HRP20180298T1 - Postupak dobivanja 3-supstituiranih estera (indol-1-il)octene kiseline - Google Patents
Postupak dobivanja 3-supstituiranih estera (indol-1-il)octene kiseline Download PDFInfo
- Publication number
- HRP20180298T1 HRP20180298T1 HRP20180298TT HRP20180298T HRP20180298T1 HR P20180298 T1 HRP20180298 T1 HR P20180298T1 HR P20180298T T HRP20180298T T HR P20180298TT HR P20180298 T HRP20180298 T HR P20180298T HR P20180298 T1 HRP20180298 T1 HR P20180298T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- fluoro
- acetic acid
- methylindol
- indol
- Prior art date
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- 238000000034 method Methods 0.000 title claims 18
- -1 3-substituted (indol-1-yl)-acetic acid Chemical class 0.000 title claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 48
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 14
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229930192474 thiophene Natural products 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
- 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 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 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
- 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
- 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
- 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
- UORHUPJFTBRWHR-UHFFFAOYSA-N 2-[3-[[5-(4-chlorophenoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C(=NN1C)C(F)(F)F)=C1OC1=CC=C(Cl)C=C1 UORHUPJFTBRWHR-UHFFFAOYSA-N 0.000 claims 1
- QILUMBJCLHPTEK-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 QILUMBJCLHPTEK-UHFFFAOYSA-N 0.000 claims 1
- RLVUYXZUNLMUAA-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(1,3-thiazol-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=NC=CS1 RLVUYXZUNLMUAA-UHFFFAOYSA-N 0.000 claims 1
- BYKXFHSGUBZCES-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(naphthalen-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=C1 BYKXFHSGUBZCES-UHFFFAOYSA-N 0.000 claims 1
- DAZGWLBGWTXSTB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(pyrazolo[1,5-a]pyridin-3-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=C2C=CC=CN2N=C1 DAZGWLBGWTXSTB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QOQCKLKHHCOPDB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-3-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN=C(C=CC=C2)C2=C1 QOQCKLKHHCOPDB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RAQFMAVUQKXQON-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinoxalin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN=C(C=CC=C2)C2=N1 RAQFMAVUQKXQON-UHFFFAOYSA-N 0.000 claims 1
- QKEZLLDSBYOMPM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinoxalin-6-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(N=CC=N2)C2=C1 QKEZLLDSBYOMPM-UHFFFAOYSA-N 0.000 claims 1
- FASXQCVTKJSFMK-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(1-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=C1S(C)(=O)=O FASXQCVTKJSFMK-UHFFFAOYSA-N 0.000 claims 1
- VDKXEDCLHYGIFI-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-methylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CSC1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 VDKXEDCLHYGIFI-UHFFFAOYSA-N 0.000 claims 1
- JTSKPPIIPCUNDB-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-pentylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CCCCCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 JTSKPPIIPCUNDB-UHFFFAOYSA-N 0.000 claims 1
- FUQCZYPTBHJSQX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-phenoxyphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=CC=C1 FUQCZYPTBHJSQX-UHFFFAOYSA-N 0.000 claims 1
- BFDRBVCOIAHTAN-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-phenylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1C1=CC=CC=C1 BFDRBVCOIAHTAN-UHFFFAOYSA-N 0.000 claims 1
- NRPMXZUNAFYCRH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-piperidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)N1CCCCC1 NRPMXZUNAFYCRH-UHFFFAOYSA-N 0.000 claims 1
- FIGQRWRMQCBMIM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-propan-2-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CC(C)S(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 FIGQRWRMQCBMIM-UHFFFAOYSA-N 0.000 claims 1
