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Last Updated: March 28, 2024

Claims for Patent: 9,931,411


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Summary for Patent: 9,931,411
Title:Microparticles containing physiologically active peptide, method for preparing the same, and pharmaceutical composition comprising the same
Abstract: Disclosed are microparticles containing physiologically active peptides, a method for preparing the same, and a pharmaceutical composition comprising the same.
Inventor(s): Yoon; Hye Jeong (Daejeon, KR), Seo; Min Hyo (Daejeon, KR), Yi; Yil Woong (Daejeon, KR), Kim; Bong Oh (Daejeon, KR)
Assignee: SAMYANG BIOPHARMACEUTICALS CORPORATION (Seoul, KR)
Application Number:15/065,261
Patent Claims:1. A method for preparing physiologically active peptide-containing microparticle comprising: 1) mixing a physiologically active peptide with an ionic water-soluble polymer in an aqueous medium to form an ionic complex of the physiologically active peptide and the water-soluble polymer; 2) drying the ionic complex of the physiologically active peptide and the water-soluble polymer obtained in step 1); 3) homogeneously mixing the ionic complex of the physiologically active peptide and the water-soluble polymer obtained in step 2) with a biodegradable, water-insoluble polymer in a non-aqueous solvent; and 4) removing the non-aqueous solvent from the resulting solution obtained in step 3) to obtain microparticles; wherein the water-soluble polymer has a number average molecular weight of 500 to 5,000 daltons, and is the compound represented by Formula 2 or 6 below: RO--CHZ--[COO--CHX].sub.p--[COO--CHY'].sub.q--COO--CHZ--COOM [Formula 2] wherein X is methyl group; Y' is hydrogen atom or phenyl group; p is an integer of 0 to 25 and q is an integer of 0 to 25 provided that p+q is an integer of 5 to 25; R is hydrogen atom, or acetyl group, benzoyl group, decanoyl group, palmitoyl group, methyl group or ethyl group; M is H, Na, K, or Li; and Z is hydrogen atom, methyl group or phenyl group, YO--[--C(O)--(CHX).sub.a--O--].sub.m--C(O)--R--C(O)--[--O--(CHX').sub.b--- C(O)--].sub.n--OZ [Formula 6] wherein each of X and X' is independently hydrogen, alkyl or aryl; each of Y and Z is independently H, Na, K, or Li; each of m and n is independently an integer of 0 to 95 provided that 5<m+n<100; each of a and b is each independently an integer of 1 to 6; and R is substituted or unsubstituted --(CH.sub.2).sub.k-- in which k is an integer of 0 to 10, divalent alkenyl having 2 to 10 carbon atoms, divalent aryl having 6 to 20 carbon atoms, or a combination thereof, wherein the biodegradable, water-insoluble polymer has a weight average molecular weight of 10,000 to 100,000 daltons, and is one or more selected from the group consisting of polylactide, polyglycolide, poly(lactide-co-glycolide), polyorthoester, polycaprolactone, polydioxanone polyalkylcarbonate, polyanhydride and copolymers thereof, and wherein the microparticle has a uniform particle size of between 30 .mu.m and 100 .mu.m, a drug encapsulation ratio of between 35% and 85%, and exhibits decreased initial drug release amounts of less than 20% and superior long-term continuous release properties of greater than 40% after 14 days.

2. The method according to claim 1, wherein the non-aqueous solvent is selected from the group consisting of methylene chloride, ethyl acetate, chloroform, acetone, N-methyl-2-pyrrolidone, N,N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, hexafluoroisopropanol and mixtures thereof.

3. The method according to claim 1, wherein step 4) comprises: 4-1) filling a plurality of microwells placed in a water-soluble microtemplate with the solution obtained in step 3); 4-2) removing the non-aqueous solvent from the solution filled in the microwells to solidify the biodegradable, water-insoluble polymer; and 4-3) collecting microparticles from the microtemplate.

4. The method according to claim 3, wherein the water-soluble microtemplate is produced from one or more water-soluble polymers selected from the group consisting of gelatin, polyvinyl alcohol, agarose, poly(N-isopropyl acrylamide), alginate and mixtures thereof.

5. The method according to claim 3, wherein, in step 4-3), the collection of microparticles is carried out by dissolving the microtemplate in an aqueous medium.

6. The method according to claim 1, wherein step 4) comprises: 4-i) adding the resulting solution obtained in step 3) dropwise to an aqueous solution of the water-soluble polymer in the presence of a surfactant with stirring to remove the non-aqueous solvent and obtain microparticle.

7. The method according to claim 1, wherein the water-soluble polymer has a number average molecular weight of 500 to 3,000 daltons.

8. The method according to claim 1, wherein the physiologically active peptide is selected from the group consisting of luteinizing hormone-releasing hormone (LHRH) agonists, somatostatin and analogs thereof, glucagon-like peptides (GLP), parathyroid hormone and analogs thereof, insulin-like growth factors, epidermal growth factors, platelet-derived growth factors, fibroblast growth factors, transforming growth factors, growth hormone releasing factors, amylin analogs, peptide YY (PYY), protein synthesis-stimulating peptides, gastrin inhibitory peptides, vasoactive intestinal peptides, and pharmaceutically acceptable salts thereof.

9. The method according to claim 1, wherein the physiologically active peptide is present in an amount of 1.0 to 10% by weight with respect to the total weight of the microparticles.

10. The method according to claim 1, wherein the content of the ionic complex is 4% by weight to 40% by weight, based on the total weight of the microparticles.

11. The method according to claim 1, wherein the physiologically active peptide and the ionic water-soluble polymer are mixed with a mixing ratio of 1:1 to 10 as a molar ratio.

12. The method according to claim 1, wherein the water-soluble polymer is the compound represented by Formula 2.

13. The method according to claim 1, wherein the water-soluble polymer is PLA-COONa.

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