# US 9,040,535 B2 · Crystalline molecular comlpexes of tadalafil

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- Number: US 9,040,535 B2
- Document ID: US9040535B2
- Status: Granted
- Kind: B2
- Application number: 14/047,463
- Filed: 2013-10-07
- Published: 2014-04-10
- Granted: 2015-05-26
- Earliest claimed: 2009-02-26
- Assignees: Thar Pharmaceuticals, Inc.
- Applicants: Thar Pharmaceuticals, Inc.
- Inventors: Mazen Hanna; Ning Shan; Miranda L. Cheney; David R. Weyna
- Web page: https://patentgrep.com/patent/US9040535B2

## CPC

- C07D 471/14: Ortho-condensed systems
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 15/10: for impotence
- 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

Crystalline molecular complexes of tadalafil are disclosed. The crystalline molecular complexes include those of tadalafil and oxalic acid, tadalafil and 4-hydroxybenzoic acid, tadalafil and 3-phenylpropanoic acid, tadalafil and malonic acid, tadalafil and methylparaben, and tadalafil and propylparaben. Pharmaceutical compositions containing the crystalline molecular complexes are also disclosed.

## Claims

### Claim 1

A crystalline molecular complex of tadalafil comprising tadalafil and a propylparaben co-former.

### Claim 2 (depends on 1)

A crystalline molecular complex of tadalafil and propylparaben according to claim 1 where the molar ratio of the tadalafil and the propylparaben in the molecular complex is 1:1.

### Claim 3 (depends on 1)

A crystalline molecular complex of tadalafil and propylparaben according to claim 1, wherein the molecular complex is characterized by at least one of the following:
an X-ray powder diffractogram in accordance with FIG. 11; or
a Fourier transform infrared spectrum in accordance with FIG. 12.

### Claim 4 (depends on 1)

A crystalline molecular complex of tadalafil and propylparaben of claim 1, wherein the molecular complex is characterized by: an X-ray powder diffractogram having peaks at 5.2, 10.5, 15.3, 18.7, 20.6, 22.0, and 24.5 °2θ±0.2 °2θ; an infrared spectrum having peaks at 747, 1098, 1271, 1433, 1645, 1700, and 3338 cm−1±cm−1; or both.

### Claim 5 (depends on 4)

A pharmaceutical composition comprising a crystalline molecular complex of tadalafil and propylparaben of claim 4 and a pharmaceutically acceptable carrier.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a crystalline molecular complex of tadalafil and propylparaben of claim 1 and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

A method for making a crystalline molecular complex of tadalafil and propylparaben according to claim 1, comprising the steps of:
grinding tadalafil and propylparaben; and
adding acetonitrile to the ground tadalafil and propylparaben.

### Claim 8 (depends on 1)

A method for making a crystalline molecular complex of tadalafil and propylparaben according to claim 1, comprising the steps of:
slurrying tadalafil, propylparaben, and acetonitrile; and
drying the slurried tadalafil, propylparaben, and acetonitrile.