US 2012/0230951 A1Published application

Antiviral compounds

OwnerMuzaffar Alam, Steven Joseph Berthel +12inventors

InventorsMuzaffar Alam, Steven Joseph Berthel, John A. Brinkman, Ronald Charles Hawley, Hongju Li, Wylie Solang Palmer, Sherrie Pietranico-Cole, Ramakanth Sarabu, Mark Smith, Sung-Sau So, Lin Yi, Yansheng Zhai, Qiang Zhang, Shu-Hai Zhao

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Abstract

The present invention provides 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.

Claims20

Dependent claims

A compound of formula I, II, or III

wherein:
each of A and E are independently selected from the group consisting of H, N(R)2, NHC(═O)OR, NHCOR, and NHCONHR;
each R is independently H or lower alkyl;
B and D are independently selected from the group consisting of
each Y is independently N or CY';
Y′ is H or halo;
L is selected from the group consisting of
each X is independently, N, CH, C(F), C(OCF3), or C(CN);
Q is CH2;
Q′ is CH2, CHOH, CHF, CH(CN), C(Q″)2, O, or CF2;
or Q and Q′ together form cycloalkyl;
both Q″ together form a spirocyclic heterocyclic ring;
r is 1 or 2;
each X′ is independently H, lower alkyl, lower alkoxy, hydroxy lower alkyl, heterocycloalkyl, lower alkyl sulfonyl lower alkyl, or (CH2)n-aryl;
or both X′ together form a spirocyclic heterocyclic ring;
n is 0, 1, or 2;
and
X″ is CH2 or C(═O);
or a pharmaceutically acceptable salt thereof.

16 more elements

A compound selected from the group consisting of:

{(2S,5S)-2-[5-(4′-{2-[(2S,4S)-4-Fluoro-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(2S,4R)-4-Fluoro-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-benzoimidazol-5-yl}-phenyl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(S)-4,4-Difluoro-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-benzoimidazol-5-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[6-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-benzoimidazol-5-yl}-phenyl)-1H-benzoimidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[6-(2-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-benzoimidazol-5-yl}-quinoxalin-6-yl)-1H-benzoimidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-benzoimidazol-5-yl}-pyridin-3-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(S)-7-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-1,4-dioxa-7-aza-spiro[4.4]non-8-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[2-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-8-oxa-2-aza-spiro[4.5]dec-3-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[6-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-1H-benzoimidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[6-(4′-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-benzoimidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic methyl ester;
((2S,5S)-2-{6-[6-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyridin-3-yl]-1H-benzoimidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{6-[6-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-4,4-difluoro-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyridin-3-yl]-1H-benzoimidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
{(2S,5S)-2-[6-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-quinoxalin-2-yl)-1H-benzoimidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyrimidin-5-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-4,4-difluoro-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-pyrimidin-5-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-pyrimidin-5-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[7-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-quinolin-3-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[7-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-4,4-difluoro-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-quinolin-3-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[7-(4-{5-Chloro-2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-quinolin-3-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{4-[4-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-quinolin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-phenyl)-quinolin-6-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{4-[6-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-pyridin-3-yl]-1 Himidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{4-[6-(5-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-pyridin-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
{(2S,5S)-9-Bromo-2-[5-(4′-{2-[(R)-1-((R)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-9-Cyano-2-[5-(4′-{2-[(R)-1-((R)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-9-Carbamoyl-2-[5-(4′-{2-[(R)-1-((R)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4,7-dioxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-7-Hydroxy-2-[5-(4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{5-Chloro-2-[(S)-1-((S)-2-methoxycarbonyl amino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{5-Chloro-2-[(S)-4,4-difluoro-1-((S)-2-methoxycarbonyl amino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(2S,4S)-4-Hydroxy-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(5-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-pyridin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
{(2S,5S)-2-[5-(2-Fluoro-4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(3-Fluoro-4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(2′-Fluoro-4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(2′-Cyano-4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(2S,4R)-4-Cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(2S,4S)-4-Cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-{5-[4-(6-{2-[(2S,4S)-4-Cyano-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-{5-[4-(6-{2-[(S)-4,4-Difluoro-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-3-Methoxy-2-methoxycarbonylamino-propionyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
5S)-2-[5-(4-{2-[(S)-1-((S)-2-Cyclopropyl-2-methoxycarbonylamino-acetyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-butyryl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-4-Methoxy-2-Methoxycarbonylamino-butyryl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-(3-Methoxycarbonylamino-oxetane-3-carbonyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(2-{(S)-1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-propionyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-3-Hydroxy-2-methoxycarbonylamino-butyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4-{2-[(S)-1-((S)-4-Methanesulfonyl-2-methoxycarbonylamino-butyl)-pyrrolidin-2-yl]-3H-imidizol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-quinoxalin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(6-{2-[(S)-1-((2S,3S)-2-Methoxycarbonylamino-3-methyl-pentanoyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-quinoxalin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3,3-dimethyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-quinoxalin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[4-(6-{2-[(S)-1-((R)-2-Methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-quinoxalin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(4-{2-[(S)-1-((2S,3S)-2-Methoxycarbonylamino-3 methyl-pentanoyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl) quinoxalin-6-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((2S,5S)-2-{4-[4-(5-{2-[(S)-4,4-Difluoro-1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-pyrimidin-2-yl)-phenyl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
((1S,2S)-1-{(S)-4,4-Difluoro-2-[5-(2-{4-[2-((2S,5S)-5-methoxycarbonylamino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-2-yl)-1H-imidazol-4-yl]-phenyl}-pyrimidin-5-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-butyl)-carbamic acid methyl ester;
((2S,5S)-2-{5-[2-(4-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-quinoxalin-6-yl]-1H-imidazol-2-yl}-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl)-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{5-[(S)-1-((R)-2-Methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-4H-[1,2,4]triazol-3-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{5-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-4H-[1,2,4]triazol-3-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{5-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-2-yl}-biphenyl-4-yl)-[1,3,4]oxadiazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(R)-4-((R)-2-Methoxycarbonylamino-2-phenyl-acetyl)-morpholin-3-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(R)-4-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-morpholin-3-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(S)-3-((R)-2-Methoxycarbonylamino-2-phenyl-acetyl)-3-aza-bicyclo [3.1.0]hex-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
{(2S,5S)-2-[5-(4′-{2-[(1S,9S)-9-methoxycarbonylamino-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2] diazepin-1-yl])-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester;
6-(6-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-naphthalen-2-yl)-2-42S,5S)-5-methoxycarbonylamino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-2-yl)-benzoimidazole-1-carboxylic acid methyl ester;
N,N′-[1,4-phenylenebis[1H-benzimidazole-6,2-diyl-(2S,5S)-1,2,4,5,6,7-hexahydro-4-oxoazepino[3,2,1-hi]indole-5,2-diyl]]biscarbamic acid C,C′dimethyl ester;
and
{(2S,5S)-2-[5-(4′-{2-[(S)-4,4-Difluoro-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-5-yl}-carbamic acid methyl ester.

68 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/414,854Filed 8 Mar 2012
Priority: 11 Mar 2011
Published: 13 Sep 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 487/06
In which the condensed system contains two hetero rings: peri-condensed systems
A61K 31/55
Having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins: having seven-membered rings, e.g. azelastine, pentylenetetrazole
A61K 31/551
Having seven-membered rings, e.g. azelastine, pentylenetetrazole: having two nitrogen atoms, e.g. dilazep
A61K 45/06
Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00: mixtures of active ingredients without…