JPWO2020231977A5 - - Google Patents
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- Publication number
- JPWO2020231977A5 JPWO2020231977A5 JP2021568200A JP2021568200A JPWO2020231977A5 JP WO2020231977 A5 JPWO2020231977 A5 JP WO2020231977A5 JP 2021568200 A JP2021568200 A JP 2021568200A JP 2021568200 A JP2021568200 A JP 2021568200A JP WO2020231977 A5 JPWO2020231977 A5 JP WO2020231977A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridazin
- pyridin
- fluoro
- oxy
- methyl
- Prior art date
- 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.)
- Granted
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- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 191
- -1 piperidin-1-olato-yl Chemical group 0.000 claims description 158
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 125
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 54
- 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 47
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 32
- BEPZJGUUEAAGDN-UHFFFAOYSA-N pyridin-3-ol dihydrochloride Chemical compound Cl.Cl.Oc1cccnc1 BEPZJGUUEAAGDN-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- FHZOTUIUSLSFDU-LJLRIERRSA-N CC1(C[C@H]([C@H](C(N1)(C)C)F)OC2=NN=C(C=C2)C3=C(C=C(C=N3)C4=CNN=C4)O)C.Cl Chemical compound CC1(C[C@H]([C@H](C(N1)(C)C)F)OC2=NN=C(C=C2)C3=C(C=C(C=N3)C4=CNN=C4)O)C.Cl FHZOTUIUSLSFDU-LJLRIERRSA-N 0.000 claims description 12
- PZJIPXYCKROSLJ-OKILXGFUSA-N C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C1=CC2=CN(N=C2C(=C1)F)C Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C1=CC2=CN(N=C2C(=C1)F)C PZJIPXYCKROSLJ-OKILXGFUSA-N 0.000 claims description 12
- FVYOVBZNDVIMHP-LPHOPBHVSA-N F[C@@H]1C(NC(C[C@@H]1OC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NNC=1)(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1OC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NNC=1)(C)C)(C)C FVYOVBZNDVIMHP-LPHOPBHVSA-N 0.000 claims description 12
- FVYOVBZNDVIMHP-VQIMIIECSA-N F[C@H]1C(NC(C[C@H]1OC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NNC=1)(C)C)(C)C Chemical compound F[C@H]1C(NC(C[C@H]1OC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NNC=1)(C)C)(C)C FVYOVBZNDVIMHP-VQIMIIECSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- BJXSAVYWDGJREZ-REWPJTCUSA-N CC=1N=C2N(N=C(C=C2C)C=2C=C(C(=NC=2)C=2N=NC(=CC=2)O[C@@H]2[C@@H](C(NC(C2)(C)C)(C)C)F)O)C=1 Chemical compound CC=1N=C2N(N=C(C=C2C)C=2C=C(C(=NC=2)C=2N=NC(=CC=2)O[C@@H]2[C@@H](C(NC(C2)(C)C)(C)C)F)O)C=1 BJXSAVYWDGJREZ-REWPJTCUSA-N 0.000 claims description 8
- BJXSAVYWDGJREZ-NFBKMPQASA-N CC=1N=C2N(N=C(C=C2C)C=2C=C(C(=NC=2)C=2N=NC(=CC=2)O[C@H]2[C@H](C(NC(C2)(C)C)(C)C)F)O)C=1 Chemical compound CC=1N=C2N(N=C(C=C2C)C=2C=C(C(=NC=2)C=2N=NC(=CC=2)O[C@H]2[C@H](C(NC(C2)(C)C)(C)C)F)O)C=1 BJXSAVYWDGJREZ-NFBKMPQASA-N 0.000 claims description 8
- UCSROBWHQSVAOQ-OKILXGFUSA-N C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=C(C=C(C=N1)C1=CC(=NC=C1)OC)O Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=C(C=C(C=N1)C1=CC(=NC=C1)OC)O UCSROBWHQSVAOQ-OKILXGFUSA-N 0.000 claims description 8
- OUTUIFKYJKSYSG-GASCZTMLSA-N C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=C(C=C(C=N1)C1=CC2=CN(N=C2C(=C1)C#N)C)O Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=C(C=C(C=N1)C1=CC2=CN(N=C2C(=C1)C#N)C)O OUTUIFKYJKSYSG-GASCZTMLSA-N 0.000 claims description 8
