# US 9,040,588 B2 · Acetamide stereoisomer

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

- Number: US 9,040,588 B2
- Document ID: US9040588B2
- Status: Granted
- Kind: B2
- Application number: 14/157,793
- Filed: 2014-01-17
- Published: 2014-05-15
- Granted: 2015-05-26
- Earliest claimed: 2007-08-28
- Assignees: Sunovion Pharmaceuticals Inc.
- Applicants: Sunovion Pharmaceuticals Inc.
- Inventors: Craig R. Abolin; H. Scott Wilkinson; Paul McGlynn; William K. McVicar
- Web page: https://patentgrep.com/patent/US9040588B2

## CPC

- C07C 233/43: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
- A61K 9/0075: {for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles}
- A61K 9/008: {comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]}
- A61K 31/167: having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A61K 31/4015: having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/08: Bronchodilators
- A61P 13/00: Drugs for disorders of the urinary system
- C07C 231/18: by stereospecific synthesis
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The compound of formula (I) is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like. Processes for making the compound of formula (I), as well as related intermediates, are disclosed.

## Claims

### Claim 1

A formulation for nebulization comprising a compound of formula (I)
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A formulation for nebulization according to claim 1 wherein said formulation for nebulization is an aqueous formulation.

### Claim 3 (depends on 2)

A formulation for nebulization according to claim 2 wherein said aqueous formulation is an aqueous solution.

### Claim 4 (depends on 2)

A formulation for nebulization according to claim 2 wherein said aqueous formulation is a suspension.

### Claim 5 (depends on 4)

A formulation for nebulization according to claim 4, wherein said suspension comprises nanoparticles, a micronized suspension of free base or an insoluble salt, or a cyclodextrin adduct of the compound of formula I.

### Claim 6 (depends on 1)

A formulation for nebulization according to claim 1, which further comprises a steroid.

### Claim 7 (depends on 6)

A formulation for nebulization according to claim 6, wherein the steroid is beclomethasone, triamcinolone, funisolide, mometasone, budesonide or fluticasone.

### Claim 8 (depends on 1)

A formulation for nebulization according to claim 1, which further comprises a muscarinic receptor antagonist.

### Claim 9 (depends on 8)

A formulation for nebulization according to claim 8, in which the muscarinic receptor antagonist is ipratropium or tiatropium.

### Claim 10 (depends on 1)

A formulation for nebulization according to claim 1, which further comprises an anticholinergic.

### Claim 11 (depends on 10)

A formulation for nebulization according to claim 10, in which the anticholinergic is glycopyrralate.

### Claim 12 (depends on 1)

A formulation for nebulization according to claim 1, which further comprises a mucolytic.

### Claim 13 (depends on 12)

A formulation for nebulization according to claim 12, in which the mucolytic is cromoglycate, acetylcysteine, arginine, or 2-mercaptoethanesulphonate.

### Claim 14 (depends on 1)

A formulation for nebulization according to claim 1, which further comprises an anti-inflammatory agent.

### Claim 15 (depends on 1)

A formulation for nebulization according to claim 1, wherein said compound of formula I is present in a mixture of isomers of N-[2-hydroxy-5-[1-hydroxy-2-[[(2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenyl]acetamide, wherein the mixture comprises at least 90% by weight of the isomer of formula I.