IP Library Granted Patent US 10,577,376
Granted Patent B2
US 10,577,376 · App. 15/843,875 · Granted Mar 3, 2020

Benzoic acid, benzoic acid derivatives and heteroaryl carboxylic acid conjugates of hydrocodone, prodrugs, methods of making and use thereof

Inventors: Travis Mickle (Kissimmee, FL); Sven Guenther (Coralville, IA); Christal Mickle (Kissimmee, FL); Guochen Chi (Coralville, IA); Jaroslaw Kanski (Blacksburg, VA); Andrea K. Martin (Fincastle, VA); Bindu Bera (Blacksburg, VA)
Assignee: KemPharm, Inc.
C07D489/02A61K9/0019A61K9/20A61K9/2054A61K31/167A61K31/485A61K45/06A61K47/48038A61K47/542A61K47/545A61K47/55A61K47/556A61P25/30C07D489/04C07D491/08A61K2300/00
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Quick Facts
Patent No.
US 10,577,376
App. No.
15/843,875
Granted
Mar 3, 2020
Kind
B2
Abstract

The presently described technology provides methods of treating a patient having moderate to severe pain, narcotic or opioid abuse or narcotic or opioid withdrawal. The presently described methods are carried out by comprising administering to the patient a pharmaceutically effective amount of a composition comprising acetaminophen and benzoate-hydrocodone hydrochloride. The composition has reduced side effects when compared with unconjugated hydrocodone.

Claims (19)

1. A method for treating a patient having moderate to severe pain, acute or chronic pain, narcotic or opioid abuse or narcotic or opioid withdrawal comprising administering to the patient a pharmaceutically effective amount of a composition comprising acetaminophen and benzoate-hydrocodone hydrochloride wherein:

a) the benzoate-hydrocodone hydrochloride has reduced side effects when compared with an equivalent molar amount of unconjugated hydrocodone, and/or

b) the benzoate-hydrocodone hydrochloride exhibits lower mean exposure to hydrocodone when administered at about more than 53 mg when compared to an equivalent molar amount of unconjugated hydrocodone.

2. The method of claim 1 , wherein the composition is a prodrug.

3. The method of claim 1 , wherein the composition is used to reduce or prevent oral, intranasal or intravenous drug abuse; or to provide oral, intranasal or parenteral drug abuse resistance.

4. The method of claim 1 , wherein the composition exhibits an improved AUC and rate of release of hydrocodone over time when compared to an equivalent molar amount of unconjugated hydrocodone over the same time period.

5. The method of claim 1 , wherein the composition is provided in a dosage form selected from the group consisting of: a tablet, a capsule, a caplet, a suppository, a troche, a lozenge, an oral powder, a solution, an oral film, a thin strip, a slurry, and a suspension.

6. The method of claim 1 , wherein one of the reduced side effects comprises a lower than normal concentration of oxygen in arterial blood of the patient.

7. The method of claim 1 , wherein one of the reduced side effects comprises reduced respiratory depression in the patient.

8. The method of claim 1 , wherein the method is for acute pain.

9. The method of claim 1 , wherein the method is for chronic pain.

10. The method of claim 5 , wherein the composition is provided in a tablet dosage.

11. The method of claim 10 , wherein the tablet comprises 6.67 mg of benzoate-hydrocodone hydrochloride.

12. The method of claim 11 , wherein the tablet comprises 6.12 mg of benzoate-hydrocodone.

13. The method of claim 1 , wherein the pharmaceutically effective amount of the composition is provided in a pharmaceutical kit comprising one or more individual doses.

14. The method of claim 13 , wherein the pharmaceutical kit comprises about 1 individual dose to about 100 individual dosages.

15. The method of claim 14 , wherein the individual dosages comprises from about 1 to about 60 individual dosages.

16. The method of claim 15 , wherein the individual dosages comprises from about 10 to about 30 individual dosages.

17. The method of claim 1 , wherein the composition further comprises one or more of microcrystalline cellulose, crospovidone, starch 1500 G, povidone K30, or stearic acid.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Mar 13, 2026
From: ALTER DOMUS (US) LLC
To: ZEVRA THERAPEUTICS, INC.
Reel/Frame 075080/0907 →
SECURITY INTEREST Recorded Apr 8, 2024
From: ZEVRA THERAPEUTICS, INC.
To: ALTER DOMUS (US) LLC
Reel/Frame 067040/0637 →
CHANGE OF NAME Recorded Feb 23, 2024
From: KEMPHARM, INC.
To: ZEVRA THERAPEUTICS, INC.
Reel/Frame 066664/0108 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2018
From: MICKLE, TRAVIS; GUENTHER, SVEN; MICKLE, CHRISTAL; CHI, GUOCHEN; KANSKI, JAROSLAW; MARTIN, ANDREA K; BERA, BINDU
To: KEMPHARM, INC.
Reel/Frame 045274/0436 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2018
From: MICKLE, TRAVIS; GUENTHER, SVEN; MICKLE, CHRISTAL; CHI, GUOCHEN; KANSKI, JAROSLAW; MARTIN, ANDREA K; BERA, BINDU
To: KEMPHARM, INC.
Reel/Frame 045253/0497 →
Continuity (6)
Division 14816915 · Aug 3, 2015
Continuation In Part 14557570 · Dec 2, 2014
Continuation 13888587 · May 7, 2013
Continuation 12828381 · Jul 1, 2010
Provisional Application 61222718 · Jul 2, 2009
Related Publication 20180104352A1 · Apr 19, 2018