CH605584A5 - Halo-cyclopropyl aryloxy alkanoic acids and esters - Google Patents
Halo-cyclopropyl aryloxy alkanoic acids and estersInfo
- Publication number
- CH605584A5 CH605584A5 CH959876A CH959876A CH605584A5 CH 605584 A5 CH605584 A5 CH 605584A5 CH 959876 A CH959876 A CH 959876A CH 959876 A CH959876 A CH 959876A CH 605584 A5 CH605584 A5 CH 605584A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methylpropionate
- formula
- compound
- phenoxy
- ethyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 30
- 150000002148 esters Chemical class 0.000 title claims abstract description 10
- 150000007513 acids Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 2- [2- methyl 4- (2,2-dichloro-1 -methylcyclopropyl) phenoxy] -2-methylpropionate Chemical compound 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- UHYJTDLWNOQAFE-UHFFFAOYSA-N ethyl 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1C(Cl)(Cl)C1 UHYJTDLWNOQAFE-UHFFFAOYSA-N 0.000 claims description 2
- ZZXDVSFTBMXRHP-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-4-prop-1-en-2-ylphenoxy)propanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C(C)=C)C=C1C ZZXDVSFTBMXRHP-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 230000000999 hypotriglyceridemic effect Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 29
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 229960001701 chloroform Drugs 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 8
- 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 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229950005228 bromoform Drugs 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 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 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000000871 hypocholesterolemic effect Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- LWLRITLSGGNJTL-UHFFFAOYSA-N methyl 2-(4-acetylphenoxy)-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC1=CC=C(C(C)=O)C=C1 LWLRITLSGGNJTL-UHFFFAOYSA-N 0.000 description 3
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- 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 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VAGIFJAZXWOOGR-UHFFFAOYSA-N 2-[3-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(C2C(C2)(Cl)Cl)=C1 VAGIFJAZXWOOGR-UHFFFAOYSA-N 0.000 description 2
- CXLSEPVPEDWYQD-UHFFFAOYSA-N 2-[4-(2,2-dichloro-3-phenylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1C1=CC=CC=C1 CXLSEPVPEDWYQD-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
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- YDTWAGLILFSFFY-UHFFFAOYSA-N ethyl 2-[4-(1-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C(C)O)C=C1 YDTWAGLILFSFFY-UHFFFAOYSA-N 0.000 description 2
- IEUPGVSABAGTLT-UHFFFAOYSA-N ethyl 2-[4-(2-chloro-2-fluorocyclopropyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1C(Cl)(F)C1 IEUPGVSABAGTLT-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 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 2
- 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 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000021590 normal diet Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 150000002989 phenols Chemical group 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 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 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- JNVXRQOSRUDXDY-UHFFFAOYSA-N 1,1-diiodoethane Chemical compound CC(I)I JNVXRQOSRUDXDY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GMTSPBYBJKGPJF-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C(Cl)=C1 GMTSPBYBJKGPJF-UHFFFAOYSA-N 0.000 description 1
- JBQTZLNCDIFCCO-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-phenylethan-1-one Chemical compound C1=CC(O)=CC=C1C(=O)CC1=CC=CC=C1 JBQTZLNCDIFCCO-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical class ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DCHXMPPXWFUMOH-UHFFFAOYSA-N 2-(4-benzoylphenoxy)-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=CC=C1 DCHXMPPXWFUMOH-UHFFFAOYSA-N 0.000 description 1
