NO780494L - Fremgangsmaate ved fremstilling av methyl-2 fenoxy-2 propionsyrederivater - Google Patents
Fremgangsmaate ved fremstilling av methyl-2 fenoxy-2 propionsyrederivaterInfo
- Publication number
- NO780494L NO780494L NO780494A NO780494A NO780494L NO 780494 L NO780494 L NO 780494L NO 780494 A NO780494 A NO 780494A NO 780494 A NO780494 A NO 780494A NO 780494 L NO780494 L NO 780494L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- methyl
- mixture
- compounds
- denotes
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 24
- 150000002576 ketones Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004926 chlorobutanol Drugs 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005646 oximino group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000002923 oximes Chemical class 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000155 melt Substances 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 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 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000000055 hyoplipidemic effect Effects 0.000 description 5
- 230000000871 hypocholesterolemic effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 230000003424 uricosuric effect Effects 0.000 description 4
- NAJMFEZOIWEPPX-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpentanoic acid Chemical compound CCCC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 NAJMFEZOIWEPPX-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
- 201000001431 Hyperuricemia Diseases 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003529 anticholesteremic agent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
- 229960001214 clofibrate Drugs 0.000 description 3
- SRKUIYSYBQKLOX-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(thiophene-2-carbonyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 SRKUIYSYBQKLOX-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- QHNHAPUTAWUKLA-UHFFFAOYSA-N furan-2-yl-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CO1 QHNHAPUTAWUKLA-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000006146 oximation reaction Methods 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- BVLDPAXUXIUXKB-UHFFFAOYSA-N (4-hydroxyphenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CS1 BVLDPAXUXIUXKB-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- VMSHMFOOCGHYKV-UHFFFAOYSA-N 2-[4-(n-hydroxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=NO)C1=CC=CS1 VMSHMFOOCGHYKV-UHFFFAOYSA-N 0.000 description 2
- NMYRVDGUADEDHI-UHFFFAOYSA-N 2-[4-(n-methoxy-c-thiophen-2-ylcarbonimidoyl)-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(OC(C)(C)C(O)=O)C(C)=CC=1C(=NOC)C1=CC=CS1 NMYRVDGUADEDHI-UHFFFAOYSA-N 0.000 description 2
- UTYFCFBXRQQMFZ-UHFFFAOYSA-N 2-[4-[n-butoxy-c-(furan-2-yl)carbonimidoyl]phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(OC(C)(C)C(O)=O)C=CC=1C(=NOCCCC)C1=CC=CO1 UTYFCFBXRQQMFZ-UHFFFAOYSA-N 0.000 description 2
- CKYOKQWVQUWCIO-UHFFFAOYSA-N 2-methyl-2-[4-(thiophene-2-carbonyl)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=CS1 CKYOKQWVQUWCIO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- -1 alkaline earth metal acetate Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- CZCHIEJNWPNBDE-UHFFFAOYSA-N benziodarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(O)C(I)=C1 CZCHIEJNWPNBDE-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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 2
- 238000004440 column chromatography Methods 0.000 description 2
- GCTZCDXYQUUNIW-UHFFFAOYSA-N ethyl 2-[2-bromo-4-(thiophene-2-carbonyl)phenoxy]-2-methylpropanoate Chemical compound C1=C(Br)C(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 GCTZCDXYQUUNIW-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PYSXWSYJYFYKGD-UHFFFAOYSA-N (3-bromo-4-hydroxyphenyl)-thiophen-2-ylmethanone Chemical compound C1=C(Br)C(O)=CC=C1C(=O)C1=CC=CS1 PYSXWSYJYFYKGD-UHFFFAOYSA-N 0.000 description 1
- HOJFEQQBPHZJIB-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl)-thiophen-2-ylmethanone Chemical compound C1=C(O)C(C)=CC(C(=O)C=2SC=CC=2)=C1 HOJFEQQBPHZJIB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- AZRGKIFZZRQBJN-UHFFFAOYSA-N 2-[4-(furan-2-carbonyl)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=CO1 AZRGKIFZZRQBJN-UHFFFAOYSA-N 0.000 description 1
- YWCLWTRBLZGPMH-UHFFFAOYSA-N 2-[4-(n-ethoxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(OC(C)(C)C(O)=O)C=CC=1C(=NOCC)C1=CC=CS1 YWCLWTRBLZGPMH-UHFFFAOYSA-N 0.000 description 1
- BZJDFXFPJDKYND-UHFFFAOYSA-N 2-[4-(n-methoxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(OC(C)(C)C(O)=O)C=CC=1C(=NOC)C1=CC=CS1 BZJDFXFPJDKYND-UHFFFAOYSA-N 0.000 description 1
- QJQNOAUGOMVLER-UHFFFAOYSA-N 2-[4-[c-(furan-2-yl)-n-hydroxycarbonimidoyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=NO)C1=CC=CO1 QJQNOAUGOMVLER-UHFFFAOYSA-N 0.000 description 1
- CWLPJPUJPBJOBQ-UHFFFAOYSA-N 2-[4-[c-(furan-2-yl)-n-propoxycarbonimidoyl]phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(OC(C)(C)C(O)=O)C=CC=1C(=NOCCC)C1=CC=CO1 CWLPJPUJPBJOBQ-UHFFFAOYSA-N 0.000 description 1
- CWBGPNNFIVKTLX-UHFFFAOYSA-N 4-[C-(furan-2-yl)-N-propoxycarbonimidoyl]phenol Chemical compound C=1C=C(O)C=CC=1C(=NOCCC)C1=CC=CO1 CWBGPNNFIVKTLX-UHFFFAOYSA-N 0.000 description 1
- DCVOAMJJIAYUGQ-UHFFFAOYSA-N 4-[N-butoxy-C-(furan-2-yl)carbonimidoyl]phenol Chemical compound C=1C=C(O)C=CC=1C(=NOCCCC)C1=CC=CO1 DCVOAMJJIAYUGQ-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020961 Hypocholesterolaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 229940116731 Uricosuric agent Drugs 0.000 description 1
- 206010046555 Urinary retention Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 229960004411 benziodarone Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- UPEHMXHGDJKISZ-UHFFFAOYSA-N butyl 2-[4-(n-butoxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OCCCC)C=CC=1C(=NOCCCC)C1=CC=CS1 UPEHMXHGDJKISZ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- MBNDFRNTNLVPQA-UHFFFAOYSA-N ethyl 2-[4-(furan-2-carbonyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=O)C1=CC=CO1 MBNDFRNTNLVPQA-UHFFFAOYSA-N 0.000 description 1
- UZHZUXROIFJVPW-UHFFFAOYSA-N ethyl 2-[4-(n-hydroxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=NO)C1=CC=CS1 UZHZUXROIFJVPW-UHFFFAOYSA-N 0.000 description 1
