SG172352A1 - Anti-viral compounds - Google Patents
Anti-viral compounds Download PDFInfo
- Publication number
- SG172352A1 SG172352A1 SG2011046240A SG2011046240A SG172352A1 SG 172352 A1 SG172352 A1 SG 172352A1 SG 2011046240 A SG2011046240 A SG 2011046240A SG 2011046240 A SG2011046240 A SG 2011046240A SG 172352 A1 SG172352 A1 SG 172352A1
- Authority
- SG
- Singapore
- Prior art keywords
- optionally substituted
- compound
- occurrence
- halogen
- hydrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 169
- 230000000840 anti-viral effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 35
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- 230000008569 process Effects 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 146
- -1 hydroxy, mercapto, amino, carboxy Chemical group 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
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- 239000001257 hydrogen Substances 0.000 claims description 83
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- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
- 229910019142 PO4 Inorganic materials 0.000 claims description 70
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 70
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 69
- 239000010452 phosphate Substances 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 67
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical class C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14026208P | 2008-12-23 | 2008-12-23 | |
| PCT/US2009/069177 WO2010075376A2 (en) | 2008-12-23 | 2009-12-22 | Anti-viral compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG172352A1 true SG172352A1 (en) | 2011-07-28 |
Family
ID=42169497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2011046240A SG172352A1 (en) | 2008-12-23 | 2009-12-22 | Anti-viral compounds |
Country Status (11)
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|---|---|
| US (2) | US8541424B2 (https=) |
| EP (1) | EP2367824B1 (https=) |
| JP (1) | JP2012513409A (https=) |
| CN (1) | CN102264737A (https=) |
| CA (1) | CA2740193A1 (https=) |
| ES (1) | ES2567047T3 (https=) |
| MX (1) | MX2011006332A (https=) |
| RU (1) | RU2505540C2 (https=) |
| SG (1) | SG172352A1 (https=) |
| WO (1) | WO2010075376A2 (https=) |
| ZA (1) | ZA201105355B (https=) |
Families Citing this family (209)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2743134A1 (en) | 2008-11-10 | 2010-05-14 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| ES2921576T3 (es) | 2008-12-19 | 2022-08-29 | Vertex Pharma | Compuestos útiles como inhibidores de la quinasa ATR |
| SG172352A1 (en) | 2008-12-23 | 2011-07-28 | Abbott Lab | Anti-viral compounds |
| US8546405B2 (en) | 2008-12-23 | 2013-10-01 | Abbott Laboratories | Anti-viral compounds |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9278922B2 (en) * | 2009-04-15 | 2016-03-08 | Abbvie Inc. | Anti-viral compounds |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| EA020031B1 (ru) | 2009-06-11 | 2014-08-29 | Эббви Бахамаз Лтд. | Противовирусные соединения |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110281910A1 (en) | 2009-11-12 | 2011-11-17 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20110152246A1 (en) * | 2009-12-18 | 2011-06-23 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US9062008B2 (en) | 2010-05-12 | 2015-06-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| EP2568984A1 (en) | 2010-05-12 | 2013-03-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CA2798760A1 (en) | 2010-05-12 | 2011-11-17 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as inhibitors of atr kinase |
| NZ603477A (en) | 2010-05-12 | 2014-09-26 | Vertex Pharma | Compounds useful as inhibitors of atr kinase |
| US8962631B2 (en) | 2010-05-12 | 2015-02-24 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| MX2013000103A (es) | 2010-06-23 | 2013-06-13 | Vertex Pharma | Derivados de pirrolo-pirazina utiles como inhibidores de cinasa art. |
| PT3012258T (pt) | 2010-06-24 | 2018-12-14 | Gilead Sciences Inc | Composição farmacêutica compreendendo um derivado de pirazolo[1,5-a]pirimidina como agente antiviral |
| CN103619171B (zh) | 2010-11-03 | 2015-11-25 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| MX2013011450A (es) | 2011-04-05 | 2014-02-03 | Vertex Pharma | Compuestos de aminopirazina utiles como inhibidores de la cinasa ataxia telangiectasia mutada y rad3 relacionados (atr). |
| US9546160B2 (en) | 2011-05-12 | 2017-01-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2835835C (en) | 2011-05-13 | 2019-04-02 | Array Biopharma Inc. | Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as trka kinase inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US9309250B2 (en) | 2011-06-22 | 2016-04-12 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-b]pyrazines as ATR kinase inhibitors |
| US8822469B2 (en) | 2011-06-22 | 2014-09-02 | Vertex Pharmaceuticals Incorporated | Pyrrolo[2,3-B]pyrazines useful as inhibitors of ATR kinase |
