JP2006514038A5 - - Google Patents
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- JP2006514038A5 JP2006514038A5 JP2004562599A JP2004562599A JP2006514038A5 JP 2006514038 A5 JP2006514038 A5 JP 2006514038A5 JP 2004562599 A JP2004562599 A JP 2004562599A JP 2004562599 A JP2004562599 A JP 2004562599A JP 2006514038 A5 JP2006514038 A5 JP 2006514038A5
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- 238000000034 method Methods 0.000 claims 78
- 239000002777 nucleoside Substances 0.000 claims 47
- 238000006243 chemical reaction Methods 0.000 claims 40
- 125000003835 nucleoside group Chemical group 0.000 claims 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 12
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 11
- 239000000243 solution Substances 0.000 claims 11
- -1 ribofuranosyl nucleoside Chemical class 0.000 claims 7
- 239000007822 coupling agent Substances 0.000 claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 5
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000001718 carbodiimides Chemical group 0.000 claims 2
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims 2
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 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 claims 2
- 229940035893 uracil Drugs 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 claims 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims 1
- SVXNJCYYMRMXNM-UHFFFAOYSA-N 5-amino-2h-1,2,4-triazin-3-one Chemical compound NC=1C=NNC(=O)N=1 SVXNJCYYMRMXNM-UHFFFAOYSA-N 0.000 claims 1
- NPYPQKXJJZZSAX-UHFFFAOYSA-N 5-benzylpyrimidine Chemical compound C=1N=CN=CC=1CC1=CC=CC=C1 NPYPQKXJJZZSAX-UHFFFAOYSA-N 0.000 claims 1
- HXXVIKZQIFTJOQ-UHFFFAOYSA-N 5-ethenylpyrimidine Chemical compound C=CC1=CN=CN=C1 HXXVIKZQIFTJOQ-UHFFFAOYSA-N 0.000 claims 1
- 150000005697 5-halopyrimidines Chemical class 0.000 claims 1
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical compound CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims 1
- NOYDQGFVFOQSAJ-UHFFFAOYSA-N 5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=CN=C1 NOYDQGFVFOQSAJ-UHFFFAOYSA-N 0.000 claims 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 claims 1
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 claims 1
- PVRBGBGMDLPYKG-UHFFFAOYSA-N 6-benzyl-7h-purine Chemical compound N=1C=NC=2N=CNC=2C=1CC1=CC=CC=C1 PVRBGBGMDLPYKG-UHFFFAOYSA-N 0.000 claims 1
- DBCMWACNZJYUHS-UHFFFAOYSA-N 6-ethenyl-7h-purine Chemical compound C=CC1=NC=NC2=C1NC=N2 DBCMWACNZJYUHS-UHFFFAOYSA-N 0.000 claims 1
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims 1
- 229930024421 Adenine Natural products 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229960000643 adenine Drugs 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052786 argon Inorganic materials 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229940104302 cytosine Drugs 0.000 claims 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims 1
- 229960004413 flucytosine Drugs 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims 1
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims 1
- 150000004944 pyrrolopyrimidines Chemical group 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 229940113082 thymine Drugs 0.000 claims 1
