WO2000054811A1 - Compositions medicamenteuses - Google Patents
Compositions medicamenteuses Download PDFInfo
- Publication number
- WO2000054811A1 WO2000054811A1 PCT/JP2000/001606 JP0001606W WO0054811A1 WO 2000054811 A1 WO2000054811 A1 WO 2000054811A1 JP 0001606 W JP0001606 W JP 0001606W WO 0054811 A1 WO0054811 A1 WO 0054811A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrochloride
- pharmaceutical composition
- composition according
- drug
- granular pharmaceutical
- Prior art date
Links
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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- 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
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
-
- 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
- A61K31/535—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 oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- 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
-
- 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
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Definitions
- the present invention relates to a granular pharmaceutical composition which masks the unpleasant taste of a drug and has a good feeling of taking, and a preparation using the same.
- JP-A-62-30909 discloses a sustained-release preparation in which a drug-containing core is coated with ethyl cellulose. It is described that the drug release rate can be adjusted by changing the thickness of the ethylcellulose membrane.
- this is a technology for sustained-release products, not a technology used for immediate-release products with unpleasant masking properties.
- those coated with a water-insoluble polymer have a problem of ingestibility, such as a foreign-body sensation when ingested in the mouth and pain when pinched in dentures.
- the method using a micro force cell has drawbacks in that the production method is complicated due to the use of an organic solvent and the yield is low and the production cost is high.
- the method with the addition of a sweetener does not have a sufficient masking effect for drugs with a strong unpleasant taste.
- Japanese Patent Application Laid-Open No. 7-242568 discloses a drug and a water-conducting agent which dissolve a hydrophobic substance and a surfactant having a melting point of 45 to 90 ° C by heating to give an unpleasant flavor.
- a granular preparation obtained by dissolving or suspending and spraying and granulating the liquid is disclosed.
- Surfactant The purpose of adding the water-conducting agent is to speed up the dissolution of the drug, and each is contained in the composition in an amount of 5 to 35%. However, from the viewpoint of safety, it is preferable that the amount of the surfactant used is small.
- Japanese Patent Application Laid-Open No. 7-267850 discloses that one or several unpleasant drugs, one or several water-soluble polymers and one or several waxy substances are mixed.
- a pharmaceutical composition obtained by granulating a heated and molten wax-like substance together with a drug and a water-soluble polymer is disclosed.
- the purpose of adding the water-soluble polymer is to speed up the dissolution of the drug in the same manner as described above, and 5 to 60% is blended in this composition.
- Tube administration is an administration method mainly used for patients who cannot swallow the drug product.
- the powder is dispersed in water and then transferred to a syringe, which is injected into the digestive tract from the user's nose or abdomen. This is a method of injecting into an inserted tube for administration. Since the administration is often prepared using a dispersion liquid at the time of use, the powder is required to be uniformly dispersed in a short time and not to be clogged in a syringe and a tube.
- powders coated with a pH-dependent polymer such as methacrylic acid copolymer aggregate in non-electrolyte solutions such as purified water and glucose, causing clogging in syringes and tubes.
- a pH-dependent polymer such as methacrylic acid copolymer aggregate in non-electrolyte solutions such as purified water and glucose
- saccharides such as lactose as an excipient are also unsuitable for tube administration because they cause clogging in syringe tubes.
- an object of the present invention is to provide a granular pharmaceutical composition which is excellent in masking of unpleasant taste of a drug, has a good feeling of taking, and can be administered by tube administration, and a preparation using the same. In that. Disclosure of the invention
- the present inventors have manufactured granules containing a drug exhibiting an unpleasant taste, and have variously studied the performance thereof. If a sugar alcohol is blended in addition to the drug exhibiting an unpleasant taste and a waxy substance, it has been surprisingly found that a pharmaceutical preparation having an excellent masking effect of unpleasant taste and a good feeling of taking can be obtained, and completed the present invention. It has also been found that this pharmaceutical preparation can be administered by tube administration.
- the present invention provides a drug exhibiting unpleasant taste, a granular pharmaceutical composition containing a waxy substance and a sugar alcohol, a method for producing the same, and an oral pharmaceutical preparation containing the granular pharmaceutical composition. It is. BEST MODE FOR CARRYING OUT THE INVENTION
- the unpleasant taste includes bitterness, astringency, pungency, irritation, and even smell felt by a user when the drug is contained in the mouth.
- the drug exhibiting unpleasant taste in the present invention is not particularly limited as long as it is a drug exhibiting the unpleasant taste and used as a medicine.
- R ′ a , R lb and R k may each independently have a substituent.
- R 2a , R 2b and R 2d each independently represent a hydrogen atom, a C, —C 6 linear or branched alkyl group or amino group which may have a substituent.
- R 3a , R 3b , R 3e and R 3d each independently represent a hydrogen atom or a halogen atom.
- R 4a or R 4e may have a hydrogen atom, a halogen atom, or a substituent — C 6 may have a linear or branched alkyl group or a substituent C, —
- R 5d represents a hydrogen atom or a 1 C 6 linear or branched alkyl group which may have a substituent.
