ES2721268T3 - Compuestos de pirazolo[1,5-a]pirimidina-5,7-diamina como inhibidores de CDK y su uso terapéutico - Google Patents
Compuestos de pirazolo[1,5-a]pirimidina-5,7-diamina como inhibidores de CDK y su uso terapéutico Download PDFInfo
- Publication number
- ES2721268T3 ES2721268T3 ES15706282T ES15706282T ES2721268T3 ES 2721268 T3 ES2721268 T3 ES 2721268T3 ES 15706282 T ES15706282 T ES 15706282T ES 15706282 T ES15706282 T ES 15706282T ES 2721268 T3 ES2721268 T3 ES 2721268T3
- Authority
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- Spain
- Prior art keywords
- piperazino
- independently
- branched
- linear
- alkyl
- 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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Links
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title 1
- GLWUDZAXMREBCZ-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical class N1=C(N)C=C(N)N2N=CC=C21 GLWUDZAXMREBCZ-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 13
- 229920006395 saturated elastomer Polymers 0.000 abstract 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 102100037241 Endoglin Human genes 0.000 abstract 1
- 101000881679 Homo sapiens Endoglin Proteins 0.000 abstract 1
- 101000799194 Homo sapiens Serine/threonine-protein kinase receptor R3 Proteins 0.000 abstract 1
- 102100034136 Serine/threonine-protein kinase receptor R3 Human genes 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61P35/04—Antineoplastic agents specific for metastasis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Un compuesto de la siguiente fórmula:**Fórmula** o una sal o un solvato farmacéuticamente aceptable del mismo; en la que: -R5X es -L5X-Q; -L5X- es independientemente un enlace covalente individual o -L5XA-; -L5XA- es independientemente alquileno C1-6 saturado, lineal o ramificado, y está opcionalmente sustituido con uno o más grupos seleccionados entre -OH y -ORL5X, en donde cada -RL5X es independientemente alquilo C1-6 saturado o cicloalquilo C3-6 saturado, lineales o ramificados; -Q es un anillo heterocíclico no aromático que tiene de 5 a 7 átomos en el anillo, incluyendo al menos un átomo de nitrógeno en el anillo, y está sustituido con "n" grupos -J, y está sustituido con "m" grupos -RQ; "n" es 1, 2 o 3; "m" es 0, 1, 2 o 3; cada -J es independientemente -OH; cada -RQ es independientemente -F, -Cl, -Br, -I, -RQA, -CF3, -OCF3, -NH2, -NHRQA, -NRQA 2, pirrolidino, piperidino, morfolino, piperazino, N-(RQA)-piperazino, -SH, -SRQA o -CN; cada -RQA es independientemente alquilo C1-6 saturado o cicloalquilo C3-6 saturado, lineales o ramificados; -R5Y es independientemente -H o -R5YA; -R5YA es independientemente alquilo C1-6 saturado, lineal o ramificado; -R7 es independientemente -R7X o -C(=O)R7X; cada -R7X es independientemente: -R7A, -R7B, -R7C, -R7D, -R7E, -L7-R7B, -L7-R7C, -L7-R7D o -L7-R7E; cada -L7- es independientemente alquileno C1-6saturado, lineal o ramificado; cada -R7A es independientemente alquilo C1-6 saturado, lineal o ramificado, y está opcionalmente sustituido con uno o más sustituyentes -W1; cada -R7B es cicloalquilo C3-6 saturado, y está opcionalmente sustituido con uno o más sustituyentes -W2; cada -R7C es heterociclilo C3-7 no aromático, y está opcionalmente sustituido con uno o más sustituyentes -W2; cada -R7D es fenilo o naftilo, y está opcionalmente sustituido con uno o más sustituyentes -W3; cada -R7E es heteroarilo C5-12, y está opcionalmente sustituido con uno o más sustituyentes -W3; cada -W1 es independientemente: -F, -Cl, -Br, -I, -CF3, -OH, -ORW1, -OCF3, -NH2, -NHRW1, -NRW1 2, pirrolidino, piperidino, morfolino, piperazino, N-(RW1)-piperazino, -C(=O)OH, -C(=O)ORW1, -C(=O)NH2, -C(=O)NHRW1, -C(=O)NRW1 2, -C(=O)-pirrolidino, - C(=O)-piperidino, -C(=O)-morfolino, -C(=O)-piperazino, -C(=O)-N-(RW1)-piperazino, -S(=O)RW1, -S(=O)2RW1, - S(=O)2NH2, -S(=O)2NHRW1, -S(=O)2NRW1 2, -S(=O)2pirrolidino, -S(=O)2-piperidino, -S(=O)2-morfolino, -S(=O)2- piperazino, -S(=O)2-N-(RW1)-piperazino, -CN o -NO2; en donde cada -RW1 es independientemente alquilo C1-6 saturado, lineal o ramificado, fenilo o -CH2-fenilo, en donde cada fenilo está opcionalmente sustituido con uno o más grupos seleccionados entre -F, -Cl, -Br, -I, - RW11, -CF3, -OH, -ORW11 y -OCF3, en donde cada -RW11 es independientemente alquilo C1-6 saturado, lineal o ramificado; cada -W2 es independientemente: -F, -Cl, -Br, -I, -RW2, -CF3, -OH, -ORW2, -OCF3, -NH2, -NHRW2, -NRW2 2, pirrolidino, piperidino, morfolino, piperazino, N-(RW2)-piperazino, -C(=O)OH, -C(=O)ORW2, -C(=O)NH2, -C(=O)NHRW2, -C(=O)NRW2 2, -C(=O)- pirrolidino, -C(=O)-piperidino, -C(=O)-morfolino, -C(=O)-piperazino, -C(=O)-N-(RW2)-piperazino, -S(=O)RW2, - S(=O)2RW2, -S(=O)2NH2, -S(=O)2NHRW2, -S(=O)2NRW2 2, -S(=O)2pirrolidino, -S(=O)2-piperidino, -S(=O)2- morfolino, -S(=O)2-piperazino, -S(=O)2-N-(RW2)-piperazino, -CN o -NO2; en donde cada -RW2 es independientemente alquilo C1-6 saturado, lineal o ramificado, fenilo o -CH2-fenilo, en donde cada fenilo está opcionalmente sustituido con uno o más grupos seleccionados entre -F, -Cl, -Br, -I, - RW22, -CF3, -OH, -ORW22 y -OCF3, en donde cada -RW22 es independientemente alquilo C1-6 saturado, lineal o ramificado; cada -W3 es independientemente: -F, -Cl, -Br, -I, -RW3, -CF3, -OH, -ORW3, -OCF3, -NH2, -NHRW3, -NRW3 2, pirrolidino, piperidino, morfolino, piperazino, N-(RW3)-piperazino, -C(=O)OH, -C(=O)ORW3, -C(=O)NH2, -C(=O)NHRW3, -C(=O)NRW3 2, -C(=O)- pirrolidino, -C(=O)-piperidino, -C(=O)-morfolino, -C(=O)-piperazino, -C(=O)-N-(RW3)-piperazino, -S(=O)RW3, - S(=O)2RW3, -S(=O)2NH2, -S(=O)2NHRW3, -S(=O)2NRW3 2, -S(=O)2pirrolidino, -S(=O)2-piperidino, -S(=O)2- morfolino, -S(=O)2-piperazino, -S(=O)2-N-(RW3)-piperazino, -CN o -NO2; en donde cada -RW3 es independientemente alquilo C1-6 saturado, lineal o ramificado, fenilo o -CH2-fenilo, en donde cada fenilo está opcionalmente sustituido con uno o más grupos seleccionados entre -F, -Cl, -Br, -I, - RW33, -CF3, -OH, -ORW33 y -OCF3, en donde cada -RW33 es independientemente alquilo C1-6 saturado, lineal o ramificado; -R3 es independientemente -R3A o -R3B; -R3A es independientemente alquilo C1-6 saturado, lineal o ramificado; -R3B es independientemente cicloalquilo C3-7 saturado; -R2 es independientemente -H o -R2A; -R2A es independientemente -F, -Cl, -Br, -I, -R2AA, -CF3, -OH, -OR2AA, -OCF3, -NH2, -NHR2AA, -NR2AA 2, pirrolidino, piperidino, morfolino, piperazino, N-(R2AA)-piperazino, -SH, -SR2AA o -CN; cada -R2AA es independientemente alquilo C1-6 saturado, lineal o ramificado; -R6 es independientemente -H o -R6A; -R6A es independientemente -F, -Cl, -Br, -I, -R6AA, -CF3, -OH, -OR6AA, -OCF3, -NH2, -NHR6AA, -NR6AA 2, pirrolidino, piperidino, morfolino, piperazino, N-(R6AA)-piperazino, -SH, -SR6AA o -CN; y cada -R6AA es independientemente alquilo C1-6 saturado, lineal o ramificado.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201403093A GB201403093D0 (en) | 2014-02-21 | 2014-02-21 | Therapeutic compounds and their use |
