JP2015500326A5 - - Google Patents
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- JP2015500326A5 JP2015500326A5 JP2014546622A JP2014546622A JP2015500326A5 JP 2015500326 A5 JP2015500326 A5 JP 2015500326A5 JP 2014546622 A JP2014546622 A JP 2014546622A JP 2014546622 A JP2014546622 A JP 2014546622A JP 2015500326 A5 JP2015500326 A5 JP 2015500326A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluoro
- acetic acid
- indol
- methylindol
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 15
- 229940124003 CRTH2 antagonist Drugs 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 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 7
- 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 7
- 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 7
- 229960003568 dexlansoprazole Drugs 0.000 claims 7
- 229960004770 esomeprazole Drugs 0.000 claims 7
- 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 7
- 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 7
- 229960003174 lansoprazole Drugs 0.000 claims 7
- 229960000381 omeprazole Drugs 0.000 claims 7
- 229960005019 pantoprazole Drugs 0.000 claims 7
- 229960004157 rabeprazole Drugs 0.000 claims 7
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims 7
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 6
- 239000003246 corticosteroid Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 206010064212 Eosinophilic oesophagitis Diseases 0.000 claims 4
- 201000000708 eosinophilic esophagitis Diseases 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229940126409 proton pump inhibitor Drugs 0.000 claims 4
- 239000000612 proton pump inhibitor Substances 0.000 claims 4
- 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 3
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 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 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229960004436 budesonide Drugs 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 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 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 238000009115 maintenance therapy Methods 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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 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
- 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 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
- 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 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
- PFAZRAQOCIMBPO-UHFFFAOYSA-N 2-[3-[(4,4-dimethyl-1,1-dioxo-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=C2S(=O)(=O)CCC(C)(C)C2=C1 PFAZRAQOCIMBPO-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
- 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
- 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 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
- BHEFOTSBJZWUIS-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)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(Cl)C=C1 BHEFOTSBJZWUIS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- JLWHNIVAJGRXQH-UHFFFAOYSA-N 2-[3-[[2-(4-cyanophenoxy)phenyl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(C#N)C=C1 JLWHNIVAJGRXQH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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Families Citing this family (35)
| 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 |
| WO2014031610A1 (en) | 2012-08-21 | 2014-02-27 | Sanofi | Methods for treating or preventing asthma by administering an il-4r antagonist |
