CA2649648A1 - Adenosine a3 receptor agonists - Google Patents
Adenosine a3 receptor agonists Download PDFInfo
- Publication number
- CA2649648A1 CA2649648A1 CA002649648A CA2649648A CA2649648A1 CA 2649648 A1 CA2649648 A1 CA 2649648A1 CA 002649648 A CA002649648 A CA 002649648A CA 2649648 A CA2649648 A CA 2649648A CA 2649648 A1 CA2649648 A1 CA 2649648A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally
- halo
- nitrogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002593 adenosine A3 receptor agonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 29
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- 230000005258 radioactive decay Effects 0.000 description 1
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- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
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- 239000012536 storage buffer Substances 0.000 description 1
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- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ZHVMTESWXXCMID-UYSODQMBSA-N tert-butyl N-[(1S,4R)-4-(2,6-dichloropurin-9-yl)cyclopent-2-en-1-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate [(1S,4R)-4-(2,6-dichloropurin-9-yl)cyclopent-2-en-1-yl] ethyl carbonate Chemical compound C(C)OC(O[C@@H]1C=C[C@@H](C1)N1C2=NC(=NC(=C2N=C1)Cl)Cl)=O.C(=O)(OC(C)(C)C)N([C@@H]1C=C[C@@H](C1)N1C2=NC(=NC(=C2N=C1)Cl)Cl)C(=O)OC(C)(C)C ZHVMTESWXXCMID-UYSODQMBSA-N 0.000 description 1
- DGCUKMKXWAJAAE-RSLMWUCJSA-N tert-butyl n-[(1s,2r,3s,4r)-4-(2,6-dichloropurin-9-yl)-2,3-dihydroxycyclopentyl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound O[C@@H]1[C@H](O)[C@@H](N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C[C@H]1N1C2=NC(Cl)=NC(Cl)=C2N=C1 DGCUKMKXWAJAAE-RSLMWUCJSA-N 0.000 description 1
- OGDBLCCEJZQMDU-NWDGAFQWSA-N tert-butyl n-[(1s,4r)-4-(2,6-dichloropurin-9-yl)cyclopent-2-en-1-yl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound C1=C[C@@H](N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C[C@H]1N1C2=NC(Cl)=NC(Cl)=C2N=C1 OGDBLCCEJZQMDU-NWDGAFQWSA-N 0.000 description 1
- OCNUBCIZNALWCA-LLHIFLOGSA-N tert-butyl n-acetyl-n-[(1s,2r,3s,4r)-4-(6-chloro-2-iodopurin-9-yl)-2,3-dihydroxycyclopentyl]carbamate Chemical compound O[C@@H]1[C@H](O)[C@@H](N(C(=O)C)C(=O)OC(C)(C)C)C[C@H]1N1C2=NC(I)=NC(Cl)=C2N=C1 OCNUBCIZNALWCA-LLHIFLOGSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- 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
- A61K31/33—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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0607944.6A GB0607944D0 (en) | 2006-04-21 | 2006-04-21 | Organic compounds |
| GB0607944.6 | 2006-04-21 | ||
| PCT/EP2007/053847 WO2007147659A1 (en) | 2006-04-21 | 2007-04-19 | Adenosine a3 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2649648A1 true CA2649648A1 (en) | 2007-12-27 |
Family
ID=36581041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002649648A Abandoned CA2649648A1 (en) | 2006-04-21 | 2007-04-19 | Adenosine a3 receptor agonists |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20090281126A1 (https=) |
| EP (1) | EP2013199A1 (https=) |
| JP (1) | JP2009534358A (https=) |
| KR (1) | KR20080110845A (https=) |
| CN (1) | CN101426785A (https=) |
| AU (1) | AU2007263237B2 (https=) |
| BR (1) | BRPI0710514A2 (https=) |
| CA (1) | CA2649648A1 (https=) |
| GB (1) | GB0607944D0 (https=) |
| MX (1) | MX2008013520A (https=) |
| RU (1) | RU2008145708A (https=) |
| WO (1) | WO2007147659A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607945D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP2322525B1 (en) * | 2006-04-21 | 2013-09-18 | Novartis AG | Purine derivatives for use as adenosin A2A receptor agonists |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| CA2669108A1 (en) * | 2006-11-10 | 2008-05-15 | Novartis Ag | Cyclopentene diol monoacetate derivatives |
| WO2009050199A1 (en) * | 2007-10-17 | 2009-04-23 | Novartis Ag | Purine derivatives as adenosine al receptor ligands |
| WO2010014921A2 (en) | 2008-08-01 | 2010-02-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor antagonists and partial agonists |
| 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 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1528382A (en) * | 1974-12-26 | 1978-10-11 | Teijin Ltd | Cyclopentene diols and acyl esters thereof and processes for their preparation |
| US4738954A (en) * | 1985-11-06 | 1988-04-19 | Warner-Lambert Company | Novel N6 -substituted-5'-oxidized adenosine analogs |
| US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
| 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 |
