IP Library Granted Patent US 7,411,073
Granted Patent B2
US 7,411,073 · App. 10/544,899 · Granted Aug 12, 2008

Selective non-steroidal glucocorticoid receptor modulators

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Quick Facts
Patent No.
US 7,411,073
App. No.
10/544,899
Granted
Aug 12, 2008
Kind
B2
Abstract

The present invention encompasses compounds of Formula (I) or pharmaceutically acceptable salts or hydrates thereof, which are useful as novel non-steroidal selective glucocorticoid receptor modulators for treating a variety of autoimmune and inflammatory diseases or conditions, and possess advantages over steroidal glucocorticoid ligands with respect to undesireable side-effects, efficacy, toxicity and/or metabolism. Pharmaceutical compositions and methods of use are also included.

Claims (617)

1. A compound of Formula II:

or a pharmaceutically acceptable salt or hydrate thereof, wherein:

X is selected from the group consisting of: —OR a , —N(R b )—Y—R c , —S(O) j -R d , wherein:

Y is selected from a bond, —C(O)—, —C(O)—O—, wherein the point of attachment of the “—O—” group is to R c forming an alkoxy moiety, —S(O) 2 — and —C(O)—N(R 12 )—, wherein the point of attachment of the nitrogen group is to R c , and

j is 0, 1 or 2,

n is 1,

R a , R b , R c , R d and R 8 are each independently selected from the group consisting of:

(1) hydrogen, except that R d is not hydrogen and R c is hydrogen only when Y is a bond or —C(O)—N(R 12 )—,

(2) C 1-6 alkyl,

(3) C 2-6 alkenyl,

(4) C 2-6 akynyl,

(5) C 3-6 cycloalkyl,

(6) aryl,

(7) aralkyl,

(8) HET 1 ,

(9) —C 1-6 alkyl-HET 2 ,

(10) aralkenyl,

(11) aralkynyl and

(12) arylsulfonylalkyl,

wherein items (2) to (5) above and the alkyl portions of items (7), (9) and (12) above and the alkenyl portion of item (10) above and the alkynyl portion of item (11) above are optionally substituted with oxo and optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 11 , N(R 12 ) 2 , C 3-6 cycloalkyl and C 1-4 alkyl-S(O) m —, wherein m is 0, 1 or 2, and

wherein items (6) and (8) above and the aryl portion of items (7), (10), (11) and (12) above and the HET 2 portion of item (9) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) OR 11 ,

(c) N(R 12 ) 2 ,

(d) C 1-6 alkyl,

(e) C 2-6 alkenyl,

(f) C 2-6 akynyl,

(g) C 1-6 alkyl-S(O) p —, wherein p is 0, 1 or 2,

(h) aryl,

(i) aryl-S(O) q —, wherein q is 0, 1 or 2,

(j) HET 3 ,

(k) aralkyl,

(l) aroyl,

(m) aryloxy,

(n) aralkoxy and

(o) CN,

wherein items (d) to (g) above and the alkyl portions of item (k) above are optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 11 and N(R 12 ) 2 , and

wherein items (h), (i), (j), (l) and (m) above and the aryl portions of items (k) and (n) above are optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 12 and C 1-4 alkyl,

each R 11 and R 12 is independently selected from the group consisting of hydrogen and C 1-4 alkyl, optionally substituted with 1 to 3 halo groups; and

HET 1 , HET 2 and HET 3 are each independently selected from the group of heterocycles consisting of: benzimidazolyl, benzofuranyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiazolyl, thienyl, triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl.

2. The compound according to claim 1 wherein

X is —OR a ,

and

R a is selected from the group consisting of:

(1) hydrogen,

(2) acetyl,

(3) benzyl,

(4) C 1-6 alkyl,

(5) C 2-6 alkenyl,

(6) C 2-6 alkynyl and

(7) C 3-6 cycloalkyl,

R 8 is selected from the group consisting of:

(1) hydrogen,

(2) C 1-6 alkyl,

(3) C 2-6 alkenyl,

(4) C 2-6 akynyl,

(5) C 3-6 cycloalkyl,

(6) aryl,

(7) aralkyl,

(8) HET 1 ,

(9) —C 1-6 alkyl-HET 2 ,

(10) aralkenyl,

(11) aralkynyl, and

(12) arylsulfonylalkyl

wherein items (2) to (5) above and the alkyl portions of items (7), (9) and (12) above and the alkenyl portion of item (10) above and the alkynyl portion of item (11) above are optionally substituted with oxo and optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 11 and C 3-6 cycloalkyl,

wherein items (6) and (8) above and aryl portion of items (7), (10), (11) and (12) above and the HET 2 portion of item (9) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) C 1-6 alkyl,

(c) C1-4alkoxy and

(d) aryl,

R 11 is selected from the group consisting of hydrogen and C 1-4 alkyl, optionally substituted with 1 to 3 halo groups; and

HET 1 and HET 2 are each independently selected from the group of heterocycles consisting of: benzimidazolyl, benzofuranyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiazolyl, thienyl, triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl.

3. The compound according to claim 2 wherein:

R 8 is selected from the group consisting of:

(1) hydrogen,

(2) C 1-6 alkyl,

(3) C 2-6 alkenyl,

(4) C 2-6 akynyl,

(5) C 3-6 cycloalkyl,

(6) phenyl or naphthyl,

(7) benzyl or phenethyl,

(8) benzothiophene,

(9) phenylethenyl,

(10) phenylethynyl, and

(11) phenylsulfonylmethyl,

wherein items (2) to (5) above are optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 11 and C 3-6 cycloalkyl,

wherein item (6) above and the phenyl portions of items (7), (9), (10) and (11) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) C 1-6 alkyl,

(c) C 1-4 alkoxy and

(d) phenyl.

4. The compound according to claim 1 wherein:

X is —N(R b )—Y—R c , wherein:

Y is selected from —C(O)—, C(O)O—, wherein the point of attachment of the “—O—” group is to R c forming an alkoxy moiety, —S(O) 2 — and —C(O)—N(R 12 )—, wherein the point of attachment of the nitrogen group is to R c , and

R 8 is hydrogen,

R b and R c are each independently selected from the group consisting of:

(1) hydrogen, except that R c is not hydrogen,

(2) C 1-6 alkyl,

(3) C 2-6 alkenyl,

(4) C 2-6 akynyl,

(5) C 3-6 cycloalkyl,

(6) aryl,

(7) aralkyl,

(8) HET 1 ,

(9) —C 1-6 alkyl-HET 2 ,

(10) aralkenyl,

(11) aralkynyl and

(12) arylsulfonylalkyl,

wherein items (2) to (5) above and the alkyl portions of items (7), (9) and (12) above and the alkenyl portion of item (10) above and the alkynyl portion of item (11) above are optionally substituted with oxo and optionally substituted with with one to three substituents independently selected from the group consisting of: halo, OR 11 , N(R 12 ) 2 , C 3-6 cycloalkyl and C 1-4 alkyl-S(O) m —, wherein m is 0, 1 or 2, and

wherein items (6) and (8) above and the aryl portion of items (7), (10), (11) and (12) above and the HET 2 portion of item (9) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) OR 11 ,

(c) N(R 12 ) 2 ,

(d) C 1-6 alkyl,

(e) C 2-6 alkenyl,

(f) C 2-6 akynyl,

(g) C 1-6 alkyl-S(O) p —, wherein p is 0, 1 or 2,

(h) aryl,

(i) aryl-S(O) q —, wherein q is 0, 1 or 2,

(j) HET 3 ,

(k) aralkyl,

(l) aroyl,

(m) aryloxy,

(n) aralkoxy and

(o) CN,

wherein items (d) to (g) above and the alkyl portions of item (k) above are optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 11 and N(R 12 ) 2 , and

wherein items (h), (i), (j), (l) and (m) above and the aryl portions of items (k) and (n) above are optionally substituted with one to three substituents independently selected from the group consisting of: halo, OR 12 and C 1-4 alkyl,

each R 11 and R 12 is independently selected from the group consisting of hydrogen and C 1-4 alkyl, optionally substituted with 1 to 3 halo groups; and

HET 1 , HET 2 and HET 3 are each independently selected from the group of heterocycles consisting of: benzimidazolyl, benzofuranyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiazolyl, thienyl, triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl.

