NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

Composés de formule (I) caractérisés en ce que .bullet. X représente oxygène ou soufre, .bullet. Y représente oxygène,-NH ou -N(C1-C6)alkyle, .bullet. Ra représente hydrogène, halogène, (C1-C3)alkyle, hydroxy, ou (C1-C3)alkoxy, .bullet. Rb représente hydrogène, halogène, ou (C1-C3)alkyle, .bullet. A...

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Hauptverfasser: BLAIS, STEPHANE, COURTE, KARINE, COMPERE, DELPHINE, DENIS, ALEXIS, DUBLANCHET, ANNE-CLAUDE, CLUZEAU, PHILIPPE, DESCAMPS, SOPHIE, DUCROT, PIERRE
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CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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creator BLAIS, STEPHANE
COURTE, KARINE
COMPERE, DELPHINE
DENIS, ALEXIS
DUBLANCHET, ANNE-CLAUDE
CLUZEAU, PHILIPPE
DESCAMPS, SOPHIE
DUCROT, PIERRE
description Composés de formule (I) caractérisés en ce que .bullet. X représente oxygène ou soufre, .bullet. Y représente oxygène,-NH ou -N(C1-C6)alkyle, .bullet. Ra représente hydrogène, halogène, (C1-C3)alkyle, hydroxy, ou (C1-C3)alkoxy, .bullet. Rb représente hydrogène, halogène, ou (C1-C3)alkyle, .bullet. A représente phényle, pyridyle, (C5-C6)cycloalkyle ou (C5-C6)cycloalkènyle, .bullet. R1 et R2 représentent chacun un groupement choisi parmi hydrogène, halogène, cyano, nitro, halogénoalkyle, halogénoalkoxy, alkyle, alkènyle, alkynyle, -OR4, -NR4R5, -S(O)nR4, -C(O)R4, -C02R4, -O-C(O)R4, -C(O)NR4R5, -N R5- C(O)R4, -NR5-S02R4, -T-CN, -T-OR4, -T-OCF3, -T-NR4R5, -T-S(O)nR4, -T-C(O)R4, - T-C02R4, -T-O-C(O)R4, -T-C(O)NR4R5, -T-NR4-C(O)R5, -T-NR4-S02R5, -R6, et -T- R6 dans lesquels n, T, R4, R5 et R6 sont tels que définis dans la description, .bullet. R3 représente un groupement -R7 ou -U-R11, dans lesquels R7 représente hydrogène, alkyle, aryle, cycloalkyle ou hétérocycle, U représent e une chaîne alkylène linéaire ou ramifiée, et R11, est tel que défini dans la description, leurs isomères optiques ou leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable, et leur utilisation en tant qu'inhibiteur de métalloprotéinase et plus spécifiquement de la métalloprotéinase -12. Thiophene-2-carboxylic acid amide and ester derivatives (I) are new. Thiophene-2-carboxylic acid amide and ester derivatives of formula (I) and their isomers and acid or base addition salts are new. X = O or S; Y = O, NH or N(alkyl); Ra = H, halo, 1-3C alkyl, OH or 1-3C alkoxy; Rb = H, halo or 1-3C alkyl; A = phenyl, 5-6C cycloalkyl or 5-6C cycloalkenyl; R1, R2 = H, halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR4SO2R5, R6 or T-R6; n = 0-2; T = 1-6C alkylene (optionally substituted (os) by =O. halo, alkoxy, OH, NH2 or mono- or dialkylamino, and optionally having one CH2 replaced by O, S, NH or N(alkyl)); R4 = H, alkyl, Ar, Cyc or Het; R5 = H or alkyl; R6 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR5SO2R4, G1 or T-G1); G1 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OH, a
