 1
- GELSOTNVVKOYAW-UHFFFAOYSA-N ethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 GELSOTNVVKOYAW-UHFFFAOYSA-N 0.000 description 1
- 208000023414 familial retinal arterial macroaneurysm Diseases 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CPMVZMIRYBRPNE-UHFFFAOYSA-N methyl 2-[4-(1-hydroxypropyl)phenoxy]-2-methylpropanoate Chemical compound CCC(O)C1=CC=C(OC(C)(C)C(=O)OC)C=C1 CPMVZMIRYBRPNE-UHFFFAOYSA-N 0.000 description 1
- MKUXXHJVSKQNHO-UHFFFAOYSA-N methyl 2-[4-(2,2-dichloro-1-ethylcyclopropyl)phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC)C=CC=1C1(CC)CC1(Cl)Cl MKUXXHJVSKQNHO-UHFFFAOYSA-N 0.000 description 1
- GHEZEWLHBUBEIZ-UHFFFAOYSA-N methyl 2-[4-(2,2-dichloro-3-methylcyclopropyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC)=CC=C1C1C(Cl)(Cl)C1C GHEZEWLHBUBEIZ-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- MVIAEGXPYBMVPT-UHFFFAOYSA-N phenyl(trichloromethyl)mercury Chemical compound ClC(Cl)(Cl)[Hg]C1=CC=CC=C1 MVIAEGXPYBMVPT-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical class Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28457772A | 1972-08-29 | 1972-08-29 | |
| US28457772 | 1972-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58629B FI58629B (fi) | 1980-11-28 |
| FI58629C true FI58629C (fi) | 1981-03-10 |
Family
ID=23090716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2675/73A FI58629C (fi) | 1972-08-29 | 1973-08-28 | Foerfarande foer framstaellning av en hypokolesterolemiskt och hypotriglyseridemiskt aktiv foerening |
Country Status (20)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2471364A1 (fr) * | 1979-12-11 | 1981-06-19 | Rhone Poulenc Agrochimie | Nouveaux derives de l'aniline et compositions regulatrices de la croissance des plantes les contenant |
| US4691042A (en) * | 1983-06-24 | 1987-09-01 | The Dow Chemical Company | Preparation of monaoalkylated dihydroxybenzenes and novel compounds prepared thereby |
| GB8330407D0 (en) * | 1983-11-15 | 1983-12-21 | Sterwin Ag | Halocyclopropyl-substituted phenoxyalkanoic acids and esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121722A (en) * | 1966-03-31 | 1968-07-31 | Ici Ltd | New carboxylic acid derivatives |
| BE754245A (fr) * | 1969-08-01 | 1970-12-31 | Sumitomo Chemical Co | Derives d'acides phenoxy carboxyliques |
-
1973
- 1973-01-01 AR AR249792A patent/AR206596A1/es active
- 1973-08-13 GB GB3831173A patent/GB1385828A/en not_active Expired
- 1973-08-20 IL IL43026A patent/IL43026A/en unknown
- 1973-08-22 AU AU59488/73A patent/AU472631B2/en not_active Expired
- 1973-08-22 ZA ZA735748A patent/ZA735748B/xx unknown
- 1973-08-22 FR FR7330434A patent/FR2197586B1/fr not_active Expired
- 1973-08-23 BE BE1005309A patent/BE803924A/xx not_active IP Right Cessation
- 1973-08-24 PH PH14951A patent/PH10530A/en unknown
- 1973-08-27 CH CH7312272A patent/CH608780A5/xx not_active IP Right Cessation
- 1973-08-27 CH CH959876A patent/CH605584A5/fr not_active IP Right Cessation
- 1973-08-27 AT AT744773A patent/AT331207B/de not_active IP Right Cessation
- 1973-08-28 NO NO3388/73A patent/NO143528C/no unknown
- 1973-08-28 CA CA179,829A patent/CA1023762A/en not_active Expired
- 1973-08-28 SE SE7311687A patent/SE417828B/xx unknown
- 1973-08-28 ES ES418283A patent/ES418283A1/es not_active Expired
- 1973-08-28 DK DK471773AA patent/DK141366B/da not_active IP Right Cessation
- 1973-08-28 FI FI2675/73A patent/FI58629C/fi active
- 1973-08-29 NL NLAANVRAGE7311903,A patent/NL180004C/xx not_active IP Right Cessation
- 1973-08-29 JP JP48096261A patent/JPS585175B2/ja not_active Expired
- 1973-08-29 DE DE2343606A patent/DE2343606C2/de not_active Expired
-
1980
- 1980-02-28 HK HK69/80A patent/HK6980A/xx unknown
-
1982
- 1982-06-02 JP JP57094644A patent/JPS60334B2/ja not_active Expired
- 1982-06-02 JP JP57094645A patent/JPS60335B2/ja not_active Expired
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