Aza- and polyaza-naphthalenyl carboxamides useful as HIV integrase inhibitors

• US 20030055071A1
• Filed: 10/10/2001
• Published: 03/20/2003
• Est. Priority Date: 10/12/2000
• Status: Active Grant

• Current Assignee: Merck Sharp & Dohme Corporation (Merck & Co., Inc.)
• Original Assignee: Merck & Co., Inc.
• Inventors: Tran, LeKhanh, Zhuang, Linghang, Wai, John S., Langford, H. Marie, Anthony, Neville J., Melamed, Jeffrey Y., Fisher, Thorsten E., Young, Steven D., Jolly, Samson M., Embrey, Mark, Egbertson, Melissa, Perlow, Debra S., Gomez, Robert P., Bennett, Jennifer J., Kuo, Michelle S., Guare, James P., Funk, Timothy W.
• Granted Patent: US 6,921,759 B2
• Time in Patent Office: Days
• US Class Current: 514/264.1
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/18 for HIV
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described. These compounds are inhibitors of HIV integrase and inhibitors of HIV replication, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

Claims

1. A compound of Formula (I):

2. The compound according to claim 1, wherein

X is N;

Y is C—

Q²;

Z¹ is C—

Q³;

Z² is C—

Q⁴; and

Z³ is CH;

or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 2, wherein

A is phenyl;

and

Q³ and Q⁴ are both —

H;

or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1, which is a compound of Formula (II):

5. The compound according to claim 4, wherein

Z¹ is CH;

Q² is

(1) —

H,

(2) —

C_1-4 alkyl,

(3) —

(CH₂)_0-2CF₃,

(4) —

O—

C_1-4 alkyl,

(5) —

O—

(CH₂)_0-2CF₃,

(6) halo selected from —

F, —

Cl and —

Br,

(7) —

CN,

(8) —

(CH₂)_1-3OR^a,

(9) —

(CH₂)_0-2C(═

O)R^a,

(10) —

(CH₂)_0-2CO₂R^a,

(11) —

(CH₂)_0-2SR^a,

(12) —

N(R^a)₂,

(13) —

(CH₂)_1-3N(R^a)₂,

(14) —

(CH₂)_0-2C(═

O)N(R^a)₂,

(15) —

G—

(CH₂)_1-2—

C(═

O)N(R^a)₂, wherein G is O, S, N(R^a), or N(SO₂R^a),

(16) —

N(R^a)—

C(R^a)═

O,

(17) —

(CH₂)_1-2—

N(R^a)—

C(R^a)═

O,

(18) —

C(═

O)—

N(R^a)—

(CH₂)_1-3—

[C(═

O)]_0-1—

N(R^a)₂,

(19) —

C(═

O)—

N(R^a)—

(CH₂)_1-2H substituted with 1 or 2-OR^a,

(20) —

SO₂R^a,

(21) —

N(R^a)SO₂R^a,

(22) —

CH═

CH—

(CH₂)_0-1—

C(═

O)—

N(R^a)₂,

(23) —

C≡

C—

CH₂OR^a,

(24) —

C≡

C—

CH₂SR^a,

(25) —

C≡

C—

CH₂SO₂R^a

(27) —

N(R^a)—

(CH₂)_1-4SR^a,

(28) —

N(R^a)—

(CH₂)_1-4OR^a,

(29) —

N(R^a)—

(CH₂)_1-4—

N(R^a)₂,

(30) —

N(R^a)—

(CH₂)_1-4N(R^a)—

C(R^a)═

O,

(31) —

N(R^a)—

(CH₂)_0-2—

[C(═

O)]_1-2N(R^a)₂,

(32) —

N(R^a)—

(CH₂)_1-4—

CO₂R^a,

(33) —

N(R^a)C(═

O)N(R^a)—

(CH₂)_1-4—

C(═

O)N(R^a)₂,

(34) —

N(R^a)C(═

O)—

(CH₂)_1-4—

N(R^a)₂,

(35) —

N(R^a)—

SO₂—

N(R^a)₂,

(36) R^k,

(37) —

(CH₂)_1-4R^k,

(38) —

C≡

C—

CH₂R

(39) —

O—

R^k,

(40) —

S(O)_n—

R^k,

(41) —

N(R^c)—

R^k,

(42) —

N(R^c)—

(CH₂)_1-4H substituted with one or two R^k groups,

(43) —

N(R^c)—

(CH₂)_1-4OR^k,

(44) —

C(═

O)—

R^k,

(45) —

C(═

O)N(R^a)—

R^k,

(46) —

N(R^a)C(═

O)—

R^k, or

(47) —

C(═

O)N(R^a)—

(CH₂)_1-4R^k; and

(48) —

N(R^a)—

S(O)_nR^k;

Q⁴ is —

H;

each of R¹ and R² is independently;

(1) —

H,

(2) —

C_1-4 alkyl,

(3) —

(CH₂)_0-2CF₃,

(4) —

O—

C_1-4 alkyl,

(5) —

O—

(CH₂)_0-2CF₃,

(6) —

OH,

(7) halo selected from —

F, —

Cl and —

Br,

(8) —

CN,

(9) —

(CH₂)_1-3OR^a,

(10) —

(CH₂)_0-2C(═

O)R^a,

(11) —

(CH₂)_0-2CO₂R^a,

(12) —

(CH₂)_0-2SR^a,

(13) —

N(R^a)₂,

(14) —

(CH₂)_1-3N(R^a)₂,

(15) —

(CH₂)_0-2C(═

O)N(R^a)₂,

(16) —

C_1-4 alkyl-N(R^a)—

C(R^a)═

O,

(17) —

SO₂R^a,

(18) —

N(R^a)SO₂R^a,

(19) —

O—

(CH₂)_1-4OR^a,

(20) —

O—

(CH₂)_1-4SR^a,

(21) —

O—

(CH₂)_1-4NH—

CO₂R^a,

(22) —

O—

(CH₂)_2-4N(R^a)₂,

(23) —

N(R^a)—

(CH₂)_1-4SR^a,

(24) —

N(R^a)—

(CH₂)_1-4OR^a,

(25) —

N(R^a)—

(CH₂)_1-4N(R^a)₂,

(26) —

N(R^a)—

(CH₂)_1-4N(R^a)—

C(R^a)═

O,

(27) —

R^k,

(28) —

(CH₂)_1-4H substituted with 1 or 2 R^k groups,

(29) —

O—

R^k,

(30) —

O—

(CH₂)_1-4R^k,

(31) —

S(O)_n—

R^k,

(32) —

S(O)_n—

(CH₂)_1-4R^k,

(33) —

O—

(CH₂)_1-4OR^k,

(34) —

O—

(CH₂)_1-4—

O—

(CH₂)_1-4R^k,

(35) —

O—

(CH₂)_1-4SR^k, or

(36) —

(CH₂)_0-4N(R^b)(R^k);

each of R³ and R⁴ is independently

(1) —

H,

(2) halo selected from —

F, —

Cl and —

Br,

(3) —

CN,

(4) —

OH,

(5) C_1-4 alkyl,

(6) —

(CH₂)_0-2CF₃,

(7) —

O—

C_1-4 alkyl, or

(8) —

O(CH₂)_0-2CF₃; and

R⁵ is

(1) —

H,

(2) —

C_1-4 alkyl,

(3) —

(CH₂)_1-4N(R^a)₂,

(4) —

(CH₂)_1-4CO₂R^a,

(5) phenyl optionally substituted with from 1 to 3 substituents independently selected from halogen, C_1-4 alkyl, —

(CH₂)₀-2CF₃, —

O—

C_1-4 alkyl, —

O(CH₂)_0-2CF₃, —

S—

C_1-4 alkyl, —

CN, and —

OH, or

(6) —

(CH₂)_1-4-phenyl;

or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 5, which is a compound of Formula (III):

7. The compound according to claim 6, wherein

L is

(i) a single bond;

(ii) —

(CH₂)_1-3—

, which is optionally substituted with 1 or 2 substituents independently selected from the group consisting of —

F, —

Cl, —

Br, —

OH, methyl, ethyl, —

CO₂CH₃, —

CO₂CH₂-phenyl, phenyl, benzyl, —

(CH₂)_1-2OH, —

CH(OH)-phenyl, and —

CH(NH₂)-phenyl;

or

(iii)

, wherein u and v are each integers having a value of from 0 to 3, provided that the sum of u+v is 1, 2, 3 or 4;

each of R¹ and R² is independently;

(1) —

H,

(2) methyl,

(3) ethyl,

(4) CF₃,

(5) methoxy,

(6) ethoxy

(7) —

OCF₃

(8) halo selected from —

F, —

Cl and —

Br,

(9) —

CN,

(10) —

CH₂OR^a,

(11) —

CO₂R^a,

(12) —

SR^a,

(13) —

N(R^a)₂,

(14) —

(CH₂)_1-3N(R^a)₂,

(15) —

SO₂R^a,

(16) —

(CH₂)_1-2N(R^a)—

C(R^a)═

O,

(17) —

R^k,

(18) —

(CH₂)_1-3H substituted with 1 or 2 R^k groups,

(19) —

O—

R^k, or

(20) —

O—

(CH₂)_1-3R^k;

R⁵ is

(1) —

H,

(2) methyl,

(3) —

(CH₂)_1-2N(R^a)₂,

(4) —

(CH₂)_1-2CO₂CH₃, or

(5) —

(CH₂)_1-2CO₂CH₂CH₃;

(6) phenyl, or

(7) benzyl;

each R^a is independently —

H or —

C_1-4 alkyl;

each R^c is independently

(1) —

H,

(2) —

C_1-4 alkyl,

(3) —

(CH₂)_1-4N(R^a)₂, or

(4) —

(CH₂)_1-4-phenyl, wherein the phenyl is optionally substituted with 1 to 3 substituents independently selected from halogen, C_1-4 alkyl, C_1-4 fluoroalkyl, —

O—

C_1-4 alkyl, —

O—

C_1-4 fluoroalkyl, —

S—

C_1-4 alkyl, —

CN, and —

OH; and

each R^k is independently;

(1) aryl selected from phenyl and naphthyl, wherein aryl is unsubstituted or substituted with from 1 to 4 substituents independently selected from;

(a) halogen,

(b) C_1-4 alkyl,

(c) C_1-4 fluoroalkyl,

(d) —

O—

C_1-4 alkyl,

(e) —

O—

C_1-4 fluoroalkyl,

(f) phenyl,

(g) —

S—

C_1-4 alkyl,

(h) —

CN,

(i) —

OH,

(j) phenyloxy, unsubstituted or substituted with from 1 to 3 substituents independently selected from;

(i) halogen,

(ii) C_1-4 alkyl,

(iii) C_1-4 fluoroalkyl, and

(iv) —

OH,

(k) —

N(R^a)₂,

(l) —

C_1-4 alkyl-N(R^a)₂,

(m) —

R^t,

(p) —

(CH₂)_0-3C(═

O)N(R^a)₂, and

(q) —

(CH₂)_0-3C(═

O)R^a;

(2) —

C_3-6 cycloalkyl, unsubstituted or substituted with from 1 to 3 substituents independently selected from;

(a) halogen,

(b) C_1-4 alkyl,

(c) —

O—

C_1-4 alkyl,

(d) C_1-4 fluoroalkyl,

(e) —

O—

C_1-4 fluoroalkyl,

(f) —

CN,

(h) phenyl, and

(j) —

OH;

(3) —

C_3-6 cycloalkyl fused with a phenyl ring, unsubstituted or substituted with from 1 to 4 substituents independently selected from;

(a) halogen,

(b) C_1-4 alkyl,

(c) —

O—

C_1-4 alkyl,

(d) C_1-4 fluoroalkyl,

(e) —

O—

C_1-4 fluoroalkyl,

(f) —

CN, and

(g) —

OH;

(4) a 5- or 6- membered heteroaromatic ring selected from thienyl, pyridyl, imidazolyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyrazinyl, pyrimidinyl, triazolyl, tetrazolyl, furanyl, and pyridazinyl, wherein the heteroaromatic ring is unsubstituted or substituted on nitrogen or carbon with from 1 to 4 substituents independently selected from;

(a) halogen,

(b) C_1-4 alkyl,

(c) C_1-4 fluoroalkyl,

(d) —

O—

C_1-4 alkyl,

(e) —

O—

C_1-4 fluoroalkyl,

(f) phenyl,

(g) —

S—

C_1-4 alkyl,

(h) —

CN,

(i) —

OH,

(j) phenyloxy, unsubstituted or substituted with from 1 to 3 substituents independently selected from;

