JP2006528199A - Ａ１アデノシン受容体拮抗薬 - Google Patents
Ａ１アデノシン受容体拮抗薬 Download PDFInfo
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- JP2006528199A JP2006528199A JP2006521248A JP2006521248A JP2006528199A JP 2006528199 A JP2006528199 A JP 2006528199A JP 2006521248 A JP2006521248 A JP 2006521248A JP 2006521248 A JP2006521248 A JP 2006521248A JP 2006528199 A JP2006528199 A JP 2006528199A
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- Prior art keywords
- formula
- ethyl
- alkyl
- compound
- purine
- Prior art date
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- 229940121359 adenosine receptor antagonist Drugs 0.000 title description 12
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title description 12
- 101150007969 ADORA1 gene Proteins 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 57
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- 201000010099 disease Diseases 0.000 claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 9
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- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 8
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- 210000002216 heart Anatomy 0.000 claims abstract description 6
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- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 5
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 5
- 230000006378 damage Effects 0.000 claims abstract description 5
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- 201000008383 nephritis Diseases 0.000 claims abstract description 5
- 230000008085 renal dysfunction Effects 0.000 claims abstract description 5
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- 206010019280 Heart failures Diseases 0.000 claims abstract description 3
- 229940002612 prodrug Drugs 0.000 claims abstract description 3
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- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 121
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 1
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- 208000014674 injury Diseases 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000004556 brain Anatomy 0.000 abstract description 4
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- 125000001072 heteroaryl group Chemical group 0.000 description 47
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- 229910052736 halogen Inorganic materials 0.000 description 23
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 125000003342 alkenyl group Chemical group 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
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- 125000000304 alkynyl group Chemical group 0.000 description 15
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229930194542 Keto Natural products 0.000 description 9
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- 125000005110 aryl thio group Chemical group 0.000 description 9
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
- 150000001540 azides Chemical class 0.000 description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
- 125000004470 heterocyclooxy group Chemical group 0.000 description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 description 8
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- 208000006673 asthma Diseases 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 125000005368 heteroarylthio group Chemical group 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 5
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
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- 239000000556 agonist Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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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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- 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
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- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- 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
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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
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
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- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
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- Emergency Medicine (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48946903P | 2003-07-22 | 2003-07-22 | |
| PCT/US2004/023632 WO2005009445A1 (en) | 2003-07-22 | 2004-07-22 | A1 adenosine receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006528199A true JP2006528199A (ja) | 2006-12-14 |
| JP2006528199A5 JP2006528199A5 (enExample) | 2007-08-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2006521248A Pending JP2006528199A (ja) | 2003-07-22 | 2004-07-22 | Ａ１アデノシン受容体拮抗薬 |
Country Status (8)
| Country | Link |
