HRP20120706T1 - Imidazolil bifenil imidazoli kao inhibitori virusa hepatitisa c - Google Patents

Imidazolil bifenil imidazoli kao inhibitori virusa hepatitisa c Download PDF

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Publication number: HRP20120706T1
Authority: HR; Croatia
Prior art keywords: imidazol; methyl; pyrrolidinyl; biphenylyl; azabicyclo
Prior art date: 2008-02-13

Application number

HRP20120706AT

Other languages

English (en)

Croatian (hr)

Inventor

Bachand Carol

Belema Makonen

H. Deon Daniel

C. Good Andrew

Goodrich Jason

A. James Clint

Lavoie Rico

D. Lopez Omar

Martel Alain

A. Meanwell Nicholas

N. Nguyen Van

Lee Romine Jeffrey

H. Ruediger Edward

B. Snyder Lawrence

R. St. Laurent Denis

Yang Fukang

R. Langley David

Wang Gan

G. Hamann Lawrence

Original Assignee

Bristol-Myers Squibb Company

Priority date (The priority date 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 date listed.)

2008-02-13

Filing date

2012-09-05

Publication date

2012-09-30

2012-09-05 Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company

2012-09-30 Publication of HRP20120706T1 publication Critical patent/HRP20120706T1/hr

Links

239000003112 inhibitor Substances 0.000 title claims 2
241000711549 Hepacivirus C Species 0.000 title 1
MZYZINVCXFAPDR-UHFFFAOYSA-N N1C=NC=C1.N1C(=NC=C1)C1=C(C=CC=C1)C1=CC=CC=C1 Chemical class N1C=NC=C1.N1C(=NC=C1)C1=C(C=CC=C1)C1=CC=CC=C1 MZYZINVCXFAPDR-UHFFFAOYSA-N 0.000 title 1
-1 hex-3-yl Chemical group 0.000 claims abstract 35
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 31
150000001875 compounds Chemical class 0.000 claims abstract 20
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims abstract 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 5
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims abstract 2
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
239000000203 mixture Substances 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
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
150000003839 salts Chemical class 0.000 claims 4
208000015181 infectious disease Diseases 0.000 claims 3
UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
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
230000000692 anti-sense effect Effects 0.000 claims 2
230000000694 effects Effects 0.000 claims 2
210000002443 helper t lymphocyte Anatomy 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
230000002401 inhibitory effect 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
229960000888 rimantadine Drugs 0.000 claims 2
FOSBSHAMRIKTBL-MYIKROSKSA-N (2r)-1-[(2s)-2-[5-methyl-4-[4-[4-[5-methyl-2-[(2s)-1-[(2r)-2-phenyl-2-piperidin-1-ylacetyl]pyrrolidin-2-yl]-1h-imidazol-4-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenyl-2-piperidin-1-ylethanone Chemical compound N1([C@@H](C(=O)N2CCC[C@H]2C=2NC(=C(N=2)C)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2NC(=NC=2C)[C@H]2N(CCC2)C(=O)[C@H](N2CCCCC2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCCCC1 FOSBSHAMRIKTBL-MYIKROSKSA-N 0.000 claims 1
VJTJCURBLMITNB-HKIUVQRKSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[4-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-5-methyl-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C2=NC(=C(N2)C)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 VJTJCURBLMITNB-HKIUVQRKSA-N 0.000 claims 1
OUAXETFAKLYQFT-UNWJUUMBSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[4-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-5-methyl-1h-imidazol-4-yl]phenyl]phenyl]-5-methyl-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2NC(=C(N=2)C)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=C(C)N=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 OUAXETFAKLYQFT-UNWJUUMBSA-N 0.000 claims 1
NPXGTKGFHDUWMF-RIQKCDLYSA-N (2r)-2-(diethylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2r)-2-(diethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-5-propyl-1h-imidazol-4-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(CC)CC)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2N=C(NC=2CCC)[C@H]2N(CCC2)C(=O)[C@H](N(CC)CC)C=2C=CC=CC=2)=CC=CC=C1 NPXGTKGFHDUWMF-RIQKCDLYSA-N 0.000 claims 1
SWGGACXWQIEZOM-XCIZVNRNSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[4-[4-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-5-methyl-1h-imidazol-4-yl]phenyl]phenyl]-5-methyl-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC(=C(N=2)C)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=C(C)N=C(N2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 SWGGACXWQIEZOM-XCIZVNRNSA-N 0.000 claims 1
WANORSOXIJEBBS-VVXXNSFSSA-N (2r)-2-hydroxy-1-[(2s,5s)-2-[5-[4-[4-[2-[(2s,5s)-1-[(2r)-2-hydroxy-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)[C@@H](O)C(=O)N1[C@@H](C)CC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H](C)CC2)C(=O)[C@H](O)C(C)C)=CN1 WANORSOXIJEBBS-VVXXNSFSSA-N 0.000 claims 1
RURSFBCJLYOAFZ-VOIOCNMVSA-N (2s)-2-(pyrimidin-2-ylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-(pyrimidin-2-ylamino)butanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]butan-1-one Chemical compound N([C@@H](CC)C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@H](CC)NC=1N=CC=CN=1)C1=NC=CC=N1 RURSFBCJLYOAFZ-VOIOCNMVSA-N 0.000 claims 1
NYAZTTUYPZNSHT-PNRIMKNJSA-N (2s)-2-(pyrimidin-2-ylamino)-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-(pyrimidin-2-ylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]propan-1-one Chemical compound N([C@@H](C)C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@H](C)NC=1N=CC=CN=1)C1=NC=CC=N1 NYAZTTUYPZNSHT-PNRIMKNJSA-N 0.000 claims 1
RRPWCNMSBCFXJK-ZQWQDMLBSA-N (2s)-2-cyclopropyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-2-cyclopropyl-2-(pyrimidin-2-ylamino)acetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-(pyrimidin-2-ylamino)ethanone Chemical compound N([C@H](C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@@H](NC=1N=CC=CN=1)C1CC1)C1CC1)C1=NC=CC=N1 RRPWCNMSBCFXJK-ZQWQDMLBSA-N 0.000 claims 1
WANORSOXIJEBBS-QACNAPGISA-N (2s)-2-hydroxy-1-[(2s,5s)-2-[5-[4-[4-[2-[(2s,5s)-1-[(2s)-2-hydroxy-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)[C@H](O)C(=O)N1[C@@H](C)CC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H](C)CC2)C(=O)[C@@H](O)C(C)C)=CN1 WANORSOXIJEBBS-QACNAPGISA-N 0.000 claims 1
COAUJYXPVPGPRZ-ZYADHFCISA-N (2s)-3-methoxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-3-methoxy-2-(pyrimidin-2-ylamino)propanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-(pyrimidin-2-ylamino)propan-1-one Chemical compound N([C@@H](COC)C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@H](COC)NC=1N=CC=CN=1)C1=NC=CC=N1 COAUJYXPVPGPRZ-ZYADHFCISA-N 0.000 claims 1
