TW201036988A - Phosphothiophene and phosphothiazole HCV polymerase inhibitors - Google Patents

Info

Publication number

TW201036988A

TW201036988A TW099106301A TW99106301A TW201036988A TW 201036988 A TW201036988 A TW 201036988A TW 099106301 A TW099106301 A TW 099106301A TW 99106301 A TW99106301 A TW 99106301A TW 201036988 A TW201036988 A TW 201036988A

Authority

TW

Taiwan

Prior art keywords

group

compound

alkyl

doc

cycloalkyl

Prior art date

2009-03-04

Links

• Espacenet
• Global Dossier
• Discuss

• DSSXOTLSYIDBSH-UHFFFAOYSA-N O=P(=O)C1=NC=CS1 Chemical compound O=P(=O)C1=NC=CS1 DSSXOTLSYIDBSH-UHFFFAOYSA-N 0.000 title abstract 2
• JCVUDCBIOSOBRZ-UHFFFAOYSA-N oxido-oxo-thiophen-2-ylphosphanium Chemical compound O=P(=O)C1=CC=CS1 JCVUDCBIOSOBRZ-UHFFFAOYSA-N 0.000 title abstract 2
• 229940124683 HCV polymerase inhibitor Drugs 0.000 title description 2
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• 238000000034 method Methods 0.000 claims abstract description 83
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• 238000011282 treatment Methods 0.000 claims abstract description 17
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• -1 dilute Chemical group 0.000 claims description 206
• 239000000203 mixture Substances 0.000 claims description 169
• 125000003118 aryl group Chemical group 0.000 claims description 161
• 125000000217 alkyl group Chemical group 0.000 claims description 158
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 111
• 125000001072 heteroaryl group Chemical group 0.000 claims description 111
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 107
• 125000000304 alkynyl group Chemical group 0.000 claims description 99
• 125000000623 heterocyclic group Chemical group 0.000 claims description 90
• 125000003342 alkenyl group Chemical group 0.000 claims description 89
• 239000000651 prodrug Substances 0.000 claims description 61
• 229940002612 prodrug Drugs 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 57
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 56
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• GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 claims description 4
• GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical compound C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 claims description 4
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• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 239000002773 nucleotide Substances 0.000 claims description 4
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 4
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• 231100000678 Mycotoxin Toxicity 0.000 claims description 3
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