WO2010027101A1 - Préparation solide pour utilisation médicale - Google Patents

Préparation solide pour utilisation médicale Download PDF

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Publication number
WO2010027101A1
WO2010027101A1 PCT/JP2009/065876 JP2009065876W WO2010027101A1 WO 2010027101 A1 WO2010027101 A1 WO 2010027101A1 JP 2009065876 W JP2009065876 W JP 2009065876W WO 2010027101 A1 WO2010027101 A1 WO 2010027101A1
Authority
WO
WIPO (PCT)
Prior art keywords
isobutoxymethyl
methylbutyl
active ingredient
oxirane
carbamoyl
Prior art date
Application number
PCT/JP2009/065876
Other languages
English (en)
Japanese (ja)
Inventor
長本降浩
安部毅宏
Original Assignee
日本ケミファ株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本ケミファ株式会社 filed Critical 日本ケミファ株式会社
Publication of WO2010027101A1 publication Critical patent/WO2010027101A1/fr

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Classifications

    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • 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
    • A61K9/20—Pills, tablets, discs, rods

Definitions

  • the present invention relates to a solid medical preparation containing (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium as an active ingredient.
  • Patent Document 2 WO 2004/96785
  • the present inventor relates to (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylic acid monosodium preparation, and a medical solid having improved stability.
  • a study on the formulation was conducted and the present invention was completed.
  • the present invention stabilizes oils using (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium as an active ingredient.
  • the present invention relates to a medical solid preparation contained as an agent.
  • the present invention also provides a mixture obtained by mixing monosodium (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate and oils.
  • the present invention relates to a medical solid preparation produced by granulating a sucrose using an alcohol.
  • the present invention also provides a mixture obtained by mixing monosodium (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate and oils.
  • the present invention relates to a solid preparation for medical use produced by granulating water with water.
  • the present invention also provides a mixture obtained by mixing monosodium (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate and oils.
  • the present invention relates to a medical solid preparation produced by dry granulation.
  • the invention also provides (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium, excipients, disintegrants, binders and It is related with the tablet manufactured by mixing oils, granulating the obtained mixture using ethanol, drying, and tableting.
  • the invention also provides (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium, excipients, disintegrants, binders and It is related with the tablet manufactured by mixing oils, granulating the obtained mixture using water, drying, and tableting.
  • the invention also provides (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium, excipients, disintegrants, binders and
  • the present invention relates to a tablet produced by mixing oils, then dry granulating the resulting mixture and then tableting.
  • the present invention also relates to a method for stabilizing a water-unstable active ingredient comprising mixing oils as stabilizers in a medical solid preparation containing a water-unstable active ingredient.
  • the present invention also relates to a tablet containing an active ingredient whose stability after tableting is significantly reduced by the pressure at the time of tableting, an active ingredient decomposed by tableting pressure comprising mixing oils as a stabilizer. It relates to a stabilization method.
  • the present invention also relates to a method for stabilizing an active ingredient that is decomposed by pressing pressure, which comprises mixing an oil as a stabilizer in a granule or tablet containing an active ingredient that is decomposed by pressing pressure of dry granulation.
  • the present invention also relates to a method for stabilizing a water-unstable active ingredient, characterized by containing oils as a stabilizer in a medical solid preparation containing a water-unstable active ingredient.