- IIJBUUJYXSWCGW-UHFFFAOYSA-N 2-(4-ethenylphenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(C=C)C=C1 IIJBUUJYXSWCGW-UHFFFAOYSA-N 0.000 description 1
- OZMWKLPYGYMDEJ-UHFFFAOYSA-N 2-[4-(1-hydroxyethyl)phenoxy]-2-methylpropanoic acid Chemical compound CC(O)C1=CC=C(OC(C)(C)C(O)=O)C=C1 OZMWKLPYGYMDEJ-UHFFFAOYSA-N 0.000 description 1
- ILHWKLFZXYVMSY-UHFFFAOYSA-N 2-[4-(2,2-dibromo-1,3-dimethylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound CC1C(Br)(Br)C1(C)C1=CC=C(OC(C)(C)C(O)=O)C=C1 ILHWKLFZXYVMSY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XWSKQJGOCCSNQL-UHFFFAOYSA-N 2-[4-(2,2-dichloro-1,3-dimethylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound CC1C(Cl)(Cl)C1(C)C1=CC=C(OC(C)(C)C(O)=O)C=C1 XWSKQJGOCCSNQL-UHFFFAOYSA-N 0.000 description 1
- GWXCYRJYWSDUKU-UHFFFAOYSA-N 2-[4-(2,2-difluoro-1-phenylcyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1(C=2C=CC=CC=2)C(F)(F)C1 GWXCYRJYWSDUKU-UHFFFAOYSA-N 0.000 description 1
- FZEDCBWKPRTPBA-UHFFFAOYSA-N 2-[4-(2-chloro-2-fluorocyclopropyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(F)C1 FZEDCBWKPRTPBA-UHFFFAOYSA-N 0.000 description 1
- XXSPGBOGLXKMDU-UHFFFAOYSA-M 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C([O-])=O XXSPGBOGLXKMDU-UHFFFAOYSA-M 0.000 description 1
- RGFOIWHHUIOAMO-UHFFFAOYSA-N 2-methyl-2-[4-(1-phenylethenyl)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=C)C1=CC=CC=C1 RGFOIWHHUIOAMO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910003019 MBH4 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- SSDZRWBPFCFZGB-UHFFFAOYSA-N TCA-ethadyl Chemical compound ClC(Cl)(Cl)C(=O)OCCOC(=O)C(Cl)(Cl)Cl SSDZRWBPFCFZGB-UHFFFAOYSA-N 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- KTZIVCLKAODOOU-UHFFFAOYSA-N [dichloro(fluoro)methyl]-phenylmercury Chemical compound FC(Cl)(Cl)[Hg]C1=CC=CC=C1 KTZIVCLKAODOOU-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SOPVVLSSDDBCBJ-UHFFFAOYSA-N bis(tribromomethyl)mercury Chemical compound BrC(Br)(Br)[Hg]C(Br)(Br)Br SOPVVLSSDDBCBJ-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UHSJGVMAYSLRQF-UHFFFAOYSA-N chloro(diazo)methane Chemical compound ClC=[N+]=[N-] UHSJGVMAYSLRQF-UHFFFAOYSA-N 0.000 description 1
- DQSHRNZTQWDMPJ-UHFFFAOYSA-N chlorosulfinyloxymethane Chemical compound COS(Cl)=O DQSHRNZTQWDMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RVLOUHMOLDOXTF-UHFFFAOYSA-N ethyl 2-(4-benzoylphenoxy)-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=CC=C1 RVLOUHMOLDOXTF-UHFFFAOYSA-N 0.000 description 1
- YVOUARUTOSMLFJ-UHFFFAOYSA-N ethyl 2-[3-(1-hydroxyethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C(C)O)=C1 YVOUARUTOSMLFJ-UHFFFAOYSA-N 0.000 description 1
- LQTQHQKWUIPKRH-UHFFFAOYSA-N ethyl 2-[4-(1-hydroxy-2-phenylethyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(O)CC1=CC=CC=C1 LQTQHQKWUIPKRH-UHFFFAOYSA-N 0.000 description 1
- UVLMCKXCKKVZFL-UHFFFAOYSA-N ethyl 2-[4-(2,2-dichloro-1-methylcyclopropyl)-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1C1(C)C(Cl)(Cl)C1 UVLMCKXCKKVZFL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- YGOAOWITOUQDQM-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(2-phenylacetyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)CC1=CC=CC=C1 YGOAOWITOUQDQM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 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
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- CXTXQBGWWMWLCK-UHFFFAOYSA-N methyl 2,2-dichloro-2-fluoroacetate Chemical compound COC(=O)C(F)(Cl)Cl CXTXQBGWWMWLCK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 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
- YJLSVCJDMFHEHC-UHFFFAOYSA-N phenylmethylene Chemical class [CH]C1=CC=CC=C1 YJLSVCJDMFHEHC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28457772A | 1972-08-29 | 1972-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH605584A5 true CH605584A5 (en) | 1978-09-29 |
