HU202519B - Process for producing 5,6-dihydro-4h-cyclopenta(b)thiophene-6-carboxylic acid derivatives - Google Patents
Process for producing 5,6-dihydro-4h-cyclopenta(b)thiophene-6-carboxylic acid derivatives Download PDFInfo
- Publication number
- HU202519B HU202519B HU852639A HU263985A HU202519B HU 202519 B HU202519 B HU 202519B HU 852639 A HU852639 A HU 852639A HU 263985 A HU263985 A HU 263985A HU 202519 B HU202519 B HU 202519B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- thiophene
- dihydro
- cyclopenta
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- YRMLJIHDPINGDB-UHFFFAOYSA-N 5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical class C1=CSC2=C1CCC2C(=O)O YRMLJIHDPINGDB-UHFFFAOYSA-N 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 35
- -1 aroyl halide Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 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 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 150000001502 aryl halides Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- PAKBOZAYRHGQAM-UHFFFAOYSA-N 4H-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound S1C2=C(C=C1)CC=C2C(=O)O PAKBOZAYRHGQAM-UHFFFAOYSA-N 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 62
- 238000000921 elemental analysis Methods 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- BDUYODWXYFKKTN-UHFFFAOYSA-N ethyl 2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylate Chemical compound C1=C(C)SC2=C1CCC2C(=O)OCC BDUYODWXYFKKTN-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000538 analytical sample Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- OCCHJENURXSHPV-UHFFFAOYSA-N 3-benzoyl-2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound CC=1SC=2C(C(O)=O)CCC=2C=1C(=O)C1=CC=CC=C1 OCCHJENURXSHPV-UHFFFAOYSA-N 0.000 description 8
- 206010030113 Oedema Diseases 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- SSLAOCXGKPBGQY-UHFFFAOYSA-N 2-methyl-4-oxo-5,6-dihydrocyclopenta[b]thiophene-6-carboxylic acid Chemical compound O=C1CC(C(O)=O)C2=C1C=C(C)S2 SSLAOCXGKPBGQY-UHFFFAOYSA-N 0.000 description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- ADTIVABFSTUJJG-UHFFFAOYSA-N 2-(5-methylthiophen-2-yl)butanedioic acid Chemical compound CC1=CC=C(C(CC(O)=O)C(O)=O)S1 ADTIVABFSTUJJG-UHFFFAOYSA-N 0.000 description 4
- GTJXZNZIJGGMKR-UHFFFAOYSA-N 2-[5-(2-methylpropyl)thiophen-2-yl]butanedioic acid Chemical compound CC(C)CC1=CC=C(C(CC(O)=O)C(O)=O)S1 GTJXZNZIJGGMKR-UHFFFAOYSA-N 0.000 description 4
- KXPYIRHLFRPCCU-UHFFFAOYSA-N 3-(5-methylthiophen-2-yl)oxolane-2,5-dione Chemical compound S1C(C)=CC=C1C1C(=O)OC(=O)C1 KXPYIRHLFRPCCU-UHFFFAOYSA-N 0.000 description 4
- ZOVFZILIQGCDPM-UHFFFAOYSA-N CC1=C(C2=C(S1)C(CC2)C(=O)OC)C(=O)C3=CC=C(C=C3)[N+](=O)[O-] Chemical compound CC1=C(C2=C(S1)C(CC2)C(=O)OC)C(=O)C3=CC=C(C=C3)[N+](=O)[O-] ZOVFZILIQGCDPM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229960000905 indomethacin Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000011044 succinic acid Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KPSCCPFCLPEIPT-UHFFFAOYSA-N 2-(2-methylpropyl)-4-oxo-5,6-dihydrocyclopenta[b]thiophene-6-carboxylic acid Chemical compound O=C1CC(C(O)=O)C2=C1C=C(CC(C)C)S2 KPSCCPFCLPEIPT-UHFFFAOYSA-N 0.000 description 3
- GIGONMGLFLHWHT-UHFFFAOYSA-N 2-(2-methylpropyl)-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound C1CC(C(O)=O)C2=C1C=C(CC(C)C)S2 GIGONMGLFLHWHT-UHFFFAOYSA-N 0.000 description 3
- IKYMMXFAWFNXJC-UHFFFAOYSA-N 2-(5-ethylthiophen-2-yl)butanedioic acid Chemical compound CCC1=CC=C(C(CC(O)=O)C(O)=O)S1 IKYMMXFAWFNXJC-UHFFFAOYSA-N 0.000 description 3
