KR101857689B1 - 9,9,10,10-테트라플루오로-9,10-디하이드로페난트렌 c형 간염 바이러스 억제제 및 그 적용 - Google Patents
9,9,10,10-테트라플루오로-9,10-디하이드로페난트렌 c형 간염 바이러스 억제제 및 그 적용 Download PDFInfo
- Publication number
- KR101857689B1 KR101857689B1 KR1020167011524A KR20167011524A KR101857689B1 KR 101857689 B1 KR101857689 B1 KR 101857689B1 KR 1020167011524 A KR1020167011524 A KR 1020167011524A KR 20167011524 A KR20167011524 A KR 20167011524A KR 101857689 B1 KR101857689 B1 KR 101857689B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- tetrafluoro
- compound
- reaction
- bis
- 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.)
- Expired - Fee Related
Links
- 0 C*(C)C(CCC1)C1=S Chemical compound C*(C)C(CCC1)C1=S 0.000 description 13
- MYPUONINDNZBTH-GMBSWORKSA-N CC(C)(C)OC(N([C@H]1C[C@@H]2CC1)[C@@H]2c1nc(ccc(B2OC(C)(C)C(C)(C)O2)c2)c2[nH]1)=O Chemical compound CC(C)(C)OC(N([C@H]1C[C@@H]2CC1)[C@@H]2c1nc(ccc(B2OC(C)(C)C(C)(C)O2)c2)c2[nH]1)=O MYPUONINDNZBTH-GMBSWORKSA-N 0.000 description 1
- BOOKKHAAGCMKAX-WVARMRFOSA-N CC(C)(C)OC(N([C@H]1C[C@@H]2CC1)[C@@H]2c1ncc(-c(cc2)cc(C(C(c3c4)(F)F)(F)F)c2-c3ccc4-c2cnc([C@H]([C@@H]3CC4CC3)N4C(OC(C)(C)C)=O)[nH]2)[nH]1)=O Chemical compound CC(C)(C)OC(N([C@H]1C[C@@H]2CC1)[C@@H]2c1ncc(-c(cc2)cc(C(C(c3c4)(F)F)(F)F)c2-c3ccc4-c2cnc([C@H]([C@@H]3CC4CC3)N4C(OC(C)(C)C)=O)[nH]2)[nH]1)=O BOOKKHAAGCMKAX-WVARMRFOSA-N 0.000 description 1
- UOBOBDFTHKTEIE-ANUHAXEZSA-N CC(C)C(C(N([C@H]1C[C@@H]2CC1)[C@@H]2c1ncc(-c(cc2)cc(C(C(c3c4)(F)F)(F)F)c2-c3ccc4-c2cnc([C@H]([C@@H]3C[C@H]4CC3)N4C(CC(C)C/[O]=C(\N)/OC)=O)[nH]2)[nH]1)=O)NC(OC)=O Chemical compound CC(C)C(C(N([C@H]1C[C@@H]2CC1)[C@@H]2c1ncc(-c(cc2)cc(C(C(c3c4)(F)F)(F)F)c2-c3ccc4-c2cnc([C@H]([C@@H]3C[C@H]4CC3)N4C(CC(C)C/[O]=C(\N)/OC)=O)[nH]2)[nH]1)=O)NC(OC)=O UOBOBDFTHKTEIE-ANUHAXEZSA-N 0.000 description 1
- PPUYUEPZGGATCN-UHFFFAOYSA-N CC(CCC1)N1C(OC(C)(C)C)=O Chemical compound CC(CCC1)N1C(OC(C)(C)C)=O PPUYUEPZGGATCN-UHFFFAOYSA-N 0.000 description 1
- STGLLFIORWBERO-HNNXBMFYSA-N CC1(C)OB(c(cc2)ccc2-c2cnc([C@H]3NCCC3)[nH]2)OC1(C)C Chemical compound CC1(C)OB(c(cc2)ccc2-c2cnc([C@H]3NCCC3)[nH]2)OC1(C)C STGLLFIORWBERO-HNNXBMFYSA-N 0.000 description 1
- HUYAWICJQNOECM-UHFFFAOYSA-N CCOC(c(cc1C(C2(F)F)(F)F)ccc1-c(cc1)c2cc1C(OCC)=C)=C Chemical compound CCOC(c(cc1C(C2(F)F)(F)F)ccc1-c(cc1)c2cc1C(OCC)=C)=C HUYAWICJQNOECM-UHFFFAOYSA-N 0.000 description 1
- GRQPNLAERMIEAR-KYJUHHDHSA-N FC(C1(F)F)(c2cc(-c3ccc4nc([C@H]5NCCC5)[nH]c4c3)ccc2-c(cc2)c1cc2-c1ccc2nc([C@H]3NCCC3)[nH]c2c1)F Chemical compound FC(C1(F)F)(c2cc(-c3ccc4nc([C@H]5NCCC5)[nH]c4c3)ccc2-c(cc2)c1cc2-c1ccc2nc([C@H]3NCCC3)[nH]c2c1)F GRQPNLAERMIEAR-KYJUHHDHSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310754318 | 2013-12-31 | ||
| CN201310754318.4 | 2013-12-31 | ||
| PCT/CN2014/095043 WO2015101215A1 (zh) | 2013-12-31 | 2014-12-26 | 9,9,10,10-四氟-9,10二氢菲类丙型肝炎病毒抑制剂及其应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160058187A KR20160058187A (ko) | 2016-05-24 |
| KR101857689B1 true KR101857689B1 (ko) | 2018-05-14 |
Family
ID=53493209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167011524A Expired - Fee Related KR101857689B1 (ko) | 2013-12-31 | 2014-12-26 | 9,9,10,10-테트라플루오로-9,10-디하이드로페난트렌 c형 간염 바이러스 억제제 및 그 적용 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9512108B2 (enExample) |
| EP (1) | EP3091010A4 (enExample) |
| JP (1) | JP2017536329A (enExample) |
| KR (1) | KR101857689B1 (enExample) |
| CN (2) | CN105873922B (enExample) |
| AU (1) | AU2014375584B2 (enExample) |
| CA (1) | CA2935089C (enExample) |
| TW (1) | TWI532735B (enExample) |
| WO (1) | WO2015101215A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266424A (zh) * | 2016-04-07 | 2017-10-20 | 南京圣和药业股份有限公司 | 二氢菲类化合物及其制备方法 |
| CN108619102A (zh) * | 2017-03-21 | 2018-10-09 | 南京圣和药业股份有限公司 | 一种包含丙型肝炎病毒抑制剂的药物组合物及其制备方法 |
| CN108623568B (zh) * | 2017-03-21 | 2022-04-19 | 南京汇诚制药有限公司 | 9,10二氢菲类丙型肝炎病毒抑制剂的盐型及其制备 |
| CN108623569A (zh) * | 2017-03-21 | 2018-10-09 | 南京圣和药业股份有限公司 | 9,10-二氢菲类化合物的制备方法 |
| CN108623570A (zh) * | 2017-03-21 | 2018-10-09 | 南京圣和药业股份有限公司 | 9,10-二氢菲类化合物、其制备方法及用途 |
| 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 |
| CN114890916A (zh) * | 2022-04-25 | 2022-08-12 | 常州吉恩药业有限公司 | 一种n-甲氧羰基-l-叔亮氨酸的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010132601A1 (en) * | 2009-05-13 | 2010-11-18 | Gilead Sciences, Inc. | Antiviral compounds |
| WO2012068234A2 (en) * | 2010-11-17 | 2012-05-24 | Gilead Sciences, Inc. | Antiviral compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| US6455744B1 (en) * | 2001-01-23 | 2002-09-24 | Air Products And Chemicals, Inc. | Synthesis of vicinal difluoro aromatics and intermediates thereof |
| EP2747569A4 (en) * | 2011-08-24 | 2015-07-08 | Glaxosmithkline Llc | COMBINATION TREATMENTS FOR HEPATITIS C |
-
2014
- 2014-12-26 CN CN201480071487.0A patent/CN105873922B/zh active Active
- 2014-12-26 WO PCT/CN2014/095043 patent/WO2015101215A1/zh not_active Ceased
- 2014-12-26 AU AU2014375584A patent/AU2014375584B2/en not_active Ceased
- 2014-12-26 KR KR1020167011524A patent/KR101857689B1/ko not_active Expired - Fee Related
- 2014-12-26 EP EP14876481.4A patent/EP3091010A4/en not_active Withdrawn
- 2014-12-26 JP JP2016531709A patent/JP2017536329A/ja active Pending
- 2014-12-26 US US15/030,990 patent/US9512108B2/en not_active Expired - Fee Related
- 2014-12-26 CA CA2935089A patent/CA2935089C/en not_active Expired - Fee Related
- 2014-12-29 CN CN201410835606.7A patent/CN104744444B/zh active Active
- 2014-12-31 TW TW103146591A patent/TWI532735B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010132601A1 (en) * | 2009-05-13 | 2010-11-18 | Gilead Sciences, Inc. | Antiviral compounds |
| WO2012068234A2 (en) * | 2010-11-17 | 2012-05-24 | Gilead Sciences, Inc. | Antiviral compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105873922A (zh) | 2016-08-17 |
| TW201524973A (zh) | 2015-07-01 |
| CN104744444B (zh) | 2019-02-26 |
| TWI532735B (zh) | 2016-05-11 |
| EP3091010A4 (en) | 2017-10-04 |
| HK1222845A1 (zh) | 2017-07-14 |
| CN105873922B (zh) | 2018-08-14 |
| US20160297804A1 (en) | 2016-10-13 |
| US9512108B2 (en) | 2016-12-06 |
| CA2935089A1 (en) | 2015-07-09 |
| EP3091010A1 (en) | 2016-11-09 |
| CN104744444A (zh) | 2015-07-01 |
| KR20160058187A (ko) | 2016-05-24 |
| AU2014375584B2 (en) | 2017-11-09 |
| JP2017536329A (ja) | 2017-12-07 |
| CA2935089C (en) | 2018-11-27 |
| WO2015101215A1 (zh) | 2015-07-09 |
| AU2014375584A1 (en) | 2016-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101857689B1 (ko) | 9,9,10,10-테트라플루오로-9,10-디하이드로페난트렌 c형 간염 바이러스 억제제 및 그 적용 | |
| SG181614A1 (en) | Analogues for the treatment or prevention of flavivirus infections | |
