IP Library Granted Patent US 9,855,269
Granted Patent B2
US 9,855,269 · App. 15/454,793 · Granted Jan 2, 2018

Aminoquinazoline and pyridopyrimidine derivatives

Inventors: Huifen Chen (Burlingame, CA); Terry Crawford (San Mateo, CA); Seth F. Harris (El Granada, CA); Steven R. Magnuson (Dublin, CA); Chudi Nbdubaku (San Francisco, CA); Lan Wang (Foster City, CA)
Assignee: Genentech, Inc.
A61K31/519A61K31/5377A61K31/551A61K31/553
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Quick Facts
Patent No.
US 9,855,269
App. No.
15/454,793
Granted
Jan 2, 2018
Kind
B2
Abstract

The invention provides a method of inhibiting angiogenesis in a patient by administering a compound of formula (I): wherein R 1 R 2 and R 3 are as defined herein, compositions including the compounds and methods of using the compounds.

Claims (342)

1. A method for the inhibition of angiogenesis which method comprises administering to a patient a therapeutically effective amount of a compound of claim formula (I)

and stereoisomers, geometric isomers, tautomers, or pharmaceutically acceptable salts thereof, wherein:

R 1 is —NR—C 1 -C 12 -hydroxyalkyl, —NR—(C 1 -C 12 -alkylenyl) n -C 3 -C 6 -cycloalkyl, —NR—(C 1 -C 12 -alkylenyl) n -heterocyclyl, —NR—(C 1 -C 12 -alkylenyl) n -C 6 -C 20 -aryl, —NR—(C 1 -C 12 -alkylenyl) n -heteroaryl, —NR—(C 1 -C 12 -alkylenyl) n -C 6 -C 20 -aryloxy, C 6 -C 20 -aryl, pyridine, N-linked piperidine, N-linked pyrrolidine, N-linked piperazine, N-linked morpholine, 1H-pyrazol-4-yl, C 6 -C 20 -aryloxy or heteroaryloxy, each of which can be unsubstituted or substituted by one or more substituent(s) selected from the group consisting of:

CN;

oxo;

OH;

NH 2 ;

halo;

C 1 -C 12 -alkyl;

(C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy, unsubstituted or substituted by one or more substituent(s) selected from the group consisting of C 3 -C 6 -cycloalkyl, heterocyclyl, aryl and heteroaryl;

C 1 -C 12 -hydroxyalkyl;

C 1 -C 12 -haloalkyl;

C 1 -C 12 -haloalkoxy;

(C 1 -C 12 -alkylenyl) n -C(O)O—C 1 -C 12 -alkyl;

—C(O)—C 1 -C 12 -alkyl;

O—R′, wherein R′ is C 3 -C 6 -cycloalkyl, heterocycloalkyl, aryl or heteroaryl, each of which are unsubstituted or substituted by one or more R g ;

—(C 1 -C 12 -alkylenyl) n -cycloalkyl or (C 1 -C 12 -alkylenyl) n -heterocyclyl unsubstituted or substituted by one or more substituent(s) selected from the group consisting of:

halo, oxo, OH, NH 2 , C 1 -C 12 -alkyl, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -haloalkyl, (C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy, —NH(C 1 -C 12 -alkyl), —N(C 1 -C 12 -alkyl) 2 , —N(C 1 -C 12 -alkyl)-C(O)—C 1 -C 12 -alkyl, —C(O)—C 1 -C 12 -alkyl, —C(O)O—C 1 -C 12 -alkyl, (C 1 -C 12 -alkylenyl) n -C(O)—NH 2 , (C 1 -C 12 -alkylenyl) n -C(O)—NH(C 1 -C 12 -alkyl), —C(O)—NH(C 1 -C 12 -hydroxyalkyl), (C 1 -C 12 -alkylenyl) n -C(O)—N(C 1 -C 12 -alkyl) 2 , —C(O)—NH(C 1 -C 12 -haloalkyl), —C(O)—NH-heterocyclyl, —S(O) 2 —C 1 -C 12 -alkyl, —S(O) 2 —N(C 1 -C 12 -alkyl) 2 , —C(O)OH, —C(O)-heterocyclyl, (C 1 -C 12 -alkylenyl) n -heterocyclyl and (C 1 -C 12 -alkylenyl) n -heteroaryl, which heterocyclyl and heteroaryl group(s) can be unsubstituted or substituted by one or more substituent(s) selected from the group consisting of:

OH, NH 2 , halo, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 12 -haloalkyl and C 1 -C 12 -hydroxyalkyl;

(C 1 -C 12 -alkylenyl) n -aryl or (C 1 -C 12 -alkylenyl) n -heteroaryl, wherein the aryl or heteroaryl is unsubstituted or substituted by one or more substituent(s) selected from the group consisting of:

halo, OH, NH 2 , C 1 -C 12 -alkyl, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -haloalkyl, (C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy, —NH(C 1 -C 12 -alkyl), —N(C 1 -C 12 -alkyl) 2 , —N(C 1 -C 12 -alkyl)C(O)—C 1 -C 12 -alkyl, —C(O)—C 1 -C 12 -alkyl, —C(O)—NH 2 , —C(O)—NH(C 1 -C 12 -alkyl), —C(O)—NH(C 1 -C 12 -hydroxyalkyl), —C(O)—N(C 1 -C 12 -alkyl) 2 , —C(O)—NH(C 1 -C 12 -haloalkyl), —C(O)—NH-heterocyclyl, —S(O) 2 —C 1 -C 12 -alkyl, —S(O) 2 —N(C 1 -C 12 -alkyl) 2 , C 1 -C 12 -alkylenyl-C(O)N(C 1 -C 12 -alkyl) 2 , —C(O)OH, —C(O)-heterocyclyl and heterocyclyl, which heterocyclyl group(s) can be unsubstituted or substituted by one or more substituent(s) selected from the group consisting of:

OH, NH 2 , halo, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 12 -haloalkyl, and C 1 -C 12 -hydroxyalkyl;

(C 1 -C 12 -alkylenyl) n -NR a R b , wherein R a and R b are independently selected from:

H,

C 1 -C 12 -alkyl,

C 1 -C 12 -hydroxyalkyl,

C 1 -C 12 -haloalkyl,

(C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy,

—S(O) 2 —(C 1 -C 12 -alkylenyl) n -heterocyclyl unsubstituted or substituted by one or more R g ,

(C 1 -C 12 -alkylenyl) n -C 6 -C 20 -aryl, which aryl is unsubstituted or substituted by one or more R g ,

(C 1 -C 12 -alkylenyl) n -C 3 -C 6 -cycloalkyl unsubstituted or substituted by one or more R g ,

(C 1 -C 12 -alkylenyl) n -heterocyclyl unsubstituted or substituted by one or more oxo, —C(O)—C 1 -C 12 -alkyl, —C(O)O—C 1 -C 12 -alkyl or R g ,

C 1 -C 12 -alkylenyl-C(O)-heteroaryl unsubstituted or substituted by one or more R g ,

C 1 -C 12 -alkylenyl-NH 2 ,

C 1 -C 12 -alkylenyl-NH(C 1 -C 12 -alkyl),

C 1 -C 12 -alkylenyl-N(C 1 -C 12 -alkyl) 2 ,

C 1 -C 12 -alkylenyl-C(O)NH 2 ,

C 1 -C 12 -alkylenyl-C(O)NH(C 1 -C 12 -alkyl), or,

C 1 -C 12 -alkylenyl-C(O)N(C 1 -C 12 -alkyl) 2 ,

(C 1 -C 12 -alkylenyl) n -C(O)NR c R d , wherein R c and R d are independently selected from:

H,

C 1 -C 12 -alkyl,

C 1 -C 12 -hydroxyalkyl,

C 1 -C 12 -haloalkyl,

(C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy,

C 1 -C 12 -alkylenyl-NH(C 1 -C 12 -alkyl),

C 1 -C 12 -alkylenyl-N(C 1 -C 12 -alkyl) 2 ,

(C 1 -C 12 -alkylenyl) n -heterocyclyl, unsubstituted or substituted by one or more substituent(s) selected from the group consisting of oxo, —C(O)—C 1 -C 12 -alkyl and R g ,

(C 1 -C 12 -alkylenyl) n -C 3 -C 6 -cycloalkyl unsubstituted or substituted by one or more R g ,

(C 1 -C 12 -alkylenyl) n -C 6 -C 20 -aryl unsubstituted or substituted by one or more R g ,

—NH—C 3 -C 6 -cycloalkyl; or

or R c and R d together with the nitrogen atom to which they are attached, form a 5 or 6 membered heterocyclyl which can or cannot comprise 1 or 2 additional heteroatom selected from N, O or S; and,

(C 1 -C 12 -alkylenyl) n -NR e C(O)R f , wherein R e is H or C 1 -C 12 -alkyl, R f is halo, CN, OH, C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, (C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -cyanoalkyl, (C 1 -C 12 -alkylenyl) n -NH 2 , (C 1 -C 12 -alkylenyl) n -NH(C 1 -C 12 -alkyl), (C 1 -C 12 -alkylenyl) n -N(C 1 -C 12 -alkyl) 2 , (C 1 -C 12 -alkylenyl) n -C 3 -C 6 -cycloalkyl, (C 1 -C 12 -alkylenyl) n -heterocyclyl, or (C 1 -C 12 -alkylenyl) n -NH—C 3 -C 6 -cycloalkyl, wherein said cycloalkyl, heterocyclyl or heteroaryl are unsubstituted or substituted by oxo, —C(O)—C 1 -C 12 -alkyl or one or more R g ;

R 2 is H, CN, —C(O)—NH(C 1 -C 12 -alkyl)-NH—C(O)—C 1 -C 12 -alkyl, —C(O)—N(C 1 -C 12 -alkyl)(C 1 -C 12 -alkoxy), —C(O)—N(C 1 -C 12 -alkyl)(C 1 -C 12 -alkylalkoxy), —C(O)—NH(heterocyclyl), —C(O)—NH(C 1 -C 12 -alkyl-heterocyclyl), —C(O)—N(C 1 -C 12 -alkyl)(heterocyclyl), or —C(O)-heterocyclyl, which heterocyclyl groups are unsubstituted or substituted by one or more R g , —N(C 1 -C 12 -alkyl)-C(O)—C 1 -C 12 -alkyl, or —N(C 1 -C 12 -alkyl) 2 ;

R 3 is H, i-butyl, C 1 -C 12 -haloalkyl, cyclobutyl, —C(O)—C 1 -C 12 -alkyl-C 3 -C 6 -cycloalkyl, —C(O)—C 1 -C 12 -alkyl-heterocyclyl —C(O)—C 1 -C 12 -alkyl-C 6 -C 20 -aryl, —C(O)—C 1 -C 12 -alkyl-heteroaryl or pyridinyl;

R is H or C 1 -C 12 -alkyl;

R g is H, OH, halo, NH 2 , C 1 -C 12 -alkyl, (C 1 -C 12 -alkylenyl) n -C 1 -C 12 -alkoxy, C 1 -C 12 -haloalkyl, C 1 -C 12 -haloalkoxy, C 1 -C 12 -hydroxyalkyl, or C 1 -C 12 -cyanoalkyl;

n is 0 or 1;

wherein in the preceeding heteroaryl groups are 5 or 6 membered heteroaryls comprising 1, 2 or 3 heteroatom(s) selected from N, O or S and heterocyclyl groups are 5 to 10 membered heterocyclyls comprising 1, 2 or 3 heteroatom(s) selected from N, O or S;

with the proviso that the compound of Formula I is not:

2. The method of claim 1 wherein the compound of formula I is selected from the group consisting of:

6-(2-fluoro-4-pyridyl)pyrido[3,2-d]pyrimidin-4-amine;

4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)pyridin-2(1H)-one;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(1-hydroxy-2-methylpropan-2-yl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-methylbenzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-cyclobutyl-5-fluorobenzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(2-hydroxyethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(3-hydroxycyclobutyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(1-hydroxypropan-2-yl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-((1-methylpiperidin-4-yl)methyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(2-morpholinoethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(dimethylamino)ethyl)-5-fluorobenzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzoic acid;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(3-hydroxycyclobutyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-hydroxyethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(1-hydroxypropan-2-yl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(1-hydroxy-2-methylpropan-2-yl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-cyclobutylbenzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-methylbenzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-morpholinoethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-((1-methylpiperidin-4-yl)methyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(dimethylamino)ethyl)benzamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide;

6-(3-fluorophenyl)-N-isopropylpyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluorophenyl)-N-methylpyrido[3,2-d]pyrimidin-4-amine;

N-(cyclobutyl)-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

N-(cyclopropylmethyl)-6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluorophenyl)-N-ethylpyrido[3,2-d]pyrimidin-4-amine;

Ethyl 4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)piperidine-1-carboxylate;

6-(3-fluoro-5-(2-(pyrrolidin-1-yl)ethylamino)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-Fluoro-5-(3-(pyrrolidin-1-ylmethyl)oxetan-3-ylamino)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

N-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorophenyl)pyrrolidine-1-sulfonamide;

2-Morpholin-4-yl-ethanesulfonic acid[3-(4-amino-pyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-phenyl]-amide;

N-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorophenyl)-2-(piperidin-1-yl)ethanesulfonamide;

N-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethanesulfonamide;

6-[3-(2-Pyrrolidin-1-ylmethyl-cyclopropyl)-phenyl]-pyrido[3,2-d]pyrimidin-4-ylamine;

6-(3-(Pyridin-2-yloxy)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-Fluoro-5-(4-methyl-1H-pyrazol-3-yl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(4-methyl-1H-pyrazol-3-yl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(Cyclopentyloxy)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

tert-butyl N-[(3S)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]carbamate;

(S)-6-(3-aminopiperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

N-[(3S)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-3-methoxy-propanamide;

N-(6-(3-amino-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-yl)-2-(pyrrolidin-1-yl)acetamide;

N-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorophenyl)-2-(pyrrolidin-1-yl)acetamide;

N6-(2-methylbenzyl)pyrido[3,2-d]pyrimidine-4,6-diamine;

6-(o-tolyloxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(2-(pyrrolidin-1-yl)ethoxyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluorophenyl)-N-isobutylpyrido[3,2-d]pyrimidin-4-amine;

1-[4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)piperazin-1-yl]ethanone;

6-[3-(4-methyl-1H-pyrazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(1,4-dimethyl-1H-pyrazol-3-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(1,4-dimethyl-1H-pyrazol-5-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

1-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-1,4-diazepan-1-yl)ethanone;

1-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperazin-1-yl)ethanone;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-4-ol;

6-(3-fluoro-5-((methyl(1-methylpiperidin-4-yl)amino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-4-yl)methanol;

2-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperazin-1-yl)ethanol;

6-(3-fluoro-5-((4-(2-methoxyethyl)piperazin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

(S)-6-(3-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N,N-dimethylpiperazine-1-carboxamide;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidine-4-carboxamide;

6-(3-((3,3-difluoroazetidin-1-yl)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N,N-dimethylpiperazine-1-sulfonamide;

6-(3-((1,4-oxazepan-4-yl)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperazin-1-yl)-N,N-dimethylacetamide;

1-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperazin-1-yl)-2-methylpropan-1-one;

6-(3-fluoro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-((methyl(1,1-dioxo-tetrahydrothiophen-3-yl)amino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-((3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)(methyl)amino)-1-morpholinoethanone;

N-(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)pyrrolidin-3-yl)-N-methylacetamide;

(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)azetidin-3-yl)(4-methylpiperazin-1-yl)methanone;

6-(3-((4-(dimethylamino)piperidin-1-yl)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-((4-methoxypiperidin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-(pyrrolidin-1-ylmethyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-((2-methylpyrrolidin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-((methyl(1-methylpyrrolidin-3-yl)amino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-((3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)(methyl)amino)-N,N-dimethylacetamide;

6-(3-fluoro-5-(((2-methoxyethyl)(methyl)amino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N,1-dimethylpiperazine-2-carboxamide;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)azetidine-3-carboxamide;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N-methylpyrrolidine-3-carboxamide;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N,N-dimethylazetidine-3-carboxamide;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-1-methylpiperazine-2-carboxamide;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N-methylazetidine-3-carboxamide;

2-(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-4-yl)-N,N-dimethylacetamide;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N-methylmorpholine-2-carboxamide;

6-(3-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-3-yl)methanol;

6-(3-fluoro-5-((3-morpholinopyrrolidin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluoro-5-((4-methylpiperazin-1-yl)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-3-ol;

(R)-1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)piperidin-3-ol;

6-(3-((cyclopropylamino)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)ethanol;

6-(3-((cyclopropylmethylamino)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((cyclobutylamino)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((oxetan-3-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((isobutylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)propan-1-ol hydrochloride;

6-(3-((cyclopentylamino)methyl)-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

N1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzyl)-N2,N2-dimethylethane-1,2-diamine hydrochloride;

6-(3-fluoro-5-((isopropylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((tetrahydro-2H-pyran-4-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-(((tetrahydrofuran-3-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)-N,N-dimethylacetamide hydrochloride;

6-(3-fluoro-5-((4-methylcyclohexylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((2-(pyrrolidin-1-yl)ethylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((1-methylpiperidin-4-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((cyclopropylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)ethanol hydrochloride;

6-(3-((cyclopropylmethylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((cyclobutylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-((oxetan-3-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-((isobutylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)propan-1-ol hydrochloride;

N1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzyl)-N2,N2-dimethylethane-1,2-diamine hydrochloride;

6-(3-((isopropylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((tetrahydro-2H-pyran-4-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-(((tetrahydrofuran-3-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-(((tetrahydro-2H-pyran-4-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)cyclohexanol;

(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)cyclopropyl)methanol hydrochloride;

6-(3-fluoro-5-(((1-methylpiperidin-2-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-(((1-methylpiperidin-4-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((2-morpholinoethylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

1-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)piperidin-1-yl)ethanone hydrochloride;

6-(3-fluoro-5-((2-methyl-1-morpholinopropan-2-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-fluoro-5-((1-methylazetidin-3-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

ethyl 4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzylamino)piperidine-1-carboxylate hydrochloride;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)propan-1-ol hydrochloride;

6-(3-((cyclopentylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

2-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)-N,N-dimethylacetamide hydrochloride;

6-(3-((4-methylcyclohexylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((2-(pyrrolidin-1-yl)ethylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((1-methylpiperidin-4-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-(((tetrahydro-2H-pyran-4-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

N1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzyl)cyclohexane-1,4-diamine hydrochloride;

(1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)cyclopropyl)methanol hydrochloride;

6-(3-(((1-methylpiperidin-2-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-(((1-methylpiperidin-4-yl)methylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((2-morpholinoethylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

1-(4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)piperidin-1-yl)ethanone hydrochloride;

6-(3-((2-methyl-1-morpholinopropan-2-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

6-(3-((1-methylazetidin-3-ylamino)methyl)phenyl)pyrido[3,2-d]pyrimidin-4-amine hydrochloride;

Ethyl 4-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzylamino)piperidine-1-carboxylate hydrochloride;

6-(3-chlorophenyl)pyrido[3,2-d]pyrimidine-2,4-diamine;

6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-methyl-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-methoxy-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(trifluoromethyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(trifluoromethyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(methoxymethyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]methanol;

N6-[2-(4-fluorophenyl)ethyl]pyrido[3,2-d]pyrimidine-4,6-diamine

6-(1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-4-piperidyl]-pyrrolidin-1-yl-methanone;

6-(3-morpholinopyrrolidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

6-[4-(2-methoxyethyl)piperazin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

N-[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)pyrrolidin-3-yl]-N-methyl-acetamide;

1-[4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)piperazin-1-yl]ethanone;

1-[4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)piperazin-1-yl]-2-methyl-propan-1-one;

6-[3-(4-methyl-1H-pyrazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

tert-butyl 4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-2-methyl-piperazine-1-carboxylate;

2[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-4-piperidyl]-N-methyl-acetamide;

6-[4-(1H-pyrazol-5-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[4-(6-methyl-2-pyridyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(3-morpholino-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(5-methyl-2-pyridyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[(1-methylimidazol-2-yl)methyl]pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(5-methyl-1,2,4-oxadiazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[4-(3-methylimidazol-4-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(3-amino-5-fluoro-phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(4-pyridylmethyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(3-methylimidazol-4-yl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-methyl-pyrrolidine-3-carboxamide;

6-[3-(2-pyridylmethyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(3-pyridylmethyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-(4-methylpiperazin-1-yl)pyrido[3,2-d]pyrimidin-4-amine;

6-(4-methoxy-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(dimethylamino)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

ethyl 4-[(4-aminopyrido[3,2-d]pyrimidin-6-yl)amino]piperidine-1-carboxylate;

6-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)pyrido[3,2-d]pyrimidin-4-amine;

N6-cyclopentylpyrido[3,2-d]pyrimidine-4,6-diamine;

4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-cyclopentyl-morpholine-2-carboxamide;

6-[3-(6-methyl-2-pyridyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

tert-butyl 4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)piperazine-1-carboxylate;

6-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

N-[3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-phenyl]-2-cyclopentyl-acetamide;

N6-benzylpyrido[3,2-d]pyrimidine-4,6-diamine;

6-[3-(4-methyl-1H-pyrazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(4,6-dimethylpyrimidin-2-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-N,N-dimethyl-pyridine-2-carboxamide;

6-[3-[(5-methyl-2-pyridyl)methyl]pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(pyrimidin-2-ylmethyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[6-(dimethylamino)-2-pyridyl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(pyrimidin-2-ylmethyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(4-methylsulfonyl-1H-pyrazol-5-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[6-(dimethylamino)pyrazin-2-yl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[[6-(methylamino)pyrimidin-4-yl]methyl]pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(2-methylpyrimidin-4-yl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[6-(dimethylamino)-2-methyl-pyrimidin-4-yl]pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[[6-(dimethylamino)pyrimidin-4-yl]methyl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(1H-pyrazol-3-yl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[[6-(dimethylamino)pyrimidin-4-yl]methyl]pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[2-(dimethylamino)pyrimidin-4-yl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]pyridine-2-carboxamide;

6-[3-[3-(dimethylamino)pyrazin-2-yl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(2-methylpyrimidin-4-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine; 6-(3-pyrimidin-4-yl-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[5-(trifluoromethyl)-1H-pyrazol-3-yl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(3-pyrazin-2-yl-1-piperidyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(pyrazin-2-ylmethyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[5-(dimethylamino)-2-pyridyl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-;amine;

6-[3-(4-methylpyrimidin-2-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(2-pyridyl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(4-methyl-1,2,4-triazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[5-(methoxymethyl)-1,2,4-oxadiazol-3-yl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-N-methyl-pyridine-2-carboxamide;

6-[3-(5-methylsulfonylpyrimidin-4-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[3-(4-pyridyl)pyrrolidin-1-yl]pyrido[3,2-d]pyrimidin-4-amine;

6-(2-ethyl-4-pyridyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(2-methyl-4-pyridyl)pyrido[3,2-d]pyrimidin-4-amine;

6-[3-[(1-methylimidazol-2-yl)methyl]-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

N-[3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-phenyl]-2-pyrrolidin-1-yl-acetamide;

N-[6-(3-amino-5-fluoro-phenyl)pyrido[3,2-d]pyrimidin-4-yl]-2-pyrrolidin-1-yl-acetamide;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)phenol;

5-[1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-2-methyl-pyrazol-3-ol

6-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyrido[3,2-d]pyrimidin-4-amine

6-[3-(1H-pyrazol-3-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine

6-[2-(1H-pyrazol-3-yl)morpholin-4-yl]pyrido[3,2-d]pyrimidin-4-amine

6-[3-(1H-imidazol-2-yl)-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine

[(3R)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]carbamate;

6-[(3S)-3-amino-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

6-[(3R)-3-amino-1-piperidyl]pyrido[3,2-d]pyrimidin-4-amine;

N-[(3S)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-3-pyrrolidin-1-yl-propanamide;

N-[(3S)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-2-(4-methylpiperazin-1-yl)acetamide;

N-[(3R)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-3-methoxy-propanamide;

N-[(3R)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-3-pyrrolidin-1-yl-propanamide;

N-[(3R)-1-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-3-piperidyl]-2-(4-methylpiperazin-1-yl)acetamide;

N6[(2-fluorophenyl)methyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-(1-phenylethyl)pyrido[3,2-d]pyrimidine-4,6-diamine;

6-[2-(trifluoromethyl)-4-pyridyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(2-methylphenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-methylphenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(4-pyridyloxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(4-methylphenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-fluorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

2-(4-aminopyrido[3,2-d]pyrimidin-6-yl)oxybenzonitrile;

6[(6-methyl-3-pyridyl)oxy]pyrido[3,2-d]pyrimidin-4-amine;

6[(2-methyl-3-pyridyl)oxy]pyrido[3,2-d]pyrimidin-4-amine;

6-phenoxypyrido[3,2-d]pyrimidin-4-amine;

6-(3-pyridyloxy)pyrido[3,2-d]pyrimidin-4-amine;

4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)oxybenzamide;

4-(4-aminopyrido[3,2-d]pyrimidin-6-yl)oxybenzonitrile;

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)oxybenzonitrile;

6-(2-chlorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(4-methoxyphenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(4-chlorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-chlorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(2,4-difluorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

6-(3,4-difluorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

N6-[(2-chlorophenyl)methyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

6-(2-fluorophenoxy)pyrido[3,2-d]pyrimidin-4-amine;

N6-[(3-chlorophenyl)methyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-[(4-chlorophenyl)methyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-(o-tolylmethyl)pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-[1-(6-methyl-2-pyridyl)ethyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-[(3-pyrrolidin-1-ylphenyl)methyl]pyrido[3,2-d]pyrimidine-4,6-diamine;

N6-(pyrazin-2-ylmethyl)pyrido[3,2-d]pyrimidine-4,6-diamine;

6-[3-(difluoromethoxy)phenyl]pyrido[3,2-d]pyrimidin-4-amine;

6-(3-(6-methylpyridin-2-yloxy)phenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-isopropoxyphenyl)pyrido[3,2-d]pyrimidin-4-amine;

6-(1H-indazol-4-yl)pyrido[3,2-d]pyrimidin-4-amine;

6-(3-methoxyphenyl)pyrido[3,2-d]pyrimidin-4-amine; and

N1-(3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorophenyl)-N3,N3-dimethylpropane-1,3-diamine formate; or,

a free base, pharmaceutically acceptable salt or a stereoisomer thereof.

Continuity (4)
Division 15184310 · Jun 16, 2016
Division 13906626 · May 31, 2013
Provisional Application 61653812 · May 31, 2012
Related Publication 20170173026A1 · Jun 22, 2017