# US 12,180,174 B2 · A2-73 crystalline polymorph compositions of matter and methods of use thereof

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- Number: US 12,180,174 B2
- Document ID: US12180174B2
- Status: Granted
- Kind: B2
- Application number: 17/978,818
- Filed: 2022-11-01
- Published: 2023-05-11
- Granted: 2024-12-31
- Earliest claimed: 2018-04-12
- Assignees: Anavex Life Sciences Corp.
- Applicants: Anavex Life Sciences Corp.
- Inventors: Christopher U. Missling; Alani Selvey
- Web page: https://patentgrep.com/patent/US12180174B2

## CPC

- C07D 307/14: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- A61K 9/28: Dragees; Coated pills or tablets {, e.g. with film or compression coating (A61K9/2072 takes precedence, e.g. partially coated tablets A61K9/2072, coated multilayer tablets A61K9/2086, tablets with drug-coated core A61K9/209)}
- A61K 9/7023: {Transdermal patches and similar drug-containing composite devices, e.g. cataplasms (galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006)}
- A61K 31/341: not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61K 9/2833: {Organic macromolecular compounds}
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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 present disclosure provides crystalline forms of tetrahydro-N,N-dimethyl-2,2-diphenyl-3-furanmethanamine (A2-73), in freebase or salt forms. Also described are pharmaceutical formulations and dosage forms comprising the disclosed crystal forms, and methods of using crystalline A2-73 in dosage forms for neuroprotection including treatment of neurodegenerative and other diseases.

## Claims

### Claim 1

A crystalline form of tetrahydro-N,N-dimethyl-2,2-diphenyl-3-furanmethanamine (A2-73), wherein the crystalline form is a dihydrogen phosphate salt characterized by the XRPD pattern shown in FIG. 25.

### Claim 2 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the dihydrogen phosphate salt is further characterized by the particle shapes depicted in FIG. 24.

### Claim 3 (depends on 1)

A dosage form comprising a therapeutically effective amount of a crystalline form of A2-73 dihydrogen phosphate salt according to claim 1.

### Claim 4 (depends on 3)

The dosage form of claim 3, wherein the dosage form is a transdermal patch.

### Claim 5 (depends on 3)

The dosage form of claim 3, wherein the transdermal patch maintains a level of A2-73 in the blood of the subject ranging from about 5 ng/ml to about 15 ng/ml.

### Claim 6 (depends on 3)

The dosage form of claim 3, wherein the dosage form is an enteric coated oral dosage form.

### Claim 7 (depends on 1)

A pharmaceutical composition for delivery of A2-73, the pharmaceutical formulation comprising a therapeutically effective amount of the crystalline form of A2-73 dihydrogen phosphate salt according to claim 1, wherein the pharmaceutical formulation comprises one or more pharmaceutically acceptable excipients.