# US 8,569,488 B2 · Crystalline pyridazine compound

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- Number: US 8,569,488 B2
- Document ID: US8569488B2
- Status: Granted
- Kind: B2
- Application number: 13/336,512
- Filed: 2011-12-23
- Published: 2012-05-03
- Granted: 2013-10-29
- Earliest claimed: 2007-07-06
- Assignees: Gilead Sciences, Inc.; K.U. Leuven Research & Development; Gerhard Puerstinger
- Applicants: Eric D. Dowdy; Kenneth M. Kent; Norma J. Tom; Vahid Zia
- Inventors: Eric D. Dowdy; Kenneth M. Kent; Norma J. Tom; Vahid Zia
- Web page: https://patentgrep.com/patent/US8569488B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 31/16: for influenza or rhinoviruses
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A crystalline compound of formula (1) and its salts and solvates are provided for the treatment or prophylaxis of hepatitis C virus infections Methods of making and formulating crystalline compound (1) are provided.

## Claims

### Claim 1

A pharmaceutical composition comprising a compound of formula (1)
and one or more fatty acids.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1 wherein the fatty acid is a saturated or unsaturated 4-22 carbon chain.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1 wherein the fatty acid is linoleic, oleic, lauric, palmitic or myristic acid.

### Claim 4 (depends on 1)

The pharmaceutical composition of claim 1 wherein the fatty acid is oleic acid.

### Claim 5 (depends on 4)

The pharmaceutical composition of claim 4 wherein compound (1) is 8% by weight and the oleic acid is 92% by weight.

### Claim 6 (depends on 1)

The pharmaceutical composition of claim 1 wherein compound (1) is 20% by weight and the oleic acid is 80% by weight.

### Claim 7 (depends on 1)

The pharmaceutical composition of claim 1 further comprising polyethylene glycols, or short, medium, or long chain mono, di, or triglycerides, or pegylated short, medium or long chain fatty acids.

### Claim 8 (depends on 3)

The pharmaceutical composition of claim 3 further comprising one or more surfactants selected from fatty acid esters of polyoxyethylene sorbitan, sorbitan fatty acid ester, polyoxyethylene castor oil derivatives, polyoxyethleneglycerol oxystearate, polyethyleneglycol 60, hydrogenated castor oil, and block copolymers of ethylene oxide and propylene oxide.

### Claim 9 (depends on 8)

The pharmaceutical composition of claim 8 wherein the fatty acid is oleic acid and the surfactant is polyoxyethylene sorbitan.

### Claim 10 (depends on 9)

The pharmaceutical composition of claim 9 comprising 8% of compound (1), 87.4% of oleic acid and 4.6% of polyoxyethylene sorbitan, by weight.

### Claim 11 (depends on 9)

The pharmaceutical composition of claim 9 comprising 20% of compound (1), 76% of oleic acid and 4% of polyoxyethylene sorbitan, by weight.

### Claim 12 (depends on 9)

The pharmaceutical composition of claim 9 comprising 8% of compound (1), 86.47% of oleic acid, 4.6% of polyoxyethylene sorbitan, 0.92% Aerosil 200, and 0.01% BHT, by weight.

### Claim 13 (depends on 9)

The pharmaceutical composition of claim 9 comprising 8% of compound (1), 85.55% of oleic acid, 4.6% of polyoxyethylene sorbitan, 1.84% Aerosil 200, and 0.01% BHT, by weight.

### Claim 14 (depends on 9)

The pharmaceutical composition of claim 9 comprising 10% of compound (1), 84.55% of oleic acid, 5.00% of polyoxyethylene sorbitan, 0.35% BHA, and 0.1% BHT, by weight.

### Claim 15 (depends on 9)

The pharmaceutical composition of claim 9 further comprising one or more alcohols selected from ethanol, benzyl alcohol, glycerol, polyethylene glycol 200, polyethylene glycol 300, and polyethylene glycol 400.

### Claim 16 (depends on 9)

The pharmaceutical composition of claim 9 comprising 8% of compound (1), 73.6% of oleic acid, 9.2% of polyoxyethylene sorbitan, and 9.2% of ethanol, by weight.

### Claim 17

A pharmaceutical dosage form comprising a compound of formula (1)
and one or more fatty acids selected from oleic, lauric, palmitic and myristic acid.

### Claim 18 (depends on 17)

The pharmaceutical dosage form of claim 17 comprising oleic acid and polyoxyethylene sorbitan.

### Claim 19 (depends on 17)

The pharmaceutical dosage form of claim 17 wherein the dosage form is a capsule.