- HHFBPVKVXQKTQL-UHFFFAOYSA-N ethyl 2-[4-(n-methoxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=NOC)C1=CC=CS1 HHFBPVKVXQKTQL-UHFFFAOYSA-N 0.000 description 1
- KDZGQOBQOQFVAW-UHFFFAOYSA-N ethyl 2-[4-[c-(furan-2-yl)-n-hydroxycarbonimidoyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(=NO)C1=CC=CO1 KDZGQOBQOQFVAW-UHFFFAOYSA-N 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GLVVAZJEKFNUBO-UHFFFAOYSA-N methyl 2-[4-(n-hydroxy-c-thiophen-2-ylcarbonimidoyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC)=CC=C1C(=NO)C1=CC=CS1 GLVVAZJEKFNUBO-UHFFFAOYSA-N 0.000 description 1
- DMFAORBTXRHZBS-UHFFFAOYSA-N methyl 2-methyl-2-[4-(thiophene-2-carbonyl)phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC)=CC=C1C(=O)C1=CC=CS1 DMFAORBTXRHZBS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- HUYRNQWVAPCTQZ-UHFFFAOYSA-N o-butylhydroxylamine;hydrochloride Chemical compound Cl.CCCCON HUYRNQWVAPCTQZ-UHFFFAOYSA-N 0.000 description 1
- FDVFCJYDSZGNLJ-UHFFFAOYSA-N o-propylhydroxylamine;hydrochloride Chemical compound Cl.CCCON FDVFCJYDSZGNLJ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- YSNHEFSQQSARGX-UHFFFAOYSA-M potassium chloroform propan-2-one hydroxide Chemical compound [OH-].[K+].C(Cl)(Cl)Cl.CC(=O)C YSNHEFSQQSARGX-UHFFFAOYSA-M 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000003383 uricosuric agent Substances 0.000 description 1
Classifications
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7704110A FR2380273A1 (fr) | 1977-02-14 | 1977-02-14 | Oximes heterocycliques derives d'acides phenoxyisobutyriques |
| FR7738633A FR2412540A2 (fr) | 1977-02-14 | 1977-12-21 | Nouveau procede de preparation de derives d'acide methyl-2 phenoxy-2 propionique, nouveaux derives d'acide methyl-2 phenoxy-2 propionique et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780494L true NO780494L (no) | 1978-08-15 |
Family
ID=26219852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780494A NO780494L (no) | 1977-02-14 | 1978-02-13 | Fremgangsmaate ved fremstilling av methyl-2 fenoxy-2 propionsyrederivater |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4259509A (fr) |
| JP (1) | JPS53103466A (fr) |
| AR (1) | AR215998A1 (fr) |
| AU (1) | AU514509B2 (fr) |
| BE (1) | BE863550A (fr) |
| BG (1) | BG29874A3 (fr) |
| CA (1) | CA1109885A (fr) |
| DD (1) | DD134094A5 (fr) |
| DE (1) | DE2804981A1 (fr) |
| DK (1) | DK64678A (fr) |
| ES (1) | ES467316A1 (fr) |
| FI (1) | FI780423A (fr) |
| FR (1) | FR2412540A2 (fr) |
| GB (1) | GB1551696A (fr) |
| GR (1) | GR66170B (fr) |
| HU (1) | HU174630B (fr) |
| IE (1) | IE46387B1 (fr) |
| IL (1) | IL53954A (fr) |
| LU (1) | LU78978A1 (fr) |
| NL (1) | NL7801610A (fr) |
| NO (1) | NO780494L (fr) |
| NZ (1) | NZ186459A (fr) |
| OA (1) | OA05887A (fr) |
| PH (1) | PH14928A (fr) |
| PL (1) | PL107875B1 (fr) |
| PT (1) | PT67649B (fr) |
| SE (1) | SE7801646L (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008035359A2 (fr) * | 2006-06-12 | 2008-03-27 | Cadila Healthcare Limited | Acide oxyminophénoxyalcanoïque et dérivés de l'acide phenylalcanoïque |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5195049A (en) * | 1975-02-12 | 1976-08-20 | * **********so*****no***tsu*****************************************ni*no | |