- 0 CC1([C@](*2c(ncnc3*)c3N=C2)O[C@@](CO)C1O)O Chemical compound CC1([C@](*2c(ncnc3*)c3N=C2)O[C@@](CO)C1O)O 0.000 description 2
- YBLBEZRLFOVGNV-UZPSGTSLSA-N CC(C12O)[C@@]1(c1c[nH]c3c1N=CNC3=O)O[C@H](CO)C2O Chemical compound CC(C12O)[C@@]1(c1c[nH]c3c1N=CNC3=O)O[C@H](CO)C2O YBLBEZRLFOVGNV-UZPSGTSLSA-N 0.000 description 1
- FBACBJBYARSDEH-PIDKGTLBSA-N CC1([C@H]([n](cc2)c(N=CN3)c2C3=O)O[C@H](CO)C1O)O Chemical compound CC1([C@H]([n](cc2)c(N=CN3)c2C3=O)O[C@H](CO)C1O)O FBACBJBYARSDEH-PIDKGTLBSA-N 0.000 description 1
- ZJTZFMDWQNPYPB-XRAILWEFSA-N CC1([C@H]([n]2c3nc(N)nc(N)c3c(C#N)c2)O[C@H](C[N+]([O-])=O)C1O)O Chemical compound CC1([C@H]([n]2c3nc(N)nc(N)c3c(C#N)c2)O[C@H](C[N+]([O-])=O)C1O)O ZJTZFMDWQNPYPB-XRAILWEFSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43615002P | 2002-12-23 | 2002-12-23 | |
| PCT/US2003/041603 WO2004058792A1 (en) | 2002-12-23 | 2003-12-23 | Process for the production of 3'-nucleoside prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006514038A JP2006514038A (ja) | 2006-04-27 |
| JP2006514038A5 true JP2006514038A5 (enExample) | 2007-01-18 |
Family
ID=32682350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004562599A Pending JP2006514038A (ja) | 2002-12-23 | 2003-12-23 | ３’−ヌクレオシドプロドラッグの生産方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20040181051A1 (enExample) |
| EP (1) | EP1575971A4 (enExample) |
| JP (1) | JP2006514038A (enExample) |
| KR (1) | KR20050110611A (enExample) |
| CN (1) | CN100335492C (enExample) |
| AU (1) | AU2003300434A1 (enExample) |
| BR (1) | BR0316868A (enExample) |
| CA (1) | CA2511616A1 (enExample) |
| IL (1) | IL169314A0 (enExample) |
| MX (1) | MXPA05006865A (enExample) |
| NO (1) | NO20053557L (enExample) |
| NZ (1) | NZ540913A (enExample) |
| PL (1) | PL377608A1 (enExample) |
| RU (1) | RU2005123395A (enExample) |
| WO (1) | WO2004058792A1 (enExample) |
| ZA (1) | ZA200505040B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| CA2410579C (en) | 2000-05-26 | 2010-04-20 | Jean-Pierre Sommadossi | Methods and compositions for treating flaviviruses and pestiviruses |
| CN101172993A (zh) | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷 |
| CN1678326A (zh) | 2002-06-28 | 2005-10-05 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2'－c－甲基－3'－o－l－缬氨酸酯核糖呋喃基胞苷 |
| JP2006519753A (ja) | 2002-11-15 | 2006-08-31 | イデニクス（ケイマン）リミテツド | ２’−分枝ヌクレオシドおよびフラビウイルス科ウイルス突然変異 |
| MXPA05006230A (es) | 2002-12-12 | 2005-09-20 | Idenix Cayman Ltd | Proceso para la produccion de nucleosidos ramificados-2'. |
| CN1812995A (zh) * | 2003-04-28 | 2006-08-02 | 艾登尼科斯（开曼）有限公司 | 工业化规模的核苷合成 |
| US7534767B2 (en) | 2004-06-15 | 2009-05-19 | Merck & Co., Inc. | C-purine nucleoside analogs as inhibitors of RNA-dependent RNA viral polymerase |
| AU2005302448B2 (en) | 2004-10-29 | 2012-07-19 | Biocryst Pharmaceuticals, Inc. | Therapeutic furopyrimidines and thienopyrimidines |
| KR20070087624A (ko) * | 2004-12-23 | 2007-08-28 | 노파르티스 아게 | Ｈｃｖ 치료용 조성물 |
| JP2008532950A (ja) | 2005-03-08 | 2008-08-21 | バイオタ サイエンティフィック マネージメント ピーティーワイ リミテッド | 治療薬としての二環式ヌクレオシドおよび二環式ヌクレオチド |
| EP2537520A1 (en) * | 2005-03-29 | 2012-12-26 | Biocryst Pharmaceuticals, Inc. | Hepatics C therapies |
