214557-84-3

Upstream product

• 214557-86-5 methyl 3,5-difluoro-7-hydroxyadamantane-1-carboxylate 
• 711-01-3 methyl adamantane-1-carboxylate 
• 68435-07-4 1-methoxycarbonyl-3-hydroxyadamantane 
• 214557-80-9 methyl 3-fluoro-5-hydroxyadamantane-1-carboxylate 
• 214557-81-0 methyl 3,5-difluoroadamantane-1-carboxylate 
• 1426-93-3 methyl 3-fluoroadamantane-1-carboxylate 

Downstream Products

• 214557-89-8 3,5,7-trifluoroadamantane-1-carboxylic acid 
• 214557-91-2 benzyl 3,5,7-trifluoroadamantane-1-carbamate 

Relevant academic research and scientific papers

Selective introduction of fluorine atoms to the tert-carbons of functionalized adamantanes by BrF3

The direct fluorination reaction of the functionalized adamantanes was achieved by using BrF3. In the reaction with methyl adamantane-1-caroxylate 1 and dimethyl adamantane-1,3-dicarboxylate 3, three and two fluorine atoms, respectively, were i

ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS

The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.

Pharmacological Evaluation of Novel Bioisosteres of an Adamantanyl Benzamide P2X7 Receptor Antagonist

Adamantanyl benzamide 1 was identified as a potent P2X7R antagonist but failed to progress further due to poor metabolic stability. We describe the synthesis and SAR of a series of bioisosteres of benzamide 1 to explore improvements in the pharmacological properties of this lead. Initial efforts investigated a series of heteroaromatic bioisosteres, which demonstrated improved physicochemical properties but reduced P2X7R antagonism. Installation of bioisosteric fluorine on the adamantane bridgeheads was well tolerated and led to a series of bioisosteres with improved physicochemical properties and metabolic stability. Trifluorinated benzamide 34 demonstrated optimal physicochemical parameters, superior metabolic stability (ten times longer than lead benzamide 1), and an improved physicokinetic profile and proved effective in the presence of several known P2X7R polymorphisms.

Electrochemical synthesis of methyl-3,5,7-trifluoroadamantane-1-carboxylate under recycling use of ionic liquid media

Methyl-3,5,7-trifluoroadamantane-1-carboxylate, a key intermediate for the synthesis of 1-amino-3,5,7-trifluoroadamantane (trifluoroamantadine), was synthesized by the electrochemical fluorination of methyl adamantane-1- caroxylate in pyridine-5HF under constant current conditions. After the reaction, the product was extracted from pyridine-5HF by hexane-CH 2Cl2, and recovered pyridine-5HF was used repeatedly.

Selective fluorination of adamantanes by an electrochemical method

(Chemical Equation Presented) Selective fluorination of adamantanes was achieved by the electrochemical fluorination method, using Et3N-5HF as electrolyte and a fluorine source. Mono-, di-, tri-, and tetrafluoroadamantanes were selectively prepared from adamantanes by controlling the oxidation potential, and the fluorine atoms were introduced selectively at the tertiary carbons. Adamantanes that have functional groups such as ester, cyano, and acetoxymethyl were also fluorinated selectively.

Fluoro-substituted adamantane derivatives

The invention relates to fluoro-substituted adamantane derivatives of the formula and to pharmaceutically acceptable salts thereof, wherein R1, R2, R3, and R4 are as defined herein. The invention also relates to methods of treating neurological disorders, such as memory loss and Parkinson's disease, and bacterial and viral infections, through administration of a therapeutically effective amount of a compound of formula I. The invention also relates to a method of increasing the metabolic stability of an adamantane-containing pharmaceutical compound by incorporating a fluoro substituent on at least one bridge-head carbon of the adamantyl group of said adamantane-containing pharmaceutical compound

Preparation of fluoroadamantane acids and amines: Impact of bridgehead fluorine substitution on the solution- and solid-state properties of functionalized adamantanes

Functionalized adamantanes are utilized as medicinal therapeutics and a practical route to novel bridgehead fluorinated adamantylamines and acids including fully fluorinated 3,5,7-tri-fluoroadamantane-1-carboxylic acid 1 and 3,5,7-trifluoroadamantane-1-am

Fluoro-substituted adamantane derivatives

The invention relates to fluoro-substituted adamantane derivatives of the formula and to pharmaceutically acceptable salts thereof, wherein R1, R2, R3, and R4are as defined herein. The invention also relates to methods of treating neurological disorders, such as memory loss and Parkinson's disease, and bacterial and viral infections, through administration of a therapeutically effective amount of a compound of formula I. The invention also relates to a method of increasing the metabolic stability of an adamantane-containing pharmaceutical compound by incorporating a fluoro substituent on at least one bridge-head carbon of the adamantyl group of said adamantane-containing pharmaceutical compound.