| EP2723747A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| CN106496173A (zh) | 2011-09-30 | 2017-03-15 | 沃泰克斯药物股份有限公司 | 用于制备可用作atr激酶抑制剂的化合物的方法 |
| CN108685922A (zh) | 2011-09-30 | 2018-10-23 | 沃泰克斯药物股份有限公司 | 用atr抑制剂治疗胰腺癌和非小细胞肺癌 |
| US8765751B2 (en) | 2011-09-30 | 2014-07-01 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| WO2013049722A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2013049720A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| EP2578582A1 (en) | 2011-10-03 | 2013-04-10 | Respivert Limited | 1-Pyrazolyl-3-(4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 MAP kinase inhibitors |
| KR101995274B1 (ko) | 2011-10-03 | 2019-07-02 | 레스피버트 리미티드 | P38 map 키나제 저해제인 1-피라졸릴-3-(4-((2-아닐리노피리미딘-4-일)옥시)나프탈렌-1-일) 우레아 |
| AP2014007606A0 (en) | 2011-10-07 | 2014-05-31 | Takeda Pharmaceutical | 1-Arylcarbonyl-4-oxy-piperidine compounds useful for the treatment of neurodegenerative diseases |
| JP6027128B2 (ja) | 2011-10-26 | 2016-11-16 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除組成物およびそれに関連した方法 |
| US8846917B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8846918B2 (en) | 2011-11-09 | 2014-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8841450B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US8841337B2 (en) | 2011-11-09 | 2014-09-23 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| JP2015502925A (ja) | 2011-11-09 | 2015-01-29 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼの阻害剤として有用なピラジン化合物 |
| JP6122868B2 (ja) | 2011-12-22 | 2017-04-26 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CN108478577A (zh) | 2012-04-05 | 2018-09-04 | 沃泰克斯药物股份有限公司 | 可用作atr激酶抑制剂的化合物及其组合疗法 |
| AU2013249280B2 (en) | 2012-04-17 | 2017-10-12 | Gilead Sciences, Inc. | Compounds and methods for antiviral treatment |
| SG11201406759YA (en) | 2012-04-26 | 2014-11-27 | Bristol Myers Squibb Co | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| EP2855489B1 (en) | 2012-04-26 | 2017-01-04 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| SI2841437T1 (sl) | 2012-04-26 | 2017-09-29 | Bristol-Myers Squibb Company | Derivati imidazotiadiazola in imidazopirazina kot proteazno aktivirani receptor 4 (PAR4) inhibitorji za zdravljenje agregacije trombocitov |
| US9282739B2 (en) | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| CN104822266B (zh) | 2012-04-27 | 2017-12-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| SG11201407919WA (en) | 2012-05-31 | 2014-12-30 | Phenex Pharmaceuticals Ag | Carboxamide or sulfonamide substituted thiazoles and related derivatives as modulators for the orphan nuclear receptor ror[gamma] |
| JO3215B1 (ar) | 2012-08-09 | 2018-03-08 | Phenex Pharmaceuticals Ag | حلقات غير متجانسة بها 5 ذرات تحتوي على النيتروجين بها استبدال بكربوكساميد أو سلفوناميد كمعدلات لمستقبل نووي غير محمي RORy |
| GB201214750D0 (en) | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| GB201215357D0 (en) | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
| DK2904406T3 (en) | 2012-10-04 | 2018-06-18 | Vertex Pharma | METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE |
| EP2909202A1 (en) | 2012-10-16 | 2015-08-26 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| RS55593B1 (sr) | 2012-11-13 | 2017-06-30 | Array Biopharma Inc | Jedinjenja biciklične uree, tiouree, guanidina i cijanoguanidina korisna za lečenje bola |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078417A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| MX374242B (es) | 2012-11-13 | 2025-03-05 | Array Biopharma Inc | Compuestos de n-pirrolidinil, n' -pirazolil-urea, tiourea, guanidina y cianoguanidina como inhibidores de trka cinasa. |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078372A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078378A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| SI2941432T1 (en) | 2012-12-07 | 2018-07-31 | Vertex Pharmaceuticals Incorporated | 2-AMINO-6-FLUORO-N- (5-FLUORO-4- (4- (4- (OXETHAN-3-YL) PIPERAZIN-1-CARBONYL) PIPERIDIN-1-YLIPRIDIN-3-YL) 1,5 ALFA) PYRIMIDINE-3-CARBOXAMIDE AS ATR KINAZE INHIBITOR |
| CA2897279C (en) | 2013-01-23 | 2020-12-29 | Astrazeneca Ab | Aminopyrazine derivatives and pharmaceutical compositions thereof for use in the treatment of cancer |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| WO2014140582A1 (en) | 2013-03-14 | 2014-09-18 | Respivert Limited | Kinase inhibitors |
| WO2014143240A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| AR096788A1 (es) | 2013-07-02 | 2016-02-03 | Bristol Myers Squibb Co | Compuestos tricíclicos de carboxamida como inhibidores potentes de rock |
| US9717712B2 (en) | 2013-07-02 | 2017-08-01 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus |
| WO2015002926A1 (en) | 2013-07-02 | 2015-01-08 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US9775831B2 (en) | 2013-07-17 | 2017-10-03 | Bristol-Myers Squibb Company | Combinations comprising biphenyl derivatives for use in the treatment of HCV |
