JP2012518000A5 - - Google Patents
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- Publication number
- JP2012518000A5 JP2012518000A5 JP2011550182A JP2011550182A JP2012518000A5 JP 2012518000 A5 JP2012518000 A5 JP 2012518000A5 JP 2011550182 A JP2011550182 A JP 2011550182A JP 2011550182 A JP2011550182 A JP 2011550182A JP 2012518000 A5 JP2012518000 A5 JP 2012518000A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidinyl
- benzimidazol
- methyl
- imidazol
- phenylacetyl
- 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.)
- Granted
Links
- -1 (2S) -2- (5- (4- (2-((2S) -1-((2S) -2-((methoxycarbonyl) amino) -3-methyl Butanoyl) -2-pyrrolidinyl) -1H-imidazol-4-yl) phenyl) -1H-benzimidazol-2-yl) -1-pyrrolidinyl Chemical group 0.000 claims 67
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 53
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 8
- 108010047761 Interferon-alpha Proteins 0.000 claims 6
- 102000006992 Interferon-alpha Human genes 0.000 claims 6
- 108010050904 Interferons Proteins 0.000 claims 6
- 102000014150 Interferons Human genes 0.000 claims 6
- 229940079322 interferon Drugs 0.000 claims 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 6
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229960000329 ribavirin Drugs 0.000 claims 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 2
- HAEJPQIATWHALX-KQYNXXCUSA-N ITP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 HAEJPQIATWHALX-KQYNXXCUSA-N 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000034303 cell budding Effects 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims 1
- XSNFELLECPQEDL-AACOOOPESA-N CC1=C(C=C(C=C1)C2=NC=C(O2)C3=CC4=C(C=C3)N=C(N4)[C@@H]5CCCN5C(=O)[C@@H](C6=CC=CC=C6)N(C)C)NC(=O)C7=NCCC7C(=O)CN(C)C Chemical compound CC1=C(C=C(C=C1)C2=NC=C(O2)C3=CC4=C(C=C3)N=C(N4)[C@@H]5CCCN5C(=O)[C@@H](C6=CC=CC=C6)N(C)C)NC(=O)C7=NCCC7C(=O)CN(C)C XSNFELLECPQEDL-AACOOOPESA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15318609P | 2009-02-17 | 2009-02-17 | |
| US61/153,186 | 2009-02-17 | ||
| US12/701,919 US8809548B2 (en) | 2009-02-17 | 2010-02-08 | Hepatitis C virus inhibitors |
| US12/701,919 | 2010-02-08 | ||
| PCT/US2010/023582 WO2010096302A1 (en) | 2009-02-17 | 2010-02-09 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012518000A JP2012518000A (ja) | 2012-08-09 |
| JP2012518000A5 true JP2012518000A5 (https=) | 2013-03-07 |
| JP5612612B2 JP5612612B2 (ja) | 2014-10-22 |
Family
ID=42631140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011550182A Expired - Fee Related JP5612612B2 (ja) | 2009-02-17 | 2010-02-09 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US8809548B2 (https=) |
| EP (1) | EP2398794B1 (https=) |
| JP (1) | JP5612612B2 (https=) |
| KR (1) | KR20110124774A (https=) |
| CN (1) | CN102395579B (https=) |
| AR (1) | AR075510A1 (https=) |
| AU (2) | AU2010216227A1 (https=) |
| BR (1) | BRPI1008846A2 (https=) |
| CA (1) | CA2752579A1 (https=) |
| CL (1) | CL2011002016A1 (https=) |
| CO (1) | CO6400192A2 (https=) |
| DK (1) | DK2398794T3 (https=) |
| EA (1) | EA019976B1 (https=) |
| ES (1) | ES2400951T3 (https=) |
| HR (1) | HRP20130063T1 (https=) |
| IL (1) | IL214098A (https=) |
| MX (1) | MX2011008045A (https=) |
| NZ (1) | NZ594068A (https=) |
| PE (1) | PE20120258A1 (https=) |
| PL (1) | PL2398794T3 (https=) |
| PT (1) | PT2398794E (https=) |
| SG (1) | SG173440A1 (https=) |
| SI (1) | SI2398794T1 (https=) |
| SM (1) | SMT201300043B (https=) |
| TW (1) | TWI438200B (https=) |
| WO (1) | WO2010096302A1 (https=) |
| ZA (1) | ZA201105722B (https=) |
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| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
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