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
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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Classifications
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- 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
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- 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
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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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- A61K39/39533—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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- 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
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- 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)
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- 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 |
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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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| Application Number | Title | Priority Date | Filing Date |
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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 (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) |
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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 |
| 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 |
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-
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 |
|---|---|
| KR20140113667A (ko) | 2014-09-24 |
| 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 |
| 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 |
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| Date | Code | Title | Description |
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Effective date: 20171214 |