JP2016510043A5 - - Google Patents
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- Publication number
- JP2016510043A5 JP2016510043A5 JP2015560536A JP2015560536A JP2016510043A5 JP 2016510043 A5 JP2016510043 A5 JP 2016510043A5 JP 2015560536 A JP2015560536 A JP 2015560536A JP 2015560536 A JP2015560536 A JP 2015560536A JP 2016510043 A5 JP2016510043 A5 JP 2016510043A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- halogenated
- alkenyl
- alkoxy
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 111
- -1 nucleoside phosphoramidate compound Chemical class 0.000 claims description 69
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 239000013078 crystal Substances 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004442 acylamino group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000005605 benzo group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 241000710781 Flaviviridae Species 0.000 claims description 5
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000002777 nucleoside Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 0 CC(C)OC([C@](C)NP(OC[C@](C(*)[C@@]1(C)F)O[C@]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1C#Cc1ccccc1)=O)=O Chemical compound CC(C)OC([C@](C)NP(OC[C@](C(*)[C@@]1(C)F)O[C@]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1C#Cc1ccccc1)=O)=O 0.000 description 2
- SSZCBROOHASCLD-XJYOMHBNSA-N CC(C)(C)OC(CNP(OC[C@H](C[C@@]1(C)F)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1c(CCCC2)c2ccc1)=O)=O Chemical compound CC(C)(C)OC(CNP(OC[C@H](C[C@@]1(C)F)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1c(CCCC2)c2ccc1)=O)=O SSZCBROOHASCLD-XJYOMHBNSA-N 0.000 description 1
- BTNUUICIPWNRRP-MVYJGKBDSA-N CC(C)OC([C@H](C)NP(OC(C1)C1([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1-c1cnc[s]1)=O)=O Chemical compound CC(C)OC([C@H](C)NP(OC(C1)C1([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1-c1cnc[s]1)=O)=O BTNUUICIPWNRRP-MVYJGKBDSA-N 0.000 description 1
- TUXNGHGYTVSDOP-OUCMYBABSA-N CC(C)OC([C@H](C)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccc(/C=C/c(cc2)ccc2F)cc1)=O)=O Chemical compound CC(C)OC([C@H](C)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccc(/C=C/c(cc2)ccc2F)cc1)=O)=O TUXNGHGYTVSDOP-OUCMYBABSA-N 0.000 description 1
- NHZRNCJCPYOACJ-AIFGFEPYSA-N CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1-c(cc1)ccc1C#N)=O)=O Chemical compound CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc(cc1)ccc1-c(cc1)ccc1C#N)=O)=O NHZRNCJCPYOACJ-AIFGFEPYSA-N 0.000 description 1
- TVBBFDJJEAVWAM-BTHPUMMZSA-N CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccc2[nH]ccc2c1)=O)=O Chemical compound CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccc2[nH]ccc2c1)=O)=O TVBBFDJJEAVWAM-BTHPUMMZSA-N 0.000 description 1
- APNPUOJOPGHINO-KAXDPSJKSA-N CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccccc1-c1cccc2c1nccn2)=O)=O Chemical compound CC(C)OC([C@H](C)NP(OC[C@H]([C@H]([C@@]1(C)F)O)O[C@H]1N(C=CC(N1)=O)C1=O)(Oc1ccccc1-c1cccc2c1nccn2)=O)=O APNPUOJOPGHINO-KAXDPSJKSA-N 0.000 description 1