| HRP20181227T1 (hr) | 2012-09-07 | 2018-10-05 | Regeneron Pharmaceuticals, Inc. | Metode za liječenje atopijskog dermatitisa primjenom antagonista il-4r |
| 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 |
| 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 |
| RU2704999C2 (ru) | 2014-02-28 | 2019-11-01 | Ридженерон Фармасьютикалз, Инк. | Способ лечения кожной инфекции путем введения антагониста il-4r |
| GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| PT3613432T (pt) | 2014-05-07 | 2025-10-29 | Regeneron Pharma | Métodos para tratar a polipose nasal através da administração de um antagonista de il-4r |
| US10066017B2 (en) | 2014-11-14 | 2018-09-04 | Sanofi Biotechnology | Methods for treating chronic sinusitis with nasal polyps by administering an IL-4R antagonist |
| ES2991300T3 (es) | 2015-02-13 | 2024-12-03 | Inserm Institut Nat De La Sante Et De Larecherche Medicale | Antagonistas de PTGDR-1 y/o PTGDR-2 para prevenir y/o tratar lupus eritematoso sistémico |
| EP4059570A1 (en) * | 2016-01-13 | 2022-09-21 | Children's Hospital Medical Center | Compositions and methods for treating allergic inflammatory conditions |
| JP7044754B2 (ja) * | 2016-07-21 | 2022-03-30 | チア タイ ティエンチン ファーマシューティカル グループ カンパニー リミテッド | Ｃｒｔｈ２阻害剤としてのインドール誘導体 |
| 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 |
| CN109789196B (zh) | 2016-09-01 | 2024-03-19 | 瑞泽恩制药公司 | 用于通过施用il-4r拮抗剂来预防或治疗变态反应的方法 |
| WO2019028367A1 (en) | 2017-08-04 | 2019-02-07 | Regeneron Pharmaceuticals, Inc. | METHODS OF TREATING ESOPHAGITIS WITH ACTIVE EOSINOPHILES |
| PT3515465T (pt) | 2017-08-18 | 2024-03-04 | Regeneron Pharma | Métodos para o tratamento de uma dermatite atópica grave mediante a administração de um inibidor de il-4r |
| PL3703818T3 (pl) | 2017-10-30 | 2024-03-25 | Sanofi Biotechnology | Antagonista IL-4R do zastosowania w sposobie leczenia lub zapobiegania astmie |
| 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 |
| 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 |
| US11859250B1 (en) | 2018-02-23 | 2024-01-02 | Children's Hospital Medical Center | Methods for treating eosinophilic esophagitis |
| WO2019204580A1 (en) | 2018-04-20 | 2019-10-24 | Children's Hospital Medical Center | Blood biomarker for eosinophilic gastrointestinal disorders |
| EP3793597A1 (en) | 2018-05-13 | 2021-03-24 | Regeneron Pharmaceuticals, Inc. | Methods for treating atopic dermatitis by administering an il-4r inhibitor |
| US12297501B2 (en) | 2019-02-25 | 2025-05-13 | Children's Hospital Medical Center | Methods for diagnosing and treating eosinophilic gastritis |
| MA55372A (fr) | 2019-03-21 | 2022-01-26 | Regeneron Pharma | Combinaison d'inhibiteurs de la voie il-4/il-13 et d'ablation de plasmocytes pour traiter une allergie |
| 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 |
| CN114173819A (zh) | 2019-08-05 | 2022-03-11 | 瑞泽恩制药公司 | 通过施用il-4r拮抗剂治疗过敏和增强过敏原特异性免疫疗法的方法 |
| AU2020326713A1 (en) | 2019-08-05 | 2022-02-17 | Regeneron Pharmaceuticals, Inc. | Methods for treating atopic dermatitis 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 |
| JP4484108B2 (ja) | 2002-05-16 | 2010-06-16 | 塩野義製薬株式会社 | Ｐｇｄ２受容体拮抗作用を有する化合物 |
| JPWO2003097042A1 (ja) | 2002-05-16 | 2005-09-15 | 塩野義製薬株式会社 | Ｐｇｄ２受容体拮抗剤 |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| MXPA05003456A (es) | 2002-10-04 | 2005-07-05 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
| CA2500083A1 (en) | 2002-10-21 | 2004-04-29 | Warner-Lambert Company Llc | Tetrahydroquinoline derivatives as crth2 antagonists |
| AU2003297398B2 (en) | 2002-12-20 | 2009-09-24 | 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 |
