HRP20110458T1 - Inhibitori rna-ovisne rna-polimeraze iz virusa hepatitisa c, te pripravci i liječenje u kojem se koriste - Google Patents
Inhibitori rna-ovisne rna-polimeraze iz virusa hepatitisa c, te pripravci i liječenje u kojem se koriste Download PDFInfo
- Publication number
- HRP20110458T1 HRP20110458T1 HR20110458T HRP20110458T HRP20110458T1 HR P20110458 T1 HRP20110458 T1 HR P20110458T1 HR 20110458 T HR20110458 T HR 20110458T HR P20110458 T HRP20110458 T HR P20110458T HR P20110458 T1 HRP20110458 T1 HR P20110458T1
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- methyl
- triazolo
- cyclopentyl
- pyran
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims 4
- 239000003112 inhibitor Substances 0.000 title claims 3
- 241000711549 Hepacivirus C Species 0.000 title claims 2
- 108060004795 Methyltransferase Proteins 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- -1 -OR6 Chemical group 0.000 claims abstract 30
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 26
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 239000012453 solvate Substances 0.000 claims abstract 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 150000002367 halogens Chemical class 0.000 claims abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims abstract 2
- XTCSVDSGUHHIRY-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(5-ethylpyridin-3-yl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound CCC1=CN=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 XTCSVDSGUHHIRY-UHFFFAOYSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 24
- SLVAPEZTBDBAPI-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(2,6-diethylpyridin-4-yl)ethyl]-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound CCC1=NC(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 SLVAPEZTBDBAPI-UHFFFAOYSA-N 0.000 claims 11
- HHXVQUXEUPSTEC-UHFFFAOYSA-N 2-[2-[2,6-bis(2,2,2-trifluoroethyl)pyridin-4-yl]ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC(CC(F)(F)F)=NC(CC(F)(F)F)=C1 HHXVQUXEUPSTEC-UHFFFAOYSA-N 0.000 claims 7
- SHNZPCPBLPOEEZ-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(5-ethoxy-2-ethylpyridin-4-yl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound CCOC1=CN=C(CC)C=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C=C(C)C=NC3=N2)=C(O)C1 SHNZPCPBLPOEEZ-UHFFFAOYSA-N 0.000 claims 7
- CDOUPZXWEKOMRI-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(5-ethoxy-2-ethylpyridin-4-yl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound CCOC1=CN=C(CC)C=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 CDOUPZXWEKOMRI-UHFFFAOYSA-N 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- QSZNBUCBMYJWFQ-UHFFFAOYSA-N 1-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]-5-ethylpyridin-2-one Chemical compound C1=C(CC)C=CC(=O)N1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 QSZNBUCBMYJWFQ-UHFFFAOYSA-N 0.000 claims 1
- OBJZLLQBRVVCFZ-UHFFFAOYSA-N 2-[2-(6-amino-5-ethyl-2-methylpyridin-3-yl)ethyl]-2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound N1=C(N)C(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1C OBJZLLQBRVVCFZ-UHFFFAOYSA-N 0.000 claims 1
- NYHBKPWOGSMOKS-UHFFFAOYSA-N 2-[2-[2,6-bis(2,2,2-trifluoroethyl)pyridin-4-yl]ethyl]-2-cyclopentyl-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound N=1N2C=C(C)C=NC2=NC=1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CC(CC(F)(F)F)=NC(CC(F)(F)F)=C1 NYHBKPWOGSMOKS-UHFFFAOYSA-N 0.000 claims 1
- WUGYLLGNMCSUQM-UHFFFAOYSA-N 2-[3-chloro-5-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]pyridin-2-yl]-2-methylpropanenitrile Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCC1=CN=C(C(C)(C)C#N)C(Cl)=C1 WUGYLLGNMCSUQM-UHFFFAOYSA-N 0.000 claims 1
- IDEGWCVLXNUCSN-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(2,6-diethylpyridin-4-yl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound CCC1=NC(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(C)C=NC4=N3)=C(O)C2)C2CCCC2)=C1 IDEGWCVLXNUCSN-UHFFFAOYSA-N 0.000 claims 1
- XSJDVMHGTQZGEX-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(2,6-dimethylpyridin-4-yl)ethyl]-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-3h-pyran-6-one Chemical compound CC1=NC(C)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 XSJDVMHGTQZGEX-UHFFFAOYSA-N 0.000 claims 1
- KPAFBURYLWOICR-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(2-ethyl-5-methoxypyridin-4-yl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound C1=NC(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(C)C=NC4=N3)=C(O)C2)C2CCCC2)=C1OC KPAFBURYLWOICR-UHFFFAOYSA-N 0.000 claims 1
- OOMDKIXNOABGDK-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(2-ethyl-5-propoxypyridin-4-yl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound CCCOC1=CN=C(CC)C=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C=C(C)C=NC3=N2)=C(O)C1 OOMDKIXNOABGDK-UHFFFAOYSA-N 0.000 claims 1
- MHCUPLMWUDBQRC-UHFFFAOYSA-N 2-cyclopentyl-2-[2-(4-ethylpyridin-2-yl)ethyl]-4-hydroxy-5-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-3h-pyran-6-one Chemical compound CCC1=CC=NC(CCC2(OC(=O)C(CC3=NN4C=C(C)C=NC4=N3)=C(O)C2)C2CCCC2)=C1 MHCUPLMWUDBQRC-UHFFFAOYSA-N 0.000 claims 1
- AMRCSUYOSNECRQ-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-[2-(2-ethylpyridin-4-yl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=NC(CC)=CC(CCC2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 AMRCSUYOSNECRQ-UHFFFAOYSA-N 0.000 claims 1
- JVHCCHFIDUHSFQ-UHFFFAOYSA-N 2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-2-[2-(5-methoxy-2-methylpyridin-4-yl)ethyl]-3h-pyran-6-one Chemical compound COC1=CN=C(C)C=C1CCC1(C2CCCC2)OC(=O)C(CC2=NN3C(C)=CC(C)=NC3=N2)=C(O)C1 JVHCCHFIDUHSFQ-UHFFFAOYSA-N 0.000 claims 1
- LSVVRTCYQRPZKJ-UHFFFAOYSA-N 5-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-2-cyclopentyl-2-[2-(2-ethylpyridin-4-yl)ethyl]-4-hydroxy-3h-pyran-6-one Chemical compound C1=NC(CC)=CC(CCC2(OC(=O)C(CC3=NN4C=C(Cl)C=NC4=N3)=C(O)C2)C2CCCC2)=C1 LSVVRTCYQRPZKJ-UHFFFAOYSA-N 0.000 claims 1
- BXJRDNRTFGJWJN-UHFFFAOYSA-N 5-bromo-1-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3h-pyran-2-yl]ethyl]pyridin-2-one Chemical compound N1=C2N=C(C)C=C(C)N2N=C1CC(C(O1)=O)=C(O)CC1(C1CCCC1)CCN1C=C(Br)C=CC1=O BXJRDNRTFGJWJN-UHFFFAOYSA-N 0.000 claims 1
- SFSXNVBMAODLGN-UHFFFAOYSA-N Ethyl-2 methyl-6 pyridine Natural products CCC1=CC=CC(C)=N1 SFSXNVBMAODLGN-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- 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
- A61K31/335—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
- A61K31/351—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 not condensed with another ring
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60261804P | 2004-08-18 | 2004-08-18 | |
PCT/IB2005/002697 WO2006018725A1 (en) | 2004-08-18 | 2005-08-05 | Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20110458T1 true HRP20110458T1 (hr) | 2011-07-31 |
