FI66369C - Foerfarande foer framstaellning av terapeutiskt anvaendbara p-2-tenoyl)fenylalkansyror och derivat av dessa - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara p-2-tenoyl)fenylalkansyror och derivat av dessa Download PDFInfo
- Publication number
- FI66369C FI66369C FI3278/73A FI327873A FI66369C FI 66369 C FI66369 C FI 66369C FI 3278/73 A FI3278/73 A FI 3278/73A FI 327873 A FI327873 A FI 327873A FI 66369 C FI66369 C FI 66369C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- alkyl
- compound
- thenoyl
- parts
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 39
- -1 2-thenoyl Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229940125890 compound Ia Drugs 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical class C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OFGUULGKDTVNML-UHFFFAOYSA-N 2-[4-(thiophene-2-carbonyl)phenyl]propanenitrile Chemical compound C1=CC(C(C#N)C)=CC=C1C(=O)C1=CC=CS1 OFGUULGKDTVNML-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 241000186359 Mycobacterium Species 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 210000003141 lower extremity Anatomy 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 159000000000 sodium salts Chemical class 0.000 description 3
- RIOUIOIZYLTJEZ-UHFFFAOYSA-N 2-(4-benzoylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 RIOUIOIZYLTJEZ-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- DULCBPIXMGRMAQ-UHFFFAOYSA-N 2-methyl-4-oxo-2-phenyl-4-thiophen-2-ylbutanoic acid Chemical compound CC(C(=O)O)(CC(C1=CC=CS1)=O)C1=CC=CC=C1 DULCBPIXMGRMAQ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MKGZCSRBJPJMKF-UHFFFAOYSA-N [4-(1-chloroethyl)phenyl]-thiophen-2-ylmethanone Chemical compound C1=CC(C(Cl)C)=CC=C1C(=O)C1=CC=CS1 MKGZCSRBJPJMKF-UHFFFAOYSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- NLTRJPXIYKYMKT-UHFFFAOYSA-N (4-fluorophenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CS1 NLTRJPXIYKYMKT-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- UKKNIUWIOBUNHA-UHFFFAOYSA-N 2-[3-methyl-4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound CC1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 UKKNIUWIOBUNHA-UHFFFAOYSA-N 0.000 description 1
- FIHWLHKCFQHPLH-UHFFFAOYSA-N 2-[4-(5-chlorothiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=C(Cl)S1 FIHWLHKCFQHPLH-UHFFFAOYSA-N 0.000 description 1
- XPVHNPDPUYZBNJ-UHFFFAOYSA-N 2-[4-(thiophene-2-carbonyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(=O)C1=CC=CS1 XPVHNPDPUYZBNJ-UHFFFAOYSA-N 0.000 description 1
- XSSMMNDGAZJDIQ-UHFFFAOYSA-N 2-[4-(thiophene-2-carbonyl)phenyl]butanoic acid Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1C(=O)C1=CC=CS1 XSSMMNDGAZJDIQ-UHFFFAOYSA-N 0.000 description 1
- ZFSIEKBHGRDVTA-UHFFFAOYSA-N 2-[4-(thiophene-2-carbonyl)phenyl]propanoyl chloride Chemical compound C1=CC(C(C(Cl)=O)C)=CC=C1C(=O)C1=CC=CS1 ZFSIEKBHGRDVTA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- OYTPNEYQSSHIQY-UHFFFAOYSA-N 2-methyl-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 OYTPNEYQSSHIQY-UHFFFAOYSA-N 0.000 description 1
- XTRVQCRYTWLWKC-UHFFFAOYSA-N 2-methyl-3-oxo-2-phenyl-3-thiophen-2-ylpropanenitrile Chemical compound C=1C=CC=CC=1C(C#N)(C)C(=O)C1=CC=CS1 XTRVQCRYTWLWKC-UHFFFAOYSA-N 0.000 description 1