| ATE316077T1 (de) | 2003-04-25 | 2006-02-15 | Actimis Pharmaceuticals Inc | Pyrimidin-essigsäure derivate geeignet zur behandlung von crth2-bedingten krankheiten |
| 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 |
| CA2542716A1 (en) | 2003-10-14 | 2005-05-06 | Oxagen Limited | Compounds having crth2 antagonist activity |
| WO2005040112A1 (en) | 2003-10-14 | 2005-05-06 | Oxagen Limited | Compounds with pgd2 antagonist activity |
| 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 |
| RU2387652C2 (ru) | 2004-03-11 | 2010-04-27 | Актелион Фармасьютиклз Лтд | Производные тетрагидропиридоиндола |
| WO2005094816A1 (en) | 2004-03-11 | 2005-10-13 | Actelion Pharmaceuticals Ltd | Indol-1-yl-acetic acid derivatives |
| AR048528A1 (es) | 2004-04-07 | 2006-05-03 | Millennium Pharm Inc | Compuestos derivados de quinolina como antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias y composiciones farmacéuticas que los contienen. |
| 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 |
| WO2005115374A1 (en) | 2004-05-29 | 2005-12-08 | 7Tm Pharma A/S | Crth2 receptor ligands for therapeutic use |
| US8022063B2 (en) | 2004-05-29 | 2011-09-20 | 7Tm Pharma A/S | CRTH2 receptor ligands for medicinal uses |
| MXPA06013924A (es) | 2004-05-29 | 2007-07-18 | 7Tm Pharma As | Acidos tiazolaceticos sustituidos como ligandos crth2. |
| 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 |
| EP1805171A4 (en) | 2004-09-21 | 2009-05-13 | Wyeth Corp | CRTH2 RECEPTOR ANTAGONISM DISPLAYING INDIGENOUS ACIDS AND APPLICATIONS THEREOF |
| GB0422057D0 (en) | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| JP5208510B2 (ja) | 2004-11-23 | 2013-06-12 | アストラゼネカ・アクチエボラーグ | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
| GB0427381D0 (en) | 2004-12-14 | 2005-01-19 | Novartis Ag | Organic compounds |
| GB0500604D0 (en) | 2005-01-13 | 2005-02-16 | Astrazeneca Ab | Novel process |
| AU2006216713A1 (en) | 2005-02-24 | 2006-08-31 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| GB0505048D0 (en) | 2005-03-11 | 2005-04-20 | Oxagen Ltd | Compounds with PGD antagonist activity |
| KR101380448B1 (ko) | 2005-04-21 | 2014-04-11 | 메르크 세로노 에스. 에이. | ２，３치환된 피라진 술폰아미드 |
| GB0510585D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| EP1891075B1 (en) | 2005-05-24 | 2011-10-19 | Merck Serono SA | Tricyclic spiro derivatives as crth2 modulators |
| GB0512944D0 (en) | 2005-06-24 | 2005-08-03 | Argenta Discovery Ltd | Indolizine compounds |
| ES2324354T3 (es) * | 2005-07-29 | 2009-08-05 | Rottapharm S.P.A. | Combinacion terapeutica de itriglumida e inhibidores de la bomba de protones en el tratamiento de trastornos gastrointestinales y relacionados. |
| US7696222B2 (en) | 2005-08-12 | 2010-04-13 | Merck Frosst Canada Ltd | Indole derivatives as CRTH2 receptor antagonists |
| US20070203209A1 (en) | 2005-08-18 | 2007-08-30 | Wilmin Bartolini | 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 |
| EA015358B1 (ru) | 2005-09-30 | 2011-06-30 | Пульмаджен Терапьютикс (Эсме) Лимитед | Хинолины и их терапевтическое применение |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| JP5155171B2 (ja) | 2005-10-06 | 2013-02-27 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| GB0521275D0 (en) | 2005-10-19 | 2005-11-30 | Argenta Discovery Ltd | 3-Aminoindole compounds |
| US20080255150A1 (en) | 2005-11-05 | 2008-10-16 | Astrazeneca Ab | Novel Compounds |
| WO2007062678A1 (en) | 2005-11-29 | 2007-06-07 | 7Tm Pharma A/S | Phenoxyacetic acid derivatives as crth2 receptor ligands |
| GB0524428D0 (en) | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of 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 |
