IP Library Granted Patent US 8,063,105
Granted Patent B2
US 8,063,105 · App. 11/988,437 · Granted Nov 22, 2011

Renin inhibitors

Assignee: Merck Canada Inc.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,063,105
App. No.
11/988,437
Granted
Nov 22, 2011
Kind
B2
Abstract

The present invention relates to novel renin inhibitors of the general Formula (I), and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds. These novel renin inhibitors are used in treating cardiovascular events and renal insufficiency.

Claims (187)

1. A compound of formula I, or a pharmaceutically acceptable salt thereof, or an optical isomer thereof, having the formula I

wherein,

m is 1 or 2;

n, in each instance in which it occurs, is independently 0, 1 or 2;

p, in each instance in which it occurs, is independently 0, 1 or 2;

X and X 1 are each independently selected from the group consisting of CH 2 , O, and S(O) p , provided that when both X and X 1 are each independently O or S(O) p , m is 2;

Y is selected from the group consisting of N(R a ), CH(R a ), O, and S(O) p ;

R 1 , R 3 , and R a are each independently selected from the group consisting of H, C 1 -C 6 alkyl and C 2 -C 6 alkenyl, wherein the alkyl and alkenyl group is unsubstituted or substituted with one, two, three or four substituents independently selected from:

1) OH,

2) CN,

3) CF 3 ,

4) COOH,

5) C 1 -C 6 alkoxy,

6) C(O)R b ,

7) C(O)N(R c ) 2 ,

8) S(O) p C 1 -C 6 alkyl,

9) SO 2 N(R c ) 2 ,

10) N(R c ) 2 ,

11) NHC(O)R b ,

12) NHC(O)NHR d ,

13) NHC(S)NHR d , and

14) NH(NR c )NHR c ;

R 4 is selected from the group consisting of H, C 1 -C 6 alkyl and C 2 -C 6 alkenyl, wherein the alkyl and alkenyl group is unsubstituted or substituted with one, two, three or four substituents independently selected from:

1) OH,

2) CN,

3) CF 3 ,

4) COOH,

5) C 1 -C 6 alkoxy,

6) C(O)R b ,

7) C(O)N(R c ) 2 ,

8) S(O) p C 1 -C 6 alkyl,

9) SO 2 N(R c ) 2 ,

10) N(R c ) 2 ,

11) NHC(O)R b ,

12) NHC(O)NHR d ,

13) NHC(S)NHR d , and

14) NH(NR c )NHR c ;

R 5 is selected from the group consisting of hydrogen and —C(NH(NH 2 ));

R 2 and R b are independently selected from the group consisting of H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, CF 3 and CH 2 CF 3 ;

R c is selected from the group consisting of H, C 1 -C 6 alkyl and CH 2 CF 3 ;

R d is selected from the group consisting of H and C 1 -C 6 alkyl, wherein the alkyl group is unsubstituted or substituted with one, two, three or four substituents selected from the group consisting of:

1) OH,

2) CN,

3) CF 3 ,

4) COOH, and

5) C(O)NHR c ;

Ar 1 is an unsubstituted or substituted aryl ring wherein the substituted aryl ring is substituted with one, two three or four substituents independently selected from the group consisting of:

1) OH,

2) CN,

3) halogen,

4) N 3 ,

5) NO 2 ,

6) COOH,

7) OCF 2 H,

8) CF 3 ,

9) C 1 -C 6 alkyl,

10) C 2 -C 6 alkenyl,

11) C 1 -C 6 alkoxy,

12) C(O)C 1 -C 6 alkyl, and

13) S(O) p C 1 -C 6 alkyl,

wherein substituents (9)-(13) are unsubstituted or substituted with one, two three or four substituents independently selected from the group consisting of:

a) OH,

b) COOH,

c) CN,

d) CF 3 ,

e) C 1 -C 6 alkoxy,

f) S(O) p C 1 -C 6 alkyl; and

Ar 2 is independently selected from the group consisting of Ar 1 and a 9- or 10-membered fused bicyclic aryl, wherein the fused bicyclic aryl is unsubstituted or substituted with one, two, three or four substituents independently selected from the group consisting of:

1) OH,

2) CN,

3) halogen,

4) N 3 ,

5) NO 2 ,

6) COOH,

7) OCF 2 H,

8) CF 3 ,

9) C 1 -C 6 alkyl,

10) C 1 -C 6 alkyl,

11) C 2 -C 6 alkenyl,

12) C 1 -C 6 alkoxy,

13) C(O)C 1 -C 6 alkyl,

14) S(O) p C 1 -C 6 alkyl,

15) —OC(O)NH(C 1 -C 6 alkylene)C(O)NH 2 , and

16) —OC(O)NH(C 1 -C 6 alkylene)(OH)R d ;

wherein substituents (10)-(14) are unsubstituted or substituted with one, two three or four substituents independently selected from the group consisting of:

a) OH,

b) COOR d ,

c) CN,

d) CF 3 ,

e) C 1 -C 6 alkoxy,

f) S(O) p C 1 -C 6 alkyl,

g) —C(O)NH 2 ,

h) —COONa,

i) —NR d R d , and

j) —NR d C(O)R d .