  • the present invention also relates to an effective ingredient for decomposing by tableting pressure, characterized by containing an oil as a stabilizer in a tablet containing an active ingredient whose stability after tableting is significantly reduced by the pressure at the time of tableting. It relates to a method for stabilizing ingredients. Furthermore, the present invention is a granule or tablet containing an active ingredient that is decomposed by the press pressure of dry granulation, and contains an oil as a stabilizer. It relates to the conversion method.
  • (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium, which is an active ingredient of the present invention, is WO 99/11640 (patent document) 1), those obtained by the production method described in WO 2004/024672, WO 2004/96785 (Patent Document 2) and the like can be used, and the drug substance is preferably crystalline.
  • the oils include stearic acid, calcium stearate, magnesium stearate, sucrose fatty acid ester, hydrogenated oil, carnauba wax, glycerin fatty acid ester, talc, polyethylene glycols (polyethylene glycol, etc.) and benzoic acid.
  • Acid esters methyl paraoxybenzoate, ethyl paraoxybenzoate, etc.
  • stearic acid calcium stearate
  • sucrose fatty acid ester hydrogenated oil
  • carnauba wax glycerin fatty acid ester
  • talc polyethylene glycols (polyethylene glycol, etc.) and benzoic acid.
  • Acid esters methyl paraoxybenzoate, ethyl paraoxybenzoate, etc.
  • stearic acid calcium stearate
  • sucrose fatty acid ester hydrogenated oil
  • carnauba wax glycerin fatty acid ester
  • talc polyethylene glycols
  • polyethylene glycols polyethylene
  • the above oils 1 or 2 or more and other known stabilizers may be used in combination.
  • the amount of oil is preferably 2 to 35% of the solid preparation, more preferably 5 to 25% of the solid preparation.
  • the dosage form of the medical solid preparation of the present invention include tablets, granules, powders, capsules and the like.
  • the active ingredient (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium is, for example, In the case of a tablet, 1 to 300 mg, preferably 30 to 150 mg is contained in one tablet.
  • (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium It can be obtained by mixing an excipient, a disintegrant, a binder and oils, granulating the resulting mixture using alcohols, and then drying.
  • alcohols ethanol or isopropyl alcohol is preferable.
  • the obtained mixture can be granulated with water and then dried.
  • (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate monosodium, excipients, disintegrants, binders and oils It can also be obtained by mixing and dry granulating the resulting mixture.
  • excipients include calcium hydrogen phosphate, sodium hydrogen phosphate, lactose, crystalline cellulose, pregelatinized starch, calcium carbonate, corn starch, sucrose, potato starch, D-mannitol, etc., preferably phosphorus
  • examples include calcium oxyhydrogen and lactose.
  • disintegrant examples include carboxymethyl starch sodium, crospovidone, low-substituted hydroxypropyl cellulose, carmellose, carmellose sodium, croscarmellose sodium, hydroxypropyl starch or corn starch, preferably carboxymethyl starch sodium.
  • binder examples include hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, methylcellulose, polyvinyl alcohol, sodium carboxymethylcellulose, pregelatinized starch, pullulan, and gelatin, and preferably hydroxypropylcellulose.
  • the solid preparation of the present invention when the solid preparation of the present invention is a tablet, it may contain a lubricant, a pigment and the like which are usually used.
  • the lubricant examples include sodium stearyl fumarate, magnesium stearate, talc and the like.
  • Granules and tablets may be coated.
  • the tablet may be an orally disintegrating tablet.
  • the capsule contains those described in the above powders and granules.
  • the medical preparation of the present invention is a capsule, the one described in (ii) is applied when the content is powdery, and the one described in (ii) is applied when granular.
  • (2R, 3S) -2,3-dihydroxy-N-[(1S) -1-isobutoxymethyl-3-methylbutyl] succinamic acid monosodium The content is preferably 1.0% or less relative to monosodium (2S, 3S) -3-[[(1S) -1-isobutoxymethyl-3-methylbutyl] carbamoyl] oxirane-2-carboxylate, More preferably, it is 0.5% or less.
  • the mixed powder of Example 1 containing oils (stearic acid) is a production amount (that is, content) of a diol body as compared with the mixed powder of Comparative Example 1 that does not contain oil. The same shall apply hereinafter).