| EP1963259B1 (en) | 2005-12-15 | 2012-02-15 | AstraZeneca AB | Substituted diphenylethers, -amines, -sulfides and -methanes for the treatment of respiratory disease |
| US7741360B2 (en) | 2006-05-26 | 2010-06-22 | Astrazeneca Ab | Bi-aryl or aryl-heteroaryl substituted indoles |
| GB0611781D0 (en) | 2006-06-14 | 2006-07-26 | Argenta Discovery Ltd | 2-Oxo-2H-Chromene Compounds |
| PT2046740E (pt) | 2006-07-22 | 2012-08-28 | Oxagen Ltd | Compostos com atividade antagonista do crth2 |
| AU2007286829B2 (en) | 2006-08-21 | 2013-05-02 | Array Biopharma, Inc. | 4-substituted phenoxyphenylacetic acid derivatives |
| MX2009006762A (es) | 2006-12-21 | 2009-08-20 | Argenta Discovery Ltd | Antagonistas crth2. |
| GB0625842D0 (en) | 2006-12-22 | 2007-02-07 | Argenta Discovery Ltd | Indolizine derivatives |
| CA2681409A1 (en) | 2007-03-21 | 2008-09-25 | Argenta Oral Therapeutics Limited | Indolizine acetic acid derivatives as crth2 antagonists |
| US20100144786A1 (en) | 2007-03-29 | 2010-06-10 | Michael Colin Cramp | Quinoline derivatives as crth2 receptor ligands |
| EP2176240A1 (en) | 2007-06-21 | 2010-04-21 | Actimis Pharmaceuticals, Inc., | Amine salts of a crth2 antagonist |
| 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 |
| CA2707785C (en) * | 2007-12-14 | 2015-11-03 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| ES2471919T3 (es) | 2007-12-19 | 2014-06-27 | Amgen, Inc | Derivados de ácido fenilac�tico como moduladores de inflamación |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| PT2250161E (pt) * | 2008-01-18 | 2014-01-21 | Atopix Therapeutics Ltd | Compostos tendo atividade antagonista de crth2 |
| JP2011509991A (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 |
| WO2009093026A1 (en) | 2008-01-22 | 2009-07-30 | Oxagen Limited | Compounds having crth2 antagonist activity |
| EP2300425A4 (en) * | 2008-06-24 | 2012-03-21 | Panmira Pharmaceuticals Llc | PROSTAGLANDIN D2 RECEPTOR CYCLOALCANEÝBINDLUCK ANTAGONISTS |
| WO2010039982A1 (en) * | 2008-10-01 | 2010-04-08 | Ironwood Pharmaceuticals, Inc. | 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 |
| EP2456439A4 (en) * | 2009-07-20 | 2012-12-26 | Vetegen Llc | STABLE PHARMACEUTICAL OMEPRAZOLE FORMULATION FOR ORAL ADMINISTRATION |
| EP2462110A4 (en) | 2009-08-05 | 2013-04-03 | Panmira Pharmaceuticals Llc | DP2 ANTAGONIST AND USES THEREOF |
| EP2467152B1 (en) * | 2009-08-17 | 2017-05-17 | The Penn State Research Foundation | Use of nkg2d inhibitors for treating cardiovascular and metabolic diseases, such as type 2 diabetes |
| AU2011203649A1 (en) | 2010-01-06 | 2012-06-14 | Brickell Biotech, Inc. | DP2 antagonist and uses thereof |
-
2012
- 2012-12-14 SG SG11201402796SA patent/SG11201402796SA/en unknown
- 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 MX MX2014007239A patent/MX2014007239A/es unknown
- 2012-12-14 CN CN201280066423.2A patent/CN104114169A/zh active Pending
- 2012-12-14 AU AU2012351342A patent/AU2012351342A1/en not_active Abandoned
- 2012-12-14 CA CA2859284A patent/CA2859284A1/en not_active Abandoned
- 2012-12-14 EA EA201491008A patent/EA026456B1/ru unknown
- 2012-12-14 US US14/365,306 patent/US20140328861A1/en not_active Abandoned
- 2012-12-14 UA UAA201407393A patent/UA112667C2/uk unknown
- 2012-12-14 JP JP2014546622A patent/JP2015500326A/ja active Pending
- 2012-12-14 BR BR112014014558A patent/BR112014014558A8/pt not_active Application Discontinuation
- 2012-12-14 KR KR1020147018762A patent/KR20140113667A/ko not_active Withdrawn
-
2014
- 2014-06-15 IL IL233131A patent/IL233131A0/en unknown
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