RU2007126761A - ПРОИЗВОДНЫЕ ПИРРОЛА, ОБЛАДАЮЩИЕ АНТАГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К РЕЦЕПТОРУ CRTh2 - Google Patents
ПРОИЗВОДНЫЕ ПИРРОЛА, ОБЛАДАЮЩИЕ АНТАГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К РЕЦЕПТОРУ CRTh2 Download PDFInfo
- Publication number
- RU2007126761A RU2007126761A RU2007126761/04A RU2007126761A RU2007126761A RU 2007126761 A RU2007126761 A RU 2007126761A RU 2007126761/04 A RU2007126761/04 A RU 2007126761/04A RU 2007126761 A RU2007126761 A RU 2007126761A RU 2007126761 A RU2007126761 A RU 2007126761A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- group
- acetic acid
- cyano
- pyrrol
- Prior art date
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- 102000009389 Prostaglandin D receptors Human genes 0.000 title 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 title 1
- 230000003042 antagnostic effect Effects 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 36
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 229910052799 carbon Inorganic materials 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 239000011593 sulfur Substances 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 16
- 239000001301 oxygen Substances 0.000 claims 16
- -1 amino, amino Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 239000012458 free base Substances 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000002837 carbocyclic group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- YJUVYHOMALZUHD-UHFFFAOYSA-N 2-(3-cyano-4-phenylpyrrol-1-yl)acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=CC=CC=2)=C1 YJUVYHOMALZUHD-UHFFFAOYSA-N 0.000 claims 1
- PTNSYGUCCHMLFH-UHFFFAOYSA-N 2-[3-(1,3-benzodioxol-4-yl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=3OCOC=3C=CC=2)=C1 PTNSYGUCCHMLFH-UHFFFAOYSA-N 0.000 claims 1
- KVANDVBZBOFONL-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=CC=2)Cl)=C1 KVANDVBZBOFONL-UHFFFAOYSA-N 0.000 claims 1
- QPSNHFIHNPXEQO-UHFFFAOYSA-N 2-[3-(3-chloro-2-fluorophenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=C(Cl)C=CC=2)F)=C1 QPSNHFIHNPXEQO-UHFFFAOYSA-N 0.000 claims 1
- UWAMJVIZSDIZQS-UHFFFAOYSA-N 2-[3-(3-chloro-5-cyanophenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)C#N)=C1 UWAMJVIZSDIZQS-UHFFFAOYSA-N 0.000 claims 1
- WPTSJPTVHDPOLW-UHFFFAOYSA-N 2-[3-(3-chloro-5-ethylsulfonylphenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound CCS(=O)(=O)C1=CC(Cl)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 WPTSJPTVHDPOLW-UHFFFAOYSA-N 0.000 claims 1
- UVWJVZZLVYDYIB-UHFFFAOYSA-N 2-[3-(3-chloro-5-morpholin-4-ylsulfonylphenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)S(=O)(=O)N2CCOCC2)=C1 UVWJVZZLVYDYIB-UHFFFAOYSA-N 0.000 claims 1
- ADSFMGHJXUZFFQ-UHFFFAOYSA-N 2-[3-(3-chloro-5-piperidin-1-ylsulfonylphenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)S(=O)(=O)N2CCCCC2)=C1 ADSFMGHJXUZFFQ-UHFFFAOYSA-N 0.000 claims 1
- BMIJYDIIIHBVEZ-UHFFFAOYSA-N 2-[3-(3-chloro-5-pyrrolidin-1-ylsulfonylphenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)S(=O)(=O)N2CCCC2)=C1 BMIJYDIIIHBVEZ-UHFFFAOYSA-N 0.000 claims 1
- QREXYXJZFJMYCT-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(Cl)C=CC=2)=C1 QREXYXJZFJMYCT-UHFFFAOYSA-N 0.000 claims 1
