JP2015525221A5 - - Google Patents
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- JP2015525221A5 JP2015525221A5 JP2015516258A JP2015516258A JP2015525221A5 JP 2015525221 A5 JP2015525221 A5 JP 2015525221A5 JP 2015516258 A JP2015516258 A JP 2015516258A JP 2015516258 A JP2015516258 A JP 2015516258A JP 2015525221 A5 JP2015525221 A5 JP 2015525221A5
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- JP
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- Prior art keywords
- alkyl
- alkoxy
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- formula
- stereoisomers
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 39
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 230000009385 viral infection Effects 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000003003 spiro group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 208000036142 Viral infection Diseases 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- -1 cyano, hydroxyl Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 241000711573 Coronaviridae Species 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound 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 claims description 4
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 239000002777 nucleoside Substances 0.000 claims description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- 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 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- 208000001490 Dengue Diseases 0.000 claims description 2
- 206010012310 Dengue fever Diseases 0.000 claims description 2
- 206010014596 Encephalitis Japanese B Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 2
- 241000711549 Hepacivirus C Species 0.000 claims description 2
- 241000700721 Hepatitis B virus Species 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 102000014150 Interferons Human genes 0.000 claims description 2
- 108010050904 Interferons Proteins 0.000 claims description 2
- 201000005807 Japanese encephalitis Diseases 0.000 claims description 2
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 2
- 201000005805 Murray valley encephalitis Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 241000315672 SARS coronavirus Species 0.000 claims description 2
- 206010041896 St. Louis Encephalitis Diseases 0.000 claims description 2
- 229940124615 TLR 7 agonist Drugs 0.000 claims description 2
- 208000004006 Tick-borne encephalitis Diseases 0.000 claims description 2
- 201000006449 West Nile encephalitis Diseases 0.000 claims description 2
- 208000003152 Yellow Fever Diseases 0.000 claims description 2
- 229960000517 boceprevir Drugs 0.000 claims description 2
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000025729 dengue disease Diseases 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 229940079322 interferon Drugs 0.000 claims description 2
- 239000002773 nucleotide Substances 0.000 claims description 2
- 125000003729 nucleotide group Chemical group 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 229960002063 sofosbuvir Drugs 0.000 claims description 2
- TTZHDVOVKQGIBA-IQWMDFIBSA-N sofosbuvir Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IQWMDFIBSA-N 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 229960002935 telaprevir Drugs 0.000 claims description 2
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims description 2
- 108010017101 telaprevir Proteins 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 1
- 241000907316 Zika virus Species 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 16
- 229940002612 prodrug Drugs 0.000 description 16
- 239000000651 prodrug Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 11
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 241000710781 Flaviviridae Species 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 1
- 108020000999 Viral RNA Proteins 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261657562P | 2012-06-08 | 2012-06-08 | |
| US61/657,562 | 2012-06-08 | ||
| PCT/US2013/044812 WO2013185093A1 (en) | 2012-06-08 | 2013-06-07 | Macrocyclic inhibitors of flaviviridae viruses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015525221A JP2015525221A (ja) | 2015-09-03 |
| JP2015525221A5 true JP2015525221A5 (enExample) | 2016-07-21 |
| JP6273268B2 JP6273268B2 (ja) | 2018-01-31 |
Family
ID=48626704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015516258A Active JP6273268B2 (ja) | 2012-06-08 | 2013-06-07 | フラビウイルス科ウイルスの大環状阻害剤 |
Country Status (33)
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9428845B1 (en) | 2010-12-28 | 2016-08-30 | Warp Drive Bio, Inc. | Identifying new therapeutic agents |
| WO2013185103A1 (en) | 2012-06-08 | 2013-12-12 | Gilead Sciences, Inc. | Macrocyclic inhibitors of flaviviridae viruses |
| AR091279A1 (es) | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| WO2013185090A1 (en) | 2012-06-08 | 2013-12-12 | Gilead Sciences, Inc. | Macrocyclic inhibitors of flaviviridae viruses |
| US9233974B2 (en) | 2012-12-21 | 2016-01-12 | Gilead Sciences, Inc. | Antiviral compounds |
| NZ729172A (en) | 2013-01-31 | 2018-06-29 | Gilead Pharmasset Llc | Combination formulation of two antiviral compounds |
| JP2016529293A (ja) | 2013-08-27 | 2016-09-23 | ギリアド ファーマセット エルエルシー | ２つの抗ウイルス化合物の組合せ製剤 |
| WO2015084741A2 (en) | 2013-12-02 | 2015-06-11 | Gilead Pharmasset Llc | Methods of treating hepatitis c virus infection in subjects with cirrhosis |
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| KR102526964B1 (ko) | 2018-02-26 | 2023-04-28 | 길리애드 사이언시즈, 인코포레이티드 | Hbv 복제 억제제로서의 치환된 피롤리진 화합물 |
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