AU2005214349B2 - Substituted azole derivatives, compositions, and methods of use - Google Patents
Substituted azole derivatives, compositions, and methods of use Download PDFInfo
- Publication number
- AU2005214349B2 AU2005214349B2 AU2005214349A AU2005214349A AU2005214349B2 AU 2005214349 B2 AU2005214349 B2 AU 2005214349B2 AU 2005214349 A AU2005214349 A AU 2005214349A AU 2005214349 A AU2005214349 A AU 2005214349A AU 2005214349 B2 AU2005214349 B2 AU 2005214349B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- dichloro
- imidazol
- biphenyl
- ylmethyl
- 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.)
- Ceased
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- 238000000034 method Methods 0.000 title claims abstract description 582
- 150000007980 azole derivatives Chemical class 0.000 title abstract description 7
- 239000000203 mixture Chemical class 0.000 title description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 162
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 62
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
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- 239000003112 inhibitor Substances 0.000 claims abstract description 14
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 423
- -1 isoxazol-3-ol-5-yl Chemical group 0.000 claims description 391
- 239000005711 Benzoic acid Substances 0.000 claims description 312
- 125000000217 alkyl group Chemical group 0.000 claims description 164
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 239000002253 acid Substances 0.000 claims description 85
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 84
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 239000003937 drug carrier Substances 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
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- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 12
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- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 5
- 229920001268 Cholestyramine Polymers 0.000 claims description 5
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims description 5
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims description 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 5
- 229940122355 Insulin sensitizer Drugs 0.000 claims description 5
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- 229960002632 acarbose Drugs 0.000 claims description 5
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 5
- 229930013930 alkaloid Natural products 0.000 claims description 5
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
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- HSROEKDCBORKAF-OVCLIPMQSA-N 4-[[4-(2,4-difluorophenyl)-2-[(e)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(F)=CC=2)F)=C1 HSROEKDCBORKAF-OVCLIPMQSA-N 0.000 claims description 3
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940126033 PPAR agonist Drugs 0.000 claims description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 230000000561 anti-psychotic effect Effects 0.000 claims description 3
- 229960003965 antiepileptics Drugs 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 3
- RIXQNBZYAOTNAH-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(trifluoromethyl)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 RIXQNBZYAOTNAH-UHFFFAOYSA-N 0.000 claims description 3
- BNJUVNAHELIDJJ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 BNJUVNAHELIDJJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 3
- KOEQTENTJFSOHT-CXUHLZMHSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(3-methylsulfonylphenyl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=CC(\C=C\C=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)CC=3C=CC(=CC=3)C(O)=O)=CC=2)=C1 KOEQTENTJFSOHT-CXUHLZMHSA-N 0.000 claims description 2
- VQCXCIIBIOEJFX-OVCLIPMQSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 VQCXCIIBIOEJFX-OVCLIPMQSA-N 0.000 claims description 2
