JP2010528987A5 - - Google Patents
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- JP2010528987A5 JP2010528987A5 JP2010507576A JP2010507576A JP2010528987A5 JP 2010528987 A5 JP2010528987 A5 JP 2010528987A5 JP 2010507576 A JP2010507576 A JP 2010507576A JP 2010507576 A JP2010507576 A JP 2010507576A JP 2010528987 A5 JP2010528987 A5 JP 2010528987A5
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- 150000001875 compounds Chemical class 0.000 claims 106
- 239000008194 pharmaceutical composition Substances 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical group 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrugs Drugs 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 241000711549 Hepacivirus C Species 0.000 claims 5
- 230000001808 coupling Effects 0.000 claims 5
- 238000010168 coupling process Methods 0.000 claims 5
- 238000005859 coupling reaction Methods 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 230000037406 food intake Effects 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 2 -cyclopropyl Chemical group 0.000 claims 4
- 101700046422 IFNA Proteins 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- 230000002194 synthesizing Effects 0.000 claims 4
- 102000033147 ERVK-25 Human genes 0.000 claims 3
- 102100016020 IFNG Human genes 0.000 claims 3
- 108091005771 Peptidases Proteins 0.000 claims 3
- 239000004365 Protease Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 201000009910 diseases by infectious agent Diseases 0.000 claims 3
- 235000013305 food Nutrition 0.000 claims 3
- 235000012631 food intake Nutrition 0.000 claims 3
- 108010010648 interferon alfacon-1 Proteins 0.000 claims 3
- 239000002777 nucleoside Substances 0.000 claims 3
- 101700086956 IFNG Proteins 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- BENKAPCDIOILGV-RQJHMYQMSA-N (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(O)=O BENKAPCDIOILGV-RQJHMYQMSA-N 0.000 claims 1
- 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 claims 1
- SUPKOOSCJHTBAH-UHFFFAOYSA-N 2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid Chemical compound NC1=NC=NC2=C1N=CN2CCOCP(O)(O)=O SUPKOOSCJHTBAH-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 230000035533 AUC Effects 0.000 claims 1
- 230000037275 AUC 0-24 Effects 0.000 claims 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N Abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N Benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
- 229960000724 Cidofovir Drugs 0.000 claims 1
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovirum Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 claims 1
- 229940014461 Combivir Drugs 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 1
- 229940090438 Infergen Drugs 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 229950003954 Isatoribine Drugs 0.000 claims 1
- 210000004185 Liver Anatomy 0.000 claims 1
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims 1
- 229960000329 Ribavirin Drugs 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N Ritonavir Chemical group N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims 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 claims 1
- HBOMLICNUCNMMY-XLPZGREQSA-N Zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims 1
- GLWHPRRGGYLLRV-XLPZGREQSA-N [[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](N=[N+]=[N-])C1 GLWHPRRGGYLLRV-XLPZGREQSA-N 0.000 claims 1
- 229960004748 abacavir Drugs 0.000 claims 1
- 229960001997 adefovir Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- WREGKURFCTUGRC-POYBYMJQSA-N ddC Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N ddIno Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims 1
- 230000002708 enhancing Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 230000003908 liver function Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 239000006186 oral dosage form Substances 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 229960000311 ritonavir Drugs 0.000 claims 1
- 239000003730 rna directed rna polymerase inhibitor Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 230000002459 sustained Effects 0.000 claims 1
- 229950006081 taribavirin Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003612 virological Effects 0.000 claims 1
- FPULJIHNWKBSCZ-UHFFFAOYSA-N CC(N(C1)Cc2c1cccc2)=O Chemical compound CC(N(C1)Cc2c1cccc2)=O FPULJIHNWKBSCZ-UHFFFAOYSA-N 0.000 description 1
- FTXOZGZEHSVRFY-IKOVWHKNSA-N CCOC(C(CNC([C@H](C[C@H](C1)O)N1C1=O)=O)=C=CCCCCC[C@@H]1NC(C(F)(F)F)=O)=O Chemical compound CCOC(C(CNC([C@H](C[C@H](C1)O)N1C1=O)=O)=C=CCCCCC[C@@H]1NC(C(F)(F)F)=O)=O FTXOZGZEHSVRFY-IKOVWHKNSA-N 0.000 description 1
- 0 CC[C@@]1C(CC(C2)C2(C(N*)=O)NC(C(CC(C2)O*)N2C(C(CC**)N*)=O)=O)C(*)C1* Chemical compound CC[C@@]1C(CC(C2)C2(C(N*)=O)NC(C(CC(C2)O*)N2C(C(CC**)N*)=O)=O)C(*)C1* 0.000 description 1
- JVKMNJPBSOZEKG-UHFFFAOYSA-N OC(C1(CCC2)N2C(CNC(C(F)(F)F)=O)=O)C1=O Chemical compound OC(C1(CCC2)N2C(CNC(C(F)(F)F)=O)=O)C1=O JVKMNJPBSOZEKG-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91589607P | 2007-05-03 | 2007-05-03 | |
| US95763007P | 2007-08-23 | 2007-08-23 | |
