ES2545907T3 - Inhibidores de proteína quinasa - Google Patents

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Publication number

ES2545907T3

ES2545907T3 ES06846085.6T ES06846085T ES2545907T3 ES 2545907 T3 ES2545907 T3 ES 2545907T3 ES 06846085 T ES06846085 T ES 06846085T ES 2545907 T3 ES2545907 T3 ES 2545907T3

Authority

ES

Spain

Prior art keywords

pyrimidin

pyrazole

amine

cyclohexyl

trans

Prior art date

2005-12-29

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.)

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• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 3
• 239000003909 protein kinase inhibitor Substances 0.000 title description 3
• -1 C (O) N (R6) 2 Proteins 0.000 claims abstract description 1133
• 150000001875 compounds Chemical class 0.000 claims abstract description 261
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 117
• 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 47
• 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 46
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
• 150000002390 heteroarenes Chemical class 0.000 claims abstract description 38
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 35
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 35
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims abstract description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 12
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims abstract description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 12
• 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims abstract description 9
• 229910006074 SO2NH2 Inorganic materials 0.000 claims abstract description 9
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
• 125000000565 sulfonamide group Chemical group 0.000 claims abstract description 9
• 102220518365 Casein kinase I isoform gamma-2_R12A_mutation Human genes 0.000 claims abstract description 6
• 102220518288 Casein kinase I isoform gamma-2_R13A_mutation Human genes 0.000 claims abstract description 6
• 102220518364 Casein kinase I isoform gamma-2_R14A_mutation Human genes 0.000 claims abstract description 6
• 125000001424 substituent group Chemical group 0.000 claims abstract description 6
• FEIACFYXEWBKHU-UHFFFAOYSA-N (2-aminopyridin-3-yl)methanol Chemical compound NC1=NC=CC=C1CO FEIACFYXEWBKHU-UHFFFAOYSA-N 0.000 claims abstract description 4
• WRXIKBHQDRMYJJ-UHFFFAOYSA-N 2-(4-bromopyrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=C(Br)C=N1 WRXIKBHQDRMYJJ-UHFFFAOYSA-N 0.000 claims abstract description 3
• 101100240521 Caenorhabditis elegans nhr-16 gene Proteins 0.000 claims abstract description 3
• 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims abstract description 3
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims abstract description 3
• GCVFCUPRTZORNH-UHFFFAOYSA-N n,n-dimethyl-3-[4-(1,10-phenanthrolin-4-yl)butoxy]aniline;2-pyridin-2-ylpyridine;ruthenium Chemical compound [Ru].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.CN(C)C1=CC=CC(OCCCCC=2C3=C(C4=NC=CC=C4C=C3)N=CC=2)=C1 GCVFCUPRTZORNH-UHFFFAOYSA-N 0.000 claims abstract description 3
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 547
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 308
• 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 252
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 115
• 239000000203 mixture Substances 0.000 claims description 104
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 102
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 85
• BNXQCDYMLTVSMA-UHFFFAOYSA-N 5-[1-[(2-fluorophenyl)methyl]indol-5-yl]-1H-pyrazol-4-amine Chemical compound NC=1C(=NNC=1)C=1C=C2C=CN(C2=CC=1)CC1=C(C=CC=C1)F BNXQCDYMLTVSMA-UHFFFAOYSA-N 0.000 claims description 60
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 20
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 14
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
• 206010009944 Colon cancer Diseases 0.000 claims description 10
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 206010014733 Endometrial cancer Diseases 0.000 claims description 9
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
• 201000005202 lung cancer Diseases 0.000 claims description 9
• 208000020816 lung neoplasm Diseases 0.000 claims description 9
