# US 10,245,264 B2 · Substituted imidazo[1,2-a]pyrazines as soluble guanylate cyclase activators

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,245,264 B2
- Document ID: US10245264B2
- Status: Granted
- Kind: B2
- Application number: 15/575,978
- Filed: 2016-05-23
- Published: 2018-05-31
- Granted: 2019-04-02
- Earliest claimed: 2015-05-27
- Assignees: Merck Sharp & Dohme Corp.
- Applicants: Merck Sharp & Dohme Corp.
- Inventors: Joie Garfunkle; Olga Ornoski; Dann L. Parker, Jr.; Subharekha Raghavan; Libo Xu
- Web page: https://patentgrep.com/patent/US10245264B2

## CPC

- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 9/08: Vasodilators for multiple indications
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A compound of Formula I or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate (“cGMP”) and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of Formula I, or pharmaceutically acceptable salt thereofs, for their use in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical compositions which comprise compounds of Formula I or pharmaceutically acceptable salts thereof.

## Claims

### Claim 1

A compound having structural Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
C* indicates a potential chiral carbon atom;
X is
(1) O, or
(2) NH;
R1 is
(1) phenyl unsubstituted or substituted by 1, 2, or 3 halo,
(2) (C1-6)alkyl unsubstituted or substituted by (C1-3)alkyl,
(3) halo(C1-6)alkyl,
(4) (C3-7)cycloalkyl unsubstituted or substituted by 1 or 2 halo,
(5) 5- or 6-membered heteroaryl containing 1, 2, or 3 heteroatoms independently selected from N, O and S, wherein the heteroaryl is unsubstituted or substituted by 1 or 2 halo, (C1-3)alkyl, or halo(C1-3)alkyl,
(6) —(C1-3)alkyl-(C3-7)cycloalkyl, wherein the cycloalkyl is unsubstituted or substituted by 1 or 2 (C1-3)alkyl, or halo,
(7) —(C1-3)alkyl-phenyl, wherein phenyl is unsubstituted or substituted by 1, 2, or 3 halo, or
(8) —(C1-3)alkyl-heterocyclyl containing 1 or 2 heteroatoms independently selected from N and O, wherein the heterocyclyl is a 4-7 membered ring;
R2 is
(1) (C1-3)alkyl, or
(2) (C3-7)cycloalkyl;
R3 is
(1) phenyl unsubstituted or substituted by 1 or 2 halo,
(2) 5- or 6-membered heteroaryl containing 1, 2, or 3 heteroatoms independently selected from N, O and S, wherein heteroaryl is unsubstituted or substituted by 1 or 2 halo, or
(3) (C1-6)alkyl; and
R4 is
(1) hydrogen,
(2) (C1-3)alkyl,
(3) halo(C1-3)alkyl, or
(4) (C3-6)cycloalkyl.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: R1 is (C1-6)alkyl; halo(C1-6)alkyl; (C3-7)cycloalkyl unsubstituted or substituted by 1 to 2 halo; —(C1-3)alkyl-(C3-7)cycloalkyl, wherein the cycloalkyl is unsubstituted or substituted by 1 or 2 (C1-3)alkyl, or halo; or —(C1-3)alkyl-heterocyclyl containing 1 or 2 heteroatoms independently selected from N and O, wherein the heterocyclyl is a 4-7 membered ring.

### Claim 3 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein: R3 is phenyl unsubstituted or substituted by 1 or 2 halo.

### Claim 4 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein: R3 is 6-membered heteroaryl containing 1 or 2 N heteroatoms, wherein heteroaryl is unsubstituted or substituted by 1 or 2 halo.

### Claim 5 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein: R3 is (C1-6)alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is phenyl unsubstituted or substituted by 1, 2, or 3 halo; 6-membered heteroaryl containing 1 or 2 N heteroatoms, wherein the heteroaryl is unsubstituted or substituted by 1 or 2 halo, (C1-3)alkyl, or halo(C1-3)alkyl; or —(C1-3)alkyl-phenyl, wherein phenyl is unsubstituted or substituted by 1, 2, or 3 halo.

### Claim 7 (depends on 6)

The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein: R3 is phenyl unsubstituted or substituted by 1 or 2 halo.

### Claim 8 (depends on 6)

The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein: R3 is 6-membered heteroaryl containing 1 or 2 N, wherein heteroaryl is unsubstituted or substituted by 1 or 2 halo.

### Claim 9 (depends on 6)

The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein: R3 is (C1-6)alkyl.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: X is O.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: X is NH.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 12)

The pharmaceutical composition of claim 12, wherein the pharmaceutical composition further comprises one or more additional active agents.

### Claim 14 (depends on 13)

The pharmaceutical composition of claim 13, wherein the one or more additional active agents is selected from the group consisting of an angiotensin converting enzyme inhibitor, an angiotensin II receptor antagonist, a neutral endopeptidase inhibitor, an aldosterone antagonist, a renin inhibitor, an endothelin receptor antagonist, an aldosterone synthase inhibitor, a phosphodiesterase-5 inhibitor, a vasodilator, a calcium channel blocker, a potassium channel activator, a diuretic, a sympatholitic, a beta-adrenergic blocking drug, an alpha adrenergic blocking drug, a central alpha adrenergic agonist, a peripheral vasodilator, a lipid lowering agent and a metabolic altering agent.