- WWPIMSSPBZCDMN-UHFFFAOYSA-N CC1=CC=C(S1)C(=O)C1=C(C=CC=C1)C(C(=O)O)C Chemical compound CC1=CC=C(S1)C(=O)C1=C(C=CC=C1)C(C(=O)O)C WWPIMSSPBZCDMN-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CDQUWVLZKXGMAZ-UHFFFAOYSA-N [4-(1-hydroxyethyl)phenyl]-thiophen-2-ylmethanone Chemical compound C1=CC(C(O)C)=CC=C1C(=O)C1=CC=CS1 CDQUWVLZKXGMAZ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WFAFWMFYLLMOON-UHFFFAOYSA-N diethyl 2-[3-chloro-4-(thiophene-2-carbonyl)phenyl]-2-methylpropanedioate Chemical compound ClC1=CC(C(C)(C(=O)OCC)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 WFAFWMFYLLMOON-UHFFFAOYSA-N 0.000 description 1
- HDQXYMXMPWWAKB-UHFFFAOYSA-N diethyl 2-ethyl-2-[4-(thiophene-2-carbonyl)phenyl]propanedioate Chemical compound C1=CC(C(CC)(C(=O)OCC)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 HDQXYMXMPWWAKB-UHFFFAOYSA-N 0.000 description 1
- RSUSQCKVKWHQFM-UHFFFAOYSA-N diethyl 2-methyl-2-[4-(thiophene-2-carbonyl)phenyl]propanedioate Chemical compound C1=CC(C(C)(C(=O)OCC)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 RSUSQCKVKWHQFM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- HBJBJEGKNCMUPK-UHFFFAOYSA-N methyl 2-[4-(thiophene-2-carbonyl)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1C(=O)C1=CC=CS1 HBJBJEGKNCMUPK-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- FKPHVZSJLXLCJF-UHFFFAOYSA-N n-hydroxy-2-[4-(thiophene-2-carbonyl)phenyl]propanamide Chemical compound C1=CC(C(C(=O)NO)C)=CC=C1C(=O)C1=CC=CS1 FKPHVZSJLXLCJF-UHFFFAOYSA-N 0.000 description 1
- RSIPQHOWTCNEBI-UHFFFAOYSA-N n-hydroxypropanamide Chemical compound CCC(=O)NO RSIPQHOWTCNEBI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- OZHOHTGAQOJLCS-UHFFFAOYSA-N oxalic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)C(O)=O OZHOHTGAQOJLCS-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
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- 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
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- 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
-
- 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
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30007972A | 1972-10-24 | 1972-10-24 | |
| US30007972 | 1972-10-24 | ||
| US39587773A | 1973-09-10 | 1973-09-10 | |
| US39587773 | 1973-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI66369B FI66369B (fi) | 1984-06-29 |
| FI66369C true FI66369C (fi) | 1984-10-10 |
Family
ID=26971576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3278/73A FI66369C (fi) | 1972-10-24 | 1973-10-23 | Foerfarande foer framstaellning av terapeutiskt anvaendbara p-2-tenoyl)fenylalkansyror och derivat av dessa |
Country Status (24)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1036466B (it) * | 1975-07-08 | 1979-10-30 | Sigurta Farmaceutici Spa | Processo per la preparazione di derivati dell acido alfa fenilpropionico |
| FR2374033A1 (fr) * | 1976-12-16 | 1978-07-13 | Rhone Poulenc Ind | Nouveaux acides thieno (3,2-b) thienylcarbonylphenylalcanoiques, leurs derives, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2345148A1 (fr) * | 1976-03-24 | 1977-10-21 | Lipha | Nouvel acide propionique substitue, preparation et application |