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fullrecord <record><control><sourceid>epo_EVB</sourceid><recordid>TN_cdi_epo_espacenet_CA2497632A1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>CA2497632A1</sourcerecordid><originalsourceid>FETCH-epo_espacenet_CA2497632A13</originalsourceid><addsrcrecordid>eNqNykEKwjAQQNFuXIh6hzmALmxFcTmkUzNgZkISuy1FohvRQr0_VvAArj4f3ry4i7Z0hmRZvSUhqClwi4lbimvwgTyG6VTAUbJaT5ICaQMoNXiLwaGhS2KDZzDqvEb-6jiNJGRhOUFER8tidusfY179uiigoWTsJg-vLo9Df83P_O4MlrvjYV-VuK3-IB_CrDVQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>patent</recordtype></control><display><type>patent</type><title>NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME</title><source>esp@cenet</source><creator>BLAIS, STEPHANE ; COURTE, KARINE ; COMPERE, DELPHINE ; DENIS, ALEXIS ; DUBLANCHET, ANNE-CLAUDE ; CLUZEAU, PHILIPPE ; DESCAMPS, SOPHIE ; DUCROT, PIERRE</creator><creatorcontrib>BLAIS, STEPHANE ; COURTE, KARINE ; COMPERE, DELPHINE ; DENIS, ALEXIS ; DUBLANCHET, ANNE-CLAUDE ; CLUZEAU, PHILIPPE ; DESCAMPS, SOPHIE ; DUCROT, PIERRE</creatorcontrib><description>Composés de formule (I) caractérisés en ce que .bullet. X représente oxygène ou soufre, .bullet. Y représente oxygène,-NH ou -N(C1-C6)alkyle, .bullet. Ra représente hydrogène, halogène, (C1-C3)alkyle, hydroxy, ou (C1-C3)alkoxy, .bullet. Rb représente hydrogène, halogène, ou (C1-C3)alkyle, .bullet. A représente phényle, pyridyle, (C5-C6)cycloalkyle ou (C5-C6)cycloalkènyle, .bullet. R1 et R2 représentent chacun un groupement choisi parmi hydrogène, halogène, cyano, nitro, halogénoalkyle, halogénoalkoxy, alkyle, alkènyle, alkynyle, -OR4, -NR4R5, -S(O)nR4, -C(O)R4, -C02R4, -O-C(O)R4, -C(O)NR4R5, -N R5- C(O)R4, -NR5-S02R4, -T-CN, -T-OR4, -T-OCF3, -T-NR4R5, -T-S(O)nR4, -T-C(O)R4, - T-C02R4, -T-O-C(O)R4, -T-C(O)NR4R5, -T-NR4-C(O)R5, -T-NR4-S02R5, -R6, et -T- R6 dans lesquels n, T, R4, R5 et R6 sont tels que définis dans la description, .bullet. R3 représente un groupement -R7 ou -U-R11, dans lesquels R7 représente hydrogène, alkyle, aryle, cycloalkyle ou hétérocycle, U représent e une chaîne alkylène linéaire ou ramifiée, et R11, est tel que défini dans la description, leurs isomères optiques ou leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable, et leur utilisation en tant qu'inhibiteur de métalloprotéinase et plus spécifiquement de la métalloprotéinase -12. Thiophene-2-carboxylic acid amide and ester derivatives (I) are new. Thiophene-2-carboxylic acid amide and ester derivatives of formula (I) and their isomers and acid or base addition salts are new. X = O or S; Y = O, NH or N(alkyl); Ra = H, halo, 1-3C alkyl, OH or 1-3C alkoxy; Rb = H, halo or 1-3C alkyl; A = phenyl, 5-6C cycloalkyl or 5-6C cycloalkenyl; R1, R2 = H, halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR4SO2R5, R6 or T-R6; n = 0-2; T = 1-6C alkylene (optionally substituted (os) by =O. halo, alkoxy, OH, NH2 or mono- or dialkylamino, and optionally having one CH2 replaced by O, S, NH or N(alkyl)); R4 = H, alkyl, Ar, Cyc or Het; R5 = H or alkyl; R6 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR5SO2R4, G1 or T-G1); G1 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OH, alkoxy, OPh, OCH2Ph, NH2, mono- or di-alkylamino, SH, alkylthio, 1-7C acyl, alkylsulfinyl, COOH, alkoxycarbonyl, Ph or Het); R3 = R7 or U-R11; R7 = H or alkyl, or Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OR8, NR8R9, S(O)mR8, COR8, COOR8, OCOR8, CONR8R9, NR8COR9, NR8SO2R9, V-CN, V-OR8, T-OCF3, V-NR8R9, V-S(O)mR8, V-COR8, V-COOR8, V-OCOR8, V-CONR8R9, V-NR8COR9, V-NR8SO2R9, R10 