Family
ID=23090716
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH959876A CH605584A5 (en) | 1972-08-29 | 1973-08-27 | Halo-cyclopropyl aryloxy alkanoic acids and esters |
| CH7312272A CH608780A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-29 | 1973-08-27 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7312272A CH608780A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-29 | 1973-08-27 |
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 ZA ZA735748A patent/ZA735748B/xx unknown
- 1973-08-22 AU AU59488/73A patent/AU472631B2/en not_active Expired
- 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 AT AT744773A patent/AT331207B/de not_active IP Right Cessation
- 1973-08-27 CH CH959876A patent/CH605584A5/fr not_active IP Right Cessation
- 1973-08-27 CH CH7312272A patent/CH608780A5/xx not_active IP Right Cessation
- 1973-08-28 CA CA179,829A patent/CA1023762A/en not_active Expired
- 1973-08-28 NO NO3388/73A patent/NO143528C/no unknown
- 1973-08-28 ES ES418283A patent/ES418283A1/es not_active Expired
- 1973-08-28 SE SE7311687A patent/SE417828B/xx unknown
- 1973-08-28 FI FI2675/73A patent/FI58629C/fi active
- 1973-08-28 DK DK471773AA patent/DK141366B/da not_active IP Right Cessation
- 1973-08-29 DE DE2343606A patent/DE2343606C2/de not_active Expired
- 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
-
1980
- 1980-02-28 HK HK69/80A patent/HK6980A/xx unknown
-
1982
- 1982-06-02 JP JP57094645A patent/JPS60335B2/ja not_active Expired
- 1982-06-02 JP JP57094644A patent/JPS60334B2/ja not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3948973A (en) | Halocyclopropyl substituted phenoxyalkanoic acids | |
| JP2559723B2 (ja) | ビニルフェノール誘導体 | |
| KR880000688B1 (ko) | 류코트리엔 길항제의 제조방법 | |
| FR2468576A1 (fr) | Procede de preparation de l'acide 2,5-bis (2,2,2-trifluorethoxy)-benzoique | |
| JPH0255408B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| Bernady et al. | Prostaglandins and congeners. 28. Synthesis of 2-(. omega.-carbalkoxyalkyl) cyclopent-2-en-1-ones, intermediates for prostaglandin syntheses | |
| CH605584A5 (en) | Halo-cyclopropyl aryloxy alkanoic acids and esters | |
| CH615414A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US5283372A (en) | Preparation of purified optical isomers of desflurane | |
| FR2698872A1 (fr) | Procédé de préparation de la vitamine A et composés intermédiaires utiles pour ce procédé. | |
| FR2483404A1 (fr) | Procede de preparation de 2,2-dihalovinyl-cyclopropanecarboxylates | |
| EP0037327A1 (fr) | Nouveaux dérivés substitués de l'acide 3-formyl 4-méthyl pentanoique, leur préparation et leur application à la préparation d'acide 3-formyl but-3-èn-1-oique substitué | |
| Durden | Syntheses of nuclearly hydroxylated 1-naphthyl methylcarbamates. 6-and 7-Isomers | |
| Naoshima et al. | A New Synthesis of (E, E)-8, 10-Dodecadien-1-ol, Sex Pheromone of Codling Moth | |
| JP3353619B2 (ja) | アシルオキシケトンの製造法 | |
| Cohn et al. | The Autoxidation of 1, 1‐Dibromo‐2, 2‐Difluoroethylene and Tribromoethylene. Preparation of Dibromofluoro‐and Fluorodibromo‐Acetic Acid | |
| JP3396097B2 (ja) | ４−イソプロピルシクロヘキサンカルボン酸エステル誘導体の製法 | |
| CH634034A5 (fr) | Acide tricyclo 4.3.1.1(2,5)undecane-1-carboxylique et ses derives, et procede pour leur preparation. | |
| FR2471360A1 (fr) | Halogenocyclobutanones, procede pour leur preparation et produits intermediaires de leur preparation | |
| EP0223620B1 (fr) | Procédé de préparation de l'acide bromo-fluoro-acétique | |
| BE661226A (fr) | Acides arylacethydroxamiques, amides correspondants et procedes de preparation. | |
| JPS58194837A (ja) | ジフエニルメタン誘導体の製法 | |
| JPH0128734B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS6011690B2 (ja) | 修酸誘導体およびその製法 | |
| FR2495139A1 (fr) | Procede pour la preparation de derives de cyclopropane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |