JP6584521B2 - 抗がん剤として有用な置換ヌクレオシド誘導体 - Google Patents
抗がん剤として有用な置換ヌクレオシド誘導体 Download PDFInfo
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- JP6584521B2 JP6584521B2 JP2017544584A JP2017544584A JP6584521B2 JP 6584521 B2 JP6584521 B2 JP 6584521B2 JP 2017544584 A JP2017544584 A JP 2017544584A JP 2017544584 A JP2017544584 A JP 2017544584A JP 6584521 B2 JP6584521 B2 JP 6584521B2
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- Prior art keywords
- cancer
- mmol
- etoac
- methyl
- alkyl
- Prior art date
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- 238000012360 testing method Methods 0.000 description 1
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- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/24—Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
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- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Peptides Or Proteins (AREA)
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| AR104326A1 (es) | 2015-05-04 | 2017-07-12 | Lilly Co Eli | Compuestos nucleósidos 5-sustituidos |
| TWI730980B (zh) | 2015-08-26 | 2021-06-21 | 比利時商健生藥品公司 | 使用作為ｐｒｍｔ５抑制劑之新穎經６-６雙環芳香環取代之核苷類似物 |
| CN108884108B (zh) | 2016-03-10 | 2021-08-31 | 詹森药业有限公司 | 用于用作prmt5抑制剂的取代核苷类似物 |
| US10898504B2 (en) | 2016-03-10 | 2021-01-26 | Janssen Pharmaceutica Nv | Substituted nucleoside analogues for use as PRMT5 inhibitors |
| AU2017326487B2 (en) | 2016-09-14 | 2021-08-05 | Janssen Pharmaceutica Nv | Spiro bicyclic inhibitors of menin-MLL interaction |
| US12084462B2 (en) | 2016-09-14 | 2024-09-10 | Janssen Pharmaceutica Nv | Spiro bicyclic inhibitors of menin-MLL interaction |
| TWI753016B (zh) | 2016-09-14 | 2022-01-21 | 比利時商健生藥品公司 | Menin-mll相互作用之稠合二環抑制劑 |
| WO2018065365A1 (en) | 2016-10-03 | 2018-04-12 | Janssen Pharmaceutica Nv | Novel monocyclic and bicyclic ring system substituted carbanucleoside analogues for use as prmt5 inhibitors |
| BR112019006414A2 (pt) * | 2016-10-03 | 2019-06-25 | Janssen Pharmaceutica Nv | análogos de carbanucleosídeos de sistema de anel monocíclico e bicíclico substituídos para uso como inibidores de prmt5 |
| KR102513564B1 (ko) | 2016-12-15 | 2023-03-22 | 얀센 파마슈티카 엔.브이. | 메닌-mll 상호작용의 아제판 억제제 |
| WO2018152501A1 (en) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| WO2018152548A1 (en) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| SG11201907607VA (en) | 2017-02-27 | 2019-09-27 | Janssen Pharmaceutica Nv | Use of biomarkers in identifying cancer patients that will be responsive to treatment with a prmt5 inhibitor |
| WO2018160855A1 (en) | 2017-03-01 | 2018-09-07 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| MA49840A (fr) * | 2017-08-09 | 2020-06-17 | Prelude Therapeutics Inc | Inhibiteurs sélectifs de la protéine arginine méthyltransférase 5 (prmt5) |
| EP3700906A1 (en) * | 2017-10-26 | 2020-09-02 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| MX2020005944A (es) * | 2017-12-08 | 2020-08-24 | Janssen Pharmaceutica Nv | Analogos espirobiciclicos novedosos. |
| CR20200263A (es) | 2017-12-13 | 2020-07-26 | Lupin Ltd | Componentes heterocíclicos bicíclicos sustituidos como inhibidores de prmt5 |
| US11396517B1 (en) | 2017-12-20 | 2022-07-26 | Janssen Pharmaceutica Nv | Exo-aza spiro inhibitors of menin-MLL interaction |
| CA3092357A1 (en) * | 2018-03-14 | 2019-09-19 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
| WO2020033285A1 (en) * | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| US20220160713A1 (en) * | 2019-02-13 | 2022-05-26 | Prelude Therapeutics, Incorporated | Selective inhibitor of protein arginine methyltransferase 5 (prmt5) |
| EP3947387B1 (en) * | 2019-03-25 | 2024-10-23 | California Institute Of Technology | Prmt5 inhibitors and uses thereof |
| WO2020206299A1 (en) | 2019-04-05 | 2020-10-08 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 |
| TW202112375A (zh) | 2019-06-06 | 2021-04-01 | 比利時商健生藥品公司 | 使用ｐｒｍｔ５抑制劑治療癌症之方法 |
