IP Library Granted Patent US 8,450,351
Granted Patent B2
US 8,450,351 · App. 11/641,284 · Granted May 28, 2013

N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase

Inventors: Andrew P. Combs (Kennett Square, PA); Amy Takvorian (Newnan, GA); Wenyu Zhu (Media, PA); Richard B. Sparks (Boothwyn, PA)
Assignee: Incyte Corporation
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Quick Facts
Patent No.
US 8,450,351
App. No.
11/641,284
Granted
May 28, 2013
Kind
B2
Abstract

The present invention is directed to N-hydroxyamidino compounds which are modulators of indoleamine 2,3-dioxygenase (IDO), as well as pharmaceutical compositions thereof and methods of use thereof relating to the treatment of cancer and other diseases.

Claims (363)

1. A compound of Formula Ia:

or a pharmaceutically acceptable salt thereof, wherein:

U is N;

V is O;

W is N, wherein the five-membered ring containing U, V, and W is an aromatic heterocycle;

A is aryl or heteroaryl, each optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c (O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c (═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR e R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with 1, 2, or 3 substitutents independently selected from Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c (O)NR c R d , NR c (O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR b R d ;

R A and R B are each H;

R is H;

Q is OR Q , OC(O)R Q , OC(O)NR 4 R Q , NR 4 R Q , NR 4 C(O)R Q , NR 4 C(O)NR 4 R Q , NR 4 C(O)OR Q , NR 4 S(O)R Q , NR 4 S(O) 2 R Q , NR 4 C(═NR i )NR 4 R Q , SR Q , S(O)R Q , S(O)NR 4 R Q , S(O) 2 R Q , S(O) 2 NR 4 R Q , C(O)R Q , C(O)R Q , C(O)NR 4 R Q , halo, cyano, azido, or nitro;

R Q is H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , sR a2 , c(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 NR d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;

or R 4 and R Q together with the N atom to which they are attached form a 4-20 membered heterocycloalkyl group or 5-20 membered heteroaryl group, each optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR a2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)-OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 ;

Cy, Cy 1 , and Cy 2 are independently selected from aryl, heteroaryl, cycloalkyl, and heterocycloalkyl, each optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , C(═NR i )NR c3 R d3 , NR c3 C(═NR i )NR c3 R d3 , P(R f3 ) 2 , P(OR e3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR e3 R d3 ;

R 1 is H or C 1-4 alkyl;

R 4 is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C(O)—R 4a , SO 2 —R 4a , aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, halosulfanyl, CN, NO 2 , OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , C(O)OR a4 , OC(O)R b4 , OC(O) NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 C(O)NR c4 R d4 , NR c4 C(O)OR a4 , C(═NR i )NR c4 R d4 , NR c4 C(═NR i )NR c4 R d4 , P(R f4 ) 2 , P(OR e4 ) 2 , P(O)R e4 R f4 , P(O)OR e4 OR f4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , NR c4 S(O) 2 R b4 , and S(O) 2 NR c4 R d4 ;

R 4a is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl;

R a , R a3 , R a4 , and R a5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

R b , R b3 , R b4 , and R b5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

R a2 is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, Cy 2 , or Cy 2 -(C 1-6 alkyl)-, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, or C 2-6 alkynyl, is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy 2 , CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR a5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 NR d5 , NR c5 C(O)R b5 , NR c5 C(O)NR c5 R d5 , NR c5 C(O)OR a5 , C(═NR i )NR c5 R d5 , NR c5 C(═NR i )NR c5 R d5 , P(R f5 ) 2 , P(OR e5 ) 2 , P(O)R e5 R f5 , P(O)OR e5 OR f5 , S(O)R b5 , S(O)NR c5 R d5 , R b2 , S(O) 2 R b5 , NR c5 S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;

R b2 is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, Cy 2 , or Cy 2 -(C 1-6 alkyl)-, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, or aryl is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy 2 , CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 c(O)NR d5 , NR c5 C(O)OR a5 , C(═NR i )NR c5 R d5 , NR c5 C(═NR i )NR c5 R d5 , P(R f5 ) 2 , P(OR e5 ) 2 , P(O)R e5 R f5 , P(O)OR e5 OR f5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , NR c5 S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;

R c and R d are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c and R d together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c2 and R d2 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, Cy 2 and Cy 2 -(C 1-6 alkyl)-, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, and C 2-6 alkynyl, is optionally substituted with 1, 2, or 3, substitutents independently selected from halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , C(═NR i )NR c3 R d3 , NR c3 C(═NR i )NR c3 R d3 , P(R f3 ) 2 , P(OR e3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

or R c2 and R d2 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3, substitutents independently selected from Cy 2 , Cy 2 -(C 1-6 alkyl)-, halo, C 3-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , C(═NR i )NR c3 R d3 , NR c3 C(═NR i )NR c3 R d3 , P(R f3 ) 2 , P(OR e3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

R c3 and R d3 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 3-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c3 and R d3 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c4 and R d4 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c4 and R d4 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c5 and R d5 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c5 and R d5 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R e , R e2 , R e3 , R e4 , and R e5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, (C 1-6 alkoxy)-C 1-6 alkyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, and heterocycloalkylalkyl;

R f , R f2 , R f3 , R f4 , and R f5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, and heterocycloalkyl;

R i is H, CN; C(O)NH 2 , or NO 2 ; and

p is 1, 2, 3, 4, or 5.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein A is phenyl optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c (O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with 1, 2, or 3 substitutents independently selected from Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d .

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein A is phenyl optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d .

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein A is phenyl optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, and C 1-6 haloalkyl.

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is CN, OR Q , C(O)OR Q , NR 4 R Q , NR 4 C(O)R Q , NR 4 C(O)NR 4 R Q , NR 4 C(O)OR Q , NR 4 S(O) 2 R Q , or OC(O)NR 4 R Q .

6. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is OR Q , OC(O)NR 4 R Q , or NR 4 R Q .

7. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is OR Q .

8. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q .

9. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form a 4-20 membered heterocycloalkyl group or 5-20 membered heteroaryl group, each optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR c2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)—OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , N c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 .

10. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form a 5-20 membered heteroaryl group, optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR c2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)-OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 .

11. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form a tetrazolyl, triazolyl, or imidazolyl group which is optionally with 1 or 2 halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 -alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR c2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)-OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C (O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 .

12. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form a tetrazolyl group which is optionally substituted with 1, 2, or 3 substitutents selected from halo, C 1-6 alkyl, C 1-6 haloalkyl, and NR c2 R d2 .

13. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form a 5- or 6-membered heterocycloalkyl group optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR c2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)-OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 .

14. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is NR 4 R Q and R 4 and R Q together with the N atom to which they are attached form piperidinyl, morpholino, piperazinyl, 2,3-dihydro-1H-isoindolyl, or 1,2,3,4-tetrahydro-isoquinoline, each optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR c2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)-OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 .

15. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R Q is H, C 1-6 alkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-6 alkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR c2 OR f2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 .

16. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R Q is C 1-6 alkyl optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 .

17. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R Q is aryl, heteroaryl, arylalkyl, or heteroarylalkyl, each optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 .

18. The compound of claim 1 , or a pharmaceutically acceptable salt thereof,

wherein R 4 is H, C 1-4 alkyl, C(O)—R 4a , SO 2 —R 4a , aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-4 alkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , C(O)OR a4 , OC(O)R b4 , OC(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 C(O)NR c4 R d4 , NR c4 C(O)OR a4 , C(═NR i )NR c4 R d4 , NR c4 C(═NR i )NR c4 R d4 , P(R f4 ) 2 , P(OR e4 ) 2 , P(O)R e4 R f4 , P(O)OR e4 OR f4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , NR c4 S(O) 2 R b4 , and S(O) 2 NR c4 R d4 .

19. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is H.

20. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is H.

21. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein p is 1 or 2.

22. The compound of claim 1 having Formula II:

or a pharmaceutically acceptable salt thereof.

23. The compound of claim 1 selected from:

N-(3-chloro-4-fluoro-phenyl)-N-hydroxy-4-hydroxymethyl-furazan-3-carboxamidine;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(phenoxymethyl)-1,2,5-oxadiazole-3-carboximidamide;

4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino]hydroxyimino)methyl]-1,2,5-oxadiazol-3-ylmethyl phenylcarbamate;

4-[(benzylamino)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(2-chlorophenoxy)methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(3-chlorophenoxy)methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(4-chlorophenoxy)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(2-methoxyphenoxy)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-M-hydroxy-4-[(3-methoxyphenoxy)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(4-methoxyphenoxy)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(3-cyanophenoxy)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(4-chloro-2-methoxyphenoxy)methyl]-N′-hydroxy-1,2,5-oxa-diazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(3,4-dimethoxyphenoxy)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

{4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl phenylcarbamate;

{4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl isopropylcarbamate;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(piperidin-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(dimethylamino)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(4-phenylpiperazin-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(isoxazol-3-ylamino)methyl]-1,2,5-oxadiazole-3-carboximidamide;

4-{[(1-benzylpiperidin-4-yl)amino]methyl}-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxa-diazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(pyridin-2-ylmethyl)amino]methyl}-1,2,5-oxa-diazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(2-phenylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(3-phenylpropyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({[(1R)-1-phenylethyl]amino}methyl)-1,2,5-oxa-diazole-3-carboximidamide;

4-{[(2-chlorobenzyl)amino]methyl}-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(4-phenylbutyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-(3,4-dihydroisoquinolin-2(1H)-ylmethyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-(2,3-dihydro-1H-indol-1-ylmethyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide; and

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(morpholin-4-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

or a pharmaceutically acceptable salt thereof.

24. A composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

25. A compound of Formula Ia:

or a pharmaceutically acceptable salt thereof, wherein:

U is N;

V is O;

W is N, wherein the five-membered ring containing U, V, and W is an aromatic heterocycle;

A is aryl or heteroaryl, each optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with 1, 2, or 3 substitutents independently selected from CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d ;

R is H;

R A and R B are each H;

Q is OR Q , OC(O)R Q , OC(O)NR 4 R Q , NR 4 R Q , NR 4 C(O)R Q , NR 4 C(O)NR 4 R Q , NR 4 C(O)OR Q , NR 4 S(O)R Q , NR 4 S(O) 2 R Q , NHS(O) 2 NH 2 , NHS(O) 2 NHCH 3 , NHS(O) 2 NHCH 2 CH 3 , NHS(O) 2 NHCH(CH 3 ) 2 , NHS(O) 2 N(CH 3 ) 2 , NR 4 C(═NR i )NR 40 , SR Q , S(O)R Q , S(O)NR 4 R Q , S(O) 2 R Q , S(O) 2 NR 4 R Q , C(O)R Q , C(O)OR Q , C(O)NR 4 R Q , halo, cyano, azido, or nitro;

R Q is H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 (O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(═NR i )NR a2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R e2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;

or R 4 and R Q together with the N atom to which they are attached form a 4-20 membered heterocycloalkyl group or 5-20 membered heteroaryl group, each optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , —(C 1-4 alkyl)-OR a2 , SR a2 , —(C 1-4 alkyl)-SR a2 , C(O)R b2 , —(C 1-4 alkyl)-C(O)R b2 , C(O)NR c2 R d2 , —(C 1-4 alkyl)-C(O)NR a2 R d2 , C(O)OR a2 , —(C 1-4 alkyl)-C(O)OR a2 , OC(O)R b2 , —(C 1-4 alkyl)—OC(O)R b2 , OC(O)NR c2 R d2 , —(C 1-4 alkyl)-OC(O)NR c2 R d2 , NR c2 R d2 , —(C 1-4 alkyl)-NR c2 R d2 , NR c2 C(O)R b2 , —(C 1-4 alkyl)-NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , —(C 1-4 alkyl)-NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , —(C 1-4 alkyl)-NR c2 C(O)OR a2 , C(═NR i )NR c2 R d2 , NR c2 C(NR i )NR c2 R d2 , P(R f2 ) 2 , P(OR e2 ) 2 , P(O)R r2 R f2 , P(O)OR e2 OR f2 , S(O)R b2 , —(C 1-4 alkyl)-S(O)R b2 , S(O)NR c2 R d2 , —(C 1-4 alkyl)-S(O)NR c2 R d2 , S(O) 2 R b2 , —(C 1-4 alkyl)-S(O) 2 R b2 , NR c2 S(O) 2 R b2 , —(C 1-4 alkyl)-NR c2 S(O) 2 R b2 , S(O) 2 NR c2 R d2 , and —(C 1-4 alkyl)-S(O) 2 NR c2 R d2 ;

Cy, Cy 1 , and Cy 1 are independently selected from aryl, heteroaryl, cycloalkyl, and heterocycloalkyl, each optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(═NR i )NR c3 R d3 , NR c3 C(═NR i )NR c3 R d3 , P(R f3 ) 2 , P(OR e3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

R 1 is H or C 1-4 alkyl;

R 4 is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C(O)—R 4a , SO 2 —R 4a , aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, halosulfanyl, CN, NO 2 , OR a4 , SR a4 , C(O)R b4 , C(O)NR c4 R d4 , C(O)OR a4 , OC(O)R b4 , OC(O)NR c4 R d4 , NR c4 R d4 , NR c4 C(O)R b4 , NR c4 C(O)NR c4 R d4 , NR c4 C(O)OR a4 , C(═NR i )NR c4 R d4 , NR c4 C(═NR i )NR c4 R d4 , P(R f4 ) 2 , P(OR e4 ) 2 P(O)R e4 R f4 , P(O)OR e4 OR f4 , S(O)R b4 , S(O)NR c4 R d4 , S(O) 2 R b4 , NR c4 S(O) 2 R b4 , and S(O) 2 NR e4 R d4 ;

