IP Library › Granted Patent US 7,884,119

Granted Patent B2

US 7,884,119 · App. 11/518,550 · Granted Feb 8, 2011

Triazole derivatives useful as Axl inhibitors

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 7,884,119
App. No.: 11/518,550
Granted: Feb 8, 2011
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

Triazole derivatives and pharmaceutical compositions containing the derivatives are disclosed as being useful in inhibiting the activity of the receptor protein tyrosine kinase Axl. Methods of using the derivatives in treating diseases or conditions associated with Axl catalytic activity are also disclosed.

Claims (432)

1. A compound of formula (Ia) or formula (Ib):

wherein, independently at each occurrence:

A is —C(O)— or —C(S)—;

R 1 is aryl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each independently hydrogen, alkyl, aryl, aralkyl, —C(O)R 10 or —C(O)N(R 6 )R 7 ;

R 3 is one of the following:

a) aryl optionally substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN; or

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O )N(R 10 ) 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 8 present in a R 3 substituent is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain, an optionally substituted straight or branched alkenylene chain and an optionally substituted straight or branched alkynylene chain;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, an optionally substituted straight or branched alkenylene chain and an optionally substituted straight or branched alkynylene chain; and

R 10 present in the R 2 , R 4 and R 5 substituents and each R 10 present in a R 3 substituent, a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, and optionally substituted heteroarylalkynyl;

as an isolated stereoisomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or N-oxide thereof.

2. The compound of claim 1 of formula (Ia):

wherein:

A is —C(O)—;

R 2 is hydrogen, alkyl or —C(O)R 10 ;

R 4 and R 5 are each hydrogen or alkyl;

R 3 is one of the following:

a) aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN; or

b) heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

R 10 present in the R 2 substituent and each R 10 present in a R 3 substituent, a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, and optionally substituted heteroarylalkynyl.

3. The compound of claim 2 wherein:

A is —C(O)—;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is one of the following:

a) aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN; or

b) heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 10 present in a R 3 substituent, a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl.

4. The compound of claim 3 wherein:

A is —C(O)—;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

5. The compound of claim 4 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O——R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 , and —R 8 —CN;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

6. The compound of claim 5 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or two substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)0R 10 and —R 8 —CN;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 8 present in a R 3 substituent is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain, and an optionally substituted straight or branched alkenylene chain;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

each R 10 present in a R 3 substituent, a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, and optionally substituted heteroarylalkyl.

7. The compound of claim 6 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 , where R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heterorayalkyl and optionally substituted aralkyl, and optionally submitted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, and alkoxy

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

8. The compound of claim 7 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 , where R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 , and —R 8 —CN;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

9. The compound of claim 8 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —OR 10 and optionally substituted with halo or alkoxy, where R 8 is a direct bond and R 10 is selected from the group consisting of 2-(pyrrolidin-1-yl)ethyl, 2-(piperidin-1-yl)ethyl, 2-(morpholin-4-yl)ethyl, 2-(1,3-dioxolan-2-yl)ethyl, 2-(thiomorpholin-4-yl)ethyl, 3-(pyrrolidin-1-yl)propyl, 2-(azepan-1-yl)ethyl, 2-(imidazol-1-yl)ethyl, 2-(pyrrolidin-2-on-1-yl)ethyl, and 2-(3-fluoropyrrolidin-1-yl)ethyl;

R 2 , R 4 and R 5 are each hydrogen or alkyl; and

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, —R 8 —OR 10 , R 8 —C(O)OR 10 , R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(O)OR 10 and —R 8 —CN, where:

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 8 is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain, and an optionally substituted straight or branched alkenylene chain;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

each R 10 is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, and optionally substituted heteroarylalkyl.

10. The compound of claim 9 selected from the group consisting of:

5-amino-1-(3-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(methyl)phenylcarbonyl-3-[3-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenylcarbonyl-3-[3-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-3-[3-[-2(1,3-dioxolan-2-yl)ethoxy]phenylamino]-1-(4-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[-4-[4-[2(1,3-dioxolan-2-yl)ethoxy]phenylamino]-1-(4-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenylcarbonyl-3-[4-2-(morpholin-4-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenylcarbonyl-3-[4-[2-(piperidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1-(4-(tert-butoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propyl)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenyl amino]-1H-1,2,4-triazole;

5-amino-1-(4-(methyl)phenyl)carbonyl-3-[4-[2-(piperidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(methyl)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenylcarbonyl-3 [2-(thiomorpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(methyl)phenylcarbonyl-3-[4-[2-(thiomorpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(cyclohexyl)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(methoxycarbonyl)phenyl)carbonyl-3-[4-[2-(piperidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(methoxy)phenyl)carbonyl-3-[4-[2-(piperidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3 ,4-(dimethoxy)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3 ,5-(dimethoxy)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(dimethylamino)phenyl)carbonyl-3-[442-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(dimethylamino)phenyl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-methylphenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yeethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3,5-(dimethoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-methylphenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamine]-1H-1,2,4-triazole;

5-amino-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1-(4-(tert-butoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-1-(3-methoxyphenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(dimethylamino)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(dimethylamino)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3 ,4-(dimethoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylaminol-1H-1,2,4-triazole;

5-amino-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1-(3-(tert-butoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1-(3-(trifluoromethoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1-(4-(trifluoromethoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3 4443-(pyrrolidin-1-yl)propoxy]phenylamino]-1-(4-(tert-butoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[443-(pyrrolidin-1-yl)propoxy]phenylamino]-1-(3-(tert-butoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-1-(4- (iso-propoxy)phenyl)carbonyl-3-[4-[3-(pyrrolidin-1-yl)propoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(dimethylamino)phenyl)carbonyl-3-[4-[3-(pyrrolidin-1-yl)propoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(dimethylamino)phenyl)carbonyl-3-[4-[3-(pyrrolidin-1-yppropoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butyl)phenyl)carbonyl-3-[4-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(morpholin-4-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(phenoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxycarbonylamino)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenyl][methyl]amino-1H-1,2,4-triazole;

5-amino-1-[4-((tert-butoxycarbonyl) aminomethyl)phenyl]carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(methylamino)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(methylthio)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(2,6-difluorophenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butylcarbonylamino)phenyl)carbonyl-3-[4-2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butyl)phenyl)carbonyl-3-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[3-fluoro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[3-fluoro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butyl)phenyl)carbonyl-3-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butyl)phenyl)carbonyl-3-[4-[2-(azepan-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(azepan-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4[2-(azepan-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(isoindolin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(isoindolin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-[4-(2-(morpholin-4-yl)ethoxy)phenyl)carbonyl-3-[442-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-2-on-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-2-on-1-yl)ethoxy]phenylamino]1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(iso-propoxy)phenyl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(dimethylamino)phenyl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(dimethylamino)phenyl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-fluoro-4-methoxyphenyl)carbonyl-3-[4-[2-(pyrrolidin-l-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(tert-butoxy)phenyl)carbonyl-3-[4-[2(S)-3-fluoropyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(dimethylamino)phenyl)carbonyl-3-[4-[2-((S)-3-fluoropyrrolidin-1-yl)ethoxylphenylamino]-1H-1,2,4-triazole;

5-amino-1-(3,5-difluoro-4-methoxyphenyl)carbonyl-3-[4-2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole; and

5-amino-3-[3-chloro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1-(3,5-dichlorophenyl)carbonyl-1H-1,2,4-triazole.

11. The compound of claim 8 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 , where R 8 is a direct bond and R 10 is optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen or alkyl;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, —R 8 —OR 10 , —R 8 —C(OOR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(OOR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(OOR 10 and —R 8 —CN;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 ,) —R 9 —N(R 10 2 , —R 9 —C(OOR 10 and)—R 9 —C(O)N(R 10 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

12. The compound of claim 11 selected from the group consisting of:

5-amino-3-[3-(benzyloxy)phenylamino]-1-(4-(methyl)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[4-(benzyloxy)phenylamino]-1-(4-methylphenyl)carbonyl-1H-1,2,4-triazole; 5-amino-3-[4-(benzyloxy)phenylamino]-1-(4-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[3-(benzyloxy)phenylamino]-1-(3-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole; and

5-3-[3-(benzyloxy)phenylamino]-1-(3-(iso-propoxy)phenyl)carbonly-1H-1,2,4-triazole.

13. The compound of claim 7 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 , where R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen or alkyl; and

R 3 is phenyl substituted with one or more substituents selected from the group consisting of cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted heterocyclyl.

14. The compound of claim 13 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —OR 10 and optionally substituted with halo, alkyl or alkoxy, where R 8 is a direct bond and R 10 is selected from the group consisting of 2-(pyrrolidin-1-yl)ethyl, 2-(piperidin-1-yl)ethyl, 2-(morpholin-4-yl)ethyl, 2-(1,3-dioxolan-2-yl)ethyl, 2-(thiomorpholin-4-yl)ethyl, 3-(pyrrolidin-1-yl)propyl, 2-(azepan-1-yl)ethyl, 2-(isoindolin-1-yl)ethyl, 2-(imidazol-1-yl)ethyl, 2-(pyrrolidin-2-on-1-yl)ethyl, and 2-(3-fluoropyrrolidin-1-yl)ethyl;

R 2 , R 4 and R 5 are each hydrogen or alkyl; and

15. The compound of claim 14 selected from the group consisting of:

5-amino-3-[4-[2-(pytTolidin-1-yl)ethoxy]-3-fluorophenyl]amino-144-(morpholin-4-yl)phenyl]carbonyl-1H-1,2,4-triazole 5-amino-1-(4-(imidazol-1-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(phenyl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-1,2,3-thiadiazol-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(pyrrol-1-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl) ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-1,2,3-thiadiazol-4-yl)phenyl)carbonyl-3-[3-fluoro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(thiazol-2-yl)phenyl)carbonyl-3-[-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(thien-2-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(thien-2-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(thien-3-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(1,2,3-thiadiazol-4-yl)phenyl)carbonyl-3-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(1,2,3-thiadiazol-4-yl)phenyl)carbonyl-3-[4-[2-(azepan-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(morpholin-4-yl)phenyl)carbonyl-3-[4-[2-(isoindolin-1-yl)ethoxy]phenylamino]1H-1,2,4-triazole;

5-amino-1-(3-(morpholin-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(44 1,2,3-thiadiazol-4-yl)phenyl)carbonyl-3 4442-(pyrrolidin-2-on-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(morpholin-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-2-on-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(morpholin-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-2-on-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(morpholin-4-yl)phenyl)carbonyl-3-[4-methoxy-442-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-(morpholin-4-yl)phenyl)carbonyl-3-[3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(morpholin-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(4-methylpiperazin-1-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(4-(1,1-dioxo-thiomorpholin-4-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylaminoi-1H-1,2,4-triazole; and

5-amino-1-(4-(piperidin-1-yl)phenyl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole.

16. The compound of claim 6 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —O—R 9 —CN where R 8 is a direct bond;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, —R 8 —OR 10 , R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

17. The compound of claim 16 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —O—R 9 —CN where R 8 is a direct bond;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of nitro, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(OOR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

18. The compound of claim 17 selected from the group consisting of:

5-amino-3-[4-(cyanomethoxy)phenylamino]-1-(4-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole; and

5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(4-(iso-propoxy)phenyl)carbonyl-1H-1,2,4-triazole.

19. The compound of claim 16 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —O—R 9 —CN where R 8 is a direct bond;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, cycloalkyl, and cycloalkylalkyl;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

20. The compound of claim 19 selected from the group consisting of:

5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(4-(methyl)phenyl)carbonyl-1H-1,2,4-triazole;

5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(2-(methyl)phenyl)carbonyl-1H-1,2,4-triazole; and

5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(3-(methyl)phenyl)carbonyl-1H-1,2,4-triazole.

21. The compound of claim 3 wherein:

A is —C(O)—;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

R 8 present in the R 3 substituent is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain, an optionally substituted straight or branched alkenylene chain and an optionally substituted straight or branched alkynylene chain;

each R 10 present in the R 3 substituent and in a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl.

22. The compound of claim 21 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy:

R 2 , R 4 and R 5 are each hydrogen;

R 3 is heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

R 8 present in the R 3 substituent is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain or an optionally substituted straight or branched alkenylene chain;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain or an optionally substituted straight or branched alkenylene chain; and

R 10 present in the R 3 substituent and each R 10 present in a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, or optionally substituted heteroarylalkyl.

23. The compound of claim 22 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —OR 10 and optionally substituted with halo or alkoxy, where R 8 is a direct bond and R 10 is selected from the group consisting of 2-(pyrrolidin-1-yl)ethyl, 2-(piperidin-1-yl)ethyl, 2-(morpholin-4-yl)ethyl, 2-(1,3-dioxolan-2-y)ethyl, 2-(thiomorpholin-4-yl)ethyl, 3-(pyrrolidin-1-yl)propyl, 2-(azepan-1-yl)ethyl, 2-(isoindolin-1-yl)ethyl, 2-(imidazol-1-yl)ethyl, 2-(pyrrolidin-2-on-1-yl)ethyl, and 2-(3-fluoropyrrolidin-l-yl)ethyl;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 16 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain or an optionally substituted straight or branched alkenylene chain; and

24. The compound of claim 23 selected from the group consisting of:

5-amino-1-(3-(iso-propoxy)pyridin-5-yl)carbonyl-3-[4-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(2,2-dimethyl-2H-benzo [13][1,4]oxazin-3(4H)-on-6-yl)carbonyl-3-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1,3-benzodioxo1-5-yl)carbonyl-3-[4-[2-(piperidin-1-yflethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1,3-benzodioxo1-5-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1,4-benzodioxan-6-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -5-yl)carbonyl-3-[4-[2-(pyrrolindin1-yl)ethoxy]phenyl amino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[4-[2-(pyrrolindin1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol-2-yl)carbonyl-3-[4-[2-(pyrrolidin1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(benzimidazol-6-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenyl amino]-1H-1,2,4-triazole;

5-amino-1-(6-(methyl)pyridin-3-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(pyridin-2-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(pyridin-4-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[4-[2-(morpholin-4-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(benzo [d]thiazol-6-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(2,3-dihydrobenzofuran-5-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-benzo[d][1,2,3]triazol-5-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(3-methylthien-2-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(5-methylthien-2-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(thien-2-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(quinolin-6-yl)carbonyl-3-[4-[2-(pyrrolidin-1-y)ethoxy]phenylaminol-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[3-fluoro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1,2,3-thiadiazol-4-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxylphenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-methoxy-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[4-[2-(azepan-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[4-[2-(isoindolin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -3-yl)carbonyl-3-[4-[2-(pyrro lidin-1-y)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(benzo[b]thiophen-2-yl)carbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(benzo [b]thiophen-5-yOcarbonyl-3-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1H-indol -6-yl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-114-1,2,4-triazole;

5-amino-1-(benzo [b]thiophen-5-yl)earbonyl-3 44-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(benzo[b]thiophen-2-yl)carbonyl-3-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

5-amino-1-(1,4-benzodioxan-6-yl)carbonyl-3-[4-[2-((S)-3-fluoropyrrolidin-1-yl)ethoxy]phenylaminol-1H-1,2,4-triazole; and

5-amino-1-(1H-indol-6-yl)carbonyl-3-[4-[2-((S)-3-fluoropyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole.

25. The compound of claim 1 of formula (Ib):

wherein:

A is —C(O)—;

R 2 is hydrogen, alkyl or —C(O)R 10 ;

R 4 and R 5 are each hydrogen or alkyl;

R 3 is one of the following:

a) aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 and —R 8 —CN;

b) heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

26. The compound of claim 25 wherein:

A is —C(O)—;

R 1 is aryl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R′° is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is one of the following:

a) aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 and —R 8 —CN;

b) heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

27. The compound of claim 26 wherein:

A is —C(O)—;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(OOR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 ,) —R 9 —N(R 10 2 , —R 9 —C(OOR 10 and)—R 9 —C(O)N(R 10 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

28. The compound of claim 27 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

29. The compound of claim 28 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or two substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 ,) —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

30. The compound of claim 29 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 , where R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is cycloalkyl optionally substituted with —R 8 —OR 10 ;

or R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)NR 6 )R 7 , —SO R 6 ( (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 ) R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

R 8 present in the R 3 substituent is independently selected from the group consisting of a direct bond, an optionally substituted straight or branched alkylene chain, and an optionally substituted straight or branched alkenylene chain;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

R 10 present in a R 3 substituent and each R 10 present in a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, and optionally substituted heteroarylalkyl.

31. The compound of claim 30 selected from the group consisting of:

3-amino-1-(4-(iso-propoxy)phenyl)carbonyl-5-[4-[2-(piperidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

3-amino-1-(4-iso-propoxyphenyl)carbonyl-5-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

3-amino-1-(4-(tert-butyl)phenyl)carbonyl-5-[4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole; and

3-amino-1-(4-(morpholin-4-yl)phenyl)carbonyl-5-[3-fluoro-4-[2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole.

32. The compound of claim 29 wherein:

A is —C(O)—;

R 1 is phenyl substituted with —R 8 —O—R 9 —CN where R 8 is a direct bond;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is phenyl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , and —R 8 —CN;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain, or an optionally substituted straight or branched alkenylene chain; and

33. The compound of claim 26 wherein:

A is —C(O)—;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

R 10 present in the R 3 substituent and each R 10 present in a R 6 substituent or a R 7 substituent is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl.

34. The compound of claim 33 wherein:

A is —C(O)—;

R 1 is phenyl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy;

R 2 , R 4 and R 5 are each hydrogen;

R 3 is heteroaryl optionally substituted with one or more substituents selected from the group consisting of alkyl, oxo, and —R 8 —OR 10 ;

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, haloalkyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, —R 9 —OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 ) and —R 9 —C(O)N(R 10 ) 2 ;

each R 9 is independently selected from the group consisting of an optionally substituted straight or branched alkylene chain or an optionally substituted straight or branched alkenylene chain; and

35. The compound of claim 34 selected from the group consisting of:

3 -amino -1-(1H-indol -5-yl)carbonyl-5-[4-2-(pyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

3-amino-1-(benzo[b]thiophen-2-yl)carbonyl-5-[4-[ 2 -(pyrrolidin-1-yl)ethoxylphenyl amino]-1H-1,2,4-triazole;

3-amino-1-(1H-indol-6-yl)carbonyl-5-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

3-amino-1-(benzo [b]thiophen-5-yl)carbonyl-5-[4-[2-(imidazol-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole;

3-amino-1-(1,4-benzodioxan-6-yecarbonyl-5 44-[2-((S)-3-fluoropyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole; and

3-amino-1-(1H-indol -6-yl)carbonyl-5-[4-[2-((S)-3-fluoropyrrolidin-1-yl)ethoxy]phenylamino]-1H-1,2,4-triazole.

36. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of formula (Ia) or formula (Ib):

wherein, independently at each occurrence:

A is —C(O)—; or —C(S)—;

R 1 is one of the following: aryl substituted with at least one of —R 8 —OR 10 or —R 8 —O—R 9 —CN, where each R 8 is a direct bond and R 10 is selected from the group consisting of optionally substituted heterocyclylalkyl, optionally substituted heteroarylalkyl and optionally substituted aralkyl, and optionally substituted with one or more substituents selected from the group consisting of halo, haloalkyl, alkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and alkoxy; p 1 R 2 , R 4 and R 5 are each independently hydrogen, alkyl, aryl, aralkyl, —C(O)R 10 or —C(O)N(R 6 )R 7 ;

R 3 is one of the following: a) aryl substituted with one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, nitro, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, —R 8 —OR 10 , —R 8 —C(O)OR 10 , —R 8 —OC(O)R 10 , —R 8 —O—R 9 —C(O)OR 10 , —R 8 —O—R 9 —C(O)N(R 6 )R 7 , —S(O) p R 6 (where p is 0, 1 or 2), —S(O) t N(R 6 )R 7 (where t is 1 or 2), —R 8 —N(R 6 )R 7 , —R 8 —N(R 6 )C(O)R 10 , —R 8 —N(R 6 )C(OOR 10 and —R 8 —CN; or

R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, hydroxyalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aralkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted cycloalkylalkenyl, optionally substituted cycloalkylalkynyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heterocyclylalkenyl, optionally substituted heterocyclylalkynyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted heteroarylalkenyl, optionally substituted heteroarylalkynyl, —R 9 OR 10 , —R 9 —CN, —R 9 —NO 2 , —R 9 —N(R 10 ) 2 , —R 9 —C(O)OR 10 and —R 9 —C(O)N(R 10 ) 2 ;

optionally, R 6 and R 7 , together with the nitrogen to which they are attached, form an optionally substituted N-heteroaryl or an optionally substituted N-heterocyclyl;

as an isolated stereoisomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or N-oxide thereof.

Assignments (3)

SECURITY INTEREST Recorded May 8, 2026

From: RIGEL PHARMACEUTICALS, INC.

To: MIDCAP FUNDING IV TRUST

Reel/Frame 075576/0880 →

SECURITY INTEREST Recorded Aug 25, 2022

From: RIGEL PHARMACEUTICALS, INC.

To: MIDCAP FINANCIAL TRUST

Reel/Frame 061327/0712 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2007

From: SINGH, RAJINDER; SYLVAIN, CATHERINE; HOLLAND, SACHA; ZHANG, JING; PARTRIDGE, JOHN J.; CLOUGH, JEFFREY; ARGADE, ANKUSH

To: RIGEL PHARMACEUTICALS, INC.

Reel/Frame 019275/0590 →