US 2013/0280211 A1Published application

Hepatitis C Virus Inhibitors

AssigneeBristol-Myers Squibb Company

InventorsCarol Bachand, Makonen Belema, Daniel H. Deon, Andrew C. Good, Jason Goodrich, Clint A. James, Rico Lavoie, Omar D. Lopez, Alain Martel, Nicholas A. Meanwell, Van N. Nguyen, Jeffrey Lee Romine, Edward H. Ruediger, Lawrence B. Snyder, Denis R. ST. Laurent, Fukang Yang, David R. Langley, Lawrence G. Hamann

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Abstract

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

Claims31

Dependent claims

A compound of Formula (I)

or a pharmaceutically acceptable salt thereof, wherein
u and v are independently 0, 1, 2, or 3;
A is selected from phenyl and a six-membered heteroaromatic ring containing two or three nitrogen atoms;
B is selected from pyrazine, pyridazine, pyridine, and triazine;
each R1 and R2 is independently selected from alkoxy, alkoxyalkyl, alkoxycarbonyl, alkyl, arylalkoxycarbonyl, carboxy, formyl, halo, haloalkyl, hydroxy, hydroxyalkyl, —NRaRb, (NRaRb)alkyl, and (NRaRb)carbonyl;
R3 and R4 are each independently selected from hydrogen, alkoxycarbonyl, alkyl, arylalkoxycarbonyl, carboxy, haloalkyl, (NRaRb)carbonyl, and trialkylsilylalkoxyalkyl;
R5 and R6 are each independently selected from hydrogen, alkenyl, alkoxyalkyl, alkyl, haloalkyl, and (NRaRb)alkyl;
or,
R5 and R6, together with the carbon atom to which they are attached, form a five or six membered saturated ring optionally containing one or two heteroatoms selected from NRz, O, and S;
wherein Rz is selected from hydrogen and alkyl;
R7 is selected from hydrogen, R9—C(O)—, and R9—C(S)—;
R8 is selected from hydrogen and alkyl;
R9 is independently selected from alkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylcarbonylalkyl, aryl, arylalkenyl, arylalkoxy, arylalkyl, aryloxyalkyl, cycloalkyl, (cycloalkyl)alkenyl, (cycloalkyl)alkyl, cycloalkyloxyalkyl, haloalkyl, heterocyclyl, heterocyclylalkenyl, heterocyclylalkoxy, heterocyclylalkyl, heterocyclyloxyalkyl, hydroxyalkyl, —NRcRd, (NRcRd)alkenyl, (NRcRd)alkyl, and (NRcRd)carbonyl;
R10 is selected from
wherein
R11 and R12 are each independently selected from hydrogen, alkenyl, alkoxyalkyl, alkyl, haloalkyl, and (NRaRb)alkyl;
or,
R11 and R12, together with the carbon atom to which they are attached, form a five or six membered saturated ring optionally containing one or two heteroatoms selected from NRz, O, and S;
wherein Rz is selected from hydrogen and alkyl;
R13 is selected from hydrogen and alkyl;
R14 is selected from hydrogen, R15—C(O)—, and R15—C(S)—;
R15 is independently selected from alkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylcarbonylalkyl, aryl, arylalkenyl, arylalkoxy, arylalkyl, aryloxyalkyl, cycloalkyl, (cycloalkyl)alkenyl, (cycloalkyl)alkyl, cycloalkyloxyalkyl, haloalkyl, heterocyclyl, heterocyclylalkenyl, heterocyclylalkoxy, heterocyclylalkyl, heterocyclyloxyalkyl, hydroxyalkyl, —NRcRd, (NRcRd)alkenyl, (NRcRd)alkyl, and (NRcRd)carbonyl;
m is 0, 1, or 2;
n is 0, 1, 2, 3, or 4;
X is selected from O, S, S(O), SO2, CH2, CHR16, and C(R16);
provided that when m is 0, X is selected from CH2, CHR16, and C(R16);
each R16 is independently selected from alkoxy, alkyl, aryl, halo, haloalkyl, hydroxy, and —NRaRb, wherein the alkyl can optionally form a fused three- to six-membered ring with an adjacent carbon atom, wherein the three- to six-membered ring is optionally substituted with one or two alkyl groups.

24 more elements

A compound selected from

(2R)-2-(dimethylamino)-N-((1S)-1-(5-(4-(5-(2-((2S)-1-((2R)-2-(dimethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-2-pyridinyl)phenyl)-1H-imidazol-2-yl)ethyl)-2-phenylacetamide;
methyl((1R)-2-((2S)-2-(5-(6-(4-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)phenyl)-3-pyridinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenylethyl)carbamate;
(2R)-2-(dimethylamino)-N-((1S)-1-(5-(4-(6-(2-((2S)-1-((2R)-2-(dimethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-3-pyridazinyl)phenyl)-1H-imidazol-2-yl)ethyl)-2-phenylacetamide;
methyl((1R)-2-((2S)-2-(5-(6-(4-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)phenyl)-3-pyridazinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenylethyl)carbamate;
(2R)-2-(dimethylamino)-N-((1S)-1-(5-(5-(4-(2-((2S)-1-((2R)-2-(dimethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)phenyl)-2-pyrazinyl)-1H-imidazol-2-yl)ethyl)-2-phenylacetamide;
methyl((1R)-2-((2S)-2-(5-(4-(5-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)-2-pyrazinyl)phenyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenylethyl)carbamate;
methyl((1R)-2-((2S)-2-(5-(4-(5-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)-2-pyridinyl)phenyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenylethyl)carbamate;
methyl((1R)-2-(((1S)-1-(5-(6-(4-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)phenyl)-3-pyridinyl)-1H-imidazol-2-yl)ethyl)amino)-2-oxo-1H-phenylethyl)carbamate;
(2R)-2-(dimethylamino)-N-((1S)-1-(5-(6-(4-(2-((1S)-1-(((2R)-2-(dimethylamino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)phenyl)-3-pyridinyl)-1H-imidazol-2-yl)ethyl)-2-phenylacetamide;
and
methyl((1R)-2-((2S)-2-(5-(5-(4-(2-((1S)-1-(((2R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)amino)ethyl)-1H-imidazol-5-yl)phenyl)-2-pyrazinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenylethyl)carbamate;
or a pharmaceutically acceptable salt thereof.

9 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/919,027Filed 17 Jun 2013
Priority: 11 Aug 2006
Published: 24 Oct 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 403/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group…
A61K 31/4178
1,3-Diazoles: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
A61K 31/4545
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol

Family

Application60/837,247Us provisional application · filed 11 Aug 2006
Application11/835,524Continuation · filed 8 Aug 2007
Application12/786,703Continuation · filed 25 May 2010
Application13/606,231Division · filed 7 Sep 2012
Application13/919,027Division
Application13/606,231Continuation
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From the US filing history. Foreign family members aren’t listed.