| PCT/GB2015/050494 WO2015124941A1 (en) | 2014-02-21 | 2015-02-20 | Pyrazolo[1,5-a]pyrimidine-5,7-diamine compounds as cdk inhibitors and their therapeutic use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2721268T3 true ES2721268T3 (es) | 2019-07-30 |
Family
ID=50482596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15706282T Active ES2721268T3 (es) | 2014-02-21 | 2015-02-20 | Compuestos de pirazolo[1,5-a]pirimidina-5,7-diamina como inhibidores de CDK y su uso terapéutico |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US9932344B2 (es) |
| EP (1) | EP3107914B8 (es) |
| JP (1) | JP6498212B2 (es) |
| CN (1) | CN106103445B (es) |
| AU (1) | AU2015220560B2 (es) |
| BR (1) | BR112016018633B1 (es) |
| CA (1) | CA2939786C (es) |
| CY (1) | CY1121588T1 (es) |
| DK (1) | DK3107914T3 (es) |
| ES (1) | ES2721268T3 (es) |
| GB (1) | GB201403093D0 (es) |
| HR (1) | HRP20190685T1 (es) |
| HU (1) | HUE043122T2 (es) |
| LT (1) | LT3107914T (es) |
| ME (1) | ME03427B (es) |
| NZ (1) | NZ724323A (es) |
| PL (1) | PL3107914T3 (es) |
| PT (1) | PT3107914T (es) |
| RS (1) | RS58704B1 (es) |
| SI (1) | SI3107914T1 (es) |
| SM (1) | SMT201900266T1 (es) |
| TR (1) | TR201905647T4 (es) |
| WO (1) | WO2015124941A1 (es) |
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| GB201403093D0 (en) | 2014-02-21 | 2014-04-09 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| WO2016068287A1 (ja) | 2014-10-31 | 2016-05-06 | 宇部興産株式会社 | 置換ジヒドロピロロピラゾール化合物 |
| EP3233842B1 (en) | 2014-12-17 | 2025-03-26 | King's College London | Bicycloheteroaryl-heteroaryl-benzoic acid compounds as retinoic acid receptor beta (rarb) agonists |
| US10913744B2 (en) * | 2015-02-13 | 2021-02-09 | Dana-Farber Cancer Institute, Inc. | LRRK2 inhibitors and methods of making and using the same |
| CN107735401B (zh) | 2015-06-15 | 2021-08-31 | 宇部兴产株式会社 | 取代二氢吡咯并吡唑衍生物 |
| WO2017096326A1 (en) | 2015-12-02 | 2017-06-08 | Massachusetts Institute Of Technology | Method for efficient generation of neurons from non-neuronal cells |
| MX390277B (es) | 2016-08-31 | 2025-03-20 | Servier Lab | Inhibidores de procesos metabolicos celulares. |
| EP3658557B1 (en) | 2017-07-28 | 2024-06-05 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors and uses thereof |
| AU2018312836B2 (en) * | 2017-08-07 | 2022-12-08 | Joint Stock Company "Biocad" | Novel heterocyclic compounds as CDK8/19 inhibitors |
| US20200197392A1 (en) * | 2017-08-15 | 2020-06-25 | The Brigham & Women's Hospital, Inc. | Compositions and methods for treating tuberous sclerosis complex |
| GB201715194D0 (en) * | 2017-09-20 | 2017-11-01 | Carrick Therapeutics Ltd | Compounds and their therapeutic use |
| TWI703149B (zh) * | 2017-11-16 | 2020-09-01 | 美商美國禮來大藥廠 | 用於抑制cdk7之化合物 |
| KR20200141487A (ko) * | 2018-04-11 | 2020-12-18 | 주식회사 큐리언트 | 사이클린 의존성 키나아제의 선택적 억제제로서의 피라졸로-트리아진 및/또는 피라졸로피리미딘 유도체 |
| US11447493B2 (en) | 2018-05-02 | 2022-09-20 | Kinnate Biopharma Inc. | Inhibitors of cyclin-dependent kinases |
| SG11202013175SA (en) | 2018-06-29 | 2021-01-28 | Kinnate Biopharma Inc | Inhibitors of cyclin-dependent kinases |
| JP7385658B2 (ja) * | 2018-10-30 | 2023-11-22 | クロノス バイオ インコーポレイテッド | Ｃｄｋ９活性を調節するための化合物、組成物、および方法 |
| EP3885347B1 (en) | 2018-11-14 | 2023-11-22 | UBE Corporation | Dihydropyrrolopyrazole derivative |
