AU2009228451A1 - Aromatic heterocyclic fused indolobenzadiazepine HCV NS5B inhibitors - Google Patents
Aromatic heterocyclic fused indolobenzadiazepine HCV NS5B inhibitors Download PDFInfo
- Publication number
- AU2009228451A1 AU2009228451A1 AU2009228451A AU2009228451A AU2009228451A1 AU 2009228451 A1 AU2009228451 A1 AU 2009228451A1 AU 2009228451 A AU2009228451 A AU 2009228451A AU 2009228451 A AU2009228451 A AU 2009228451A AU 2009228451 A1 AU2009228451 A1 AU 2009228451A1
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- Australia
- Prior art keywords
- hcv
- inhibitors
- compound
- mmol
- cyclohexyl
- 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.)
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- 108700008776 hepatitis C virus NS-5 Proteins 0.000 title claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 title 1
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- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229940038850 rebif Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 239000002336 ribonucleotide Substances 0.000 description 1
- 125000002652 ribonucleotide group Chemical group 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 description 1
- 229950006081 taribavirin Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- SXFXBQJKPSXOLZ-UHFFFAOYSA-N tert-butyl 2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound C(=O)(OC(C)(C)C)C1=C(C=CC=C1N)B1OC(C)(C)C(C)(C)O1 SXFXBQJKPSXOLZ-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
- 229960004231 thymalfasin Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3996108P | 2008-03-27 | 2008-03-27 | |
| US61/039,961 | 2008-03-27 | ||
| PCT/US2009/038010 WO2009120650A1 (en) | 2008-03-27 | 2009-03-24 | Aromatic heterocyclic fused indolobenzadiazepine hcv ns5b inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009228451A1 true AU2009228451A1 (en) | 2009-10-01 |
Family
ID=40810527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009228451A Abandoned AU2009228451A1 (en) | 2008-03-27 | 2009-03-24 | Aromatic heterocyclic fused indolobenzadiazepine HCV NS5B inhibitors |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8431568B2 (https=) |
| EP (1) | EP2278977B1 (https=) |
| JP (1) | JP2011517673A (https=) |
| KR (1) | KR20100124848A (https=) |
| CN (1) | CN101980711B (https=) |
| AT (1) | ATE531373T1 (https=) |
| AU (1) | AU2009228451A1 (https=) |
| ES (1) | ES2374870T3 (https=) |
| MX (1) | MX2010010060A (https=) |
| WO (1) | WO2009120650A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103288828A (zh) * | 2012-02-24 | 2013-09-11 | 中国科学院大连化学物理研究所 | 一种合成手性二氢-6H-吲哚并[2,1-c][1,4]-苯并二氮杂卓的方法 |
| CN103539723A (zh) * | 2013-10-29 | 2014-01-29 | 南方医科大学 | 一种3-氨基-2-芳甲酰基-1h-吲哚类衍生物的合成方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4897392A (en) * | 1989-07-03 | 1990-01-30 | Hoechst-Roussel Pharmaceuticals, Inc. | 4H-indolo(1,2-d)(1,2,4)triazolo(4,3-A)(1,4)benzodiazepines |
| HRP20090250T1 (hr) | 2004-02-24 | 2009-06-30 | Japan Tobacco | Kondenzirani heterociklički spojevi i njihova upotreba kao inhibitora hcv polimeraze |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| US7348425B2 (en) | 2004-08-09 | 2008-03-25 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| EP1807403A2 (en) | 2004-10-26 | 2007-07-18 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) * | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7399758B2 (en) | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| GB0608928D0 (en) * | 2006-05-08 | 2006-06-14 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| WO2007140200A2 (en) | 2006-05-25 | 2007-12-06 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| JP5205370B2 (ja) | 2006-05-25 | 2013-06-05 | ブリストル−マイヤーズ スクイブ カンパニー | シクロプロピル縮合インドロベンゾアゼピンｈｃｖｎｓ５ｂ阻害剤 |
| US7452876B2 (en) | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| AR062827A1 (es) * | 2006-07-20 | 2008-12-10 | Genelabs Tech Inc | Inhibidores virales policiclicos, una composicion farmaceutica que los comprende y su uso en la preparacion de medicamentos para el tratamiento de una infeccion viral mediada porl el virus de la hepatitis c |
| US7642251B2 (en) | 2007-08-09 | 2010-01-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8143243B2 (en) | 2007-08-09 | 2012-03-27 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7652004B2 (en) | 2007-08-09 | 2010-01-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8138171B2 (en) | 2008-03-27 | 2012-03-20 | Bristol-Myers Squibb Company | Dioxolane and dioxolanone fused indolobenzadiazepine HCV NS5B inhibitors |
| US8133884B2 (en) | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
-
2009
- 2009-03-24 KR KR1020107023917A patent/KR20100124848A/ko not_active Withdrawn
- 2009-03-24 AU AU2009228451A patent/AU2009228451A1/en not_active Abandoned
- 2009-03-24 WO PCT/US2009/038010 patent/WO2009120650A1/en not_active Ceased
- 2009-03-24 US US12/922,801 patent/US8431568B2/en active Active
- 2009-03-24 MX MX2010010060A patent/MX2010010060A/es active IP Right Grant
- 2009-03-24 EP EP09725965A patent/EP2278977B1/en not_active Not-in-force
- 2009-03-24 JP JP2011501963A patent/JP2011517673A/ja active Pending
- 2009-03-24 ES ES09725965T patent/ES2374870T3/es active Active
- 2009-03-24 AT AT09725965T patent/ATE531373T1/de active
- 2009-03-24 CN CN2009801109761A patent/CN101980711B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE531373T1 (de) | 2011-11-15 |
| US20110014154A1 (en) | 2011-01-20 |
| US8431568B2 (en) | 2013-04-30 |
| MX2010010060A (es) | 2010-09-30 |
| WO2009120650A1 (en) | 2009-10-01 |
| KR20100124848A (ko) | 2010-11-29 |
| EP2278977B1 (en) | 2011-11-02 |
| ES2374870T3 (es) | 2012-02-22 |
| JP2011517673A (ja) | 2011-06-16 |
| CN101980711B (zh) | 2012-10-31 |
| CN101980711A (zh) | 2011-02-23 |
| EP2278977A1 (en) | 2011-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |