IP Library Granted Patent US 10,011,615
Granted Patent B2
US 10,011,615 · App. 15/423,238 · Granted Jul 3, 2018

Heterobicyclo-substituted [1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with A2A anatagonist properties

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Quick Facts
Patent No.
US 10,011,615
App. No.
15/423,238
Granted
Jul 3, 2018
Kind
B2
Abstract

Disclosed are compounds of Formula G1: where “R G3 ”. “R d1 ” to “R d4 ”, “n”, “m”, “p”, “W”, “X”, “Y”, and “Z” are defined herein, which compounds are antagonists of A 2A receptor. Disclosed herein also are uses of the compounds described herein as antagonists of the A2A receptor in the potential treatment or prevention of neurological disorders and diseases in which A 2A receptors are involved. Disclosed herein also are pharmaceutical compositions comprising these compounds and uses of these pharmaceutical compositions.

Claims (542)

1. A compound of Formula GI:

or a pharmaceutically acceptable salt thereof, wherein:

W is nitrogen or carbon;

m is 1, 2, 3, or 4; n is an integer of from 0 to 4, wherein the sum of n+m is at least 2 up to 4, and wherein, when W is N, m is at least 2;

G d1 through G d4 are independently hydrogen or a C 1-6 -alkyl;

p is 1 or 2, wherein, p is not elected to be 1 when the values of m+n=2;

X, Y, and Z together with W and the carbon to which X and W are bonded form a 5 to 6 member aromatic or heteroaromatic moiety, and are independently:

(a) (R G1 )C═, wherein R G1 is:

(i) hydrogen;

(ii) C 1-8 -alkyl, optionally substituted with one or more halogen atoms;

(iii) —C(O)—C 1-8 -alkyl;

(iv) —CN;

(v) —S—C 1-8 -alkyl;

(vi) —O—C 1-6 -alkyl;

(vii) —(CH 2 ) q1 —(C═O) q2 —N(R 2 ) 2 , where R 2 is independently for each occurrence hydrogen, C 1-6 -alkyl or heteroaryl, and wherein q1 is 0 or 1 and q2 is 0 or 1;

(viii) —C(O)O—C 1-8 -alkyl;

(ix) halogen;

(x) a mono- or polycyclic heterocyclic moiety comprising up to 10 carbon atoms and one or more heteroatoms selected from N, S, or O, optionally substituted with one or more C 1-6 -alkyl, morpholino, phenyl (optionally substituted with halogen), heteroaryl or halogen;

(xi) aryl, which is optionally substituted with one or more substituents which are: (1) halogen; or (2) C 1-6 -alkyl which is optionally substituted with one or more halogen atoms;

(xii) —NH—C(O)—R 3 , wherein R 3 is C 1-6 -alkyl or heteroaryl; or,

(xiii) heteroaryl, which is optionally substituted with: (ai) a C 1-6 -alkyl moiety, which alkyl moiety is optionally substituted with one or more halogen atoms; or (bi) amino; or

(b) >NR G2 , wherein R G2 is: (i) hydrogen; (ii) C 1-8 -alkyl; or (iii) an aromatic moiety of up to 10 carbon atoms;

(c) N═;

(d) —O—; or,

(e) —S—; and,

R G3 is a moiety of the structure:

wherein:

t is 0, 1 or 2;

R G5 and R G6 are independently for each occurrence:

(a) H;

(b) C 1-10 -alkyl, optionally substituted with one or more fluorine atoms; or,

(c) R G5 and R G6 taken together form a carbonyl moiety (C═O), with the proviso that if t=2, R G5 and R G6 are not selected to provide two adjacent carbonyl moieties; and

R Ga1 is 1 to 3 substituents replacing an H on a ring carbon atom that are independently for each occurrence:

(a) C 1-4 -alkoxy, wherein the alkyl portion of the alkoxy moiety is optionally substituted with one or more halogen;

(b) C 1-8 -alkyl, optionally substituted with one or more halogen atoms;

(c) halogen;

(d) —CN; or

(e) —N(R G4 ) 2 , wherein at least one of R G4 is C 1-6 alkyl and the other is H or C 1-6 -alkyl.

