IP Library › Granted Patent US 12,629,343
Granted Patent B2
US 12,629,343 · App. 17/292,387 · Granted May 19, 2026

Multi-layer transdermal drug delivery system containing ibuprofen or structural analogue thereof

Inventors: Wenwei Xie (Beijing, CN); Song Lu (Beijing, CN); Shuangjiang He (Beijing, CN); Nan Chen (Beijing, CN)
Assignee: Demotech, Inc.
A61K9/7023A61K9/7084A61K31/192A61K47/02
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 12,629,343
App. No.
17/292,387
Granted
May 19, 2026
Kind
B2
Abstract

A multi-layer transdermal drug delivery system containing ibuprofen or a structural analogue thereof, comprising a transdermal patch containing ibuprofen or a structural analogue thereof and a second combined layer. The transdermal patch comprises a polymer matrix layer, the polymer matrix layer comprising an active ingredient, a compound containing at least one amino group, and a pressure-sensitive adhesive. All or some of active ingredient-amino compound salts or all or some of free active ingredients formed in the polymer matrix layer are kept in a uniform dissolution state in the polymer matrix, and can be stably stored before use, without recrystallization. The transdermal drug delivery system can continuously and controllably deliver a therapeutically effective amount of ibuprofen or a structural analogue thereof for 12 to 24 hours in the absence of a transdermal enhancer, has excellent wearing ability, and avoids a cold flow phenomenon.

Claims (38)

1 . A transdermal patch containing ibuprofen, wherein the transdermal patch comprises a polymer matrix layer comprising:

an active ingredient,

a compound containing at least one amino group, wherein the compound containing at least one amino group is an unprotonated fatty amine,

a pressure-sensitive adhesive, and

a filler in an amount of from 0.5% to 10% by weight of the total dry polymer matrix, wherein the filler comprises colloidal silicon dioxide;

wherein the active ingredient is ibuprofen;

wherein in the polymer matrix layer, part of the active ingredient forms a salt with the unprotonated fatty amine; a molar ratio of the active ingredient in the polymer matrix layer to the amino group in the compound containing at least one amino group is 12:1 to 1:1; and a content by weight of the active ingredient in the polymer matrix layer is 15% to 45%.

2 . The transdermal patch according to claim 1 , wherein the fatty amine comprises one or more of ethanolamine, diethanolamine, triethanolamine, diethylamine, triethylamine, propane diamine, N-ethylmorpholine, N-ethylpiperidine, N-ethylpiperazine, N-hydroxyethylpiperidine, N-hydroxyethylpyrrole, dimethylpropanediamine, tetramethylpropanediamine, N-dodecylpyrrole, trihexylamine, N-dodecyl homopiperidine, pyridin-2-yl-methanol, ethylenediamine, tetramethyl ethylenediamine, spermidine, spermine, cyclen, 3-(piperazin-1-yl) propan-1,2-diol, N-hydroxyethylpiperazine, N-methylmorpholine, triethylenediamine, tris(2-aminoethyl)amine, 2-piperazinone, 3-aminopiperidine, 1,3-cyclohexanedimethylamine, propylene glycol bis(3-aminopropyl) ether, and ethylene glycol bis(3-aminoethyl) ether.

3 . The transdermal patch according to claim 2 , wherein

the melting point of the formed active ingredient-amino compound salt is lower than the melting point of ibuprofen.

4 . The transdermal patch according to claim 2 , wherein a surface area of the filler ranges from 1.5 m 2 /g to 15 m 2 /g.

5 . The transdermal patch according to claim 2 , wherein the polymer matrix layer does not contain a transdermal enhancer, wherein the transdermal enhancer is selected from the group consisting of propylene glycol, PEG600, olive oil, squalene, silicone oil, mineral oil, oleic acid, isopropyl myristate, cetyl palmitate, propylene glycol monocaprylate, caprylic/capric triglyceride, ethyl oleate, oleoyl polyoxyl-6 glyceride, urea, azone, N-methylpyrrolidone, dimethyl sulfoxide and glycerin.

