KR20140113667A - 호산구성 식도염의 치료를 위한 crth2 길항제 및 양성자 펌프 저해제의 조합 - Google Patents
호산구성 식도염의 치료를 위한 crth2 길항제 및 양성자 펌프 저해제의 조합 Download PDFInfo
- Publication number
- KR20140113667A KR20140113667A KR1020147018762A KR20147018762A KR20140113667A KR 20140113667 A KR20140113667 A KR 20140113667A KR 1020147018762 A KR1020147018762 A KR 1020147018762A KR 20147018762 A KR20147018762 A KR 20147018762A KR 20140113667 A KR20140113667 A KR 20140113667A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- acetic acid
- fluoro
- indol
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229940124003 CRTH2 antagonist Drugs 0.000 title claims abstract description 89
- 229940126409 proton pump inhibitor Drugs 0.000 title claims abstract description 19
- 239000000612 proton pump inhibitor Substances 0.000 title claims abstract description 19
- 206010064212 Eosinophilic oesophagitis Diseases 0.000 title claims description 43
- 201000000708 eosinophilic esophagitis Diseases 0.000 title claims description 43
- 238000011282 treatment Methods 0.000 title claims description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 176
- 239000000203 mixture Substances 0.000 claims abstract description 28
- -1 2- (5-Fluoro-2-methyl-3- (3- (pyridin-l-ylsulfonyl) benzyl) -indol-l-yl) -acetic acid Chemical compound 0.000 claims description 241
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 208
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000008194 pharmaceutical composition Substances 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 49
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229960003174 lansoprazole Drugs 0.000 claims description 36
- 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 34
- 239000003246 corticosteroid Substances 0.000 claims description 33
- 229960005019 pantoprazole Drugs 0.000 claims description 33
- 229960004157 rabeprazole Drugs 0.000 claims description 33
- 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 33
- 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 31
- 229960000381 omeprazole Drugs 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 25
- 229960004770 esomeprazole Drugs 0.000 claims description 22
- 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 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 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 18
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 17
- 239000005557 antagonist Substances 0.000 claims description 17
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- VURBJTJUNFTLRH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound 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 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 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
- 239000012453 solvate Substances 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- GIKLOMGMVNCZNU-UHFFFAOYSA-N 2-[5-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical group 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 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- 239000003814 drug Substances 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- WCTVXETZWJHJQD-UHFFFAOYSA-N 2-[3-[(4-ethylsulfanylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(SCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 WCTVXETZWJHJQD-UHFFFAOYSA-N 0.000 claims description 6
- GHYFLKZMAHTBNE-UHFFFAOYSA-N 2-[3-[[2-(benzenesulfonyl)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=C1S(=O)(=O)C1=CC=CC=C1 GHYFLKZMAHTBNE-UHFFFAOYSA-N 0.000 claims description 6
- CHVRKCOTGVTUSL-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-propylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(SCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 CHVRKCOTGVTUSL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 229940079593 drug Drugs 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
- 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 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 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 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 229960004436 budesonide Drugs 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- SFESJDVHISLSIZ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[1-[4-(trifluoromethyl)phenyl]ethyl]indol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(C(F)(F)F)C=C1 SFESJDVHISLSIZ-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 238000009115 maintenance therapy Methods 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 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
- RJDBTFKKUDPQCO-UHFFFAOYSA-N 2-[3-[(1-benzylpyrazol-4-yl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(=C1)C=NN1CC1=CC=CC=C1 RJDBTFKKUDPQCO-UHFFFAOYSA-N 0.000 claims description 3
- YVLZYLQOFHWRHB-UHFFFAOYSA-N 2-[3-[(2-benzylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1CC1=CC=CC=C1 YVLZYLQOFHWRHB-UHFFFAOYSA-N 0.000 claims description 3
- VHZQRDXTXVSINR-UHFFFAOYSA-N 2-[3-[(2-benzylsulfonylphenyl)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)CC1=CC=CC=C1 VHZQRDXTXVSINR-UHFFFAOYSA-N 0.000 claims description 3
- AVMIPJYSHKQHCN-UHFFFAOYSA-N 2-[3-[(2-butan-2-ylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CCC(C)S(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 AVMIPJYSHKQHCN-UHFFFAOYSA-N 0.000 claims description 3
- KTZAXDGOJAJDPM-UHFFFAOYSA-N 2-[3-[(2-butylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CCCCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 KTZAXDGOJAJDPM-UHFFFAOYSA-N 0.000 claims description 3
- DJBHJFYUQAZFRB-UHFFFAOYSA-N 2-[3-[(2-cyclobutylsulfonylphenyl)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)C1CCC1 DJBHJFYUQAZFRB-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
- DSIZPFACZSRXAM-UHFFFAOYSA-N 2-[3-[(2-cyclopentylsulfonylphenyl)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)C1CCCC1 DSIZPFACZSRXAM-UHFFFAOYSA-N 0.000 claims description 3
- DMLDQWFRMAXMNY-UHFFFAOYSA-N 2-[3-[(2-ethylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 DMLDQWFRMAXMNY-UHFFFAOYSA-N 0.000 claims description 3
- NFXQLCUFDMEXQW-UHFFFAOYSA-N 2-[3-[(2-tert-butylsulfonylphenyl)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)C(C)(C)C NFXQLCUFDMEXQW-UHFFFAOYSA-N 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 3
- 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 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
- GRCSJFWAKMMIDQ-UHFFFAOYSA-N 2-[3-[(4-cyclohexylsulfonylphenyl)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)C1CCCCC1 GRCSJFWAKMMIDQ-UHFFFAOYSA-N 0.000 claims description 3
- JZSPIXAOOJTSGW-UHFFFAOYSA-N 2-[3-[(4-cyclopentylsulfonylphenyl)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)C1CCCC1 JZSPIXAOOJTSGW-UHFFFAOYSA-N 0.000 claims description 3
- CJRMMJVISVGLBQ-UHFFFAOYSA-N 2-[3-[(4-ethylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 CJRMMJVISVGLBQ-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
- SKBKQJHNXXMPON-UHFFFAOYSA-N 2-[3-[(4-tert-butylsulfanylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(SC(C)(C)C)C=C1 SKBKQJHNXXMPON-UHFFFAOYSA-N 0.000 claims description 3
- GFKLIKDQNJMYMM-UHFFFAOYSA-N 2-[3-[(4-tert-butylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(=O)(=O)C(C)(C)C)C=C1 GFKLIKDQNJMYMM-UHFFFAOYSA-N 0.000 claims description 3
- XYLOSFUTUBOLNB-UHFFFAOYSA-N 2-[3-[1-(4-tert-butylphenyl)ethyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(C(C)(C)C)C=C1 XYLOSFUTUBOLNB-UHFFFAOYSA-N 0.000 claims description 3
- HGJOOXHUFSXPAI-UHFFFAOYSA-N 2-[3-[[1-(2,4-dichlorophenyl)sulfonylpyrrol-2-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN1S(=O)(=O)C1=CC=C(Cl)C=C1Cl HGJOOXHUFSXPAI-UHFFFAOYSA-N 0.000 claims description 3
- JNXAGAQABMLZMP-UHFFFAOYSA-N 2-[3-[[1-(benzenesulfonyl)indol-2-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JNXAGAQABMLZMP-UHFFFAOYSA-N 0.000 claims description 3
- VWGGTNDVKYOBCN-UHFFFAOYSA-N 2-[3-[[2-(2,4-dichlorophenoxy)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(Cl)C=C1Cl VWGGTNDVKYOBCN-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
- SJMSBIALXVPNAQ-UHFFFAOYSA-N 2-[3-[[2-(4-chlorophenoxy)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(Cl)C=C1 SJMSBIALXVPNAQ-UHFFFAOYSA-N 0.000 claims description 3
- YCQINVWJJWUOHH-UHFFFAOYSA-N 2-[3-[[2-(4-chlorophenyl)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=C1C1=CC=C(Cl)C=C1 YCQINVWJJWUOHH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- RENDLZVWZMAZHA-UHFFFAOYSA-N 2-[3-[[2-(butylsulfamoyl)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RENDLZVWZMAZHA-UHFFFAOYSA-N 0.000 claims description 3
- GGFNCDSUSUQDDS-UHFFFAOYSA-N 2-[3-[[3-(butylsulfamoyl)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CCCCNS(=O)(=O)C1=CC=CC(CC=2C3=CC(F)=CC=C3N(CC(O)=O)C=2C)=C1 GGFNCDSUSUQDDS-UHFFFAOYSA-N 0.000 claims description 3
- VGKDMJLXTGOBSW-UHFFFAOYSA-N 2-[3-[[4-(butylsulfamoyl)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)NCCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 VGKDMJLXTGOBSW-UHFFFAOYSA-N 0.000 claims description 3
- XEMQERDSGQCFTB-UHFFFAOYSA-N 2-[3-[[4-(cyclopropylmethylsulfanyl)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=C1SCC1CC1 XEMQERDSGQCFTB-UHFFFAOYSA-N 0.000 claims description 3
- PPQGJXPEAGLKQH-UHFFFAOYSA-N 2-[3-[[4-(cyclopropylmethylsulfonyl)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)CC1CC1 PPQGJXPEAGLKQH-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
- 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 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
- 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 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
- 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 3
- FASXQCVTKJSFMK-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(1-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=C1S(C)(=O)=O FASXQCVTKJSFMK-UHFFFAOYSA-N 0.000 claims description 3
- JTSKPPIIPCUNDB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-pentylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CCCCCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 JTSKPPIIPCUNDB-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
- BFDRBVCOIAHTAN-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-phenylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1C1=CC=CC=C1 BFDRBVCOIAHTAN-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- FIGQRWRMQCBMIM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-propan-2-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CC(C)S(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 FIGQRWRMQCBMIM-UHFFFAOYSA-N 0.000 claims description 3
- RVDPKGJUYVNWKL-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-propylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CCCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RVDPKGJUYVNWKL-UHFFFAOYSA-N 0.000 claims description 3
- PAKMLKICQKNIQV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-pyrrolidin-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)N1CCCC1 PAKMLKICQKNIQV-UHFFFAOYSA-N 0.000 claims description 3