(i) halogen,

(ii) C_1-4 alkyl,

(iii) C_1-4 fluoroalkyl, and

(iv) —

OH,

(k) —

N(R^a)₂,

(l) —

C_1-4 alkyl-N(R^a)₂,

(m) —

R^t,

(n) oxo,

(o) —

(CH₂)_0-3C(═

O)N(R^a)₂, and

(p) —

(CH₂)_0-3C(═

O)R^a;

(5) a 5- or 6- or 7- membered saturated heterocyclic ring selected from piperidinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isooxazolidinyl, pyrrolidinyl, imidazolidinyl, piperazinyl, tetrahydrofuranyl, pyrazolidinyl, hexahydropyrimidinyl, thiazinanyl, thiazepanyl, azepanyl, thiadiazepanyl, dithiazepanyl, diazepanyl, and thiadiazinanyl, and wherein the heterocyclic ring is unsubstituted or substituted with from 1 to 4 substituents independently selected from;

(a) halogen,

(b) C_1-6 alkyl,

(c) —

O—

C_1-6 alkyl,

(d) C_1-6 fluoroalkyl,

(e) —

O—

C_1-6 fluoroalkyl,

(f) —

CN,

(g) oxo,

(h) phenyl

(i) benzyl,

(j) phenylethyl,

(k) —

OH,

(l) —

(CH₂)_0-3C(═

O)N(R^a)₂,

(m) —

(CH₂)_0-3C(═

O)R^a,

(n) —

N(R^a)—

C(═

O)R^a,

(o) —

N(R^a)—

CO₂R^a,

(p) —

(CH₂)_1-3N(R^a)—

C(═

O)R^a,

(q) —

N(R^a)₂,

(r) —

(CH₂)_1-3N(R^a)₂,

(s) —

(CH₂)_1-3—

OR^a,

(t) —

(CH₂)_0-3CO₂R^a,

(u) —

(CH₂)_0-3—

O—

(CH₂)_1-3—

OR^a,

(v) —

SO₂R^a,

(w) —

SO₂N(R^a)₂,

(x) —

(CH₂)_0-3C(═

O)O(CH₂)_1-2CH═

CH₂,

(y) —

R^t,

(z) —

(CH₂)_0-3C(═

O)R^t,

(aa) —

N(R^a)R^t, and

(bb) —

(CH₂)_1-3R^t;

or

(6) an 8- to 10- membered heterobicyclic ring selected from indolyl, benzotriazolyl, benzoimidazolyl, imidazo[4,5-b]pyridinyl, dihydroimidazo[4,5-b]pyridinyl, pyrazolo[4,3-c]pyridinyl, dihydropyrazolo[4,3-c]pyridinyl, tetrahydropyrazolo[4,3-c]pyridinyl, pyrrolo[1,2-a]pyrazinyl, dihydropyrrolo[1,2-a]pyrazinyl, tetrahydropyrrolo[1,2-a]pyrazinyl, octahydropyrrolo[1,2-a]pyrazinyl, isoindolyl, indazolyl, indolinyl, isoindolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, chromanyl, isochromanyl, hexahydropyrazolo[4,3-c]pyridinyl, hexahydropurinyl, hexahydrooxazolo[3,4a]pyrazinyl, and 1,2,3,4-tetrahydro-1,8-naphthyridinyl; and

wherein the bicyclic ring is unsubstituted or substituted with from 1 to 3 substituents independently selected from;

(a) halogen,

(b) C_1-4 alkyl,

(c) —

O—

C_1-4 alkyl,

(d) C_1-4 fluoroalkyl,

(e) —

O—

C_1-4 fluoroalkyl,

(f) —

CN,

(g) ═

O, and

(h) —

OH;

R^t is naphthyl or a 5- or 6-membered heteromonocylic ring selected from pyrrolidinyl, pyrazolidinyl, imidazolinyl, piperidinyl, piperazinyl, pyrrolyl, pyridyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyrazinyl, pyrimidinyl, and pyradizinyl; and

wherein the naphthyl or the heteromonocyclic ring is unsubstituted or substituted with 1 or 2 substituents independently selected from halogen, oxo, C_1-4 alkyl, and —

O—

C_1-4 alkyl;

or a pharmaceutically acceptable salt thereof.

16. The compound according to claim 4, which is a compound of Formula (IX):

17. The compound according to claim 16, which is a compound of Formula (X):

18. The compound according to claim 17, which is a compound of Formula (XI):

19. The compound according to claim 18, which is a compound of Formula (XII):

20. The compound according to claim 19, wherein

R⁶ is:

(1) —

H

(2) methyl,

(3) ethyl

(4) —

CF₃,

(4) —

(CH₂)_1-3—

OR^a,

(5) —

(CH₂)_1-3—

SR^a,

(6) —

(CH₂)_1-3—

SO₂R^a,

(7) —

(CH₂)_1-3—

N(R^a)₂,

(8) —

(CH₂)_1-3—

C(═

O)—

N(R^a)₂, or

(9) —

(CH₂)_1-3—

CO₂R^a;

R⁹ is;

(1) —

H

(2) methyl,

(3) ethyl,

(4) —

CF₃,

(4) —

(CH₂)_1-3—

OR^a,

(5) —

(CH₂)_1-3—

SR^a,

(6) —

(CH₂)_1-3—

SO₂R^a,

(7) —

(CH₂)_1-3—

N(R^a)₂,

(8) —

(CH₂)_1-3—

C(═

O)—

N(R^a)₂,

(9) —

(CH₂)_1-3—

CO₂R^a, or

(10) —

(CH₂)_1-3-R^k;

each R^a is independently —

H, methyl, or ethyl;

R^k is a saturated heterocyclic ring selected from piperidinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isooxazolidinyl, pyrrolidinyl, imidazolidinyl, piperazinyl, tetrahydrofuranyl, and pyrazolidinyl; and

wherein the heterocyclic ring is unsubstituted or substituted with from 1 to 3 substituents independently selected from;

(a) halogen selected from —

F, —

Cl, and —

Br,

(b) methyl,

(c) —

CF₃,

(d) methoxy,

(e) —

OCF₃,

(f) —

CN, and

(g) ═

O;

or a pharmaceutically acceptable salt thereof.

