IP Library Granted Patent US 7,812,016
Granted Patent B2
US 7,812,016 · App. 10/556,311 · Granted Oct 12, 2010

Naphthyridine integrase inhibitors

Assignee: SmithKline Beecham Corporation
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Quick Facts
Patent No.
US 7,812,016
App. No.
10/556,311
Granted
Oct 12, 2010
Kind
B2
Abstract

The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

Claims (23)

1. A compound of formula (I)

wherein R 1 is selected from 1,2-thiazinan-2-yl optionally substituted with one or more substituents independently selected from group consisting of halogen, hydroxy, C 1-8 alkyl, C 1-8 haloalkyl, —OR 3 , —SR 3 , —CN, hydroxy, oxo, —R 3 C(O)N(R 4 ) 2 , —C(O)N(R 4 ) 2 , —R 3 C(O)R 4 , —R 3 OR 3 OH, —C(O)R 4 , —N(R 4 )C(O)R 4 , —N(R 4 )C(O)R 4 , —R 3 N(R 4 )C(O)R 4 , —N(R 4 ) 2 , —R 3 N(R 4 ) 2 , C 6-14 aryl, C 6-14 aryloxy, and R 3 optionally substituted with C 6-14 aryl;

R 2 is C 3-6 cycloalkyl, or C 6-14 aryl optionally substituted with one or more substituents independently selected from the group consisting of hydrogen, halogen, hydroxy, C 1-8 alkyl, —OR 5 , and NR 5 R 6 ;

R 3 is C 1-8 alkyl, C 3-6 cycloalkyl, haloC 1-8 alkyl, C 2-6 alkenyl, C 3-6 cycloalkenyl, or C 3-6 alkenyl;

R 4 is hydrogen, C 1-8 alkyl, C 3-8 cycloalkyl, C 1-6 haloalkyl, C 6-14 aryl, C 6-14 aralkyl, C 2-6 alkenyl, or C 3-6 cycloalkenyl, C 3-6 alkynyl;

R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1-8 haloalkyl, C 1-8 alkylC 3-6 cycloalkyl, C 6-14 aryl, C 6-14 aralkyl, —C(O) m R 7 , —C(O)C(O) m R 7 , and Y optionally substituted with one or more —OR 7 , —C(O) m R 7 , —S(O) n R 7 , —S(O) n R 7 , —C(O)C(O) m R 7 ,

R 7 is hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, —Ycycloalkyl, —YOH, —Y(OY) w where w is 1-10;

m is 1 or 2;

n is 0, 1, or 2;

p is 0, or 1;

A is 1,3,4-oxadiazolyl;

Q is C 1-3 alkyl, —NR 4 , —O—, —C(O), —C(OR 4 )—, S(O) 2 , or —CF 2 ;

Y is a C 1-5 al kylene chain, wherein said C 1-5 alkylene chain is optionally subsituted by one or more groups independently selected from ═O, ═S, and halo, and wherein said C 1-5 alkylene chain optionally contains 1-3 heteroatoms selected from oxygen, sulfur, and nitrogen;

or pharmaceutically acceptable salt thereof.

2. 5-(1,1-Dioxido-1,2-thiazinan-2-yl)-7[5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl]-1,6-naphthyridin-8-ol or pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising an effective amount of a compound according to claim 1 together with a pharmaceutically acceptable carrier.

4. A pharmaceutical composition according to claim 3 in the form of a tablet or capsule.

5. A pharmaceutical composition according to claim 3 in the form of a liquid or suspension.

6. A pharmaceutical composition comprising an effective amount of a compound according to claim 2 together with a pharmaceutically acceptable carrier.

7. A pharmaceutical composition according to claim 6 in the form of a tablet or capsule.

8. A pharmaceutical composition according to claim 6 in the form of a liquid or suspension.

9. A method of treatment of an HIV infection in a human comprising administering to said human an antiviral effective amount of a compound according to claim 2 .

10. A method of treatment of an HIV infection in a human comprising administering to said human an antiviral effective amount of a compound according to claim 1 .

Assignments (1)
CHANGE OF NAME Recorded Sep 21, 2010
From: SMITHKLINE BEECHAM CORPORATION
To: GSK LLC
Reel/Frame 025020/0261 →
Continuity (2)
Provisional Application 6047005900 · May 13, 2003
Related Publication 20070142365A1 · Jun 21, 2007