JP2014520822A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014520822A5 JP2014520822A5 JP2014519378A JP2014519378A JP2014520822A5 JP 2014520822 A5 JP2014520822 A5 JP 2014520822A5 JP 2014519378 A JP2014519378 A JP 2014519378A JP 2014519378 A JP2014519378 A JP 2014519378A JP 2014520822 A5 JP2014520822 A5 JP 2014520822A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- aliphatic
- aryl
- heterocyclyl
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 125000000623 heterocyclic group Chemical group 0.000 claims description 110
- 125000003118 aryl group Chemical group 0.000 claims description 109
- 125000001072 heteroaryl group Chemical group 0.000 claims description 91
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 56
- 229910052801 chlorine Inorganic materials 0.000 claims description 54
- 229910052731 fluorine Inorganic materials 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- -1 hydroxy, amino Chemical group 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 42
- 125000001931 aliphatic group Chemical group 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 40
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 26
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 24
- 125000001769 aryl amino group Chemical group 0.000 claims description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 14
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 14
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 14
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003003 spiro group Chemical group 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 12
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 9
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 239000002207 metabolite Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 108010050904 Interferons Proteins 0.000 claims 4
- 102000014150 Interferons Human genes 0.000 claims 4
- 229940079322 interferon Drugs 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 108010047761 Interferon-alpha Proteins 0.000 claims 2
- 102000006992 Interferon-alpha Human genes 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
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 108020005544 Antisense RNA Proteins 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims 1
- 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 1
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 1
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 108090001005 Interleukin-6 Proteins 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims 1
- JTTHKOPSMAVJFE-VIFPVBQESA-N L-homophenylalanine Chemical compound OC(=O)[C@@H](N)CCC1=CC=CC=C1 JTTHKOPSMAVJFE-VIFPVBQESA-N 0.000 claims 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- JZKXXXDKRQWDET-QMMMGPOBSA-N L-m-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-QMMMGPOBSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 108010077895 Sarcosine Proteins 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 230000005867 T cell response Effects 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims 1
- 229960000517 boceprevir Drugs 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- FKRSSPOQAMALKA-CUPIEXAXSA-N daclatasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)=CN1 FKRSSPOQAMALKA-CUPIEXAXSA-N 0.000 claims 1