- YYY e and Y d each independently represent a nitrogen-containing group.
- R 1 is a C, 1 C 4 alkyl group, a halogen atom, a fluoro-substituted 1 C, 1 C 4 7 alkyl group, a 1 C 4 alkoxyl group, a fluoro substituted 1 C 4 alkoxyl group, a cyano group and a nitro group.
- a phenyl group which may have 1 to 3 substituents selected from the group consisting of
- R 2 represents a hydrogen atom, a carboxy group, a C 6 alkoxycarbonyl group, or a C, C 7 aliphatic acryl group which may be substituted with a halogen atom, a hydroxyl group, a Ci—C 6 alkoxyl group or a cyano group.
- R 3 is a hydroxyl group, a C, 1C 4 alkoxyl group, a C, —C 4 alkoxyl group or a C,
- JP-A-11-294680 JP-A-2-28178, JP-A-2-124873, JP-A-2-231475, JP-A-5-271229 Gazette, JP-A-7-309864, JP-A-8-309
- the compounds represented by the above general formulas (1) to (5) or salts thereof may exist as hydrates or solvates, and these are also included in the present invention.
- the drug having an unpleasant taste is preferably poorly soluble in a box-like substance from the viewpoint of a masking effect, and more preferably water-soluble and hardly soluble in a box-like substance.
- Preferred examples of the compounds represented by the above general formulas (1) to (4) or salts thereof include the following compounds or salts thereof.
- bitaf loxacin Moxif loxacin hydrochloride Sitafloxacin Moxifloxacin hydrochloride
- WQ-3034 Preferred examples of the compound represented by the general formula (5) or a salt thereof include the following.
- the drug exhibiting an unpleasant taste ofloxacin, repo-floxacin, cynofloxacin hydrate, cetraxate hydrochloride, nefiracetam, ticlopidine hydrochloride and clopidogrel sulfate are particularly preferable.
- waxy substance specifically, melting point of 40 to 150 ° C
- various hardened oils such as hardened castor oil, hardened soybean oil, hardened naney oil, hardened cottonseed oil, vegetable or animal fats and oils such as carnaupa wax, beeswax, beef tallow, etc .
- Higher alcohols such as stearyl alcohol and ceanol
- polyethylene glycols such as macrogol 400 and macrogol 600
- higher fatty acids such as stearic acid and palmitic acid
- Glycerin fatty acid esters such as fatty acid glycerin and trifatty acid glycerin and sucrose fatty acid esters; or a mixture of two or more thereof.
- hardened oils, fatty acids, and derivatives of fatty acids are preferable, and hardened oils, higher fatty acids, and fatty acid esters are more preferable, and hardened oils, glyceryl monofatty acid, glycerin trifatty acid, and stearic acid are particularly preferable.
- the melting point of the waxy substance is preferably lower than the melting point of the drug.
- sugar alcohol in the present invention those having a low heat of solution are preferable, and for example, erythritol, xylitol, sorbyl, maltyl, or a mixture of two or more thereof is preferable. From the viewpoint of taking feeling, sugar alcohol having a heat of dissolution of not more than 3 O cal Zg is preferable, and erythritol and xylitol are particularly preferable.
- the weight ratio of the drug exhibiting unpleasant taste to the waxy substance is preferably 1: 1 to 1: 5, more preferably 1: 2 to 1 from the viewpoint of the balance between the masking effect of unpleasant taste and the dissolution property. : Range of 3.
- the amount of the sugar alcohol is preferably at least 10% by weight, more preferably from 10 to 99.9% by weight, more preferably from 10 to 99.9% by weight, from the viewpoint of masking effect of unpleasant taste, dissolution property and feeling of taking. 0 to 80% by weight is more preferable, and 30 to 70% by weight is particularly preferable.
- the granular pharmaceutical composition of the present invention comprises a granulated product obtained by heating and melting a wax-like substance, dispersing or dissolving a drug exhibiting an unpleasant taste, and then performing primary granulation using a dispersion or solution and a sugar alcohol. And secondary granulation.
- primary granulation means include spray granulation, melt granulation and dispersion or solution. May be ground after cooling and solidification, but spray granulation is preferred.
- spray granulation is preferred.
- the spray chilling method and the spray drying method are preferable because even if the granulated material is placed on the tongue, it can be easily formed into fine particles having a particle size that does not cause a feeling of foreign matter such as roughness.
- the particle size is
- a small amount of a surfactant may be added for the purpose of reducing adhesion to the inner wall of the manufacturing machine in the spray chilling step.
- the amount of the surfactant added is preferably about 0.5 to 5% by weight, particularly about 1 to 4% by weight, based on the primary granules.
- Means for secondary granulation of the granular material obtained by primary granulation and sugar alcohol include wet fluidized bed granulation using a binder solution such as hydroxypropylcellulose, hydroxypropylmethylcellulose, and polyvinylpyrrolidone, and polyethylene.
- a melt granulation method using a low-melting substance such as glycol or glyceryl monostearate as a binder can be used.
