IP Library › Granted Patent US 8,894,970
Granted Patent B2
US 8,894,970 · App. 13/191,160 · Granted Nov 25, 2014

Arginase inhibitors and methods of use thereof

Inventors: Bruce Edward Tomczuk (Collegeville, PA); Gary Lee Olson (Mountainside, NJ); Richard Scott Pottorf (Belle Mead, NJ); Lijuan Jane Wang (Wildwood, MO); Bhaskara Rao Nallaganchu (Hillsborough, NJ); Yanqun Zhang (East Brunswick, NJ)
Assignee: Corridor Pharmaceuticals, Inc.
A61K31/69A61K51/044A61K49/0004C07F5/02
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Quick Facts
Patent No.
US 8,894,970
App. No.
13/191,160
Granted
Nov 25, 2014
Kind
B2
Abstract

The present invention includes arginase enzyme inhibitors, compositions comprising these arginase inhibitors, and methods of treating or diagnosing conditions characterized either by abnormally high arginase activity or abnormally low nitric oxide levels in a mammal, comprising administering compositions of the invention to the mammal.

Claims (169)

1. A compound selected from the group consisting of:

2-amino-6-borono-2-(2-(piperazin-1-yl)ethyl)hexanoic acid;

2-amino-2-(3-(4-benzylpiperazin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(4-(2-chlorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(2-cyanobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(2,4-difluorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(2,3-difluorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-dichlorobenzyl)piperazin-1-yl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3-(trifluoromethyl)benzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-fluorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-difluorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,5-difluorobenzyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-phenethylpiperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(2-(4-(3,4-dichlorobenzyl)piperazin-1-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-dichlorophenyl)piperazin-1yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-(4-fluorophenyl)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(2-(piperidin-2-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(2-(1-(3,4-dichlorobenzyl)piperidin-2-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(2-(1-(3,5-difluorobenzyl)piperidin-2-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(2-(1-(3,4-difluorobenzyl)piperidin-2-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(2-(1-(3,4-dichlorobenzyl)piperidin-3-yl)ethyl)hexanoic acid;

2-amino-6-borono-2-(3-(1-(3,4-dichlorobenzyl)piperidin-2-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(1-(3,4-difluorobenzyl)piperidin-2-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(1-(3,5-difluorobenzyl)piperidin-2-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-phenylpiperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-(5-fluoro-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-difluorobenzyl)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(pyrimidin-2-ylmethyl)piperidin-1-yl)propyl)hexanoic acid;

2-(3-(3H-spiro[isobenzofuran-1,4′piperidine]-1′-yl)propyl)-2-amino-6-boronohexanoic acid;

2-amino-6-borono-2(3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-(2-chlorophenyl)-1H-pyrazol-1-yl)piperidin-1-yl) propylhexanoic acid;

2-amino-6-borono-2-(3-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-(trifluoromethyl)phenoxy)piperidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-(2-isopropylphenoxy)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-fluorophenyl)piperidin-1-yl)propylhexanoic acid;

2-amino-6-borono-2-(3-(4-(4-methoxyphenyl)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-chlorophenyl)-5,6-dihydropyridin-1(2H)-yl)propyl) hexanoic acid;

2-amino-2-(3-(4-benzyl-4-hydroxypiperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-hydroxypiperidin-1-yl)propyl)hexanoic acid;

2-amino-2-(3-(4-((S)-2-amino-3-methylbutanoyloxy)piperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-2-(3-(4-benzamidopiperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(3,4-dihydroisoquinolin-2(1H)-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-methyl-2-phenylpiperazin-1-yl)propyl)hexanoic acid;

2-amino-2-(3-(2-benzylpiperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(2-(4-methoxyphenyl)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-(3-methoxylphenyl)pyrrolidin-1l-yl)propyl)hexanoic acid 2-amino-6-borono-2-(3-(2-(2-fluorobenzyl)pyrrolidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-(2-(trifluoromethyl)phenyl)pyrrolidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(2-(4-fluorophenyl)pyrrolidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-(3-chlorophenyl)pyrrolidin-1-yl)propyl)hexanoic acid;

2-amino-2-(3-(2-(biphenyl-4-yl)pyrrolidin-1-yl)propyl)-6-borono-hexanoic acid;

2-amino-6-borono-2-(3-(2-(3,4-dichlorophenyl)pyrrolidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(pyrrolidin-1-yl)propyl)hexanoic acid;

2-amino-2-(3-(azetidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(3-phenylazetidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-p-tolylazetidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-(3-(3,4-dichlorophenyl)ureido)azetidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(3-(3-(4-fluorophenyl)ureido)azetidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(3-(-chloro-2-fluorobenzamido)azetidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-ethylpiperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-morpholinopropyl)hexanoic acid;

