# US 11,304,945 B2 · Pharmaceutical composition and method for preparing same

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- Number: US 11,304,945 B2
- Document ID: US11304945B2
- Status: Granted
- Kind: B2
- Application number: 16/626,910
- Filed: 2018-07-03
- Published: 2020-06-04
- Granted: 2022-04-19
- Earliest claimed: 2017-07-04
- Assignees: Jiangsu Hengrui Medicine Co., Ltd.
- Applicants: Jiangsu Hengrui Medicine Co., Ltd.
- Inventors: Daimei Zhang; Tingting Zhang; Huan Ding
- Web page: https://patentgrep.com/patent/US11304945B2

## CPC

- A61K 9/146: {with organic macromolecular compounds}
- A61K 31/5025: ortho- or peri-condensed with heterocyclic ring systems
- A61K 9/10: Dispersions; Emulsions
- A61K 9/2018: {Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates}
- A61K 47/38: Cellulose; Derivatives thereof
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 35/00: Antineoplastic agents
- 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

A solid dispersion, a method for preparing same, and a solid preparation including the solid dispersion. The solid dispersion contains (R)-4-amino-1-(1-(but-2-ynylacyl)pyrrolidin-3-yl)-3-(4-(2,6-difluorophenoxy)phenyl)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazine-7-one or a pharmaceutically acceptable salt thereof, and a carrier material. The carrier material is selected from hydroxypropyl methylcellulose acetate succinate and hydroxypropyl methylcellulose phthalate.

## Claims

### Claim 1

A solid dispersion comprising an active ingredient (R)-4-amino-1-(1-(but-2-ynoyl)pyrrolidin-3-yl)-3-(4-(2,6-difluorophenoxy)phenyl)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one or a pharmaceutically acceptable salt thereof and a carrier material, wherein the carrier material is selected from the group consisting of hydroxypropyl methylcellulose acetate succinate and hydroxypropyl methylcellulose phthalate.

### Claim 2 (depends on 1)

The solid dispersion according to claim 1, wherein the weight ratio of the carrier material to the active ingredient is not less than 0.5:1.

### Claim 3 (depends on 1)

The solid dispersion according to claim 1, wherein the weight ratio of the carrier material to the active ingredient is 0.5:1 to 4:1.

### Claim 4 (depends on 1)

The solid dispersion according to claim 1, wherein the solid dispersion consists of the active ingredient (R)-4-amino-1-(1-(but-2-ynoyl)pyrrolidin-3-yl)-3-(4-(2,6-difluorophenoxy)phenyl)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one or a pharmaceutically acceptable salt thereof and the carrier material.

### Claim 5 (depends on 1)

A method for preparing the solid dispersion according to claim 1, the method comprising the steps of dissolving the carrier material and the active ingredient or a pharmaceutically acceptable salt thereof together in an organic solvent, removing the organic solvent to obtain the solid dispersion.

### Claim 6 (depends on 5)

The method according to claim 5, wherein the organic solvent is removed by a solvent-precipitating method.

### Claim 7 (depends on 1)

A solid formulation selected from the group consisting of a tablet, pill, granule and capsule, wherein the solid formation comprises the solid dispersion according to claim 1.

### Claim 8 (depends on 7)

The solid formulation according to claim 7, wherein the solid formulation further comprises at least one pharmaceutically acceptable excipient selected from the group consisting of a disintegrant, filler, binder and lubricant.

### Claim 9 (depends on 8)

The solid formulation according to claim 8, wherein the solid formulation comprises:
1) 10 mg to 500 mg of the active ingredient or a pharmaceutically acceptable salt thereof;
2) 5 to 15% by weight of a disintegrant;
3) 30 to 90% by weight of a filler;
4) 0.5 to 10% by weight of a binder; and
5) 0.1 to 5% by weight of a lubricant.

### Claim 10 (depends on 7)

The solid formulation according to claim 7, wherein when in a medium of 0.15% aqueous solution of sodium dodecyl sulfate (SDS), the dissolution rate (%) of the active ingredient in the solid formulation is 85% or more in 45 min.

### Claim 11 (depends on 1)

A method for preparing the solid dispersion according to claim 1, the method comprising suspending and dispersing the carrier material in an organic solvent of the active ingredient or a pharmaceutically acceptable salt thereof, and removing the organic solvent to obtain the solid dispersion.

### Claim 12 (depends on 11)

The method according to claim 11, wherein the organic solvent is removed by a solvent-precipitating method.

### Claim 13 (depends on 1)

The solid dispersion according to claim 1, wherein the carrier material is hydroxypropyl methylcellulose acetate succinate.

### Claim 14 (depends on 1)

The solid dispersion according to claim 1, wherein the weight ratio of the carrier material to the active ingredient is 0.8:1 to 3:1.

### Claim 15 (depends on 1)

The solid dispersion according to claim 1, wherein the weight ratio of the carrier material to the active ingredient is 1:1 to 2:1.

### Claim 16 (depends on 7)

The solid formulation according to claim 7, wherein when in a medium of 0.15% aqueous solution of sodium dodecyl sulfate (SDS), the dissolution rate (%) of the active ingredient in the solid formulation is 90% or more in 45 min.