# US 11,299,477 B2 · Process for the preparation of Pazopanib or a pharmaceutically acceptable salt thereof

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- Number: US 11,299,477 B2
- Document ID: US11299477B2
- Status: Granted
- Kind: B2
- Application number: 16/802,273
- Filed: 2020-02-26
- Published: 2020-08-20
- Granted: 2022-04-12
- Earliest claimed: 2013-11-05
- Assignees: Laurus Labs Limited
- Applicants: Laurus Labs Limited
- Inventors: Satyanarayana Chava; Seeta Rama Anjaneyulu Gorantla; Venkata Sunil Kumar Indukuri; Sanjay Kumar Dehury; Nagaraju Mekala; Jahangeer Baba Shaik; Durga Prasad Kuchipudi
- Web page: https://patentgrep.com/patent/US11299477B2

## CPC

- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention is relates to an improved process for the preparation of pazopanib or a pharmaceutically acceptable salts thereof. The present invention also relates to novel polymorphic Forms of pazopanib hydrochloride, and its intermediates thereof.

## Claims

### Claim 1

Crystalline Form-K1 of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine, characterized by a powder X-Ray diffraction (PXRD) pattern substantially in accordance with FIG. 22.

### Claim 2

A process for preparation of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine Form-K1 characterized by a powder X-Ray diffraction (PXRD) pattern according to FIG. 22, comprising:
a) reacting a compound of Formula II with methyl iodide in presence of potassium tert butoxide in dimethylformamide to obtain a compound of Formula III Form-K1,
and
b) isolating the Formula III Form-K1.

### Claim 3 (depends on 2)

The process of claim 2, wherein the step a) is carried out at a temperature of about 25° C. to about reflux temperature.

### Claim 4

Crystalline Form-K2 of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine, characterized by a powder X-Ray diffraction (PXRD) pattern substantially in accordance with FIG. 23.

### Claim 5

A process for preparation of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine Form-K2 characterized by a powder X-Ray diffraction (PXRD) pattern according to FIG. 23, comprising:
a) reacting a compound of Formula II with methyl iodide in presence of potassium tert butoxide in tetrahydrofuran to obtain a compound of Formula III,
b) concentrating the reaction mass to obtain a residue;
c) adding water to the residue of step b); and
d) isolating the Formula III Form-K2.

### Claim 6 (depends on 5)

The process of claim 5, wherein the step a) is carried out at a temperature of about 25° C. to about reflux temperature.

### Claim 7 (depends on 5)

The process of claim 5, wherein the step b) is carried out by removing the solvent under vacuum at 40° C. to about 45° C.

### Claim 8

Crystalline Form-K3 of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine, characterized by a powder X-Ray diffraction (PXRD) pattern substantially in accordance with FIG. 24.

### Claim 9

A process for preparation of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine Form-K3 characterized by a powder X-Ray diffraction (PXRD) pattern according to FIG. 24, comprising:
a) reacting a compound of Formula II with methyl iodide in presence of potassium tert butoxide in acetonitrile to obtain a compound of Formula III,
and
b) isolating the Formula III Form-K3.

### Claim 10 (depends on 9)

The process of claim 9, wherein the step a) is carried out at a temperature of about 25° C. to about reflux temperature.

### Claim 11

Crystalline Form-K4 of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine, characterized by a powder X-Ray diffraction (PXRD) pattern substantially in accordance with FIG. 25.

### Claim 12

A process for preparation of N-(2-chloropyrimidin-4-yl)-N-2,3-trimethyl-2H-indazol-6-amine Form-K4 characterized by a powder X-Ray diffraction (PXRD) pattern according to FIG. 25, comprising:
a) reacting compound of Formula II with methyl iodide in presence of potassium tert butoxide in dimethylsulfoxide to obtain a compound of Formula III,
b) concentrating the reaction mass to obtain a residue;
c) adding water to the residue of step b); and
d) isolating the Formula III Form-K4.

### Claim 13 (depends on 12)

The process of claim 12, wherein the step a) is carried out at a temperature of about 25° C. to about reflux temperature.

### Claim 14 (depends on 7)

The process of claim 7, wherein the step b) is carried out by removing the solvent under vacuum at 40° C. to about 45° C.