or V-R10); m = 0-2; V = 1-6C alkylene, 2-6C alkenylene or cyclopropylene, or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R8 = H, alkyl, Ar, Cyc or Het; R9 = H or alkyl; R10 = Ar, Cyc or Het; U = 1-6C alkylene; or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R11 = halo, OR12, NR12R13, S(O)pR12, COR12, COOR12, OCOR12, CONR12R13, NR12COR13 or NR13SO2R12, or R14 (os by 1 or 2 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR15, NR15R16, S(O)qR15, COR15, COOR15, OCOR15, CONR15R16, NR16COR15, NR16SO2R15, W-CN, W-OR15, W-NR15R16, W-S(O)qR15, W-COR15, W-COOR15, W-OCOR15, W-CONR15R16, W-NR16COR15, W-NR16SO2R15, W-R17 or CO-W1-COOR15); R12, R15 = H, alkyl, Ar, Cyc or Het; R13, R16 = H or alkyl; R14, R17 = Ar, Cyc or Het; p, q = 0-2; W = as defined for V; W1 = 1-6C alkylene; Ar = 4-10C mono- or bi-cyclic aryl (one ring optionally being non-aromatic in the case of bicyclic systems); Cyc = optionally partially unsaturated, monocyclic or fused or bridged bicyclic 3-12C cycloalkyl; Het = saturated, unsaturated or aromatic, monocyclic or fused or bridged bicyclic 3-12 membered heterocycle, containing 1-4 of O, S and/or N heteroatoms and optionally containing 1 or 2 =O or =S groups; alkyl moieties have 1-6C and alkenyl or alkynyl moieties 2-6C unless specified otherwise; haloalkyl moieties contain 1-6 halo atoms; provided that: (1) the following compounds are excluded: 5-methyl-4-phenyl-thiophene-2-carboxylic acid and its ethyl ester, methyl 3-hydroxy-4-phenyl-thiophene-2-carboxylate, 3-methoxy-4-phenyl-thiophene-2-carboxylic acid and its methyl ester, 4-(4-methoxyphenyl)-thiophene-2-carboxylic acid and its methyl ester, 4-phenyl-thiophene-2-carboxylic acid and its methyl and ethyl esters, 4-(4-tert. butylphenyl)-thiophene-2-carboxylic acid, methyl 5-chloro-3-hydroxy-4-phenyl-thiophene-2-carboxylate, 4-(3,5-dimethylphenyl)-thiophene-2-carboxylic acid, methyl 4-((4-acetylamino)-phenyl)-thiophene-2-carboxylic acid, 4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, 5-methyl-4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, methyl 2-((4-(4-methoxyphenyl)-thiophen-2-yl)-carboxamido)-benzoate and N-(3-(trifluoromethyl)-phenyl)-4-(4-methoxyphenyl)-thiophene-2-carboxamide; (2) if Ra = H and A = cyclopenten-1-yl substituted in the 2-position by os thienyl as R1, then Rb = H, halo or 2-3C alkyl; (3) if R3 = Het as R7, then</description><edition>7</edition><language>eng ; fre</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; HUMAN NECESSITIES ; HYGIENE ; MEDICAL OR VETERINARY SCIENCE ; METALLURGY ; ORGANIC CHEMISTRY ; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><creationdate>2004</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20040304&amp;DB=EPODOC&amp;CC=CA&amp;NR=2497632A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20040304&amp;DB=EPODOC&amp;CC=CA&amp;NR=2497632A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>BLAIS, STEPHANE</creatorcontrib><creatorcontrib>COURTE, KARINE</creatorcontrib><creatorcontrib>COMPERE, DELPHINE</creatorcontrib><creatorcontrib>DENIS, ALEXIS</creatorcontrib><creatorcontrib>DUBLANCHET, ANNE-CLAUDE</creatorcontrib><creatorcontrib>CLUZEAU, PHILIPPE</creatorcontrib><creatorcontrib>DESCAMPS, SOPHIE</creatorcontrib><creatorcontrib>DUCROT, PIERRE</creatorcontrib><title>NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME</title><description>Composés