R 4a is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl;

R a3 , R a4 , and R a5 are in dependently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

R b , R b3 , R b4 , and R b5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

R a2 is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, Cy 2 , or Cy 2 -(C 1-6 alkyl)-, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, or C 2-6 alkynyl, is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 . haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy 2 , CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)NR c5 R d5 , NR c5 C(O)OR a5 ,

C(═NR i )NR c2 R d5 , NR c5 C(═NR i )NR c5 R d5 , P(R f5 ) 2 , P(OR e5 ) 2 , P(O)R e5 R f5 , P(O)OR e5 OR f5 , S(O)R b5 , S(O)NR e5 R d5 , R b2 , S(O) 2 R b5 , NR c5 S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;

R b2 is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, Cy 2 , or Cy 2 -(C 1-6 alkyl)-, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, or aryl is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, halosulfanyl, Cy 2 , CN, NO 2 , OR a5 , SR a5 , C(O)R b5 , C(O)NR c5 R d5 , C(O)OR a5 , OC(O)R b5 , OC(O)NR c5 R d5 , NR c5 R d5 , NR c5 C(O)R b5 , NR c5 C(O)NR c5 R d5 , NR c5 C(O)OR a5 , C(═NR i )NR c5 R d5 , NR c5 C(═NR i )NR c5 R d5 , P(R f5 ) 2 , P(OR e5 ) 2 , P(O)R e5 e, P(O)OR e5 OR f5 , S(O)R b5 , S(O)NR c5 R d5 , S(O) 2 R b5 , NR c5 S(O) 2 R b5 , and S(O) 2 NR c5 R d5 ;

R c and R d are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 . haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c and R d together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c2 and R d2 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, Cy 2 and Cy 2 -(C 1-6 alkyl)-, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, and C 2-6 alkynyl, is optionally substituted with 1, 2, or 3, substitutents independently selected from halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , C(═NR i )NR c3 R d3 , NR c3 C(═NR i )NR c2 R d3 , P(R f3 ) 2 , P(OR f3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

or R c2 and R d2 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3, substitutents independently selected from Cy 2 , Cy 2 -(C 1-6 alkyl)-, halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, halosulfanyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , C(═NR i )NR c2 R d3 , NR c3 C(═NR i )NR c3 R d3 , P(R f3 ) 2 , P(OR e3 ) 2 , P(O)R e3 R f3 , P(O)OR e3 OR f3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

R c3 and R d3 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c3 and R d3 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c4 and R d4 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c4 and R d4 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c5 and R d5 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, or heterocycloalkyl;

or R c5 and R d5 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R e , R e2 , R e3 , R e4 , and R e5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, (C 1-6 alkoxy)-C 1-6 alkyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, and heterocycloalkylalkyl;

R f , R f2 , R f3 , R f4 , and R f5 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, and heterocycloalkyl;

R i is H, CN, C(O)NH 2 , or NO 2 ; and

p is 1, 2, 3, 4, or 5.

26. A compound of claim 25 selected from:

4-[(aminosulfonyl)amino]methyl-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-([(methylamino)-sulfonyl]aminomethyl)-1,2,5-oxadiazole-3-carboximidamide;

4-{2-[(aminosulfonyl)amino]ethyl}-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-{3-[(aminosulfonyl)amino]propyl}-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-{[(aminosulfonyl)amino]methyl}-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-{[(aminosulfonyl)amino]methyl}-N′-hydroxy-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-({[(isopropylamino)sulfonyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N-hydroxy-4-({[(methylamino)sulfonyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(ethylamino)sulfonyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(dimethylamino)sulfonyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N[3-(difluoromethyl)phenyl]-N′-hydroxy-4-({[(methylamino)sulfonyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

4-{[(aminosulfonyl)amino]methyl}-N-[3-(difluoromethyl)phenyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide; and

4-{2-[(aminosulfonyl)amino]ethyl}-N-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide; or a pharmaceutically acceptable salt thereof.

27. A compound of claim 25 , wherein A is phenyl optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, hydroxyalkyl, C 1-6 cyanoalkyl, Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d , wherein said C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with 1, 2, or 3 substitutents independently selected from Cy 1 , CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c n d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , C(═NR i )NR c R d , NR c C(═NR i )NR c R d , P(R f ) 2 , P(OR e ) 2 , P(O)R e R f , P(O)OR e OR f , S(O)R b , S(O)NR c n d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d .

28. A compound of claim 1 , having Formula IIa:

or a pharmaceutically acceptable salt thereof; wherein:

A is aryl or heteroaryl, each optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, CN, NO 2 , OR a , SR a , C(O)R b , C(O)NR c R d , C(O)OR a , OC(O)R b , OC(O)NR c R d , NR c R d , NR c C(O)R b , NR c C(O)NR c R d , NR c C(O)OR a , S(O)R b , S(O)NR c R d , S(O) 2 R b , NR c S(O) 2 R b , and S(O) 2 NR c R d ;

R is H;

R A and R B are each H;

Q is OR Q , OC(O)R Q , OC(O)NR 4 R Q , NR 4 R Q , NR 4 C(O)R Q , NR 4 C(O)NR 4 R Q , SR Q , S(O)R Q , S(O)NR 4 R Q , S(O) 2 R Q , or S(O) 2 NR 4 R Q ;

R Q is H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteroarylalkyl, or heterocycloalkylalkyl is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 1-6 cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , S(O)R b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;

or R 4 and R Q together with the N atom to which they are attached form a 4-20 membered heterocycloalkyl group optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, cyanoalkyl, Cy, —(C 1-4 alkyl)-Cy, CN, NO 2 , OR a2 , SR a2 , C(O)R b2 , C(O)NR c2 R d2 , C(O)OR a2 , OC(O)R b2 , OC(O)NR c2 R d2 , NR c2 R d2 , NR c2 C(O)R b2 , NR c2 C(O)NR c2 R d2 , NR c2 C(O)OR a2 , S(O)OR b2 , S(O)NR c2 R d2 , S(O) 2 R b2 , NR c2 S(O) 2 R b2 , and S(O) 2 NR c2 R d2 ;

Cy is aryl, heteroaryl, cycloalkyl, or heterocycloalkyl, each optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from halo, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, CN, NO 2 , OR a3 , SR a3 , C(O)R b3 , C(O)NR c3 R d3 , C(O)OR a3 , OC(O)R b3 , OC(O)NR c3 R d3 , NR c3 R d3 , NR c3 C(O)R b3 , NR c3 C(O)OR a3 , S(O)R b3 , S(O)NR c3 R d3 , S(O) 2 R b3 , and S(O) 2 NR c3 R d3 ;

R 1 is H or C 1-4 alkyl;

R 4 is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, or C(O)—(C 1-4 alkyl);

R a , R a2 , and R a3 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl;

R b , R b2 , and R b3 are independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl and heterocycloalkylalkyl, wherein said C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl;

R c and R d are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl and heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl;

or R c and R d together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group;

R c2 and R d2 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl;

or R c2 and R d2 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group; and

R c3 and R d3 are independently selected from H, C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl, wherein said C 1-10 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl or heterocycloalkylalkyl is optionally substituted with OH, amino, halo, C 1-6 alkyl, C 1-6 haloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl;

or R c3 and R d3 together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group.

29. The compound of claim 1 , selected from:

3-(4-[(2-morpholin-4-ylethyl)amino]methyl-1,2,5-oxadiazol-3-yl)-4-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5(4H)-one;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(methylsulfonyl)(2-morpholin-4-ylethyl)amino]-methyl-1,2,5-oxadiazole-3-carboximidamide;

N-{4-[N-(3-chloro-4-fluoro-phenyl)-N-hydroxy-carbamimidoyl]-furazan-3-ylmethyl}-benzamide;

N-(3-chloro-4-fluoro-phenyl)-N′-hydroxy-4-[(3-phenyl-ureido)-methyl]-furazan-3-carbox-amidine;

4-(benzenesulfonylamino-methyl)-N-(3-chloro-4-fluoro-phenyl)-N′-hydroxy-furazan-3-carbox-amidine;

benzyl({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)carbamate;

4-[(5-amino-1H-tetrazol-1-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-2H-tetrazol-2-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(1H-tetrazol-5-ylamino)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-({[3-(1H-imidazol-1-yl)propyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(2-morpholin-4-ylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[(4-hydroxypiperidin-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[4-(2-hydroxyethyl)piperazin-1-yl]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(1R)-2-hydroxy-1-phenylethyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(2-hydroxyethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[(2-pyridin-4-ylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(tetrahydrofuran-2-ylmethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(1,3-thiazol-2-ylmethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

4-({[4-(aminosulfonyl)benzyl]amino}methyl)-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

{4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl dimethylcarbamate;

4-{[4-(aminosulfonyl)phenoxy]methyl}-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-/V′-hydroxy-4-{[4-(methylsulfonyl)phenoxy]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(1H-imidazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(1H-1,2,4-triazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

4-[({2-[4-(aminosulfonyl)phenyl]ethyl}amino)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(2H-tetrazol-2-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(1H-tetrazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

{4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl morpholine-4-carboxylate;