Family
ID=35429645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20110458T HRP20110458T1 (hr) | 2004-08-18 | 2011-06-17 | Inhibitori rna-ovisne rna-polimeraze iz virusa hepatitisa c, te pripravci i liječenje u kojem se koriste |
Country Status (43)
Families Citing this family (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE506364T1 (de) * | 2004-08-18 | 2011-05-15 | Pfizer | Inhibitoren der rna-abhängigen rna-polymerase des hepatitis-c-virus und zusammensetzungen und behandlungen, bei denen diese verwendet werden |
WO2007023381A1 (en) * | 2005-08-24 | 2007-03-01 | Pfizer Inc. | Methods for the preparation of hcv polymerase inhibitors |
ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
EP2008996A1 (en) * | 2007-06-27 | 2008-12-31 | Syngeta Participations AG | Process for the production of pyrazoles |
CN102083852A (zh) | 2008-06-06 | 2011-06-01 | 西尼克斯公司 | 环孢菌素类似物及其在治疗hcv感染中的应用 |
JP2011530562A (ja) | 2008-08-11 | 2011-12-22 | グラクソスミスクライン エルエルシー | アレルギー性、炎症性及び感染性疾患治療用のプリン誘導体 |
UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
HUE033645T2 (en) | 2008-08-11 | 2017-12-28 | Glaxosmithkline Llc | New adenine derivatives |
UY32940A (es) | 2009-10-27 | 2011-05-31 | Bayer Cropscience Ag | Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas |
MX2012004971A (es) | 2009-10-30 | 2012-06-12 | Boehringer Ingelheim Int | Regimenes de dosificacion para terapia combinada del vhc, que comprende b1201335, interferon alfa y ribavirina. |
EP2325173A1 (de) | 2009-11-19 | 2011-05-25 | Bayer CropScience AG | Verfahren zum Herstellen von 5-Fluor-1-alkyl-3-fluoralkyl-1H-pyrazol-4-carbonsäurechloriden |
KR20120116404A (ko) | 2009-12-18 | 2012-10-22 | 베링거 인겔하임 인터내셔날 게엠베하 | Hcv 병용 요법 |
US8703754B2 (en) | 2010-02-10 | 2014-04-22 | Glaxosmithkline Llc | 6-amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)-7,9-dihydro-8H-purin-8-one maleate |
WO2011098451A1 (en) | 2010-02-10 | 2011-08-18 | Glaxosmithkline Llc | Purine derivatives and their pharmaceutical uses |
ES2528646T3 (es) * | 2010-05-20 | 2015-02-11 | Bayer Intellectual Property Gmbh | Procedimiento para la fabricación de 1-alquil-3-difluorometil-5-hidroxipirazoles |
US8987307B2 (en) | 2011-03-03 | 2015-03-24 | Hoffmann-La Roche Inc. | 3-amino-pyridines as GPBAR1 agonists |
FR2972452B1 (fr) | 2011-03-09 | 2013-03-15 | Rhodia Operations | Procede de preparation du difluoroacetonitrile et de ses derives |
MX348274B (es) | 2012-05-14 | 2017-06-02 | Bayer Cropscience Ag | Procedimiento de preparacion de cloruros de 1-alquil-3-fluoroalqui l-1h-pirazol-4-carbonilo. |
US9163027B2 (en) | 2012-11-21 | 2015-10-20 | Stategics, Inc. | Substituted triazolo-pyrimidine compounds for modulating cell proliferation differentiation and survival |
JP6349329B2 (ja) | 2013-01-17 | 2018-06-27 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 5−フルオロ−1−メチル−3−ジフルオロメチル−1h−ピラゾール−4−カルバルデヒドを調製する方法 |
NO2953942T3 (ja) | 2013-02-06 | 2018-03-24 | ||
JP2017502964A (ja) | 2014-01-03 | 2017-01-26 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 殺有害生物剤としての新規ピラゾリル−ヘテロアリールアミド類 |
EP3097081B1 (en) | 2014-01-24 | 2018-01-10 | Bayer CropScience Aktiengesellschaft | Method for preparing 1-alkyl-3-difluoromethyl-5-fluor-1h-pyrazole-4-carbaldehydes and 1-alkyl-3-difluoromethyl-5-fluor-1h-pyrazole-4-carboxylates |