| LT3043803T (lt) | 2013-09-11 | 2022-08-10 | Emory University | Nukleotidų ir nukleozidų kompozicijos ir jų panaudojimas |
| SG10202103278TA (en) | 2013-10-14 | 2021-04-29 | Eisai R&D Man Co Ltd | Selectively substituted quinoline compounds |
| ES2670550T3 (es) | 2013-10-14 | 2018-05-30 | Eisai R&D Management Co., Ltd. | Derivados de quinolina selectivamente sustituidos |
| CN105636440A (zh) | 2013-10-17 | 2016-06-01 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| WO2015058028A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058022A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| US9085564B2 (en) | 2013-10-17 | 2015-07-21 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| US9174962B2 (en) | 2013-10-17 | 2015-11-03 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| TW201519779A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（十二） |
| MX2016005304A (es) | 2013-10-22 | 2017-03-01 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
| JP2016536307A (ja) | 2013-10-22 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物および関連する方法 |
| RU2016119560A (ru) | 2013-10-22 | 2017-11-28 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Синергетические пестицидные композиции и относящиеся к ним способы |
| TW201519786A (zh) | 2013-10-22 | 2015-06-01 | 陶氏農業科學公司 | 殺蟲組成物及相關方法（一） |
| MX385974B (es) | 2013-10-22 | 2025-03-18 | Corteva Agriscience Llc | Composiciones pesticidas y métodos relacionados. |
| TW201517797A (zh) | 2013-10-22 | 2015-05-16 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（十一） |
| KR20160074633A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 상승작용적 살충 조성물 및 관련 방법 |
| MX2016005317A (es) | 2013-10-22 | 2016-08-12 | Dow Agrosciences Llc | Composiciones pesticidas y metodos relacionados. |
| TW201519771A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（三） |
| KR20160074640A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 관련 방법 |
| US9788545B2 (en) | 2013-10-22 | 2017-10-17 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| CN105828608A (zh) | 2013-10-22 | 2016-08-03 | 美国陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| AU2014340437B2 (en) | 2013-10-22 | 2017-09-07 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| JP2016538266A (ja) | 2013-10-22 | 2016-12-08 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
| KR20160074635A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 상승작용적 살충 조성물 및 관련 방법 |
| US9282740B2 (en) | 2013-10-22 | 2016-03-15 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| PT3077397T (pt) | 2013-12-06 | 2020-01-22 | Vertex Pharma | Composto de 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inibidor da atr quinase, a sua preparação, diferentes formas sólidas e derivados radiomarcados do mesmo |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| MA40434B1 (fr) | 2014-05-15 | 2019-09-30 | Array Biopharma Inc | 1-((3s,4r)-4-(3-fluorophényl)-1-(2-méthoxyéthyl)pyrrolidin-3-yl)-3-(4-méthyl-3-(2-méthylpyrimidin-5-yl)-1-phényl-1h-pyrazol-5-yl)urée comme inhibiteur de la kinase trka |
| CN106414429B (zh) | 2014-06-03 | 2020-01-03 | 爱杜西亚药品有限公司 | 吡唑化合物及其作为t型钙通道阻断剂的用途 |
| MX373102B (es) | 2014-06-05 | 2020-04-17 | Vertex Pharma | Derivados radiomarcados de un compuesto de 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-carboxamida útil como inhibidor de ataxia telangiectasia mutada y rad3 relacionado (atr) cinasa, preparación de tal compuesto y diferentes formas sólidas del mismo. |
| RU2016149812A (ru) | 2014-06-06 | 2018-07-17 | Флексус Байосайенсиз, Инк. | Иммунорегулирующие средства |
| SG11201610500WA (en) | 2014-06-17 | 2017-01-27 | Vertex Pharma | Method for treating cancer using a combination of chk1 and atr inhibitors |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017000565A2 (pt) | 2014-07-31 | 2017-11-07 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| EP3180335B1 (en) | 2014-08-11 | 2021-05-05 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| EP3183238A4 (en) | 2014-08-19 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017004613A2 (pt) | 2014-09-12 | 2017-12-05 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| US10246426B2 (en) | 2014-09-15 | 2019-04-02 | Idorsia Pharmaceuticals Ltd | Triazole compounds as T-type calcium channel blockers |
| DK3209655T3 (da) | 2014-10-24 | 2020-09-28 | Landos Biopharma Inc | Lanthioninsyntease C-lignende 2-baserede Therapeutica |
| BR112017008809A2 (pt) | 2014-11-05 | 2017-12-19 | Flexus Biosciences Inc | agentes imunorreguladores |
| UY36391A (es) | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido1), sus métodos de síntesis y composiciones farmacèuticas que las contienen |
| UY36390A (es) | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen |
| US10351532B2 (en) | 2014-12-29 | 2019-07-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Small molecule inhibitors of lactate dehydrogenase and methods of use thereof |
