IP Library › Granted Patent US 7,491,826
Granted Patent B2
US 7,491,826 · App. 10/890,829 · Granted Feb 17, 2009

Compounds, compositions and methods

Assignee: Cytokinetics, Inc.
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Quick Facts
Patent No.
US 7,491,826
App. No.
10/890,829
Granted
Feb 17, 2009
Kind
B2
Abstract

Certain substituted urea derivatives selectively modulate the cardiac sarcomere, for example by potentiating cardiac myosin, and are useful in the treatment of systolic heart failure including congestive heart failure.

Claims (129)

1. A compound represented by Formula I:

wherein:

R 1 is represented by Formula II:

wherein:

R 1.1 is 1-acyl-pyrrolidin-3-yl, 1-alkoxycarbonyl-pyrrolidin-3-yl, 1-amidino-pyrrolidin-3-yl, 1-sulfonyl-pyrrolidin-3-yl, 3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-6-yl, 1-acyl-piperidin-3-yl, 1-alkoxycarbonyl-piperidin-3-yl, 1-amidino-piperidin-3-yl or 1-sulfonyl-piperidin-3-yl, each of which is optionally substituted with an additional lower alkoxy or lower alkoxyalkyl ring substituent;

R 2 is pyridin-3-yl or pyridin-3-yl substituted with one or two substituents chosen from lower alkoxy and lower alkyl;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 where R 1.1 is 1-acetyl-piperidin -3-yl, 1-methoxyacetyl-piperidin-3-yl, 1-(azetidine-1-carbonyl)-piperidin-3-yl, 1-methoxycarbonyl-piperidin-3-yl, 1-ethoxycarbonyl-piperidin-3-yl, 1-dimethylaminocarbonyl-piperidin-3-yl, 1-methanesulfonyl-piperidin-3-yl, 1-(ethane-2-sulfonyl)-piperidin-3-yl 1-(propane-2-sulfonyl)-piperidin-3-yl, 1-(azetidin-1-yl-sulfonyl) -piperidin-3-yl, 1-dimethylaminosulfonyl-piperidin-3-yl, 1-(N 1 -azetidin-1-yl-N 2 -cyano -amidino)-piperidin-3-yl, 1-(N 2 -cyano-N 1 ,N 1 -dimethyamidino)-piperidine-3-yl, 1-acetyl -pyrrolidin-3-yl, 1-acetyl-5-methoxymethyl-pyrrolidin-3-yl, 1-methoxyacetyl-pyrrolidin-3-yl, 1-(azetidine-1-carbonyl)-pyrrolidin-3-yl, 1-methoxycarbonyl-pyrrolidin-3-yl, 1-methoxycarbonyl-2-methoxymethyl-pyrrolidin-4-yl, 1-methanesulfonyl-pyrrolidin-3-yl, 1-(ethane-2-sulfonyl)-pyrrolidin-3-yl, 1-(ethane-2-sulfonyl)-4-methoxy-pyrrolidin-3-yl, 1-(ethane-2-sulfonyl)-5-methoxymethyl-pyrrolidin-3-yl, 1-(propane-2-sulfonyl)-pyrrolidin-3-yl, 1-(azetidin-1-yl-sulfonyl)-pyrrolidin-3-yl, 1-dimethylaminosulfonyl-pyrrolidin-3-yl, 1-dimethylaminosulfonyl-2-methoxymethyl-pyrrolidin-4-yl, 1-(N 1 -azetidin-1-yl-N 2 -cyano -amidino)-pyrrolidin-3-yl, 1-(N 2 -cyano-N 1 ,N 1 -dimethyamidino)-pyrrolidin-3-yl, or 3-oxo -tetrahydro-pyrrolo[1,2-c]oxazol-6-yl.

3. The compound of claim 1 where R 1.1 is 1-acyl -pyrrolidin-3-yl, 1-acetyl-5-methoxymethyl-pyrrolidin-3-yl, 1-sulfonyl-pyrrolidin-3-yl, 3-oxo -tetrahydro-pyrrolo[1,2-c]oxazol-6-yl, 1-alkoxycarbonyl-piperidin-3-yl or 1-sulfonyl -piperidin-3-yl.

4. The compound of claim 3 where R 1.1 is 1-methoxycarbonyl-2-methoxymethyl-pyrrolidin-4-yl, 1-(ethane-2-sulfonyl)-pyrrolidin-3-yl, 1-(ethane-2-sulfonyl)-5-methoxymethyl-pyrrolidin-3-yl, 1-dimethylaminosulfonyl-pyrrolidin-3-yl, 1-dimethylaminosulfonyl-2-methoxymethyl-pyrrolidin-4-yl, 3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-6-yl, 1-methoxycarbonyl-piperidin-3-yl, 1-methanesulfonyl-piperidin-3-yl, or 1-(ethane-2-sulfonyl)-piperidin-3-yl.

