# US 11,897,879 B2 · Heterocyclic compound

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- Number: US 11,897,879 B2
- Document ID: US11897879B2
- Status: Granted
- Kind: B2
- Application number: 17/528,677
- Filed: 2021-11-17
- Published: 2022-03-24
- Granted: 2024-02-13
- Earliest claimed: 2018-11-28
- Assignees: Takeda Pharmaceutical Company Limited
- Applicants: Takeda Pharmaceutical Company Limited
- Inventors: Takaharu Hirayama; Yoshiteru Ito; Noriyuki Nii; Youichi Kawakita; Shinichi Imamura
- Web page: https://patentgrep.com/patent/US11897879B2

## CPC

- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- A61K 9/4858: {Organic compounds}
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/5025: ortho- or peri-condensed with heterocyclic ring systems
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 487/04: Ortho-condensed systems
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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)

## Abstract

Provided is a compound that can have an effect of inhibiting MALT1 and is expected as useful as a prophylactic or therapeutic drug for cancer, etc. A compound represented by formula (I) [wherein each symbol is as defined in the description], a salt thereof, or a cocrystal, a hydrate or a solvate of the same.

## Claims

### Claim 1

A compound represented by a formula (I):
(wherein
A represents
R1 represents 1) a hydrogen atom, 2) a halogen atom, 3) a cyano group, 4) a C1-3 alkyl group which may be substituted with 1 to 3 halogen atoms, 5) a C1-3 alkoxy group, 6) a C3-6 cycloalkyl group, or 7) a phenyl group;
R2 represents 1) a hydrogen atom or 2) a halogen atom;
R3 represents 1) a C1-6 alkyl group which may be substituted with 1 to 3 substituents selected from a C1-3 alkoxy group, a hydroxyl group and a halogen atom, 2) a pyrazolyl group which may be substituted with 1 to 3 substituents selected from a C1-3 alkyl group and a halogen atom, 3) a C3-6 cycloalkyl group, 4) an amino group di-substituted with a C1-3 alkyl group, or 5) a phenyl group which may be substituted with 1 to 3 halogen atoms;
R4 and R6 represent 1) a hydrogen atom, 2) a halogen atom, 3) a C1-3 alkyl group which may be substituted with 1 to 3 substituents selected from a) a hydroxyl group, b) a C1-3 alkoxy group which may be substituted with a 4-methoxyphenyl group and c) a halogen atom, or 4) a C1-3 alkoxy group which may be substituted with 1 to 3 halogen atoms;
R5, R7 and R9 represent 1) a C1-6 alkyl group which may be substituted with 1 to 3 C1-3 alkoxy groups or 2) a phenyl group which may be substituted with 1 to 3 halogen atoms;
R8 represents a C1-3 alkyl group; and
B represents
1) a phenyl group which may be substituted with 1 to 3 substituents selected from a) a halogen atom, b) a cyano group, c) a C1-3 alkoxy group which may be substituted with 1 to 3 halogen atoms, and d) a triazolyl group,
2) A C3-6 cycloalkyl group which may be substituted with 1 to 3 substituents selected from a) a C1-3 alkyl group which may be substituted with 1 to 3 halogen atoms and b) a halogen atom,
3) A pyridyl group which may be substituted with 1 to 3 substituents selected from a) a halogen atom, b) a cyano group, c) a C1-3 alkyl group which may be substituted with 1 to 3 halogen atoms, d) a C1-3 alkoxy group which may be substituted with 1 to 3 substituents selected from a halogen atom and a C1-3 alkoxy group, e) a pyrazolyl group which may be substituted with 1 to 3 C1-3 alkyl groups, 0 an imidazolyl group which may be substituted with 1 to 3 C1-3 alkyl groups, g) a triazolyl group which may be substituted with 1 to 3 C1-3 alkyl groups which may be substituted with 1 to 3 substituents selected from a C1-3 alkoxy group and a halogen atom, h) an azetidinyl group, i) a pyrrolidonyl group, j) a tetrazolyl group which may be substituted with 1 to 3 C1-3 alkyl groups, k) a pyrimidinyl group, and 1) an oxazolyl group,
4) A pyrazolyl group which may be substituted with 1 to 3 substituents selected from a) a C1-3 alkyl group which may be substituted with 1 to 3 halogen atoms, b) a C1-3 alkoxy group which may be substituted with 1 to 3 halogen atoms, c) a cyano group, and d) a halogen atom, or
5) An imidazopyridyl group which may be substituted with 1 to 3 halogen atoms) or a salt thereof, or a co-crystal, a hydrate or a solvate thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein A is

### Claim 3 (depends on 1)

The compound according to claim 1, wherein A is

### Claim 4 (depends on 1)

The compound according to claim 1, wherein A is
R1 is 1) a halogen atom or 2) a C1-3 alkyl group;
R2 is a hydrogen atom;
R3 is a C1-6 alkyl group which may be substituted with 1 to 3 C1-3 alkoxy groups;
R4 is 1) a halogen atom or 2) a C1-3 alkyl group;
R5 is a C1-6 alkyl group which may be substituted with 1 to 3 C1-3 alkoxy groups; and
B is a pyridyl group which may be substituted with 1 to 3 substituents selected from a) a halogen atom, b) a cyano group, c) a C1-3 alkyl group which may be substituted with 1 to 3 halogen atoms, d) a C1-3 alkoxy group which may be substituted with 1 to 3 halogen atoms, and e) a triazolyl group.

### Claim 5 (depends on 1)

The compound according to claim 1, being (S)-N-(5-chloro-6-(difluoromethoxy)pyridin-3-yl)-N′-(8-(1-methoxyethyl)-2-methylimidazo[1,2-b]pyridazin-7-yl)urea,
(S)-N-(6-chloro-4-(1-methoxyethyl)-1,5-naphthyridin-3-yl)-N′-(6-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl)urea,
(S)-N-(4-(1-methoxyethyl)-6-methyl-1,5-naphthyridin-3-yl)-N′-(6-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl)urea,
(S)-N-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-N′-(8-(1-methoxyethyl)-2-methylimidazo[1,2-b]pyridazin-7-yl)urea,
(S)-N-(5-cyano-6-(difluoromethoxy)pyridin-3-yl)-N′-(8-(1-methoxyethyl)-2-methylimidazo[1,2-b]pyridazin-7-yl)urea,
(S)-N-(8-(1-methoxyethyl)-2-methylimidazo[1,2-b]pyridazin-7-yl)-N′-(6-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl)urea,
N-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-N′-(8-(2-methoxypropan-2-yl)-2-methylimidazo[1,2-b]pyridazin-7-yl)urea,
N-(5-chloro-6-(difluoromethoxy)pyridin-3-yl)-N′-(2-chloro-8-(propan-2-yl)imidazo[1,2-b]pyridazin-7-yl)urea, or
N-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-N′-(2-methyl-8-(propan-2-yl)imidazo[1,2-b]pyridazin-7-yl)urea.

### Claim 6 (depends on 1)

The compound according to claim 1, being (S)-N-(5-chloro-6-(difluoromethoxy)pyridin-3-yl)-N′-(8-(1-methoxyethyl)-2-methylimidazo[1,2-b]pyridazin-7-yl)urea.

### Claim 7 (depends on 1)

The compound according to claim 1, being (S)-N-(6-chloro-4-(1-methoxyethyl)-1,5-naphthyridin-3-yl)-N′-(6-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl)urea.

### Claim 8 (depends on 1)

A medicine comprising the compound according to claim 1, or a salt thereof, or a co-crystal, a hydrate or a solvate thereof.

### Claim 9 (depends on 8)

The medicine according to claim 8, being a MALT1 inhibitor.