6 . The transdermal patch according to claim 2 , wherein a molar ratio of the active ingredient in the polymer matrix layer to the amino group in the compound containing at least one amino group is 10:1 to 1.5:1; and/or,

a content by weight of the compound containing at least one amino group in the polymer matrix layer is 1% to 15%; and/or,

a content by weight of the active ingredient in the polymer matrix layer is 20% to 40%; and/or

a content by weight of the pressure-sensitive adhesive in the polymer matrix layer is 40% to 80%.

7 . The transdermal patch according to claim 2 , wherein the patch further comprises a backing layer and a protective layer; and the polymer matrix layer is located between the backing layer and the protective layer.

8 . The transdermal patch according to claim 1 , wherein

the melting point of the formed active ingredient-amino compound salt is lower than the melting point of ibuprofen.

9 . The transdermal patch according to claim 8 , wherein a surface area of the filler ranges from 1.5 m 2 /g to 15 m 2 /g.

10 . The transdermal patch according to claim 8 , wherein the polymer matrix layer does not contain a transdermal enhancer.

11 . The transdermal patch according to claim 8 , wherein a molar ratio of the active ingredient in the polymer matrix layer to the amino group in the compound containing at least one amino group is 10:1 to 1.5:1; and/or,

a content by weight of the compound containing at least one amino group in the polymer matrix layer is 1% to 15%; and/or,

a content by weight of the active ingredient in the polymer matrix layer is 20% to 40%; and/or,

a content by weight of the pressure-sensitive adhesive in the polymer matrix layer is 40% to 80%.

12 . The transdermal patch according to claim 1 , wherein a surface area of the filler ranges from 1.5 m 2 /g to 15 m 2 /g.

13 . The transdermal patch according to claim 12 , wherein the polymer matrix layer does not contain a transdermal enhancer.

14 . The transdermal patch according to claim 1 , wherein the polymer matrix layer does not contain a transdermal enhancer.

15 . The transdermal patch according to claim 1 , wherein a molar ratio of the active ingredient in the polymer matrix layer to the amino group in the compound containing at least one amino group is 10:1 to 1.5:1; and/or,

a content by weight of the compound containing at least one amino group in the polymer matrix layer is 1% to 15%; and/or,

a content by weight of the active ingredient in the polymer matrix layer is 20% to 40%; and/or,

a content by weight of the pressure-sensitive adhesive in the polymer matrix layer is 40% to 80%.

16 . The transdermal patch according to claim 1 , wherein the patch further comprises a backing layer and a protective layer; and the polymer matrix layer is located between the backing layer and the protective layer.

17 . A multi-layer transdermal drug delivery system containing ibuprofen, wherein the multi-layer transdermal drug delivery system comprises the transdermal patch according to claim 1 , and further comprises a second combined layer; the second combined layer comprises a backing layer, a protective layer, and a polymer matrix layer located between the backing layer and the protective layer; and the polymer matrix layer comprises a pressure-sensitive adhesive.

18 . The multi-layer transdermal drug delivery system according to claim 17 , wherein the polymer matrix layer of the second combined layer further comprises a pharmaceutically acceptable auxiliary material, and/or further comprises ibuprofen; and

a content by weight of ibuprofen in the polymer matrix layer of the second combined layer is ≤15%.

19 . The multi-layer transdermal drug delivery system according to claim 18 , wherein a peripheral width of the second combined layer is 0.5 cm to 1.0 cm wider than the peripheral width of the transdermal patch.

20 . The multi-layer transdermal drug delivery system according to claim 17 , wherein a peripheral width of the second combined layer is 0.5 cm to 1.0 cm wider than the peripheral width of the transdermal patch.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2021
From: XIE, WENWEI; LU, SONG; HE, SHUANGJIANG; CHEN, NAN
To: DEMOTECH, INC.
Reel/Frame 057055/0464 →
Priority Claims (1)
CN 201811332928.4 · Nov 9, 2018 · national
Continuity (1)
Related Publication 20220008351A1 · Jan 13, 2022
References Cited (87)
US 10966936B2 · Lee · 2021 [cited by examiner]
US 20050032900A1 · Krauser · 2005 [cited by applicant]
US 20060034904A1 · Weimann · 2006 [cited by examiner]
US 20060172002A1 · Takada · 2006 [cited by examiner]
US 20070219171A1 · Lulla et al. · 2007 [cited by applicant]
US 20070259029A1 · McEntire · 2007 [cited by examiner]
US 20090022987A1 · Hashino et al. · 2009 [cited by applicant]
US 20090062754A1 · Tang · 2009 [cited by applicant]
US 20090161065A1 · Smith, III et al. · 2009 [cited by applicant]
US 20130005816A1 · Chen · 2013 [cited by examiner]
US 20130005817A1 · Tani · 2013 [cited by applicant]
US 20170087098A1 · Ritzdorf et al. · 2017 [cited by applicant]
US 20180163014A1 · Tinkl · 2018 [cited by examiner]
US 20180369174A1 · Frangakis · 2018 [cited by examiner]
CN 1162260A · 1997 [cited by applicant]
CN 1387842A · 2003 [cited by applicant]
CN 1443532A · 2003 [cited by applicant]
CN 1582142A · 2005 [cited by applicant]
CN 1827094A · 2006 [cited by applicant]
CN 1886105A · 2006 [cited by applicant]
CN 1897927A · 2007 [cited by applicant]
CN 101045041A · 2007 [cited by applicant]
CN 101347417A · 2009 [cited by applicant]
CN 101437500A · 2009 [cited by applicant]
CN 101455654A · 2009 [cited by applicant]
CN 101489985A · 2009 [cited by applicant]
CN 101502499A · 2009 [cited by applicant]
CN 101522178A · 2009 [cited by applicant]
CN 101842065A · 2010 [cited by applicant]
CN 101961418A · 2011 [cited by applicant]
CN 102000043A · 2011 [cited by applicant]
CN 102370631A · 2012 [cited by applicant]
CN 102630160A · 2012 [cited by applicant]
CN 102940618A · 2013 [cited by applicant]
CN 102949382A · 2013 [cited by applicant]
CN 104825567A · 2015 [cited by applicant]
CN 105030864A · 2015 [cited by applicant]
CN 105250243A · 2016 [cited by applicant]
CN 105520921A · 2016 [cited by applicant]
CN 106692114A · 2017 [cited by applicant]
CN 106913560A · 2017 [cited by applicant]
CN 107441063A · 2017 [cited by applicant]
CN 108078961A · 2018 [cited by applicant]
CN 109432061A · 2019 [cited by applicant]
EP 2094250A1 · 2009 [cited by applicant]
EP 2545912A1 · 2013 [cited by applicant]
JP 2013514347 · 2013 [cited by applicant]
JP 2013173805A · 2013 [cited by applicant]
JP 2016084308A · 2016 [cited by applicant]
JP 2017105724A · 2017 [cited by applicant]
JP 2018140970A · 2018 [cited by applicant]
WO 9300058A1 · 1993 [cited by applicant]
WO 2005123046A1 · 2005 [cited by applicant]
WO 2008010025A1 · 2008 [cited by applicant]
WO 2008061677A1 · 2008 [cited by applicant]
WO 2011034323A2 · 2011 [cited by applicant]
WO 2012151427A1 · 2012 [cited by applicant]
WO 2017117554A1 · 2017 [cited by applicant]
WO 2018070406A1 · 2018 [cited by applicant]
European Communication pursuant to Article 94(3) EPC for European Application No. 19881630, dated Jan. 26, 2023, 11 pages. [cited by applicant]
Hui, M., et al., “The effect of ion-pair formation combined with penetration enhancers on the skin permeation of loxoprofen”, Drug Deliv., vol. 23, No. 5, 2016, pp. 1550-1557. [cited by applicant]
Notice of Reasons for Refusal received for Japanese Patent Application No. 2021-525301, mailed on Jul. 11, 2022, 14 pages (7 pages of English Translation and 7 pages of Original Document). [cited by applicant]
Supplementary European Search Report and Opinion for European Application No. 19881630, dated Aug. 6, 2021, 14 pages. [cited by applicant]
Berton et al., “Transdermal Bioavailability in Rats of Lidocaine in the Forms of lonic Liquids, Salts, and Deep Eutectic”, ACS Med. Chem. Lett., vol. 8, (2017), pp. 498-503. [cited by applicant]
Chinese Pharmacopoeia, 2015 edition, vol. IV, general principle 0512. [cited by applicant]
Chinese Pharmacopoeia, 2015 edition, vol. IV, general principle 0931, Fourth method-paddle over disk. [cited by applicant]
Cilurzo et al., “Polymethacrylates as crystallization inhibitors in monolayer transdermal patches containing ibuprofen”, European Journal of Pharmaceutics and Biopharmaceutics, vol. 60, (2005), pp. 61-66. [cited by applicant]
Comyn, Handbook of Pressure Sensitive Adhesive Technology, Book Review, International Journal of Adhesion & Adhesives, vol. 20, (2000), pp. 427. [cited by applicant]
Gee et al., “Transdermal Delivery of Ibuprofen Utilizing a Novel Solvent-Free Pressure-sensitive Adhesive (PSA): Tepi® Technology”, Journal of Pharmaceutical Sciences, vol. 103, (2014), pp. 909-919. [cited by applicant]
International Search Report for International Application No. PCT/CN2019/113909, mailed Jan. 23, 2020, 7 pages with English Translation. [cited by applicant]
International Written Opinion for International Application No. PCT/CN2019/113909, mailed Jan. 23, 2020, 12 pages with English Translation. [cited by applicant]
Jannat et al., “Formulation and Evaluation of Sustained Release Matrix Type Transdermal Film of Ibuprofen”, Bangladesh Pharmaceutical Journal, vol. 15, Issue 1, (2012), pp. 17-21. [cited by applicant]
Jiang et al., “Ion-pair formation combined with a penetration enhancer as a dual strategy to improve the transdermal delivery of meloxicam”, Drug Deliv. and Transl. Res., vol. 8, (2018), pp. 64-72. [cited by applicant]
Michaelis et al., “Mixture design approach for early stage formulation development of a transdermal delivery system”, Drug Dev. Ind. Pharm. Early Online, (2014), pp. 1-9. [cited by applicant]
Technology of Pressure-Sensitive Adhesives and Process, Istvan Benedek, Mikhail M Feldstein, CRC press, 2009. [cited by applicant]
Tombs et al., “Transdermal Delivery of Ibuprofen Utilizing a Novel Solvent-Free Pressure-sensitive Adhesive (PSA): Tepi® Technology”, Journal of Pharmaceutical Innovation, vol. 13, (2018), pp. 48-57. [cited by applicant]
Chinese First Office Action for Application No. 202010983262.X dated Jul. 21, 2020, 14 pages with machine translation. [cited by applicant]
Chinese Second Office Action for Application No. 202010983262.X dated Jul. 28, 2022, 13 pages. [cited by applicant]
Chinese Third Office Action for Application No. 202010983262.X dated Sep. 28, 2022, 14 pages. [cited by applicant]
Japanese Decision of Refusal for Application No. 2021-525301 dated Feb. 6, 2023, 17 pages. [cited by applicant]
Japanese Notice of Refusal for Application No. 2021-525301 dated Jul. 11, 2022, 18 pages. [cited by applicant]
Japanese Notice of Refusal for Application No. 2021-525301 dated Jul. 12, 2023, 9 pages. [cited by applicant]
Japanese Notice of Refusal for Application No. 2021-525301 dated Nov. 21, 2022, 9 pages. [cited by applicant]
European Communication pursuant to Article 94(3) EPC for European Application No. 19881630, dated Jun. 26, 2024, 3 pages. [cited by applicant]
Chinese Search Report for Chinese Application No. 202010983262, dated Feb. 7, 2022, 1 page. [cited by applicant]
European Communication pursuant to Article 94(3) EPC for European Application No. 19881630, dated Jan. 21, 2025, 17 pages. [cited by applicant]
Michaelis et al., Plasticization and Antiplasticization of an Acrylic Pressure Sensitive Adhesive by Ibuprofen and Their Effect on the Adhesion Properties, European Journal of Pharmaceutics and Biopharmaceutics, (2014),… [cited by applicant]