AU2010238985B2 - Novel 7-deazapurine nucleosides for therapeutic uses - Google Patents
Novel 7-deazapurine nucleosides for therapeutic uses Download PDFInfo
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- AU2010238985B2 AU2010238985B2 AU2010238985A AU2010238985A AU2010238985B2 AU 2010238985 B2 AU2010238985 B2 AU 2010238985B2 AU 2010238985 A AU2010238985 A AU 2010238985A AU 2010238985 A AU2010238985 A AU 2010238985A AU 2010238985 B2 AU2010238985 B2 AU 2010238985B2
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- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 229950005839 vinzolidine Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2015205885A AU2015205885B2 (en) | 2009-04-22 | 2015-07-22 | Novel 7-deazapurine nucleosides for therapeutic uses |
| AU2017204148A AU2017204148B2 (en) | 2009-04-22 | 2017-06-19 | Novel 7-deazapurine nucleosides for therapeutic uses |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17165609P | 2009-04-22 | 2009-04-22 | |
| US61/171,656 | 2009-04-22 | ||
| PCT/CZ2010/000050 WO2010121576A2 (en) | 2009-04-22 | 2010-04-19 | Novel 7-deazapurine nucleosides for therapeutic uses |
Related Child Applications (1)
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|---|---|---|---|
| AU2015205885A Division AU2015205885B2 (en) | 2009-04-22 | 2015-07-22 | Novel 7-deazapurine nucleosides for therapeutic uses |
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| AU2010238985A1 AU2010238985A1 (en) | 2011-12-01 |
| AU2010238985B2 true AU2010238985B2 (en) | 2015-04-23 |
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| AU2010238985A Active AU2010238985B2 (en) | 2009-04-22 | 2010-04-19 | Novel 7-deazapurine nucleosides for therapeutic uses |
| AU2015205885A Active AU2015205885B2 (en) | 2009-04-22 | 2015-07-22 | Novel 7-deazapurine nucleosides for therapeutic uses |
| AU2017204148A Active AU2017204148B2 (en) | 2009-04-22 | 2017-06-19 | Novel 7-deazapurine nucleosides for therapeutic uses |
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| AU2015205885A Active AU2015205885B2 (en) | 2009-04-22 | 2015-07-22 | Novel 7-deazapurine nucleosides for therapeutic uses |
| AU2017204148A Active AU2017204148B2 (en) | 2009-04-22 | 2017-06-19 | Novel 7-deazapurine nucleosides for therapeutic uses |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US9321800B2 (OSRAM) |
| EP (1) | EP2421879B1 (OSRAM) |
| JP (2) | JP5721275B2 (OSRAM) |
| CN (2) | CN104497084B (OSRAM) |
| AU (3) | AU2010238985B2 (OSRAM) |
| CA (2) | CA2759131C (OSRAM) |
| DK (1) | DK2421879T3 (OSRAM) |
| ES (1) | ES2437917T3 (OSRAM) |
| HR (1) | HRP20131021T1 (OSRAM) |
| MX (1) | MX2011011160A (OSRAM) |
| NZ (2) | NZ596301A (OSRAM) |
| PL (1) | PL2421879T3 (OSRAM) |
| PT (1) | PT2421879E (OSRAM) |
| SI (1) | SI2421879T1 (OSRAM) |
| WO (1) | WO2010121576A2 (OSRAM) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2759131C (en) * | 2009-04-22 | 2017-06-20 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 7-deazapurine nucleosides for therapeutic uses |
| US20130023491A1 (en) * | 2009-12-18 | 2013-01-24 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| 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 |
| EA039885B1 (ru) | 2014-11-14 | 2022-03-23 | НЕРВИАНО МЕДИКАЛ САЙЕНСИЗ С.р.л. | Производные 6-амино-7-бицикло-7-деазапурина в качестве ингибиторов протеинкиназы |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| EP3478701B1 (en) | 2016-06-29 | 2022-08-10 | 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 |
| EP3571203B1 (en) | 2017-01-18 | 2023-06-07 | Array BioPharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| CN110769822A (zh) | 2017-06-20 | 2020-02-07 | 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 |
| EP3697800A1 (en) | 2017-10-19 | 2020-08-26 | Universiteit Gent | Nucleoside analogues for the treatment of parasitic infections |
| CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| EP3740491A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds 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 |
| AU2019317549A1 (en) | 2018-08-07 | 2021-02-25 | Msd International Gmbh | PRMT5 inhibitors |
| JP2022500383A (ja) | 2018-09-10 | 2022-01-04 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての縮合複素環式化合物 |
