IL236986A - N - Alkyl 2 - (Pretty Converted) - Google Patents
N - Alkyl 2 - (Pretty Converted)Info
- Publication number
- IL236986A IL236986A IL236986A IL23698615A IL236986A IL 236986 A IL236986 A IL 236986A IL 236986 A IL236986 A IL 236986A IL 23698615 A IL23698615 A IL 23698615A IL 236986 A IL236986 A IL 236986A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- independently selected
- alkyl
- pharmaceutically acceptable
- stereoisomer
- Prior art date
Links
- 239000000556 agonist Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 155
- 150000003839 salts Chemical class 0.000 claims description 85
- -1 cyclopropyl-methylene, cyclobutyl Chemical group 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 46
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 102000007471 Adenosine A2A receptor Human genes 0.000 claims description 26
- 108010085277 Adenosine A2A receptor Proteins 0.000 claims description 26
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 26
- 229910003827 NRaRb Inorganic materials 0.000 claims description 25
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 230000000694 effects Effects 0.000 claims description 23
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
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- 229910052794 bromium Inorganic materials 0.000 claims description 12
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- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 230000008733 trauma Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 230000002107 myocardial effect Effects 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
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- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
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- 101710084578 Short neurotoxin 1 Proteins 0.000 claims description 2
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- 101710182532 Toxin a Proteins 0.000 claims description 2
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 36
- 125000004093 cyano group Chemical group *C#N 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 25
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 24
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- 239000007787 solid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- 108020003175 receptors Proteins 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 230000004410 intraocular pressure Effects 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 7
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- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 231100000252 nontoxic Toxicity 0.000 description 7
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Landscapes
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| US201361787188P | 2013-03-15 | 2013-03-15 | |
| PCT/US2013/053053 WO2014022577A1 (en) | 2012-08-01 | 2013-07-31 | N-alkyl 2-(disubstituted)alkynyladenosine-5-uronamides as a2a agonists |
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| ZA (1) | ZA201501350B (OSRAM) |
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| ES2393768T3 (es) | 2005-05-26 | 2012-12-27 | Neuron Systems, Inc | Derivado de quinolina para el tratamiento de enfermedades retinianas |
| WO2011072141A1 (en) | 2009-12-11 | 2011-06-16 | Neuron Systems, Inc. | 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 |
| CN117045653A (zh) | 2013-01-23 | 2023-11-14 | 奥尔德拉医疗公司 | 与毒性醛相关的疾病和治疗 |
| JP6947406B2 (ja) | 2015-08-21 | 2021-10-13 | アルデイラ セラピューティクス， インコーポレイテッド | 重水素化化合物およびその使用 |
| WO2017196881A1 (en) | 2016-05-09 | 2017-11-16 | Aldeyra Therapeutics, Inc. | Combination treatment of ocular inflammatory disorders and diseases |
| AU2018234919A1 (en) | 2017-03-16 | 2019-09-19 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| JP7311162B2 (ja) | 2017-10-10 | 2023-07-19 | アルデイラ セラピューティクス， インコーポレイテッド | 炎症性障害の処置 |
| 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 |
| EP3962894A4 (en) | 2019-05-02 | 2023-01-11 | Aldeyra Therapeutics, Inc. | POLYMORPHIC COMPOUNDS AND USES THEREOF |
| WO2020223717A1 (en) | 2019-05-02 | 2020-11-05 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| 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 |
| CA3175856A1 (en) | 2020-05-13 | 2021-11-18 | Todd Brady | 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 |
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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 |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| 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 |
| EP0444196B1 (en) | 1988-11-15 | 1994-06-08 | Yamasa Shoyu Kabushiki Kaisha | Agent for treatment and prophylaxis of ischemic disease of heart or brain |
| EP0429681B1 (en) | 1989-06-20 | 1995-09-06 | Yamasa Shoyu Kabushiki Kaisha (Yamasa Corporation) | 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 |
| HK1052349B (zh) | 2000-03-23 | 2005-09-23 | 索尔瓦药物有限公司 | 具有cb1-拮抗活性的4，5-二氢-1h-吡唑衍生物 |
| EP1434782A2 (en) | 2001-10-01 | 2004-07-07 | University of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
| ATE449782T1 (de) | 2002-09-09 | 2009-12-15 | Cv Therapeutics Inc | Adenosin a3 rezeptor agonisten |
| US7605143B2 (en) | 2004-08-02 | 2009-10-20 | University Of Virginia Patent Foundation | 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 |
| US8178509B2 (en) * | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| CA2657973A1 (en) * | 2006-06-27 | 2008-01-03 | Biovitrum Ab (Publ) | Therapeutic compounds |
| WO2008124150A1 (en) * | 2007-04-09 | 2008-10-16 | University Of Virginia Patent Foundation | Method of treating enteritis, intestinal damage, and diarrhea from c. difficile with an a2a adenosine receptor agonist |
| PT2158208E (pt) | 2007-05-17 | 2015-06-11 | Gilead Sciences Inc | Processo para preparar um agonista de recetor de adenosina-a2a e seus polimorfos |
| 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 |
| EA201270102A1 (ru) * | 2009-06-30 | 2012-08-30 | Форест Лэборетериз Холдингз Лимитед | Соединения алкокси-карбонил-амино-алкинил-аденозина и их производные в качестве агонистов ar |
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| ZA201501350B (en) | 2016-12-21 |
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| EP2879683A4 (en) | 2016-04-20 |
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| US9067963B2 (en) | 2015-06-30 |
| EP2879683B1 (en) | 2020-01-22 |
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