- RVDPKGJUYVNWKL-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-propylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CCCS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RVDPKGJUYVNWKL-UHFFFAOYSA-N 0.000 claims 1
- PAKMLKICQKNIQV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(2-pyrrolidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1S(=O)(=O)N1CCCC1 PAKMLKICQKNIQV-UHFFFAOYSA-N 0.000 claims 1
- RQECSAJXDRUDCC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-methylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound CSC1=CC=CC(CC=2C3=CC(F)=CC=C3N(CC(O)=O)C=2C)=C1 RQECSAJXDRUDCC-UHFFFAOYSA-N 0.000 claims 1
- RYCRNWCEBLPJQH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC2=CC=CC=C2C=C1S(C)(=O)=O RYCRNWCEBLPJQH-UHFFFAOYSA-N 0.000 claims 1
- JRUNFSWRTCZPQT-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-phenoxyphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1OC1=CC=CC=C1 JRUNFSWRTCZPQT-UHFFFAOYSA-N 0.000 claims 1
- VLTVKWWEZRRUFD-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-phenoxythiophen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC=1SC=CC=1OC1=CC=CC=C1 VLTVKWWEZRRUFD-UHFFFAOYSA-N 0.000 claims 1
- UFWCTHMEWOEIES-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-piperidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 UFWCTHMEWOEIES-UHFFFAOYSA-N 0.000 claims 1
- XUYPKIUZNJXPOQ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(3-pyrrolidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=1)=CC=CC=1S(=O)(=O)N1CCCC1 XUYPKIUZNJXPOQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NRTLJAWOQSWCBN-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-methylsulfonylquinolin-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC(S(C)(=O)=O)=C(C=CC=C2)C2=N1 NRTLJAWOQSWCBN-UHFFFAOYSA-N 0.000 claims 1
- APDITWSWQRJDEE-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentan-3-ylsulfanylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(SC(CC)CC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 APDITWSWQRJDEE-UHFFFAOYSA-N 0.000 claims 1
- FMYBOBSOMRVPFO-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentan-3-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C(CC)CC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 FMYBOBSOMRVPFO-UHFFFAOYSA-N 0.000 claims 1
- WZTBSIYFAISTJO-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-pentylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CCCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 WZTBSIYFAISTJO-UHFFFAOYSA-N 0.000 claims 1
- HJLPNIQIMSEBHY-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-phenylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1C1=CC=CC=C1 HJLPNIQIMSEBHY-UHFFFAOYSA-N 0.000 claims 1
- ZENZJBGBJVAPCX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-piperidin-1-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 ZENZJBGBJVAPCX-UHFFFAOYSA-N 0.000 claims 1
- BIJAGBRNXUAAFU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-propan-2-ylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 BIJAGBRNXUAAFU-UHFFFAOYSA-N 0.000 claims 1
- JZKXRUBGLBERCX-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-propylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 JZKXRUBGLBERCX-UHFFFAOYSA-N 0.000 claims 1
- FPSINLWYMKVWQA-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(5-methylsulfonylthiophen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)S1 FPSINLWYMKVWQA-UHFFFAOYSA-N 0.000 claims 1
- BSTMWSBBRAJYHU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(6-methylsulfonylnaphthalen-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(C=C2)S(C)(=O)=O)C2=C1 BSTMWSBBRAJYHU-UHFFFAOYSA-N 0.000 claims 1
- DUSVRFQPDLUVJU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(6-methylsulfonylquinolin-2-yl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(C=C2)S(C)(=O)=O)C2=N1 DUSVRFQPDLUVJU-UHFFFAOYSA-N 0.000 claims 1
- APNCETQETTYWJQ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(4-methylphenoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(C)C=C1 APNCETQETTYWJQ-UHFFFAOYSA-N 0.000 claims 1
- WAUSUVRQJFOPKH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(4-methylphenoxy)pyridin-3-yl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CN=C1OC1=CC=C(C)C=C1 WAUSUVRQJFOPKH-UHFFFAOYSA-N 0.000 claims 1
- SSVHGPAUAVUSSR-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(4-methylphenyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1C1=CC=C(C)C=C1 SSVHGPAUAVUSSR-UHFFFAOYSA-N 0.000 claims 1