| EA000884B1 (ru) * | 1996-01-02 | 2000-06-26 | Рон-Пуленк Рорер Фармасьютикалз Инк. | Способ получения 2,4-дигидроксипиридина и 2,4-дигидрокси-3-нитропиридина |
| US6376472B1 (en) * | 1996-07-08 | 2002-04-23 | Aventis Pharmaceuticals, Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| GB9813554D0 (en) * | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| CN1383427A (zh) * | 1998-12-31 | 2002-12-04 | 阿温蒂斯药物公司 | 制备n6－取代的脱氮杂一腺苷衍生物的方法 |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US6403567B1 (en) * | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| 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 |
| JP4012070B2 (ja) * | 2001-01-16 | 2007-11-21 | カン−フィテ・バイオファーマ・リミテッド | ウイルスの複製を阻害するためのアデノシンａ３受容体アゴニストの使用 |
| US20040162422A1 (en) * | 2001-03-20 | 2004-08-19 | Adrian Hall | Chemical compounds |
| EP1258247A1 (en) * | 2001-05-14 | 2002-11-20 | Aventis Pharma Deutschland GmbH | Adenosine analogues for the treatment of insulin resistance syndrome and diabetes |
| US7414036B2 (en) * | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
| DE602004006895T2 (de) * | 2003-12-29 | 2008-01-31 | Can-Fite Biopharma Ltd. | Verfahren zur behandlung von multipler sklerose |
| EP1778239B1 (en) * | 2004-07-28 | 2013-08-21 | Can-Fite Biopharma Ltd. | Adenosine a3 receptor agonists for the treatment of dry eye disorders including sjogren's syndrome |
| US7825102B2 (en) * | 2004-07-28 | 2010-11-02 | Can-Fite Biopharma Ltd. | Treatment of dry eye conditions |
| JP2008512457A (ja) * | 2004-09-09 | 2008-04-24 | アメリカ合衆国 | Ａ３及びａ１アデノシン受容体作用薬としてのプリン誘導体 |
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| US7176172B2 (en) * | 2004-10-25 | 2007-02-13 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Quaternary ammonium polyol salts as anti-aging actives in personal care compositions |
| US20080051364A1 (en) * | 2004-11-08 | 2008-02-28 | Pninna Fishman | Therapeutic Treatment of Accelerated Bone Resorption |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| RS52458B (sr) * | 2005-02-04 | 2013-02-28 | Millennium Pharmaceuticals Inc. | Inhibitori e1 aktivirajućih enzima |
| JP5339916B2 (ja) * | 2005-11-30 | 2013-11-13 | キャン−ファイト・バイオファーマ・リミテッド | 骨関節炎の治療におけるａ３アデノシン受容体アゴニストの使用 |
| CN101410114B (zh) * | 2006-01-26 | 2012-07-04 | 美国政府卫生与公共服务部 | A3腺苷受体别构调节剂 |
| EA024006B1 (ru) * | 2006-02-02 | 2016-08-31 | Миллениум Фармасьютикалз, Инк. | Ингибиторы е1 активирующих ферментов |
| EP2322525B1 (en) * | 2006-04-21 | 2013-09-18 | Novartis AG | Purine derivatives for use as adenosin A2A receptor agonists |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607951D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607945D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP1889846A1 (en) * | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| US8008307B2 (en) * | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| CA2669108A1 (en) * | 2006-11-10 | 2008-05-15 | Novartis Ag | Cyclopentene diol monoacetate derivatives |
| WO2009050199A1 (en) * | 2007-10-17 | 2009-04-23 | Novartis Ag | Purine derivatives as adenosine al receptor ligands |
| US20090181934A1 (en) * | 2007-10-17 | 2009-07-16 | Novartis Ag | Organic Compounds |
-
2006
- 2006-04-21 GB GBGB0607944.6A patent/GB0607944D0/en not_active Ceased
-
2007
- 2007-04-19 BR BRPI0710514-2A patent/BRPI0710514A2/pt not_active IP Right Cessation
- 2007-04-19 CA CA002649648A patent/CA2649648A1/en not_active Abandoned
- 2007-04-19 KR KR1020087025605A patent/KR20080110845A/ko not_active Withdrawn
- 2007-04-19 WO PCT/EP2007/053847 patent/WO2007147659A1/en not_active Ceased
- 2007-04-19 EP EP07845239A patent/EP2013199A1/en not_active Withdrawn
- 2007-04-19 MX MX2008013520A patent/MX2008013520A/es not_active Application Discontinuation
- 2007-04-19 AU AU2007263237A patent/AU2007263237B2/en not_active Ceased
- 2007-04-19 US US12/296,714 patent/US20090281126A1/en not_active Abandoned
- 2007-04-19 JP JP2009505894A patent/JP2009534358A/ja active Pending
- 2007-04-19 RU RU2008145708/04A patent/RU2008145708A/ru not_active Application Discontinuation
- 2007-04-19 CN CNA2007800142903A patent/CN101426785A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB0607944D0 (en) | 2006-05-31 |
| CN101426785A (zh) | 2009-05-06 |
| JP2009534358A (ja) | 2009-09-24 |
| EP2013199A1 (en) | 2009-01-14 |
| RU2008145708A (ru) | 2010-05-27 |
| KR20080110845A (ko) | 2008-12-19 |
| AU2007263237A1 (en) | 2007-12-27 |
| WO2007147659A1 (en) | 2007-12-27 |
| US20090281126A1 (en) | 2009-11-12 |
| BRPI0710514A2 (pt) | 2011-08-16 |
| MX2008013520A (es) | 2008-10-29 |
| AU2007263237B2 (en) | 2010-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130419 |