CA3127268A1 - Heterocyclic derivatives - Google Patents
Heterocyclic derivatives Download PDFInfo
- Publication number
- CA3127268A1 CA3127268A1 CA3127268A CA3127268A CA3127268A1 CA 3127268 A1 CA3127268 A1 CA 3127268A1 CA 3127268 A CA3127268 A CA 3127268A CA 3127268 A CA3127268 A CA 3127268A CA 3127268 A1 CA3127268 A1 CA 3127268A1
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- CA
- Canada
- Prior art keywords
- denotes
- compound
- mixture
- mmol
- ethoxy
- 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.)
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- 125000000623 heterocyclic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 305
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- 238000011282 treatment Methods 0.000 claims abstract description 32
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- 239000000203 mixture Substances 0.000 claims description 219
- 238000000034 method Methods 0.000 claims description 200
- -1 1,2-oxazinan-2-yl Chemical group 0.000 claims description 171
- 238000002360 preparation method Methods 0.000 claims description 110
- 150000003839 salts Chemical class 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 13
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
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- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
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- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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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
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| US12293809B2 (en) | 2019-08-23 | 2025-05-06 | Insilico Medicine Ip Limited | Workflow for generating compounds with biological activity against a specific biological target |
| CA3213624A1 (en) * | 2021-03-28 | 2022-10-06 | Canwell Biotech Limited | Metap-2 inhibitors, pharmaceutical compositions and therapeutic methods thereof |
| US20250032625A1 (en) | 2021-11-02 | 2025-01-30 | Merck Patent Gmbh | Heterobifunctional molecules as tead inhibitors |
| WO2023144053A1 (en) | 2022-01-26 | 2023-08-03 | Merck Patent Gmbh | Heterocyclic derivatives |
| CN116854604B (zh) * | 2023-06-27 | 2026-03-24 | 中国科学院微生物研究所 | 一种ω-氨基脂肪酸甲酯、长链尼龙的制备方法 |
| CN119569617A (zh) * | 2025-02-07 | 2025-03-07 | 成都普康唯新生物科技有限公司 | 一种磷酸酯脂肪烷酸及其中间体的合成方法 |
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| WO2002020740A2 (en) | 2000-09-08 | 2002-03-14 | California Institute Of Technology | Proteolysis targeting chimeric pharmaceutical |
| JP2010531896A (ja) * | 2007-06-26 | 2010-09-30 | チルドレンズ メディカル センター コーポレーション | 治療的投与のためのＭｅｔＡＰ−２阻害剤ポリマーソーム |
| DE102009005193A1 (de) * | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Neue heterocyclische Verbindungen als MetAP-2 Inhibitoren |
| DE102010048374A1 (de) * | 2010-10-13 | 2012-04-19 | Merck Patent Gmbh | Pyrrolidinone als MetAP-2 Inhibitoren |
| DE102012006884A1 (de) * | 2012-04-04 | 2013-10-10 | Merck Patent Gmbh | Cyclische Amide als MetAP-2 Inhibitoren |
| WO2014180524A1 (en) * | 2013-05-06 | 2014-11-13 | Merck Patent Gmbh | Macrocycles as kinase inhibitors |
| US20180228907A1 (en) * | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| KR102485537B1 (ko) | 2014-08-04 | 2023-01-05 | 메르크 파텐트 게엠베하 | Metap-2 저해제로서의 피롤리디논 유도체 |
| KR20180132861A (ko) * | 2016-04-12 | 2018-12-12 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | Bet 단백질 분해제 |
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| CN107540608B (zh) | 2017-07-17 | 2021-10-19 | 大连理工大学 | 4-取代萘酰亚胺类化合物及其应用 |
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