JP2006516641A5 - - Google Patents
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- Publication number
- JP2006516641A5 JP2006516641A5 JP2006503239A JP2006503239A JP2006516641A5 JP 2006516641 A5 JP2006516641 A5 JP 2006516641A5 JP 2006503239 A JP2006503239 A JP 2006503239A JP 2006503239 A JP2006503239 A JP 2006503239A JP 2006516641 A5 JP2006516641 A5 JP 2006516641A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxymethyl
- oxolan
- amino
- purin
- compound
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 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 1
- KKNKYIHFOMMLCJ-LZGVZRDRSA-N (2r,3r,5s)-2-[2-chloro-6-[[(1r)-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(Cl)=NC(N[C@H]3C(CCC3)O)=C2N=C1 KKNKYIHFOMMLCJ-LZGVZRDRSA-N 0.000 claims 1
- 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 1
- IKZMGOBTEUJYCD-QOBXEIRBSA-N (2r,3r,5s)-5-(hydroxymethyl)-2-[6-[[(3r)-oxolan-3-yl]amino]purin-9-yl]oxolan-3-ol Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3COCC3)=C2N=C1 IKZMGOBTEUJYCD-QOBXEIRBSA-N 0.000 claims 1
- WJSZXZVZJFVOPD-UHFFFAOYSA-N (3-fluorophenyl)-pyrrolidin-1-ylmethanone Chemical compound FC1=CC=CC(C(=O)N2CCCC2)=C1 WJSZXZVZJFVOPD-UHFFFAOYSA-N 0.000 claims 1
- JMBRGZCUPSPMRD-UHFFFAOYSA-N (4-ethylphenyl)-pyrrolidin-1-ylmethanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCCC1 JMBRGZCUPSPMRD-UHFFFAOYSA-N 0.000 claims 1
- YAUUECFHRSHLAF-UHFFFAOYSA-N (4-fluorophenyl)-pyrrolidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCCC1 YAUUECFHRSHLAF-UHFFFAOYSA-N 0.000 claims 1
- QTVNUTRPVMDAJC-UHFFFAOYSA-N (4-methoxyphenyl)-pyrrolidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCCC1 QTVNUTRPVMDAJC-UHFFFAOYSA-N 0.000 claims 1
- SHSCEZIUPOISRQ-JNIYBQFBSA-N 1-[(3r)-3-[[2-chloro-9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1NC1=NC(Cl)=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 SHSCEZIUPOISRQ-JNIYBQFBSA-N 0.000 claims 1
- BTGPDOWEODPVLC-SJBDTSRBSA-N 1-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)C)CC[C@H]1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 BTGPDOWEODPVLC-SJBDTSRBSA-N 0.000 claims 1
- KFGXJHQSLQFNQM-AZKPJATDSA-N 1-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 KFGXJHQSLQFNQM-AZKPJATDSA-N 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010052840 Cardiac flutter Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000007718 Stable Angina Diseases 0.000 claims 1
- 208000003734 Supraventricular Tachycardia Diseases 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 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
- VACCDLQQNSXQLB-XZWCOCNFSA-N [(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-naphthalen-2-ylmethanone Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=C4C=CC=CC4=CC=3)=C2N=C1 VACCDLQQNSXQLB-XZWCOCNFSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- FZCFGTYSKJLRRR-UHFFFAOYSA-N heptan-1-one Chemical compound CCCCCC[C]=O FZCFGTYSKJLRRR-UHFFFAOYSA-N 0.000 claims 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VIQDUCBDZPYNNX-UHFFFAOYSA-N phenyl(pyrrolidin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCCC1 VIQDUCBDZPYNNX-UHFFFAOYSA-N 0.000 claims 1
- -1 pyrrolidinyl 4- (trifluoromethyl) Phenyl Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44452603P | 2003-02-03 | 2003-02-03 | |
| PCT/US2004/002868 WO2004069185A2 (en) | 2003-02-03 | 2004-02-02 | Partial and full agonists of a1 adenosine receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006516641A JP2006516641A (ja) | 2006-07-06 |
| JP2006516641A5 true JP2006516641A5 (https=) | 2007-03-22 |
Family
ID=32850877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006503239A Pending JP2006516641A (ja) | 2003-02-03 | 2004-02-02 | アデノシン受容体の完全アゴニストおよび部分アゴニスト |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7163928B2 (https=) |
| EP (1) | EP1590359A2 (https=) |
| JP (1) | JP2006516641A (https=) |
| KR (1) | KR20050097971A (https=) |
| AU (1) | AU2004209986C1 (https=) |
| CA (1) | CA2515068A1 (https=) |
| NZ (1) | NZ541651A (https=) |