- the granular pharmaceutical composition of the present invention is preferably one obtained by a method of secondary granulation of a granular material obtained by primary granulation and a sugar alcohol.
- the sugar alcohol used for the secondary granulation is dissolved by saliva in about 10 seconds, so only the wax-like substance particles obtained by the primary granulation and in which the drug is dispersed remain. Since the dust particles are fine spheres, they do not feel foreign matter.
- the drug is uniformly dispersed in the box-like substance to form particles, and the dissolution in the mouth is extremely small, so that the unpleasant taste of the drug is well masked.
- sugar alcohols especially erythritol and xylitol
- sweet taste in the mouth and have a refreshing sensation, which contributes to masking the unpleasant taste of drugs.
- the wax-like substance particles release the drug in the digestive tract, and the released drug is absorbed into the living body.
- the granular pharmaceutical composition of the present invention can be used as it is or by mixing other additives as needed to prepare oral pharmaceutical preparations such as powders, granules, dry syrups, tablets and capsules. Among them, powders, granules and dry syrups are preferred.
- additives used herein include binders such as polyvinylpyrrolidone, polyvinyl alcohol, hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, polyethyleneglycol, glyceryl monostearate; aspartame, sodium saccharin, saccharin, Sweeteners such as somatatin and stevia; fragrances such as dl-menthol and 1-menthol; glidants such as light gay anhydride, magnesium aluminate metasilicate, talc, synthetic aluminum gaylate, and ethyl cellulose; Disintegrators such as sodium lactate, sodium starch glycolate, and low-substituted hydroxypropylcellulose; and pH regulators such as sodium citrate and sodium hydrogen carbonate.
- the additive contains a water-soluble polymer.
- the amount is preferably as small as 0.1 to 5% by weight, particularly 1 to 4% by weight in the preparation.
- Glycerin monostearate 200 parts by weight was melted at about 90 ° C., and lepofloxacin (100 parts by weight) was uniformly dispersed. The dispersion was spray-cooled using a spray dryer to obtain fine granules. To 300 parts by weight of the granulated product, 630 parts by weight of erythritol was added, and the mixture was mixed using a fluidized bed granulator. Then, an aqueous solution of 10 parts by weight of 10 parts by weight of polyvinyl alcohol as polyvinyl alcohol was added. Sprayed and fluid granulated. After the spraying was completed, drying was performed in a fluidized bed granulator to obtain a granulated product. The granulated product was sieved using a No. 30 sieve (opening: 500 im) to obtain a powder.
- Glycerin monostearate (197 parts by weight) was melted at about 90 ° C, and polyoxyethylene (20) sorbinone monooleate (polysorbate 80) was added thereto. Parts by weight were mixed. Further, 100 parts by weight of levofloxacin was uniformly dispersed in the mixed solution. This dispersion was spray-cooled using a spray drier to obtain fine granules. To 300 parts by weight of the granulated product was added 630 parts by weight of erythritol, and the mixture was mixed using a fluidized bed granulator. Then, as a polyvinyl alcohol, 20 parts by weight of 10 WZ V% of polypinyl was added.
- Example 2 A sensory test was carried out on 940 mg of the powder obtained in Example 1 and 950 mg of the powder obtained in Example 2. Levofloxacin was actually contained in the mouth in an amount equivalent to 10 mg of powder as a levofloxacin, and the taste and feeling of ingestion were evaluated. In all powders, it was confirmed that the extremely unpleasant taste of the drug was masked for 30 seconds or more. After 10 seconds, no foreign body sensation was felt in the mouth.
- a powdery masking test was performed on 94.0 mg of the powder obtained in Example 1 and 95 Omg of the powder obtained in Example 2.
- the unpleasant taste masking test was performed using a dissolution tester, using 50 OmL of purified water as the test solution, at a test solution temperature of 37 ° C, a paddle method, and a rotation speed of 100 rpm. Drug alone was used as a control.
- the results (elution rate (%)) are shown in Table 1. The initial elution of the drug from the powder was significantly suppressed as compared to the drug alone.
- Table 1 Dissolution test results are shown in Table 1. The initial elution of the drug from the powder was significantly suppressed as compared to the drug alone.
- Example 1 and Example 2 did not cause clogging and could be smoothly administered.
- Dissolution tests were performed on 94 Omg of the powder obtained in Example 1 and 95 Omg of the powder obtained in Example 2.
- the dissolution test uses a dissolution test apparatus, and the test solution is the 13th revised Japan
- the disintegration test of Pharmacopoeia was performed using 90 OmL of the first liquid, the test liquid temperature was 37 ° C, the paddle method, and the rotation speed was 5 Orpm. As a result, as shown in Table 3, it was confirmed that these powders exhibited good dissolution properties.
- Example 5 2 16 parts by weight of trifatty acid glycerin was dissolved in dichloromethane. Further, 97.8 parts by weight of clopidogrel sulfate and 32.6 parts by weight of ethyl cellulose were uniformly dispersed in this liquid. The dispersion was spray-cooled using a spray drier to obtain fine granules. A powder was obtained by adding 144.6 parts by weight of erythritol and 5 parts by weight of aspartame to 346.4 parts by weight of the granulated product.
