AU2014233390B2 - Macrocyclic and bicyclic inhibitors of hepatitis C virus - Google Patents
Macrocyclic and bicyclic inhibitors of hepatitis C virus Download PDFInfo
- Publication number
- AU2014233390B2 AU2014233390B2 AU2014233390A AU2014233390A AU2014233390B2 AU 2014233390 B2 AU2014233390 B2 AU 2014233390B2 AU 2014233390 A AU2014233390 A AU 2014233390A AU 2014233390 A AU2014233390 A AU 2014233390A AU 2014233390 B2 AU2014233390 B2 AU 2014233390B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- optionally substituted
- carbocyclyl
- groups
- membered
- 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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- 125000002619 bicyclic group Chemical group 0.000 title claims 14
- 241000711549 Hepacivirus C Species 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract 69
- 150000003839 salts Chemical class 0.000 claims abstract 60
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 68
- 125000004452 carbocyclyl group Chemical group 0.000 claims 58
- 125000003118 aryl group Chemical group 0.000 claims 44
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 22
- 125000004450 alkenylene group Chemical group 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- 125000002947 alkylene group Chemical group 0.000 claims 19
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 125000004474 heteroalkylene group Chemical group 0.000 claims 18
- 125000003342 alkenyl group Chemical group 0.000 claims 16
- 125000004043 oxo group Chemical group O=* 0.000 claims 15
- -1 -CONHSO2Z2 Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000003003 spiro group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 101100060033 Drosophila melanogaster cic gene Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100060035 Mus musculus Cic gene Proteins 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/02—Preparation by ring-closure
-
- 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
-
- 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
- C07D487/02—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 two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361798961P | 2013-03-15 | 2013-03-15 | |
| US61/798,961 | 2013-03-15 | ||
| PCT/US2014/029765 WO2014145095A1 (en) | 2013-03-15 | 2014-03-14 | Macrocyclic and bicyclic inhibitors of hepatitis c virus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014233390A1 AU2014233390A1 (en) | 2015-09-03 |
| AU2014233390B2 true AU2014233390B2 (en) | 2018-03-01 |
Family
ID=50694007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014233390A Active AU2014233390B2 (en) | 2013-03-15 | 2014-03-14 | Macrocyclic and bicyclic inhibitors of hepatitis C virus |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US9617310B2 (enExample) |
| EP (1) | EP2970335B1 (enExample) |
| JP (2) | JP6511432B2 (enExample) |
| KR (1) | KR102215400B1 (enExample) |
| CN (1) | CN105073758B (enExample) |
| AU (1) | AU2014233390B2 (enExample) |
| BR (1) | BR112015021768A2 (enExample) |
| CA (1) | CA2902569A1 (enExample) |
| EA (1) | EA029088B1 (enExample) |
| ES (1) | ES2735355T3 (enExample) |
| IL (1) | IL240662A0 (enExample) |
| MX (1) | MX2015013224A (enExample) |
| SG (1) | SG11201507223TA (enExample) |
| WO (1) | WO2014145095A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| JP7381190B2 (ja) | 2014-12-26 | 2023-11-15 | エモリー・ユニバーシテイ | Ｎ４－ヒドロキシシチジン及び誘導体並びにそれに関連する抗ウイルス用途 |
| CN105503751B (zh) * | 2015-12-22 | 2018-06-05 | 广西师范大学 | 一种喹喔啉衍生物的高效合成方法 |
| KR102626210B1 (ko) | 2017-12-07 | 2024-01-18 | 에모리 유니버시티 | N4-하이드록시사이티딘 및 유도체 및 이와 관련된 항-바이러스 용도 |
| CN108329332A (zh) * | 2018-03-16 | 2018-07-27 | 安徽华昌高科药业有限公司 | 一种制备Glecaprevir的方法 |
| CN111004188B (zh) * | 2019-12-18 | 2021-04-20 | 安徽红杉生物医药科技有限公司 | Ns3/4a蛋白酶抑制剂中间体及其合成方法、应用 |
| CN111018795B (zh) * | 2019-12-25 | 2023-03-28 | 上海彩迩文生化科技有限公司 | 一种碱性条件下合成喹喔啉-3-酮的方法 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010011566A1 (en) * | 2008-07-22 | 2010-01-28 | Merck & Co., Inc. | Macrocyclic quinoxaline compounds as hcv ns3 protease inhibitors |
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| DE60138567D1 (de) | 2000-12-12 | 2009-06-10 | Schering Corp | Diarylrest entfassende peptide als inhibitoren des ns-3 serinproteases von hepatitis c virus |
| MXPA04003954A (es) | 2001-10-26 | 2004-11-29 | Aventis Pharma Inc | Bencimidazoles. |
| ATE481106T1 (de) | 2002-05-20 | 2010-10-15 | Bristol Myers Squibb Co | Heterocyclische sulfonamid-hepatitis-c-virus- hemmer |
| ES2361011T3 (es) | 2002-05-20 | 2011-06-13 | Bristol-Myers Squibb Company | Inhibidores del virus de la hepatitis c. |
| AU2003301959A1 (en) | 2002-05-20 | 2004-06-03 | Bristol-Myers Squibb Company | Substituted cycloalkyl p1' hepatitis c virus inhibitors |
| JP4733023B2 (ja) | 2003-04-16 | 2011-07-27 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎ウイルスの大環状イソキノリンペプチド阻害剤 |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| DE602004023924D1 (en) | 2003-04-18 | 2009-12-17 | Enanta Pharm Inc | Ease-hemmer |
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- 2014-03-14 KR KR1020157028437A patent/KR102215400B1/ko active Active
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| KR102215400B1 (ko) | 2021-02-10 |
| KR20150130456A (ko) | 2015-11-23 |
| BR112015021768A2 (pt) | 2016-02-02 |
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| EP2970335A1 (en) | 2016-01-20 |
| US9617310B2 (en) | 2017-04-11 |
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| AU2014233390A1 (en) | 2015-09-03 |
| JP2019059775A (ja) | 2019-04-18 |
| MX2015013224A (es) | 2015-12-11 |
| EA029088B1 (ru) | 2018-02-28 |
| ES2735355T3 (es) | 2019-12-18 |
| WO2014145095A1 (en) | 2014-09-18 |
| EP2970335B1 (en) | 2019-05-08 |
| CN105073758B (zh) | 2017-08-11 |
| SG11201507223TA (en) | 2015-10-29 |
| HK1217196A1 (en) | 2016-12-30 |
| CN105073758A (zh) | 2015-11-18 |
| JP6511432B2 (ja) | 2019-05-15 |
| JP2016516069A (ja) | 2016-06-02 |
| CA2902569A1 (en) | 2014-09-18 |
| IL240662A0 (en) | 2015-10-29 |
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