ES2980537T3 - Análogos de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona - Google Patents
Análogos de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona Download PDFInfo
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- ES2980537T3 ES2980537T3 ES18842344T ES18842344T ES2980537T3 ES 2980537 T3 ES2980537 T3 ES 2980537T3 ES 18842344 T ES18842344 T ES 18842344T ES 18842344 T ES18842344 T ES 18842344T ES 2980537 T3 ES2980537 T3 ES 2980537T3
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- JTNQNHQPENYUGB-UHFFFAOYSA-N 1,2-dihydropyrazolo[3,4-d]pyrimidin-3-one Chemical class C1=NC=C2C(O)=NNC2=N1 JTNQNHQPENYUGB-UHFFFAOYSA-N 0.000 title description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 85
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
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- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 42
- 150000001412 amines Chemical class 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
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- 125000002947 alkylene group Chemical group 0.000 claims description 17
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
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- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
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- 230000004663 cell proliferation Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 151
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 101000621390 Homo sapiens Wee1-like protein kinase Proteins 0.000 description 101
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- 230000000694 effects Effects 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- 210000004027 cell Anatomy 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
- 238000000034 method Methods 0.000 description 68
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 47
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- 125000004432 carbon atom Chemical group C* 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
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- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical group C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 description 1
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- OLOIFCYZWOTWRO-UHFFFAOYSA-N tert-butyl 6-amino-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound NC1=CC=C2CN(C(=O)OC(C)(C)C)CCC2=C1 OLOIFCYZWOTWRO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762539734P | 2017-08-01 | 2017-08-01 | |
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| US10807994B2 (en) | 2017-10-09 | 2020-10-20 | Nuvation Bio Inc. | Heterocyclic compounds and uses thereof |
| WO2019074979A1 (en) * | 2017-10-09 | 2019-04-18 | Girafpharma, Llc | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
| EP3758706A4 (en) * | 2018-02-28 | 2021-11-24 | The Regents Of The University Of Colorado | WEE1 KINASE INHIBITORS AND METHODS OF TREATING CANCER USING THEREOF |
| KR20250073542A (ko) | 2018-03-09 | 2025-05-27 | 리커리엄 아이피 홀딩스, 엘엘씨 | 치환된 1,2-다이하이드로-3H-피라졸로[3,4-d]피리미딘-3-온 |
| CN110872296B (zh) * | 2018-08-31 | 2023-05-23 | 上海弘翊生物科技有限公司 | 一种二氢异吲哚-1H-吡唑并[3,4-d]嘧啶酮化合物、其制备方法和应用 |
| KR20210150476A (ko) * | 2019-04-09 | 2021-12-10 | 누베이션 바이오 인크. | 헤테로시클릭 화합물 및 그의 용도 |
| EP3952875A4 (en) * | 2019-04-09 | 2022-12-28 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
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| CN112142748B (zh) | 2019-06-28 | 2023-07-04 | 上海医药集团股份有限公司 | 一种吡唑酮并嘧啶类化合物、其制备方法及应用 |
| CA3145344A1 (en) | 2019-06-28 | 2020-12-30 | Shanghai Pharmaceuticals Holding Co., Ltd. | Pyrazolopyrimidine compound, preparation method for same and applications thereof |
| CN112442049A (zh) * | 2019-09-03 | 2021-03-05 | 微境生物医药科技(上海)有限公司 | 作为Wee1抑制剂的嘧啶衍生物 |
| US12410204B2 (en) | 2019-11-15 | 2025-09-09 | Recurium Ip Holdings, Llc | Chiral synthesis of a tertiary alcohol |
| JP7631348B2 (ja) * | 2019-12-20 | 2025-02-18 | リキュリウム アイピー ホールディングス リミテッド ライアビリティー カンパニー | 組み合わせ |
| NZ793883A (en) * | 2020-05-15 | 2025-11-28 | Recurium Ip Holdings Llc | Mono- and combination therapies |
| EP4169919A4 (en) * | 2020-06-17 | 2024-07-17 | Wigen Biomedicine Technology (Shanghai) Co., Ltd. | PYRAZOLO[3,4-D]PYRIMIDINE-3-KETONE DERIVATIVE USED AS WEE-1 INHIBITOR |
| CN114805357B (zh) * | 2021-01-21 | 2023-12-19 | 四川大学 | 一种靶向setdb1-ttd的小分子抑制剂及其制药用途 |
| CA3214894A1 (en) * | 2021-04-30 | 2022-11-03 | Yuli Xie | Fused ring compound as wee-1 inhibitor, and preparation method therefor and use thereof |
| WO2023016417A1 (zh) * | 2021-08-11 | 2023-02-16 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的1,2-二氢-3H-吡唑[3,4-d]嘧啶-3-酮化合物 |
| CN117940430B (zh) * | 2021-09-22 | 2025-10-31 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的1,2-二氢-3H-吡唑[3,4-d]嘧啶-3-酮化合物 |
| WO2023166080A1 (en) | 2022-03-01 | 2023-09-07 | Step Pharma S.A.S. | Combination treatments comprising a ctps1 inhibitor and a wee1 inhibitor |
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| AR060635A1 (es) * | 2006-04-27 | 2008-07-02 | Banyu Pharma Co Ltd | Derivados de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona, composiciones farmaceuticas que los comprenden y su uso en el tratamiento del cancer |
| JPWO2009054332A1 (ja) | 2007-10-23 | 2011-03-03 | 萬有製薬株式会社 | ピリドン置換ジヒドロピラゾロピリミジノン誘導体 |
| SMT201900344T1 (it) * | 2012-09-10 | 2019-07-11 | Principia Biopharma Inc | Composti di pirazolopirimidina come inibitori di chinasi |
| GB201612092D0 (en) * | 2016-07-12 | 2016-08-24 | Almac Discovery Ltd | Pharmaceutical compounds |
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