- 229960005449 daclatasvir Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 108700003601 dimethylglycine Proteins 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 235000004554 glutamine Nutrition 0.000 claims 1
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 229960002591 hydroxyproline Drugs 0.000 claims 1
- 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 1
- 229960002751 imiquimod Drugs 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 230000009545 invasion Effects 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- JZKXXXDKRQWDET-UHFFFAOYSA-N meta-tyrosine Natural products OC(=O)C(N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-UHFFFAOYSA-N 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 229940078490 n,n-dimethylglycine Drugs 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 235000013930 proline Nutrition 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- 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 1
- 229960000888 rimantadine Drugs 0.000 claims 1
- 229940043230 sarcosine Drugs 0.000 claims 1
- 235000004400 serine Nutrition 0.000 claims 1
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims 1
- 229960002935 telaprevir Drugs 0.000 claims 1
- 108010017101 telaprevir Proteins 0.000 claims 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 235000014393 valine Nutrition 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 0 N=*C1=CCCCC=CCC2CC1C2 Chemical compound N=*C1=CCCCC=CCC2CC1C2 0.000 description 26
- 125000004122 cyclic group Chemical group 0.000 description 6
- MVHOAOSHABGEFL-UHFFFAOYSA-N Cc1nc(cc(C)cc2)c2[nH]1 Chemical compound Cc1nc(cc(C)cc2)c2[nH]1 MVHOAOSHABGEFL-UHFFFAOYSA-N 0.000 description 4
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N Cc1cnc(C)[nH]1 Chemical compound Cc1cnc(C)[nH]1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FRXLGXNJLKYPBM-UHFFFAOYSA-N Cc1nc(ccc(-c2ccc(C)cc2)c2)c2[nH]1 Chemical compound Cc1nc(ccc(-c2ccc(C)cc2)c2)c2[nH]1 FRXLGXNJLKYPBM-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- NNETVVVKJRQFFF-UHFFFAOYSA-N CC(C)=NC(C)=N Chemical compound CC(C)=NC(C)=N NNETVVVKJRQFFF-UHFFFAOYSA-N 0.000 description 1
- RAPTZNFAMIHBTG-UHFFFAOYSA-N CC(C)CC(N1CCCC1)=O Chemical compound CC(C)CC(N1CCCC1)=O RAPTZNFAMIHBTG-UHFFFAOYSA-N 0.000 description 1
- XHVZYDYZAWTRNC-VUWPPUDQSA-N CC(C)[C@@H](C(N1CC2(CC2)CC1)O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N1CC2(CC2)CC1)O)NC(OC)=O XHVZYDYZAWTRNC-VUWPPUDQSA-N 0.000 description 1
- WXPDONXQEMHKRQ-SHUZPENHSA-N CC(C)[C@@H](C(N1[C@H](c2ncc(-c(c3c4CC5(CCCC5)C3)ccc4-c(cc3)ccc3-c3cnc(C=C)[nH]3)[nH]2)SCC1)=O)NC(OC)=O Chemical compound CC(C)[C@@H](C(N1[C@H](c2ncc(-c(c3c4CC5(CCCC5)C3)ccc4-c(cc3)ccc3-c3cnc(C=C)[nH]3)[nH]2)SCC1)=O)NC(OC)=O WXPDONXQEMHKRQ-SHUZPENHSA-N 0.000 description 1
- ZPDGQGUHCOIMBK-ZCFIWIBFSA-N CC(C)[C@@H](C)NC=O Chemical compound CC(C)[C@@H](C)NC=O ZPDGQGUHCOIMBK-ZCFIWIBFSA-N 0.000 description 1
- GINNNRQOBSAUHS-UHFFFAOYSA-N CC(CC1)CCC1c1cnc(C)[nH]1 Chemical compound CC(CC1)CCC1c1cnc(C)[nH]1 GINNNRQOBSAUHS-UHFFFAOYSA-N 0.000 description 1
- YICAMJWHIUMFDI-UHFFFAOYSA-N CC(Nc1ccc(C)cc1)=O Chemical compound CC(Nc1ccc(C)cc1)=O YICAMJWHIUMFDI-UHFFFAOYSA-N 0.000 description 1
- TVSMLBGFGKLKOO-UHFFFAOYSA-N CC1CCN(C)CC1 Chemical compound CC1CCN(C)CC1 TVSMLBGFGKLKOO-UHFFFAOYSA-N 0.000 description 1
- ZEBFPAXSQXIPNF-UHFFFAOYSA-N CC1NC(C)CC1 Chemical compound CC1NC(C)CC1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 description 1
- LIWSUETYYMPTRY-IAXJKZSUSA-N CCO[C@@](CC1)(CN1C(C(C(C)C)NC(OC)=O)=O)OC Chemical compound CCO[C@@](CC1)(CN1C(C(C(C)C)NC(OC)=O)=O)OC LIWSUETYYMPTRY-IAXJKZSUSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- DTZQNEGIDKMTEN-UHFFFAOYSA-N COC(NCCN(CC1(CC1)C1)C1c1ncc(-c(cc2)ccc2-c(c2c3CC4(CCCC4)C2)ccc3-c(cc2)ccc2-c2cnc[nH]2)[nH]1)=O Chemical compound COC(NCCN(CC1(CC1)C1)C1c1ncc(-c(cc2)ccc2-c(c2c3CC4(CCCC4)C2)ccc3-c(cc2)ccc2-c2cnc[nH]2)[nH]1)=O DTZQNEGIDKMTEN-UHFFFAOYSA-N 0.000 description 1
- DMJJJHIFADRWEF-UHFFFAOYSA-N Cc([nH]1)nc2c1nc(C)cc2 Chemical compound Cc([nH]1)nc2c1nc(C)cc2 DMJJJHIFADRWEF-UHFFFAOYSA-N 0.000 description 1
- GHKLCVJTEJBCBX-UHFFFAOYSA-N Cc([nH]c1c2)nc1cc1c2cc(C)cc1 Chemical compound Cc([nH]c1c2)nc1cc1c2cc(C)cc1 GHKLCVJTEJBCBX-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N Cc1cc(C)n[nH]1 Chemical compound Cc1cc(C)n[nH]1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- CAVYFFVMODYNTB-UHFFFAOYSA-N Cc1ccc(-c2cnc(C)[nH]2)[s]1 Chemical compound Cc1ccc(-c2cnc(C)[nH]2)[s]1 CAVYFFVMODYNTB-UHFFFAOYSA-N 0.000 description 1
- UWXXUKDLTRPMMF-UHFFFAOYSA-N Cc1nc(COc2c-3ccc(C)c2)c-3[nH]1 Chemical compound Cc1nc(COc2c-3ccc(C)c2)c-3[nH]1 UWXXUKDLTRPMMF-UHFFFAOYSA-N 0.000 description 1
- RYBQCQMZQAUIQN-UHFFFAOYSA-N Cc1nc(ccc2c3ccc(C)c2)c3[nH]1 Chemical compound Cc1nc(ccc2c3ccc(C)c2)c3[nH]1 RYBQCQMZQAUIQN-UHFFFAOYSA-N 0.000 description 1
- BHTLHVMHQVCJCE-UHFFFAOYSA-N Cc1nc(cnc(C)c2)c2[nH]1 Chemical compound Cc1nc(cnc(C)c2)c2[nH]1 BHTLHVMHQVCJCE-UHFFFAOYSA-N 0.000 description 1
- LZSXKOQVSYULPZ-UHFFFAOYSA-N Cc1nc2cc(C)cnc2[nH]1 Chemical compound Cc1nc2cc(C)cnc2[nH]1 LZSXKOQVSYULPZ-UHFFFAOYSA-N 0.000 description 1
- RYCGXZAXJPAXDX-UHFFFAOYSA-N Cc1ncc(-c2ccc(C)cc2)[nH]1 Chemical compound Cc1ncc(-c2ccc(C)cc2)[nH]1 RYCGXZAXJPAXDX-UHFFFAOYSA-N 0.000 description 1
- ZTPXKLMKGWAUMQ-UHFFFAOYSA-N Cc1ncc(-c2ccc(cc(C)cc3)c3c2)[nH]1 Chemical compound Cc1ncc(-c2ccc(cc(C)cc3)c3c2)[nH]1 ZTPXKLMKGWAUMQ-UHFFFAOYSA-N 0.000 description 1
- BGDOKDIEVXQWSS-UHFFFAOYSA-N Cc1ncc(C(CC2)C=NC3=C2[I]=CC(C)=C3)[nH]1 Chemical compound Cc1ncc(C(CC2)C=NC3=C2[I]=CC(C)=C3)[nH]1 BGDOKDIEVXQWSS-UHFFFAOYSA-N 0.000 description 1
- WDEGVMDTYMVHTC-UHFFFAOYSA-N Cc1ncc(C2CCN(C)CC2)[nH]1 Chemical compound Cc1ncc(C2CCN(C)CC2)[nH]1 WDEGVMDTYMVHTC-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110195113 | 2011-07-09 | ||
| CN201110195113.8 | 2011-07-09 | ||
| PCT/CN2012/000945 WO2013007106A1 (zh) | 2011-07-09 | 2012-07-09 | 作为丙型肝炎病毒抑制剂的螺环化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014520822A JP2014520822A (ja) | 2014-08-25 |
| JP2014520822A5 true JP2014520822A5 (enExample) | 2015-06-18 |
Family
ID=47442590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014519378A Pending JP2014520822A (ja) | 2011-07-09 | 2012-07-09 | Ｃ型肝炎ウイルス阻害剤としてのスピロ化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9303061B2 (enExample) |
| EP (1) | EP2730572B1 (enExample) |
| JP (1) | JP2014520822A (enExample) |
| KR (1) | KR20140053166A (enExample) |
| CN (1) | CN102863428B (enExample) |
| AU (1) | AU2012283609B2 (enExample) |
| BR (1) | BR112014000563A2 (enExample) |
| CA (1) | CA2841095A1 (enExample) |
| TW (1) | TWI482766B (enExample) |
| WO (1) | WO2013007106A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2013011932A1 (ja) | 2011-07-15 | 2013-01-24 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するアザベンズイミダゾール誘導体 |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI610916B (zh) * | 2012-08-03 | 2018-01-11 | 廣東東陽光藥業有限公司 | 作爲丙型肝炎抑制劑的橋環化合物及其在藥物中的應用 |
