JP5690286B2 - ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 - Google Patents
ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 Download PDFInfo
- Publication number
- JP5690286B2 JP5690286B2 JP2011553059A JP2011553059A JP5690286B2 JP 5690286 B2 JP5690286 B2 JP 5690286B2 JP 2011553059 A JP2011553059 A JP 2011553059A JP 2011553059 A JP2011553059 A JP 2011553059A JP 5690286 B2 JP5690286 B2 JP 5690286B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- cycloalkyl
- aryl
- heteroaryl
- 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 *c1c(*)[s]c(*)n1 Chemical compound *c1c(*)[s]c(*)n1 0.000 description 39
- KLGGKIMOTMKYEF-UHFFFAOYSA-N C=[N]=CCC(CC1)CCC1=NO Chemical compound C=[N]=CCC(CC1)CCC1=NO KLGGKIMOTMKYEF-UHFFFAOYSA-N 0.000 description 1
- RMFAIOVNOKQKPO-UHFFFAOYSA-N CCC(C)C(C)CNN=N Chemical compound CCC(C)C(C)CNN=N RMFAIOVNOKQKPO-UHFFFAOYSA-N 0.000 description 1
- RSPLNBUCFYBLLS-UHFFFAOYSA-O CCCC(CC[NH2+]O)I Chemical compound CCCC(CC[NH2+]O)I RSPLNBUCFYBLLS-UHFFFAOYSA-O 0.000 description 1
- JKSQFAAELXEAQT-UHFFFAOYSA-N CCCP(c(ccc(Cl)c1)c1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2-c2n[n](cccn3)c3c2)c1)=O Chemical compound CCCP(c(ccc(Cl)c1)c1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2-c2n[n](cccn3)c3c2)c1)=O JKSQFAAELXEAQT-UHFFFAOYSA-N 0.000 description 1
- LOOZHKGIZBEGPP-KGVAIUNMSA-N CCOC(C1C(C=C2)=CCC2Cl)([C@H]1Nc1c(C)[s]c(-c2ccc(CCCC(c3c[s]cn3)=O)cc2)c1)OC Chemical compound CCOC(C1C(C=C2)=CCC2Cl)([C@H]1Nc1c(C)[s]c(-c2ccc(CCCC(c3c[s]cn3)=O)cc2)c1)OC LOOZHKGIZBEGPP-KGVAIUNMSA-N 0.000 description 1
- VTMRHTMLFWLELY-UHFFFAOYSA-N CCOP(c(c(Cl)c1)ccc1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2C#Cc2c[s]cn2)c1)=O Chemical compound CCOP(c(c(Cl)c1)ccc1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2C#Cc2c[s]cn2)c1)=O VTMRHTMLFWLELY-UHFFFAOYSA-N 0.000 description 1
- MEEWFOUSXABVGX-UHFFFAOYSA-N CCOP(c(ccc(Cl)c1)c1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2Cl)c1)=O Chemical compound CCOP(c(ccc(Cl)c1)c1Cl)(Nc1c(C(O)=O)[s]c(-c(cc2)ccc2Cl)c1)=O MEEWFOUSXABVGX-UHFFFAOYSA-N 0.000 description 1
- UXKBSUKGHCALOR-UHFFFAOYSA-N CCOP(c1c(C)cc(C)cc1)(N(C(C)C)c1c(C(O)=O)[s]c(-c(cc2)ccc2F)c1)=O Chemical compound CCOP(c1c(C)cc(C)cc1)(N(C(C)C)c1c(C(O)=O)[s]c(-c(cc2)ccc2F)c1)=O UXKBSUKGHCALOR-UHFFFAOYSA-N 0.000 description 1
- XGGJHCFZALANKI-UHFFFAOYSA-N CCO[N+](c(ccc(Cl)c1)c1Cl)(NC(C=C1c(cc2)ccc2-c2n[n]3c(N=N)ccnc3c2)=C(C(O)=O)C1=C)[O-] Chemical compound CCO[N+](c(ccc(Cl)c1)c1Cl)(NC(C=C1c(cc2)ccc2-c2n[n]3c(N=N)ccnc3c2)=C(C(O)=O)C1=C)[O-] XGGJHCFZALANKI-UHFFFAOYSA-N 0.000 description 1
- CSYCHISMXVGXFW-UHFFFAOYSA-N COC(c([s]c(-c(cc1)ccc1-c1n[n](cccn2)c2c1)n1)c1Cl)=O Chemical compound COC(c([s]c(-c(cc1)ccc1-c1n[n](cccn2)c2c1)n1)c1Cl)=O CSYCHISMXVGXFW-UHFFFAOYSA-N 0.000 description 1
- CICQUFBZCADHHX-UHFFFAOYSA-N COc(ccc(Cl)c1)c1Cl Chemical compound COc(ccc(Cl)c1)c1Cl CICQUFBZCADHHX-UHFFFAOYSA-N 0.000 description 1
- ROCGMCUXLYBSQC-UHFFFAOYSA-O C[NH+](CC1)CCC1I Chemical compound C[NH+](CC1)CCC1I ROCGMCUXLYBSQC-UHFFFAOYSA-O 0.000 description 1
- IELOUGOZFCNFEG-UHFFFAOYSA-O C[NH+](CCC1)CC1I Chemical compound C[NH+](CCC1)CC1I IELOUGOZFCNFEG-UHFFFAOYSA-O 0.000 description 1
- BMVSEJIZKZEYJZ-UHFFFAOYSA-N Cc([nH]nc1CCc(cc(C)cc2)c2P(Nc2c(C(O)=O)[s]c(-c3c[nH]nc3C(F)(F)F)c2)(OC)=O)c1-c1cc(NP(c2c(C)cc(C)cc2)(OC)=O)c(C(O)=O)[s]1 Chemical compound Cc([nH]nc1CCc(cc(C)cc2)c2P(Nc2c(C(O)=O)[s]c(-c3c[nH]nc3C(F)(F)F)c2)(OC)=O)c1-c1cc(NP(c2c(C)cc(C)cc2)(OC)=O)c(C(O)=O)[s]1 BMVSEJIZKZEYJZ-UHFFFAOYSA-N 0.000 description 1
- FDBWNBSNBMFXQA-UHFFFAOYSA-N Cc(cc1)cc(C)c1P(Nc1c(C(O)=O)[s]c(-c2ccccc2)c1)(OC)=O Chemical compound Cc(cc1)cc(C)c1P(Nc1c(C(O)=O)[s]c(-c2ccccc2)c1)(OC)=O FDBWNBSNBMFXQA-UHFFFAOYSA-N 0.000 description 1
- USKYODXIRSRZMH-UHFFFAOYSA-N Cc(cc1)cc(C)c1P(Nc1c(P(O)(O)=O)[s]c(-c(cc2)ccc2-c2cc(cccc3)c3[o]2)c1)(OC)=O Chemical compound Cc(cc1)cc(C)c1P(Nc1c(P(O)(O)=O)[s]c(-c(cc2)ccc2-c2cc(cccc3)c3[o]2)c1)(OC)=O USKYODXIRSRZMH-UHFFFAOYSA-N 0.000 description 1
- YRASFZRMMMREBJ-UHFFFAOYSA-N Cc(cc1)cc(C)c1[O](Nc1c(C(O)=O)[s]c(-c(cc2)ccc2F)c1)(O)=O Chemical compound Cc(cc1)cc(C)c1[O](Nc1c(C(O)=O)[s]c(-c(cc2)ccc2F)c1)(O)=O YRASFZRMMMREBJ-UHFFFAOYSA-N 0.000 description 1
- YSMMEPHYCONYCV-UHFFFAOYSA-N Cc(cc1)ccc1-c1cc(NC[O](C)c2c(C)cc(C)cc2)c(C(O)=O)[s]1 Chemical compound Cc(cc1)ccc1-c1cc(NC[O](C)c2c(C)cc(C)cc2)c(C(O)=O)[s]1 YSMMEPHYCONYCV-UHFFFAOYSA-N 0.000 description 1
- PQDTWGNPARQQSF-UHFFFAOYSA-N Cc(cc1C)ccc1P(NC(C1)=C(C(O)=O)SC1c(cc1)ccc1-c1n[n](cccn2)c2c1)(OC)=O Chemical compound Cc(cc1C)ccc1P(NC(C1)=C(C(O)=O)SC1c(cc1)ccc1-c1n[n](cccn2)c2c1)(OC)=O PQDTWGNPARQQSF-UHFFFAOYSA-N 0.000 description 1
- YCHPGWNDZBJQGO-UHFFFAOYSA-N Cc1n[o]c(C)c1-c1cc(NP(c2c(C)cc(C)cc2)(OC)=O)c(C(O)=O)[s]1 Chemical compound Cc1n[o]c(C)c1-c1cc(NP(c2c(C)cc(C)cc2)(OC)=O)c(C(O)=O)[s]1 YCHPGWNDZBJQGO-UHFFFAOYSA-N 0.000 description 1
- SVSXWPPDLLEGKG-UHFFFAOYSA-N OC(C1SC(c(cc2)ccc2-c2n[n](cccn3)c3c2)=CC1N[O](c(ccc(Cl)c1)c1Cl)(O)=O)=O Chemical compound OC(C1SC(c(cc2)ccc2-c2n[n](cccn3)c3c2)=CC1N[O](c(ccc(Cl)c1)c1Cl)(O)=O)=O SVSXWPPDLLEGKG-UHFFFAOYSA-N 0.000 description 1
- AMEPJXXVIJZMJL-UHFFFAOYSA-N OC(c([s]c(Cl)n1)c1Cl)=O Chemical compound OC(c([s]c(Cl)n1)c1Cl)=O AMEPJXXVIJZMJL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15721109P | 2009-03-04 | 2009-03-04 | |
| US61/157,211 | 2009-03-04 | ||
| PCT/US2010/025991 WO2010101967A2 (en) | 2009-03-04 | 2010-03-03 | Phosphothiophene and phosphothiazole hcv polymerase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012519691A JP2012519691A (ja) | 2012-08-30 |
| JP2012519691A5 JP2012519691A5 (enExample) | 2013-04-11 |
| JP5690286B2 true JP5690286B2 (ja) | 2015-03-25 |
Family
ID=42123028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011553059A Expired - Fee Related JP5690286B2 (ja) | 2009-03-04 | 2010-03-03 | ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8193372B2 (enExample) |
| EP (1) | EP2403860B1 (enExample) |
| JP (1) | JP5690286B2 (enExample) |
| TW (1) | TW201036988A (enExample) |
| WO (1) | WO2010101967A2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012116050A2 (en) * | 2011-02-24 | 2012-08-30 | Eternity Bioscience Inc. | Phosphorus containing compounds as protein kinase inhibitors |
| HK1247829A1 (zh) | 2015-03-06 | 2018-10-05 | Atea Pharmaceuticals, Inc. | 用於治疗HCV的β-D-2'-脱氧-2'Α-氟-2'-β-C-取代-2-改性N6-取代的嘌呤核苷酸 |
| WO2016188943A1 (en) | 2015-05-27 | 2016-12-01 | Idenix Pharmaceuticals Llc | Nucleotides for the treatment of cancer |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| LU100724B1 (en) | 2016-07-14 | 2018-07-31 | Atea Pharmaceuticals Inc | Beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substituted-4'-fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection |
| EP3512863B1 (en) | 2016-09-07 | 2021-12-08 | ATEA Pharmaceuticals, Inc. | 2'-substituted-n6-substituted purine nucleotides for rna virus treatment |
| AR110768A1 (es) | 2017-01-31 | 2019-05-02 | Gilead Sciences Inc | Formas cristalinas de tenofovir alafenamida |
| EP4450129A3 (en) | 2017-02-01 | 2025-03-19 | ATEA Pharmaceuticals, Inc. | Nucleotide hemi-sulfate salt for the treatment of hepatitis c virus |
| CN110769822A (zh) | 2017-06-20 | 2020-02-07 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| TW202012001A (zh) | 2018-04-10 | 2020-04-01 | 美商亞堤製藥公司 | C型肝炎病毒(hcv)感染硬化之患者的治療 |
| CN108586527B (zh) * | 2018-06-01 | 2020-03-31 | 郑州大学 | 芳基膦酸酯类化合物及其制备方法 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| CN111196823A (zh) * | 2020-03-10 | 2020-05-26 | 郑州大学 | 一种3-膦酰化苯并噻吩类化合物及制备方法 |
| CN117500494A (zh) | 2021-06-17 | 2024-02-02 | 阿堤亚制药公司 | 有利的抗hcv联合疗法 |
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| FR2135690A5 (en) * | 1971-03-17 | 1972-12-22 | Roussel Uclaf | O,o-dialkyl o-(5-alkoxycarbonyl-2-methyl-4-thiazolyl) - phosphates and thiophosphates - as acaricides and insecticides |
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-
2010
- 2010-03-03 EP EP10707186.2A patent/EP2403860B1/en not_active Not-in-force
- 2010-03-03 JP JP2011553059A patent/JP5690286B2/ja not_active Expired - Fee Related
- 2010-03-03 US US12/716,278 patent/US8193372B2/en active Active
- 2010-03-03 WO PCT/US2010/025991 patent/WO2010101967A2/en not_active Ceased
- 2010-03-04 TW TW099106301A patent/TW201036988A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2403860B1 (en) | 2015-11-04 |
| EP2403860A2 (en) | 2012-01-11 |
| WO2010101967A2 (en) | 2010-09-10 |
| US20100233123A1 (en) | 2010-09-16 |
| TW201036988A (en) | 2010-10-16 |
| US8193372B2 (en) | 2012-06-05 |
| JP2012519691A (ja) | 2012-08-30 |
| WO2010101967A3 (en) | 2010-11-11 |
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