JPWO2020239999A5 - - Google Patents
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- JPWO2020239999A5 JPWO2020239999A5 JP2021570919A JP2021570919A JPWO2020239999A5 JP WO2020239999 A5 JPWO2020239999 A5 JP WO2020239999A5 JP 2021570919 A JP2021570919 A JP 2021570919A JP 2021570919 A JP2021570919 A JP 2021570919A JP WO2020239999 A5 JPWO2020239999 A5 JP WO2020239999A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ethynyl
- pyrimidin
- hydroxy
- amino
- 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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- 150000001875 compounds Chemical class 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 18
- IRWCCQNHZKTMBC-HXUWFJFHSA-N NC1=NC=NC2=C1N=C(N=C2C)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O Chemical compound NC1=NC=NC2=C1N=C(N=C2C)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O IRWCCQNHZKTMBC-HXUWFJFHSA-N 0.000 claims description 9
- RLDYBDXGTWEFJZ-NRFANRHFSA-N NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O RLDYBDXGTWEFJZ-NRFANRHFSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- SYDSHTZOHFOVFO-VXQWRZFRSA-N (3R)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O SYDSHTZOHFOVFO-VXQWRZFRSA-N 0.000 claims description 8
- DZTZPLQFQOSNIE-FQEVSTJZSA-N NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)Cl Chemical compound NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)Cl DZTZPLQFQOSNIE-FQEVSTJZSA-N 0.000 claims description 8
- FKVSVHKPLBGNQS-FQEVSTJZSA-N NC1=NC=CC2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC1=NC=CC2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O FKVSVHKPLBGNQS-FQEVSTJZSA-N 0.000 claims description 8
- LJGVSTKZALQANF-SHKVTDPKSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C([2H])([2H])[2H] Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C([2H])([2H])[2H] LJGVSTKZALQANF-SHKVTDPKSA-N 0.000 claims description 8
- CIRHIKZELFNGMU-NRFANRHFSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)NC Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)NC CIRHIKZELFNGMU-NRFANRHFSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- SYDSHTZOHFOVFO-WRLIODQTSA-N (3S)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O SYDSHTZOHFOVFO-WRLIODQTSA-N 0.000 claims description 7
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- CXTMHGLFUDUJLE-IBGZPJMESA-N NC=1C2=C(N=CN=1)SC(=N2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=CN=1)SC(=N2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O CXTMHGLFUDUJLE-IBGZPJMESA-N 0.000 claims description 7
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- RLDYBDXGTWEFJZ-OAQYLSRUSA-N NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O RLDYBDXGTWEFJZ-OAQYLSRUSA-N 0.000 claims description 6
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- LZAUFLQEOZGLBG-WNBCCLPKSA-N (3R)-3-[2-[3-(2-deuterio-8-ethyl-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)CC LZAUFLQEOZGLBG-WNBCCLPKSA-N 0.000 claims description 5
- DYUIILDYMFTFPP-MUPYNFCXSA-N (3R)-3-[2-[3-(8-cyclopentyl-2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C1CCCC1 DYUIILDYMFTFPP-MUPYNFCXSA-N 0.000 claims description 5
- DRSHHHLTFNAOGN-KIKSHYFBSA-N (3R,5R)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1,5-dimethylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N([C@@H](C1)C)C)=O)O DRSHHHLTFNAOGN-KIKSHYFBSA-N 0.000 claims description 5
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 201000011152 Pemphigus Diseases 0.000 claims description 3
- 206010037575 Pustular psoriasis Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 208000002557 hidradenitis Diseases 0.000 claims description 3
- 201000007162 hidradenitis suppurativa Diseases 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 208000030159 metabolic disease Diseases 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 201000001976 pemphigus vulgaris Diseases 0.000 claims description 3
- 201000010914 pustulosis of palm and sole Diseases 0.000 claims description 3
- 208000011797 pustulosis palmaris et plantaris Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
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- 125000000217 alkyl group Chemical group 0.000 description 38
- 125000001188 haloalkyl group Chemical group 0.000 description 6
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| KR20220030222A (ko) | 2019-05-31 | 2022-03-10 | 이케나 온콜로지, 인코포레이티드 | Tead 억제제 및 이의 용도 |
| IL316886A (en) * | 2022-05-11 | 2025-01-01 | Janssen Pharmaceutica Nv | History of pyrrolidinones as NF kappa B kinase inhibitors |
| CA3257152A1 (en) * | 2022-05-11 | 2023-11-16 | Janssen Pharmaceutica Nv | Pyrrolidine derivatives useful as NF-κB induction kinase inhibitors |
| EP4637773A1 (en) | 2022-12-22 | 2025-10-29 | Boehringer Ingelheim International GmbH | Crystalline forms of a her2 inhibitor |
| WO2025020886A1 (zh) * | 2023-07-27 | 2025-01-30 | 浙江星浩澎博医药有限公司 | 氮杂喹唑啉环衍生物及其用途 |
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| WO2025235874A1 (en) * | 2024-05-10 | 2025-11-13 | Schrödinger, Inc. | Heterocyclics as egfr inhibitors |
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