New carboxylic acid compounds useful e.g. as antiinflammatory or antithrombotic agents

Carboxylic acid derivatives of formula A-B-C-D-E-Ra (I) and their tautomers, stereoisomers and salts are new. A = a 5-7 membered azacycloalkyl coupled to B via one of its C atoms, which is 1-substituted by Rb and optionally substituted on its C by 1-3 1-3C alkyl groups or A = 5-7 membered biazacyclo...

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Hauptverfasser: GUTH, BRIAN., 88447 WARTHAUSEN, DE, HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE, LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE, PIEPER, HELMUT. DR., 88400 BIBERACH, DE, WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE, AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE
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creator GUTH, BRIAN., 88447 WARTHAUSEN, DE
HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE
LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE
PIEPER, HELMUT. DR., 88400 BIBERACH, DE
WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE
AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE
description Carboxylic acid derivatives of formula A-B-C-D-E-Ra (I) and their tautomers, stereoisomers and salts are new. A = a 5-7 membered azacycloalkyl coupled to B via one of its C atoms, which is 1-substituted by Rb and optionally substituted on its C by 1-3 1-3C alkyl groups or A = 5-7 membered biazacycloalkyl where a methylene may be replaced by CO and which is coupled to B via the second N atom in the 3- or 4-position and is substituted as before; Rb = H, 1-3C alkyl, phenyl-(1-3C alkyl), 1-3C alkylcarbonyl, COCF3, 1-5C alkoxycarbonyl, phenyl-(1-3C alkoxycarbonyl) or CO-O-(CHR2)-O-CO-R1; R1 = 1-5C alkyl, 5-7C cycloalkyl, phenyl-(1-3C alkyl), 1-5C alkoxy, 5-7C cycloalkoxy or phenyl; R2 = H, 1-4C alkyl, 5-7C cycloalkyl or phenyl; B = a 5-7 membered azacycloalkylene which is coupled to A and C in the 1,3- or 1,4-position and is optionally substituted by 1-3 1-3C alkyl groups; C = -O-CO-, -CHR3-CO-, -CHR3-CH2-CO-, -CH2-CHR3-CO-, -CHR3-CO-NR3-, -CHR3-CH2-CO-NR3-, -CH2-CHR3-CO-NR3-, -CO-CHR3-CO-, -CO-CHR3-CO-NR3- or -O-CO-NR3-; R3 = H, 1-5C alkyl, phenyl-(1-3C alkyl) or phenyl; D = phenylene, cyclohexylene or 1,4-piperidinylene or 1,4-piperazinyl optionally substituted by R4 and in which a methylene group may be replaced by CO; E = -CO-, -(CHR3)n-CO-, -NR3-(CHR5)m-CO- or -O-CHR5-CO-; R5 = H, 1-5C alkyl, phenyl-(1-3C alkyl), phenyl, pyridyl or ethynyl; n = 1-3; m = 1 or 2; Ra = OH, 1-6C alkoxy, phenyl-(1-3C alkoxy), 3-9C cycloalkoxy (if the cycloalkyl group has 5-8C atoms it may be substituted by 1 or 2 1-3C alkyl groups), 5-8C cycloalkoxy (where the CH2 group in the 3- or 4-position may be replaced by an O atom or an NH group optionally substituted by 1-3C alkyl, phenyl-(1-3C alkyl), phenyl-(1-3C alkoxycarbonyl) or 2-6C alkanoyl and whose cycloalkyl ring may be substituted by 1 or 2 1-3C alkyl groups), 4-7C cycloalkenyloxy, 3-8C cycloalkyl-(1-3C alkoxy), 3-5C alkenyloxy, phenyl-(3-5C alkenyloxy), 3-5C alkynyloxy or phenyl-(3-5C alkynyloxy) provided that there is no bond to an O atom from a C atom that contains a double or triple bond; Ra may also be 8-10C bicycloalkoxy (optionally substituted by 1 or 2 1-3C alkyl groups), 1,3-dihydro-3-oxo-1-isobenzofuranyloxy, -O-(CR6R7)-O-CO-R8 or the side chain of a natural alpha -amino acid or one of its esters; R6 = H, 1-6C alkyl, 3-7C cycloalkyl or phenyl; R7 = H or 1-6C alkyl, R8 = 1-5C alkyl, 1-5C alkoxy, 5-7C cycloalkyl or 5-7C cycloalkyloxy. All the above phenyl and phenylene groups may be substituted by 1-3 F, Cl, Br, I, 1