| MA56544A (fr) * | 2019-06-18 | 2022-04-27 | Taiho Pharmaceutical Co Ltd | Nouveau compose ester d'acide phosphorique possedant un squelette pyrolo-pyrimidine ou sel pharmaceutiquement acceptable de celui-ci |
| EP4106763A1 (en) * | 2020-02-17 | 2022-12-28 | Katholieke Universiteit Leuven KU Leuven Research & Development | 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 |
| CN118355022A (zh) | 2021-09-28 | 2024-07-16 | 安特卫普大学 | 用于治疗寄生虫感染的核苷类似物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SK286630B6 (sk) * | 2001-01-22 | 2009-02-05 | Merck & Co., Inc. | Nukleozidové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
| WO2003051899A1 (en) * | 2001-12-17 | 2003-06-26 | Ribapharm Inc. | Deazapurine nucleoside libraries and compounds |
| CA2484921A1 (en) * | 2002-05-06 | 2003-11-13 | Genelabs Technologies, Inc. | Nucleoside derivatives for treating hepatitis c virus infection |
| US20040157892A1 (en) | 2003-02-12 | 2004-08-12 | Crompton Co./Cie | Pesticidal fluoroethyl pyrazoles |
| 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 |
| US7202223B2 (en) * | 2003-10-27 | 2007-04-10 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| EP1680436A1 (en) * | 2003-10-27 | 2006-07-19 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| WO2006033709A2 (en) * | 2004-07-29 | 2006-03-30 | Metabasis Therapeutics, Inc. | Novel nucleoside derivatives |
| JP5485172B2 (ja) * | 2008-01-18 | 2014-05-07 | 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， アカデミー オブ サイエンシズ オブ ザ チェコ リパブリック | 新規な細胞増殖抑制性７−デアザプリンヌクレオシド |
| MX2010014501A (es) * | 2008-06-23 | 2011-02-25 | Janssen Pharmaceutica Nv | Antagonistas de piperidil acrilamida de receptor 2 de citocina quimioatrayente. |
| CA2759131C (en) * | 2009-04-22 | 2017-06-20 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 7-deazapurine nucleosides for therapeutic uses |
-
2010
- 2010-04-19 CA CA2759131A patent/CA2759131C/en active Active
- 2010-04-19 WO PCT/CZ2010/000050 patent/WO2010121576A2/en not_active Ceased
- 2010-04-19 PL PL10734433T patent/PL2421879T3/pl unknown
- 2010-04-19 US US14/394,262 patent/US9321800B2/en active Active
- 2010-04-19 HR HRP20131021AT patent/HRP20131021T1/hr unknown
- 2010-04-19 ES ES10734433.5T patent/ES2437917T3/es active Active
- 2010-04-19 PT PT107344335T patent/PT2421879E/pt unknown
- 2010-04-19 CN CN201410643709.3A patent/CN104497084B/zh active Active
- 2010-04-19 MX MX2011011160A patent/MX2011011160A/es active IP Right Grant
- 2010-04-19 CA CA2966647A patent/CA2966647A1/en not_active Abandoned
- 2010-04-19 NZ NZ596301A patent/NZ596301A/en unknown
- 2010-04-19 NZ NZ700583A patent/NZ700583A/en active IP Right Revival
- 2010-04-19 CN CN201080027802.1A patent/CN102459300B/zh active Active
- 2010-04-19 DK DK10734433.5T patent/DK2421879T3/da active
- 2010-04-19 EP EP10734433.5A patent/EP2421879B1/en active Active
- 2010-04-19 JP JP2012506333A patent/JP5721275B2/ja active Active
- 2010-04-19 SI SI201030450T patent/SI2421879T1/sl unknown
- 2010-04-19 AU AU2010238985A patent/AU2010238985B2/en active Active
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2014
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2015
- 2015-07-22 AU AU2015205885A patent/AU2015205885B2/en active Active
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2016
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2017
- 2017-03-08 US US15/453,702 patent/US10294262B2/en active Active
- 2017-06-19 AU AU2017204148A patent/AU2017204148B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (3)
| Title |
|---|
| L. Zhang et al.: "Studies on synthesis of derivatives of 7-deaza-adenosine and their biological activities", retrieved from ; & ZHONGGUO YAOWU HUAXUE ZAZHI, vol. 13, no. 2, 2003, pages 63-66, * |
| SCHRAM KARL H ET AL: "Pyrrolopyrimidine nucleosides. VIII. Synthesis of sangivamycin derivatives possessing exocyclic heterocycles at C5", JOURNAL OF CARBOHYDRATES. NUCLEOSIDES NUCLEOTIDES, vol. 1, no. 1, 1 January 1974, pages 39-54, * |
| ZHANG, L. ET AL.: "Study on the synthesis and PKA-1 binding activities of 5-alkynyl tubercidin analogues", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 10, 2002, pages 907-912, * |
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