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
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
  • A61K31/4164—1,3-Diazoles
  • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
• • 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
  • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
  • A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
• • 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
  • A61K9/0012—Galenical forms characterised by the site of application
  • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
• • 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
  • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
• • 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
  • A61K9/08—Solutions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • 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 pharmaceutical composition.
• the present invention relates to a pharmaceutical composition which is useful as an antimycotic agent.
• R 2 chlorine atom
• a serious problem also arises in relation to the production technique such that the crystals are deposited during the use in a low temperature region and the content is decreased on account of the storage in a high temperature region.
• any pharmaceutical medicament preparation which contains 1) a compound represented by the following general formula (1) and/or a salt thereof and 2) an acylated derivative, an etherified derivative, or an oxolane derivative of a polyhydric alcohol.
• R x , R 2 are halogen atoms.
• Patent Documents
• Patent Document 1 International Publication No.
• Patent Document 2 International Publication No.
• Patent Document 3 Japanese Patent Application Laid-open No. 08-245377.
• the present invention has been made in the circumstances as described above, an object of which is to provide a medicament preparation or pharmaceutical
• the present inventors have diligently performed repeated studies and efforts in order to seek for a component of medicament preparation which is capable of replacing such as N-methyl-2-pyrrolidone and propylene carbonate and which has the action to enhance the
• polyhydric alcohol has such a characteristic, and the invention has been finally completed. That is, the present invention is as follows.
• a pharmaceutical composition comprising: 1) a compound represented by the following general formula (1) and/or a ' salt thereof and 2) a polyhydric alcohol derivative.
• Ri , R 2 independently represent
• R3, R 4 , R5, R6 independently represent hydrogen atom, oxygen atom, carboxyl group, hydroxyalkyl group having a number of carbon atom or atoms of 1 to 4, or alkyl group having a number of carbon atom or atoms of 1 to 4, R 3 , R 4 and/or R 5 , R6 may represent the same atom
• X represents carbon atom to which hydrogen atom is bonded or oxygen atom
• bond indicated by a broken line may be either present or absent, and R 6 is absent when the bond indicated by the broken line is present, provided that propylene carbonate is excluded.
• ⁇ 4> The pharmaceutical composition as defined in ⁇ 3>, wherein the oxolane derivative represented by the general formula (2) is selected from tetrahydrofuran, 1,3- dioxolane, 2-oxo-l , 3-dioxolane, 5-oxotetrahydrofuran-2- carboxylic acid, ⁇ -crotonolactone, and 2 , 2-dimethyl-l , 3- dioxolane-4-methanol .
• the oxolane derivative represented by the general formula (2) is selected from tetrahydrofuran, 1,3- dioxolane, 2-oxo-l , 3-dioxolane, 5-oxotetrahydrofuran-2- carboxylic acid, ⁇ -crotonolactone, and 2 , 2-dimethyl-l , 3- dioxolane-4-methanol .
• ⁇ 5> The pharmaceutical composition as defined in ⁇ 1> or ⁇ 2>, wherein the polyhydric alcohol derivative is an acylated compound or an etherified compound of polyhydric alcohol .
• acylated compound of polyhydric alcohol is a triglyceride of short chain or middle chain fatty acid or an ester of short chain or long chain fatty acid and
• triglyceride of short chain or middle chain fatty acid is selected from triacetin, tricaprilin,
• glycerol trioctanoate glycerol trioctanoate
• glycerol tri caprylate/caprate
• ester of short chain or long chain fatty acid and (poly) ethylene glycol is selected from ethylene glycol monoacetate, polyethylene glycol monolaurate, and
• polyoxyethylene alkyl ether polyoxyethylene- polyoxypropylene alkyl ether.
• the polyethylene glycol alkyl ether is selected from diethylene glycol monoethyl ether, diethylene glycol monobenzyl ether, diethylene glycol diethyl ether, and triethylene glycol dimethyl ether;
• the polyoxyethylene alkyl ether is selected from polyoxyethylene lauryl ether and polyoxyethylene cetyl ether;
• polyoxyethylene-polyoxypropylene alkyl ether is polyoxyethylene-polyoxypropylene cetyl ether.
• ⁇ 12> The pharmaceutical composition as defined in ⁇ 11>, wherein the hydroxyalkylbenzene is benzyl alcohol.
• composition as defined in any one of ⁇ 1> to ⁇ 12>, further comprising a-hydroxy acid and/or phosphoric acid.
• composition comprising 1) a compound represented by the following general formula (1) and/or a salt thereof, 2) a polyhydric alcohol derivative, and 3) hydroxyalkylbenzene, the method comprising:
• Ri , R 2 independently represent
• the medicament preparation which is excellent in the solubilization stability in relation to the compound represented by the general formula (1) during the storage in the low temperature region and the high temperature region.
• the pharmaceutical composition of the present invention has such a feature that the compound represented by the general formula (1), such as luliconazole, is usually contained by 0.5 to 15% by mass and preferably 1 to 10% by mass.
• a method for producing such a component is already known (for example, Japanese Patent Application Laid-open No. 09-100279).
• Luliconazole is excellent in the crystallization property or crystallization performance. Crystals are deposited in some cases when luliconazole is contained by not less than 4% by mass in the case of the storage at a low temperature, for example, 5°C depending on the type of the used solvent, even in such a state that hydroxy carboxylic acid such as lactic acid or the like is added to suppress the crystallization.
• the deposition as described above is suppressed in a combination of the medicament preparation containing the polyhydric alcohol derivative as described later on so that the biological usefulness is enhanced, especially the transfer into the nail is enhanced, and thus the treatment effect on the trichophytosis unguium is enhanced.
• the ordinary mycosis (fungal disease) of the foot in the case of the ordinary mycosis (fungal disease) of the foot
• the content is preferably not less than 5% by mass and more preferably not less than 6% by mass. Further, it is preferable that the content is not more than 10% by mass which is the upper limit of the suppression of the crystal deposition at the low temperature. In view of the above, it is preferable that the content of the
• compound represented by the general formula (1) in the pharmaceutical composition for the nail is about 6 to 10% by mass.
• the compound represented by the general formula (1) is especially preferably
• lanoconazole exemplified by lanoconazole .
• the preferred content of lanoconazole is in conformity with the case of luliconazole as well.
• the salt is not specifically limited, provided that the salt is pharmaceutically acceptable. It is especially preferable to use salt of mineral acid such as salt of phosphoric acid (phosphate) or the like and salt of a-hydroxy acid such as glycolic acid, lactic acid or the like .
• the pharmaceutical composition of the present invention has such a feature that the polyhydric alcohol derivative is contained.
• a derivative is exemplified by the oxolane derivative (dehydrated compound of diol or cyclic acetal compound) , acylated polyhydric alcohol, and etherified polyhydric alcohol. It is possible to use any one of them.
• Polyhydric alcohol may be preferably
• glycerol (poly) ethylene glycol, and (poly) propylene glycol.
• the oxolane derivative may be preferably
• R 3 , R4, R5, R6 independently represent hydrogen atom, oxygen atom, carboxyl group, hydroxyalkyl group having a number of carbon atom or atoms of 1 to 4, or alkyl group having a number of carbon atom or atoms of 1 to 4, and R 3 , R 4 and/or R5, R6 may represent the same atom together.
• the atomic species is oxygen.
• X represents carbon atom to which hydrogen atom is bonded or oxygen atom. X is
• Bond indicated by a broken line may be either present or absent.
• R6 is absent when the bond indicated by the broken line is present.
• propylene carbonate is excluded.
• the derivative is in a liquid state under a condition of 1 atmosphere (atm) at 25°C.
• Specified compounds of the oxolane derivative may be preferably exemplified, for example, by tetrahydrofuran, 2- methyltetrahydrofuran, 1, 3-dioxolane, 2 , 2-dimethyl-l , 3- dioxolane, 2-oxo-l, 3-dioxolane, 5-oxotetrahydrofuran-2- carboxylic acid, ⁇ -crotonolactone, and 2 , 2-dimethyl-l , 3- dioxolane-4-methanol .
• the oxolane derivative is especially preferably selected from tetrahydrofuran, 1 , 3-dioxolane, 5- oxotetrahydrofuran-2-carboxylic acid, and 2 , 2-dimethyl-l , 3- dioxolane-4-methanol .
• One of the derivative as described above can be used, or two or more of the derivatives as described above can be used in combination.
• the acylated polyhydric alcohol it is preferable to select, for example, ethylene glycol, polyethylene glycol, glycerol, polyglycerol , propylene glycol, polypropylene glycol, and 1 , 3-butanediol as the polyhydric alcohol base material to introduce short chain or middle chain carboxylic acid residue including, for example, acetyl group, caprylic acid residue, capric acid residue, and octanoic acid residue, or long chain fatty acid residue including, for example, lauric acid residue and oleic acid residue.
• carboxylic acid residue including, for example, acetyl group, caprylic acid residue, capric acid residue, and octanoic acid residue
• long chain fatty acid residue including, for example, lauric acid residue and oleic acid residue.
• the short chain fatty acid herein means those having a number of carbon atom or atoms of, for example, 1 to 4
• the middle chain fatty acid means those having a number of carbon atom or atoms of, for example, 5 to 11
• the long chain fatty acid means those having a number of carbon atom or atoms of, for example, 12 to 30.
• the fatty acid residue preferably has a number of carbon atoms of not less than 3.
• the unsaturated bond may be either present or absent in the fatty acid residue.
• the acylated polyhydric alcohol especially preferably has the fluidity at 1 atm at 25°C.
• the polymerization degrees of polyethylene glycol and polypropylene glycol are preferably about 5 to 300.
• the polymerization degree of polyglycerol is preferably about 2 to 20.
• acylated polyhydric alcohol is preferably exemplified, for example, by triacetin,
• tri (caprylate/caprate) ethylene glycol monoacetate, polyethylene glycol monolaurate, polyethylene glycol monooleate, ethylene glycol diacetate, polyethylene glycol dilaurate, polyethylene glycol dioleate, and ethylene glycol diacetate. It is especially preferable to use the compound selected from triacetin, tricaprilin, glycerol trioctanoate, glycerol tri (caprylate/caprate) , ethylene glycol monoacetate, polyethylene glycol monolaurate, and polyethylene glycol monooleate.
• One of the derivative as described above can be used, or two or more of the derivatives as described above can be used in combination.
• the etherified polyhydric alcohol it is preferable to select, for example, polyethylene glycol, polyoxyethylene polymer, and polyoxyethylene- polyoxypropylene copolymer as the polyhydric alcohol base material to form an ether, for example, with alkyl group having a number of carbon atom or atoms of 1 to 20 or alkyl group which may be substituted with aromatic group. Phenyl group is preferred as the aromatic group.
• the etherified polyhydric alcohol especially preferably has the fluidity at 1 atm at 25°C.
• polyoxyethylene polymer and polyoxyethylene- polyoxypropylene copolymer are preferably about 2 to 20.
• the etherified polyhydric alcohol is preferably exemplified, for example, by diethylene glycol monoethyl ether, diethylene glycol monobenzyl ether, diethylene glycol diethyl ether, triethylene glycol
• polyoxyethylene lauryl ether polyoxyethylene cetyl ether
• polyoxyethylene cetyl ether polyoxyethylene-polyoxypropylene cetyl ether. It is especially preferable to use the compound selected from diethylene glycol monoethyl ether, diethylene glycol diethyl ether, and polyethylene glycol lauryl ether.
• One of the derivative as described above can be used, or two or more of the derivatives as described above can be used in combination.
• one or two or more of the compound or compounds selected from the polyhydric alcohol derivative as described above is/are preferably contained by 0.1 to 50% by mass, more preferably 1 to 20% by mass, and much more preferably 2 to 10% by mass with respect to the total amount of the
• the mass as described above is preferably 1/2 to 20 times the mass and more preferably 1 to 10 times the mass of the compound represented by the general formula (1) .
• medicament preparation pharmaceutical preparation
• pharmaceutical preparation pharmaceutical preparation
• formulate the medicament preparation are preferably exemplified, for example, by alcohols including, for example, ethanol and isopropanol; ketones including, for example, acetone; nonionic surfactants including, for example, polyoxyethylene cured castor oil and
• cellulose, ethylcellulose, and higher alcohols such as isostearyl alcohol, oleyl alcohol and the like; polyhydric alcohols including, for example, propylene glycol; diesters of dibasic acids including, for example, diethyl sebacate, dipropyl sebacate, and diethyl adipate; hydroxyalkylbenzene including, for example, benzyl alcohol, phenethyl alcohol, and phenyl propanol; stabilizers or stabilizing agents including, for example, -hydroxy acids such as lactic acid, glycolic acid, citric acid and the like and mineral acids such as phosphoric acid and the like; and solvents including, for example, alkylene carbonate such as
• NMP -methyl-2-pyrrolidone
• crotamiton hydroxyalkylbenzene, and the stabilizer, which is exemplified, for example, by a-hydroxy acid, and phosphoric acid, act together with the polyhydric alcohol derivative to exhibit the excellent solubilization performance for the compound represented by the general formula (1) and/or the salt thereof and the action to suppress the formation of stereoisomer. Therefore, it is especially preferable to contain a combination of such compounds.
• the alkyl group which has a number of carbon atom or atoms of 1 to 4, is preferred in relation to the hydroxyalkylbenzene.
• benzyl alcohol phenethyl
• the component as described above is preferably contained by 5 to 99% by mass in a total amount and more preferably 10 to 99% by mass with respect to the total amount of the pharmaceutical composition.
• the function or action, in which the formation of stereoisomer of the compound represented by the general formula (1) is suppressed is provided.
• the crystal deposition is suppressed in the low temperature region. Therefore, it is preferable to use the component or components as described above as the
• the production is preferably performed as follows.
• the compound represented by the general formula (1) and/or the salt thereof is/are wetted or immersed (infiltrated) with hydroxyalkylbenzene, followed by being agitated (stirred) and solubilized, with being heated in order to effect the solubilization, if desired.
• the polyhydric alcohol derivative is added thereto, so as to dilute a mixture and to cause the solvation.
• the remaining solvent is added thereto, followed by being heated, if desired, agitated (stirred) , and solubilized,
• the means for replacing propylene carbonate, N-methyl-2-pyrrolidone, and crotamiton can be provided by using the polyhydric alcohol derivative or combining the polyhydric alcohol derivative and
• the medicament preparation can be prepared or formulated without using propylene carbonate, N-methyl-2- pyrrolidone, and crotamiton.
• propylene carbonate N-methyl-2- pyrrolidone
• crotamiton N-methyl-2- pyrrolidone
• the component can be contained preferably by 1 to 30% by mass and more preferably 2 to 15% by mass with respect to the total amount of the pharmaceutical composition.
• stabilizer or stabilizing agent including, for example, a- hydroxy acids such as lactic acid, glycolic acid, citric acid and the like and mineral acids such as phosphoric acid and the like by 0.1 to 20% by mass, more preferably 1 to 10% by mass with respect to the total amount of the
• solubilizing performance in order to improve the solubilizing performance (solubility) and the stability, it is also preferable to contain higher alcohol such as isostearyl alcohol or the like which is in a form of liquid at 1 atm at 25°C by 10 to 30% by mass, more preferably 15 to 25% by mass. Additionally, in order to improve the solubilizing performance (solubility) , it is also preferable to contain polyhydric alcohol such as propylene glycol by 1 to 30% by mass, more preferably 5 to 20% by mass with respect to the total amount of the
• composition of the present invention can be produced by treating the essential amino acids
• any agent form, which is used in the pharmaceutical composition can be applied without any special limitation.
• the oral administration medicament preparation including, for example, the tablet or pill, the capsule, the granule, the film coating agent, the powder, and the syrup
• the non-oral administration medicament including, for example, the injection, the suppository, the inhalant or inhalation, the embrocation or liniment, the patch, the aerosol, the percutaneous absorbent, the eye drop or eye lotion, and the nose drop.
• the skin external preparation including, for example, the embrocation or liniment, the patch, the aerosol, and the percutaneous absorbent.
• the form of the skin external preparation is preferably exemplified, for example, by the lotion, the emulsion or emulsified lotion, the gel, the cream, the aerosol, the nail enamel, and the hydrogel patch.
• the lotion is especially preferred.
• the pharmaceutical composition of the present invention is preferably used to treat the disease caused by the fungus or the prevention of the deterioration of the disease by utilizing the characteristics of the
• the disease caused by the fungus is exemplified by the foot trichophytosis such as the athlete's foot or dermatophytosis , the body
• the pharmaceutical composition of the present invention is especially preferably used to treat the hard keratin portion such as the trichophytosis unguium, because the effect is especially remarkable.
• the pharmaceutical composition of the present invention is especially preferably expressed on the nail.
• the effect is also exerted on the ordinary skin mycosis or fungal disease. Therefore, the pharmaceutical composition, which is directed to the skin mycosis or fungal disease and which satisfies the requirement of the present invention, also belongs to the technical scope of the present
• the skin mycosis as described above can be exemplified, for example, by the foot trichophytosis and the keratin proliferation type trichophytosis which
• the present invention is preferably applied to the keratin proliferation type trichophytosis on which any effect is hardly obtained by any ordinary medicament (agent or drug) , because the effect of the present invention remarkably appears thereon.
• the mode of use can be appropriately selected by considering, for example, the weight, the age, the sex, and the disease condition of the patient. However, in the case of the ordinary adult, it is preferable to administrate 0.01 to 1 g per day of the compound represented by the general formula (1) and/or the salt thereof. It is
• antimycotic agent drug
• the pharmaceutical composition of the present invention in the case of the trichophytosis unguium, a serious problem arises in relation to the recrudesce and the reinfection.
• the pharmaceutical composition of the present invention in the form as described above, the pharmaceutical composition of the present invention
• compositions of the present invention were produced in accordance with the following
• Comparative Example 1 was also prepared by performing the process in the same manner as described above. The preparations were stored for 3 weeks at 60°C. The amounts of SE isomer and Z isomer produced as the stereoisomers of luliconazole were
• Results are shown in Table 1. According to Table 1, it is shown that the acylated derivative of polyhydric alcohol has the action which is the same as or equivalent to those of propylene carbonate, N-methyl-2-pyrrolidone (NMP) and crotamiton.
• NMP N-methyl-2-pyrrolidone
• compositions 11 to 20 were prepared in accordance with the following formulations in the same manner as in Example 1. Comparative Example 2 was also prepared in accordance with the same or equivalent process.
• Results are shown in Table 2. It is shown that the pharmaceutical composition of the present invention has the excellent solubilizing performance (solubility) and the excellent stabilizing action even in the case of the use of the oxolane derivative of polyhydric alcohol corresponding to the cyclic acetal compound or the dehydrated compound of diol .
• compositions 21 to 33 were prepared in accordance with the following formulations in the same manner as in Example 1. Comparative Example 3 was also prepared in accordance with the same or equivalent process.
• Results are shown in Table 3. It is shown that the pharmaceutical composition of the present invention has the excellent solubilizing performance (solubility) and the excellent stabilizing action even in the case of the use of the etherified derivative of the polyhydric alcohol.
• the present invention is applicable to the pharmaceutical composition.

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• 2011
  • 2011-06-10 US US13/703,300 patent/US8962669B2/en active Active
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