JP2016515545A5 - - Google Patents
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- JP2016515545A5 JP2016515545A5 JP2016504279A JP2016504279A JP2016515545A5 JP 2016515545 A5 JP2016515545 A5 JP 2016515545A5 JP 2016504279 A JP2016504279 A JP 2016504279A JP 2016504279 A JP2016504279 A JP 2016504279A JP 2016515545 A5 JP2016515545 A5 JP 2016515545A5
- Authority
- JP
- Japan
- Prior art keywords
- furan
- oxo
- pyrimidin
- tetrahydro
- phenoxy
- 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 2-dimethylamino-acetylamino Chemical group 0.000 claims description 119
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 110
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 30
- 229940017219 methyl propionate Drugs 0.000 claims description 23
- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 claims description 14
- CWLQUGTUXBXTLF-YFKPBYRVSA-N N-methylproline Chemical compound CN1CCC[C@H]1C(O)=O CWLQUGTUXBXTLF-YFKPBYRVSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- 235000019260 propionic acid Nutrition 0.000 description 14
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 12
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000711549 Hepacivirus C Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002777 nucleoside Substances 0.000 description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 229960002118 asunaprevir Drugs 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- FKRSSPOQAMALKA-CUPIEXAXSA-N daclatasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)=CN1 FKRSSPOQAMALKA-CUPIEXAXSA-N 0.000 description 1
- 229960005449 daclatasvir Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960002091 simeprevir Drugs 0.000 description 1
- JTZZSQYMACOLNN-VDWJNHBNSA-N simeprevir Chemical compound O=C([C@@]12C[C@H]1\C=C/CCCCN(C)C(=O)[C@H]1[C@H](C(N2)=O)C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1SC=C(N=1)C(C)C)C)OC)NS(=O)(=O)C1CC1 JTZZSQYMACOLNN-VDWJNHBNSA-N 0.000 description 1
- 229960002063 sofosbuvir Drugs 0.000 description 1
- TTZHDVOVKQGIBA-IQWMDFIBSA-N sofosbuvir Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IQWMDFIBSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2013112744 | 2013-03-22 | ||
| RU2013112744/04A RU2534613C2 (ru) | 2013-03-22 | 2013-03-22 | Алкил 2-{ [(2r,3s,5r)-5-(4-амино-2-оксо-2н-пиримидин-1-ил)- -гидрокси-тетрагидро-фуран-2-илметокси]-фенокси-фосфориламино} -пропионаты, нуклеозидные ингибиторы рнк-полимеразы hcv ns5b, способы их получения и применения |
| PCT/RU2014/000104 WO2014148949A1 (ru) | 2013-03-22 | 2014-02-19 | Алкил 2-{[(2r,3s,5r)-5-(4-амино-2-оксо-2н-пиримидин-1-ил)-3-гидрокси-тетрагидро-фуран-2-илметокси]-фенокси-фосфориламино}-пропионаты, нуклеозидные ингибиторы рнк-полимеразы hcv ns5b, способы их получения и применения |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016515545A JP2016515545A (ja) | 2016-05-30 |
| JP2016515545A5 true JP2016515545A5 (enExample) | 2016-07-07 |
Family
ID=51580483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016504279A Pending JP2016515545A (ja) | 2013-03-22 | 2014-02-19 | Ｈｃｖのｒｎａ−ポリメラーゼｎｓ５ｂのヌクレオシド阻害剤、２−｛［（２ｒ，３ｓ，５ｒ）−５−（４−アミノ−２−オキソ−２ｈ−ピリミジン−１−イル）−３−ヒドロキシ−テトラヒドロ−フラン−２−イルメトキシ］−フェノキシ−ホスホリルアミノ｝−プロピオン酸アルキル、その調製の方法及び使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20160031927A1 (enExample) |
| EP (1) | EP2977379A1 (enExample) |
| JP (1) | JP2016515545A (enExample) |