- LRRHUBLNVLGYCO-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=CC(Cl)=CC=2)=C1 LRRHUBLNVLGYCO-UHFFFAOYSA-N 0.000 claims 1
- DQSBVIFHCQLGIZ-UHFFFAOYSA-N 2-[3-[2,5-bis(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=C(C=2)C(F)(F)F)C(F)(F)F)=C1 DQSBVIFHCQLGIZ-UHFFFAOYSA-N 0.000 claims 1
- DRAHOOXBWFOGPU-UHFFFAOYSA-N 2-[3-[2-chloro-3-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 DRAHOOXBWFOGPU-UHFFFAOYSA-N 0.000 claims 1
- AKFOWPWOLZROCF-UHFFFAOYSA-N 2-[3-[2-chloro-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 AKFOWPWOLZROCF-UHFFFAOYSA-N 0.000 claims 1
- FFBKASIWFMZZLG-UHFFFAOYSA-N 2-[3-[3,5-bis(trifluoromethyl)phenyl]-4-(dimethylcarbamoyl)pyrrol-1-yl]acetic acid Chemical compound CN(C)C(=O)C1=CN(CC(O)=O)C=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FFBKASIWFMZZLG-UHFFFAOYSA-N 0.000 claims 1
- OAFAGCNQKIENPF-UHFFFAOYSA-N 2-[3-[3,5-bis(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 OAFAGCNQKIENPF-UHFFFAOYSA-N 0.000 claims 1
- LNGOZLGOFMFFHM-UHFFFAOYSA-N 2-[3-[3,5-bis(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]propanoic acid Chemical compound OC(=O)C(C)N1C=C(C#N)C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 LNGOZLGOFMFFHM-UHFFFAOYSA-N 0.000 claims 1
- CHKQKEZYJIJDGD-UHFFFAOYSA-N 2-[3-[3-(butylsulfamoyl)-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)NCCCC)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 CHKQKEZYJIJDGD-UHFFFAOYSA-N 0.000 claims 1
- ATMOSMKZQQJYJW-UHFFFAOYSA-N 2-[3-[3-[butyl(methyl)sulfamoyl]-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)N(C)CCCC)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 ATMOSMKZQQJYJW-UHFFFAOYSA-N 0.000 claims 1
- QLVWPNRSAWXSJV-UHFFFAOYSA-N 2-[3-[3-butylsulfonyl-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)CCCC)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 QLVWPNRSAWXSJV-UHFFFAOYSA-N 0.000 claims 1
- LRNQXCQQIXFMJC-UHFFFAOYSA-N 2-[3-[3-chloro-2-fluoro-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=C(Cl)C=C(C=2)C(F)(F)F)F)=C1 LRNQXCQQIXFMJC-UHFFFAOYSA-N 0.000 claims 1
- VFDPMBJXNWARNK-UHFFFAOYSA-N 2-[3-[3-chloro-5-(trifluoromethyl)phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)C(F)(F)F)=C1 VFDPMBJXNWARNK-UHFFFAOYSA-N 0.000 claims 1
- CGDSGZVQOSTXLM-UHFFFAOYSA-N 2-[3-[3-chloro-5-[2-hydroxyethyl(methyl)sulfamoyl]phenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OCCN(C)S(=O)(=O)C1=CC(Cl)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 CGDSGZVQOSTXLM-UHFFFAOYSA-N 0.000 claims 1
- PAFIUVAQVSWDKA-UHFFFAOYSA-N 2-[3-[3-chloro-5-[4-(2-cyanoethyl)piperazin-1-yl]sulfonylphenyl]-4-cyanopyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(Cl)C=2)S(=O)(=O)N2CCN(CCC#N)CC2)=C1 PAFIUVAQVSWDKA-UHFFFAOYSA-N 0.000 claims 1
- FHVUOMXGRCJLHY-UHFFFAOYSA-N 2-[3-cyano-4-(2,3-dichlorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=C(Cl)C=CC=2)Cl)=C1 FHVUOMXGRCJLHY-UHFFFAOYSA-N 0.000 claims 1
- XUQWSVJVBJAPLP-UHFFFAOYSA-N 2-[3-cyano-4-(2,5-dichlorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=C(Cl)C=2)Cl)=C1 XUQWSVJVBJAPLP-UHFFFAOYSA-N 0.000 claims 1
