US 2005/0239769 A1Published application

Therapeutic compounds for treating dyslipidemic conditions

AssigneeMerck & Co., Inc.

InventorsA. Jones, Alan Adams, Ahren Green, Shaei Huang, Bruno Tse, Clare Gutteridge, Yuan Cheng

Life of this patent

Estimating the term…

Abstract

The present invention relates to novel LXR ligands of Formula I and the pharmaceutically acceptable salts, esters and tautomers thereof, which are useful in the treatment of dyslipidemic conditions, particularly depressed levels of HDL cholesterol.

Claims24

Dependent claims

A compound of formula I

and the pharmaceutically acceptable salts, esters and tautomers thereof, wherein
R1 is selected from the group consisting of:
(a) —CF3,
(b) —CH2C(CH3)3,
(c) phenyl, unsubstituted, mono- or poly-substituted with halo,
(d) —C1-6 alkyl, and
(e) —C1-2alkyl-phenyl;
R2 is selected from the group consisting of:
(a) —C1-6 alkyl,
(b) —COOR3,
(c) —CR3R4—O—R5,
(d) —CR3R4—S—R5, and
(e) —COR3;
R3, R4 and R5 are independently selected at each occurrence from the group consisting of —H, phenyl, and C1-6 alkyl;
Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I to which Y is respectively attached, to form a heterocyclic ring selected from:
(a) a 5-membered heterocyclic ring selected from the group consisting of:
(b) a 6-membered heterocyclic ring selected from the group consisting of:
(d) a bicyclic heterocyclic ring selected from the group consisting of:
wherein each carbon atom in the heterocyclic ring, formed when Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I, is independently unsubstituted, mono- or di-substituted with a substituent independently selected at each occurrence from R7;
R6 is independently selected at each occurrence from the group consisting of:
(a) —H,
(b) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —NR3R4, —OR3, —COOR3, and —CN,
(c) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(d) —C3-6cycloalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —OR3, —COOR3, and —CN,
(e) —C3-6cycloheteroalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —(CH2)nOR3, —OR3, —COOR3, and —CN, wherein n is an integer selected from 2, 3, 4, 5 and 6,
(f) —C2-6alkenyl,
(g) —C(O)C1-6alkyl,
(h) —COOR3,
(i) —C(O)(CH2)p—COOR3, wherein p is an integer selected from 2, 3 and 4,
(j) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(l) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(m) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(n) thiazolyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
R7 is independently selected at each occurrence from the group consisting of:
(a) ═O,
(b) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —CN, —COOR3, —COR3, and —OH,
(c) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —COOR3, tetrazole and —CN,
(d) —C3-6 cycloalkyl,
(e) —C3-6 spiroalkyl,
(f) —COOR3,
(g) halo,
(h) —NR3R4,
(i) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —COOR3 and —C1-4alkyl,
(j) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(l) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
and
Z is selected from the group consisting of:
(a) —C1-6alkyl-,
(b) —C1-6alkyl-O—,
(c) —C3-6cycloalkyl-, and
(d) —C3-6cycloalkyl-O—.

50 more elements

A compound of formula I

and the pharmaceutically acceptable salts, esters and tautomers thereof, wherein
R1 is selected from the group consisting of:
(a) —CF3,
(b) —CH2C(CH3)3,
(c) phenyl, unsubstituted, mono- or poly-substituted with halo,
(d) —C1-6 alkyl, and
(e) —C1-2alkyl-phenyl;
R2 is selected from the group consisting of:
(a) —C1-6 alkyl,
(b) —COOR3,
(c) —CR3R4—O—R5,
(d) —CR3R4—S—R5, and
(e) —COR3;
R3, R4 and R5 are independently selected at each occurrence from the group consisting of —H, phenyl, and C1-6 alkyl;
Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I to which Y is respectively attached, to form a heterocyclic ring selected from:
(a) a 5-membered heterocyclic ring selected from the group consisting of:
(b) a 6-membered heterocyclic ring selected from the group consisting of:
provided that when R1 is —CF3, R2 is n-propyl, and Z is n-propyloxy, the 6-membered heterocyclic ring is not unsubstituted 5,6 dihydrouracil,
(d) a bicyclic heterocyclic ring selected from the group consisting of:
wherein each carbon atom in the heterocyclic ring, formed when Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I, is independently unsubstituted, mono- or di-substituted with a substituent independently selected at each occurrence from R7;
R6 is independently selected at each occurrence from the group consisting of:
(a) —H,
(b) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —NR3R4, —OR3, —COOR3, and —CN,
(c) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(d) —C3-6cycloalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —OR3, —COOR3, and —CN,
(e) —C3-6cycloheteroalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —(CH2)nOR3, —OR3, —COOR3, and —CN, wherein n is an integer selected from 2, 3, 4, 5 and 6,
(f) —C2-6alkenyl,
(g) —C(O)C1-6alkyl,
(h) —COOR3,
(i) —C(O)—(CH2)p—COOR3, wherein p is an integer selected from 2, 3 and 4,
(j) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(l) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(m) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(n) thiazolyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
R7 is independently selected at each occurrence from the group consisting of:
(a) ↑O,
(b) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —CN, —COOR3, —COR3, and —OH,
(c) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —COOR3, tetrazole and —CN,
(d) —C3-6 cycloalkyl,
(e) —C3-6 spiroalkyl,
(f) —COOR3,
(g) halo,
(h) —NR3R4,
(i) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —COOR3 and —C1-4alkyl,
(j) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(l) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
and
Z is selected from the group consisting of:
(a) —C1-6alkyl-,
(b) —C1-6alkyl-O—,
(c) —C3-6cycloalkyl-, and
(d) —C3-6cycloalkyl-O—.

51 more elements

A compound selected from:

(1) 1-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione;
(2) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione;
(3) 2-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1H-isoindole-1,3(2H)-dione;
(4) 3,3-dimethyl-1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione;
(5) 3-methyl-3-phenyl-1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)pyrrolidine-2,5-dione;
(6) 3-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)thiazolidine-2,4-dione;
(7) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)thiazolidine-2,4-dione;
(8) 5,5-dimethyl-3-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)thiazolidine-2,4-dione;
(9) [2,4-dioxo-3-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1,3-thiazolidin-5-yl]acetic acid;
(10) 3-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(11) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(12) 1-methyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(13) 5(R)-methyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(14) 5,5-dimethyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(15) 1-(2-pyridyl)-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(16) 5-methyl-5-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(17) 5-methyl-5-phenyl-3-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(18) 5-methyl-5-phenyl-3-(3-{[7-propyl-3-(phenyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(19) 5-methyl-5-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}butyl)imidazolidine-2,4-dione;
(20) 5-methyl-5-(3-carboxyphenyl)-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(21) 5-methyl-5-(4-pyridyl)-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(22) 5-methyl-5-(3-pyridyl)-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(23) 5-methyl-5-(2-pyridyl)-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(24) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1-pyrimidin-2-ylimidazolidine-2,4-dione;
(25) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1-pyrazin-2-ylimidazolidine-2,4-dione;
(26) 3-[2,5-dioxo-4-phenyl-1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-4-yl]propanoic acid;
(27) 4-[5,5-dimethyl-2,4-dioxo-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-1-yl]butanoic acid;
(28) 4-[5,5-dimethyl-2,4-dioxo-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-1-yl]pentanoic acid;
(29) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-2-one;
(30) methyl 2-[2-oxo-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-1-yl]propanoate;
(31) 2-[2-oxo-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidin-1-yl]propanoic acid;
(32) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(33) 5,5-dimethyl-1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)imidazolidine-2,4-dione;
(34) 1-[cis-2-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}cyclohexyl)methyl]dihydropyrimidine-2,4(1H,3H)-dione;
(35) 1-[trans-2-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}cyclopentyl)methyl]dihydropyrimidine-2,4(1H,3H)-dione;
(36) 1-{4-[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl}dihydropyrimidine-2,4(1H,3H)-dione;
(37) 5-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(38) 6-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(39) 5-Methyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(40) 1,5-Dimethyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(41) 1-phenyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(42) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1-pyridin-2-yldihydropyrimidine-2,4(1H,3H)-dione;
(43) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-5,6-dihydro-2H-1,2′-bipyrimidine-2,4(3H)-dione;
(44) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-5,6-dihydro-2H-1,5′-bipyrimidine-2,4(3H)-dione;
(45) 1-(3-{[7-propyl-3-(neopentyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperidin-2-one;
(46) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperidin-2-one;
(47) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperidin-2,6-dione;
(48) 1-(3-{[7-propyl-3-(phenyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperidin-2,5-dione;
(49) 4-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)morpholine-3,5-dione;
(50) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperazine-2,5-dione;
(51) 4-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)piperazine-2-one;
(52) 3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)-1,3,5-triazinane-2,4-dione;
(53) 3-(3-{[7-propyl-3-(phenyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
(54) 6-methyl-3-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)dihydropyrimidine-2,4(1H,3H)-dione;
and
(55) 1-(3-{[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]oxy}propyl)azepan-2-one;
and pharmaceutically acceptable salts, esters and tautomers thereof.