- UUWVTNCNELQWLK-FZSIALSZSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UUWVTNCNELQWLK-FZSIALSZSA-N 0.000 claims description 2
- GGOIDUCNVZOMHK-UHFFFAOYSA-N 4-[[4-(2,4-dichlorophenyl)-2-[2-[4-[4-(trifluoromethyl)phenyl]phenyl]ethyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(CCC=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 GGOIDUCNVZOMHK-UHFFFAOYSA-N 0.000 claims description 2
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- XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims 1
- PAGBHTZDVXZRCN-OVCLIPMQSA-N 4-[[2-[(e)-2-[4-(3-cyanophenyl)phenyl]ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C#N)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 PAGBHTZDVXZRCN-OVCLIPMQSA-N 0.000 claims 1
- ASXCPWOLCBTNNI-UFWORHAWSA-N 4-[[2-[(e)-2-[4-(4-butoxyphenyl)phenyl]ethenyl]-4-(2,4-difluorophenyl)imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(OCCCC)=CC=C1C(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(F)=CC=2)F)=CN1CC1=CC=C(C(O)=O)C=C1 ASXCPWOLCBTNNI-UFWORHAWSA-N 0.000 claims 1
- UQBKDKHIBOFDGF-CXUHLZMHSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(2-fluoro-6-methoxyphenyl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1CC1=CC=C(C(O)=O)C=C1 UQBKDKHIBOFDGF-CXUHLZMHSA-N 0.000 claims 1
- DTMSWCICBXBSAP-UBKPWBPPSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(4-methylsulfonylphenyl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1CC1=CC=C(C(O)=O)C=C1 DTMSWCICBXBSAP-UBKPWBPPSA-N 0.000 claims 1
- IMHWADHAWYAYOF-CXUHLZMHSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(methanesulfonamido)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C=CC(\C=C\C=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)CC=3C=CC(=CC=3)C(O)=O)=CC=2)=C1 IMHWADHAWYAYOF-CXUHLZMHSA-N 0.000 claims 1
- KRSFENHPGWHVTP-OVCLIPMQSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(trifluoromethylsulfonylamino)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(NS(=O)(=O)C(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 KRSFENHPGWHVTP-OVCLIPMQSA-N 0.000 claims 1
- SXCDIMQFEGHCBV-UBKPWBPPSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(4,4,4-trifluorobutoxy)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(OCCCC(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 SXCDIMQFEGHCBV-UBKPWBPPSA-N 0.000 claims 1
- UANLRKGBZGLHHY-UBKPWBPPSA-N 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(methanesulfonamido)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1CC1=CC=C(C(O)=O)C=C1 UANLRKGBZGLHHY-UBKPWBPPSA-N 0.000 claims 1
- HMUKGHJJVPAMQT-LICLKQGHSA-N methyl 3-[4-[(e)-2-[4-(2,4-dichlorophenyl)-1-[(4-methoxycarbonylphenyl)methyl]imidazol-2-yl]ethenyl]phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(=O)OC)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 HMUKGHJJVPAMQT-LICLKQGHSA-N 0.000 claims 1
- VQAWPDCWVWTFIX-LICLKQGHSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(3-methylsulfonylphenyl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 VQAWPDCWVWTFIX-LICLKQGHSA-N 0.000 claims 1
- XPOFBHIORQFYGE-CNHKJKLMSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(4-methylsulfonylphenyl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 XPOFBHIORQFYGE-CNHKJKLMSA-N 0.000 claims 1
- ZFTXBNKZVLNXEK-CNHKJKLMSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(4,4,4-trifluorobutoxy)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(OCCCC(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ZFTXBNKZVLNXEK-CNHKJKLMSA-N 0.000 claims 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
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- 239000000787 lecithin Substances 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960000485 methotrexate Drugs 0.000 description 2
- APXOMRFLJBRHNX-UHFFFAOYSA-N methyl 2-[4-(bromomethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(CBr)C=C1 APXOMRFLJBRHNX-UHFFFAOYSA-N 0.000 description 2
