CA2859284A1 - Combination of a crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis - Google Patents
Combination of a crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis Download PDFInfo
- Publication number
- CA2859284A1 CA2859284A1 CA2859284A CA2859284A CA2859284A1 CA 2859284 A1 CA2859284 A1 CA 2859284A1 CA 2859284 A CA2859284 A CA 2859284A CA 2859284 A CA2859284 A CA 2859284A CA 2859284 A1 CA2859284 A1 CA 2859284A1
- Authority
- CA
- Canada
- 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.)
- Abandoned
Links
- 229940124003 CRTH2 antagonist Drugs 0.000 title claims abstract description 84
- 206010064212 Eosinophilic oesophagitis Diseases 0.000 title claims abstract description 53
- 201000000708 eosinophilic esophagitis Diseases 0.000 title claims abstract description 53
- 229940126409 proton pump inhibitor Drugs 0.000 title claims abstract description 24
- 239000000612 proton pump inhibitor Substances 0.000 title claims abstract description 24
- 238000011282 treatment Methods 0.000 title claims description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 178
- 238000000034 method Methods 0.000 claims abstract description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 573
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
- -1 6-fluoroquinolin-2-yl Chemical group 0.000 claims description 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 239000008194 pharmaceutical composition Substances 0.000 claims description 57
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 52
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
- 229960004770 esomeprazole Drugs 0.000 claims description 40
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 38
- 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 37
- 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 37
- MJIHNNLFOKEZEW-RUZDIDTESA-N dexlansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1C[S@@](=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-RUZDIDTESA-N 0.000 claims description 37
- 229960003568 dexlansoprazole Drugs 0.000 claims description 37
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 37
- 229960003174 lansoprazole Drugs 0.000 claims description 37
- 229960000381 omeprazole Drugs 0.000 claims description 37
- 229960005019 pantoprazole Drugs 0.000 claims description 37
- 229960004157 rabeprazole Drugs 0.000 claims description 37
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 239000003246 corticosteroid Substances 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=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 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 9
- 229960004436 budesonide Drugs 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 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
- 239000012453 solvate Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 6
- 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 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000009115 maintenance therapy Methods 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 3
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229960003957 dexamethasone Drugs 0.000 claims description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
- 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
- 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
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-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 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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 2
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims description 2
- 229960005127 montelukast Drugs 0.000 claims description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 7
- HKWZIRZRRMVZLR-UHFFFAOYSA-N 2-[3-[[2-(benzenesulfonyl)pyridin-3-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound 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 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 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 4
- 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 4
- YPOOGOPKCXZNGP-UHFFFAOYSA-N CC1=C(C2=C(N1)C=CC(=C2CC(=O)O)F)CC3=NC4=CC=CC=C4C=C3 Chemical group CC1=C(C2=C(N1)C=CC(=C2CC(=O)O)F)CC3=NC4=CC=CC=C4C=C3 YPOOGOPKCXZNGP-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- FJGYKUGWEQGURY-UHFFFAOYSA-N 2-[3-[(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(SCCC2(C)C)C2=C1 FJGYKUGWEQGURY-UHFFFAOYSA-N 0.000 claims 1
- BRNIUXLBABJPPA-UHFFFAOYSA-N 2-[3-[(4-benzylsulfonylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)CC1=CC=CC=C1 BRNIUXLBABJPPA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- YSVZRJDOEFUDEM-UHFFFAOYSA-N 2-[3-[[1-(benzenesulfonyl)pyrrol-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=CC=C1 YSVZRJDOEFUDEM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 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
- 229960005294 triamcinolone Drugs 0.000 description 1
- 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 1