- RQECSAJXDRUDCC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-methylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CSC1=CC=CC(CC=2C3=CC(F)=CC=C3N(CC(O)=O)C=2C)=C1 RQECSAJXDRUDCC-UHFFFAOYSA-N 0.000 claims description 3
- RYCRNWCEBLPJQH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC2=CC=CC=C2C=C1S(C)(=O)=O RYCRNWCEBLPJQH-UHFFFAOYSA-N 0.000 claims description 3
- JRUNFSWRTCZPQT-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-phenoxyphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 JRUNFSWRTCZPQT-UHFFFAOYSA-N 0.000 claims description 3
- VLTVKWWEZRRUFD-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-phenoxythiophen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC=1SC=CC=1OC1=CC=CC=C1 VLTVKWWEZRRUFD-UHFFFAOYSA-N 0.000 claims description 3
- XUYPKIUZNJXPOQ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-pyrrolidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1S(=O)(=O)N1CCCC1 XUYPKIUZNJXPOQ-UHFFFAOYSA-N 0.000 claims description 3
- NRTLJAWOQSWCBN-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-methylsulfonylquinolin-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC(S(C)(=O)=O)=C(C=CC=C2)C2=N1 NRTLJAWOQSWCBN-UHFFFAOYSA-N 0.000 claims description 3
- APDITWSWQRJDEE-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentan-3-ylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(SC(CC)CC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 APDITWSWQRJDEE-UHFFFAOYSA-N 0.000 claims description 3
- FMYBOBSOMRVPFO-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentan-3-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C(CC)CC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 FMYBOBSOMRVPFO-UHFFFAOYSA-N 0.000 claims description 3
- WZTBSIYFAISTJO-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CCCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 WZTBSIYFAISTJO-UHFFFAOYSA-N 0.000 claims description 3
- HJLPNIQIMSEBHY-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-phenylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1C1=CC=CC=C1 HJLPNIQIMSEBHY-UHFFFAOYSA-N 0.000 claims description 3
- ZENZJBGBJVAPCX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-piperidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 ZENZJBGBJVAPCX-UHFFFAOYSA-N 0.000 claims description 3
- BIJAGBRNXUAAFU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-propan-2-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 BIJAGBRNXUAAFU-UHFFFAOYSA-N 0.000 claims description 3
- JZKXRUBGLBERCX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-propylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 JZKXRUBGLBERCX-UHFFFAOYSA-N 0.000 claims description 3
- FPSINLWYMKVWQA-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(5-methylsulfonylthiophen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)S1 FPSINLWYMKVWQA-UHFFFAOYSA-N 0.000 claims description 3
- BSTMWSBBRAJYHU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(6-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(C=C2)S(C)(=O)=O)C2=C1 BSTMWSBBRAJYHU-UHFFFAOYSA-N 0.000 claims description 3
- DUSVRFQPDLUVJU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(6-methylsulfonylquinolin-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(C=C2)S(C)(=O)=O)C2=N1 DUSVRFQPDLUVJU-UHFFFAOYSA-N 0.000 claims description 3
- JSXSFKOJCMWLDV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[1-(4-methylsulfonylphenyl)ethyl]indol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(S(C)(=O)=O)C=C1 JSXSFKOJCMWLDV-UHFFFAOYSA-N 0.000 claims description 3
- APNCETQETTYWJQ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(4-methylphenoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(C)C=C1 APNCETQETTYWJQ-UHFFFAOYSA-N 0.000 claims description 3
- SSVHGPAUAVUSSR-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(4-methylphenyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1C1=CC=C(C)C=C1 SSVHGPAUAVUSSR-UHFFFAOYSA-N 0.000 claims description 3
- IBZMKRPBSLWMMP-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound CCCNS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 IBZMKRPBSLWMMP-UHFFFAOYSA-N 0.000 claims description 3
- ZPBFXCOEUXPALM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[3-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound CCCNS(=O)(=O)C1=CC=CC(CC=2C3=CC(F)=CC=C3N(CC(O)=O)C=2C)=C1 ZPBFXCOEUXPALM-UHFFFAOYSA-N 0.000 claims description 3
- QRVBQQHQTFGLNY-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 QRVBQQHQTFGLNY-UHFFFAOYSA-N 0.000 claims description 3
- SSASRHIVLKIODJ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(trifluoromethoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(OC(F)(F)F)C=C1 SSASRHIVLKIODJ-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
- MHDHXDHJMCCXBG-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-methylsulfonyl-3-(trifluoromethoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C(OC(F)(F)F)=C1 MHDHXDHJMCCXBG-UHFFFAOYSA-N 0.000 claims description 3
- ILFQESBYFFSFOP-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-methylsulfonyl-3-(trifluoromethyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 ILFQESBYFFSFOP-UHFFFAOYSA-N 0.000 claims description 3
- QYJBPNZUHBMCDT-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[6-[[3-(trifluoromethyl)phenyl]methyl]pyridin-3-yl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=N1)=CC=C1CC1=CC=CC(C(F)(F)F)=C1 QYJBPNZUHBMCDT-UHFFFAOYSA-N 0.000 claims description 3
- CJKAKAXEOWFTDV-UHFFFAOYSA-N 2-[5-fluoro-3-(imidazo[1,2-a]pyridin-2-ylmethyl)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN(C=CC=C2)C2=N1 CJKAKAXEOWFTDV-UHFFFAOYSA-N 0.000 claims description 3
- RZEGYTODLNWOFL-UHFFFAOYSA-N 2-[5-fluoro-3-[(4-methoxyphenyl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RZEGYTODLNWOFL-UHFFFAOYSA-N 0.000 claims description 3
- FOJBXYNSYGEMCI-UHFFFAOYSA-N 2-[5-fluoro-3-[(6-fluoroquinolin-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=C(F)C=C2)C2=N1 FOJBXYNSYGEMCI-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
- UEGRDEKJWGHDCV-UHFFFAOYSA-N 2-[5-fluoro-3-[[4-(4-fluorobenzoyl)-1-methylpyrrol-2-yl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(N(C=1)C)=CC=1C(=O)C1=CC=C(F)C=C1 UEGRDEKJWGHDCV-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
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 150000002148 esters Chemical class 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
- 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
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 23
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229960003387 progesterone Drugs 0.000 claims 2
- 239000000186 progesterone Substances 0.000 claims 2
- HKWZIRZRRMVZLR-UHFFFAOYSA-N 2-[3-[[2-(benzenesulfonyl)pyridin-3-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical group C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN=C1S(=O)(=O)C1=CC=CC=C1 HKWZIRZRRMVZLR-UHFFFAOYSA-N 0.000 claims 1
- 102100021904 Potassium-transporting ATPase alpha chain 1 Human genes 0.000 claims 1
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims 1
- 108010083204 Proton Pumps Proteins 0.000 claims 1
- 229920000333 poly(propyleneimine) Polymers 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000035755 proliferation Effects 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 93
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 44
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 37
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 30
- 125000000524 functional group Chemical group 0.000 description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 210000003979 eosinophil Anatomy 0.000 description 13
- SIXIIKVOZAGHPV-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=C[CH]C2=N1 SIXIIKVOZAGHPV-UHFFFAOYSA-N 0.000 description 13
- 210000003238 esophagus Anatomy 0.000 description 12
- 206010014950 Eosinophilia Diseases 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 229940068196 placebo Drugs 0.000 description 10
- 239000000902 placebo Substances 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 210000004241 Th2 cell Anatomy 0.000 description 8
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 8
- 210000003630 histaminocyte Anatomy 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
- 206010030216 Oesophagitis Diseases 0.000 description 6
- 208000006881 esophagitis Diseases 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- KWUOZCQDBYFKRM-UHFFFAOYSA-N 2-methylsulfinyl-1h-benzimidazole Chemical compound C1=CC=C2NC(S(=O)C)=NC2=C1 KWUOZCQDBYFKRM-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- VFINORKTHQRPLO-UHFFFAOYSA-N [4-(2-ethylbenzimidazol-1-yl)piperidin-1-yl]-(5-methoxy-1h-indol-2-yl)methanone Chemical compound COC1=CC=C2NC(C(=O)N3CCC(CC3)N3C4=CC=CC=C4N=C3CC)=CC2=C1 VFINORKTHQRPLO-UHFFFAOYSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 239000013566 allergen Substances 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000002327 eosinophilic effect Effects 0.000 description 4
- 235000013305 food Nutrition 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
- 230000001404 mediated effect Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 4
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 229960004793 sucrose Drugs 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- OCKJFOHZLXIAAT-UHFFFAOYSA-N 2-methylsulfanyl-1h-benzimidazole Chemical compound C1=CC=C2NC(SC)=NC2=C1 OCKJFOHZLXIAAT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 240000007472 Leucaena leucocephala Species 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 3
- 229940014259 gelatin Drugs 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 230000008673 vomiting Effects 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VCEJYVQRYMOKCH-UHFFFAOYSA-N 2-(2-benzoyl-8-bromo-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1C=2C3=CC(Br)=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CC=C1 VCEJYVQRYMOKCH-UHFFFAOYSA-N 0.000 description 2
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PNYMKZXVOIBSMP-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 PNYMKZXVOIBSMP-UHFFFAOYSA-N 0.000 description 2
- LLXYOGQIDMFBMS-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-5-cyano-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(C#N)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 LLXYOGQIDMFBMS-UHFFFAOYSA-N 0.000 description 2
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 206010008479 Chest Pain Diseases 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 208000019505 Deglutition disease Diseases 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 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
