WO1994010982A1 - Sustained-release microsphere containing antipsychotic and process for producing the same - Google Patents
Sustained-release microsphere containing antipsychotic and process for producing the same Download PDFInfo
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- WO1994010982A1 WO1994010982A1 PCT/JP1993/001673 JP9301673W WO9410982A1 WO 1994010982 A1 WO1994010982 A1 WO 1994010982A1 JP 9301673 W JP9301673 W JP 9301673W WO 9410982 A1 WO9410982 A1 WO 9410982A1
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- WIPO (PCT)
- Prior art keywords
- sustained
- acid
- antipsychotic
- release microsphere
- release
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4515—Non condensed piperidines, e.g. piperocaine having a butyrophenone group in position 1, e.g. haloperidol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Definitions
- the present invention relates to a sustained-release microsphere containing a hydrophobic antipsychotic as an active ingredient and a method for producing the same.
- decanoic acid esters of haloperidol and bromoperidol are described in JP-A-56-8318, and decanoic acid esters or enanthic acid esters of flufenadine are also known, and are used in treatment sites. ing.
- Japanese Patent Application Laid-Open Nos. Sho 62-210-18 disclose one week for water-soluble drugs. Describes a sustained-release microcapsule that can be administered once a month and a method for producing the same.
- Japanese Patent Application Laid-Open No. 55-33414 discloses that a hydrophobic drug and polylactic acid are dissolved in a common organic solvent, a phase separation agent is added, the mixture is emulsified, and then the solvent is distilled off. A so-called submerged drying method for obtaining fine particles has been disclosed.
- the present inventors have conducted intensive studies with the aim of developing a sustained-release preparation containing the active ingredient itself without chemical modification of the drug in order to enhance the compliance during maintenance therapy with a hydrophobic antipsychotic drug. Has been repeated.
- a hydrophobic antipsychotic drug is incorporated into a base made of a biocompatible high molecular weight biopolymer having a biodegradable function to form a sustained-release microsphere preparation, which is administered subcutaneously or intramuscularly.
- drug release was possible at a substantially constant rate over a week or more, and completed the present invention.
- the present invention provides (1) an antipsychotic-containing sustained-release microsphere obtained by incorporating a hydrophobic antipsychotic in a base comprising a biocompatible high molecular weight polymer, and (2) a hydrophobic microsphere containing a hydrophobic antipsychotic.
- a solution of a biocompatible polymer containing in vivo histocompatibility containing an antipsychotic drug is used as an oil layer. This oil layer is added to an aqueous layer, and then an emulsification operation is performed to form an OZW emulsion, and then the solvent in the oil layer is removed.
- the present invention relates to a method for producing a sustained-release microphone mouth Xa containing an antipsychotic, which is detached by a submerged drying method.
- hydrophobic antipsychotics applicable to the present invention include haloperidol, bromperidol, flufenadine, chlorpromazine, sulpiride, carpipramine, clocabramine, mosapramine, risperidone, clozapine, olanzapine and sertindole, or pharmaceutically acceptable drugs thereof.
- the base constituting the sustained-release microphone mouth sphere of the present invention must maintain a constant plasma concentration by a single administration and impart a function of stably exerting the effect over a long period of time.
- Has a biodegradable function as a base having such a function The biocompatible high molecular weight biopolymer is used.
- the sustained-release microsphere of the present invention is configured to include a hydrophobic antipsychotic drug. Examples of such biocompatible histocompatibility polymers include fatty acid ester polymers or copolymers thereof, polyacrylic esters, polyhydroxybutyric acids, polyalkylene oxalates, polyolz esters, polycarbonates and polyamino acids. These can be used alone or in combination of two or more.
- the fatty acid ester polymer or its copolymer includes polylactic acid, polyglycolic acid, polycunic acid, polymalic acid, and lactic acid / glycolic acid copolymer. Used as a mixture of more than one species.
- one kind of polyhydroxy acrylate, poly; 8-hydroxybutyric acid, poly trimethylene oxalate, polyorthoester, polyorthocarbonate, polyethylene carbonate, poly 7-benzyl-L-glutamic acid and poly-L-alanine Or two or more types can be used.
- polylactic acid, polyglycolic acid or lactic acid 'glycolic acid copolymer is used.
- the average molecular weight of these in vivo histocompatible high molecular weight polymers used in the present invention is preferably from about 2000 to about 800,000, more preferably from about 500 to about 2000. It is selected from the range of 0000.
- the composition ratio of lactic acid to glycolic acid should be in the range of about 100: 0: 0, 50:50. It can be used and is preferably 75:25 and 50:50.
- the amount of these high molecular weight polymers is determined by the speed and duration of drug release, and is adjusted in an amount of about 0.2 to about 1000 times by weight of the drug, but is preferably used. It is preferable to use about 1 to 1000 times by weight of a high molecular weight polymer as the base of the microsphere preparation of the present invention.
- the solution (oil layer) containing the polymer a solution in which the polymer is dissolved in a solvent is used.
- the concentration of the high molecular weight polymer in the oil layer is selected from about 0.5 to about 90% (WZW), more preferably from about 2 to about 60% (W / W).
- the solvent may be any solvent having a boiling point of about 12 (TC or less and not miscible with water and capable of dissolving a high molecular weight polymer, such as a halogenated alkane (dichloromethane). Chloromethane, chlorohonolem, chloromethane, dichloroethane, trichloroethane, etc.), ethyl acetate, ethyl ether, cyclohexane, benzene, n-hexane, toluene and the like. You may.
- Microspheres are produced by dissolving or dispersing a biocompatible biopolymer in a solvent and adding a hydrophobic antipsychotic to the solvent to form an oil layer.
- the oil layer thus obtained is added to the aqueous layer, and then emulsification is performed to produce an OZW emulsion. Then, the solvent in the oil layer is eliminated by a submerged drying method to prepare a microsphere.
- the drug When a drug is dispersed to form an oil layer, the drug may be used after being refined. By using microcrystals, the surface of the microsphere becomes smoother, and the release of the drug becomes closer to zero order. This is due to the decrease in the initial release rate due to the increase in the interaction due to the increase in the contact area between the polymer and the drug, and the increase in the release rate due to the increase in the surface area of the drug in the late stage of the release. It is considered to be as shown.
- the average particle size of the finely divided drug is in the range of 10 m or less, more preferably in the range of 5 im or less (about 0.1 to about 5 m, preferably 0.5 to 5 m). m).
- a jet mill, a ball mill, a vibration mill, a hammer mill, a colloid mill and the like are used.
- an emulsifier to the aqueous layer, and any examples may be used as long as they generally form a stable OZW type emulsion.
- Surfactants sodium oleate, sodium stearate, sodium lauryl sulfate, etc.
- nonionic surfactants polyoxyethylene sorbitan fatty acid ester, polyoxyethylene castor oil derivative, etc.
- polyvinylpyrrolidone polyvinyl alcohol, calcium Examples include boxymethylcellulose, lecithin, and gelatin, and one or a combination of these may be used.
- the concentration at the time of use can be appropriately selected from the range of about 0.01% to about 20%, and is more preferably used within the range of about 0.05% to about 10%.
- Removal of the solvent from the oil layer can be performed by a commonly used method (drying method in liquid: Tamotsu Kondo “Micro Capsule Function and Application ”, p. 78, Japan Standards Association, published March 20, 1991).
- drying method in liquid Tamotsu Kondo “Micro Capsule Function and Application ”, p. 78, Japan Standards Association, published March 20, 1991.
- the pressure is gradually reduced while stirring with a propeller type stirrer or a magnetic stirrer, or desorption is performed while adjusting the degree of vacuum using a rotary evaporator.
- microspheres thus obtained are separated by centrifugation or filtration, and then the free drug, emulsifier, etc. adhering to the surface of the microspheres are repeatedly washed several times with distilled water. Heat, if necessary, and remove the water in the microspheres and the solvent in the microspheres more completely under reduced pressure.
- the microspheres obtained above are lightly ground, if necessary, and then sieved to remove microspheres that are too large.
- the particle size of the microspheres may be within a range that satisfies the dispersibility and needle penetration property.
- the average diameter is about 0.5 to about 400. m, more preferably in the range of about 0.5 to about 200 ⁇ m.
- the microspheres of the present invention include a dispersant (polysorbate 80, sodium carboxymethyl cellulose, sodium alginate, etc.), a preservative (methyl paraben, propyl paraben, benzyl alcohol, chlorobutanol, etc.), a tonicity agent (sodium chloride). Glycerin, sorbitol, glucose, etc.) to form an aqueous suspension, or disperse in olive oil, sesame oil, peanut oil, cottonseed oil, vegetable oils such as corn oil, propylene glycol, etc. By doing so, a sustained release injection can be prepared. In order to reduce the feeling of resistance upon injection, the sustained-release microsphere preparation of the present invention is preferably used as an aqueous suspension.
- the sustained-release injection of microspheres of the present invention is obtained by adding an excipient (mannitol, sorbitol, lactose, glucose, etc.) in addition to the above composition, redispersing, and freeze-drying or spray-drying. It can be prepared by adding distilled water for injection or an appropriate dispersion medium at the time of use, and in this case, a more stable sustained-release injection can be obtained.
- an excipient mannitol, sorbitol, lactose, glucose, etc.
- the dosage of the hydrophobic antipsychotic drug which is the active ingredient of the sustained-release microphone ⁇ -sphere of the present invention, can be determined according to the disease to be treated, the condition of the patient, the age, etc. Usually, the dose is 5 to 500 mg, preferably 10 to 2.00 mg per adult. Since the preparation of the present invention releases the active ingredient depending on the hydrolysis of the high molecular weight polymer with water, there is little individual difference, and not only intramuscular but also subcutaneous administration is possible.
- FIG. 1 is a graph showing the remaining amount of bromoperidol at the administration site after the microspheres obtained in Examples 1 to 3 were intramuscularly administered to rats.
- FIG. 2 is a graph showing changes in plasma concentration after intramuscular administration of the haloperidol-containing microspheres obtained in Example 4 to rat muscles.
- FIG. 3 is a diagram showing the results of a release test at the invit opening of the microspheres obtained in Experimental Example 3.
- the OZW type emulsion was gently stirred with an ordinary stirrer, and after the microspheres solidified with the volatilization of dichloromethane, the microspheres were collected by a centrifugal separator, and simultaneously washed with distilled water. The collected microspheres were obtained as a powder by freeze-drying.
- d1-polylactic acid (molecular weight: about 1000) was dissolved in 4 ml of dichloromethane to prepare a 30% solution.
- haloperidol (average particle size: 3.0 zm) 38 Omg was suspended to prepare a mixed solution.
- the haloperide was produced in the same manner as in Example 1.
- Bromperidol-containing microspheres obtained in the above Examples 1 to 3 were suspended in physiological saline, and the bromperidol was administered at a dose of 12.5 mg into the thigh muscle of an SD Rad male rat (15-week-old). Was administered. After a certain period of time, the microspheres remaining at the administration site were collected every hour, and the remaining amount of bromperidol was measured. As a result, it was confirmed that the drug was released at a substantially constant rate as shown in FIG.
- the haloperidol-containing microsphere obtained in Example 4 was suspended in a 0.5% sodium carboxymethylcellulose solution isotonic with mannitol, and the SD male rat (13 weeks) was administered at a dose of 25 mg as haloperidol. Aged). After a certain time, blood was collected from the ocular vein at each time, and the plasma concentration was measured. As a result, as shown in FIG. 2, it was confirmed that the plasma concentration of haloperidol was maintained.
- Bromperidol-containing microspheres 25 m obtained from the following formulations A and B g was dispersed in 2 Om 1 of physiological saline, and the mixture was shaken at 37 ° C and 80 times in a shaking thermostat (Yamato Scientific). The test solution was collected over time, and the release rate was calculated by ultraviolet absorption spectrophotometry (245 nm). As a result, as shown in FIG. 3, it was confirmed that the microspheres of Formulation A composed of micronized bromperidol released the drug in almost zero order.
- Unmilled buperperidone (average particle size: 13.0 urn) was used in place of 2.5 / m bromperidol in Formula A.
- the sustained-release microsphere preparation containing a hydrophobic antipsychotic drug of the present invention has, for example, the following characteristics, and therefore, a remarkable improvement in compliance in maintenance therapy for psychiatric patients can be expected.
- the desired pharmacological effect can be sustained by injection once every 1 to 8 weeks instead of daily administration.
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93924827A EP0669128B1 (en) | 1992-11-17 | 1993-11-15 | Sustained-release microsphere containing antipsychotic and process for producing the same |
KR1019950701853A KR100333115B1 (ko) | 1992-11-17 | 1993-11-15 | 항정신병약함유서방성마이크로스피어및이의제조방법 |
AT93924827T ATE188375T1 (de) | 1992-11-17 | 1993-11-15 | Ein antipsychotikum enthaltende mikrokugel zur verzögerten freisetzung und verfahren für ihre herstellung |
DE0669128T DE669128T1 (de) | 1992-11-17 | 1993-11-15 | Ein antipsychotikum enthaltende mikrokugel zur verzögerten freisetzung und verfahren für ihre herstellung. |
DE69327542T DE69327542T2 (de) | 1992-11-17 | 1993-11-15 | Ein antipsychotikum enthaltende mikrokugel zur verzögerten freisetzung und verfahren für ihre herstellung |
DK93924827T DK0669128T3 (da) | 1992-11-17 | 1993-11-15 | Sustained-release mikrosfære indeholdende antipsykotikum og fremgangsmåde til at fremstille samme |
GR960300020T GR960300020T1 (en) | 1992-11-17 | 1996-03-31 | Sustained-release microsphere containing antipsychotic and process for producing the same. |
US08/812,544 US5871778A (en) | 1992-11-17 | 1997-03-07 | Sustained release microsphere preparation containing antipsychotic drug |
GR20000400702T GR3033016T3 (en) | 1992-11-17 | 2000-03-21 | Sustained-release microsphere containing antipsychotic and process for producing the same. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4/332441 | 1992-11-17 | ||
JP33244192 | 1992-11-17 |
Publications (1)
Publication Number | Publication Date |
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WO1994010982A1 true WO1994010982A1 (en) | 1994-05-26 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1993/001673 WO1994010982A1 (en) | 1992-11-17 | 1993-11-15 | Sustained-release microsphere containing antipsychotic and process for producing the same |
Country Status (11)
Country | Link |
---|---|
US (2) | US5656299A (ja) |
EP (1) | EP0669128B1 (ja) |
KR (1) | KR100333115B1 (ja) |
AT (1) | ATE188375T1 (ja) |
CA (1) | CA2148823C (ja) |
DE (2) | DE669128T1 (ja) |
DK (1) | DK0669128T3 (ja) |
ES (1) | ES2077547T3 (ja) |
GR (2) | GR960300020T1 (ja) |
PT (1) | PT669128E (ja) |
WO (1) | WO1994010982A1 (ja) |
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US5650173A (en) * | 1993-11-19 | 1997-07-22 | Alkermes Controlled Therapeutics Inc. Ii | Preparation of biodegradable microparticles containing a biologically active agent |
US5654008A (en) * | 1993-11-19 | 1997-08-05 | Alkermes Controlled Therapeutics Inc. Ii | Preparation of biodegradable microparticles containing a biologically active agent |
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US6331317B1 (en) | 1999-11-12 | 2001-12-18 | Alkermes Controlled Therapeutics Ii Inc. | Apparatus and method for preparing microparticles |
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US6379704B2 (en) | 2000-05-19 | 2002-04-30 | Alkermes Controlled Therapeutics Inc. Ii | Method for preparing microparticles having a selected polymer molecular weight |
JP2002525330A (ja) * | 1998-09-30 | 2002-08-13 | イーライ・リリー・アンド・カンパニー | 2−メチル−チエノ−ベンゾジアゼピン製剤 |
US6495166B1 (en) | 1999-11-12 | 2002-12-17 | Alkermes Controlled Therapeutics Inc. | Apparatus and method for preparing microparticles using in-line solvent extraction |
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Also Published As
Publication number | Publication date |
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US5871778A (en) | 1999-02-16 |
US5656299A (en) | 1997-08-12 |
EP0669128A1 (en) | 1995-08-30 |
KR100333115B1 (ko) | 2002-12-02 |
DE669128T1 (de) | 1996-03-14 |
GR3033016T3 (en) | 2000-08-31 |
CA2148823A1 (en) | 1994-05-26 |
CA2148823C (en) | 1999-03-09 |
PT669128E (pt) | 2000-06-30 |
DK0669128T3 (da) | 2000-06-19 |
EP0669128A4 (en) | 1996-09-25 |
DE69327542D1 (de) | 2000-02-10 |
DE69327542T2 (de) | 2000-07-06 |
GR960300020T1 (en) | 1996-03-31 |
ES2077547T1 (es) | 1995-12-01 |
ES2077547T3 (es) | 2000-06-16 |
ATE188375T1 (de) | 2000-01-15 |
KR950703936A (ko) | 1995-11-17 |
EP0669128B1 (en) | 2000-01-05 |
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