5. The compound according to claim 4 wherein:

R b and R c are each independently selected from the group consisting of:

(1) hydrogen, except that R c is hydrogen only when Y is a bond or —C(O)—N(R 12 )—,

(2) C 1-6 alkyl,

(3) C 2-6 alkenyl,

(4) C 2-6 akynyl,

(5) C 3-6 cycloalkyl,

(6) aryl,

(7) aralkyl,

(8) HET 1 ,

(9) —C 1-6 alkyl-HET 2 ,

(10) aralkenyl, and

(11) aralkynyl,

wherein items (2) to (5) above are optionally substituted with 1-3 halo groups, and

wherein items (6) and (8) and aryl portion of items (7), (10) and (11) above and the HET 2 portion of item (9) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) C 1-4 alkyl, optionally substituted with 1-3 halo groups, and

(c) C 1-4 alkylthio,

HET 1 and HET 2 are each independently selected from the group of heterocycles consisting of: benzimidazolyl, benzofuranyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiazolyl, thienyl, triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl.

6. The compound according to claim 5 wherein:

R b is selected from the group consisting of: hydrogen and C 1-4 alkyl, and

R c is selected from the group consisting of:

(1) C 1-4 alkyl,

(2) phenyl or benzyl, each optionally substituted with 1 to 5 groups independently selected from fluoro, chloro and trifluoromethyl,

(3) naphthyl,

(4) thiopheneyl,

(5) pyridyl,

(6) isoquinolyl,

(7) pyrimidyl and

(8) pyrazyl,

wherein items (4) to (8) above are optionally substitited with 1 to 5 groups independently selected from fluoro, chloro, methyl, methylthio and trifluoromethyl.

7. The compound according to claim 6 , wherein R c is phenyl, optionally substituted with 1 to 5 groups independently selected from fluoro, chloro and trifluoromethyl.

8. The compound according to claim 1 , wherein:

X is —S(O) j -R d , wherein j is 0, 1 or 2,

R 8 is hydrogen, and

R d is selected from the group consisting of:

(1) C 1-6 alkyl,

(2) C 2-6 alkenyl,

(3) C 2-6 akynyl,

(4) C 3-6 cycloalkyl,

(5) aryl,

(6) aralkyl,

(7) HET 1 ,

(8) —C 1-6 alkyl-HET 2 ,

(9) aralkenyl, and

(10) aralkynyl,

wherein items (1) to (4) above are optionally substituted with 1-3 halo groups, and

wherein items (5) and (7) and aryl portion of items (6), (9) and (10) above and the HET 2 portion of item (8) above are optionally substituted with one to five substituents independently selected from the group consisting of:

(a) halo,

(b) C 1-4 alkyl, optionally substituted with 1-3 halo groups, and

(c) C 1-4 alkylthio, and

HET 1 and HET 2 are each independently selected from the group of heterocycles consisting of: benzimidazolyl, benzofuranyl, benzopyrazolyl, benzotriazolyl, benzothiophenyl, benzoxazolyl, carbazolyl, carbolinyl, cinnolinyl, furanyl, imidazolyl, indolinyl, indolyl, indolazinyl, indazolyl, isobenzofuranyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridopyridinyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, thiadiazolyl, thiazolyl, thienyl, triazolyl, azetidinyl, 1,4-dioxanyl, hexahydroazepinyl, piperazinyl, piperidinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dihydrobenzimidazolyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydrobenzoxazolyl, dihydrofuranyl, dihydroimidazolyl, dihydroindolyl, dihydroisooxazolyl, dihydroisothiazolyl, dihydrooxadiazolyl, dihydrooxazolyl, dihydropyrazinyl, dihydropyrazolyl, dihydropyridinyl, dihydropyrimidinyl, dihydropyrrolyl, dihydroquinolinyl, dihydrotetrazolyl, dihydrothiadiazolyl, dihydrothiazolyl, dihydrothienyl, dihydrotriazolyl, dihydroazetidinyl, methylenedioxybenzoyl, tetrahydrofuranyl, and tetrahydrothienyl.

9. The compound according to claim 8 , wherein

R d is phenyl, optionally substituted with 1 to 5 groups independently selected from fluoro, chloro and trifluoromethyl.

10. A compound selected from the following group:

n

R Group

1

Vinyl

1

Allyl

1

3-butenyl

1

n-pentyl

1

3-methylbutyl

1

2-cyclohexylethyl

1

3,3-dimethylbutyl

1

4-methyl-3-pentenyl

1

4,4,4-trifluorobutyl

1

3,4,4-trifluoro-3-butenyl

1

3-methoxypropyl

1

2-(2-chlorophenyl)ethyl

1

2-(4-chlorophenyl)ethyl

1

2-(4-fluorophenyl)ethyl

2

2-(4-fluorophenyl)ethyl

1

2-(2,5-difluorophenyl)ethyl

1

2-(2,3-difluorophenyl)ethyl

1

2-(3,5-difluorophenyl)ethyl

1

2-(4-methoxyphenyl)ethyl

1

2-(2-naphthyl)ethyl

1

2-(3-(trifluoromethyl)phenyl)ethyl

1

2-(2-methoxyphenyl)ethyl

1

2-(4-tert-butylphenyl)ethyl

1

2-(4-methylphenyl)ethyl

1

2-(1-naphthyl)ethyl

1

2-(2-methylphenyl)ethyl

1

2-(3-methylphenyl)ethyl

1

2-(2-fluorophenyl)ethyl

1

2-(3-fluorophenyl)ethyl

1

2-(3,4-dichlorophenyl)ethyl

1

2-(2-chloro-4-fluorophenyl)ethyl

1

2-(3-thiopheneyl)ethyl

1

3-(N-pyrrolyl)propyl

1

E-2-phenylethenyl

1

Z-2-phenylethenyl

1

2-(2,4-difluorophenyl)ethynyl

1

2-(2-thiopheneyl)ethyl

1

2-(3,4-difluorophenyl)ethyl

1

2-(3,4,5-trifluorophenyl)ethyl

1

H

n

R i Group

R ii Group

1

H

n-propyl

1

phenethyl

cyclopropylmethyl

1

phenethyl

E-2-butenyl

1

2-(2,4-dichlorophenyl)ethyl

methyl

1

2-(2-chlorophenyl)ethyl

methyl

1

2-(3-chlorophenyl)ethyl

methyl

1

n-pentyl

methyl

1

2-(4-fluorophenyl)ethyl

methyl

1

2-(2,4-dichlorophenyl)ethyl

benzyl

1

2-(2,4-dichlorophenyl)ethyl

allyl

1

2-(2,4-dichlorophenyl)ethyl

n-propyl

1

2-(2-chlorophenyl)ethyl

n-propyl

1

phenethyl

n-propyl

1

phenethyl

methyl

1

2-(3-chlorophenyl)ethynyl

allyl

1

2-(3-chlorophenyl)ethynyl

n-propyl

1

2-(2,4-difluorophenyl)ethyl

methyl

1

phenethyl

E-2-pentenyl

1

trifluoromethyl

allyl

1

trifluoromethyl

n-propyl

1

2-(3-methylphenyl)ethyl

methyl

1

phenethyl

n-butyl

1

phenethyl

n-pentyl

1

2-(3,4-difluorophenyl)ethyl

n-propyl

1

2-(3-fluorophenyl)ethyl

methyl

n

R iii Group

R iv Group

1

CO(3,3,3-trifluoropropyl)

H

1

CO(2-(trifluoromethyl)phenyl)

H

1

CO(3-chlorophenyl)

H

1

COCH 2 (2-(trifluoromethyl)phenyl)

H

1

CO(2,4,5-trifluorophenyl)

H

1

CO(3-thiopheneyl)

H

1

COCH 2 (2,4-difluorophenyl)

H

1

COCH 2 (3-chlorophenyl)

H

1

CO(3-chloro-4-fluorophenyl)

H

1

COCH 2 (2,5-difluorophenyl)

H

1

COCH 2 (2-thiopheneyl)

H

1

COCH 2 (3-thiopheneyl)

H

1

CO(2-chloro-5-fluorophenyl)

H

1

COCH 2 (3-chloro-4-fluorophenyl)

H

1

CO(2,4,5-trifluorophenyl)

methyl

1

CO(2-(trifluoromethyl)phenyl)

methyl

1

CO(2-thiopheneyl)

methyl

1

CO(3-chlorophenyl)

methyl

1

CO(phenyl)

H

1

CO(2,4-difluorophenyl)

H

1

COCH 2 (3-chloro-4-fluorophenyl)

methyl

1

CO(2,4-difluorophenyl)

methyl

1

COCH 2 (2-(trifluoromethyl)phenyl)

methyl

1

CO(2-fluorophenyl)

