Process for preparing antiviral compounds
AssigneeAbbVie Inc.
InventorsShashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
Life of this patent
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Abstract
This disclosure is directed to: (a) processes for preparing compounds and salts thereof that, inter alia, are useful for inhibiting hepatitis C virus (HCV); (b) intermediates useful for the preparation of the compounds and salts; (c) pharmaceutical compositions comprising the compounds or salts; and (d) methods of use of such compositions.
Claims30
A process for preparing compound (5-I), comprising:
- reacting a compound of formula (4) or salt thereof with a sulfonylating agent in the presence of a solvent and a base:
- wherein
- R1a is, at each occurrence, independently selected from the group consisting of aryl, alkyl, fluoroalkyl, -fluoroalkyl-O-fluoroalkyl, —N(alkyl)2, fluoro and imidazolyl;
- R4 is selected from the group consisting of C1-C6-alkyl, C1-C6-fluoroalkyl, phenyl, 2-thienyl, 3-thienyl, 2-furanyl, and 3-furanyl;
- and
- R5 is selected from the group consisting of hydrogen, fluoro, chloro, C1-C6-alkyl, and C1-C6-alkyloxy;
- wherein the sulfonylating agent corresponds in structure to
- or
- and X1 is selected from the group consisting of bromine, chlorine, and fluorine.
A compound or salt thereof, wherein the compound corresponds in structure to formula (5-I):
- wherein R4 is selected from the group consisting of C1-C6-alkyl, C1-C6-fluoroalkyl, C1-C6-hydroxyalkyl, phenyl, 2-thienyl, 3-thienyl, 2-furanyl, and 3-furanyl;
- R5 is selected from the group consisting of hydrogen, fluoro, chloro, C1-C6-alkyl, and C1-C6-alkyloxy;
- and
- R1a is selected from the group consisting of aryl, alkyl, fluoroalkyl, -fluoroalkyl-O-fluoroalkyl, —N(alkyl)2, fluoro and imidazolyl.
A composition comprising 6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate and N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide or a salt thereof.
Dependencies are inferred from the claim text.