IE44414B1 - Phenoxyacetic aci derivatives - Google Patents
Phenoxyacetic aci derivativesInfo
- Publication number
- IE44414B1 IE44414B1 IE60/77A IE6077A IE44414B1 IE 44414 B1 IE44414 B1 IE 44414B1 IE 60/77 A IE60/77 A IE 60/77A IE 6077 A IE6077 A IE 6077A IE 44414 B1 IE44414 B1 IE 44414B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- together represent
- thenoyl
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 10
- 150000002923 oximes Chemical class 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- -1 amine salt Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- WBMCWSIOIADDFA-UHFFFAOYSA-N 2-[2,6-diiodo-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(I)C(OCC(=O)O)=C(I)C=C1C(=O)C1=CC=CS1 WBMCWSIOIADDFA-UHFFFAOYSA-N 0.000 claims description 3
- SJBAOKCYATWJCP-UHFFFAOYSA-N 2-[2-iodo-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(I)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 SJBAOKCYATWJCP-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- TVOBRYWLDOXFER-UHFFFAOYSA-N 2-[2,6-dibromo-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(Br)C(OCC(=O)O)=C(Br)C=C1C(=O)C1=CC=CS1 TVOBRYWLDOXFER-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 3
- RCEOAGIOBKXQRZ-UHFFFAOYSA-N 2-(4-oxocyclohexa-1,5-dien-1-yl)oxyacetic acid Chemical class OC(=O)COC1=CCC(=O)C=C1 RCEOAGIOBKXQRZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 150000002148 esters Chemical group 0.000 description 12
- 150000002576 ketones Chemical group 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229940116731 Uricosuric agent Drugs 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 239000003383 uricosuric agent Substances 0.000 description 4
- 230000003424 uricosuric effect Effects 0.000 description 4
- BXKOJNCPVLHZGQ-UHFFFAOYSA-N (4-hydroxy-3,5-diiodophenyl)-thiophen-2-ylmethanone Chemical compound C1=C(I)C(O)=C(I)C=C1C(=O)C1=CC=CS1 BXKOJNCPVLHZGQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BMJPPNRKVDPZJO-UHFFFAOYSA-N 2-[2,6-dimethyl-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound CC1=C(OCC(O)=O)C(C)=CC(C(=O)C=2SC=CC=2)=C1 BMJPPNRKVDPZJO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002934 diuretic Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 3
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WUEDLUDGQHRZBX-UHFFFAOYSA-N (4-hydroxy-3-iodophenyl)-thiophen-2-ylmethanone Chemical compound C1=C(I)C(O)=CC=C1C(=O)C1=CC=CS1 WUEDLUDGQHRZBX-UHFFFAOYSA-N 0.000 description 2
- UXASOSNDAVIULO-UHFFFAOYSA-N 2-[2,3-dimethyl-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=C(C)C(C(=O)C=2SC=CC=2)=C1 UXASOSNDAVIULO-UHFFFAOYSA-N 0.000 description 2
- NMBCZDBCZNIBEA-UHFFFAOYSA-N 2-[2,6-dibromo-4-(furan-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(Br)C(OCC(=O)O)=C(Br)C=C1C(=O)C1=CC=CO1 NMBCZDBCZNIBEA-UHFFFAOYSA-N 0.000 description 2
- VJRYHEGIVPJHLM-UHFFFAOYSA-N 2-[2-bromo-4-(thiophene-2-carbonyl)phenoxy]acetic acid Chemical compound C1=C(Br)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 VJRYHEGIVPJHLM-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- IFLMOOGAONFANA-UHFFFAOYSA-N ethyl 2-[2,6-dibromo-4-(furan-2-carbonyl)phenoxy]acetate Chemical compound C1=C(Br)C(OCC(=O)OCC)=C(Br)C=C1C(=O)C1=CC=CO1 IFLMOOGAONFANA-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- SQJSPLHLGSWNPE-UHFFFAOYSA-N (3,5-dibromo-4-hydroxyphenyl)-(furan-2-yl)methanone Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(=O)C1=CC=CO1 SQJSPLHLGSWNPE-UHFFFAOYSA-N 0.000 description 1
- 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
- MIUNHWSLWKSFPX-UHFFFAOYSA-N (4-hydroxy-2,3-dimethylphenyl)-thiophen-2-ylmethanone Chemical compound CC1=C(O)C=CC(C(=O)C=2SC=CC=2)=C1C MIUNHWSLWKSFPX-UHFFFAOYSA-N 0.000 description 1
- NWBATPAOQPYQNU-UHFFFAOYSA-N (4-hydroxy-3,5-dimethylphenyl)-thiophen-2-ylmethanone Chemical compound CC1=C(O)C(C)=CC(C(=O)C=2SC=CC=2)=C1 NWBATPAOQPYQNU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GJCGWCJCGNEZSF-UHFFFAOYSA-N (4-methoxy-2,3-dimethylphenyl)-thiophen-2-ylmethanone Chemical compound CC1=C(C)C(OC)=CC=C1C(=O)C1=CC=CS1 GJCGWCJCGNEZSF-UHFFFAOYSA-N 0.000 description 1
