TWI698436B - 作為泛素特異性蛋白酶７抑制劑之吡咯并及吡唑并嘧啶 - Google Patents

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Publication number

TWI698436B

TWI698436B TW104144096A TW104144096A TWI698436B TW I698436 B TWI698436 B TW I698436B TW 104144096 A TW104144096 A TW 104144096A TW 104144096 A TW104144096 A TW 104144096A TW I698436 B TWI698436 B TW I698436B

Authority

TW

Taiwan

Prior art keywords

methyl

alkyl

pyrimidin

aryl

pyrazolo

Prior art date

2014-12-30

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• 239000003112 inhibitor Substances 0.000 title abstract description 11
• 102000018390 Ubiquitin-Specific Proteases Human genes 0.000 title description 10
• 108010066496 Ubiquitin-Specific Proteases Proteins 0.000 title description 10
• APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title 1
• -1 -OH Chemical group 0.000 claims description 844
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 417
• 125000003118 aryl group Chemical group 0.000 claims description 352
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 293
• 125000000623 heterocyclic group Chemical group 0.000 claims description 256
• 229910020008 S(O) Inorganic materials 0.000 claims description 232
• 125000001072 heteroaryl group Chemical group 0.000 claims description 209
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 205
• 125000000217 alkyl group Chemical group 0.000 claims description 151
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 144
• 150000001875 compounds Chemical class 0.000 claims description 140
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 136
• 229910052736 halogen Inorganic materials 0.000 claims description 128
• 150000002367 halogens Chemical class 0.000 claims description 127
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 119
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 117
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 104
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 101
• 125000001424 substituent group Chemical group 0.000 claims description 81
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 79
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 71
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 67
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 67
• 125000002947 alkylene group Chemical group 0.000 claims description 64
• NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims description 60
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 59
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 58
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 53
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 46
• 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 37
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
• 229940124530 sulfonamide Drugs 0.000 claims description 20
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 16
• 125000003003 spiro group Chemical group 0.000 claims description 14
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
• 238000006467 substitution reaction Methods 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
• NYTMGUJYTBEOGY-IBGZPJMESA-N 5-[[1-[(3S)-4,4-difluoro-3-pyrazol-1-ylbutanoyl]-4-hydroxypiperidin-4-yl]methyl]-1-(4-fluorophenyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC([C@H](CC(=O)N1CCC(CC1)(O)CN1C=NC2=C(C1=O)C=NN2C1=CC=C(C=C1)F)N1N=CC=C1)F NYTMGUJYTBEOGY-IBGZPJMESA-N 0.000 claims 1
• FWROEPKLZWRGHB-UHFFFAOYSA-N CC=CN(CC1)C1C(N(CC1)CCC1(CN(C=NC1=C2C=NN1C(C=C1)=CC=C1C1=CC=CC=C1)C2=O)O)=O Chemical compound CC=CN(CC1)C1C(N(CC1)CCC1(CN(C=NC1=C2C=NN1C(C=C1)=CC=C1C1=CC=CC=C1)C2=O)O)=O FWROEPKLZWRGHB-UHFFFAOYSA-N 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 57
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• 206010028980 Neoplasm Diseases 0.000 abstract description 19
• 230000009385 viral infection Effects 0.000 abstract description 16
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• 230000004770 neurodegeneration Effects 0.000 abstract description 12
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• 101150020913 USP7 gene Proteins 0.000 abstract 1
• 102000052151 Ubiquitin-Specific Peptidase 7 Human genes 0.000 abstract 1
• 229940126752 Ubiquitin-specific protease 7 inhibitor Drugs 0.000 abstract 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 861
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 64
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 62
• 238000000034 method Methods 0.000 description 59
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• 239000002585 base Substances 0.000 description 36
• 239000000651 prodrug Substances 0.000 description 36
• 229940002612 prodrug Drugs 0.000 description 36
• 239000012453 solvate Substances 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
• JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 33
• 239000000543 intermediate Substances 0.000 description 31
• 229910052739 hydrogen Inorganic materials 0.000 description 30
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
• 229910052805 deuterium Inorganic materials 0.000 description 28
• 239000002904 solvent Substances 0.000 description 26
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 24
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 23
• 241000009298 Trigla lyra Species 0.000 description 23
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
• 239000000203 mixture Substances 0.000 description 22
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 19
• 150000004677 hydrates Chemical class 0.000 description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
• 239000004202 carbamide Substances 0.000 description 14
• 235000013877 carbamide Nutrition 0.000 description 14
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
• 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 230000008878 coupling Effects 0.000 description 13
• 238000010168 coupling process Methods 0.000 description 13
• 238000005859 coupling reaction Methods 0.000 description 13
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 12
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
• 201000011510 cancer Diseases 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 229910052717 sulfur Inorganic materials 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 208000035475 disorder Diseases 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
• 108090000623 proteins and genes Proteins 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
• 125000005842 heteroatom Chemical group 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 8
• 108091027076 Spiegelmer Proteins 0.000 description 8
• 150000001412 amines Chemical class 0.000 description 8
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 8
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
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• 125000003545 alkoxy group Chemical group 0.000 description 7
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• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
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• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
• FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 7
• 230000034512 ubiquitination Effects 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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• 230000033228 biological regulation Effects 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 5
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• 239000000126 substance Substances 0.000 description 5
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• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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