1256383-53-5

Upstream product

• 1256383-51-3 3-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 
• 5467-72-1 α-amino-4-bromoacetophenone hydrochloride 
• 134795-25-8 (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 
• 220093-41-4 (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester 
• 1181573-36-3 (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 134984-63-7 (1S,3S,4R)-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester 
• 1273592-34-9 (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 3-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 2-tert-butyl ester 
• 214910-41-5 (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester 
• 192461-70-4 ethyl (1R,3S,4S)-2-<(R)-1-phenylethyl>-2-azabicyclo<2.2.1>heptane-3-exo-carboxylate 
• 448949-65-3 (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid hydrochloride 
• 188057-41-2 ethyl (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylate hydrochloride 

Downstream Products

• 1256384-66-3 3-(5-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 
• 1273588-86-5 C₃₈H₄₆N₆O₄ 
• 1256383-58-0 methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate 
• 1321849-08-4 C₂₀H₂₆BN₃O₄ 
• 1256383-55-7 methyl ((S)-1-((1R,3S,4S)-3-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-3-methyl-1-oxobutan-2-yl)carbamate 
• 1321849-82-4 C₄₈H₅₄N₈O₆ 
• 1256383-56-8 methyl ((S)-3-methyl-1-oxo-1-((1R,3S,4S)-3-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)butan-2-yl)carbamate 
• 1322211-73-3 C₁₅H₁₆BrN₃ 

Relevant academic research and scientific papers

FUSED TRICYCLIC SILYL COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

no abstract published

Discovery of ledipasvir (GS-5885): A potent, once-daily oral NS5A inhibitor for the treatment of hepatitis C virus infection

A new class of highly potent NS5A inhibitors with an unsymmetric benzimidazole-difluorofluorene-imidazole core and distal [2.2.1]azabicyclic ring system was discovered. Optimization of antiviral potency and pharmacokinetics led to the identification of 39 (ledipasvir, GS-5885). Compound 39 (GT1a replicon EC50 = 31 pM) has an extended plasma half-life of 37-45 h in healthy volunteers and produces a rapid >3 log viral load reduction in monotherapy at oral doses of 3 mg or greater with once-daily dosing in genotype 1a HCV-infected patients. 39 has been shown to be safe and efficacious, with SVR12 rates up to 100% when used in combination with direct-acting antivirals having complementary mechanisms.

HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formulas (I) or (II): wherein the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are inhibitors of replication of the hepatitis C virus. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat hepatitis C viral infections, and processes and intermediates useful for preparing such compounds.

NOVEL HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of Formula (I): wherein R1, R2, RA, RB, Z1, Z2, Z3, Z4, Z5 and Z6 are defined herein. The compounds are useful as inhibitors of the function of NS5A protein encoded by HCV for the treatment of hepatitis C viral infection.

HEPATITIS C VIRUS INHIBITORS

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The present invention relates to novel antiviral compounds represented herein above, pharmaceutical compositions comprising such compounds, and methods for the treatment or prophylaxis of viral (particularly HCV) infection in a subject in need of such therapy with said compounds.

ANTIVIRAL COMPOUNDS

The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.