- IBZMKRPBSLWMMP-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[2-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound CCCNS(=O)(=O)C1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 IBZMKRPBSLWMMP-UHFFFAOYSA-N 0.000 claims 1
- ZPBFXCOEUXPALM-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[3-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound CCCNS(=O)(=O)C1=CC=CC(CC=2C3=CC(F)=CC=C3N(CC(O)=O)C=2C)=C1 ZPBFXCOEUXPALM-UHFFFAOYSA-N 0.000 claims 1
- QRVBQQHQTFGLNY-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(propylsulfamoyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 QRVBQQHQTFGLNY-UHFFFAOYSA-N 0.000 claims 1
- SSASRHIVLKIODJ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(trifluoromethoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(OC(F)(F)F)C=C1 SSASRHIVLKIODJ-UHFFFAOYSA-N 0.000 claims 1
- FSYLFZCDQZBNBD-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(trifluoromethyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C(F)(F)F)C=C1 FSYLFZCDQZBNBD-UHFFFAOYSA-N 0.000 claims 1
- MHDHXDHJMCCXBG-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-methylsulfonyl-3-(trifluoromethoxy)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C(OC(F)(F)F)=C1 MHDHXDHJMCCXBG-UHFFFAOYSA-N 0.000 claims 1
- ILFQESBYFFSFOP-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-methylsulfonyl-3-(trifluoromethyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 ILFQESBYFFSFOP-UHFFFAOYSA-N 0.000 claims 1
- QYJBPNZUHBMCDT-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[6-[[3-(trifluoromethyl)phenyl]methyl]pyridin-3-yl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=N1)=CC=C1CC1=CC=CC(C(F)(F)F)=C1 QYJBPNZUHBMCDT-UHFFFAOYSA-N 0.000 claims 1
- CJKAKAXEOWFTDV-UHFFFAOYSA-N 2-[5-fluoro-3-(imidazo[1,2-a]pyridin-2-ylmethyl)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN(C=CC=C2)C2=N1 CJKAKAXEOWFTDV-UHFFFAOYSA-N 0.000 claims 1
- RZEGYTODLNWOFL-UHFFFAOYSA-N 2-[5-fluoro-3-[(4-methoxyphenyl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RZEGYTODLNWOFL-UHFFFAOYSA-N 0.000 claims 1
- FOJBXYNSYGEMCI-UHFFFAOYSA-N 2-[5-fluoro-3-[(6-fluoroquinolin-2-yl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(F)C=C2)C2=N1 FOJBXYNSYGEMCI-UHFFFAOYSA-N 0.000 claims 1
- CIBHTCADKNJJQS-UHFFFAOYSA-N 2-[5-fluoro-3-[(8-hydroxyquinolin-2-yl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2O)C2=N1 CIBHTCADKNJJQS-UHFFFAOYSA-N 0.000 claims 1
- UDKGCWQLDVCYAR-UHFFFAOYSA-N 2-[5-fluoro-3-[[2-(4-fluorophenoxy)phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=CC=C1OC1=CC=C(F)C=C1 UDKGCWQLDVCYAR-UHFFFAOYSA-N 0.000 claims 1
- CCZUSMXZUULADP-UHFFFAOYSA-N 2-[5-fluoro-3-[[2-(4-methoxyphenoxy)phenyl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 CCZUSMXZUULADP-UHFFFAOYSA-N 0.000 claims 1
- UEGRDEKJWGHDCV-UHFFFAOYSA-N 2-[5-fluoro-3-[[4-(4-fluorobenzoyl)-1-methylpyrrol-2-yl]methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(N(C=1)C)=CC=1C(=O)C1=CC=C(F)C=C1 UEGRDEKJWGHDCV-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JJIUISYYTFDATN-UHFFFAOYSA-N 5-fluoro-2-methyl-1h-indole Chemical compound FC1=CC=C2NC(C)=CC2=C1 JJIUISYYTFDATN-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Postupak dobivanja spoja opće formule (I):
[image]
,
gdje je R1 fluor, klor ili brom;
R2 je C1-C6 alkil ili benzil; i
R3 je aril ili heteroaril, koji može biti supstituiran s jednim ili više supstituenata koje se bira između halogena, OH, CN, R4, COR4, CH2R4, OR4, SR4, SO2R4 ili SO2YR4;
R4 je C1-C6 alkil, C3-C8 cikloalkil, heterociklil, aril ili heteroaril, od kojih bilo koji može biti supstituiran s jednim ili više supstituenata koje se bira između halogena, OH, CN, NO2, C1-C6 alkila ili O(C1-C6 alkila); i
Y je NH ili nerazgranati ili razgranati C1-C4 alkilenski lanac;
naznačen time što se postupak sastoji u:
i. reakciji spoja opće formule (II):
[image]
,
gdje su R1 i R2 definirani kao za opću formulu (I);
sa spojem opće formule (III)
[image]
,
gdje je R3 definiran kao za opću formulu (I);
u pogodnom otapalu i u prisutnosti titanijevog tetraklorida, gdje se omjer između spoja opće formule (II) i otapala kreće od 1:8 to 1:20 težinski/volumno; i
ii. reakciji produkta iz koraka (i) s redukcijskim sredstvom kako bi se dobilo spoj opće formule (I).
