JP2005524627A5 - - Google Patents
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- Publication number
- JP2005524627A5 JP2005524627A5 JP2003562091A JP2003562091A JP2005524627A5 JP 2005524627 A5 JP2005524627 A5 JP 2005524627A5 JP 2003562091 A JP2003562091 A JP 2003562091A JP 2003562091 A JP2003562091 A JP 2003562091A JP 2005524627 A5 JP2005524627 A5 JP 2005524627A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyrimidine
- oxo
- methyl
- ethynyl
- trimethylsilyl
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- IRQCRYKFGZBSMD-UHFFFAOYSA-N 5-hydroxy-1-methyl-6-oxo-2-(2-trimethylsilylethynyl)pyrimidine-4-carboxylic acid Chemical compound CN1C(C#C[Si](C)(C)C)=NC(C(O)=O)=C(O)C1=O IRQCRYKFGZBSMD-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- JMCTYXFDNXPMET-UHFFFAOYSA-N N1CN=C(C=C1)C(=O)OCC Chemical compound N1CN=C(C=C1)C(=O)OCC JMCTYXFDNXPMET-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0201179.9A GB0201179D0 (en) | 2002-01-18 | 2002-01-18 | Therapeutic agents |
| PCT/GB2003/000124 WO2003062211A1 (en) | 2002-01-18 | 2003-01-15 | Pyrimidinone viral polymerase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005524627A JP2005524627A (ja) | 2005-08-18 |
| JP2005524627A5 true JP2005524627A5 (https=) | 2010-02-04 |
| JP4498745B2 JP4498745B2 (ja) | 2010-07-07 |
Family
ID=9929352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003562091A Expired - Fee Related JP4498745B2 (ja) | 2002-01-18 | 2003-01-15 | ピリミジノンウイルスポリメラーゼ阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20050130997A1 (https=) |
| EP (1) | EP1470113B1 (https=) |
| JP (1) | JP4498745B2 (https=) |
| AT (1) | ATE420078T1 (https=) |
| CA (1) | CA2473508A1 (https=) |
| DE (1) | DE60325692D1 (https=) |
| GB (1) | GB0201179D0 (https=) |
| WO (1) | WO2003062211A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004062613A2 (en) | 2003-01-13 | 2004-07-29 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| EP1658302B1 (en) | 2003-07-25 | 2010-08-25 | IDENIX Pharmaceuticals, Inc. | Purine nucleoside analogues for treating diseases caused by flaviviridae including hepatitis c |
| AU2003304416A1 (en) * | 2003-08-13 | 2005-03-07 | Bf Research Institute, Inc. | Probe for disease with amyloid deposit, amyloid-staining agent, remedy and preventive for disease with amyloid deposit and diagnostic probe and staining agent for neurofibril change |
| AR046938A1 (es) * | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
| HRP20130971T1 (hr) | 2004-02-20 | 2013-11-08 | Boehringer Ingelheim International Gmbh | Inhibitori virusne polimeraze |
| CA2606195C (en) | 2005-05-02 | 2015-03-31 | Merck And Co., Inc. | Hcv ns3 protease inhibitors |
| AR057456A1 (es) | 2005-07-20 | 2007-12-05 | Merck & Co Inc | Inhibidores de la proteasa ns3 del vhc |
| NZ565269A (en) | 2005-08-01 | 2010-03-26 | Merck & Co Inc | Macrocyclic peptides as HCV NS3 protease inhibitors |
| CA2622639C (en) * | 2005-10-04 | 2012-01-03 | Istituto Di Recerche Di Biologia Molecolare P. Angeletti S.P.A. | Hiv integrase inhibitors |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| AU2007309488B2 (en) | 2006-10-24 | 2012-10-11 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| CA2667146C (en) | 2006-10-24 | 2016-01-19 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| AU2007309546A1 (en) | 2006-10-24 | 2008-05-02 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | HCV NS3 protease inhibitors |
| BRPI0718161A2 (pt) | 2006-10-27 | 2013-11-26 | Merck & Co Inc | Composto, composição farmacêutica, e, uso do composto. |
| US8377874B2 (en) | 2006-10-27 | 2013-02-19 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| CA2672250C (en) | 2006-12-20 | 2013-04-30 | Ian Stansfield | Antiviral indoles |
| GB0625345D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB0625349D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| US7763630B2 (en) | 2007-06-06 | 2010-07-27 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| JP2010533699A (ja) | 2007-07-17 | 2010-10-28 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | Ｃ型肝炎感染症の治療のための大環状インドール誘導体 |
| AU2008277377B2 (en) | 2007-07-19 | 2013-08-01 | Msd Italia S.R.L. | Macrocyclic compounds as antiviral agents |
| US8242140B2 (en) * | 2007-08-03 | 2012-08-14 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| WO2009134624A1 (en) | 2008-04-28 | 2009-11-05 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| EA019327B1 (ru) | 2008-07-22 | 2014-02-28 | Мерк Шарп Энд Домэ Корп. | Макроциклическое хиноксалиновое соединение в качестве ингибитора протеазы вгс ns3 |
| CN102271699A (zh) | 2009-01-07 | 2011-12-07 | 西尼克斯公司 | 用于治疗hcv和hiv感染的环孢菌素衍生物 |
| MX2011008276A (es) | 2009-02-06 | 2011-12-14 | Elan Pharm Inc | Inhibidores de quinasa jun n-terminal. |
| US8143244B2 (en) | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| CA2755023C (en) * | 2009-03-25 | 2016-12-13 | Abbott Laboratories | Antiviral compounds and uses thereof |
| US8828930B2 (en) | 2009-07-30 | 2014-09-09 | Merck Sharp & Dohme Corp. | Hepatitis C virus NS3 protease inhibitors |
| US8383639B2 (en) | 2009-10-15 | 2013-02-26 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| MX2013001273A (es) * | 2010-08-13 | 2013-04-10 | Hoffmann La Roche | Compuestos heterociclicos antivirales. |
| WO2012151567A1 (en) * | 2011-05-05 | 2012-11-08 | St. Jude Children's Research Hospital | Pyrimidinone compounds and methods for preventing and treating influenza |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2260319B (en) * | 1991-10-07 | 1995-12-06 | Norsk Hydro As | Acyl derivatives of nucleosides and nucleoside analogues having anti-viral activity |
| DE19817265A1 (de) * | 1998-04-18 | 1999-10-21 | Bayer Ag | Verwendung von Dihydropyrimidinen als Arzneimittel und neue Stoffe |
| BR9913406A (pt) * | 1998-09-04 | 2002-01-29 | Viropharma Inc | Processo de tratamento de infecção causada por pelo menos um vìrus da famìlia flaviviridae e de doença associada com a citada infecção em um hospedeiro vivo possuindo a citada infecção |
| GB0017676D0 (en) * | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
-
2002
- 2002-01-18 GB GBGB0201179.9A patent/GB0201179D0/en not_active Ceased
-
2003
- 2003-01-15 CA CA002473508A patent/CA2473508A1/en not_active Abandoned
- 2003-01-15 AT AT03700366T patent/ATE420078T1/de not_active IP Right Cessation
- 2003-01-15 EP EP03700366A patent/EP1470113B1/en not_active Expired - Lifetime
- 2003-01-15 WO PCT/GB2003/000124 patent/WO2003062211A1/en not_active Ceased
- 2003-01-15 DE DE60325692T patent/DE60325692D1/de not_active Expired - Lifetime
- 2003-01-15 JP JP2003562091A patent/JP4498745B2/ja not_active Expired - Fee Related
- 2003-01-15 US US10/500,971 patent/US20050130997A1/en not_active Abandoned
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