- ONVXIBFXWDIHIQ-UHFFFAOYSA-N (4-methoxy-3,5-dimethylphenyl)-thiophen-2-ylmethanone Chemical compound C1=C(C)C(OC)=C(C)C=C1C(=O)C1=CC=CS1 ONVXIBFXWDIHIQ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 1
- YPJVJVIQWWXEHO-UHFFFAOYSA-N 2,3-diiodophenol Chemical class OC1=CC=CC(I)=C1I YPJVJVIQWWXEHO-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- GFNZJAUVJCGWLW-UHFFFAOYSA-N 2-methoxy-1,3-dimethylbenzene Chemical compound COC1=C(C)C=CC=C1C GFNZJAUVJCGWLW-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- KTVFFDPAOWAOBS-UHFFFAOYSA-N 4-hydroxycyclohexa-2,4-dien-1-one Chemical compound OC1=CCC(=O)C=C1 KTVFFDPAOWAOBS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 201000005569 Gout 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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 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 1
- 229960004411 benziodarone Drugs 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
- 239000002775 capsule Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- YAXQECBIJVYBRG-UHFFFAOYSA-N ethyl 2-[2,6-diiodo-4-(thiophene-2-carbonyl)phenoxy]acetate Chemical compound C1=C(I)C(OCC(=O)OCC)=C(I)C=C1C(=O)C1=CC=CS1 YAXQECBIJVYBRG-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012429 reaction media 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
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—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
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7630584A FR2367490A1 (fr) | 1976-10-12 | 1976-10-12 | Derives d'acides phenoxyacetiques, leur preparation et leur utilisation comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44414L IE44414L (en) | 1978-04-12 |
| IE44414B1 true IE44414B1 (en) | 1981-11-18 |
Family
ID=9178621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE60/77A IE44414B1 (en) | 1976-10-12 | 1977-01-13 | Phenoxyacetic aci derivatives |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2412540A2 (fr) * | 1977-02-14 | 1979-07-20 | Rolland Sa A | 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 |
-
1976
- 1976-10-12 FR FR7630584A patent/FR2367490A1/fr active Granted
-
1977
- 1977-01-12 BE BE174011A patent/BE850305A/xx not_active IP Right Cessation
- 1977-01-13 DE DE19772701231 patent/DE2701231A1/de not_active Withdrawn
- 1977-01-13 LU LU76563A patent/LU76563A1/xx unknown
- 1977-01-13 CH CH43477A patent/CH618696A5/fr not_active IP Right Cessation
- 1977-01-13 IE IE60/77A patent/IE44414B1/en unknown
- 1977-01-14 GB GB1537/77A patent/GB1544771A/en not_active Expired
- 1977-01-14 NL NL7700388A patent/NL7700388A/xx not_active Application Discontinuation
- 1977-01-17 ZA ZA770237A patent/ZA77237B/xx unknown
- 1977-01-17 NZ NZ183095A patent/NZ183095A/xx unknown
- 1977-01-17 JP JP384377A patent/JPS5346958A/ja active Pending
- 1977-01-20 AU AU21470/77A patent/AU503556B2/en not_active Expired
- 1977-01-20 PT PT66091A patent/PT66091B/pt unknown
- 1977-01-21 CA CA270,210A patent/CA1095526A/en not_active Expired
-
1978
- 1978-01-30 ES ES466458A patent/ES466458A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2701231A1 (de) | 1978-04-20 |
| PT66091A (fr) | 1977-02-01 |
| FR2367490A1 (fr) | 1978-05-12 |
| ES466458A1 (es) | 1978-10-01 |
| LU76563A1 (enrdf_load_stackoverflow) | 1977-07-27 |
| NL7700388A (nl) | 1978-04-14 |
| AU2147077A (en) | 1978-07-27 |
| JPS5346958A (en) | 1978-04-27 |
| CA1095526A (en) | 1981-02-10 |
| GB1544771A (en) | 1979-04-25 |
| NZ183095A (en) | 1978-04-28 |
| PT66091B (fr) | 1978-06-26 |
| FR2367490B1 (enrdf_load_stackoverflow) | 1980-11-07 |
| AU503556B2 (en) | 1979-09-06 |
| BE850305A (fr) | 1977-07-12 |
| CH618696A5 (en) | 1980-08-15 |
| IE44414L (en) | 1978-04-12 |
| ZA77237B (en) | 1977-11-30 |
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