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što, u spoju opće formule (I), neovisno ili u bilo kojoj kombinaciji:
R1 je fluor;
R2 je C1-C4 alkil, primjerice metil ili etil; i
R3 je kinolin, kinoksalin, izokinolin, tiazol, fenil, naftalen, tiofen, pirol ili piridin, od kojih bilo koji može biti supstituiran kao što je iznijeto u patentnom zahtjevu 1.
3. Postupak u skladu s patentnim zahtjevom 1 ili patentnim zahtjevom 2, naznačen time što je, u spoju opće formule (I), R3 kinolin, izokinolin, fenil, naftalen, tiofen, pirol ili piridin, od kojih bilo koji može biti supstituiran kao što je iznijeto u patentnom zahtjevu 1.
4. Postupak u skladu s patentnim zahtjevom 4, naznačen time što, u spoju opće formule (I):
R3 je kinolin ili izokinolin, od kojih bilo koji nije supstituiran ili je supstituiran s jednim ili više halogena kao supstituenata; ili
R3 je fenil, naftalen, tiofen, pirol ili piridin, od kojih bilo koji može biti supstituiran s jednim ili više supstituenata, koje se bira između OR4, SO2R4 ili SO2YR4;
gdje R4 i Y su definirani kao u patentnom zahtjevu 1.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u dobivanju spojeva formule (Ia):
[image]
,
gdje su R1 i R2 definirani kao u patentnom zahtjevu 1; i
R5 je vodik halogen, -CN, -C1-C6 alkil, -SOR7, -SO2R7, -SO2N(R6)2, -N(R6)2, -NR6C(O)R7, -CO2R6, -CONR6R7, -NO2, -OR6, -SR6, -O(CH2)pOR6, te -O(CH2)pO(CH2)qOR6, gdje
svaki R6 je neovisno vodik, -C1-C6 alkil, -C3-C8 cikloalkil, aril ili heteroaril;
svaki R7 je neovisno, -C1-C6 alkil, -C3-C8 cikloalkil, aril ili heteroaril;
svaki od p i q je neovisno cijeli broj od 1 do 3.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time što, u spoju opće formule (Ia), neovisno ili u kombinaciji:
R1 je fluor; i
R2 je metil ili etil; i
R5 je vodik, fluor ili klor.
7. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je namijenjen dobivanju C1-C6 alkilnog ili benzilnog estera:
(5-fluor-2-metil-3-kinolin-2-ilmetilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-naftalen-2-ilmetilindol-1-il)octene kiseline;
[5-fluor-3-(8-hidroksikinolin-2-ilmetil)-2-metilindol-1-il]octene kiseline;
[5-fluor-2-metil-3-(kinoksalin-2-ilmetil)indol-1-il]octene kiseline;
[5-fluor-3-(4-metoksibenzil)-2-metilindol-1-il]octene kiseline;
[5-fluor-2-metil-3-(1,3-tiazol-2-ilmetil)indol-1-il]octene kiseline;
[3-(4-klorbenzil)-5-fluor-2-metilindol-1-il]octene kiseline;
[5-fluor-2-metil-3-(4-trifluormetilbenzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(4-tert-butilbenzil)indol-1-il]octene kiseline;
{5-fluor-2-metil-3-[(4-fenilfenil)metil]indol-1-il}octene kiseline;
[5-fluor-3-(4-metansulfonilbenzil)-2-metilindol-1-il]octene kiseline;
{5-fluor-3-[(6-fluorkinolin-2-il)metil]-2-metilindol-1-il}octene kiseline;
(2-metil-3-kinolin-2-ilmetilindol-1-il)octene kiseline;
(5-klor-2-metil-3-kinolin-2-ilmetilindol-1-il)octene kiseline;
(3-{[1-(benzensulfonil)pirol-2-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
[5-fluor-2-metil-3-({1-[(4-metilbenzen)sulfonil]pirol-2-il}metil)indol-1-il]octene kiseline;
[3-({1-[(2,4-difluorbenzen)sulfonil]pirol-2-il}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
(3-{[2-(benzensulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
[3-({2-[(4-klorbenzen)sulfonil]fenil}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
[5-fluor-3-({2-[(4-fluorbenzen)sulfonil]fenil}metil)-2-metilindol-1-il]octene kiseline;
(3-{[2-(benzensulfonil)piridin-3-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
[5-fluor-3-({2-[(4-fluorbenzen)sulfonil]piridin-3-il}metil)-2-metilindol-1-il]octene kiseline;
[3-({2-[(4-klorbenzen)sulfonil]piridin-3-il}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
2-(3-(2-(cikloheksilsulfonil)benzil)-5-fluor-2-metilindol-1-il)octene kiseline;
2-(5-fluor-2-metil-3-(2-(piperidin-1-ilsulfonil)benzil)indol-1-il)octene kiseline;
2-(3-(2-(ciklopentilsulfonil)benzil)-5-fluor-2-metilindol-1-il)octene kiseline;
2-(5-fluor-2-metil-3-(3-(piperidin-1-ilsulfonil)benzil)indol-1-il)octene kiseline;
2-(5-fluor-2-metil-3-(2-(pirolidin-1-ilsulfonil)benzil)indol-1-il)octene kiseline;
2-(3-(4-(cikloheksilsulfonil)benzil)-5-fluor-2-metilindol-1-il)octene kiseline;
2-(3-(4-(ciklopentilsulfonil)benzil)-5-fluor-2-metilindol-1-il)octene kiseline;
2-(3-(2-(ciklobutilsulfonil)benzil)-5-fluor-2-metilindol-1-il)octene kiseline;
2-(5-fluor-2-metil-3-(3-(pirolidin-1-ilsulfonil)benzil)indol-1-il)octene kiseline;
2-(5-fluor-2-metil-3-(4-(piperidin-1-ilsulfonil)benzil)indol-1-il)octene kiseline;
[5-fluor-2-metil-3-(2-fenoksibenzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(4-metoksifenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(4-metilfenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(2,4-diklorfenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(4-fluorfenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(3,4-difluorfenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(4-cijanofenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(4-klorfenoksi)benzil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(2-(2-cijanofenoksi)benzil)indol-1-il]octene kiseline;
(5-fluor-2-metil-3-{[2-(4-metilfenoksi)piridin-3-il]metil}indol-1-il)octene kiseline;
{5-fluor-3-[(3-metansulfonilnaftalen-2-il)metil]-2-metilindol-1-il}octene kiseline;
{5-fluor-3-[(1-metansulfonilnaftalen-2-il)metil]-2-metilindol-1-il}octene kiseline;
{5-fluor-3-[(6-metansulfonilnaftalen-2-il)metil]-2-metilindol-1-il}octene kiseline;
[5-fluor-2-metil-3-(kinolin-3-ilmetil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(kinoksalin-6-ilmetil)indol-1-il]octene kiseline;
[5-fluor-2-metil-3-(kinolin-7-ilmetil)indol-1-il]octene kiseline;
{5-fluor-3-[(6-metansulfonilkinolin-2-il)metil]-2-metilindol-1-il}octene kiseline;
{5-fluor-3-[(4-metansulfonilkinolin-2-il)metil]-2-metilindol-1-il}octene kiseline;
(5-fluor-2-metil-3-{pirazolo[1,5-a]piridin-3-ilmetil}indol-1-il)octene kiseline;