| CA2970819A1 (en) | 2014-12-31 | 2016-07-07 | Angion Biomedica Corp. | Methods and agents for treating disease |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| SI3302448T1 (sl) | 2015-06-04 | 2024-03-29 | Aurigene Oncology Limited | Substituirani heterociklični derivati kot inhibitorji cdk |
| WO2017007756A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc | Hetero-halo inhibitors of histone deacetylase |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| WO2017023631A1 (en) | 2015-08-06 | 2017-02-09 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA44075A (fr) | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EA201892448A1 (ru) | 2016-04-28 | 2019-06-28 | Эмори Юниверсити | Алкинсодержащие нуклеотидные и нуклеозидные терапевтические композиции и связанные с ними способы применения |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CN106279120A (zh) * | 2016-07-15 | 2017-01-04 | 谢阳 | 一种n‑芳基氨基甲酰基脯氨酸类化合物及其药物组合物和应用 |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| JOP20190080A1 (ar) | 2016-10-14 | 2019-04-11 | Bayer Pharma AG | مركبات مشتقة من 6-(1h-بيرازول-1-يل) بيريميدين-4- أمين مستبدل واستخداماتها |
| MX388586B (es) | 2016-12-16 | 2025-03-20 | Idorsia Pharmaceuticals Ltd | Combinacion farmaceutica que comprende un bloqueador del canal de calcio de tipo t. |
| JP7101678B2 (ja) | 2016-12-22 | 2022-07-15 | インサイト・コーポレイション | 免疫調節剤としての複素環式化合物 |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| LT3558990T (lt) | 2016-12-22 | 2022-12-27 | Incyte Corporation | Tetrahidroimidazo[4,5-c]piridino dariniai kaip pd-l1 internalizavimo induktoriai |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018122746A1 (en) | 2016-12-28 | 2018-07-05 | Minoryx Therapeutics S.L. | Isoquinoline compounds, methods for their preparation, and therapeutic uses thereof in conditions associated with the alteration of the activity of beta galactosidase |
| WO2018125815A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
| HUE057849T2 (hu) | 2017-01-11 | 2022-06-28 | Alkermes Inc | Hiszton deacetiláz biciklusos gátlói |
| CA3050348A1 (en) | 2017-02-06 | 2018-08-09 | Idorsia Pharmaceuticals Ltd | A novel process for the synthesis of 1-aryl-1-trifluoromethylcyclopropanes |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| WO2019028440A1 (en) | 2017-08-04 | 2019-02-07 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICING |
| LT3664802T (lt) | 2017-08-07 | 2022-06-27 | Alkermes, Inc. | Bicikliniai histonų deacetilazės inhibitoriai |
| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| CR20200347A (es) | 2018-02-13 | 2020-09-23 | Gilead Sciences Inc | Inhibidores pd-1/pd-l1 |
| TWI877770B (zh) | 2018-02-27 | 2025-03-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之咪唑并嘧啶及三唑并嘧啶 |
| SMT202500157T1 (it) | 2018-03-30 | 2025-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| TWI712412B (zh) | 2018-04-19 | 2020-12-11 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| EP3810610A1 (en) | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| WO2020010197A1 (en) | 2018-07-05 | 2020-01-09 | Incyte Corporation | Fused pyrazine derivatives as a2a / a2b inhibitors |
| SG11202012425QA (en) | 2018-07-13 | 2021-01-28 | Gilead Sciences Inc | Pd-1/pd-l1 inhibitors |
| US12180205B2 (en) | 2018-09-19 | 2024-12-31 | Biogen Ma Inc. | O-glycoprotein-2-acetamido-2-deoxy-3-d-glucopyranosidase inhibitors |
| JP7530889B2 (ja) | 2018-10-05 | 2024-08-08 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ３０（ｕｓｐ３０）阻害剤として作用する縮合ピロリン |
| WO2020086556A1 (en) | 2018-10-24 | 2020-04-30 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| WO2020163248A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| EP3920915A4 (en) | 2019-02-05 | 2022-10-05 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICE |
| CN114126613A (zh) | 2019-02-05 | 2022-03-01 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| CN113661162A (zh) | 2019-02-06 | 2021-11-16 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| WO2020163544A1 (en) | 2019-02-06 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Ｐｄ－１／ｐｄ－ｌ１阻害剤の塩 |
| PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
| CA3160131A1 (en) | 2019-11-11 | 2021-05-20 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| KR20230026522A (ko) | 2019-12-20 | 2023-02-24 | 란도스 바이오파마, 인크. | 란티오닌 c-유사 단백질 2 리간드, 이로 제조된 세포, 및 이를 사용하는 치료법 |
| CN115210229A (zh) | 2020-01-03 | 2022-10-18 | 博格有限责任公司 | 多环酰胺作为治疗癌症的ube2k调节剂 |
| US12234578B2 (en) | 2020-01-29 | 2025-02-25 | Wisconsin Alumni Research Foundation | Tannin composite fibers |
| EP4118081A1 (en) | 2020-03-27 | 2023-01-18 | Landos Biopharma, Inc. | Plxdc2 ligands |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
| TW202309022A (zh) | 2021-04-13 | 2023-03-01 | 美商努法倫特公司 | 用於治療具egfr突變之癌症之胺基取代雜環 |
| CA3226162A1 (en) | 2021-07-09 | 2023-01-12 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate ikzf2 |