21. A compound according to claim 1, which is a compound selected from the group consisting of

N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-[(1R,S)-2,3-dihydro-1H-inden-1-yl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-[2-(3-chlorophenyl)ethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-[2-(2-chlorophenyl)ethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-[2-(1,1′

-biphenyl-4-yl)ethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-[2-(4-phenoxyphenyl)ethyl]-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(3-phenylpropyl)-1,6-naphthyridine-7-carboxamide;

N-(1,1′

-biphenyl-2-ylmethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(1,1′

-biphenyl-3-ylmethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-phenyl-1,6-naphthyridine-7-carboxamide;

8 N-(2-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-benzyl-8-hydroxy-N-methyl-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(1-methyl-1-phenylethyl)-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(2-phenylethyl)-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(1-naphthylmethyl)-1,6-naphthyridine-7-carboxamide;

N-benzyl-8-hydroxy-N-phenyl-1,6-naphthyridine-7-carboxamide;

N-(3-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-chlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

Methyl (2S)-{[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]amino}(phenyl)ethanoate;

Ethyl N-benzyl-N-[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]glycinate;

N-benzyl-8-hydroxy-N-(2-phenylethyl)-1,6-naphthyridine-7-carboxamide;

N-(1,2-diphenylethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2,3-dihydro-1H-inden-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-benzyl-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2-anilinoethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2,2-diphenylethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,3-diphenylpropyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2-chloro-6-phenoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

Methyl (2R)-{[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]amino}(phenyl)ethanoate;

8-hydroxy-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,6-naphthyridine-7-carboxamide;

N-(2,3-dihydro-1H-inden-1-ylmethyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(6,7,8,9-tetrahydro-5H-benzo [a][7]annulen-6-ylmethyl)-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-[2-(1′

-naphthylamino)ethyl]-1,6-naphthyridine-7-carboxamide;

N-(2,3-dihydro-1H-inden-2-yl methyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-[(R)-1-phenylethyl]-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-[(1S)-1-phenylethyl]1-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(3-hydroxy-1-phenylpropyl)-1,6-naphthyridine-7-carboxamide;

N-[2-(4-chlorophenyl)ethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-[(1R)-2-hydroxy-1-phenylethyl]-1,6-naphthyridine-7-carboxamide;

N-[(1S)-1-benzyl-2-hydroxyethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-[(1R)-1-benzyl-2-hydroxyethyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(2-hydroxy-2-phenylethyl)-1,6-naphthyridine-7-carboxamide;

5-chloro-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-piperidin-1-yl-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-phenyl-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(1H-imidazol-1-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-morpholin-4-yl-1,6-naphthyridine-7-carboxamide;

(±

)-8-hydroxy-N-[(cis)-3-phenyl-2,3-dihydro-1H-inden-1-yl]-1,6-naphthyridine-7-carboxamide

5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(benzyl)-8-hydroxy-5-phenyl-1,6-naphthyridine-7-carboxamide;

N-(2,3-dihydro-1H-inden-1-yl)-8-hydroxy-5-phenyl-1,6-naphthyridine-7-carboxamide;

8-hydroxy-N-(1-naphthylmethyl)-5-phenyl-1,6-naphthyridine-7-carboxamide;

N-(2,5-dichlorobenzyl)-8-hydroxy-5-phenyl-1,6-naphthyridine-7-carboxamide;

N-(3-chlorobenzyl)-8-hydroxy-5-phenyl-1,6-naphthyridine-7-carboxamide;

N-[(1S)-2,3-dihydro-1H-inden-1-yl]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-phenoxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-methylpiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

5-(4-benzylpiperazin-1-yl)-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-{4-[2-(formylamino)ethyl]piperazin-1-yl}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-pyridin-2-ylpiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-pyrrolidin-1-ylpiperidin-1-yl)-1,6-naphthyridine-7-carboxamide;

5-anilino-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-{[3-(formylamino)propyl]amino}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-{[2-(dimethylamino)ethyl]amino}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-morpholin-4-ylethyl)amino]-1,6-naphthyridine-7-carboxamide;

5-[(1-benzylpiperidin-4-yl)amino]-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-[[2-(dimethylamino)ethyl](methyl)amino]-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-Hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide;

5-benzenesulfonyl-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide;

tert-butyl 1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)pyrrolidin-3-ylcarbamate;

5-(3-aminopyrrolidin-1-yl)-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide trifluoroacetate;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4H-1,2,4-triazol-4-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(1H-1,2,4-triazol-1-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(3-hydroxypyrrolidin-1-yl)-1,6-naphthyridine-7-carboxamide;

5-[3-(acetylamino)pyrrolidin-1-yl]-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-(4-formylpiperazin-1-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)piperazine;

8-Hydroxy-5-(3-hydroxy-prop-1-ynyl)-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide;

1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazine;

8-Hydroxy-5-(3-piperidin-1-yl-prop-1-ynyl)-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-thiomorpholin-4-yl-1,6-naphthyridine-7-carboxamide;

5-[3-(aminocarbonyl)piperidin-1-yl]-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-(2-phenylethyl)piperazine;

4-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]pyridine;

5-[(cyclopropylmethyl)amino]-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-{[2-(formylamino)ethyl]amino}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

2-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]ethanamine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-methoxyethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-{[2-(methylthio)ethyl]amino}-1,6-naphthyridine-7-carboxamide;

1-{2-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]ethyl}pyrrolidine;

1 N-(3,5-dichlorobenzyl)-8-hydroxy-5-pyrrolidin-1-yl-1,6-naphthyridine-7-carboxamide;

3-{2-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]ethyl}pyridine;

1-{3-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]propyl}-1H-imidazoline;

1-{3-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]propyl}pyrrolidine;

1-(2-aminoethyl)-4-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)piperazine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-phenoxyethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-{[3-(2-oxopyrrolidin-1-yl)propyl]amino}-1,6-naphthyridine-7-carboxamide;

2-[benzyl(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]ethanamine;

1-{3-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)amino]propyl}-4-methylpiperazine;

1;

1 mixture of 1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-1H-imidazo[4,5-b]pyridine and 3-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-3H-imidazo[4,5-b]pyridine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-{[4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]amino}-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-({[(2R)-5-oxopyrrolidin-2-yl]methyl}amino)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-{[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}-1,6-naphthyridine-7-carboxamide;

2-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)octahydropyrrolo[1,2-a]pyrazine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[4-(pyrimidin-2-ylamino)piperidin-1-yl]-1,6-naphthyridine-7-carboxamide

2-{2-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)(methyl)amino]ethyl}pyridine;

N-(3,5-dichlorobenzyl)-5-(dimethylamino)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-Hydroxy-5-(3-morpholin-4-yl-prop-1-ynyl)-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide;

N-(3,5-difluorobenzyl)-8-hydroxy-5-(methylsulfonyl)-1,6-naphthyridine-7-carboxamide;

5-cyano-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxyamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-thien-2-yl-1,6-naphthyridine-7-carboxamide;

8-hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 2-methylsulfanylbenzylamide;

N-(2,3-dimethoxybenzyl)-8-hydroxy-5-(methylsulfonyl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-hydroxyethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(propylamino)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(1H-imidazol-4-ylethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(3-phenylprop-1-yl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(3-morpholin-4-ylpropyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[4-(pyridin-2-ylmethyl)piperazin-1-yl]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-morpholin-4-yl-2-pyridin-3-ylethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(2,3-dimethoxybenzyl)-5-{[4-(dimethylamino)phenyl]thio}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide;

8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid 4-fluoro-benzylamide;

5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-methylpiperazine;

1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)piperazine;

5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-N-1-,N-2-,N-2-trimethylethanediamide;

N-(4-fluorobenzyl)-5-(2,6-dioxohexahydropyrimidin-4-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

5-(1,3-dimethyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

5-(1-methyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

5-(3-methyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(5-oxo-1,4-thiazepan-7-yl)[1,6]naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1-oxido-5-oxo-1,4-thiazepan-7-yl)-[1,6]naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1,1-dioxido-5-oxo-1,4-thiazepan-7-yl)[1,6]-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl]sulfanyl}-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(dimethylamino)-2-oxoethoxy]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl](methylsulfonyl)amino}-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[3-(dimethylamino)-3-oxopropyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[(1E)-3-(dimethylamino)-3-oxo-1-propenyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(3-oxo-1-piperazinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(2-oxo-1-imidazolidinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(2-oxo-1-piperazinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

5-(1,1-dioxido-1,2-thiazinan-2-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

5-(1,1-dioxidoisothiazolidin-2-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide;

5-[acetyl(methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

5-[[(dimethylamino)carbonyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-6-hydroxy-3-methyl-1-(2-morpholin-4-ylethyl)-2-oxo-2,3-dihydro-1H-pyrimido[4,5,6-de]-1,6-naphthyridine-5-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-thiomorpholin-4-yl-1,6-naphthyridine-7-carboxamide;

5-(1,1-dioxidothiomorpholin-4-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(4-methyl-3-oxopiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

1-(7-{[4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl-L-prolinamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(2-oxotetrahydropyrimidin-1 (2H)-yl)-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(2-oxoimidazolidin-1-yl)-1,6-naphthyridine-7-carboxamide;

N-7-(4-fluorobenzyl)-8-hydroxy-N 5, N 5-dimethyl-1,6-naphthyridine-5,7-dicarboxamide;

N-7-(4-fluorobenzyl)-8-hydroxy-N 5-isopropyl-N 5-methyl-1,6-naphthyridine-5,7-dicarboxamide;

N-7-(4-fluorobenzyl)-8-hydroxy-N 5-(2-morpholin-4-ylethyl)-1,6-naphthyridine-5,7-dicarboxamide;

N 5-[2-(dimethylamino)-2-oxoethyl]-N 7-(4-fluorobenzyl)-8-hydroxy-N 5-methyl-1,6-naphthyridine-5,7-dicarboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-5-methyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-5-ethyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-1,5,2-dithiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1,5,5-tetraoxido-1,5,2-dithiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,4-dimethyl-7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1-methyl-7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide;

N-(4-Fluorobenzyl)-5-(7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)thiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)-1-oxidothiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)-1,1-dioxidothiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(2-Acetyl-1-methylpyrazolidin-3-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-[5-(methylsulfonyl)-1,1-dioxido-1,2,5-thiadiazepan-2-yl]-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2yl)-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxamide;

N-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxamide;

N-7-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-N-5-,N-5-dimethyl-1,6-naphthyridine-5,7-dicarboxamide;

N-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-5-(1,1-dioxido-1,2-thiazinan-2-yl)-1,6-naphthyridine-7-carboxamide

N-(2-(methylsulfonyl)benzyl)-5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2-[(dimethylaminosulfonyl]-4-fluorobenzyl)-5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1-methyl-5-oxopyrrolidin-3-yl)-1,6-naphthyridine-7-carboxamide;

and pharmaceutically acceptable salts thereof.

22. A compound according to claim 21, which is a compound selected from the group consisting of

1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-methylpiperazine;

1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)piperazine;

N-(3,5-dichlorobenzyl)-5-(4-formylpiperazin-1-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-5-{4-[2-(formylamino)ethyl]piperazin-1-yl}-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[4-(pyridin-2-ylmethyl)piperazin-1-yl]-1,6-naphthyridine-7-carboxamide;

1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazine;

1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)piperazine;

2-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)octahydropyrrolo[1,2-a]pyrazine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-{[4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]amino}-1,6-naphthyridine-7-carboxamide;

5-[3-(aminocarbonyl)piperidin-1-yl]-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-pyrrolidin-1-ylpiperidin-1-yl)-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-morpholin-4-ylethyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-methylpiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[4-(pyrimidin-2-ylamino)piperidin-1-yl]-1,6-naphthyridine-7-carboxamide

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(3-morpholin-4-ylpropyl)amino]-1,6-naphthyridine-7-carboxamide;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-[(2-morpholin-4-yl-2-pyridin-3-ylethyl)amino]-1,6-naphthyridine-7-carboxamide;

2-{2-[(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)(methyl)amino]ethyl}pyridine;

N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-pyridin-2-ylpiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

and pharmaceutically acceptable salts thereof.

23. A compound according to claim 21, which is a compound selected from the group consisting of

5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-1-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-N-1-,N-2-,N-2-trimethylethanediamide;

N-(4-fluorobenzyl)-5-(2,6-dioxohexahydropyrimidin-4-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

5-(1,3-dimethyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

5-(1-methyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

5-(3-methyl-2,6-dioxohexahydro-4-pyrimidinyl)-N-(4-fluorobenzyl)-8-hydroxy[1,6]-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(5-oxo-1,4-thiazepan-7-yl) [1,6]naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1-oxido-5-oxo-1,4-thiazepan-7-yl)-[1,6]naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1,1-dioxido-5-oxo-1,4-thiazepan-7-yl)[1,6]-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl]sulfanyl}-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(dimethylamino)-2-oxoethoxy]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-{[2-(dimethylamino)-2-oxoethyl](methylsulfonyl)amino}-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[3-(dimethylamino)-3-oxopropyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[(1E)-3-(dimethylamino)-3-oxo-1-propenyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(3-oxo-1-piperazinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(2-oxo-1-imidazolidinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[2-(2-oxo-1-piperazinyl)ethyl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

5-(1,1-dioxido-1,2-thiazinan-2-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

5-(1,1-dioxidoisothiazolidin-2-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide;

5-[acetyl(methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

5-[[(dimethylamino)carbonyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-6-hydroxy-3-methyl-1-(2-morpholin-4-ylethyl)-2-oxo-2,3-dihydro-1H-pyrimido[4,5,6-de]-1,6-naphthyridine-5-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-thiomorpholin-4-yl-1,6-naphthyridine-7-carboxamide;

5-(1,1-dioxidothiomorpholin-4-yl)-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(4-methyl-3-oxopiperazin-1-yl)-1,6-naphthyridine-7-carboxamide;

1-(7-{[4-fluorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl-L-prolinamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(2-oxotetrahydropyrimidin-1 (2H)-yl)-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(2-oxoimidazolidin-1-yl)-1,6-naphthyridine-7-carboxamide;

N-7-(4-fluorobenzyl)-8-hydroxy-N 5, N 5-dimethyl-1,6-naphthyridine-5,7-dicarboxamide;

N 7-(4-fluorobenzyl)-8-hydroxy-N 5-isopropyl-N 5-methyl-1,6-naphthyridine-5,7-dicarboxamide;

N 7-(4-fluorobenzyl)-8-hydroxy-N 5-(2-morpholin-4-ylethyl)-1,6-naphthyridine-5,7-dicarboxamide;

N 5-[2-(dimethylamino)-2-oxoethyl]-N 7-(4-fluorobenzyl)-8-hydroxy-N 5-methyl-1,6-naphthyridine-5,7-dicarboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

and pharmaceutically acceptable salts thereof.

24. A compound according to claim 21, which is a compound selected from the group consisting of

N-(4-fluorobenzyl)-5-(1,1-dioxido-5-methyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-5-ethyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-1,5,2-dithiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1,5,5-tetraoxido-1,5,2-dithiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,4-dimethyl-7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1-methyl-7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide;

N-(4-Fluorobenzyl)-5-(7-oxo-1,4-diazepan-5-yl)-8-hydroxy-[1,6]-napthyridine-7-carboxamide

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)thiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)-1-oxidothiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-[4-(methylsulfonyl)-1,1-dioxidothiomorpholin-2-yl]-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(2-Acetyl-1-methylpyrazolidin-3-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-5-(1,1-dioxido-1,2,5-thiadiazepan-2-yl)-8-hydroxy-[1,6]napthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-[5-(methylsulfonyl)-1,1-dioxido-1,2,5-thiadiazepan-2-yl]-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5(6-methyl-1,1-dioxido-1,2,6-thiadiazinan-2yl)-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxamide;

N-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxamide;

N-7-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-N-5-,N-5-dimethyl-1,6-naphthyridine-5,7-dicarboxamide;

N-[4-fluoro-2-(methylsulfonyl)benzyl]-8-hydroxy-5-(1,1-dioxido-1,2-thiazinan-2-yl)-1,6-naphthyridine-7-carboxamide

N-(2-(methylsulfonyl)benzyl)-5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(2-[(dimethylaminosulfonyl]-4-fluorobenzyl)-5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide;

N-(4-fluorobenzyl)-8-hydroxy-5-(1-methyl-5-oxopyrrolidin-3-yl)-1,6-naphthyridine-7-carboxamide;

and pharmaceutically acceptable salts thereof.

25. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

26. A method of inhibiting HIV integrase in a subject in need thereof which comprises administering to the subject a therapeutically effective amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

27. A method for preventing or treating infection by HIV or for preventing, treating or delaying the onset of AIDS in a subject in need thereof which comprises administering to the subject a therapeutically effective amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

28. The method according to claim 27, wherein the compound is administered in combination with a therapeutically effective amount of at least one HIV infection/AIDS treatment agent selected from the group consisting of HIV/AIDS antiviral agents, immunomodulators, and anti-infective agents.

29. The method according to claim 27, wherein the compound is administered in combination with a therapeutically effective amount of at least one antiviral selected from the group consisting of HIV protease inhibitors, non-nucleoside HIV reverse transcriptase inhibitors and nucleoside HIV reverse transcriptase inhibitors.

30. A method of inhibiting HIV integrase in a subject in need thereof which comprises administering to the subject a therapeutically effective amount of the composition according to claim 25.

31. A method for preventing or treating infection by HIV or for preventing, treating, or delaying the onset of AIDS in a subject in need thereof which comprises administering to the subject a therapeutically effective amount of the composition according to claim 25.

32. A pharmaceutical composition which comprises the product prepared by combining an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

33. A combination useful for inhibiting HIV integrase, for treating or preventing infection by HIV, or for preventing, treating or delaying the onset of AIDS, which is a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a therapeutically effective amount of an HIV infection/AIDS treatment agent selected from the group consisting of HIV/AIDS antiviral agents, immunomodulators, and anti-infective agents.

34. The combination according to claim 33, wherein the HIV infection/AIDS treatment agent is an antiviral selected from the group consisting of IEV protease inhibitors, non-nucleoside HIV reverse transcriptase inhibitors and nucleoside HIV reverse transcriptase inhibitors.

