# US 2021/0330666 A1 · Oral solid formulation containing irinotecan and method of preparing the same

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- Number: US 2021/0330666 A1
- Document ID: US20210330666A1
- Status: Published application
- Kind: A1
- Application number: 17/370,709
- Filed: 2021-07-08
- Published: 2021-10-28
- Earliest claimed: 2015-06-30
- Assignees: Hanmi Pharm. Co., Ltd.
- Applicants: Hanmi Pharm. Co., Ltd.
- Inventors: Caleb Hyung Min PARK; Myeong Ki JUNG; Jin Cheul KIM; Yong Il KIM; Jae Hyun PARK; Jong Soo WOO
- Web page: https://patentgrep.com/patent/US20210330666A1

## CPC

- A61K 31/4745: condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines (yohimbine derivatives, vinblastine A61K31/475; ergoline derivatives A61K31/48)
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/1682: {Processes}
- A61K 9/2013: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- A61K 9/2027: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/20: containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
- A61P 35/00: Antineoplastic agents
- A61K 9/4858: {Organic compounds}
- A61K 2300/00: Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

An oral solid formulation includes irinotecan or a pharmaceutically acceptable salt thereof as an active ingredient, and an acidifying agent. A method of preparing an oral solid formulation includes forming granules containing irinotecan or a pharmaceutically acceptable salt thereof, a diluent, and a binder, mixing the granules with a disintegrant and a lubricant to obtain a mixture, and includes adding an acidifying agent in step of forming granules and/or mixing the granules.

## Claims

### Claim 1

An oral solid formulation comprising:
irinotecan or a pharmaceutically acceptable salt thereof; and
an acidifying agent.

### Claim 2 (depends on 1)

The oral solid formulation of claim 1, wherein the acidifying agent is a C2-C20 organic acid including a carboxyl group (COOH) or a sulfonic acid group (SO3H).

### Claim 3 (depends on 2)

The oral solid formulation of claim 2, wherein the acidifying agent is selected from the group consisting of acetic acid, adipic acid, citric acid, ascorbic acid, erythorbic acid, lactic acid, propionic acid, tartaric acid, fumaric acid, formic acid, oxalic acid, camsylic acid, malic acid, maleic acid, edisylic acid, palmitic acid, stearic acid, and any combinations thereof.

### Claim 4 (depends on 2)

The oral solid formulation of claim 2, wherein the acidifying agent is selected from the group consisting of acetic acid, citric acid, lactic acid, and any combinations thereof.

### Claim 5 (depends on 1)

The oral solid formulation of claim 1, wherein, when a dissolution test takes place using the paddle method in the U.S. Pharmacopoeia (USP) with 900 mL of purified water, the dissolution medium of the oral solid formulation has a pH of about 1 to 5 in 30 minutes of the dissolution test.

### Claim 6 (depends on 1)

The oral solid formulation of claim 1, wherein the amount of the acidifying agent is from about 0.2 parts to about 10 parts by weight based on 1 part by weight of the irinotecan or pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1)

The oral solid formulation of claim 1, wherein the oral solid formulation is in the form of granules, a capsule, or a tablet.

### Claim 8 (depends on 1)

The oral solid formulation of claim 1, wherein the oral solid formulation further comprises a pharmaceutically acceptable additive selected from the group consisting of a diluent, a binder, a disintegrant, a lubricant, and any combinations thereof.

### Claim 9 (depends on 8)

The oral solid formulation of claim 8, wherein the oral solid formulation comprises about 20 wt % to about 80 wt % of the diluent, about 1 wt % to about 10 wt % of the binder, about 2 wt % to about 7 wt % of the disintegrant, or about 0.5 wt % to about 5 wt % of the lubricant based on a total weight of the oral solid formulation.

### Claim 10 (depends on 1)

The oral solid formulation of claim 1, wherein, when a dissolution test takes place using the paddle method in the U.S. Pharmacopoeia (USP) with 900 mL of purified water, a dissolution rate of an active ingredient in the solid formulation is about 80% or greater in 30 minutes of the dissolution test.

### Claim 11 (depends on 1)

The oral solid formulation of claim 1, wherein the oral solid formulation is for the treatment of cancer.

### Claim 12 (depends on 1)

A method of preparing an oral solid formulation according to claim 1, the method comprising:
forming granules comprising irinotecan or a pharmaceutically acceptable salt thereof, a diluent, and a binder;
mixing the granules with a disintegrant and a lubricant to obtain a mixture; and
optionally, formulating the resultant mixture,
wherein, in the step of forming granules and/or mixing the granules, an acidifying agent is added.

### Claim 13 (depends on 12)

The method of claim 12, wherein the step of forming granules is performed by wet granulation or dry granulation.

### Claim 14 (depends on 13)

The method of claim 13, wherein the wet granulation comprises forming granules by granulating a mixture of the irinotecan or pharmaceutically acceptable salt thereof and the diluent in combination with a binding solution including the binder, wherein the acidifying agent is added to the mixture and/or the binding solution.