JP2007520471A

JP2007520471A - Ｐｐａｒ受容体調節物質としての二環式誘導体

Ｐｐａｒ受容体調節物質としての二環式誘導体 Download PDF

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Publication number: JP2007520471A
Authority: JP; Japan
Prior art keywords: methyl; alkyl; trifluoromethylphenyl; indazol; propionic acid
Prior art date: 2003-12-22
Legal status : Pending

Application number

JP2006547017A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007520471A5 (https=

Inventor

スコット・ユージーン・コナー

ネイサン・ブライアン・マントロ

チュ・グオシン

ロバート・ジェイソン・ハー

Original Assignee

イーライリリーアンドカンパニー

Priority date

2003-12-22

Filing date

2004-12-16

Publication date

2007-07-26

2004-12-16 Application filed by イーライリリーアンドカンパニー filed Critical イーライリリーアンドカンパニー

2007-07-26 Publication of JP2007520471A publication Critical patent/JP2007520471A/ja

2007-11-29 Publication of JP2007520471A5 publication Critical patent/JP2007520471A5/ja

Status Pending legal-status Critical Current

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102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title claims description 21
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title claims description 21
125000002619 bicyclic group Chemical group 0.000 title claims description 16
229910052799 carbon Inorganic materials 0.000 claims abstract description 73
125000000217 alkyl group Chemical group 0.000 claims abstract description 57
125000001424 substituent group Chemical group 0.000 claims abstract description 34
229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 23
239000012453 solvate Substances 0.000 claims abstract description 11
150000004677 hydrates Chemical class 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 236
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 139
229910052739 hydrogen Inorganic materials 0.000 claims description 91
239000001257 hydrogen Substances 0.000 claims description 90
-1 -C 0-4 - alkyl Chemical group 0.000 claims description 85
229910052757 nitrogen Inorganic materials 0.000 claims description 75
238000000034 method Methods 0.000 claims description 71
150000002431 hydrogen Chemical class 0.000 claims description 69
238000004519 manufacturing process Methods 0.000 claims description 66
125000003118 aryl group Chemical group 0.000 claims description 52
238000011282 treatment Methods 0.000 claims description 42
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 28
125000004104 aryloxy group Chemical group 0.000 claims description 27
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
239000004480 active ingredient Substances 0.000 claims description 24
229920006395 saturated elastomer Polymers 0.000 claims description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
241000124008 Mammalia Species 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 15
230000002265 prevention Effects 0.000 claims description 15
108010015181 PPAR delta Proteins 0.000 claims description 14
125000004043 oxo group Chemical group O=* 0.000 claims description 13
150000003536 tetrazoles Chemical class 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
206010012601 diabetes mellitus Diseases 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
229940124530 sulfonamide Drugs 0.000 claims description 12
150000003456 sulfonamides Chemical class 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
235000019260 propionic acid Nutrition 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 8
208000001145 Metabolic Syndrome Diseases 0.000 claims description 8
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
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 description 7
150000001721 carbon Chemical group 0.000 claims description 7
150000003857 carboxamides Chemical class 0.000 claims description 7
208000024172 Cardiovascular disease Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
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 description 6
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 description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
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 description 4
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 description 4
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 description 4
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 description 4