| AU2022328634A1 (en) | 2021-08-18 | 2024-02-22 | Chemocentryx, Inc. | Aryl sulfonyl compounds as ccr6 inhibitors |
| WO2023023532A2 (en) | 2021-08-18 | 2023-02-23 | Chemocentryx, Inc. | Aryl sulfonyl (hydroxy) piperidines as ccr6 inhibitors |
| AR127064A1 (es) | 2021-09-15 | 2023-12-13 | Hua Medicine Shanghai Ltd | Prodroga de derivados de pirrolidona como activador de glucoquinasa |
| CN117327000A (zh) * | 2023-10-07 | 2024-01-02 | 海南因瑞生物医药科技有限公司 | 一种联苯四氢吡咯化合物及其制备方法和用途 |
Family Cites Families (182)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE75755C (de) | 1894-06-14 | DAHL & COMP, in Barmen | Verfahren zur Darstellung von aromatisch substituirten Amidodinaphtylmethanen. | |
| JPH09504266A (ja) * | 1993-05-24 | 1997-04-28 | スミスクライン・ビーチャム・コーポレイション | 血液調節ペプチド |
| US6037157A (en) * | 1995-06-29 | 2000-03-14 | Abbott Laboratories | Method for improving pharmacokinetics |
| US5935982A (en) * | 1997-02-28 | 1999-08-10 | The University Of North Carolina At Chapel Hill | Methods of treating retroviral infection and compounds useful therefor |
| US6235493B1 (en) * | 1997-08-06 | 2001-05-22 | The Regents Of The University Of California | Amino acid substituted-cresyl violet, synthetic fluorogenic substrates for the analysis of agents in individual in vivo cells or tissue |
| BR9815899A (pt) | 1998-05-20 | 2001-02-20 | Lilly Co Eli | Compostos antivirais |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6369091B1 (en) * | 1998-05-22 | 2002-04-09 | Avanir Pharmaceuticals | Benzimidazole analogs as down-regulators of IgE |
| BR9910642A (pt) | 1998-05-22 | 2001-10-09 | Avanir Pharmaceuticals | Análogos de benzimidazol como reguladores descendentes de ige |
| US6387885B1 (en) | 1998-08-26 | 2002-05-14 | Abbott Laboratories | 3′,3′-N-bis-desmethyl-3′-N-cycloalkyl erythromycin derivatives as LHRH antagonists |
| CO5271715A1 (es) * | 1999-12-21 | 2003-04-30 | Sugen Inc | 7-aza-indolin-2-onas sustituidas en 4 y su uso como inhibidores de proteiuna quinasa |
| EP1309591B1 (en) | 2000-08-14 | 2007-01-24 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| ATE301653T1 (de) | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| JP4169246B2 (ja) | 2001-03-16 | 2008-10-22 | 富士フイルム株式会社 | ヘテロ環化合物及びそれを用いた発光素子 |
| US6881741B2 (en) * | 2001-06-11 | 2005-04-19 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| EP2335700A1 (en) * | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| RU2286343C2 (ru) | 2001-08-10 | 2006-10-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы |
| MY151199A (en) | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| JP3925265B2 (ja) | 2002-03-25 | 2007-06-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
| TW200304820A (en) | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| EP1515724B1 (en) * | 2002-06-14 | 2009-10-21 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2005531638A (ja) * | 2002-07-01 | 2005-10-20 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | Ｈｃｖｎｓ５ｂポリメラーゼ阻害剤 |
| US7361665B2 (en) | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| AU2003264038A1 (en) * | 2002-08-12 | 2004-02-25 | Bristol-Myers Squibb Company | Combination pharmaceutical agents as inhibitors of hcv replication |
| GB0229518D0 (en) * | 2002-12-19 | 2003-01-22 | Astrazeneca Ab | Chemical compounds |
| TW200508224A (en) * | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| RS20060018A (sr) * | 2003-07-14 | 2007-12-31 | Arena Pharmaceuticals Inc., | Derivati spojenih arila i heteroarila kao modulatori metabolizma u profilaksi i lečenju sa njima povezanih stanja |
| JP2007501189A (ja) | 2003-08-01 | 2007-01-25 | ジェネラブス テクノロジーズ，インコーポレイテッド | フラビウイルス科に対する二環式イミダゾール誘導体 |
| US8084457B2 (en) * | 2003-09-15 | 2011-12-27 | Lead Discovery Center Gmbh | Pharmaceutically active 4,6-disubstituted aminopyrimidine derivatives as modulators of protein kinases |
| JP2007509950A (ja) * | 2003-10-27 | 2007-04-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｈｃｖ処置の組合せ剤 |
| CA2545422C (en) * | 2003-12-03 | 2015-06-02 | Cytopia Research Pty Ltd | Tubulin inhibitors |
| BRPI0401908A (pt) | 2004-06-04 | 2006-01-17 | Univ Rio De Janeiro | Compostos inibidores de serina protease, processo de obtenção e uso para tratamento de flaviviroses |
| WO2006009876A2 (en) | 2004-06-17 | 2006-01-26 | Cengent Therapeutics, Inc. | Trisubstituted nitrogen modulators of tyrosine phosphatases |
| US7772271B2 (en) * | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| BRPI0513811A (pt) | 2004-07-27 | 2008-07-15 | Gilead Sciences Inc | imidazo [4,5-d] pirimidinas, seus usos e processos de preparação |
| MX2007001661A (es) * | 2004-08-13 | 2007-04-23 | Praecis Pharm Inc | Metodos y composiciones para modular la actividad del receptor de esfingosina -1 fosfato (sip). |
| CN101018761A (zh) * | 2004-08-13 | 2007-08-15 | 普雷西斯药品公司 | 调节鞘氨醇－1－磷酸（s1p）受体活性的方法和组合物 |
| GB0501964D0 (en) | 2005-01-31 | 2005-03-09 | Arrow Therapeutics Ltd | Chemical compounds |