- 241000124008 Mammalia Species 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 238000001574 biopsy Methods 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- WQJFIWXYPKYBTO-UHFFFAOYSA-N indole-1-acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1 WQJFIWXYPKYBTO-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229960001375 lactose Drugs 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 229960001855 mannitol Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 229950010765 pivalate Drugs 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Chemical class 0.000 description 2
- 229940083542 sodium Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 229960005294 triamcinolone Drugs 0.000 description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical class CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- UAOUEEZZRWXXFV-ZDUSSCGKSA-N (2s)-2-[3-[[2-chloro-4-(cyclobutylcarbamoyl)phenyl]methyl]-4-(difluoromethoxy)-2-ethyl-8-fluoroquinolin-5-yl]oxypropanoic acid Chemical compound CCC1=NC2=C(F)C=CC(O[C@@H](C)C(O)=O)=C2C(OC(F)F)=C1CC(C(=C1)Cl)=CC=C1C(=O)NC1CCC1 UAOUEEZZRWXXFV-ZDUSSCGKSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical group OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 description 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 description 1
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 description 1
- OPBQKJZMUAITIZ-UHFFFAOYSA-N 1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound C1=C2OC=COC2=CC2=C1N=CN2 OPBQKJZMUAITIZ-UHFFFAOYSA-N 0.000 description 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 1
- LNDWMQWLWGXEET-UHFFFAOYSA-N 2-(1h-indol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2NC=CC2=C1 LNDWMQWLWGXEET-UHFFFAOYSA-N 0.000 description 1
- LMGMINBSBGUQCT-UHFFFAOYSA-N 2-(2,5-dimethyl-3-quinolin-4-ylindol-1-yl)acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC=CC=C12 LMGMINBSBGUQCT-UHFFFAOYSA-N 0.000 description 1
- SJSNYYXMOAPKKO-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1C=2C3=CC=CC(Cl)=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CC=C1 SJSNYYXMOAPKKO-UHFFFAOYSA-N 0.000 description 1
- LWSSNAISVQXGSU-UHFFFAOYSA-N 2-(2-benzoyl-6-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1CC=2N(CC(O)=O)C=3C(C)=CC=CC=3C=2CN1C(=O)C1=CC=CC=C1 LWSSNAISVQXGSU-UHFFFAOYSA-N 0.000 description 1
- RHOGGIYINLWQJJ-UHFFFAOYSA-N 2-(2-benzoyl-7,8-dichloro-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1C=2C3=CC(Cl)=C(Cl)C=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CC=C1 RHOGGIYINLWQJJ-UHFFFAOYSA-N 0.000 description 1
- XUFIAROJUKEWSZ-UHFFFAOYSA-N 2-(2-benzoyl-7,8-dimethyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1CC=2N(CC(O)=O)C=3C=C(C)C(C)=CC=3C=2CN1C(=O)C1=CC=CC=C1 XUFIAROJUKEWSZ-UHFFFAOYSA-N 0.000 description 1
- BLONTEOHZMQKDF-UHFFFAOYSA-N 2-(2-benzoyl-7-chloro-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1CC=2N(CC(O)=O)C=3C=C(Cl)C(C)=CC=3C=2CN1C(=O)C1=CC=CC=C1 BLONTEOHZMQKDF-UHFFFAOYSA-N 0.000 description 1
- GMSNGAAHZCRDTP-UHFFFAOYSA-N 2-(2-benzoyl-8-chloro-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1C=2C3=CC(Cl)=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CC=C1 GMSNGAAHZCRDTP-UHFFFAOYSA-N 0.000 description 1
- VXRDEYZQIIXKQG-UHFFFAOYSA-N 2-(2-benzoyl-8-tert-butyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl)acetic acid Chemical compound C1C=2C3=CC(C(C)(C)C)=CC=C3N(CC(O)=O)C=2CCN1C(=O)C1=CC=CC=C1 VXRDEYZQIIXKQG-UHFFFAOYSA-N 0.000 description 1
- HPCATFFLWWRKLI-UHFFFAOYSA-N 2-(2-methyl-1H-pyridin-2-yl)acetic acid Chemical compound CC1(C=CC=CN1)CC(=O)O HPCATFFLWWRKLI-UHFFFAOYSA-N 0.000 description 1
- ORRYGHOZQYKHGF-UHFFFAOYSA-N 2-(2-methyl-3-quinolin-4-ylindol-1-yl)acetic acid Chemical class C12=CC=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC=CC=C12 ORRYGHOZQYKHGF-UHFFFAOYSA-N 0.000 description 1
- MGICLRNAZXDKAT-UHFFFAOYSA-N 2-(2-methylindol-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(C)=CC2=C1 MGICLRNAZXDKAT-UHFFFAOYSA-N 0.000 description 1
- UAFFMZYXTLDFAS-UHFFFAOYSA-N 2-(4-methylpyridin-2-yl)acetic acid Chemical compound CC1=CC=NC(CC(O)=O)=C1 UAFFMZYXTLDFAS-UHFFFAOYSA-N 0.000 description 1
- WWWCAQVRFBRIOU-UHFFFAOYSA-N 2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-6,7-dihydro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC=4OCCOC=4C=C3N=2)=C1OC WWWCAQVRFBRIOU-UHFFFAOYSA-N 0.000 description 1
- XARXMWDEYLBKMF-UHFFFAOYSA-N 2-[(4,5-dimethoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound CC1=C(OC)C(OC)=CN=C1CS(=O)C1=NC2=CC(OC(F)(F)C(F)F)=CC=C2N1 XARXMWDEYLBKMF-UHFFFAOYSA-N 0.000 description 1
- PMPBIIJSWDDUHQ-UHFFFAOYSA-N 2-[(4,5-dimethoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound CC1=C(OC)C(OC)=CN=C1CS(=O)C1=NC2=CC(OC(F)(F)F)=CC=C2N1 PMPBIIJSWDDUHQ-UHFFFAOYSA-N 0.000 description 1
- OBOZCZVETSEGBE-UHFFFAOYSA-N 2-[(4,5-dimethoxypyridin-2-yl)methylsulfinyl]-6,7-dihydro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound C1=C(OC)C(OC)=CN=C1CS(=O)C(NC1=C2)=NC1=CC1=C2OCCO1 OBOZCZVETSEGBE-UHFFFAOYSA-N 0.000 description 1
- GTZJAVFSFKBXLB-UHFFFAOYSA-N 2-[(4,5-dimethoxypyridin-2-yl)methylsulfinyl]-6-(1,1,2,2-tetrafluoroethoxy)-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CN=C1CS(=O)C1=NC2=CC(OC(F)(F)C(F)F)=CC=C2N1 GTZJAVFSFKBXLB-UHFFFAOYSA-N 0.000 description 1
- SYCOQCPQOMIAGW-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(2-methylphenyl)sulfonylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=CC=C1C SYCOQCPQOMIAGW-UHFFFAOYSA-N 0.000 description 1
- AMNJIGMMUQRKOL-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 AMNJIGMMUQRKOL-UHFFFAOYSA-N 0.000 description 1
- LJSREZMFZRABNJ-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(7-methylquinolin-4-yl)indol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(C)=CC=C12 LJSREZMFZRABNJ-UHFFFAOYSA-N 0.000 description 1
- PYCNZTVHCBCNPY-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(8-methylquinolin-4-yl)indol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 PYCNZTVHCBCNPY-UHFFFAOYSA-N 0.000 description 1
- CUBGOGRTKCMGGK-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(8-methylsulfonylquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(S(C)(=O)=O)C=CC=C12 CUBGOGRTKCMGGK-UHFFFAOYSA-N 0.000 description 1
- PVTFROQXBBAJHP-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(8-nitroquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C([N+]([O-])=O)C=CC=C12 PVTFROQXBBAJHP-UHFFFAOYSA-N 0.000 description 1
- UYLVLPRFGZUQIF-UHFFFAOYSA-N 2-[2,5-dimethyl-3-[7-(trifluoromethyl)quinolin-4-yl]indol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(C(F)(F)F)=CC=C12 UYLVLPRFGZUQIF-UHFFFAOYSA-N 0.000 description 1
- HYJFNTQMONCVNH-UHFFFAOYSA-N 2-[2,5-dimethyl-3-[8-(trifluoromethyl)quinolin-4-yl]indol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C(F)(F)F)C=CC=C12 HYJFNTQMONCVNH-UHFFFAOYSA-N 0.000 description 1
- CWLQJOKHXSQQMU-UHFFFAOYSA-N 2-[2-(1-benzothiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2SC(C(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC2=C1 CWLQJOKHXSQQMU-UHFFFAOYSA-N 0.000 description 1
- ACUGKRRVWZPYKX-UHFFFAOYSA-N 2-[2-(2,2-diphenylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 ACUGKRRVWZPYKX-UHFFFAOYSA-N 0.000 description 1
- BDQAKNAGGWFVIM-UHFFFAOYSA-N 2-[2-(2-ethoxynaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OCC BDQAKNAGGWFVIM-UHFFFAOYSA-N 0.000 description 1
- NOIURXGAJIXXQA-UHFFFAOYSA-N 2-[2-(2-ethoxynaphthalene-1-carbonyl)-7-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=C(C)C=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OCC NOIURXGAJIXXQA-UHFFFAOYSA-N 0.000 description 1
- HNBUXZIRGGMBIL-UHFFFAOYSA-N 2-[2-(2-ethoxynaphthalene-1-carbonyl)-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OCC HNBUXZIRGGMBIL-UHFFFAOYSA-N 0.000 description 1
- KAFTYEZWTWMRNA-UHFFFAOYSA-N 2-[2-(2-methoxynaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OC KAFTYEZWTWMRNA-UHFFFAOYSA-N 0.000 description 1
- UJMJXLIAZBYBEL-UHFFFAOYSA-N 2-[2-(2-methoxynaphthalene-1-carbonyl)-7-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=C(C)C=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OC UJMJXLIAZBYBEL-UHFFFAOYSA-N 0.000 description 1
- SICUCZBWMPNMIV-UHFFFAOYSA-N 2-[2-(2-methoxynaphthalene-1-carbonyl)-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OC SICUCZBWMPNMIV-UHFFFAOYSA-N 0.000 description 1
- UEOKOMALGUPODH-UHFFFAOYSA-N 2-[2-(2-methylfuran-3-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound O1C=CC(C(=O)N2CC3=C(N(C4=CC=CC=C43)CC(O)=O)CC2)=C1C UEOKOMALGUPODH-UHFFFAOYSA-N 0.000 description 1
- PKONUCYNAIYNPG-UHFFFAOYSA-N 2-[2-(2-naphthalen-1-ylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(CC(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=CC2=C1 PKONUCYNAIYNPG-UHFFFAOYSA-N 0.000 description 1
- HDKVUGZMDGNZDT-UHFFFAOYSA-N 2-[2-(2-naphthalen-2-ylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=CC2=CC(CC(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=C21 HDKVUGZMDGNZDT-UHFFFAOYSA-N 0.000 description 1
- AMDOZDVOCKPGOL-UHFFFAOYSA-N 2-[2-(3-chlorobenzoyl)-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC(C)=CC=C3N(CC(O)=O)C=2CCN1C(=O)C1=CC=CC(Cl)=C1 AMDOZDVOCKPGOL-UHFFFAOYSA-N 0.000 description 1
- QRFOICDAXVXKJE-UHFFFAOYSA-N 2-[2-(3-methylthiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CSC(C(=O)N2CC3=C(N(C4=CC=CC=C43)CC(O)=O)CC2)=C1C QRFOICDAXVXKJE-UHFFFAOYSA-N 0.000 description 1
- RGRJVXNIKOJOAH-UHFFFAOYSA-N 2-[2-(3-phenylbenzoyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 RGRJVXNIKOJOAH-UHFFFAOYSA-N 0.000 description 1
- DJDJWPWRTDGTPB-UHFFFAOYSA-N 2-[2-(4-fluoronaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(C(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=C(F)C2=C1 DJDJWPWRTDGTPB-UHFFFAOYSA-N 0.000 description 1
- XFXOTWZNQYOJHV-UHFFFAOYSA-N 2-[2-(4-methoxynaphthalene-1-carbonyl)-7-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)N1CC(C=2C(=CC(C)=CC=2)N2CC(O)=O)=C2CC1 XFXOTWZNQYOJHV-UHFFFAOYSA-N 0.000 description 1
- DRJXMZNLVIQROH-UHFFFAOYSA-N 2-[2-(4-methoxynaphthalene-1-carbonyl)-8-methyl-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)N1CC(C=2C(=CC=C(C)C=2)N2CC(O)=O)=C2CC1 DRJXMZNLVIQROH-UHFFFAOYSA-N 0.000 description 1
- IIZDRJZPDVPWCM-UHFFFAOYSA-N 2-[2-(4-methylnaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2C(C)=CC=C1C(=O)N1CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 IIZDRJZPDVPWCM-UHFFFAOYSA-N 0.000 description 1
- ANVJOOBPQZYQFR-UHFFFAOYSA-N 2-[2-(4-phenylbenzoyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ANVJOOBPQZYQFR-UHFFFAOYSA-N 0.000 description 1
- SRNLVTGWPVWYBP-UHFFFAOYSA-N 2-[2-(5-bromofuran-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=C(Br)O1 SRNLVTGWPVWYBP-UHFFFAOYSA-N 0.000 description 1
- SMWFYEMIRMVHMN-UHFFFAOYSA-N 2-[2-(5-bromonaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(C(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=CC2=C1Br SMWFYEMIRMVHMN-UHFFFAOYSA-N 0.000 description 1
- GZLMENYDEXYFOP-UHFFFAOYSA-N 2-[2-(5-chlorothiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=C(Cl)S1 GZLMENYDEXYFOP-UHFFFAOYSA-N 0.000 description 1
- LMGLLBFXYOXOMU-UHFFFAOYSA-N 2-[2-(5-methylthiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound S1C(C)=CC=C1C(=O)N1CC(C=2C(=CC=CC=2)N2CC(O)=O)=C2CC1 LMGLLBFXYOXOMU-UHFFFAOYSA-N 0.000 description 1
