TW202140477A - 雜環ｐａｄ４抑制劑 - Google Patents

Info

Publication number

TW202140477A

TW202140477A TW110105125A TW110105125A TW202140477A TW 202140477 A TW202140477 A TW 202140477A TW 110105125 A TW110105125 A TW 110105125A TW 110105125 A TW110105125 A TW 110105125A TW 202140477 A TW202140477 A TW 202140477A

Authority

TW

Taiwan

Prior art keywords

substituted

optionally

independently selected

alkyl

pyridin

Prior art date

2020-02-12

Links

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• Global Dossier
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• 125000000623 heterocyclic group Chemical group 0.000 title claims description 164
• 239000003112 inhibitor Substances 0.000 title abstract description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 213
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
• 102100035731 Protein-arginine deiminase type-4 Human genes 0.000 claims abstract description 55
• 201000010099 disease Diseases 0.000 claims abstract description 52
• 238000011282 treatment Methods 0.000 claims abstract description 43
• 230000000694 effects Effects 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• -1 -NR a C( =O) OR b Chemical group 0.000 claims description 551
• 125000000217 alkyl group Chemical group 0.000 claims description 449
• 229910052731 fluorine Inorganic materials 0.000 claims description 306
• 229910052801 chlorine Inorganic materials 0.000 claims description 280
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 234
• 229910052739 hydrogen Inorganic materials 0.000 claims description 227
• 125000001424 substituent group Chemical group 0.000 claims description 204
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 152
• 150000003839 salts Chemical class 0.000 claims description 104
• 229910052794 bromium Inorganic materials 0.000 claims description 85
• 125000002837 carbocyclic group Chemical group 0.000 claims description 73
• 239000000203 mixture Substances 0.000 claims description 66
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 64
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 55
• 150000002576 ketones Chemical class 0.000 claims description 52
• 125000003342 alkenyl group Chemical group 0.000 claims description 44
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 43
• 229910052760 oxygen Inorganic materials 0.000 claims description 40
• 125000000304 alkynyl group Chemical group 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 24
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
• PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 13
• 206010025135 lupus erythematosus Diseases 0.000 claims description 13
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 11
• RMDZEYGVJXVEHQ-MQNHUJCZSA-N N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)OC Chemical compound N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)OC RMDZEYGVJXVEHQ-MQNHUJCZSA-N 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• WMHGLLZEVOPGQD-UHFFFAOYSA-N 2h-pyridine-1-carbaldehyde Chemical compound O=CN1CC=CC=C1 WMHGLLZEVOPGQD-UHFFFAOYSA-N 0.000 claims description 8
• QBXBCMGLHGMKAG-GWQXNCQPSA-N N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)F Chemical compound N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)F QBXBCMGLHGMKAG-GWQXNCQPSA-N 0.000 claims description 8
• XOLAWWUOASQDJW-GWQXNCQPSA-N N[C@H]1CN(CCC1)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=C(N=CC=2)OCC2CC(NC2)=O)N1CC1CC1 Chemical compound N[C@H]1CN(CCC1)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=C(N=CC=2)OCC2CC(NC2)=O)N1CC1CC1 XOLAWWUOASQDJW-GWQXNCQPSA-N 0.000 claims description 8
• SISWABZROHQKSF-KAYWLYCHSA-N N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)C1CCN(CC1)C(C)=O)CC1CC1 Chemical compound N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)C1CCN(CC1)C(C)=O)CC1CC1 SISWABZROHQKSF-KAYWLYCHSA-N 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
• VCRPZYSWYJNSSU-GQVVIVCQSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC=C3CNC(C3=C2)=O)N1CC1CC1)F Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC=C3CNC(C3=C2)=O)N1CC1CC1)F VCRPZYSWYJNSSU-GQVVIVCQSA-N 0.000 claims description 6
• QWQNRWYTWVVVKW-CDHPUSFOSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C=C3CNC(C3=CC=2)=O)N1CC1CC1)F Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C=C3CNC(C3=CC=2)=O)N1CC1CC1)F QWQNRWYTWVVVKW-CDHPUSFOSA-N 0.000 claims description 6
• IGZIDTNYUHLUDZ-GWQXNCQPSA-N N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=C(N=CC=2)OCC2CC(NC2)=O)N1CC1CC1)OC Chemical compound N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=C(N=CC=2)OCC2CC(NC2)=O)N1CC1CC1)OC IGZIDTNYUHLUDZ-GWQXNCQPSA-N 0.000 claims description 6
• IKTYIDRYTBVZJC-CGCOGMFASA-N N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)C1CCN(CC1)C(=O)C1CC(C1)O)CC1CC1)OC Chemical compound N[C@H]1CN(CCC1)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)C1CCN(CC1)C(=O)C1CC(C1)O)CC1CC1)OC IKTYIDRYTBVZJC-CGCOGMFASA-N 0.000 claims description 6
• QJNIOIAUPWMKOU-QENMJEOYSA-N N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)F Chemical compound N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)F QJNIOIAUPWMKOU-QENMJEOYSA-N 0.000 claims description 6