| CN101268092B (zh) * | 2005-09-22 | 2012-07-04 | 弗·哈夫曼-拉罗切有限公司 | 核苷的选择性o-酰基化 |
| US7879815B2 (en) * | 2006-02-14 | 2011-02-01 | Merck Sharp & Dohme Corp. | Nucleoside aryl phosphoramidates for the treatment of RNA-dependent RNA viral infection |
| EP2004634A1 (en) | 2006-04-04 | 2008-12-24 | F.Hoffmann-La Roche Ag | 3',5'-di-o-acylated nucleosides for hcv treatment |
| WO2010015637A1 (en) * | 2008-08-06 | 2010-02-11 | Novartis Ag | New antiviral modified nucleosides |
| CL2009002208A1 (es) | 2008-12-23 | 2010-10-29 | Gilead Pharmasset Llc | Un compuesto (2s)-2-((((2r,3r,4r,5r)-5-(2-amino-6-etoxi-9h-purin-9-il)-4-fluoro-3-hidroxi-4-metiltetrahidrofuran-2-il)metoxi)(hidroxi)fosforilamino)propanoico, inhibidores de la replicacion de arn viral; composicion farmaceutica; y su uso en el tratamiento de infeccion por hepatitis c, virus del nilo occidental, entre otras. |
| CL2009002207A1 (es) | 2008-12-23 | 2011-02-18 | Gilead Pharmasset Llc | Compuestos derivados de 3-hidroxi-5-(9h-purin-9-il)tetrahidrofuran-2-il, inhibidor de la replicacion de arn viral dependiente de arn; composicion farmaceutica; uso para el tratamiento de hepatitis c. |
| KR20110104074A (ko) | 2008-12-23 | 2011-09-21 | 파마셋 인코포레이티드 | 퓨린 뉴클레오시드의 합성 |
| WO2010081082A2 (en) * | 2009-01-09 | 2010-07-15 | University College Of Cardiff Consultants Limited | Phosphoramidate derivatives of guanosine nucleoside compounds for treatment of viral infections |
| MX2012011171A (es) | 2010-03-31 | 2013-02-01 | Gilead Pharmasset Llc | Fosforamidatos de nucleosido. |
| EP3865136A1 (en) | 2016-09-07 | 2021-08-18 | ATEA Pharmaceuticals, Inc. | 2'-substituted-n6-substituted purine nucleotides for corona virus treatment |
| EP3883947A4 (en) * | 2018-11-25 | 2022-08-24 | TNT Medical Corporation | ORAL ACTIVE PRODRUG OF GEMCITABIN |
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-
2003
- 2003-12-23 JP JP2004562599A patent/JP2006514038A/ja active Pending
- 2003-12-23 NZ NZ540913A patent/NZ540913A/en unknown
- 2003-12-23 US US10/746,395 patent/US20040181051A1/en not_active Abandoned
- 2003-12-23 AU AU2003300434A patent/AU2003300434A1/en not_active Abandoned
- 2003-12-23 MX MXPA05006865A patent/MXPA05006865A/es unknown
- 2003-12-23 CA CA002511616A patent/CA2511616A1/en not_active Abandoned
- 2003-12-23 EP EP03814400A patent/EP1575971A4/en not_active Withdrawn
- 2003-12-23 KR KR1020057011749A patent/KR20050110611A/ko not_active Withdrawn
- 2003-12-23 PL PL377608A patent/PL377608A1/pl not_active Application Discontinuation
- 2003-12-23 BR BR0316868-9A patent/BR0316868A/pt not_active IP Right Cessation
- 2003-12-23 WO PCT/US2003/041603 patent/WO2004058792A1/en not_active Ceased
- 2003-12-23 CN CNB2003801098204A patent/CN100335492C/zh not_active Expired - Fee Related
- 2003-12-23 RU RU2005123395/04A patent/RU2005123395A/ru not_active Application Discontinuation
-
2005
- 2005-06-21 ZA ZA200505040A patent/ZA200505040B/en unknown
- 2005-06-21 IL IL169314A patent/IL169314A0/en unknown
- 2005-07-20 NO NO20053557A patent/NO20053557L/no not_active Application Discontinuation
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