| CR20220010A (es) | 2019-06-10 | 2022-05-13 | Lupin Ltd | Inhibidores de prmt5 |
| PH12021553075A1 (en) | 2019-06-12 | 2023-09-11 | Janssen Pharmaceutica Nv | Novel spirobicyclic intermediates |
| SI4299135T1 (sl) | 2019-06-18 | 2025-12-31 | Pfizer Inc. | Benzizoksazolni sulfonamidni derivati |
| CA3154566A1 (en) | 2019-09-18 | 2021-03-25 | Prelude Therapeutics Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| GEP20247638B (en) | 2019-10-22 | 2024-07-10 | Lupin Ltd | Pharmaceutical combination of prmt5 inhibitors |
| EP4069698A1 (en) | 2019-12-03 | 2022-10-12 | Lupin Limited | Substituted nucleoside analogs as prmt5 inhibitors |
| UY38988A (es) | 2019-12-19 | 2021-06-30 | Janssen Pharmaceutica Nv | Derivados espiráncos sustituidos de cadena lineal |
| IL300555A (en) | 2020-08-18 | 2023-04-01 | Incyte Corp | Process and intermediates for preparing a JAK inhibitor |
| CA3192055A1 (en) | 2020-08-18 | 2022-02-24 | Incyte Corporation | Process and intermediates for preparing a jak1 inhibitor |
| US20240101589A1 (en) * | 2020-10-08 | 2024-03-28 | Strom Therapeutics Limited | Inhibitors of mettl3 |
| CN112679505B (zh) * | 2020-12-25 | 2022-04-22 | 杭州澳赛诺生物科技有限公司 | 一种4-甲基-7H-吡咯并[2,3-d]嘧啶的合成方法 |
| WO2022153161A1 (en) | 2021-01-14 | 2022-07-21 | Pfizer Inc. | Treatment of cancer using a prmt5 inhibitor |
| CA3226714A1 (en) | 2021-07-12 | 2023-01-19 | Incyte Corporation | Process and intermediates for preparing baricitinib |
| WO2023017152A1 (en) * | 2021-08-13 | 2023-02-16 | Albert-Ludwigs-Universität Freiburg | Specific small molecule inhibitors that block kmt9 methyltransferase activity and function |
| WO2024170488A1 (en) | 2023-02-13 | 2024-08-22 | Astrazeneca Ab | Prmt5 inhibitor for use in cancer therapy |
| WO2026008533A1 (en) | 2024-07-01 | 2026-01-08 | Janssen Pharmaceutica Nv | Prmt5 inhibitors for treating adenomas |
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| US5646128A (en) * | 1989-09-15 | 1997-07-08 | Gensia, Inc. | Methods for treating adenosine kinase related conditions |
| US5864033A (en) * | 1989-09-15 | 1999-01-26 | Metabasis Therapeutics, Inc. | Adenosine kinase inhibitors |
| US5795977A (en) * | 1989-09-15 | 1998-08-18 | Metabasis Therapeutics, Inc. | Water soluble adenosine kinase inhibitors |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035298A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Chewing gum containing medicament active agents |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| GB9813554D0 (en) * | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| US6831069B2 (en) * | 1999-08-27 | 2004-12-14 | Ribapharm Inc. | Pyrrolo[2,3-d]pyrimidine nucleoside analogs |
| AU2003263846B2 (en) * | 2002-08-15 | 2009-12-17 | Gilead Palo Alto, Inc. | Partial and full agonists of A1 adenosine receptors |
| WO2010108140A1 (en) * | 2009-03-20 | 2010-09-23 | Alios Biopharma, Inc. | Substituted nucleoside and nucleotide analogs |
| US20120077814A1 (en) | 2010-09-10 | 2012-03-29 | Zhong Wang | Sulfonamide, sulfamate, and sulfamothioate derivatives |
| WO2013009735A1 (en) * | 2011-07-13 | 2013-01-17 | Merck Sharp & Dohme Corp. | 5'-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| US8575119B2 (en) * | 2011-09-23 | 2013-11-05 | Enanta Pharmaceuticals, Inc. | 2′-chloroacetylenyl substituted nucleoside derivatives |
| WO2015200680A2 (en) * | 2014-06-25 | 2015-12-30 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
| AR104326A1 (es) * | 2015-05-04 | 2017-07-12 | Lilly Co Eli | Compuestos nucleósidos 5-sustituidos |
| AU2016301188A1 (en) * | 2015-08-06 | 2018-02-15 | Chimerix, Inc. | Pyrrolopyrimidine nucleosides and analogs thereof useful as antiviral agents |
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2016
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2017
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2018
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