| MX2007010067A (es) * | 2005-02-16 | 2007-12-07 | Schering Corp | Compuestos heterociclicos novedosos sustituidos con piridina o fenilo con actividad antagonista de cxcr3. |
| WO2006093867A1 (en) * | 2005-02-28 | 2006-09-08 | The Rockefeller University | Structure of the hepatitits c virus ns5a protein |
| WO2006113769A1 (en) * | 2005-04-15 | 2006-10-26 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US8143288B2 (en) | 2005-06-06 | 2012-03-27 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| US7541359B2 (en) * | 2005-06-30 | 2009-06-02 | Janssen Pharmaceutica N.V. | N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase |
| JP2009501217A (ja) * | 2005-07-15 | 2009-01-15 | アストラゼネカ アクチボラグ | 治療薬 |
| RU2008128453A (ru) * | 2005-12-12 | 2010-01-20 | Дженелабс Текнолоджис, Инк. (Us) | Соединение n-(5-членных арил)-амидов, фармацевтическая композиция с противовирусной активностью на их основе, способ лечения или профилактики вирусной инфекции с их помощью и способ их получения |
| CA2633541A1 (en) * | 2005-12-12 | 2007-06-21 | Genelabs Technologies, Inc. | N-(6-membered aromatic ring)-amido anti-viral compounds |
| RU2441010C2 (ru) * | 2005-12-21 | 2012-01-27 | Эбботт Лэборетриз | Противовирусные соединения |
| WO2007081517A2 (en) * | 2005-12-21 | 2007-07-19 | Abbott Laboratories | Anti-viral compounds |
| EP1979349B1 (en) * | 2005-12-21 | 2010-07-28 | Abbott Laboratories | Anti-viral compounds |
| CA2634699A1 (en) * | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of lta4h for treating inflammation |
| US7910595B2 (en) * | 2005-12-21 | 2011-03-22 | Abbott Laboratories | Anti-viral compounds |
| WO2007082554A1 (en) | 2006-01-23 | 2007-07-26 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Modulators of hcv replication |
| CN101535300B (zh) | 2006-05-16 | 2014-05-28 | 埃格拉医疗公司 | Iap bir域结合化合物 |
| EA015127B1 (ru) * | 2006-06-08 | 2011-06-30 | Эли Лилли Энд Компани | Антагонисты мсн-рецепторов |
| AR061603A1 (es) | 2006-06-16 | 2008-09-10 | Syngenta Ltd | Derivados de etenilcarboxamidas microbicidas |
| US20100143499A1 (en) * | 2006-07-24 | 2010-06-10 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
| US20100056495A1 (en) | 2006-07-24 | 2010-03-04 | Tetralogic Pharmaceuticals Corporation | Dimeric iap inhibitors |
| US7759495B2 (en) | 2006-08-11 | 2010-07-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7745636B2 (en) * | 2006-08-11 | 2010-06-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) * | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20100158862A1 (en) * | 2006-08-11 | 2010-06-24 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| PE20080906A1 (es) * | 2006-08-17 | 2008-07-05 | Kemia Inc | Derivados heteroarilo como inhibidores de citocina |
| JP2010510245A (ja) | 2006-11-21 | 2010-04-02 | スミスクライン ビーチャム コーポレーション | 抗ウイルス化合物 |
| EP2099778A2 (en) | 2006-11-21 | 2009-09-16 | Smithkline Beecham Corporation | Amido anti-viral compounds |
| WO2008074450A2 (en) | 2006-12-20 | 2008-06-26 | Nicox S.A. | Non-peptidic renin inhibitors nitroderivatives |
| US8236950B2 (en) | 2006-12-20 | 2012-08-07 | Abbott Laboratories | Anti-viral compounds |
| JP5454943B2 (ja) * | 2007-04-12 | 2014-03-26 | ジョイアント ファーマスーティカルズ、インク． | 抗癌剤として有用なｓｍａｃ模倣二量体及び三量体 |
| US7741347B2 (en) | 2007-05-17 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| TW200901969A (en) * | 2007-06-06 | 2009-01-16 | Smithkline Beecham Corp | Chemical compounds |
| US20090004140A1 (en) | 2007-06-26 | 2009-01-01 | Yao-Ling Qiu | 4-substituted pyrrolidine as anti-infectives |
| WO2009020534A2 (en) | 2007-08-03 | 2009-02-12 | Schering Corporation | Method of treating cxcr3 mediated diseases using heterocyclic substituted piperazines |
| US8629171B2 (en) * | 2007-08-08 | 2014-01-14 | Bristol-Myers Squibb Company | Crystalline form of methyl ((1S)-1-((25)-2-(5-(4'-(2-((25)-1((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt |
| US7728027B2 (en) * | 2007-08-08 | 2010-06-01 | Bristol-Myers Squibb Company | Process for synthesizing compounds useful for treating hepatitis C |
| US20090047247A1 (en) | 2007-08-13 | 2009-02-19 | Yao-Ling Qiu | Pyrrolidine Derivatives |
| GB0801199D0 (en) | 2008-01-23 | 2008-02-27 | Acal Energy Ltd | Fuel cells |
| US9029411B2 (en) | 2008-01-25 | 2015-05-12 | Millennium Pharmaceuticals, Inc. | Thiophenes and uses thereof |
| DK2250163T3 (da) | 2008-02-12 | 2012-07-16 | Bristol Myers Squibb Co | Hepatitis C-virusinhibitorer |
| KR20100123717A (ko) | 2008-02-12 | 2010-11-24 | 브리스톨-마이어스 스큅 컴퍼니 | Ｃ형 간염 바이러스 억제제로서의 헤테로시클릭 유도체 |
| WO2009102325A1 (en) | 2008-02-13 | 2009-08-20 | Bristol-Myers Squibb Company | Imidazolyl biphenyl imidazoles as hepatitis c virus inhibitors |
| US7704992B2 (en) | 2008-02-13 | 2010-04-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8034966B1 (en) * | 2008-02-20 | 2011-10-11 | Cell Viable Corporation | Phenoxyisobutyric acid compounds and methods for synthesis |