5. The compound of claim 1 where R 2 is pyridin-3-yl or 6-methyl-pyridin-3-yl.

6. A compound of claim 1 wherein the compound represented by Formula I is selected from:

1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methoxy-pyridin-3-yl)-urea;

1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-pyridin-3-yl-urea;

(R)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methoxy-pyridin-3-yl) -urea;

(S)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methoxy-pyridin-3-yl) -urea;

(R)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

(S)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(R)-1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-pyridin-3-yl -urea;

(S)-1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-pyridin-3-yl -urea;

(R)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl) -urea;

(S)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl) -urea;

(R)-1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-(6-methyl -pyridin-3-yl)-urea;

(S)-1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-(6-methyl -pyridin-3-yl)-urea;

(R)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(S)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(R)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(S)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(R)-1-[3-(1-ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

(S)-1-[3-(1-ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

(R)-1-[3-(1-Ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin -3-yl)-urea;

(S)-1-[3-(1-Ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin -3-yl)-urea;

(R)-3-[3-Fluoro-5-(pyridin-3-yl-ureido)-phenoxy]-piperidine-1-N,N-dimethyl-N -cyano-carboxamidine;

(S)-3-[3-Fluoro-5-(pyridin-3-yl-ureido)-phenoxy]-piperidine-1-N,N-dimethyl-N -cyano-carboxamidine;

(R)-3-[3-Fluoro-5-(2-methyl-pyridin-5-yl-ureido)-phenoxy]-piperidine-1-N,N -dimethyl-N-cyano-carboxamidine;

(S)-3-[3-Fluoro-5-(2-methyl-pyridin-5-yl-ureido)-phenoxy]-piperidine-1-N,N -dimethyl-N-cyano-carboxamidine;

(R)-1-[3-(1-Ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl -pydridin-3-yl)-urea;

(S)-1-[3-(1-Ethanesulfonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl -pydridin-3-yl)-urea;

(R)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-sulfonic acid dimethylamide;

1-[(R)-3-(1-Acetyl-(R)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

1-[(S)-3-(1-Acetyl-(S)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

1-[(R)-3-(1-Acetyl-(S)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

1-[(S)-3-(1-Acetyl-(R)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

4-{3-fluoro-5-[(R)-3-(6-methyl-pyridin-3-yl)-ureido]phenoxy}-(R)-2-methoxymethyl -pyrrolidine-1-carboxylic acid methyl ester;

4-{3-fluoro-5-[(S)-3-(6-methyl-pyridin-3-yl)-ureido]phenoxy}-(S)-2-methoxymethyl -pyrrolidine-1-carboxylic acid methyl ester;

4-{3-fluoro-5-[(R)-3-(6-methyl-pyridin-3-yl)-ureido]phenoxy}-(S)-2-methoxymethyl -pyrrolidine-1-carboxylic acid methyl ester;

4-{3-fluoro-5-[(S)-3-(6-methyl-pyridin-3-yl)-ureido]phenoxy}-(R)-2-methoxymethyl -pyrrolidine-1-carboxylic acid methyl ester;

1-[(R)-3-(1-Acetyl-(R)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl)-urea;

1-[(S)-3-(1-Acetyl-(S)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl)-urea;

1-[(R)-3-(1-Acetyl-(S)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl)-urea; and

1-[(S)-3-(1-Acetyl-(R)-5-methoxymethyl-pyrrolidin-3-yloxy)-5-fluoro-phenyl]-3-(6-methyl-pyridin-3-yl)-urea

3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-piperidine-1-carboxylic acid methyl ester.

7. A compound of claim 1 wherein the compound represented by Formula I is selected from:

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-3-[3-Fluoro-5-(2-methyl-pyridin-5-yl-ureido)-phenoxy]-pyrrolidine-1-N,N -dimethyl-N-cyano-carboxam idine;

(R)-3-[3-Fluoro-5-(2-methyl-pyridin-5-yl-ureido)-phenoxy]-pyrrolidine-1-N,N -dimethyl-N-cyano-carboxamidine;

(S)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-3-[3-Fluoro-5-(pyridin-2-yl-ureido)-phenoxy]-pyrrolidine-1-N,N-dimethyl-N -cyano-carboxamidine;

(R)-3-[3-Fluoro-5-(pyridin-2-yl-ureido)-phenoxy]-pyrrolidine-1-N,N-dimethyl-N -cyano-carboxamidine;

(S)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-carboxylic acid methyl ester;

(R)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-carboxylic acid methyl ester;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-carboxylic acid methyl ester;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-carboxylic acid methyl ester;

(S)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(R)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(S)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(R)-1-{3-Fluoro-5-[1-(propane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(S)-1-{3-Fluoro-5-[1-(ethane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(R)-1-{3-Fluoro-5-[1-(ethane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-pyridin-3-yl-urea;

(S)-1-{3-Fluoro-5-[1-(ethane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(R)-1-{3-Fluoro-5-[1-(ethane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(S)-1-{3-Fluoro-5-[1-(methane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(R)-1-{3-Fluoro-5-[1-(methane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(R)-2-methoxymethyl]-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(R)-2-methoxymethyl]-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-carboxylic acid methyl ester;

(R)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(R)-2-methoxymethyl]-pyrrolidine-1-carboxylic acid methyl ester;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(R)-2-methoxymethyl]-pyrrolidine-1-carboxylic acid methyl ester;