US10202386B2 (en) | 2014-02-20 | 2019-02-12 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pyrrolo[3,2-D]pyrimidine derivatives as inducers of human interferon |
TWI675827B (zh) | 2014-06-03 | 2019-11-01 | 瑞士商愛杜西亞製藥有限公司 | 吡唑化合物 |
EP3218377B1 (en) | 2014-11-13 | 2022-04-13 | GlaxoSmithKline Biologicals SA | Adenine derivatives which are useful in the treatment of allergic diseases or other inflammatory conditions |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
MX363780B (es) | 2015-12-03 | 2019-04-03 | Glaxosmithkline Ip Dev Ltd | Dinucleótidos de purina cíclica como moduladores del estimulador de los genes de interferón. |
HRP20220936T1 (hr) | 2016-04-07 | 2022-10-28 | Glaxosmithkline Intellectual Property Development Limited | Heterociklički amidi korisni kao modulatori proteina |
CN109563081A (zh) | 2016-04-07 | 2019-04-02 | 葛兰素史克知识产权开发有限公司 | 可用作蛋白调节剂的杂环酰胺类 |
WO2018033455A1 (de) | 2016-08-15 | 2018-02-22 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP3301094A1 (en) * | 2016-09-30 | 2018-04-04 | Mutabilis | Heterocyclic compounds and their use in preventing or treating bacterial infections |
BR112019011208A2 (pt) | 2016-12-16 | 2019-10-15 | Idorsia Pharmaceuticals Ltd | combinação farmacêutica, composição farmacêutica, e, kit de partes. |
JP6972144B2 (ja) | 2017-02-06 | 2021-11-24 | イドーシア ファーマシューティカルズ リミテッドIdorsia Pharmaceuticals Ltd | 1−アリール−1−トリフルオロメチルシクロプロパンを合成するための新規な方法 |
BR112020006659B1 (pt) | 2017-10-04 | 2022-01-25 | Bayer Aktiengesellschaft | Derivados de compostos heterocíclicos, formulação agroquímica, método para controlar uma ou mais pragas animais, e produto |
US20210238172A1 (en) | 2017-10-05 | 2021-08-05 | Glaxosmithkline Intellectual Property Development Limited | Heterocyclic amides useful as protein modulators and methods of using the same |
EP3692034A1 (en) | 2017-10-05 | 2020-08-12 | GlaxoSmithKline Intellectual Property Development Limited | Modulators of stimulator of interferon genes (sting) |
ES2925914T3 (es) | 2018-03-12 | 2022-10-20 | Bayer Ag | Derivados heterocíclicos condensados como plaguicidas |
KR20210005081A (ko) | 2018-04-20 | 2021-01-13 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로시클렌 유도체 |
GB201807924D0 (en) | 2018-05-16 | 2018-06-27 | Ctxt Pty Ltd | Compounds |
JP2022533390A (ja) | 2019-05-16 | 2022-07-22 | スティングセラ インコーポレイテッド | オキソアクリジニル酢酸誘導体および使用方法 |
EP3969452A1 (en) | 2019-05-16 | 2022-03-23 | Stingthera, Inc. | Benzo[b][1,8]naphthyridine acetic acid derivatives and methods of use |
GB201910305D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
GB201910304D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
CN112194620B (zh) * | 2020-12-04 | 2021-02-26 | 苏州开元民生科技股份有限公司 | 一种2-乙基-4-氰基吡啶的制备方法 |
CN113563167B (zh) * | 2021-07-16 | 2023-09-08 | 南通华祥医药科技有限公司 | 一种2-甲基-1-四氢萘酮的制备方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3786063A (en) | 1971-05-24 | 1974-01-15 | Universal Oil Prod Co | Thiazolethiosulfonates |
DE2155360C3 (de) * | 1971-11-08 | 1980-04-03 | Cassella Ag, 6000 Frankfurt | Verfahren zur Herstellung von Acylbernsteinsäuredialkylestern |
CA1144937A (en) | 1977-12-22 | 1983-04-19 | Dke J.E. Helgstrand | Aromatic derivatives, pharmaceutical compositions and methods for combatting virus infections |
US4326058A (en) | 1979-02-05 | 1982-04-20 | Sumitomo Chemical Company, Limited | Organo-phosphoric esters and their production and use |
US4489077A (en) | 1983-03-23 | 1984-12-18 | Warner-Lambert Company | 3-Isoxa-zolyl-2H-1,2-benzothiazine-3-carboxamide, 1,1-dioxides |