| CN109860354B (zh) * | 2018-12-28 | 2020-05-19 | 南京邮电大学 | 同质集成红外光子芯片及其制备方法 |
| US20220144841A1 (en) * | 2019-03-13 | 2022-05-12 | The Translational Genomics Research Institute | Trisubstituted pyrazolo [1,5-a] pyrimidine compounds as cdk7 inhibitors |
| WO2021003517A1 (en) * | 2019-07-10 | 2021-01-14 | Aucentra Therapeutics Pty Ltd | Derivatives of 4-(imidazo[l,2-a]pyridin-3-yl)-n-(pyridinyl)pyrimidin- 2-amine as therapeutic agents |
| CA3156610A1 (en) * | 2019-10-29 | 2021-05-06 | J. Graeme HODGSON | Methods of treating cancer in biomarker-identified patients with inhibitors of cyclin-dependent kinase 7 (cdk7) |
| GB201918541D0 (en) | 2019-12-16 | 2020-01-29 | Carrick Therapeutics Ltd | Therapeutic compounds and their use |
| AU2021231312A1 (en) * | 2020-03-06 | 2022-08-25 | Bayer Aktiengesellschaft | Imidazotriazines acting on cancer via inhibition of CDK12 |
| WO2021216828A1 (en) * | 2020-04-24 | 2021-10-28 | Massachusetts Institute Of Technology | Chimeric degraders of cyclin-dependent kinase 9 and uses thereof |
| WO2022156779A1 (zh) * | 2021-01-22 | 2022-07-28 | 上海海雁医药科技有限公司 | 取代的吡唑并[1,5-a]嘧啶-7-胺衍生物、其组合物及医药上的用途 |
| US12097261B2 (en) | 2021-05-07 | 2024-09-24 | Kymera Therapeutics, Inc. | CDK2 degraders and uses thereof |
| GB202108572D0 (en) * | 2021-06-16 | 2021-07-28 | Carrick Therapeutics Ltd | Therapeutic compounds and their use |
| WO2023001061A1 (en) * | 2021-07-17 | 2023-01-26 | Jingrui Biopharma Co., Ltd. | Cdk7 selective inhibitors as anticancer agents |
| KR20240110634A (ko) * | 2021-11-24 | 2024-07-15 | 크로노스 바이오, 인코포레이티드 | (1s,3s)-n1-(5-(펜탄-3-일)피라졸로[1,5-a]피리미딘-7-일)시클로펜탄-1,3-디아민의다형체 및 염 형태 |
| WO2024102447A1 (en) * | 2022-11-10 | 2024-05-16 | Emory University | Uses of hydroimidazopyridopyrimidinone derivatives for managing aneurysms or other vascular conditions or diseases |
| CN120752238A (zh) * | 2023-02-20 | 2025-10-03 | 江苏正大丰海制药有限公司 | 作为cdk7激酶抑制剂的杂芳环化合物及其制备和应用 |
| WO2024175024A1 (zh) * | 2023-02-21 | 2024-08-29 | 杭州德睿智药科技有限公司 | 作为CDKs抑制剂的新型并杂环类新化合物及其应用 |
| TW202500147A (zh) | 2023-06-27 | 2025-01-01 | 美商亞文納營運公司 | 雌激素受體降解劑與ｃｄｋ７抑制劑之組合 |
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| WO2025208097A1 (en) * | 2024-03-29 | 2025-10-02 | The Translational Genomics Research Institute | Cdk7 inhibitors and methods of use thereof |
| WO2025208104A1 (en) * | 2024-03-29 | 2025-10-02 | The Translational Genomics Research Institute | Cdk7 inhibitors and methods of use thereof |
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| EP1592689A4 (en) | 2003-01-31 | 2008-12-24 | Merck & Co Inc | 3-AMINO-4-PHENYLBUTANEAN DERIVATIVES AS DIPEPTIDYLPEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES |
| AU2004215481B2 (en) | 2003-02-28 | 2010-11-11 | Teijin Pharma Limited | Pyrazolo(1,5-A)pyrimidine derivatives |
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2014
- 2014-02-21 GB GB201403093A patent/GB201403093D0/en not_active Ceased
-
2015
- 2015-02-20 JP JP2016553387A patent/JP6498212B2/ja active Active
- 2015-02-20 ES ES15706282T patent/ES2721268T3/es active Active
- 2015-02-20 SI SI201530714T patent/SI3107914T1/sl unknown
- 2015-02-20 PL PL15706282T patent/PL3107914T3/pl unknown
- 2015-02-20 HU HUE15706282A patent/HUE043122T2/hu unknown
- 2015-02-20 DK DK15706282.9T patent/DK3107914T3/en active
- 2015-02-20 US US15/117,982 patent/US9932344B2/en active Active
- 2015-02-20 AU AU2015220560A patent/AU2015220560B2/en active Active
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