- FBOGUMANEFNEEK-MDWZMJQESA-N methyl 2-[4-[[2-[(e)-2-(4-bromophenyl)ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(Br)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 FBOGUMANEFNEEK-MDWZMJQESA-N 0.000 description 2
- PERDKFBHSOQYMK-UHFFFAOYSA-N methyl 2-[4-[[4-(2,4-dichlorophenyl)-2-[2-[4-(trifluoromethyl)phenyl]ethyl]imidazol-1-yl]methyl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1CN1C(CCC=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 PERDKFBHSOQYMK-UHFFFAOYSA-N 0.000 description 2
- ZYCPSZGMMFTLHZ-UHFFFAOYSA-N methyl 2-[4-[[4-(2,4-dichlorophenyl)-2-[[3-(trifluoromethyl)phenyl]methyl]imidazol-1-yl]methyl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1CN1C(CC=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ZYCPSZGMMFTLHZ-UHFFFAOYSA-N 0.000 description 2
- BWJAYAJQJMIDEJ-UHFFFAOYSA-N methyl 2-amino-4-[4-[4-[[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]methyl]phenyl]phenoxy]benzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1CC(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(C(=O)OC)C(N)=C1 BWJAYAJQJMIDEJ-UHFFFAOYSA-N 0.000 description 2
- NNOMOPNBYWJNKH-UHFFFAOYSA-N methyl 2-amino-5-[4-[4-[[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]methyl]phenyl]phenoxy]benzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1CC(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(N)C(C(=O)OC)=C1 NNOMOPNBYWJNKH-UHFFFAOYSA-N 0.000 description 2
- QVNYNHCNNGKULA-UHFFFAOYSA-N methyl 2-amino-5-bromobenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1N QVNYNHCNNGKULA-UHFFFAOYSA-N 0.000 description 2
- CWVHAMGUQQAOJZ-UHFFFAOYSA-N methyl 4-[2-[(4-bromophenyl)methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC=C1N1C(CC=2C=CC(Br)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CWVHAMGUQQAOJZ-UHFFFAOYSA-N 0.000 description 2
- QETCIIHNNGRKPI-UHFFFAOYSA-N methyl 4-[2-[[4-[4-(4-tert-butylphenoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-(methanesulfonamido)benzoate Chemical compound C1=C(NS(C)(=O)=O)C(C(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(=CC=3)C(C)(C)C)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 QETCIIHNNGRKPI-UHFFFAOYSA-N 0.000 description 2
- JBCIJAWTRPGKRR-UHFFFAOYSA-N methyl 4-[4-(2,4-dichlorophenyl)-2-[[4-(4-hydroxyphenyl)phenyl]methyl]imidazol-1-yl]-2-(methanesulfonamido)benzoate Chemical compound C1=C(NS(C)(=O)=O)C(C(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 JBCIJAWTRPGKRR-UHFFFAOYSA-N 0.000 description 2
- RQTCBMPWHHKCLK-UHFFFAOYSA-N methyl 4-[4-(2,4-dichlorophenyl)-2-[[4-[4-[[3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]phenyl]methyl]imidazol-1-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(NS(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 RQTCBMPWHHKCLK-UHFFFAOYSA-N 0.000 description 2
- CEXRSWQZYOSPBE-UHFFFAOYSA-N methyl 4-[[2-[(4-bromophenoxy)methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(COC=2C=CC(Br)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CEXRSWQZYOSPBE-UHFFFAOYSA-N 0.000 description 2
- GHIPTZSEJVZIOH-AWNIVKPZSA-N methyl 4-[[2-[(e)-2-(4-bromophenyl)ethenyl]-4-(2,4-difluorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(Br)=CC=2)=NC(C=2C(=CC(F)=CC=2)F)=C1 GHIPTZSEJVZIOH-AWNIVKPZSA-N 0.000 description 2
- NCJMBJLSGCNUFW-KPKJPENVSA-N methyl 4-[[2-[(e)-2-(5-bromo-2-methoxyphenyl)ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C(=CC=C(Br)C=2)OC)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 NCJMBJLSGCNUFW-KPKJPENVSA-N 0.000 description 2
- COSYXXJRENETQM-CIAFOILYSA-N methyl 4-[[2-[(e)-2-[4-[(4-butylphenyl)sulfonylamino]phenyl]ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1CC1=CC=C(C(=O)OC)C=C1 COSYXXJRENETQM-CIAFOILYSA-N 0.000 description 2
- IYFIHMSVLMVLPX-UHFFFAOYSA-N methyl 4-[[2-[4-(3-aminophenyl)phenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(=CC=2)C=2C=C(N)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 IYFIHMSVLMVLPX-UHFFFAOYSA-N 0.000 description 2
