IP Library › Granted Patent US 12,485,099
Granted Patent B2
US 12,485,099 · App. 17/660,313 · Granted Dec 2, 2025

Transdermal therapeutic system containing asenapine and polysiloxane or polyisobutylene

Inventors: Patrick Mohr (Bad Breisig, DE); René Rietscher (Andernach, DE); René Eifler (Koblenz, DE); Olga Bourquain (Dürrholz, DE)
Assignee: LTS LOHMANN Therapie-Systeme AG
A61K9/7069A61K9/7053A61K31/407
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Quick Facts
Patent No.
US 12,485,099
App. No.
17/660,313
Granted
Dec 2, 2025
Kind
B2
Abstract

The present invention relates to a transdermal therapeutic system (TTS) for the transdermal administration of asenapine comprising a self-adhesive layer structure comprising a therapeutically effective amount of asenapine, said self-adhesive layer structure comprising: A) a backing layer; B) an asenapine-containing layer comprising: 1. asenapine in the form of the free base; and 2. a polymer selected from the group consisting of polysiloxanes and polyisobutylenes in an amount of more than 50% by weight based on the total weight of the asenapine-containing layer; and C) optionally an additional skin contact layer.

Claims (74)

1 . A transdermal therapeutic system for the transdermal administration of asenapine comprising a self-adhesive layer structure comprising a therapeutically effective amount of asenapine, said self-adhesive layer structure comprising:

A) a backing layer;

B) an asenapine-containing layer comprising:

i) asenapine in free base form; and

ii) a polysiloxane or polyisobutylene polymer, wherein the polysiloxane or polyisobutylene polymer comprises more than 50% by weight of the asenapine-containing layer; and

C) optionally an additional skin contact layer; and

wherein the asenapine-containing layer comprises an additional acrylic polymer.

2 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer is an asenapine-containing matrix layer.

3 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer is obtainable by incorporating the asenapine free base.

4 . The transdermal therapeutic system according to claim 1 ,

wherein at least 90 mol % of the asenapine in the asenapine-containing layer are present in free base form.

5 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine is present in the asenapine-containing layer in an amount ranging from 1 to 10% by weight, based on the total weight of the asenapine-containing layer.

6 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine is present in the transdermal therapeutic system in an amount ranging from 3 to 21 mg.

7 . The transdermal therapeutic system according to claim 1 ,

wherein the polysiloxane or polyisobutylene polymer comprises from 55 to 98% by weight of the asenapine-containing layer.

8 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer comprises polysiloxane.

9 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer comprises polyisobutylene.

10 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer further comprises at least one additive or excipient selected from the group consisting of crystallization inhibitors, solubilizers, fillers, substances for skincare, pH regulators, preservatives, tackifiers, softeners, stabilizers, and permeation enhancers.

11 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer further comprises a crystallization inhibitor, and wherein the crystallization inhibitor is polyvinylpyrrolidone.

12 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer further comprises a stabilizer, and wherein the stabilizer is selected from the group consisting of tocopherol and ester derivatives thereof and ascorbic acid and ester derivatives thereof.

13 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer further comprises a permeation enhancer, and wherein the permeation enhancer is selected from the group consisting of diethylene glycol monoethyl ether, diisopropyl adipate, isopropyl myristate, isopropyl palmitate, lauryl lactate, and dimethylpropylene urea.

14 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer does not comprise isopropyl palmitate.

15 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer does not comprise a permeation enhancer selected from oleic acids, oleic alcohols, and triglycerides.

16 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer does not comprise a permeation enhancer.

17 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer further comprises a copolymer based on dimethylaminoethyl methacrylate, butyl methacrylate and methyl methacrylate.

18 . The transdermal therapeutic system according to claim 1 ,

wherein the transdermal therapeutic system has an area of release ranging from 5 to 60 cm 2 .

19 . The transdermal therapeutic system according to claim 1 ,

wherein the asenapine-containing layer has an area weight ranging from 50 to 120 g/m 2 .

20 . The transdermal therapeutic system according to claim 1 ,

wherein the transdermal therapeutic system provides a skin permeation rate of asenapine as measured in a Franz diffusion cell with dermatomed human skin of

0 μg/(cm 2 *h) to 12 μg/(cm 2 *h) in the first 4 hours;

1 μg/(cm 2 *h) to 22 μg/(cm 2 *h) from hour 4 to hour 8;

6 μg/(cm 2 *h) to 25 μg/(cm 2 *h) from hour 8 to hour 12;

5 μg/(cm 2 *h) to 20 μg/(cm 2 *h) from hour 12 to hour 16;

4 μg/(cm 2 *h) to 18 μg/(cm 2 *h) from hour 16 to hour 20; and

2 μg/(cm 2 *h) to 12 μg/(cm 2 *h) from hour 20 to hour 24.

21 . The transdermal therapeutic system according to claim 1 ,

wherein the transdermal therapeutic system provides a cumulative permeated amount of asenapine as measured in a Franz diffusion cell with dermatomed human skin of 120 μg/cm 2 to 380 μg/cm 2 over a time period of 24 hours.

22 . The transdermal therapeutic system according to claim 1 ,

wherein the transdermal therapeutic system provides a permeated amount of asenapine as measured in a Franz diffusion cell with dermatomed human skin of

0 μg/cm 2 to 50 μg/cm 2 in the first 4 hours;

20 μg/cm 2 to 120 μg/cm 2 from hour 4 to hour 8;

40 μg/cm 2 to 220 μg/cm 2 from hour 8 to hour 12;

60 μg/cm 2 to 290 μg/cm 2 from hour 12 to hour 16;

80 μg/cm 2 to 340 μg/cm 2 from hour 16 to hour 20; and

100 μg/cm 2 to 380 μg/cm 2 from hour 20 to hour 24.

23 . The transdermal therapeutic system according to claim 1 ,

wherein the transdermal therapeutic system provides a mean release rate of from 0.5 to 20 mg/day of asenapine over at least 24 hours of administration.

24 . A method of treating a disorder in a human patient in need thereof, the method comprising applying the transdermal therapeutic system of claim 1 to the skin of the human patient in need thereof.

25 . The method of claim 24 , wherein the disorder is bipolar disorder, schizophrenia, or both.

26 . The method claim 24 , wherein the method comprises applying the transdermal therapeutic system to the skin of the patient for a dosing interval of from 20 to 30 hours.

27 . A process for manufacturing the asenapine-containing layer according to claim 1 , the process comprising the steps of:

1) combining at least

a) asenapine free base;

b) a polysiloxane or polyisobutylene polymer, wherein the polysiloxane or polyisobutylene polymer comprises more than 50% by weight of the asenapine-containing layer; and

c) optionally at least one additive;

 to obtain a coating composition;

2) coating the coating composition onto a backing layer or release liner or any intermediate liner; and

3) drying the coated coating composition to form the asenapine-containing layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2023
From: MOHR, PATRICK; RIETSCHER, RENÉ; EIFLER, RENÉ; BOURQUAIN, OLGA
To: LTS LOHMANN THERAPIE-SYSTEME AG
Reel/Frame 065333/0156 →
Priority Claims (2)
EP 16205502 · Dec 20, 2016 · regional
EP 17178268 · Jun 28, 2017 · regional
Continuity (2)
Continuation 16470322
Related Publication 20220323370A1 · Oct 13, 2022
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