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III |||||||||| USOO5290752A United States Patent (19) 11 Patent Number: 5,290,752 Kifune Et Al III |||||||||| USOO5290752A United States Patent (19) 11 Patent Number: 5,290,752 Kifune et al. 45 Date of Patent: Mar. 1, 1994 (54) METHOD FOR PREPARATION OF A SHAPED CHITN BODY CONTAINING A OTHER PUBLICATIONS PHYSOLOGICALLY ACTIVE SUBSTANCE Chemical Abstracts, vol. 101, No. 14, Oct. 1, 1984, p. 66 No. 112325v. 75 Inventors: Koji Kifune, Nara; Kenzo Motosugi; Patent Abstracts of Japan, vol. 3, No. 55 (C-45), May Hiroyuki Tanae, both of Kyoto, all of 11, 1979, p. 141 C 45 and JP-A-5431 458 of Mar. 8, Japan 1979. McCormick I. CAS 96:81186x, 1980. 73 Assignee: Unitika Ltd., Hyogo, Japan McCormick, C. L. IV et al (1984) CA 101:186132b. McCormick et al V, "Homogenous Solution, etc" J. (21) Appl. No.: 963,256 Polymer Science 17494 (1979). Unitika, "Chitin dopes." (1984) CA 101:112326w (22 Filed: Oct. 19, 1992 (1984). Miyazaki et al, "The use of chitin, etc;' (1981) Chem. Related U.S. Application Data Pharm. Bull, vol. 29, pp. 3067-3069 (1981). 63 Continuation of Ser. No. 526,942, May 21, 1990, which Teijin, "Solubilizing drugs by size, etc.," (1984) CA is a continuation of Ser. No. 712,489, Mar. 8, 1985, 100:126927.j(1984). abandoned. Chang et al, "Effects of water removal, etc;' (1980) CA 94:15261.4g (1981). (30) Foreign Application Priority Data Primary Examiner-Richard L. Raymond Mar. 16, 1984 (JP) Japan .................................. 59-51880 Assistant Examiner-S. Mark Clardy Attorney, Agent, or Firm-Sughrue, Mion, Zinn, 51) Int. Cl. ............................................. AON 25/10 Macpeak & Seas 52 U.S. Cl. .................................... 504/116; 424/408; 424/488; 514/777 57 ABSTRACT 58) Field of Search ............. 71/DIG. 1; 514/55, 777; A shaped chitin body containing a high content of a 424/488, 408; 504/116; A01N 25/10 physiologically active substance, such as a drug to be used for the cure or prevention of disease, is prepared 56 References Cited by incorporating said physiologically active substance U.S. PATENT DOCUMENTS into a dope comprising (a) a water-insoluble chitin, (b) 3,911,098 10/1975 Capozza .............................. 424/428 lithium chloride, and (c) N-methylpyrrolidone and/or 4,007,258 2/1977 Cohen et al. .......................... 424/22 dimethylacetamide, with the amount of said physiologi 4,059,457 1/1977 Austin .............. ... 106/203 cally active substance incorporated being 0.5 wt.% or 4,267,280 5/1981 McCormick, II ..................... 52.5/56 more with respect to the amount of the chitin contained 4,267,281 5/1981 McCormick, III ................... 525/61 in said dope, and thereafter coagulating the resulting 4,282,209 8/1981 Tocker ............. ... 514/477 mixture with a coagulant to obtain a shaped body. 4,376,199 3/1983 Koshugi ........... ... 536/20 4,378,017 3/1983 Koshugi et al. ..... ... 424/35 The high content of the physiologically active sub stance thus incorporated in the shaped chitin can be 4,389,331 6/1983 Samejima et al. ....... 424/35 slowly released therefrom over a long period of time. 4,536,207 8/1985 McCandliss et al. ................... 7/88 The shaped-chitin of the present invention is character 4,704,268 11/1987 Kifune ................................. 424/488 ized by long duration of the physiological activity of the FOREIGN PATENT DOCUMENTS active substance contained therein. 0013181 7/1980 European Pat. Off. ... C08B 37/08 0021750 7/1981 European Pat. Off. 12 Claims, No Drawings 5,290,752 2 less, and the duration for releasing the active substance METHOD FOR PREPARATION OF A SHAPEO is almost within 24 hours. CHTIN BODY CONTAINING A U.S. Pat. No. 4,059,457 discloses a method for prepar PHYSOLOGICALLY ACTIVE SUBSTANCE ing a shaped chitin body, wherein a chitin is dissolved in 5 a lithium chloride-containing dimethylacetamide solu This is a continuation of application Ser. No. tion or in a lithium chloride-containing N-methylpyr 07/526,942, filed May 21, 1990, which is a continuation rolidone solution, and the resulting chitin-dope is coag application of application Ser. No. 06/712,489, filed ulated with a coagulant to obtain a shaped chitin body. Mar. 18, 1985, now abandoned. However, there is no disclosure in U.S. Pat. No. 10 4,059,457 with respect to a method where a physiologi FIELD OF THE INVENTION cally active substance is incorporated in a chitin-dope. The present invention relates to a method for prepa ration of a shaped chitin body containing a high content SUMMARY OF THE INVENTION of a physiologically active substance, which substance The present inventors have conducted further studies can be slowly released therefrom and lasts for a long S in order to be able to increase the concentration of period of time. physiologically active substance that can be incorpo rated in a water-insoluble chitin and to obtain a drug BACKGROUND OF THE INVENTION containing chitin which may slowly release the active Various methods have heretofore been proposed for ingredient therefrom for a long period of time. As a the purpose of prolonging the effective life of physio 20 result, the inventors have found that a shaped chitin logically active substances, where a physiologically body which may contain a large amount of a physiolog active substance is contained in a carrier of a polymeric ically active substance can be obtained by incorporating substance. In particular, a natural polymeric substance said active substance in a dope obtained by dissolving a such as a cellulose or a starch is proposed as being pref water-insoluble chitin in a specific solvent, and thereaf 25 ter coagulating the resulting mixture with a coagulant, erable as a carrier in such case in a form wherein the and furthermore that the physiologically active sub physiologically active substance-containing carrier is stance contained in the shaped chitin body is not sub used as found in nature and therefore must be safe. Such stantially deactivated, and may therefore be slowly natural polymeric substances include a chitin of an released from the shaped chitin body for a long period amino-polysaccharide. In this connection, U.S. Pat. No. 30 of time. 3,911,098, corresponding to Japanese Patent Applica The present invention, therefore, provides a method tion (OPI) No. 123815/75 (The term "OPI" as used for preparing a shaped chitin body containing a physio herein refers to a "published unexamined Japanese pa logically active substance, comprising incorporating a tent application'.) discloses a drug-releasing instru physiologically active substance in a dope comprising ment, where a drug is incorporated in a chitin solution 35 (a) a water-insoluble chitin, (b) lithium chloride, and (c) and the resulting mixture is shaped to form a shaped N-methylpyrrolidone and/or dimethylacetamide, the body which may slowly release the effective ingredient amount of said physiologically active substance being of the incorporated drug. This prior art technique, how 0.5 wt.% or more with respect to the amount of the ever, has some problems, in that the chitin component chitin in said dope, and then the resulting mixture is used therein is a water-soluble chitin derivative, and coagulated with a coagulant to form a shaped body. therefore, when said drug-releasing instrument is used in the presence of water, the carrier itself is dissolved DETAILED DESCRIPTION OF THE and the effect of the physiologically active substance INVENTION contained therein does not last for a long period of time. “Water-insoluble chitin' as used in the present inven The present inventors have conducted extensive 45 tion includes poly(N-acetyl-D-glucosamine) obtained studies to overcome the above-mentioned problem and from crustaceans or insects by treating with hydrochlo to obtain a biolytic drug-releasing body comprising a ric acid or sodium hydroxide to remove proteins and water-insoluble chitin as a carrier, and as a result, previ calcium contents therefrom for purification, and deriva ously proposed a method where a physiologically ac tives of said chitin which are insoluble in water. Such tive substance is incorporated in a swelled body of a 50 derivatives include partly deacetylated chitins (or a part water-insoluble chitin, as described in U.S. application of the acetylamino groups in the chitin are deacetyl Ser. No. 637,191, filed Feb. 8, 1984, now U.S. Pat. No. ated), and etherified, esterified, hydroxyethylated, or 4,704,268, corresponding to Japanese Patent Applica O-ethylated chitins. Examples of these chitin deriva tion No. 145428/83). However, this prior art process tives include poly(N-acetyl-6-O-(2'-hydroxyethyl)-D- still involves a problem in that a physiologically active 55 glucosamine, poly N-acetyl-6-O-(ethyl)-D-glucosa substance can generally not be incorporated in the car mine, etc. rier at a desirably high concentration. In order to obtain a shaped chitin body according to A shaped chitin body containing a physiologically the present invention, a dope is first prepared, compris active substance at a high concentration is disclosed in ing (a) said water-insoluble chitin, (b) lithium chloride, Chem. Pharm. Bull, Vol. 29, pp. 3067-3069 (1981), and (c) N-methylpyrrolidone or dimethylacetamide or where a chitin is dissolved in hexafluoro-2-propanol, the mixture thereof. The concentration of the lithium and a drug is added thereto in an amount of 200 wt.% chloride is preferably 5 wt.% or more, as this is well with respect to the amount of the chitin, and thereafter soluble in a chitin. Next, a physiologically active sub the solvent is evaporated to obtain drug-containing stance is incorporated in the thus prepared dope. chitin-tablets. However, the solvent used in this method 65 "Physiologically active substance' as used in the is extremely specific and expensive, and is highly toxic.
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