# US 11,440,935 B2 · 3″,5″-dimethoxybenzoyl-3′-amino-3′-deoxy adenosine-5′-triphosphates and pharmaceutical uses thereof

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- Number: US 11,440,935 B2
- Document ID: US11440935B2
- Status: Granted
- Kind: B2
- Application number: 16/981,242
- Filed: 2019-03-14
- Published: 2021-02-25
- Granted: 2022-09-13
- Earliest claimed: 2018-03-15
- Assignees: Merck Patent GmbH
- Applicants: Danmir Therapeutics, LLC
- Inventors: Amir Pelleg; Anu Mahadevan; Jie Li; Cynthia Morency
- Web page: https://patentgrep.com/patent/US11440935B2

## CPC

- C07H 19/20: with the saccharide radical esterified by phosphoric or polyphosphoric acids
- A61K 31/706: containing six-membered rings with nitrogen as a ring hetero atom
- A61P 11/08: Bronchodilators
- A61P 11/14: Antitussive agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/10: Antimycotics
- A61P 31/12: Antivirals
- C07H 1/04: Introducing polyphosphoric acid radicals
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- 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

## Abstract

Provided are compounds compound according to Formula (I), or a pharmaceutically acceptable salt, solvate, coordination complex or prodrug thereof: wherein, R1 and R2 are independently selected from (C1-C6) alkyl. The compounds have P2X3 receptor or P2X2/3 receptor antagonist activity and are useful for the treatment of diseases and disorders characterized by activation of those receptors.

## Claims

### Claim 1

A compound according to Formula (I), or a pharmaceutically acceptable salt thereof:
wherein:
R1 and R2 are independently selected from (C1-C6) alkyl.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein R1 and R2 are methyl, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the compound is a sodium salt of the following formula:

### Claim 4 (depends on 1)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1, or pharmaceutically acceptable salt prodrug thereof.

### Claim 5 (depends on 1)

A method of treating respiratory disease in which extracellular ATP plays a mechanistic role comprising administering to the subject in need of such treatment a therapeutically effective amount of a compound according to claim 1, or pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 5)

The method according to claim 5 wherein the respiratory disease is a cough related respiratory disease.

### Claim 7 (depends on 6)

The method according to claim 6 wherein cough-related the respiratory disease is chronic obstructive pulmonary disorder (COPD), bronchospasm or asthma.

### Claim 8 (depends on 5)

The method according to claim 5 wherein the respiratory disease is disease is sub-acute cough, chronic cough, treatment-resistant cough, idiopathic chronic cough, cough associated with upper respiratory infection, post-viral cough, iatrogenic cough, idiopathic pulmonary fibrosis or cough associated with smoking or a form of bronchitis.

### Claim 9 (depends on 5)

The method according to claim 5, wherein R1 and R2 are methyl in the compound of Formula (I), or in the pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

A method of treating bladder overactivity or urinary incontinence comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound according to claim 1, or pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 10)

The method according to claim 10 wherein the bladder overactivity comprises one or more of urinary urgency, urinary frequency, altered bladder capacity, micturition threshold, unstable bladder contractions, sphincteric spasticity, detrusor hyperreflexia and detrusor instability.

### Claim 12 (depends on 10)

The method according to claim 10 where in the disorder of the bladder is interstitial cystitis.

### Claim 13 (depends on 10)

The method according to claim 10, wherein R1 and R2 are methyl in the compound of Formula (I), or in the pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 1)

A method of treating pain comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound according to claim 1, or pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 14)

The method according to claim 14 wherein the pain is nociceptive pain.

### Claim 16 (depends on 14)

The method according to claim 14 wherein the pain is neuropathic pain.

### Claim 17 (depends on 14)

The method according to claim 14, wherein R1 and R2 are methyl in the compound of Formula (I), or in the pharmaceutically acceptable salt thereof.

### Claim 18

A process for preparing a compound according to Formula (I),
wherein:
R1 and R2 are independently selected from (C1-C6) alkyl;
the process comprising:
(a) reacting the compound 1
with a compound of Formula (IIa)
to form a compound according to Formula (III);
(b) 5′-phosphorylating the compound according to Formula (III) to provide a compound according to Formula (I).

### Claim 19 (depends on 18)

The process according to claim 18 wherein R1 and R2 are methyl.