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| US (1) | US7022710B2 (enExample) |
| EP (1) | EP1646390B1 (enExample) |
| JP (1) | JP2006528199A (enExample) |
| KR (1) | KR20060037383A (enExample) |
| AT (1) | ATE410168T1 (enExample) |
| CA (1) | CA2533402A1 (enExample) |
| DE (1) | DE602004017005D1 (enExample) |
| WO (1) | WO2005009445A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005047268A2 (en) * | 2003-11-10 | 2005-05-26 | X-Ceptor Therapeutics, Inc. | Substituted pyrimidine compositions and methods of use |
| US20080280926A1 (en) * | 2003-12-16 | 2008-11-13 | Palle Venkata P | Phosphodiesterase Inhibitors |
| US7795427B2 (en) * | 2006-02-14 | 2010-09-14 | New York University | Methods for inhibiting osteoclast differentiation, formation, or function and for increasing bone mass |
| ES2361886T3 (es) * | 2006-06-27 | 2011-06-24 | Cbt Development Limited | Profármacos adenosina acetil 2',3'-metilideno novedosos para uso como profármacos para agonistas del receptor adenosina. |
| WO2009052310A1 (en) * | 2007-10-16 | 2009-04-23 | Cv Therapeutics, Inc | A3 adenosine receptor antagonists |
| BRPI0909157A2 (pt) * | 2008-03-26 | 2015-11-24 | Advinus Therapeutics Private Ltd | compostos heterocíclicos como antagonistas de receptores de adenosina |
| DE102008039083A1 (de) * | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Aminopyrazole und ihre Verwendung |
| US20130109645A1 (en) | 2010-03-31 | 2013-05-02 | The united States of America,as represented by Secretary,Dept.,of Health and Human Services | Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| WO2024105159A1 (en) * | 2022-11-16 | 2024-05-23 | University Of Zurich | Ligands of the m6a-rna readers |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002512246A (ja) * | 1998-04-16 | 2002-04-23 | ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト | 非対称的に置換した新規キサンチン誘導体、その製造方法及びそのアデノシン拮抗作用を有する医薬としての使用 |
| WO2002044991A1 (en) * | 2000-11-30 | 2002-06-06 | Digital Agent, Inc. | Method and system for emotion perception from text |
| WO2003002566A1 (en) * | 2001-06-29 | 2003-01-09 | Cv Therapeutics, Inc. | Purine derivatives as a2b adenosine receptor antagonists |
| JP2003501356A (ja) * | 1999-06-01 | 2003-01-14 | ユニバーシティ オブ バージニア パテント ファウンデーション | Ａ２ｂアデノシンレセプターのアンタゴニストとして有用な置換８−フェニルキサンチン |
| WO2003006465A1 (en) * | 2001-07-13 | 2003-01-23 | Cv Therapeutics, Inc. | Partial and full agonist of a adenosine receptors |
| JP2003508398A (ja) * | 1999-08-31 | 2003-03-04 | ヴァンダービルト ユニヴァーシティ | Ａ２ｂアデノシン受容体の選択的アンタゴニスト |
| WO2003053973A1 (de) * | 2001-12-21 | 2003-07-03 | Jsw-Research Forschungslabor Gmbh | Pyrazolyl-substituierte triazolochinoxaline |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7968523B2 (en) | 2001-07-23 | 2011-06-28 | Senesco Technologies, Inc. | Method for inducing apoptosis using apoptosis-specific EIF5-A |
-
2004
- 2004-07-22 WO PCT/US2004/023632 patent/WO2005009445A1/en not_active Ceased
- 2004-07-22 KR KR1020067001373A patent/KR20060037383A/ko not_active Ceased
- 2004-07-22 JP JP2006521248A patent/JP2006528199A/ja active Pending
- 2004-07-22 CA CA002533402A patent/CA2533402A1/en not_active Abandoned
- 2004-07-22 AT AT04778924T patent/ATE410168T1/de not_active IP Right Cessation
- 2004-07-22 US US10/897,047 patent/US7022710B2/en not_active Expired - Fee Related
- 2004-07-22 EP EP04778924A patent/EP1646390B1/en not_active Expired - Lifetime
- 2004-07-22 DE DE602004017005T patent/DE602004017005D1/de not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002512246A (ja) * | 1998-04-16 | 2002-04-23 | ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト | 非対称的に置換した新規キサンチン誘導体、その製造方法及びそのアデノシン拮抗作用を有する医薬としての使用 |
| JP2003501356A (ja) * | 1999-06-01 | 2003-01-14 | ユニバーシティ オブ バージニア パテント ファウンデーション | Ａ２ｂアデノシンレセプターのアンタゴニストとして有用な置換８−フェニルキサンチン |
| JP2003508398A (ja) * | 1999-08-31 | 2003-03-04 | ヴァンダービルト ユニヴァーシティ | Ａ２ｂアデノシン受容体の選択的アンタゴニスト |
| WO2002044991A1 (en) * | 2000-11-30 | 2002-06-06 | Digital Agent, Inc. | Method and system for emotion perception from text |
| WO2003002566A1 (en) * | 2001-06-29 | 2003-01-09 | Cv Therapeutics, Inc. | Purine derivatives as a2b adenosine receptor antagonists |
| WO2003006465A1 (en) * | 2001-07-13 | 2003-01-23 | Cv Therapeutics, Inc. | Partial and full agonist of a adenosine receptors |
| WO2003053973A1 (de) * | 2001-12-21 | 2003-07-03 | Jsw-Research Forschungslabor Gmbh | Pyrazolyl-substituierte triazolochinoxaline |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE410168T1 (de) | 2008-10-15 |
| CA2533402A1 (en) | 2005-02-03 |
| HK1093422A1 (en) | 2007-03-02 |
| WO2005009445A1 (en) | 2005-02-03 |
| US20050059683A1 (en) | 2005-03-17 |
| DE602004017005D1 (de) | 2008-11-20 |
| EP1646390A1 (en) | 2006-04-19 |
| US7022710B2 (en) | 2006-04-04 |
| EP1646390B1 (en) | 2008-10-08 |
| KR20060037383A (ko) | 2006-05-03 |
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