CA2822062A1 - Inhibitors of influenza viruses replication - Google Patents
Inhibitors of influenza viruses replication Download PDFInfo
- Publication number
- CA2822062A1 CA2822062A1 CA2822062A CA2822062A CA2822062A1 CA 2822062 A1 CA2822062 A1 CA 2822062A1 CA 2822062 A CA2822062 A CA 2822062A CA 2822062 A CA2822062 A CA 2822062A CA 2822062 A1 CA2822062 A1 CA 2822062A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- independently
- group
- compound
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 241000712461 unidentified influenza virus Species 0.000 title claims abstract description 45
- 230000010076 replication Effects 0.000 title claims abstract description 16
- 239000003112 inhibitor Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 361
- 150000003839 salts Chemical class 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 78
- 206010022000 influenza Diseases 0.000 claims abstract description 64
- 239000012472 biological sample Substances 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 239000003937 drug carrier Substances 0.000 claims abstract description 16
- 239000003981 vehicle Substances 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 239000002671 adjuvant Substances 0.000 claims abstract description 8
- -1 cyano, hydroxy Chemical group 0.000 claims description 205
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 183
- 229910052736 halogen Inorganic materials 0.000 claims description 138
- 150000002367 halogens Chemical class 0.000 claims description 95
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 125000004043 oxo group Chemical group O=* 0.000 claims description 71
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 125000001931 aliphatic group Chemical group 0.000 claims description 62
- 125000002837 carbocyclic group Chemical group 0.000 claims description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000001188 haloalkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
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- 125000004429 atom Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 26
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 26
- 229940124597 therapeutic agent Drugs 0.000 claims description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 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 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 9
- 125000003003 spiro group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 229960003971 influenza vaccine Drugs 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
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- 230000015572 biosynthetic process Effects 0.000 description 82
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- 239000000047 product Substances 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 57
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- 238000002360 preparation method Methods 0.000 description 38
- 241000700605 Viruses Species 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- 239000002904 solvent Substances 0.000 description 30
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- 239000012043 crude product Substances 0.000 description 27
- 238000000746 purification Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 101150041968 CDC13 gene Proteins 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 23
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 22
- 208000015181 infectious disease Diseases 0.000 description 22
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 21
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 13
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US42393310P | 2010-12-16 | 2010-12-16 | |
| US61/423,933 | 2010-12-16 | ||
| US201161527277P | 2011-08-25 | 2011-08-25 | |
| US61/527,277 | 2011-08-25 | ||
| PCT/US2011/065389 WO2012083122A1 (en) | 2010-12-16 | 2011-12-16 | Inhibitors of influenza viruses replication |
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| CA2822062A1 true CA2822062A1 (en) | 2012-06-21 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2822062A Abandoned CA2822062A1 (en) | 2010-12-16 | 2011-12-16 | Inhibitors of influenza viruses replication |
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| EP (1) | EP2651938A1 (enExample) |
| JP (1) | JP2013545818A (enExample) |
| KR (1) | KR20130128435A (enExample) |
| CN (1) | CN103562205A (enExample) |
| AU (1) | AU2011343647A1 (enExample) |
| CA (1) | CA2822062A1 (enExample) |
| MX (1) | MX2013006840A (enExample) |
| RU (1) | RU2013132683A (enExample) |
| WO (1) | WO2012083122A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11345700B2 (en) | 2013-11-13 | 2022-05-31 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
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| RU2435769C2 (ru) * | 2005-05-20 | 2011-12-10 | Вертекс Фармасьютикалз Инкорпорейтед | Пирролопиридины, полезные в качестве ингибиторов протеинкиназы |
| NZ597059A (en) | 2009-06-17 | 2014-01-31 | Vertex Pharma | Inhibitors of influenza viruses replication |
| RU2013132681A (ru) | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| SG10201804026WA (en) | 2013-11-13 | 2018-06-28 | Vertex Pharma | Inhibitors of influenza viruses replication |
| EP3082819B1 (en) | 2013-12-20 | 2020-06-17 | Signal Pharmaceuticals, LLC | Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith |
| WO2016020526A1 (en) * | 2014-08-08 | 2016-02-11 | Janssen Sciences Ireland Uc | Indoles for use in influenza virus infection |
| DK3191489T3 (da) * | 2014-09-08 | 2021-03-29 | Janssen Sciences Ireland Unlimited Co | Pyrrolopyrimidiner til anvendelse ved influenzavirusinfektion |
| EP3929293A3 (en) | 2015-04-03 | 2022-03-16 | University Of Massachusetts | Fully stabilized asymmetric sirna |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| MA42422A (fr) | 2015-05-13 | 2018-05-23 | Vertex Pharma | Inhibiteurs de la réplication des virus de la grippe |
| US10633653B2 (en) | 2015-08-14 | 2020-04-28 | University Of Massachusetts | Bioactive conjugates for oligonucleotide delivery |
| CA3005514A1 (en) * | 2015-11-27 | 2017-06-01 | Janssen Sciences Ireland Uc | Heterocyclic indoles for use in influenza virus infection |
| RU2737190C2 (ru) | 2015-12-09 | 2020-11-25 | Саншайн Лейк Фарма Ко., Лтд. | Ингибиторы репликации вируса гриппа, способы их применения и использование |
| JP6989509B2 (ja) * | 2016-01-20 | 2022-01-05 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | インフルエンザウイルス感染における使用のためのアリール置換ピリミジン |
| US10478503B2 (en) | 2016-01-31 | 2019-11-19 | University Of Massachusetts | Branched oligonucleotides |
| WO2017133664A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Bicyclic pyridine and pyrimidine derivatives and their use in the treatment， amelioration or prevention of influenza |
| WO2017133670A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Pyridine and pyrimidine derivatives and their use in treatment, amelioration or prevention of influenza |
| WO2017133658A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | 4, 7-diazaindole and 4, 7-diazaindazole derivatives and their use in the treatment, amelioration or prevention of influenza |
| WO2017133667A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Pyrimidine and pyridine derivatives and use in treatment, amelioration or prevention of influenza thereof |
| WO2017133665A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | 6,7-diazaindazole and 6,7-diazaindole derivatives and use in treatment, amelioration or prevention of influenza thereof |
| WO2017133657A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Pyridine and pyrimidine derivatives and their use in treatment, amelioration or prevention of influenza |
| CN107759571B (zh) | 2016-08-16 | 2021-03-02 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其使用方法和用途 |
| US10647693B2 (en) * | 2016-08-30 | 2020-05-12 | North & South Brother Pharmacy Investment Company Limited | Inhibitors of influenza virus replication, application methods and uses thereof |
| US10987354B2 (en) | 2016-12-15 | 2021-04-27 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication and uses thereof |
| US11098042B2 (en) | 2017-01-05 | 2021-08-24 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication and uses thereof |
| CN110446711B (zh) | 2017-03-02 | 2022-02-15 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其用途 |
| CN108727369B (zh) * | 2017-04-25 | 2023-06-09 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其用途 |
| US10844377B2 (en) | 2017-06-23 | 2020-11-24 | University Of Massachusetts | Two-tailed self-delivering siRNA |
| EP3829719B1 (en) | 2018-07-27 | 2025-04-02 | Cocrystal Pharma, Inc. | Pyrrolo[2,3-b]pyridin derivatives as inhibitors of influenza virus replication |
| JP7627042B2 (ja) | 2018-08-23 | 2025-02-05 | ユニバーシティー オブ マサチューセッツ | Ｏ－メチルリッチ完全安定化オリゴヌクレオチド |
| CN109678738B (zh) * | 2018-12-26 | 2021-11-30 | 深圳市华先医药科技有限公司 | 一种合成(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法 |
| WO2020150636A1 (en) | 2019-01-18 | 2020-07-23 | University Of Massachusetts | Dynamic pharmacokinetic-modifying anchors |
| WO2020198509A2 (en) | 2019-03-26 | 2020-10-01 | University Of Massachusetts | Modified oligonucleotides with increased stability |
| CN114502730A (zh) | 2019-08-09 | 2022-05-13 | 马萨诸塞大学 | 经化学修饰的靶向snp的寡核苷酸 |
| US12365894B2 (en) | 2019-09-16 | 2025-07-22 | University Of Massachusetts | Branched lipid conjugates of siRNA for specific tissue delivery |
| CN115666659B (zh) | 2020-03-26 | 2026-03-03 | 马萨诸塞大学 | 稳定性增加的修饰的寡核苷酸的合成 |
| US20230159453A1 (en) * | 2020-04-10 | 2023-05-25 | Cocrystal Pharma, Inc. | Inhibitors of norovirus and coronavirus replication |
| EP4157289A4 (en) | 2020-05-26 | 2024-06-26 | University Of Massachusetts | Synthetic oligonucleotides having regions of block and cluster modifications |
| CN112063726A (zh) * | 2020-09-21 | 2020-12-11 | 杭州市疾病预防控制中心 | 一种用于检测奥司他韦耐药突变的引物、探针及检测方法 |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
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| AU2001294518A1 (en) | 2000-09-22 | 2002-04-02 | Eli Lilly And Company | Stereoselective process for preparing cyclohexyl amine derivatives |
| CA2456292A1 (en) | 2001-08-14 | 2003-02-27 | Toyama Chemical Co., Ltd. | Novel virus growth inhibitor and/or virucidal method, and novel pyrazine nucleotide or pirazine nucleoside analog |
| TWI339206B (en) * | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| EP2311837B1 (en) | 2004-03-30 | 2014-05-21 | Vertex Pharmaceuticals Inc. | Azaindoles useful as inhibitors of jak and other protein kinases |
| UA87494C2 (en) * | 2004-03-30 | 2009-07-27 | Вертекс Фармасьютикалс Инкорпорейтед | Azaindoles useful as inhibitors of jak and other protein kinases |
| US20060161001A1 (en) * | 2004-12-20 | 2006-07-20 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| CA2608333A1 (en) * | 2005-05-16 | 2006-11-23 | Irm Llc | Pyrrolopyridine derivatives as protein kinase inhibitors |
| RU2008117151A (ru) * | 2005-09-30 | 2009-11-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Деазапурины, пригодные в качестве ингибиторов янус-киназ |
| JP5591471B2 (ja) | 2006-01-17 | 2014-09-17 | 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 | ヤヌスキナーゼ阻害剤として有用なアザインドール |
| JP5406039B2 (ja) | 2006-12-21 | 2014-02-05 | 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 | タンパク質キナーゼ阻害剤として有用な５−シアノ−４−（ピロロ［２，３ｂ］ピリジン−３−イル）−ピリミジン誘導体 |
| US8173635B2 (en) | 2007-11-02 | 2012-05-08 | Vertex Pharmaceuticals Incorporated | Kinase inhibitors |
| AU2009274023A1 (en) | 2008-07-23 | 2010-01-28 | Vertex Pharmaceuticals Incorporated | Tri-cyclic pyrazolopyridine kinase inhibitors |
| MX2011000843A (es) | 2008-07-23 | 2011-04-11 | Vertex Pharma | Inhibidores de pirazolopiridin cinasa triciclicos. |
| MX2011000839A (es) | 2008-07-23 | 2011-04-05 | Vertex Pharma | Inhibidores de pirazolpiridina cinasa. |
| US20100038988A1 (en) | 2008-08-12 | 2010-02-18 | Gannon Ramy | Stator and Method of Making the Same |
| NZ597059A (en) * | 2009-06-17 | 2014-01-31 | Vertex Pharma | Inhibitors of influenza viruses replication |
| CA2767089A1 (en) * | 2009-07-15 | 2011-01-20 | Abbott Laboratories | Pyrrolopyridine inhibitors of kinases |
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2011
- 2011-12-16 WO PCT/US2011/065389 patent/WO2012083122A1/en not_active Ceased
- 2011-12-16 EP EP11806096.1A patent/EP2651938A1/en not_active Withdrawn
- 2011-12-16 CN CN201180066551.2A patent/CN103562205A/zh active Pending
- 2011-12-16 CA CA2822062A patent/CA2822062A1/en not_active Abandoned
- 2011-12-16 AU AU2011343647A patent/AU2011343647A1/en not_active Abandoned
- 2011-12-16 JP JP2013544810A patent/JP2013545818A/ja active Pending
- 2011-12-16 MX MX2013006840A patent/MX2013006840A/es not_active Application Discontinuation
- 2011-12-16 RU RU2013132683/04A patent/RU2013132683A/ru not_active Application Discontinuation
- 2011-12-16 KR KR1020137018522A patent/KR20130128435A/ko not_active Withdrawn
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2013
- 2013-06-14 US US13/918,115 patent/US20130345218A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11345700B2 (en) | 2013-11-13 | 2022-05-31 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103562205A (zh) | 2014-02-05 |
| WO2012083122A8 (en) | 2013-12-05 |
| KR20130128435A (ko) | 2013-11-26 |
| JP2013545818A (ja) | 2013-12-26 |
| EP2651938A1 (en) | 2013-10-23 |
| WO2012083122A1 (en) | 2012-06-21 |
| RU2013132683A (ru) | 2015-01-27 |
| US20130345218A1 (en) | 2013-12-26 |
| AU2011343647A1 (en) | 2013-05-02 |
| MX2013006840A (es) | 2014-01-31 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20151216 |