de formule (I) caractérisés en ce que .bullet. X représente oxygène ou soufre, .bullet. Y représente oxygène,-NH ou -N(C1-C6)alkyle, .bullet. Ra représente hydrogène, halogène, (C1-C3)alkyle, hydroxy, ou (C1-C3)alkoxy, .bullet. Rb représente hydrogène, halogène, ou (C1-C3)alkyle, .bullet. A représente phényle, pyridyle, (C5-C6)cycloalkyle ou (C5-C6)cycloalkènyle, .bullet. R1 et R2 représentent chacun un groupement choisi parmi hydrogène, halogène, cyano, nitro, halogénoalkyle, halogénoalkoxy, alkyle, alkènyle, alkynyle, -OR4, -NR4R5, -S(O)nR4, -C(O)R4, -C02R4, -O-C(O)R4, -C(O)NR4R5, -N R5- C(O)R4, -NR5-S02R4, -T-CN, -T-OR4, -T-OCF3, -T-NR4R5, -T-S(O)nR4, -T-C(O)R4, - T-C02R4, -T-O-C(O)R4, -T-C(O)NR4R5, -T-NR4-C(O)R5, -T-NR4-S02R5, -R6, et -T- R6 dans lesquels n, T, R4, R5 et R6 sont tels que définis dans la description, .bullet. R3 représente un groupement -R7 ou -U-R11, dans lesquels R7 représente hydrogène, alkyle, aryle, cycloalkyle ou hétérocycle, U représent e une chaîne alkylène linéaire ou ramifiée, et R11, est tel que défini dans la description, leurs isomères optiques ou leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable, et leur utilisation en tant qu'inhibiteur de métalloprotéinase et plus spécifiquement de la métalloprotéinase -12. Thiophene-2-carboxylic acid amide and ester derivatives (I) are new. Thiophene-2-carboxylic acid amide and ester derivatives of formula (I) and their isomers and acid or base addition salts are new. X = O or S; Y = O, NH or N(alkyl); Ra = H, halo, 1-3C alkyl, OH or 1-3C alkoxy; Rb = H, halo or 1-3C alkyl; A = phenyl, 5-6C cycloalkyl or 5-6C cycloalkenyl; R1, R2 = H, halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR4SO2R5, R6 or T-R6; n = 0-2; T = 1-6C alkylene (optionally substituted (os) by =O. halo, alkoxy, OH, NH2 or mono- or dialkylamino, and optionally having one CH2 replaced by O, S, NH or N(alkyl)); R4 = H, alkyl, Ar, Cyc or Het; R5 = H or alkyl; R6 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR5SO2R4, G1 or T-G1); G1 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OH, alkoxy, OPh, OCH2Ph, NH2, mono- or di-alkylamino, SH, alkylthio, 1-7C acyl, alkylsulfinyl, COOH, alkoxycarbonyl, Ph or Het); R3 = R7 or U-R11; R7 = H or alkyl, or Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OR8, NR8R9, S(O)mR8, COR8, COOR8, OCOR8, CONR8R9, NR8COR9, NR8SO2R9, V-CN, V-OR8, T-OCF3, V-NR8R9, V-S(O)mR8, V-COR8, V-COOR8, V-OCOR8, V-CONR8R9, V-NR8COR9, V-NR8SO2R9, R10 or V-R10); m = 0-2; V = 1-6C alkylene, 2-6C alkenylene or cyclopropylene, or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R8 = H, alkyl, Ar, Cyc or Het; R9 = H or alkyl; R10 = Ar, Cyc or Het; U = 1-6C alkylene; or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R11 = halo, OR12, NR12R13, S(O)pR12, COR12, COOR12, OCOR12, CONR12R13, NR12COR13 or NR13SO2R12, or R14 (os by 1 or 2 