MX2014007239A - Combinacion de un antagonista crth2 y un inhibidor de bomba de proton para el tratamiento de esofagitis eosinofilica. - Google Patents

Info

Publication number

MX2014007239A

MX2014007239A MX2014007239A MX2014007239A MX2014007239A MX 2014007239 A MX2014007239 A MX 2014007239A MX 2014007239 A MX2014007239 A MX 2014007239A MX 2014007239 A MX2014007239 A MX 2014007239A MX 2014007239 A MX2014007239 A MX 2014007239A

Authority

MX

Mexico

Prior art keywords

methyl

fluoro

acetic acid

indol

acid

Prior art date

2011-12-16

Links

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• Global Dossier
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• 229940124003 CRTH2 antagonist Drugs 0.000 title claims abstract description 84
• 206010064212 Eosinophilic oesophagitis Diseases 0.000 title claims abstract description 52
• 201000000708 eosinophilic esophagitis Diseases 0.000 title claims abstract description 52
• 229940126409 proton pump inhibitor Drugs 0.000 title claims abstract description 24
• 239000000612 proton pump inhibitor Substances 0.000 title claims abstract description 24
• 238000011282 treatment Methods 0.000 title claims description 16
• 150000003839 salts Chemical class 0.000 claims abstract description 178
• 238000000034 method Methods 0.000 claims abstract description 24
• -1 Ci-C6 alkyl / aryl Chemical group 0.000 claims description 345
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 299
• 239000002253 acid Substances 0.000 claims description 191
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 178
• 125000000217 alkyl group Chemical group 0.000 claims description 86
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 239000008194 pharmaceutical composition Substances 0.000 claims description 57
• 125000005843 halogen group Chemical group 0.000 claims description 54
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
• 125000001072 heteroaryl group Chemical group 0.000 claims description 49
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 41
• 229960004770 esomeprazole Drugs 0.000 claims description 40
• SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 claims description 40
• IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 claims description 38
• MJIHNNLFOKEZEW-RUZDIDTESA-N dexlansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1C[S@@](=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-RUZDIDTESA-N 0.000 claims description 38
• 150000001875 compounds Chemical class 0.000 claims description 37
• 229960003568 dexlansoprazole Drugs 0.000 claims description 37
• MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 37
• 229960003174 lansoprazole Drugs 0.000 claims description 37
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 37
• 229960005019 pantoprazole Drugs 0.000 claims description 37
• 229960004157 rabeprazole Drugs 0.000 claims description 37
• YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 37
• SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 36
• 229960000381 omeprazole Drugs 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 239000003246 corticosteroid Substances 0.000 claims description 32
• 239000005557 antagonist Substances 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 27
• 108050000258 Prostaglandin D receptors Proteins 0.000 claims description 25
• FATGTHLOZSXOBC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 FATGTHLOZSXOBC-UHFFFAOYSA-N 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• VURBJTJUNFTLRH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical group C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C=C1 VURBJTJUNFTLRH-UHFFFAOYSA-N 0.000 claims description 13
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
• GIKLOMGMVNCZNU-UHFFFAOYSA-N 2-[5-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NC(=O)C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 GIKLOMGMVNCZNU-UHFFFAOYSA-N 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
• VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 8
• 229960004436 budesonide Drugs 0.000 claims description 8
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 6
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 229930192474 thiophene Natural products 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 238000009115 maintenance therapy Methods 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• AUHRDYPGCRKIKZ-UHFFFAOYSA-N 2-[2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 AUHRDYPGCRKIKZ-UHFFFAOYSA-N 0.000 claims description 3
• WIOOBYGJMHMUPJ-UHFFFAOYSA-N 2-[3-[(2-cyclohexylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)C1CCCCC1 WIOOBYGJMHMUPJ-UHFFFAOYSA-N 0.000 claims description 3
• CMUBATJXNUXZRE-UHFFFAOYSA-N 2-[3-[(4-chlorophenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(Cl)C=C1 CMUBATJXNUXZRE-UHFFFAOYSA-N 0.000 claims description 3
• ZCUYLCQVFFSXST-UHFFFAOYSA-N 2-[3-[(4-tert-butylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C(C)(C)C)C=C1 ZCUYLCQVFFSXST-UHFFFAOYSA-N 0.000 claims description 3
• MFBFOHDTIVFHIJ-UHFFFAOYSA-N 2-[3-[[2-(2-cyanophenoxy)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=CC=C1C#N MFBFOHDTIVFHIJ-UHFFFAOYSA-N 0.000 claims description 3
• BQDOCSADMAOQIR-UHFFFAOYSA-N 2-[3-[[2-(3,4-difluorophenoxy)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(F)C(F)=C1 BQDOCSADMAOQIR-UHFFFAOYSA-N 0.000 claims description 3
• JLWHNIVAJGRXQH-UHFFFAOYSA-N 2-[3-[[2-(4-cyanophenoxy)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(C#N)C=C1 JLWHNIVAJGRXQH-UHFFFAOYSA-N 0.000 claims description 3
• RCDLAJQERQUBRP-UHFFFAOYSA-N 2-[3-[[4-[(4-chlorophenyl)methylsulfonyl]phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=C(Cl)C=C1 RCDLAJQERQUBRP-UHFFFAOYSA-N 0.000 claims description 3
• QILUMBJCLHPTEK-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 QILUMBJCLHPTEK-UHFFFAOYSA-N 0.000 claims description 3
• RLVUYXZUNLMUAA-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(1,3-thiazol-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=NC=CS1 RLVUYXZUNLMUAA-UHFFFAOYSA-N 0.000 claims description 3
• BYKXFHSGUBZCES-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(naphthalen-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=C1 BYKXFHSGUBZCES-UHFFFAOYSA-N 0.000 claims description 3
• TWGDPIFDMDRPJW-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-7-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=N2)C2=C1 TWGDPIFDMDRPJW-UHFFFAOYSA-N 0.000 claims description 3
• RAQFMAVUQKXQON-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinoxalin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN=C(C=CC=C2)C2=N1 RAQFMAVUQKXQON-UHFFFAOYSA-N 0.000 claims description 3
• FUQCZYPTBHJSQX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-phenoxyphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=CC=C1 FUQCZYPTBHJSQX-UHFFFAOYSA-N 0.000 claims description 3
• FSYLFZCDQZBNBD-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(trifluoromethyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C(F)(F)F)C=C1 FSYLFZCDQZBNBD-UHFFFAOYSA-N 0.000 claims description 3
• CIBHTCADKNJJQS-UHFFFAOYSA-N 2-[5-fluoro-3-[(8-hydroxyquinolin-2-yl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2O)C2=N1 CIBHTCADKNJJQS-UHFFFAOYSA-N 0.000 claims description 3
• UDKGCWQLDVCYAR-UHFFFAOYSA-N 2-[5-fluoro-3-[[2-(4-fluorophenoxy)phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(F)C=C1 UDKGCWQLDVCYAR-UHFFFAOYSA-N 0.000 claims description 3
• CCZUSMXZUULADP-UHFFFAOYSA-N 2-[5-fluoro-3-[[2-(4-methoxyphenoxy)phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 CCZUSMXZUULADP-UHFFFAOYSA-N 0.000 claims description 3
• WYZCOQATIZDSDW-UHFFFAOYSA-N 2-[5-fluoro-3-[[3-[(4-fluorophenyl)methylsulfonyl]phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1S(=O)(=O)CC1=CC=C(F)C=C1 WYZCOQATIZDSDW-UHFFFAOYSA-N 0.000 claims description 3
• NVXAOBKIOMYHKS-UHFFFAOYSA-N 2-[5-fluoro-3-[[4-[(4-fluorophenyl)methylsulfonyl]phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=C(F)C=C1 NVXAOBKIOMYHKS-UHFFFAOYSA-N 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 3
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 3
• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 229960003957 dexamethasone Drugs 0.000 claims description 3
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
• 229960002714 fluticasone Drugs 0.000 claims description 3
• MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 3
• 229960000890 hydrocortisone Drugs 0.000 claims description 3
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 3
• VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims description 3
• 229960004584 methylprednisolone Drugs 0.000 claims description 3
• 229960005127 montelukast Drugs 0.000 claims description 3
• 229960005205 prednisolone Drugs 0.000 claims description 3
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• OJAHKYMVSLLQPG-UHFFFAOYSA-N 2-[3-[(3-benzylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1S(=O)(=O)CC1=CC=CC=C1 OJAHKYMVSLLQPG-UHFFFAOYSA-N 0.000 claims description 2
• BRNIUXLBABJPPA-UHFFFAOYSA-N 2-[3-[(4-benzylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=CC=C1 BRNIUXLBABJPPA-UHFFFAOYSA-N 0.000 claims description 2
• MBFPGMJHQDRALK-UHFFFAOYSA-N 2-[3-[(4-butylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 MBFPGMJHQDRALK-UHFFFAOYSA-N 0.000 claims description 2
• XBJNKUJGGZDKGY-UHFFFAOYSA-N 2-[3-[[2-(benzenesulfonyl)-1,3-thiazol-5-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(S1)=CN=C1S(=O)(=O)C1=CC=CC=C1 XBJNKUJGGZDKGY-UHFFFAOYSA-N 0.000 claims description 2
• JWGPBCUWRFVNDU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(1-naphthalen-2-ylethyl)indol-1-yl]acetic acid Chemical compound C1=CC=CC2=CC(C(C=3C4=CC(F)=CC=C4N(CC(O)=O)C=3C)C)=CC=C21 JWGPBCUWRFVNDU-UHFFFAOYSA-N 0.000 claims description 2
• QOQCKLKHHCOPDB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-3-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN=C(C=CC=C2)C2=C1 QOQCKLKHHCOPDB-UHFFFAOYSA-N 0.000 claims description 2
• QKEZLLDSBYOMPM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinoxalin-6-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(N=CC=N2)C2=C1 QKEZLLDSBYOMPM-UHFFFAOYSA-N 0.000 claims description 2
• NRPMXZUNAFYCRH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-piperidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)N1CCCCC1 NRPMXZUNAFYCRH-UHFFFAOYSA-N 0.000 claims description 2
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