JP2012526838A5 - - Google Patents
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- JP2012526838A5 JP2012526838A5 JP2012510987A JP2012510987A JP2012526838A5 JP 2012526838 A5 JP2012526838 A5 JP 2012526838A5 JP 2012510987 A JP2012510987 A JP 2012510987A JP 2012510987 A JP2012510987 A JP 2012510987A JP 2012526838 A5 JP2012526838 A5 JP 2012526838A5
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- JP
- Japan
- Prior art keywords
- alkyl
- independently
- item
- aryl
- independently selected
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 178
- 150000003839 salts Chemical class 0.000 claims description 21
- 229940002612 prodrug Drugs 0.000 claims description 19
- 239000000651 prodrug Substances 0.000 claims description 19
- 208000005176 Hepatitis C Diseases 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 6
- 230000000069 prophylactic effect Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 613
- 125000000623 heterocyclic group Chemical group 0.000 description 362
- 125000003118 aryl group Chemical group 0.000 description 285
- 125000003710 aryl alkyl group Chemical group 0.000 description 215
- 125000000753 cycloalkyl group Chemical group 0.000 description 200
- 125000001188 haloalkyl group Chemical group 0.000 description 200
- 125000005843 halogen group Chemical group 0.000 description 170
- 125000003545 alkoxy group Chemical group 0.000 description 168
- 125000003342 alkenyl group Chemical group 0.000 description 129
- 125000004438 haloalkoxy group Chemical group 0.000 description 126
- 125000000304 alkynyl group Chemical group 0.000 description 105
- 229910052739 hydrogen Inorganic materials 0.000 description 105
- 239000001257 hydrogen Substances 0.000 description 105
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 105
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 104
- 125000004093 cyano group Chemical group *C#N 0.000 description 99
- 125000004043 oxo group Chemical group O=* 0.000 description 99
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 97
- -1 carboxy, formyl Chemical group 0.000 description 86
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 86
- 125000004966 cyanoalkyl group Chemical group 0.000 description 76
- 125000004122 cyclic group Chemical group 0.000 description 71
- 125000001072 heteroaryl group Chemical group 0.000 description 67
- 229920006395 saturated elastomer Polymers 0.000 description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 60
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 57
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 54
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 52
- 229910052717 sulfur Inorganic materials 0.000 description 49
- 229910052799 carbon Inorganic materials 0.000 description 48
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 46
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 46
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 45
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 44
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 44
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 43
- 125000005129 aryl carbonyl group Chemical group 0.000 description 43
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 43
- 125000003302 alkenyloxy group Chemical group 0.000 description 42
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 42
- 125000004103 aminoalkyl group Chemical group 0.000 description 42
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 42
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 42
- 125000000392 cycloalkenyl group Chemical group 0.000 description 40
- 125000001424 substituent group Chemical group 0.000 description 38
- 125000004429 atom Chemical group 0.000 description 37
- 125000005842 heteroatom Chemical group 0.000 description 36
- 125000000033 alkoxyamino group Chemical group 0.000 description 35
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 35
- 150000001721 carbon Chemical group 0.000 description 31
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 31
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 28
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 28
- 229910052760 oxygen Inorganic materials 0.000 description 27
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 23
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 22
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 22
- 125000005180 haloalkoxyalkyloxy group Chemical group 0.000 description 20
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 description 19
- 125000000000 cycloalkoxy group Chemical group 0.000 description 19
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 18
- 125000005159 cyanoalkoxy group Chemical group 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 12
- 125000002619 bicyclic group Chemical group 0.000 description 12
- 125000005339 cyanocycloalkoxy group Chemical group 0.000 description 10
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 description 8
- 125000002837 carbocyclic group Chemical group 0.000 description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 6
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 6
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 description 6
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 6
- 125000005282 allenyl group Chemical group 0.000 description 6
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 6
- 125000005347 halocycloalkyl group Chemical group 0.000 description 6
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 102000014150 Interferons Human genes 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002777 nucleoside Substances 0.000 description 3
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 description 2
- 125000005163 aryl sulfanyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
- 150000001602 bicycloalkyls Chemical group 0.000 description 2
- 125000004965 chloroalkyl group Chemical group 0.000 description 2
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000013160 medical therapy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 description 1
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 description 1
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229950003954 isatoribine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229940127073 nucleoside analogue Drugs 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 description 1
- 229950006081 taribavirin Drugs 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17797209P | 2009-05-13 | 2009-05-13 | |
| US61/177,972 | 2009-05-13 | ||
| US22474509P | 2009-07-10 | 2009-07-10 | |
| US61/224,745 | 2009-07-10 | ||
| US23876009P | 2009-09-01 | 2009-09-01 | |
| US61/238,760 | 2009-09-01 | ||
| PCT/US2010/034600 WO2010132601A1 (en) | 2009-05-13 | 2010-05-12 | Antiviral compounds |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014107359A Division JP5744283B2 (ja) | 2009-05-13 | 2014-05-23 | 抗ウイルス化合物 |
| JP2014124325A Division JP5745727B2 (ja) | 2009-05-13 | 2014-06-17 | 抗ウイルス化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012526838A JP2012526838A (ja) | 2012-11-01 |
| JP2012526838A5 true JP2012526838A5 (enExample) | 2014-07-10 |
| JP5582662B2 JP5582662B2 (ja) | 2014-09-03 |
Family
ID=42645241
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012510987A Active JP5582662B2 (ja) | 2009-05-13 | 2010-05-12 | 抗ウイルス化合物 |
| JP2014107359A Active JP5744283B2 (ja) | 2009-05-13 | 2014-05-23 | 抗ウイルス化合物 |
| JP2014124325A Active JP5745727B2 (ja) | 2009-05-13 | 2014-06-17 | 抗ウイルス化合物 |
| JP2015091474A Withdrawn JP2015157842A (ja) | 2009-05-13 | 2015-04-28 | 抗ウイルス化合物 |
| JP2017095523A Withdrawn JP2017145254A (ja) | 2009-05-13 | 2017-05-12 | 抗ウイルス化合物 |
| JP2018240826A Withdrawn JP2019104732A (ja) | 2009-05-13 | 2018-12-25 | 抗ウイルス化合物 |
| JP2020159623A Pending JP2021001214A (ja) | 2009-05-13 | 2020-09-24 | 抗ウイルス化合物 |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014107359A Active JP5744283B2 (ja) | 2009-05-13 | 2014-05-23 | 抗ウイルス化合物 |
| JP2014124325A Active JP5745727B2 (ja) | 2009-05-13 | 2014-06-17 | 抗ウイルス化合物 |
| JP2015091474A Withdrawn JP2015157842A (ja) | 2009-05-13 | 2015-04-28 | 抗ウイルス化合物 |
| JP2017095523A Withdrawn JP2017145254A (ja) | 2009-05-13 | 2017-05-12 | 抗ウイルス化合物 |
| JP2018240826A Withdrawn JP2019104732A (ja) | 2009-05-13 | 2018-12-25 | 抗ウイルス化合物 |
| JP2020159623A Pending JP2021001214A (ja) | 2009-05-13 | 2020-09-24 | 抗ウイルス化合物 |
Country Status (40)
Families Citing this family (208)
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- 2014-07-17 IL IL233679A patent/IL233679B/en active IP Right Grant
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2015
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- 2015-11-17 CY CY20151101032T patent/CY1116942T1/el unknown
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2016
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- 2016-01-11 LT LTPA2016002C patent/LTC2430014I2/lt unknown
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2017
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2018
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2020
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