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DR., 88400 BIBERACH, DE ; AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</creator><creatorcontrib>GUTH, BRIAN., 88447 WARTHAUSEN, DE ; HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE ; LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE ; PIEPER, HELMUT. DR., 88400 BIBERACH, DE ; WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE ; AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</creatorcontrib><description>Carboxylic acid derivatives of formula A-B-C-D-E-Ra (I) and their tautomers, stereoisomers and salts are new. A = a 5-7 membered azacycloalkyl coupled to B via one of its C atoms, which is 1-substituted by Rb and optionally substituted on its C by 1-3 1-3C alkyl groups or A = 5-7 membered biazacycloalkyl where a methylene may be replaced by CO and which is coupled to B via the second N atom in the 3- or 4-position and is substituted as before; Rb = H, 1-3C alkyl, phenyl-(1-3C alkyl), 1-3C alkylcarbonyl, COCF3, 1-5C alkoxycarbonyl, phenyl-(1-3C alkoxycarbonyl) or CO-O-(CHR2)-O-CO-R1; R1 = 1-5C alkyl, 5-7C cycloalkyl, phenyl-(1-3C alkyl), 1-5C alkoxy, 5-7C cycloalkoxy or phenyl; R2 = H, 1-4C alkyl, 5-7C cycloalkyl or phenyl; B = a 5-7 membered azacycloalkylene which is coupled to A and C in the 1,3- or 1,4-position and is optionally substituted by 1-3 1-3C alkyl groups; C = -O-CO-, -CHR3-CO-, -CHR3-CH2-CO-, -CH2-CHR3-CO-, -CHR3-CO-NR3-, -CHR3-CH2-CO-NR3-, -CH2-CHR3-CO-NR3-, -CO-CHR3-CO-, -CO-CHR3-CO-NR3- or -O-CO-NR3-; R3 = H, 1-5C alkyl, phenyl-(1-3C alkyl) or phenyl; D = phenylene, cyclohexylene or 1,4-piperidinylene or 1,4-piperazinyl optionally substituted by R4 and in which a methylene group may be replaced by CO; E = -CO-, -(CHR3)n-CO-, -NR3-(CHR5)m-CO- or -O-CHR5-CO-; R5 = H, 1-5C alkyl, phenyl-(1-3C alkyl), phenyl, pyridyl or ethynyl; n = 1-3; m = 1 or 2; Ra = OH, 1-6C alkoxy, phenyl-(1-3C alkoxy), 3-9C cycloalkoxy (if the cycloalkyl group has 5-8C atoms it may be substituted by 1 or 2 1-3C alkyl groups), 5-8C cycloalkoxy (where the CH2 group in the 3- or 4-position may be replaced by an O atom or an NH group optionally substituted by 1-3C alkyl, phenyl-(1-3C alkyl), phenyl-(1-3C alkoxycarbonyl) or 2-6C alkanoyl and whose cycloalkyl ring may be substituted by 1 or 2 1-3C alkyl groups), 4-7C cycloalkenyloxy, 3-8C cycloalkyl-(1-3C alkoxy), 3-5C alkenyloxy, phenyl-(3-5C alkenyloxy), 3-5C alkynyloxy or phenyl-(3-5C alkynyloxy) provided that there is no bond to an O atom from a C atom that contains a double or triple bond; Ra may also be 8-10C bicycloalkoxy (optionally substituted by 1 or 2 1-3C alkyl groups), 1,3-dihydro-3-oxo-1-isobenzofuranyloxy, -O-(CR6R7)-O-CO-R8 or the side chain of a natural alpha -amino acid or one of its esters; R6 = H, 1-6C alkyl, 3-7C cycloalkyl or phenyl; R7 = H or 1-6C alkyl, R8 = 1-5C alkyl, 1-5C alkoxy, 5-7C cycloalkyl or 5-7C cycloalkyloxy. All the above phenyl and phenylene groups may be substituted by 1-3 F, Cl, Br, I, 1-3C alkyl, OH, 1-3C alkoxy, phenyl-(1-3C alkoxy) or NH2 groups.</description><edition>6</edition><language>eng ; ger</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1997</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=19970904&amp;DB=EPODOC&amp;CC=DE&amp;NR=19607436A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25543,76293</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=19970904&amp;DB=EPODOC&amp;CC=DE&amp;NR=19607436A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>GUTH, BRIAN., 88447 WARTHAUSEN, DE</creatorcontrib><creatorcontrib>HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE</creatorcontrib><creatorcontrib>LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE</creatorcontrib><creatorcontrib>PIEPER, HELMUT. DR., 88400 BIBERACH, DE</creatorcontrib><creatorcontrib>WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE</creatorcontrib><creatorcontrib>AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</creatorcontrib><title>New carboxylic acid compounds useful e.g. as antiinflammatory or antithrombotic agents</title><description>Carboxylic acid derivatives