# US 2019/0314448 A1 · Treatment of degenerative joint disease

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- Number: US 2019/0314448 A1
- Document ID: US20190314448A1
- Status: Published application
- Kind: A1
- Application number: 16/279,667
- Filed: 2019-02-19
- Published: 2019-10-17
- Earliest claimed: 2011-10-10
- Assignees: Ampio Pharmaceuticals, Inc.
- Applicants: Ampio Pharmaceuticals, Inc.
- Inventors: David Bar-Or; James V. Winkler
- Web page: https://patentgrep.com/patent/US20190314448A1

## CPC

- A61K 38/12: Cyclic peptides {, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C (A61K38/043 - A61K38/046 take precedence)}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 31/167: having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A61K 31/20: having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K 31/405: Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- A61K 31/495: having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53})
- A61K 31/573: substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- 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

The invention provides a method of treating a degenerative joint disease. The method comprises administering an effective amount of a pharmaceutical composition comprising a diketopiperazine with amino acid side chains of aspartic acid and alanine (DA-DKP). The invention also provides a pharmaceutical product as well as a kit comprising DA-DKP.

## Claims

### Claim at position 1

-27. (canceled)

### Claim 28

A method of treating joint pain in a human comprising administering to a joint of the human selected from the group consisting of a shoulder joint, a hand joint and a spinal joint, an intra-articular injection of an effective amount of a pharmaceutical composition comprising DA-DKP prepared by removing albumin from a solution of a human serum albumin composition.

### Claim 29 (depends on 28)

The method of claim 28 wherein the composition is administered at a frequency selected from the group consisting of:
a. no more frequently than once every six months,
b. no more frequently than once every 5 months,
c. no more frequently than once every 4 months,
d. no more frequently than once every 3 months, and
e. no more frequently than once every 2 months.

### Claim 30 (depends on 28)

The method of claim 28, wherein the composition administered by intra-articular injection is a composition having a concentration of DA-DKP from 50 μM to 350 μM.

### Claim 31 (depends on 28)

The method of claim 28, wherein the composition further comprises N-acetyl-tryptophan (NAT), caprylic acid, caprylate or combinations thereof.

### Claim 32 (depends on 31)

The method of claim 31, wherein the composition is a composition having a concentration of NAT, caprylic acid, caprylate or combinations thereof from 4 mM to 20 mM.

### Claim 33 (depends on 28)

The method of claim 28, wherein the step of removing the albumin comprises treating the human serum albumin composition by a separation method selected from the group consisting of ultrafiltration, sucrose gradient centrifugation, chromatography, salt precipitation, and sonication.

### Claim 34 (depends on 33)

The method of claim 33, wherein the step of removing comprises passing the human serum albumin composition over an ultrafiltration membrane with a molecular weight cut off that retains the albumin, and wherein the resulting filtrate comprises DA-DKP.

### Claim 35 (depends on 34)

The method of claim 34, wherein the ultrafiltration membrane has a molecular weight cutoff selected from the group consisting of less than 50 kDa, less than 40 kDa, less than 30 kDa, less than 20 kDa, less than 10 kDa, less than 5 kDa and less than 3 kDa.

### Claim 36 (depends on 28)

The method of claim 28, wherein the pharmaceutical composition further comprises a second drug selected from the group consisting of an analgesic, an anti-inflammatory drug, and combinations thereof.

### Claim 37

A method of treating joint pain in a human comprising administering to a joint of the human selected from the group consisting of a shoulder joint, a hand joint and a spinal joint, an intra-articular injection of an effective amount of a pharmaceutical composition comprising DA-DKP at a concentration of from 50 μM to 350 μM prepared by passing the human serum albumin composition over an ultrafiltration membrane with a molecular weight cut off that retains the albumin, and wherein the resulting filtrate comprises DA-DKP.

### Claim 38 (depends on 37)

The method of claim 37, wherein the composition is a composition having a concentration of NAT, caprylic acid, caprylate or combinations thereof from 4 mM to 20 mM.

### Claim 39 (depends on 37)

The method of claim 37, wherein the ultrafiltration membrane has a molecular weight cutoff selected from the group consisting of less than 50 kDa, less than 40 kDa, less than 30 kDa, less than 20 kDa, less than 10 kDa, less than 5 kDa and less than 3 kDa.

### Claim 40 (depends on 37)

The method of claim 37, wherein the ultrafiltration membrane has a molecular weight cutoff of less than 5 kDa.

### Claim 41

A method of treating osteoarthritis in a human comprising administering to a joint of the human selected from the group consisting of a shoulder joint, a hand joint and a spinal joint, an effective amount of a pharmaceutical composition comprising DA-DKP prepared by removing albumin from a solution of a human serum albumin composition.

### Claim 42 (depends on 41)

The method of claim 41, wherein the composition is a composition having a concentration of NAT, caprylic acid, caprylate or combinations thereof from 4 mM to 20 mM.

### Claim 43 (depends on 41)

The method of claim 41, wherein the ultrafiltration membrane has a molecular weight cutoff selected from the group consisting of less than 50 kDa, less than 40 kDa, less than 30 kDa, less than 20 kDa, less than 10 kDa, less than 5 kDa and less than 3 kDa.

### Claim 44 (depends on 41)

The method of claim 41, wherein the ultrafiltration membrane has a molecular weight cutoff of less than 5 kDa.

### Claim 45 (depends on 41)

The method of claim 41, wherein the pharmaceutical injection is by intra-articular injection to the joint selected from the group consisting of a shoulder joint, a hand joint and a spinal joint of the human.