WO1997039740A1 - Timbre contenant des derives du 1,2-ethanediol ou leurs sels - Google Patents

Timbre contenant des derives du 1,2-ethanediol ou leurs sels Download PDF

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Publication number
WO1997039740A1
WO1997039740A1 PCT/JP1997/001363 JP9701363W WO9739740A1 WO 1997039740 A1 WO1997039740 A1 WO 1997039740A1 JP 9701363 W JP9701363 W JP 9701363W WO 9739740 A1 WO9739740 A1 WO 9739740A1
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WO
WIPO (PCT)
Prior art keywords
group
nitrogen
patch
ester
patch according
Prior art date
Application number
PCT/JP1997/001363
Other languages
English (en)
Japanese (ja)
Inventor
Tetsumi Yamakawa
Keiko Takakura
Yoshiko Kubo
Yoko Shimada
Masahiro Kodani
Masaru Tai
Original Assignee
Toyama Chemical Co., Ltd.
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 Toyama Chemical Co., Ltd. filed Critical Toyama Chemical Co., Ltd.
Priority to AU25767/97A priority Critical patent/AU2576797A/en
Publication of WO1997039740A1 publication Critical patent/WO1997039740A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms

Definitions

  • the present invention provides a compound represented by the following general formula:
  • R ' represents a hydrogen atom, a halogen atom or an alkyl group;.
  • R 2 and R 3 are the same or different represent an alkyl group” 1 represented by the 2-Etanjio Lumpur derivative or a salt thereof It relates to a patch contained as an active ingredient.
  • Transdermal preparations are known to be easy to administer, have a clear presence or absence of administration, and allow patients and caregivers to easily control the administration.
  • 1,2-ethanediol derivatives or salts thereof described in JP-A-3-232830 and JP-A-495070 are useful compounds as cerebral function improving agents, and in particular, (R) 1-1 (benzo [ b) Thiofen-15-yl) 1-2- [2- (N, N-Jetylamino) ethoxy] ethanol hydrochloride (hereinafter referred to as T15888) is a preferred compound.
  • T15888 ethanol hydrochloride
  • the transdermal formulation is not known.
  • 1,2-Ethanediol derivatives or salts thereof of general formula [1] having a cerebral function improving effect can be administered even if the patient has severe cerebral dysfunction (eg, dementia) and does not intend to take the drug.
  • severe cerebral dysfunction eg, dementia
  • the skin permeability of a drug depends on the intrinsic physicochemical properties of the drug, and is closely related to the interaction between the drug, base, and skin, and is extremely complicated. Development of skin and transmucosal absorbable preparations and new tests, experiments, and evaluation methods, pages 5 to 61, 1986, Technoy Publishing Division).
  • An object of the present invention is to show that it has the same or higher absorbability as an oral preparation, has physical properties suitable for use as a patch, has low skin irritation, and is stable over time.
  • the 1,2-ethanediol derivative of the general formula [1] or a salt thereof, urea By using a combination of polyethylene glycol and a nitrogen-containing polymer coating agent, it is possible to obtain a patch with excellent percutaneous absorption, low skin irritation, and good physical properties and stability over time. Find out the present invention This has led to the formation.
  • the present invention is a patch wherein a plaster layer containing the following components (a) to (d) is provided on one surface of a support.
  • R 1 is a hydrogen atom, a halogen atom or an alkyl group
  • halogen atom of R 1 in the general formula [1] examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the alkyl group for R ′, R 2 and R 3 include methyl, ethyl, propynole, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, Examples include straight-chain or branched C ,, 2- alkyl groups such as decyl and pendecyl.
  • R 1 is a hydrogen atom or a fluorine atom
  • R 3 is a straight-chain C 4 compound such as methyl, ethyl or propyl.
  • a compound or a salt thereof that is an alkyl group is preferable, and a compound or a salt thereof in which R 1 is a hydrogen atom or a fluorine atom, and IT and R 3 are an ethyl group is preferable.
  • the 1,2-ethanediol derivative of the general formula [1] or a salt thereof is disclosed in JP-A-3-23230, JP-A-4-95070, JP-A-6-9615 and W096 / 12717 (PCT / JP95 / 2162). Can be produced by the method described in (1).
  • the amount of the 1,2-ethanediol derivative of the general formula [1] or a salt thereof used in the patch of the present invention is preferably 0.1 to 20% by weight, more preferably 0.5 to 12% by weight. %.
  • the polyethylene glycol used in the patch of the present invention has the following formula
  • the amount of polyethylene glycol used in the patch of the present invention is preferably It is 1 to 30% by weight, more preferably 2.5 to 20% by weight.
  • the amount of urea used in the patch of the present invention is preferably 0.5 to 10% by weight, and more preferably 2 to 8% by weight.
  • the nitrogen-containing polymer coating agent used in the patch of the present invention contains a (meth) acrylate ester having no nitrogen in the ester residue and a (meth) acrylate ester having a nitrogen in the ester residue. It is a copolymer.
  • the ester residue of a (meth) acrylate ester that does not contain nitrogen in the ester residue is a straight-chain or branched C, 1 that may be substituted with one or two hydroxyl groups.
  • alkyl groups, and preferred groups include methyl group, ethyl group, 2-hydroxyethyl group, butyl group, hexyl group, octyl group, 2-ethylhexyl group, decyl group, and lauryl group. Particularly, a methyl group, an ethyl group and a butyl group are preferred.
  • alkyl groups of the C, H alkylammonioethyl group include methyl, ethyl, propyl, butyl, hexyl, octyl, and 2-ethylhexyl groups.
  • a methyl group is preferred. More specifically, examples include dimethylaminoethyl, dimethylammonioethyl and trimethylammonioethyl groups.
  • nitrogen-containing polymer coating agent examples include methyl methacrylate “butyl methacrylate” 2-dimethylaminoethyl copolymer (trade name: Odragit E) 00: Laem Pharma Co., Ltd. And methacrylic acid trimethylammonium metholcobolima-1 (trade name: Eudragit RS30D: Laem manufactured by Pharma).
  • the compounding amount of the nitrogen-containing polymer coating agent used in the patch of the present invention is preferably 0.5 to 20% by weight, more preferably 2 to 17% by weight, and particularly preferably 2 to 10% by weight. is there.
  • the patch of the present invention may contain C (i ⁇ alcohol and / or C Ester of fatty acid and alcohol is blended.
  • Cr, 'Alcohols include hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, pendecyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, cetyl alcohol, oleyl alcohol, 9-Decene-1-ol, linoleyl alcohol, linolenyl alcohol,], 2-dodecanediol and 1,2,6-hexantriol are preferred, but oleyl alcohol is particularly preferred.
  • the compounding amount of the ester of C alcohol and Z or C fatty acid and alcohol of C used in the patch of the present invention is preferably 0.1 to 20% by weight, more preferably 3 to 10% by weight. It is.
  • the patch of the present invention may further contain, if necessary, a plasticizer, a skin irritation reducing agent, a pH adjuster, and the like.
  • a plasticizer e.g., ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, sodium hydroxide, diisopropanolamine, and genamine are used as pH adjusters.
  • Examples of the base used in the patch of the present invention include an acrylic pressure-sensitive adhesive composed of a monomer having no carboxyl group.
  • Acrylic adhesives include homopolymers or copolymers of (meth) acrylates and copolymers of (meth) acrylates with one or more other polymerizable monomers, (Meth) acrylate esters containing nitrogen as a residue are excluded.
  • Examples of the polymerizable monomer include vinyl acetate.
  • Examples of the acrylic pressure-sensitive adhesive include methyl acrylate′-acrylic acid-2-ethylhexyl copolymer resin emulsion (trade name: Nikkisol TS— 62: Nippon Carbide Co., Ltd.), Ethyl acrylate 'methyl methacrylate copolymer emulsion (trade name: Oydragit) NE 30 D: Laem-Falma) or a mixture thereof.
  • the support of the patch of the present invention is not particularly limited as long as it is drug-impermeable and can form and support a plaster layer.
  • the patch of the present invention has a release paper on the sticking surface to protect the plaster layer surface until use.
  • the release paper is not particularly limited, but polyethylene terephthalate or paper subjected to a release treatment with silicone resin or the like is used.
  • the patch of the present invention can be produced by a method usually used in this field.
  • Examples of the production method include (1) pulverizing a nitrogen-containing polymer coating agent, and then emulsifying a base emulsion. (2) a method of mixing an aqueous dispersion of the nitrogen-containing polymer coating agent and an emulsion of the base, (3) a method of dissolving the nitrogen-containing polymer coating agent with an acid, and then emulsifying the base. There is a method of adding a liquid.
  • an aqueous dispersion of the nitrogen-containing polymer film agent is mixed with an aqueous solution of polyethylene glycol, a drug and urea, and then, if necessary, an emulsion of the base, whose pH has been adjusted in advance, is prepared. Add and stir.
  • a nitrogen-containing polymer coating agent and an acid are heated in an aqueous solution to form a uniform solution.
  • An aqueous solution of the drug and urea is added to the obtained solution to make it uniform, and then polyethylene glycol is further added to make a uniform solution.
  • an emulsion of the base whose pH has been adjusted in advance is added and stirred.
  • Examples of the acid used in the method (3) include acetic acid, caprylic acid, capric acid, lauric acid, oleic acid, succinic acid, adipic acid, suberic acid, sebacic acid, lactic acid, gluconic acid, Organic acids, such as mono-, di-, and tricarboxylic acids, such as malic acid, tartaric acid, and citric acid; one of inorganic acids, such as hydrochloric acid, sulfuric acid, and phosphoric acid Species or a combination of two or more species may be mentioned, but acetic acid, lauric acid, adipic acid, lactic acid and hydrochloric acid are preferred.
  • the amount of acid used is 0.8-2.0 times equivalent to the nitrogen-containing polymer film agent.
  • the plaster solution obtained by the respective methods C '"Arco Ichiru and / or C 2 3 ⁇ 4 2 fatty acids and the C 2 2 alcohols emulsified in water using a pre-surfactant Add the ester and stir evenly.
  • surfactant examples include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene ethylene ether, polyoxyethylene stearyl ether, polyoxyethylene behenyl ether, polyoxyethylene castor oil, and polyoxyethylene cured.
  • Castor oil polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene sorbit beeswax, polyoxyethylene phytosterol, polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene monooleate Sorbitan, polyoxyethylene lanolin, polyethylene glycol monolaurate, polyethylene glycol monostearate, monooleic acid Although ethylene glycolate one Le and the like, monolaurate polyethylene glycol, polyoxyethylene O lipped Ruch We sulfonyl ether are preferably used.
  • the amount of surfactant is C 6 2 2 alcohols and Z or C ⁇ 2 2 fatty acid and c,. 01 to 1 ⁇ 0. respect 2 2 esters with alcohols (weight ratio).
  • the plaster solution obtained by mixing the respective prescription components according to the above method is applied onto a support, dried and then affixed with release paper, or the plaster solution is applied on release paper and dried, and the resulting plaster layer is obtained.
  • a patch can be produced by bringing the adhesive into close contact with the support.
