JP6545618B2 - Ａ２ａアゴニストとしてのｎ−アルキル２−（二置換）アルキニルアデノシン−５’−ウロンアミド - Google Patents
Ａ２ａアゴニストとしてのｎ−アルキル２−（二置換）アルキニルアデノシン−５’−ウロンアミド Download PDFInfo
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- JP6545618B2 JP6545618B2 JP2015525562A JP2015525562A JP6545618B2 JP 6545618 B2 JP6545618 B2 JP 6545618B2 JP 2015525562 A JP2015525562 A JP 2015525562A JP 2015525562 A JP2015525562 A JP 2015525562A JP 6545618 B2 JP6545618 B2 JP 6545618B2
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- pharmaceutically acceptable
- stereoisomer
- acceptable salt
- alkyl
- compound
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261678605P | 2012-08-01 | 2012-08-01 | |
| US61/678,605 | 2012-08-01 | ||
| US201361787188P | 2013-03-15 | 2013-03-15 | |
| US61/787,188 | 2013-03-15 | ||
| PCT/US2013/053053 WO2014022577A1 (en) | 2012-08-01 | 2013-07-31 | N-alkyl 2-(disubstituted)alkynyladenosine-5-uronamides as a2a agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015524440A JP2015524440A (ja) | 2015-08-24 |
| JP6545618B2 true JP6545618B2 (ja) | 2019-07-17 |
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| AU2006249866B2 (en) | 2005-05-26 | 2011-10-13 | Aldeyra Therapeutics, Inc. | Compositions and methods of treating retinal disease |
| CA2782015C (en) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Topical ophthalmic compositions and methods for the treatment of macular degeneration |
| US9822141B2 (en) * | 2012-08-01 | 2017-11-21 | Lewis And Clark Pharmaceuticals, Inc. | N-alkyl 2-(disubstituted)alkynyladenosine-5-uronamides as A2A agonists |
| CN111135171B (zh) | 2013-01-23 | 2023-09-08 | 奥尔德拉医疗公司 | 与毒性醛相关的疾病和治疗 |
| CN118724806A (zh) | 2015-08-21 | 2024-10-01 | 奥尔德拉医疗公司 | 氘化化合物和其用途 |
| CN109152774A (zh) | 2016-05-09 | 2019-01-04 | 奥尔德拉医疗公司 | 眼部炎性病症和疾病的组合治疗 |
| WO2018170476A1 (en) | 2017-03-16 | 2018-09-20 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| CN111356451A (zh) | 2017-10-10 | 2020-06-30 | 奥尔德拉医疗公司 | 炎性病症的治疗 |
| CN112714762A (zh) | 2018-08-06 | 2021-04-27 | 奥尔德拉医疗公司 | 多晶型化合物及其用途 |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| CN113784954A (zh) | 2019-05-02 | 2021-12-10 | 奥尔德拉医疗公司 | 多晶型化合物和其用途 |
| US20220332750A1 (en) * | 2019-06-21 | 2022-10-20 | Academy Of Military Medical Sciences | Adenosine compound, its pharmaceutically acceptable salt or its stereoisomer and use thereof |
| WO2021231792A1 (en) | 2020-05-13 | 2021-11-18 | Aldeyra Therapeutics, Inc. | Pharmaceutical formulations and uses thereof |
| WO2024258897A1 (en) | 2023-06-13 | 2024-12-19 | Dem Biopharma, Inc. | Alkoxypyridinyl and related compounds and their use in therapy |
| WO2025194015A1 (en) | 2024-03-15 | 2025-09-18 | Dem Biopharma, Inc. | Heteroaryl modulators of gpr84 and uses thereof |
| WO2025194014A1 (en) | 2024-03-15 | 2025-09-18 | Dem Biopharma, Inc. | Hetero aryl modulators of apmap and uses thereof |
| US20260183268A1 (en) | 2024-12-27 | 2026-07-02 | Alphina Therapeutics, Inc. | Heteroaryl Compounds and Their Use in Treating Medical Conditions |
Family Cites Families (26)
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|---|---|---|---|---|
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| JPS6299395A (ja) | 1985-10-25 | 1987-05-08 | Yamasa Shoyu Co Ltd | ２−アルキニルアデノシンおよび抗高血圧剤 |
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| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| JPH02104783A (ja) * | 1988-10-11 | 1990-04-17 | Kanai Hiroyuki | スチールコードおよびタイヤ |