- NNOZPIFDRSJMPZ-UHFFFAOYSA-N 2-[2-(9h-fluorene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C(=O)N1CCC(N(C2=CC=CC=C22)CC(=O)O)=C2C1 NNOZPIFDRSJMPZ-UHFFFAOYSA-N 0.000 description 1
- WBLULCSZTZKDTC-UHFFFAOYSA-N 2-[2-(furan-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CO1 WBLULCSZTZKDTC-UHFFFAOYSA-N 0.000 description 1
- NFKMANKAQJAQRR-UHFFFAOYSA-N 2-[2-(furan-3-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C=1C=COC=1 NFKMANKAQJAQRR-UHFFFAOYSA-N 0.000 description 1
- YSAYJRVWHPJTRJ-UHFFFAOYSA-N 2-[2-(naphthalen-2-ylcarbamoyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=CC2=CC(NC(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=C21 YSAYJRVWHPJTRJ-UHFFFAOYSA-N 0.000 description 1
- NVIBILUEGHHNNI-UHFFFAOYSA-N 2-[2-(naphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(C(=O)N3CCC=4N(C5=CC=CC=C5C=4C3)CC(=O)O)=CC=CC2=C1 NVIBILUEGHHNNI-UHFFFAOYSA-N 0.000 description 1
- PTYUYIZWRJVUBO-UHFFFAOYSA-N 2-[2-(pyrazine-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CN=CC=N1 PTYUYIZWRJVUBO-UHFFFAOYSA-N 0.000 description 1
- KMNYEHZREHUSCP-UHFFFAOYSA-N 2-[2-(pyridine-4-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=NC=C1 KMNYEHZREHUSCP-UHFFFAOYSA-N 0.000 description 1
- NOBOIUJXNXWHPY-UHFFFAOYSA-N 2-[2-(thiophene-3-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC=C3N(CC(=O)O)C=2CCN1C(=O)C=1C=CSC=1 NOBOIUJXNXWHPY-UHFFFAOYSA-N 0.000 description 1
- GQRFQYQBVWRBOC-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylsulfonylphenoxy)-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 GQRFQYQBVWRBOC-UHFFFAOYSA-N 0.000 description 1
- VKEBOQVDNYVANJ-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylsulfonylphenyl)sulfanyl-4-thiophen-2-ylindol-1-yl]acetic acid Chemical compound C12=C(C=3SC=CC=3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 VKEBOQVDNYVANJ-UHFFFAOYSA-N 0.000 description 1
- NQTUBTSVBJAJJA-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylsulfonylphenyl)sulfanyl-5-pyridin-3-ylindol-1-yl]acetic acid Chemical compound C12=CC(C=3C=NC=CC=3)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 NQTUBTSVBJAJJA-UHFFFAOYSA-N 0.000 description 1
- NKZIUFSYOVXVQH-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylsulfonylphenyl)sulfanyl-5-pyrimidin-5-ylindol-1-yl]acetic acid Chemical compound C12=CC(C=3C=NC=NC=3)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 NKZIUFSYOVXVQH-UHFFFAOYSA-N 0.000 description 1
- ZKQCOIFXJDQOQG-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylsulfonylphenyl)sulfanyl-5-thiophen-3-ylindol-1-yl]acetic acid Chemical compound C12=CC(C3=CSC=C3)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 ZKQCOIFXJDQOQG-UHFFFAOYSA-N 0.000 description 1
- NHAKRBNTJVWOJY-UHFFFAOYSA-N 2-[2-methyl-3-(8-methylquinolin-4-yl)-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 NHAKRBNTJVWOJY-UHFFFAOYSA-N 0.000 description 1
- KUIAAQPJXKKBOF-UHFFFAOYSA-N 2-[2-methyl-3-(8-methylquinolin-4-yl)-5-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 KUIAAQPJXKKBOF-UHFFFAOYSA-N 0.000 description 1
- XEGKRKDTXIWDIO-UHFFFAOYSA-N 2-[2-methyl-5-methylsulfonyl-3-[8-(trifluoromethyl)quinolin-4-yl]indol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C(F)(F)F)C=CC=C12 XEGKRKDTXIWDIO-UHFFFAOYSA-N 0.000 description 1
- QNJFGASBHPJLDO-UHFFFAOYSA-N 2-[3-(2,6-dichlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=C(Cl)C=CC=C1Cl QNJFGASBHPJLDO-UHFFFAOYSA-N 0.000 description 1
- RDXWQMSCRIJHDJ-UHFFFAOYSA-N 2-[3-(2,8-dimethylquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC(C)=NC2=C(C)C=CC=C12 RDXWQMSCRIJHDJ-UHFFFAOYSA-N 0.000 description 1
- ULXGUWXWBUXGSP-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)sulfanyl-5-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1Cl ULXGUWXWBUXGSP-UHFFFAOYSA-N 0.000 description 1
- FHWUZSJSQKGOMJ-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=CC=C1Cl FHWUZSJSQKGOMJ-UHFFFAOYSA-N 0.000 description 1
- WTXWVKRBJGHPFW-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)-2,4-dimethylindol-1-yl]acetic acid Chemical class C12=C(C)C=CC=C2N(CC(O)=O)C(C)=C1C1=CC(Cl)=NC2=CC=CC=C12 WTXWVKRBJGHPFW-UHFFFAOYSA-N 0.000 description 1
- GTAWSTRELDMZLI-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC(Cl)=NC2=CC=CC=C12 GTAWSTRELDMZLI-UHFFFAOYSA-N 0.000 description 1
- GEDIVZWJJNJULG-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)-2,6-dimethylindol-1-yl]acetic acid Chemical class C12=CC=C(C)C=C2N(CC(O)=O)C(C)=C1C1=CC(Cl)=NC2=CC=CC=C12 GEDIVZWJJNJULG-UHFFFAOYSA-N 0.000 description 1
- GVNRQDCWXZDCRP-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)-2-methylindol-1-yl]acetic acid Chemical class C12=CC=CC=C2N(CC(O)=O)C(C)=C1C1=CC(Cl)=NC2=CC=CC=C12 GVNRQDCWXZDCRP-UHFFFAOYSA-N 0.000 description 1
- WJGYTGOSWKIDGY-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)-5-methoxy-2-methylindol-1-yl]acetic acid Chemical class C1=CC=C2C(C3=C(C)N(CC(O)=O)C4=CC=C(C=C43)OC)=CC(Cl)=NC2=C1 WJGYTGOSWKIDGY-UHFFFAOYSA-N 0.000 description 1
- SBTVBCDPBKMJAL-UHFFFAOYSA-N 2-[3-(2-chloroquinolin-4-yl)indol-1-yl]acetic acid Chemical class C12=CC=CC=C2N(CC(=O)O)C=C1C1=CC(Cl)=NC2=CC=CC=C12 SBTVBCDPBKMJAL-UHFFFAOYSA-N 0.000 description 1
- VTYJZDVMTAZIMU-UHFFFAOYSA-N 2-[3-(2-ethylphenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound CCC1=CC=CC=C1S(=O)(=O)C1=C(C)N(CC(O)=O)C2=CC=C(C)C=C12 VTYJZDVMTAZIMU-UHFFFAOYSA-N 0.000 description 1
- BTHQODNIBDSKDK-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)sulfanyl-4-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC(Cl)=C1 BTHQODNIBDSKDK-UHFFFAOYSA-N 0.000 description 1
- JFCZSBJDIZUXLZ-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=CC(Cl)=C1 JFCZSBJDIZUXLZ-UHFFFAOYSA-N 0.000 description 1
- FENOYGMYRQEBGU-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)sulfonyl-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=CC(Cl)=C1 FENOYGMYRQEBGU-UHFFFAOYSA-N 0.000 description 1
- LTZIPSVUUPYNGF-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound COC1=CC=CC(S(=O)(=O)C=2C3=CC(C)=CC=C3N(CC(O)=O)C=2C)=C1 LTZIPSVUUPYNGF-UHFFFAOYSA-N 0.000 description 1
- NWUQJWTVYYUAAJ-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methyl-4-(propan-2-ylsulfonylamino)indol-1-yl]acetic acid Chemical compound C1=2C(NS(=O)(=O)C(C)C)=CC=CC=2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 NWUQJWTVYYUAAJ-UHFFFAOYSA-N 0.000 description 1
- JFDVCWFRJKHBAG-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methyl-5-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 JFDVCWFRJKHBAG-UHFFFAOYSA-N 0.000 description 1
- XFTAGJLXIIDEIQ-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-4-(dimethylsulfamoylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NS(=O)(=O)N(C)C)=CC=CC=2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 XFTAGJLXIIDEIQ-UHFFFAOYSA-N 0.000 description 1
- CMGUAOOJGFBGME-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-4-(ethylsulfonylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NS(=O)(=O)CC)=CC=CC=2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 CMGUAOOJGFBGME-UHFFFAOYSA-N 0.000 description 1
- YYXNJDGFOGUERM-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-4-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 YYXNJDGFOGUERM-UHFFFAOYSA-N 0.000 description 1
- DUVMLXJCMMEJBQ-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-5-(ethylsulfonylamino)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NS(=O)(=O)CC)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 DUVMLXJCMMEJBQ-UHFFFAOYSA-N 0.000 description 1
- XTXGTLNSIXIKNG-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-5-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 XTXGTLNSIXIKNG-UHFFFAOYSA-N 0.000 description 1
- VHTADBIQRDFSEO-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 VHTADBIQRDFSEO-UHFFFAOYSA-N 0.000 description 1
- FXWMWMLFUMJXSQ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-(3-oxobutylamino)indol-1-yl]acetic acid Chemical compound C1=2C(NCCC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 FXWMWMLFUMJXSQ-UHFFFAOYSA-N 0.000 description 1
- HZHKLHVZKUBUJU-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-[(1-methylimidazol-4-yl)sulfonylamino]indol-1-yl]acetic acid Chemical compound C12=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 HZHKLHVZKUBUJU-UHFFFAOYSA-N 0.000 description 1
- MHBLRRVMUPLWSD-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-pyrazin-2-ylindol-1-yl]acetic acid Chemical compound C12=C(C=3N=CC=NC=3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 MHBLRRVMUPLWSD-UHFFFAOYSA-N 0.000 description 1
- OJARILCKAFKCLI-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-(dimethylsulfamoylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NS(=O)(=O)N(C)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 OJARILCKAFKCLI-UHFFFAOYSA-N 0.000 description 1
- YXMFHGXAVZBCJC-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-(ethylcarbamoylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)NCC)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 YXMFHGXAVZBCJC-UHFFFAOYSA-N 0.000 description 1
- NLMZDXPIFBHDQM-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-[[2-(dimethylamino)acetyl]amino]-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)CN(C)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 NLMZDXPIFBHDQM-UHFFFAOYSA-N 0.000 description 1
- SFZUWPLSLIVZMS-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 SFZUWPLSLIVZMS-UHFFFAOYSA-N 0.000 description 1
- MGHHQQUYPDDOIS-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-2-methyl-4-nitroindol-1-yl]acetic acid Chemical compound C12=C([N+]([O-])=O)C=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 MGHHQQUYPDDOIS-UHFFFAOYSA-N 0.000 description 1
- ZQEDEGGYGPOLKS-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-2-methyl-4-phenylindol-1-yl]acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(C)=C(S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=C1C1=CC=CC=C1 ZQEDEGGYGPOLKS-UHFFFAOYSA-N 0.000 description 1
- KWONLMJTAFZUCM-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-4-(ethylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NCC)=CC=CC=2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 KWONLMJTAFZUCM-UHFFFAOYSA-N 0.000 description 1
- CNMKJYVZCCEGHW-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-4-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 CNMKJYVZCCEGHW-UHFFFAOYSA-N 0.000 description 1
- ZBCFOZZTSVOUNE-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonyl-4-ethylsulfonyl-7-methoxy-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)CC)=CC=C(OC)C=2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 ZBCFOZZTSVOUNE-UHFFFAOYSA-N 0.000 description 1
- XFMGOBWEKPIIEZ-UHFFFAOYSA-N 2-[3-(4-cyanophenoxy)-2-methyl-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C#N)C=C1 XFMGOBWEKPIIEZ-UHFFFAOYSA-N 0.000 description 1
- LPWWVNDAGZXRJB-UHFFFAOYSA-N 2-[3-(4-cyanophenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C#N)C=C1 LPWWVNDAGZXRJB-UHFFFAOYSA-N 0.000 description 1
