# US 2014/0194624 A1 · Process for Preparation of Erlotinib and its Pharmaceutically Acceptable Salts

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- Number: US 2014/0194624 A1
- Document ID: US20140194624A1
- Status: Published application
- Kind: A1
- Application number: 14/153,594
- Filed: 2014-01-13
- Published: 2014-07-10
- Earliest claimed: 2007-04-04
- Assignees: Cipla Limited
- Applicants: Cipla Limited
- Inventors: Dharmaraj Ramachandra RAO; Rajendra Narayanrao KANKAN
- Web page: https://patentgrep.com/patent/US20140194624A1

## CPC

- C07D 239/94: Nitrogen atoms
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A process for the preparation of a salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine comprising reacting a 4-halo-6,7-bis(2-methoxyethoxy)quinazoline with 3-aminophenyl acetylene or an acid salt thereof under acidic conditions to form the corresponding acid salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine, the process optionally further comprising converting the acid salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine to N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine.

## Claims

### Claim 1

A sulphate salt, an oxalate salt, or a tosylate salt, or a succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine prepared by a process comprising reacting a 4halo-6,7-bis(2-methoxyethoxy)quinazoline with 3-aminophenyl acetylene or an acid salt thereof under acidic conditions to form the corresponding acid salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin4-amine.

### Claim 2 (depends on 1)

The sulphate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the acidic conditions are obtained using sulphuric acid.

### Claim 3 (depends on 1)

The oxalate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the acidic conditions are obtained using, oxalic acid.

### Claim 4 (depends on 1)

The tosylate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin4-amine of claim 1, wherein the acidic conditions are obtained using p-toluene sulphonic acid.

### Claim 5 (depends on 1)

The succinate salt of N-(3-ethynylphenyl)-6,7-bis(2.-methoxyethoxy)quinazolin4-amine of claim 1, wherein the acidic conditions are obtained using succinic acid.

### Claim 6 (depends on 1)

The sulphate salt, the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the process further comprises converting the acid salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine to N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine.

### Claim 7 (depends on 1)

The sulphate salt, the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the process further comprises basifying the acid salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine in the presence of a base to obtain N-(3-ethynylphenyl)-6,7-bis-methoxyethoxy)quinazolin-4-amine.

### Claim 8 (depends on 1)

The sulphate salt, the oxalate ash, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the process further comprises converting the N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine to the sulphate salt, the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine.

### Claim 9 (depends on 1)

The sulphate salt, the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin of claim 1, wherein the process is not carried out under an inert atmosphere.

### Claim 10 (depends on 1)

The sulphate salt the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the process is carried out at a temperature below 40° C.

### Claim 11 (depends on 1)

The sulphate salt, the oxalate salt, the tosylate salt, or the succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1, wherein the process is carried out in the presence of a solvent selected from the group consisting of water, C1-C4 alcohols, ketones, hydrocarbons or mixtures thereof.

### Claim 12 (depends on 1)

The sulphate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxyl)quinazolin-4-amine of claim 1.

### Claim 13 (depends on 1)

The oxalate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1.

### Claim 14 (depends on 1)

The tosylate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1.

### Claim 15 (depends on 1)

The succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 1.

### Claim 16

A sulphate salt, an oxalate salt, a tosylate salt, or a succinate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine.

### Claim 17 (depends on 16)

The sulphate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 16.

### Claim 18 (depends on 16)

The oxalate salt of 3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 16.

### Claim 19 (depends on 16)

The tosylate salt of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine of claim 16.

### Claim 20 (depends on 16)

The succinate salt of N-(3-ethynylphenyl)-6,7-bis(-methoxyethoxy)quinazolin-4-amine of claim 16.