BUMSXOMPQQXECH-QCHLLITLSA-N (2s)-3-methyl-1-[(1r,3s,5r)-3-[5-[4-[4-[2-[(1r,3s,5r)-2-[(2s)-3-methyl-2-(pyrimidin-2-ylamino)butanoyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-(pyrimidin-2-ylamino)butan-1-one Chemical compound N([C@@H](C(C)C)C(=O)N1[C@@H](C[C@H]2C[C@H]21)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N([C@@H]2C[C@@H]2C1)C(=O)[C@@H](NC=1N=CC=CN=1)C(C)C)C1=NC=CC=N1 BUMSXOMPQQXECH-QCHLLITLSA-N 0.000 claims 1
UUJAVTXTPYGDJX-ZQWQDMLBSA-N (2s)-3-methyl-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s)-3-methyl-2-(pyrimidin-2-ylamino)butanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-(pyrimidin-2-ylamino)butan-1-one Chemical compound N([C@@H](C(C)C)C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@@H](NC=1N=CC=CN=1)C(C)C)C1=NC=CC=N1 UUJAVTXTPYGDJX-ZQWQDMLBSA-N 0.000 claims 1
SLCVLAVBMUQSGL-VRANXALZSA-N (2s,3r)-3-methoxy-1-[(2s)-2-[5-[4-[4-[2-[(2s)-1-[(2s,3r)-3-methoxy-2-(pyrimidin-2-ylamino)butanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-(pyrimidin-2-ylamino)butan-1-one Chemical compound N([C@@H]([C@@H](C)OC)C(=O)N1[C@@H](CCC1)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N(CCC1)C(=O)[C@@H](NC=1N=CC=CN=1)[C@@H](C)OC)C1=NC=CC=N1 SLCVLAVBMUQSGL-VRANXALZSA-N 0.000 claims 1
RUNIWNMLQKXLMB-OSFLMINUSA-N 1-[(2s,5s)-2-methyl-5-[5-[4-[4-[2-[(2s,5s)-5-methyl-1-(2-phenylacetyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound N1([C@@H](CC[C@@H]1C)C=1NC=C(N=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1N=C(NC=1)[C@H]1N([C@@H](C)CC1)C(=O)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1 RUNIWNMLQKXLMB-OSFLMINUSA-N 0.000 claims 1
GLEIAWWPZOIZES-SFTDATJTSA-N 2-[(2s)-4,4-difluoropyrrolidin-2-yl]-5-[4-[3-fluoro-4-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazole Chemical compound FC1=CC(C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2NCC(F)(F)C2)=CC=C1C(N=1)=CNC=1[C@@H]1CCCN1 GLEIAWWPZOIZES-SFTDATJTSA-N 0.000 claims 1
DMUVMGXDLWCSSG-PNRIMKNJSA-N 3-methyl-1-[(2s,5s)-2-methyl-5-[5-[4-[4-[2-[(2s,5s)-5-methyl-1-(3-methylbutanoyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]butan-1-one Chemical compound CC(C)CC(=O)N1[C@@H](C)CC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H](C)CC2)C(=O)CC(C)C)=CN1 DMUVMGXDLWCSSG-PNRIMKNJSA-N 0.000 claims 1
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BHMNCNOLYUCUHY-KYJUHHDHSA-N COC(=O)NCC(=O)N([C@@H](C1)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CC3(CC3)C2)C(=O)CNC(=O)OC)CC21CC2 Chemical compound COC(=O)NCC(=O)N([C@@H](C1)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CC3(CC3)C2)C(=O)CNC(=O)OC)CC21CC2 BHMNCNOLYUCUHY-KYJUHHDHSA-N 0.000 claims 1
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DDOPWQFSAZQKFU-ATUXXYJQSA-N O=C([C@H](NC(=O)OC)C=1C=CC=CC=1)N([C@@H](C1)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CC3(CC3)C2)C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)CC21CC2 Chemical compound O=C([C@H](NC(=O)OC)C=1C=CC=CC=1)N([C@@H](C1)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CC3(CC3)C2)C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)CC21CC2 DDOPWQFSAZQKFU-ATUXXYJQSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
OMIRCVODJLIUSE-KYJUHHDHSA-N ethyl 2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-4-[4-[4-[2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C=1N=C([C@H]2N(CCC2)C(=O)OC(C)(C)C)NC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(N1)=CN=C1[C@@H]1CCCN1C(=O)OC(C)(C)C OMIRCVODJLIUSE-KYJUHHDHSA-N 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 1
QPLLQWMCPNSDMZ-PTOQVCFTSA-N methyl n-[(1r)-2-[(1r,3s,5r)-3-[5-[4-[4-[2-[(1r,3s,5r)-2-[(2r)-2-(methoxycarbonylamino)-2-phenylacetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2[C@@H]3C[C@@H]3C[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2C[C@H]3C[C@H]3N2C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)=CC=CC=C1 QPLLQWMCPNSDMZ-PTOQVCFTSA-N 0.000 claims 1
XLLHEEKLVBNNRG-WZIOGPPVSA-N methyl n-[(1r)-2-[(2s)-2-[4-[4-[4-[2-[(2s)-1-[(2r)-2-(methoxycarbonylamino)-2-phenylacetyl]pyrrolidin-2-yl]-5-methyl-1h-imidazol-4-yl]phenyl]phenyl]-5-methyl-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound C1([C@@H](NC(=O)OC)C(=O)N2CCC[C@H]2C=2NC(=C(N=2)C)C2=CC=C(C=C2)C2=CC=C(C=C2)C2=C(C)N=C(N2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)OC)C=2C=CC=CC=2)=CC=CC=C1 XLLHEEKLVBNNRG-WZIOGPPVSA-N 0.000 claims 1
JAVCBMGFRXOPTD-TUKGZPIISA-N methyl n-[(1s)-1-cyclopropyl-2-[(1r,3s,5r)-3-[5-[4-[4-[2-[(1r,3s,5r)-2-[(2s)-2-cyclopropyl-2-(methoxycarbonylamino)acetyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]carbamate Chemical compound C1([C@H](NC(=O)OC)C(=O)N2[C@@H](C[C@H]3C[C@H]32)C=2NC=C(N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@@H](NC(=O)OC)C2CC2)CC1 JAVCBMGFRXOPTD-TUKGZPIISA-N 0.000 claims 1
JOBHKKGSQRSMHJ-FCFAFEMMSA-N methyl n-[(2s)-1-[(1r,3s,5r)-3-[5-[4-[4-[2-[(1r,3s,5r)-2-[(2s)-2-(methoxycarbonylamino)butanoyl]-2-azabicyclo[3.1.0]hexan-3-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]-2-azabicyclo[3.1.0]hexan-2-yl]-1-oxobutan-2-yl]carbamate Chemical compound C=1NC([C@@H]2C[C@H]3C[C@H]3N2C(=O)[C@@H](NC(=O)OC)CC)=NC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C1=CNC([C@H]2N([C@@H]3C[C@@H]3C2)C(=O)[C@H](CC)NC(=O)OC)=N1 JOBHKKGSQRSMHJ-FCFAFEMMSA-N 0.000 claims 1
OTCUSGSIFGGXCM-LQJZCPKCSA-N tert-butyl (2s)-2-[5-[4-[4-[5-(1,3-dioxan-2-ylmethyl)-2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1h-imidazol-4-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C2=C(N=C(N2)[C@H]2N(CCC2)C(=O)OC(C)(C)C)CC2OCCCO2)=CN1 OTCUSGSIFGGXCM-LQJZCPKCSA-N 0.000 claims 1
WPWJRVIXJQFACS-ACHIHNKUSA-N tert-butyl (2s)-2-[5-[4-[4-[5-(1,3-dioxolan-2-ylmethyl)-2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1h-imidazol-4-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C2=C(N=C(N2)[C@H]2N(CCC2)C(=O)OC(C)(C)C)CC2OCCO2)=CN1 WPWJRVIXJQFACS-ACHIHNKUSA-N 0.000 claims 1
ZBCGSIOFZITJMT-CONSDPRKSA-N tert-butyl (2s)-2-[5-[4-[4-[5-(2-methoxy-2-oxoethyl)-2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1h-imidazol-4-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound COC(=O)CC=1NC([C@H]2N(CCC2)C(=O)OC(C)(C)C)=NC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(N=1)=CNC=1[C@@H]1CCCN1C(=O)OC(C)(C)C ZBCGSIOFZITJMT-CONSDPRKSA-N 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
JHFINHOBWIGQHJ-UHFFFAOYSA-N cyclopropylcarbamic acid Chemical compound OC(=O)NC1CC1 JHFINHOBWIGQHJ-UHFFFAOYSA-N 0.000 abstract 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1

