IP Library Granted Patent US 9,670,186
Granted Patent B2
US 9,670,186 · App. 14/812,095 · Granted Jun 6, 2017

Neprilysin inhibitors

Inventors: Melissa Fleury (Brisbane, CA); Adam D. Hughes (Half Moon Bay, CA)
Assignee: Theravance Biopharma R&D IP, LLC
C07D405/12A61K31/415A61K31/4192A61K31/42A61K31/421A61K45/06C07D231/14C07D231/20C07D249/04C07D261/18C07D263/38
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Quick Facts
Patent No.
US 9,670,186
App. No.
14/812,095
Granted
Jun 6, 2017
Kind
B2
Abstract

In one aspect, the invention relates to compounds having the formula: where X, R a , R b , R 2 , and R 7 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds are prodrugs of compounds having neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising these compounds; methods of using these compounds; and processes and intermediates for preparing these compounds.

Claims (24)

1. A compound selected from:

(a) (2S,4R)-5-(3′-chlorobiphenyl-4-yl)-2-hydroxymethyl-4-[(3-methoxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(b) (2S,4R)-5-(3′-chlorobiphenyl-4-yl)-4-[(3-methoxyisoxazole-5-carbonyl)amino]-2-methoxymethyl-2-methylpentanoic acid;

(c) (2S,4R)-5-(3′-chlorobiphenyl-4-yl)-2-ethoxymethyl-4-[(3-methoxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(d) (2S,4R)-5-biphenyl-4-yl-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-hydroxymethyl-2-methylpentanoic acid;

(e) (2S,4R)-5-biphenyl-4-yl-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-methoxymethyl-2-methylpentanoic acid;

(f) (2S,4R)-5-biphenyl-4-yl-4-[(3-methoxyisoxazole-5-carbonyl)amino]-2-methoxymethyl-2-methylpentanoic acid;

(g) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxymethyl-4-[(3-methoxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(h) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-4-[(3-ethylisoxazole-5-carbonyl)amino]-2-hydroxymethyl-2-methylpentanoic acid;

(i) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxymethyl-4-[(3-isobutylisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(j) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methyl-4-[(3-propylisoxazole-5-carbonyl)amino]pentanoic acid;

(k) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-methoxymethyl-2-methylpentanoic acid;

(l) (2S,4R)-5-(3′-chlorobiphenyl-4-yl)-2-(2-hydroxyethoxymethyl)-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(m) (2S,4R)-5-(3′-chlorobiphenyl-4-yl)-2-ethoxymethyl-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(n) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-ethoxymethyl-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(o) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-ethoxymethyl-4-[(3-ethylisoxazole-5-carbonyl)amino]-2-methylpentanoic acid;

(p) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-4-[(3-hydroxyisoxazole-5-carbonyl)amino]-2-hydroxymethyl-2-methylpentanoic acid; and

(q) (2S,4R)-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-4-[(3-ethylisoxazole-5-carbonyl)amino]-2-methoxymethyl-2-methylpentanoic acid.

2. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound of claim 1 .

3. A pharmaceutical composition comprising a pharmaceutically acceptable carrier, a compound of claim 1 , and an AT 1 receptor antagonist.

4. The pharmaceutical composition comprising a pharmaceutically acceptable carrier, a compound of claim 1 , and a phosphodiesterase (PDE) inhibitor.

5. The pharmaceutical composition comprising a pharmaceutically acceptable carrier, a compound of claim 1 , and a renin inhibitor.

6. The pharmaceutical composition comprising a pharmaceutically acceptable carrier, a compound of claim 1 , and a diuretic.

7. A method for treating hypertension, heart failure, or renal disease, comprising administering to a patient a therapeutically effective amount of the compound of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2026
From: THERAVANCE BIOPHARMA R&D IP, LLC
To: EONHF, INC.
Reel/Frame 075494/0756 →
Continuity (4)
Continuation 13961269 · Aug 7, 2013
Provisional Application 61774163 · Mar 7, 2013
Provisional Application 61680804 · Aug 8, 2012
Related Publication 20160083372A1 · Mar 24, 2016