- SMMTWUDQNLDSHP-UHFFFAOYSA-N 2-[3-cyano-4-(2-cyanophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=CC=2)C#N)=C1 SMMTWUDQNLDSHP-UHFFFAOYSA-N 0.000 claims 1
- DIQFFWLQMHWDCP-UHFFFAOYSA-N 2-[3-cyano-4-(3,5-dichlorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(Cl)C=C(Cl)C=2)=C1 DIQFFWLQMHWDCP-UHFFFAOYSA-N 0.000 claims 1
- MOHZDZZHFPLKLJ-UHFFFAOYSA-N 2-[3-cyano-4-(3,5-difluorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(F)C=C(F)C=2)=C1 MOHZDZZHFPLKLJ-UHFFFAOYSA-N 0.000 claims 1
- KNJQLFWWPBIONI-UHFFFAOYSA-N 2-[3-cyano-4-(3-cyanophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=CC=2)C#N)=C1 KNJQLFWWPBIONI-UHFFFAOYSA-N 0.000 claims 1
- XJRCBKQMSIQHSO-UHFFFAOYSA-N 2-[3-cyano-4-(3-fluorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(F)C=CC=2)=C1 XJRCBKQMSIQHSO-UHFFFAOYSA-N 0.000 claims 1
- YDGCCGPGWJYIHF-UHFFFAOYSA-N 2-[3-cyano-4-(3-methylsulfonylphenyl)pyrrol-1-yl]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 YDGCCGPGWJYIHF-UHFFFAOYSA-N 0.000 claims 1
- JODJYCSNPQUAKK-UHFFFAOYSA-N 2-[3-cyano-4-(4-fluorophenyl)pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=CC(F)=CC=2)=C1 JODJYCSNPQUAKK-UHFFFAOYSA-N 0.000 claims 1
- CSVCPBLCHNEISH-UHFFFAOYSA-N 2-[3-cyano-4-[2-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=CC=CC=2)C(F)(F)F)=C1 CSVCPBLCHNEISH-UHFFFAOYSA-N 0.000 claims 1
- GLSHONRTDYSKQH-UHFFFAOYSA-N 2-[3-cyano-4-[2-fluoro-3-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C(=C(C=CC=2)C(F)(F)F)F)=C1 GLSHONRTDYSKQH-UHFFFAOYSA-N 0.000 claims 1
- IYMACIXIPSGPBQ-UHFFFAOYSA-N 2-[3-cyano-4-[3-(2,2-dimethylpropylsulfamoyl)-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)NCC(C)(C)C)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 IYMACIXIPSGPBQ-UHFFFAOYSA-N 0.000 claims 1
- XCUKWUPHLJGLHH-UHFFFAOYSA-N 2-[3-cyano-4-[3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C=2C=CC(F)=CC=2)C(F)(F)F)=C1 XCUKWUPHLJGLHH-UHFFFAOYSA-N 0.000 claims 1
- FIZLDJYRPHMZHQ-UHFFFAOYSA-N 2-[3-cyano-4-[3-(dimethylsulfamoyl)-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)N(C)C)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 FIZLDJYRPHMZHQ-UHFFFAOYSA-N 0.000 claims 1
- ZKPOAYTYYUIIQI-UHFFFAOYSA-N 2-[3-cyano-4-[3-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 ZKPOAYTYYUIIQI-UHFFFAOYSA-N 0.000 claims 1
- AWXSHLGXUHELDP-UHFFFAOYSA-N 2-[3-cyano-4-[3-(trifluoromethylsulfanyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(SC(F)(F)F)C=CC=2)=C1 AWXSHLGXUHELDP-UHFFFAOYSA-N 0.000 claims 1
- AWEBWIKQIPVNDD-UHFFFAOYSA-N 2-[3-cyano-4-[3-[ethyl(methyl)sulfamoyl]-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)N(C)CC)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 AWEBWIKQIPVNDD-UHFFFAOYSA-N 0.000 claims 1
- XKGCUFXVLVDZCC-UHFFFAOYSA-N 2-[3-cyano-4-[3-cyano-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C#N)C(F)(F)F)=C1 XKGCUFXVLVDZCC-UHFFFAOYSA-N 0.000 claims 1
- KFOAQYZXQGKDJQ-UHFFFAOYSA-N 2-[3-cyano-4-[3-ethylsulfonyl-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)CC)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 KFOAQYZXQGKDJQ-UHFFFAOYSA-N 0.000 claims 1
- AVFJEAAZFHVNNT-UHFFFAOYSA-N 2-[3-cyano-4-[3-fluoro-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(F)C=2)C(F)(F)F)=C1 AVFJEAAZFHVNNT-UHFFFAOYSA-N 0.000 claims 1