- FODXHUOUFHFGLZ-UHFFFAOYSA-N methyl 4-[[2-[[4-[4-(4-tert-butylphenoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(=CC=3)C(C)(C)C)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 FODXHUOUFHFGLZ-UHFFFAOYSA-N 0.000 description 2
- LQOYHZLVZICDFZ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-(4-methoxyphenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 LQOYHZLVZICDFZ-UHFFFAOYSA-N 0.000 description 2
- YSECQFCRYDNOQJ-VIZOYTHASA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(6-methoxypyridin-3-yl)phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=NC(OC)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 YSECQFCRYDNOQJ-VIZOYTHASA-N 0.000 description 2
- CGJWAZHYLVJAKL-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[1-(4-hydroxyphenyl)cyclopropyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C2(CC2)C=2C=CC(O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CGJWAZHYLVJAKL-UHFFFAOYSA-N 0.000 description 2
- SDCKMMUDPCNNMJ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[3-(4-iodophenyl)propyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CCCC=2C=CC(I)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 SDCKMMUDPCNNMJ-UHFFFAOYSA-N 0.000 description 2
- HCEQSWDHNQCDCJ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[3-[4-[3-(trifluoromethyl)phenyl]phenyl]propyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CCCC=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 HCEQSWDHNQCDCJ-UHFFFAOYSA-N 0.000 description 2
- UUOYUBDTKHUYBO-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-(2-methoxyphenyl)phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)OC)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UUOYUBDTKHUYBO-UHFFFAOYSA-N 0.000 description 2
- AJJZKZNYSQPFQK-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(propylsulfonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)CC=3C=CC(=CC=3)C(=O)OC)=CC=2)=C1 AJJZKZNYSQPFQK-UHFFFAOYSA-N 0.000 description 2
- CCQVLKRSNSURLU-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(trifluoromethoxy)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(OC(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CCQVLKRSNSURLU-UHFFFAOYSA-N 0.000 description 2
- OOIDFCGDYKXQRT-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(COC=2C=CC(=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 OOIDFCGDYKXQRT-UHFFFAOYSA-N 0.000 description 2
- PMWLHXJTGFJLLL-UHFFFAOYSA-N methyl 5-[2-[(4-bromophenyl)methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(Br)=CC=2)=C1 PMWLHXJTGFJLLL-UHFFFAOYSA-N 0.000 description 2
- OCYHWDSMRNTEFU-UHFFFAOYSA-N methyl 5-[2-[[4-[4-(4-tert-butylphenoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(=CC=3)C(C)(C)C)=CC=2)=C1 OCYHWDSMRNTEFU-UHFFFAOYSA-N 0.000 description 2
- KSEVAVIZZSHYFG-UHFFFAOYSA-N methyl 5-[3-[4-[[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]methoxy]phenyl]phenoxy]-2-(trifluoromethyl)benzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1COC(C=C1)=CC=C1C(C=1)=CC=CC=1OC1=CC=C(C(F)(F)F)C(C(=O)OC)=C1 KSEVAVIZZSHYFG-UHFFFAOYSA-N 0.000 description 2
- YLBYAQYAYGADMW-UHFFFAOYSA-N methyl 5-[4-(2,4-dichlorophenyl)-2-[[4-(4-hydroxyphenyl)phenyl]methyl]imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 YLBYAQYAYGADMW-UHFFFAOYSA-N 0.000 description 2
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- AFNKLOMOEKMEOJ-UHFFFAOYSA-N methyl 2-[4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(methanesulfonamido)phenyl]phenyl]methyl]imidazol-1-yl]methyl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(NS(C)(=O)=O)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 AFNKLOMOEKMEOJ-UHFFFAOYSA-N 0.000 description 1
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- QAFJIJWLEBLXHH-UHFFFAOYSA-N methyl 2-fluorobenzoate Chemical compound COC(=O)C1=CC=CC=C1F QAFJIJWLEBLXHH-UHFFFAOYSA-N 0.000 description 1
- YUHSMQQNPRLEEJ-UHFFFAOYSA-N methyl 3-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CBr)=C1 YUHSMQQNPRLEEJ-UHFFFAOYSA-N 0.000 description 1