2. A compound of claim 1 or a pharmaceutically acceptable salt thereof wherein R G3 is a moiety of the structure:

wherein:

t is 0, 1 or 2;

R G5 and R G6 are independently for each occurrence:

(a) H;

(b) C 1-10 -alkyl, optionally substituted with one or more fluorine atoms; or

(c) R G5 and R G6 taken together form a carbonyl moiety (C═O), with the proviso that if t=2, R G5 and R G6 are not selected to provide two adjacent carbonyl moieties; and,

R Ga , R Gb , and R Gc are independently:

(a) H;

(b) C 1-4 -alkoxy, wherein the alkyl portion of the alkoxy moiety is optionally substituted with one or more halogen;

(c) C 1-8 alkyl, optionally substituted with one or more halogen atoms;

(d) a halogen which is: F; or Cl;

(e) —N(R G4 ) 2 , wherein at least one of R G4 is C 1-6 -alkyl and the other is H or C 1-6 -alkyl; or,

(f) —CN;

with the proviso that at least one of R Ga , R Gb , or R Gc is H, and at least one of R Ga , R Gb , or R Gc is not H.

3. A compound of claim 1 or a pharmaceutically acceptable salt thereof wherein, when X, Y, or Z is —C(R G1 )═, and R G1 is selected to be a halogen substituted C 1-6 -alkyl moiety, the halogen is F or Cl.

4. A compound of claim 1 or a pharmaceutically acceptable salt thereof wherein at least one of X, Y, or Z is —N═, and at least one of X, Y, or Z is —O— or —S—.

5. A compound of claim 1 or a pharmaceutically acceptable salt thereof having the structure of Formula GII:

or a pharmaceutically acceptable salt thereof, wherein:

R Gaa , R Gba , and R Gca are independently for each occurrence:

(a) H;

(b) C 1-6 -alkyl;

(c) C 1-4 -alkoxy, optionally substituted with one or more fluorine atoms;

(d) F;

(e) Cl;

(f) Br;

(g) —CN; or,

(h) —N(R G9 ) 2 , wherein R G9 is independently for each occurrence C 1-6 -alkyl or H; and wherein R Gaa , R Gba , and R Gca are selected such that at least one of R Gaa , R Gba , and R Gca is H, and at least one of R Gaa , G Gba , and R Gca is not H;

R Gf is:

(a) —CH 2 —;

(b) -ethyl-, which is optionally substituted with one or more: C 1-6 -alkyl, which substituent is optionally substituted with one or more fluorine atoms;

(c) -propyl-; or,

(d) —C(O)—CH 2 —; and,

R Ge is a heteroaryl bicyclic moiety comprising up to 12 ring atoms, of the structure:

wherein:

W′ is nitrogen or carbon;

m′ is 1, 2, 3, or 4;

n′ is an integer of from 0 to 4, wherein the sum of n′+m′ is at least 2 up to 4, and wherein, when W′ is N, m′ is at least 2;

p′ is 1 or 2; wherein, p′ is not elected to be 1 when the values of m′+n′=2;

G d1′ through G d4′ are independently H or C 1-6 -alkyl;

X′, Y′, and Z′ together with W′ and the carbon to which X′ and W′ are bonded form a 5 to 6 member aromatic or heteroaromatic moiety, and are independently:

(a) —(R G1′ )C═, wherein R G1′ is:

(i) H;

(ii) C 1-8 -alkyl, optionally substituted with one or more halogen atoms;

(iii) —C(O)—C 1-8 -alkyl;

(iv) —CN;

(v) —S—C 1-8 -alkyl;

(vi) —O—C 1-6 -alkyl;

(vii) —(CH 2 ) q —C(O)—N(R 2′ ) 2 , wherein R 2 is independently for each occurrence H, C 1-4 -alkyl or pyridyl, and wherein q is 0 or 1;

(viii) —C(O)O—C 1-8 -alkyl;

