AU2007211319B9 - Substituted imidazole derivatives and their use as PTPase inhibitors - Google Patents

Info

Publication number

AU2007211319B9

AU2007211319B9 AU2007211319A AU2007211319A AU2007211319B9 AU 2007211319 B9 AU2007211319 B9 AU 2007211319B9 AU 2007211319 A AU2007211319 A AU 2007211319A AU 2007211319 A AU2007211319 A AU 2007211319A AU 2007211319 B9 AU2007211319 B9 AU 2007211319B9

Authority

AU

Australia

Prior art keywords

phenyl

imidazol

dichloro

dioxide

biphenyl

Prior art date

2006-01-30

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

Links

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• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 title abstract description 45
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 title abstract description 45
• 150000002460 imidazoles Chemical class 0.000 title abstract description 10
• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 5
• 239000003112 inhibitor Substances 0.000 title description 16
• 238000000034 method Methods 0.000 claims abstract description 390
• 150000001875 compounds Chemical class 0.000 claims abstract description 193
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
• 201000010099 disease Diseases 0.000 claims abstract description 38
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 238000002360 preparation method Methods 0.000 claims abstract description 20
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 15
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 10
• -1 3,3-dimethyl-butyl Chemical group 0.000 claims description 320
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 136
• 239000000203 mixture Substances 0.000 claims description 103
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 239000011734 sodium Substances 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 230000015572 biosynthetic process Effects 0.000 claims description 24
• 238000003786 synthesis reaction Methods 0.000 claims description 21
• 108010051696 Growth Hormone Proteins 0.000 claims description 18
• 239000000122 growth hormone Substances 0.000 claims description 18
• 239000003937 drug carrier Substances 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
• 208000026278 immune system disease Diseases 0.000 claims description 15
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 13
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 150000002500 ions Chemical class 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 208000024827 Alzheimer disease Diseases 0.000 claims description 10
• 208000035473 Communicable disease Diseases 0.000 claims description 10
• 102000004127 Cytokines Human genes 0.000 claims description 10
• 108090000695 Cytokines Proteins 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 239000003102 growth factor Substances 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052708 sodium Inorganic materials 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 8
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
• 208000015181 infectious disease Diseases 0.000 claims description 7
• 229910052700 potassium Chemical group 0.000 claims description 7
• 239000011591 potassium Chemical group 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• UFYGBSOSGMSRFG-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethylsulfanyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(SCC3CCCCC3)C=CC=2)=N1 UFYGBSOSGMSRFG-UHFFFAOYSA-N 0.000 claims description 4
• CLICTJKGRVHEPA-UHFFFAOYSA-N 5-[3-[2-[[4-[4-(cyclohexylmethoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(OCC3CCCCC3)=CC=2)=N1 CLICTJKGRVHEPA-UHFFFAOYSA-N 0.000 claims description 4
• CENWRJLRKOPSID-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[3-(3,3-dimethylbutoxy)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(C)CCOC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)C=3C=C(C=CC=3)N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 CENWRJLRKOPSID-UHFFFAOYSA-N 0.000 claims description 4
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• ROPVMNGPSLXSCA-UHFFFAOYSA-N 5-[3-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=N1 ROPVMNGPSLXSCA-UHFFFAOYSA-N 0.000 claims description 3
• BHLLGPUOHKTNMM-UHFFFAOYSA-N 5-[3-[2-[[4-[4-(cyclohexylmethylsulfanyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(SCC3CCCCC3)=CC=2)=N1 BHLLGPUOHKTNMM-UHFFFAOYSA-N 0.000 claims description 3
• LGRJRZLTNCHYCZ-UHFFFAOYSA-N 5-[3-[2-[[4-(4-tert-butylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=CC(N2S(NC(=O)C2)(=O)=O)=C1 LGRJRZLTNCHYCZ-UHFFFAOYSA-N 0.000 claims description 2
• BHRVRCUAQMSZBF-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[3-(3,3-dimethylbutylsulfonyl)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(C)CCS(=O)(=O)C1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)C=3C=C(C=CC=3)N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 BHRVRCUAQMSZBF-UHFFFAOYSA-N 0.000 claims description 2
• 102000018997 Growth Hormone Human genes 0.000 claims 6
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 3
• BIIHQKKOUVZRBW-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(2-cyclohexylethylsulfonyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(C=CC=2)S(=O)(=O)CCC2CCCCC2)=N1 BIIHQKKOUVZRBW-UHFFFAOYSA-N 0.000 claims 1
• UKRPUOPDTNRJGU-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(OCC3CCCCC3)C=CC=2)=N1 UKRPUOPDTNRJGU-UHFFFAOYSA-N 0.000 claims 1
• RNLJJRIMAAXDKB-UHFFFAOYSA-N 5-[3-[2-[[4-[3-(cyclohexylmethylsulfonyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=C(C=CC=2)S(=O)(=O)CC2CCCCC2)=N1 RNLJJRIMAAXDKB-UHFFFAOYSA-N 0.000 claims 1
• CYTHGJRRRWBPCX-UHFFFAOYSA-N 5-[3-[2-[[4-[4-(2-cyclohexylethyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(=CC=2)C=2C=CC(CCC3CCCCC3)=CC=2)=N1 CYTHGJRRRWBPCX-UHFFFAOYSA-N 0.000 claims 1
• YUJICGNAQYBSOM-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[3-(3,3-dimethylbutylsulfanyl)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound CC(C)(C)CCSC1=CC=CC(C=2C=CC(CC=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)C=3C=C(C=CC=3)N3S(NC(=O)C3)(=O)=O)=CC=2)=C1 YUJICGNAQYBSOM-UHFFFAOYSA-N 0.000 claims 1
• QVNJMALMSISSON-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[4-(3,3-dimethylbutoxy)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(OCCC(C)(C)C)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=CC(N2S(NC(=O)C2)(=O)=O)=C1 QVNJMALMSISSON-UHFFFAOYSA-N 0.000 claims 1
• UPTXGRLHROGISK-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[4-(3,3-dimethylbutylsulfanyl)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(SCCC(C)(C)C)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=CC(N2S(NC(=O)C2)(=O)=O)=C1 UPTXGRLHROGISK-UHFFFAOYSA-N 0.000 claims 1
• JVKJRJRAQPIGEN-UHFFFAOYSA-N 5-[3-[4-(2,4-dichlorophenyl)-2-[[4-[4-(4,4-dimethylpent-1-enyl)phenyl]phenyl]methyl]imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound C1=CC(C=CCC(C)(C)C)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=CC(N2S(NC(=O)C2)(=O)=O)=C1 JVKJRJRAQPIGEN-UHFFFAOYSA-N 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 13
• 230000001404 mediated effect Effects 0.000 abstract description 9
• 208000035475 disorder Diseases 0.000 abstract description 6
• 241001465754 Metazoa Species 0.000 abstract description 3
• 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 abstract description 2
• 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 abstract 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 190
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 169
• 125000000217 alkyl group Chemical group 0.000 description 141
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 89
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 88
• 239000000243 solution Substances 0.000 description 78
• 235000019439 ethyl acetate Nutrition 0.000 description 77
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
• 229910052757 nitrogen Inorganic materials 0.000 description 55
• 125000004188 dichlorophenyl group Chemical group 0.000 description 51
• 239000010410 layer Substances 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 239000012267 brine Substances 0.000 description 48
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 46
• 239000012044 organic layer Substances 0.000 description 44
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
• 239000000047 product Substances 0.000 description 36
• 125000003118 aryl group Chemical group 0.000 description 32
• 229910052799 carbon Inorganic materials 0.000 description 32
• 238000010898 silica gel chromatography Methods 0.000 description 32
• 239000000706 filtrate Substances 0.000 description 28
• 239000002904 solvent Substances 0.000 description 25
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
• 238000006467 substitution reaction Methods 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 239000000460 chlorine Substances 0.000 description 23
• 125000000753 cycloalkyl group Chemical group 0.000 description 23
• 125000001424 substituent group Chemical group 0.000 description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 125000003342 alkenyl group Chemical group 0.000 description 21
• 125000000623 heterocyclic group Chemical group 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• 125000000304 alkynyl group Chemical group 0.000 description 20
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
• IVLHRVBKAGAZSY-UHFFFAOYSA-N 5-[3-[2-[(4-bromophenyl)methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound ClC1=CC(Cl)=CC=C1C1=CN(C=2C=C(C=CC=2)N2S(NC(=O)C2)(=O)=O)C(CC=2C=CC(Br)=CC=2)=N1 IVLHRVBKAGAZSY-UHFFFAOYSA-N 0.000 description 16
• 239000000284 extract Substances 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• 229910052727 yttrium Inorganic materials 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 125000001188 haloalkyl group Chemical group 0.000 description 15
• 229910052721 tungsten Inorganic materials 0.000 description 15
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 14
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
• 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 13
• 229910052736 halogen Inorganic materials 0.000 description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 13
• KNQVRFYNQWNYPU-UHFFFAOYSA-N (4-cyclohexylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1CCCCC1 KNQVRFYNQWNYPU-UHFFFAOYSA-N 0.000 description 12
• HOPFEDLIYBPKII-UHFFFAOYSA-N 1,2,5-thiadiazolidin-3-one Chemical compound O=C1CNSN1 HOPFEDLIYBPKII-UHFFFAOYSA-N 0.000 description 12
• 102100038803 Somatotropin Human genes 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• JSZAZZQHDRHICK-UHFFFAOYSA-N 1,1-dioxo-1,2,5-thiadiazolidin-3-one Chemical compound O=C1CNS(=O)(=O)N1 JSZAZZQHDRHICK-UHFFFAOYSA-N 0.000 description 11
• 125000002947 alkylene group Chemical group 0.000 description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 125000001072 heteroaryl group Chemical group 0.000 description 11
• 230000002401 inhibitory effect Effects 0.000 description 11
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• FWYKGSRTTOQQHT-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(2-cyclohexylethenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(C=CC3CCCCC3)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 FWYKGSRTTOQQHT-UHFFFAOYSA-N 0.000 description 1
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• TXWKHORQOBMSQC-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 TXWKHORQOBMSQC-UHFFFAOYSA-N 0.000 description 1
• NURTVXGLMVLMBR-UHFFFAOYSA-N methyl 2-[4-[2-[[4-(4-cyclohexylphenyl)phenyl]methyl]-4-(4-methylsulfonylphenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C2CCCCC2)=NC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 NURTVXGLMVLMBR-UHFFFAOYSA-N 0.000 description 1
• SYLNJUFYNSSFAI-UHFFFAOYSA-N methyl 2-[4-[2-[[4-[4-(2-cyclopentyl-1-hydroxyethyl)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C(O)CC2CCCC2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 SYLNJUFYNSSFAI-UHFFFAOYSA-N 0.000 description 1
• YHJHOAMPPZPUBG-UHFFFAOYSA-N methyl 2-[4-[2-[[4-[4-(cyclohexylmethoxy)phenyl]phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]anilino]acetate Chemical compound C1=CC(NCC(=O)OC)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(OCC3CCCCC3)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 YHJHOAMPPZPUBG-UHFFFAOYSA-N 0.000 description 1
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