JPS6028920A - External preparation for skin - Google Patents

External preparation for skin

Info

Publication number
JPS6028920A
JPS6028920A JP13674883A JP13674883A JPS6028920A JP S6028920 A JPS6028920 A JP S6028920A JP 13674883 A JP13674883 A JP 13674883A JP 13674883 A JP13674883 A JP 13674883A JP S6028920 A JPS6028920 A JP S6028920A
Authority
JP
Japan
Prior art keywords
skin
drug
external preparation
cosmetic
active ingredient
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
JP13674883A
Other languages
Japanese (ja)
Other versions
JPH0623101B2 (en
Inventor
Kazuo Kikazawa
気賀沢 和雄
Mineji Hiiragi
柊木 峯治
Takashi Sawabe
沢辺 隆司
Kikuo Wakizaka
脇坂 菊雄
Yuu Murayama
村山 涌
Kiyoshi Ishii
潔 石井
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PAAMAKEMU ASIA KK
Permachem Asia Ltd
Aska Pharmaceutical Co Ltd
Original Assignee
PAAMAKEMU ASIA KK
Grelan Pharmaceutical Co Ltd
Permachem Asia 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 PAAMAKEMU ASIA KK, Grelan Pharmaceutical Co Ltd, Permachem Asia Ltd filed Critical PAAMAKEMU ASIA KK
Priority to JP58136748A priority Critical patent/JPH0623101B2/en
Publication of JPS6028920A publication Critical patent/JPS6028920A/en
Publication of JPH0623101B2 publication Critical patent/JPH0623101B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

PURPOSE:An external preparation for the skin useful for remedying and preventing skin diseases such as humid tetter, acne, wound, or protecting the skin as a drug, quasi-drug, or cosmetic, containing dipyruvic triureide. CONSTITUTION:An external preparation for the skin containing dipyruvic triuredie as an active ingredient. The external preparation for the skin has remedy promoting action on damaged parts such as wound, ulcer, burn, etc., astringent action, and covering action. It is useful for remedying erosion of the skin or mucosa, ulcer, and skin diseases such as humid tetter, etc., and used as drug or guasi-drug having the above-mentioned medicinal effects. Since the active ingredient has no irritation to the skin, it may be blended with cosmetic, it prevents skin irritations of lips and chapped skin, is expected to have soft feeling in use, to make people undergo rejuvenation, etc. An amount of the active ingredient added is 0.01-20wt% based on the whole amount of pharmaceutical preparation, preferably 0.01-5wt% in the case of cosmetic, and 1-20wt% in the case of quasi-drug.

Description

【発明の詳細な説明】 本発明は、ジビルビックトリウレイドを配合することを
Ir!f徴とする皮膚外用剤に門するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for incorporating dibilvic triureide into Ir! It is classified as a topical skin preparation for treating f symptoms.

ジビルビックトリウレイド(riipyruvic t
riurerle)は、例えばBulletin of
 t、he C1+cmj、cal 5ocietyo
f Japan(プレティン・オブ・ザ拳ケミカル・ン
サイティーオプ・ジャパン)第39巻 1559頁(1
966年)に製造法が記載されているように古くから知
られているにもかかわらず、その薬理作用は報告されて
いなかった。
dibilvic triureide
For example, Bulletin of
t,he C1+cmj,cal 5ocietyo
f Japan (Pretin of the Fist of Chemical Science Op Japan) Volume 39 Page 1559 (1
Although it has been known for a long time, as its production method was described in 1996), its pharmacological effects had not been reported.

本発明者らは、今まで種々のアラントイン関連化合物を
合成し、その生理活性および物性について鋭意研究を行
い、先に5−メチルアラントインにきわめてすぐれた消
化性潰瘍治療効果を見出し、特許出願中であるが(特願
昭57−48129号)、今回その中間体であるジビル
ビックトリウレイドにすぐれた皮膚に対する作用効果を
見出したのである。すなわち、ジビルビックトリウレイ
ドは湿疹、座蒼あるいは損傷部位への治療、さらに角質
抑制作用、その他一般皮膚灸の治療にも有効であり、さ
らに化粧料への用途も見出し、さらに研究を重ねること
によって本発明を完成させるに至った。
The present inventors have synthesized various allantoin-related compounds and conducted intensive research on their physiological activities and physical properties, and have previously discovered that 5-methylallantoin has an extremely excellent therapeutic effect on peptic ulcers, and is currently applying for a patent. (Japanese Patent Application No. 57-48129), but we have now discovered that its intermediate, dibilbic triureide, has excellent effects on the skin. In other words, dibilbic triureide is effective for treating eczema, acne, and damaged areas, as well as for suppressing keratin and for other general skin moxibustion treatments.Furthermore, it has found applications in cosmetics, and further research is needed. This led to the completion of the present invention.

従って、ジビルビックトリウレイドを配合した本発明の
皮膚外用剤は創傷、潰瘍、火傷等の損傷部位の治癒促進
作用を示し、合せて収斂、被覆作用が存在し、皮膚、粘
膜などのビラン、潰瘍の治療に有益に用いられ、さらに
湿疹等皮膚科疾患に用いられ、薬効を目的とした医薬品
Therefore, the skin external preparation of the present invention containing dibilbic triureide exhibits a healing promoting effect on damaged areas such as wounds, ulcers, and burns, and also has an astringent and covering effect, and has an effect on the skin, mucous membranes, etc. A drug that is beneficially used in the treatment of ulcers, and is also used for dermatological diseases such as eczema, and has medicinal properties.

医薬部外ルンの用途が可能である。さらにジビルビツク
トリウレイドは皮膚刺激性がないため多くの化粧品類へ
の配合が可61′、である。例え(・よ口紅に例をとる
と、口紅はし1.l: L ?−じ人によっ〔刺激を感
じるものであるが、ジビルビックトリウレイドを配合す
ることによって刺激やアレルギー反応を示さないし、ま
た脣のgれや割目をきれいになおすことができる。
Non-pharmaceutical applications are possible. Furthermore, dibilubitric triureide does not cause skin irritation, so it can be incorporated into many cosmetic products. For example, if we take a lipstick as an example, the lipstick tip is 1.L: L. In addition, it is possible to cleanly repair wrinkles and cracks on the lips.

本発明の皮膚外用剤を得るKは、ジビルビックトリウレ
イドを@薬品、医薬部外品あるいは化粧石の軟膏、クリ
ーノ1.乳液、ゲル9液剤、1)k剤等の基剤に直接添
加するか、またはそれらの油相部分に予め溶解し、Aす
るいはアルコール等の溶剤にてあらかじめ溶解したもの
を配合し、乳化、混合1分散、溶解等の処理を行うこと
に」って得られる。また散剤の場合も直接ジビルビック
トリウレイドを添加し、混合1分散などの通常の゛処理
で得られる。こ゛)tらの製造法においては、医薬品、
医薬部外品および化粧品ηの分野における公知の方法を
採用することがてきる。
To obtain the skin external preparation of the present invention, dibilbic triureide is added to @drugs, quasi-drugs, cosmetic ointments, and 1. Emulsification is achieved by adding directly to a base such as an emulsion, gel 9 solution, 1) K agent, or by pre-dissolving it in the oil phase thereof and blending it with a solvent such as A or alcohol. , by performing processes such as mixing, dispersion, and dissolution. In the case of a powder, dibilbic triureide is directly added, and the powder can be obtained by ordinary processing such as mixing and dispersion. In the manufacturing method of these companies, pharmaceuticals,
Known methods in the field of quasi-drugs and cosmetics η can be employed.

かくして得られた本発明外用剤は、医摺、医薬部外品ま
たは化粧品として、ヒトまたは哺乳動物に対して、皮膚
疾患の治療・予防、皮膚面の保護などの目的で使用され
る。
The thus obtained external preparation of the present invention can be used as a medical product, quasi-drug, or cosmetic for humans or mammals for the purpose of treating and preventing skin diseases, protecting the skin surface, and the like.