2. A compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Y is CH(R a ) and R 1 is H.

3. A compound of claim 2 , or a pharmaceutically acceptable salt thereof, wherein Y is CH(R a ), R 1 is H, and n is 1.

4. A compound of claim 3 , or a pharmaceutically acceptable salt thereof, wherein Y is CH 2 and R 2 is C 1 -C 6 alkyl or C 2 -C 6 alkenyl.

5. A compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is C 1 -C 6 alkyl or C 2 -C 6 alkenyl.

6. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R 2 is C 3 -C 6 cycloalkyl.

7. A compound or a pharmaceutically acceptable salt thereof, selected from the group consisting of:

N-{3-[(Acetyl-methyl-amino)-methyl]-benzyl}-2-aminomethyl-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propionamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-benzyl}-N-(2,3-dimethyl-benzyl)-propionamide,

2-Aminomethyl-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-N-[3-(2-methanesulfonyl-ethyl)-benzyl]-propionamide,

5-(2-[Cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamino)-pentanoic acid methyl ester,

6-(2-[Cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamino)-hexanoic acid,

6-(2-[Cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamino)-hexanoic acid methyl ester,

N-Cyclopropyl-N-(2,3-dichloro-benzyl)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-2-[(2,2,2-trifluoro-ethylamino)-methyl]-propionamide,

2-Aminomethyl-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-N-[3-(3-methoxy-propyl)-benzyl]-propionamide,

2-Aminomethyl-N-[2-chloro-5-(3-methoxy-propyl)-benzyl]-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propionamide,

2-[(2-[Cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamino)-methyl]-cyclopropanecarboxylic acid,

2-[(2-[Cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester,

2-Aminomethyl-3-{4-[3-(2-chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-cyclopropyl-N-[3-(3-methoxy-propyl)-benzyl]-propionamide,

2-Aminomethyl-3-{4-[3-(2-chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-[2-chloro-5-(3-methoxy-propyl)-benzyl]-N-cyclopropyl-propionamide,

3-Amino-N-cyclopropyl-N-(2,3-dichloro-benzyl)-2-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethyl]-benzyl}-propionamide,

2-Aminomethyl-3-{4-[3-(2-chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-cyclopropyl-N-(2,3-dichloro-benzyl)-2-methyl-propionamide,

3-Amino-N-cyclopropyl-N-(2,3-dichloro-benzyl)-2-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-benzyl}-propionamide,

2-Aminomethyl-N-cyclopropyl-N-(2,3-dichloro-benzyl)-3-{4-[3-(2,6-dichloro-4-methyl-phenoxy)-propyl]-phenyl}-propionamide,

3-{4-[3-(2-Chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-cyclopropyl-N-(2,3-dichloro-benzyl)-2-methylaminomethyl-propionamide,

2-(Benzylamino-methyl)-3-{4-[3-(2-chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-cyclopropyl-N-(2,3-dichloro-benzyl)-propionamide,

2-Aminomethyl-3-{4-[3-(2-chloro-3,6-difluoro-phenoxy)-propyl]-phenyl}-N-cyclopropyl-N-(2,3-dichloro-benzyl)-propionamide,

2-Aminomethyl-N-[2-chloro-5-(2-methoxy-ethyl)-benzyl]-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propionamide,

Methyl (2R)-2-{2-[(3-[cyclopropyl(2,3-dichlorobenzyl)amino]-2-{4-[2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)amino]ethyl}-3-methylbutanoate,

Methyl (2S)-2-{2-[(3-[cyclopropyl(2,3-dichlorobenzyl)amino]-2-{4-[2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)amino]ethyl}-3-methylbutanoate,

N-Cyclopropyl-N-(2,3-dichlorobenzyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-{[2-(2-napthyl)ethyl]amino}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}butanamide,

3-Amino-N-[2-chloro-5-(3-hydroxypropyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethoxy)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethyl]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethyl]benzyl}propanamide,

3-Amino-N-{2-chloro-5-[3-(dimethylamino)propyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-N-[2,3-dichloro-5-[3-methoxypropyl)benzyl}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-N-[2,3-dichloro-5-[3-methoxypropyl)benzyl}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethyl]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-cyanoethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[5-(3-methoxypropyl)-2-methylbenzyl]propanamide,