| KR (1) | KR20150132879A (enExample) |
| CN (1) | CN105263941A (enExample) |
| AU (1) | AU2014238517A1 (enExample) |
| CA (1) | CA2907455A1 (enExample) |
| EA (1) | EA025878B1 (enExample) |
| RU (1) | RU2534613C2 (enExample) |
| WO (1) | WO2014148949A1 (enExample) |
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| AR088441A1 (es) | 2011-09-12 | 2014-06-11 | Idenix Pharmaceuticals Inc | Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales |
| AP3913A (en) | 2012-05-22 | 2016-11-26 | Idenix Pharamaceuticals Inc | D-amino acid compounds for liver disease |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| SG11201502750UA (en) | 2012-10-08 | 2015-06-29 | Idenix Pharmaceuticals Inc | 2'-chloro nucleoside analogs for hcv infection |
| US9309275B2 (en) | 2013-03-04 | 2016-04-12 | Idenix Pharmaceuticals Llc | 3′-deoxy nucleosides for the treatment of HCV |
| EP2970357B1 (en) | 2013-03-13 | 2025-01-01 | Idenix Pharmaceuticals LLC | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| EP2981542B1 (en) | 2013-04-01 | 2021-09-15 | Idenix Pharmaceuticals LLC | 2',4'-fluoro nucleosides for the treatment of hcv |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
| WO2015017713A1 (en) | 2013-08-01 | 2015-02-05 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| WO2015061683A1 (en) * | 2013-10-25 | 2015-04-30 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate and d-alanine thiophosphoramidate pronucleotides of nucleoside compounds useful for the treatment of hcv |
| RU2553996C1 (ru) * | 2013-11-27 | 2015-06-20 | Андрей Александрович Иващенко | Замещенные (2r,3r,5r)-3-гидрокси-(5-пиримидин-1-ил)тетрагидрофуран-2-илметил арил фосфорамидаты |
| BR112016011949A8 (pt) | 2013-11-27 | 2020-04-28 | Idenix Pharmaceuticals Llc | composto, composição farmacêutica, e, uso dos mesmos |
| WO2015161137A1 (en) | 2014-04-16 | 2015-10-22 | Idenix Pharmaceuticals, Inc. | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| WO2016078160A1 (zh) * | 2014-11-17 | 2016-05-26 | 常州方圆制药有限公司 | 胞苷衍生物及其应用 |
| CN104546783A (zh) * | 2014-12-12 | 2015-04-29 | 安徽一灵药业有限公司 | 一种索非布韦薄膜包衣片制剂及其制备方法 |
| CN106132972B (zh) * | 2015-02-06 | 2018-08-31 | 银杏树药业(苏州)有限公司 | 用于治疗hcv感染的氨基磷酸酯 |
| CN106310269B (zh) * | 2015-07-03 | 2021-01-29 | 中国药科大学 | 一种具有抗丙型肝炎病毒作用的药物组合物 |
| CN108472308A (zh) * | 2015-10-20 | 2018-08-31 | 埃默里大学 | 应答指导型hcv疗法 |
| RU2606951C1 (ru) * | 2015-11-19 | 2017-01-10 | Закрытое акционерное общество "Р-Фарм" (ЗАО "Р-Фарм") | Дихлорацетаты замещенных N4-[2-(диметилфосфорил)фенил]-N2-(2-метокси-4-пиперидин-1-илфенил)-5-хлорпиримидин-2,4-диаминов в качестве модуляторов ALK и EGFR, предназначенных для лечения рака |
| US20190185507A1 (en) * | 2016-08-19 | 2019-06-20 | Sandoz Ag | Sofosbuvir Derivatives for the Treatment of Hepatitis C |
| US10266558B2 (en) * | 2016-10-07 | 2019-04-23 | Alexandre Vasilievich Ivachtchenko | Macroheterocyclic nucleoside derivatives and their analogues, production and use thereof |
| CN108732280B (zh) * | 2017-04-18 | 2022-07-08 | 广东东阳光药业有限公司 | 一种分离检测盐酸达卡他韦及其光学异构体的方法 |
| KR20190090301A (ko) * | 2018-01-24 | 2019-08-01 | 에스티팜 주식회사 | 신규한 뉴클레오사이드 또는 뉴클레오타이드 유도체 및 이들의 용도 |
| CN110045108B (zh) * | 2019-05-28 | 2021-10-29 | 江南大学 | 一种基于辣椒碱指标的地沟油酶联免疫检测试剂盒及其检测方法 |
| KR102145025B1 (ko) * | 2020-02-20 | 2020-08-14 | 에스티팜 주식회사 | 신규한 뉴클레오사이드 또는 뉴클레오타이드 유도체 및 이들의 용도 |
| CN111233955B (zh) * | 2020-02-28 | 2022-06-10 | 南京缘聚医药科技有限公司 | 一类噻唑酮甲酰胞嘧啶衍生物及其药物用途 |
| CN116751241B (zh) * | 2022-08-12 | 2026-05-01 | 杭州爱科瑞思生物医药有限公司 | 2’-去氧-2’,2’-二氟胞苷ProTide的制备及其应用 |
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| WO2003007945A1 (en) | 2001-07-20 | 2003-01-30 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| US6899700B2 (en) | 2001-08-29 | 2005-05-31 | Kimberly-Clark Worldwide, Inc. | Therapeutic agent delivery tampon |
| EP1438054A4 (en) | 2001-09-28 | 2006-07-26 | Idenix Cayman Ltd | METHODS AND COMPOSITIONS FOR TREATING FLAVIVIRUS AND PESTIVIRUS USING MODIFIED NUCLEOSIDE AT 4 'POSITION |
| AU2002330154A1 (en) | 2001-09-28 | 2003-04-07 | Centre National De La Recherche Scientifique | Methods and compositions for treating hepatitis c virus using 4'-modified nucleosides |
| AU2002359320A1 (en) | 2001-10-29 | 2003-05-12 | Smithkline Beecham Corporation | Novel anit-infectives |
| WO2003099801A1 (en) | 2002-05-24 | 2003-12-04 | Smithkline Beecham Corporation | Novel anti-infectives |
| CA2488842A1 (en) | 2002-06-17 | 2003-12-24 | Merck & Co., Inc. | Carbocyclic nucleoside analogs as rna-antivirals |
| PT1523489E (pt) | 2002-06-28 | 2014-06-24 | Centre Nat Rech Scient | Profármacos de nucleósido modificado em 2' e 3' para tratamento de infecções por flaviridae |
| EP1525209B1 (en) | 2002-06-28 | 2017-11-15 | Idenix Pharmaceuticals LLC | 1'-, 2'- and 3' -modified nucleoside derivatives for treating flaviviridae infections |
| US7323449B2 (en) | 2002-07-24 | 2008-01-29 | Merck & Co., Inc. | Thionucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| WO2004041818A1 (en) | 2002-11-01 | 2004-05-21 | Abbott Laboratories | Anti-infective agents |
| RU2005118421A (ru) | 2002-11-15 | 2006-01-20 | Айденикс (Кайман) Лимитед (Ky) | 2'-разветвленные нуклеозиды и мутация flaviviridae |
| WO2004052312A2 (en) | 2002-12-11 | 2004-06-24 | Smithkline Beecham Corporation | Anti-infectives |
| AU2003300957A1 (en) | 2002-12-11 | 2004-06-30 | Smithkline Beecham Corporation | Anti-infectives |
| WO2004087577A1 (ja) | 2003-03-31 | 2004-10-14 | Toto Ltd. | 表面改質二酸化チタン微粒子とその分散液、およびその製造方法 |
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| US7964580B2 (en) * | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US9156872B2 (en) * | 2011-04-13 | 2015-10-13 | Merck Sharp & Dohme Corp. | 2′-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| CN102775458B (zh) * | 2011-05-09 | 2015-11-25 | 中国人民解放军军事医学科学院毒物药物研究所 | β-D-(2’R)-2’-脱氧—2’-氟-2’-C-甲基胞苷衍生物的制备及用途 |
-
2013
- 2013-03-22 RU RU2013112744/04A patent/RU2534613C2/ru not_active IP Right Cessation
-
2014
- 2014-02-19 KR KR1020157030455A patent/KR20150132879A/ko not_active Withdrawn
- 2014-02-19 US US14/772,818 patent/US20160031927A1/en not_active Abandoned
- 2014-02-19 AU AU2014238517A patent/AU2014238517A1/en not_active Abandoned
- 2014-02-19 EP EP14770263.3A patent/EP2977379A1/en not_active Withdrawn
- 2014-02-19 JP JP2016504279A patent/JP2016515545A/ja active Pending
- 2014-02-19 WO PCT/RU2014/000104 patent/WO2014148949A1/ru not_active Ceased
- 2014-02-19 CN CN201480024794.3A patent/CN105263941A/zh active Pending
- 2014-02-19 EA EA201401063A patent/EA025878B1/ru not_active IP Right Cessation
- 2014-02-19 CA CA2907455A patent/CA2907455A1/en not_active Abandoned
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