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
- Japan
- Prior art keywords
- alkyl
- alkoxy
- halo
- formula
- stereoisomers
- 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 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 (2) | 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)
| Country | Link |
|---|---|
| US (4) | US9062092B2 (2) |
| EP (2) | EP3392253B1 (2) |
| JP (1) | JP6273268B2 (2) |
| KR (1) | KR102185152B1 (2) |
| CN (1) | CN104781261B (2) |
| AP (1) | AP2015008189A0 (2) |
| AR (1) | AR091279A1 (2) |
| AU (1) | AU2013270670B2 (2) |
| BR (1) | BR112014030639A2 (2) |
| CA (1) | CA2875690C (2) |
| CL (1) | CL2014003337A1 (2) |
| CR (1) | CR20150018A (2) |
| EA (1) | EA027134B1 (2) |
| EC (1) | ECSP15000435A (2) |
| ES (2) | ES2894269T3 (2) |
| IL (1) | IL236007B (2) |
| IN (1) | IN2014MN02657A (2) |
| MA (1) | MA37712B1 (2) |
| MD (1) | MD20140135A2 (2) |
| MX (1) | MX358372B (2) |
| NO (1) | NO2885641T3 (2) |
| NZ (1) | NZ703062A (2) |
| PE (1) | PE20150862A1 (2) |
| PH (1) | PH12014502739A1 (2) |
| PL (1) | PL2861601T3 (2) |
| PT (1) | PT2861601T (2) |
| SG (2) | SG10201703969PA (2) |
| SI (1) | SI2861601T1 (2) |
| TW (1) | TWI616448B (2) |
| UA (1) | UA115664C2 (2) |
| UY (1) | UY34851A (2) |
| WO (1) | WO2013185093A1 (2) |
| ZA (1) | ZA201409215B (2) |
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| US9428845B1 (en) | 2010-12-28 | 2016-08-30 | Warp Drive Bio, Inc. | Identifying new therapeutic agents |
| AR091279A1 (es) | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| PT2861604T (pt) | 2012-06-08 | 2017-05-05 | Gilead Sciences Inc | Inibidores macrocíclicos de vírus flaviridae |
| BR112014030649A2 (pt) | 2012-06-08 | 2017-06-27 | Gilead Sciences Inc | inibidores macrocíclicos da flaviviridae vírus |
| US9233974B2 (en) | 2012-12-21 | 2016-01-12 | Gilead Sciences, Inc. | Antiviral compounds |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| PT3038601T (pt) | 2013-08-27 | 2020-06-30 | Gilead Pharmasset Llc | Formulação combinada de dois compostos antivirais |
| WO2015084741A2 (en) | 2013-12-02 | 2015-06-11 | Gilead Pharmasset Llc | Methods of treating hepatitis c virus infection in subjects with cirrhosis |
| TW201609785A (zh) | 2013-12-23 | 2016-03-16 | 吉李德製藥公司 | 固體型之抗病毒化合物 |
| EA030849B1 (ru) | 2014-01-06 | 2018-10-31 | Бристол-Маерс Сквибб Компани | ПИРРОЛИДИНИЛСУЛЬФОНОВЫЕ МОДУЛЯТОРЫ RORγ |
| JP7381190B2 (ja) | 2014-12-26 | 2023-11-15 | エモリー・ユニバーシテイ | Ｎ４－ヒドロキシシチジン及び誘導体並びにそれに関連する抗ウイルス用途 |
| EP3247378B8 (en) | 2015-01-09 | 2023-08-23 | Revolution Medicines, Inc. | Macrocyclic compounds that participate in cooperative binding and medical uses thereof |
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| EA201892375A1 (ru) | 2016-05-27 | 2019-08-30 | Джилид Сайэнс, Инк. | Способы лечения инфекций, вызываемых вирусом гепатита b |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
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| AU2017318601B2 (en) | 2016-09-02 | 2020-09-03 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
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| WO2018136559A1 (en) * | 2017-01-17 | 2018-07-26 | The Regents Of The University Of California | Methods for treating flaviviruses and zika infections |
| TW202510891A (zh) | 2017-01-31 | 2025-03-16 | 美商基利科學股份有限公司 | 替諾福韋埃拉酚胺(tenofovir alafenamide)之晶型 |
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| WO2018172250A1 (en) | 2017-03-21 | 2018-09-27 | Bayer Pharma Aktiengesellschaft | 2-methyl-quinazolines |
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