  • the preparation powder of Example 2 containing oils (stearic acid) produced less diol than the preparation powder of Comparative Example 2 which did not contain oil.
  • the medical solid preparation of the present invention containing oils is a useful preparation in which decomposition of Compound A is suppressed as compared with a solid preparation not containing oils. Moreover, the following result was obtained from Table 1, 3 regarding the production amount of the diol body.
  • a stable medical use in which degradation by moisture is suppressed by providing a coating on the active ingredient by blending oils in the mixing process of the preparation A solid formulation can be obtained.
  • oils can be used as a cushioning material in tableting at the end of the preparation to prevent decomposition of the active ingredients by blending oils in the formulation mixing process.
  • a stable medical solid preparation can be obtained.
  • the medical solid preparation containing the compound A of the present invention as an active ingredient can be used as a compounding agent by blending with other known rheumatoid arthritis therapeutic agents, osteoporosis therapeutic agents and the like.
  • the mixed powder described in the Examples can be used as a powder by using it as a powder or as the contents of a capsule, or by continuously granulating.
  • the powdered powder can be used as a tablet by continuing tableting in addition to use as a granule or as the contents of a capsule.
  • the stability of compound A is evaluated by using the following measuring instrument and evaluation method, and the diol form ((2R, 3S) -2,3-dihydroxy-N-[(1S) -1- (Isobutoxymethyl-3-methylbutyl] succinamic acid monosodium) was measured.
  • the compound A described in the following Reference Examples and Examples was a crystalline compound obtained by the production method described in WO 2004/96785 (Patent Document 2).
  • the solution is filtered through a 0.45 ⁇ m membrane filter. Remove 15 ml of the first filtrate and use the rest as the sample solution.
  • Tablet hardness measurement measuring instrument Kiyama digital hardness tester (Fujiwara Seisakusho) Evaluation method Accelerated test (40C, 75% RH, aluminum pyro packaging (with desiccant)) Evaluation was made by the amount (%) of diol produced with respect to Compound A after 12 weeks.
  • Comparative Example 2 150.0 g of lactose, 63.0 g of calcium hydrogenphosphate, 12.0 g of sodium carboxymethyl starch, 9.0 g of hydroxypropylcellulose, 6.0 g of sodium stearyl fumarate are uniformly mixed with 150.0 g of compound A, and a dry granulator Was used to obtain a dispensing powder.
  • Example 1 Compound A 150.0 g was mixed uniformly with lactose 60.0 g, calcium hydrogen phosphate 63.0 g, sodium carboxymethyl starch 12.0 g, hydroxypropylcellulose 9.0 g, stearic acid 90 g, and sodium stearyl fumarate 6.0 g. A mixed powder was obtained.
  • Example 2 Compound A 150.0 g was mixed uniformly with lactose 60.0 g, calcium hydrogen phosphate 63.0 g, sodium carboxymethyl starch 12.0 g, hydroxypropylcellulose 9.0 g, stearic acid 90 g, and sodium stearyl fumarate 6.0 g. Granulation was performed using a dry granulator to obtain a dispensing powder. Stability test 1 Table 1 shows the amount of diol produced after 12 weeks of the acceleration test for the mixed powders and preparation powders obtained in Comparative Examples 1 and 2 and Examples 1 and 2. Test result 1 As apparent from Table 1, the mixed powder of Example 1 containing oils (stearic acid) produced less diol than the mixed powder of Comparative Example 1 that did not contain oil.
  • Example 2 the preparation powder of Example 2 containing oils (stearic acid) produced less diol than the preparation powder of Comparative Example 2 which did not contain oil. It was found that the compound A was decomposed by granulation by comparing Comparative Examples 1 and 2 before and after the granulation step. In Examples 1 and 2, the decomposition of the compound A by granulation was effective. Was held down. Comparative Example 3 Compound A (150.0 g) was mixed with lactose (114.0 g), calcium hydrogen phosphate (90.0 g), carboxymethyl starch sodium (15.0 g), and hydroxypropylcellulose (18.0 g), and granulated with ethanol. Subsequently, the obtained preparation powder was dried.
  • an uncoated tablet having a tablet weight of 130.0 mg was obtained.
  • the hardness of the tablet was set to be 1 to 2 kg.
  • the amount of sodium stearyl fumarate used was 1/10 of Compound A.
  • Comparative Example 5 Compound A (150.0 g) was mixed with lactose (114.0 g), calcium hydrogen phosphate (90.0 g), carboxymethyl starch sodium (15.0 g), and hydroxypropylcellulose (18.0 g), and granulated with ethanol. Subsequently, the obtained preparation powder was dried. After drying, sieving with a 16M sieve, sodium stearyl fumarate was added, mixed and tableted. As a result, an uncoated tablet having a tablet weight of 130.0 mg was obtained.
  • the hardness of the tablet was set to 4 to 5 kg. (The amount of sodium stearyl fumarate used was 1/10 of Compound A.) Comparative Example 6 Compound A (150.0 g) was mixed with lactose (114.0 g), calcium hydrogen phosphate (90.0 g), carboxymethyl starch sodium (15.0 g), and hydroxypropylcellulose (18.0 g), and granulated with ethanol. Subsequently, the obtained preparation powder was dried. After drying, sieving with a 16M sieve, sodium stearyl fumarate was added, mixed and tableted. As a result, an uncoated tablet having a tablet weight of 130.0 mg was obtained. The tablet hardness was set to 7-8 kg.
  • Table 2 shows the amount of diol produced after 12 weeks of the acceleration test for the powders and tablets obtained in Comparative Examples 3 to 7. As is apparent from Table 2, the amount of the diol compound, which is a related substance, was smaller in the preparation powder of Comparative Example 3 than in the tablets of Comparative Examples 4-7. Further, from Comparative Examples 4 to 7, it was found that the tablets containing Compound A were more unstable as the hardness was higher, and the more unstable.
  • Comparative Example 8 Compound A (5.0 g) was mixed with lactose (5.3 g), calcium hydrogen phosphate (1.5 g), carboxymethyl starch sodium (0.4 g), and hydroxypropyl cellulose (0.3 g), and granulated with ethanol. Subsequently, the obtained preparation powder was dried. After drying, the mixture was sieved with a 16M sieve, and then sodium stearyl fumarate was added and mixed to obtain a dispensing powder.
  • Example 3 Compound A (5.0 g) is mixed with lactose (2.3 g), calcium hydrogen phosphate (1.5 g), carboxymethyl starch sodium (0.4 g), hydroxypropyl cellulose (0.3 g), and stearic acid (3.0 g), and granulated using ethanol. did. Subsequently, the obtained preparation powder was dried. After drying, sieving with a 16M sieve, sodium stearyl fumarate was added, mixed and tableted. As a result, an uncoated tablet having a tablet weight of 130.0 mg was obtained.
  • Example 4 Compound A 5.0 g is mixed with lactose 2.3 g, calcium hydrogen phosphate 1.5 g, carboxymethyl starch sodium 0.4 g, hydroxypropylcellulose 0.3 g, stearic acid 3.0 g, and purified water is used. Grained. Subsequently, the obtained preparation powder was dried. After drying, sieving with a 16M sieve, sodium stearyl fumarate was added, mixed and tableted. As a result, an uncoated tablet having a tablet weight of 130.0 mg was obtained.
  • Example 5 Compound A 5.0 g is mixed with lactose 2.3 g, calcium hydrogen phosphate 1.5 g, carboxymethyl starch sodium 0.4 g, hydroxypropylcellulose 0.3 g, stearic acid 3.0 g, and purified water is used. Grained. Subsequently, the obtained preparation powder was dried. After drying, the mixture was sieved with a 16M sieve, and then sodium stearyl fumarate was added and mixed to obtain a dispensing powder.
  • Example 6 Compound A 100.0 g was mixed uniformly with lactose 66.0 g, calcium hydrogen phosphate 40.0 g, sodium carboxymethyl starch 8.0 g, hydroxypropyl cellulose 6.0 g, stearic acid 30 g, and sodium stearyl fumarate 10.0 g. Granulation was performed using a dry granulator to obtain a dispensing powder. The obtained preparation powder was sieved with a 16M sieve, sodium stearyl fumarate was added again, mixed and tableted.
  • Example 7 Lactose, calcium hydrogen phosphate, sodium carboxymethyl starch, and hydroxypropylcellulose were uniformly mixed with Compound A, and granulated using ethanol. Subsequently, the obtained preparation powder was dried.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une préparation solide pour utilisation médicale, qui est obtenue par mélange d’un stabilisant tel que l’acide stéarique, d'ester d’acide gras de saccharose, d’huile hydrogénée, de cire de carnauba ou de talc dans du sel monosodique d’acide (2S,3S)-3-[[(1S)-1-isobutoxyméthyl-3-méthylbutyl]carbamoyl]oxirane-2-carboxylique, et a ainsi une stabilité de conservation améliorée.
PCT/JP2009/065876 2008-09-08 2009-09-04 Préparation solide pour utilisation médicale WO2010027101A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008230144A JP2011241148A (ja) 2008-09-08 2008-09-08 医療用固形製剤
JP2008-230144 2008-09-08

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WO2010027101A1 true WO2010027101A1 (fr) 2010-03-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013006797A (ja) * 2011-06-24 2013-01-10 Nippon Chemiphar Co Ltd カンデサルタンシレキセチル製剤
JP2018141011A (ja) * 2018-05-24 2018-09-13 日本ケミファ株式会社 カンデサルタン シレキセチル製剤

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017075136A (ja) * 2015-06-08 2017-04-20 ロート製薬株式会社 内服組成物
JP7304691B2 (ja) * 2018-12-06 2023-07-07 日本ケミファ株式会社 ゾピクロン、その光学異性体又はこれらの塩の何れかを有効成分として含有する錠剤

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57145659A (en) * 1981-03-06 1982-09-08 Chugai Pharmaceutical Co Ltd Production of tablet
JPH0769889A (ja) * 1993-09-03 1995-03-14 Kobayashi Kako Kk ニコランジル錠剤の製法
WO1999011640A1 (fr) * 1997-09-04 1999-03-11 Nippon Chemiphar Co., Ltd. Derives d'epoxysuccinamide
JP2000007585A (ja) * 1998-06-16 2000-01-11 Toho Shinyaku Kk 耐湿性固形製剤及びその製造方法
JP2002234832A (ja) * 2002-02-18 2002-08-23 Dai Ichi Seiyaku Co Ltd 錠 剤
WO2004096785A1 (fr) * 2003-04-25 2004-11-11 Nippon Chemiphar Co., Ltd. Sel d'acide (2s,3s)-3-[[(1s)-1-isobutoxymethyl-3-methylbutyl]carbamoyl]oxyrane-2-carboxylique
JP2005104972A (ja) * 2003-09-08 2005-04-21 Nof Corp Ｌ−カルニチン圧縮成形体、及びその製造方法
JP2005200372A (ja) * 2004-01-16 2005-07-28 Nof Corp 油性成分被覆ｌ−カルニチン塩粉末およびその用途

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57145659A (en) * 1981-03-06 1982-09-08 Chugai Pharmaceutical Co Ltd Production of tablet
JPH0769889A (ja) * 1993-09-03 1995-03-14 Kobayashi Kako Kk ニコランジル錠剤の製法
WO1999011640A1 (fr) * 1997-09-04 1999-03-11 Nippon Chemiphar Co., Ltd. Derives d'epoxysuccinamide
JP2000007585A (ja) * 1998-06-16 2000-01-11 Toho Shinyaku Kk 耐湿性固形製剤及びその製造方法
JP2002234832A (ja) * 2002-02-18 2002-08-23 Dai Ichi Seiyaku Co Ltd 錠 剤
WO2004096785A1 (fr) * 2003-04-25 2004-11-11 Nippon Chemiphar Co., Ltd. Sel d'acide (2s,3s)-3-[[(1s)-1-isobutoxymethyl-3-methylbutyl]carbamoyl]oxyrane-2-carboxylique
JP2005104972A (ja) * 2003-09-08 2005-04-21 Nof Corp Ｌ−カルニチン圧縮成形体、及びその製造方法
JP2005200372A (ja) * 2004-01-16 2005-07-28 Nof Corp 油性成分被覆ｌ−カルニチン塩粉末およびその用途

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013006797A (ja) * 2011-06-24 2013-01-10 Nippon Chemiphar Co Ltd カンデサルタンシレキセチル製剤
JP2018141011A (ja) * 2018-05-24 2018-09-13 日本ケミファ株式会社 カンデサルタン シレキセチル製剤

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