JP2008516969A5 - - Google Patents
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- JP2008516969A5 JP2008516969A5 JP2007536923A JP2007536923A JP2008516969A5 JP 2008516969 A5 JP2008516969 A5 JP 2008516969A5 JP 2007536923 A JP2007536923 A JP 2007536923A JP 2007536923 A JP2007536923 A JP 2007536923A JP 2008516969 A5 JP2008516969 A5 JP 2008516969A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- optionally substituted
- propyl
- dione
- trihydropurine
- 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
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- -1 n- propyl Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 206010035664 Pneumonia Diseases 0.000 claims description 10
- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
- 208000036065 Airway Remodeling Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 238000007912 intraperitoneal administration Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 70
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 150000004866 oxadiazoles Chemical class 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- YTNFLFXQFWBCKN-UHFFFAOYSA-N 1,3-dipropyl-8-[1-[[5-[4-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(=C1)C=NN1CC(=NO1)C=C1C1=CC=C(C(F)(F)F)C=C1 YTNFLFXQFWBCKN-UHFFFAOYSA-N 0.000 claims 1
- FOPDIVBIDYTGMD-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-ethyl-8-[1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound O=C1N(CC)C=2N=C(C3=CN(CC=4C=NC(=CC=4)C(F)(F)F)N=C3)NC=2C(=O)N1CC1CC1 FOPDIVBIDYTGMD-UHFFFAOYSA-N 0.000 claims 1
- TXEFUDYEMBGBMN-UHFFFAOYSA-N 3-ethyl-1-propyl-8-[1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC)C=2N=C1C(=C1)C=NN1CC1=CC=C(C(F)(F)F)N=C1 TXEFUDYEMBGBMN-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 1
- PSHSAHVUUAGSSH-UHFFFAOYSA-N 8-[1-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methyl]pyrazol-4-yl]-3-ethyl-1-propyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC)C=2N=C1C(=C1)C=NN1CC(=NO1)C=C1C1=CC=C(Cl)C=C1 PSHSAHVUUAGSSH-UHFFFAOYSA-N 0.000 claims 1
- JNJWKLSCJORTLT-UHFFFAOYSA-N 8-[4-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=CC=C1OC JNJWKLSCJORTLT-UHFFFAOYSA-N 0.000 claims 1
- AHJHSANRNGKAFS-UHFFFAOYSA-N 8-[4-[[5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=CC(OC)=C1 AHJHSANRNGKAFS-UHFFFAOYSA-N 0.000 claims 1
- LHMYROXNDKDUQN-UHFFFAOYSA-N 8-[4-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=C(F)C=C1 LHMYROXNDKDUQN-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Chemical group 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 102000055025 Adenosine deaminases Human genes 0.000 description 29
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 28
- 241000699670 Mus sp. Species 0.000 description 22
- 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 14
- 239000003981 vehicle Substances 0.000 description 8
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 7
- 102000008186 Collagen Human genes 0.000 description 7
- 108010035532 Collagen Proteins 0.000 description 7
- 229960005305 adenosine Drugs 0.000 description 7
- 210000004072 lung Anatomy 0.000 description 7
- 229920001436 collagen Polymers 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 208000004852 Lung Injury Diseases 0.000 description 2
- 208000019693 Lung disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010069363 Traumatic lung injury Diseases 0.000 description 2
- 229940121359 adenosine receptor antagonist Drugs 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000037319 collagen production Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000010339 dilation Effects 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 2
- KOYXXLLNCXWUNF-UHFFFAOYSA-N 3-ethyl-1-propyl-8-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC)C=2N=C1C(=C1)C=NN1CC1=CC=CC(C(F)(F)F)=C1 KOYXXLLNCXWUNF-UHFFFAOYSA-N 0.000 description 1