8. A compound of Formula (IV):

9. The compound according to claim 8, wherein

Q² is

(1) —

H,

(2) methyl,

(3) ethyl,

(4) CF₃,

(5) methoxy,

(6) ethoxy

(7) —

OCF₃

(8) halo selected from —

F, —

Cl and —

Br,

(9) —

CN,

(10) —

CH₂OH,

(11) —

CH₂OCH₃,

(12) —

(CH₂)_0-2C(═

O)CH₃,

(13) —

(CH₂)_0-2CO₂CH₃,

(14) —

SR^a,

(15) —

N(R^a)₂,

(16) —

(CH₂)_1-2N(R^a)₂,

(17) —

(CH₂)_0-2C(═

O)N(R^a)₂,

(18) —

S—

CH₂—

C(═

O)N(R^a)₂,

(19) —

O—

CH₂—

C(═

O)N(R^a)₂,

(20) —

N(SO₂R^a)—

CH₂—

C(═

O)N(R^a)₂,

(21) —

N(R^a)—

C(R^a)═

O,

(22) —

C(═

O)—

N(R^a)—

(CH₂)_1-2—

C(═

O)N(R^a)₂,

(23) —

C(═

O)—

N(R^a)—

(CH₂)_1-2OR^a,

(24) —

C(═

O)—

N(R^a)—

(CH₂)_1-3—

N(R^a)₂,

(25) —

SO₂R^a,

(26) —

N(R^a)SO₂R^a,

(27) —

CH═

CH—

C(═

O)—

N(R^a)₂,

(28) —

C≡

C—

CH₂OR^a,

(29) —

C≡

C—

CH₂SR^a,

(30) —

C≡

C—

CH₂SO₂R

(32) —

N(R^a)—

(CH₂)_1-3 SR^a,

(33) —

N(R^a)—

(CH₂)_1-3OR^a,

(34) —

N(R^a)—

(CH₂)_1-3N(R^a)₂,

(35) —

N(R^a)—

(CH₂)_1-3N(R^a)—

C(R^a)═

O,

(36) —

N(R^a)CH₂—

C(═

O)N(R^a)₂,

(37) —

N(R^a)—

C(═

O)—

C(═

O)—

N(R^a)₂,

(38) —

N(R^a)—

C(═

O)—

N(R^a)₂,

(39) —

N(R^a)—

(CH₂)_1-2—

CO₂R^a,

(40) —

N(R^a)—

C(═

O)—

N(R^a)—

(CH₂)_1-2—

C(═

O)—

N(R^a)₂,

(41) —

N(R^a)—

C(═

O)—

(CH₂)_1-2—

C(═

O)—

N(R^a)₂,

(42) —

N(R^a)—

SO₂—

N(R^a)₂,

(43) R^k,

(44) —

(CH₂)_1-4R^k,

(45) —

C≡

C—

CH₂R^k,

(46) —

O—

R^k,

(47) —

S—

R^k,

(48) —

SO₂—

R^k,

(49) —

N(R^c)—

R^k,

(50) —

N(R^c)—

(CH₂)_1-4H substituted with one or two R^k groups,

(51) —

N(R^c)—

(CH₂)_1-4OR^k,

(52) —

C(═

O)—

R^k,

(53) —

C(═

O)N(R^a)—

R^k,

(54) —

N(R^a)—

C(═

O)—

R^k,

(55) —

C(═

O)N(R^a)—

(CH₂)_1-4R^k, or

(56) —

N(R^a)—

SO₂R^k,

each of R¹ and R² is independently;

(1) —

H,

(2) methyl,

(3) ethyl,

(4) CF₃,

(5) methoxy,

(6) ethoxy

(7) —

OCF₃

(8) halo selected from —

F and —

Cl,

(9) —

CN,

(10) —

CH₂OR^a,

(11) —

CO₂R^a,

(12) —

SR^a,

(13) —

N(R^a)₂,

(14) —

(CH₂)_1-3N(R^a)₂,

(15) —

SO₂R^a,

(16) —

R^k,

(17) —

(CH₂)_1-3R^k,

(18) —

O—

R^k, or

(19) —

O—

(CH₂)_1-3R^k;

each R^a is independently —

H or —

C_1-4 alkyl;

each R^c is independently —

H, —

C_1-4 alkyl, or —

(CH₂)_1-3N(R^a)₂;

each R^k is independently;

(1) phenyl which is unsubstituted or substituted with from 1 to 4 substituents independently selected from;

(a) halogen selected from —

F, —

Cl, and —

Br,

(b) methyl or ethyl,

(c) —

CF₃,

(d) methoxy,

(e) —

OCF₃,

(f) phenyl,

(g) —

S—

CH₃,

(h) —

CN,

(i) —

OH,

(j) phenyloxy

(k) —

N(R^a)₂,

(l) —

(CH₂)_1-3N(R^a)₂,

(m) —

R^t,

(p) —

(CH₂)_0-3C(═

O)N(R^a)₂, and

(q) —

(CH₂)_0-3C(═

O)R^a;

(2) —

C_3-6 cycloalkyl,

(3) a 5- or 6- membered heteroaromatic ring selected from thienyl, pyridyl, imidazolyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyrazinyl, pyrimidinyl, triazolyl, tetrazolyl, furanyl, and pyridazinyl, wherein the heteroaromatic ring is unsubstituted or substituted on nitrogen or carbon with 1 or 2 substituents independently selected from;

(a) halogen selected from —

F, —

Cl, and —

Br,

(b) methyl or ethyl,

(c) —

CF₃,

(d) methoxy,

(e) —

OCF₃,

(f) —

S—

C_1-6 alkyl,

(g) —

CN,

(h) —

OH,

(i) —

N(R^a)₂,

(j) —

C_1-6 alkyl-N(R^a)₂,

(k) —

R^t,

(l) oxo,

(m) —

(CH₂)_0-3C(═

O)N(R^a)₂, and

(n) —

(CH₂)_0-3C(═

O)R^a;

(4) a 5- or 6- or 7- membered saturated heterocyclic ring selected from piperidinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isooxazolidinyl, pyrrolidinyl, imidazolidinyl, piperazinyl, tetrahydrofuranyl, pyrazolidinyl, hexahydropyrimidinyl, thiazinanyl, thiazepanyl, azepanyl, thiadiazepanyl, dithiazepanyl, diazepanyl, and thiadiazinanyl; and

wherein the heterocyclic ring is unsubstituted or substituted with 1 to 4 substituents independently selected from;

(a) halogen selected from —

F, —

Cl, and —

Br,

(b) methyl or ethyl,

(c) —

CF₃,

(d) methoxy,

(e) —

OCF₃,

(f) —

CN,

(g) ═

O,

(h) phenyl,

(i) benzyl,

(j) phenylethyl,

(k) —

OH,

(l) —

(CH₂)_0-3C(═

O)N(R^a)₂,

(m) —

(CH₂)_0-3C(═

O)R^a,

(n) N(R^a)—

C(═

O)R^a,

(o) N(R^a)—

CO₂R^a,

(p) (CH₂)_1-3N(R^a)—

C(═

O)R^a,

(q) N(R^a)₂,

(r) (CH₂)_1-3N(R^a)₂,

(s) SO₂R^a,

(t) —

(CH₂)_0-3C(═

O)R^t,

(u) —

R^t,

(v) —

N(R^a)R^t, and

(w) —

(CH₂)_1-3R^t; and

(5) an 8- to 10- membered heterobicyclic ring selected from indolyl, benzotriazolyl, benzoimidazolyl, imidazo[4,5-b]pyridinyl, dihydroimidazo[4,5-b]pyridinyl, pyrazolo[4,3-c]pyridinyl, dihydropyrazolo[4,3-c]pyridinyl, tetrahydropyrazolo[4,3-c]pyridinyl, pyrrolo[1,2-a]pyrazinyl, dihydropyrrolo[1,2-a]pyrazinyl, tetrahydropyrrolo[1,2-a]pyrazinyl, octahydropyrrolo[1,2-a]pyrazinyl, isoindolyl, indazolyl, indolinyl, isoindolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, chromanyl, isochromanyl, and 1,2,3,4-tetrahydro-1,8-naphthyridinyl, wherein the bicyclic ring is unsubstituted or substituted with 1 or 2 substituents independently selected from;

