# US 11,306,061 B2 · Crystalline forms of plasma kallikrein inhibitors

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- Number: US 11,306,061 B2
- Document ID: US11306061B2
- Status: Granted
- Kind: B2
- Application number: 16/922,064
- Filed: 2020-07-07
- Published: 2021-01-14
- Granted: 2022-04-19
- Earliest claimed: 2019-07-08
- Assignees: Rezolute, Inc.; Activesite Pharmaceuticals, Inc.
- Applicants: Rezolute, Inc.; ActiveSite Pharmaceuticals, Inc.
- Inventors: Sukanto Sinha; Tamie Chilcote; Julian Scott Northen; Jamie Marshall
- Web page: https://patentgrep.com/patent/US11306061B2

## CPC

- C07D 231/14: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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

Pure crystalline forms of 1-benzyl-N-(4-carbamimidoylbenzyl)-1H-pyrazole-4-carboxamide acetate, and an amorphous form, pharmaceutical compositions thereof, and methods for making the same, are disclosed.

## Claims

### Claim 1

Crystalline Form I of anhydrous 1-benzyl-N-(4-carbamimidoylbenzyl)-1H-pyrazole-4-carboxamide acetate characterized by an X-ray powder diffraction (XRPD) pattern that comprises peaks at 10.0, 18.1, 18.6, 20.1, and 23.9 degrees, ±0.5 degrees, 2θ, wherein said XRPD is made using Cu Kα radiation, and Crystalline Form I is substantially free of other polymorphic forms of 1-benzyl-N-(4-carbamimidoylbenzyl)-1H-pyrazole-4-carboxamide acetate.

### Claim 2 (depends on 1)

The crystalline form of claim 1, further characterized by a melting point of about 253° C., and an aqueous solubility of about 8.3 mg/mL at 25° C.

### Claim 3 (depends on 1)

The crystalline form of claim 1, wherein the XRPD pattern further comprises a peak at 20.5 degrees, ±0.5 degrees, 2θ.

### Claim 4 (depends on 1)

The crystalline form of claim 1, wherein the XRPD pattern is substantially similar to the pattern of FIG. 1.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising crystalline Form I according to claim 1, and a pharmaceutically acceptable carrier.

### Claim 6 (depends on 4)

A pharmaceutical composition comprising crystalline Form I according to claim 4, and a pharmaceutically acceptable carrier.