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR15, NR15R16, S(O)qR15, COR15, COOR15, OCOR15, CONR15R16, NR16COR15, NR16SO2R15, W-CN, W-OR15, W-NR15R16, W-S(O)qR15, W-COR15, W-COOR15, W-OCOR15, W-CONR15R16, W-NR16COR15, W-NR16SO2R15, W-R17 or CO-W1-COOR15); R12, R15 = H, alkyl, Ar, Cyc or Het; R13, R16 = H or alkyl; R14, R17 = Ar, Cyc or Het; p, q = 0-2; W = as defined for V; W1 = 1-6C alkylene; Ar = 4-10C mono- or bi-cyclic aryl (one ring optionally being non-aromatic in the case of bicyclic systems); Cyc = optionally partially unsaturated, monocyclic or fused or bridged bicyclic 3-12C cycloalkyl; Het = saturated, unsaturated or aromatic, monocyclic or fused or bridged bicyclic 3-12 membered heterocycle, containing 1-4 of O, S and/or N heteroatoms and optionally containing 1 or 2 =O or =S groups; alkyl moieties have 1-6C and alkenyl or alkynyl moieties 2-6C unless specified otherwise; haloalkyl moieties contain 1-6 halo atoms; provided that: (1) the following compounds are excluded: 5-methyl-4-phenyl-thiophene-2-carboxylic acid and its ethyl ester, methyl 3-hydroxy-4-phenyl-thiophene-2-carboxylate, 3-methoxy-4-phenyl-thiophene-2-carboxylic acid and its methyl ester, 4-(4-methoxyphenyl)-thiophene-2-carboxylic acid and its methyl ester, 4-phenyl-thiophene-2-carboxylic acid and its methyl and ethyl esters, 4-(4-tert. butylphenyl)-thiophene-2-carboxylic acid, methyl 5-chloro-3-hydroxy-4-phenyl-thiophene-2-carboxylate, 4-(3,5-dimethylphenyl)-thiophene-2-carboxylic acid, methyl 4-((4-acetylamino)-phenyl)-thiophene-2-carboxylic acid, 4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, 5-methyl-4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, methyl 2-((4-(4-methoxyphenyl)-thiophen-2-yl)-carboxamido)-benzoate and N-(3-(trifluoromethyl)-phenyl)-4-(4-methoxyphenyl)-thiophene-2-carboxamide; (2) if Ra = H and A = cyclopenten-1-yl substituted in the 2-position by os thienyl as R1, then Rb = H, halo or 2-3C alkyl; (3) if R3 = Het as R7, then</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HUMAN NECESSITIES</subject><subject>HYGIENE</subject><subject>MEDICAL OR VETERINARY SCIENCE</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><subject>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2004</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNykEKwjAQQNFuXIh6hzmALmxFcTmkUzNgZkISuy1FohvRQr0_VvAArj4f3ry4i7Z0hmRZvSUhqClwi4lbimvwgTyG6VTAUbJaT5ICaQMoNXiLwaGhS2KDZzDqvEb-6jiNJGRhOUFER8tidusfY179uiigoWTsJg-vLo9Df83P_O4MlrvjYV-VuK3-IB_CrDVQ</recordid><startdate>20040304</startdate><enddate>20040304</enddate><creator>BLAIS, STEPHANE</creator><creator>COURTE, KARINE</creator><creator>COMPERE, DELPHINE</creator><creator>DENIS, ALEXIS</creator><creator>DUBLANCHET, ANNE-CLAUDE</creator><creator>CLUZEAU, PHILIPPE</creator><creator>DESCAMPS, SOPHIE</creator><creator>DUCROT, PIERRE</creator><scope>EVB</scope></search><sort><creationdate>20040304</creationdate><title>NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME</title><author>BLAIS, STEPHANE ; COURTE, KARINE ; COMPERE, DELPHINE ; DENIS, ALEXIS ; DUBLANCHET, ANNE-CLAUDE ; CLUZEAU, PHILIPPE ; DESCAMPS, SOPHIE ; DUCROT, PIERRE</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_CA2497632A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; fre</language><creationdate>2004</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HUMAN