# US 12,109,192 B2 · Organic acid addition salts of S-pindolol

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- Number: US 12,109,192 B2
- Document ID: US12109192B2
- Status: Granted
- Kind: B2
- Application number: 17/995,621
- Filed: 2021-03-31
- Published: 2023-06-22
- Granted: 2024-10-08
- Earliest claimed: 2020-04-07
- Assignees: Actimed Therapeutics Limited
- Applicants: Actimed Therapeutics Ltd
- Inventors: Robin Chandra Bhattacherjee; Andrew Justin Stewart Coats; Elaine Morten; Ronnie Maxwell Lawrence; Jaclyn Raeburn; Kiara Marissa Lobato; Jonathan James Loughrey
- Web page: https://patentgrep.com/patent/US12109192B2

## CPC

- A61K 31/404: Indoles, e.g. pindolol
- C07D 209/32: Oxygen atoms
- A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)}
- A61K 31/194: having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 25/22: Anxiolytics
- A61P 27/06: Antiglaucoma agents or miotics
- A61K 9/20: Pills, tablets, {discs, rods (A61K9/0004, A61K9/0007, A61K9/0056, A61K9/0065 take precedence; for reconstitution of a drink A61K9/0095)}
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to a pharmaceutically acceptable acid addition salt of: (i) S-pindolol; and (ii) an organic acid, wherein the organic acid has: a pKal of greater than or equal to 2.5; and a chemical formula of CxHy(CO2H)z, where x is from 1 to 10, y is from 2 to 20 and z is 1 or 2. The pharmaceutically acceptable acid addition salt is useful in treating conditions such as cachexia, sarcopenia, a neuromuscular disorder and muscle weakness.

## Claims

### Claim 1

A pharmaceutically acceptable acid addition salt of:
(i) S-pindolol; and
(ii) benzoic acid,
wherein the salt is S-pindolol benzoate; and
wherein:
the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 1 having an x-ray powder diffraction pattern comprising peaks at 8.1°, 11.4°, 12.5°, 12.8°, 15.4° and 17.0°±0.2°2θ; or
the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 2 having an x-ray powder diffraction pattern comprising peaks at 16.9°, 18.9° and 20.1°±0.2°2θ.

### Claim 2 (depends on 1)

A pharmaceutically acceptable acid addition salt according to claim 1, wherein the S-pindolol benzoate is S-pindolol monobenzoate.

### Claim 3 (depends on 1)

A pharmaceutically acceptable acid addition salt according to claim 1, wherein the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 1,
wherein the x-ray powder diffraction pattern further comprises peaks at 5.7°and 18.4°±0.2°2θ.

### Claim 4 (depends on 1)

A pharmaceutically acceptable acid addition salt according to claim 1, wherein the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 2,
wherein the x-ray powder diffraction pattern further comprises peaks at 9.2°, 13.9° and 20.7°±0.2 2θ.

### Claim 5 (depends on 1)

A composition comprising at least 60 wt % of a pharmaceutically acceptable acid addition salt as defined in claim 1, relative to the total weight of the composition.

### Claim 6 (depends on 5)

A composition according to claim 5, wherein the composition comprises no more than 30 wt % of R-pindolol or a salt thereof relative to the total weight of the composition.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising (a) a pharmaceutically acceptable acid addition salt as defined in claim 1 and (b) a pharmaceutically acceptable excipient, carrier or diluent.

### Claim 8 (depends on 7)

A pharmaceutical composition according to claim 7, wherein the pharmaceutical composition is a tablet.

### Claim 9 (depends on 7)

A pharmaceutical composition according to claim 7, wherein the pharmaceutical composition comprises less than 1.0 wt % of R-pindolol or a salt thereof.

### Claim 10 (depends on 1)

A pharmaceutically acceptable acid addition salt according to claim 1, wherein the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 1 having an x-ray powder diffraction pattern comprising peaks at 8.1°, 11.4°, 12.5°, 12.8°, 15.4° and 17.0°±0.2°2θ.

### Claim 11 (depends on 1)

A pharmaceutically acceptable acid addition salt according to claim 1, wherein the S-pindolol benzoate is in the form of S-pindolol benzoate crystalline polymorph Pattern 2 having an x-ray powder diffraction pattern comprising peaks at 16.9°, 18.9° and 20.1°±0.2°2θ.