(R)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-carboxylic acid methyl ester;

(S)-1-{3-(1-Ethanesulfonyl-[(S)-4-methoxy]-pyrrolidin-3-yloxy)-5-fluoro-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(R)-4-methoxy]-pyrrolidin-3-yloxy)-5-fluoro-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(S)-1-{3-(1-Ethanesulfonyl-[(R)-4-methoxy]-pyrrolidin-3-yloxy)-5-fluoro-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(S)-4-methoxy]-pyrrolidin-3-yloxy)-5-fluoro-phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(S)-1-{3-(1-Ethanesulfonyl-[(S)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-pyridin-3-yl-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(R)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-pyridin-3-yl-urea;

(S)-1-{3-(1-Ethanesulfonyl-[(R)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-pyridin-3-yl-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(S)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-pyridin-3-yl-urea;

(S)-1-{3-(1-Ethanesulfonyl-[(S)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(R)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(S)-1-{3-(1-Ethanesulfonyl-[(R)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

(R)-1-{3-(1-Ethanesulfonyl-[(S)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-(6-methyl-pyridin-3-yl)-urea;

1-[3-Fluoro-5-(S)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(R)-(3-oxo-(R)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(S)-(3-oxo-(R)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(R)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(S)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea;

1-[3-Fluoro-5-(R)-(3-oxo-(R)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea;

1-[3-Fluoro-5-(S)-(3-oxo-(R)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea; and

1-[3-Fluoro-5-(R)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea.

8. A compound of claim 1 wherein the compound represented by Formula I is selected from:

(R)-1-[3-(1-Acetyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(S)-3-[3-Fluoro-5-(3-pyrldin-3-yl-ureido)-phenoxy]-pyrrolidlne-1-sulfonic acid dimethylamide;

1-[(R)-3-(1-Acetyl-(R)-5-methoxymethyl-pyrrodin-3-yloxy)-5-fluoro-phenyl]-3-pyridin-3-yl-urea;

4-{3-fluoro-5-[(R)3-(6-methyl-pyridin-3-yl)-ureido]phenoxy}-(R)-2-methoxymethyl -pyrrolidine-1-carboxylic acid methyl ester;

(S)-1-[3-(1-Ethanesulonyl-piperidin-3-yloxy)-5-fluoro-phenyl]-3-(6methyl -pydridin-3-yl)-urea;

(R)-1-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-piperidine-1-carboxylic acid methyl ester;

(S)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-carboxylic acid methyl ester;

(R)-3-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-pyrrolidine-1-carboxylic acid methyl ester;

(S)-1-[3-Fluoro-5-(1-methanesulfonyl-piperidin-3-yloxy)-phenyl]-3-pyridin-3-yl -urea;

(R)-3-[3-Fluoro-5-(3-pyridin-3-yl-ureido)-phenoxy]-pyrrolidine-1-sulfonic acid dimethylamide;

(R)-1-{3-Fluoro-5-[1-(ethane-2-sulfonyl)-pyrrolidin-3-yloxy]-phenyl}-3-(6-methyl -pyridin-3-yl)-urea;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-sulfonic acid dimethylamide;

(S)-4-{3-Fluoro-5-[3-(6-methyl-pyridin-3-yl)-ureido]-phenoxy}-[(S)-2-methoxymethyl]-pyrrolidine-1-carboxylic acid methyl ester;

(R)-1-{3-(1-Ethanesulfonyl-[(S)-5-methoxymethyl]-pyrrolidin-3-yloxy)-5-fluoro -phenyl}-3-pyridin-3-yl-urea;

1-[3-Fluoro-5-(R)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-pyridin-3-yl-urea; and

1-[3-Fluoro-5-(R)-(3-oxo-(S)-tetrahydro-pyrrolo[1,2-c]oxazol-6-yloxy)-phenyl]-3-(6-methyl-pyridin-3-yl)-urea.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jan 26, 2017
From: AMGEN INC.
To: CYTOKINETICS, INCORPORATED
Reel/Frame 041094/0653 →
SECURITY AGREEMENT Recorded Jan 3, 2007
From: CYTOKINETICS, INCORPORATED
To: AMGEN, INC.
Reel/Frame 018700/0104 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2005
From: MORGAN, BRADLEY PAUL; ELIAS, KATHLEEN A.; KRAYNACK, ERICA ANNE; LU, PU-PING; MALIK, FADY; MUCI, ALEX; QIAN, XIANGPING; SMITH, WHITNEY WALTER; TOCHIMOTO, TODD; TOMASI, ADAM LEWIS; MORGANS, DAVID J. JR.
To: CYTOKINETICS, INC.
Reel/Frame 015976/0281 →
Continuity (7)
Continuation In Part PCTUS200400106900 · Jan 14, 2004
Provisional Application 6050137600 · Sep 8, 2003
Provisional Application 6047651700 · Jun 5, 2003
Provisional Application 6047608600 · Jun 4, 2003
Provisional Application 6044018300 · Jan 14, 2003
Provisional Application 6044013300 · Jan 14, 2003
Related Publication 20050159416A1 · Jul 21, 2005