- QTDQRYVHWDDHAN-KUVPSTBASA-N C[C@@]1([C@H](N(C=CC(N2)=O)C2=O)O[C@H](COP(NCC(OC)=O)(Oc2c(CCCC3)c3ccc2)=O)[C@H]1O)F Chemical compound C[C@@]1([C@H](N(C=CC(N2)=O)C2=O)O[C@H](COP(NCC(OC)=O)(Oc2c(CCCC3)c3ccc2)=O)[C@H]1O)F QTDQRYVHWDDHAN-KUVPSTBASA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310075423 | 2013-03-08 | ||
| CN201310075423.5 | 2013-03-08 | ||
| PCT/CN2014/073004 WO2014135107A1 (zh) | 2013-03-08 | 2014-03-06 | 新的核苷氨基磷酸酯化合物及其应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016510043A JP2016510043A (ja) | 2016-04-04 |
| JP2016510043A5 true JP2016510043A5 (enExample) | 2016-05-19 |
| JP6219414B2 JP6219414B2 (ja) | 2017-10-25 |
Family
ID=51462121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015560536A Active JP6219414B2 (ja) | 2013-03-08 | 2014-03-06 | 新規なヌクレオシドホスホロアミデート化合物およびその使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9963480B2 (enExample) |
| EP (1) | EP2940031B1 (enExample) |
| JP (1) | JP6219414B2 (enExample) |
| KR (1) | KR101857337B1 (enExample) |
| CN (4) | CN108546277B (enExample) |
| AU (1) | AU2014225052B2 (enExample) |
| BR (1) | BR112015020472B1 (enExample) |
| CA (1) | CA2899763C (enExample) |
| MX (1) | MX374244B (enExample) |
| RU (1) | RU2621709C2 (enExample) |
| WO (1) | WO2014135107A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014225052B2 (en) | 2013-03-08 | 2016-11-10 | Nanjing Sanhome Pharmaceutical Co., Ltd. | Novel nucleoside phosphoramidate compound and use thereof |
| CN104761604A (zh) * | 2014-01-02 | 2015-07-08 | 江苏豪森药业股份有限公司 | 尿嘧啶核苷酸类似物及其制备方法和应用 |
| CN105315319B (zh) * | 2014-07-30 | 2020-11-20 | 南京圣和药业股份有限公司 | 丙型肝炎病毒抑制剂及其应用 |
| WO2016023522A2 (en) * | 2014-08-15 | 2016-02-18 | Merck Sharp & Dohme Corp. | Substituted phosphoramidate compounds and uses thereof |
| WO2016044243A1 (en) * | 2014-09-16 | 2016-03-24 | Achillion Pharmaceuticals, Inc. | Pyrimidine nucleoside phosphoramidate |
| CN105348342B (zh) * | 2014-09-30 | 2018-09-21 | 南京正大天晴制药有限公司 | 核苷氨基磷酸酯化合物及药物组合物和用途 |
| CN106132972B (zh) * | 2015-02-06 | 2018-08-31 | 银杏树药业(苏州)有限公司 | 用于治疗hcv感染的氨基磷酸酯 |
| CN106866737B (zh) * | 2015-12-11 | 2020-11-20 | 南京圣和药物研发有限公司 | 膦酸衍生物及其应用 |
| AU2017324939B2 (en) * | 2016-09-07 | 2021-10-14 | Atea Pharmaceuticals, Inc. | 2'-substituted-N6-substituted purine nucleotides for RNA virus treatment |
| CN108602842B (zh) * | 2016-11-02 | 2020-10-09 | 四川科伦博泰生物医药股份有限公司 | 杂环化合物及其制备方法和用途 |
| WO2018093717A1 (en) * | 2016-11-17 | 2018-05-24 | Abbvie Inc. | Compositions and methods for treating hcv infection |
| CN108218936B (zh) * | 2016-12-13 | 2022-06-07 | 南京圣和药业股份有限公司 | 联苯核苷氨基磷酸酯化合物的异构体及其无定型物 |
| CN108218940A (zh) * | 2016-12-13 | 2018-06-29 | 南京圣和药业股份有限公司 | 核苷氨基磷酸酯类化合物、其制备方法及用途 |
| CN116492363A (zh) * | 2016-12-13 | 2023-07-28 | 南京汇诚制药有限公司 | 新的核苷氨基磷酸脂化合物的组合物及其制备方法 |
| CN108218939B (zh) * | 2016-12-13 | 2022-05-17 | 南京汇诚制药有限公司 | 联苯核苷氨基磷酸酯化合物的新晶型及制备方法 |
| CN108218938B (zh) * | 2016-12-13 | 2022-06-07 | 南京圣和药业股份有限公司 | 联苯核苷氨基磷酸酯化合物的晶型及其制备方法与用途 |