### Claim 15 (depends on 1)

A method for activating soluble guanylate cyclase in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 1)

A method for treating hypertension in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 17 (depends on 1)

A method for treating heart failure in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 18

A compound selected from the group consisting of:
4-Amino-2-[8-(3-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2,2,3,3,3-pentafluoropropoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-methyl-2-[8-(2,2,3,3,3-pentafluoropropoxy)imidazo[1,2-a]pyrazin-6-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2,3,6-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-methyl-5-phenyl-2-[8-(2,3,6-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(3-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-(8-phenoxyimidazo[1,2-a]pyrazin-6-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-methyl-2-(8-phenoxyimidazo[1,2-a]pyrazin-6-yl)-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-methyl-5-phenyl-2-[8-(2,3,4-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-methyl-5-phenyl-2-[8-(2,3,5-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2,3-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-cyclopropyl-5-(4-fluorophenyl)-2-[8-(2,2,3,3,3-pentafluoropropoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2,3-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2,3,4-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2,3,5-trifluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(3,4-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2,4-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(4-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-(8-{[5-(trifluoromethyl)pyridin-3-yl]oxy}imidazo[1,2-a]pyrazin-6-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(cyclohexyloxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(3,5-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(3,5-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2,5-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2,5-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-[8-(2,5-difluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-{8-[(4,4-difluorocyclohexyl)oxy]imidazo[1,2-a]pyrazin-6-yl}-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(pyridin-3-yloxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(pyridin-3-yloxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-{8-[(3,3-difluorocyclobutyl)methoxy]imidazo[1,2-a]pyrazin-6-yl}-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-{8-[(3,3-difluorocyclobutyl)methoxy]imidazo[1,2-a]pyrazin-6-yl}-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-{8-[(3,3-difluorocyclobutyl)methoxy]imidazo[1,2-a]pyrazin-6-yl}-5-(5-fluoropyridin-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-{8-[(2,2,3,3,3-pentafluoropropyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-Amino-2-(8-(3-fluorophenoxy)-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-(8-phenoxy-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one,
4-amino-2-(8-(2,3-difluorophenoxy)-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one,
4-amino-2-[2-cyclopropyl-8-(3-fluorophenoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-Amino-5-(4-fluorophenyl)-5-methyl-2-(8-propoxyimidazo[1,2-a]pyrazin-6-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-Amino-5-(4-chlorophenyl)-2-{8-[(2-methoxyethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-{8-[2-(2,2-difluorocyclopropyl)ethoxy]imidazo[1,2-a]pyrazin-6-yl}-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-{8-[2-(3,3-difluorocyclobutyl)ethoxy]imidazo[1,2-a]pyrazin-6-yl}-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(cyclohexylmethoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(2-cyclopropylethoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(cyclopentylmethoxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(cyclopentyloxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(2,2,3,3,3-pentafluoropropoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(benzyloxy)imidazo[1,2-a]pyrazin-6-yl]-5-(4-chlorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-(8-propoxyimidazo[1,2-a]pyrazin-6-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-[8-(2-cyclopropylethoxy)imidazo[1,2-a]pyrazin-6-yl]-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(2-methylpropoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-2-{8-[(2-methoxyethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-(8-{[(3,3-difluorocyclobutyl)methyl]amino}imidazo[1,2-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-(8-{[(1-ethylcyclopropyl)methyl]amino}imidazo[1,2-a]pyrazin-6-yl)-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-{8-[(cyclohexylmethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-(8-{[(2,2-dimethylcyclopropyl)methyl]amino}imidazo[1,2-a]pyrazin-6-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-(8-{[(1-ethylcyclopropyl)methyl]amino}imidazo[1,2-a]pyrazin-6-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-2-(8-{[(3,3-difluorocyclobutyl)methyl]amino}imidazo[1,2-a]pyrazin-6-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(tetrahydro-2H-pyran-4-ylmethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-2-[8-(benzylamino)imidazo[1,2-a]pyrazin-6-yl]-5-(4-chlorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(2,2,3,3,3-pentafluoropropyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(propylsulfanyl)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-{8-[(2-methylpropyl)sulfanyl]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-{8-[(3,3,3-trifluoropropyl)sulfanyl]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-fluorophenyl)-5-methyl-2-[8-(1-methylbutoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(tetrahydro-2H-pyran-3-ylmethoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(tetrahydro-2H-pyran-3-ylmethoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-[8-(tetrahydro-2H-pyran-2-ylmethoxy)imidazo[1,2-a]pyrazin-6-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(1S)-1-phenylethoxy]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(tetrahydro-2H-pyran-2-ylmethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(tetrahydro-2H-pyran-3-ylmethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(1-phenylethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one, and
4-amino-5-(4-chlorophenyl)-5-methyl-2-{8-[(1-phenylethyl)amino]imidazo[1,2-a]pyrazin-6-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
or a pharmaceutically acceptable salt thereof.