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Classifications
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
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- 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
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- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Endocrinology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201161576640P | 2011-12-16 | 2011-12-16 | |
| US61/576640 | 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)
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| CA2859284A1 true CA2859284A1 (en) | 2013-06-20 |
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| CA2859284A Abandoned CA2859284A1 (en) | 2011-12-16 | 2012-12-14 | Combination of a crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
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| EP (1) | EP2790696A1 (enExample) |
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| 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 |
| KR102307248B1 (ko) | 2012-08-21 | 2021-10-01 | 사노피 바이오테크놀로지 | Il-4r 길항제의 투여에 의한 천식의 치료 또는 예방 방법 |
| NZ630178A (en) | 2012-09-07 | 2017-06-30 | Regeneron Pharma | Methods for treating atopic dermatitis by administering an il-4r antagonist |
| TWI755763B (zh) | 2013-06-04 | 2022-02-21 | 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 |
| MX368068B (es) | 2013-06-21 | 2019-09-18 | Sanofi Biotechnology | Antagonista de il-4r para usarse para tratar la poliposis nasal. |
| TWI682781B (zh) | 2013-07-11 | 2020-01-21 | 美商再生元醫藥公司 | 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 |
| KR20160120735A (ko) | 2014-02-28 | 2016-10-18 | 리제너론 파아마슈티컬스, 인크. | Ｉｌ-4ｒ 길항제의 투여에 의한 피부 감염의 치료 방법 |
| 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 |
| CA2967602C (en) | 2014-11-14 | 2024-09-24 | Regeneron Pharmaceuticals, Inc. | METHODS OF TREATMENT OF CHRONIC SINUSITIS WITH NASAL POLYPOSIS BY ADMINISTRATION OF AN IL-4R ANTAGONIST |
| JP6770522B2 (ja) | 2015-02-13 | 2020-10-14 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 全身性エリテマトーデスを予防し、及び／又は、治療するためのｐｔｇｄｒ−１及び／又はｐｔｇｄｒ−２アンタゴニスト |
| EP3402572B1 (en) * | 2016-01-13 | 2022-03-16 | Children's Hospital Medical Center | Compositions and methods for treating allergic inflammatory conditions |
| EP3489233B1 (en) | 2016-07-21 | 2022-01-12 | 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 |
| US11771743B2 (en) | 2016-09-01 | 2023-10-03 | 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 |
| EP4344706A3 (en) | 2017-10-30 | 2024-05-22 | Sanofi Biotechnology | Methods for treating or preventing asthma by administering an il-4r antagonist |
| 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 |
| 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 |
| 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 |
| 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 |
| CN120227453A (zh) | 2018-05-13 | 2025-07-01 | 瑞泽恩制药公司 | 用于通过施用il-4r抑制剂治疗特应性皮炎的方法 |
| US12297501B2 (en) | 2019-02-25 | 2025-05-13 | Children's Hospital Medical Center | Methods for diagnosing and treating eosinophilic gastritis |
| KR20210143246A (ko) | 2019-03-21 | 2021-11-26 | 리제너론 파아마슈티컬스, 인크. | 알레르기 치료용 il-4/il-13 경로 억제제 및 형질 세포 절제의 병용 |
| BR112022000740A2 (pt) | 2019-07-16 | 2022-07-05 | Sanofi Biotechnology | Métodos para tratamento ou prevenção de asma por administração de um antagonista de il-4r |
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| KR20220042217A (ko) | 2019-08-05 | 2022-04-04 | 리제너론 파아마슈티컬스, 인크. | Il-4r 길항제를 투여함에 의해 알레르기를 치료하고 알레르겐-특이적 면역치료요법을 증진시키기 위한 방법 |
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-
2012
- 2012-12-14 WO PCT/GB2012/000904 patent/WO2013088109A1/en not_active Ceased
- 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 UA UAA201407393A patent/UA112667C2/uk unknown
- 2012-12-14 JP JP2014546622A patent/JP2015500326A/ja active Pending
- 2012-12-14 CN CN201280066423.2A patent/CN104114169A/zh active Pending
- 2012-12-14 US US14/365,306 patent/US20140328861A1/en not_active Abandoned
- 2012-12-14 EA EA201491008A patent/EA026456B1/ru unknown
- 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 MX MX2014007239A patent/MX2014007239A/es unknown
- 2012-12-14 AU AU2012351342A patent/AU2012351342A1/en not_active Abandoned
- 2012-12-14 SG SG11201402796SA patent/SG11201402796SA/en unknown
-
2014
- 2014-06-15 IL IL233131A patent/IL233131A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014014558A8 (pt) | 2017-07-04 |
| NZ626990A (en) | 2016-01-29 |
| IL233131A0 (en) | 2014-07-31 |
| AU2012351342A1 (en) | 2014-07-24 |
| EP2790696A1 (en) | 2014-10-22 |
| SG11201402796SA (en) | 2014-06-27 |
| EA201491008A1 (ru) | 2015-02-27 |
| US20140328861A1 (en) | 2014-11-06 |
| WO2013088109A1 (en) | 2013-06-20 |
| CN104114169A (zh) | 2014-10-22 |
| KR20140113667A (ko) | 2014-09-24 |
| MX2014007239A (es) | 2014-08-08 |
| EA026456B1 (ru) | 2017-04-28 |
| UA112667C2 (uk) | 2016-10-10 |
| JP2015500326A (ja) | 2015-01-05 |
| BR112014014558A2 (pt) | 2017-06-13 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20171214 |