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(12) United States Patent (10) Patent No.: US 9.480,772 B2 Goto Et Al

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(12) United States Patent (10) Patent No.: US 9.480,772 B2 Goto Et Al US0094.80772B2 (12) United States Patent (10) Patent No.: US 9.480,772 B2 Goto et al. (45) Date of Patent: Nov. 1, 2016 (54) GEL SHEET CONTAINING LIPID PEPTIDE (56) References Cited GELATOR AND POLYMERC COMPOUND U.S. PATENT DOCUMENTS (75) Inventors: Masahiro Goto, Fukuoka (JP); 5,503,776 A * 4/1996 Murase ................. A23L 3,3526 Takayuki Imoto, Funabashi (JP); 252/.397 Tsubasa Kashino, Funabashi (JP); 2003/0.165560 A1* 9, 2003 Otsuka et al. ................ 424,445 2009/0297587 A1 12/2009 Yang et al. Takehisa Iwama, Funabashi (JP); 2010/0279955 A1 * 1 1/2010 Miyachi et al. ............. 514,219 Nobuhide Miyachi, Tokyo (JP) 2010/0291210 Al 11/2010 Miyachi et al. (73) Assignees: NISSAN CHEMICAL INDUSTRIES, FOREIGN PATENT DOCUMENTS LTD., Tokyo (JP). KYUSHU EP 2 494. 953 A1 9, 2012 UNIVERSITY, Fukuoka-shi (JP) JP A-6-313.064 11, 1994 JP A-9-267453 10, 1997 (*) Notice: Subject to any disclaimer, the term of this JP B2-3107488 11 2000 patent is extended or adjusted under 35 JP A-2009-102228 5, 2009 JP A-2010-95586 4/2010 U.S.C. 154(b) by 411 days. WO WO O2/22182 A1 3, 2002 WO WO 2009/005151 A1 1, 2009 (21) Appl. No.: 13/885,099 WO WO 2009/005152 A1 1, 2009 WO WO 2010/O13555 A1 2, 2010 WO WO 2011/052613 A1 5, 2011 (22) PCT Filed: Nov. 11, 2011 OTHER PUBLICATIONS (86). PCT No.: PCT/UP2011/076109 S 371 (c)(1), Takamura et al., “Drug Release from Freeze-Thaw Poly(vinyl (2), (4) Date: Jul. 15, 2013 alcohol) Gel.” Yakugaku Zasshi, 1987, vol. 107, No. 3, pp. 233-237 (with Abstract). Matsumoto et al., “The Supramolecular Hydrogel toward The (87) PCT Pub. No.: WO2012/063947 Smart Biomaterials.” Dojin News, 2006, No. 118, pp. 1-16 (with PCT Pub. Date: May 18, 2012 Abstract). Estroff et al., “Water Gelation by Small Organic Molecules.” Chemical Reviews, 2004, vol. 104, No. 3, pp. 1201-1217. (65) Prior Publication Data Suzuki et al., “Supramolecular Hydrogels Formed by -Lysine US 2013/0296761 A1 Nov. 7, 2013 Derivatives.” Chemistry Letters, 2004, vol. 33, No. 11, pp. 1496 1497. Jung et al., “Self-Assembly of a Sugar-Based Gelator in Water: Its (30) Foreign Application Priority Data Remarkable Diversity in Gelation Ability and Aggregate Structure.” Langmuir, 2001, vol. 17, pp. 7229-7232. Nov. 12, 2010 (JP) ................................. 2010-253736 Itaru et al., “Solid-Phase Lipid Synthesis (SPLS)-2: Incidental Discovery of Organogelators Based on Artificial Glycolipids.” (51) Int. Cl. Tetrahedron Letters, 2001, vol. 42, pp. 6141-6145. A6IL 26/00 (2006.01) Hamachi et al., “Solid Phase Lipid Synthesis (SPLS) for Construc A6 IK 9/00 (2006.01) tion of an Artificial Glycolipid Library.” Chem. Commun., 2000, pp. A6 IK 9/06 (2006.01) 1281-1282. A6 IK 8/65 (2006.01) (Continued) A6 IK 8/73 (2006.01) A61O 19/00 (2006.01) Primary Examiner — Amber D Steele A6 IK 8/8 (2006.01) A6 IK 8/02 (2006.01) (74) Attorney, Agent, or Firm — Oliff PLC A 6LX 9/70 (2006.01) (57) ABSTRACT A6 IK 8/49 (2006.01) A6 IK 8/04 (2006.01) There is provided a gel sheet that has high biocompatibility (52) U.S. Cl. and safety, can contain both a hydrophilic medicinal agent CPC .......... A61L 26/0095 (2013.01); A61K 8/0216 and a hydrophobic medicinal agent, and provides an excel (2013.01); A61K 8/042 (2013.01); A61 K lent feel in use during the application onto human skin or 8/4946 (2013.01); A61K 8/65 (2013.01); A61 K others. A gel sheet including: a lipid peptide gelator includ 8/73 (2013.01); A61K 8/8129 (2013.01); A61 K ing a low molecular weight lipid peptide having a molecular 9/0014 (2013.01); A61K 9/06 (2013.01); A61 K weight of 1,000 or less or a pharmaceutically usable salt of 9/7015 (2013.01); A61L 26/008 (2013.01); the lipid peptide; and a polymeric compound, wherein the A61L 26/0052 (2013.01); A61O 19/00 polymeric compound is included in an amount of more than (2013.01); A61 K 2800/10 (2013.01) 1% (w/w) and less than 50% (w/w) with respect to the total (58) Field of Classification Search mass of the gel sheet. CPC ................................................... A61L 26/OO95 See application file for complete search history. 22 Claims, 6 Drawing Sheets US 9,480.772 B2 Page 2 (56) References Cited Matsuzawa et al., “Assembly and Photoinduced Organization of Mono- and Oligopeptide Molecules Containing an Azobenzene Moiety.” Advanced Functional Materials, 2007, vol. 17, pp. 1507 OTHER PUBLICATIONS 1514. International Search Report issued in International Patent Applica tion No. PCT/JP2011/076109 dated Dec. 6, 2011. Suzuki et al., “Supramolecular Hydrogel Formed by Jun. 18, 2015 Supplementary European Search Report issued in Glucoheptonamide of -Lysine: Simple Preparation and Excellent European Application No. 11839325.5. Hydorgelation Ability.” Tetrahedron, 2007, vol. 63, pp. 7302-73.08. * cited by examiner U.S. Patent Nov. 1, 2016 Sheet 1 of 6 US 9,480,772 B2 F.G. 1 miliQ GUMARABC Š WITHOUT N-PALMITOYL G Y-HIS Š &S Š & S LOW WISCOSTY -GH WISCOSTY COUDY OUE TO PARTICLES WITH N-PALMTOYL s & SS WHITE GEL FORMED WHITE GEL FORMED SLIGHTLY WHITE GEL FORMED SHEET SHAPE SHEET SHAPE F.G. 2 F.G. 3 F.G. 4 U.S. Patent Nov. 1, 2016 Sheet 2 of 6 US 9,480,772 B2 F.G. 5 F.G. 6 REFERENCE EXAMPLE 1 COMPARATIVE REFERENCE EXAMPLE1 WHEN DEHYDRATED F.G. 7 PPTIDEMOETY (HYDROPHILIC Sl(2. (HYDROPHOBICPDMOY MOIETY)%IS (a) (b) (c) (d) U.S. Patent Nov. 1, 2016 Sheet 3 of 6 US 9.480,772 B2 F.G. 8 Yorosty Ny/ LAV/ t LJPIDMOley () C) C) A ) (HYDR OPHOBiCMOIETY) A f \\ i-A-1 (a) (e) (f) (g) FG. 9 - PEPTIDE MOIETY (HYDROPHILIC MOIETY) - PDMOY (HYDROPHOBIC SELF-ASSEMBLING MOIETY) AMELLAR STRUCTURE FIG 10 STRESS/10 Pa s BREAKING STRESS 0. 10 20 30 ---- 40 -50 ETHANOL-IMMERSED SHEET WATER-SUBSTITUTED SHEET AFTER ETHANO IMMERSON BREAKING DEFORMATION DEFORMATION/mm. DISTANCE O 2 4 6 8 10 ETHANOL-MMERSED SHEET H WATER-SUBSTITUTED SHEET AFTER H ETHANOLIMMERSION U.S. Patent Nov. 1, 2016 Sheet 4 of 6 US 9,480,772 B2 F.G. 1 a BREAKING STRESS STRESS/10 Pa O 10 - 20 30 40 - 50 METHANOL-MMERSED SHEET -- WAER-SUBSTITUTED SHEE AFTER METHANOL MMERSON a BREAKING DEFORMATON DISTANCE DEFORMATION/mm O 2 4. 6 8 m O WATER-SUBSTITUTED SHEET AFTER METHANOL MVERSION F.G. 12 F.G. 13 - - - - - - HYDROCOLODMATERAL 2O - a PWA CROSS-LINKED HYDROGEL ... PVA GEL FROZEN-THAWEDGEL 100 - N-PALMITOYL-GLY-HIS GEL FROZEN-THAWEDGELSHEET 6.8 OO 4.O 2 O sk O 2 4. 6 8 10 12 14 ELAPSED DAYS AFTER TREATMENT WITH SHEET (DAY) U.S. Patent Nov. 1, 2016 Sheet S of 6 US 9,480,772 B2 F.G. 14 AVERAGE NUMBER OF DAYS FOR 50% WOUND HEALING O 2 3 A. 5 6 7 PWA CROSS-LENKED HYDROGE PWAFROZEN-HAWEDGE N-PALMITOYL-GLY HIS FROZEN-THAWED SHEET FG 15 Š S & & Š SSRAIUM GRANULCSUM Š ..." Š EPIDERMIS SS SRAMSEN FG 16 (A) the straturwi. CORNEJMGREWANO Siis, He GRANULAIONALSO GREW StratS. S ŠS S RAf GRANLCSU SS. (D) rAM &S S S U.S. Patent Nov. 1, 2016 Sheet 6 of 6 US 9,480,772 B2 FiG 17 ( B) F.G. 18 US 9,480,772 B2 1. 2 GEL. SHEET CONTAINING LIPID PEPTIDE So as to afford a PVA hydrogel laminate having an increased GELATOR AND POLYMERC COMPOUND strength (Patent Document 5), but such a method includes too complicated processes to be industrialized. TECHNICAL FIELD PVA is commonly used as a thickener and a coating and film forming agent and is difficult to prepare a gel having The present invention relates to a gel sheet and more high strength. Thus, known methods for preparing a sheet specifically relates to a gel sheet including a low molecular from such PVA include a complicated production method of weight lipid peptide gelator and a polymeric compound. repeating a freezing and thawing process and a production BACKGROUND ART 10 method of cross-linking PVA with glutaraldehyde (Non Patent Document 1). However, such a method involves A sheet-shaped gel that is obtained by forming a gel, complicated procedures or may cause a monomer (glutar especially a hydrogel, into a sheet shape has been used in aldehyde) to be mixed in the gel, which has a risk of cosmetic and medical care fields, for example, as a pack and stimulating skins or wounds when the gel is used as cos an adhesive patch for beauty, skin treatment, and other 15 metics or external preparations. On this account, there is a purposes, as a carrier of an active component Such as a skin demand for a gel that is produced by a simple method and penetrating component and an anti-inflammatory analgesic, that includes highly safe materials. as a pressure-sensitive adhesive tape for living bodies for A carboxy vinyl polymer or a carboxy vinyl polymer wound protection, pharmaceutical drug immobilization, and other purposes, and as a wound dressing. In these applica derivative is often used for gel formation from the stand tions, a sheet-shaped gel is typically formed as a water point of easy production and flexibility. The gelation of the containing gel layer on a sheet-shaped Support medium to be carboxy vinyl polymer requires a neutralizing agent, so skin used, and the Support medium commonly used is a nonwo irritation and instability caused by the neutralizing agent is ven fabric made of polyester, polypropylene, or the like required to be improved.
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