JP2020534374A5 - - Google Patents
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- JP2020534374A5 JP2020534374A5 JP2020538752A JP2020538752A JP2020534374A5 JP 2020534374 A5 JP2020534374 A5 JP 2020534374A5 JP 2020538752 A JP2020538752 A JP 2020538752A JP 2020538752 A JP2020538752 A JP 2020538752A JP 2020534374 A5 JP2020534374 A5 JP 2020534374A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amino
- compound
- alaninate
- phosphoryl
- 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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- -1 4-amino-2-oxopyrimidine-1 (2H) -yl Chemical group 0.000 claims 84
- 150000001875 compounds Chemical class 0.000 claims 46
- 239000000203 mixture Substances 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000847 cytosin-1-yl group Chemical group [*]N1C(=O)N=C(N([H])[H])C([H])=C1[H] 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 4
- VOWPVJACXJNHBC-UHFFFAOYSA-N methyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC)OC1=CC=CC=C1 VOWPVJACXJNHBC-UHFFFAOYSA-N 0.000 claims 4
- 229940122604 HCV protease inhibitor Drugs 0.000 claims 2
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- 101800000440 Non-structural protein NS3A Proteins 0.000 claims 1
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims 1
- 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 1
- FKRSSPOQAMALKA-CUPIEXAXSA-N daclatasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)=CN1 FKRSSPOQAMALKA-CUPIEXAXSA-N 0.000 claims 1
- 229960005449 daclatasvir Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- 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 1
- 0 C[C@@]1[C@](N(C=CC(N)=N2)C2=O)O[C@](*)(COP(*)(*)=*)[C@@]1O Chemical compound C[C@@]1[C@](N(C=CC(N)=N2)C2=O)O[C@](*)(COP(*)(*)=*)[C@@]1O 0.000 description 17
- KTXAFRDFKKNLLB-UKZBMLMBSA-N C[C@@H](C(OC1CCCCC1)=N)/N=C\[P@](OC[C@](C[C@@H]1C)(O[C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O Chemical compound C[C@@H](C(OC1CCCCC1)=N)/N=C\[P@](OC[C@](C[C@@H]1C)(O[C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O KTXAFRDFKKNLLB-UKZBMLMBSA-N 0.000 description 3
- CNMZIOBNQMYSPI-XWFOKKAGSA-N CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O)=N Chemical compound CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O)=N CNMZIOBNQMYSPI-XWFOKKAGSA-N 0.000 description 2
- QDQVXVRZVCTVHE-YFKPBYRVSA-N CC(C)OC([C@H](C)N)=O Chemical compound CC(C)OC([C@H](C)N)=O QDQVXVRZVCTVHE-YFKPBYRVSA-N 0.000 description 2
- DYLSZPQUPRDHPC-IIEDWPIASA-N CC(C)OC([C@H](C)N[P@@](Oc1ccccc1)([U]C[C@](C[C@@H]1C)(O[C@H]1N(C=CC(N1)=O)C1=O)F)=O)=O Chemical compound CC(C)OC([C@H](C)N[P@@](Oc1ccccc1)([U]C[C@](C[C@@H]1C)(O[C@H]1N(C=CC(N1)=O)C1=O)F)=O)=O DYLSZPQUPRDHPC-IIEDWPIASA-N 0.000 description 2
- JKNSNVFEMWTSSL-OGTHKYEHSA-N CC(C)OC([C@H](C)/N=C/[P@](OCC(C[C@@H]1C)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC([C@H](C)/N=C/[P@](OCC(C[C@@H]1C)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccccc1)=O)=O JKNSNVFEMWTSSL-OGTHKYEHSA-N 0.000 description 1
- OTXDPFGLPIQLGO-RIEPGIFKSA-N CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1cccc2ccccc12)=O)=N Chemical compound CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1cccc2ccccc12)=O)=N OTXDPFGLPIQLGO-RIEPGIFKSA-N 0.000 description 1
- SGRMHUQFYMFOQM-LRQOYWODSA-N CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC([C@H](C)/N=C\[P@](OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)(Oc1ccccc1)=O)=O SGRMHUQFYMFOQM-LRQOYWODSA-N 0.000 description 1
- PJRSPBLUQVTYAQ-RGMNGODLSA-N CC(C)OC([C@H](C)N)=[U] Chemical compound CC(C)OC([C@H](C)N)=[U] PJRSPBLUQVTYAQ-RGMNGODLSA-N 0.000 description 1
- VJHHGWFJYRMRNH-LURJTMIESA-N CC(C)OC([C@H](C)N=C)=O Chemical compound CC(C)OC([C@H](C)N=C)=O VJHHGWFJYRMRNH-LURJTMIESA-N 0.000 description 1
- QCUHYVKRXXSMQE-WZJZPTLQSA-N CC(C)OC([C@H](C)N[P@](OCC(C[C@@H]1C)[U][C@H]1N(C=CC(NC)=N1)C1=O)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC([C@H](C)N[P@](OCC(C[C@@H]1C)[U][C@H]1N(C=CC(NC)=N1)C1=O)(Oc1ccccc1)=O)=O QCUHYVKRXXSMQE-WZJZPTLQSA-N 0.000 description 1
- LDCPPPWYJMJKIX-UHFFFAOYSA-N CC(C1)C(N(C=CC(N)=N2)C2=O)OC1(COP(Oc1ccccc1)=O)F Chemical compound CC(C1)C(N(C=CC(N)=N2)C2=O)OC1(COP(Oc1ccccc1)=O)F LDCPPPWYJMJKIX-UHFFFAOYSA-N 0.000 description 1
- HAJXAUQYFJBWOD-UHFFFAOYSA-N CC(C1O)(C(N(C=CC(N)=N2)C2=O)OC1(COP(Oc1ccccc1)=O)F)F Chemical compound CC(C1O)(C(N(C=CC(N)=N2)C2=O)OC1(COP(Oc1ccccc1)=O)F)F HAJXAUQYFJBWOD-UHFFFAOYSA-N 0.000 description 1
- GIPKUCBOGCOBQN-UHFFFAOYSA-N CC1(C(N(C=CC(N2)=O)C2=O)OC(COP(Oc2ccccc2)=O)C1O)F Chemical compound CC1(C(N(C=CC(N2)=O)C2=O)OC(COP(Oc2ccccc2)=O)C1O)F GIPKUCBOGCOBQN-UHFFFAOYSA-N 0.000 description 1
- AKEYUWUEAXIBTF-UHFFFAOYSA-N CNc1c(cccc2)c2ccc1 Chemical compound CNc1c(cccc2)c2ccc1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N CNc1ccccc1 Chemical compound CNc1ccccc1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- LKIBFKFRKYOEMC-WRKKGLQKSA-N C[C@@H](C(OC1CCCCC1)=O)NP(N[C@@H](C)C(OC1CCCCC1)=O)(OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)=[U] Chemical compound C[C@@H](C(OC1CCCCC1)=O)NP(N[C@@H](C)C(OC1CCCCC1)=O)(OC[C@](C[C@@H]1C)([O-2][C@H]1N(C=CC(N)=N1)C1=O)F)=[U] LKIBFKFRKYOEMC-WRKKGLQKSA-N 0.000 description 1
- JWNOXSHZFLRHFH-CORIIIEPSA-O C[C@@H]1[C@H](N(C=CC(N2)=O)C2=O)O[C@H](CO[P+](Oc2ccccc2)=O)C1 Chemical compound C[C@@H]1[C@H](N(C=CC(N2)=O)C2=O)O[C@H](CO[P+](Oc2ccccc2)=O)C1 JWNOXSHZFLRHFH-CORIIIEPSA-O 0.000 description 1
