AU2014236711A1 - Histone demethylase inhibitors - Google Patents

Info

Publication number

AU2014236711A1

AU2014236711A1 AU2014236711A AU2014236711A AU2014236711A1 AU 2014236711 A1 AU2014236711 A1 AU 2014236711A1 AU 2014236711 A AU2014236711 A AU 2014236711A AU 2014236711 A AU2014236711 A AU 2014236711A AU 2014236711 A1 AU2014236711 A1 AU 2014236711A1

Authority

AU

Australia

Prior art keywords

pyridine

imidazol

methyl

carboxylic acid

preparation

Prior art date

2013-03-14

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.)

Abandoned

Links

• Espacenet
• Global Dossier
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• 108010074870 Histone Demethylases Proteins 0.000 title claims abstract description 19
• 102000008157 Histone Demethylases Human genes 0.000 title claims abstract description 19
• 239000003112 inhibitor Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 459
• 238000000034 method Methods 0.000 claims abstract description 274
• 239000000203 mixture Substances 0.000 claims abstract description 46
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 149
• 229910052739 hydrogen Inorganic materials 0.000 claims description 141
• 239000001257 hydrogen Substances 0.000 claims description 139
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 135
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 116
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 125000000623 heterocyclic group Chemical group 0.000 claims description 68
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 58
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 58
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 57
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 53
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 44
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims 3
• -1 imidazole-pyridine derivative compounds Chemical class 0.000 abstract description 178
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
• 238000011282 treatment Methods 0.000 abstract description 13
• 201000010099 disease Diseases 0.000 abstract description 11
• 230000005764 inhibitory process Effects 0.000 abstract description 10
• 206010006187 Breast cancer Diseases 0.000 abstract description 7
• 208000026310 Breast neoplasm Diseases 0.000 abstract description 7
• 206010005003 Bladder cancer Diseases 0.000 abstract description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 abstract description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 abstract description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 abstract description 5
• 201000005202 lung cancer Diseases 0.000 abstract description 5
• 208000020816 lung neoplasm Diseases 0.000 abstract description 5
• 201000005112 urinary bladder cancer Diseases 0.000 abstract description 5
• 206010060862 Prostate cancer Diseases 0.000 abstract description 4
• 201000001441 melanoma Diseases 0.000 abstract description 4
• 230000001613 neoplastic effect Effects 0.000 abstract description 3
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 334
• 238000002360 preparation method Methods 0.000 description 321
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 288
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 167
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 155
• 238000005481 NMR spectroscopy Methods 0.000 description 123
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 103
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 75
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 61
• 125000002947 alkylene group Chemical group 0.000 description 55
• REQFDBXEACLQPU-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2N=CNC=2)=C1 REQFDBXEACLQPU-UHFFFAOYSA-N 0.000 description 52
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 239000000243 solution Substances 0.000 description 47
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 238000003786 synthesis reaction Methods 0.000 description 44
• ZCJVFVODASCOHD-UHFFFAOYSA-N 2-(5-bromo-1-methylimidazol-4-yl)pyridine-4-carbonitrile Chemical compound CN1C=NC(C=2N=CC=C(C=2)C#N)=C1Br ZCJVFVODASCOHD-UHFFFAOYSA-N 0.000 description 37
• 229910052757 nitrogen Inorganic materials 0.000 description 35
• 101150043532 CISH gene Proteins 0.000 description 33
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 33
• 125000004432 carbon atom Chemical group C* 0.000 description 32
• BMTXJJVXXUHJQZ-UHFFFAOYSA-N methyl 2-[1-(2-methylsulfonyloxyethyl)imidazol-4-yl]pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C=2N=CN(CCOS(C)(=O)=O)C=2)=C1 BMTXJJVXXUHJQZ-UHFFFAOYSA-N 0.000 description 31
• 150000003254 radicals Chemical class 0.000 description 31
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 28
• 239000007787 solid Substances 0.000 description 28
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• 101000613625 Homo sapiens Lysine-specific demethylase 4A Proteins 0.000 description 27
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• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 27
• 101001088893 Homo sapiens Lysine-specific demethylase 4C Proteins 0.000 description 26
• 102100033230 Lysine-specific demethylase 4C Human genes 0.000 description 26
• 239000000126 substance Substances 0.000 description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 125000001207 fluorophenyl group Chemical group 0.000 description 22
• 239000002253 acid Substances 0.000 description 21
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• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 20
• 238000003556 assay Methods 0.000 description 19
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 19
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 18
• 125000000068 chlorophenyl group Chemical group 0.000 description 18
• 230000007062 hydrolysis Effects 0.000 description 18
• 238000006460 hydrolysis reaction Methods 0.000 description 18
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 102000006947 Histones Human genes 0.000 description 17
• 210000004027 cell Anatomy 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 102000004169 proteins and genes Human genes 0.000 description 16
• 125000001424 substituent group Chemical group 0.000 description 16
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 15
• 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 15
• 238000001514 detection method Methods 0.000 description 15
• 238000010438 heat treatment Methods 0.000 description 15
• 235000018102 proteins Nutrition 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
• 125000003709 fluoroalkyl group Chemical group 0.000 description 13
• 239000000651 prodrug Substances 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 102100040584 Lysine-specific demethylase 2B Human genes 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
• 235000019439 ethyl acetate Nutrition 0.000 description 12
• 238000003818 flash chromatography Methods 0.000 description 12
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
• 101000614013 Homo sapiens Lysine-specific demethylase 2B Proteins 0.000 description 11
• 101001088892 Homo sapiens Lysine-specific demethylase 5A Proteins 0.000 description 11
• 125000004450 alkenylene group Chemical group 0.000 description 11
• 125000004122 cyclic group Chemical group 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 11
• 238000007069 methylation reaction Methods 0.000 description 11
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• 239000000047 product Substances 0.000 description 11
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• LQWXEEDCMLEVHU-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)pyridine Chemical compound N1=CC=CC=C1C1=NNN=N1 LQWXEEDCMLEVHU-UHFFFAOYSA-N 0.000 description 10
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 10
• 102100033246 Lysine-specific demethylase 5A Human genes 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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• 235000018977 lysine Nutrition 0.000 description 10
• 230000011987 methylation Effects 0.000 description 10
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• NZHDJNMKYDTLEC-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2N=CNC=2)=C1 NZHDJNMKYDTLEC-UHFFFAOYSA-N 0.000 description 9
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 9
• 239000004472 Lysine Substances 0.000 description 9
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• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 8
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