IP Library Granted Patent US 10,376,587
Granted Patent B2
US 10,376,587 · App. 16/151,678 · Granted Aug 13, 2019

High capacity diketopiperazine microparticles and methods

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Quick Facts
Patent No.
US 10,376,587
App. No.
16/151,678
Granted
Aug 13, 2019
Kind
B2
Abstract

Disclosed herein are diketopiperazine microparticles having high capacity for adsorbing a drug or active agent. In particular, the diketopiperazine microparticle are formed using fumaryl diketopiperazine and can comprise a drug in large doses for the treatment of disease or disorders by pulmonary delivery via oral inhalation.

Claims (14)

1. A method of delivering a drug or an active agent to a patient in need thereof comprising administering to the patient in need thereof using a reusable inhaler an inhalable composition comprising a drug or active agent and diketopiperazine microparticles, each of the diketopiperazine microparticles comprising a plurality of structural domains, each of the plurality of structural domains comprising a nucleus surrounded by layers of a porous crystalline material, and each of the diketopiperazine microparticles have a mass-weighted average particle size of about 33,000 to about 216,000 voxels measured by X-ray tomography for particle sizes measuring from about 0.5 pm to about 4 pm in geometric diameter.

2. The method of claim 1 , wherein said diketopiperazine is fumaryl diketopiperazine or 3,6-bis(N-fumaryl-4-aminobutyl)-2,5-diketopiperazine; or salt thereof.

3. The method of claim 1 , wherein the diketopiperazine microparticles comprise structural domains ranging in number-weighted size from about 250 voxels to about 1,400 voxels.

4. The method of claim 1 , wherein the diketopiperazine microparticles comprise structural domains ranging in voxel-weighted size from about 500 voxels to about 2,000 voxels.

5. The method of claim 1 , wherein the diketopiperazine microparticles have a specific surface area greater than 70 m 2 /g.

6. The method according to claim 1 , further comprising a surfactant.

7. The method according to claim 6 , wherein said surfactant is polysorbate 80.

8. The method of claim 1 , wherein said drug or active agent is a small organic molecule, peptide or protein, a lipid, or a nucleic acid molecule, or combinations thereof.

9. The method according to claim 1 , wherein said active agent is insulin.

10. The method of claim 8 , wherein said peptide or protein is insulin, parathyroid hormone, calcitonin, glucagon, glucagon-like peptide 1, oxyntomodulin, oxytocin, CCK-8, PYY3-36, ghrelin, vasoactive intestinal peptide, leuprolide, growth hormone, RGD (Arg-Gly-Assp) peptide, growth hormone releasing peptide, DDAVP (desamino-Cys-1, D-arg8) vasopressin peptide, cyclosporine, detirelex, somatostatin, interferon-.alpha., granulocyte colony stimulating factor, IgG, an analog or active fragment thereof.

11. The method of claim 8 , wherein the small organic molecule is a neurotransmitter agonist, a neurotransmitter antagonist, a pain inhibitory agent, a vaccine, an anti-inflammatory agent, an anti-cancer agent, a cell receptor agonist molecule, cell receptor antagonist molecule, an immunosuppressant, a vasodilator, a statin or an anti-infective agent.

12. The method of claim 1 , wherein the inhalable composition is in dry powder form.

13. A dry powder inhaler for use with the method according to claim 1 , and wherein said inhalable composition is in dry powder form.

14. The dry powder inhaler of claim 13 , wherein the inhalable composition is provided in a unit dose cartridge for using with a reusable inhaler.

Assignments (5)
PATENT SECURITY AGREEMENT Recorded Aug 12, 2025
From: MANNKIND CORPORATION
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 072444/0525 →
RELEASE OF SECURITY INTEREST Recorded Apr 5, 2024
From: MIDCAP FINANCIAL TRUST, AS AGENT
To: MANNKIND CORPORATION; MANNKIND LLC
Reel/Frame 067024/0082 →
RELEASE OF SECURITY INTEREST Recorded Aug 13, 2019
From: DEERFIELD PRIVATE DESIGN FUND II, L.P.; DEERFIELD PRIVATE DESIGN INTERNATIONAL II, L.P.; HORIZON SANTE FLML SARL
To: MANNKIND CORPORATION
Reel/Frame 050044/0138 →
SECURITY INTEREST Recorded Aug 13, 2019
From: MANNKIND CORPORATION; MANNKIND LLC
To: MIDCAP FINANCIAL TRUST, AS AGENT
Reel/Frame 050044/0181 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2018
From: GRANT, MARSHALL; MENKIN, PAUL; STOWELL, GRAYSON W.
To: MANNKIND CORPORATION
Reel/Frame 047070/0774 →