NECESSITIES</topic><topic>HYGIENE</topic><topic>MEDICAL OR VETERINARY SCIENCE</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><topic>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</topic><toplevel>online_resources</toplevel><creatorcontrib>BLAIS, STEPHANE</creatorcontrib><creatorcontrib>COURTE, KARINE</creatorcontrib><creatorcontrib>COMPERE, DELPHINE</creatorcontrib><creatorcontrib>DENIS, ALEXIS</creatorcontrib><creatorcontrib>DUBLANCHET, ANNE-CLAUDE</creatorcontrib><creatorcontrib>CLUZEAU, PHILIPPE</creatorcontrib><creatorcontrib>DESCAMPS, SOPHIE</creatorcontrib><creatorcontrib>DUCROT, PIERRE</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>BLAIS, STEPHANE</au><au>COURTE, KARINE</au><au>COMPERE, DELPHINE</au><au>DENIS, ALEXIS</au><au>DUBLANCHET, ANNE-CLAUDE</au><au>CLUZEAU, PHILIPPE</au><au>DESCAMPS, SOPHIE</au><au>DUCROT, PIERRE</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME</title><date>2004-03-04</date><risdate>2004</risdate><abstract>Composés de formule (I) caractérisés en ce que .bullet. X représente oxygène ou soufre, .bullet. Y représente oxygène,-NH ou -N(C1-C6)alkyle, .bullet. Ra représente hydrogène, halogène, (C1-C3)alkyle, hydroxy, ou (C1-C3)alkoxy, .bullet. Rb représente hydrogène, halogène, ou (C1-C3)alkyle, .bullet. A représente phényle, pyridyle, (C5-C6)cycloalkyle ou (C5-C6)cycloalkènyle, .bullet. R1 et R2 représentent chacun un groupement choisi parmi hydrogène, halogène, cyano, nitro, halogénoalkyle, halogénoalkoxy, alkyle, alkènyle, alkynyle, -OR4, -NR4R5, -S(O)nR4, -C(O)R4, -C02R4, -O-C(O)R4, -C(O)NR4R5, -N R5- C(O)R4, -NR5-S02R4, -T-CN, -T-OR4, -T-OCF3, -T-NR4R5, -T-S(O)nR4, -T-C(O)R4, - T-C02R4, -T-O-C(O)R4, -T-C(O)NR4R5, -T-NR4-C(O)R5, -T-NR4-S02R5, -R6, et -T- R6 dans lesquels n, T, R4, R5 et R6 sont tels que définis dans la description, .bullet. R3 représente un groupement -R7 ou -U-R11, dans lesquels R7 représente hydrogène, alkyle, aryle, cycloalkyle ou hétérocycle, U représent e une chaîne alkylène linéaire ou ramifiée, et R11, est tel que défini dans la description, leurs isomères optiques ou leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable, et leur utilisation en tant qu'inhibiteur de métalloprotéinase et plus spécifiquement de la métalloprotéinase -12. Thiophene-2-carboxylic acid amide and ester derivatives (I) are new. Thiophene-2-carboxylic acid amide and ester derivatives of formula (I) and their isomers and acid or base addition salts are new. X = O or S; Y = O, NH or N(alkyl); Ra = H, halo, 1-3C alkyl, OH or 1-3C alkoxy; Rb = H, halo or 1-3C alkyl; A = phenyl, 5-6C cycloalkyl or 5-6C cycloalkenyl; R1, R2 = H, halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR4SO2R5, R6 or T-R6; n = 0-2; T = 1-6C alkylene (optionally substituted (os) by =O. halo, alkoxy, OH, NH2 or mono- or dialkylamino, and optionally having one CH2 replaced by O, S, NH or N(alkyl)); R4 = H, alkyl, Ar, Cyc or Het; R5 = H or alkyl; R6 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, OR4, NR4R5, S(O)nR4, COR4, COOR4, OCOR4, CONR4R5, NR5COR4, NR5SO2R4, T-CN, T-OR4, T-OCF3, T-NR4R5, T-S(O)nR4, T-COR4, T-COOR4, T-OCOR4, T-CONR4R5, T-NR4COR5, T-NR5SO2R4, G1 or T-G1); G1 = Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OH, alkoxy, OPh, OCH2Ph, NH2, mono- or di-alkylamino, SH, alkylthio, 1-7C acyl, alkylsulfinyl, COOH, alkoxycarbonyl, Ph or Het); R3 = R7 or U-R11; R7 = H or alkyl, or Ar, Cyc or Het (all os by 1-5 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, OR8, NR8R9, S(O)mR8, COR8, COOR8, OCOR8, CONR8R9, NR8COR9, NR8SO2R9, V-CN, V-OR8, T-OCF3, V-NR8R9, V-S(O)mR8, V-COR8, V-COOR8, V-OCOR8, V-CONR8R9, V-NR8COR9, V-NR8SO2R9, R10 or V-R10); m = 0-2; V = 1-6C alkylene, 2-6C alkenylene or cyclopropylene, or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R8 = H, alkyl, Ar, Cyc or Het; R9 = H or alkyl; R10 = Ar, Cyc or Het; U = 1-6C alkylene; or 2-6C alkylene having one CH2 replaced by O, S, NH or N(alkyl); R11 = halo, OR12, NR12R13, S(O)pR12, COR12, COOR12, OCOR12, CONR12R13, NR12COR13 or NR13SO2R12, or R14 (os by 1 or 2 of halo, CN, NO2, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, OR15, NR15R16, S(O)qR15, COR15, COOR15, OCOR15, CONR15R16, NR16COR15, NR16SO2R15, W-CN, W-OR15, W-NR15R16, W-S(O)qR15, W-COR15, W-COOR15, W-OCOR15, W-CONR15R16, W-NR16COR15, W-NR16SO2R15, W-R17 or CO-W1-COOR15); R12, R15 = H, alkyl, Ar, Cyc or Het; R13, R16 = H or alkyl; R14, R17 = Ar, Cyc or Het; p, q = 0-2; W = as defined for V; W1 = 1-6C alkylene; Ar = 4-10C mono- or bi-cyclic aryl (one ring optionally being non-aromatic in the case of bicyclic systems); Cyc = optionally partially unsaturated, monocyclic or fused or bridged bicyclic 3-12C cycloalkyl; Het = saturated, unsaturated or aromatic, monocyclic or fused or bridged bicyclic 3-12 membered heterocycle, containing 1-4 of O, S and/or N heteroatoms and optionally containing 1 or 2 =O or =S groups; alkyl moieties have 1-6C and alkenyl or alkynyl moieties 2-6C unless specified otherwise; haloalkyl moieties contain 1-6 halo atoms; provided that: (1) the following compounds are excluded: 5-methyl-4-phenyl-thiophene-2-carboxylic acid and its ethyl ester, methyl 3-hydroxy-4-phenyl-thiophene-2-carboxylate, 3-methoxy-4-phenyl-thiophene-2-carboxylic acid and its methyl ester, 4-(4-methoxyphenyl)-thiophene-2-carboxylic acid and its methyl ester, 4-phenyl-thiophene-2-carboxylic acid and its methyl and ethyl esters, 4-(4-tert. butylphenyl)-thiophene-2-carboxylic acid, methyl 5-chloro-3-hydroxy-4-phenyl-thiophene-2-carboxylate, 4-(3,5-dimethylphenyl)-thiophene-2-carboxylic acid, methyl 4-((4-acetylamino)-phenyl)-thiophene-2-carboxylic acid, 4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, 5-methyl-4-phenyl-thiophene-2-carboxamide and its N-methyl and N,N-dimethyl derivatives, methyl 2-((4-(4-methoxyphenyl)-thiophen-2-yl)-carboxamido)-benzoate and N-(3-(trifluoromethyl)-phenyl)-4-(4-methoxyphenyl)-thiophene-2-carboxamide; (2) if Ra = H and A = cyclopenten-1-yl substituted in the 2-position by os thienyl as R1, then Rb = H, halo or 2-3C alkyl; (3) if R3 = Het as R7, then</abstract><edition>7</edition><oa>free_for_read</oa></addata></record>
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subjects CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
title NOVEL THIOPHENE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
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