- JNXMCBVBGUEQID-UHFFFAOYSA-N methyl 3-amino-4-[2-[(4-bromophenyl)methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-methylsulfonylbenzoate Chemical compound NC1=C(S(C)(=O)=O)C(C(=O)OC)=CC=C1N1C(CC=2C=CC(Br)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 JNXMCBVBGUEQID-UHFFFAOYSA-N 0.000 description 1
- BTQDOXCVNCBUIU-UHFFFAOYSA-N methyl 3-amino-4-[4-[4-[[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]methyl]phenyl]phenoxy]benzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1CC(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(C(=O)OC)C=C1N BTQDOXCVNCBUIU-UHFFFAOYSA-N 0.000 description 1
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 1
- RLYSYOXXBFYVEQ-UHFFFAOYSA-N methyl 4-[3-[4-[[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]methoxy]phenyl]phenoxy]butanoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1COC(C=C1)=CC=C1C1=CC=CC(OCCCC(=O)OC)=C1 RLYSYOXXBFYVEQ-UHFFFAOYSA-N 0.000 description 1
- VUWGHTRKLHLNSD-OVCLIPMQSA-N methyl 4-[4-[3-[(e)-2-[4-(2,4-dichlorophenyl)-1-(2-methoxy-2-oxoethyl)imidazol-2-yl]ethenyl]phenyl]phenoxy]butanoate Chemical compound C1=CC(OCCCC(=O)OC)=CC=C1C1=CC=CC(\C=C\C=2N(C=C(N=2)C=2C(=CC(Cl)=CC=2)Cl)CC(=O)OC)=C1 VUWGHTRKLHLNSD-OVCLIPMQSA-N 0.000 description 1
- UGCAKJYKJNVXEO-UBKPWBPPSA-N methyl 4-[4-[4-[(e)-2-[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]ethenyl]phenyl]phenoxy]-3-nitrobenzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1\C=C\C(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(C(=O)OC)C=C1[N+]([O-])=O UGCAKJYKJNVXEO-UBKPWBPPSA-N 0.000 description 1
- OOKVCICGCSFDQA-KGENOOAVSA-N methyl 4-[[2-[(e)-2-[4-[(4-butylphenyl)methylamino]phenyl]ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(CCCC)=CC=C1CNC(C=C1)=CC=C1\C=C\C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1CC1=CC=C(C(=O)OC)C=C1 OOKVCICGCSFDQA-KGENOOAVSA-N 0.000 description 1
- BIGSSZXESOTIMP-AERZKKPOSA-N methyl 4-[[2-[(e)-2-[4-[4-(4-aminophenoxy)phenyl]phenyl]ethenyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 BIGSSZXESOTIMP-AERZKKPOSA-N 0.000 description 1
- SLVDIMWWVKRNKQ-UHFFFAOYSA-N methyl 4-[[2-[4-bromo-n-[(2-methylpropan-2-yl)oxycarbonyl]anilino]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(N(C(=O)OC(C)(C)C)C=2C=CC(Br)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 SLVDIMWWVKRNKQ-UHFFFAOYSA-N 0.000 description 1
- ZVTSGEBBLHWLED-UHFFFAOYSA-N methyl 4-[[2-[[6-(4-tert-butylphenoxy)isoquinoline-3-carbonyl]amino]-4-(2,4-dichlorophenyl)imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(NC(=O)C=2N=CC3=CC=C(OC=4C=CC(=CC=4)C(C)(C)C)C=C3C=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ZVTSGEBBLHWLED-UHFFFAOYSA-N 0.000 description 1
- HZQXEKRDIBGTTJ-AWNIVKPZSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-(4-nitrophenyl)ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)[N+]([O-])=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 HZQXEKRDIBGTTJ-AWNIVKPZSA-N 0.000 description 1
- CSCPMRAWAHKXMX-GIJQJNRQSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[(4-methylphenyl)sulfonylamino]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(NS(=O)(=O)C=3C=CC(C)=CC=3)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 CSCPMRAWAHKXMX-GIJQJNRQSA-N 0.000 description 1
- SLIQMTGCCDLTPU-GIDUJCDVSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[2-fluoro-5-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 SLIQMTGCCDLTPU-GIDUJCDVSA-N 0.000 description 1
- YZHKDQFYEJDSKU-CXUHLZMHSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 YZHKDQFYEJDSKU-CXUHLZMHSA-N 0.000 description 1
- NISHDXVJUPEAHC-CXUHLZMHSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(trifluoromethylsulfonylamino)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=C(NS(=O)(=O)C(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 NISHDXVJUPEAHC-CXUHLZMHSA-N 0.000 description 1
- QVEZNCJLYJCUNL-AERZKKPOSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(4-nitrophenoxy)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 QVEZNCJLYJCUNL-AERZKKPOSA-N 0.000 description 1
- BBAIVJGWQKWJHJ-CNHKJKLMSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[4-(methanesulfonamido)phenyl]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(=CC=2)C=2C=CC(NS(C)(=O)=O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 BBAIVJGWQKWJHJ-CNHKJKLMSA-N 0.000 description 1
- XTSJZYWQZZPFKF-CXUHLZMHSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[[3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(NS(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 XTSJZYWQZZPFKF-CXUHLZMHSA-N 0.000 description 1
- KXGIEMQAODXKLI-UBKPWBPPSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[[4-(trifluoromethyl)phenyl]sulfonylamino]phenyl]ethenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(\C=C\C=2C=CC(NS(=O)(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 KXGIEMQAODXKLI-UBKPWBPPSA-N 0.000 description 1
- BKOJINSLGOWTML-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[1-(4-methoxyphenyl)cyclopropyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C2(CC2)C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 BKOJINSLGOWTML-UHFFFAOYSA-N 0.000 description 1
- AHGHPDGCMRJYOQ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[3-[4-(3-methylsulfonylphenyl)phenyl]propyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CCCC=2C=CC(=CC=2)C=2C=C(C=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 AHGHPDGCMRJYOQ-UHFFFAOYSA-N 0.000 description 1
- AJOXNCBETRAYJD-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[4-(3-methylsulfonylphenoxy)phenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(OC=3C=C(C=CC=3)S(C)(=O)=O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 AJOXNCBETRAYJD-UHFFFAOYSA-N 0.000 description 1
- ZHRCTCXOZKABNO-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[4-(3-methylsulfonylphenyl)phenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(=CC=2)C=2C=C(C=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ZHRCTCXOZKABNO-UHFFFAOYSA-N 0.000 description 1
- RIJNCXDCJBIELM-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 RIJNCXDCJBIELM-UHFFFAOYSA-N 0.000 description 1
- NVCIHIIUTVGVOM-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[4-[3-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]phenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(=CC=2)C=2C=C(OC)C(NC(=O)OC(C)(C)C)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 NVCIHIIUTVGVOM-UHFFFAOYSA-N 0.000 description 1
- FNRRFFYYYMQJAB-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[4-[4-(methanesulfonamido)-3-methoxyphenyl]phenyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(C=2C=CC(=CC=2)C=2C=C(OC)C(NS(C)(=O)=O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 FNRRFFYYYMQJAB-UHFFFAOYSA-N 0.000 description 1
- KNGNLJIZOMPIHL-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-(3-methylsulfonylphenyl)phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(C=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 KNGNLJIZOMPIHL-UHFFFAOYSA-N 0.000 description 1
- ZDMYBHIPSNQUPD-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-(4-methylsulfonylphenyl)phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ZDMYBHIPSNQUPD-UHFFFAOYSA-N 0.000 description 1
- UPFFSHVBPIZRBC-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(2,2,2-trifluoroethylsulfonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(NS(=O)(=O)CC(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UPFFSHVBPIZRBC-UHFFFAOYSA-N 0.000 description 1
- MWWIFCCFBWBNIT-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(ethylsulfonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)CC=3C=CC(=CC=3)C(=O)OC)=CC=2)=C1 MWWIFCCFBWBNIT-UHFFFAOYSA-N 0.000 description 1
- PHHPWOZWGAYRCN-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(methanesulfonamido)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(NS(C)(=O)=O)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 PHHPWOZWGAYRCN-UHFFFAOYSA-N 0.000 description 1
