CN112585129A - 杂环化合物,其制备方法和用途 - Google Patents
杂环化合物,其制备方法和用途 Download PDFInfo
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- CN112585129A CN112585129A CN202080004519.0A CN202080004519A CN112585129A CN 112585129 A CN112585129 A CN 112585129A CN 202080004519 A CN202080004519 A CN 202080004519A CN 112585129 A CN112585129 A CN 112585129A
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- optionally substituted
- alkyl
- compound
- hydrogen
- pharmaceutically acceptable
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 152
- 239000001257 hydrogen Substances 0.000 claims description 152
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
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- 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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Abstract
Description
Claims (49)
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PCT/CN2020/091274 WO2020233592A1 (en) | 2019-05-21 | 2020-05-20 | Heterocyclic compounds, preparation methods and uses thereof |
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Cited By (7)
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---|---|---|---|---|
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WO2021249563A1 (zh) * | 2020-06-12 | 2021-12-16 | 苏州泽璟生物制药股份有限公司 | 芳基或杂芳基并吡啶酮或嘧啶酮类衍生物及其制备方法和应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018119183A2 (en) * | 2016-12-22 | 2018-06-28 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
WO2018217651A1 (en) * | 2017-05-22 | 2018-11-29 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
WO2019051291A1 (en) * | 2017-09-08 | 2019-03-14 | Amgen Inc. | KRAS G12C INHIBITORS AND METHODS OF USE |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108658972A (zh) | 2017-03-28 | 2018-10-16 | 中国海洋大学 | 一种取代内酰胺类化合物及其制备方法和用途 |
AU2019262589B2 (en) * | 2018-05-04 | 2022-07-07 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
MX2020012261A (es) * | 2018-06-12 | 2021-03-31 | Amgen Inc | Inhibidores de kras g12c que comprenden un anillo de piperazina y uso de estos en el tratamiento del cancer. |
AU2019377130B2 (en) | 2018-11-09 | 2022-03-17 | F. Hoffmann-La Roche Ag | Fused ring compounds |
JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのkrasg12c阻害剤及び1種以上の薬学的に活性な追加の薬剤を含む併用療法 |
CN110256421A (zh) | 2019-06-26 | 2019-09-20 | 微境生物医药科技(上海)有限公司 | Kras-g12c抑制剂 |
CN111377918B (zh) | 2019-11-29 | 2021-03-02 | 苏州信诺维医药科技有限公司 | 一种kras抑制剂化合物 |
CN111205286B (zh) | 2020-01-13 | 2022-12-13 | 中科苏州药物研究院 | 作为kras g12c突变蛋白抑制剂的腈甲基哌嗪类衍生物及其应用 |
-
2020
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- 2020-05-20 CN CN202080004519.0A patent/CN112585129B/zh active Active
- 2020-05-20 CA CA3139348A patent/CA3139348A1/en active Pending
- 2020-05-20 AU AU2020279287A patent/AU2020279287A1/en active Pending
- 2020-05-20 KR KR1020217041335A patent/KR20220010542A/ko unknown
- 2020-05-20 MX MX2021014096A patent/MX2021014096A/es unknown
- 2020-05-20 WO PCT/CN2020/091274 patent/WO2020233592A1/en unknown
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-
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- 2022-06-30 JP JP2022105508A patent/JP2022130631A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018119183A2 (en) * | 2016-12-22 | 2018-06-28 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
WO2018217651A1 (en) * | 2017-05-22 | 2018-11-29 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
WO2019051291A1 (en) * | 2017-09-08 | 2019-03-14 | Amgen Inc. | KRAS G12C INHIBITORS AND METHODS OF USE |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114846006A (zh) * | 2019-12-18 | 2022-08-02 | 益方生物科技(上海)股份有限公司 | 杂环化合物及其制备方法和用途 |
CN114846006B (zh) * | 2019-12-18 | 2024-04-26 | 益方生物科技(上海)股份有限公司 | 杂环化合物及其制备方法和用途 |
CN113105448A (zh) * | 2020-01-13 | 2021-07-13 | 苏州泽璟生物制药股份有限公司 | 芳基或杂芳基并吡啶酮或嘧啶酮类衍生物及其制备方法和应用 |
WO2021249563A1 (zh) * | 2020-06-12 | 2021-12-16 | 苏州泽璟生物制药股份有限公司 | 芳基或杂芳基并吡啶酮或嘧啶酮类衍生物及其制备方法和应用 |
WO2022111521A1 (zh) * | 2020-11-24 | 2022-06-02 | 杭州多域生物技术有限公司 | 一种芳香化合物、其制备方法及应用 |
WO2022135591A1 (zh) * | 2020-12-25 | 2022-06-30 | 苏州泽璟生物制药股份有限公司 | 芳基或杂芳基并吡啶酮或嘧啶酮类衍生物及其制备方法和应用 |
WO2024017316A1 (zh) * | 2022-07-20 | 2024-01-25 | 益方生物科技(上海)股份有限公司 | 药物组合产品以及组合疗法 |
WO2024081674A1 (en) | 2022-10-11 | 2024-04-18 | Aadi Bioscience, Inc. | Combination therapies for the treatment of cancer |
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US20210355125A1 (en) | 2021-11-18 |
JP2022130631A (ja) | 2022-09-06 |
MX2021014096A (es) | 2022-02-11 |
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WO2020233592A1 (en) | 2020-11-26 |
CN112585129B (zh) | 2022-03-01 |
BR112021023136A2 (pt) | 2022-01-04 |
US20210198255A1 (en) | 2021-07-01 |
US11091481B2 (en) | 2021-08-17 |
AU2020279287A1 (en) | 2021-12-16 |
CN114437065A (zh) | 2022-05-06 |
JP7100210B2 (ja) | 2022-07-12 |
JP2022525247A (ja) | 2022-05-11 |
ZA202110422B (en) | 2024-03-27 |
EP3972967A1 (en) | 2022-03-30 |
IL288104A (en) | 2022-01-01 |
CA3139348A1 (en) | 2020-11-26 |
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