# US 2025/0144072 A9 · Sulcardine salts

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- Number: US 2025/0144072 A9
- Document ID: US20250144072A9
- Status: Published application
- Kind: A9
- Application number: 17/862,117
- Filed: 2022-07-11
- Published: 2025-05-08
- Earliest claimed: 2019-01-29
- Assignees: HUYABIO International, LLC
- Applicants: HUYABIO International, LLC
- Inventors: Suzanne J. ROMANO; Hayley Ann REECE; Joseph Edward Gordon BENSON; Sarah COLLINS; Gary T. ELLIOTT; Mireille GILLINGS; Robert GOODENOW; Curtis TYREE
- Web page: https://patentgrep.com/patent/US20250144072A9

## CPC

- A61K 31/4025: not condensed and containing further heterocyclic rings, e.g. cromakalim
- C07D 295/135: with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Sulcardine salts other than sulfuric acid salts of sulcardine, including crystalline sulcardine salts, are provided herein. Pharmaceutical compositions comprising such salts and methods of treating arrhythmias comprising administering effective amounts of such salts are also provided.

## Claims

### Claim 1

A solid form comprising an acid salt of sulcardine, wherein the acid is ethane-1,2-disulfonic acid, naphthalene-1,5-disulfonic acid, 1-hydroxy-2-naphthoic acid, naphthalene-2-sulfonic acid, hydrochloric acid, or hydrobromic acid.

### Claim 2 (depends on 1)

The solid form of claim 1, which is crystalline.

### Claim 3 (depends on 1)

The solid form of claim 1, comprising an ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 4 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern comprising peaks at approximately 18.8, 20.2, and 21.2° 2θ.

### Claim 5 (depends on 4)

The solid form of claim 4, wherein the XRPD pattern further comprises peaks at approximately 9.2, 10.4, and 13.8° 2θ.

### Claim 6 (depends on 5)

The solid form of claim 5, wherein the XRPD pattern further comprises peaks at approximately 9.6, 14.2, and 14.9° 2θ.

### Claim 7 (depends on 4)

The solid form of claim 4, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 26.

### Claim 8 (depends on 3)

The solid form of claim 3, characterized by an XRPD peak at about 14.2° 2θ and an FT-IR spectrum comprising a peak above about 3500 cm−1.

### Claim 9 (depends on 8)

The solid form of claim 8, characterized by an XRPD peak at about 14.2° 2θ with the absence of a peak at about 5.2° 2θ, and an FT-IR spectrum comprising a peak above about 3500 cm−1, and further optionally comprising one or more FT-IR peaks at about 1206 cm−1 and about 814 cm−1.

### Claim 10 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern having two peaks between about 9.0° 2θ and about 9.8° 2θ, optionally wherein the difference between the two peaks is about 0.4° 2θ, and an FT-IR spectrum comprising a peak above about 3500 cm−1, and further optionally comprising one or more FT-IR peaks at about 1206 cm−1 and about 814 cm−1.

### Claim 11 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern comprising one or more peaks at about 9.2° 2θ, about 9.6° 2θ, about 10.4° 2θ, about 13.8° 2θ, about 14.2° 2θ, and about 14.9° 2θ, and an FT-IR spectrum comprising a peak above about 3500 cm−1, and further optionally comprising one or more FT-IR peaks at about 1206 cm−1 and about 814 cm−1.

### Claim 12 (depends on 8, 9, 10, 11)

The solid form of any one of claims 8 to 11, wherein the peak at above about 3500 cm−1 is at about 3556 cm−1.

### Claim 13 (depends on 4, 5, 6, 7, 8, 9, 10, 11, 12)

The solid form of any one of claims 4 to 12, which is a mono-ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 14 (depends on 13)

The solid form of claim 13, which is a mono-hydrate of a mono-ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 15 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern comprising peaks at approximately 15.7, 16.9, and 23.6° 2θ.

### Claim 16 (depends on 15)

The solid form of claim 15, wherein the XRPD pattern further comprises peaks at approximately 5.2, 9.1, and 11.3° 2θ.

### Claim 17 (depends on 16)

The solid form of claim 16, wherein the XRPD pattern further comprises peaks at approximately 17.6 and 19.2° 2θ.

### Claim 18 (depends on 15)

The solid form of claim 15, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 28.

### Claim 19 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern having a peak at about 5.2° 2θ, and an FT-IR spectrum comprising no peak above about 3500 cm−1, and further optionally comprising one or more peaks at about 3374 cm−1 and about 826 cm−1.

### Claim 20 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern comprising one or more peaks at about 5.2° 2θ, about 9.1° 2θ, about 10.2° 2θ, about 10.8° 2θ, about 11.3° 2θ, about 13.6° 2θ, and about 15.7° 2θ, and an FT-IR spectrum comprising no peak above about 3500 cm−1, and further optionally comprising one or more peaks at about 3374 cm−1 and about 826 cm−1.

### Claim 21 (depends on 15, 16, 17, 18, 19, 20)

The solid form of any one of claims 15 to 20, which is a mono-ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 22 (depends on 21)

The solid form of claim 21, which is a di-hydrate of a mono-ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 23 (depends on 3)

The solid form of claim 3, characterized by an XRPD pattern comprising peaks at approximately 14.1, 17.8, and 23.7° 2θ.

### Claim 24 (depends on 23)

The solid form of claim 23, wherein the XRPD pattern further comprises peaks at approximately 5.6 and 14.9° 2θ.

### Claim 25 (depends on 24)

The solid form of claim 24, wherein the XRPD pattern further comprises peaks at approximately 11.0 and 13.0° 2θ.

### Claim 26 (depends on 23)

The solid form of claim 23, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 19.

### Claim 27 (depends on 23, 24, 25, 26)

The solid form of any one of claims 23 to 26, which is a hemi-ethane-1,2-disulfonic acid salt of sulcardine.

### Claim 28 (depends on 1)

The solid form of claim 1, comprising a naphthalene-1,5-disulfonic acid salt of sulcardine.

### Claim 29 (depends on 28)

The solid form of claim 28, characterized by an XRPD pattern comprising peaks at approximately 14.9, 15.9, and 23.6° 2θ.

### Claim 30 (depends on 29)

The solid form of claim 29, wherein he XRPD pattern further comprises peaks at approximately 4.9 and 10.4° 2θ.

### Claim 31 (depends on 30)

The solid form of claim 30, wherein the XRPD pattern further comprises peaks at approximately 11.3, 12.3, and 19.0° 2θ.

### Claim 32 (depends on 29)

The solid form of claim 29, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 1.

### Claim 33 (depends on 1)

The solid form of claim 1, comprising a 1-hydroxy-2-naphthoic acid salt of sulcardine.

### Claim 34 (depends on 33)

The solid form of claim 33, characterized by an XRPD pattern comprising peaks at approximately 16.8, 18.6, and 18.9° 2θ.

### Claim 35 (depends on 34)

The solid form of claim 34, wherein the XRPD pattern further comprises peaks at approximately 6.7 and 6.9° 2θ.

### Claim 36 (depends on 35)

The solid form of claim 35, wherein the XRPD pattern further comprises peaks at approximately 13.8, 20.3, and 20.8° 2θ.

### Claim 37 (depends on 34)

The solid form of claim 34, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 6.

### Claim 38 (depends on 33)

The solid form of claim 33, characterized by an XRPD pattern comprising peaks at approximately 5.8, 18.6, and 19.9° 2θ.

### Claim 39 (depends on 38)

The solid form of claim 38, wherein the XRPD pattern further comprises peaks at approximately 10.6, 17.8, and 21.4° 2θ.

### Claim 40 (depends on 39)

The solid form of claim 39, wherein the XRPD pattern further comprises peaks at approximately 20.6 and 25.3° 2θ.

### Claim 41 (depends on 38)

The solid form of claim 38, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 9.

### Claim 42 (depends on 38, 39, 40, 41)

The solid form of any one of claims 38 to 41, which has approximately unit cell dimensions of: a=10.2 Å, b=29.9 Å, c=10.8 Å, α==90°, β=103.4°, and γ=90°.

### Claim 43 (depends on 1)

The solid form of claim 1, comprising a naphthalene-2-sulfonic acid salt of sulcardine.

### Claim 44 (depends on 43)

The solid form of claim 43, characterized by an XRPD pattern comprising peaks at approximately 17.2, 17.8, and 21.3° 2θ.

### Claim 45 (depends on 44)

The solid form of claim 44, wherein the XRPD pattern further comprises peaks at approximately 13.3, 13.5, 16.6, and 16.9° 2θ.

### Claim 46 (depends on 45)

The solid form of claim 45, wherein the XRPD pattern further comprises peaks at approximately 9.4 and 10.6° 2θ.

### Claim 47 (depends on 44)

The solid form of claim 44, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 13.

### Claim 48 (depends on 1)

The solid form of claim 1, comprising a sulcardine hydrochloride salt.

### Claim 49 (depends on 48)

The solid form of claim 48, characterized by an XRPD pattern comprising peaks at approximately 12.3, 13.0, and 17.8° 2θ.

### Claim 50 (depends on 49)

The solid form of claim 49, wherein the XRPD pattern further comprises peaks at approximately 13.9, 17.4, and 23.9° 2θ.

### Claim 51 (depends on 50)

The solid form of claim 50, wherein the XRPD pattern further comprises peaks at approximately 20.3 and 21.9° 2θ.

### Claim 52 (depends on 49)

The solid form of claim 49, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 17.

### Claim 53 (depends on 48)

The solid form of claim 48, characterized by an XRPD pattern comprising peaks at approximately 13.5, 19.6, and 20.6° 2θ.

### Claim 54 (depends on 53)

The solid form of claim 53, wherein the XRPD pattern further comprises peaks at approximately 10.1, 11.8, and 16.4° 2θ.

### Claim 55 (depends on 54)

The solid form of claim 54, wherein the XRPD pattern further comprises peaks at approximately 17.8, 19.4, and 25.5° 2θ.

### Claim 56 (depends on 53)

The solid form of claim 53, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 17A.

### Claim 57 (depends on 1)

The solid form of claim 1, comprising a sulcardine hydrobromide salt.

### Claim 58 (depends on 57)

The solid form of claim 57, characterized by an XRPD pattern comprising peaks at approximately 17.9, 19.7, and 24.0° 2θ.

### Claim 59 (depends on 58)

The solid form of claim 58, wherein the XRPD pattern further comprises peaks at approximately 14.1 and 14.9° 2θ.

### Claim 60 (depends on 59)

The solid form of claim 59, wherein the XRPD pattern further comprises peaks at approximately 5.7, 13.0, and 16.2° 2θ.

### Claim 61 (depends on 58)

The solid form of claim 58, characterized by an XRPD pattern that matches the XRPD pattern presented in FIG. 23.

### Claim 62 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61)

A pharmaceutical composition comprising a solid form of any one of claims 1 to 61, and one or more pharmaceutically acceptable excipients.

### Claim 63 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62)

A method of treating arrhythmia, comprising administering to a subject in need thereof a therapeutically effective amount of a solid form of any one of claims 1 to 61, or a pharmaceutical composition of claim 62.

### Claim 64 (depends on 63)

The method of claim 63, wherein the arrhythmia is atrial fibrillation, supraventricular tachyarrhythmia, premature ventricular contraction, ventricular tachycardia, or ventricular fibrillation.