| TW201412709A (zh) | 2012-09-28 | 2014-04-01 | Sunshine Lake Pharma Co Ltd | 作為丙型肝炎抑制劑的螺環化合物及其在藥物中的應用 |
| TWI585082B (zh) * | 2012-11-29 | 2017-06-01 | 廣東東陽光藥業有限公司 | 作爲丙型肝炎抑制劑的螺環化合物、藥物組合物及它們的用途 |
| TW201439060A (zh) * | 2013-02-27 | 2014-10-16 | Sunshine Lake Pharma Co Ltd | 作爲丙型肝炎抑制劑的橋環化合物及其藥物組合物和用途 |
| CN111116563B (zh) * | 2013-06-06 | 2023-07-04 | 上海爱博医药科技有限公司 | 抑制丙肝病毒的化合物、药物组合物及其应用 |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US9717712B2 (en) | 2013-07-02 | 2017-08-01 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus |
| CN105530933B (zh) | 2013-07-17 | 2018-12-11 | 百时美施贵宝公司 | 用于治疗hcv的包含联苯衍生物的组合产品 |
| US9738629B2 (en) | 2014-01-23 | 2017-08-22 | Sunshine Lake Pharma Co., Ltd. | Bridged ring compounds as Hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof |
| CN104860931A (zh) * | 2014-02-21 | 2015-08-26 | 常州寅盛药业有限公司 | 丙肝病毒抑制剂及其制药用途 |
| CN105085493A (zh) * | 2014-04-15 | 2015-11-25 | 广东东阳光药业有限公司 | 作为丙型肝炎抑制剂的螺环化合物及其在药物中的应用 |
| WO2015184644A1 (zh) * | 2014-06-06 | 2015-12-10 | 爱博新药研发(上海)有限公司 | 抑制丙肝病毒的化合物、药物组合物及其应用 |
| WO2016045587A1 (zh) | 2014-09-26 | 2016-03-31 | 常州寅盛药业有限公司 | 作为ns4b抑制剂的苯并呋喃类似物 |
| WO2017023631A1 (en) | 2015-08-06 | 2017-02-09 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| CN106432195B (zh) * | 2015-08-12 | 2020-01-14 | 杭州民生药物研究院有限公司 | 一种制备(r)-2-(2-甲基吡咯烷-2-基)-1h-苯并咪唑-4-甲酰胺的方法 |
| CN105461701A (zh) * | 2015-12-14 | 2016-04-06 | 上海步越化工科技有限公司 | 一种抗丙肝新药达卡他韦新的合成方法 |
| CN105622583A (zh) * | 2015-12-22 | 2016-06-01 | 苏州步跃医药科技有限公司 | 一种抗丙肝新药达卡他韦新的制备方法 |
| CN112225778A (zh) * | 2020-10-26 | 2021-01-15 | 辰欣药业股份有限公司 | 一种马来酸依那普利的制备方法 |
| CN116120272A (zh) * | 2022-12-31 | 2023-05-16 | 淮北师范大学 | 一种合成咯菌腈中间体2,2-二氟-1,3-苯并二噁茂-4-甲醛的方法 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2999098A (en) * | 1957-11-13 | 1961-09-05 | Universal Oil Prod Co | Bis-halocycloalkenyl derivatives of alkylidenedioxybenzenes |
| FR2707982B1 (fr) * | 1993-07-20 | 1995-09-01 | Adir | Nouveaux dérivés de benzospiroalcène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8642660B2 (en) * | 2007-12-21 | 2014-02-04 | The University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US7704992B2 (en) | 2008-02-13 | 2010-04-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| BRPI0922366B8 (pt) * | 2008-12-03 | 2021-05-25 | Presidio Pharmaceuticals Inc | composto, composição farmacêutica e uso de um composto |
| US8314135B2 (en) | 2009-02-09 | 2012-11-20 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole antivirals |
| US8426458B2 (en) | 2009-02-27 | 2013-04-23 | Enanta Pharmaceuticals, Inc. | Hepatitis C Virus inhibitors |
| CN102427729B (zh) | 2009-03-27 | 2014-09-03 | 默沙东公司 | 丙型肝炎病毒复制的抑制剂 |
| US8709999B2 (en) | 2009-03-27 | 2014-04-29 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic HCV inhibitors |
| MX2011010132A (es) | 2009-03-27 | 2011-10-14 | Presidio Pharmaceuticals Inc | Inhibidores de anillo fusionado de hepatitis c. |
| US8796466B2 (en) * | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2419404B1 (en) * | 2009-04-15 | 2015-11-04 | AbbVie Inc. | Anti-viral compounds |
| US9139569B2 (en) | 2009-05-12 | 2015-09-22 | Merck Sharp & Dohme Corp. | Fused tricyclic aryl compounds useful for the treatment of viral diseases |
