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(19) 11 Patent Number: 6165500

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(19) 11 Patent Number: 6165500 USOO6165500A United States Patent (19) 11 Patent Number: 6,165,500 Cevc (45) Date of Patent: *Dec. 26, 2000 54 PREPARATION FOR THE APPLICATION OF WO 88/07362 10/1988 WIPO. AGENTS IN MINI-DROPLETS OTHER PUBLICATIONS 75 Inventor: Gregor Cevc, Heimstetten, Germany V.M. Knepp et al., “Controlled Drug Release from a Novel Liposomal Delivery System. II. Transdermal Delivery Char 73 Assignee: Idea AG, Munich, Germany acteristics” on Journal of Controlled Release 12(1990) Mar., No. 1, Amsterdam, NL, pp. 25–30. (Exhibit A). * Notice: This patent issued on a continued pros- C.E. Price, “A Review of the Factors Influencing the Pen ecution application filed under 37 CFR etration of Pesticides Through Plant Leaves” on I.C.I. Ltd., 1.53(d), and is subject to the twenty year Plant Protection Division, Jealott's Hill Research Station, patent term provisions of 35 U.S.C. Bracknell, Berkshire RG12 6EY, U.K., pp. 237-252. 154(a)(2). (Exhibit B). K. Karzel and R.K. Liedtke, “Mechanismen Transkutaner This patent is Subject to a terminal dis- Resorption” on Grandlagen/Basics, pp. 1487–1491. (Exhibit claimer. C). Michael Mezei, “Liposomes as a Skin Drug Delivery Sys 21 Appl. No.: 07/844,664 tem” 1985 Elsevier Science Publishers B.V. (Biomedical Division), pp 345-358. (Exhibit E). 22 Filed: Apr. 8, 1992 Adrienn Gesztes and Michael Mazei, “Topical Anesthesia of 30 Foreign Application Priority Data the Skin by Liposome-Encapsulated Tetracaine” on Anesth Analg 1988; 67: pp 1079–81. (Exhibit F). Aug. 24, 1990 DE) Germany ............................... 40 26834 Harish M. Patel, "Liposomes as a Controlled-Release Sys Aug. 24, 1990 IDE Germany ... 40 26833 tem” on Biomecial Society Transactions 609th Meeting, Mar. 6, 1991 DEI Germany ... Aug. 22, 1991 WO WIPO ....................... PCTEP91/O1596- - - - - - - - - E. Leeds, pp 513–516. (Exhibit G). (List continued on next page.) (51) Int. Cl." ..................................................... A61K 9/127 Primary Examiner-Gollamudi S. Kishore 52 U.S. Cl. ....................... 424/450; 428/4022; 424/94.3 Attorney, Agent, or Firm-Davidson, Davidson & Kappel, 58 Field of Search .................................... 424/450, 1.21, LLC 424/9.321, 9.51, 417, 96.3; 428/402.2; 57 ABSTRACT 436/829; 935/54 The invention relates to a preparation for the application of 56) References Cited agents in the form of minuscule droplets of fluid, in par ticular provided with membrane-like Structures consisting of U.S. PATENT DOCUMENTS one or Several layers of amphiphilic molecules, or an 4,911,928 3/1990 Wallach .................................. 4244so amphiphilic carrier Substance, in particular for transporting the agent into and through natural barrierS Such as skin and FOREIGN PATENT DOCUMENTS Similar materials. The preparation contains a concentration 0 102 324 3/1984 European Pat. Off.. of edge active substances which amounts to up to 99 mol-% O 211647 2/1987 European Pat. Off.. of the agent concentration which is required for the induc O 220 797 5/1987 European Pat. Off.. tion of droplet Solubilization. Such preparations are Suitable, 0220797 5/1987 European Pat. Off.. for example, for the non-invasive applications of 0 280 492 8/1988 European Pat. Off.. antidiabetics, in particular of insulin. The invention, O 475 160 3/1992 European Pat. Off.. moreover, relates to the methods for the preparation of Such 30 16976 11/1980 Germany. formulations. 37 13 494 10/1987 Germany. WO 87/O1938 4/1987 WIPO. 35 Claims, 21 Drawing Sheets 100 PERCUTANEOUS 80 UPTAKE 6O 5 MIN EFFECT 10MINEFFECT 4.O 5 MIN EFFECT 20 O 0.125 0.67 0.283 0.5 t NaCHOLiS100 (mol/mol) 6,165,500 Page 2 OTHER PUBLICATIONS Ovais Siddiqui et al., “Nonparenteral Administration of Peptide and Protein Drugs” on CRC Critical Reviews in Philip G. Green, et al., “In Vitro and in Vivo Enhancement of Skin Permeation with Oleic and Lauric Acids” on Inter Therapeutic Drug Carrier Systems, Vol. 3, ISSue 3, pp national Journal of Pharmaceutics, 48 (1988), pp 103-111. 195-208. (Exhibit M). (Exhibit H). Abstract searched from Derwent World Patents Index Latest. Guia M. Golden et al., “Role of Stratum Corneum Lipid (Exhibit N). Fluidity in Transdermal Drug Flux' on Journal of Pharma Cevic, G. et al., “Ultraflexible vesicles, TransferSomes, have ceutical Sciences vol. 76, No. 1, Jan. 1987, American an extremely low pore penetration resistance and transport Pharmaceitucal Association, pp. 25-28. (Exhibit I). therapeutic amounts of insulin acroSS the intact mammalian Bruce J. Aungst et al., “Enhancement of Naloxone Penetra skin', Biochinica et biophysica acta, 1368 pp. 201-215 tion Through Human Skin in Vitro Using Fatty Acids, Fatty (1998). Alcohols, Surfactants, Sulfoxides and Amides' on Interna Cevc, G., “Material Transport Across Permeability Barriers tional Journal of Pharmaceutics, 33(1986), pp. 225-234. by Means of Lipid Vesicles”, Handbook of Biological Phys (Exhibit J). ics, vol. 1, pp. 465-490 (1995). Ronald R. Burnette et al., “Characterization of the Permse Mayer, L.D. et al., “Vesicles of variable sizes produced by lective Properties of Excised Human Skin During Lonto a rapid extrusion procedure', Biochimica et Biophysica phoresis” on Journal of Pharmaceutical Sciences vol. 76, Acta, 858 pp. 161-165 (1986). No. 10, Oct. 1987, American Pharmaceutical ASSociation, pp. 765-773. (Exhibit K). Patel, H. M. et al., “Oral Administration of Insulin by E.C. Katoulis et al., “Efficacy of a New Needleless Insulin Encapsulation Within Liposomes”, FEBS Letters, Delivery System Monitoring of Blood Glucose Fluctuations 62(1):60–63 (Feb. 1976). and Free Insulin Levels” on International Journal of Artifical Mayer BBA858 (1986) p. 161-168. Organs vol. 12, No. 5, 1989, pp. 333-338. (Exhibit L). Patel FEBS Letters 62 #1, Feb. 1976, p 60. U.S. Patent Dec. 26, 2000 Sheet 1 of 21 6,165,500 x 2N O E G Cd O O O C Co cd 9 coO OO Or CY)O cNO S2 5 (uu) NOLLWAOO&WONWLS "YWWIO SN S2 3ONVLSIS32 (+) Ha U.S. Patent Dec. 26, 2000 Sheet 2 of 21 6,165,500 L O - aC n Z a. L S 1s 5 Cd O O Co C C O o CN 3 3 S. S S S2 S CD (uu) 13WWIO a. L O S Se CMO L n CO 2 CC D O Cd Cd O O Od O O O O O O Cd CO D u cy CN v (uuu) LWWIO U.S. Patent Dec. 26, 2000 Sheet 3 of 21 6,165,500 N CfO 2 CC L d s O E s C O o C C c. 9 O o Cd C C E D r r CN v- se ( uu) NOLIVIAOO&WONWLS'y WWI s Sn Se cC CO r CN Co ONWISIS (+)Hd U.S. Patent Dec. 26, 2000 Sheet 5 of 21 6,165,500 n CVO Z CC O d O S C O O O Co O C to S. S. S S2 S (uu) NOILVIAO OWGNWLS "LWW O U 3 Z e S o BONWISIS U.S. Patent Dec. 26, 2000 Sheet 6 of 21 6,165,500 N CfO Z CC s N O S S O O O Cd Cd C 9. Co O O o Cd E d r CY) CN ve Ya' s ONWISISY "(...) Ha U.S. Patent Dec. 26, 2000 Sheet 7 of 21 6,165,500 s 2 r- O O NOWWO TOSSAO BW U.S. Patent Dec. 26, 2000 Sheet 8 of 21 6,165,500 O v us n CO 3. Ng d d as E O S. O O Cd Od O cd 9 L) O ld C ld E S 9 N ld CN N (uu) LWWIO s ONWISIS U.S. Patent Dec. 26, 2000 Sheet 9 of 21 6,165,500 L N C/O Z C L D C S s O Cd O Cd O Cd o 9 COO Cld rC cyCd CNO 9 5 (uu) NOLIVIN3OO&WONWLS' 33WWIO s ONWISIS U.S. Patent Dec. 26, 2000 Sheet 10 of 21 6,165,500 t t i I N % IW S % I s s s I ZP 3 U.S. Patent Dec. 26, 2000 Sheet 11 of 21 6,165,500 (%)OOO19N3SOO U.S. Patent Dec. 26, 2000 Sheet 12 of 21 6,165,500 CfO d O CfO n1 L L COs H CN ves O (%) OOO19 NISOO U.S. Patent Dec. 26, 2000 Sheet 13 of 21 6,165,500 3. 2 - D CO 4. me Z CC 4. d O s N1 LL Y s s D O O O d 9 Y S. (IP/6u) OOO19 NINOLTdO3SOOn 19 U.S. Patent Dec. 26, 2000 Sheet 14 of 21 6,165,500 U N CO 2. CC L d s S SL rS. CYS SN 8w s Ysa N- (uu) NOLIVIAO O&WONWLS "WWI Vs 9 3. l d O O o Lo O Cl co n d S N ONWISIS U.S. Patent Dec. 26, 2000 Sheet 15 of 21 6,165,500 LL N CMO 2. c L d as S O Co O C 2 lc) 33 S. S Ne' \ (uu) NO WINOO&WONWLS "3LWWIO O U SR s 2 S. o ONWISIS U.S. Patent Dec. 26, 2000 Sheet 16 of 21 6,165,500 079909GZ0ZG?0||G (Ou|Ou])08NEEMLJOOLS ( uu OOv) OO U.S. Patent Dec. 26, 2000 Sheet 17 Of 21 6,165,500 g 4. - D CfO 4. s H Z CC 4. d O NC U Y s o O s Se va g (p/6u) OOOT9 NINOIL dO3SOOnTS) U.S. Patent Dec. 26, 2000 Sheet 18 of 21 6,165,500 3 4. - D 3 CO 2 Ol Z D CC Z CNS2 isan C O & CO Na VN L esa 1.
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