IP Library Granted Patent US 9,949,941
Granted Patent B2
US 9,949,941 · App. 15/359,321 · Granted Apr 24, 2018

GABA analog prodrug sustained release oral dosage forms

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Quick Facts
Patent No.
US 9,949,941
App. No.
15/359,321
Granted
Apr 24, 2018
Kind
B2
Abstract

Sustained release oral dosage forms of a gabapentin prodrug, 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid, are disclosed. The dosage forms are useful for treating or preventing diseases and disorders for which gabapentin is therapeutically effective.

Claims (18)

1. A method of treating panic in a patient, comprising administering to the patient in need of such treatment one or more sustained release oral tablets comprising:

(a) 10 wt % to 65 wt % of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid;

(b) 5 wt % to 20 wt % of a diluent consisting of microcrystalline cellulose;

(c) 1 wt % to 50% of a release rate-modifying polymer consisting of a methacrylic acid copolymer;

wherein wt % is based on the total dry weight of the dosage form, which one or more tablets:

when administered to one or more fasted human patients in need of a method of treating panic at a dose of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from about 1100 mg to about 1300 mg provides a gabapentin plasma concentration profile characterized by a C max ranging from about 3 μg/mL to about 6 μg/mL, a T max ranging from about 4 hours to about 7 hours, and a AUC ranging from about 30 μg·hr/mL to about 70 μg·hr/mL; or

when administered to one or more fed human patients in need of a method of treating panic at a dose of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from about 1100 mg to about 1300 mg provides a gabapentin plasma concentration profile characterized by a C max ranging from about 5 μg/mL to about 8 μg/mL, a T max ranging from about 6 hours to about 11 hours, and a AUC ranging from about 60 μg·hr/mL to about 110 μg·hr/mL.

2. The method of claim 1 , the tablet comprising an amount of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 300 mg to 700 mg.

3. The method of claim 1 , wherein the 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid is in a crystalline form.

4. The method of claim 1 , wherein the dosing comprises frequency of twice per day.

5. A method of treating panic in a patient, comprising administering to the patient in need of such treatment one or more sustained release oral tablets comprising:

(a) 10 wt % to 65 wt % of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid;

(b) 5 wt % to 20 wt % of a diluent consisting of microcrystalline cellulose;

(c) 1 wt % to 50% of a release rate-modifying polymer consisting of a methacrylic acid copolymer;

wherein wt % is based on the total dry weight of the dosage form, which tablet, when placed in 10 mM monobasic potassium phosphate buffer and 1% (wt/volume) sodium lauryl sulfate at pH 7.4 and 37° C. and agitated at 50 rpm (USP, Type II), releases 20% of the 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid after 2 hours, 50% after 5 hours and 80% after 8 hours.

6. The method of claim 5 , the tablet comprising an amount of 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 300 mg to 700 mg.

7. The method of claim 5 , wherein the 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid is in a crystalline form.

8. The method of claim 5 , wherein the dosing comprises frequency of twice per day.

Assignments (6)
CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Mar 17, 2025
From: ARBOR PHARMACEUTICALS, LLC; AZURITY PHARMACEUTICALS, INC.; AZURITY PHARMACEUTICALS IRELAND LIMITED; SILVERGATE PHARMACEUTICALS, INC.
To: HPS INVESTMENT PARTNERS, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 070531/0487 →
RELEASE OF SECURITY INTEREST Recorded Mar 14, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: AZURITY PHARMACEUTICALS, INC.; SILVERGATE PHARMACEUTICALS, INC.; ARBOR PHARMACEUTICALS, LLC; SLAYBACK PHARMA LIMITED LIABILITY COMPANY
Reel/Frame 070521/0299 →
SECURITY INTEREST Recorded Sep 20, 2021
From: ARBOR PHARMACEUTICALS, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057544/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2018
From: XENOPORT, INC.
To: ARBOR PHARMACEUTICALS, LLC
Reel/Frame 046633/0753 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2018
From: ARBOR PHARMACEUTICALS, LLC
To: XENOPORT, INC.
Reel/Frame 046449/0306 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 30, 2016
From: CUNDY, KENNETH C.; SASTRY, SRIKONDA; LEUNG, MANSHIU; KADRI, BALAJI V.; STACH, PAUL E.
To: XENOPORT, INC.
Reel/Frame 040471/0018 →