54 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/522,114Filed 21 Jul 2003
Priority: US 6039871625 Jul 2002
Published: 27 Oct 2005
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 413/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 261/20
Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings: condensed with carbocyclic rings or ring systems
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

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US 2005/0239769 A1This patent

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Abstract

A compound of formula I

and the pharmaceutically acceptable salts, esters and tautomers thereof, wherein
R1 is selected from the group consisting of:
(a) —CF3,
(b) —CH2C(CH3)3,
(c) phenyl, unsubstituted, mono- or poly-substituted with halo,
(d) —C1-6 alkyl, and
(e) —C1-2alkyl-phenyl;
R2 is selected from the group consisting of:
(a) —C1-6 alkyl,
(b) —COOR3,
(c) —CR3R4—O—R5,
(d) —CR3R4—S—R5, and
(e) —COR3;
R3, R4 and R5 are independently selected at each occurrence from the group consisting of —H, phenyl, and C1-6 alkyl;
Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I to which Y is respectively attached, to form a heterocyclic ring selected from:
(a) a 5-membered heterocyclic ring selected from the group consisting of:
(b) a 6-membered heterocyclic ring selected from the group consisting of:
(d) a bicyclic heterocyclic ring selected from the group consisting of:
wherein each carbon atom in the heterocyclic ring, formed when Y is joined together with the nitrogen and the carbonyl carbon shown in Formula I, is independently unsubstituted, mono- or di-substituted with a substituent independently selected at each occurrence from R7;
R6 is independently selected at each occurrence from the group consisting of:
(a) —H,
(b) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —NR3R4, —OR3, —COOR3, and —CN,
(c) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(d) —C3-6cycloalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —OR3, —COOR3, and —CN,
(e) —C3-6cycloheteroalkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —(CH2)nOR3, —OR3, —COOR3, and —CN, wherein n is an integer selected from 2, 3, 4, 5 and 6,
(f) —C2-6alkenyl,
(g) —C(O)C1-6alkyl,
(h) —COOR3,
(i) —C(O)(CH2)p—COOR3, wherein p is an integer selected from 2, 3 and 4,
(j) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(l) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(m) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(n) thiazolyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
R7 is independently selected at each occurrence from the group consisting of:
(a) ═O,
(b) —C1-6alkyl-phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —CN, —COOR3, —COR3, and —OH,
(c) —C1-6alkyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —OH, —COOR3, tetrazole and —CN,
(d) —C3-6 cycloalkyl,
(e) —C3-6 spiroalkyl,
(f) —COOR3,
(g) halo,
(h) —NR3R4,
(i) phenyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —COOR3 and —C1-4alkyl,
(j) pyridyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3,
(k) pyrimidinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3, and
(l) pyrazinyl, unsubstituted, mono- or poly-substituted with a substituent selected from the group consisting of halo, —C1-3alkyl, and —COOR3;
and
Z is selected from the group consisting of:
(a) —C1-6alkyl-,
(b) —C1-6alkyl-O—,
(c) —C3-6cycloalkyl-, and
(d) —C3-6cycloalkyl-O—.

50 more elements

Facts

Application

10/522,114Filed 21 Jul 2003

Priority

US 6039871625 Jul 2002

Published

27 Oct 2005

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 413/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 261/20
Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings: condensed with carbocyclic rings or ring systems
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links