- DTMSVMZVVXXPAM-GASCZTMLSA-N C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C1=CC2=CN(N=C2C(=C1)OC)C Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C1=CC2=CN(N=C2C(=C1)OC)C DTMSVMZVVXXPAM-GASCZTMLSA-N 0.000 claims description 8
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- DIIFYEYNCPMKSM-OKILXGFUSA-N C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=CC=2N(C=1)N=CN=2 Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=CC=2N(C=1)N=CN=2 DIIFYEYNCPMKSM-OKILXGFUSA-N 0.000 claims description 8
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- USEFMPQBPUTANG-DUFSSLHGSA-N C[C@@H]1CN(C[C@@H](N1)C)C2=NN=C(C=C2)C3=C(C=C(C=N3)C4=CC5=C(C=C4)NN=C5)O.Cl.Cl Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C2=NN=C(C=C2)C3=C(C=C(C=N3)C4=CC5=C(C=C4)NN=C5)O.Cl.Cl USEFMPQBPUTANG-DUFSSLHGSA-N 0.000 claims description 8
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- DECYQCLCPJBWDO-CRAIPNDOSA-N FC1=C(C=NN1)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)O[C@H]1[C@H](C(NC(C1)(C)C)(C)C)F)O Chemical compound FC1=C(C=NN1)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)O[C@H]1[C@H](C(NC(C1)(C)C)(C)C)F)O DECYQCLCPJBWDO-CRAIPNDOSA-N 0.000 claims description 8
- AESVNQVEJBWRDI-GASCZTMLSA-N FC1=CC(=CC2=CN(N=C12)C)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)N1C[C@H](N([C@H](C1)C)C)C)O Chemical compound FC1=CC(=CC2=CN(N=C12)C)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)N1C[C@H](N([C@H](C1)C)C)C)O AESVNQVEJBWRDI-GASCZTMLSA-N 0.000 claims description 8
- WFYVRQWCNYKKIM-BETUJISGSA-N N1N=CC(=C1)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)N1C[C@H](N([C@H](C1)C)C)C)O Chemical compound N1N=CC(=C1)C=1C=C(C(=NC=1)C=1N=NC(=CC=1)N1C[C@H](N([C@H](C1)C)C)C)O WFYVRQWCNYKKIM-BETUJISGSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- BZHFIHYFXXRPQM-UHFFFAOYSA-N CC1CN(CCN1)C1=CC=C(N=N1)C1=NC=C(C=C1O)NCC1=CC=NC=C1 Chemical compound CC1CN(CCN1)C1=CC=C(N=N1)C1=NC=C(C=C1O)NCC1=CC=NC=C1 BZHFIHYFXXRPQM-UHFFFAOYSA-N 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- LMFOXRKPQPWMBX-CYQFQFRFSA-N 2-[6-[(3R,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]oxypyridazin-3-yl]-5-(2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyridin-3-ol trihydrochloride Chemical compound CC1=NN2C=C(C=CC2=N1)C3=CC(=C(N=C3)C4=NN=C(C=C4)O[C@H]5CC(NC([C@H]5F)(C)C)(C)C)O.Cl.Cl.Cl LMFOXRKPQPWMBX-CYQFQFRFSA-N 0.000 claims description 4
- MZHUYPDLNAQKKT-CPEHYTGNSA-N 2-[6-[(3R,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]oxypyridazin-3-yl]-5-(2-methylimidazo[1,2-a]pyridin-6-yl)pyridin-3-ol trihydrochloride Chemical compound CC1=CN2C=C(C=CC2=N1)C3=CC(=C(N=C3)C4=NN=C(C=C4)O[C@H]5CC(NC([C@H]5F)(C)C)(C)C)O.Cl.Cl.Cl MZHUYPDLNAQKKT-CPEHYTGNSA-N 0.000 claims description 4
- OASWFGLMIQVGCL-CESJSFPBSA-N 2-[6-[(3R,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]oxypyridazin-3-yl]-5-(2-methylimidazo[1,2-a]pyrimidin-6-yl)pyridin-3-ol trihydrochloride Chemical compound CC1=CN2C=C(C=NC2=N1)C3=CC(=C(N=C3)C4=NN=C(C=C4)O[C@H]5CC(NC([C@H]5F)(C)C)(C)C)O.Cl.Cl.Cl OASWFGLMIQVGCL-CESJSFPBSA-N 0.000 claims description 4