| WO (1) | WO2004069185A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7338964B2 (en) | 2004-09-09 | 2008-03-04 | Solvay Pharmaceuticals, B.V. | 2-substituted-1-deaza purine derivatives with adenosine receptor modulating activity |
| 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. |
| ATE497960T1 (de) * | 2005-10-13 | 2011-02-15 | Cv Therapeutics Inc | A1-adenosinrezeptoragonisten |
| EA015683B1 (ru) * | 2005-11-30 | 2011-10-31 | Инотек Фармасьютикалз Корпорейшн | Производные пурина и способы их применения |
| AU2008340421B2 (en) * | 2007-12-21 | 2013-12-19 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| WO2009087127A1 (en) | 2008-01-11 | 2009-07-16 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| JP5328816B2 (ja) | 2008-02-22 | 2013-10-30 | エフ．ホフマン−ラ ロシュ アーゲー | アミロイドβの調節薬 |
| WO2010040661A1 (en) | 2008-10-09 | 2010-04-15 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| AU2009312856A1 (en) | 2008-11-10 | 2010-05-14 | F. Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
| BRPI1014224A2 (pt) | 2009-06-30 | 2019-09-24 | Forest Laboratories Holdings Ltd | composto, composição farmacêutica,e, método para tratar um estado. |
| 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 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS55160796A (en) * | 1979-06-01 | 1980-12-13 | Yamasa Shoyu Co Ltd | Preparation of n6-alkyl cordycepin |
| AU575438B2 (en) | 1984-10-26 | 1988-07-28 | Warner-Lambert Company | N6 - substituted deoxyribose analogues of adenosines |
| US5432164A (en) * | 1991-10-24 | 1995-07-11 | Novo Nordisk A/S | C2,N6 -disubstituted adenosine derivatives |
| 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 |
| WO1998001459A1 (en) * | 1996-07-05 | 1998-01-15 | Novo Nordisk A/S | Novel n-alkoxyadenine derivatives acting as cytokine inhibitors |
| US5789416B1 (en) * | 1996-08-27 | 1999-10-05 | Cv Therapeutics Inc | N6 mono heterocyclic substituted adenosine derivatives |
| EP0929218A4 (en) * | 1996-10-30 | 2001-05-16 | Univ North Carolina | P2Y RECEPTOR ANTAGONISTS |
| US6211165B1 (en) * | 1997-05-09 | 2001-04-03 | The Trustees Of The University Of Pennsylvania | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
| AU1363699A (en) * | 1997-10-23 | 1999-05-10 | National Institute Of Health | Methods for reducing ischemic injury of the heart via the sequential administ ration of monophosphoryl lipid a and adenosine receptor agents |
| GB9723590D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723589D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723566D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| EP1069903A1 (en) * | 1998-03-11 | 2001-01-24 | Lipitek International, Inc. | Novel nucleoside analogs and uses in treating disease |
| GB9813554D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| US6258793B1 (en) * | 1999-12-03 | 2001-07-10 | Cv Therapeutics, Inc. | N6 heterocyclic 5′ modified adenosine derivatives |
| US6605597B1 (en) | 1999-12-03 | 2003-08-12 | Cv Therapeutics, Inc. | Partial or full A1agonists-N-6 heterocyclic 5′-thio substituted adenosine derivatives |
| US6946449B2 (en) * | 2001-07-13 | 2005-09-20 | Cv Therapeutics, Inc. | Partial and full agonists of A1 adenosine receptors |
| WO2004050678A2 (en) * | 2002-12-03 | 2004-06-17 | Baylor University | Compounds resistant to metabolic deactivation and methods of use |
-
2004
- 2004-02-02 NZ NZ541651A patent/NZ541651A/en unknown
- 2004-02-02 KR KR1020057014259A patent/KR20050097971A/ko not_active Ceased
- 2004-02-02 US US10/770,542 patent/US7163928B2/en not_active Expired - Lifetime
- 2004-02-02 JP JP2006503239A patent/JP2006516641A/ja active Pending
- 2004-02-02 WO PCT/US2004/002868 patent/WO2004069185A2/en not_active Ceased
- 2004-02-02 AU AU2004209986A patent/AU2004209986C1/en not_active Ceased
- 2004-02-02 EP EP04707373A patent/EP1590359A2/en not_active Withdrawn
- 2004-02-02 CA CA002515068A patent/CA2515068A1/en not_active Abandoned
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