# US 11,897,874 B2 · Compounds and methods for modulating Interleukin-2-inducible T-cell kinase

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- Number: US 11,897,874 B2
- Document ID: US11897874B2
- Status: Granted
- Kind: B2
- Application number: 17/224,410
- Filed: 2021-04-07
- Published: 2022-11-17
- Granted: 2024-02-13
- Earliest claimed: 2016-11-03
- Assignees: Corvus Pharmaceuticals, Inc.
- Applicants: Corvus Pharmaceuticals, Inc.
- Inventors: Ryan Hudson; Anne-Marie Beausoleil
- Web page: https://patentgrep.com/patent/US11897874B2

## CPC

- C07D 277/54: Nitrogen and either oxygen or sulfur atoms
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 417/14: containing three or more hetero rings
- C07D 471/08: Bridged systems
- C07D 487/04: Ortho-condensed systems
- C07D 487/08: Bridged systems
- C07D 487/10: Spiro-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Provided herein, inter alia, are methods and compounds for modulating Interleukin-2-inducible T-cell kinase.

## Claims

### Claim 1

A compound of Formula (IIA):
wherein:
R1 is hydrogen, halogen, —CX13, —CHX12, —CH2X1, —OCX13, —OCH2X1, —OCHX12, —CN, —SOn1R1D, —SOv1NR1AR1B, —NHC(O)NR1AR1B, —N(O)m1, —NR1AR1B, —C(O)R1C, —C(O)—OR1C, —C(O)NR1AR1B, —OR1D, —NR1ASO2R1D, —NR1AC(O)R1C, —NR1AC(O)OR1C, —NR1AOR1C, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R3 is hydrogen, halogen, —CX33, —CHX32, —CH2X3, —OCX33, —OCH2X3, —OCHX32, —CN, —SOn3R3D, —SOv3NR3AR3B, —NHC(O)NR3AR3B, —N(O)m3, —NR3AR3B, —C(O)R3C, —C(O)—OR3C, —C(O)NR3AR3B, —OR3D, —NR3ASO2R3D, —NR3AC(O)R3C, —NR3AC(O)OR3C, —NR3AOR3C, unsubstituted or substituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R5 is unsubstituted or substituted cycloalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L3 is —C(O)—, a bond, —N(R6)—, or —C(O)N(R6)—;
R6 is hydrogen or methyl;
L4 is substituted or unsubstituted 5 to 8 membered monocyclic heterocycloalkylene;
E is —C(O)CH═CH2;
R1A, R1B, R1C, R1D, R3A, R3B, R3C, and R3D are each independently hydrogen, —CX3, —CN, —COOH, —CONH2, —CHX2, —CH2X, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, or unsubstituted heteroaryl;
X, X1, and X3 are each independently —F, —Cl, —Br, or —I;
n1 and n3 are independently an integer from 0 to 4; and
m1, m3, v1, and v3 are independently 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1 wherein:
R1 is hydrogen, halogen, —CX13, —CH12, CH2X1, —OCX13, —OCH2X1, —OCHX12, unsubstituted alkyl, or unsubstituted heteroalkyl; and
R3 is hydrogen, halogen, —CX33, —CHX32, —CH2X3, —OCX33, —OCH2X3, —OCHX32, —CN, unsubstituted alkyl, or unsubstituted heteroalkyl.

### Claim 3 (depends on 2)

The compound of claim 2, wherein:
R1 is hydrogen, halogen, —CH3, —CH2CH3, —CX13, —CHX12, —CH2X1, —OCH3, —OCX13, —OCH2X1, or —OCHX12; and
R3 is hydrogen, halogen, —CH3, —CH2CH3, —CX33, —CHX32, —CH2X3, —OCH3, —OCX33, —OCH2X3, —OCHX32, or CN.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1A, R1B, R1C, R1D, R3A, R3B, R3C, and R3D are hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R5 is substituted or unsubstituted cycloalkyl.

### Claim 6 (depends on 5)

The compound of claim 5, wherein R5 is unsubstituted cyclopropyl, unsubstituted cyclobutyl, or unsubstituted cyclopentyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R5 is substituted or unsubstituted (C1-C4) alkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R5 is substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted oxazolyl, or substituted or unsubstituted isoxazolyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein L3 is —C(O)—.

### Claim 10 (depends on 1)

The compound of claim 1, wherein L4 is a methyl-substituted 5 to 8 membered monocyclic heterocycloalkylene, an ethyl-substituted 5 to 8 membered monocyclic heterocycloalkylene, a cyano-substituted 5 to 8 membered monocyclic heterocycloalkylene, a halo-substituted 5 to 8 membered monocyclic heterocycloalkylene, or an unsubstituted 5 to 8 membered monocyclic heterocycloalkylene.

### Claim 11 (depends on 1)

The compound of claim 1, wherein L4 is

### Claim 12 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

### Claim 13 (depends on 1)

A method of treating T-cell lymphoma in a patient in need thereof, the method comprising administering to the patient an effective amount of the compound of claim 1.

### Claim 14 (depends on 13)

The method of claim 13, wherein the T-cell lymphoma is cutaneous T-cell lymphoma or peripheral T-cell lymphoma.

### Claim 15

A method of treating T-cell lymphoma in a patient in need thereof, the method comprising administering to the patient an effective amount of a compound; wherein the compound is

### Claim 16 (depends on 15)

The method of claim 15, wherein the T-cell lymphoma is cutaneous T-cell lymphoma.

### Claim 17 (depends on 15)

The method of claim 15, wherein the T-cell lymphoma is peripheral T-cell lymphoma.

### Claim 18

A pharmaceutical composition comprising a compound and a pharmaceutically acceptable excipient; wherein the compound is

### Claim 19 (depends on 18)

A method of treating T-cell lymphoma in a patient in need thereof, the method comprising administering to the patient an effective amount of the pharmaceutical composition of claim 18.

### Claim 20 (depends on 19)

The method of claim 19, wherein the T-cell lymphoma is cutaneous T-cell lymphoma or peripheral T-cell lymphoma.

### Claim 21

A method of treating T-cell lymphoma in a patient in need thereof, the method comprising administering to the patient an effective amount of a compound having the formula:

### Claim 22 (depends on 21)

The method of claim 21, wherein the T-cell lymphoma is cutaneous T-cell lymphoma.

### Claim 23 (depends on 21)

The method of claim 21, wherein the T-cell lymphoma is peripheral T-cell lymphoma.

### Claim 24 (depends on 21)

The method of claim 21, wherein the T-cell lymphoma is peripheral T-cell lymphoma, unspecified.

### Claim 25

A pharmaceutical composition comprising a compound and a pharmaceutically acceptable excipient; wherein the compound is:

### Claim 26 (depends on 25)

A method of treating T-cell lymphoma in a patient in need thereof, the method comprising administering to the patient an effective amount of the pharmaceutical composition of claim 25.

### Claim 27 (depends on 26)

The method of claim 26, wherein the T-cell lymphoma is cutaneous T-cell lymphoma.

### Claim 28 (depends on 26)

The method of claim 26, wherein the T-cell lymphoma is peripheral T-cell lymphoma.

### Claim 29 (depends on 26)

The method of claim 26, wherein the T-cell lymphoma is peripheral T-cell lymphoma, unspecified.