- KRSULBRCZUXZAX-UHFFFAOYSA-N 2-[3-cyano-4-[3-iodo-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(I)C=2)C(F)(F)F)=C1 KRSULBRCZUXZAX-UHFFFAOYSA-N 0.000 claims 1
- QOWWDOFGCWJVQR-UHFFFAOYSA-N 2-[3-cyano-4-[3-methylsulfonyl-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)C)=CC(C=2C(=CN(CC(O)=O)C=2)C#N)=C1 QOWWDOFGCWJVQR-UHFFFAOYSA-N 0.000 claims 1
- JOEVFESFEJVZRA-UHFFFAOYSA-N 2-[3-cyano-4-[3-morpholin-4-ylsulfonyl-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C(F)(F)F)S(=O)(=O)N2CCOCC2)=C1 JOEVFESFEJVZRA-UHFFFAOYSA-N 0.000 claims 1
- FNROMQUPSYPNRU-UHFFFAOYSA-N 2-[3-cyano-4-[3-piperidin-1-ylsulfonyl-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C(F)(F)F)S(=O)(=O)N2CCCCC2)=C1 FNROMQUPSYPNRU-UHFFFAOYSA-N 0.000 claims 1
- GLUOXGPMVZDVFL-UHFFFAOYSA-N 2-[3-cyano-4-[3-pyrrolidin-1-ylsulfonyl-5-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=C(C=C(C=2)C(F)(F)F)S(=O)(=O)N2CCCC2)=C1 GLUOXGPMVZDVFL-UHFFFAOYSA-N 0.000 claims 1
- YWQFHLWUZBVPRP-UHFFFAOYSA-N 2-[3-cyano-4-[4-(trifluoromethyl)phenyl]pyrrol-1-yl]acetic acid Chemical compound OC(=O)CN1C=C(C#N)C(C=2C=CC(=CC=2)C(F)(F)F)=C1 YWQFHLWUZBVPRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- PZHHLCQPEDBCLA-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-1-(carboxymethyl)pyrrole-3-carboxylic acid Chemical compound OC(=O)CN1C=C(C(O)=O)C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 PZHHLCQPEDBCLA-UHFFFAOYSA-N 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 229940124623 antihistamine drug Drugs 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 239000003434 antitussive agent Substances 0.000 claims 1
- 229940124584 antitussives Drugs 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 229940124630 bronchodilator Drugs 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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| GB0427381.9 | 2004-12-14 |
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| RU2007126761A true RU2007126761A (ru) | 2009-01-27 |
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| PE20120056A1 (es) * | 2009-02-24 | 2012-02-05 | Merck Sharp & Dohme | Derivados de indol como antagonistas del receptor crth2 |
| SG181900A1 (en) | 2009-12-23 | 2012-08-30 | Ironwood Pharmaceuticals Inc | Crth2 modulators |
| PT2558447E (pt) | 2010-03-22 | 2014-11-25 | Actelion Pharmaceuticals Ltd | Derivados de 3-(heteroarilamino)-1,2,3,4-tetrahidro-9hcarbazol e o seu uso como moduladores do receptor de prostaglandina d2 |
| WO2011117184A1 (de) | 2010-03-24 | 2011-09-29 | Bayer Cropscience Ag | Fludioxonil-derivate |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| US20140187795A1 (en) * | 2010-12-08 | 2014-07-03 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators and preparation thereof |
| DK2697223T3 (en) | 2011-04-14 | 2016-09-05 | Actelion Pharmaceuticals Ltd | 7- (heteroaryl-amino) -6,7,8,9-tetrahydro-pyrido [1,2-a] indole-acetic acid derivatives and their use as prostaglandin D2 receptor |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| JP6097765B2 (ja) | 2011-12-21 | 2017-03-15 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | ヘテロシクリル誘導体及びプロスタグランジンｄ２受容体調節剤としてのそれらの使用 |
