# US 10,501,462 B2 · Pyrrolo[3,2-c]pyridine-6-amino derivatives

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- Number: US 10,501,462 B2
- Document ID: US10501462B2
- Status: Granted
- Kind: B2
- Application number: 16/064,297
- Filed: 2016-12-20
- Published: 2019-01-03
- Granted: 2019-12-10
- Earliest claimed: 2015-12-21
- Assignees: Cancer Research Technology Limited
- Applicants: Cancer Research Technology Limited
- Inventors: Sebastien Gaston Andre Naud; Julian Blagg
- Web page: https://patentgrep.com/patent/US10501462B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel pyrrolo[3,2-c]pyridine-6-amino derivatives that inhibit the spindle checkpoint function of Monospindle 1 (Mps1—also known as TTK) kinases. In particular, the present invention relates to isopropyl 6-(2-methoxy-4-(1-methyl-1H-1,2,3-triazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate and isopropyl 6-(2-methoxy-4-(1-methyl-1H-tetrazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate and their use as therapeutic agents for the treatment and/or prevention of proliferative diseases, such as cancer. The present invention also relates to processes for the preparation of these compounds and to pharmaceutical compositions comprising them.

## Claims

### Claim 1

A compound which is one of the following:
isopropyl 6-(2-methoxy-4-(1-methyl-1H-1,2,3-triazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate; or
isopropyl 6-(2-methoxy-4-(1-methyl-1H-tetrazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate;
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 2

A compound which is:
isopropyl 6-(2-methoxy-4-(1-methyl-1H-1,2,3-triazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 3

A compound which is:
isopropyl 6-(2-methoxy-4-(1-methyl-1H-tetrazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutically acceptable excipient.

### Claim 5 (depends on 1)

A method of treating a proliferative disorder in a patient in need of such treatment, said method comprising administering to said patient a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt or solvate thereof, according to claim 1, wherein the proliferative disorder is breast, ovarian, lung or colon cancer.

### Claim 6 (depends on 1)

A method of synthesising a compound according to claim 1, the method comprising:
a) reacting an intermediate of formula A:
wherein LG is a suitable leaving group;
with an intermediate of formula B:
wherein x is N or CH; and
optionally thereafter:
i) removing any protecting groups present; and/or
ii) forming a pharmaceutically acceptable salt or solvate thereof.

### Claim 7 (depends on 5)

The method of claim 5, wherein the compound is isopropyl 6-(2-methoxy-4-(1-methyl-1H-1,2,3-triazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate or a pharmaceutically acceptable salt or solvate thereof.

### Claim 8 (depends on 5)

The method of claim 5, wherein the compound is isopropyl 6-(2-methoxy-4-(1-methyl-1H-tetrazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate or a pharmaceutically acceptable salt or solvate thereof.

### Claim 9 (depends on 6)

The method of claim 6, wherein the compound is isopropyl 6-(2-methoxy-4-(1-methyl-1H-1,2,3-triazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate or a pharmaceutically acceptable salt or solvate thereof.

### Claim 10 (depends on 6)

The method of claim 6, wherein the compound is isopropyl 6-(2-methoxy-4-(1-methyl-1H-tetrazol-5-yl)phenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate or a pharmaceutically acceptable salt or solvate thereof.