2-amino-6-borono-2-(3-thiomorpholinopropyl)hexanoic acid;

2-amino-6-borono-2-(3-(thiazolidin-2-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(phenethylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(methyl(phenethyl)aminopropyl)hexanoic acid;

2-amino-6-borono-2-(3-(ethyl(naphthalen-1-ylmethyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(methyl(naphthalen-1-ylmethyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((cyclohexylmethyl)(ethyl)amino)propyl)hexanoic acid;

2-amino-2-(3-(benzyl(ethyl)amino)propyl)-6-boronohexanoic acid;

2-amino-2-(3-(benzyl(ethyl)amino)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-((4-chlorobenzyl)(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((3,4-dichlorobenzyl)(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((3,4-dichlorobenzyl)(ethyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(cyclohexylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(cyclohexyl(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(methyl(tetrahydro-2H-pyran-4-yl)amino)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(cyclopentyl(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((3-chlorobenzyl)(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((6-fluorochroman-4-yl)(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-methoxyethylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((2-methoxyethyl)(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((S)-1-methoxypropan-2-ylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(dimethylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((2-(dimethylamino)ethyl(methyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(2-(dimethylamino)ethylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(diethylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((1R,4R)-5-(3,4-dichlorophenylcarbamoyl)-2,5-diazabicyclo[2.2.2]heptan-2-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-((S)-3-methyl-2-4((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenathren-17-yl)pentanamido)butanoyloxy)piperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(4-(piperazin-1-yl)butyl)hexanoic acid;

2-amino-6-borono-2-(4-(4-(3,4-dichlorophenyl)piperazin-1-yl)butyl)hexanoic acid;

2-amino-6-borono-2-(4-(4-(3,4-difluorobenzyl)piperidin-1-yl)butyl)hexanoic acid;

2-amino-6-borono-2-(4-(3,4-dihydroisoquinolin-2(1H)-yl)butyl)hexanoic acid;

2-amino-6-borono-2-(4-(2-(4-fluorophenyl)piperidin-1-yl)butyl)hexanoic acid;

2-amino-6-borono-2-(3-(carboxymethylamino)propyl)hexanoic acid;

2-amino-2-(3-(4-(biphenyl-4-ylmethyl)piperazin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-2-(3-(4-benzhydrylpiperazin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(4-(4-fluorobenzoyl)piperidin-1-yl)propyl)hexanoic acid;

2-(3-(3-(1H-benzo[d]imidazol-1-yl)-8-azabicyclo[3.2.1]octan-8-yl)propyl)-2-amino-6-boronohexanoic acid;

2-amino-6-borono-2(3-(4-(phenylamino)piperdin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-dichlorobenzylamino)piperidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-((3,4-dichlorobenzyl)(ethyl)amino)piperidin-1-yl) propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-methylpiperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-fluoro-4-phenylpiperidin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(N-(3,4-dichlorobenzyl)octanamido)piperidin-1-yl)propyl)hexanoic acid;

2-amino-3-(3-(4-benzyl-4-(decanoyloxy)piperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-2-(3-(3-(benzo[d]oxazol-2-yl)piperidin-1-yl)propyl)-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(2-phenylpyrrolin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(3-(3-(3,4-dichlorophenyl)ureido)pyrrolidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(3-(3-(4-fluorophenyl)ureido)pyrrolidin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(3-(3,4-dichlorophenylsulfonamido)pyrrolidin-1-yl) propyl)hexanoic acid;

2-(3-(1H-imidazol-1-yl)propyl)-2-amino-6-boronohexanoic acid;

2-(3-(1H-benzo[d]imidazol-1-yl)propyl)-2-amino-6-boronohexanoic acid;

2-amino-6-borono-2-(3-(cyclopentylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(tetrahydro-2H-pyran-4-ylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((3R)-3-methoxytetrahydro-2H-pyran-4-ylamino)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(methyl(naphthalen-2-ylmethyl)amino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(methyl((4-methylnaphthalen-1-yl)methyl)amino)propyl) hexanoic acid;

2-amino-6-borono-2-(3-((4-(3,4-dichlorophenoxy)benzyl)(methyl)amino)propyl) hexanoic acid;

2-amino-6-borono-2-(3-((3′,4′-dichlorobiphenyl-4-yl)methyl)(methyl)amino) propyl)hexanoic acid;

2-amino-6-borono-2-(3-((3′,4′-dichlorobiphenyl)-4-yl)methylamino)propyl) hexanoic acid;

(S)-2-amino-6-borono-2-(3-(1-carboxylethylamino)propyl)hexanoic acid;

(S)-2-amino-6-borono-2-(3-(1-carboxy-3-methylbutylamino)propyl)hexanoic acid;

2-amino-6-borono-2-(3-((S)-1-methoxy-1-oxopropan-2-ylamino)propyl)hexanoic acid;

(S)-2-amino-6-borono-2-(3-(1-methoxy-4-methyl-1-oxopentan-2-ylamino)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-(3,4-dichlorobenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-methoxybenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3-methoxybenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-methylbenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(4-fluorobenzoyl)piperazin-1yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(2-fluorobenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(2-chlorobenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-(3-fluorobenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-4-(trifluoromethyl)benzoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-4-carbamoylbenzoyl)piperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-3,4-dichlorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-2-fluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-3-fluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-4-fluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-3,4-difluorophenylcarbamoyl)piperazin-1-yl)propyl hexanoic acid;

2-amino-6-borono-2-(3-(4-2,5-difluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-2,4-difluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-2,3-difluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-3,5-difluorophenylcarbamoyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-tosylpiperazin-1-yl)propyl)hexanoic acid;

2-amino-6-borono-2-(3-(4-4-fluorophenylsulfonyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-3-fluorophenylsulfonyl)piperazin-1-yl)propyl) hexanoic acid;

2-amino-6-borono-2-(3-(4-3,4-dichlorophenylsulfonyl)piperazin-1-yl)propyl) hexanoic acid;

a salt thereof, an ester thereof and a mixture thereof.

2. A compound selected from the group consisting of:

5-amino-8-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-5-(isopropoxycarbonyl)octylboronic acid;

5-amino-8-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-5-(isopentyloxycarbonyl)octylboronic acid;

5-amino-8-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-5-((2-(piperidin-1-yl)ethoxy) carbonyl) octylboronic acid;

5-amino-8-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-5-((2-morpholinoethoxy) carbonyl) octylboronic acid;

5-amino-5-(methoxycarbonyl)-8-(4-(4-methylsulfonyl)benzyl)piperazin-1-yl)octylboronic acid;

5-amino-5-(ethoxycarbonyl)-8-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)octylboronic acid;

5-amino-8-(4-(4-(methylsulfonyl)benzyl)piperazine-1-yl)-5-(propoxycarbonyl) octylboronic acid;

5-amino-5-(isopropoxycarbonyl)-8-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)octylboronic acid;

5-amino-5-(isobutoxycarbonyl)-8-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)octylboronic acid;

5-amino-5-(isopentyloxycarbonyl)-8-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)octylboronic acid;

5-amino-8-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)-5-((pentan-3-yloxy)carbonyl) octylboronic acid;

5-amino-5-((3-methylbutan-2-yloxy)carbonyl)-8-(4-(4-(methylsulfonyl) benzylpiperazin-1-yl) octylboronic acid;

5-amino-5-((2-methoxyethoxy)carbonyl)-8-(4-(4-(methylsulfonyl)benzyl) piperazin-1-yl) octylboronic acid;

5-amino-5-((2-hydroxyethoxy)carbonyl)-8-(4-(4-(methylsulfonyl)benzyl) piperazin-1-yl) octylboronic acid;

5-amino-8-(4-(4-(methylsulfonyl)benzyl)piperazine-1-yl-5((2-morpholinoethoxy)carbonyl) octylboronic acid;

5-amino-8-(4-(3,4-dichlorophenyl)piperazin-1-yl-5-(methoxycarbonyl) octylboronic acid;

a salt thereof and a mixture thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2015
From: CORRIDOR PHARMACEUTICALS, INC
To: ASTRAZENECA UK LIMITED
Reel/Frame 035190/0039 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2015
From: ASTRAZENECA UK LIMITED
To: ASTRAZENECA AB
Reel/Frame 035190/0121 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2014
From: ZHANG, YANQUN
To: CORRIDOR PHARMACEUTICALS, INC.
Reel/Frame 033931/0306 →
MERGER Recorded Oct 26, 2011
From: IMMUNE CONTROL INC.; ARGINETIX, INC.
To: CORRIDOR PHARMACEUTICALS, INC.
Reel/Frame 027121/0692 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2011
From: TOMCZUK, BRUCE E.; OLSON, GARY L.; POTTORF, RICHARD S.; WANG, LIJUAN JANE; NALLAGANCHU, BHASKARA R.
To: CORRIDOR PHARMACEUTICALS, INC.
Reel/Frame 027038/0181 →
Continuity (3)
Provisional Application 61428894 · Dec 31, 2010
Provisional Application 61450804 · Mar 9, 2011
Related Publication 20120171116A1 · Jul 5, 2012