CH618696A5 - Process for the preparation of phenoxyacetic acid derivatives - Google Patents
Process for the preparation of phenoxyacetic acid derivatives Download PDFInfo
- Publication number
- CH618696A5 CH618696A5 CH43477A CH43477A CH618696A5 CH 618696 A5 CH618696 A5 CH 618696A5 CH 43477 A CH43477 A CH 43477A CH 43477 A CH43477 A CH 43477A CH 618696 A5 CH618696 A5 CH 618696A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- ester
- salts
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 159000000011 group IA salts Chemical class 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229960004592 isopropanol Drugs 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 3
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 150000002576 ketones Chemical group 0.000 abstract description 9
- 150000002923 oximes Chemical class 0.000 abstract description 6
- 230000003424 uricosuric effect Effects 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract 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 abstract description 2
- 201000005569 Gout Diseases 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- 239000000243 solution Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 15
- -1 2-thenoyl Chemical group 0.000 description 14
- 239000000155 melt Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000001953 recrystallisation 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
- 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 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229940116731 Uricosuric agent Drugs 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 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
- 239000003383 uricosuric agent Substances 0.000 description 3
- 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 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- 239000002934 diuretic Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000047 product Substances 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
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 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
- 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
- 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 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
- SFTDDFBJWUWKMN-UHFFFAOYSA-N 2-(4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C=C1 SFTDDFBJWUWKMN-UHFFFAOYSA-N 0.000 description 1
- 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 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- 231100000111 LD50 Toxicity 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 238000003556 assay 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
- HPDJOPVEPSPVPX-UHFFFAOYSA-N bis(3,5-dibromo-4-hydroxyphenyl)methanone Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(=O)C1=CC(Br)=C(O)C(Br)=C1 HPDJOPVEPSPVPX-UHFFFAOYSA-N 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical compound C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 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
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- ZUGZAGVRSXHCOA-UHFFFAOYSA-N propan-2-yl 2-phenoxyacetate Chemical compound CC(C)OC(=O)COC1=CC=CC=C1 ZUGZAGVRSXHCOA-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 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
- 238000001228 spectrum Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (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 (1)
| Publication Number | Publication Date |
|---|---|
| CH618696A5 true CH618696A5 (en) | 1980-08-15 |
Family
ID=9178621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH43477A CH618696A5 (en) | 1976-10-12 | 1977-01-13 | Process for the preparation of phenoxyacetic acid 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 LU LU76563A patent/LU76563A1/xx unknown
- 1977-01-13 DE DE19772701231 patent/DE2701231A1/de not_active Withdrawn
- 1977-01-13 IE IE60/77A patent/IE44414B1/en unknown
- 1977-01-13 CH CH43477A patent/CH618696A5/fr not_active IP Right Cessation
- 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 NZ NZ183095A patent/NZ183095A/xx unknown
- 1977-01-17 JP JP384377A patent/JPS5346958A/ja active Pending
- 1977-01-17 ZA ZA770237A patent/ZA77237B/xx unknown
- 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 |
|---|---|
| FR2367490A1 (fr) | 1978-05-12 |
| DE2701231A1 (de) | 1978-04-20 |
| NZ183095A (en) | 1978-04-28 |
| ES466458A1 (es) | 1978-10-01 |
| AU2147077A (en) | 1978-07-27 |
| FR2367490B1 (enrdf_load_stackoverflow) | 1980-11-07 |
| GB1544771A (en) | 1979-04-25 |
| CA1095526A (en) | 1981-02-10 |
| PT66091A (fr) | 1977-02-01 |
| BE850305A (fr) | 1977-07-12 |
| AU503556B2 (en) | 1979-09-06 |
| JPS5346958A (en) | 1978-04-27 |
| IE44414B1 (en) | 1981-11-18 |
| IE44414L (en) | 1978-04-12 |
| NL7700388A (nl) | 1978-04-14 |
| ZA77237B (en) | 1977-11-30 |
| PT66091B (fr) | 1978-06-26 |
| LU76563A1 (enrdf_load_stackoverflow) | 1977-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |