# US 2021/0330664 A1 · Pharmaceutical compositions

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- Number: US 2021/0330664 A1
- Document ID: US20210330664A1
- Status: Published application
- Kind: A1
- Application number: 16/624,860
- Filed: 2017-06-23
- Published: 2021-10-28
- Earliest claimed: 2017-06-23
- Assignees: Birdie Biopharmaceuticals, Inc.
- Applicants: Birdie Biopharmaceuticals, Inc.
- Inventors: Lixin Li
- Web page: https://patentgrep.com/patent/US20210330664A1

## 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)
- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure relates to new crystal forms of chemical compounds, formulations including, methods of forming, and methods of using same.

## Claims

### Claim 1

A composition comprising resiquimod in the form of a sulfate salt in crystal form A.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the sulfate salt is a monosulfate salt.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the sulfate salt is an anhydrate.

### Claim 4 (depends on 1)

The composition of claim 1, wherein crystal form A is characterized by x-ray powder diffraction spectrum that comprises peaks at about 7 to about 8 degrees 2θ, about 13.5 to about 14.5 degrees 2θ, about 19 to about 20 degrees 2θ, and about 19.5 to about 20.5 degrees 2θ.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the crystal form A is stable at room temperature at least about 2 days.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the crystal form A is stable at room temperature at least about 1 week.

### Claim 7 (depends on 1)

A dosage form comprising the composition of claim 1.

### Claim 8

A composition comprising a crystal form of a compound of Formula I:
wherein R1 is hydrogen; C1-C10 straight chain or branched chain substituted or unsubstituted alkyl, wherein the substituent is C3-C6 cycloalkyl or C3-C6 cycloalkyl substituted by straight chain or branched chain C1-C4 alkyl; straight chain or branched chain C2-C10 alkenyl; or substituted straight chain or branched chain C2-C10 alkenyl, wherein the substituent is C3-C6 cycloalkyl or C3-C6 cycloalkyl substituted by straight chain or branched chain C1-C4 alkyl; C1-C6 hydroxyalkyl; alkoxyalkyl wherein the alkoxy moiety contains one to about four carbon atoms and the alkyl moiety contains one to about six carbon atoms; acyloxyalkyl wherein the acyloxy moiety is alkanoyloxy of two to about four carbon atoms or benzoyloxy, and the alkyl moiety contains one to about six carbon atoms; benzyl; (phenyl)ethyl; or phenyl; the benzyl, (phenyl)ethyl, or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from C1-C4 alkyl, C1-C4 alkoxy, or halogen, with the proviso that if the benzene ring is substituted by two moieties, then the moieties together contain no more than six carbon atoms;
R2 and R3 are independently selected from hydrogen, C1-C4 alkyl, phenyl, or substituted phenyl, wherein the substituent is C1-C4 alkyl, C1-C4 alkoxy, or halogen;
X is C1-C4 alkoxy, alkoxyalkyl wherein the alkoxy moiety contains one to about four carbon atoms and the alkyl moiety contains one to about four carbon atoms, C1-C4 hydroxyalkyl, C1-C4 haloalkyl, alkylamido wherein the alkyl group contains one to about four carbon atoms, amino, substituted amino wherein the substituent is C1-C4 alkyl or C1-C4 hydroxyalkyl, azide, chloro, hydroxy, 1-morpholino, 1-pyrrolidino, or C1-C4 alkylthio; and
R is hydrogen, straight chain or branched chain C1-C4 alkoxy, halogen, or straight chain or branched chain C1-C4 alkyl; and
wherein the crystal form is a hydrochloric acid salt, a sulfate salt, a phosphate salt, a maleate salt, a malate salt, an adipate salt, a glycolate salt, a hippurate salt, a tartrate salt, a fumarate salt, a citrate salt, a lactate salt, a succinate salt, a tosylate salt, mesylate salt, an oxalate salt, a gentisate salt, a benzoate salt, or a nitrate salt in crystalline form A, B, C, D, E, F or G.

### Claim 9 (depends on 8)

The composition of claim 8, wherein R1 is 2-methylpropyl or benzyl.

### Claim 10 (depends on 8)

The composition of claim 8, wherein X is azido, hydroxy, ethoxy, methoxy, 1-morpholino, or methylthio.

### Claim 11 (depends on 8)

The composition of claim 8, wherein R is hydrogen.

### Claim 12 (depends on 8)

The composition of claim 8, wherein the compound is 4-amino-α-butyl-1-(2-methylpropyl)-1H-imidazo-[4,5-c]-quinoline-2-methanol hemihydrate, 4-amino-α, α-dimethyl-2-ethoxymethyl-1H-imidazo-[4,5-c]-quinoline-1-ethanol, 2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo-[4,5-c]-quinolin-4-amine, or 4-amino-1-phenylmethyl-1H-imidazo-[4,5-c]-quinoline-2-methanol.

### Claim 13 (depends on 8)

The composition of claim 8, wherein the compound is resiquimod.

### Claim 14 (depends on 8)

The composition of claim 8, wherein the crystal form is form A.

### Claim 15 (depends on 8)

The composition of claim 8, wherein the crystal form is in a sulfate salt.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the sulfate salt is a monosulfate salt.

### Claim 17 (depends on 15)

The pharmaceutical composition of claim 15, wherein the sulfate salt is an anhydrate.

### Claim 18 (depends on 8)

A method of treating a cancer in a subject in need thereof, comprising administering a composition including a crystal form of a compound having a Formula of claim 8 to a subject in need thereof.

### Claim 19 (depends on 8)

A method of treating a tumor in a subject in need thereof, comprising administering a composition including a crystal form of a compound having a Formula of claim 8 to a subject in need thereof.

### Claim 20 (depends on 18)

The method of claim 18, wherein the tumor is a carcinoma, a sarcoma, or a blastoma.