680974-15-6

Usage

Chemical Class

Imidazolidinedione derivatives

Molecular Weight

117.10 g/mol

Stereochemistry

(5S)-(9CI)

Chirality

Chiral compound

Potential Applications

Pharmaceuticals and agrochemicals

Importance

Unique structure and properties require further study for potential applications.

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 598-50-5 N-Methylurea 
• 680974-14-5 (5S,1'R)-1'-methyl-5-(1'-phenylethoxy)hydantoin 
• 680974-12-3 (5S,1'S)-1-methyl-5-(1'-phenylethoxy) hydantoin 
• 680976-39-0 (5R,1'R)-1-methyl-5-(1'-phenylethoxy)hydantoin 
• 680976-43-6 (5R,1'S)-1-methyl-5-(1'-phenylethoxy)hydantoin 
• 113259-78-2 5-Bromo-1-methyl-imidazolidine-2,4-dione 
• 298-12-4 Glyoxilic acid 
• 563-96-2 2,2-dihydroxyacetic acid 
• 122641-44-5 5-acetoxy-1-methylimidazolidine-2,4-dione 
• 615-77-0 1-methyluracil 

Relevant academic research and scientific papers

Optically active (S)-hydantoin derivative

(S)-(?)-5-hydroxy-1-methylhydantoin is useful as a drug having high safety. Since the compound of the present invention, (S)-(?)-5-hydroxy-1-methylhydantoin, rarely changes to the metabolite having high toxicity compared with the R-form and the racemate,

Optically active (R)-hydantoin derivative

(R)-(+)-5-hydroxy-1-methylhydantoin is an optically active substance having an excellent suppressive action of the progression of renal failure. At an administration to a model animal of renal failure, (R)-(+)-5-hydroxy-1-methylhydantoin significantly sup

NOVEL CRYSTAL FORM OF 5-HYDROXY-1-METHYLHYDANTOIN

Conventional I-form crystals of 5-hydroxy-1-methylhydantoin contain, remaining therein in a considerable amount, the organic solvent used in a purification step. In contrast, in II-form crystals, the amount of the organic solvent remaining therein is smaller than the detection limit. Namely, the II-form crystals contain substantially no residual organic solvent. The novel II-form crystals of 5-hydroxy-1-methylhydantoin obtained through recrystallization from water not only contain substantially no residual organic solvent, but also have a high bulk density and are hence advantageous for pharmaceutical preparation. They further have properties advantageous for production, such as low adhesion. The crystals are significantly useful as a material for medicines required to have high safety, such as drugs for renal insufficiency.

Process for preparing 1-substituted 5-hydroxy-imidazoline-2,4-diones and 1-substituted 5-alkoxy-imidazoline-2,4-diones

A process for preparing specific 1-substituted 5-hydroxy-imidazoline-2,4-diones by reacting glyoxylic acid with N-substituted ureas is provided, where this process is carried out in a 10-80% strength aqueous solution and in the presence of an acid catalyst. The 1-substituted 5-hydroxy-imidazoline-2,4-diones can subsequently be converted in a further reaction step to give 1-substituted 5-alkoxy-imidazoline-2,4-diones.

The Stepwise Mammalian Oxidation of the Hydantoin 1-Methylimidazolidine-2,4-dione into Methylimidazolidinetrione via 5-Hydroxy-1-methyl-imidazolidine-2,4-dione

The metabolism of 1-methylhydantoin (2) is described.The major and general metabolic route in mammals, represented by formulae (2) to (7), includes two consecutive stepwise oxidations giving 5-hydroxy-1-methylhydantoin (3) and thence 1-methylparabanic acid (4).Since the first oxidation proved to be stereoselective, the step was thought to be enzymatic.Although enantiomeric products (3a) and (3b) (ca. 3:1) could not be separated directly, the mixture was converted into (S)- and (R)-5-(N-benzyloxycarbonyl-L-prolyloxy)-1-methylhydantoins (13a) and (13b) which proved separable and were identified by X-ray analysis of the (R)-diastereoisomer.The regioselective ring-fission of the second product (4) into the methyloxaluric acid (5) is discussed.Two minor oxidative routes from the substrate (2) into sarcosine (9) and parabanic acid (10) were also shown to exist.

Ozonolysis of Uracils in Water

The ozonolysis of uracils unsubstituted at the 1-position gave new 1-acyl-5-hydroxyhydantoins and 5-hydroxyhydantoins in water, while that of 1-substituted uracils gave the corresponding 5-hydroxyhydantoins in low yields.The structure of 1-acetyl-5-hydroxy-5-methylhydantoin was determined by X-ray crystallography.

Hypoglycemic hydantoin derivatives

The present invention relates to novel hydantoin derivatives represented by the general formula (I) and pharmaceutical compositions containing them as an active ingredient. STR1 In the formula (I), X is hydrogen or a group having the formula --OR 4, and each of R 1, R 2, R 3 and R 4, which may be the same or different, is hydrogen, an alkyl group or a cycloalkyl group.Hydantoin derivatives and pharmaceutically acceptable salts thereof of the present invention have excellent hypoglycemic, hypolipidemic and diuretic effects, as well as low toxicity and great safety. Therefore, the compounds of the present invention are not only useful as antidiabetics but also as drugs for hyperlipidemia.