| RS56654B8 (sr) | 2009-05-13 | 2021-06-30 | Gilead Pharmasset Llc | Antiviralna jedinjenja |
| KR101724765B1 (ko) | 2009-05-18 | 2017-04-07 | 액테리온 파마슈티칼 리미티드 | Ａｌｘ 수용체 및/또는 ｆｐｒｌ2 아고니스트로서의 브릿지 스피로［2.4］헵탄 유도체 |
| US8772505B2 (en) | 2009-05-29 | 2014-07-08 | Merck Sharp & Dohme Corp. | Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis C |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011004276A1 (en) | 2009-07-06 | 2011-01-13 | Pfizer Limited | Hepatitis c virus inhibitors |
| EP2454254A2 (en) * | 2009-07-16 | 2012-05-23 | Vertex Pharmaceuticals Incorporated | Benzimidazole analogues for the treatment or prevention of flavivirus infections |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| AU2010324871A1 (en) | 2009-11-25 | 2012-06-14 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases |
| SG181797A1 (en) | 2009-12-18 | 2012-07-30 | Idenix Pharmaceuticals Inc | 5,5-fused arylene or heteroarylene hepatitis c virus inhibitors |
| CA2785488A1 (en) | 2009-12-22 | 2011-07-21 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases |
| US20130072523A1 (en) | 2009-12-24 | 2013-03-21 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| WO2011119870A1 (en) | 2010-03-24 | 2011-09-29 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
| MX2012010918A (es) | 2010-03-24 | 2013-01-18 | Vertex Pharma | Analogos para el tratamiento o prevencion de infecciones por flavivirus. |
| US20110312996A1 (en) | 2010-05-17 | 2011-12-22 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| EP2575866A4 (en) | 2010-05-24 | 2013-10-16 | Presidio Pharmaceuticals Inc | HCV NS5A INHIBITORS |
| TW201201801A (en) | 2010-06-09 | 2012-01-16 | Presidio Pharmaceuticals Inc | Inhibitors of HCV NS5A protein |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| WO2012003642A1 (en) | 2010-07-09 | 2012-01-12 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and use thereof for treating viral diseases |
| WO2012018534A2 (en) | 2010-07-26 | 2012-02-09 | Schering Corporation | Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases |
| WO2012013643A1 (en) | 2010-07-26 | 2012-02-02 | Tibotec Pharmaceuticals | Hetero-bicyclic derivatives as hcv inhibitors |
| US20120195857A1 (en) | 2010-08-12 | 2012-08-02 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| WO2012020036A1 (en) | 2010-08-13 | 2012-02-16 | F. Hoffmann-La Roche Ag | Hepatitis c virus inhibitors |
| BR112013007696A2 (pt) | 2010-09-29 | 2019-09-24 | Merck Sharp & Dohme | composto, composição farmacêutica, usos do referido composto e da referida composição |
| EP2621279B1 (en) | 2010-09-29 | 2018-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012040923A1 (en) | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012041227A1 (en) | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds for treating hepatitis c viral infection |
| WO2012040924A1 (en) | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Fused tetracyclic heterocycle compounds and methods of use thereof for treatment of viral diseases |
| WO2012050918A2 (en) | 2010-09-29 | 2012-04-19 | Presidio Pharmaceutical, Inc. | Tricyclic fused ring inhibitors of hepatitis c |
| WO2012075140A1 (en) * | 2010-11-30 | 2012-06-07 | Pharmasset, Inc. | Compounds |
| WO2012083053A2 (en) | 2010-12-15 | 2012-06-21 | Abbott Laboratories | Anti-viral compounds |
