TW201249827A - Novel inhibitors of hepatitis C virus - Google Patents
Novel inhibitors of hepatitis C virus Download PDFInfo
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- TW201249827A TW201249827A TW100140412A TW100140412A TW201249827A TW 201249827 A TW201249827 A TW 201249827A TW 100140412 A TW100140412 A TW 100140412A TW 100140412 A TW100140412 A TW 100140412A TW 201249827 A TW201249827 A TW 201249827A
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- Prior art keywords
- alkyl
- group
- mmol
- methyl
- cycloalkyl
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- 241000711549 Hepacivirus C Species 0.000 title claims abstract description 41
- 239000003112 inhibitor Substances 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 31
- 230000010076 replication Effects 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 279
- 125000000217 alkyl group Chemical group 0.000 claims description 264
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 105
- -1 1-cyclopropyl-2-mercaptopyrrolidine Chemical compound 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 239000000126 substance Substances 0.000 claims description 76
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 239000007789 gas Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
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- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
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- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
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- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 7
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- 125000006413 ring segment Chemical group 0.000 claims description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A61K31/495—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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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US201161492267P | 2011-06-01 | 2011-06-01 |
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TW201249827A true TW201249827A (en) | 2012-12-16 |
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TW100140412A TW201249827A (en) | 2010-11-04 | 2011-11-04 | Novel inhibitors of hepatitis C virus |
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TWI577672B (zh) * | 2011-11-03 | 2017-04-11 | 施萬生物製藥研發Ip有限責任公司 | C型肝炎病毒抑制劑 |
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CA2690559A1 (en) * | 2007-06-12 | 2008-12-24 | Technolines, Llc | High speed and high power laser scribing methods and systems |
CA2737601C (en) * | 2009-06-11 | 2014-10-21 | Abbott Laboratories | Anti-viral compounds |
US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
CA2814534A1 (en) * | 2010-11-04 | 2012-05-10 | Theravance, Inc. | Novel inhibitors of hepatitis c virus |
US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
US9546160B2 (en) | 2011-05-12 | 2017-01-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
RS55701B1 (sr) | 2011-06-22 | 2017-07-31 | Purdue Pharma Lp | Trpv1 antagonisti koji uključuju dihidroksi supstituent i njihove upotrebe |
US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
EP2850072B1 (en) | 2012-04-25 | 2016-08-31 | Theravance Biopharma R&D IP, LLC | Hepatitis c virus inhibitors |
SI2850075T1 (sl) * | 2012-04-25 | 2017-06-30 | Theravance Biopharma R&D Ip, Llc | Piperazin-piperidinske spojine kot inhibitorji virusa hepatitisa C |
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- 2011-11-03 EP EP11784875.4A patent/EP2635571B1/en active Active
- 2011-11-03 CN CN201180053127.4A patent/CN103189371B/zh not_active Expired - Fee Related
- 2011-11-03 JP JP2013537808A patent/JP5891235B2/ja not_active Expired - Fee Related
- 2011-11-03 US US13/288,216 patent/US8921372B2/en not_active Expired - Fee Related
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- 2011-11-04 TW TW100140412A patent/TW201249827A/zh unknown
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2014
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI577672B (zh) * | 2011-11-03 | 2017-04-11 | 施萬生物製藥研發Ip有限責任公司 | C型肝炎病毒抑制劑 |
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EP2635571B1 (en) | 2015-08-12 |
US8921372B2 (en) | 2014-12-30 |
ES2548286T3 (es) | 2015-10-15 |
JP2013544812A (ja) | 2013-12-19 |
CN103189371A (zh) | 2013-07-03 |
CN103189371B (zh) | 2015-04-01 |
US20150071878A1 (en) | 2015-03-12 |
EP2635571A1 (en) | 2013-09-11 |
US9260414B2 (en) | 2016-02-16 |
JP5891235B2 (ja) | 2016-03-22 |
US20120114600A1 (en) | 2012-05-10 |
CA2814534A1 (en) | 2012-05-10 |
WO2012061552A1 (en) | 2012-05-10 |
AR083757A1 (es) | 2013-03-20 |
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