JP2010518125A5 - - Google Patents
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- JP2010518125A5 JP2010518125A5 JP2009549295A JP2009549295A JP2010518125A5 JP 2010518125 A5 JP2010518125 A5 JP 2010518125A5 JP 2009549295 A JP2009549295 A JP 2009549295A JP 2009549295 A JP2009549295 A JP 2009549295A JP 2010518125 A5 JP2010518125 A5 JP 2010518125A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- aralkyl
- aryl
- solution
- alkyl
- 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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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 239000000243 solution Substances 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 33
- 230000000694 effects Effects 0.000 claims 29
- 238000000034 method Methods 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims 20
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 20
- 108091006112 ATPases Proteins 0.000 claims 18
- 102000057290 Adenosine Triphosphatases Human genes 0.000 claims 18
- 239000003550 marker Substances 0.000 claims 16
- -1 -C (O) H Chemical group 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 6
- 229920004890 Triton X-100 Polymers 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 6
- 229920000728 polyester Polymers 0.000 claims 6
- 239000004094 surface-active agent Substances 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 5
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical group CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 108060004795 Methyltransferase Proteins 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 230000003247 decreasing effect Effects 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 2
- UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 claims 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims 2
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 claims 2
- 108091005804 Peptidases Proteins 0.000 claims 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims 2
- 239000004365 Protease Substances 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- NLEBIOOXCVAHBD-QKMCSOCLSA-N dodecyl beta-D-maltoside Chemical compound O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NLEBIOOXCVAHBD-QKMCSOCLSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 239000007850 fluorescent dye Substances 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229920001992 poloxamer 407 Polymers 0.000 claims 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 108700004121 sarkosyl Proteins 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 239000012089 stop solution Substances 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- ZRKZFNZPJKEWPC-UHFFFAOYSA-N decylamine-N,N-dimethyl-N-oxide Chemical compound CCCCCCCCCC[N+](C)(C)[O-] ZRKZFNZPJKEWPC-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- YYRMITYYFKZLLJ-UHFFFAOYSA-N n,n-dimethylhexan-1-amine oxide Chemical group CCCCCC[N+](C)(C)[O-] YYRMITYYFKZLLJ-UHFFFAOYSA-N 0.000 claims 1
- XZEZLJBGDNUAQX-UHFFFAOYSA-N n,n-dimethylnonan-1-amine oxide Chemical compound CCCCCCCCC[N+](C)(C)[O-] XZEZLJBGDNUAQX-UHFFFAOYSA-N 0.000 claims 1
- RSVIRMFSJVHWJV-UHFFFAOYSA-N n,n-dimethyloctan-1-amine oxide Chemical compound CCCCCCCC[N+](C)(C)[O-] RSVIRMFSJVHWJV-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000002085 persistent effect Effects 0.000 claims 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims 1
- 229960000311 ritonavir Drugs 0.000 claims 1
- 230000002459 sustained effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88943307P | 2007-02-12 | 2007-02-12 | |
| PCT/US2008/053617 WO2008100867A2 (en) | 2007-02-12 | 2008-02-11 | Novel inhibitors hepatitis c virus replication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010518125A JP2010518125A (ja) | 2010-05-27 |
| JP2010518125A5 true JP2010518125A5 (https=) | 2011-03-31 |
Family
ID=39590457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009549295A Pending JP2010518125A (ja) | 2007-02-12 | 2008-02-11 | Ｃ型肝炎ウイルス複製の新規な阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20090047246A1 (https=) |
| EP (1) | EP2134683A2 (https=) |
| JP (1) | JP2010518125A (https=) |
| CN (1) | CN101687789A (https=) |
| AU (1) | AU2008216382A1 (https=) |
| CA (1) | CA2676906A1 (https=) |
| MX (1) | MX2009008439A (https=) |
| WO (1) | WO2008100867A2 (https=) |
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| KR102507287B1 (ko) | 2011-09-02 | 2023-03-07 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
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- 2008-02-11 CA CA002676906A patent/CA2676906A1/en not_active Abandoned
- 2008-02-11 WO PCT/US2008/053617 patent/WO2008100867A2/en not_active Ceased
- 2008-02-11 EP EP08729562A patent/EP2134683A2/en not_active Withdrawn
- 2008-02-11 MX MX2009008439A patent/MX2009008439A/es not_active Application Discontinuation
- 2008-02-11 US US12/029,399 patent/US20090047246A1/en not_active Abandoned
- 2008-02-11 JP JP2009549295A patent/JP2010518125A/ja active Pending
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