CN104497084B - 用于治疗用途的7-脱氮嘌呤核苷 - Google Patents
用于治疗用途的7-脱氮嘌呤核苷 Download PDFInfo
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- CN104497084B CN104497084B CN201410643709.3A CN201410643709A CN104497084B CN 104497084 B CN104497084 B CN 104497084B CN 201410643709 A CN201410643709 A CN 201410643709A CN 104497084 B CN104497084 B CN 104497084B
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| JP5721275B2 (ja) * | 2009-04-22 | 2015-05-20 | インスティチュート オブ オーガニック ケミストリー アンド バイオケミストリー エーエス シーアール， ブイ．ブイ．アイ． | 治療的使用のための新規７−デアザプリンヌクレオシド |
| EA201270661A1 (ru) * | 2009-12-18 | 2013-06-28 | Президент Энд Феллоуз Оф Гарвард Колледж | УСИЛИВАЮЩИЕ РАЗМНОЖЕНИЕ β-КЛЕТОК СОЕДИНЕНИЯ И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| CN102319254B (zh) * | 2011-07-20 | 2013-06-19 | 上海交通大学 | 5-碘代杀菌核素在制备抗肿瘤药物中的应用 |
| CZ305466B6 (cs) * | 2013-11-04 | 2015-10-14 | Ústav organické chemie a biochemie Akademie věd České republiky, v. v. i. | Substituované 7-deazapurinové ribonukleosidy pro terapeutické použití |
| CA2967125C (en) | 2014-11-14 | 2022-10-25 | Nerviano Medical Sciences S.R.L. | 6-amino-7-bicyclo-7-deaza-purine derivatives as protein kinase inhibitors |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| US10414788B2 (en) | 2016-06-29 | 2019-09-17 | Ustav Organicke Chemie A Biochemie Av Cr, V.V.I. | Substituted thienopyrrolopyrimidine ribonucleosides for therapeutic use |
| CZ307334B6 (cs) | 2016-08-02 | 2018-06-13 | Ăšstav organickĂ© chemie a biochemie AV ÄŚR, v.v.i. | Substituované heteropentadieno-pyrrolopyrimidinové ribonukleosidy pro terapeutické použití |
| CA3049136C (en) | 2017-01-18 | 2022-06-14 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| CN118440096A (zh) | 2017-06-20 | 2024-08-06 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| US11072628B2 (en) | 2017-10-19 | 2021-07-27 | Universiteit Gent | Nucleoside analogues for the treatment of parasitic infections |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| CA3087354C (en) * | 2018-01-18 | 2023-01-03 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| WO2019143994A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridinecompounds as ret kinase inhibitors |
| CZ308104B6 (cs) | 2018-03-12 | 2020-01-08 | Ăšstav organickĂ© chemie a biochemie AV ÄŚR, v. v. i. | Pyridinopyrrolopyrimidinové ribonukleosidy pro terapeutické použití |
| EP3833355A4 (en) | 2018-08-07 | 2022-05-11 | Merck Sharp & Dohme Corp. | PRMT5 INHIBITORS |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| MX2021015772A (es) * | 2019-06-18 | 2022-01-31 | Taiho Pharmaceutical Co Ltd | Compuesto de carbonato novedoso que tiene esqueleto de pirrolopirimidina o sal farmaceuticamente aceptable del mismo. |
| US20230104311A1 (en) * | 2020-02-17 | 2023-04-06 | Katholieke Universiteit Leuven | Novel 6-substituted 7-deazapurines and corresponding nucleosides as medicaments |
| KR102639275B1 (ko) * | 2021-06-08 | 2024-02-21 | 퓨쳐메디신 주식회사 | 다중 표적 인산화효소 저해 활성을 갖는 뉴클레오사이드 유도체 및 이를 포함하는 암의 예방 및 치료용 약학적 조성물 |