- the t unpleasant taste masking test conducted powders 5 0 O mg diary unpleasant taste masking test obtained in Example 3-6 using a dissolution testing apparatus, the test liquid had use of purified water 3 0 O mL, test solution The test was performed at a temperature of 37 ° C, a paddle method, and a rotation speed of 100 rpm. As a result, it was confirmed that the initial elution of the drug from the powder was remarkably suppressed as compared with the drug alone in all Examples.
- Control Example 1 and Example 5 were evaluated for tube administration suitability. 50 O mg each was dispersed in purified water at 2 O mL. The dispersion was transferred to a disposable syringe, and an enteral feeding tube ("Argyle” Nutriental Feeding Tube, manufactured by Nippon Shearwood, Inc., having an inner diameter of 1.0 dragon) was connected. Injecting a dispersion liquid syringe, shows the c The results of evaluating the clogging of the syringe tip and the tube tip in Table 4.
- Control Example 1 The powder obtained in Control Example 1 was difficult to administer, and its suitability for tube administration could not be confirmed. In contrast, the powder obtained in Example 5 did not cause clogging, and it was confirmed that smooth administration was possible.
- Example 3 The powder obtained in Example 3 was subjected to a dissolution test of 36.5 rag.
- the dissolution test was performed using a dissolution tester, 90 mL of the 13th revised Japanese Pharmacopoeia Disintegration Test Solution 1 with 1% sodium lauryl sulfate added at 1%, and a paddle method with a test solution temperature of 37 ° C. , The rotation was performed at 50 rpm. As a result, as shown in Table 5, it was confirmed that Example 3 exhibited good dissolution.
- the pharmaceutical preparation which is excellent in the masking property of the unpleasant taste which a drug has, and has a good feeling of ingestion, and which can be easily taken by elderly people, children, and patients who have difficulty swallowing is obtained.
- This formulation is also suitable for tube administration.
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN008050538A CN1343128B (zh) | 1999-03-17 | 2000-03-16 | 药物组合物 |
CA2367373A CA2367373C (en) | 1999-03-17 | 2000-03-16 | Medicinal compositions |
AU31927/00A AU3192700A (en) | 1999-03-17 | 2000-03-16 | Medicinal compositions |
EP00909677A EP1161956A4 (en) | 1999-03-17 | 2000-03-16 | DRUG COMPOSITIONS |
NO20014490A NO20014490L (no) | 1999-03-17 | 2001-09-14 | Medisinske blandinger |
HK02106154.7A HK1044476B (zh) | 1999-03-17 | 2002-08-22 | 藥物組合物 |
US10/959,297 US20050152975A1 (en) | 1999-03-17 | 2004-10-07 | Pharmaceutical composition |
US11/565,733 US20070148235A1 (en) | 1999-03-17 | 2006-12-01 | Pharmaceutical composition |
US12/985,476 US20110159049A1 (en) | 1999-03-17 | 2011-01-06 | Pharmaceutical composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7214599 | 1999-03-17 | ||
JP11/72145 | 1999-03-17 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/959,297 Continuation US20050152975A1 (en) | 1999-03-17 | 2004-10-07 | Pharmaceutical composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000054811A1 true WO2000054811A1 (fr) | 2000-09-21 |
Family
ID=13480822
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2000/001606 WO2000054811A1 (fr) | 1999-03-17 | 2000-03-16 | Compositions medicamenteuses |
Country Status (12)
Country | Link |
---|---|
US (3) | US20050152975A1 (ja) |
EP (2) | EP2275141A1 (ja) |
JP (2) | JP4694669B2 (ja) |
KR (1) | KR100768034B1 (ja) |
CN (1) | CN1343128B (ja) |
AU (1) | AU3192700A (ja) |
CA (1) | CA2367373C (ja) |
HK (1) | HK1044476B (ja) |
NO (1) | NO20014490L (ja) |
RU (1) | RU2270695C2 (ja) |
TW (1) | TWI251495B (ja) |
WO (1) | WO2000054811A1 (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001288117A (ja) * | 2000-04-05 | 2001-10-16 | Otsuka Pharmaceut Co Ltd | 医薬製剤用組成物 |
WO2002024167A1 (fr) * | 2000-09-19 | 2002-03-28 | Daiichi Pharmaceutical Co., Ltd. | Composition medicinale |
JP2002138034A (ja) * | 2000-10-27 | 2002-05-14 | Kyoto Pharmaceutical Industries Ltd | 苦味マスキングチュアブル錠およびその製造方法 |
EP1333807A2 (en) * | 2000-10-13 | 2003-08-13 | Advancis Pharmaceuticals | Extended release erythromycin derivatives |
US6806256B2 (en) | 2001-03-05 | 2004-10-19 | Ortho -Mcneil Pharmaceutical, Inc. | Taste masked liquid pharmaceutical compositions |
WO2005025622A1 (ja) * | 2003-09-12 | 2005-03-24 | Ryukakusan Co. Ltd. | 苦みマスキング粒状ゼリー飲料 |
JP2006515592A (ja) * | 2002-12-23 | 2006-06-01 | アベンティス・ファーマ・ソシエテ・アノニム | 味覚マスキングが必要な活性物質の経口調剤のための化合物 |
WO2011052500A1 (ja) * | 2009-10-28 | 2011-05-05 | 第一三共株式会社 | ワックス安定製剤 |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040146553A1 (en) | 2002-12-23 | 2004-07-29 | Aventis Pharma S.A. | Compositions for oral administration of active principles requiring masking of taste |
DE10305984A1 (de) * | 2003-02-13 | 2004-09-02 | Helm Ag | Salze organischer Säuren mit Clopidogrel und deren Verwendung zur Herstellung phamazeutischer Formulierungen |
EP1608333A1 (en) * | 2003-04-02 | 2005-12-28 | Pliva Istrazivanje i Razvoj d.o.o. | Pharmaceutical compositions having reduced bitter taste |
JP4385802B2 (ja) * | 2004-03-16 | 2009-12-16 | 味の素株式会社 | 粉末透析剤の製造方法 |
US20070020330A1 (en) | 2004-11-24 | 2007-01-25 | Medpointe Healthcare Inc. | Compositions comprising azelastine and methods of use thereof |
LT2486942T (lt) * | 2004-11-24 | 2019-01-25 | Meda Pharmaceuticals Inc. | Kompozicijos, apimančios azelastiną ir jų panaudojimo būdai |
US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
RS53624B1 (en) | 2006-03-16 | 2015-04-30 | Euro-Celtique S.A. | PHARMACEUTICAL SFEROIDS |
WO2008001201A2 (en) * | 2006-06-28 | 2008-01-03 | Wockhardt Ltd | Pharmaceutical compositions of clopidogrel |
EP1900358A1 (en) * | 2006-09-16 | 2008-03-19 | Cimex Pharma AG | Pharmaceutical formulations comprising clopidogrel |
US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
JP5318400B2 (ja) * | 2006-11-20 | 2013-10-16 | 第一三共株式会社 | レボフロキサシン含有錠剤 |
US20090028935A1 (en) * | 2006-12-01 | 2009-01-29 | Kristin Arnold | Carvedilol forms, compositions, and methods of preparation thereof |
WO2008070072A2 (en) * | 2006-12-01 | 2008-06-12 | Mutual Pharmaceutical Company, Inc. | Carvedilol forms, compositions, and methods of preparation thereof |
FR2913884A1 (fr) * | 2007-03-21 | 2008-09-26 | Oralance Pharma Sa | Systeme galenique hydrophobe non ionisable |
EP2095815B1 (en) | 2008-02-26 | 2011-10-26 | Laboratorios Lesvi, S.L. | Pharmaceutical formulations containing clopidogrel |
EP2198859A1 (en) * | 2008-12-17 | 2010-06-23 | Losan Pharma GmbH | Melt-coated pharmaceutical composition with fast release |
US20110021591A1 (en) | 2009-07-21 | 2011-01-27 | Gordon Douglas J | Phenylbutazone carrier formulation showing increased bioactivity in animals |
JP5725884B2 (ja) * | 2011-01-27 | 2015-05-27 | 理研ビタミン株式会社 | 経口用製剤 |
US9119793B1 (en) | 2011-06-28 | 2015-09-01 | Medicis Pharmaceutical Corporation | Gastroretentive dosage forms for doxycycline |
CN103181885A (zh) * | 2011-12-30 | 2013-07-03 | 北京韩美药品有限公司 | 氯吡格雷的固体制剂及制备方法 |
US10842802B2 (en) | 2013-03-15 | 2020-11-24 | Medicis Pharmaceutical Corporation | Controlled release pharmaceutical dosage forms |
HUP1400294A2 (hu) | 2014-06-13 | 2015-12-28 | Skillpharm Kft | Clopidogrel új alkalmazása |
CN107335058B (zh) * | 2017-07-31 | 2021-01-08 | 暨南大学 | 一种2,6-二取代吡啶-4-硫代甲酰胺的新用途 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993017667A1 (en) * | 1992-03-12 | 1993-09-16 | Taisho Pharmaceutical Co., Ltd. | Composition for oral preparations |
JPH07285838A (ja) * | 1994-04-15 | 1995-10-31 | Lion Corp | 口腔用組成物 |
EP0826376A1 (en) * | 1995-05-02 | 1998-03-04 | Taisho Pharmaceutical Co. Ltd | Composition for oral administration |
JPH1135486A (ja) * | 1997-07-23 | 1999-02-09 | Lion Corp | 薬用固形製剤 |
Family Cites Families (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2215948B1 (ja) | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
JPS53141286A (en) | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
JPS5531042A (en) | 1978-08-25 | 1980-03-05 | Dainippon Pharmaceut Co Ltd | 1,8-naphthylidine derivative and its salt |
JPS5746986A (en) | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
DE3033157A1 (de) | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
FR2508459A1 (fr) | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation de derives de la tetrahydro-5,6,7,7a 4h thieno (3,2-c) pyridinone-2 |
FR2530247B1 (fr) | 1982-07-13 | 1986-05-16 | Sanofi Sa | Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique |
FR2548664B1 (fr) | 1983-07-06 | 1986-03-21 | Provesan Sa | Derives 7-(pyrrol-l-yl) des acides l-ethyl-1,4-dihydro-4-oxoquinoleine-3-carboxyliques et l-ethyl-1,4-dihydro-4-oxo-(1,8-naphtyridine)-3-carboxyliques substitues, leur preparation et leur application en tant que medicaments |
JPS6064979A (ja) | 1983-09-19 | 1985-04-13 | Hokuriku Seiyaku Co Ltd | 7−ピペラジン置換−6−フルオロ−4−オキソ−1,4−ジヒドロキノリン−3−カルボン酸誘導体 |
JPS60228479A (ja) | 1984-04-26 | 1985-11-13 | Toyama Chem Co Ltd | 1,4−ジヒドロ−4−オキソナフチリジン誘導体およびその塩 |
ZA864518B (en) | 1985-06-20 | 1987-03-25 | Daiichi Seiyaku Co | Optically active pyridobenzoxazine derivatives and intermediates thereof |
GB8518301D0 (en) | 1985-07-19 | 1985-08-29 | Fujisawa Pharmaceutical Co | Hydrodynamically explosive systems |
AU594983B2 (en) | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
JPH089597B2 (ja) | 1986-01-21 | 1996-01-31 | 杏林製薬株式会社 | 選択毒性に優れた8‐アルコキシキノロンカルボン酸およびその塩並びにその製造方法 |
US5591744A (en) | 1987-04-16 | 1997-01-07 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
NL193682C (nl) * | 1987-05-14 | 2000-07-04 | Glaxo Group Ltd | Beklede cefuroximaxetilsamenstelling. |
JPH0751579B2 (ja) | 1987-11-07 | 1995-06-05 | 日本新薬株式会社 | キノリンカルボン酸誘導体 |
JPH0228178A (ja) | 1988-04-23 | 1990-01-30 | Toyama Chem Co Ltd | 新規なピリドンカルボン酸誘導体およびその塩並びにそれらの製造法 |
IL90062A (en) | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | History of pyridonecarboxylic acid, their preparation and pharmaceutical preparations containing them |
JPH0645601B2 (ja) | 1988-07-20 | 1994-06-15 | 三共株式会社 | キノロンカルボン酸誘導体 |
JPH01258666A (ja) | 1988-08-18 | 1989-10-16 | Kyorin Pharmaceut Co Ltd | 新規置換キノリンカルボン酸 |
IE66202B1 (en) | 1989-08-16 | 1995-12-13 | Pfizer | Azabicyclo quinolone carboxylic acids |
WO1992021328A1 (en) * | 1991-05-28 | 1992-12-10 | Affinity Biotech, Inc. | Chewable drug-delivery composition |
FI101150B (fi) | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
TW209865B (ja) | 1992-01-10 | 1993-07-21 | Bayer Ag | |
KR100218700B1 (ko) * | 1992-03-12 | 1999-09-01 | 우에하라 아끼라 | 경구용조성물 |
KR0168715B1 (ko) * | 1992-11-30 | 1999-01-15 | 밋첼 아이. 커시너 | 맛을 차단하는 약제학적 조성물 |
WO1994014794A1 (en) | 1992-12-28 | 1994-07-07 | Yoshitomi Pharmaceutical Industries, Ltd. | 8-methoxyquinolonecarboxylic acid derivative |
US5527910A (en) | 1992-12-30 | 1996-06-18 | Cheil Foods & Chemicals, Inc. | Pyridone carboxylic acid compounds and their uses for treating infectious diseases caused by bacteria |
WO1995005373A1 (en) | 1993-08-13 | 1995-02-23 | Dong Wha Pharmaceutical Industrial Co., Ltd. | Novel quinolone carboxylic acid derivatives |
TW252107B (ja) | 1993-08-27 | 1995-07-21 | Hokuriku Pharmacetical Co Ltd | |
JPH07242568A (ja) | 1994-03-04 | 1995-09-19 | Eisai Co Ltd | 苦味隠蔽製剤 |
JPH07267850A (ja) | 1994-03-28 | 1995-10-17 | Eisai Co Ltd | 不快味を防止した医薬組成物及びその製造方法 |
DE69509442T2 (de) | 1994-06-16 | 1999-09-02 | Lg Chemical Ltd | Chinolincarbonsäurederivate mit 7-(4-Amino-methyl-3-oxim)-pyrrolidin-Substituenten und Verfahren zu ihrer Herstellung |
US5602254A (en) | 1995-05-26 | 1997-02-11 | Warner-Lambert Company | Method for making quinoline carboxylic acids or naphthyridine carboxylic acids in free base form |
CA2222322A1 (en) | 1995-06-06 | 1996-12-12 | Abbott Laboratories | Quinolizinone type compounds |
PT841062E (pt) * | 1995-07-21 | 2005-03-31 | Daiichi Seiyaku Co | Processo para a producao de uma preparacao granular |
DK0911328T3 (da) | 1995-11-22 | 2006-06-06 | Daiichi Seiyaku Co | Substituerede aminocycloalkylpyrrolidinderivater |
IT1276160B1 (it) * | 1995-11-22 | 1997-10-27 | Recordati Chem Pharm | Composizioni farmaceutiche orali a pronto rilascio per sospensioni estemporanee |
HU228567B1 (en) | 1996-02-09 | 2013-04-29 | Toyama Chemical Co Ltd | Quinolonecarboxylic acid derivatives or salts thereof |
ID16655A (id) | 1996-04-24 | 1997-10-30 | Daiichi Seiyaku Co | Turunan-turunan sikloalkilaminometilpirolidina |
AU3459797A (en) | 1996-07-12 | 1998-02-09 | Daiichi Pharmaceutical Co., Ltd. | Cis-substituted aminocyclopropane derivatives |
TW519542B (en) | 1996-09-27 | 2003-02-01 | Daiichi Seiyaku Co | Bicyclic amine derivative |
US6384050B1 (en) | 1996-10-25 | 2002-05-07 | Daiichi Pharmaceutical Co., Ltd. | Tricyclic amine derivatives |
WO1998024781A1 (fr) | 1996-12-04 | 1998-06-11 | Daiichi Pharmaceutical Co., Ltd. | Derives d'aminomethylpyrrolidine substitue |
DE69829682T2 (de) | 1997-05-21 | 2006-03-09 | Daiichi Pharmaceutical Co., Ltd. | Cis-disubstituierte aminocycloalkyl-pyrrolidin-derivate |
ZA984527B (en) | 1997-05-30 | 1998-12-03 | Daiichi Seiyaku Co | Substituted cyclobutylamine derivative |
WO1998058923A1 (fr) | 1997-06-24 | 1998-12-30 | Daiichi Pharmaceutical Co., Ltd. | Derives cis-substitues de fluoromethylpyrrolidine |
US6432442B1 (en) * | 1998-02-23 | 2002-08-13 | Mcneil-Ppc, Inc. | Chewable product |
-
2000
- 2000-03-16 KR KR1020017011627A patent/KR100768034B1/ko not_active IP Right Cessation
- 2000-03-16 CN CN008050538A patent/CN1343128B/zh not_active Expired - Fee Related
- 2000-03-16 EP EP10010622A patent/EP2275141A1/en not_active Withdrawn
- 2000-03-16 RU RU2001128071/15A patent/RU2270695C2/ru not_active IP Right Cessation
- 2000-03-16 AU AU31927/00A patent/AU3192700A/en not_active Abandoned
- 2000-03-16 CA CA2367373A patent/CA2367373C/en not_active Expired - Fee Related
- 2000-03-16 JP JP2000073572A patent/JP4694669B2/ja not_active Expired - Lifetime
- 2000-03-16 WO PCT/JP2000/001606 patent/WO2000054811A1/ja not_active Application Discontinuation
- 2000-03-16 EP EP00909677A patent/EP1161956A4/en not_active Withdrawn
- 2000-03-17 TW TW089104960A patent/TWI251495B/zh not_active IP Right Cessation
-
2001
- 2001-09-14 NO NO20014490A patent/NO20014490L/no not_active Application Discontinuation
-
2002
- 2002-08-22 HK HK02106154.7A patent/HK1044476B/zh not_active IP Right Cessation
-
2004
- 2004-10-07 US US10/959,297 patent/US20050152975A1/en not_active Abandoned
-
2006
- 2006-12-01 US US11/565,733 patent/US20070148235A1/en not_active Abandoned
-
2010
- 2010-10-08 JP JP2010228566A patent/JP2011006481A/ja active Pending
-
2011
- 2011-01-06 US US12/985,476 patent/US20110159049A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993017667A1 (en) * | 1992-03-12 | 1993-09-16 | Taisho Pharmaceutical Co., Ltd. | Composition for oral preparations |
JPH07285838A (ja) * | 1994-04-15 | 1995-10-31 | Lion Corp | 口腔用組成物 |
EP0826376A1 (en) * | 1995-05-02 | 1998-03-04 | Taisho Pharmaceutical Co. Ltd | Composition for oral administration |
JPH1135486A (ja) * | 1997-07-23 | 1999-02-09 | Lion Corp | 薬用固形製剤 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1161956A4 * |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001288117A (ja) * | 2000-04-05 | 2001-10-16 | Otsuka Pharmaceut Co Ltd | 医薬製剤用組成物 |
JP4570725B2 (ja) * | 2000-04-05 | 2010-10-27 | 大塚製薬株式会社 | 医薬製剤用組成物 |
WO2002024167A1 (fr) * | 2000-09-19 | 2002-03-28 | Daiichi Pharmaceutical Co., Ltd. | Composition medicinale |
EP1333807A2 (en) * | 2000-10-13 | 2003-08-13 | Advancis Pharmaceuticals | Extended release erythromycin derivatives |
JP2004528272A (ja) * | 2000-10-13 | 2004-09-16 | アドバンシス ファーマスーティカルス | 持続型放出エリスロマイシン誘導体 |
EP1333807A4 (en) * | 2000-10-13 | 2005-06-29 | Advancis Pharmaceuticals | ERYTHROMYCIN DERIVATIVES WITH PROLONGED RELEASE |
JP2002138034A (ja) * | 2000-10-27 | 2002-05-14 | Kyoto Pharmaceutical Industries Ltd | 苦味マスキングチュアブル錠およびその製造方法 |
US6806256B2 (en) | 2001-03-05 | 2004-10-19 | Ortho -Mcneil Pharmaceutical, Inc. | Taste masked liquid pharmaceutical compositions |
JP2006515592A (ja) * | 2002-12-23 | 2006-06-01 | アベンティス・ファーマ・ソシエテ・アノニム | 味覚マスキングが必要な活性物質の経口調剤のための化合物 |
JP4676763B2 (ja) * | 2002-12-23 | 2011-04-27 | アベンティス・ファーマ・ソシエテ・アノニム | 味覚マスキングが必要な活性物質の経口調剤のための化合物 |
JPWO2005025622A1 (ja) * | 2003-09-12 | 2006-11-16 | 株式会社龍角散 | 苦みマスキング粒状ゼリー飲料 |
AU2004271853B2 (en) * | 2003-09-12 | 2009-03-12 | Ryukakusan Co. Ltd. | Granular jelly drink capable of masking bitter |
WO2005025622A1 (ja) * | 2003-09-12 | 2005-03-24 | Ryukakusan Co. Ltd. | 苦みマスキング粒状ゼリー飲料 |
JP4647493B2 (ja) * | 2003-09-12 | 2011-03-09 | 株式会社龍角散 | 苦みマスキング粒状ゼリー飲料 |
US8287897B2 (en) | 2003-09-12 | 2012-10-16 | Ryukakusan Co., Ltd. | Bitterness-masking particulate jelly beverage |
WO2011052500A1 (ja) * | 2009-10-28 | 2011-05-05 | 第一三共株式会社 | ワックス安定製剤 |
Also Published As
Publication number | Publication date |
---|---|
HK1044476B (zh) | 2010-09-17 |
EP1161956A1 (en) | 2001-12-12 |
US20050152975A1 (en) | 2005-07-14 |
EP1161956A4 (en) | 2005-03-16 |
CN1343128A (zh) | 2002-04-03 |
TWI251495B (en) | 2006-03-21 |
RU2270695C2 (ru) | 2006-02-27 |
HK1044476A1 (en) | 2002-10-25 |
AU3192700A (en) | 2000-10-04 |
US20110159049A1 (en) | 2011-06-30 |
JP2000327590A (ja) | 2000-11-28 |
JP2011006481A (ja) | 2011-01-13 |
JP4694669B2 (ja) | 2011-06-08 |
KR100768034B1 (ko) | 2007-10-17 |
CA2367373C (en) | 2011-09-20 |
NO20014490D0 (no) | 2001-09-14 |
EP2275141A1 (en) | 2011-01-19 |
US20070148235A1 (en) | 2007-06-28 |
NO20014490L (no) | 2001-11-14 |
KR20010102571A (ko) | 2001-11-15 |
CA2367373A1 (en) | 2000-09-21 |
CN1343128B (zh) | 2010-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4694669B2 (ja) | 医薬組成物 | |
JP4439499B2 (ja) | アムロジピン含有粒子およびそれからなる口腔内崩壊錠 | |
JP2014132022A (ja) | 医薬組成物 | |
JP2006502156A (ja) | 風味を遮断された投与形態およびそれらの製剤の方法 | |
JP2006528181A (ja) | 酸分泌を阻害するために有用な薬学的製剤ならびにそれらを作製および使用する方法 | |
CA2689486C (en) | Extrudates with improved taste masking | |
TW201204415A (en) | Method for preparing pharmaceutical compositions intended for oral administration comprising one or more active ingredients and the compositions comprising same | |
WO2007011018A1 (ja) | 口腔内速崩壊性錠 | |
WO2019130749A1 (ja) | 新規微粒子コーティング(薬物含有中空粒子及びその製法) | |
KR102090135B1 (ko) | 솔리페나신 또는 이의 약제학적으로 허용가능한 염을 포함하는 구강 붕해정 및 이의 제조방법 | |
ITUA20163981A1 (it) | Composizioni farmaceutiche comprendenti safinamide | |
JP7148319B2 (ja) | プラスグレルを含む口腔内崩壊錠 | |
JP5241681B2 (ja) | アムロジピン含有粒子およびそれからなる口腔内崩壊錠 | |
JP2021001122A (ja) | 不快な官能的性質をもつ薬剤をマスキングした医薬固形製剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 00805053.8 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 09926123 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2000909677 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020017011627 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: 2367373 Country of ref document: CA Ref document number: 2367373 Country of ref document: CA Kind code of ref document: A |
|
WWP | Wipo information: published in national office |
Ref document number: 1020017011627 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 2000909677 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWR | Wipo information: refused in national office |
Ref document number: 1020017011627 Country of ref document: KR |