| US20150158909A1 (en) | 2010-12-15 | 2015-06-11 | Abbevie Inc. | Anti-viral compounds |
| MX2013006828A (es) | 2010-12-16 | 2014-10-14 | Abbvie Inc | Compuestos antivirales. |
| WO2012122716A1 (en) | 2011-03-17 | 2012-09-20 | Merck Sharp & Dohme Corp. | Tetracyclic xanthene derivatives and methods of use thereof for treatment of viral diseases |
| PH12014500311A1 (en) | 2011-08-08 | 2014-03-31 | Lupin Ltd | Antiviral compounds with a fused tricyclic ring |
| WO2013022810A1 (en) | 2011-08-08 | 2013-02-14 | Glaxosmithkline Llc | Chemical compounds |
| PT2907816T (pt) | 2011-11-16 | 2018-10-18 | Gilead Pharmasset Llc | Imidazolilimidazóis condensados como compostos antivirais |
| BR112014016157A8 (pt) | 2011-12-28 | 2017-07-04 | Janssen R&D Ireland | derivados heterobicíclicos como inibidores de vhc |
| IN2014MN01547A (enExample) | 2012-02-10 | 2015-05-08 | Lupin Ltd |
-
2012
- 2012-07-09 CA CA2841095A patent/CA2841095A1/en not_active Abandoned
- 2012-07-09 KR KR1020147002974A patent/KR20140053166A/ko not_active Withdrawn
- 2012-07-09 WO PCT/CN2012/000945 patent/WO2013007106A1/zh not_active Ceased
- 2012-07-09 TW TW101124685A patent/TWI482766B/zh not_active IP Right Cessation
- 2012-07-09 BR BR112014000563-0A patent/BR112014000563A2/pt not_active Application Discontinuation
- 2012-07-09 CN CN201210239748.8A patent/CN102863428B/zh active Active
- 2012-07-09 US US14/130,320 patent/US9303061B2/en not_active Expired - Fee Related
- 2012-07-09 EP EP12811420.4A patent/EP2730572B1/en not_active Not-in-force
- 2012-07-09 AU AU2012283609A patent/AU2012283609B2/en not_active Ceased
- 2012-07-09 JP JP2014519378A patent/JP2014520822A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2449540T3 (es) | Inhibidores macrocíclicos del virus de la hepatitis C | |
| ES2555230T3 (es) | Productos intermedios para la preparación de inhibidores macrocíclicos del virus de la hepatitis C | |
| ES2640063T3 (es) | Derivados de n-fenil-carboxamida y su uso como medicamentos para el tratamiento de la hepatitis B | |
| ES2470568T3 (es) | Inhibidores macroc�clicos del virus de la hepatitis C | |
| ES2670984T3 (es) | Composiciones y métodos para modular receptores X farnesoides | |
| ES2761824T3 (es) | Compuestos de carboximidamida de benzimidazol y imidazopiridina que tienen actividad como inhibidores de indoleamina 2,3-dioxigenasa | |
| RU2015107043A (ru) | Соединенные циклические соединения как ингибиторы вируса гепатита с (вгс) и их фармацевтическое применение | |
| US10160743B2 (en) | Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis B | |
| ES2359939T3 (es) | Inhibidores macrocíclicos del virus de la hepatitis c. | |
| JP2010508361A5 (enExample) | ||
| ES2541660T3 (es) | Inhibidores del VHC macrocíclicos sustituidos con pirimidina | |
| JP2021534124A5 (enExample) | ||
| JP2010508362A5 (enExample) | ||
| ES2564906T3 (es) | Inhibidores de NS5A del VHC | |
| JP2012523415A5 (enExample) | ||
| JP2010508360A5 (enExample) | ||
| JP2012533630A5 (enExample) | ||
| JP5808496B2 (ja) | 抗ウイルス化合物 | |
| CA2875690A1 (en) | Macrocyclic inhibitors of flaviviridae viruses | |
| JP2013517286A5 (enExample) | ||
| CN111433210A (zh) | 作为抗病毒药的稠合三环吡唑并-二氢吡嗪基-吡啶酮化合物 | |
| JP2011511841A5 (enExample) | ||
| JP2011511840A5 (enExample) | ||
| JP2015529652A5 (enExample) | ||
| WO2019097479A1 (en) | Novel dihydroisoxazole compounds and their use for the treatment of hepatitis b |