| US5270304A (en) | 1988-11-15 | 1993-12-14 | Yamasa Shoyu Kabushiki Kaisha | Therapeutic 2-alkynyl adenosine agent for ischemic diseases of the heart or brain |
| WO1990015812A1 (en) | 1989-06-20 | 1990-12-27 | Yamasa Shoyu Kabushiki Kaisha | Intermediate for 2-alkynyladenosine synthesis, production of said intermediate, production of 2-alkynyladenosine from said intermediate, and stable 2-alkynyladenosine derivative |
| US5189027A (en) | 1990-11-30 | 1993-02-23 | Yamasa Shoyu Kabushiki Kaisha | 2-substituted adenosine derivatives and pharmaceutical compositions for circulatory diseases |
| JP3025557B2 (ja) * | 1991-06-28 | 2000-03-27 | ヤマサ醤油株式会社 | ２‐アルキニルアデノシン誘導体 |
| IT1254915B (it) | 1992-04-24 | 1995-10-11 | Gloria Cristalli | Derivati di adenosina ad attivita' a2 agonista |
| JP2002173427A (ja) * | 1998-09-01 | 2002-06-21 | Yamasa Shoyu Co Ltd | 眼疾患治療用医薬組成物 |
| US6322771B1 (en) * | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| PL208098B1 (pl) | 2000-03-23 | 2011-03-31 | Solvay Pharm Bv | Pochodne 4,5-dihydro-1H-pirazolu, kompozycja farmaceutyczna, sposób wytwarzania związków oraz ich zastosowanie |
| AU2002362443B2 (en) | 2001-10-01 | 2008-05-15 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| US6914053B2 (en) | 2002-09-09 | 2005-07-05 | Cv Therapeutics, Inc. | Adenosine A3 receptor agonists |
| NZ585697A (en) | 2004-08-02 | 2011-12-22 | Univ Virginia Patent Found | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| WO2006091896A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyridyl substituted xanthines |
| WO2007120972A2 (en) * | 2006-02-10 | 2007-10-25 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| US7906518B2 (en) * | 2006-06-27 | 2011-03-15 | Cbt Development Limited | Therapeutic compounds |
| US20080312160A1 (en) * | 2007-04-09 | 2008-12-18 | Guerrant Richard L | Method of treating enteritis, intestinal damage, and diarrhea from c. difficile with an a2a adenosine receptor agonist |
| KR20140041965A (ko) | 2007-05-17 | 2014-04-04 | 씨브이 쎄러퓨틱스, 인코포레이티드 | Ａ2ａ-아데노신 수용체 효능제 및 이의 다형체의 제조 방법 |
| US8058259B2 (en) | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| US8293720B2 (en) | 2007-12-20 | 2012-10-23 | Dogwood Pharmaceuticals, Inc. | Substituted 4-{3-[6-amino-9-(3, 4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| EP2448953A1 (en) * | 2009-06-30 | 2012-05-09 | Forest Laboratories Holdings Limited | Alkoxy-carbonyl-amino-alkynyl-adenosine compounds and derivatives thatreof as a2ar agonists |
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| EA201590205A1 (ru) | 2015-06-30 |
| KR20150036767A (ko) | 2015-04-07 |
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| WO2014022577A1 (en) | 2014-02-06 |
| MX367879B (es) | 2019-09-10 |
| AU2013296420B2 (en) | 2017-12-07 |
| US20140037538A1 (en) | 2014-02-06 |
| CA2880040A1 (en) | 2014-02-06 |
| AU2013296420A1 (en) | 2015-02-12 |
| EP2879683A4 (en) | 2016-04-20 |
| MX2015001370A (es) | 2016-04-26 |
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| EA027174B1 (ru) | 2017-06-30 |
| JP2015524440A (ja) | 2015-08-24 |
| US9067963B2 (en) | 2015-06-30 |
| CN104582709A (zh) | 2015-04-29 |
| EP2879683A1 (en) | 2015-06-10 |
| BR112015002249A2 (pt) | 2017-07-04 |
| IN2015DN00538A (enExample) | 2015-06-26 |
| EP2879683B1 (en) | 2020-01-22 |
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