H

1

CO(2,6-difluorophenyl)

H

1

CO(2-chlorophenyl)

H

1

CO(1-naphthyl)

H

1

CO(2-(trifluoromethyl)-4-fluorophenyl)

H

1

CO(2,5-difluorophenyl)

H

1

CO(2,3-difluorophenyl)

H

1

CO(2-chloro-4-fluorophenyl)

H

1

CO(2-chloro-3-fluorophenyl)

H

1

CO(tert-butyl)

H

1

CO(isopropyl)

H

1

CO(2-chloro-3-fluorophenyl)

methyl

1

CO(2-(trifluoromethyl)-4-fluorophenyl)

methyl

1

CO(2,6-difluorophenyl)

methyl

1

CO(2-chloro-4-fluorophenyl)

methyl

1

SO 2 (phenyl)

H

1

CO(2,6-dichlorophenyl)

methyl

1

CO(2,6-dichlorophenyl)

H

1

SO 2 (2,4-difluorophenyl)

H

1

CO(2,4-difluorophenyl)

n-propyl

1

SO 2 (3-chlorophenyl)

H

2

CO(3-chlorophenyl)

H

1

SO 2 (2-chloro-4-fluorophenyl)

H

1

CO 2 (phenyl)

methyl

1

CO 2 (phenyl)

H

1

CONH(phenyl)

H

1

SO 2 (2-fluorophenyl)

H

1

SO 2 (2-chlorophenyl)

H

1

CONH(phenyl)

methyl

1

SO 2 (2-(trifluoromethyl)phenyl)

H

1

SO 2 (3-fluorophenyl)

H

1

CO(2-chloro-4-fluorophenyl)

n-propyl

1

CO(2-(trifluoromethyl)-4-fluorophenyl)

n-propyl

1

SO 2 (3-chlorophenyl)

methyl

1

SO 2 (2-chloro-4-fluorophenyl)

methyl

1

SO 2 (3-chlorophenyl)

n-propyl

R v Group

R vi Group

CO(phenyl)

H

SO 2 (2-chloro-4-fluorophenyl)

H

CO(2-chlorophenyl)

H

CO(3-chlorophenyl)

H

CO(2-(trifluoromethyl)phenyl)

H

CO(isopropyl)

H

CO(tert-butyl)

H

CO(3-thiopheneyl)

H

CO(2-thiopheneyl)

H

CO(2,4,5-trifluorophenyl)

H

CO(2,5-difluorophenyl)

H

CO 2 (phenyl)

H

SO 2 (phenyl)

H

CO(2-chlorophenyl)

methyl

CO(2-(trifluoromethyl)phenyl)

methyl

CO(3-chlorophenyl)

methyl

CONH(phenyl)

H

CO(2,6-difluorophenyl)

H

COCH 2 (2,4-difluorophenyl)

H

CO(2,4-difluorophenyl)

H

CO(2-fluorophenyl)

H

CO(2-(trifluoromethyl)-4-fluorophenyl)

n-propyl

n

Het (Heterocycle)

R vii Group

1

2-pyridyl

H

1

4-isoquinolyl

H

1

2-(4-methyl)pyridyl

H

1

5-pyrimidyl

H

1

3-pyridyl

H

1

2-pyrimidyl

H

1

2-pyrimidyl

methyl

1

2-pyrimidyl

n-propyl

1

4-(2-methylthio)pyrimidyl

H

1

2-(4-trifluoromethyl)pyridyl

H

1

2-pyrazinyl

H

1

4-(2,3,5,6-tetrafluoro)pyridyl

H

Ar Group

2-chlorophenyl

3-chlorophenyl

2-(trifluoromethyl)phenyl

2,6-dichlorophenyl

2,4-dichlorophenyl

or a pharmaceutically acceptable salt of any compound selected from any of the tables above.

11. A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.

Assignments (2)
CHANGE OF NAME Recorded Jan 29, 2010
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 023861/0910 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2005
From: ALI, AMJAD; BERESIS, RICHARD; COLLETTI, STEVEN L.; GRAHAM, DONALD W.; TATA, JAMES R.; THOMPSON, CHRISTOPHER F.
To: MERCK & CO., INC.
Reel/Frame 017085/0924 →