JP2007520471A5 - - Google Patents
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- JP2007520471A5 JP2007520471A5 JP2006547017A JP2006547017A JP2007520471A5 JP 2007520471 A5 JP2007520471 A5 JP 2007520471A5 JP 2006547017 A JP2006547017 A JP 2006547017A JP 2006547017 A JP2006547017 A JP 2006547017A JP 2007520471 A5 JP2007520471 A5 JP 2007520471A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- indazol
- trifluoromethylphenyl
- propionic acid
- phenoxy
- 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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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 235000019260 propionic acid Nutrition 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- -1 -C 0-4 - alkyl Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- GMMOIQSFPBOOTI-UHFFFAOYSA-N 2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]propan-2-ylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SC(C)(C)C=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 GMMOIQSFPBOOTI-UHFFFAOYSA-N 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- HEYFPYHYFHXAGU-UHFFFAOYSA-N 2-[2-ethyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HEYFPYHYFHXAGU-UHFFFAOYSA-N 0.000 claims 1
- VCJCZRTWAWRMON-UHFFFAOYSA-N 2-[2-ethyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]propan-2-ylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SC(C)(C)C=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 VCJCZRTWAWRMON-UHFFFAOYSA-N 0.000 claims 1
- BNUQKCHWJZTIRF-UHFFFAOYSA-N 2-[2-ethyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC=2C=3C=NN(C=3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 BNUQKCHWJZTIRF-UHFFFAOYSA-N 0.000 claims 1
- XOEGGOQAHZGSMM-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC=2C3=CN(N=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 XOEGGOQAHZGSMM-UHFFFAOYSA-N 0.000 claims 1
- SRVKTRVJFZTRQK-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 SRVKTRVJFZTRQK-UHFFFAOYSA-N 0.000 claims 1
- DHLKCFVQRRXHQT-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 DHLKCFVQRRXHQT-UHFFFAOYSA-N 0.000 claims 1
- BAXSFWOVOKKTPB-UHFFFAOYSA-N 2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 BAXSFWOVOKKTPB-UHFFFAOYSA-N 0.000 claims 1
- ADZWRPXAVGJZAA-UHFFFAOYSA-N 2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C=3C=NN(C=3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ADZWRPXAVGJZAA-UHFFFAOYSA-N 0.000 claims 1
- UCBVPBLQBCGADY-UHFFFAOYSA-N 2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C=3N(C=4C=CC(=CC=4)C(F)(F)F)N=CC=3C=CC=2)=C1 UCBVPBLQBCGADY-UHFFFAOYSA-N 0.000 claims 1
- MNHXIMPCRADUFN-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C3=CN(N=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MNHXIMPCRADUFN-UHFFFAOYSA-N 0.000 claims 1
- JZMXGHPFKXLNLM-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 JZMXGHPFKXLNLM-UHFFFAOYSA-N 0.000 claims 1
- NGALIMPWXCFKGZ-UHFFFAOYSA-N 2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 NGALIMPWXCFKGZ-UHFFFAOYSA-N 0.000 claims 1
- IUCCPORPLJVARU-UHFFFAOYSA-N 2-[3-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(SCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 IUCCPORPLJVARU-UHFFFAOYSA-N 0.000 claims 1
- CEIZPPQGLOXSJV-UHFFFAOYSA-N 2-[6-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]propan-2-ylsulfanyl]-1-benzothiophen-3-yl]acetic acid Chemical compound C=1C=C2C(CC(O)=O)=CSC2=CC=1SC(C)(C)C(C1=N2)=CC=CC1=CN2C1=CC=C(C(F)(F)F)C=C1 CEIZPPQGLOXSJV-UHFFFAOYSA-N 0.000 claims 1
- NOTVSFJORAFKLS-UHFFFAOYSA-N 2-[6-[[2-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]-1-benzothiophen-3-yl]acetic acid Chemical compound C=1C=C2C(CC(=O)O)=CSC2=CC=1SCC(C1=C2)=CC=CC1=NN2C1=CC=C(C(F)(F)F)C=C1 NOTVSFJORAFKLS-UHFFFAOYSA-N 0.000 claims 1
- KLXPEKYHCMKVDT-UHFFFAOYSA-N 2-[6-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]-1-benzothiophen-3-yl]acetic acid Chemical compound C=1C=C2C(CC(=O)O)=CSC2=CC=1OCC(=CC1=N2)C=CC1=CN2C1=CC=C(C(F)(F)F)C=C1 KLXPEKYHCMKVDT-UHFFFAOYSA-N 0.000 claims 1
- XITVJBWTMPLXHV-UHFFFAOYSA-N 2-[6-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]-1-benzothiophen-3-yl]acetic acid Chemical compound C=1C=C2C(CC(=O)O)=CSC2=CC=1SCC(=CC1=N2)C=CC1=CN2C1=CC=C(C(F)(F)F)C=C1 XITVJBWTMPLXHV-UHFFFAOYSA-N 0.000 claims 1
- FZSGXKBSICCODJ-UHFFFAOYSA-N 2-[6-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]-1-benzothiophen-3-yl]acetic acid Chemical compound C=1C=C2C(CC(=O)O)=CSC2=CC=1SCC(C1=N2)=CC=CC1=CN2C1=CC=C(C(F)(F)F)C=C1 FZSGXKBSICCODJ-UHFFFAOYSA-N 0.000 claims 1
- CBYOTDJCGUYQEJ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 CBYOTDJCGUYQEJ-UHFFFAOYSA-N 0.000 claims 1
- GHROGUFFYOWKPT-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 GHROGUFFYOWKPT-UHFFFAOYSA-N 0.000 claims 1
- CREVTZMIQPBDJM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2C=3C=NN(C=3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 CREVTZMIQPBDJM-UHFFFAOYSA-N 0.000 claims 1
- LFTYTQVEKLEMNM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2C=3C=NN(C=3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 LFTYTQVEKLEMNM-UHFFFAOYSA-N 0.000 claims 1
- LIULBYXLJAUJMJ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2C=3N(C=4C=CC(=CC=4)C(F)(F)F)N=CC=3C=CC=2)=C1 LIULBYXLJAUJMJ-UHFFFAOYSA-N 0.000 claims 1
- BIVLGXYFZSQSRR-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2C=3N(C=4C=CC(=CC=4)C(F)(F)F)N=CC=3C=CC=2)=C1 BIVLGXYFZSQSRR-UHFFFAOYSA-N 0.000 claims 1
- MFUHATHPSKBWOJ-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2C3=CN(N=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MFUHATHPSKBWOJ-UHFFFAOYSA-N 0.000 claims 1
- OBDFDFWYSGTNLA-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-5-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC2=CC3=CN(N=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 OBDFDFWYSGTNLA-UHFFFAOYSA-N 0.000 claims 1
- SZMUBBJXRMEHKE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=CC3=CN(N=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 SZMUBBJXRMEHKE-UHFFFAOYSA-N 0.000 claims 1
- OPAXOYQIWNMWFR-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 OPAXOYQIWNMWFR-UHFFFAOYSA-N 0.000 claims 1
- VLUMATJUAYOJFX-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 VLUMATJUAYOJFX-UHFFFAOYSA-N 0.000 claims 1
- CHFARYBOBCZMJY-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 CHFARYBOBCZMJY-UHFFFAOYSA-N 0.000 claims 1
- HJNQHFMIVPKWEO-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HJNQHFMIVPKWEO-UHFFFAOYSA-N 0.000 claims 1
- CVGCLGWIYDAFKX-UHFFFAOYSA-N 2-methyl-2-[4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCCC1=CC=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C12 CVGCLGWIYDAFKX-UHFFFAOYSA-N 0.000 claims 1
- RAEHVCAGKCCWEW-UHFFFAOYSA-N 2-methyl-2-[4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]ethylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCCC1=CC=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C12 RAEHVCAGKCCWEW-UHFFFAOYSA-N 0.000 claims 1
- JFVSAJUYMOZBCV-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=C1C=NN2C1=CC=C(C(F)(F)F)C=C1 JFVSAJUYMOZBCV-UHFFFAOYSA-N 0.000 claims 1
- ZBAJBWNXONTYOM-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=C1C=NN2C1=CC=C(C(F)(F)F)C=C1 ZBAJBWNXONTYOM-UHFFFAOYSA-N 0.000 claims 1
- PDHDRQVCHFPHLK-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=CC=CC2=C1C=NN2C1=CC=C(C(F)(F)F)C=C1 PDHDRQVCHFPHLK-UHFFFAOYSA-N 0.000 claims 1
- QQCXVXNHDASMEY-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=C1N(C=1C=CC(=CC=1)C(F)(F)F)N=C2 QQCXVXNHDASMEY-UHFFFAOYSA-N 0.000 claims 1
- XIKURQVVIGSZPO-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=C1N(C=1C=CC(=CC=1)C(F)(F)F)N=C2 XIKURQVVIGSZPO-UHFFFAOYSA-N 0.000 claims 1
- KSPHSMYGMLZPEL-UHFFFAOYSA-N 2-methyl-2-[4-[[1-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=CC=CC2=C1N(C=1C=CC(=CC=1)C(F)(F)F)N=C2 KSPHSMYGMLZPEL-UHFFFAOYSA-N 0.000 claims 1
- ICQBZCXONGKJSG-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-5-yl]methoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SC(C)(C)C(O)=O)=CC=C1OCC1=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C2C=C1 ICQBZCXONGKJSG-UHFFFAOYSA-N 0.000 claims 1
- MWHZEMQECNDBJA-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-5-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C2C=C1 MWHZEMQECNDBJA-UHFFFAOYSA-N 0.000 claims 1
- SLILNTZNRZDVNY-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCC1=CC2=NN(C=3C=CC(=CC=3)C(F)(F)F)C=C2C=C1 SLILNTZNRZDVNY-UHFFFAOYSA-N 0.000 claims 1
- QAFSSMFURMQHHT-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SC(C)(C)C(O)=O)=CC=C1OCC1=CC2=NN(C=3C=CC(=CC=3)C(F)(F)F)C=C2C=C1 QAFSSMFURMQHHT-UHFFFAOYSA-N 0.000 claims 1
- FMSUJTYAPFQQRP-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxymethyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1COCC1=CC2=NN(C=3C=CC(=CC=3)C(F)(F)F)C=C2C=C1 FMSUJTYAPFQQRP-UHFFFAOYSA-N 0.000 claims 1
- KHOMIEGIJBHNEZ-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=CC2=NN(C=3C=CC(=CC=3)C(F)(F)F)C=C2C=C1 KHOMIEGIJBHNEZ-UHFFFAOYSA-N 0.000 claims 1
- JMMCHBMNIHXLTJ-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C12 JMMCHBMNIHXLTJ-UHFFFAOYSA-N 0.000 claims 1
- VXGUKZZEEJIOLV-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C12 VXGUKZZEEJIOLV-UHFFFAOYSA-N 0.000 claims 1
- JBMZYUOCHDHYOF-UHFFFAOYSA-N 2-methyl-2-[4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1SCC1=CC=CC2=CN(C=3C=CC(=CC=3)C(F)(F)F)N=C12 JBMZYUOCHDHYOF-UHFFFAOYSA-N 0.000 claims 1
- QLBMLIXYQOYNPA-UHFFFAOYSA-N 3-[2-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(CC)=CC(OCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 QLBMLIXYQOYNPA-UHFFFAOYSA-N 0.000 claims 1
- ADHYCPCVLOYACY-UHFFFAOYSA-N 3-[2-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(CC)=CC(OCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ADHYCPCVLOYACY-UHFFFAOYSA-N 0.000 claims 1