- PALBXULMPBKEOM-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(C#N)C=C1 PALBXULMPBKEOM-UHFFFAOYSA-N 0.000 description 1
- QWEDSNMFNSHPJW-UHFFFAOYSA-N 2-[3-(4-ethylsulfonylphenoxy)-2-methyl-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(C(F)(F)F)C=C12 QWEDSNMFNSHPJW-UHFFFAOYSA-N 0.000 description 1
- PEWWUPWEOHLXHO-UHFFFAOYSA-N 2-[3-(4-ethylsulfonylphenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 PEWWUPWEOHLXHO-UHFFFAOYSA-N 0.000 description 1
- CEAPSAMHQSAQLY-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)sulfonyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C(C)N(CC(O)=O)C2=CC=C(C)C=C12 CEAPSAMHQSAQLY-UHFFFAOYSA-N 0.000 description 1
- DGUMPIRIOJBFSA-UHFFFAOYSA-N 2-[3-(4-methylsulfonylphenyl)sulfanyl-4-pyrimidin-5-ylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1SC1=CN(CC(O)=O)C2=CC=CC(C=3C=NC=NC=3)=C12 DGUMPIRIOJBFSA-UHFFFAOYSA-N 0.000 description 1
- IOQWSIKRMSNYNH-UHFFFAOYSA-N 2-[3-(6,8-dimethylquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=C(C)C=C12 IOQWSIKRMSNYNH-UHFFFAOYSA-N 0.000 description 1
- FDHCUENRKQAIPG-UHFFFAOYSA-N 2-[3-(6-fluoroquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC=C(F)C=C12 FDHCUENRKQAIPG-UHFFFAOYSA-N 0.000 description 1
- LVUHPSMXFCXPEB-UHFFFAOYSA-N 2-[3-(6-methoxyquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C1=C(C)C=C2C(C3=CC=NC4=CC=C(C=C43)OC)=C(C)N(CC(O)=O)C2=C1 LVUHPSMXFCXPEB-UHFFFAOYSA-N 0.000 description 1
- DHWTVRVYTNGDGQ-UHFFFAOYSA-N 2-[3-(7-chloroquinolin-4-yl)-2,5-dimethyl-6-methylsulfonylindol-1-yl]acetic acid Chemical class C12=CC(C)=C(S(C)(=O)=O)C=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 DHWTVRVYTNGDGQ-UHFFFAOYSA-N 0.000 description 1
- KDRKEDVDJAVBAR-UHFFFAOYSA-N 2-[3-(7-chloroquinolin-4-yl)-2-methyl-5-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 KDRKEDVDJAVBAR-UHFFFAOYSA-N 0.000 description 1
- XBXOVKXPEXRXHT-UHFFFAOYSA-N 2-[3-(7-chloroquinolin-4-yl)-2-methyl-5-nitroindol-1-yl]acetic acid Chemical class C12=CC([N+]([O-])=O)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 XBXOVKXPEXRXHT-UHFFFAOYSA-N 0.000 description 1
- HKAMIGKYIVLHOT-UHFFFAOYSA-N 2-[3-(7-chloroquinolin-4-yl)-5-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 HKAMIGKYIVLHOT-UHFFFAOYSA-N 0.000 description 1
- HLIDFOBANPRHRY-UHFFFAOYSA-N 2-[3-(7-chloroquinolin-4-yl)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 HLIDFOBANPRHRY-UHFFFAOYSA-N 0.000 description 1
- NGISXSDIUBODBB-UHFFFAOYSA-N 2-[3-(8-bromo-2-methylquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC(C)=NC2=C(Br)C=CC=C12 NGISXSDIUBODBB-UHFFFAOYSA-N 0.000 description 1
- IGAKOCYZIOYZOG-UHFFFAOYSA-N 2-[3-(8-chloroquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(Cl)C=CC=C12 IGAKOCYZIOYZOG-UHFFFAOYSA-N 0.000 description 1
- XUGPSRPVEIUUDA-UHFFFAOYSA-N 2-[3-(8-cyanoquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C#N)C=CC=C12 XUGPSRPVEIUUDA-UHFFFAOYSA-N 0.000 description 1
- XONPFUGOIKOYNU-UHFFFAOYSA-N 2-[3-(8-fluoroquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(F)C=CC=C12 XONPFUGOIKOYNU-UHFFFAOYSA-N 0.000 description 1
- KGWGHTDRAPNYKZ-UHFFFAOYSA-N 2-[3-(8-methoxy-2-methylquinolin-4-yl)-2,5-dimethylindol-1-yl]acetic acid Chemical class C1=C(C)C=C2C(C3=C4C=CC=C(C4=NC(C)=C3)OC)=C(C)N(CC(O)=O)C2=C1 KGWGHTDRAPNYKZ-UHFFFAOYSA-N 0.000 description 1
- PQVKEJVYPMEMRT-UHFFFAOYSA-N 2-[3-[(2,4-dichlorophenyl)methyl]-2-(difluoromethoxy)-8-fluoro-4-methylquinolin-5-yl]oxypropanoic acid Chemical compound CC1=C2C(OC(C)C(O)=O)=CC=C(F)C2=NC(OC(F)F)=C1CC1=CC=C(Cl)C=C1Cl PQVKEJVYPMEMRT-UHFFFAOYSA-N 0.000 description 1
- FXMXPIWJXFMMSW-UHFFFAOYSA-N 2-[3-[(4-chloro-2-fluorophenyl)methyl]-2-(difluoromethoxy)-8-fluoro-4-methylquinolin-5-yl]oxyacetic acid Chemical compound FC(F)OC1=NC2=C(F)C=CC(OCC(O)=O)=C2C(C)=C1CC1=CC=C(Cl)C=C1F FXMXPIWJXFMMSW-UHFFFAOYSA-N 0.000 description 1
- DBOLBTFGTCAKQL-UHFFFAOYSA-N 2-[3-[4-(2-aminoethylcarbamoyl)phenoxy]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C(=O)NCCN)C=C1 DBOLBTFGTCAKQL-UHFFFAOYSA-N 0.000 description 1
- DNYBPUDMWWJUCW-UHFFFAOYSA-N 2-[3-[4-(dimethylsulfamoyl)phenoxy]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 DNYBPUDMWWJUCW-UHFFFAOYSA-N 0.000 description 1
- RVPWZGPSADICIM-UHFFFAOYSA-N 2-[3-[4-(ethylcarbamoyl)phenoxy]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NCC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RVPWZGPSADICIM-UHFFFAOYSA-N 0.000 description 1
- DHLXIJFLSPNUQR-UHFFFAOYSA-N 2-[3-[8-(difluoromethoxy)quinolin-4-yl]-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(OC(F)F)C=CC=C12 DHLXIJFLSPNUQR-UHFFFAOYSA-N 0.000 description 1
- HVPWTLUFRMXERC-UHFFFAOYSA-N 2-[4-(furan-3-yl)-2-methyl-3-(4-methylsulfonylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C12=C(C3=COC=C3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 HVPWTLUFRMXERC-UHFFFAOYSA-N 0.000 description 1
- FKBVZNUICXFYJI-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-2-methyl-3-(2-propan-2-ylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound CC(C)C1=CC=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=CC(NS(C)(=O)=O)=C12 FKBVZNUICXFYJI-UHFFFAOYSA-N 0.000 description 1
- BYCQYDRJWXSSQG-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-2-methyl-3-(4-methylsulfonylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 BYCQYDRJWXSSQG-UHFFFAOYSA-N 0.000 description 1
- XKFRGYUIWIJRNS-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-2-methyl-3-[2-(trifluoromethyl)phenyl]sulfanylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1C(F)(F)F XKFRGYUIWIJRNS-UHFFFAOYSA-N 0.000 description 1
- XWGKXIDGHLYRGF-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-2-methyl-3-quinolin-8-ylsulfanylindol-1-yl]acetic acid Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC2=CC=CN=C12 XWGKXIDGHLYRGF-UHFFFAOYSA-N 0.000 description 1
- NTFYOCIPUWDUGJ-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-3-(3-methoxyphenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound COC1=CC=CC(SC=2C3=C(NS(C)(=O)=O)C=CC=C3N(CC(O)=O)C=2C)=C1 NTFYOCIPUWDUGJ-UHFFFAOYSA-N 0.000 description 1
- SRUFDVUBFJETHA-UHFFFAOYSA-N 2-[4-(methanesulfonamido)-3-(4-methoxyphenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=CC(NS(C)(=O)=O)=C12 SRUFDVUBFJETHA-UHFFFAOYSA-N 0.000 description 1
- PLHWKTXZRRUSCX-UHFFFAOYSA-N 2-[4-acetamido-2-methyl-3-(4-methylsulfonylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 PLHWKTXZRRUSCX-UHFFFAOYSA-N 0.000 description 1
- BXSDULPHPLBIRO-UHFFFAOYSA-N 2-[4-acetamido-3-(2-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1Cl BXSDULPHPLBIRO-UHFFFAOYSA-N 0.000 description 1
- HALVQXLHSWSFJM-UHFFFAOYSA-N 2-[4-acetamido-3-(3-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=CC(Cl)=C1 HALVQXLHSWSFJM-UHFFFAOYSA-N 0.000 description 1
- KVULPJIQOUYTAM-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 KVULPJIQOUYTAM-UHFFFAOYSA-N 0.000 description 1
- JWYIGNODXSRKGP-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JWYIGNODXSRKGP-UHFFFAOYSA-N 0.000 description 1
- HVQKOBAIHCZZMN-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenyl)sulfonyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 HVQKOBAIHCZZMN-UHFFFAOYSA-N 0.000 description 1
- IFNCJLZZWYUVEE-UHFFFAOYSA-N 2-[4-acetamido-3-(4-ethylsulfonylphenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=CC(NC(C)=O)=C12 IFNCJLZZWYUVEE-UHFFFAOYSA-N 0.000 description 1
- JBSXHPWTRHKLAH-UHFFFAOYSA-N 2-[4-benzamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=C(NC(=O)C=3C=CC=CC=3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JBSXHPWTRHKLAH-UHFFFAOYSA-N 0.000 description 1
- GXILJFXVNKPFQO-UHFFFAOYSA-N 2-[4-chloro-3-(4-chlorophenyl)sulfonyl-2-methylindol-1-yl]acetic acid Chemical compound C12=C(Cl)C=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GXILJFXVNKPFQO-UHFFFAOYSA-N 0.000 description 1
- KUQKSRKRZGRWJN-UHFFFAOYSA-N 2-[5-(methanesulfonamido)-2-methyl-3-(2-methylsulfonylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1S(C)(=O)=O KUQKSRKRZGRWJN-UHFFFAOYSA-N 0.000 description 1
- MGFCKFUBAHUJPN-UHFFFAOYSA-N 2-[5-acetamido-3-(7-chloroquinolin-4-yl)-2-methylindol-1-yl]acetic acid Chemical compound ClC1=CC=C2C(C3=C(C)N(CC(O)=O)C4=CC=C(C=C43)NC(=O)C)=CC=NC2=C1 MGFCKFUBAHUJPN-UHFFFAOYSA-N 0.000 description 1
- RGYQTNOUXRALCM-UHFFFAOYSA-N 2-[5-amino-3-(7-chloroquinolin-4-yl)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(N)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 RGYQTNOUXRALCM-UHFFFAOYSA-N 0.000 description 1
- IZFCDILCIBKYGC-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(8-methylquinolin-4-yl)indol-1-yl]acetic acid Chemical class C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 IZFCDILCIBKYGC-UHFFFAOYSA-N 0.000 description 1
- YMKOSJMAEBUVLT-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(8-methylsulfonylquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(S(C)(=O)=O)C=CC=C12 YMKOSJMAEBUVLT-UHFFFAOYSA-N 0.000 description 1
- USPBPSZVNVSASZ-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-[4-(methylcarbamoyl)phenoxy]indol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(Cl)C=C12 USPBPSZVNVSASZ-UHFFFAOYSA-N 0.000 description 1
- RYTCSGULAPWMLR-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)sulfonyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 RYTCSGULAPWMLR-UHFFFAOYSA-N 0.000 description 1
- OSHHALJSGLLREH-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)sulfonyl-4-cyano-2-methylindol-1-yl]acetic acid Chemical compound C12=C(C#N)C(Cl)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 OSHHALJSGLLREH-UHFFFAOYSA-N 0.000 description 1
- XUMXJMQEBJLMKC-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)sulfonyl-6-cyano-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(Cl)=C(C#N)C=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 XUMXJMQEBJLMKC-UHFFFAOYSA-N 0.000 description 1
- FUVTXEXQSCGWMI-UHFFFAOYSA-N 2-[5-chloro-3-(4-methoxycarbonylphenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(Cl)C=C12 FUVTXEXQSCGWMI-UHFFFAOYSA-N 0.000 description 1
- LCHNQSHWHSXOIB-UHFFFAOYSA-N 2-[5-chloro-3-(6-methoxy-2-methylquinolin-4-yl)-2-methylindol-1-yl]acetic acid Chemical class C1=C(Cl)C=C2C(C3=CC(C)=NC4=CC=C(C=C43)OC)=C(C)N(CC(O)=O)C2=C1 LCHNQSHWHSXOIB-UHFFFAOYSA-N 0.000 description 1
- OJBCTDMMAARQHI-UHFFFAOYSA-N 2-[5-chloro-3-(7-chloroquinolin-4-yl)-2-methylindol-1-yl]acetic acid Chemical class C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=CC(Cl)=CC=C12 OJBCTDMMAARQHI-UHFFFAOYSA-N 0.000 description 1
- XVOAUDOQFYVQPH-UHFFFAOYSA-N 2-[5-chloro-3-[4-(ethylcarbamoyl)phenoxy]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NCC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(Cl)C=C12 XVOAUDOQFYVQPH-UHFFFAOYSA-N 0.000 description 1
- KOLQHEXKKSYHIH-UHFFFAOYSA-N 2-[5-cyano-2-methyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(C#N)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 KOLQHEXKKSYHIH-UHFFFAOYSA-N 0.000 description 1