• DIJJZENEBLRQKH-BPAKYRGESA-N N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)OC Chemical compound N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1)OC DIJJZENEBLRQKH-BPAKYRGESA-N 0.000 claims description 6
• ZMFZTCYELZMIET-FQLXRVMXSA-N N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=C(C=C2C=1)F)C1CCN(CC1)C(CC(C)C)=O)CC1CC1 Chemical compound N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=C(C=C2C=1)F)C1CCN(CC1)C(CC(C)C)=O)CC1CC1 ZMFZTCYELZMIET-FQLXRVMXSA-N 0.000 claims description 6
• JNZBVJKZOKYVKZ-BPAKYRGESA-N N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1 Chemical compound N[C@H]1CN(C[C@@H](C1)F)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C=1N(C2=C(C=CC=C2C=1)OCC1CC(NC1)=O)CC1CC1 JNZBVJKZOKYVKZ-BPAKYRGESA-N 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 150000001924 cycloalkanes Chemical class 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• VTVMQRLFFHMHQN-STHVYQTBSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C=C3CNC(C3=CC=2)=O)N1CC1CC1)OC Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C=C3CNC(C3=CC=2)=O)N1CC1CC1)OC VTVMQRLFFHMHQN-STHVYQTBSA-N 0.000 claims description 5
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
• HMDXLSRPXZDELQ-FQLXRVMXSA-N C1(CC1)CN1C(=CC2=CC=C(C=C12)N1CCC(CC1)C(=O)N1CCCC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C Chemical compound C1(CC1)CN1C(=CC2=CC=C(C=C12)N1CCC(CC1)C(=O)N1CCCC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C HMDXLSRPXZDELQ-FQLXRVMXSA-N 0.000 claims description 4
• ZWMCVIZGYFDPSW-JWQCQUIFSA-N N1(C=NC=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C Chemical compound N1(C=NC=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C ZWMCVIZGYFDPSW-JWQCQUIFSA-N 0.000 claims description 4
• ZWCHQONPPFWELH-XMMPIXPASA-N N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](CCC2)N)OC)=C1C)CC1CC1 Chemical compound N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](CCC2)N)OC)=C1C)CC1CC1 ZWCHQONPPFWELH-XMMPIXPASA-N 0.000 claims description 4
• CZVROBPEHUHFMR-XMMPIXPASA-N N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](CCC2)N)=C1C)CC1CC1 Chemical compound N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](CCC2)N)=C1C)CC1CC1 CZVROBPEHUHFMR-XMMPIXPASA-N 0.000 claims description 4
• XXDNUMUDDCAXNQ-DNQXCXABSA-N N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C)CC1CC1 Chemical compound N1(C=NC=C1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C)CC1CC1 XXDNUMUDDCAXNQ-DNQXCXABSA-N 0.000 claims description 4
• GNLNNCWVFJCDTI-XMMPIXPASA-N N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](CCC2)N)OC)=C1C Chemical compound N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](CCC2)N)OC)=C1C GNLNNCWVFJCDTI-XMMPIXPASA-N 0.000 claims description 4
• CQVIRQXKSDGPOF-DNQXCXABSA-N N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)OC)=C1C Chemical compound N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C(=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)OC)=C1C CQVIRQXKSDGPOF-DNQXCXABSA-N 0.000 claims description 4
• YZCLJWRMRRFTHD-DNQXCXABSA-N N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C Chemical compound N1(N=CN=C1)CCOC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](C[C@H](C2)F)N)=C1C YZCLJWRMRRFTHD-DNQXCXABSA-N 0.000 claims description 4
• GGMCVRJPNGHOEL-HSZRJFAPSA-N N=1N=CN(C=1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](CCC2)N)=C1C)CC1CC1 Chemical compound N=1N=CN(C=1)CCOC=1N=CC=C2C=1N(C(=C2)C1=NN2C(C=CC(=C2)C(=O)N2C[C@@H](CCC2)N)=C1C)CC1CC1 GGMCVRJPNGHOEL-HSZRJFAPSA-N 0.000 claims description 4
• PDNLGXZOAZNKIK-SGAJGPLNSA-N N[C@H]1C2N(CC1CC2)C(=O)C1=CC2=C(C(=C(O2)C2=CC=3C(=NC(=CC=3)C=3C=C4CNC(C4=CC=3)=O)N2CC2CC2)C)C=C1 Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C1=CC2=C(C(=C(O2)C2=CC=3C(=NC(=CC=3)C=3C=C4CNC(C4=CC=3)=O)N2CC2CC2)C)C=C1 PDNLGXZOAZNKIK-SGAJGPLNSA-N 0.000 claims description 4
• BVRLFUCIQFLHLF-GNTVVGMTSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C(=C(C=CC=2)O)C)N1CC1CC1)F Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=C(C=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C=2C(=C(C=CC=2)O)C)N1CC1CC1)F BVRLFUCIQFLHLF-GNTVVGMTSA-N 0.000 claims description 4
• QKTGQAATUHYPAK-CDHPUSFOSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC(=C(C(=O)N)C=C2)F)N1CC1CC1 Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC(=C(C(=O)N)C=C2)F)N1CC1CC1 QKTGQAATUHYPAK-CDHPUSFOSA-N 0.000 claims description 4
• DSHBRCUJDMKWOP-WJBWUKACSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC(=C(C(=O)N)C=C2C)F)N1CC1CC1 Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC(=C(C(=O)N)C=C2C)F)N1CC1CC1 DSHBRCUJDMKWOP-WJBWUKACSA-N 0.000 claims description 4
• PYJNYZBYHLTDKK-ZVHXTAQDSA-N N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC=C(C=C2)N2C(CCC2)=O)N1CC1CC1 Chemical compound N[C@H]1C2N(CC1CC2)C(=O)C=1C=CC=2N(C=1)N=C(C=2C)C1=CC=2C(=NC(=CC=2)C2=CC=C(C=C2)N2C(CCC2)=O)N1CC1CC1 PYJNYZBYHLTDKK-ZVHXTAQDSA-N 0.000 claims description 4
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