  • methyl acrylate 'acrylic acid-2-ethylhexyl copolymer resin emulsion [trade name: Nikkiso TS-620, solid content 57-6]% (W / W): Nippon Power —Bide Co.] 3. 20 g was added and stirred at room temperature for 1 hour to obtain a plaster solution. The obtained plaster solution was uniformly coated on a polyester support so as to have a T-588 content of 2 mg / 10 cm 2 / plast 50 mg, dried at 40 ° C. for 15 hours, and then separated with a silicone resin. A treated release paper made of polyethylene terephthalate was adhered to obtain a patch.
  • Aqueous solution containing fatty acids of Eudragit E100 [trade name: Plastoid E35M, solid content 27-33% (W / W): manufactured by Laem Pharmaceutical Co.] 500mg, T-588mg and 500mg 3 ml of an aqueous solution containing 125 mg of urea was added and stirred uniformly. Further, 250 mg of triethylen glycol was added to make a uniform solution, and then 2.07 g of TS-620 was added and stirred to obtain a plaster solution. Thereafter, a patch was obtained in the same manner as in Example 1.
  • Example 1 instead of Eudragit E100, an aqueous dispersion of ethyl acrylate, methyl methacrylate, and methacrylate-modified trimethylammonium mucotyl copolymer (trade name: Eudragit RS30D, solid Min. 30! 3 ⁇ 4 (W / W): Patch by the same operation as in Example 1 except that 0.83 g of Rame Pharma Co., Ltd. was used, and 2.91 g of TS-6620 was added. I got
  • Example 1 1 To 500 mg of Plastoid E3, 3 mL of an aqueous solution containing T-588 lOOmg and 125 mg of urea was added and stirred uniformly. Further, 250 mg of triethylene glycol and 125 mg of urea were added to make a uniform solution, and 2.87 g of TS-620 was added and stirred to obtain a plaster solution. Thereafter, a patch was obtained in the same manner as in Example 1.
  • Example 1 1 To 500 mg of Plastoid E3, 3 mL of an aqueous solution containing T-588 lOOmg and 125 mg of urea was added and stirred uniformly. Further, 250 mg of triethylene glycol and 125 mg of urea were added to make a uniform solution, and 2.87 g of TS-620 was added and stirred to obtain a plaster solution. Thereafter, a patch was obtained in the same manner as in Example 1.
  • Example 1 1 To 500 mg of Plastoid E3, 3 mL of an
  • a patch was obtained in the same manner as in Example 2, except that 25 mg of triethylene glycol and 3.44 g of Nitrosol TS-620 were added.
  • a patch was obtained in the same manner as in Example 2, except that 500 mg of triethylene glycol and 2.66 g of Nitrosol TS-620 were added.
  • a patch was obtained in the same manner as in Example 2, except that 2.5 pounds of plus toe E 3 1 1 ⁇ was added and 2.09 g of two-stroke solvent TS-620 was added.
  • a patch was obtained in the same manner as in Example 1 except that 12.5 mg of Eudragit E100 and 3.30 g of Nikkisol TS-620 were added.
  • a patch was obtained in the same manner as in Example 2 except that the amount of T-588 contained in the added aqueous solution was 2.5 mg, and that 3.23 of TS-620 was added.
  • T-588 was extracted from the serum, and the blood concentration was measured by high performance liquid chromatography. Table 1 shows the area under the one-hour blood concentration curve (AUC0-4) for each sample.
  • the patch containing the 1,2-ethanediol derivative represented by the general formula [1] of the present invention or a salt thereof has an absorbability more than that of oral administration, and is excellent in persistence in blood concentration. Furthermore, good percutaneous absorption can be expected even for skin that has a prominent drying tendency and that has a high stratum corneum barrier function as seen in the elderly, who is the subject of administration of this drug. Moreover, the physical properties of the plaster layer such as adhesive strength, adhesive strength, cohesive strength and anchoring strength are good, and no skin irritation is observed. It also has excellent stability over time of the drug in the plaster layer.

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

Abstract

L'invention concerne un timbre comprenant un substrat et une couche d'un emplâtre contenant les composés (a) à (d): (a) est un dérivé du 1,2-éthandiol, ayant la formule générale (1) ou un sel de celui-ci, R1 dans cette formule étant hydrogène, halogéno ou alkyle et R2 et R3 étant chacun indépendamment alkyle), (b) est de l'urée, (c) est un polyéthylène glycol et (d) est un polymère azoté filmogène. Cet emplâtre permet une absorption de médicament plus élevée que par l'administration orale et permet de maintenir plus longtemps un certain niveau de médicament dans le sang.
PCT/JP1997/001363 1996-04-22 1997-04-21 Timbre contenant des derives du 1,2-ethanediol ou leurs sels WO1997039740A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU25767/97A AU2576797A (en) 1996-04-22 1997-04-21 Patch containing 1,2-ethanediol derivatives or salts thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/124041 1996-04-22
JP12404196 1996-04-22

Publications (1)

Publication Number Publication Date
WO1997039740A1 true WO1997039740A1 (fr) 1997-10-30

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PCT/JP1997/001363 WO1997039740A1 (fr) 1996-04-22 1997-04-21 Timbre contenant des derives du 1,2-ethanediol ou leurs sels

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AU (1) AU2576797A (fr)
WO (1) WO1997039740A1 (fr)
ZA (1) ZA973394B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002029969A (ja) * 2000-07-17 2002-01-29 Nitto Denko Corp 経皮吸収製剤
JP2002521393A (ja) * 1998-07-23 2002-07-16 レーム ゲゼルシヤフト ミツト ベシユレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフト 経口及び皮膚投与形用被覆剤及び結合剤
WO2009095057A3 (fr) * 2008-01-30 2010-03-04 Lts Lohmann Therapie-Systeme Ag Système thérapeutique transdermique à base d'urée

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383281A1 (fr) * 1989-02-14 1990-08-22 Toyama Chemical Co., Ltd. Dérivés du éthanediol-1,2 et leur sels, procédé pour leur préparation et agents rétablissant la fonction cérébrale les contenant
JPH049570A (ja) * 1990-04-26 1992-01-14 Nippon Kentetsu Co Ltd 冷凍冷蔵オープンショーケース
EP0565965A2 (fr) * 1992-04-13 1993-10-20 Toyama Chemical Co., Ltd. Dérivé de benzo(b)thiophén-5-yle et procédé pour sa préparation
WO1996012717A1 (fr) * 1994-10-25 1996-05-02 Toyama Chemical Co., Ltd. Potentialisateur de l'activite du facteur de croissance nerveuse contenant un derive de 1,2-ethanediol ou un sel de celui-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383281A1 (fr) * 1989-02-14 1990-08-22 Toyama Chemical Co., Ltd. Dérivés du éthanediol-1,2 et leur sels, procédé pour leur préparation et agents rétablissant la fonction cérébrale les contenant
JPH049570A (ja) * 1990-04-26 1992-01-14 Nippon Kentetsu Co Ltd 冷凍冷蔵オープンショーケース
EP0565965A2 (fr) * 1992-04-13 1993-10-20 Toyama Chemical Co., Ltd. Dérivé de benzo(b)thiophén-5-yle et procédé pour sa préparation
WO1996012717A1 (fr) * 1994-10-25 1996-05-02 Toyama Chemical Co., Ltd. Potentialisateur de l'activite du facteur de croissance nerveuse contenant un derive de 1,2-ethanediol ou un sel de celui-ci

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 43, No. 9, (1995), ONO SATOSHI et al., "Studies on Cognitive Enhancing Agents. III", p. 1492-1496. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002521393A (ja) * 1998-07-23 2002-07-16 レーム ゲゼルシヤフト ミツト ベシユレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフト 経口及び皮膚投与形用被覆剤及び結合剤
JP4636687B2 (ja) * 1998-07-23 2011-02-23 エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング 経口及び皮膚投与形用被覆剤及び結合剤
JP2002029969A (ja) * 2000-07-17 2002-01-29 Nitto Denko Corp 経皮吸収製剤
WO2009095057A3 (fr) * 2008-01-30 2010-03-04 Lts Lohmann Therapie-Systeme Ag Système thérapeutique transdermique à base d'urée
US9066887B2 (en) 2008-01-30 2015-06-30 Lts Lohmann Therapie-Systeme Ag Transdermal therapeutic system having urea components

Also Published As

Publication number Publication date
ZA973394B (en) 1997-11-20
AU2576797A (en) 1997-11-12

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