JP2007512335A5 - - Google Patents
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- Publication number
- JP2007512335A5 JP2007512335A5 JP2006541295A JP2006541295A JP2007512335A5 JP 2007512335 A5 JP2007512335 A5 JP 2007512335A5 JP 2006541295 A JP2006541295 A JP 2006541295A JP 2006541295 A JP2006541295 A JP 2006541295A JP 2007512335 A5 JP2007512335 A5 JP 2007512335A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- ethyl
- propyl
- optionally substituted
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 29
- -1 pyrazol-4-yl Chemical group 0.000 claims 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 239000012442 inert solvent Substances 0.000 claims 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 239000000543 intermediate Substances 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 239000007822 coupling agent Substances 0.000 claims 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 239000003586 protic polar solvent Substances 0.000 claims 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000002346 iodo group Chemical group I* 0.000 claims 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 3
- 235000010288 sodium nitrite Nutrition 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
- 235000011130 ammonium sulphate Nutrition 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SPJDDRUDFQBAOY-UHFFFAOYSA-N n'-(3-ethyl-2,6-dioxo-1-propylpyrimidin-4-yl)-n,n-dimethylmethanimidamide Chemical compound CCCN1C(=O)C=C(N=CN(C)C)N(CC)C1=O SPJDDRUDFQBAOY-UHFFFAOYSA-N 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 0 *N(C(N)=CC(N1)=O)C1=O Chemical compound *N(C(N)=CC(N1)=O)C1=O 0.000 description 2
- UQTQGPHSLQEVSM-UHFFFAOYSA-N CCCN(C(C(NC(c1c[n](Cc2cccc(C(F)(F)F)c2)nc1)=O)=C(N)N1CC)=O)C1=O Chemical compound CCCN(C(C(NC(c1c[n](Cc2cccc(C(F)(F)F)c2)nc1)=O)=C(N)N1CC)=O)C1=O UQTQGPHSLQEVSM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/719,102 | 2003-11-21 | ||
| US10/719,102 US7125993B2 (en) | 2001-11-09 | 2003-11-21 | A2B adenosine receptor antagonists |
| PCT/US2004/038136 WO2005051951A1 (en) | 2003-11-21 | 2004-11-15 | A2b adenosine receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007512335A JP2007512335A (ja) | 2007-05-17 |
| JP2007512335A5 true JP2007512335A5 (https=) | 2007-12-13 |
| JP4769728B2 JP4769728B2 (ja) | 2011-09-07 |
Family
ID=34633233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541295A Expired - Fee Related JP4769728B2 (ja) | 2003-11-21 | 2004-11-15 | Ａ２ｂアデノシンレセプターアンタゴニスト |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US7125993B2 (https=) |
| EP (1) | EP1685132B1 (https=) |
| JP (1) | JP4769728B2 (https=) |
| KR (1) | KR101140186B1 (https=) |
| CN (1) | CN100415748C (https=) |
| AU (1) | AU2004292529B2 (https=) |
| CA (1) | CA2546733C (https=) |
| ES (1) | ES2391178T3 (https=) |
| IL (1) | IL175759A0 (https=) |
| MX (1) | MXPA06005637A (https=) |
| NZ (1) | NZ547357A (https=) |
| RU (1) | RU2374247C2 (https=) |
| TW (1) | TWI365879B (https=) |
| WO (1) | WO2005051951A1 (https=) |
| ZA (1) | ZA200604046B (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| US6403567B1 (en) | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| AU2001238665A1 (en) | 2000-02-23 | 2001-09-03 | Cv Therapeutics, Inc. | Method of identifying partial agonists of the a2a receptor |
| US7125993B2 (en) * | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US20080318983A1 (en) * | 2001-11-09 | 2008-12-25 | Rao Kalla | A2b adenosine receptor antagonists |
| MXPA03008967A (es) * | 2002-02-01 | 2004-02-12 | King Pharmaceuticals Res & Dev | Antagonistas receptores de 8-heteroarilo xantina adenosina a-2b. |
| US8470801B2 (en) | 2002-07-29 | 2013-06-25 | Gilead Sciences, Inc. | Myocardial perfusion imaging methods and compositions |
| 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 |
| US20050020915A1 (en) * | 2002-07-29 | 2005-01-27 | Cv Therapeutics, Inc. | Myocardial perfusion imaging methods and compositions |
| EP1799221A1 (en) * | 2004-10-15 | 2007-06-27 | Cv Therapeutics, Inc. | Method of preventing and treating airway remodeling and pulmonary inflammation using a2b adenosine receptor antagonists |
| 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 |
| EP1891070A1 (en) * | 2005-06-16 | 2008-02-27 | Cv Therapeutics, Inc. | Prodrugs of a2b adenosine receptor antagonists |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| ES2274712B1 (es) * | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| WO2007092372A1 (en) | 2006-02-03 | 2007-08-16 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| AU2007227021B2 (en) | 2006-03-17 | 2012-12-20 | Gilead Sciences, Inc. | Method of preventing and treating hepatic disease using A2B adenosine 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 |
| ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
| WO2008086096A2 (en) * | 2007-01-03 | 2008-07-17 | Cv Therapeutics, Inc. | Myocardial perfusion imaging |
| JP2011528364A (ja) * | 2008-07-16 | 2011-11-17 | キング・ファーマシューティカルズ・リサーチ・アンド・デベロプメント・インコーポレイティッド | アテローム性動脈硬化症の治療 |
| 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. |
| 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 |
| ES2975753T3 (es) | 2018-03-05 | 2024-07-12 | Teon Therapeutics Inc | Antagonistas del receptor de adenosina y usos de los mismos |
| US20200345725A1 (en) | 2019-01-11 | 2020-11-05 | Omeros Corporation | Methods and Compositions for Treating Cancer |
| 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 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452788A (en) | 1982-04-21 | 1984-06-05 | Warner-Lambert Company | Substituted 8-phenylxanthines |
| US4539707A (en) * | 1982-06-01 | 1985-09-03 | Aerotron, Inc. | Compressed single side band communications system and method |
| US4593095A (en) | 1983-02-18 | 1986-06-03 | The Johns Hopkins University | Xanthine derivatives |
| US4558051A (en) | 1983-10-11 | 1985-12-10 | Richardson-Vicks, Inc. | Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same |
| GB8510758D0 (en) | 1985-04-27 | 1985-06-05 | Wellcome Found | Compounds |
| DE8817122U1 (de) | 1988-12-22 | 1993-02-04 | Boehringer Ingelheim Kg, 55218 Ingelheim | Neue Xanthinderivate mit Adenosinantogenistischer Wirkung |
| IT1229195B (it) | 1989-03-10 | 1991-07-25 | Poli Ind Chimica Spa | Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche. |
| DE4019892A1 (de) | 1990-06-22 | 1992-01-02 | Boehringer Ingelheim Kg | Neue xanthinderivate |
| TW252044B (https=) * | 1992-08-10 | 1995-07-21 | Boehringer Ingelheim Kg | |
| US5446046A (en) * | 1993-10-28 | 1995-08-29 | University Of Florida Research Foundation | A1 adenosine receptor agonists and antagonists as diuretics |
| WO1995011681A1 (en) | 1993-10-29 | 1995-05-04 | Merck & Co., Inc. | Human adenosine receptor antagonists |
| DE19535504A1 (de) | 1995-09-25 | 1997-03-27 | Bayer Ag | Substituierte Xanthine |
| GB9703044D0 (en) | 1997-02-14 | 1997-04-02 | Glaxo Group Ltd | Phenyl xanthine esters and amides |
| US6117878A (en) | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| ES2189079T3 (es) | 1998-04-24 | 2003-07-01 | Leuven K U Res & Dev | Efectos inmunosupresores de derivados de xantina 8-sustituidos. |
| US6060481A (en) | 1998-05-28 | 2000-05-09 | The Penn State Research Foundation | Method for improving insulin sensitivity using an adenosine receptor antagonist |
| CA2333947C (en) | 1998-06-01 | 2010-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compounds as adenosine a1 antagonist for male sterility |
| GB9817623D0 (en) | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| US6545002B1 (en) | 1999-06-01 | 2003-04-08 | University Of Virginia Patent Foundation | Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors |
| DK1444233T3 (da) * | 2001-11-09 | 2011-10-17 | Gilead Palo Alto Inc | A2B-adenosinreceptorantagonister |
| US7125993B2 (en) * | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US6977300B2 (en) * | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
-
2003
- 2003-11-21 US US10/719,102 patent/US7125993B2/en not_active Expired - Lifetime
-
2004
- 2004-11-15 CN CNB2004800342770A patent/CN100415748C/zh not_active Expired - Fee Related
- 2004-11-15 ES ES04811022T patent/ES2391178T3/es not_active Expired - Lifetime
- 2004-11-15 RU RU2006117349/04A patent/RU2374247C2/ru not_active IP Right Cessation
- 2004-11-15 NZ NZ547357A patent/NZ547357A/xx not_active IP Right Cessation
- 2004-11-15 WO PCT/US2004/038136 patent/WO2005051951A1/en not_active Ceased
- 2004-11-15 CA CA2546733A patent/CA2546733C/en not_active Expired - Fee Related
- 2004-11-15 KR KR1020067009840A patent/KR101140186B1/ko not_active Expired - Fee Related
- 2004-11-15 EP EP04811022A patent/EP1685132B1/en not_active Expired - Lifetime
- 2004-11-15 MX MXPA06005637A patent/MXPA06005637A/es active IP Right Grant
- 2004-11-15 JP JP2006541295A patent/JP4769728B2/ja not_active Expired - Fee Related
- 2004-11-15 AU AU2004292529A patent/AU2004292529B2/en not_active Ceased
- 2004-11-19 TW TW093135764A patent/TWI365879B/zh not_active IP Right Cessation
-
2006
- 2006-05-18 IL IL175759A patent/IL175759A0/en active IP Right Grant
- 2006-05-19 ZA ZA200604046A patent/ZA200604046B/en unknown
- 2006-08-22 US US11/508,592 patent/US7521554B2/en not_active Expired - Fee Related
-
2009
- 2009-01-28 US US12/361,409 patent/US20090137802A1/en not_active Abandoned
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