JP2012517444A5 - - Google Patents
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- JP2012517444A5 JP2012517444A5 JP2011549324A JP2011549324A JP2012517444A5 JP 2012517444 A5 JP2012517444 A5 JP 2012517444A5 JP 2011549324 A JP2011549324 A JP 2011549324A JP 2011549324 A JP2011549324 A JP 2011549324A JP 2012517444 A5 JP2012517444 A5 JP 2012517444A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- independently
- aryl
- alkynyl
- 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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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 100
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 82
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 49
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000003107 substituted aryl group Chemical group 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 31
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 30
- 239000003112 inhibitor Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- -1 -C (= O) oR 11 Chemical compound 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 239000002777 nucleoside Substances 0.000 claims description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 4
- 241000710781 Flaviviridae Species 0.000 claims description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 4
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 4
- 241000711549 Hepacivirus C Species 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 101800001014 Non-structural protein 5A Proteins 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
- 229940124615 TLR 7 agonist Drugs 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003623 enhancer Substances 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002773 nucleotide Substances 0.000 claims description 4
- 125000003729 nucleotide group Chemical group 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 102000001493 Cyclophilins Human genes 0.000 claims description 3
- 108010068682 Cyclophilins Proteins 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 241000725619 Dengue virus Species 0.000 claims description 2
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 2
- 241000710912 Kunjin virus Species 0.000 claims description 2
- 241000710908 Murray Valley encephalitis virus Species 0.000 claims description 2
- 241000725177 Omsk hemorrhagic fever virus Species 0.000 claims description 2
- 241000710888 St. Louis encephalitis virus Species 0.000 claims description 2
- 241000710771 Tick-borne encephalitis virus Species 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 241000710886 West Nile virus Species 0.000 claims description 2
- 241000710772 Yellow fever virus Species 0.000 claims description 2
- 241000907316 Zika virus Species 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229940051021 yellow-fever virus Drugs 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000000134 cyclophilin inhibitor Substances 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 241000124008 Mammalia Species 0.000 description 1
- 229910019946 S-S Inorganic materials 0.000 description 1
- 229910019939 S—S Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15124809P | 2009-02-10 | 2009-02-10 | |
| US61/151,248 | 2009-02-10 | ||
| PCT/US2010/023586 WO2010093608A1 (en) | 2009-02-10 | 2010-02-09 | Carba-nucleoside analogs for antiviral treatment |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014139374A Division JP5951690B2 (ja) | 2009-02-10 | 2014-07-07 | 抗ウイルス処置のためのカルバ−ヌクレオシドアナログ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012517444A JP2012517444A (ja) | 2012-08-02 |
| JP2012517444A5 true JP2012517444A5 (enExample) | 2013-03-07 |
| JP5746638B2 JP5746638B2 (ja) | 2015-07-08 |
Family
ID=42333309
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011549324A Expired - Fee Related JP5746638B2 (ja) | 2009-02-10 | 2010-02-09 | 抗ウイルス処置のためのカルバ−ヌクレオシドアナログ |
| JP2014139374A Expired - Fee Related JP5951690B2 (ja) | 2009-02-10 | 2014-07-07 | 抗ウイルス処置のためのカルバ−ヌクレオシドアナログ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014139374A Expired - Fee Related JP5951690B2 (ja) | 2009-02-10 | 2014-07-07 | 抗ウイルス処置のためのカルバ−ヌクレオシドアナログ |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8012942B2 (enExample) |
| EP (2) | EP2396340B1 (enExample) |
| JP (2) | JP5746638B2 (enExample) |
| KR (2) | KR101834707B1 (enExample) |
| CN (1) | CN102348713B (enExample) |
| AP (1) | AP2922A (enExample) |
| AU (3) | AU2010213873B2 (enExample) |
| BR (1) | BRPI1013643A2 (enExample) |
| CA (1) | CA2751277C (enExample) |
| CL (1) | CL2011001906A1 (enExample) |
| CO (1) | CO6420354A2 (enExample) |
| DK (1) | DK2396340T3 (enExample) |
| EA (1) | EA025085B1 (enExample) |
| ES (2) | ES2453078T3 (enExample) |
| HR (1) | HRP20140219T1 (enExample) |
| IL (1) | IL214396A (enExample) |
| MX (2) | MX2011008409A (enExample) |
| NZ (1) | NZ594370A (enExample) |
| PE (3) | PE20160858A1 (enExample) |
| PL (1) | PL2396340T3 (enExample) |
| PT (2) | PT2719701T (enExample) |
| SG (1) | SG173186A1 (enExample) |
| SI (1) | SI2396340T1 (enExample) |
| SM (1) | SMT201400056B (enExample) |
| UA (2) | UA112140C2 (enExample) |
| WO (1) | WO2010093608A1 (enExample) |
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| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| CN1849142A (zh) | 2002-11-15 | 2006-10-18 | 埃迪尼克斯(开曼)有限公司 | 2′－支链核苷和黄病毒突变 |
| CN102046626A (zh) | 2008-04-23 | 2011-05-04 | 吉里德科学公司 | 用于抗病毒治疗的carba-核苷类似物 |
| DK2480559T3 (da) * | 2009-09-21 | 2013-08-05 | Gilead Sciences Inc | Fremgangsmåder og mellemprodukter til fremstillingen af 1'-cyano-carbanukleosid-analoger |
| PH12013500033A1 (en) | 2010-07-19 | 2017-07-26 | Gilead Sciences Inc | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| MA34470B1 (fr) | 2010-07-22 | 2013-08-01 | Gilead Sciences Inc | Procédés et composés pour traiter des infections à virus paramyxoviridae |
| AU2011306066B2 (en) * | 2010-09-20 | 2015-01-29 | Gilead Sciences, Inc. | 2' -fluoro substituted carba-nucleoside analogs for antiviral treatment |
| US8841275B2 (en) | 2010-11-30 | 2014-09-23 | Gilead Pharmasset Llc | 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections |
| CA2843324A1 (en) | 2011-03-31 | 2012-11-15 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
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| CN107427530B (zh) | 2015-03-06 | 2020-09-08 | 阿堤亚制药公司 | 用于HCV治疗的β-D-2’-脱氧-2’α-氟-2’-β-C-取代的-2-改性的-N6-取代的嘌呤核苷酸 |
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