# US 11,026,943 B2 · Aminoquinoline derivatives and uses thereof

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

- Number: US 11,026,943 B2
- Document ID: US11026943B2
- Status: Granted
- Kind: B2
- Application number: 15/404,964
- Filed: 2017-01-12
- Published: 2017-07-27
- Granted: 2021-06-08
- Earliest claimed: 2012-03-07
- Assignees: The McLean Hospital Corporation; University of Delhi
- Applicants: University of Delhi; The Mclean Hospital Corporation
- Inventors: Diwan S. Rawat; Sunny Manohar; Ummadisetty Chinna Rajesh; Deepak Kumar; Anuj Thakur; Mohit Tripathi; Panyala Linga Reddy; Shamseer Kulangara Kandi; Satyapavan Vardhineni; Kwang-Soo Kim; Chun-Hyung Kim
- Web page: https://patentgrep.com/patent/US11026943B2

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/5355: Non-condensed oxazines and containing further heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C12N 5/0619: {Neurons}
- C12N 2506/02: from embryonic cells
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Described herein are aminoquinoline and aminoacridine based hybrids, pharmaceutical compositions and medicaments that include such aminoquinoline and aminoacridine based hybrids, and methods of using such compounds for diagnosing and/or treating infections, neurodegenerative diseases or disorders, inflammation, inflammation associated diseases and disorders, and/or diseases or disorders that are treatable with dopamine agonists such as the restless leg syndrome.

## Claims

### Claim 1

A method of ameliorating symptoms of Parkinson's disease, the method comprising administering to a subject in need thereof a therapeutically effective amount of a compound selected from the group consisting of Formula (1)-Formula (X) and any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof, where
wherein:
X, Y, and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine;
R10-R15 and R17-R18 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted; and
L is a linker
wherein:
X and Y are independently CR18, N, O, or S;
A and B are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine;
R11-R15 and R17-R18 are independently H, linear or branched alkyl, linear or branched
alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
----- forms a cyclyl, heterocyclyl, aryl, or heteroaryl, each of which can be optionally substituted; and
L is a linker;
wherein:
A and B are independently CR18 or N;
Z1 is N and Z2 is CR14;
R16 is chlorine;
R, R10-R15 and R17-R18 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted; and
L is a linker;
wherein:
X and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine;
R11-R15 and R17-R18 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
----- forms a cyclyl, heterocyclyl, aryl, or heteroaryl, each of which can be optionally substituted; and
L is a linker;
wherein:
X, Y, and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine; and
R11-R15 and R17-R18 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted; and
R10 is linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
wherein:
X, Y, and Z are independently CR18, N, O, or S;
R27 is chlorine;
R10, R11, R18, R21-R26 and R28 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted; and
L is a linker;
wherein:
X, Y, and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine; and
R10-R15 and R17-R22 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
wherein:
X, Y, and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine; and
R10-R15 and R17-R21 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
wherein:
X, Y, and Z are independently CR18, N, O, or S;
Z1 is N and Z2 is CR14;
R16 is chlorine; and
R10-R15 and R17-R22 are independently H, linear or branched alkyl, linear or branched alkenyl, linear or branched alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halogen, trifluoromethyl, alkoxy, nitro, cyano, carbonyl, hydroxyl, phenoxy, amino, alkylamino, thiol, or alkylthio, each of which can be optionally substituted;
wherein:
R is hydrogen, CH3, Cl, CF3 or CN;
R1 is cyclic or acylic amine; and
L is an optionally substituted C2-C30 alkyl, optionally substituted aromatic ring, optionally substituted heteroaryl ring, saturated cyclic ring; amino acid, or peptide.

### Claim 2 (depends on 1)

The method of claim 1, further comprising co-administering forskolin, colforsin, or a dopamine agonist to the subject.

### Claim 3 (depends on 2)

The method of claim 2, wherein the dopamine agonist is L-DOPA.

### Claim 4 (depends on 1)

The method of claim 1, wherein the compound has formula:
or any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the compound has formula:
or any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof.

### Claim 6 (depends on 1)

The method of claim 1, wherein the compound has formula:
or any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the compound has formula:
or any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof.

### Claim 8 (depends on 1)

The method of claim 1, wherein the compound has formula:
or any pharmaceutically acceptable salt, hydrate, solvate, ester, stereoisomer mixture, or enantiomer thereof.