JP2014514308A5 - - Google Patents
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- JP2014514308A5 JP2014514308A5 JP2014505381A JP2014505381A JP2014514308A5 JP 2014514308 A5 JP2014514308 A5 JP 2014514308A5 JP 2014505381 A JP2014505381 A JP 2014505381A JP 2014505381 A JP2014505381 A JP 2014505381A JP 2014514308 A5 JP2014514308 A5 JP 2014514308A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- alkynyl
- alkenyl
- substituted
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 31
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 29
- 150000001721 carbon Chemical group 0.000 claims description 28
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 24
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 24
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 24
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 18
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 229940035893 uracil Drugs 0.000 claims description 12
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 229940104302 cytosine Drugs 0.000 claims description 10
- 239000002777 nucleoside Substances 0.000 claims description 10
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 8
- 230000003612 virological effect Effects 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- -1 R 8 is H Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 5
- 229940122806 Cyclophilin inhibitor Drugs 0.000 claims description 5
- 241000711549 Hepacivirus C Species 0.000 claims description 5
- 102000014150 Interferons Human genes 0.000 claims description 5
- 108010050904 Interferons Proteins 0.000 claims description 5
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 5
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 5
- 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 claims description 5
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 5
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 229940079322 interferon Drugs 0.000 claims description 5
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- DKSVBVKHUICELN-UHFFFAOYSA-N 3-ethoxy-6-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]-1,2-benzoxazole Chemical compound C=1C=C2C(OCC)=NOC2=CC=1OCCC(CC1)CCN1C1=CC=C(C)N=N1 DKSVBVKHUICELN-UHFFFAOYSA-N 0.000 claims description 4
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 229940125400 channel inhibitor Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- KQOXLKOJHVFTRN-UHFFFAOYSA-N pleconaril Chemical compound O1N=C(C)C=C1CCCOC1=C(C)C=C(C=2N=C(ON=2)C(F)(F)F)C=C1C KQOXLKOJHVFTRN-UHFFFAOYSA-N 0.000 claims description 4
- 229960000471 pleconaril Drugs 0.000 claims description 4
- 239000002911 sialidase inhibitor Substances 0.000 claims description 4
- 229940113082 thymine Drugs 0.000 claims description 4
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 claims description 3
- 241000725619 Dengue virus Species 0.000 claims description 3
- 241000710781 Flaviviridae Species 0.000 claims description 3
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 3
- 241000710912 Kunjin virus Species 0.000 claims description 3
- 241000710908 Murray Valley encephalitis virus Species 0.000 claims description 3
- 241000725177 Omsk hemorrhagic fever virus Species 0.000 claims description 3
- 241000710888 St. Louis encephalitis virus Species 0.000 claims description 3
- 241000710771 Tick-borne encephalitis virus Species 0.000 claims description 3
- 241000710886 West Nile virus Species 0.000 claims description 3
- 241000710772 Yellow fever virus Species 0.000 claims description 3
- 208000020329 Zika virus infectious disease Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 229940051021 yellow-fever virus Drugs 0.000 claims description 3
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 2
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical compound IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- QNRRHYPPQFELSF-CNYIRLTGSA-N Laninamivir Chemical compound OC[C@@H](O)[C@@H](OC)[C@@H]1OC(C(O)=O)=C[C@H](N=C(N)N)[C@H]1NC(C)=O QNRRHYPPQFELSF-CNYIRLTGSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003805 amantadine Drugs 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229950004244 laninamivir Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical group CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims description 2
- 229960003752 oseltamivir Drugs 0.000 claims description 2
- XRQDFNLINLXZLB-CKIKVBCHSA-N peramivir Chemical compound CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N XRQDFNLINLXZLB-CKIKVBCHSA-N 0.000 claims description 2
- 229960001084 peramivir Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229960000888 rimantadine Drugs 0.000 claims description 2
- 229960001028 zanamivir Drugs 0.000 claims description 2
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 241000124008 Mammalia Species 0.000 description 3
- 229910019946 S-S Inorganic materials 0.000 description 3
- 229910019939 S—S Inorganic materials 0.000 description 3
- 241000711557 Hepacivirus Species 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 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 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161474848P | 2011-04-13 | 2011-04-13 | |
