69684-83-9

Usage

Uses

Used in Pharmaceutical Industry:
6-FLUORO-4-CHROMANONE HYDANTOIN is used as a potential anticonvulsant agent for the treatment of epilepsy and other neurological disorders. Its ability to modulate the activity of ion channels in the brain makes it a promising candidate for further research and development in this area.
Used in Medicinal Chemistry Research:
6-FLUORO-4-CHROMANONE HYDANTOIN serves as a valuable compound for medicinal chemistry research, aiding in the exploration of new drug development pathways and the understanding of its pharmacological effects. More research is needed to fully comprehend its potential applications and therapeutic benefits.

Upstream product

• 151-50-8 potassium cyanide 
• 66892-34-0 6-fluoro-4-chromanone 
• 371-41-5 4-Fluorophenol 
• 103834-11-3 (S)-4-amino-6-fluoro-chromane-4-carboxylic acid 
• 79791-46-1 (S)-4-cyano-2,3-dihydro-6-fluoro-4-<(S)-(1-phenylethyl)amino>-4H-1-benzopyran 
• 79791-44-9 (S)-2,3-dihydro-6-fluoro-4-<(1-phenylethyl)imino>-4H-1-benzopyran 
• 82799-12-0 (S)-1'-chloro-6-fluoro-2,3-dihydro-5'-imino-3'-<(S)-1-phenylethyl>spiro<4H-1-benzopyran-4,4'-imidazolidin>-2'-one hydrochloride 
• 103197-13-3 (S)-methyl 4-amino-6-fluorochroman-4-carboxylate 
• 103197-09-7 4-amino-2,3-dihydro-6-fluoro-4H-1-benzopyran-4-carboxylic acid, hydrochloride 
• 103197-05-3 N-acetyl-2-(2-bromoethoxy)-5-fluorophenylglycine 
• 103197-08-6 4-acetamido-2,3-dihydro-6-fluoro-4H-1-benzopyran-4-carboxylic acid 
• 103196-96-9 C₁₂H₁₀FNO₃ 
• 332-48-9 2-(4-fluorophenoxy)-ethylbromide 
• 85169-02-4 3-(4-fluoro-phenoxy)propionitrile 

Downstream Products

• 66892-34-0 6-fluoro-4-chromanone 
• 90477-45-5 6-fluoro-4-iminochlorochromane 
• 67146-05-8 sorbinil 
• 90477-46-6 (RS)-4-amino-6-fluorochroman-4-carboxylic acid 
• 99599-58-3 6-fluoro-1'-[3-(4-phenylpiperidino)propyl]spiro[chroman-4,4'-imidazolidine]-2',5'-dione 

Relevant academic research and scientific papers

USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS

The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula

General and practical catalytic enantioselective Strecker reaction of ketoimines: Significant improvement through catalyst tuning by protic additives

Significant improvement in enantioselectivity and catalyst activity was achieved for the catalytic enantioselective Strecker reaction. Using a catalyst (1-2.5mol%) prepared from Gd(OiPr)3 and D-glucose derived ligand 1, and in the pr

Lipase-catalyzed resolution of 5,5-disubstituted hydantoins

Chiral non-racemic 5,5-disubstituted hydantoins were prepared by lipase-catalyzed enantioselective hydrolyses of their N-acyloxymethyl groups or esterification of their N-hydroxymethyl groups.

Novel resolution process for racemic spiro-hydantoins

A novel three-step process for resolving a racemic spiro-hydantoin compound into its optical antipodes is disclosed, which involves (1) reacting said racemic compound with an optically-active asymmetric isocyanate of the formula RNCO, wherein R is (S)- or (R)-1-phenylethyl or (S) or (R)-1-(1-naphthyl)ethyl, to form the corresponding diastereomeric uredio compound; (2) separating the resulting diastereomeric mixture into its component parts, and (3) thereafter converting the separated ureido diastereomers obtained in step (b) to the corresponding asymmetric hydantoin compounds by treatment with an alkali metal lower alkoxide (C1 -C4), followed by acidification, whereupon the desired optical isomer is obtained. The final products so obtained, such as (4S)-(+)-6-fluoro-2,3-dihydro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2', 5'-dione (sorbinil) and (5'S)-3'-chloro-5', 6', 7', 8'-tetra-hydro-spiro[imidazolidine-4,5'-quinoline]-2,5-dione, are known to be useful in preventing or alleviating certain chronic diabetic complications. The aforementioned diastereomeric uredio intermediates are novel compounds.

Process for the production of asymmetric hydantoins

An improved process for preparing (4S)-6-fluorospiro-[chroman-4,4''-imidazolidine]-2'',5''-dione (sorbinil) or its (2R)-methyl derivative (2-methylsorbinil) is disclosed herein, starting from p-fluorophenol in each instance. The final products obtained ha

Spiro hydantoin aldose reductase inhibitors

Sorbitol formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoin derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of streptozotocinized rats. Optimum in vivo activity is reached in spiro hydantoins derived from 6-halogenated 2,3-dihydro-4H-1-benzopyran-4-ones (4-chromanones). In 2,4-dihydro-6-fluorospirol[4H-1-benzopyran-4,4'-imidazolidine]-2',5'- ione, the activity resides exclusively in the 4S isomer, compound 115 (CP-45,634, USAN: sorbinil). This compound is currently being used to test, in humans, the value of aldose reductase inhibitors in the therapy of diabetic complications.

Substituted spiro-2',4'-diones as aldose reductase inhibitors

Aldose reductase (EC 1.1.1.21) is believed to be involved in the pathogenesis of diabetic complications.Inhibitors of this enzyme could be useful for the treatment of diabetic cataracts and neuropathies.A series of spiro-2',4'-d

S-6-fluoro-4-aminochroman-4-carboxylic acid derivatives useful as intermediates for sorbinil

Chiral sorbinil intermediates of the formula STR1 wherein R is hydrogen or benzyloxycarbonyl and Y is hydroxy or amino, processes therefor, and processes for the conversion thereof to sorbinil.

Regeneration of 6-fluoro-4-chromanone from 6-fluoro-4-ureidochroman-4-carboxylic acid

6-Fluoro-4-chromanone can be regenerated from (R)-6-fluoro-4-ureidochroman-4-carboxylic acid, or from mixtures of (R)-6-fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification, by oxidation with a permanganate, especially potassium permanganate. 6-Fluoro-4-chromanone is a chemical intermediate useful for preparing sorbinil, an aldose reductase inhibitor which can be used in clinical medicine for the control of the chronic complications of diabetes. (R)-6-Fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification are by-products from the production of sorbinil from 6-fluoro-4-chromanone.