- UUFYWTLYUGRALJ-DUVNUKRYSA-O C[C@@H]1[C@H](N(C=CC(NC)=N2)C2=O)O[C@H](CO[P+](Oc2ccccc2)=O)C1 Chemical compound C[C@@H]1[C@H](N(C=CC(NC)=N2)C2=O)O[C@H](CO[P+](Oc2ccccc2)=O)C1 UUFYWTLYUGRALJ-DUVNUKRYSA-O 0.000 description 1
- AFBBDSOIWBNYLL-DQYAHDQKSA-N C[C@H](CN(C)P(N[C@@H](C)C(OC1CCCCC1)=O)(OC[C@](C[C@@H]1C)(O[C@H]1N(/C=C\C(C)=C)C(C)=O)F)=O)C(OC1CCCCC1)=O Chemical compound C[C@H](CN(C)P(N[C@@H](C)C(OC1CCCCC1)=O)(OC[C@](C[C@@H]1C)(O[C@H]1N(/C=C\C(C)=C)C(C)=O)F)=O)C(OC1CCCCC1)=O AFBBDSOIWBNYLL-DQYAHDQKSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762561237P | 2017-09-21 | 2017-09-21 | |
| US62/561,237 | 2017-09-21 | ||
| PCT/US2018/052239 WO2019060740A1 (en) | 2017-09-21 | 2018-09-21 | 4'-FLUORO-2'-METHYL SUBSTITUTED NUCLEOSIDE DERIVATIVES AS INHIBITORS OF HCV RNA REPLICATION |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020534374A JP2020534374A (ja) | 2020-11-26 |
| JP2020534374A5 true JP2020534374A5 (enExample) | 2021-11-04 |
| JP7299897B2 JP7299897B2 (ja) | 2023-06-28 |
Family
ID=65810030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020538752A Active JP7299897B2 (ja) | 2017-09-21 | 2018-09-21 | Ｈｃｖのｒｎａ複製阻害剤としての４’－フルオロ－２’－メチル置換ヌクレオシド誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US10682369B2 (enExample) |
| EP (1) | EP3684374B1 (enExample) |
| JP (1) | JP7299897B2 (enExample) |
| KR (1) | KR102735678B1 (enExample) |
| CN (1) | CN111194217B (enExample) |
| AR (1) | AR112702A1 (enExample) |
| AU (1) | AU2018335411B2 (enExample) |
| CA (1) | CA3075645A1 (enExample) |
| IL (1) | IL273398B2 (enExample) |
| SG (1) | SG11202002431SA (enExample) |
| TW (1) | TWI860279B (enExample) |
| WO (1) | WO2019060740A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180200280A1 (en) * | 2013-05-16 | 2018-07-19 | Riboscience Llc | 4'-Fluoro-2'-Methyl Substituted Nucleoside Derivatives as Inhibitors of HCV RNA Replication |
| EP3684374B1 (en) | 2017-09-21 | 2025-07-30 | Riboscience LLC | 4'-fluoro-2'-methyl substituted nucleoside derivatives as inhibitors of hcv rna replication |
| EP3865535A1 (en) | 2020-02-11 | 2021-08-18 | Bosti Trading Ltd. | New method of synthesis of chitosan derivatives and uses thereof |
| TW202144465A (zh) | 2020-02-11 | 2021-12-01 | 瑞士商諾和席卓股份有限公司 | 合成聚葡萄胺糖衍生物之新方法及其用途 |
| WO2022174179A1 (en) * | 2021-02-15 | 2022-08-18 | Emory University | 4'-halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| AR126678A1 (es) | 2021-08-06 | 2023-11-01 | Novochizol Sa | Composiciones para el cuidado de las plantas y usos de las mismas |
| CN117835822A (zh) | 2021-08-06 | 2024-04-05 | 诺和席卓股份有限公司 | 包含可溶性交联壳聚糖的复合凝胶、聚合物支架、聚集体和薄膜的制备及其用途 |
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