# US 11,077,090 B2 · Compounds and compositions and uses thereof

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- Number: US 11,077,090 B2
- Document ID: US11077090B2
- Status: Granted
- Kind: B2
- Application number: 15/663,672
- Filed: 2017-07-28
- Published: 2018-02-01
- Granted: 2021-08-03
- Earliest claimed: 2016-07-29
- Assignees: Sunovion Pharmaceuticals Inc.; PGI Drug Discovery LLC
- Applicants: Sunovion Pharmaceuticals Inc.; PGI Drug Discovery LLC
- Inventors: Vadim Alexandrov; Carrie A. Bowen; Taleen G. Hanania; Noel Aaron Powell
- Web page: https://patentgrep.com/patent/US11077090B2

## CPC

- A61K 31/353: 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K 31/13: Amines {(A61K31/04 takes precedence)}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 311/76: Benzo[c]pyrans
- C07D 313/08: condensed with one six-membered ring
- C12P 17/06: containing a six-membered hetero ring, e.g. fluorescein
- 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)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}

## Abstract

Compounds of formula I: are disclosed, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric diseases and disorders in a subject in need thereof are also disclosed.

## Claims

### Claim 1

A composition comprising a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof, and wherein said composition is greater than 90% enantiomerically pure.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein said composition is greater than 95% enantiomerically pure.

### Claim 3

A composition comprising a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof, and wherein said composition is greater than 90% enantiomerically pure.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein said composition is greater than 95% enantiomerically pure.

### Claim 5

A pharmaceutical composition comprising a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant, or vehicle.

### Claim 6

A pharmaceutical composition comprising a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant, or vehicle.

### Claim 7 (depends on 6)

The pharmaceutical composition of claim 6, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 5)

The pharmaceutical composition of claim 5, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 5)

The pharmaceutical composition of claim 5, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 5)

The pharmaceutical composition of claim 5, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 5)

The pharmaceutical composition of claim 5, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 12

A method for alleviating or inhibiting the progress of a neurological or psychiatric disease or disorder selected from the group consisting of depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, a movement disorder, epilepsy, Alzheimer's disease, Parkinson's disease, autism and cognitive impairments in a subject in need thereof, comprising administering to said subject an effective amount of a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is depression.

### Claim 14 (depends on 13)

The method of claim 13, wherein the depression is treatment-resistant depression (TRD), major depressive disorder (MDD), unipolar depression, bipolar depression or depression associated with another disease or disorder.

### Claim 15 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is bipolar disorder.

### Claim 16 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is pain.

### Claim 17 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is schizophrenia.

### Claim 18 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is obsessive compulsive disorder.

### Claim 19 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is addiction.

### Claim 20 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is social disorder.

### Claim 21 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is attention deficit hyperactivity disorder.

### Claim 22 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is an anxiety disorder.

### Claim 23 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is a movement disorder.

### Claim 24 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is Alzheimer's disease.

### Claim 25 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is Parkinson's disease.

### Claim 26 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is autism.

### Claim 27 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is cognitive impairments.

### Claim 28

A method of alleviating or inhibiting the progress of a neurological or psychiatric disease or disorder selected from the group consisting of depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, a movement disorder, epilepsy, Alzheimer's disease, Parkinson's disease, autism and cognitive impairments in a subject in need thereof, comprising administering to said subject an effective amount of a compound, wherein said compound is:
or a pharmaceutically acceptable salt thereof.

### Claim 29 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is depression.

### Claim 30 (depends on 29)

The method of claim 29, wherein the depression is treatment-resistant depression (TRD), major depressive disorder (MDD), unipolar depression, bipolar depression or depression associated with another disease or disorder.

### Claim 31 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is bipolar disorder.

### Claim 32 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is pain.

### Claim 33 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is schizophrenia.

### Claim 34 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is obsessive compulsive disorder.

### Claim 35 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is addiction.

### Claim 36 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is social disorder.

### Claim 37 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is attention deficit hyperactivity disorder.

### Claim 38 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is an anxiety disorder.

### Claim 39 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is a movement disorder.

### Claim 40 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is Alzheimer's disease.

### Claim 41 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is Parkinson's disease.

### Claim 42 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is autism.

### Claim 43 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is cognitive impairments.

### Claim 44 (depends on 12)

The method of claim 12, wherein said neurological or psychiatric disorder is epilepsy.

### Claim 45 (depends on 28)

The method of claim 28, wherein said neurological or psychiatric disorder is epilepsy.