# US 12,215,094 B2 · Solid forms of 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl]amino}-1,3,5-triazin-2-yl) amino]propan-2-ol

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- Number: US 12,215,094 B2
- Document ID: US12215094B2
- Status: Granted
- Kind: B2
- Application number: 17/290,240
- Filed: 2019-11-01
- Published: 2021-12-30
- Granted: 2025-02-04
- Earliest claimed: 2018-11-02
- Assignees: Celgene Corporation
- Applicants: Celgene Corporation
- Inventors: Eric A. Fromme; Kevin J. Klopfer
- Web page: https://patentgrep.com/patent/US12215094B2

## CPC

- C07D 401/14: containing three or more hetero rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- 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

Solid forms comprising 2-methyl-1-[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl] amino-1,3,5-triazin-2-yl)amino]propan-2-ol, compositions comprising the solid forms, methods of making the solid forms and methods of using the solid forms are disclosed.

## Claims

### Claim 1

A crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl) pyridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the crystalline form is characterized by an X-ray powder diffraction pattern presented in FIG. 1.

### Claim 2

A crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl) pyridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the crystalline form is characterized by an X-ray powder diffraction pattern presented in FIG. 4.

### Claim 3

A crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl) pyridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the crystalline form is characterized by an X-ray powder diffraction pattern having peaks at 2θ angles of 16.58, 18.49, and 24.32°±0.2° 2θ.

### Claim 4 (depends on 3)

The crystalline form of claim 3, characterized by an X-ray powder diffraction pattern presented in FIG. 7.

### Claim 5

A crystalline form of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl) pyridin-4-yl] amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, wherein the crystalline form is characterized by an X-ray powder diffraction pattern having peaks at 2θ angles of 21.29 and 21.79°±0.2° 2θ.

### Claim 6 (depends on 5)

The crystalline form of claim 5, characterized by an X-ray powder diffraction pattern presented in FIG. 9.

### Claim 7 (depends on 1)

A pharmaceutical composition, comprising the crystalline form of claim 1, and a pharmaceutically acceptable excipient.

### Claim 8 (depends on 1)

A method of treating or ameliorating one or more symptoms of a disease selected from the group consisting of a hematological malignancy and a solid tumor, each characterized by the presence of a mutant allele of IDH2, comprising administering to a subject having the disease a therapeutically effective amount of the crystalline form of claim 1.

### Claim 9 (depends on 8)

The method of claim 8, wherein the disease is characterized by the presence of a mutant allele of IDH2 and the absence of a mutant allele of FLT3.

### Claim 10 (depends on 8)

The method of claim 8, wherein the disease is characterized by the presence of a mutant allele of IDH2 and the absence of a mutant allele of NRAS.

### Claim 11 (depends on 8)

The method of claim 8, wherein the disease is a hematological malignancy.

### Claim 12 (depends on 11)

The method of claim 11, wherein the hematological malignancy is selected from the group consisting of acute myelogenous leukemia, myelodysplastic syndrome, chronic myelomonocytic leukemia, myeloid sarcoma, multiple myeloma, lymphoma, angioimmunoblastic T-cell lymphoma, blastic plasmacytoid dendritic cell neoplasm and myeloproliferative neoplasm, each characterized by the presence of a mutant allele of IDH2.

### Claim 13 (depends on 12)

The method of claim 12, wherein the hematological malignancy is acute myelogenous leukemia.

### Claim 14 (depends on 12)

The method of claim 12, wherein the hematological malignancy is myelodysplastic syndrome.

### Claim 15 (depends on 8)

The method of claim 8, wherein the disease is characterized by the presence of a mutant allele of IDH2 and a mutant allele of at least one second gene, wherein the second gene is selected from the group consisting of ASXL1 and SRSF2.

### Claim 16 (depends on 15)

The method of claim 15, wherein the disease is characterized by the presence of a mutant allele of IDH2 and the absence of a mutant allele of at least one other gene, wherein the other gene is selected from the group consisting of KRAS, TP53, SETBP1, U2AF1, TCF3, STAG2, NRAS, JAK2 and BRAF.

### Claim 17 (depends on 8)

The method of claim 8, wherein the solid tumor is selected from the group consisting of glioma, melanoma, chondrosarcoma, and cholangiocarcinoma, each characterized by the presence of a mutant allele of IDH2.

### Claim 18 (depends on 8)

The method of claim 8, wherein the disease is relapsed or refractory.

### Claim 19 (depends on 8)

The method of claim 8, further comprising administering a second active agent.

### Claim 20 (depends on 8)

The method of claim 8, wherein the subject is a pediatric patient.

### Claim 21 (depends on 2)

A method of treating or ameliorating one or more symptoms of a disease selected from the group consisting of a hematological malignancy and a solid tumor, each characterized by the presence of a mutant allele of IDH2, comprising administering to a subject having the disease a therapeutically effective amount of the crystalline form of claim 2.

### Claim 22 (depends on 3)

A method of treating or ameliorating one or more symptoms of a disease selected from the group consisting of a hematological malignancy and a solid tumor, each characterized by the presence of a mutant allele of IDH2, comprising administering to a subject having the disease a therapeutically effective amount of the crystalline form of claim 3.

### Claim 23 (depends on 5)

A method of treating or ameliorating one or more symptoms of a disease selected from the group consisting of a hematological malignancy and a solid tumor, each characterized by the presence of a mutant allele of IDH2, comprising administering to a subject having the disease a therapeutically effective amount of the crystalline form of claim 5.