| WO2013155422A1 (en) * | 2012-04-12 | 2013-10-17 | Ironwood Pharmaceuticals, Inc. | Methods of treating alopecia and acne |
| WO2014006585A1 (en) | 2012-07-05 | 2014-01-09 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| ES2461415B1 (es) * | 2012-10-16 | 2015-03-16 | Consejo Superior De Investigaciones Científicas (Csic) | Derivados funcionalizados e inmunorreactivos para el fungicida fludioxonil |
| CN103588686B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 一种用卤素卤化制备2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| CN103553991B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 一种制备2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| CN103553990B (zh) * | 2013-11-08 | 2016-01-20 | 苏州诚和医药化学有限公司 | 用卤素卤化合成2－甲氧基－4－氨基－5－乙砜基苯甲酸甲酯的方法 |
| AR099767A1 (es) | 2014-03-17 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados del ácido acético azaindol y su uso como moduladores del receptor de prostaglandina d2 |
| KR20160133536A (ko) | 2014-03-18 | 2016-11-22 | 액테리온 파마슈티칼 리미티드 | 아자인돌 아세트산 유도체 및 프로스타글란딘 d2 수용체 조절제로서의 이의 용도 |
| AU2016323262B2 (en) | 2015-09-15 | 2020-11-19 | Idorsia Pharmaceuticals Ltd | Crystalline forms |
| CN108164502B (zh) * | 2018-03-06 | 2021-04-13 | 苏州华一新能源科技有限公司 | 1,3-丙烷磺酸内酯的制备方法 |
| CN112602714B (zh) * | 2020-12-23 | 2021-11-16 | 华南农业大学 | 一类咯菌腈羧酸衍生物在用于植物维管组织靶向药剂中的应用 |
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| EP1466902A4 (en) * | 2001-12-28 | 2005-11-09 | Takeda Pharmaceutical | ANTAGONISTS OF THE ANDROGEN RECEPTOR |
| JP4316232B2 (ja) * | 2001-12-28 | 2009-08-19 | 武田薬品工業株式会社 | アンドロゲン受容体拮抗剤 |
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| US20080119456A1 (en) * | 2004-05-29 | 2008-05-22 | Trond Ulven | Substituted Thiazoleacetic Acid as Crth2 Ligands |
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- 2005-12-12 ES ES05815747T patent/ES2335519T3/es not_active Expired - Lifetime
- 2005-12-12 AR ARP050105197A patent/AR052266A1/es not_active Application Discontinuation
- 2005-12-12 CA CA002587934A patent/CA2587934A1/en not_active Abandoned
- 2005-12-12 MX MX2007007098A patent/MX2007007098A/es active IP Right Grant
- 2005-12-12 PL PL05815747T patent/PL1828172T3/pl unknown
- 2005-12-13 TW TW094143970A patent/TW200635921A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101072773B (zh) | 2011-01-19 |
| JP2008523130A (ja) | 2008-07-03 |
| DE602005017935D1 (de) | 2010-01-07 |
| AU2005315881C1 (en) | 2010-03-11 |
| EP1828172B1 (en) | 2009-11-25 |
| PE20060736A1 (es) | 2006-09-08 |
| ATE449772T1 (de) | 2009-12-15 |
| MX2007007098A (es) | 2007-06-22 |
| AU2005315881A1 (en) | 2006-06-22 |
| US20100087432A1 (en) | 2010-04-08 |
| ES2335519T3 (es) | 2010-03-29 |
| PT1828172E (pt) | 2010-02-17 |
| GB0427381D0 (en) | 2005-01-19 |
| AR052266A1 (es) | 2007-03-07 |
| TW200635921A (en) | 2006-10-16 |
| GT200500360A (es) | 2006-08-07 |
| AU2005315881B2 (en) | 2009-09-24 |
| WO2006063763A1 (en) | 2006-06-22 |
| PL1828172T3 (pl) | 2010-05-31 |
| CN101072773A (zh) | 2007-11-14 |
| BRPI0518607A2 (pt) | 2008-11-25 |
| EP1828172A1 (en) | 2007-09-05 |
| CA2587934A1 (en) | 2006-06-22 |
| KR20070087605A (ko) | 2007-08-28 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110825 |