- HNCCGJDDXJSTQI-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(methoxycarbonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound COC(=O)NC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)CC=3C=CC(=CC=3)C(=O)OC)=CC=2)=C1 HNCCGJDDXJSTQI-UHFFFAOYSA-N 0.000 description 1
- UKZNXQBBZBYEFF-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(propan-2-yloxycarbonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(NC(=O)OC(C)C)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UKZNXQBBZBYEFF-UHFFFAOYSA-N 0.000 description 1
- GNMSIDSVLMFOEV-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-(trifluoromethylsulfonylamino)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(NS(=O)(=O)C(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 GNMSIDSVLMFOEV-UHFFFAOYSA-N 0.000 description 1
- ONCFCMFSHLIPOE-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[3-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=C(OC)C(NC(=O)OC(C)(C)C)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 ONCFCMFSHLIPOE-UHFFFAOYSA-N 0.000 description 1
- AQGCIPZRSTYBSV-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[4-(methanesulfonamido)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=CC(NS(C)(=O)=O)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 AQGCIPZRSTYBSV-UHFFFAOYSA-N 0.000 description 1
- FEXQADVTIYXZFJ-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methyl]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(CC=2C=CC(=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 FEXQADVTIYXZFJ-UHFFFAOYSA-N 0.000 description 1
- UZXYNGWNCWPYBC-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[n-[(2-methylpropan-2-yl)oxycarbonyl]-4-[3-(trifluoromethyl)phenyl]anilino]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(N(C(=O)OC(C)(C)C)C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UZXYNGWNCWPYBC-UHFFFAOYSA-N 0.000 description 1
- RIFQXVRRMBZFLF-UHFFFAOYSA-N methyl 4-[[4-(2,4-dichlorophenyl)-2-[n-methyl-4-[3-(trifluoromethyl)phenyl]anilino]imidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(N(C)C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 RIFQXVRRMBZFLF-UHFFFAOYSA-N 0.000 description 1
- YGDGZDGRCWHDOU-UHFFFAOYSA-N methyl 4-[[5-chloro-4-(2-hydroxyphenyl)thiophen-2-yl]sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC(C=2C(=CC=CC=2)O)=C(Cl)S1 YGDGZDGRCWHDOU-UHFFFAOYSA-N 0.000 description 1
- YBAZOLISUXINHV-UHFFFAOYSA-N methyl 4-fluoro-2-nitrobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1[N+]([O-])=O YBAZOLISUXINHV-UHFFFAOYSA-N 0.000 description 1
- CNJJSTPBUHAEFH-UHFFFAOYSA-N methyl 4-fluoro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 CNJJSTPBUHAEFH-UHFFFAOYSA-N 0.000 description 1
- UKSBPFGECWNXCC-UHFFFAOYSA-N methyl 5-[2-[[4-[4-(4-aminophenoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)=C1 UKSBPFGECWNXCC-UHFFFAOYSA-N 0.000 description 1
- TWOONNZENPVPLV-UHFFFAOYSA-N methyl 5-[4-(2,4-dichlorophenyl)-2-[[4-[4-(4-nitrophenoxy)phenyl]phenyl]methyl]imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=C1 TWOONNZENPVPLV-UHFFFAOYSA-N 0.000 description 1
- YNUHUKFMJNQTDX-UHFFFAOYSA-N methyl 5-[4-(2,4-dichlorophenyl)-2-[[4-[4-[4-(2-methylpropylsulfonylamino)phenoxy]phenyl]phenyl]methyl]imidazol-1-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(NS(=O)(=O)CC(C)C)=CC=3)=CC=2)=C1 YNUHUKFMJNQTDX-UHFFFAOYSA-N 0.000 description 1
- BQRFYYMQQKPDGK-UHFFFAOYSA-N methyl 5-[4-[3-[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]propyl]phenoxy]-2-nitrobenzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1CCCC(C=C1)=CC=C1OC1=CC=C([N+]([O-])=O)C(C(=O)OC)=C1 BQRFYYMQQKPDGK-UHFFFAOYSA-N 0.000 description 1
- SYCRWDVQRHHKSY-UBKPWBPPSA-N methyl 5-[4-[4-[(e)-2-[4-(2,4-dichlorophenyl)-1-ethylimidazol-2-yl]ethenyl]phenyl]phenoxy]-2-(trifluoromethyl)benzoate Chemical compound CCN1C=C(C=2C(=CC(Cl)=CC=2)Cl)N=C1\C=C\C(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C(C(=O)OC)=C1 SYCRWDVQRHHKSY-UBKPWBPPSA-N 0.000 description 1