- FUUHQFJOTGHDLH-UHFFFAOYSA-N 2-[5-cyano-2-methyl-3-(8-methylquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(C#N)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 FUUHQFJOTGHDLH-UHFFFAOYSA-N 0.000 description 1
- NLBZRKXSZWWBEU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 NLBZRKXSZWWBEU-UHFFFAOYSA-N 0.000 description 1
- VUJRIDRKLRUVEH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(8-methylquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C)C=CC=C12 VUJRIDRKLRUVEH-UHFFFAOYSA-N 0.000 description 1
- PKAAMSYPRABOCI-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(8-methylsulfonylquinolin-4-yl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(S(C)(=O)=O)C=CC=C12 PKAAMSYPRABOCI-UHFFFAOYSA-N 0.000 description 1
- GOVOMGOBTOATIQ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[4-(methylcarbamoyl)phenoxy]indol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 GOVOMGOBTOATIQ-UHFFFAOYSA-N 0.000 description 1
- DFJVMPUTMSLQDA-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[4-(propan-2-ylcarbamoyl)phenoxy]indol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 DFJVMPUTMSLQDA-UHFFFAOYSA-N 0.000 description 1
- QXXYBAMSVHKDPS-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[4-(trifluoromethyl)phenyl]sulfonylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 QXXYBAMSVHKDPS-UHFFFAOYSA-N 0.000 description 1
- VQIFPBRPJAGUFB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[8-(trifluoromethyl)quinolin-4-yl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1C1=CC=NC2=C(C(F)(F)F)C=CC=C12 VQIFPBRPJAGUFB-UHFFFAOYSA-N 0.000 description 1
- YKZVMXZHFUBANW-UHFFFAOYSA-N 2-[5-fluoro-3-(4-methoxycarbonylphenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 YKZVMXZHFUBANW-UHFFFAOYSA-N 0.000 description 1
- SGESAEZHNVTYPA-UHFFFAOYSA-N 2-[6-chloro-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=CC(Cl)=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CS1 SGESAEZHNVTYPA-UHFFFAOYSA-N 0.000 description 1
- FYKNBWHFPWFVCD-UHFFFAOYSA-N 2-[6-chloro-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC(Cl)=C2N(CC(O)=O)C2=C1CN(C(=O)OC(C)(C)C)CC2 FYKNBWHFPWFVCD-UHFFFAOYSA-N 0.000 description 1
- ZZDMFZHPXFLHPJ-UHFFFAOYSA-N 2-[6-chloro-3-(4-chlorophenyl)sulfonyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC=C(Cl)C=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 ZZDMFZHPXFLHPJ-UHFFFAOYSA-N 0.000 description 1
- UGTGWXBXQGYJJU-UHFFFAOYSA-N 2-[7-chloro-2-(2-naphthalen-1-ylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(CC(=O)N3CCC=4N(C5=CC(Cl)=CC=C5C=4C3)CC(=O)O)=CC=CC2=C1 UGTGWXBXQGYJJU-UHFFFAOYSA-N 0.000 description 1
- BVJRUNXSNZWZOC-UHFFFAOYSA-N 2-[7-chloro-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC=C(Cl)C=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CS1 BVJRUNXSNZWZOC-UHFFFAOYSA-N 0.000 description 1
- YPACSVJVZANLPR-UHFFFAOYSA-N 2-[7-chloro-3-(4-chlorophenyl)sulfonyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC=CC(Cl)=C2N(CC(O)=O)C(C)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 YPACSVJVZANLPR-UHFFFAOYSA-N 0.000 description 1
- DKEVCGUDZIOITN-UHFFFAOYSA-N 2-[7-methyl-2-(2-naphthalen-1-ylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(CC(=O)N3CC=4C5=CC=C(C=C5N(CC(O)=O)C=4CC3)C)=CC=CC2=C1 DKEVCGUDZIOITN-UHFFFAOYSA-N 0.000 description 1
- MEJQQJURZAVBIH-UHFFFAOYSA-N 2-[7-methyl-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1CC=2N(CC(O)=O)C3=CC(C)=CC=C3C=2CN1C(=O)C1=CC=CS1 MEJQQJURZAVBIH-UHFFFAOYSA-N 0.000 description 1
- LQMYXLPDQVTPME-UHFFFAOYSA-N 2-[7-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C1=CC=C(C)C=C1N2CC(O)=O LQMYXLPDQVTPME-UHFFFAOYSA-N 0.000 description 1
- YRHNNKHRHATRJO-UHFFFAOYSA-N 2-[8-bromo-2-(2-naphthalen-1-ylacetyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1=CC=C2C(CC(=O)N3CCC=4N(C5=CC=C(Br)C=C5C=4C3)CC(=O)O)=CC=CC2=C1 YRHNNKHRHATRJO-UHFFFAOYSA-N 0.000 description 1
- TVYJJXWJKCTCSI-UHFFFAOYSA-N 2-[8-bromo-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC(Br)=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CS1 TVYJJXWJKCTCSI-UHFFFAOYSA-N 0.000 description 1
- WJQCZBYPXHEWHJ-UHFFFAOYSA-N 2-[8-chloro-2-(2-ethoxynaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OCC WJQCZBYPXHEWHJ-UHFFFAOYSA-N 0.000 description 1
- SMRDGCJEGFVXRO-UHFFFAOYSA-N 2-[8-chloro-2-(2-methoxynaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(CC2)=C1CN2C(=O)C1=C2C=CC=CC2=CC=C1OC SMRDGCJEGFVXRO-UHFFFAOYSA-N 0.000 description 1
- MXQXFVXHUMIGHD-UHFFFAOYSA-N 2-[8-chloro-2-(4-methoxynaphthalene-1-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)N1CC(C=2C(=CC=C(Cl)C=2)N2CC(O)=O)=C2CC1 MXQXFVXHUMIGHD-UHFFFAOYSA-N 0.000 description 1
- OEAGSOOMZDGXRC-UHFFFAOYSA-N 2-[8-chloro-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC(Cl)=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CS1 OEAGSOOMZDGXRC-UHFFFAOYSA-N 0.000 description 1
- UOARRVGRCHCVKI-UHFFFAOYSA-N 2-[8-chloro-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C2=C1CN(C(=O)OC(C)(C)C)CC2 UOARRVGRCHCVKI-UHFFFAOYSA-N 0.000 description 1
- LZLJEKKWOIJMSR-UHFFFAOYSA-N 2-[8-chloro-3-[(4-chlorophenyl)methyl]-4-(difluoromethoxy)-2-ethylquinolin-5-yl]oxyacetic acid Chemical compound CCC1=NC2=C(Cl)C=CC(OCC(O)=O)=C2C(OC(F)F)=C1CC1=CC=C(Cl)C=C1 LZLJEKKWOIJMSR-UHFFFAOYSA-N 0.000 description 1
- VXAZUHZNPMCSLD-UHFFFAOYSA-N 2-[8-fluoro-2-(thiophene-2-carbonyl)-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1C=2C3=CC(F)=CC=C3N(CC(=O)O)C=2CCN1C(=O)C1=CC=CS1 VXAZUHZNPMCSLD-UHFFFAOYSA-N 0.000 description 1
- DQEASAYLAGYTLU-UHFFFAOYSA-N 2-[8-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CC2=C1N(CC(O)=O)C1=CC=C(C)C=C12 DQEASAYLAGYTLU-UHFFFAOYSA-N 0.000 description 1
- SXKVRQAZCKBMOD-UHFFFAOYSA-N 2-[[4-(3-methoxypropyl)-3-methylpyridin-2-yl]methylsulfinyl]-1h-benzimidazole Chemical compound COCCCC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C SXKVRQAZCKBMOD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZVTIAITWLNAGSU-UHFFFAOYSA-N 2-methylsulfanyl-6-(trifluoromethoxy)-1H-benzimidazole Chemical compound C1=C(OC(F)(F)F)C=C2NC(SC)=NC2=C1 ZVTIAITWLNAGSU-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
- WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 description 1
- UEQNORVJOPEYFO-UHFFFAOYSA-N 3-methylsulfanyl-[1,4]dioxino[2,3-f]benzimidazole Chemical compound CSN1C=NC2=C1C=C1C(=C2)OC=CO1 UEQNORVJOPEYFO-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- SDLPHEXAFHVQDC-UHFFFAOYSA-N 4,6-dimethyl-2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N=1C2=CC(C)=CC(C)=C2NC=1S(=O)CC1=CC=CC=N1 SDLPHEXAFHVQDC-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- JZRIZGDEYMWJKQ-UHFFFAOYSA-N 4-[1-(carboxymethyl)-5-chloro-2-methylindol-3-yl]oxybenzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C(O)=O)C=C1 JZRIZGDEYMWJKQ-UHFFFAOYSA-N 0.000 description 1
- YVXQADDGUVCRDQ-UHFFFAOYSA-N 4-[1-(carboxymethyl)-5-fluoro-2-methylindol-3-yl]oxybenzoic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C(O)=O)C=C1 YVXQADDGUVCRDQ-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- VIVBPSGVMCIZQN-UHFFFAOYSA-N 4-methylsulfinyl-2-[3-methyl-4-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl]-1h-benzimidazole Chemical compound CC1=C(OCC(F)(F)C(F)F)C=CN=C1C1=NC2=C(S(C)=O)C=CC=C2N1 VIVBPSGVMCIZQN-UHFFFAOYSA-N 0.000 description 1
- RYXMZRAREWWLDM-UHFFFAOYSA-N 5,6-bis(difluoromethoxy)-2-[(3,4-dimethoxy-5-methylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound COC1=C(C)C=NC(CS(=O)C=2NC3=CC(OC(F)F)=C(OC(F)F)C=C3N=2)=C1OC RYXMZRAREWWLDM-UHFFFAOYSA-N 0.000 description 1
- LUECRHLGGVPFNS-UHFFFAOYSA-N 5-methoxy-4-methylsulfanyl-2-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1H-benzimidazole Chemical compound FC(COC1=CC(=NC=C1)C=1NC2=C(N=1)C=CC(=C2SC)OC)(F)F LUECRHLGGVPFNS-UHFFFAOYSA-N 0.000 description 1
- WERQRLHRZGPICN-UHFFFAOYSA-N 6,7-dihydro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound C1=C2OCCOC2=CC2=C1N=CN2 WERQRLHRZGPICN-UHFFFAOYSA-N 0.000 description 1
- AEATZNMGIBRCMX-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxy-5-methylpyridin-2-yl)methylsulfanyl]-5-methoxy-1h-benzimidazole Chemical compound N=1C=2C=C(OC(F)F)C(OC)=CC=2NC=1SCC1=NC=C(C)C(OC)=C1OC AEATZNMGIBRCMX-UHFFFAOYSA-N 0.000 description 1
- VLNAFGFWMVYDRP-UHFFFAOYSA-N 6-[(3,4-diethoxy-5-methylpyridin-2-yl)methylsulfanyl]-2,2-difluoro-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound CCOC1=C(C)C=NC(CSC=2NC3=CC=4OC(F)(F)OC=4C=C3N=2)=C1OCC VLNAFGFWMVYDRP-UHFFFAOYSA-N 0.000 description 1
- AJCVUUBHYHKRFE-UHFFFAOYSA-N 6-[(3,4-dimethoxy-5-methylpyridin-2-yl)methylsulfinyl]-2,2-difluoro-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound COC1=C(C)C=NC(CS(=O)C=2NC3=CC=4OC(F)(F)OC=4C=C3N=2)=C1OC AJCVUUBHYHKRFE-UHFFFAOYSA-N 0.000 description 1
- GFELOGATYRJGQC-UHFFFAOYSA-N 6-[(4,5-diethoxy-3-methylpyridin-2-yl)methylsulfanyl]-2,2-difluoro-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound CC1=C(OCC)C(OCC)=CN=C1CSC(NC1=C2)=NC1=CC1=C2OC(F)(F)O1 GFELOGATYRJGQC-UHFFFAOYSA-N 0.000 description 1
- JMVGRWJTKURXIT-UHFFFAOYSA-N 6-chloro-2-[(3,4-dimethoxy-5-methylpyridin-2-yl)methylsulfanyl]-6,7,7-trifluoro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound COC1=C(C)C=NC(CSC=2NC3=CC=4OC(F)(F)C(F)(Cl)OC=4C=C3N=2)=C1OC JMVGRWJTKURXIT-UHFFFAOYSA-N 0.000 description 1
- HUBDPOGLSLRDMK-UHFFFAOYSA-N 6-chloro-2-[(4,5-dimethoxypyridin-2-yl)methylsulfinyl]-6,7,7-trifluoro-1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound C1=C(OC)C(OC)=CN=C1CS(=O)C(NC1=C2)=NC1=CC1=C2OC(F)(F)C(F)(Cl)O1 HUBDPOGLSLRDMK-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000282979 Alces alces Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UMNVHGRYGGJADE-UHFFFAOYSA-N FC(COC1=CC(=NC=C1)C=1NC2=C(N=1)C=CC=C2S(=O)C)(F)F Chemical compound FC(COC1=CC(=NC=C1)C=1NC2=C(N=1)C=CC=C2S(=O)C)(F)F UMNVHGRYGGJADE-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 102000011652 Formyl peptide receptors Human genes 0.000 description 1
- 108010076288 Formyl peptide receptors Proteins 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 102100030612 Mast cell carboxypeptidase A Human genes 0.000 description 1
- 101710119290 Mast cell carboxypeptidase A Proteins 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 102000001400 Tryptase Human genes 0.000 description 1
- 108060005989 Tryptase Proteins 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960003099 amcinonide Drugs 0.000 description 1
- ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000001374 aryl-fused-cycloalkyl group Chemical group 0.000 description 1
- 125000000461 aryl-fused-heterocycloalkyl group Chemical group 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- IPPQWPAJJVAOAB-UHFFFAOYSA-N benzenesulfonic acid;4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=C(Cl)C=C1 IPPQWPAJJVAOAB-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone 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-DVTGEIKXSA-N 0.000 description 1
- PLCQGRYPOISRTQ-LWCNAHDDSA-L betamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-LWCNAHDDSA-L 0.000 description 1