3-Amino-N-[2-chloro-5-(2-cyanomethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[5-(3-methoxyethyl)-2-methylbenzyl]propanamide,

3-Amino-N-[2,5-bis(trifluoromethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-(1-phenylethyl)propanamide,

3-Amino-N-benzyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-methylpropanamide,

3-Amino-N-benzyl-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-benzyl-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-(2-phenylethyl)propanamide,

3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-methyl-N-(2-phenylethyl)propanamide,

3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-methyl-N-(1-phenylethyl)propanamide,

3-Amino-N-(2,3-dichlorobenzyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-(2,2,2-trifluoroethyl)propanamide,

3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-methyl-N-(1-methyl-1-phenylethyl)propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-N-(cyclopropyl)methyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-methylpropanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-N-(cyclobutylmethyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-isopropylpropanamide,

N-Allyl-3-amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-N-cyclobutyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[2-chloro-5-(2-methoxyethyl)benzyl]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-ethylpropanamide,

3-{[Amino(imino)methyl]amino}-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

2-{[Amino(imino)methyl]amino}-N-cyclopropyl-N-(2,3-dichlorobenzyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

2-Amino-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

2-{[Amino(imino)methyl]amino}-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[3-hydroxy-5-(3-methoxypropyl)benzyl]propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[3-(2-methoxyethoxy)-5-(3-methoxypropyl)benzyl]propanamide,

3-Amino-N-[3-(3-cyanopropoxy)-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-{3-(3-methoxypropyl)-5-[(3-methylthio)propoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-{3-(3-methoxypropyl)-5-[(3-methylsulfonyl)propoxy]benzyl}propanamide,

3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[3-(3-methoxypropyl)-5-{[4-(methylsulfonyl)benzyl]oxy}benzyl)propanamide,

Ethyl 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate,

Sodium 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate,

Ethyl 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-chloro-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate,

Sodium 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-chloro-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate,

Ethyl 2-[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]-2-methylpropanoate,

Sodium 2-[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]-2-methylpropanoate,

3-Amino-N-[3,5-bis(2-methoxyethoxy)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[3,5-bis(4,4,4-trifluorobutoxy)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-Amino-N-[3-(2-amino-2-oxoethoxy)-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

3-{[(3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl ethylcarbamate,

3-{[(3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl(3-amino-2,2-dimethyl-3-oxopropyl)carbamate,

3-{[(3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl (2-hydroxypropyl)carbamate,

Ethyl 3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-bromophenoxy)acetate,

Ethyl 3-(3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-bromophenoxy)propanoate,

Ethyl 5-(3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-bromophenoxy)pentanoate,

Sodium 3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-bromophenoxy)acetate,

Sodium 5-(3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-2-bromophenoxy)pentanoate,

2-{4-[2-(4-Allyl-2,6-dichlorophenoxy)ethoxy]benzyl}-3-amino-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropanamide,

3-Amino-N-[2-chloro-5-(3-methoxypropyl)benzyl]-N-cyclopropyl-2-(4-{2-[2,6-dichloro-4-(3-hydroxypropyl)phenoxy]ethoxy}benzyl}propanamide,

N-(5-{[Acetyl(methyl)amino]methyl}-2-chlorobenzyl)-3-amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide,

4-Amino-N-cyclopropyl-N-(2,3-dichlorobenzyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}butanamide,

4-Amino-N-cyclopropyl-N-(2,3-dichlorobenzyl)-2-{4-[3-(2,6-dichloro-4-methylphenoxy)propyl]benzyl}butanamide, and

N-Cyclopropyl-N-(2,3-dichlorobenzyl)-O-[2-(2,6-dichloro-4-methylphenoxy)ethyl]tyrosinamide.

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

Assignments (2)
CHANGE OF NAME Recorded Jul 26, 2011
From: MERCK FROSST CANADA LTD.
To: MERCK CANADA INC.
Reel/Frame 026653/0495 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2008
From: BAYLY, CHRISTOPHER I.; DUBE, DANIEL; GALLANT, MICHEL; CHEN, AUSTIN C.; LACOMBE, PATRICK; MCKAY, DANIEL; GRIMM, ERICH L.; MACDONALD, DWIGHT; POWELL, DAVID A.; DUBE, LAURENCE
To: MERCK FROSST CANADA LTD.
Reel/Frame 021221/0377 →
Continuity (2)
Provisional Application 60702026 · Jul 22, 2005
Related Publication 20090281103A1 · Nov 12, 2009