| CN108218937B (zh) * | 2016-12-13 | 2022-06-07 | 南京圣和药业股份有限公司 | 核苷氨基磷酸酯类化合物的光学异构体及其应用 |
| CN108201539B (zh) * | 2016-12-16 | 2022-04-19 | 南京汇诚制药有限公司 | 联苯核苷氨基磷酸酯化合物的应用 |
| CN109419806B (zh) * | 2017-08-23 | 2023-06-20 | 南京圣和药业股份有限公司 | 抗病毒组合物及其应用 |
| CN108997426B (zh) * | 2018-07-19 | 2020-11-13 | 大连理工大学 | 靶向Hsp60的黄酮烷氧基氨基磷酸酯衍生物、制备及应用 |
| JP2022540585A (ja) | 2019-07-12 | 2022-09-16 | キャノピー グロウス コーポレイション | カンナビノイド誘導体 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020147175A1 (en) * | 2000-11-16 | 2002-10-10 | Shepard H. Michael | Synergistic ECTA compositions |
| JP5069463B2 (ja) * | 2003-04-25 | 2012-11-07 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス性ホスホネート類似物 |
| WO2006065335A2 (en) | 2004-10-21 | 2006-06-22 | Merck & Co., Inc. | Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides for the treatment of rna-dependent rna viral infection |
| GB0503642D0 (en) | 2005-02-22 | 2005-03-30 | Younane Paul P M | An exercise apparatus |
| WO2006116557A1 (en) | 2005-04-25 | 2006-11-02 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| PA8852101A1 (es) * | 2008-12-08 | 2010-07-27 | Medivir Ab | Nucleótidos uracil ciclopropílicos |
| MX2011006891A (es) | 2008-12-23 | 2011-10-06 | Pharmasset Inc | Fosforamidatos de nucleosidos. |
| JO3027B1 (ar) * | 2009-05-14 | 2016-09-05 | Janssen Products Lp | نيوكليوسيدات يوراسيل سبيرواوكسيتان |
| SG188497A1 (en) * | 2010-09-22 | 2013-05-31 | Alios Biopharma Inc | Substituted nucleotide analogs |
| JP2014526474A (ja) * | 2011-09-12 | 2014-10-06 | アイディニックス ファーマシューティカルズ インコーポレイテッド | ウイルス感染の治療のための化合物および薬学的組成物 |
| PL2794629T3 (pl) * | 2011-12-20 | 2018-02-28 | Riboscience Llc | 2',4'-difluoro-2'-metylo-podstawione pochodne nukleozydowe jako inhibitory replikacji rna hcv |
| AU2014225052B2 (en) | 2013-03-08 | 2016-11-10 | Nanjing Sanhome Pharmaceutical Co., Ltd. | Novel nucleoside phosphoramidate compound and use thereof |
| CN104761604A (zh) | 2014-01-02 | 2015-07-08 | 江苏豪森药业股份有限公司 | 尿嘧啶核苷酸类似物及其制备方法和应用 |
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2014
- 2014-03-06 AU AU2014225052A patent/AU2014225052B2/en active Active
- 2014-03-06 JP JP2015560536A patent/JP6219414B2/ja active Active
- 2014-03-06 EP EP14760567.9A patent/EP2940031B1/en active Active
- 2014-03-06 CA CA2899763A patent/CA2899763C/en active Active
- 2014-03-06 RU RU2015142682A patent/RU2621709C2/ru active
- 2014-03-06 KR KR1020157027466A patent/KR101857337B1/ko active Active
- 2014-03-06 US US14/764,865 patent/US9963480B2/en active Active
- 2014-03-06 MX MX2015011473A patent/MX374244B/es active IP Right Grant
- 2014-03-06 WO PCT/CN2014/073004 patent/WO2014135107A1/zh not_active Ceased
- 2014-03-06 BR BR112015020472-4A patent/BR112015020472B1/pt active IP Right Grant
- 2014-03-07 CN CN201810261317.9A patent/CN108546277B/zh active Active
- 2014-03-07 CN CN201810261269.3A patent/CN108314697B/zh active Active
- 2014-03-07 CN CN201410081865.5A patent/CN104031104B/zh active Active
- 2014-03-07 CN CN201810261299.4A patent/CN109503686B/zh active Active