Topical formulations of (1S)-1-phenyl-2-pyridin-2-ylethanamine

Patent metadata

Field	Value
Publication number	US-12564579-B2
Application number	US-202117923585-A
Country	US
Kind code	B2
Filing date	Jun 23, 2021
Priority date	Jun 23, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

Provided is a pharmaceutical formulation including (1S)-1-phenyl-2-pyridin-2-ylethanamine, a pharmaceutically acceptable salt thereof, a solvate thereof, or a prodrug thereof; and a pharmaceutically acceptable topical carrier. Also provided is a method for treating neuropathic pain by administering to a patient in need of such treatment a therapeutically effective amount of the pharmaceutical formulation.

First claim

What is claimed is:

1 . A pharmaceutical formulation, comprising:
a pharmaceutically acceptable salt of (1S)-1-phenyl-2-pyridin-2-ylethanamine, or a prodrug (1S)-1-phenyl-2-pyridin-2-ylethanamine; and a pharmaceutically acceptable topical carrier, wherein the pharmaceutically acceptable salt is a salt of a fatty acid selected from a C6-C12 carboxylic acid, a C13-C21 carboxylic acid, and a C22-C30 carboxylic acid.

2 . The pharmaceutical formulation of claim 1 , wherein the fatty acid is a saturated fatty acid selected from caprylic acid, capric acid, lauric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and cerotic acid.

3 . The pharmaceutical formulation of claim 1 , wherein the fatty acid is an unsaturated fatty acid.

4 . The pharmaceutical formulation of claim 3 , wherein the unsaturated fatty acid is a cis-unsaturated fatty acid selected from myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, linoleic acid, -linoleic acid, arachidonic acid, eicosapentaenoic acid, erusic acid, and docosahexaenoic acid.

5 . The pharmaceutical formulation of claim 3 , wherein the unsaturated fatty acid is a trans-unsaturated fatty acid selected from elaidic acid, vaccenic acid, and linoelaedic acid.

6 . The pharmaceutical formulation of claim 1 , wherein the fatty acid is a linear chain carboxylic acid comprising an even number of carbon atoms selected from caprylic acid, capric acid, lauric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, linoleic acid, α-linoleic acid, arachidonic acid, eicosapentaenoic acid, erusic acid, and docosahexaenoic acid.

7 . The pharmaceutical formulation of claim 1 , wherein the fatty acid is a linear chain carboxylic acid comprising an odd number of carbon atoms selected from a pentadecanoic acid and a heptadecanoic acid.

8 . The pharmaceutical formulation of claim 1 , wherein the fatty acid is an omega-3 fatty acid selected from α-linoleic acid, stearidonic acid, natural eicosatetraenoic acid, eicosapentaenoic acid, clupanodonic acid, tetracosapentaenoic acid, tetracosahexaenoic acid, and docosahexaenoic acid.

9 . The pharmaceutical formulation of claim 2 , wherein the naturally occurring fatty acid is an omega-6 fatty acid selected from linoleic acid, γ-linoleic acid, dihomo-γ-linoleic acid, arachidonic acid, tetracosatetraenoic acid, tetracosapentaenoic acid, and osbond acid.

10 . The pharmaceutical formulation of claim 1 , comprising a prodrug of (1S)-1-phenyl-2-pyridin-2-ylethanamine represented by Chemical Formula 2:

or a pharmaceutically acceptable salt thereof,
wherein, in Chemical Formula 2,
R 1 is a lipophilic moiety derived from a C1-C30 carboxylic acid having formula R 1 —CO 2 H, and
R 2 is H or a C1-C10 unsubstituted or substituted hydrocarbon group.

11 . The pharmaceutical formulation of claim 10 , wherein R 1 is a lipophilic moiety derived from a C8-C30 carboxylic acid having formula R 1 —CO 2 H.

12 . The pharmaceutical formulation of claim 10 , wherein R 2 is selected from the group consisting of a C1-C10 alkyl group, a C1-C10 alkenyl group, and a C1-C10 alkynyl group.

13 . The pharmaceutical formulation of claim 1 , further comprising an analgesic, an anesthetic, a medicinal agent selected from the group consisting of an antifungal agent, an antibiotic, an antiseptic, an anti-inflammatory agent and a neuroprotective agent, or a combination thereof.

14 . A method for treating neuropathic pain, comprising administering to a patient in need of such treatment a therapeutically effective amount of a pharmaceutical formulation, comprising:
a pharmaceutically salt of (1S)-1-phenyl-2-pyridin-2-ylethanamine, or a prodrug (1S)-1-phenyl-2-pyridin-2-ylethanamine; and a pharmaceutically acceptable topical carrier, wherein the pharmaceutically acceptable salt is a salt of a fatty acid selected from a C6-C12 carboxylic acid, a C13-C21 carboxylic acid, and a C22-C30 carboxylic acid.

15 . The method of claim 14 , wherein the neuropathic pain is peripheral neuropathy, mononeuropathy, mononeuritis multiplex, polyneuropathy, autonomic neuropathy, neuritis, phantom limb pain, reflex-sympathetic dystrophy, causalgia, syringomyelia, painful scar, specific neuralgias at any location of the body, back pain, diabetic neuropathy, alcoholic neuropathy, metabolic neuropathy, inflammatory neuropathy, chemotherapy-induced neuropathy, herpetic neuralgias, traumatic odontalgia, endodontic odontalgia, thoracic-outlet syndrome, cervical, thoracic or lumbar radiculopathy with nerve compression, cancer with nerve invasion, traumatic-avulsion injury, mastectomy, thoracotomy pain, spinal-cord-injury, stroke, abdominal-cutaneous nerve entrapments, tumors of neural tissues, arachnoiditis, stump pain, fibromyalgia, regional sprains or strains, myofascial pain, psoriatic arthropathy, polyarteritis nodosa, osteomyelitis, burns involving nerve damage, AIDS-related pain syndromes, sunburn associated syndromes, or connective tissue disorders.

Assignees

• Biohaven Therapeutics Ltd

Inventors

• Berman Robert
• Kumar Rajesh
• Conway Charles M
• Donohue Mary K
• Reka Ajaya Kumar

Classifications

• A61K47/44

  Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14) · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61K9/0014 Primary

  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) · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title