of formula A-B-C-D-E-Ra (I) and their tautomers, stereoisomers and salts are new. A = a 5-7 membered azacycloalkyl coupled to B via one of its C atoms, which is 1-substituted by Rb and optionally substituted on its C by 1-3 1-3C alkyl groups or A = 5-7 membered biazacycloalkyl where a methylene may be replaced by CO and which is coupled to B via the second N atom in the 3- or 4-position and is substituted as before; Rb = H, 1-3C alkyl, phenyl-(1-3C alkyl), 1-3C alkylcarbonyl, COCF3, 1-5C alkoxycarbonyl, phenyl-(1-3C alkoxycarbonyl) or CO-O-(CHR2)-O-CO-R1; R1 = 1-5C alkyl, 5-7C cycloalkyl, phenyl-(1-3C alkyl), 1-5C alkoxy, 5-7C cycloalkoxy or phenyl; R2 = H, 1-4C alkyl, 5-7C cycloalkyl or phenyl; B = a 5-7 membered azacycloalkylene which is coupled to A and C in the 1,3- or 1,4-position and is optionally substituted by 1-3 1-3C alkyl groups; C = -O-CO-, -CHR3-CO-, -CHR3-CH2-CO-, -CH2-CHR3-CO-, -CHR3-CO-NR3-, -CHR3-CH2-CO-NR3-, -CH2-CHR3-CO-NR3-, -CO-CHR3-CO-, -CO-CHR3-CO-NR3- or -O-CO-NR3-; R3 = H, 1-5C alkyl, phenyl-(1-3C alkyl) or phenyl; D = phenylene, cyclohexylene or 1,4-piperidinylene or 1,4-piperazinyl optionally substituted by R4 and in which a methylene group may be replaced by CO; E = -CO-, -(CHR3)n-CO-, -NR3-(CHR5)m-CO- or -O-CHR5-CO-; R5 = H, 1-5C alkyl, phenyl-(1-3C alkyl), phenyl, pyridyl or ethynyl; n = 1-3; m = 1 or 2; Ra = OH, 1-6C alkoxy, phenyl-(1-3C alkoxy), 3-9C cycloalkoxy (if the cycloalkyl group has 5-8C atoms it may be substituted by 1 or 2 1-3C alkyl groups), 5-8C cycloalkoxy (where the CH2 group in the 3- or 4-position may be replaced by an O atom or an NH group optionally substituted by 1-3C alkyl, phenyl-(1-3C alkyl), phenyl-(1-3C alkoxycarbonyl) or 2-6C alkanoyl and whose cycloalkyl ring may be substituted by 1 or 2 1-3C alkyl groups), 4-7C cycloalkenyloxy, 3-8C cycloalkyl-(1-3C alkoxy), 3-5C alkenyloxy, phenyl-(3-5C alkenyloxy), 3-5C alkynyloxy or phenyl-(3-5C alkynyloxy) provided that there is no bond to an O atom from a C atom that contains a double or triple bond; Ra may also be 8-10C bicycloalkoxy (optionally substituted by 1 or 2 1-3C alkyl groups), 1,3-dihydro-3-oxo-1-isobenzofuranyloxy, -O-(CR6R7)-O-CO-R8 or the side chain of a natural alpha -amino acid or one of its esters; R6 = H, 1-6C alkyl, 3-7C cycloalkyl or phenyl; R7 = H or 1-6C alkyl, R8 = 1-5C alkyl, 1-5C alkoxy, 5-7C cycloalkyl or 5-7C cycloalkyloxy. All the above phenyl and phenylene groups may be substituted by 1-3 F, Cl, Br, I, 1-3C alkyl, OH, 1-3C alkoxy, phenyl-(1-3C alkoxy) or NH2 groups.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1997</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNjEsKwjAUALNxIeodngewWCotLkUrrlyJ2_KavtRAkhfyQXt7UTyAq4FhmLm4X-kJEkPPr8loCSj1AJKt5-yGCDmSygaoGAvACOiS1k4ZtBYThwk4fF16BLY9p89gJJfiUswUmkirHxdifW5vx8uGPHcUPUpylLpTW-7rbbOr6kNZ_dO8ATDmOdM</recordid><startdate>19970904</startdate><enddate>19970904</enddate><creator>GUTH, BRIAN., 88447 WARTHAUSEN, DE</creator><creator>HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE</creator><creator>LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE</creator><creator>PIEPER, HELMUT. DR., 88400 BIBERACH, DE</creator><creator>WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE</creator><creator>AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</creator><scope>EVB</scope></search><sort><creationdate>19970904</creationdate><title>New carboxylic acid compounds useful e.g. as antiinflammatory or antithrombotic agents</title><author>GUTH, BRIAN., 88447 WARTHAUSEN, DE ; HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE ; LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE ; PIEPER, HELMUT. DR., 88400 BIBERACH, DE ; WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE ; AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_DE19607436A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; ger</language><creationdate>1997</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>GUTH, BRIAN., 