| US61/474,848 | 2011-04-13 | ||
| PCT/US2012/033675 WO2012142523A2 (en) | 2011-04-13 | 2012-04-13 | 1'-substituted pyrimidine n-nucleoside analogs for antiviral treatment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014514308A JP2014514308A (ja) | 2014-06-19 |
| JP2014514308A5 true JP2014514308A5 (enExample) | 2015-05-28 |
| JP6043338B2 JP6043338B2 (ja) | 2016-12-14 |
Family
ID=46001834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014505381A Expired - Fee Related JP6043338B2 (ja) | 2011-04-13 | 2012-04-13 | 抗ウイルス治療用の１’−置換ピリミジンｎ−ヌクレオシド類似体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8877733B2 (enExample) |
| EP (1) | EP2697241B1 (enExample) |
| JP (1) | JP6043338B2 (enExample) |
| KR (1) | KR20140019832A (enExample) |
| CN (1) | CN103476783A (enExample) |
| AU (1) | AU2012242517B2 (enExample) |
| BR (1) | BR112013026219A2 (enExample) |
| CA (1) | CA2830689A1 (enExample) |
| EA (1) | EA201391264A1 (enExample) |
| ES (1) | ES2744587T3 (enExample) |
| IL (1) | IL228680A0 (enExample) |
| MX (1) | MX2013011915A (enExample) |
| WO (1) | WO2012142523A2 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| US9676797B2 (en) * | 2015-09-02 | 2017-06-13 | Abbvie Inc. | Anti-viral compounds |
| HRP20130862T1 (hr) | 2009-09-21 | 2013-10-25 | Gilead Sciences, Inc. | Procesi i intermedijeri za pripravu analoga 1'-cijanokarbanukleozida |
| UA111163C2 (uk) | 2010-07-22 | 2016-04-11 | Гайлід Сайєнсіз, Інк. | Способи й сполуки для лікування вірусних інфекцій paramyxoviridae |
| WO2013039920A1 (en) | 2011-09-12 | 2013-03-21 | Idenix Pharmaceuticals, Inc. | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2013056046A1 (en) | 2011-10-14 | 2013-04-18 | Idenix Pharmaceuticals, Inc. | Substituted 3',5'-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections |
| EP2852605B1 (en) | 2012-05-22 | 2018-01-31 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphate prodrugs for hcv infection |
| BR112014029115A8 (pt) | 2012-05-22 | 2018-04-03 | Idenix Pharmaceuticals Inc | Composto, composição farmacêutica, e, uso de um composto ou composição |
| EP2852604B1 (en) * | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| MX2014014323A (es) | 2012-05-25 | 2015-02-12 | Janssen R & D Ireland | Nucleosidos de espirooxetano de uracilo. |
| EP2890704B1 (en) | 2012-08-31 | 2018-02-28 | Novartis AG | 2'-ethynyl nucleoside derivatives for treatment of viral infections |
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| WO2014099941A1 (en) * | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| JP6284547B2 (ja) | 2012-12-21 | 2018-02-28 | アリオス バイオファーマ インク． | 置換ヌクレオシド、置換ヌクレオチドおよびそれらの類似体 |
| US9339541B2 (en) | 2013-03-04 | 2016-05-17 | Merck Sharp & Dohme Corp. | Thiophosphate nucleosides for the treatment of HCV |
| WO2014137926A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | 3'-deoxy nucleosides for the treatment of hcv |
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| CN105705511A (zh) * | 2013-04-12 | 2016-06-22 | 艾其林医药公司 | 用于治疗hcv的氘化核苷前药 |
| EP3004130B1 (en) | 2013-06-05 | 2019-08-07 | Idenix Pharmaceuticals LLC. | 1',4'-thio nucleosides for the treatment of hcv |
| EP3027636B1 (en) | 2013-08-01 | 2022-01-05 | Idenix Pharmaceuticals LLC | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| EP3055319A4 (en) | 2013-10-11 | 2018-01-10 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| WO2015061683A1 (en) * | 2013-10-25 | 2015-04-30 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate and d-alanine thiophosphoramidate pronucleotides of nucleoside compounds useful for the treatment of hcv |
| EP3131914B1 (en) | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| TWI767201B (zh) * | 2014-10-29 | 2022-06-11 | 美商基利科學股份有限公司 | 絲狀病毒科病毒感染之治療 |
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| TWI890963B (zh) | 2020-03-12 | 2025-07-21 | 美商基利科學股份有限公司 | 1'-氰基核苷之製備方法 |
| CN111548384B (zh) * | 2020-03-29 | 2021-04-27 | 常州安蒂卫生物科技有限公司 | 用于抗病毒治疗的被取代的n4-羟基胞苷衍生物及其前药 |
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2012
- 2012-04-13 CN CN2012800181025A patent/CN103476783A/zh active Pending
- 2012-04-13 CA CA2830689A patent/CA2830689A1/en not_active Abandoned
- 2012-04-13 US US13/447,017 patent/US8877733B2/en active Active
- 2012-04-13 AU AU2012242517A patent/AU2012242517B2/en not_active Ceased
- 2012-04-13 EA EA201391264A patent/EA201391264A1/ru unknown
- 2012-04-13 JP JP2014505381A patent/JP6043338B2/ja not_active Expired - Fee Related
- 2012-04-13 MX MX2013011915A patent/MX2013011915A/es not_active Application Discontinuation
- 2012-04-13 KR KR1020137029678A patent/KR20140019832A/ko not_active Withdrawn
- 2012-04-13 ES ES12716969T patent/ES2744587T3/es active Active
- 2012-04-13 WO PCT/US2012/033675 patent/WO2012142523A2/en not_active Ceased
- 2012-04-13 EP EP12716969.6A patent/EP2697241B1/en active Active
- 2012-04-13 BR BR112013026219A patent/BR112013026219A2/pt not_active IP Right Cessation
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- 2013-10-02 IL IL228680A patent/IL228680A0/en unknown
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