NZ590638A - MACROCYCLIC QUINOXALINE COMPOUNDS AS Hepatitis C Virus NS3 PROTEASE INHIBITORS - Google Patents
MACROCYCLIC QUINOXALINE COMPOUNDS AS Hepatitis C Virus NS3 PROTEASE INHIBITORSInfo
- Publication number
- NZ590638A NZ590638A NZ590638A NZ59063809A NZ590638A NZ 590638 A NZ590638 A NZ 590638A NZ 590638 A NZ590638 A NZ 590638A NZ 59063809 A NZ59063809 A NZ 59063809A NZ 590638 A NZ590638 A NZ 590638A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- hcv
- methyl
- ifd
- irb
- Prior art date
Links
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title abstract description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title abstract description 4
- 108700012707 hepatitis C virus NS3 Proteins 0.000 title abstract 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 239000003814 drug Substances 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims description 40
- 208000015181 infectious disease Diseases 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910001868 water Inorganic materials 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229940124597 therapeutic agent Drugs 0.000 claims description 14
- 102000004169 proteins and genes Human genes 0.000 claims description 13
- 108090000623 proteins and genes Proteins 0.000 claims description 13
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 229940124772 HCV-NS5B polymerase inhibitor Drugs 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
- 239000012496 blank sample Substances 0.000 claims description 4
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- 229940122604 HCV protease inhibitor Drugs 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
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- 238000011088 calibration curve Methods 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims 1
- -1 quinoxaline compound Chemical class 0.000 abstract description 17
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 abstract 1
- 241000711549 Hepacivirus C Species 0.000 description 66
- 239000000243 solution Substances 0.000 description 38
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- 239000003443 antiviral agent Substances 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000003112 inhibitor Substances 0.000 description 11
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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- 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
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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| US13555908P | 2008-07-22 | 2008-07-22 | |
| PCT/US2009/050915 WO2010011566A1 (en) | 2008-07-22 | 2009-07-17 | Macrocyclic quinoxaline compounds as hcv ns3 protease inhibitors |
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