88447 WARTHAUSEN, DE</creatorcontrib><creatorcontrib>HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE</creatorcontrib><creatorcontrib>LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE</creatorcontrib><creatorcontrib>PIEPER, HELMUT. DR., 88400 BIBERACH, DE</creatorcontrib><creatorcontrib>WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE</creatorcontrib><creatorcontrib>AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>GUTH, BRIAN., 88447 WARTHAUSEN, DE</au><au>HIMMELSBACH, FRANK. DR., 88441 MITTELBIBERACH, DE</au><au>LINZ, GUENTER. DR., 88441 MITTELBIBERACH, DE</au><au>PIEPER, HELMUT. DR., 88400 BIBERACH, DE</au><au>WEISENBERGER, JOHANNES. DR., 88400 BIBERACH, DE</au><au>AUSTEL, VOLKHARD, .. DR., 88400 BIBERACH, DE</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>New carboxylic acid compounds useful e.g. as antiinflammatory or antithrombotic agents</title><date>1997-09-04</date><risdate>1997</risdate><abstract>Carboxylic acid derivatives of formula A-B-C-D-E-Ra (I) and their tautomers, stereoisomers and salts are new. A = a 5-7 membered azacycloalkyl coupled to B via one of its C atoms, which is 1-substituted by Rb and optionally substituted on its C by 1-3 1-3C alkyl groups or A = 5-7 membered biazacycloalkyl where a methylene may be replaced by CO and which is coupled to B via the second N atom in the 3- or 4-position and is substituted as before; Rb = H, 1-3C alkyl, phenyl-(1-3C alkyl), 1-3C alkylcarbonyl, COCF3, 1-5C alkoxycarbonyl, phenyl-(1-3C alkoxycarbonyl) or CO-O-(CHR2)-O-CO-R1; R1 = 1-5C alkyl, 5-7C cycloalkyl, phenyl-(1-3C alkyl), 1-5C alkoxy, 5-7C cycloalkoxy or phenyl; R2 = H, 1-4C alkyl, 5-7C cycloalkyl or phenyl; B = a 5-7 membered azacycloalkylene which is coupled to A and C in the 1,3- or 1,4-position and is optionally substituted by 1-3 1-3C alkyl groups; C = -O-CO-, -CHR3-CO-, -CHR3-CH2-CO-, -CH2-CHR3-CO-, -CHR3-CO-NR3-, -CHR3-CH2-CO-NR3-, -CH2-CHR3-CO-NR3-, -CO-CHR3-CO-, -CO-CHR3-CO-NR3- or -O-CO-NR3-; R3 = H, 1-5C alkyl, phenyl-(1-3C alkyl) or phenyl; D = phenylene, cyclohexylene or 1,4-piperidinylene or 1,4-piperazinyl optionally substituted by R4 and in which a methylene group may be replaced by CO; E = -CO-, -(CHR3)n-CO-, -NR3-(CHR5)m-CO- or -O-CHR5-CO-; R5 = H, 1-5C alkyl, phenyl-(1-3C alkyl), phenyl, pyridyl or ethynyl; n = 1-3; m = 1 or 2; Ra = OH, 1-6C alkoxy, phenyl-(1-3C alkoxy), 3-9C cycloalkoxy (if the cycloalkyl group has 5-8C atoms it may be substituted by 1 or 2 1-3C alkyl groups), 5-8C cycloalkoxy (where the CH2 group in the 3- or 4-position may be replaced by an O atom or an NH group optionally substituted by 1-3C alkyl, phenyl-(1-3C alkyl), phenyl-(1-3C alkoxycarbonyl) or 2-6C alkanoyl and whose cycloalkyl ring may be substituted by 1 or 2 1-3C alkyl groups), 4-7C cycloalkenyloxy, 3-8C cycloalkyl-(1-3C alkoxy), 3-5C alkenyloxy, phenyl-(3-5C alkenyloxy), 3-5C alkynyloxy or phenyl-(3-5C alkynyloxy) provided that there is no bond to an O atom from a C atom that contains a double or triple bond; Ra may also be 8-10C bicycloalkoxy (optionally substituted by 1 or 2 1-3C alkyl groups), 1,3-dihydro-3-oxo-1-isobenzofuranyloxy, -O-(CR6R7)-O-CO-R8 or the side chain of a natural alpha -amino acid or one of its esters; R6 = H, 1-6C alkyl, 3-7C cycloalkyl or phenyl; R7 = H or 1-6C alkyl, R8 = 1-5C alkyl, 1-5C alkoxy, 5-7C cycloalkyl or 5-7C cycloalkyloxy. All the above phenyl and phenylene groups may be substituted by 1-3 F, Cl, Br, I, 1-3C alkyl, OH, 1-3C alkoxy, phenyl-(1-3C alkoxy) or NH2 groups.</abstract><edition>6</edition><oa>free_for_read</oa></addata></record>
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title New carboxylic acid compounds useful e.g. as antiinflammatory or antithrombotic agents
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