4-(aminomethyl)-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-1H-tetrazol-1-yl)methyl]-N-[3-(trifluoromethyl)phenyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-benzyl-1H-tetrazol-1-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-benzyl-2H-tetrazol-2-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

[2-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyamino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-2H-tetrazol-5-yl]acetic acid;

N-(3-chloro-4-fluorophenyl)-4-(cyanomethyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[2-(dimethylamino)ethyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(3-morpholin-4-ylpropyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-pyridin-4-yl-2H-tetrazol-2-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

4-([4-(aminosulfonyl)benzyl]aminomethyl)-N-[3-(trifluoromethyl)phenyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(trifluoromethyl)phenyl]-N′-hydroxy-4-(1H-tetrazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(trifluoromethyl)phenyl]-N′-hydroxy-4-(2H-tetrazol-2-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(trifluoromethyl)phenyl]-N′-hydroxy-4-{[(2-morpholin-4-ylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(pyridin-3-ylmethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(2-pyrrolidin-1-ylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({[2-(1H-imidazol-4-yl)ethyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({[2-(2-oxopyrrolidin-1-yl)ethyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-choro-4-fluorophenyl)-N-hydroxy-4-[(5-methyl-1H-tetrazol-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-methyl-2H-tetrazol-2-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino]hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-N-(2-morpholin-4-ylethyl)acetamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[5-(methylthio)-2H-tetrazol-2-yl]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[5-(methylthio)-1H-tetrazol-1-yl]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-phenyl-1H-tetrazol-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-phenyl-2H-tetrazol-2-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({5-[3-(trifluoromethoxy)phenyl]-2H-tetrazol-2-yl}-methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-pyridin-3-yl-2H-tetrazol-2-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(5-pyrrolidin-1-yl-2H-tetrazol-2-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({5-[3-(trifluoromethoxy)phenyl]-1H-tetrazol-1-yl}-methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[(5-pyridin-2-yl-1H-tetrazol-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[(5-pyrrolidin-1-yl-1H-tetrazol-1-yl)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-{[5-(4-fluorophenyl)-1H-tetrazol-1-yl]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({5-[2-(dimethylamino)ethyl]-1H-tetrazol-1-yl}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide

N-(3-chloro-4-fluorophenyl)-4-{[5-(4-fluorophenyl)-2H-tetrazol-2-yl]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({5-[2-(4-chlorophenoxy)ethyl]-2H-tetrazol-2-yl}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({5-[5-(trifluoromethyl)pyridin-2-yl]-2H-tetrazol-2-yl}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({5-[2-(4-chlorophenoxy)ethyl]-1H-tetrazol-1-yl}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({2-[(2R,6S)-2,6-dimethylmorpholin-4-yl)ethyl]amino)methyl}-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({[2-(2-methylpiperidin-1-yl)ethyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[(1,1-dimethyl-2-morpholin-4-ylethyl)amino]methyl-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(2-piperazin-1-ylethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(1-ethylpyrrolidin-2-yl)methyl]amino}methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[2-(dimethylamino)propyl]amino}methyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(2-methyl-2-morpholin-4-ylpropyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(2-methyl-2-piperidin-1-ylpropyl)amino]methyl 1-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(piperidin-2-ylmethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[2-(1,1-dioxidothiomorpholin-4-yl)ethyl]-amino}-methyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(piperidin-3-ylamino)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(pyrrolidin-3-ylmethyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-2-methylpropanamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-2,2-dimethylpropanamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-2-phenylacetamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-3-phenylpropanamide;

N-(4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1,3-thiazole-5-carboxamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino]hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)cyclopentanecarboxamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(methylsulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

4-({[(benzylamino)carbonyl]amino}methyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[({[(2-phenylethyl)-amino]carbonyl}-amino)methyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-({[(isopropylamino)-carbonyl]amino}-methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)morpholine-4-carboxamide;

N-(3-chloro-4-fluorophenyl)-4-({[(dimethylamino)carbonyl]amino}methyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)acetamide;

methyl ({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino]hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)carbamate;

isobutyl ({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)carbamate;

benzyl ({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)carbamate;

N-(3-chloro-4-fluorophenyl)-4-{[(ethylsulfonyl)amino]methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(5-{[({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl}-1,2,5-oxadiazol-3-yl}methyl)amino]sulfonyl}-4-methyl-1,3-thiazol-2-yl)acetamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[({5-[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-thienyl}sulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-({[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(3,5-dimethylisoxazol-4-yl)sulfonyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-({[(1,3,5-trimethyl-1H-pyrazol-4-yl)sulfonyl]amino}-methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(1,2-dimethyl-1H-imidazol-4-yl)sulfonyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{[(propylsulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-{[(cyclopropylsulfonyl)amino]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-{[(3-methylisothiazol-5-yl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

ethyl 3-4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-ylpropanoate; and

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboximidamide; or

a pharmaceutically acceptable salt thereof.

30. A compound of claim 1 , selected from:

N-(3-chloro-4-fluorophenyl)-4-([(E/Z)-(cyanoimino)(methylamino)methyl]aminomethyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(aminocarbonyl)amino]methyl-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-([(tert-butylamino)carbonyl]aminomethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-([(3-morpholin-4-ylpropyl)sulfonyl]aminomethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[(piperidin-4-ylsulfonyl)amino]methyl-1,2,5-oxadiazole-3-carboximidamide;

4-{([1-(aminosulfonyl)piperidin-4-yl]sulfonylamino)methyl}-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-([(1-acetylpiperidin-4-yl)sulfonyl]aminomethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[5-(morpholin-4-ylmethyl)-2H-tetrazol-2-yl]methyl-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[5-(morpholin-4-ylmethyl)-1H-tetrazol-1-yl]methyl-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]methyl-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-4H-1,2,4-triazol-3-yl)thio]methyl-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-4H-1,2,4-triazol-3-yl)sulfonyl]methyl-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({(E/Z)-(cyanoimino)[(4-methoxybenzyl)amino]methyl} amino)-methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[({(E/Z)-[(aminocarbonyl)imino][(4-methoxybenzyl)amino]methyl}amino)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-amino(nitroimino)methyl]amino}methyl)-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[amino(imino)methyl]amino}methyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(4H-1,2,4-triazol-4-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

4-[2-(5-amino-1H-tetrazol-1-yl)ethyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[2-(5-amino-2H-tetrazol-2-yl)ethyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[2-(1H-imidazol-1-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(2-morpholin-4-ylethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[2-(4-methylpiperazin-1-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[2-(4H-1,2,4-triazol-4-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[2-(1H-1,2,4-triazol-1-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[2-(1H-tetrazol-1-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[2-(2H-tetrazol-2-yl)ethyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[2-(dimethylamino)ethyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-(2-thiomorpholin-4-ylethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-(2-pyrrolidin-1-ylethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{2-[isopropyl(methyl)amino]ethyl}-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-{2-[(methylsulfonyl)amino]ethyl}-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(E/Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-N′-cyanomorpholine-4-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[({(E/Z)-(cyanoimino)[(2-morpholin-4-ylethyl)amino]methyl}-amino)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[({(E/Z)-[(aminocarbonyl)imino][(2-morpholin-4-ylethyl)amino]methyl]amino)methyl}-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-{R(E/Z)-(cyanoimino) {[2-(dimethylamino)ethyl]amino}methyl)-amino]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-{R(E/Z)-(cyanoimino){[2-(1H-imidazol-5-yl)ethyl]amino}-methyl)amino]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-{[((E/Z)-[(aminocarbonyl)imino]{[2-(1H-imidazol-5-yl)ethyl]amino}methyl)amino]methyl}-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[((E/Z)-(cyanoimino)[(2-hydroxy-1-methylethyl)amino]methyl}-amino)methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(isopropylamino)methyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[({(E/Z)-(cyanoimino)[(2-methoxy-1-methylethyl)amino]-methyl}amino)methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[({(E/Z)-(cyanoimino)[(2-methoxyethyl)amino]methyl}amino)-methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(tetrahydro-2H-pyran-4-ylamino)methyl]-amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-{[((E/Z)-(cyanoimino){[(1-ethylpyrrolidin-2-yl)methyl]amino}-methyl)amino]methyl}-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-amino(cyanoimino)methyl]amino}methyl)-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-[({(E/Z)-(cyanoimino)[(2-hydroxyethyl)amino]methyl}amino)-methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(dimethylamino)methyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(ethylamino)methyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(ethylamino)methyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-(cyanoimino)(dimethylamino)methyl]amino}methyl)-N-hydroxy-N-[3-(trifluoro-methyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-(cyanoimino)(ethylamino)methyl]amino}methyl)-N′-hydroxy-N-[3-(trifluoromethyl)-phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-4-({[(E/Z)-(cyanoimino)(dimethylamino)methyl]amino}methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-(cyanoimino)(methylamino)methyl]amino}methyl)-N′-hydroxy-N-[3-(trifluoro-methyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-4-{[(E/Z)-(cyanoimino)(methylamino)methyl]amino}methyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-amino(cyanoimino)methyl]amino}methyl)-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-({[(E/Z)-amino(cyanoimino)methyl]amino}methyl)-N-hydroxy-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N[3-(difluoromethyl)phenyl]-N-hydroxy-4-(1H-tetrazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(difluoromethyl)phenyl]-N′-hydroxy-4-(2H-tetrazol-2-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N′-hydroxy-4-(4H-1,2,4-triazol-4-ylmethyl)-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N-hydroxy-4-(4H-1,2,4-triazol-4-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-1H-tetrazol-1-yl)methyl]-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-2H-tetrazol-2-yl)methyl]-N-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1H-imidazole-2-carboxamide;

