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Last Updated: October 15, 2019

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Claims for Patent: 6,930,106

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Summary for Patent: 6,930,106
Title: Inhibitors of HCV NS5B polymerase
Abstract:The present invention provides compounds of Formula I, compositions and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases. ##STR1##
Inventor(s): Finzel; Barry Craig (Dexter, MI), Funk; Lee A. (Chula Vista, CA), Kelly; Robert Charles (Augusta, MI), Reding; Matthew T. (University City, MO), Wicnienski; Nancy Anne (Kalamazoo, MI)
Assignee: Pharmacia & UpJohn Company (Kalamazoo, MI)
Application Number:10/610,096
Patent Claims:1. A method for treating a viral infection comprising administering to an animal in need thereof an effective amount of a compound of Formula I: ##STR22## wherein ##STR23## represents a substituted or unsubstituted five or six membered saturated, partially unsaturated or aromatic ring optionally containing 1 or 2 heteroatoms of O, N or S; R.sub.2 and R.sub.3 represent 1 to three substituents independently selected from the group consisting of halogen, --CN, N(R)(R'), --NO.sub.2, fluoro-C.sub.1 -C.sub.8 -alkyl, fluoro-C.sub.1 -C.sub.8 -alkyloxy, C.sub.1 -C.sub.8 -alkyl, aryl, ara-C.sub.1 -C.sub.8 -alkyl, arlyoxy, ara-C.sub.1 -C.sub.8 -alkyloxy, --C.sub.1 -C.sub.8 -alkylthio, arylthio, and hetero-C.sub.1 -C.sub.8 -alkyl; R, R' and R" are independently H or C.sub.1 -C.sub.8 alkyl; R and R' may be taken together to form a 3 to 7 membered ring optionally containing an additional heteroatom of --O--, --NR"--, --S-- or --SO.sub.n --; R.sub.1 is selected from the group consisting of H, --CN, and --(CH.sub.2).sub.n --N(R.sub.5)R.sub.6 ; R.sub.5 is H or C.sub.1 -C.sub.8 alkyl; R.sub.6 is selected from the group consisting of H, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, ara-C.sub.1 -C.sub.8 -alkyl, heteroaryl, heteroara-C.sub.1 -C.sub.8 -alkyl, hetero-C.sub.1 -C.sub.8 -alkyl and substituted hetero-C.sub.1 -C.sub.8 -alkyl; R.sub.5 and R.sub.6 may be joined together to form a 5 to 7 membered ring optionally containing an additional heteroatom of --NR--, --O--, --S-- or --SO.sub.n --; M and Q are independently --C-- or --S(.dbd.O)--; Each n is independently 0, 1 or 2.

2. The method of claim 1, wherein said viral infection is hepatitis infection.

3. The method of claim 1, wherein said viral infection is hepatitis C virus infection.

4. The method of claim 1, wherein: R.sub.1 is --(CH.sub.2).sub.n --N(R.sub.5)R.sub.6 ; R.sub.5 is H or C.sub.1 -C.sub.8 alkyl; R.sub.6 is selected from the group consisting of H, C.sub.1 -C.sub.8 alkyl, --C(.dbd.NH)NH.sub.2, aryl, substituted aryl, ara-C.sub.1 -C.sub.8 -alkyl, heteroaryl, heteroara-C.sub.1 -C.sub.8 -alkyl, hetero-C.sub.1 -C.sub.8 -alkyl and substituted hetero-C.sub.1 -C.sub.8 -alkyl; R.sub.5 and R.sub.6 may be joined together to form a 5 to 7 membered ring optionally containing an additional heteroatom of --NR--, --O--, --S-- or --SO.sub.n --; Each n is independently 0, 1 or 2.

5. A method for treating a viral infection comprising administering, to an animal in need thereof, an effective amount of 1-3 compounds of Formula 1 in combination with other antiviral agents which are either therapeutic or prophylactic agents.

6. The method of claim 5, wherein the other antiviral agents are interferon alfa-2b, interferon alfa-2a, interferon alfacon-1 and ribavarin.

7. The method of claim 5, wherein the other antiviral agent is interferon alfa-2b, interferon alfa-2a, or interferon alfacon-1.

8. The method of claim 5, wherein the other antiviral agent is ribavarin.

9. A compound of Formula 1 ##STR24## wherein ##STR25## represents a substituted or unsubstituted five or six membered saturated, partially unsaturated or aromatic ring optionally containing 1 or 2 heteroatoms of O, N or S; R.sub.2 and R.sub.3 represent 1 to three substituents independently selected from the group consisting of halogen, --CN, N(R)(R'), --NO.sub.2, fluoro-C.sub.1 -C.sub.8 -alkyl, fluoro-C.sub.1 -C.sub.8 -alkyloxy, --C.sub.1 -C.sub.8 -alkyl, aryl, ara-C.sub.1 -C.sub.8 -alkyl, arlyoxy, ara-C.sub.1 -C.sub.8 -alkyloxy, --C.sub.1 -C.sub.8 -alkylthio, arylthio, and hetero-C.sub.1 -C.sub.8 -alkyl; R, R' and R" are independently H or C.sub.1 -C.sub.8 alkyl; R and R' may be taken together to form a 3 to 7 membered ring optionally containing an additional heteroatom of --O--, --NR"--, --S-- or --SO.sub.n --; R.sub.1 is selected from the group consisting of H, --CN, and --(CH.sub.2).sub.n --N(R.sub.5)R.sub.6 ; R.sub.5 is H or C.sub.1 -C.sub.8 alkyl; R.sub.6 is selected from the group consisting of H, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, ara-C.sub.1 -C.sub.8 -alkyl, heteroaryl, heteroara-C.sub.1 -C.sub.8 -alkyl, hetero-C.sub.1 -C.sub.8 -alkyl and substituted hetero-C.sub.1 -C.sub.8 -alkyl; R.sub.5 and R.sub.6 may be joined together to form a 5 to 7 membered ring optionally containing an additional heteroatom of --NR--, --O--, --S-- or --SO.sub.n --; M and Q are independently --C-- or --S(.dbd.O)--; Each n is independently 0, 1 or 2.

10. A compound of claim 9, wherein: R.sub.1 is --(CH.sub.2).sub.n --N(R.sub.5)R.sub.6 ; R.sub.5 is H or C.sub.1 -C.sub.8 alkyl; R.sub.6 is selected from the group consisting of H, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, aralkyl, heteroaryl, hetero-C.sub.1 -C.sub.8 -aralkyl, hetero-C.sub.1 -C.sub.8 -alkyl, and substituted hetero-C.sub.1 -C.sub.8 -alkyl; R.sub.5 and R.sub.6 may be joined together to form a 5 to 7 membered ring optionally containing an additional heteroatom of --NR--, --O--, --S-- or --SO.sub.n --; Each n is independently 0, 1 or 2.

11. A compound according to claim 10 selected from the group comprised of: 2-[[[2-[[4-(aminomethyl)phenyl]amino]-5-(trifluoromethyl)phenyl]amino]carbo nyl]-4,5-dichlorobenzoic acid monohydrochloride; 2-({[2-({4-[(benzylamino)methyl]phenyl}amino)-5-(trifluoromethyl)phenyl]ami no}carbonyl)-4,5-dichlorobenzoic acid; N-{5-tert-butyl-2-[(4-cyanophenyl)amino]phenyl}-4,5-dichloro-2-hydroxybenza mide; (4-{[2-[(2,3,4,5-tetrabromo-6-sulfobenzoyl)amino]-4-(trifluoromethyl)phenyl ]amino}phenyl)methanaminium chloride; 4,5-dichloro-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino} carbonyl)benzoic acid; 3,6-dichloro-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino} carbonyl)benzoic acid; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)-3,4 ,5,6-tetrafluorobenzoic acid; 2,3,4,5-tetrabromo-6-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl] amino}-carbonyl)benzenesulfonic acid; 2,3,4,5-tetrachloro-6-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl ]amino}-carbonyl)benzoic acid; (4-{[2-[(2-sulfobenzoyl)amino]-4-(trifluoromethyl)phenyl]amino}phenyl)metha naminium chloride; (4-{[2-({[(1S,2S)-2-carboxycyclohexyl]carbonyl}amino)-4-(trifluoromethyl)ph enyl]amino}phenyl)methanaminium chloride; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}-carbonyl)ben zenesulfonic acid; 2,3,4,5-tetrabromo-6-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl] amino}-carbonyl)benzoic acid; (1R,2R)-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbo nyl)-cyclohexanecarboxylic acid disodium 2-{[2-{[(6-carboxylatocyclohex-3-en-1-yl)carbonyl]amino}-4-(trifluoromethy l)phenyl]amino}benzoate; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)-3,6 -dimethoxybenzoic acid; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)benz oic acid; (1S,2S)-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbo nyl)cyclohexanecarboxylic acid; 4,5-dichloro-2-({[2-[(4-{[(morpholin-4-ylcarbonyl)amino]methyl}phenyl)amino ]-5-(trifluoromethyl)phenyl]amino}carbonyl)benzoic acid; disodium 2-{[2-({[(1S,2R)-2-carboxylato-4,5-dihydroxycyclohexyl]-carbonyl}amino)-4- (trifluoromethyl)phenyl]amino}benzoate; (1R,2R)-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbo nyl)cyclohexanecarboxylic acid; 3-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}-carbonyl)-5, 6-dihydro-1,4-dithiine-2-carboxylic acid; 3-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)ison icotinic acid; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}sulfonyl)benz oic acid; 2,3,4,5-tetrabromo-6-[({5-tert-butyl-2-[(4-cyanophenyl)amino]phenyl}amino)c arbonyl]-benzenesulfonic acid; 2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)cycl opent-1-ene-1-carboxylic acid; 3-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)pyra zine-2-carboxylic acid; 2-({[2-[[4-(aminomethyl)phenyl](methyl)amino]-5-(trifluoromethyl)phenyl]ami no}-carbonyl)-4,5-dichlorobenzoic acid; (1R,2S)-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}-carb onyl)cyclohexanecarboxylic acid and 4-tert-butyl-2-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino} -carbonyl)benzoic acid.

12. A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically or prophylactically effective amount of a compound of any one of claims 9-11.

Details for Patent 6,930,106

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Schering INTRON A interferon alfa-2b VIAL 103132 001 1986-06-04   See Pricing Pharmacia & UpJohn Company (Kalamazoo, MI) 2022-07-01 RX search
Schering INTRON A interferon alfa-2b VIAL 103132 002 1986-06-04   See Pricing Pharmacia & UpJohn Company (Kalamazoo, MI) 2022-07-01 RX search
Schering INTRON A interferon alfa-2b VIAL 103132 003 1986-06-04   See Pricing Pharmacia & UpJohn Company (Kalamazoo, MI) 2022-07-01 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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