# US 10,370,337 B2 · Oxy-cyanoquinolinone PDE9 inhibitors

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- Number: US 10,370,337 B2
- Document ID: US10370337B2
- Status: Granted
- Kind: B2
- Application number: 15/745,850
- Filed: 2016-07-27
- Published: 2018-09-13
- Granted: 2019-08-06
- Earliest claimed: 2015-07-29
- Assignees: Merck Sharp & Dohme Corp.
- Applicants: Merck Sharp & Dohme Corp.; Antonella Converso; Mildred L. Kaufman; Kevin Rodzinak
- Inventors: Antonella Converso; Mildred L. Kaufman; Kevin Rodzinak
- Web page: https://patentgrep.com/patent/US10370337B2

## CPC

- C07D 215/56: with oxygen atoms in position 4
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- C07D 215/54: attached in position 3
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)

## Abstract

The present invention is directed to oxycyanoquinolinone compounds which may be useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 9 (PDE9). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

## Claims

### Claim 1

A compound of the formula I, or a pharmaceutically acceptable salt thereof:
wherein:
R5 is selected from the group consisting of:
(1) —C1-6alkyl, which is unsubstituted or substituted with hydroxy, oxetane, or allyl,
(2) -tetrahydropyranyl, and
(3) —C6-7cycloalkyl;
with the proviso that the compound is other than:
4-(cyclohexyloxy)-2-oxo-1,2-dihydroquinoline-3-carbonitrile.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R5 is C1-6alkyl, which is unsubstituted or substituted with hydroxy, oxetane, or allyl.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R5 is -tetrahydropyranyl.

### Claim 4

A compound which is selected from the group consisting of:
4-(cycloheptyloxy)-2-oxo-1,2-dihydroquinoline-3-carbonitrile;
2-oxo-4-tetrahydropyran-4-yloxy-1H-quinoline-3-carbonitrile;
2-oxo-4-(2-hydroxymethyl-2-methyl-1-butyloxy)-1H-quinoline-3-carbonitrile; and
4-((3-allyloxetan-3-yl)methoxy)-2-oxo-1,2-dihydroquinoline-3-carbonitrile;
or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

A pharmaceutical composition which comprises an inert carrier and a compound of claim 1 or a pharmaceutically acceptable salt thereof.