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 8
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 8
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 8
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 8
• 201000010881 cervical cancer Diseases 0.000 claims description 8
• 208000029742 colonic neoplasm Diseases 0.000 claims description 8
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 8
• 201000004101 esophageal cancer Diseases 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 206010060862 Prostate cancer Diseases 0.000 claims description 7
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 7
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 6
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 6
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 6
• 229960004063 propylene glycol Drugs 0.000 claims description 6
• 235000013772 propylene glycol Nutrition 0.000 claims description 6
• 201000000849 skin cancer Diseases 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• FYSYBMQPDNBXKS-UHFFFAOYSA-N 1-(4-morpholin-4-ylcyclohexyl)pyrazol-4-amine Chemical compound NC=1C=NN(C1)C1CCC(CC1)N1CCOCC1 FYSYBMQPDNBXKS-UHFFFAOYSA-N 0.000 claims description 4
• MHTTYAMILIUWTG-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-5-[1-[1-[1-(2-methoxyethyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]-1H-indole Chemical compound FC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CCOC)C=CC=C1 MHTTYAMILIUWTG-UHFFFAOYSA-N 0.000 claims description 4
• YISUJHXQWDDJCW-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-5-[1-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]-1H-indole Chemical compound FC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CC(C)C)C=CC=C1 YISUJHXQWDDJCW-UHFFFAOYSA-N 0.000 claims description 4
• KMNYBGNIQZHIFL-UHFFFAOYSA-N 4-[[4-[3-[1-[(2-fluorophenyl)methyl]indol-5-yl]pyrazol-1-yl]phenyl]methyl]morpholine Chemical compound FC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2=CC=C(C=C2)CN2CCOCC2)C=CC=C1 KMNYBGNIQZHIFL-UHFFFAOYSA-N 0.000 claims description 4
• 206010005003 Bladder cancer Diseases 0.000 claims description 4
• JRWWOTSZBYMLRD-WXUXXXNLSA-N COC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)[C@@H]2CC[C@H](CC2)N2CCN(CC2)CCCOC)C=CC=C1 Chemical compound COC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)[C@@H]2CC[C@H](CC2)N2CCN(CC2)CCCOC)C=CC=C1 JRWWOTSZBYMLRD-WXUXXXNLSA-N 0.000 claims description 4
• JIXJZSWKWSJLGS-UHFFFAOYSA-N CS(=O)(=O)N1CCC(CC1)N2C=CC(=N2)C3=CC4=C(C=C3)N=C(N4)CC5=CC=CC=C5 Chemical compound CS(=O)(=O)N1CCC(CC1)N2C=CC(=N2)C3=CC4=C(C=C3)N=C(N4)CC5=CC=CC=C5 JIXJZSWKWSJLGS-UHFFFAOYSA-N 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
• 206010017758 gastric cancer Diseases 0.000 claims description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 201000001275 rectum cancer Diseases 0.000 claims description 4
• 201000011549 stomach cancer Diseases 0.000 claims description 4
• 201000002510 thyroid cancer Diseases 0.000 claims description 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
• UZECUZGUPZYUKK-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-[1-(2-methoxyethyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CCOC)C=CC=C1 UZECUZGUPZYUKK-UHFFFAOYSA-N 0.000 claims description 3
• ZEQZCROSBIAVQN-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-5-[1-[1-[1-(3-methoxypropyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]-1H-indole Chemical compound FC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CCCOC)C=CC=C1 ZEQZCROSBIAVQN-UHFFFAOYSA-N 0.000 claims description 3
• HGUBIGHNJCUFEM-WXUXXXNLSA-N FC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)[C@@H]2CC[C@H](CC2)N2CCN(CC2)CCOCCOC)C=CC=C1 Chemical compound FC1=C(CC=2NC3=CC=C(C=C3C=2)C2=NN(C=C2)[C@@H]2CC[C@H](CC2)N2CCN(CC2)CCOCCOC)C=CC=C1 HGUBIGHNJCUFEM-WXUXXXNLSA-N 0.000 claims description 3
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• FSHOAPNTGPOGEO-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CC)C=CC=C1 FSHOAPNTGPOGEO-UHFFFAOYSA-N 0.000 claims description 2
• SKCXAGGADMOHRJ-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)C)C=CC=C1 SKCXAGGADMOHRJ-UHFFFAOYSA-N 0.000 claims description 2
• DFZGIYADBXPGDQ-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)C(C)C)C=CC=C1 DFZGIYADBXPGDQ-UHFFFAOYSA-N 0.000 claims description 2
• KVCGTJGULYMPCO-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-(1-propylpiperidin-4-yl)piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CCC)C=CC=C1 KVCGTJGULYMPCO-UHFFFAOYSA-N 0.000 claims description 2
• YUWSIFRLYLIRGE-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCN(CC2)C2CCN(CC2)CC(C)C)C=CC=C1 YUWSIFRLYLIRGE-UHFFFAOYSA-N 0.000 claims description 2
• JHVAFTOXBMVGNI-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[4-[4-(2-ethoxyethyl)piperazin-1-yl]cyclohexyl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCC(CC2)N2CCN(CC2)CCOCC)C=CC=C1 JHVAFTOXBMVGNI-UHFFFAOYSA-N 0.000 claims description 2
• OHJYJQIAIVVGHW-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-[1-[4-[[4-(3-methoxypropyl)piperazin-1-yl]methyl]phenyl]pyrazol-3-yl]indole Chemical compound ClC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2=CC=C(C=C2)CN2CCN(CC2)CCCOC)C=CC=C1 OHJYJQIAIVVGHW-UHFFFAOYSA-N 0.000 claims description 2
• NLPAEJDFSQRJBN-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-[1-[4-[4-(3-methoxypropyl)piperazin-1-yl]cyclohexyl]pyrazol-3-yl]indole Chemical compound FC1=C(CN2C=CC3=CC(=CC=C23)C2=NN(C=C2)C2CCC(CC2)N2CCN(CC2)CCCOC)C=CC=C1 NLPAEJDFSQRJBN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• YHPMOMMCYKOPFH-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-5-[1-[4-[4-(3-methoxypropyl)piperazin-1-yl]cyclohexyl]pyrazol-3-yl]-1h-indole Chemical compound C1CN(CCCOC)CCN1C1CCC(N2N=C(C=C2)C=2C=C3C=C(CC=4C(=CC=CC=4)F)NC3=CC=2)CC1 YHPMOMMCYKOPFH-UHFFFAOYSA-N 0.000 claims description 2
• BJHYSXILBVXLTO-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-6-[1-[1-(2-methylsulfonylethyl)piperidin-4-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound FC1=C(CC2=NC3=C(N2)C=CC(=C3)C2=NN(C=C2)C2CCN(CC2)CCS(=O)(=O)C)C=CC=C1 BJHYSXILBVXLTO-UHFFFAOYSA-N 0.000 claims description 2
• KLMYIBBMLBINDA-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-6-[1-[1-(2-methylsulfonylethyl)pyrrolidin-3-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound FC1=C(CC2=NC3=C(N2)C=CC(=C3)C2=NN(C=C2)C2CN(CC2)CCS(=O)(=O)C)C=CC=C1 KLMYIBBMLBINDA-UHFFFAOYSA-N 0.000 claims description 2
• QSTZAWWSVVZDSO-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]-6-[1-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]pyrazol-3-yl]-1H-benzimidazole Chemical compound COC1=C(CC2=NC3=C(N2)C=CC(=C3)C2=NN(C=C2)C2=CC=C(C=C2)CN2CCN(CC2)S(=O)(=O)C)C=CC=C1 QSTZAWWSVVZDSO-UHFFFAOYSA-N 0.000 claims description 2
• JELJCTDCFXNKEJ-UHFFFAOYSA-N 2-benzyl-6-(1-tert-butylpyrazol-3-yl)-1H-benzimidazole Chemical compound CC(C)(C)N1C=CC(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)=N1 JELJCTDCFXNKEJ-UHFFFAOYSA-N 0.000 claims description 2
• WDLQPBTUEBIXLU-UHFFFAOYSA-N 2-benzyl-6-[1-(1-methylpiperidin-4-yl)pyrazol-3-yl]-1H-benzimidazole Chemical compound C(C1=CC=CC=C1)C1=NC2=C(N1)C=CC(=C2)C1=NN(C=C1)C1CCN(CC1)C WDLQPBTUEBIXLU-UHFFFAOYSA-N 0.000 claims description 2
• UZORBXGWLGGZNW-UHFFFAOYSA-N 2-benzyl-6-[1-(1-pyrimidin-2-ylpiperidin-4-yl)pyrazol-3-yl]-1H-benzimidazole Chemical compound C1CN(CCC1N2C=CC(=N2)C3=CC4=C(C=C3)N=C(N4)CC5=CC=CC=C5)C6=NC=CC=N6 UZORBXGWLGGZNW-UHFFFAOYSA-N 0.000 claims description 2
• JMDRTEAJGQFNSE-UHFFFAOYSA-N 2-benzyl-6-[1-[1-(2-methylsulfonylethyl)pyrrolidin-3-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound C1N(CCS(=O)(=O)C)CCC1N1N=C(C=2C=C3NC(CC=4C=CC=CC=4)=NC3=CC=2)C=C1 JMDRTEAJGQFNSE-UHFFFAOYSA-N 0.000 claims description 2
• LWPIUARYOVJJGF-UHFFFAOYSA-N 2-benzyl-6-[1-[1-(3-methoxypropyl)pyrrolidin-3-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound C(C1=CC=CC=C1)C1=NC2=C(N1)C=CC(=C2)C1=NN(C=C1)C1CN(CC1)CCCOC LWPIUARYOVJJGF-UHFFFAOYSA-N 0.000 claims description 2
• GIIYVDZMUPUHOF-UHFFFAOYSA-N 2-benzyl-6-[1-[1-[1-(2-methoxyethyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound C(C1=CC=CC=C1)C1=NC2=C(N1)C=C(C=C2)C1=NN(C=C1)C1CCN(CC1)C1CCN(CC1)CCOC GIIYVDZMUPUHOF-UHFFFAOYSA-N 0.000 claims description 2
• CWHXQDAZBOZPIU-UHFFFAOYSA-N 2-benzyl-6-[1-[1-[1-(3-methoxypropyl)piperidin-4-yl]piperidin-4-yl]pyrazol-3-yl]-1H-benzimidazole Chemical compound C(C1=CC=CC=C1)C1=NC2=C(N1)C=C(C=C2)C1=NN(C=C1)C1CCN(CC1)C1CCN(CC1)CCCOC CWHXQDAZBOZPIU-UHFFFAOYSA-N 0.000 claims description 2
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