(ix) halogen;

(x) morpholine, optionally substituted on any carbon atom thereof by one or more C 1-6 -alkyl moieties;

(xi) piperazine, wherein the 4-N nitrogen is bonded to a substituent which is: (ai) H; (aii) C 1-6 -alkyl; (aiii) morpholino; (aiv) phenyl, optionally substituted with a halogen; (av) halogen; or (avi) heteroaryl;

(xii) piperidinyl, optionally substituted by C 1-6 -alkyl or a morpholine moiety;

(xiii) pyrrolidine, optionally substituted with one or more halogen atoms;

(xiv) phenyl, which is optionally substituted with one or more halogen atoms or C 1-6 -alkyl; or

(xv) —NH—C(O)—R 3′ , wherein R 3′ is C 1-4 -alkyl or pyridinyl;

(xvi) heteroaryl, which is optionally substituted with CF 3 , C 1-6 -alkyl or amino; or

(xvii) —N(R 4′ ) 2 , wherein R 4′ is independently for each occurrence H or C 1-6 -alkyl;

(b) >NR G2′ , wherein R G2′ is: (i) H; (ii) C 1-8 alkyl; or (iii) an aromatic moiety of up to 10 carbon atoms;

(c) —N═;

(d) —O—; or

(e) —S—.

6. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R Ge is a moiety of Formula R GeA :

and wherein the compound is selected from a group of compounds where X 1 , Y 1 and Z 1 are as defined in Table CA:

TABLE CA

X 1

Y 1

Z 1

N

C(H)

Cl

N

N

CF 3

N

N

H

N

N

CH 3

C(H)

C(H)

H

C(H)

C(H)

CF 3

C(H)

C(H)

F

N

C(H)

H

C(F)

C(H)

H

C(F)

C(F)

H

7. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R Ge is a moiety of Formula R GeB :

and wherein the compound is selected from a group of compounds where A 2 , X 2 , Y 2 and Z 2 are as defined in Table CB:

TABLE CB

X 2

Y 2

Z 2

A 2

—C(—S—CH 3 )═

—N═

—N═

—N<

—C(—C(O)—NH—Propyl)═

—N═

—N═

—N<

—C(Br)═

—N═

—N═

—N<

—C(C(O)—O-ethyl)═

—N═

—N═

—N<

>N(cyclopropyl)

—C(H)═

—N═

>C═

—C(isopropyl)═

—C(H)═

—N═

—N<

—C(—C(O)-cyclopropyl)═

—N═

—C(H)═

—N<

—N═

—N═

—C(—CF 3 )═

—N<

—N═

—N═

—C(cyclopropyl)═

—N<

—C(ethyl)═

—C(H)═

—N═

—N<

—N═

—N(H)—

—C(—CF 3 )═

>C═

—C(—CF 3 )═

—N═

—N═

—N<

—C(ethyl)═

—N═

—N═

—N<

—N(CH 3 )—

—C(—CF 3 )═

—N═

>C═

—N(H)—

—C(H)═

—N═

>C═

—N(H)—

—C(CH 3 )═

—N═

>C═

—N(H)—

—C(CF 3 )═

—N═

>C═

—C(isopropyl)═

—N(H)—

—N═

>C═

—N═

—C(H)═

—C(CH 3 )═

—N<

—C(—CF 3 )═

—N(H)—

—N═

>C═

—C(H)═

—N═

—C(CF 3 )═

—N<

—C(ethyl)═

—N═

—N═

—N<

8. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R Ge is a moiety of Formula R GeC :

and wherein the compound is selected from a group of compounds where X 3 , Y 3 , Z 3 and A 3 are as defined in Table CC:

TABLE CC

X 3

Y 3

Z 3

A 3

N

C(Br)

C(H)

CH 2

C(H)

C(F)

C(H)

CH 2

N

C(H)

C(H)

CH 2

C(H)

C(—OCH 3 )

C(H)

CH 2

N

N

C(H)

CH 2

N

C(H)

N

CH 2

C(H)

C(H)

C(H)

C(CH 3 ) 2

N

C(H)

C(—Br)

CH 2

N

C(H)

CH 2

N

C(H)

CH 2

N

C(H)

CH 2

9. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R Ge is a moiety of Formula R GeD :

and wherein the compound is selected from a group of compounds where X 4 , Y 4 and Z 4 are as defined in Table CD:

TABLE CD

X 4

Y 4

Z 4

—N═

—O—

—C(CF 3 )═

—C(—CN)═

—C(-cyclopropyl)═

—S—

—S—

—C(CH 3 )═

—N═

—S—

—C(CF 3 )═

—N═

—O—

—C(CH 3 )═

—N═

—N═

—C(CH 3 )═

—O—

—N═

—C(CH 3 )═

—S—

—N═

—C(-isopropyl)═

—S—

—N═

—C(-isopropyl)═

—O—

—O—

—N═

—C(H)═

—S—

—C(H)═

—C(H)═

—N═

—C(H)═

—S—

—S—

—C(H)═

—N═

—N═

—C(H)═

—O—

—N═

—C(CHF 2 )═

—O—

—N═

—C(CH 2 OCH 3 )═

—O—

10. A compound of claim 5 , or a pharmaceutically acceptable salt thereof, wherein R Ge is the following moiety:

11. A compound, or a pharmaceutically acceptable salt thereof, claim 5 wherein R Gf is —CH(CH 3 )—CH 2 —; —CH 2 —CH 2 —; or —CH 2 —.

12. A compound which is:

7-methoxy-2-(2-(3-(methylthio)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-(2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl)-N-tert-butyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide;

2-(2-(3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

ethyl 7-(2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylate;

2-(2-(2-chloro-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(4-bromo-5,6-dihydro-1,7-naphthyridin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(1-cyclopropyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-isopropyl-5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(3-(trifluoromethyl)-6,7-dihydroisoxazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(7-(2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)(cyclopropyl)methanone;

7-methoxy-2-(2-(2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-cyclopropyl-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-ethyl-5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

6-(2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl)-2-cyclopropyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbonitrile;

7-methoxy-2-(2-(2-(trifluoromethyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(trifluoromethyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(7,8-dihydro-5H-pyrido[2,3-b]azepin-9(6H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-ethyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(isoindolin-2-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(trifluoromethyl)-6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-cyclopropyl-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-cyclopropyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(1-methyl-3-(trifluoromethyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydroisoxazolo[4,5-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(3-methyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(3-(trifluoromethyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-cyclopropyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(1-methyl-3-(trifluoromethyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5,6-dihydro-1,7-naphthyridin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(5-(trifluoromethyl)isoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5-fluoroisoindolin-2-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-cyclopropyl-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(7,8-dihydropyrido[4,3-b]pyrazin-6(5H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(trifluoromethyl)-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(6,7-dihydropyrazolo[1,5-a]pyrimidin-4(5H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-7,8-dihydro-4H-pyrazolo[1,5-a][1,4]diazepin-5(6H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

5-(2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carbonitrile;

2-(2-(4,4-dimethyl-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(4-methylpiperazin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-morpholino-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(pyrrolidin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-(4-ethylpiperazin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-(2,2-dimethylmorpholino)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-((2S,6R)-2,6-dimethylmorpholino)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-(4-(cyclopropylmethyl)piperazin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2-(4-(4-fluorophenyl)piperazin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(4-morpholinopiperidin-1-yl)-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(4-(4-ethylpiperazin-1-yl)-5,6-dihydro-1,7-naphthyridin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(4-(diethylamino)-5,6-dihydro-1,7-naphthyridin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(4-(3,3-difluoropyrrolidin-1-yl)-5,6-dihydro-1,7-naphthyridin-7(8H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethanone;

2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)-1-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7-(fluoromethoxy)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-chloro-2-(2-(5-fluoroisoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-chloro-2-(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-[2-(5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)ethyl]-7-fluoro[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-fluoro-2-(2-(5-fluoroisoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-ethyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-fluoro-2-(2-(2-(trifluoromethyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-fluoro-2-(2-(4-fluoroisoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-7-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

8-fluoro-2-(2-(5-fluoroisoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(3-ethyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)ethyl)-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

8-fluoro-2-(2-(4-fluoroisoindolin-2-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7,8-dimethoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-9-fluoro-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-8,9-difluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)ethyl)-7,9-difluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(3,3-difluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-2-(3,3-difluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-2-(3,3-difluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(3-fluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(3,3,3-trifluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(3,3,3-trifluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(3,3,3-trifluoro-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)butyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)butyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)butyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5-fluoroisoindolin-2-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pentyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5-fluoroisoindolin-2-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydroquinolin-1(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((2H-benzo[b][1,4]oxazin-4(3H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-methoxy-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydro-2,7-naphthyridin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((8-((4-(pyridin-2-yl)piperazin-1-yl)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-(trifluoromethyl)isoindolin-2-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((4,5-dihydro-1H-benzo[c]azepin-2(3H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydro-1,5-naphthyridin-1(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydro-1,6-naphthyridin-1(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydro-1,7-naphthyridin-1(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((7-chloro-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-1-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((2-chloro-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((3-(methylthio)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

ethyl 7-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylate;

2-((3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3-ethyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-N-tert-butyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide;

7-methoxy-2-((3-methoxy-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,5-dimethyl-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((8,8-dimethyl-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((4-bromo-5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((7,8-dihydropyrido[4,3-b]pyrazin-6(5H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((2-(trifluoromethyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-methyl-3,4-dihydro-1,8-naphthyridin-1(2H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((7,8-dihydro-5H-pyrido[2,3-b]azepin-9(6H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((2-chloro-7,8-dihydro-5H-pyrido[2,3-b]azepin-9(6H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((3,4-dihydro-1,8-naphthyridin-1(2H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((2-(pyridin-2-yl)-7,8-dihydro-5H-pyrido[2,3-b]azepin-9(6H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((4,4-dimethyl-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-9-fluoro-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

N-(2-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)picolinamide;

N-(2-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)acetamide;

2-((7-(3,4-difluorophenyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(7-(pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-((5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-N-(pyridine-3-yl)acetamide;

7-methoxy-2-((5-(pyrimidin-5-yl)isoindolin-2-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((8-(pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(2-(trifluoromethyl)pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-((7-(2-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((7-(2-amino-4-(trifluoromethyl)pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(7-(2-(trifluoromethyl)pyrimidin-5-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-bromo-2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-bromo-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

5-amino-2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-[1,2,4]triazolo[1,5-c]quinazoline-7-carbonitrile;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-5-amino-[1,2,4]triazolo[1,5-c]quinazoline-7-carbonitrile;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-(methoxymethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-(methoxymethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-(2-fluoroethoxy)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)methyl)-7-ethoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-ethoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-((5,6-dihydro-1,7-naphthyridin-7(8H)-yl)methyl)-7-(fluoromethoxy)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-methyl-6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-7-methoxy-2-(2-(2-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-2-(2-(2-(difluoromethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-2-(2-(2-(difluoromethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(R)-2-(2-(2-(difluoromethyl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

(S)-7-methoxy-2-(2-(2-(trifluoromethyl)-6,7-dihydrothiazolo[4,5-c]pyridin-5(4H)-yl) propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(3-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl) propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(3-(4-fluoroisoindolin-2-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(3-(5-fluoroisoindolin-2-yl)propyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(3-(5-(trifluoromethyl)isoindolin-2-yl)propyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

7-methoxy-2-(2-(2,7,7-trimethyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2,4-dimethyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;

2-(2-(2,6-dimethyl-6,7-dihydrooxazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine; or

7-methoxy-2-(2-(2,7,7-trimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)ethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine,

or any of the foregoing in the form of a pharmaceutically acceptable salt.

13. A pharmaceutical composition comprising an inert carrier and a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

14. A dosage form comprising the composition of claim 13 .

Assignments (1)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →