CA2886138C - Mek inhibitors in the treatment of virus diseases - Google Patents
Mek inhibitors in the treatment of virus diseases Download PDFInfo
- Publication number
- CA2886138C CA2886138C CA2886138A CA2886138A CA2886138C CA 2886138 C CA2886138 C CA 2886138C CA 2886138 A CA2886138 A CA 2886138A CA 2886138 A CA2886138 A CA 2886138A CA 2886138 C CA2886138 C CA 2886138C
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- inhibitor
- oseltamivir
- mek
- 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.)
- Active
Links
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title claims abstract 12
- 238000011282 treatment Methods 0.000 title claims abstract 5
- 201000010099 disease Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 241000700605 Viruses Species 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 9
- 229940124647 MEK inhibitor Drugs 0.000 claims 8
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims 6
- GFMMXOIFOQCCGU-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 GFMMXOIFOQCCGU-UHFFFAOYSA-N 0.000 claims 4
- 229960003752 oseltamivir Drugs 0.000 claims 3
- 229960002194 oseltamivir phosphate Drugs 0.000 claims 3
- 241000712461 unidentified influenza virus Species 0.000 claims 3
- QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-UHFFFAOYSA-N 0.000 claims 2
- RWEVIPRMPFNTLO-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-3-pyridinecarboxamide Chemical compound CN1C(=O)C(C)=CC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F RWEVIPRMPFNTLO-UHFFFAOYSA-N 0.000 claims 2
- FIMYFEGKMOCQKT-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-5-[(3-oxooxazinan-2-yl)methyl]benzamide Chemical compound FC=1C(F)=C(NC=2C(=CC(I)=CC=2)F)C(C(=O)NOCCO)=CC=1CN1OCCCC1=O FIMYFEGKMOCQKT-UHFFFAOYSA-N 0.000 claims 2
- RCLQNICOARASSR-SECBINFHSA-N 3-[(2r)-2,3-dihydroxypropyl]-6-fluoro-5-(2-fluoro-4-iodoanilino)-8-methylpyrido[2,3-d]pyrimidine-4,7-dione Chemical compound FC=1C(=O)N(C)C=2N=CN(C[C@@H](O)CO)C(=O)C=2C=1NC1=CC=C(I)C=C1F RCLQNICOARASSR-SECBINFHSA-N 0.000 claims 2
- LMMJFBMMJUMSJS-UHFFFAOYSA-N CH5126766 Chemical compound CNS(=O)(=O)NC1=NC=CC(CC=2C(OC3=CC(OC=4N=CC=CN=4)=CC=C3C=2C)=O)=C1F LMMJFBMMJUMSJS-UHFFFAOYSA-N 0.000 claims 2
- VIUAUNHCRHHYNE-JTQLQIEISA-N N-[(2S)-2,3-dihydroxypropyl]-3-(2-fluoro-4-iodoanilino)-4-pyridinecarboxamide Chemical compound OC[C@@H](O)CNC(=O)C1=CC=NC=C1NC1=CC=C(I)C=C1F VIUAUNHCRHHYNE-JTQLQIEISA-N 0.000 claims 2
- SUDAHWBOROXANE-VIFPVBQESA-N PD 0325901-Cl Chemical compound OC[C@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-VIFPVBQESA-N 0.000 claims 2
- BSMCAPRUBJMWDF-KRWDZBQOSA-N cobimetinib Chemical compound C1C(O)([C@H]2NCCCC2)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F BSMCAPRUBJMWDF-KRWDZBQOSA-N 0.000 claims 2
- 229960002271 cobimetinib Drugs 0.000 claims 2
- RDSACQWTXKSHJT-NSHDSACASA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[(2s)-2,3-dihydroxypropyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(C[C@H](O)CO)S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F RDSACQWTXKSHJT-NSHDSACASA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- CYOHGALHFOKKQC-UHFFFAOYSA-N selumetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl CYOHGALHFOKKQC-UHFFFAOYSA-N 0.000 claims 2
- LIRYPHYGHXZJBZ-UHFFFAOYSA-N trametinib Chemical compound CC(=O)NC1=CC=CC(N2C(N(C3CC3)C(=O)C3=C(NC=4C(=CC(I)=CC=4)F)N(C)C(=O)C(C)=C32)=O)=C1 LIRYPHYGHXZJBZ-UHFFFAOYSA-N 0.000 claims 2
- GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical group CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 claims 2
- 229960003862 vemurafenib Drugs 0.000 claims 2
- 241000712431 Influenza A virus Species 0.000 claims 1
- 241000713196 Influenza B virus Species 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- 229940123424 Neuraminidase inhibitor Drugs 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 239000002911 sialidase inhibitor Substances 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
- 230000003612 virological effect Effects 0.000 abstract 1
Classifications
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
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- A61K31/18—Sulfonamides
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- 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
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- A—HUMAN NECESSITIES
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- A61K31/4375—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 six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4458—Non condensed piperidines, e.g. piperocaine only substituted in position 2, e.g. methylphenidate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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- A—HUMAN NECESSITIES
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Emergency Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261711136P | 2012-10-08 | 2012-10-08 | |
| US61/711,136 | 2012-10-08 | ||
| PCT/EP2013/070917 WO2014056894A1 (en) | 2012-10-08 | 2013-10-08 | Mek inhibitors in the treatment of virus diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2886138A1 CA2886138A1 (en) | 2014-04-17 |
| CA2886138C true CA2886138C (en) | 2021-10-12 |
Family
ID=49552318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2886138A Active CA2886138C (en) | 2012-10-08 | 2013-10-08 | Mek inhibitors in the treatment of virus diseases |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9566281B2 (OSRAM) |
| EP (1) | EP2903649A1 (OSRAM) |
| JP (2) | JP6294889B2 (OSRAM) |
| KR (1) | KR102174576B1 (OSRAM) |
| CN (2) | CN105101999B (OSRAM) |
| AU (1) | AU2013328824B2 (OSRAM) |
| BR (1) | BR112015007616B1 (OSRAM) |
| CA (1) | CA2886138C (OSRAM) |
| EA (1) | EA028605B1 (OSRAM) |
| WO (1) | WO2014056894A1 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9181329B2 (en) * | 2007-08-31 | 2015-11-10 | The University Of Chicago | Methods and compositions related to immunizing against Staphylococcal lung diseases and conditions |
| US9566281B2 (en) * | 2012-10-08 | 2017-02-14 | Atriva Therapeutics Gmbh | MEK inhibitors in the treatment of virus diseases |
| CN116942832A (zh) | 2014-05-16 | 2023-10-27 | 归属疗法有限公司 | 抗流感病毒和金黄色葡萄球菌合并感染的新型抗感染策略 |
| US20190183855A1 (en) * | 2016-08-10 | 2019-06-20 | Riken | Composition for treating hepatitis b, and method for evaluating replication activity of hepatitis b virus |
| TW201818936A (zh) * | 2016-11-25 | 2018-06-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 一種吡啶酮類衍生物醫藥組成物及其製備方法 |
| US11040027B2 (en) | 2017-01-17 | 2021-06-22 | Heparegenix Gmbh | Protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| US11903917B2 (en) * | 2017-10-17 | 2024-02-20 | Atriva Therapeutics Gmbh | MEK-inhibitor for the treatment of viral and bacterial infections |
| US20190298669A1 (en) * | 2018-03-29 | 2019-10-03 | Atriva Therapeutics Gmbh | Ci-1040 for the treatment of viral diseases |
| DK3860598T3 (da) * | 2018-10-03 | 2023-10-16 | Jyvaeskylaen Yliopisto | Vemurafenib og salte heraf til anvendelse til behandling af enterovirusinfektioner |
| CN109765324B (zh) * | 2018-11-27 | 2021-03-30 | 苏州科技大学 | 一种mek1蛋白潜在抑制剂的筛选方法 |
| US20220152080A1 (en) | 2019-03-19 | 2022-05-19 | Atriva Therapeutics Gmbh | Rsk inhibitors in the treatment of virus diseases |
| LU101183B1 (en) | 2019-04-16 | 2020-10-16 | Atriva Therapeutics Gmbh | Novel mek-inhibitor for the treatment of viral and bacterial infections |
| CA3149588A1 (en) | 2019-08-27 | 2021-03-04 | Oliver Planz | Combinations of mek inhibitors with cap-dependent endonuclease inhibitors |
| BR112022005896A2 (pt) * | 2019-10-08 | 2022-06-28 | Atriva Therapeutics Gmbh | Inibidores da mek para o tratamento de infecções causadas por hantavírus |
| WO2021214296A1 (en) * | 2020-04-24 | 2021-10-28 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Treatment of corona virus infections |
| CN111494620A (zh) * | 2020-05-05 | 2020-08-07 | 华中科技大学同济医学院附属协和医院 | 曲美替尼在制备疫苗中的应用 |
| CN111529532A (zh) * | 2020-05-05 | 2020-08-14 | 华中科技大学同济医学院附属协和医院 | 曲美替尼在制备治疗肺部炎症性疾病药物及促进Tfh细胞分化药物中的应用 |
| CN112137994B (zh) * | 2020-09-15 | 2022-10-14 | 中山大学 | 小分子化合物在制备抗丝状病毒药物中的应用 |
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|---|---|---|---|---|
| WO1992002484A1 (en) | 1990-07-30 | 1992-02-20 | Alder Research Center Limited Partnership | Protein kinase c modulators with anti-inflammatory and antiviral activity |
| US5866601A (en) | 1995-02-27 | 1999-02-02 | Gilead Sciences, Inc. | Carbocyclic compounds |
| US5763483A (en) | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
| EP1140067A1 (en) * | 1999-01-07 | 2001-10-10 | Warner-Lambert Company | Antiviral method using mek inhibitors |
| DE10017480A1 (de) * | 2000-04-07 | 2001-10-11 | Transmit Technologietransfer | Verwendung von Substanzen, die als MEK Inhibitor wirken, zur Herstellung eines Arneimittels gegen DNA- und RNA-Viren |
| DE10138912A1 (de) | 2001-08-08 | 2003-02-27 | Medinnova Ges Med Innovationen | Verwendung von Wirksubstanzen zur Prophylaxe und/oder Therapie von Viruserkrankungen sowie Testsystem zum Auffinden solcher Wirksubstanzen |
| UA95244C2 (ru) * | 2005-06-22 | 2011-07-25 | Плексикон, Инк. | Соединения и способ модулирования активности киназ, и показания для их применения |
| CN105363034A (zh) * | 2008-05-23 | 2016-03-02 | 香港大学 | 治疗流感的联合疗法 |
| US9566281B2 (en) * | 2012-10-08 | 2017-02-14 | Atriva Therapeutics Gmbh | MEK inhibitors in the treatment of virus diseases |
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| US9566281B2 (en) | 2017-02-14 |
| BR112015007616A2 (pt) | 2017-08-08 |
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| CA2886138A1 (en) | 2014-04-17 |
| CN109276716B (zh) | 2021-06-08 |
| JP2018118971A (ja) | 2018-08-02 |
| EA201590703A1 (ru) | 2015-07-30 |
| EA028605B1 (ru) | 2017-12-29 |
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| US20170209450A1 (en) | 2017-07-27 |
| JP6294889B2 (ja) | 2018-03-14 |
| US20150224103A1 (en) | 2015-08-13 |
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| EP2903649A1 (en) | 2015-08-12 |
| JP2015534562A (ja) | 2015-12-03 |
| AU2013328824B2 (en) | 2018-04-05 |
| CN109276716A (zh) | 2019-01-29 |
| AU2013328824A1 (en) | 2015-04-30 |
| WO2014056894A1 (en) | 2014-04-17 |
| CN105101999B (zh) | 2018-07-17 |
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