IP Library Granted Patent US 12,350,281
Granted Patent B2
US 12,350,281 · App. 16/879,626 · Granted Jul 8, 2025

Long-acting injectable formulations and use thereof

Inventors: Gail L. Dempsey (Greensboro, NC); Douglas L. Hepler (Greensboro, NC); Dorothea Erxleben (Greensboro, NC); Michael S. Daniel (Greensboro, NC); Neil E. Paulsen (Greensboro, NC)
Assignee: Dechra Veterinary Products, LLC
A61K31/7048A61K9/0019A61K31/137A61K31/497A61K31/573A61K47/14A61K47/26A61K47/28
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,350,281
App. No.
16/879,626
Granted
Jul 8, 2025
Kind
B2
Abstract

Provided herein are long-acting, non-aqueous pharmaceutically acceptable compositions of active ingredients for subcutaneous injection.

Claims (33)

1. A non-aqueous, extended release, injectable pharmaceutically acceptable composition, comprising:

a) a pharmaceutically active agent present at about 1.0 to 25% w/w;

b) glycerol monooleate present at about 5.0 to 40.0% w/w;

c) a C8 triglyceride, a C10 triglyceride, or a combination thereof present at about 5.0 to 80.0% w/w;

d) ethanol and benzyl alcohol present at about 1 to 25% w/w in combination; and

e) a surfactant present in an amount of about 0.5 to 5.0% w/w,

wherein the composition forms a water-insoluble depot upon injection wherein the pharmaceutically acceptable active agent is selected from a fluroquinolone and florfenicol, and wherein upon subcutaneous injection, at least 90% of the pharmaceutically active agent is released by about 150 hours.

2. The composition of claim 1 , comprising:

the glycerol monooleate present at about 20% w/w;

C8 triglyceride, a C10 triglyceride, or a combination thereof present at about 60% w/w; and

the ethanol and benzyl alcohol present at about 10% w/w in combination.

3. The composition of claim 1 , wherein the fluoroquinolone is benofloxacin, binfloxacin, cinoxacin, ciprofloxacin, danofloxacin, difloxacin, enoxacin, enrofloxacin, fleroxacin, ibafloxacin, levofloxacin, lomefloxacin, marbofloxacin, moxifloxacin, norfloxacin, ofloxacin, orbifloxacin, pefloxacin, pipemidic acid, temafloxacin, tosufloxacin, sarafloxacin, sparfloxacin, or combination thereof.

4. The composition of claim 1 , further comprising an excipient.

5. The composition of claim 1 , further comprising polyoxyl castor oil.

6. The composition of claim 1 , further comprising hydrogenated phosphatidylcholine from soybean lecithin.

7. The composition of claim 1 , further comprising an anti-oxidant.

8. The composition of claim 1 , further comprising cholesterol.

9. The composition of claim 1 , wherein the C8 triglyceride is caprylic acid, and the C10 triglyceride is capric acid.

10. The composition of claim 1 , wherein at least about 100, 500, 1,000, 2,000, 3,000, 4,000, 5,000, 10,000, 15,000 or 20,000 ng/ml of the pharmaceutically active agent is present in the blood stream of a subject for at least about 48, 60, 72, 84, 96, 108, 120, 132, 144, 156, 168 hours or greater upon administration to a mammal.

11. A method of treating a disease or disorder in a subject, comprising administering to the subject an effective amount of the composition of claim 1 .

12. The method of claim 11 , wherein the subject is a mammal.

13. The method of claim 12 , wherein the subject is a canine.

14. The method of claim 11 , wherein the subject is a feline.

15. The method of claim 11 , wherein the disease or disorder is an infection.

16. The method of claim 11 , wherein at least about 100, 500, 1,000, 2,000, 3,000, 4,000, 5,000, 10,000, 15,000 or 20,000 ng/ml of the pharmaceutically active agent is present in the blood stream of the subject for at least about 48, 60, 72, 84, 96, 108, 120, 132, 144, 156, 168 hours or greater upon administration to a mammal.

17. An extended release, injectable pharmaceutically acceptable composition comprising:

a) a pharmaceutically active agent that is marbofloxacin present at about 15 to 25% w/w;

b) glycerol monooleate present at about 15 to 40% w/w;

c) a C8 triglyceride, a C10 triglyceride, or a combination thereof present at about 40 to 55% w/w;

d) ethanol present at about 1 to 10% w/w; and

e) benzyl alcohol present at about 1 to 10% w/w;

wherein the composition forms a water-insoluble depot upon injection,

wherein the composition is suitable for either subcutaneous or intramuscular injection and wherein upon subcutaneous injection, at least 90% of the pharmaceutically active agent is released by about 150 hours.

Assignments (3)
CHANGE OF NAME Recorded Dec 8, 2023
From: PIEDMONT ANIMAL HEALTH INC.
To: PIEDMONT ANIMAL HEALTH LLC
Reel/Frame 065842/0188 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 15, 2022
From: PIEDMONT ANIMAL HEALTH LLC
To: DECHRA VETERINARY PRODUCTS, LLC
Reel/Frame 061769/0452 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2020
From: DEMPSEY, GAIL L.; HEPLER, DOUGLAS I.; ERXLEBEN, DOROTHEA; DANIEL, MICHAEL S.; PAULSEN, NEIL E.
To: PIEDMONT ANIMAL HEALTH INC.
Reel/Frame 054513/0486 →
Continuity (2)
Provisional Application 62852527 · May 24, 2019
Related Publication 20200368263A1 · Nov 26, 2020
References Cited (40)
US 6552002B2 · Steber et al. · 2003 [cited by applicant]
US 9956164B2 · Zaremba et al. · 2018 [cited by applicant]
US 20080085263A1 · Thuresson · 2008 [cited by examiner]
US 20120058187A1 · Lallemand · 2012 [cited by examiner]
US 20130156853A1 · Zhang et al. · 2013 [cited by applicant]
US 20140275261A1 · Okumu et al. · 2014 [cited by applicant]
US 20150290322A1 · Yoon et al. · 2015 [cited by applicant]
US 20160000797A1 · Checcone · 2016 [cited by examiner]
US 20180117016A1 · Tamraz et al. · 2018 [cited by applicant]
US 20180256622A1 · Hepler et al. · 2018 [cited by applicant]
US 20180344629A1 · Hepler et al. · 2018 [cited by applicant]
CN 1686156 · 2005 [cited by examiner]
CN 1895262A · 2007 [cited by applicant]
CN 102617595 · 2012 [cited by examiner]
CN 109310680A · 2019 [cited by applicant]
CN 2019048799 · 2019 [cited by examiner]
JP S54132223A · 1979 [cited by applicant]
JP H11507278A · 1999 [cited by applicant]
JP 2001261558A · 2001 [cited by applicant]
JP 2001524510A · 2001 [cited by applicant]
JP 2003508449A · 2003 [cited by applicant]
JP 2003525892A · 2003 [cited by applicant]
JP 2005537280A · 2005 [cited by applicant]
JP 2009519253A · 2009 [cited by applicant]
JP 2013536805A · 2013 [cited by applicant]
JP 2016504352A · 2016 [cited by applicant]
JP 2017506671A · 2017 [cited by applicant]
WO WO2010129622 · 2010 [cited by examiner]
WO WO2013057208A1 · 2013 [cited by applicant]
WO WO2017023694 · 2017 [cited by examiner]
WO WO2018005777 · 2018 [cited by examiner]
Zhang, CN 1686156, puclished: Oct. 26, 2005, English machine translation obtained Sep. 26, 2022. (Year: 2022). [cited by examiner]
Yoshida, CN 2019048799, published: Mar. 28, 2019, English machine translation obtained on May 29, 2023. (Year: 2023). [cited by examiner]
Zejin et al. CN 102617595, published: Aug. 1, 2012; English machine translation obtained on Sep. 18, 2024. (Year: 2024). [cited by examiner]
International Search Report issued on Aug. 17, 2020, regarding PCT/US2020/033839. [cited by applicant]
Extended European Search Report for EP 20815338.7 dated May 17, 2023, 13 pages. [cited by applicant]
Matschke et al., “Sustained-Release Injectables Formed In Situ And Their Potential Use For Veterinary Products,” Journal of Controlled Release, vol. 85, pp. 1-15, 2002. [cited by applicant]
CN Office Action in Chinese Application No. 202080035528.6, dated Nov. 28, 2022, 15 pages (with English translation). [cited by applicant]
JP Office Action in Japanese Application No. 2021-569299, dated Jan. 23, 2024, 12 pages (with English translation). [cited by applicant]
JP Office Action in Japanese Application No. 2021-569299, dated Jul. 29, 2024, 8 pages (with English translation). [cited by applicant]