本発明におけるジビルビックトリウレイドの配合量は、
製剤全体に対して0.01〜20重員パー重量トの範囲
であるが、化粧料や医薬品外用剤の形態や使用方法など
に応じ配合量を適宜選択出来る。一般的には化粧料にお
いては0.01〜5重量パーセント、医薬品外用剤にお
いては1〜20重量パーセントが好ましい。医薬品外用
剤に配合した場合は、上述の薬効が期待でき、また化粧
料に配合した場合は、例えば皮膚の肌荒れを防ぎ、しっ
とりとした使用感とともに、きめの細かい弾力性のある
若々しくみずみずしい肌をつくることが期待できる。
The blending amount of dibilbic triureide in the present invention is:
The amount is in the range of 0.01 to 20 parts by weight based on the entire formulation, but the amount can be selected as appropriate depending on the form and usage method of the cosmetic or external pharmaceutical preparation. Generally, it is preferably 0.01 to 5% by weight for cosmetics and 1 to 20% by weight for external pharmaceutical preparations. When added to external pharmaceutical preparations, the above-mentioned medicinal effects can be expected, and when added to cosmetics, for example, it prevents skin roughness, provides a moist feeling, and provides a youthful and fresh feeling with fine elasticity. You can expect it to improve your skin.

本発明のジビルビックトリウレイドを合成するには、尿
素とピルビン酸とを脱水剤(好ましくは酸触媒)の存在
下に反応させる方法が採用される。本反応は室温下ない
し若干の加温下に行われ、酸触媒としては、塩酸、硫酸
などの無機酸が用いられる。反応は通常で3日間で終了
し、反応後目的物は自体公知の手段(抽出、洗浄。
To synthesize the dibilvic triureide of the present invention, a method is employed in which urea and pyruvic acid are reacted in the presence of a dehydrating agent (preferably an acid catalyst). This reaction is carried out at room temperature or under slight heating, and an inorganic acid such as hydrochloric acid or sulfuric acid is used as the acid catalyst. The reaction usually completes in 3 days, and after the reaction, the desired product is extracted by means known per se (extraction, washing).

再結晶など)によっ”C容易に単離される。ここで得ら
れたジビリビックトリウレ・rドは、文献K11l′l
!点と元素分析の記載しかないため、名種スペクトルの
測定によってこの構造を確認し7だ。
"C" is easily isolated by recrystallization, etc.). The dibilibic triuret r-do obtained here is
! Since there are only descriptions of dots and elemental analysis, we confirmed this structure by measuring the spectra and got 7.

次に本発明の皮膚外用剤の、ltl!造法、効果を実施
例によって説明する。
Next, LTL! of the skin external preparation of the present invention! The manufacturing method and effects will be explained using examples.

合成例 ジピリビノクトリウレ・fドの製造法濃塩酸8
.5 ml K尿素7.5gを溶解し、これにピルビン
酸5.0&を室温・攪拌[:に滴下した後、さらに攪拌
な続けた。10時間程で反応混合物は白濁し、約3日後
に殆ど固化しブこ。
Synthesis example Method for producing dipyribinoctriurene f-do Concentrated hydrochloric acid 8
.. 5 ml 7.5 g of K urea was dissolved, and 5.0 g of pyruvic acid was added dropwise to the solution at room temperature with stirring, followed by further stirring. The reaction mixture became cloudy in about 10 hours and almost solidified after about 3 days.

r過して得られた無色固体な稀′アンモニ′ア水と酢酸
から書結することにより分解点:300 U以」二の無
色剣状結晶を69g W) lニー、 、、元素分析値
 (%) (!oHx2N60i・21hn計算値 C
,33,75;H,5,o3;、!?、26.a4実験
値 c、34.oo;n、4.6a;n、2a:58薄
層クロマトグラフィー(展開溶媒 n−ブタノール:ジ
オキサン:水=4 : 1 : 2 )Rf値= 0.
50 核磁気共鳴スペクトル δ(rn、+5o−ds)1.
33(−重線、 CBS ) 6.62.’i’、90および10.27(各−重線。
By combining the colorless solid dilute ammonia water obtained by filtration with acetic acid, 69 g of colorless sword-shaped crystals with a decomposition point of 300 U or more were obtained. %) (!oHx2N60i・21hn calculated value C
,33,75;H,5,o3;,! ? , 26. a4 Experimental value c, 34. oo;n, 4.6a;n, 2a:58 thin layer chromatography (developing solvent n-butanol:dioxane:water = 4:1:2) Rf value = 0.
50 Nuclear magnetic resonance spectrum δ(rn, +5o-ds)1.
33 (- double line, CBS) 6.62. 'i', 90 and 10.27 (each - double line.