| US1564407P | 2007-12-20 | 2007-12-20 | |
| PCT/US2008/062552 WO2008137779A2 (en) | 2007-05-03 | 2008-05-02 | Novel macrocyclic inhibitors of hepatitis c virus replication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010528987A JP2010528987A (ja) | 2010-08-26 |
| JP2010528987A5 true JP2010528987A5 (US06780888-20040824-C00057.png) | 2011-06-16 |
Family
ID=39638815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010507576A Pending JP2010528987A (ja) | 2007-05-03 | 2008-05-02 | Ｃ型肝炎ウイルス複製の新規大環状阻害剤 |
Country Status (22)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2003007697A (ja) * | 2001-06-21 | 2003-01-10 | Hitachi Kokusai Electric Inc | 半導体装置の製造方法、基板処理方法および基板処理装置 |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| SG166791A1 (en) * | 2005-07-25 | 2010-12-29 | Intermune Inc | Novel macrocyclic inhibitors of hepatitis c virus replication |
| DE602006019323D1 (de) * | 2005-10-11 | 2011-02-10 | Intermune Inc | Verbindungen und verfahren zur inhibierung der replikation des hepatitis-c-virus |
| RU2008152171A (ru) * | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| BRPI0811447A2 (pt) | 2007-05-10 | 2014-10-29 | Intermune Inc | Compostos, composição farmacêutica e métodos de inibição da atividade da protease ns3/ns4, de tratamento da fibrose hepática e de intensificação da função hepática num indivíduo tendo infecção de vírus da hepatite c. |
| EP2282762A2 (en) * | 2008-04-15 | 2011-02-16 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| US20090285773A1 (en) * | 2008-05-15 | 2009-11-19 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20090285774A1 (en) * | 2008-05-15 | 2009-11-19 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
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| AR075584A1 (es) * | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| JP2012523419A (ja) | 2009-04-08 | 2012-10-04 | イデニク プハルマセウティカルス，インコーポレイテッド | 大環状セリンプロテアーゼ阻害剤 |
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| KR20120110090A (ko) * | 2009-09-28 | 2012-10-09 | 에프. 호프만-라 로슈 리미티드 | Ｃ형 간염 바이러스 복제의 신규한 마크로시클릭 저해제 |
| IN2012DN02693A (US06780888-20040824-C00057.png) | 2009-09-28 | 2015-09-04 | Intermune Inc | |
| WO2012082672A2 (en) * | 2010-12-14 | 2012-06-21 | Merck Sharp & Dohme Corp. | Process and intermediates for preparing macrolactams |
| WO2012092409A2 (en) * | 2010-12-30 | 2012-07-05 | Enanta Phararmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
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| AU2013226944B2 (en) * | 2012-02-29 | 2017-03-23 | Toray Industries, Inc. | Inhibitory agent for body cavity fluid accumulation |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| KR20150074051A (ko) * | 2012-10-19 | 2015-07-01 | 브리스톨-마이어스 스큅 컴퍼니 | C형 간염 바이러스 억제제 |
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| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| JP6342922B2 (ja) | 2013-03-07 | 2018-06-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
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| US11192914B2 (en) | 2016-04-28 | 2021-12-07 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
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| KR20220070005A (ko) | 2019-09-26 | 2022-05-27 | 노파르티스 아게 | 항바이러스성 피라졸로피리디논 화합물 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
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2008
- 2008-05-02 WO PCT/US2008/062552 patent/WO2008137779A2/en active Application Filing
- 2008-05-02 MX MX2009011867A patent/MX2009011867A/es not_active Application Discontinuation
- 2008-05-02 SG SG2011065919A patent/SG174809A1/en unknown
- 2008-05-02 EA EA200971026A patent/EA200971026A1/ru unknown
- 2008-05-02 EP EP09177761A patent/EP2177523A1/en not_active Withdrawn
- 2008-05-02 EP EP08755035A patent/EP2160392A2/en not_active Withdrawn
- 2008-05-02 AU AU2008247509A patent/AU2008247509A1/en not_active Abandoned
- 2008-05-02 BR BRPI0811020-4A patent/BRPI0811020A2/pt not_active IP Right Cessation
- 2008-05-02 US US12/114,639 patent/US20090155209A1/en not_active Abandoned
- 2008-05-02 KR KR1020097024599A patent/KR20100024920A/ko not_active Application Discontinuation
- 2008-05-02 NZ NZ581606A patent/NZ581606A/xx not_active IP Right Cessation
- 2008-05-02 AP AP2009005053A patent/AP2009005053A0/en unknown
- 2008-05-02 JP JP2010507576A patent/JP2010528987A/ja active Pending
- 2008-05-02 CA CA002686138A patent/CA2686138A1/en not_active Abandoned
- 2008-05-02 CN CN200880018710A patent/CN101784549A/zh active Pending
- 2008-05-02 CL CL2008001274A patent/CL2008001274A1/es unknown
- 2008-05-05 TW TW097116495A patent/TW200906830A/zh unknown
- 2008-05-05 AR ARP080101901A patent/AR066448A1/es unknown
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2009
- 2009-10-26 IL IL201757A patent/IL201757A0/en unknown
- 2009-10-30 TN TNP2009000457A patent/TN2009000457A1/fr unknown
- 2009-11-26 MA MA32378A patent/MA31496B1/fr unknown
- 2009-11-30 CO CO09136460A patent/CO6251243A2/es not_active Application Discontinuation
- 2009-12-02 EC EC2009009780A patent/ECSP099780A/es unknown
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