AU2004209986C1 - Partial and full agonists of A1 adenosine receptors - Google Patents
Partial and full agonists of A1 adenosine receptors Download PDFInfo
- Publication number
- AU2004209986C1 AU2004209986C1 AU2004209986A AU2004209986A AU2004209986C1 AU 2004209986 C1 AU2004209986 C1 AU 2004209986C1 AU 2004209986 A AU2004209986 A AU 2004209986A AU 2004209986 A AU2004209986 A AU 2004209986A AU 2004209986 C1 AU2004209986 C1 AU 2004209986C1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- oxolan
- hydroxymethyl
- hydroxy
- purin
- 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.)
- Ceased
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- 101150007969 ADORA1 gene Proteins 0.000 title description 15
- 239000000556 agonist Substances 0.000 title description 13
- 230000036961 partial effect Effects 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 133
- -1 pyrrolidinyl 4-(trifluoromethyl)phenyl ketone Chemical compound 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- AFUIROHXZUNVTG-KXUBAAQCSA-N (2-fluorophenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C(=CC=CC=3)F)=C2N=C1 AFUIROHXZUNVTG-KXUBAAQCSA-N 0.000 claims description 2
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- SDFGTAJVYBDLPM-VTLCSEFTSA-N (2r,3r,5s)-2-[6-[[(1s,2s)-2-hydroxycyclopentyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@@H]3[C@H](CCC3)O)=C2N=C1 SDFGTAJVYBDLPM-VTLCSEFTSA-N 0.000 claims description 2
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- BKTHVDXBRSAQQK-DXEZIKHYSA-N (3-fluorophenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=C(F)C=CC=3)=C2N=C1 BKTHVDXBRSAQQK-DXEZIKHYSA-N 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- XDPCNPCKDGQBAN-UHFFFAOYSA-N 3-hydroxytetrahydrofuran Chemical compound OC1CCOC1 XDPCNPCKDGQBAN-UHFFFAOYSA-N 0.000 claims 2
- FZCFGTYSKJLRRR-UHFFFAOYSA-N heptan-1-one Chemical compound CCCCCC[C]=O FZCFGTYSKJLRRR-UHFFFAOYSA-N 0.000 claims 2
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- QTZPEVRTTPHQIN-WVWCEFAQSA-N [(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-naphthalen-1-ylmethanone Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C4=CC=CC=C4C=CC=3)=C2N=C1 QTZPEVRTTPHQIN-WVWCEFAQSA-N 0.000 claims 1
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Classifications
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- C07D473/00—Heterocyclic compounds containing purine ring systems
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- 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
- C07H19/16—Purine radicals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Neurology (AREA)
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- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US44452603P | 2003-02-03 | 2003-02-03 | |
| US60/444,526 | 2003-02-03 | ||
| PCT/US2004/002868 WO2004069185A2 (en) | 2003-02-03 | 2004-02-02 | Partial and full agonists of a1 adenosine receptors |
Publications (3)
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| AU2004209986A1 AU2004209986A1 (en) | 2004-08-19 |
| AU2004209986B2 AU2004209986B2 (en) | 2009-01-22 |
| AU2004209986C1 true AU2004209986C1 (en) | 2009-08-13 |
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| US (1) | US7163928B2 (enExample) |
| EP (1) | EP1590359A2 (enExample) |
| JP (1) | JP2006516641A (enExample) |
| KR (1) | KR20050097971A (enExample) |
| AU (1) | AU2004209986C1 (enExample) |
| CA (1) | CA2515068A1 (enExample) |
| NZ (1) | NZ541651A (enExample) |
| WO (1) | WO2004069185A2 (enExample) |
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| US7371737B2 (en) | 2004-09-09 | 2008-05-13 | Solvay Pharmaceuticals, B.V. | 2-substituted-6-trifluoromethyl purine derivatives with adenosine-A3 antagonistic activity |
| AR050630A1 (es) * | 2004-09-09 | 2006-11-08 | Solvay Pharm Bv | DERIVADOS DE 6- TRIFLUOROMETIL PURINA 2- SUSTITUIDA CON ACTIVIDAD ANTAGONISTA DE ADENOSINA-A3. PROCESOS DE OBTENCIoN Y COMPOSICIONES FARMACÉUTICAS. |
| US7338964B2 (en) | 2004-09-09 | 2008-03-04 | Solvay Pharmaceuticals, B.V. | 2-substituted-1-deaza purine derivatives with adenosine receptor modulating activity |
| WO2007047401A2 (en) * | 2005-10-13 | 2007-04-26 | Cv Therapeutics, Inc. | A1 adenosine receptor agonists |
| JP5203214B2 (ja) * | 2005-11-30 | 2013-06-05 | イノテック ファーマシューティカルズ コーポレイション | プリン化合物およびその使用方法 |
| BRPI0821141A2 (pt) * | 2007-12-21 | 2015-06-16 | Hoffmann La Roche | Derivados de heteroarila como antagonistas do receptor de orexina |
| CA2703824C (en) | 2008-01-11 | 2016-06-07 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| MX2010008700A (es) | 2008-02-22 | 2010-08-30 | Hoffmann La Roche | Moduladores de beta-amiloide. |
| AU2009301210B2 (en) | 2008-10-09 | 2014-05-15 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| CN102209537A (zh) | 2008-11-10 | 2011-10-05 | 弗·哈夫曼-拉罗切有限公司 | 杂环γ分泌酶调节剂 |
| 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 |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| US20240247001A1 (en) | 2022-12-16 | 2024-07-25 | Astrazeneca Ab | 2,6,9-trisubstituted purines |
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| US3346560A (en) * | 1965-01-29 | 1967-10-10 | Merck & Co Inc | Purine 3-deoxynucleosides |
| JPS55160794A (en) * | 1979-06-01 | 1980-12-13 | Yamasa Shoyu Co Ltd | N6-substituted cordycepin and its preparation |
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-
2004
- 2004-02-02 KR KR1020057014259A patent/KR20050097971A/ko not_active Ceased
- 2004-02-02 WO PCT/US2004/002868 patent/WO2004069185A2/en not_active Ceased
- 2004-02-02 CA CA002515068A patent/CA2515068A1/en not_active Abandoned
- 2004-02-02 EP EP04707373A patent/EP1590359A2/en not_active Withdrawn
- 2004-02-02 NZ NZ541651A patent/NZ541651A/en unknown
- 2004-02-02 JP JP2006503239A patent/JP2006516641A/ja active Pending
- 2004-02-02 AU AU2004209986A patent/AU2004209986C1/en not_active Ceased
- 2004-02-02 US US10/770,542 patent/US7163928B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004209986B2 (en) | 2009-01-22 |
| EP1590359A2 (en) | 2005-11-02 |
| AU2004209986A1 (en) | 2004-08-19 |
| US7163928B2 (en) | 2007-01-16 |
| US20040198691A1 (en) | 2004-10-07 |
| WO2004069185A2 (en) | 2004-08-19 |
| KR20050097971A (ko) | 2005-10-10 |
| JP2006516641A (ja) | 2006-07-06 |
| CA2515068A1 (en) | 2004-08-19 |
| NZ541651A (en) | 2009-01-31 |
| WO2004069185A3 (en) | 2004-09-23 |
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