| WO2009136290A1 (en) | 2008-05-05 | 2009-11-12 | Aegera Therapeutics, Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| WO2009143361A1 (en) | 2008-05-22 | 2009-11-26 | Smithkline Beecham Corporation | Amido anti-viral compounds |
| AU2009261919A1 (en) | 2008-06-27 | 2009-12-30 | Pharmascience Inc. | Bridged secondary amines and use thereof as IAP BIR domain binding compounds |
| US20100068197A1 (en) | 2008-07-11 | 2010-03-18 | Myriad Pharmaceuticals, Inc. | Pharmaceutical compounds as inhibitors of cell proliferation and the use thereof |
| US7906655B2 (en) | 2008-08-07 | 2011-03-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20120009141A1 (en) | 2008-08-07 | 2012-01-12 | Pharmascience Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| US8383094B2 (en) * | 2008-10-01 | 2013-02-26 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8946289B2 (en) | 2008-11-19 | 2015-02-03 | Duke University | Manassatin compounds and methods of making and using the same |
| JP2010126571A (ja) | 2008-11-26 | 2010-06-10 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子材料および有機エレクトロルミネッセンス素子 |
| US8729077B2 (en) | 2008-11-28 | 2014-05-20 | Glaxosmithkline Llc | Anti-viral compounds, compositions, and methods of use |
| WO2010065674A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| CA2750577A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| SG172352A1 (en) | 2008-12-23 | 2011-07-28 | Abbott Lab | Anti-viral compounds |
| US8546405B2 (en) * | 2008-12-23 | 2013-10-01 | Abbott Laboratories | Anti-viral compounds |
| US8314135B2 (en) * | 2009-02-09 | 2012-11-20 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole antivirals |
| EP2393359A4 (en) | 2009-02-09 | 2012-10-03 | Enanta Pharm Inc | COMPOUND DIBENZIMIDAZOLE DERIVATIVES |
| US8637561B2 (en) * | 2009-02-17 | 2014-01-28 | Enanta Pharmaceuticals, Inc. | Linked diimidazole derivatives |
| US8394968B2 (en) * | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI438200B (zh) | 2009-02-17 | 2014-05-21 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| US8420686B2 (en) * | 2009-02-17 | 2013-04-16 | Enanta Pharmaceuticals, Inc. | Linked diimidazole antivirals |
| US8242156B2 (en) * | 2009-02-17 | 2012-08-14 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| WO2010096462A1 (en) | 2009-02-17 | 2010-08-26 | Enanta Pharmaceuticals, Inc | Linked diimidazole derivatives |
| US8188132B2 (en) * | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| WO2010094977A1 (en) * | 2009-02-23 | 2010-08-26 | Arrow Therapeutics Limited | Novel biphenyl compounds useful for the treatment of hepatitis c |
| US20120040977A1 (en) * | 2009-02-23 | 2012-02-16 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| RU2544010C2 (ru) | 2009-02-27 | 2015-03-10 | Энанта Фармасьютикалс, Инк. | Ингибиторы вируса гепатита с |
| US8101643B2 (en) * | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8426458B2 (en) * | 2009-02-27 | 2013-04-23 | Enanta Pharmaceuticals, Inc. | Hepatitis C Virus inhibitors |
| US8507522B2 (en) * | 2009-03-06 | 2013-08-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| SG174883A1 (en) | 2009-03-27 | 2011-11-28 | Presidio Pharmaceuticals Inc | Fused ring inhibitors of hepatitis c |
| US8709999B2 (en) * | 2009-03-27 | 2014-04-29 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic HCV inhibitors |
| DK2410844T3 (en) | 2009-03-27 | 2016-07-04 | Merck Sharp & Dohme | Inhibitors of hepatitis C virus replication |
| US8796466B2 (en) * | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI476190B (zh) * | 2009-03-30 | 2015-03-11 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| US20110237636A1 (en) * | 2009-03-30 | 2011-09-29 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| WO2010115767A1 (en) | 2009-04-08 | 2010-10-14 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9278922B2 (en) * | 2009-04-15 | 2016-03-08 | Abbvie Inc. | Anti-viral compounds |
| MX2011011136A (es) | 2009-04-24 | 2011-11-18 | Tibotec Pharm Ltd | Eteres diarilicos. |
| EP2430015B1 (en) | 2009-05-12 | 2015-06-17 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds useful for the treatment of viral diseases |
| HUE030465T2 (hu) | 2009-05-13 | 2017-05-29 | Antivirális vegyületek | |
| EP2435421A1 (en) | 2009-05-29 | 2012-04-04 | Schering Corporation | Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis c |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP2012528195A (ja) | 2009-05-29 | 2012-11-12 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｃ型肝炎などの疾患を処置するための３つの結合アリール部分で構成された抗菌性化合物 |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EA020031B1 (ru) * | 2009-06-11 | 2014-08-29 | Эббви Бахамаз Лтд. | Противовирусные соединения |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US9394279B2 (en) * | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2010148006A1 (en) | 2009-06-16 | 2010-12-23 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| US8609648B2 (en) * | 2009-07-02 | 2013-12-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011004276A1 (en) * | 2009-07-06 | 2011-01-13 | Pfizer Limited | Hepatitis c virus inhibitors |