| AU2011232331A1 (en) | Analogues for the treatment or prevention of Flavivirus infections | |
| MX2012000695A (es) | Análogos de bencimidazol para el tratamiento o la prevención de infecciones por flavivirus. | |
| KR20140053166A (ko) | C형 간염 바이러스 억제제로서 스피로 화합물 | |
| TW201200522A (en) | Analogues for the treatment or prevention of flavivirus infections | |
| SG171890A1 (en) | Inhibitors of hcv ns5a | |
| CN104725365B (zh) | 丙型肝炎病毒抑制剂及其应用 | |
| AU2011284857A1 (en) | Hetero-bicyclic derivatives as HCV inhibitors | |
| CN106008552B (zh) | 苯并[e]吡唑并[1,5-c][1,3]噁嗪类化合物及其应用 | |
| HK1222845B (zh) | 9，9，10，10-四氟-9，10二氢菲类丙型肝炎病毒抑制剂及其应用 | |
| CN105985355B (zh) | 稠合三环类肝炎病毒抑制剂及其应用 | |
| WO2017076201A1 (zh) | Hcv抑制剂、其制备方法与应用 | |
| JP2020512331A (ja) | 抗ｃ型肝炎ウイルス感染のためのケイ素含有化合物 | |
| TW201238961A (en) | Analogues for the treatment or prevention of flavivirus infections | |
| HK1191935B (en) | Spiro compounds as hepatitis c virus inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| AMND | Amendment | ||
| E13-X000 | Pre-grant limitation requested |
St.27 status event code: A-2-3-E10-E13-lim-X000 |
|
| P11-X000 | Amendment of application requested |
St.27 status event code: A-2-2-P10-P11-nap-X000 |
|
| P13-X000 | Application amended |
St.27 status event code: A-2-2-P10-P13-nap-X000 |
|
| PA0105 | International application |
St.27 status event code: A-0-1-A10-A15-nap-PA0105 |
|
| PA0201 | Request for examination |
St.27 status event code: A-1-2-D10-D11-exm-PA0201 |
|
| PG1501 | Laying open of application |
St.27 status event code: A-1-1-Q10-Q12-nap-PG1501 |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
St.27 status event code: A-1-2-D10-D21-exm-PE0902 |
|
| AMND | Amendment | ||
| P11-X000 | Amendment of application requested |
St.27 status event code: A-2-2-P10-P11-nap-X000 |
|
| P13-X000 | Application amended |
St.27 status event code: A-2-2-P10-P13-nap-X000 |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
St.27 status event code: N-2-6-B10-B15-exm-PE0601 |
|
| AMND | Amendment | ||
| E13-X000 | Pre-grant limitation requested |
St.27 status event code: A-2-3-E10-E13-lim-X000 |
|
| P11-X000 | Amendment of application requested |
St.27 status event code: A-2-2-P10-P11-nap-X000 |
|
| P13-X000 | Application amended |
St.27 status event code: A-2-2-P10-P13-nap-X000 |
|
| PX0901 | Re-examination |
St.27 status event code: A-2-3-E10-E12-rex-PX0901 |
|
| PX0701 | Decision of registration after re-examination |
St.27 status event code: A-3-4-F10-F13-rex-PX0701 |
|
| X701 | Decision to grant (after re-examination) | ||
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
St.27 status event code: A-2-4-F10-F11-exm-PR0701 |
|
| PR1002 | Payment of registration fee |
St.27 status event code: A-2-2-U10-U12-oth-PR1002 Fee payment year number: 1 |
|
| PG1601 | Publication of registration |
St.27 status event code: A-4-4-Q10-Q13-nap-PG1601 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 4 |
|
| PC1903 | Unpaid annual fee |
St.27 status event code: A-4-4-U10-U13-oth-PC1903 Not in force date: 20220509 Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE |
|
| PC1903 | Unpaid annual fee |
St.27 status event code: N-4-6-H10-H13-oth-PC1903 Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE Not in force date: 20220509 |