- SBBKJFMLZNJVNX-JXFKEZNVSA-N 2-[6-[(3R,4S)-3-fluoro-2,2,6,6-tetramethylpiperidin-4-yl]oxypyridazin-3-yl]-5-([1,2,4]triazolo[1,5-a]pyrazin-2-yl)pyridin-3-ol Chemical compound F[C@@H]1C(NC(C[C@@H]1OC1=CC=C(N=N1)C1=NC=C(C=C1O)C1=NN2C(C=NC=C2)=N1)(C)C)(C)C SBBKJFMLZNJVNX-JXFKEZNVSA-N 0.000 claims description 4
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- XTNDDOMTDGOHPB-HPRDVNIFSA-N CC1(NC2(CC2)CC(C1)N(C1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])C)C Chemical compound CC1(NC2(CC2)CC(C1)N(C1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])C)C XTNDDOMTDGOHPB-HPRDVNIFSA-N 0.000 claims 2
- XNPOOULYYABWIZ-QMYZHSFRSA-N F[C@@H]1C(NC(C[C@@H]1NC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1NC1=CC=C(N=N1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])(C)C)(C)C XNPOOULYYABWIZ-QMYZHSFRSA-N 0.000 claims 2
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- BNLHGAIVTUIFDA-RNHVAZJGSA-N [2H]C([2H])([2H])N1C=C(C=N1)C2=CC(=C(N=C2)C3=NN=C(C=C3)N(C)C4CC(NC5(C4)CC5)(C)C)O.Cl.Cl Chemical compound [2H]C([2H])([2H])N1C=C(C=N1)C2=CC(=C(N=C2)C3=NN=C(C=C3)N(C)C4CC(NC5(C4)CC5)(C)C)O.Cl.Cl BNLHGAIVTUIFDA-RNHVAZJGSA-N 0.000 claims 2
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- PZNKFJASJZVUPT-GKOSEXJESA-N C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H] Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=NC(=CN=1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H] PZNKFJASJZVUPT-GKOSEXJESA-N 0.000 claims 1
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- OMQHXLCATZKFCT-PPTCOAGHSA-N F[C@@H]1C(NC(C[C@@H]1NC=1N=NC(=CN=1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])(C)C)(C)C Chemical compound F[C@@H]1C(NC(C[C@@H]1NC=1N=NC(=CN=1)C1=NC=C(C=C1O)C=1C=NN(C=1)C([2H])([2H])[2H])(C)C)(C)C OMQHXLCATZKFCT-PPTCOAGHSA-N 0.000 claims 1
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| EP3634953B1 (en) | 2017-06-05 | 2024-01-03 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
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| EA202092001A1 (ru) | 2018-03-27 | 2021-01-29 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения болезни гентингтона |
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| CN115768762A (zh) * | 2020-04-09 | 2023-03-07 | Ptc医疗公司 | 用于治疗亨廷顿氏病的化合物 |
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2020
- 2020-05-12 JP JP2021568200A patent/JP7649257B2/ja active Active
- 2020-05-12 EP EP23162466.9A patent/EP4219466A1/en active Pending
- 2020-05-12 CA CA3139821A patent/CA3139821A1/en active Pending
- 2020-05-12 EP EP20729481.0A patent/EP3969446B1/en active Active
- 2020-05-12 US US17/610,617 patent/US12577226B2/en active Active
- 2020-05-12 AU AU2020277027A patent/AU2020277027A1/en not_active Abandoned
- 2020-05-12 BR BR112021022624A patent/BR112021022624A2/pt not_active Application Discontinuation
- 2020-05-12 KR KR1020217036718A patent/KR20220022114A/ko active Pending
- 2020-05-12 MX MX2021013854A patent/MX2021013854A/es unknown
- 2020-05-12 IL IL287945A patent/IL287945B2/en unknown
- 2020-05-12 CN CN202080050837.0A patent/CN114245794B/zh active Active
- 2020-05-12 WO PCT/US2020/032446 patent/WO2020231977A1/en not_active Ceased
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