(a) halogen selected from —

F, —

Cl, and —

Br,

(b) methyl or ethyl,

(c) —

CF₃,

(d) methoxy,

(e) —

OCF₃,

(f) —

CN,

(g) ═

O, and

(h) —

OH;

R^t is selected from pyrrolidinyl, pyrazolidinyl, imidazolinyl, piperidinyl, piperazinyl, pyrrolyl, pyridyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyrazinyl, pyrimidinyl, and pyradizinyl;

any one of which is unsubstituted or substituted with 1 or 2 substituents independently selected from —

F, —

Cl, —

Br, oxo, methyl, and methoxy;

or a pharmaceutically acceptable salt thereof.

10. The compound according to claim 9, which is a compound of Formula (VI):

11. A compound of Formula (V-A):

12. The compound according to claim 11, wherein R¹ is H or F, and R² is H or —

SO₂CH₃, with the proviso that R¹ and R² are not both H;

or a pharmaceutically acceptable salt thereof.

13. The compound according to claim 12, which is a compound of Formula (VIII):

14. The compound according to claim 12, wherein

Q² is:

(1) —

C(═

O)N(R^a)₂,

(2) —

CH₂C(═

O)N(R^a)₂,

(3) —

CH₂CH₂C(═

O)N(R^a)₂,

(4) —

S—

CH₂—

C(═

O)N(R^a)₂,

(5) —

O—

CH₂—

C(═

O)N(R^a)₂,

(6) —

N(R^a)—

C(R^a)═

O,

(7) —

N(SO₂R^a)—

CH₂—

C(═

O)N(R^a)₂,

(8) —

N(R^a)—

C(═

O)—

C(═

O)—

N(R^a)₂,

(9) —

N(R^a)SO₂R^a,

(10) —

CH═

CH—

C(═

O)—

N(R^a)₂,

(11) —

N(R^a)CH₂—

C(═

O)N(R^a)₂,

(12) —

N(R^a)—

C(═

O)—

N(R^a)₂,

(13) —

R^k,

(14) —

(CH₂)_1-3R^k, or

(15) —

N(R^c)—

(CH₂)_1-3R^k,

each R^a is independently —

H or —

C_1-4 alkyl;

each R^c is independently —

H or —

C_1-4 alkyl; and

R^k is a saturated heterocyclic ring selected from piperidinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isooxazolidinyl, pyrrolidinyl, imidazolidinyl, piperazinyl, tetrahydrofuranyl, pyrazolidinyl, hexahydropyrimidinyl, 1,2-thiazinanyl, 1,4-thiazepanyl, 1,2,5-thiadiazepanyl, 1,5,2-dithiazepanyl, 1,4-diazepanyl, and 1,2,6-thiadiazinanyl, wherein the heterocyclic ring is unsubstituted or substituted with 1 to 4 substituents independently selected from;

(a) methyl or ethyl,

(b) ═

O,

(c) —

C(═

O)N(R^a)₂,

(d) —

CH₂C(═

O)N(R^a)₂,

(e) —

C(═

O)R^a, or

(f) —

SO₂R^a;

or a pharmaceutically acceptable salt thereof.

15. The compound according to claim 14, wherein

Q² is:

(1) —

C(═

O)N(R^a)₂,

(2) —

CH₂C(═

O)N(R^a)₂,

(3) —

CH₂CH₂C(═

O)N(R^a)₂,

(4) —

S—

CH₂—

C(═

O)N(R^a)₂,

(5) —

O—

CH₂—

C(═

O)N(R^a)₂,

(6) —

N(SO₂R^a)—

CH₂—

C(═

O)N(R^a)₂,

(7) —

N(R^a)—

C(═

O)—

C(═

O)—

N(R^a)₂,

(8) —

N(R^a)SO₂R^a,

(9) —

CH═

CH—

C(═

O)—

N(R^a)₂,

(10) —

N(R^a)CH₂—

C(═

O)N(R^a)₂,

(11) —

N(R^a)—

C(═

O)—

N(R^a)₂,

(12) —

R^k,

(13) —

(CH₂)_1-2R^k, or

(14) —

NH—

(CH₂)_1-2R^k;

each R^a is independently methyl, ethyl, or isopropyl; and

R^k is a saturated heterocyclic ring selected from piperidinyl, morpholinyl, thiomorpholinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isooxazolidinyl, pyrrolidinyl, imidazolidinyl, piperazinyl, tetrahydrofuranyl, pyrazolidinyl, hexahydropyrimidinyl, 1,2-thiazinanyl, 1,4-thiazepanyl, 1,2,5-thiadiazepanyl, 1,5,2-dithiazepanyl, 1,4-diazepanyl, and 1,2,6-thiadiazinanyl, wherein the heterocyclic ring is unsubstituted or substituted with 1 to 4 substituents independently selected from;

(a) methyl or ethyl,

(b) ═

O,

(c) —

C(═

O)NH₂,

(d) —

C(═

O)CH₃, or

(e) —

SO₂CH₃;

or a pharmaceutically acceptable salt thereof.

35. A method of inhibiting HIV integrase, for preventing or treating infection by HIV or for preventing, treating or delaying the onset of AIDS in a subject in need thereof, which comprises administering to the subject a therapeutically effective amount of a compound of Formula (I-A):

36. The method according to claim 35, wherein the compound is selected from the group consisting of:

benzyl 8-hydroxyquinoline-7-carboxamide;

1-Methyl-3-phenylpropyl 8-hydroxyquinoline-7-carboxamide;

2-Phenylcyclopropyl 8-hydroxyquinoline-7-carboxamide;

1-Indanyl 8-hydroxyquinoline-7-carboxamide;

N-[(2E)-3-Phenyl-2-propenyl]8-hydroxyquinoline-7-carboxamide;

Benzyl 8-Hydroxyquinoline-7-carboxamide;

and pharmaceutically acceptable salts thereof.