| CA3233416A1 (en) | 2021-09-28 | 2023-04-06 | Universiteit Antwerpen | Nucleoside analogues for the treatment of parasitic infections |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005044835A1 (en) * | 2003-10-27 | 2005-05-19 | Genelabs Technologies, Inc. | METHODS FOR PREPARING 7-(2'-SUBSTITUTED-ß-D-RIBOFURANOSYL)-4-(NR2R3)-5-(SUBSTITUTED ETHYN-1-YL)-PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES |
| CN1653077A (zh) * | 2002-05-06 | 2005-08-10 | 健亚生物科技公司 | 治疗c型肝炎病毒感染的核苷衍生物 |
| US20060079468A1 (en) * | 2003-10-27 | 2006-04-13 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| WO2010026153A1 (en) * | 2008-09-03 | 2010-03-11 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Nucleoside derivatives as inhibitors of viral polymerases |
Family Cites Families (9)
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| IL108523A0 (en) * | 1993-02-03 | 1994-05-30 | Gensia Inc | Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain |
| HUP0400726A3 (en) * | 2001-01-22 | 2007-05-29 | Merck & Co Inc | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| AU2002353165A1 (en) * | 2001-12-17 | 2003-06-30 | Ribapharm Inc. | Deazapurine nucleoside libraries and compounds |
| US20040157892A1 (en) | 2003-02-12 | 2004-08-12 | Crompton Co./Cie | Pesticidal fluoroethyl pyrazoles |
| US7157434B2 (en) * | 2003-10-27 | 2007-01-02 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| WO2006033709A2 (en) * | 2004-07-29 | 2006-03-30 | Metabasis Therapeutics, Inc. | Novel nucleoside derivatives |
| TR201815961T4 (tr) * | 2008-01-18 | 2018-11-21 | Inst Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Yeni sitostatik 7-deazapürin nükleozidleri. |
| BRPI0914626A2 (pt) * | 2008-06-23 | 2015-10-20 | Janssen Pharmaceutica Nv | antagonistas de piperidil acrilamida de ccr2 |
| JP5721275B2 (ja) * | 2009-04-22 | 2015-05-20 | インスティチュート オブ オーガニック ケミストリー アンド バイオケミストリー エーエス シーアール， ブイ．ブイ．アイ． | 治療的使用のための新規７−デアザプリンヌクレオシド |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1653077A (zh) * | 2002-05-06 | 2005-08-10 | 健亚生物科技公司 | 治疗c型肝炎病毒感染的核苷衍生物 |
| WO2005044835A1 (en) * | 2003-10-27 | 2005-05-19 | Genelabs Technologies, Inc. | METHODS FOR PREPARING 7-(2'-SUBSTITUTED-ß-D-RIBOFURANOSYL)-4-(NR2R3)-5-(SUBSTITUTED ETHYN-1-YL)-PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES |
| US20060079468A1 (en) * | 2003-10-27 | 2006-04-13 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| WO2010026153A1 (en) * | 2008-09-03 | 2010-03-11 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Nucleoside derivatives as inhibitors of viral polymerases |
Non-Patent Citations (4)
| Title |
|---|
| 7-Functionalized 7-deazapurine β-D and β-L-ribonucleosides related to tubercidin and 7-deazainosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D or β-L-ribofuranose;Frank Seela，等;《Tetrahedron》;20070924;第63卷(第39期);第9850–9861页 * |
| 7-去氮腺苷衍生物的合成及生物活性研究;张亮仁，等;《中国药物化学杂志》;20030430;第13卷(第2期);第63-66页 * |
| Pyrrolopyrimidine Nucleosides VIII. Synthesis of sangivamycin derivatives possessing exocyclic heterocycles at C5;Karl H. Schram，等;《J. Carbohydrates Nucleosides Nucleotides》;19741231;第1卷(第1期);第39-54页 * |
| Study on the Synthesis and PKA-I Binding Activities of 5-Alkynyl Tubercidin Analogues;Liangren Zhang，等;《Bioorganic & Medicinal Chemistry》;20020430;第10卷(第4期);第907–912页 * |
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