N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1H-pyrazole-4-carboxamide;

N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide;

N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1H-imidazole-4-carboxamide;

N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1,2,3-thiadiazo1e-4-carboxamide;

5-amino-N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)-1,3,4-thiadiazole-2-carboxamide;

5-amino-N-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxamide;

4-(aminomethyl)-N-(3-bromo-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N-hydroxy-4-{[(methylsulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

4-(aminomethyl)-N′-hydroxy-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximid-amide;

N′-hydroxy-4-{[(methylsulfonyl)amino]methyl}-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-({[(2,2,2-trifluoroethyl)sulfonyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N-hydroxy-4-(1H-tetrazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

[1-({4-[(Z)-[(3-chloro-4-fluorophenyl)amino](hydroxyimino)methyl]-1,2,5-oxadiazol-3-yl}-methyl)-1H-tetrazol-5-yl]acetic acid;

N-(3-chloro-4-fluorophenyl)-4-({[(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)sulfonyl]amino}-methyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-({[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-sulfonyl]amino}methyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[3-(1H-tetrazol-1-yl)propyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[3-(2H-tetrazol-2-yl)propyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-4-[3-(4H-1,2,4-triazol-4-yl)propyl]-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-4-(3-{[(E/Z)-(cyanoimino)(methylamino)methyl]amino}propyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(3-amino-4H-1,2,4-triazol-4-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-1H-1,2,4-triazol-1-yl)methyl]-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[(1,3,4-thiadiazol-2-ylamino)methyl]-1,2,5-oxadia-zole-3-carboximidamide;

4-[(5-amino-1H-tetrazol-1-yl)methyl]-N-[3-(difluoromethyl)phenyl]-N′-hydroxy-1,2,5-oxadia-zole-3-carboximidamide;

4-[(5-amino-2H-tetrazol-2-yl)methyl]-N-(4-fluoro-3-methylphenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(difluoromethyl)phenyl]-N-hydroxy-4-(1H-tetrazol-1-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(difluoromethyl)phenyl]-N-hydroxy-4-(2H-tetrazol-2-ylmethyl)-1,2,5-oxadiazole-3-carboximidamide;

N[3-(difluoromethyl)phenyl]-N-hydroxy-4-{[(methylsulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

N-[3-(difluoromethyl)phenyl]-N-hydroxy-4-({[(trifluoromethyl)sulfonyl]amino}methyl)-1,2,5-oxadiazole-3-carboximidamide;

4-{[bis(methylsulfonyl)amino]methyl}-N-[3-(difluoromethyl)phenyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-[(5-amino-1H-tetrazol-1-yl)methyl]-N-(4-fluoro-3-methylphenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

4-{[(6-aminohexyl)amino]methyl}-N-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide;

N-(4-fluoro-3-methylphenyl)-N′-hydroxy-4-{[(methylsulfonyl)amino]methyl}-1,2,5-oxadiazole-3-carboximidamide;

4-[2-(5-amino-1H-tetrazol-1-yl)ethyl]-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide; and

N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{2-[(methylsulfonyl)amino]ethyl}-1,2,5-oxadiazole-3-carboximidamide;

or a pharmaceutically acceptable salt thereof.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY INFORMATION PREVIOUSLY RECORDED ON REEL 035920 FRAME 0576. ASSIGNOR(S) HEREBY CONFIRMS THE RECEIVING PARTY NAME SHOULD BE RECORDED AS TWO PARTIES. Recorded Jul 2, 2015
From: INCYTE CORPORATION
To: INCYTE HOLDINGS CORPORATION; INCYTE CORPORATION
Reel/Frame 036054/0740 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2015
From: INCYTE CORPORATION
To: INCYTE HOLDINGS CORPORATION AND INCYTE CORPORATION
Reel/Frame 035920/0576 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2007
From: COMBS, ANDREW P.; TAKVORIAN, AMY; ZHU, WENYU; SPARKS, RICHARD B.
To: INCYTE CORPORATION
Reel/Frame 019199/0006 →
Continuity (4)
Provisional Application 60751854 · Dec 20, 2005
Provisional Application 60801337 · May 18, 2006
Provisional Application 60857558 · Nov 8, 2006
Related Publication 20070185165A1 · Aug 9, 2007