# US 2014/0194508 A1 · Synthesis, methods of using, and compositions of cycloalkylmethylamines

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

- Number: US 2014/0194508 A1
- Document ID: US20140194508A1
- Status: Published application
- Kind: A1
- Application number: 14/203,364
- Filed: 2014-03-10
- Published: 2014-07-10
- Earliest claimed: 2006-09-15
- Assignees: Reviva Pharmaceuticals, Inc.
- Applicants: Reviva Pharmaceuticals, Inc.
- Inventors: Laxminarayan BHAT; Seema Rani Bhat
- Web page: https://patentgrep.com/patent/US20140194508A1

## CPC

- C07C 229/34: the carbon skeleton containing six-membered aromatic rings
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 7/12: Antidiuretics, e.g. drugs for diabetes insipidus (ADH A61P5/10)
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/08: for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A61P 15/10: for impotence
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/06: Antimigraine agents
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 25/30: for treating abuse or dependence
- A61P 25/36: Opioid-abuse
- C07C 229/14: to carbon atoms of carbon skeletons containing rings
- C07C 271/16: to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
- C07C 2601/04: with a four-membered ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides novel cycloalkylmethylamine analogs, and methods of preparing cycloalkylmethylamine analogs. The present invention also provides methods of using cycloalkylmethylamine analogs and compositions of cycloalkylmethylamine analogs. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications.

## Claims

### Claim 1

A cycloalkylmethylamine derivative of structural Formula (IV):
or a pharmaceutically acceptable salt thereof, wherein:
n is 1;
SP is a spacer selected from the group consisting of propylene, methylpropylene, and butylene;
X is O, S, or NH;
R2 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl;
R4 is hydrogen, alkyl, or substituted alkyl;
R5 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy;
R6 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl; and
R7 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy; wherein substituted means that one or more hydrogen atoms of the chemical moiety are each independently replaced with halogen, alkyl, alkoxy, or amino.

### Claim 2 (depends on 1)

The cycloalkylmethylamine derivative of claim 1, wherein
R2 is hydrogen, alkyl, aryl, or arylalkyl;
R4 is hydrogen or alkyl;
R5 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy;
R6 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, or substituted arylalkyl; and
R7 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy.

### Claim 3 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein SP is propylene or butylene.

### Claim 4 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein and X is O.

### Claim 5 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein and X is NH.

### Claim 6 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R2 is ethyl, n-propyl, isopropyl or n-butyl, s-butyl, or t-butyl.

### Claim 7 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R4 is H.

### Claim 8 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R5 is hydroxyl, alkoxy or halogen.

### Claim 9 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R6 is alkyl or substituted alkyl.

### Claim 10 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R7 is hydrogen, alkoxy, or halogen.

### Claim 11 (depends on 2)

The cycloalkylmethylamine derivative of claim 2, wherein R5 and R7 are halogen.

### Claim 12 (depends on 11)

The cycloalkylmethylamine derivative of claim 11, wherein R5 and R7 are chloro.

### Claim 13 (depends on 1)

The cycloalkylmethylamine derivative of claim 1, wherein SP=—(CH2)3— or —(CH2)4—; R2 is alkyl; R4 is hydrogen; R5 is halogen; R6 is alkyl, aryl, arylalkyl; and R7 is hydrogen.

### Claim 14 (depends on 1)

The cycloalkylmethylamine derivative of claim 1, which is
wherein n=2 or 3.

### Claim 15 (depends on 2)

A method of treating obesity, comprising administering to a subject the cycloalkylmethylamine derivative according to claim 2.

### Claim 16 (depends on 2)

A method of treating depression, comprising administering to a subject the cycloalkylmethylamine derivative according to claim 2.

### Claim 17

A cycloalkylmethylamine derivative of Compound 54a,

### Claim 18

A cycloalkylmethylamine derivative of structural Formula (IV):
or a pharmaceutically acceptable salt thereof, wherein:
n is 1;
SP is a direct bond;
X is O, S, or NH;
R2 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl;
R4 is hydrogen, alkyl, or substituted alkyl;
R5 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy;
R6 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl; and
R7 is hydrogen, alkyl, halogen, hydroxyl, or alkoxy; wherein substituted means that one or more hydrogen atoms of the chemical moiety are each independently replaced with halogen, alkyl, alkoxy, or amino.

### Claim 19 (depends on 18)

The cycloalkylmethylamine derivative of claim 18, wherein R2 is ethyl, n-propyl, isopropyl or n-butyl, s-butyl, or t-butyl; and R4 is H.

### Claim 20 (depends on 18)

The cycloalkylmethylamine derivative of claim 18, wherein R5 is hydroxyl, alkoxy or halogen; R6 is alkyl or substituted alkyl; and R7 is hydrogen, alkoxy, or halogen.