US6174868B1 (en) | 1992-09-10 | 2001-01-16 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of hepatitis C virus-associated diseases |
CA2167537A1 (en) | 1993-07-19 | 1995-02-02 | Tsuneo Ozeki | Hepatitis c virus proliferation inhibitor |
RO117850B1 (ro) | 1993-11-19 | 2002-08-30 | Parke Davis & Co | Derivati de 5,6-dihidropirona ca inhibitori de proteaza si agenti antivirali |
US5504104A (en) | 1993-11-19 | 1996-04-02 | Warner-Lambert Company | Tricyclic pyrone derivatives as protease inhibitors and antiviral agents |
WO1995014012A1 (en) | 1993-11-19 | 1995-05-26 | Parke, Davis & Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
US5808062A (en) | 1993-11-19 | 1998-09-15 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
US5789440A (en) | 1993-11-19 | 1998-08-04 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
US5834506A (en) * | 1996-11-01 | 1998-11-10 | Warner-Lambert Company | Dihydropyrones with improved antiviral activity |
NZ510013A (en) | 1998-09-11 | 2003-11-28 | Warner Lambert Co | Dihydropyrones with selected heterocycles replacing the phenyls bearing polar substituents used as HIV protease inhibitors |
US6512006B1 (en) | 1999-12-09 | 2003-01-28 | Warner-Lambert Company | HIV protease inhibitors |
EP1256628A3 (en) | 2001-05-10 | 2003-03-19 | Agouron Pharmaceuticals, Inc. | Hepatitis c virus (hcv) ns5b rna polymerase and mutants thereof |
DOP2003000641A (es) | 2002-05-10 | 2003-11-15 | Pfizer | Inhibidores de las arn polimerasa dependiente de arn del virus de las hepatitis c y composiciones y tratamiento que los usan |
US7148226B2 (en) * | 2003-02-21 | 2006-12-12 | Agouron Pharmaceuticals, Inc. | Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same |
ATE506364T1 (de) * | 2004-08-18 | 2011-05-15 | Pfizer | Inhibitoren der rna-abhängigen rna-polymerase des hepatitis-c-virus und zusammensetzungen und behandlungen, bei denen diese verwendet werden |
-
2005
- 2005-08-05 AT AT05775853T patent/ATE506364T1/de active
- 2005-08-05 EP EP05775853A patent/EP1781662B1/en active Active
- 2005-08-05 GE GEAP20059868A patent/GEP20094751B/en unknown
- 2005-08-05 AP AP2007003918A patent/AP2313A/xx active
- 2005-08-05 PL PL05775853T patent/PL1781662T3/pl unknown
- 2005-08-05 CN CN2005800280919A patent/CN101006092B/zh active Active
- 2005-08-05 NZ NZ552874A patent/NZ552874A/en not_active IP Right Cessation
- 2005-08-05 RS RS20110257A patent/RS51794B/en unknown
- 2005-08-05 UA UAA200700852A patent/UA88909C2/ru unknown
- 2005-08-05 DK DK05775853.4T patent/DK1781662T3/da active
- 2005-08-05 MX MX2007001527A patent/MX2007001527A/es active IP Right Grant
- 2005-08-05 GE GEAP200510998A patent/GEP20115305B/en unknown
- 2005-08-05 PT PT05775853T patent/PT1781662E/pt unknown
- 2005-08-05 AU AU2005273619A patent/AU2005273619B2/en not_active Ceased
- 2005-08-05 DE DE602005027580T patent/DE602005027580D1/de active Active
- 2005-08-05 SI SI200531314T patent/SI1781662T1/sl unknown
- 2005-08-05 CN CN2009101381353A patent/CN101538268B/zh active Active
- 2005-08-05 CA CA2577525A patent/CA2577525C/en not_active Expired - Fee Related
- 2005-08-05 BR BRPI0514425-6A patent/BRPI0514425A/pt not_active IP Right Cessation
- 2005-08-05 KR KR1020077006118A patent/KR100851178B1/ko active IP Right Grant
- 2005-08-05 JP JP2007526609A patent/JP4372195B2/ja not_active Expired - Fee Related
- 2005-08-05 EA EA200700338A patent/EA012605B1/ru not_active IP Right Cessation
- 2005-08-05 WO PCT/IB2005/002697 patent/WO2006018725A1/en active Application Filing
- 2005-08-05 ES ES05775853T patent/ES2361845T3/es active Active
- 2005-08-12 MY MYPI20053809A patent/MY146123A/en unknown
- 2005-08-15 UY UY29068A patent/UY29068A1/es not_active Application Discontinuation
- 2005-08-15 PE PE2005000945A patent/PE20060677A1/es not_active Application Discontinuation
- 2005-08-15 US US11/204,269 patent/US7151105B2/en not_active Expired - Fee Related
- 2005-08-16 AR ARP050103438A patent/AR050699A1/es active IP Right Grant
- 2005-08-16 GT GT200500221A patent/GT200500221A/es unknown
- 2005-08-17 NL NL1029755A patent/NL1029755C2/nl not_active IP Right Cessation
- 2005-08-17 TW TW094128016A patent/TWI376379B/zh active
- 2005-08-18 HN HN2005000449A patent/HN2005000449A/es unknown
- 2005-08-18 SV SV2005002202A patent/SV2007002202A/es not_active Application Discontinuation
-
2006
- 2006-09-06 US US11/470,540 patent/US7622605B2/en not_active Expired - Fee Related
-
2007
- 2007-01-24 IL IL180933A patent/IL180933A/en not_active IP Right Cessation
- 2007-01-26 ZA ZA200700779A patent/ZA200700779B/xx unknown
- 2007-02-15 NI NI200700043A patent/NI200700043A/es unknown
- 2007-02-16 MA MA29684A patent/MA28803B1/fr unknown
- 2007-02-16 CR CR8935A patent/CR8935A/es unknown
- 2007-02-16 EC EC2007007264A patent/ECSP077264A/es unknown
- 2007-02-16 TN TNP2007000066A patent/TNSN07066A1/fr unknown
- 2007-03-08 NO NO20071274A patent/NO20071274L/no not_active Application Discontinuation
-
2008
- 2008-01-07 HK HK08100120.5A patent/HK1109617A1/xx not_active IP Right Cessation
- 2008-07-20 IL IL192919A patent/IL192919A0/en unknown
-
2009
- 2009-07-15 US US12/503,286 patent/US8268835B2/en not_active Expired - Fee Related
-
2011
- 2011-03-21 CR CR20110153A patent/CR20110153A/es unknown
- 2011-05-17 CY CY20111100486T patent/CY1111480T1/el unknown
- 2011-06-17 HR HR20110458T patent/HRP20110458T1/hr unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20110458T1 (hr) | Inhibitori rna-ovisne rna-polimeraze iz virusa hepatitisa c, te pripravci i liječenje u kojem se koriste | |
JP5911638B2 (ja) | ベンゾチアゾール−6−イル酢酸誘導体およびhiv感染を処置するためのそれらの使用 | |
JP7335003B2 (ja) | Shp2ホスファターゼアロステリック阻害物質 | |
AU2016368317B2 (en) | Inhibitors of influenza virus replication, application methods and uses thereof | |
RU2380101C2 (ru) | Бициклические пиримидины, ингибирующие hcv | |
KR101967172B1 (ko) | 인플루엔자 바이러스 복제의 억제제 | |
TW202122387A (zh) | Mta協同性之prmt5抑制劑 | |
KR20150000871A (ko) | 4,4,-이치환-1,4-디하이드로피리미딘 및 b형 간염의 치료를 위한 약제로서 이의 용도 | |
JP7159307B2 (ja) | Atrキナーゼの複素環式阻害剤 | |
JP2020527588A5 (ja) | ||
EP3197883A1 (en) | Novel compounds | |
AU2017376541B2 (en) | Inhibitors of influenza virus replication and uses thereof | |
CA2429728A1 (en) | Tyrosine kinase inhibitors | |
JP2012501312A5 (ja) | ||
KR20120089648A (ko) | 결핵 억제제로서의 피리미딘 화합물 | |
JP2012528166A5 (ja) | ||
RU2007130896A (ru) | Индольные производные для лечения вирусных инфекций | |
KR20140024203A (ko) | 피리돈 및 아자-피리돈 화합물 및 사용 방법 | |
JP2009513571A (ja) | ヤヌスキナーゼ阻害剤として有用なデアザプリン | |
KR102440843B1 (ko) | Hiv 역전사효소 억제제의 전구약물 | |
CN101918079A (zh) | 蛋白激酶抑制剂及其用途 | |
JP2020527593A5 (ja) | ||
JP2021529815A (ja) | 肝再生促進又は肝細胞死の抑制もしくは防止のためのプロテインキナーゼ阻害剤 | |
CA3213088A1 (en) | Substituted 1-aryl-1'-heteroaryl compounds, substituted 1,1'-biheteroaryl compounds, and methods using same | |
JP2011524359A (ja) | 3環式インドール誘導体およびその使用方法 |