NH) 実施例1 外用散剤 ジビルビックトリウレイド 60重置部炭酸マグネシウ
ム 4073(置部 パラオキシ安息香酸エチル 2重量部 合 ii 1..000重量部 あらかじめ60pKて16時間乾燥したトウモロコシデ
ンプンとそれぞれの原料を秤量し、■合せしめる。
NH) Example 1 Powder for external use Dibilbic triureide 60 parts Magnesium carbonate 4073 (part 2 parts by weight Ethyl paraoxybenzoate ii 1.000 parts by weight Corn starch previously dried at 60 pK for 16 hours and each raw material Weigh and ■combine.

実施例2 外用軟膏 ジビルビックトリウレイドO1gを笛十改正1」本薬局
方の処方および製造法に従って製した吸水軟膏に均一に
分散し、全体をI C1gとした。
Example 2 External ointment 1 g of dibilvic triureide O was uniformly dispersed in a water-absorbing ointment prepared in accordance with the prescription and manufacturing method of the Pharmacopoeia ``Fueju Revised 1'' to give a total of 1 g of ICl.

ここで吸水軟膏の処方は次の通り。The prescription for the water-absorbing ointment is as follows.

白色ワセリン4g、十タノール:t、sg、ヒスキオレ
イン酸ソルビタン0.5g、ラウロマクロゴールo、o
sg、バラオキシ安息香酸エチル001g、バラオギシ
安息香酸ブチル001gおよび全景をlogとするに十
5)な精製水。
White petrolatum 4g, tentanol: t, sg, sorbitan hiskioleate 0.5g, lauromacrogol o, o
sg, 001 g of ethyl benzoate, 001 g of butyl benzoate, and 15) purified water with the whole view as log.

実施例3 口紅 ミ ツ ロ ウ 10 カルナウバロウ 5 キャンデリラロウ 4 ラ ノ リ ン 8 流動パラフイン 2() イーンプロビリミリステート 15 ミリスチン酸2−オクチルドデシル 10顔 料 1.
4 香 料 15 酸化防止剤 適量 実施例4 皮膚用クリーム ジビルピックトリウレイド 1.0% スクワラン 100 ワ セ リ ン 9,0 ミ ツ ロ ウ 4.0 マイクロワツクス 8.0 イソプロピルミリステート 5.0 ミリスチン酸2−オクチルドデシル 10.0ポリオギ
シエチレンモノステアレート4.0ソルビタンモノステ
アレー) a、O プロピレングリコール 10.0 蒸 留 水 35.0 実施例5 薬効薬理 創傷治療におよほす作用。
Example 3 Lipstick Beeswax 10 Carnauba wax 5 Candelilla wax 4 Lanolin 8 Liquid paraffin 2() Een probilimiristate 15 2-octyldodecyl myristate 10 Pigment 1.
4 Fragrance 15 Antioxidant Appropriate amount Example 4 Skin cream Divirpic triureide 1.0% Squalane 100 Vaseline 9.0 Beeswax 4.0 Microwax 8.0 Isopropyl myristate 5. 0 2-octyldodecyl myristate 10.0 Polyoxyethylene monostearate 4.0 Sorbitan monostearate) a, O Propylene glycol 10.0 Distilled water 35.0 Example 5 Effect on pharmacological wound treatment .