(5-fluor-3-{imidazo[1,2-a]piridin-2-ilmetil}-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(metilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[3-(metilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(etilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(3-{[4-(etilsulfanil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(n-propilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(i-propilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(t-butilsulfanil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(pentan-3-ilsulfanil)fenil]metil}indol-1-il)octene kiseline;
[3-({4-[(ciklopropilmetil)sulfanil]fenil}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
{3-[(4,4-dimetil-2,3-dihidro-1-benzotiopiran-6-il)metil]-5-fluor-2-metilindol-1-il}octene kiseline;
(3-{[2-(etansulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(propan-1-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(propan-2-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(3-{[2-(butan-1-sulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(3-{[2-(butan-2-sulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(2-metilpropan-2-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(pentan-1-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(3-{[2-(ciklopropilmetan)sulfonilfenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(propilsulfamoil)fenil]metil}indol-1-il)octene kiseline;
(3-{[2-(butilsulfamoil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[3-(propilsulfamoil)fenil]metil}indol-1-il)octene kiseline;
(3-{[3-(butilsulfamoil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(trifluormetan)sulfonilfenil]metil}indol-1-il)octene kiseline;
(3-{[4-(etansulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(propan-1-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(propan-2-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(3-{[4-(butan-1-sulfonil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(2-metilpropan-2-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(pentan-1-sulfonil)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(pentan-3-ilsulfonil)fenil]metil}indol-1-il)octene kiseline;
[3-({4-[(ciklopropilmetil)sulfonil]fenil}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
(5-fluor-2-metil-3-{[4-(propilsulfamoil)fenil]metil}indol-1-il)octene kiseline;
(3-{[4-(butilsulfamoil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[4-(trifluormetoksi)fenil]metil}indol-1-il)octene kiseline;
(5-fluor-3-{[4-metansulfonil-3-(trifluormetil)fenil]metil}-2-metilindol-1-il)octene kiseline;
(5-fluor-3-{[4-metansulfonil-3-(trifluormetoksi)fenil]metil}-2-metilindol-1-il)octene kiseline;
{5-fluor-3-[(5-metansulfoniltiofen-2-il)metil]-2-metilindol-1-il}octene kiseline;
{3-[(4,4-dimetil-1,1-diokso-2,3-dihidro-1λ6-benzotiopiran-6-il)metil]-5-fluor-2-metilindol-1-il}octene kiseline;
[3-({1-[(4-klorbenzen)sulfonil]pirol-2-il}metil)-5-fluor-2-metilindol-1il]octene kiseline;
[5-fluor-3-({1-[(4-fluorbenzen)sulfonil]pirol-2-il}metil)-2-metilindol-1-il]octene kiseline;
[5-fluor-3-({1-[(4-metoksibenzen)sulfonil]pirol-2-il}metil)-2-metilindol-1-il]octene kiseline;
{3-[1-(2,4-diklorbenzensulfonil)pirol-2-ilmetil]-5-fluor-2-metilindol-1-il}octene kiseline;
[5-fluor-3-({1-[(4-metansulfonilbenzen)sulfonil]pirol-2-il}metil)-2-metilindol-1-il]octene kiseline;
{5-fluor-2-metil-3-[(2-fenilfenil)metil]indol-1-il}octene kiseline;
(3-{[1-(benzensulfonil)indol-2-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(3-{[2-(4-klorfenil)fenil]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
(5-fluor-2-metil-3-{[2-(4-metilfenil)fenil]metil}indol-1-il)octene kiseline;
{5-fluor-2-metil-3-[(3-fenoksifenil)metil]indol-1-il}octene kiseline;
[5-fluor-3-({4-[(4-fluorfenil)karbonil]-1-metilpirol-2-il}metil)-2-metilindol-1-il]octene kiseline;
{5-fluor-2-metil-3-[(6-{[3-(trifluormetil)fenil]metil}piridin-3-il)metil]indol-1-il}octene kiseline;
{5-fluor-2-metil-3-[(3-fenoksitiofen-2-il)metil]indol-1-il}octene kiseline;
(3-{[2-(benzensulfonil)-1,3-tiazol-5-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
{3-[(1-benzilpirazol-4-il)metil]-5-fluor-2-metilindol-1-il}octene kiseline;
(3-{[5-(4-klorfenoksi)-1-metil-3-(trifluormetil)pirazol-4-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
[3-({5-[(4-klorbenzen)sulfonil]furan-2-il}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
[3-({5-[(4-klorbenzen)sulfonil]tiofen-2-il}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
[3-({3-[(4-klorbenzen)sulfonil]tiofen-2-il}metil)-5-fluor-2-metilindol-1-il]octene kiseline;
{3-[(2-benzilfenil)metil]-5-fluor-2-metilindol-1-il}octena kiselina.
8. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je namijenjen dobivanju C1-C6 alkilnog ili benzilnog estera:
(3-{[2-(benzensulfonil)piridin-3-il]metil}-5-fluor-2-metilindol-1-il)octene kiseline;
[5-fluor-3-({2-[(4-fluorbenzen)sulfonil]piridin-3-il}metil)-2-metilindol-1-il]octene kiseline.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time što je otapalo halogenirano otapalo poput diklormetana.
10. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se omjer između spoja opće formule (II) i otapala kreće od 1:10 do 1:12 težinski/volumno.
11. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se molarni omjer između titanijevog tetraklorida i spoja formule (II) kreće od 1:1 do 3:1, primjerice otprilike 1,8:1 do 2,2:1.
12. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je reakcijska temperatura u koraku (i) –10 do 25 °C; i/ili
nakon dodavanja spojeva općih formula (II) i (III), gdje se reakcijsku smjesu miješa otprilike 12 do 18 sati.
13. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se, u koraku (ii), reduciranje provodi uz upotrebu trietilsilana.
14. Postupak u skladu s patentnim zahtjevom 13, naznačen time što se molarni omjer između trietilsilana i spoja opće formule (II) kreće od otprilike 2:1 do 4:1.
15. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što dodatno uključuje jedan ili više koraka:
(iii) izdvajanja i pročišćavanje spoja opće formule (I); i/ili
(iv) prevođenja spoja formule (I) u spoj opće formule (V):
gdje su R1 i R3 definirani kao u patentnom zahtjevu 1; i/ili
prije koraka (i), dobivanja spoja formule (II) postupkom koji se sastoji u:
reakciji 5-fluor-2-metilindola sa spojem formule (VI):
X-CH2-COOR1 (VI)
gdje je X izlazna skupina, a R1 je definiran kao za formulu (I).
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| GBGB1322273.2A GB201322273D0 (en) | 2013-12-17 | 2013-12-17 | Process |
| EP14814989.1A EP3083557B1 (en) | 2013-12-17 | 2014-12-12 | Process for the preparation of 3-substituted (indol-1-yl)-acetic acid esters |
| PCT/GB2014/053686 WO2015092372A1 (en) | 2013-12-17 | 2014-12-12 | Process for the preparation of 3-substituted (indol-1-yl)-acetic acid esters |
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| EP (1) | EP3083557B1 (hr) |
| JP (1) | JP6312179B2 (hr) |
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| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| WO2018014869A1 (zh) * | 2016-07-21 | 2018-01-25 | 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 |
| US20220184059A1 (en) | 2018-12-27 | 2022-06-16 | Chiesi Farmaceutici S.P.A. | Process for preparing spherical agglomerates of timapiprant |
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| JP2001247570A (ja) | 2000-03-08 | 2001-09-11 | Japan Tobacco Inc | インドール酢酸化合物及びその製造方法 |
| US6878522B2 (en) | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| AU2003231509A1 (en) | 2002-05-16 | 2003-12-02 | Shionogi And Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
| WO2003097042A1 (fr) | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Antagoniste de recepteur de pdg2 |
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| DE60306547T2 (de) | 2002-12-10 | 2007-06-28 | Wyeth | Substituierte 3-alkyl- und 3-arylalkyl-1h-indol-1-yl-essigsäure-derivate als plasminogen-aktivator |
| US7321001B2 (en) | 2002-12-20 | 2008-01-22 | Amgen Inc. | Asthma and allergic inflammation modulators |
| CA2542716A1 (en) | 2003-10-14 | 2005-05-06 | Oxagen Limited | Compounds having crth2 antagonist activity |
| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| GB0504150D0 (en) * | 2005-03-01 | 2005-04-06 | Oxagen Ltd | Microcrystalline material |
| GB0505048D0 (en) * | 2005-03-11 | 2005-04-20 | Oxagen Ltd | Compounds with PGD antagonist activity |
| GB0605743D0 (en) | 2006-03-22 | 2006-05-03 | Oxagen Ltd | Salts with CRTH2 antagonist activity |
| PL2046740T3 (pl) | 2006-07-22 | 2012-10-31 | Oxagen Ltd | Związki o aktywności antagonisty CRTH2 |
| US20110124683A1 (en) | 2007-11-13 | 2011-05-26 | Oxagen Limited | Use of CRTH2 Antagonist Compounds |
| EP2327693B9 (en) * | 2007-12-14 | 2012-10-24 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| AU2009204700B2 (en) | 2008-01-18 | 2013-07-04 | Atopix Therapeutics Limited | Compounds having CRTH2 antagonist activity |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| 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 |
| EP2265581A1 (en) * | 2008-01-22 | 2010-12-29 | Oxagen Limited | Compounds having crth2 antagonist activity |
| WO2010142934A1 (en) * | 2009-06-12 | 2010-12-16 | Pulmagen Therapeutics (Asthma) Limited | Indole derivatives as ligands of crth2 receptors |
| WO2011055270A1 (en) * | 2009-11-04 | 2011-05-12 | Wyeth Llc | Indole based receptor crth2 antagonists |
| 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 |
| 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 |
-
2013
- 2013-12-17 GB GBGB1322273.2A patent/GB201322273D0/en not_active Ceased
-
2014
- 2014-12-12 WO PCT/GB2014/053686 patent/WO2015092372A1/en active Application Filing
- 2014-12-12 DK DK14814989.1T patent/DK3083557T3/en active
- 2014-12-12 HU HUE14814989A patent/HUE036184T2/hu unknown
- 2014-12-12 EP EP14814989.1A patent/EP3083557B1/en active Active
- 2014-12-12 JP JP2016560049A patent/JP6312179B2/ja not_active Expired - Fee Related
- 2014-12-12 TR TR2018/02657T patent/TR201802657T4/tr unknown
- 2014-12-12 RU RU2016125326A patent/RU2676332C1/ru active
- 2014-12-12 PT PT148149891T patent/PT3083557T/pt unknown
- 2014-12-12 NO NO14814989A patent/NO3083557T3/no unknown
- 2014-12-12 PL PL14814989T patent/PL3083557T3/pl unknown
- 2014-12-12 SI SI201430614T patent/SI3083557T1/en unknown
- 2014-12-12 ES ES14814989.1T patent/ES2660467T3/es active Active
- 2014-12-12 US US15/307,998 patent/US9828359B2/en active Active
- 2014-12-12 UA UAA201607416A patent/UA117849C2/uk unknown
-
2018
- 2018-02-19 HR HRP20180298TT patent/HRP20180298T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3083557A1 (en) | 2016-10-26 |
| PT3083557T (pt) | 2018-03-05 |
| NO3083557T3 (hr) | 2018-04-28 |
| DK3083557T3 (en) | 2018-03-12 |
| EP3083557B1 (en) | 2017-11-29 |
| PL3083557T3 (pl) | 2018-05-30 |
| JP2017501222A (ja) | 2017-01-12 |
| US9828359B2 (en) | 2017-11-28 |
| UA117849C2 (uk) | 2018-10-10 |
| SI3083557T1 (en) | 2018-04-30 |
| JP6312179B2 (ja) | 2018-04-18 |
| WO2015092372A1 (en) | 2015-06-25 |
| HUE036184T2 (hu) | 2018-06-28 |
| RU2676332C1 (ru) | 2018-12-28 |
| ES2660467T3 (es) | 2018-03-22 |
| GB201322273D0 (en) | 2014-01-29 |
| TR201802657T4 (tr) | 2018-03-21 |
| US20170305879A1 (en) | 2017-10-26 |
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