- 229960005354 betamethasone sodium phosphate Drugs 0.000 description 1
- 229960004311 betamethasone valerate Drugs 0.000 description 1
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate 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)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- QPAXMPYBNSHKAK-UHFFFAOYSA-N chloro(difluoro)methane Chemical compound F[C](F)Cl QPAXMPYBNSHKAK-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate 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)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 1
- 229960004703 clobetasol propionate Drugs 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 description 1
- FZCHYNWYXKICIO-FZNHGJLXSA-N cortisol 17-valerate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O FZCHYNWYXKICIO-FZNHGJLXSA-N 0.000 description 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
- 229960003290 cortisone acetate Drugs 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229960003662 desonide Drugs 0.000 description 1
- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 description 1
- 229960002344 dexamethasone sodium phosphate Drugs 0.000 description 1
- PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 230000009266 disease activity Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940069417 doxy Drugs 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 206010016165 failure to thrive Diseases 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960003973 fluocortolone Drugs 0.000 description 1
- 229960002650 fluprednidene acetate Drugs 0.000 description 1
- DEFOZIFYUBUHHU-IYQKUMFPSA-N fluprednidene acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC(=C)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O DEFOZIFYUBUHHU-IYQKUMFPSA-N 0.000 description 1
- 239000013568 food allergen Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000000455 heteroaryl-fused-cycloalkyl group Chemical group 0.000 description 1
- 125000000643 heteroaryl-fused-heterocycloalkyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229960001067 hydrocortisone acetate Drugs 0.000 description 1
- 229960001524 hydrocortisone butyrate Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 238000011419 induction treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000006749 inflammatory damage Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960000829 kaolin Drugs 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000011418 maintenance treatment Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 229960001664 mometasone Drugs 0.000 description 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000000820 nonprescription drug Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000003076 paracrine Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 125000005541 phosphonamide group Chemical group 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000000955 prescription drug Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000003979 response to food Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010181 skin prick test Methods 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- GZJPDRMQUMFPTR-UHFFFAOYSA-M sodium 2-[2-(3-phenylpropyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl]acetate Chemical compound [Na+].C1C=2C3=CC=CC=C3N(CC(=O)[O-])C=2CCN1CCCC1=CC=CC=C1 GZJPDRMQUMFPTR-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- RUDMWCOSLLQDPK-UHFFFAOYSA-M sodium;2-[5-chloro-2-methyl-3-[4-(propan-2-ylcarbamoyl)phenoxy]indol-1-yl]acetate Chemical compound [Na+].C1=CC(C(=O)NC(C)C)=CC=C1OC1=C(C)N(CC([O-])=O)C2=CC=C(Cl)C=C12 RUDMWCOSLLQDPK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229960003114 tixocortol pivalate Drugs 0.000 description 1
- BISFDZNIUZIKJD-XDANTLIUSA-N tixocortol pivalate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)C(C)(C)C)(O)[C@@]1(C)C[C@@H]2O BISFDZNIUZIKJD-XDANTLIUSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/18—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans
- C07K16/24—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material from animals or humans against cytokines, lymphokines or interferons
- C07K16/244—Interleukins [IL]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161576640P | 2011-12-16 | 2011-12-16 | |
| US61/576,640 | 2011-12-16 | ||
| PCT/GB2012/000904 WO2013088109A1 (en) | 2011-12-16 | 2012-12-14 | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140113667A true KR20140113667A (ko) | 2014-09-24 |
Family
ID=47470031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147018762A Withdrawn KR20140113667A (ko) | 2011-12-16 | 2012-12-14 | 호산구성 식도염의 치료를 위한 crth2 길항제 및 양성자 펌프 저해제의 조합 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20140328861A1 (OSRAM) |
| EP (1) | EP2790696A1 (OSRAM) |
| JP (1) | JP2015500326A (OSRAM) |
| KR (1) | KR20140113667A (OSRAM) |
| CN (1) | CN104114169A (OSRAM) |
| AU (1) | AU2012351342A1 (OSRAM) |
| BR (1) | BR112014014558A8 (OSRAM) |
| CA (1) | CA2859284A1 (OSRAM) |
| EA (1) | EA026456B1 (OSRAM) |
| IL (1) | IL233131A0 (OSRAM) |
| MX (1) | MX2014007239A (OSRAM) |
| SG (1) | SG11201402796SA (OSRAM) |
| UA (1) | UA112667C2 (OSRAM) |
| WO (1) | WO2013088109A1 (OSRAM) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7608693B2 (en) | 2006-10-02 | 2009-10-27 | Regeneron Pharmaceuticals, Inc. | High affinity human antibodies to human IL-4 receptor |
| GB201103837D0 (en) | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| GB201121557D0 (en) | 2011-12-15 | 2012-01-25 | Oxagen Ltd | Process |
| RU2690675C2 (ru) | 2012-08-21 | 2019-06-05 | Санофи Байотекнолоджи | Способы лечения или предотвращения астмы посредством введения антагониста il-4r |
| TWI697334B (zh) | 2013-06-04 | 2020-07-01 | 美商再生元醫藥公司 | 藉由投與il-4r抑制劑以治療過敏及增強過敏原-特異之免疫療法的方法 |
| EP3613432B1 (en) | 2013-06-21 | 2025-08-06 | Sanofi Biotechnology | Methods for treating nasal polyposis by administering an il-4r antagonist |
| TWI634900B (zh) | 2013-07-11 | 2018-09-11 | 再生元醫藥公司 | 藉由投與il-4r抑制劑治療嗜酸性食道炎的方法 |
| WO2015034678A2 (en) | 2013-09-06 | 2015-03-12 | Aptalis Pharmatech, Inc. | Corticosteroid containing orally disintegrating tablet compositions for eosinophilic esophagitis |
| WO2015130975A1 (en) | 2014-02-28 | 2015-09-03 | Regeneron Pharmaceuticals, Inc. | Methods for treating skin infection by administering an il-4r antagonist |
| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| MX2017006286A (es) | 2014-11-14 | 2018-01-23 | Sanofi Biotechnology | Metodos para tratar sinusitis cronica con polipos nasales por administracion de un antagonista de il-4r. |
| US20180021302A1 (en) | 2015-02-13 | 2018-01-25 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus |
| EP3402572B1 (en) | 2016-01-13 | 2022-03-16 | Children's Hospital Medical Center | Compositions and methods for treating allergic inflammatory conditions |
| US10800765B2 (en) | 2016-07-21 | 2020-10-13 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Indole derivative used as CRTH2 inhibitor |
| TWI777515B (zh) | 2016-08-18 | 2022-09-11 | 美商愛戴爾製藥股份有限公司 | 治療嗜伊紅性食道炎之方法 |
| EP4442323A3 (en) | 2016-09-01 | 2025-01-01 | Regeneron Pharmaceuticals, Inc. | Methods for preventing or treating allergy by administering an il-4r antagonist |
| US10485844B2 (en) | 2016-09-22 | 2019-11-26 | Regeneron Pharmaceuticals, Inc. | Methods for treating severe atopic dermatitis by administering an IL-4R inhibitor |
| WO2019028367A1 (en) | 2017-08-04 | 2019-02-07 | Regeneron Pharmaceuticals, Inc. | METHODS OF TREATING ESOPHAGITIS WITH ACTIVE EOSINOPHILES |
| KR20250044796A (ko) | 2017-10-30 | 2025-04-01 | 사노피 바이오테크놀로지 | Il-4r 길항제를 투여하여 천식을 치료 또는 예방하는 방법 |
| CN107954995B (zh) * | 2017-11-30 | 2020-05-05 | 正大天晴药业集团股份有限公司 | 具有crth2抑制剂活性的吲哚衍生物 |
| CN107987072B (zh) * | 2017-11-30 | 2020-06-26 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚类化合物 |
| CN107987066B (zh) * | 2017-11-30 | 2020-06-26 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚衍生物 |
| CN107936004B (zh) * | 2017-11-30 | 2020-05-05 | 正大天晴药业集团股份有限公司 | 作为crth2抑制剂的吲哚类衍生物 |
| US11859250B1 (en) | 2018-02-23 | 2024-01-02 | Children's Hospital Medical Center | Methods for treating eosinophilic esophagitis |
| EP3781588B1 (en) | 2018-04-20 | 2024-10-30 | Children's Hospital Medical Center | Blood biomarker for eosinophilic gastrointestinal disorders |
| MA52624A (fr) | 2018-05-13 | 2021-03-24 | Regeneron Pharma | Méthodes de traitement de la dermatite atopique par administration d'un inhibiteur de l'il-4r |
| US12297501B2 (en) | 2019-02-25 | 2025-05-13 | Children's Hospital Medical Center | Methods for diagnosing and treating eosinophilic gastritis |
| PH12021552123A1 (en) | 2019-03-21 | 2022-08-22 | Regeneron Pharma | Combination of il-4/il-13 pathway inhibitors and plasma cell ablation for treating allergy |
| JP7592064B2 (ja) | 2019-07-16 | 2024-11-29 | サノフィ・バイオテクノロジー | Il-4rアンタゴニストを投与することにより喘息を治療するまたは予防するための方法 |
| AU2020326713A1 (en) | 2019-08-05 | 2022-02-17 | Regeneron Pharmaceuticals, Inc. | Methods for treating atopic dermatitis by administering an il-4r antagonist |
| US11504426B2 (en) | 2019-08-05 | 2022-11-22 | Regeneron Pharmaceuticals, Inc. | Methods for treating allergy and enhancing allergen-specific immunotherapy by administering an IL-4R antagonist |
| WO2022020464A1 (en) * | 2020-07-21 | 2022-01-27 | Ellodi Pharmaceuticals, L.P. | Modified release rapidly disintegrating compositions of proton pump inhibitors |
| EP4595953A1 (en) * | 2024-01-30 | 2025-08-06 | Dr. Falk Pharma Gmbh | Orally applicable suspension for the treatment of eosinophilic esophagitis in children |
Family Cites Families (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416649B (sv) | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| IL75400A (en) | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| JPS6150978A (ja) | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| GB2189699A (en) | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated acid-labile medicaments |
| FI90544C (fi) | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Menetelmä lääkeaineina käyttökelpoisten 2-pyridin-2-yyli-metyylitio- ja sulfinyyli-1H-bensimidatsolijohdannaisten valmistamiseksi |
| JPH0768125B2 (ja) | 1988-05-18 | 1995-07-26 | エーザイ株式会社 | 酸不安定化合物の内服用製剤 |
| SE9301830D0 (sv) | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| TWI275587B (en) | 1999-06-17 | 2007-03-11 | Takeda Chemical Industries Ltd | A crystal of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| WO2003097042A1 (en) | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Pgd2 receptor antagonist |
| US7534897B2 (en) | 2002-05-16 | 2009-05-19 | Shionogi & Co., Ltd. | Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| KR20050055747A (ko) | 2002-10-04 | 2005-06-13 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | 염증 질환 치료용의 pgd2 수용체 길항제 |
| ES2263015T3 (es) | 2002-10-21 | 2006-12-01 | Warner-Lambert Company Llc | Derivados de tetrahidroquinolina como antagonistas de crth2. |