- DGAAKQOVJUYCGW-UHFFFAOYSA-N 2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound C1CC(C(O)=O)C2=C1C=C(C)S2 DGAAKQOVJUYCGW-UHFFFAOYSA-N 0.000 description 3
- UOGHRKNCEXFWNI-UHFFFAOYSA-N 5,6-dihydro-4h-cyclopenta[b]thiophene-4-carboxylic acid Chemical class S1C=CC2=C1CCC2C(=O)O UOGHRKNCEXFWNI-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 229940113118 carrageenan Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- KUPDIEGEFKMXES-UHFFFAOYSA-N methyl 2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylate Chemical compound C1=C(C)SC2=C1CCC2C(=O)OC KUPDIEGEFKMXES-UHFFFAOYSA-N 0.000 description 3
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003444 succinic acids Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- AMARKEGDFSBLFC-TWGQIWQCSA-N (z)-3-(4-methoxyphenyl)-2-sulfanylprop-2-enoic acid Chemical compound COC1=CC=C(\C=C(/S)C(O)=O)C=C1 AMARKEGDFSBLFC-TWGQIWQCSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
- QHYCNCVALAOFEO-UHFFFAOYSA-N 2-ethyl-4-oxo-5,6-dihydrocyclopenta[b]thiophene-6-carboxylic acid Chemical compound O=C1CC(C(O)=O)C2=C1C=C(CC)S2 QHYCNCVALAOFEO-UHFFFAOYSA-N 0.000 description 2
- BXLGTJKHLPBWOC-UHFFFAOYSA-N 3-[4-(dimethylamino)benzoyl]-2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=C(C)SC2=C1CCC2C(O)=O BXLGTJKHLPBWOC-UHFFFAOYSA-N 0.000 description 2
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- OGYGIDQNSWNPQU-UHFFFAOYSA-N 3-benzoyl-2-(2-methylpropyl)-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound CC(C)CC=1SC=2C(C(O)=O)CCC=2C=1C(=O)C1=CC=CC=C1 OGYGIDQNSWNPQU-UHFFFAOYSA-N 0.000 description 2
- UBAMDBUMKBVJEQ-UHFFFAOYSA-N 3-benzoyl-2-ethyl-5,6-dihydro-4h-cyclopenta[b]thiophene-6-carboxylic acid Chemical compound CCC=1SC=2C(C(O)=O)CCC=2C=1C(=O)C1=CC=CC=C1 UBAMDBUMKBVJEQ-UHFFFAOYSA-N 0.000 description 2
- OGGGZOWWKJJGEF-UHFFFAOYSA-N 3-benzoyl-2-methyl-5,6-dihydro-4h-cyclopenta[b]thiophene-4-carboxylic acid Chemical compound CC=1SC=2CCC(C(O)=O)C=2C=1C(=O)C1=CC=CC=C1 OGGGZOWWKJJGEF-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
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- 206010061218 Inflammation Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 150000001500 aryl chlorides Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- PJYFEMRXRXRMSS-UHFFFAOYSA-N tert-butyl n-(thiophen-2-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CS1 PJYFEMRXRXRMSS-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- 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
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8410861A FR2567125B1 (fr) | 1984-07-09 | 1984-07-09 | Acides dihydro-5,6-4h-cyclopenta (b) thiophenecarboxylique-6, procedes de preparation et medicaments les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38331A HUT38331A (en) | 1986-05-28 |
| HU202519B true HU202519B (en) | 1991-03-28 |
Family
ID=9305925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU852639A HU202519B (en) | 1984-07-09 | 1985-07-08 | Process for producing 5,6-dihydro-4h-cyclopenta(b)thiophene-6-carboxylic acid derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4649153A (en, 2012) |
| EP (1) | EP0172041B1 (en, 2012) |
| JP (1) | JPH072733B2 (en, 2012) |
| AR (1) | AR242381A1 (en, 2012) |
| AT (1) | ATE36329T1 (en, 2012) |
| AU (1) | AU573147B2 (en, 2012) |
| CA (1) | CA1249834A (en, 2012) |
| CS (1) | CS255887B2 (en, 2012) |
| DD (1) | DD235454A5 (en, 2012) |
| DE (1) | DE3564268D1 (en, 2012) |
| DK (1) | DK161321C (en, 2012) |
| ES (1) | ES8604550A1 (en, 2012) |
| FR (1) | FR2567125B1 (en, 2012) |
| GR (1) | GR851609B (en, 2012) |
| HU (1) | HU202519B (en, 2012) |
| IE (1) | IE58362B1 (en, 2012) |
| IL (1) | IL75527A (en, 2012) |
| IN (1) | IN166471B (en, 2012) |
| MA (1) | MA20481A1 (en, 2012) |
| MX (1) | MX162258A (en, 2012) |
| NO (1) | NO171499C (en, 2012) |
| NZ (1) | NZ212619A (en, 2012) |
| OA (1) | OA08076A (en, 2012) |
| SU (1) | SU1402261A3 (en, 2012) |
| YU (1) | YU113885A (en, 2012) |
| ZA (1) | ZA854519B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692460A (en) * | 1986-12-24 | 1987-09-08 | Mcneilab, Inc. | Cyclopenta[b]thiophenes having anti-inflammatory activity similar to steroids |
| IL103106A (en) * | 1991-09-25 | 1998-06-15 | Sanofi Elf | Ethers of thienocyclopentanone oximes, their preparation and pharmaceutical compositions containing them |
| WO2009158380A1 (en) * | 2008-06-24 | 2009-12-30 | Bristol-Myers Squibb Company | Cyclopentathiophene modulators of the glucocorticoid receptor, ap-1, and/or nf-kappa b activity and use thereof |
| RU2389724C1 (ru) * | 2008-12-25 | 2010-05-20 | Государственное образовательное учреждение высшего профессионального образования "Пермский государственный университет" | 4-(4-метилфенил)-4-оксо-2-[3-этоксикарбонил-4,5-r2,r1-тиофен-2-иламино]бут-2-еновые кислоты, обладающие противовоспалительной и анальгетической активностью |
| RU2661151C1 (ru) * | 2017-12-14 | 2018-07-12 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Селективные ингибиторы глицеральдегид-3-фосфатдегидрогеназы микобактерий |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2167334A1 (en) * | 1972-01-13 | 1973-08-24 | Roussel Uclaf | 4-aroyl-5-alkylthiophene-2-acetic acids - with analgesic and antiinflammatory activity |
| NO743135L (en, 2012) * | 1973-09-11 | 1975-04-07 | Sandoz Ag |
-
1984
- 1984-07-09 FR FR8410861A patent/FR2567125B1/fr not_active Expired
-
1985
- 1985-06-11 DE DE8585401139T patent/DE3564268D1/de not_active Expired
- 1985-06-11 EP EP85401139A patent/EP0172041B1/fr not_active Expired
- 1985-06-11 AT AT85401139T patent/ATE36329T1/de not_active IP Right Cessation
- 1985-06-13 AU AU43625/85A patent/AU573147B2/en not_active Ceased
- 1985-06-14 IE IE148685A patent/IE58362B1/en not_active IP Right Cessation
- 1985-06-14 ZA ZA854519A patent/ZA854519B/xx unknown
- 1985-06-14 IL IL75527A patent/IL75527A/xx not_active IP Right Cessation
- 1985-06-20 US US06/746,785 patent/US4649153A/en not_active Expired - Fee Related
- 1985-06-27 CA CA000485580A patent/CA1249834A/fr not_active Expired
- 1985-07-01 GR GR851609A patent/GR851609B/el unknown
- 1985-07-02 NZ NZ212619A patent/NZ212619A/en unknown
- 1985-07-04 MA MA20706A patent/MA20481A1/fr unknown
- 1985-07-05 MX MX8652A patent/MX162258A/es unknown
- 1985-07-05 AR AR85300926A patent/AR242381A1/es active
- 1985-07-08 CS CS855107A patent/CS255887B2/cs unknown
- 1985-07-08 ES ES544961A patent/ES8604550A1/es not_active Expired
- 1985-07-08 HU HU852639A patent/HU202519B/hu not_active IP Right Cessation
- 1985-07-08 SU SU853917559A patent/SU1402261A3/ru active
- 1985-07-08 OA OA58634A patent/OA08076A/xx unknown
- 1985-07-08 JP JP60148462A patent/JPH072733B2/ja not_active Expired - Lifetime
- 1985-07-08 DK DK310685A patent/DK161321C/da not_active IP Right Cessation
- 1985-07-08 NO NO852741A patent/NO171499C/no unknown
- 1985-07-09 YU YU01138/85A patent/YU113885A/xx unknown
- 1985-07-09 DD DD85278415A patent/DD235454A5/de not_active IP Right Cessation
- 1985-08-02 IN IN630/DEL/85A patent/IN166471B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |