JPS5935398B2 - Novel hydantoin derivatives - Google Patents
Novel hydantoin derivativesInfo
- Publication number
- JPS5935398B2 JPS5935398B2 JP880377A JP880377A JPS5935398B2 JP S5935398 B2 JPS5935398 B2 JP S5935398B2 JP 880377 A JP880377 A JP 880377A JP 880377 A JP880377 A JP 880377A JP S5935398 B2 JPS5935398 B2 JP S5935398B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydantoin derivatives
- compound
- novel hydantoin
- derivative represented
- 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.)
- Expired
Links
- 150000001469 hydantoins Chemical class 0.000 title claims description 4
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 5- Benzyl-5-ureidohydantoin Chemical compound 0.000 description 2
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229960000458 allantoin Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
Description
【発明の詳細な説明】 本発明は、次式 ＣＨ２−Ｃ６Ｈ５ ＮＨ＝Ｃ−ＮＨＣ０ＮＨ２１ ０−ｃ／ ： ＼ ＮＨ−Ｃ＝０ で表わされる新規なヒダントイン誘導体に関する。[Detailed description of the invention] The present invention is based on the following formula CH2-C6H5 NH=C-NHC0NH21 0-c/: \ NH-C=0 This invention relates to a novel hydantoin derivative represented by:
式Ｉの化合物は、次式Ｃ６Ｈ５−ＣＨ２−ＣＯＣＯＯＨ
■
で表わされる化合物を尿素と、脱水剤好ましくは酸触媒
の存在下に反応させることにより製造することができる
。Compounds of formula I have the following formula C6H5-CH2-COCOOH
It can be produced by reacting the compound represented by (2) with urea in the presence of a dehydrating agent, preferably an acid catalyst.
新規化合物は不斉炭素原子を有し、通常はラセミ体とし
て得られるが、それぞれの光学活性体に分割して使用す
ることができる。The new compound has an asymmetric carbon atom and is usually obtained as a racemate, but it can be used by dividing into each optically active form.
本発明の化合物は、アラントインと類似の生理作用たと
えば抗炎症作用、角質化抑制作用等を有し、医薬品及び
化粧品として有用である。The compound of the present invention has physiological effects similar to those of allantoin, such as anti-inflammatory effects and keratinization-inhibiting effects, and is useful as pharmaceuticals and cosmetics.
本化合物はアラントインよりも無機性が少なく有機性を
有するため、脂質との親和性に優れている。実施例５−
ベンジルー５−ウレイドヒダントイン（ベンジルアラン
トイン）。This compound is less inorganic and more organic than allantoin, so it has excellent affinity with lipids. Example 5-
Benzyl-5-ureidohydantoin (benzyllantoin).
尿素１５Ｖを濃塩酸１７ｍｉに溶解し、フェニルピルビ
ン酸１６ｙを加え、よく攪拌したのち３０℃で５日間反
応させる。Urea 15V was dissolved in concentrated hydrochloric acid 17mi, phenylpyruvic acid 16y was added, and after stirring well, the mixture was allowed to react at 30°C for 5 days.
生成した白色結晶を吸引沢過し、エタノールで洗浄した
のち、結晶をエタノール１００ｍ１中に浸漬する。０．
５日後に吸引沢過し、エタノールで洗浄すると、５−ベ
ンジル５−ウレイドヒダントインの白色結晶４７が得ら
れる。The produced white crystals are filtered under suction, washed with ethanol, and then immersed in 100 ml of ethanol. 0.
After 5 days, the mixture is filtered under suction and washed with ethanol to obtain white crystals 47 of 5-benzyl-5-ureidohydantoin.
この化合物は下記の性質を有する。融点：２１４℃（分
解）
元素分析：
赤外線吸収スペクトル：
第１図に示すとおりで、ヒダン
ンゼン核の存在が認められた。This compound has the following properties. Melting point: 214°C (decomposition) Elemental analysis: Infrared absorption spectrum: As shown in Figure 1, the presence of hydanzene nuclei was observed.
聰スペクトル（溶媒ＩＳＯ
ＴＭＳ）
トーン核及びべ
ｄぃ基準物質
溶解性：
水に難溶で、有機溶媒にはほとんど不溶であるが、ジメ
チルスルホキシド及びジメチルホルムアミドには若干溶
解する。Solubility spectrum (solvent ISO TMS) Tone nucleus and solid standard substance solubility: Slightly soluble in water, almost insoluble in organic solvents, but slightly soluble in dimethyl sulfoxide and dimethyl formamide.
第１図は、本発明の化合物の赤外線吸収スペクトル図で
ある。FIG. 1 is an infrared absorption spectrum diagram of the compound of the present invention.
Claims (1)
せることを特徴とする、次式▲数式、化学式、表等があ
ります▼ で表わされるヒダントイン誘導体の製法。[Claims] A hydantoin derivative represented by a primary formula ▲ Numerical formula, chemical formula, table, etc. ▼. A method for producing a hydantoin derivative represented by the following formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, which is characterized by reacting a compound represented by the secondary formula C_6H_5-CH_2-COCOOH with urea in the presence of a dehydrating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP880377A JPS5935398B2 (en) | 1977-01-31 | 1977-01-31 | Novel hydantoin derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP880377A JPS5935398B2 (en) | 1977-01-31 | 1977-01-31 | Novel hydantoin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5395972A JPS5395972A (en) | 1978-08-22 |
| JPS5935398B2 true JPS5935398B2 (en) | 1984-08-28 |
Family
ID=11702999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP880377A Expired JPS5935398B2 (en) | 1977-01-31 | 1977-01-31 | Novel hydantoin derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5935398B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6036463A (en) * | 1983-08-08 | 1985-02-25 | Grelan Pharmaceut Co Ltd | Allantoin derivative |
-
1977
- 1977-01-31 JP JP880377A patent/JPS5935398B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5395972A (en) | 1978-08-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Stewart | The chemistry of the sydnones | |
| ATE46164T1 (en) | 1,4:3,6-DIANHYDRO-HEXITOL DERIVATIVES, PROCESSES FOR THEIR PRODUCTION AND THEIR USE AS MEDICINES. | |
| DK149025B (en) | ANALOGY PROCEDURE FOR PREPARING WATER SOLUBLE SALTS OF N- (2-PYRIDYL) -2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE-1,1-DIOXIDE | |
| SE7609986L (en) | N-ALKYLDIPHENYLAMINE DERIVATIVES WITH RODENTICID EFFICIENCY, COMPOSITIONS CONTAINING THE SAME, AND THEIR USE FOR CONTROLING RATS AND MOSS | |
| CH612431A5 (en) | Process for the preparation of novel indole derivatives | |
| ATE118217T1 (en) | SODIUM N-ACETYLNEURAMINATE TRIHYDRATE AND METHOD FOR THE PRODUCTION THEREOF. | |
| JPS5935398B2 (en) | Novel hydantoin derivatives | |
| JPS6440467A (en) | Novel substituted diphenylimidazole derivative | |
| ES403486A1 (en) | Procedure for the preparation of piperazine derivatives. (Machine-translation by Google Translate, not legally binding) | |
| US3895022A (en) | Anti-inflammatory agents, cosmetic preparations and method of preventing inflammation | |
| Youinou et al. | Copper complexes of a flexible binucleating ligand. Syntheses and spectroscopic, thermodynamic, and kinetic studies | |
| EP0008950A3 (en) | Pyrimido(1,6-a)indole derivatives and intermediates therefor, processes for their preparation, pharmaceutical compositions containing the derivatives and their use | |
| DE2521347B2 (en) | Hydroxyl-substituted 2-chloro-a - (tert-butylaminomethyl-benzyl alcohols, manufacturing processes and pharmaceuticals | |
| SE8300432D0 (en) | REACTIVE CINNIC ACID DERIVATIVES FOR THE PREPARATION OF BIOLOGICALLY ACTIVE AMIDES | |
| JPH0459874A (en) | Polymethyne compound | |
| JPS58124766A (en) | Sulfamoylbenzoic acid derivative and curative composition containing the same as active ingredient | |
| Manogaran et al. | 1H and 13C NMR and infrared spectroscopic study of the conformational equilibria in S-methyl dithiocarbazate | |
| Johnson et al. | Synthesis of substituted 2-aminopyrrole analogs of lidocaine I | |
| FR2451365A1 (en) | ISOINDOLINE DERIVATIVE, PROCESS FOR ITS PREPARATION AND THERAPEUTIC COMPOSITIONS CONTAINING THE SAME AS ACTIVE INGREDIENT | |
| JPS62201967A (en) | Diarylmethane compounds | |
| SU694495A1 (en) | 1 -adamantylammonium beta -chloroethyloxaminate exhibiting anticholinergic activity | |
| Barrett et al. | The circular dichroism of N-thiobenzoyl-L-α-amino-acids. Part VI. Assessment of the resolution of amino-acids as their N-thiobenzoyl derivatives | |
| JPS572271A (en) | Preparation of 2-aminoindolenine derivative | |
| JPS55139346A (en) | Preparation of bis(8-guanidinooctyl)amine acetic acid salt | |
| JPS5955874A (en) | Novel hydrantoin derivative |