| EP1585511B1 (en) | 2002-12-20 | 2013-01-23 | Amgen Inc. | Asthma and allergic inflammation modulators |
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301009D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| DK1471057T3 (da) | 2003-04-25 | 2006-05-15 | Actimis Pharmaceuticals Inc | Pyrimidinyleddikesyrederivater, der er egnede til behandlingen af sygdomme medieret af CRTH2 |
| SE0301569D0 (sv) | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| US20050038070A1 (en) | 2003-07-09 | 2005-02-17 | Amgen Inc. | Asthma and allergic inflammation modulators |
| SE0302232D0 (sv) | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| WO2005040112A1 (en) | 2003-10-14 | 2005-05-06 | Oxagen Limited | Compounds with pgd2 antagonist activity |
| RU2006109108A (ru) | 2003-10-14 | 2007-11-20 | Оксаген Лимитед (GB) | Соединения, обладающие активностью антагонистов crth2 рецепторов |
| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| NZ548396A (en) | 2004-01-31 | 2010-06-25 | Actimis Pharmaceuticals Inc | Imidazo[1,2-C]pyrimidinylacetic acid derivatives |
| KR101165863B1 (ko) | 2004-03-11 | 2012-07-13 | 액테리온 파마슈티칼 리미티드 | 인돌-1-일-아세트산 유도체 |
| WO2005095397A1 (en) | 2004-03-11 | 2005-10-13 | Actelion Pharmaceuticals Ltd | Tetrahydropyridoindole derivatives |
| MXPA06011540A (es) | 2004-04-07 | 2007-01-26 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
| US20050234030A1 (en) | 2004-04-20 | 2005-10-20 | Wilmin Bartolini | Modulators of CRTH2, COX-2 and FAAH |
| GB0409921D0 (en) | 2004-05-04 | 2004-06-09 | Novartis Ag | Organic compounds |
| CA2568742A1 (en) | 2004-05-29 | 2005-12-08 | 7Tm Pharma A/S | Substituted thiazoleacetic as crth2 ligands |
| JP2008500991A (ja) | 2004-05-29 | 2008-01-17 | 7ティーエム ファーマ エイ/エス | 医学的使用のためのcrth2レセプターリガンド |
| US20090105218A1 (en) | 2004-05-29 | 2009-04-23 | 7Tm Pharma A/S | CRTH2 Receptor Ligands For Therapeutic Use |
| MY144903A (en) | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| EA200700712A1 (ru) | 2004-09-21 | 2008-02-28 | Эсерсис, Инк. | Производные индолуксусной кислоты, способ получения таких производных (варианты), фармацевтическая композиция, набор на их основе, способ ингибирования связывания эндогенных лигандов и способ лечения заболеваний и расстройств, восприимчивых к ингибированию связывания эндогенных лигандов с рецептором crth-2 |
| GB0422057D0 (en) | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| US8524715B2 (en) | 2004-11-23 | 2013-09-03 | Astrazeneca Ab | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| GB0427381D0 (en) | 2004-12-14 | 2005-01-19 | Novartis Ag | Organic compounds |
| GB0500604D0 (en) | 2005-01-13 | 2005-02-16 | Astrazeneca Ab | Novel process |
| JP2008543726A (ja) | 2005-02-24 | 2008-12-04 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症性疾患の処置のためのpgd2受容体アンタゴニスト |
| GB0505048D0 (en) | 2005-03-11 | 2005-04-20 | Oxagen Ltd | Compounds with PGD antagonist activity |
| RU2453540C2 (ru) | 2005-04-21 | 2012-06-20 | Лаборатуар Сероно С.А. | 2,3-замещенные пиразинсульфонамиды в качестве ингибиторов crth2 |
| GB0510585D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| PT1891075E (pt) | 2005-05-24 | 2011-11-10 | Merck Serono Sa | Derivados espiro tricíclicos como moduladores do crth2 |
| GB0512944D0 (en) | 2005-06-24 | 2005-08-03 | Argenta Discovery Ltd | Indolizine compounds |
| ATE425791T1 (de) * | 2005-07-29 | 2009-04-15 | Rottapharm Spa | Kombination aus itriglumid und ppi zur behandlung von gastrointestinalen- und assozierten krankheiten |
| EP1915372B1 (en) | 2005-08-12 | 2013-11-20 | Merck Canada Inc. | Indole derivatives as crth2 receptor antagonists |
| WO2007022501A2 (en) | 2005-08-18 | 2007-02-22 | Microbia, Inc. | Useful indole compounds |
| GB0518494D0 (en) | 2005-09-09 | 2005-10-19 | Argenta Discovery Ltd | Thiazole compounds |
| GB0518783D0 (en) | 2005-09-14 | 2005-10-26 | Argenta Discovery Ltd | Indolizine compounds |
| EP1928457B1 (en) | 2005-09-30 | 2012-12-12 | Pulmagen Therapeutics (Asthma) Limited | Quinolines and their therapeutic use |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| EP1937632A1 (en) | 2005-10-06 | 2008-07-02 | Astra Zeneca AB | Novel compounds |
| GB0521275D0 (en) | 2005-10-19 | 2005-11-30 | Argenta Discovery Ltd | 3-Aminoindole compounds |
| JP2009514935A (ja) | 2005-11-05 | 2009-04-09 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| WO2007062678A1 (en) | 2005-11-29 | 2007-06-07 | 7Tm Pharma A/S | Phenoxyacetic acid derivatives as crth2 receptor ligands |
| GB0524427D0 (en) | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Use of receptor ligands in threapy |
| WO2007062677A1 (en) | 2005-11-30 | 2007-06-07 | 7Tm Pharma A/S | Thiazolyl- and pyrimidinyl-acetic acids and their use as crth2 receptor ligands |
| GB0524428D0 (en) | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of receptor ligands |
| US20080293775A1 (en) | 2005-12-15 | 2008-11-27 | Astrazeneca Ab | Substituted Diphenylethers, -Amines, -Sulfides and -Methanes for the Treatment of Respiratory Disease |
| CN101454284A (zh) | 2006-05-26 | 2009-06-10 | 阿斯利康(瑞典)有限公司 | 联芳基或芳基-杂芳基取代的吲哚类化合物 |
| GB0611781D0 (en) | 2006-06-14 | 2006-07-26 | Argenta Discovery Ltd | 2-Oxo-2H-Chromene Compounds |
| EP2046740B1 (en) | 2006-07-22 | 2012-05-23 | Oxagen Limited | Compounds having crth2 antagonist activity |
| NZ575507A (en) | 2006-08-21 | 2011-10-28 | Array Biopharma Inc | 4-substituted phenoxyphenylacetic acid derivatives |
| CA2673356A1 (en) | 2006-12-21 | 2008-06-26 | Argenta Discovery Limited | Crth2 antagonists |
| GB0625842D0 (en) | 2006-12-22 | 2007-02-07 | Argenta Discovery Ltd | Indolizine derivatives |
| AU2007349641A1 (en) | 2007-03-21 | 2008-09-25 | Argenta Oral Therapeutics Limited | Indolizine acetic acid derivatives as CRTH2 antagonists |
| EP2129661B1 (en) | 2007-03-29 | 2012-02-08 | Pulmagen Therapeutics (Asthma) Limited | Quinoline derivatives as crth2 receptor ligands |
| CN101772489B (zh) | 2007-06-21 | 2013-02-20 | 艾克提麦斯医药品有限公司 | 一种crth2拮抗剂的胺盐 |
| US20110124683A1 (en) | 2007-11-13 | 2011-05-26 | Oxagen Limited | Use of CRTH2 Antagonist Compounds |
| GB0722216D0 (en) * | 2007-11-13 | 2007-12-27 | Oxagen Ltd | Use of crth2 antagonist compounds |
| ATE502920T1 (de) * | 2007-12-14 | 2011-04-15 | Pulmagen Therapeutics Asthma Ltd | Indole und ihre therapeutische verwendung |
| EA201001029A1 (ru) | 2007-12-19 | 2011-06-30 | Амген Инк. | Производные фенилуксусной кислоты в качестве модуляторов процесса воспаления |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| MX2010007833A (es) * | 2008-01-18 | 2010-08-11 | Oxagen Ltd | Compuestos que tienen actividad antagonista de crth2. |
| EP2240444A1 (en) | 2008-01-22 | 2010-10-20 | Oxagen Limited | Compounds having crth2 antagonist activity |
| JP2011509990A (ja) | 2008-01-22 | 2011-03-31 | オキサジェン リミテッド | Crth2アンタゴニスト活性を有する化合物 |
| EP2300425A4 (en) * | 2008-06-24 | 2012-03-21 | Panmira Pharmaceuticals Llc | PROSTAGLANDIN D2 RECEPTOR CYCLOALCANEÝBINDLUCK ANTAGONISTS |
| US20110312945A1 (en) * | 2008-10-01 | 2011-12-22 | James Jia | Crth2 modulators |
| WO2010042652A2 (en) * | 2008-10-08 | 2010-04-15 | Amira Pharmaceuticals, Inc. | Heteroalkyl biphenyl antagonists of prostaglandin d2 receptors |
| JP2012072061A (ja) * | 2009-01-29 | 2012-04-12 | Eisai R & D Management Co Ltd | 新規組成物 |
| IN2012DN00359A (OSRAM) * | 2009-07-20 | 2015-05-22 | Vetegen Llc | |
| SG10201404662YA (en) | 2009-08-05 | 2014-10-30 | Panmira Pharmaceuticals Llc | Dp2 antagonist and uses thereof |
| RU2015138677A (ru) * | 2009-08-17 | 2018-12-25 | Дзе Пенн Стейт Рисерч Фаундейшн | Применение ингибиторов nkg2d для лечения сердечно-сосудистых и метаболических заболеваний, таких как диабет 2 типа |
| AU2011203649A1 (en) | 2010-01-06 | 2012-06-14 | Brickell Biotech, Inc. | DP2 antagonist and uses thereof |
-
2012
- 2012-12-14 JP JP2014546622A patent/JP2015500326A/ja active Pending
- 2012-12-14 MX MX2014007239A patent/MX2014007239A/es unknown
- 2012-12-14 EP EP12808859.8A patent/EP2790696A1/en not_active Withdrawn
- 2012-12-14 BR BR112014014558A patent/BR112014014558A8/pt not_active Application Discontinuation
- 2012-12-14 US US14/365,306 patent/US20140328861A1/en not_active Abandoned
- 2012-12-14 CA CA2859284A patent/CA2859284A1/en not_active Abandoned
- 2012-12-14 KR KR1020147018762A patent/KR20140113667A/ko not_active Withdrawn
- 2012-12-14 AU AU2012351342A patent/AU2012351342A1/en not_active Abandoned
- 2012-12-14 SG SG11201402796SA patent/SG11201402796SA/en unknown
- 2012-12-14 UA UAA201407393A patent/UA112667C2/uk unknown
- 2012-12-14 EA EA201491008A patent/EA026456B1/ru unknown
- 2012-12-14 CN CN201280066423.2A patent/CN104114169A/zh active Pending
- 2012-12-14 WO PCT/GB2012/000904 patent/WO2013088109A1/en not_active Ceased
-
2014
- 2014-06-15 IL IL233131A patent/IL233131A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2014007239A (es) | 2014-08-08 |
| SG11201402796SA (en) | 2014-06-27 |
| BR112014014558A8 (pt) | 2017-07-04 |
| CN104114169A (zh) | 2014-10-22 |
| EA026456B1 (ru) | 2017-04-28 |
| CA2859284A1 (en) | 2013-06-20 |
| IL233131A0 (en) | 2014-07-31 |
| NZ626990A (en) | 2016-01-29 |
| EA201491008A1 (ru) | 2015-02-27 |
| BR112014014558A2 (pt) | 2017-06-13 |
| EP2790696A1 (en) | 2014-10-22 |
| US20140328861A1 (en) | 2014-11-06 |
| AU2012351342A1 (en) | 2014-07-24 |
| WO2013088109A1 (en) | 2013-06-20 |
| JP2015500326A (ja) | 2015-01-05 |
| UA112667C2 (uk) | 2016-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20140113667A (ko) | 호산구성 식도염의 치료를 위한 crth2 길항제 및 양성자 펌프 저해제의 조합 | |
| JP7235816B2 (ja) | 核内受容体調節剤 | |
| JP6342393B2 (ja) | 置換型ピラゾロン化合物及び使用方法 | |
| JP5707518B2 (ja) | 置換型キノリン化合物及び使用方法 | |
| JP2019535672A (ja) | インダゾール−3−カルボキサミドの使用方法およびwnt/β−カテニンシグナル伝達経路阻害剤としてのそれらの使用 | |
| JP2024072291A (ja) | 同種抗体により駆動される慢性移植片対宿主病を処置及び予防する方法 | |
| JP2015500326A5 (OSRAM) | ||
| JP2015515989A (ja) | 1H−ピラゾロ[3,4−b]ピリジンおよびそれらの治療的使用 | |
| WO2015002754A2 (en) | Novel bicyclic bromodomain inhibitors | |
| KR20180013851A (ko) | 치환된 2,3-디히드로이미다조[1,2-c]퀴나졸린-함유 조합물 | |
| KR20150083833A (ko) | Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 및 이의 이용 방법 | |
| KR20180013850A (ko) | 치환된 2,3-디히드로이미다조[1,2-c]퀴나졸린의 용도 | |
| JP2018513140A (ja) | 新規医薬用途 | |
| TW202320792A (zh) | 包含fgfr抑制劑及kras抑制劑之組合療法 | |
| CN115776890A (zh) | 作为眼病治疗剂的trpv4抑制剂 | |
| CA2524268A1 (en) | Proton pump inhibitors for the treatment of lower abdominal disorders | |
| TW202448460A (zh) | Dgk(二醯基甘油激酶)抑制劑之組合 | |
| AU2003282696A1 (en) | Method of treating snoring and other obstructive breathing disorders | |
| NZ626990B2 (en) | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis | |
| CA2478958A1 (en) | Use of proton pump inhibitors for the treatment of airway disorders | |
| JP2005523298A (ja) | 非心臓性胸痛の治療のためのプロトンポンプ阻害剤の使用 | |
| CN118632696A (zh) | 包含fgfr抑制剂和kras抑制剂的组合疗法 | |
| Udupa | Proton Pump Inhibitors–An Overview |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20140707 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |