# US 10,865,198 B2 · Solid forms of cerdulatinib

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- Number: US 10,865,198 B2
- Document ID: US10865198B2
- Status: Granted
- Kind: B2
- Application number: 16/402,684
- Filed: 2019-05-03
- Published: 2020-01-30
- Granted: 2020-12-15
- Earliest claimed: 2018-05-04
- Assignees: Alexion Pharmaceuticals, Inc.
- Applicants: Portola Pharmaceuticals, Inc.
- Inventors: Anjali Pandey; Julian Scott Northen; Philippe Fernandes; Ying Chen; Yuelie Lu; Sami Karaborni; Gus Kodersha
- Web page: https://patentgrep.com/patent/US10865198B2

## CPC

- C07D 239/48: Two nitrogen atoms
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- A61P 35/00: Antineoplastic agents
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

Forms of cerdulatinib and salts or co-crystals thereof were prepared and characterized in the solid state. Also provided are processes of manufacture and methods of using the forms cerdulatinib and salts or co-crystals thereof.

## Claims

### Claim 1

A crystalline mono-hydrochloride salt of Compound I:
characterized by an X-ray powder diffractogram comprising peaks at 8.7, 15.9, and 20.0°2θ, each ±0.2°2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I HCl Form I).

### Claim 2 (depends on 1)

The salt of claim 1, further characterized by one or more peaks at 11.5, 22.5, and 25.5°2θ, each ±0.2°2θ.

### Claim 3 (depends on 1)

The salt of claim 1, further characterized by a differential scanning calorimetry curve comprising an endotherm with onset at about 288° C.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising one or more pharmaceutically acceptable carriers, and a therapeutically effective amount of a salt of claim 1.

### Claim 5 (depends on 1, 4)

The pharmaceutical composition of claim 4, wherein the salt comprises at least about 50% w/w of Compound I HCl Form I of claim 1.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the salt of claim 1, and another therapeutic agent.

### Claim 7 (depends on 1)

A method for treating a disease or condition mediated by a protein kinase in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a salt of claim 1.

### Claim 8 (depends on 7)

The method of claim 7, wherein the protein kinase is JAK or any mutation thereof.

### Claim 9 (depends on 7)

The method of claim 7, wherein the protein kinase is SYK or any mutation thereof.

### Claim 10 (depends on 7)

The method of claim 7, wherein the disease or condition is chronic lymphocytic leukemia (CLL), small lymphocytic lymphoma (SLL), follicular lymphoma (FL), transformed follicular lymphoma (tFL), diffuse large B-cell lymphoma (DLBCL), mantle cell lymphoma (MCL), B-cell non-Hodgkin's lymphoma (NHL), peripheral T-cell lymphoma (PTCL) cutaneous T-cell lymphoma (CTCL), marginal zone lymphoma, mucosa-associated lymphoid tissue (MALT), or Waldenstrom macroglobulinemia (WM).

### Claim 11 (depends on 10)

The method of claim 10, wherein the disease or condition is chronic lymphocytic leukemia (CLL).

### Claim 12 (depends on 10)

The method of claim 10, wherein the disease or condition is small lymphocytic lymphoma (SLL).

### Claim 13 (depends on 10)

The method of claim 10, wherein the disease or condition is follicular lymphoma (FL) or transformed follicular lymphoma (tFL).

### Claim 14 (depends on 10)

The method of claim 10, wherein the disease or condition is diffuse large B-cell lymphoma (DLBCL).

### Claim 15 (depends on 10)

The method of claim 10, wherein the disease or condition is mantle cell lymphoma (MCL).

### Claim 16 (depends on 10)

The method of claim 10, wherein the disease or condition is B-cell non-Hodgkin's lymphoma (NHL).

### Claim 17 (depends on 10)

The method of claim 10, wherein the disease or condition is peripheral T-cell lymphoma (PTCL) or cutaneous T-cell lymphoma (CTCL).

### Claim 18 (depends on 10)

The method of claim 10, wherein the disease or condition is marginal zone lymphoma.

### Claim 19 (depends on 10)

The method of claim 10, wherein the disease or condition is mucosa-associated lymphoid tissue (MALT).

### Claim 20 (depends on 10)

The method of claim 10, wherein the disease or condition is Waldenstrom macroglobulinemia (WM).

### Claim 21

A crystalline hydrochloride salt of Compound I:
characterized by an X-ray powder diffractogram comprising peaks at 7.9, 19.6, and 13.3°2θ, each ±0.2°2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I HCl Type B).

### Claim 22 (depends on 21)

The salt of claim 21, further characterized by one or more peaks at 22.5, 17.2, and 9.7°2θ, each ±0.2°2θ.

### Claim 23 (depends on 21)

The salt of claim 21, further characterized by a differential scanning calorimetry curve comprising an endotherm with onset at about 286° C.

### Claim 24 (depends on 21)

A pharmaceutical composition comprising one or more pharmaceutically acceptable carriers, and a therapeutically effective amount of a salt of claim 21.

### Claim 25 (depends on 21, 24)

The pharmaceutical composition of claim 24, wherein the salt comprises at least about 50% w/w of Compound I HCl Type B of claim 21.

### Claim 26 (depends on 21)

A pharmaceutical composition comprising the salt of claim 21, and another therapeutic agent.

### Claim 27 (depends on 21)

A method for treating a disease or condition mediated by a protein kinase in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a salt of claim 21.

### Claim 28 (depends on 27)

The method of claim 27, wherein the protein kinase is JAK or any mutation thereof.

### Claim 29 (depends on 27)

The method of claim 27, wherein the protein kinase is SYK or any mutation thereof.

### Claim 30 (depends on 27)

The method of claim 27, wherein the disease or condition is chronic lymphocytic leukemia (CLL), small lymphocytic lymphoma (SLL), follicular lymphoma (FL), transformed follicular lymphoma (tFL), diffuse large B-cell lymphoma (DLBCL), mantle cell lymphoma (MCL), B-cell non-Hodgkin's lymphoma (NHL), peripheral T-cell lymphoma (PTCL) cutaneous T-cell lymphoma (CTCL), marginal zone lymphoma, mucosa-associated lymphoid tissue (MALT), or Waldenstrom macroglobulinemia (WM).

### Claim 31 (depends on 30)

The method of claim 30, wherein the disease or condition is chronic lymphocytic leukemia (CLL).

### Claim 32 (depends on 30)

The method of claim 30, wherein the disease or condition is small lymphocytic lymphoma (SLL).

### Claim 33 (depends on 30)

The method of claim 30, wherein the disease or condition is follicular lymphoma (FL) or transformed follicular lymphoma (tFL).

### Claim 34 (depends on 30)

The method of claim 30, wherein the disease or condition is diffuse large B-cell lymphoma (DLBCL).

### Claim 35 (depends on 30)

The method of claim 30, wherein the disease or condition is mantle cell lymphoma (MCL).

### Claim 36 (depends on 30)

The method of claim 30, wherein the disease or condition is B-cell non-Hodgkin's lymphoma (NHL).

### Claim 37 (depends on 30)

The method of claim 30, wherein the disease or condition is peripheral T-cell lymphoma (PTCL) or cutaneous T-cell lymphoma (CTCL).

### Claim 38 (depends on 30)

The method of claim 30, wherein the disease or condition is marginal zone lymphoma.

### Claim 39 (depends on 30)

The method of claim 30, wherein the disease or condition is mucosa-associated lymphoid tissue (MALT).

### Claim 40 (depends on 30)

The method of claim 30, wherein the disease or condition is Waldenstrom macroglobulinemia (WM).