230000001404 mediated effect Effects 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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229960005542 ethidium bromide Drugs 0.000 description 1
VAOSKCGWYDFNMS-UHFFFAOYSA-N ethyl 2-(2-ethyl-4-phenylmethoxyphenyl)sulfanylacetate Chemical compound C1=C(CC)C(SCC(=O)OCC)=CC=C1OCC1=CC=CC=C1 VAOSKCGWYDFNMS-UHFFFAOYSA-N 0.000 description 1
CQIYJSOLYQGGCQ-UHFFFAOYSA-N ethyl 2-(2-ethyl-4-sulfanylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(S)C=C1CC CQIYJSOLYQGGCQ-UHFFFAOYSA-N 0.000 description 1
YTGXRXMYWHMTHT-UHFFFAOYSA-N ethyl 2-(2-formyl-4-phenylmethoxyphenoxy)-2-methylpropanoate;2-hydroxy-5-phenylmethoxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1OCC1=CC=CC=C1.C1=C(C=O)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 YTGXRXMYWHMTHT-UHFFFAOYSA-N 0.000 description 1
XOUAZXWNXSRHIP-UHFFFAOYSA-N ethyl 2-(2-formyl-4-phenylmethoxyphenoxy)-2-methylpropanoate;ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(O)C=C1C.C1=C(C=O)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 XOUAZXWNXSRHIP-UHFFFAOYSA-N 0.000 description 1
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PSCHCBLKRYUWHK-UHFFFAOYSA-N ethyl 2-(4-hydroxy-1-benzothiophen-3-yl)acetate Chemical compound C1=CC(O)=C2C(CC(=O)OCC)=CSC2=C1 PSCHCBLKRYUWHK-UHFFFAOYSA-N 0.000 description 1
RFSIKEBTOFOSPM-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(O)C=C1C RFSIKEBTOFOSPM-UHFFFAOYSA-N 0.000 description 1
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PBQNKBWWOXOAOE-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(O)C=C1 PBQNKBWWOXOAOE-UHFFFAOYSA-N 0.000 description 1
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QYBCKYRNAYJTMC-UHFFFAOYSA-N ethyl 2-(4-phenylmethoxy-2-propylphenoxy)acetate Chemical compound C1=C(OCC(=O)OCC)C(CCC)=CC(OCC=2C=CC=CC=2)=C1 QYBCKYRNAYJTMC-UHFFFAOYSA-N 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
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238000005040 ion trap Methods 0.000 description 1
LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
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AQLZXFRETNWDQU-UHFFFAOYSA-N methyl 2-(3-chloro-4-sulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(S)C(Cl)=C1 AQLZXFRETNWDQU-UHFFFAOYSA-N 0.000 description 1
NLPRPUVYIZIMMA-UHFFFAOYSA-N methyl 2-(3-hydroxy-4-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C(O)=C1 NLPRPUVYIZIMMA-UHFFFAOYSA-N 0.000 description 1
AMDDOQIUPAINLH-UHFFFAOYSA-N methyl 2-(3-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(O)=C1 AMDDOQIUPAINLH-UHFFFAOYSA-N 0.000 description 1
BSVIOYCZTJRBDB-UHFFFAOYSA-N methyl 2-(3-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(OC)=C1 BSVIOYCZTJRBDB-UHFFFAOYSA-N 0.000 description 1
FWHNDYVYVYLGPZ-UHFFFAOYSA-N methyl 2-(4-bromo-2-methylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(Br)C=C1C FWHNDYVYVYLGPZ-UHFFFAOYSA-N 0.000 description 1
ZBQBSRXDNRKDPZ-UHFFFAOYSA-N methyl 2-(4-hydroxy-2-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1C ZBQBSRXDNRKDPZ-UHFFFAOYSA-N 0.000 description 1
XXTWNWQHEGVDMQ-UHFFFAOYSA-N methyl 2-(4-methoxy-2-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C=C1C XXTWNWQHEGVDMQ-UHFFFAOYSA-N 0.000 description 1
BRYPZFFZTRQJSU-UHFFFAOYSA-N methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate Chemical compound OC1=CC=C2C(CC(=O)OC)=COC2=C1 BRYPZFFZTRQJSU-UHFFFAOYSA-N 0.000 description 1
HIZAWDWPLNYOKB-UHFFFAOYSA-N methyl 2-(6-hydroxy-1-benzofuran-3-yl)propanoate Chemical compound OC1=CC=C2C(C(C)C(=O)OC)=COC2=C1 HIZAWDWPLNYOKB-UHFFFAOYSA-N 0.000 description 1
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
YQEYSEPPEQWDFF-UHFFFAOYSA-N methyl 2-[4-(trifluoromethyl)phenyl]indazole-7-carboxylate Chemical compound N1=C2C(C(=O)OC)=CC=CC2=CN1C1=CC=C(C(F)(F)F)C=C1 YQEYSEPPEQWDFF-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
XFKHALKYWCYHCD-UHFFFAOYSA-N methyl 3-(2-methyl-4-nitrophenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C([N+]([O-])=O)C=C1C XFKHALKYWCYHCD-UHFFFAOYSA-N 0.000 description 1
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IIFOKIAATXLZIB-UHFFFAOYSA-N methyl 3-(3-hydroxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC(O)=C1 IIFOKIAATXLZIB-UHFFFAOYSA-N 0.000 description 1
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