- 229940123407 Androgen receptor antagonist Drugs 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003449 adenosine A2 receptor antagonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61943904P | 2004-10-15 | 2004-10-15 | |
| PCT/US2005/036950 WO2006044610A1 (en) | 2004-10-15 | 2005-10-14 | Method of preventing and treating airway remodeling and pulmonary inflammation using a2b adenosine receptor antagonists |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011277345A Division JP2012056965A (ja) | 2004-10-15 | 2011-12-19 | Ａ２ｂアデノシン受容体アンタゴニストを使用した、気道のリモデリングおよび肺の炎症の予防および処置の方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008516969A JP2008516969A (ja) | 2008-05-22 |
| JP2008516969A5 true JP2008516969A5 (https=) | 2009-12-24 |
Family
ID=35677798
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007536923A Pending JP2008516969A (ja) | 2004-10-15 | 2005-10-14 | Ａ２ｂアデノシン受容体アンタゴニストを使用した、気道のリモデリングおよび肺の炎症の予防および処置の方法 |
| JP2011277345A Withdrawn JP2012056965A (ja) | 2004-10-15 | 2011-12-19 | Ａ２ｂアデノシン受容体アンタゴニストを使用した、気道のリモデリングおよび肺の炎症の予防および処置の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011277345A Withdrawn JP2012056965A (ja) | 2004-10-15 | 2011-12-19 | Ａ２ｂアデノシン受容体アンタゴニストを使用した、気道のリモデリングおよび肺の炎症の予防および処置の方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20060159627A1 (https=) |
| EP (2) | EP1799221A1 (https=) |
| JP (2) | JP2008516969A (https=) |
| KR (1) | KR20070063548A (https=) |
| CN (1) | CN101039677A (https=) |
| AU (1) | AU2005295654B2 (https=) |
| CA (1) | CA2583986A1 (https=) |
| IL (1) | IL182493A0 (https=) |
| MX (1) | MX2007004373A (https=) |
| NO (1) | NO20072466L (https=) |
| NZ (2) | NZ554485A (https=) |
| RU (1) | RU2391103C2 (https=) |
| WO (1) | WO2006044610A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6403567B1 (en) | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| AU2001238665A1 (en) | 2000-02-23 | 2001-09-03 | Cv Therapeutics, Inc. | Method of identifying partial agonists of the a2a receptor |
| JP2005538190A (ja) * | 2002-07-29 | 2005-12-15 | シーブイ・セラピューティクス・インコーポレイテッド | 心筋潅流イメージング |
| ES2557310T3 (es) * | 2003-08-25 | 2016-01-25 | Dogwood Pharmaceuticals, Inc. | 8-heteroaril xantinas substituidas |
| CN101076343A (zh) * | 2004-10-20 | 2007-11-21 | Cv医药有限公司 | A2a腺苷受体激动剂的应用 |
| WO2006091898A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
| US7598379B2 (en) | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| US7579348B2 (en) * | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| EP1891070A1 (en) * | 2005-06-16 | 2008-02-27 | Cv Therapeutics, Inc. | Prodrugs of a2b adenosine receptor antagonists |
| WO2007084485A2 (en) * | 2006-01-13 | 2007-07-26 | Battelle Memorial Institute | Markers for assessing copd-related diseases |
| WO2007092372A1 (en) | 2006-02-03 | 2007-08-16 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| US7884100B2 (en) * | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
| US7767685B2 (en) * | 2006-06-29 | 2010-08-03 | King Pharmaceuticals Research And Development, Inc. | Adenosine A2B receptor antagonists |
| US20090081120A1 (en) * | 2006-09-01 | 2009-03-26 | Cv Therapeutics, Inc. | Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods |
| WO2008028140A1 (en) * | 2006-09-01 | 2008-03-06 | Cv Therapeutics, Inc. | Methods and compositions for increasing patient tolerability during myocardial imaging methods |
| US20080170990A1 (en) * | 2006-09-29 | 2008-07-17 | Cv Therapeutics, Inc. | Methods for Myocardial Imaging in Patients Having a History of Pulmonary Disease |
| WO2008086096A2 (en) * | 2007-01-03 | 2008-07-17 | Cv Therapeutics, Inc. | Myocardial perfusion imaging |