| GB1569404A (en) * | 1977-04-22 | 1980-06-11 | Soc D Etudes Prod Chimique | (2-isopropyl-4-(2'-theonyl)-5-methyl) phenoxy acetic acid |
| JPS5538340A (en) * | 1978-09-12 | 1980-03-17 | Taiyo Yakuhin Kogyo Kk | Preparation of 2- 4-(2-thienylcarbonyl)phenyl propionic acid |
| GB2030131B (en) * | 1978-09-12 | 1982-12-22 | Taiyo Pharma Ind | Process for producing 2-(4-(2-thienyl-carbonyl) phenyl) propionic acid |
| JPS5538339A (en) * | 1978-09-12 | 1980-03-17 | Taiyo Yakuhin Kogyo Kk | Preparation of 2- 4-(2-thienylcarbonyl)phenyl propionic acid |
| JPS5823873B2 (ja) * | 1979-02-02 | 1983-05-18 | 財団法人相模中央化学研究所 | 置換フェニル酢酸誘導体の製造方法 |
| JPS5825675B2 (ja) * | 1979-02-02 | 1983-05-28 | 財団法人相模中央化学研究所 | ケタ−ル誘導体 |
| ES479300A1 (es) * | 1979-04-04 | 1979-07-01 | Cusi Lab | Procedimiento de obtencio de &-metil, 4(2'tienil carbonilz) fenil acetato de p-acetamido fenol. |
| EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
| US5191112A (en) * | 1989-10-17 | 1993-03-02 | Nissan Chemical Industries, Ltd. | Process for optical resolution of (±)-2-(3-benzoyl)-phenylpropionic acid |
| JP2000297086A (ja) * | 1999-02-08 | 2000-10-24 | Sankyo Co Ltd | ヘテロアリールヒドラゾン化合物 |
| JP6290947B2 (ja) * | 2016-02-05 | 2018-03-07 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1226344A (enrdf_load_stackoverflow) * | 1967-07-31 | 1971-03-24 | ||
| FR2113760A1 (en) * | 1970-11-10 | 1972-06-30 | Roussel Uclaf | 5-Arylcarbonyl-3(or 4)-methylthien-2-yl alkanoic acids and esters - with antiinflammatory and analgesic activity |
-
1973
- 1973-10-17 CA CA183,576A patent/CA1007643A/en not_active Expired
- 1973-10-18 PH PH15118A patent/PH12124A/en unknown
- 1973-10-19 FR FR7337487A patent/FR2203635B1/fr not_active Expired
- 1973-10-22 DK DK572273A patent/DK154899C/da active
- 1973-10-22 LU LU68666A patent/LU68666A1/xx unknown
- 1973-10-23 JP JP48118585A patent/JPS5940811B2/ja not_active Expired
- 1973-10-23 CH CH1496073A patent/CH597219A5/xx not_active IP Right Cessation
- 1973-10-23 NO NO4105/73A patent/NO141651C/no unknown
- 1973-10-23 SE SE7314366A patent/SE403911B/xx unknown
- 1973-10-23 BE BE136954A patent/BE806389A/xx not_active IP Right Cessation
- 1973-10-23 ES ES419871A patent/ES419871A1/es not_active Expired
- 1973-10-23 FI FI3278/73A patent/FI66369C/fi active
- 1973-10-23 SU SU731973680A patent/SU719490A3/ru active
- 1973-10-23 YU YU2759/73A patent/YU37106B/xx unknown
- 1973-10-23 IE IE1896/73A patent/IE38402B1/xx unknown
- 1973-10-24 BG BG024830A patent/BG25209A3/xx unknown
- 1973-10-24 NL NLAANVRAGE7314629,A patent/NL179583C/xx not_active IP Right Cessation
- 1973-10-24 CS CS7300007333A patent/CS183719B2/cs unknown
- 1973-10-24 GB GB4958073A patent/GB1446239A/en not_active Expired
- 1973-10-24 AT AT900773A patent/AT333269B/de not_active IP Right Cessation
- 1973-10-24 DE DE2353357A patent/DE2353357C2/de not_active Expired
- 1973-10-24 DD DD174327A patent/DD110044A5/xx unknown
- 1973-10-24 HU HUJA691A patent/HU168046B/hu unknown
- 1973-11-05 IL IL43570A patent/IL43570A/en unknown
-
1982
- 1982-06-02 JP JP57093264A patent/JPS5938237B2/ja not_active Expired
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