# US 10,765,624 B2 · Amino-pyrimidine skeletal muscle modulators

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- Number: US 10,765,624 B2
- Document ID: US10765624B2
- Status: Granted
- Kind: B2
- Application number: 16/352,626
- Filed: 2019-03-13
- Published: 2019-10-10
- Granted: 2020-09-08
- Earliest claimed: 2010-04-23
- Assignees: Cytokinetics, Inc.
- Applicants: Cytokinetics, Inc.
- Inventors: Zhe Yang; Alex R. Muci; Jeffrey Warrington; Gustave Bergnes; Bradley P. Morgan; Chihyuan Chuang; Antonio Romero; Scott Collibee; Xiangping Qian; Pu-Ping Lu
- Web page: https://patentgrep.com/patent/US10765624B2

## CPC

- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0034: {Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants}
- A61K 9/0043: {Nose}
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/006: {Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays}
- A61K 9/007: {Pulmonary tract; Aromatherapy}
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 21/04: for myasthenia gravis
- A61P 25/02: for peripheral neuropathies
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 239/48: Two nitrogen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- 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)

## Abstract

Provided are compounds of Formula I: or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, X and m are as defined herein. Also provided is a pharmaceutically acceptable composition comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof. Also provided are methods of using a compound of Formula I, or a pharmaceutically acceptable salt thereof.

## Claims

### Claim 1

A compound of formula

### Claim 2 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1.

### Claim 3

A pharmaceutical composition comprising a compound of formula
or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient selected from the group consisting of mannitol, lactose, starch, magnesium stearate, sodium saccharine, talcum, cellulose, sodium crosscarmellose, glucose, gelatin, sucrose, and magnesium carbonate.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, further comprising one or more wetting agent, emulsifying agent, solubilizing agent, pH buffering agent, or any combination thereof.

### Claim 5 (depends on 3)

The pharmaceutical composition of claim 3, further comprising sodium acetate, sodium citrate, a cyclodextrine derivative, sorbitan monolaurate, triethanolamine acetate, triethanolamine oleate, or any combination thereof.

### Claim 6 (depends on 3)

The pharmaceutical composition of claim 3, wherein the pharmaceutical composition comprises from about 0.5% to about 50% by weight of the compound of formula

### Claim 7 (depends on 3)

The pharmaceutical composition of claim 3, wherein the pharmaceutical composition is in the form of a tablet, a capsule, a powder, a liquid, a suspension, a suppository, or an aerosol.

### Claim 8 (depends on 7)

The pharmaceutical composition of claim 7, wherein the pharmaceutical composition is in the form of a tablet.

### Claim 9 (depends on 7)

The pharmaceutical composition of claim 7, wherein the pharmaceutical composition is in the form of a suspension.

### Claim 10 (depends on 3)

A method for treating a disease or condition selected from the group consisting of neuromuscular disorders, conditions of muscle wasting, muscular myopathies, rehabilitation-related deficits, muscle atrophy and fatigue, metabolic syndrome, chronic fatigue syndrome, Amyotrophic Lateral Sclerosis (ALS), Spinal Muscular Atrophy (SMA), myasthenia gravis, peripheral vascular disease, peripheral arterial disease, chronic pulmonary obstructive disorder (COPD), heart failure, frailty, and obesity, comprising administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition of claim 3.

### Claim 11 (depends on 10)

The method of claim 10, wherein the disease or condition is Amyotrophic Lateral Sclerosis (ALS).

### Claim 12 (depends on 10)

The method of claim 10, wherein the disease or condition is Spinal Muscular Atrophy (SMA).

### Claim 13 (depends on 10)

The method of claim 10, wherein the disease or condition is myasthenia gravis.

### Claim 14 (depends on 10)

The method of claim 10, wherein the disease or condition is peripheral vascular disease or peripheral arterial disease.

### Claim 15 (depends on 10)

The method of claim 10, wherein the disease or condition is chronic pulmonary obstructive disorder (COPD).

### Claim 16 (depends on 10)

The method of claim 10, wherein the disease or condition is heart failure.

### Claim 17 (depends on 10)

The method of claim 10, wherein the disease or condition is frailty.