- ZPGOIRJLLNBVNA-UHFFFAOYSA-N 3-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]propan-2-ylsulfanyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(SC(C)(C)C=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ZPGOIRJLLNBVNA-UHFFFAOYSA-N 0.000 claims 1
- GIXLVJLJWLCHDG-UHFFFAOYSA-N 3-[2-methyl-4-[[1-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(SCC=2C=3C=NN(C=3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 GIXLVJLJWLCHDG-UHFFFAOYSA-N 0.000 claims 1
- LJTXVVQVENUQTJ-UHFFFAOYSA-N 3-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-4-yl]methylsulfanyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(SCC=2C3=CN(N=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 LJTXVVQVENUQTJ-UHFFFAOYSA-N 0.000 claims 1
- LSTJQEADFSLMIW-UHFFFAOYSA-N 3-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 LSTJQEADFSLMIW-UHFFFAOYSA-N 0.000 claims 1
- SVFGMPRWUSSUMR-UHFFFAOYSA-N 3-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-6-yl]methylsulfanyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(SCC2=CC3=NN(C=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 SVFGMPRWUSSUMR-UHFFFAOYSA-N 0.000 claims 1
- CKQXWDXMVJIQHX-UHFFFAOYSA-N 3-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(OCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 CKQXWDXMVJIQHX-UHFFFAOYSA-N 0.000 claims 1
- PUTFMSLXIMINGD-UHFFFAOYSA-N 3-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]indazol-7-yl]methylsulfanyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(C)=CC(SCC=2C3=NN(C=C3C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 PUTFMSLXIMINGD-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
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| US53213903P | 2003-12-22 | 2003-12-22 | |
| US58667704P | 2004-07-09 | 2004-07-09 | |
| PCT/US2004/039773 WO2005066136A1 (en) | 2003-12-22 | 2004-12-16 | Bicyclic derivatives as ppar modulators |
Publications (2)
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| JP2007520471A JP2007520471A (ja) | 2007-07-26 |
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| CA2624176A1 (en) * | 2005-09-29 | 2007-04-05 | Inpharmatica Limited | Condensed pyrazole derivatives as ppar agonists ii |
| GB0606663D0 (en) * | 2006-04-03 | 2006-05-10 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| CA2647545C (en) * | 2006-04-03 | 2016-02-23 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Amide substituted indazole and benzotriazole derivatives as poly(adp-ribose)polymerase (parp) inhibitors |
| EP2805945B1 (en) | 2007-01-10 | 2019-04-03 | MSD Italia S.r.l. | Amide substituted indazoles as poly(ADP-ribose)polymerase (PARP) inhibitors |
| JP5989965B2 (ja) | 2008-01-08 | 2016-09-07 | メルク シャープ エンド ドーム リミテッド | ２−｛４−［（３ｓ）−ピペリジン−３−イル］フェニル｝−２ｈ−インダゾール−７−カルボキサミドの薬学的に許容される塩 |
| MX2010013608A (es) * | 2008-06-11 | 2011-03-29 | Genentech Inc Star | Pirroles sustituidos y metodos de uso. |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| WO2012030165A2 (ko) | 2010-08-31 | 2012-03-08 | 서울대학교산학협력단 | P P A R δ 활성물질의 태자재프로그래밍용도 |
| US8957093B2 (en) | 2011-06-06 | 2015-02-17 | The Scripps Research Institute | N-biphenylmethylindole modulators of PPARG |
| US9051265B2 (en) | 2011-06-06 | 2015-06-09 | The Scripps Research Institute | N-benzylindole modulators of PPARG |
| WO2013078240A1 (en) * | 2011-11-22 | 2013-05-30 | Ripka Amy S | N-biphenylmethylbenzimidazole modulators of pparg |
| US20140288090A1 (en) * | 2011-11-22 | 2014-09-25 | Theodore Mark Kamenecka | N-arylylmethylindazole modulators of pparg |
| TWI692469B (zh) | 2012-11-09 | 2020-05-01 | 南韓商Ｌｇ化學股份有限公司 | Ｇｐｒ４０受體促效劑，製造該促效劑的方法以及含有該促效劑作爲活性劑的醫藥組成物 |
| CA2905729C (en) | 2013-03-14 | 2021-11-09 | Janssen Pharmaceutica Nv | Bicyclic pyrrole derivatives useful as agonists of gpr120 |
| WO2014159054A1 (en) | 2013-03-14 | 2014-10-02 | Janssen Pharmaceutica Nv | Gpr120 agonists for the treatment of type ii diabetes |
| EP2970157B1 (en) | 2013-03-14 | 2018-04-25 | Janssen Pharmaceutica NV | Benzo-fused heterocyclic derivatives useful as agonists of gpr120 |
| CN103508895B (zh) * | 2013-09-18 | 2015-01-21 | 苏州乔纳森新材料科技有限公司 | 一种4-醛基-3-硝基苯甲酸甲酯的制备方法 |
| TW201609722A (zh) * | 2013-12-13 | 2016-03-16 | 美國禮來大藥廠 | 新穎三唑并吡啶化合物 |
| US9067898B1 (en) | 2014-03-07 | 2015-06-30 | Janssen Pharmaceutica Nv | Isothiazole derivatives as GPR120 agonists for the treatment of type II diabetes |
| US8912227B1 (en) | 2014-03-07 | 2014-12-16 | Janssen Pharmaceutica Nv | Bicyclic pyrrole derivatives useful as agonists of GPR120 |
| WO2015161108A1 (en) | 2014-04-16 | 2015-10-22 | The Scripps Research Institute | Pparg modulators for treatment of osteoporosis |
| JP2019006680A (ja) * | 2015-11-13 | 2019-01-17 | 国立大学法人大阪大学 | ピラゾロピリジン誘導体およびその使用 |
| TW201815766A (zh) | 2016-09-22 | 2018-05-01 | 美商普雷辛肯公司 | 用於ｉｄｏ及ｔｄｏ調節之化合物及方法以及其適應症 |
| JP2021518367A (ja) | 2018-03-20 | 2021-08-02 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | Ｉｄｏおよびｔｄｏ調節のための化合物および方法、ならびにそれらのための兆候 |
| WO2020072796A1 (en) | 2018-10-03 | 2020-04-09 | Tesaro, Inc. | Crystalline forms of niraparib freebase |
| CN110407704B (zh) * | 2019-08-19 | 2022-05-17 | 常州沃腾化工科技有限公司 | 一种3-甲酰基-2-硝基苯甲酸甲酯的合成方法 |
| FI4097099T3 (fi) | 2020-02-07 | 2024-07-30 | Gasherbrum Bio Inc | Heterosyklisiä glp-1-agonisteja |
| CN113387971B (zh) * | 2021-04-19 | 2023-10-27 | 安徽普利药业有限公司 | 克立硼罗的合成方法 |
| AU2024222719A1 (en) | 2023-02-16 | 2025-08-21 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| KR102925481B1 (ko) * | 2023-09-05 | 2026-02-10 | 광주과학기술원 | 신규 화합물 및 이의 건선 치료 용도 |
Family Cites Families (5)
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| ATE236137T1 (de) * | 1996-02-02 | 2003-04-15 | Merck & Co Inc | Heterocyclische verbindungen als antidiabetische mittel und für die behandlung von fettleibigkeit |
| US6897231B2 (en) * | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
| AU2002255263B2 (en) | 2001-04-16 | 2006-12-14 | Eisai R&D Management Co., Ltd. | Novel 1H-indazole compound |
| US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| WO2004063155A1 (en) * | 2003-01-06 | 2004-07-29 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
-
2004
- 2004-12-16 WO PCT/US2004/039773 patent/WO2005066136A1/en not_active Ceased
- 2004-12-16 US US10/596,322 patent/US7544707B2/en not_active Expired - Fee Related
- 2004-12-16 JP JP2006547017A patent/JP2007520471A/ja active Pending
- 2004-12-16 EP EP04812319A patent/EP1706386A1/en not_active Withdrawn
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