- RWVOYTWWPRFBLB-CNHKJKLMSA-N methyl 5-[4-[4-[(e)-2-[4-(2,4-difluorophenyl)-1-ethylimidazol-2-yl]ethenyl]phenyl]phenoxy]-2-(methanesulfonamido)benzoate Chemical compound CCN1C=C(C=2C(=CC(F)=CC=2)F)N=C1\C=C\C(C=C1)=CC=C1C(C=C1)=CC=C1OC1=CC=C(NS(C)(=O)=O)C(C(=O)OC)=C1 RWVOYTWWPRFBLB-CNHKJKLMSA-N 0.000 description 1
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- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54397104P | 2004-02-12 | 2004-02-12 | |
| US60/543,971 | 2004-02-12 | ||
| PCT/US2005/004590 WO2005080346A1 (en) | 2004-02-12 | 2005-02-11 | Substituted azole derivatives, compositions, and methods of use |
Publications (2)
| Publication Number | Publication Date |
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| AU2005214349A1 AU2005214349A1 (en) | 2005-09-01 |
| AU2005214349B2 true AU2005214349B2 (en) | 2011-11-03 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2005214349A Ceased AU2005214349B2 (en) | 2004-02-12 | 2005-02-11 | Substituted azole derivatives, compositions, and methods of use |
Country Status (10)
| Country | Link |
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| US (2) | US20050187277A1 (https=) |
| EP (1) | EP1730118A1 (https=) |
| JP (1) | JP4898458B2 (https=) |
| CN (1) | CN1922151A (https=) |
| AU (1) | AU2005214349B2 (https=) |
| CA (1) | CA2551909C (https=) |
| IL (1) | IL176571A0 (https=) |
| NZ (1) | NZ548208A (https=) |
| WO (1) | WO2005080346A1 (https=) |
| ZA (1) | ZA200605526B (https=) |
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| JP2007527920A (ja) * | 2004-03-08 | 2007-10-04 | ワイス | イオンチャンネルモジュレーター |
| EP1723120A4 (en) * | 2004-03-08 | 2007-09-26 | Wyeth Corp | MODULATORS OF THE ION CHANNEL FUNCTION |
| RU2361872C2 (ru) * | 2004-05-26 | 2009-07-20 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Циннамидное соединение |
| BRPI0510929A (pt) * | 2004-06-18 | 2007-07-17 | Chiron Corp | derivados de n-(1-(1-benzil-4-fenil-1h-imidazol-2-il)-2,2-dimetilpropil) benzamida e compostos relacionados como inibidores de proteìna de eixo de kinesin (ksp) para o tratamento de cáncer |
| DE602005019602D1 (de) | 2004-10-26 | 2010-04-08 | Eisai R&D Man Co Ltd | Amorphe form einer zimtsäureamidverbindung |
| JP2008530197A (ja) * | 2005-02-18 | 2008-08-07 | イノディア インク． | ４−ヒドロキシイソロイシンの類似体及びその使用 |
| EP1874287A2 (en) * | 2005-03-22 | 2008-01-09 | Innodia Inc. | Compounds and compositions for use in the prevention and treatment of obesity and related syndromes |
| US20090048448A1 (en) * | 2005-11-18 | 2009-02-19 | Ikuo Kushida | Salts of cynnamide compound or solvates thereof |
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| KR20230084530A (ko) * | 2020-10-09 | 2023-06-13 | 브리스톨-마이어스 스큅 컴퍼니 | 아미노이미다졸 fpr2 효능제 |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
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2005
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- 2005-02-11 JP JP2006553310A patent/JP4898458B2/ja not_active Expired - Fee Related
- 2005-02-11 ZA ZA200605526A patent/ZA200605526B/en unknown
- 2005-02-11 CN CNA2005800048601A patent/CN1922151A/zh active Pending
- 2005-02-11 NZ NZ548208A patent/NZ548208A/en not_active IP Right Cessation
- 2005-02-11 US US11/056,498 patent/US20050187277A1/en not_active Abandoned
- 2005-02-11 WO PCT/US2005/004590 patent/WO2005080346A1/en not_active Ceased
- 2005-02-11 AU AU2005214349A patent/AU2005214349B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| US20050187277A1 (en) | 2005-08-25 |
| IL176571A0 (en) | 2006-10-31 |
| NZ548208A (en) | 2010-09-30 |
| US20110092553A1 (en) | 2011-04-21 |
| JP4898458B2 (ja) | 2012-03-14 |
| CA2551909C (en) | 2011-10-11 |
| CN1922151A (zh) | 2007-02-28 |
| AU2005214349A1 (en) | 2005-09-01 |
| EP1730118A1 (en) | 2006-12-13 |
| CA2551909A1 (en) | 2005-09-01 |
| ZA200605526B (en) | 2007-11-28 |
| JP2007523903A (ja) | 2007-08-23 |
| WO2005080346A1 (en) | 2005-09-01 |
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