Classifications

- 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
- 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
- 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
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

HRP20120706AT 2008-02-13 2012-09-05 Imidazolil bifenil imidazoli kao inhibitori virusa hepatitisa c HRP20120706T1 (hr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US2008/053779 WO2009102325A1 (en)	2008-02-13	2008-02-13	Imidazolyl biphenyl imidazoles as hepatitis c virus inhibitors

Publications (1)

Publication Number	Publication Date
HRP20120706T1 true HRP20120706T1 (hr)	2012-09-30

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ID=39661448

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Application Number	Title	Priority Date	Filing Date
HRP20120706AT HRP20120706T1 (hr)	2008-02-13	2012-09-05	Imidazolil bifenil imidazoli kao inhibitori virusa hepatitisa c

Country Status (21)

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EP (1)	EP2242752B1 (pl)
JP (1)	JP5312486B2 (pl)
KR (1)	KR101492672B1 (pl)
CN (1)	CN102007122B (pl)
AU (1)	AU2008350334B2 (pl)
BR (1)	BRPI0822323A2 (pl)
CA (1)	CA2715839C (pl)
CY (1)	CY1113259T1 (pl)
DK (1)	DK2242752T3 (pl)
EA (1)	EA018088B1 (pl)
ES (1)	ES2391600T3 (pl)
HK (1)	HK1144194A1 (pl)
HR (1)	HRP20120706T1 (pl)
IL (1)	IL207469A (pl)
MX (1)	MX2010008863A (pl)
NZ (1)	NZ587557A (pl)
PL (1)	PL2242752T3 (pl)
PT (1)	PT2242752E (pl)
SI (1)	SI2242752T1 (pl)
WO (1)	WO2009102325A1 (pl)
ZA (1)	ZA201005573B (pl)

Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7906655B2 (en)	2008-08-07	2011-03-15	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8383094B2 (en)	2008-10-01	2013-02-26	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
CN102264737A (zh)	2008-12-23	2011-11-30	雅培制药有限公司	抗病毒化合物
US8546405B2 (en)	2008-12-23	2013-10-01	Abbott Laboratories	Anti-viral compounds
US8242156B2 (en)	2009-02-17	2012-08-14	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole derivatives
TWI438200B (zh)	2009-02-17	2014-05-21	必治妥美雅史谷比公司	Ｃ型肝炎病毒抑制劑
US8188132B2 (en)	2009-02-17	2012-05-29	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole derivatives
US8394968B2 (en)	2009-02-17	2013-03-12	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
SG10201400235PA (en)	2009-02-27	2014-07-30	Enanta Pharm Inc	Hepatitis c virus inhibitors
US9765087B2 (en)	2009-02-27	2017-09-19	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US8673954B2 (en)	2009-02-27	2014-03-18	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US8101643B2 (en)	2009-02-27	2012-01-24	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US8507522B2 (en)	2009-03-06	2013-08-13	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US20190127365A1 (en)	2017-11-01	2019-05-02	Merck Sharp & Dohme Corp.	Inhibitors of hepatitis c virus replication
SG10201402969QA (en)	2009-03-27	2014-09-26	Merck Sharp & Dohme	Inhibitors of hepatitis c virus replication
US8796466B2 (en)	2009-03-30	2014-08-05	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
TW201038559A (en)	2009-04-09	2010-11-01	Bristol Myers Squibb Co	Hepatitis C virus inhibitors
US8143414B2 (en)	2009-04-13	2012-03-27	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
CA2758484A1 (en)	2009-04-15	2010-10-21	David A. Degoey	Anti-viral compounds
PL3309157T3 (pl)	2009-05-13	2020-03-31	Gilead Pharmasset Llc	Związki przeciwwirusowe
US8138215B2 (en)	2009-05-29	2012-03-20	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8211928B2 (en)	2009-05-29	2012-07-03	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US9394279B2 (en)	2009-06-11	2016-07-19	Abbvie Inc.	Anti-viral compounds
US8716454B2 (en)	2009-06-11	2014-05-06	Abbvie Inc.	Solid compositions
US8937150B2 (en)	2009-06-11	2015-01-20	Abbvie Inc.	Anti-viral compounds
TWI402070B (zh)	2009-06-11	2013-07-21	Abbott Lab	抗病毒化合物
US8221737B2 (en)	2009-06-16	2012-07-17	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8609648B2 (en)	2009-07-02	2013-12-17	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
IN2012DN00999A (pl)	2009-07-16	2015-04-10	Vertex Pharma
AU2010289762B2 (en)	2009-09-04	2015-06-11	Janssen Pharmaceuticals, Inc.	Chemical compounds
US8703938B2 (en)	2009-09-11	2014-04-22	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8927709B2 (en)	2009-09-11	2015-01-06	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8822700B2 (en)	2009-09-11	2014-09-02	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
WO2011031904A1 (en)	2009-09-11	2011-03-17	Enanta Pharmaceuticals, Inc	Hepatitis c virus inhibitors
US8759332B2 (en)	2009-09-11	2014-06-24	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8815928B2 (en)	2009-09-11	2014-08-26	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8415374B2 (en)	2009-10-12	2013-04-09	Bristol-Myers Squibb Company	Combinations of hepatitis C virus inhibitors
UA108211C2 (uk)	2009-11-04	2015-04-10	Янссен Рід Айрленд	Бензімідазолімідазольні похідні
US20110269956A1 (en)	2009-11-11	2011-11-03	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110274648A1 (en)	2009-11-11	2011-11-10	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110281910A1 (en)	2009-11-12	2011-11-17	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
WO2011081918A1 (en)	2009-12-14	2011-07-07	Enanta Pharmaceuticals, Inc	Hepatitis c virus inhibitors
US8377980B2 (en) *	2009-12-16	2013-02-19	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8362020B2 (en)	2009-12-30	2013-01-29	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8933110B2 (en)	2010-01-25	2015-01-13	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
KR20120107529A (ko)	2010-01-25	2012-10-02	이난타 파마슈티칼스, 인코포레이티드	Ｃ형 간염 바이러스 억제제
US8178531B2 (en)	2010-02-23	2012-05-15	Enanta Pharmaceuticals, Inc.	Antiviral agents
US8623814B2 (en)	2010-02-23	2014-01-07	Enanta Pharmaceuticals, Inc.	Antiviral agents
US9060971B2 (en)	2010-03-04	2015-06-23	Enanta Pharmaceuticals, Inc.	Combination pharmaceutical agents as inhibitors of HCV replication
WO2011119853A1 (en)	2010-03-24	2011-09-29	Vertex Pharmaceuticals Incorporated	Analogues for the treatment or prevention of flavivirus infections
WO2011127350A1 (en)	2010-04-09	2011-10-13	Enanta Pharmaceuticals, Inc.	Hepatitis c virus inhibitors
WO2011153396A1 (en)	2010-06-04	2011-12-08	Enanta Pharmaceuticals, Inc	Hepatitis c virus inhibitors
NZ605440A (en)	2010-06-10	2014-05-30	Abbvie Bahamas Ltd	Solid compositions comprising an hcv inhibitor
JP2013529684A (ja)	2010-06-28	2013-07-22	バーテックスファーマシューティカルズインコーポレイテッド	フラビウイルス感染の処置または予防のための化合物および方法
WO2012006060A1 (en)	2010-06-28	2012-01-12	Vertex Pharmaceuticals Incorporated	Compounds and methods for the treatment or prevention of flavivirus infections
US8697704B2 (en)	2010-08-12	2014-04-15	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
EP2606041A2 (en)	2010-08-17	2013-06-26	Vertex Pharmaceuticals Incorporated	Compounds and methods for the treatment or prevention of flaviviridae viral infections
CA2809261A1 (en)	2010-08-26	2012-03-01	Rfs Pharma, Llc	Potent and selective inhibitors of hepatitis c virus
JP2013540122A (ja)	2010-09-29	2013-10-31	メルク・シャープ・エンド・ドーム・コーポレイション	縮合四環式化合物誘導体およびウィルス疾患治療のためのそれの使用方法
CA3095528C (en) *	2010-11-17	2023-07-18	Gilead Pharmasset Llc	Antiviral compounds
US20150031884A1 (en) *	2010-12-15	2015-01-29	Abbvie Inc.	Anti-viral compounds
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
US10201584B1 (en)	2011-05-17	2019-02-12	Abbvie Inc.	Compositions and methods for treating HCV
EP2709455A4 (en)	2011-05-18	2014-11-05	Enanta Pharm Inc	PROCESSES FOR THE PREPARATION OF 5-AZASPIRO [2.4] HEPTANE-6-CARBOXYLIC ACID AND ITS DERIVATIVES
TW201317223A (zh)	2011-07-26	2013-05-01	Vertex Pharma	噻吩化合物
WO2013016499A1 (en)	2011-07-26	2013-01-31	Vertex Pharmaceuticals Incorporated	Methods for preparation of thiophene compounds
WO2013030750A1 (en)	2011-09-01	2013-03-07	Lupin Limited	Antiviral compounds
WO2013039876A1 (en)	2011-09-14	2013-03-21	Merck Sharp & Dohme Corp.	Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases
RS56975B1 (sr)	2011-09-16	2018-05-31	Gilead Pharmasset Llc	Metode za lečenje hcv-a
US9512073B2 (en)	2011-10-27	2016-12-06	Massachusetts Institute Of Technology	Amino acid-, peptide-and polypeptide-lipids, isomers, compositions, and uses thereof
SG10201700947UA (en)	2011-11-16	2017-03-30	Gilead Pharmasset Llc	Condensed imidazolylimidazoles as antiviral compounds
IN2014MN01465A (pl)	2011-12-28	2015-04-17	Janssen R & D Ireland
US9034832B2 (en)	2011-12-29	2015-05-19	Abbvie Inc.	Solid compositions
IN2014MN01547A (pl)	2012-02-10	2015-05-08	Lupin Ltd
CN103304551B (zh) *	2012-03-14	2017-06-13	北京凯因科技股份有限公司	丙肝聚合酶抑制剂
NZ630805A (en)	2012-03-22	2016-01-29	Alios Biopharma Inc	Pharmaceutical combinations comprising a thionucleotide analog
US20130309196A1 (en)	2012-05-16	2013-11-21	Gilead Sciences, Inc.	Antiviral compounds
US9056860B2 (en) *	2012-06-05	2015-06-16	Gilead Pharmasset Llc	Synthesis of antiviral compound
WO2014110687A1 (en)	2013-01-16	2014-07-24	Merck Sharp & Dohme Corp.	Thiazolyl-substitued tetracyclic compounds and methods of use thereof for treatment of viral diseases
MY172166A (en)	2013-01-31	2019-11-15	Gilead Pharmasset Llc	Combination formulation of two antiviral compounds
WO2014134251A1 (en)	2013-02-28	2014-09-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical compositions
US11484534B2 (en)	2013-03-14	2022-11-01	Abbvie Inc.	Methods for treating HCV
EP4005560A1 (en)	2013-08-27	2022-06-01	Gilead Pharmasset LLC	Combination formulation of two antiviral compounds
WO2015103490A1 (en)	2014-01-03	2015-07-09	Abbvie, Inc.	Solid antiviral dosage forms
KR20170002407A (ko)	2014-04-15	2017-01-06	코크리스탈 파마, 아이엔씨.	C형 간염 바이러스의 강력하고 선택적인 저해제
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
TWI721947B (zh)	2014-06-11	2021-03-21	美商基利法瑪席特有限責任公司	抗病毒化合物的固態形式
RS64331B1 (sr)	2015-06-19	2023-08-31	Massachusetts Inst Technology	Alkenil supstituisani 2,5-piperazindioni i njihova primena u sastavima za isporuku agensa u organizam ili ćeliju subjekta
CN106008316B (zh) *	2016-06-17	2018-04-27	成都百事兴科技实业有限公司	一种合成雷迪帕韦手性中间体的方法
CN105967990A (zh) *	2016-07-05	2016-09-28	南京红杉生物科技有限公司	一种4,4’-二(2-溴乙酰基)联苯的合成方法
WO2018007984A1 (en) *	2016-07-08	2018-01-11	Lupin Limited	Crystalline forms of daclatasvir dihydrochloride
WO2020117849A1 (en)	2018-12-04	2020-06-11	Bristol-Myers Squibb Company	Methods of analysis using in-sample calibration curve by multiple isotopologue reaction monitoring
CN111825659A (zh) *	2019-04-19	2020-10-27	扬子江药业集团有限公司	一种盐酸达拉他韦杂质盐酸盐及其制备方法和用途
EP4341266A1 (en)	2021-05-21	2024-03-27	Gilead Sciences, Inc.	Pentacyclic derivatives as zika virus inhibitors

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6080870A (en) *	1996-04-03	2000-06-27	Merck & Co., Inc.	Biaryl substituted imidazole compounds useful as farnesyl-protein transferase inhibitors
AU2003249977A1 (en) *	2002-07-05	2004-01-23	Axxima Pharmaceuticals Ag	Imidazole compounds for the treatment of hepatitis c virus infections
GB0416396D0 (en) *	2004-07-22	2004-08-25	Angeletti P Ist Richerche Bio	Therapeutic agents
US8143288B2 (en) *	2005-06-06	2012-03-27	Bristol-Myers Squibb Company	Inhibitors of HCV replication
US7659270B2 (en) *	2006-08-11	2010-02-09	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8329159B2 (en) *	2006-08-11	2012-12-11	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US7759495B2 (en) *	2006-08-11	2010-07-20	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors

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Publication number	Publication date
HK1144194A1 (en)	2011-02-02
EA018088B1 (ru)	2013-05-30
DK2242752T3 (da)	2012-11-19
ES2391600T3 (es)	2012-11-28
PT2242752E (pt)	2012-10-29
EP2242752B1 (en)	2012-08-08
IL207469A0 (en)	2010-12-30
IL207469A (en)	2016-03-31
JP5312486B2 (ja)	2013-10-09
EP2242752A1 (en)	2010-10-27
ZA201005573B (en)	2012-01-25
WO2009102325A1 (en)	2009-08-20
AU2008350334B2 (en)	2013-10-17
PL2242752T3 (pl)	2012-12-31
BRPI0822323A2 (pt)	2015-06-16
AU2008350334A1 (en)	2009-08-20
EA201001274A1 (ru)	2011-06-30
CN102007122B (zh)	2013-09-04
NZ587557A (en)	2012-04-27
CA2715839C (en)	2014-12-09
KR101492672B1 (ko)	2015-02-16
CY1113259T1 (el)	2016-04-13
CN102007122A (zh)	2011-04-06
MX2010008863A (es)	2010-09-07
KR20100113629A (ko)	2010-10-21
JP2011511833A (ja)	2011-04-14
SI2242752T1 (sl)	2013-03-29
CA2715839A1 (en)	2009-08-20

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