# US 11,993,584 B2 · Solid forms of an azolopyrimidine compound

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- Number: US 11,993,584 B2
- Document ID: US11993584B2
- Status: Granted
- Kind: B2
- Application number: 17/260,847
- Filed: 2019-07-17
- Published: 2021-09-02
- Granted: 2024-05-28
- Earliest claimed: 2018-07-18
- Assignees: Arcus Biosciences, Inc.
- Applicants: Arcus Biosciences, Inc.
- Inventors: Jenna Leigh Jeffrey; Manmohan Reddy Leleti; Dillon Harding Miles; Jay Patrick Powers
- Web page: https://patentgrep.com/patent/US11993584B2

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- C07D 401/14: containing three or more hetero rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- C07K 16/2818: {against CD28 or CD152}
- C07K 16/2827: {against B7 molecules, e.g. CD80, CD86}
- 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)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention provides solid forms, solvates and hydrates of 3-[2-amino-6-(1-{[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl}-1H-1,2,3-triazol-4-yl)pyrimidin-4-yl]-2-methylbenzonitrile (Compound I), and methods of making and using the same.

## Claims

### Claim 1

A solid form of Compound I:
wherein the solid form is characterized by an XRPD pattern comprising one or more peaks at 6.9, 8.0, 8.2, 12.5, 12.7, 14.8, 15.0, 15.7, 16.8, 18.1, 18.8, 19.2, 20.6, 21.1, 21.8, 24.9, 27.1, or 27.7 degrees 2θ (±0.1 degrees 2θ), wherein the XRPD is made using CuKα1 radiation, or a hydrate or solvate thereof.

### Claim 2 (depends on 1)

The solid form of claim 1, characterized by an XRPD pattern comprising peaks at 6.9, 8.2, and 15.7 degrees 2θ (±0.1 degrees 2θ), wherein the XRPD is made using CuKα1 radiation.

### Claim 3 (depends on 2)

The solid form of claim 2, further comprising one or more peaks at 14.8, 15.0, 18.8, or 21.1 degrees 2θ (±0.1 degrees 2θ), wherein the XRPD is made using CuKα1 radiation.

### Claim 4 (depends on 1)

The solid form of claim 1, characterized by an X-ray powder diffraction pattern (XRPD) having peaks at 6.9, 8.0, 8.2, 12.5, 12.7, 14.8, 15.0, 15.7, 16.8, 18.1, 18.8, 19.2, 20.6, 21.1, 21.8, 24.9, 27.1, and 27.7 degrees 2θ (±0.1 degrees 2θ), wherein the XRPD is made using CuKα1 radiation.

### Claim 5 (depends on 1)

The solid form of claim 1, characterized by an X-ray powder diffraction pattern (XRPD) substantially in accordance with that of FIG. 1.

### Claim 6 (depends on 1)

The solid form of claim 1, characterized by a unit cell as determined by single crystal X-ray crystallography of the following dimensions: a=15.1880 (7)Å; b=20.9125 (11)Å; c=7.5242 (4)Å; α=90°; β=90.7720 (10) °; and γ=90°.

### Claim 7 (depends on 1)

The solid form of claim 1, characterized by a differential scanning calorimetry (DSC) pattern having an endotherm at about 193° C.

### Claim 8 (depends on 1)

The solid form of claim 1, characterized by a differential scanning calorimetry (DSC) pattern substantially in accordance with that of FIG. 2.

### Claim 9 (depends on 1)

A pharmaceutical composition comprising a solid form of claim 1 and a pharmaceutically acceptable excipient.

### Claim 10 (depends on 1)

A method of treating a disease, disorder, or condition, mediated at least in part by the adenosine A2A receptor (A2AR) or the adenosine A2B receptor (A2BR), or both the A2AR and A2BR receptors, said method comprising administering a therapeutically effective amount of a solid form of claim 1 to a subject in need thereof.

### Claim 11 (depends on 10)

The method of claim 10, wherein said disease, disorder, or condition is cancer, or an immune-related disease, disorder or condition.

### Claim 12 (depends on 11)

The method of claim 11, wherein said cancer is a cancer of the prostate, colon, rectum, pancreas, cervix, stomach, endometrium, brain, liver, bladder, ovary, testis, head, neck, skin, mesothelial lining, white blood cell, esophagus, breast, muscle, connective tissue, lung, adrenal gland, thyroid, kidney, or bone; or is glioblastoma, mesothelioma, renal cell carcinoma, gastric carcinoma, sarcoma, choriocarcinoma, cutaneous basocellular carcinoma, or testicular seminoma.

### Claim 13 (depends on 11)

The method of claim 11, further comprising administering at least one additional therapeutic agent to the subject in need thereof.

### Claim 14 (depends on 13)

The method of claim 13, wherein said at least one additional therapeutic agent comprises an immune checkpoint inhibitor that blocks the activity of at least one of PD-1, PD-L1, TIGIT, or CTLA-4.

### Claim 15 (depends on 11)

The method of claim 11, wherein said cancer is non-small-cell lung carcinoma.

### Claim 16 (depends on 11)

The method of claim 11, wherein said cancer is prostate cancer.

### Claim 17 (depends on 11)

The method of claim 11, wherein said cancer is colon cancer or rectal cancer.

### Claim 18 (depends on 11)

The method of claim 11, wherein said cancer is pancreatic cancer.

### Claim 19

A solid form of Compound I:
characterized by an X-ray powder diffraction pattern (XRPD) substantially in accordance with that of FIG. 5.

### Claim 20

A solid form of Compound I,
characterized by an X-ray powder diffraction pattern (XRPD) substantially in accordance with that of FIG. 7.

### Claim 21 (depends on 11)

The method of claim 11, wherein said cancer is melanoma, basal cell carcinoma, lymphoma, leukemia, small-cell lung carcinoma, or Kaposi's sarcoma.