| EP2268641B1 (en) * | 2008-03-26 | 2014-09-03 | Advinus Therapeutics Pvt. Ltd. | Heterocyclic compounds as adenosine receptor antagonist |
| MX2011003168A (es) * | 2008-09-29 | 2011-05-19 | Gilead Sciences Inc | Combinaciones de un agente de control de cantidad y un antagonista del receptor a-2-alfa para utilizarse en metodos de tomografia computarizada de detectores multiples. |
| JP5765239B2 (ja) * | 2009-03-13 | 2015-08-19 | アドヴィナス・セラピューティックス・リミテッド | 置換縮合ピリミジン化合物 |
| BR112012032766A2 (pt) * | 2010-06-30 | 2019-09-24 | Gilead Sciences Inc | uso de antagonistas do receptor de adenosina a2b para o tratamento da hipertensão pulmonar |
| AR085942A1 (es) | 2011-04-07 | 2013-11-06 | Gilead Sciences Inc | Uso de receptor de aadenosina para tratar la insuficiencia cardiaca y la arritmia en pacientes posinfarto de miocardio |
| WO2016083304A1 (en) * | 2014-11-24 | 2016-06-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Treatment of acute exacerbations of chronic obstructive pulmonary disease by antagonism of the il-20r. |
| ES2580702B1 (es) | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| ES2975753T3 (es) | 2018-03-05 | 2024-07-12 | Teon Therapeutics Inc | Antagonistas del receptor de adenosina y usos de los mismos |
| CN116322698A (zh) * | 2020-09-04 | 2023-06-23 | 泰昂治疗公司 | 腺苷a2b受体拮抗剂的共晶 |
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| US6977300B2 (en) * | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US6933298B2 (en) * | 2001-12-08 | 2005-08-23 | Aventis Pharma Deutschland Gmbh | Pyridine-2,4-dicarboxylic acid diamides and pyrimidine-4,6-dicarboxylic acid diamides and the use thereof for selectively inhibiting collagenases |
| CN1620294A (zh) * | 2001-12-20 | 2005-05-25 | Osi药物公司 | 嘧啶a2b选择性拮抗剂化合物,它们的合成及用途 |
| ES2229928B1 (es) | 2003-10-02 | 2006-07-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de pirimidin-2-amina. |
| CA2544193C (en) | 2003-10-31 | 2012-03-27 | Cv Therapeutics, Inc. | A2b adenosine receptor antagonists |
| MX2007002437A (es) | 2004-09-01 | 2007-08-14 | Cv Therapeutics Inc | Metodo para el sanado de heridas utilizando antagonistas del receptor de adenosina a2b. |
| EP1891070A1 (en) | 2005-06-16 | 2008-02-27 | Cv Therapeutics, Inc. | Prodrugs of a2b adenosine receptor antagonists |
| AU2007227021B2 (en) | 2006-03-17 | 2012-12-20 | Gilead Sciences, Inc. | Method of preventing and treating hepatic disease using A2B adenosine receptor antagonists |
-
2005
- 2005-10-14 EP EP05808733A patent/EP1799221A1/en not_active Withdrawn
- 2005-10-14 CA CA002583986A patent/CA2583986A1/en not_active Abandoned
- 2005-10-14 JP JP2007536923A patent/JP2008516969A/ja active Pending
- 2005-10-14 AU AU2005295654A patent/AU2005295654B2/en not_active Ceased
- 2005-10-14 CN CNA200580034824XA patent/CN101039677A/zh active Pending
- 2005-10-14 WO PCT/US2005/036950 patent/WO2006044610A1/en not_active Ceased
- 2005-10-14 MX MX2007004373A patent/MX2007004373A/es unknown
- 2005-10-14 NZ NZ554485A patent/NZ554485A/en not_active IP Right Cessation
- 2005-10-14 RU RU2007117907/14A patent/RU2391103C2/ru not_active IP Right Cessation
- 2005-10-14 EP EP10011664A patent/EP2311462A1/en not_active Withdrawn
- 2005-10-14 KR KR1020077008536A patent/KR20070063548A/ko not_active Ceased
- 2005-10-14 US US11/251,450 patent/US20060159627A1/en not_active Abandoned
- 2005-10-14 NZ NZ589657A patent/NZ589657A/en not_active IP Right Cessation
-
2007
- 2007-04-12 IL IL182493A patent/IL182493A0/en unknown
- 2007-05-14 NO NO20072466A patent/NO20072466L/no not_active Application Discontinuation
-
2009
- 2009-10-26 US US12/605,783 patent/US8466129B2/en active Active
-
2011
- 2011-12-19 JP JP2011277345A patent/JP2012056965A/ja not_active Withdrawn
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