| AU2010274001A1 (en) | 2009-07-16 | 2012-02-23 | Vertex Pharmaceuticals Incorporated | Benzimidazole analogues for the treatment or prevention of Flavivirus infections |
| WO2011015658A1 (en) | 2009-08-07 | 2011-02-10 | Tibotec Pharmaceuticals | Bis-benzimidazole derivatives as hepatitis c virus inhibitors |
| AU2010291215A1 (en) | 2009-09-03 | 2012-02-23 | Janssen Sciences Ireland Uc | Bis-benzimidazole derivatives |
| CN102480971B (zh) | 2009-09-04 | 2014-11-26 | 杨森制药公司 | 化合物 |
| US8703938B2 (en) * | 2009-09-11 | 2014-04-22 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8759332B2 (en) * | 2009-09-11 | 2014-06-24 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8815928B2 (en) * | 2009-09-11 | 2014-08-26 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US9156818B2 (en) * | 2009-09-11 | 2015-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8927709B2 (en) * | 2009-09-11 | 2015-01-06 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8822700B2 (en) * | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011031934A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| WO2011050146A1 (en) | 2009-10-23 | 2011-04-28 | Glaxosmithkline Llc | Chemical compounds |
| UA108211C2 (uk) | 2009-11-04 | 2015-04-10 | Янссен Рід Айрленд | Бензімідазолімідазольні похідні |
| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110281910A1 (en) | 2009-11-12 | 2011-11-17 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| EP2503881B1 (en) | 2009-11-25 | 2015-05-13 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases |
| TWI429645B (en) | 2009-12-04 | 2014-03-11 | Proline derivatives | |
| US8653070B2 (en) * | 2009-12-14 | 2014-02-18 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| MX2012006877A (es) | 2009-12-18 | 2012-08-31 | Idenix Pharmaceuticals Inc | Inhibidores de virus de hepatitis c de arileno o heteroarileno 5, 5 - fusionado. |
| US20110152246A1 (en) * | 2009-12-18 | 2011-06-23 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| AU2010341537A1 (en) | 2009-12-22 | 2012-08-09 | Merck Sharp & Dohme Corp. | Fused Tricyclic Compounds and methods of use thereof for the treatment of viral diseases |
| MX2012007420A (es) | 2009-12-24 | 2012-07-23 | Vertex Pharma | Analogos para el tratamiento o prevencion de infecciones de flavivirus. |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2011091446A1 (en) | 2010-01-22 | 2011-07-28 | Glaxosmithkline Llc | Chemical compounds |
| PE20130244A1 (es) * | 2010-01-25 | 2013-03-10 | Enanta Pharm Inc | Inhibidores del virus de la hepatitis c |
| JP2013518062A (ja) | 2010-01-28 | 2013-05-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃ型肝炎阻害化合物 |
| US8178531B2 (en) * | 2010-02-23 | 2012-05-15 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| CN102858157A (zh) * | 2010-03-04 | 2013-01-02 | 埃南塔制药公司 | 作为hcv复制的抑制剂的组合药物活性剂 |
| EP2545060B1 (en) * | 2010-03-09 | 2015-11-25 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
| AU2011232348A1 (en) | 2010-03-24 | 2012-10-11 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of Flavivirus infections |
| EP2550268A1 (en) | 2010-03-24 | 2013-01-30 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| CN102869657A (zh) | 2010-03-24 | 2013-01-09 | 沃泰克斯药物股份有限公司 | 用于治疗或预防黄病毒感染的类似物 |
| TW201139438A (en) | 2010-03-24 | 2011-11-16 | Vertex Pharma | Analogues for the treatment or prevention of flavivirus infections |
| EP2555622A4 (en) | 2010-04-09 | 2013-09-18 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US20110312996A1 (en) | 2010-05-17 | 2011-12-22 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| US20130296311A1 (en) | 2010-05-28 | 2013-11-07 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| AR081848A1 (es) | 2010-06-09 | 2012-10-24 | Presidio Pharmaceuticals Inc | Inhibidores de la proteina ns5a del vhc |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| WO2012083164A1 (en) | 2010-12-16 | 2012-06-21 | Abbott Laboratories | Anti-viral compounds |
| JP5906253B2 (ja) | 2010-12-16 | 2016-04-20 | アッヴィ・インコーポレイテッド | 抗ウイルス性化合物 |
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| ES2567047T3 (es) | 2016-04-19 |
| EP2367824B1 (en) | 2016-03-23 |
| HK1159619A1 (zh) | 2012-08-03 |
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| US9163017B2 (en) | 2015-10-20 |
| WO2010075376A2 (en) | 2010-07-01 |
| ZA201105355B (en) | 2012-03-28 |
| MX2011006332A (es) | 2011-06-27 |
| WO2010075376A3 (en) | 2010-09-30 |
| US20100168138A1 (en) | 2010-07-01 |
| US8541424B2 (en) | 2013-09-24 |
| CA2740193A1 (en) | 2010-07-01 |
| JP2012513409A (ja) | 2012-06-14 |
| CN102264737A (zh) | 2011-11-30 |
| US20140213601A1 (en) | 2014-07-31 |
| RU2505540C2 (ru) | 2014-01-27 |
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