AU2005285284B2 - Purine derivatives as A3 and A1 adenosine receptor agonists - Google Patents
Purine derivatives as A3 and A1 adenosine receptor agonists Download PDFInfo
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- AU2005285284B2 AU2005285284B2 AU2005285284A AU2005285284A AU2005285284B2 AU 2005285284 B2 AU2005285284 B2 AU 2005285284B2 AU 2005285284 A AU2005285284 A AU 2005285284A AU 2005285284 A AU2005285284 A AU 2005285284A AU 2005285284 B2 AU2005285284 B2 AU 2005285284B2
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- Prior art keywords
- alkyl
- hydroxy
- halo
- group
- alkoxy
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- 101150046889 ADORA3 gene Proteins 0.000 title claims description 40
- 239000003379 purinergic P1 receptor agonist Substances 0.000 title description 11
- 101150007969 ADORA1 gene Proteins 0.000 title description 3
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 2
- 150000003212 purines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 120
- -1 hydroxy, amino Chemical group 0.000 claims description 114
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
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- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000000556 agonist Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
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- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D473/00—Heterocyclic compounds containing purine ring systems
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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- 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
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| PCT/US2005/031678 WO2006031505A1 (en) | 2004-09-09 | 2005-09-02 | Purine derivatives as a3 and a1 adenosine receptor agonists |
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| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| US8410078B2 (en) | 2006-05-23 | 2013-04-02 | University Of Connecticut | Composition and methods to treat cardiac diseases |
| AU2007263726A1 (en) * | 2006-06-27 | 2008-01-03 | Biovitrum Ab (Publ) | Novel 2',3'-methylidene acetyl adenosine prodrugs for use as prodrugs for adenosine receptor agonists |
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| WO2008023362A2 (en) * | 2006-08-21 | 2008-02-28 | Can-Fite Biopharma Ltd. | Use of a combination of methotrexate and an a3ar agonist for the treatment of cancer |
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| NZ601866A (en) | 2007-06-29 | 2013-12-20 | Acucela Inc | Alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders |
| DK2227234T3 (da) | 2007-10-15 | 2014-08-11 | Can Fite Biopharma Ltd | Fremgangsmåde til induktion af hepatocytproliferering og anvendelserderaf |
| US8916570B2 (en) | 2008-03-31 | 2014-12-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists and antagonists |
| CA2720037C (en) | 2008-03-31 | 2016-08-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Purine derivatives as a3 adenosine receptor-selective agonists |
| US9181253B2 (en) | 2008-08-01 | 2015-11-10 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Adenosine receptor agonists, partial agonists, and antagonists |
| AU2009276411B2 (en) * | 2008-08-01 | 2014-08-07 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor antagonists and partial agonists |
| EP2507241A1 (en) | 2009-12-02 | 2012-10-10 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Methanocarba adenosine derivatives and dendrimer conjugates thereof |
| CN102985432B (zh) | 2010-02-22 | 2016-11-02 | 康涅狄格大学 | 用于治疗心脏病的amp衍生物 |
| US20130109645A1 (en) | 2010-03-31 | 2013-05-02 | The united States of America,as represented by Secretary,Dept.,of Health and Human Services | Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders |
| CN103429605B (zh) * | 2011-01-26 | 2017-11-07 | 北京康倍得医药技术开发有限公司 | 呋喃核糖基嘌呤类化合物及其制备方法和应用 |
| WO2015051244A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN105934433B (zh) * | 2013-11-27 | 2019-03-22 | 美国卫生和人力服务部 | A3腺苷受体激动剂 |
| EP3119397B1 (en) | 2014-03-19 | 2022-03-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN114230571B (zh) | 2015-09-14 | 2025-07-08 | 无限药品股份有限公司 | 异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法 |
| ES2989621T3 (es) | 2016-04-21 | 2024-11-27 | Astrocyte Pharmaceuticals Inc | Compuestos y métodos para el tratamiento de afecciones neurológicas y cardiovasculares |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR101820909B1 (ko) * | 2017-07-07 | 2018-01-23 | 퓨쳐메디신 주식회사 | 아데노신 유도체를 포함하는 만성신장질환 예방 및 치료용 약학적 조성물 |
| CN112218638A (zh) | 2018-02-09 | 2021-01-12 | 阿斯特罗赛特制药公司 | 用于治疗成瘾和相关病症的化合物和方法 |
| BR112021005290A2 (pt) | 2018-09-26 | 2021-06-22 | Astrocyte Pharmaceuticals, Inc. | compostos polimórficos e usos dos mesmos |
| EP4329773A4 (en) * | 2021-04-28 | 2025-06-04 | Astrocyte Pharmaceuticals, Inc. | PURINE NUCLEOSIDES, THEIR INTERMEDIATES AND PROCESSES FOR THEIR PREPARATION |
| US20220396830A1 (en) * | 2021-05-13 | 2022-12-15 | Promega Corporation | Bioluminescent detection of dna synthesis |
| WO2025019529A1 (en) * | 2023-07-17 | 2025-01-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | 5-ht 2b serotonin receptor antagonists, pharmaceutical compositions thereof, and methods of use thereof |
| CN117503766B (zh) * | 2024-01-04 | 2024-04-26 | 中国康复研究中心 | Pld抑制剂在制备治疗脊髓损伤的药物中的用途 |
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| WO2001051490A1 (en) * | 2000-01-14 | 2001-07-19 | The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Methanocarba cycloalkyl nucleoside analogues |
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| US5688774A (en) | 1993-07-13 | 1997-11-18 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5773423A (en) * | 1993-07-13 | 1998-06-30 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| GB9723589D0 (en) * | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| US6586413B2 (en) * | 1999-11-05 | 2003-07-01 | The United States Of America As Represented By The Department Of Health And Human Services | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
| EP1241176A1 (en) * | 2001-03-16 | 2002-09-18 | Pfizer Products Inc. | Purine derivatives for the treatment of ischemia |
| US20050261237A1 (en) * | 2003-04-25 | 2005-11-24 | Boojamra Constantine G | Nucleoside phosphonate analogs |
| US20090192077A1 (en) * | 2005-04-15 | 2009-07-30 | Shizuko Sei | North-2'deoxy -methanocarbathymidines as antiviral agents for treatment of kaposi's sarcoma-associated herpes virus |
| US7867983B2 (en) * | 2007-03-29 | 2011-01-11 | The University Of Connecticut | Methods to protect skeletal muscle against injury |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001051490A1 (en) * | 2000-01-14 | 2001-07-19 | The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Methanocarba cycloalkyl nucleoside analogues |
Non-Patent Citations (1)
| Title |
|---|
| LEE, K. ET AL., "Ring-constrained (N)-methanocarba nucleosides as adenosine receptor agonists: independent 5'-uronamide and 2'-deoxy modifications", Bioorganic & Medicinal Chemistry Letters, 2001, vol. 11, pages 1333-1337. * |
Also Published As
| Publication number | Publication date |
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| EP1794162A1 (en) | 2007-06-13 |
| BRPI0515030A (pt) | 2008-07-01 |
| CN101056879A (zh) | 2007-10-17 |
| WO2006031505A1 (en) | 2006-03-23 |
| CA2601996A1 (en) | 2006-03-23 |
| AU2005285284A1 (en) | 2006-03-23 |
| IL181716A0 (en) | 2007-07-04 |
| CN101056879B (zh) | 2011-10-05 |
| US20070232626A1 (en) | 2007-10-04 |
| JP2012229215A (ja) | 2012-11-22 |
| KR20070050484A (ko) | 2007-05-15 |
| US7825126B2 (en) | 2010-11-02 |
| JP2008512457A (ja) | 2008-04-24 |
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