TW202438498A - 雜環化合物之用途 - Google Patents
雜環化合物之用途 Download PDFInfo
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- TW202438498A TW202438498A TW113120662A TW113120662A TW202438498A TW 202438498 A TW202438498 A TW 202438498A TW 113120662 A TW113120662 A TW 113120662A TW 113120662 A TW113120662 A TW 113120662A TW 202438498 A TW202438498 A TW 202438498A
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- compound
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- substituted
- pyridin
- acid
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 346
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 201000011510 cancer Diseases 0.000 claims abstract description 26
- -1 6-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl Chemical group 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 63
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- 238000011282 treatment Methods 0.000 claims description 8
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 57
- 239000013078 crystal Substances 0.000 abstract description 11
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 230000009471 action Effects 0.000 abstract description 5
- 102000057613 Mucosa-Associated Lymphoid Tissue Lymphoma Translocation 1 Human genes 0.000 abstract description 4
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- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- 101150113681 MALT1 gene Proteins 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 312
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 150
- 125000005843 halogen group Chemical group 0.000 description 133
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 84
- 230000002829 reductive effect Effects 0.000 description 81
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- 239000000203 mixture Substances 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 63
- 125000001424 substituent group Chemical group 0.000 description 61
- 125000001153 fluoro group Chemical group F* 0.000 description 60
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- 229910052731 fluorine Inorganic materials 0.000 description 48
- 125000001309 chloro group Chemical group Cl* 0.000 description 47
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
- 125000001425 triazolyl group Chemical group 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
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- 230000003213 activating effect Effects 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- 125000003277 amino group Chemical class 0.000 description 13
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- 125000003226 pyrazolyl group Chemical group 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
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- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 6
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
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| GB202018412D0 (en) | 2020-11-23 | 2021-01-06 | Exscientia Ltd | Malt-1 modulators ii |
| KR20240130085A (ko) | 2021-12-30 | 2024-08-28 | 상하이 한서 바이오메디컬 컴퍼니 리미티드 | 트리시클릭 유도체 억제제, 이의 제조 방법 및 응용 |
| WO2023149450A1 (ja) | 2022-02-02 | 2023-08-10 | 小野薬品工業株式会社 | Ｍａｌｔ１阻害薬を有効成分として含むがん治療剤 |
| WO2025123039A1 (en) * | 2023-12-08 | 2025-06-12 | Shaman Pharma, LLC | Method for Production of Spiro-Oxindole and Indoxyl Derivatives of Mitragynine |
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| AU699091B2 (en) * | 1995-05-31 | 1998-11-19 | Dainippon Sumitomo Pharma Co., Ltd. | Novel naphthyridine derivatives |
| GB9720052D0 (en) * | 1997-09-19 | 1997-11-19 | Smithkline Beecham Plc | Novel compounds |
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| US20200289514A1 (en) | 2015-11-13 | 2020-09-17 | Novartis Ag | Novel Pyrazolo Pyrimidine Derivatives |
| KR20190033607A (ko) | 2016-07-29 | 2019-03-29 | 루핀 리미티드 | Malt1 저해제로서의 치환 티아졸로-피리딘 화합물 |
| US10689366B2 (en) * | 2016-11-01 | 2020-06-23 | Cornell University | Compounds for MALT1 degredation |
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| US20200111087A1 (en) * | 2018-10-08 | 2020-04-09 | Jinlei Zhou | Method for encrypting digital contract document between contractors |
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