| US4017632A (en) * | 1975-10-22 | 1977-04-12 | Centre European De Recherches Pharmacologiques C.E.R.P.H.A. | Phenoxyacetic acid derivatives |
| FR2367490A1 (fr) * | 1976-10-12 | 1978-05-12 | Rolland Sa A | Derives d'acides phenoxyacetiques, leur preparation et leur utilisation comme medicaments |
-
1977
- 1977-12-21 FR FR7738633A patent/FR2412540A2/fr active Granted
-
1978
- 1978-02-01 IL IL53954A patent/IL53954A/xx unknown
- 1978-02-01 BE BE184818A patent/BE863550A/fr unknown
- 1978-02-02 US US05/874,479 patent/US4259509A/en not_active Expired - Lifetime
- 1978-02-02 LU LU78978A patent/LU78978A1/fr unknown
- 1978-02-02 IE IE218/78A patent/IE46387B1/en unknown
- 1978-02-03 BG BG7828578A patent/BG29874A3/xx unknown
- 1978-02-06 DE DE19782804981 patent/DE2804981A1/de not_active Withdrawn
- 1978-02-09 GR GR55399A patent/GR66170B/el unknown
- 1978-02-09 AU AU33165/78A patent/AU514509B2/en not_active Expired
- 1978-02-09 FI FI780423A patent/FI780423A/fi not_active Application Discontinuation
- 1978-02-13 CA CA296,950A patent/CA1109885A/fr not_active Expired
- 1978-02-13 OA OA56408A patent/OA05887A/fr unknown
- 1978-02-13 PL PL1978204590A patent/PL107875B1/pl unknown
- 1978-02-13 DK DK64678A patent/DK64678A/da not_active Application Discontinuation
- 1978-02-13 DD DD78203681A patent/DD134094A5/xx unknown
- 1978-02-13 NL NL7801610A patent/NL7801610A/xx not_active Application Discontinuation
- 1978-02-13 SE SE7801646A patent/SE7801646L/xx unknown
- 1978-02-13 NO NO780494A patent/NO780494L/no unknown
- 1978-02-13 NZ NZ186459A patent/NZ186459A/xx unknown
- 1978-02-13 HU HU78RO962A patent/HU174630B/hu unknown
- 1978-02-13 JP JP1530078A patent/JPS53103466A/ja active Pending
- 1978-02-13 PT PT67649A patent/PT67649B/fr unknown
- 1978-02-14 ES ES467316A patent/ES467316A1/es not_active Expired
- 1978-02-14 PH PH20783A patent/PH14928A/en unknown
- 1978-02-14 GB GB5847/78A patent/GB1551696A/en not_active Expired
-
1979
- 1979-03-12 AR AR275772A patent/AR215998A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| GR66170B (fr) | 1981-01-21 |
| DK64678A (da) | 1978-08-15 |
| PH14928A (en) | 1982-01-29 |
| PL107875B1 (pl) | 1980-03-31 |
| BG29874A3 (en) | 1981-02-16 |
| GB1551696A (en) | 1979-08-30 |
| DD134094A5 (de) | 1979-02-07 |
| AR215998A1 (es) | 1979-11-15 |
| ES467316A1 (es) | 1978-10-16 |
| HU174630B (hu) | 1980-02-28 |
| LU78978A1 (fr) | 1978-06-26 |
| NZ186459A (en) | 1979-06-08 |
| IL53954A0 (en) | 1978-04-30 |
| DE2804981A1 (de) | 1978-08-17 |
| BE863550A (fr) | 1978-08-01 |
| IE780218L (en) | 1978-08-14 |
| FI780423A (fi) | 1978-08-15 |
| PL204590A1 (pl) | 1978-12-04 |
| PT67649B (fr) | 1979-07-18 |
| OA05887A (fr) | 1981-05-31 |
| CA1109885A (fr) | 1981-09-29 |
| AU514509B2 (en) | 1981-02-12 |
| US4259509A (en) | 1981-03-31 |
| IL53954A (en) | 1981-09-13 |
| AU3316578A (en) | 1979-08-16 |
| SE7801646L (sv) | 1978-08-14 |
| NL7801610A (nl) | 1978-08-16 |
| FR2412540B2 (fr) | 1981-12-18 |
| FR2412540A2 (fr) | 1979-07-20 |
| IE46387B1 (en) | 1983-05-18 |
| JPS53103466A (en) | 1978-09-08 |
| PT67649A (fr) | 1978-03-01 |
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