ラット背皮屑に円形の皮膚欠損部を作製し、実施例1で
得られた外用剤および実施f?+ 1の5−メブールア
ラントインを除いた基剤のみを創面l−に°りき0.0
4 gを治癒する才で散布することにより創傷治癒作用
を検討し2だ。
A circular skin defect was created on rat back skin scraps, and the external preparation obtained in Example 1 and Example f? + Apply only the base excluding 5-mebulallantoin of 1 to the wound surface 0.0
The wound healing effect was investigated by spraying 4g with a healing agent, and the result was 2.

実施例1で得られた外用剤の処信にJ:り創傷の治癒は
促進し、治癒日数短縮が見られ、またその効果の程度に
おいて基剤群より優れた成績を示した。その結果を第1
表に示した。
Treatment with the external preparation obtained in Example 1 accelerated the healing of the wound, shortened the healing time, and showed better results than the base group in terms of the degree of effect. The result is the first
Shown in the table.

第1表 創傷治癒日数にお」:はず影響′。Table 1: Impact on wound healing time.

注)[N、s、J有意差なし [P〈0.OlおよびP<0.05Jはそれぞれ「危険
率1%および5%で有意差あり」を意味する。
Note) [N, s, J no significant difference [P<0. Ol and P<0.05J mean "significant difference at risk rates of 1% and 5%", respectively.

「s、 E、 J標準誤差 実施例6 局所刺激性 刺激性物質に対する感受性の高いウサギの眼粘膜、健常
皮膚および角層を剥離した有傷皮膚を用いて、実施例1
で得た外用剤の局所刺激作用を観察した。その結果、眼
粘膜では結膜の軽微な一過性の発赤を示す例がみられた
が、角膜への影響は全く認められなかった。
"s, E, J standard error Example 6 Local irritation Example 1 was carried out using ocular mucosa, healthy skin, and injured skin from which the stratum corneum was removed from rabbits, which are highly sensitive to irritating substances.
The local irritation effect of the external preparation obtained was observed. As a result, some cases of slight temporary redness of the conjunctiva were observed in the ocular mucosa, but no effect on the cornea was observed.

皮膚におけるバッチテストにおいても、軽微な発赤を示
す例が発現したが、いずれも一過性であり、有傷皮膚に
おいても出血やビランなどはみられなかった。
In a batch test on the skin, slight redness was observed in some cases, but it was only temporary, and no bleeding or irritation was observed even on damaged skin.

以上の結果より、実施例1で得られた外用剤(・シは危
惧すべき局所刺激作用は認められない。
From the above results, the external preparation obtained in Example 1 does not exhibit any worrying local irritation effects.

ジビルピックトリウレイドの急性毒性(ddY系マツマ
ウス1!FF10 特許出願人 グレラン製薬株式会社 株式会社パーマヶム・アジア
Acute Toxicity of Dibilpic Triureide (ddY Pine Mouse 1! FF10 Patent Applicant: Grelan Pharmaceutical Co., Ltd. Permagam Asia Co., Ltd.

Claims (1)

【特許請求の範囲】[Claims] ジビルビックトリウレイドを配合することを特徴とする
皮膚外用剤
External skin preparation characterized by containing dibilvic triureide
JP58136748A 1983-07-28 1983-07-28 External skin preparation Expired - Lifetime JPH0623101B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP58136748A JPH0623101B2 (en) 1983-07-28 1983-07-28 External skin preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58136748A JPH0623101B2 (en) 1983-07-28 1983-07-28 External skin preparation

Publications (2)

Publication Number Publication Date
JPS6028920A true JPS6028920A (en) 1985-02-14
JPH0623101B2 JPH0623101B2 (en) 1994-03-30

Family

ID=15182581

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58136748A Expired - Lifetime JPH0623101B2 (en) 1983-07-28 1983-07-28 External skin preparation

Country Status (1)

Country Link
JP (1) JPH0623101B2 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59172421A (en) * 1983-03-18 1984-09-29 Grelan Pharmaceut Co Ltd Remedy for peptic ulcer

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59172421A (en) * 1983-03-18 1984-09-29 Grelan Pharmaceut Co Ltd Remedy for peptic ulcer

Also Published As

Publication number Publication date
JPH0623101B2 (en) 1994-03-30

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