201987-81-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Bromobenzyl)hydantoin is utilized as an intermediate in the production of pharmaceuticals, specifically for the synthesis of antiepileptic drugs. Its unique chemical structure allows it to be a key component in the development of medications that help manage and treat epilepsy.
Used in Organic Synthesis:
1-(4-BroMobenzyl)hydantoin also serves as a reagent in organic synthesis, a field that involves the chemical reactions intended to convert organic compounds from one form to another. Its properties make it suitable for use in creating a variety of organic compounds for different applications.
Used in Chemical Manufacturing:
1-(4-Bromobenzyl)hydantoin is further employed in the manufacturing of other chemicals, contributing to the development of new products and enhancing existing ones. Its versatility in chemical processes highlights its importance in the broader chemical industry.
It is important to handle 1-(4-Bromobenzyl)hydantoin with care due to its potential health hazards and environmental impacts. Proper safety measures should be taken to minimize risks during its production, use, and disposal.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 850859-09-5 2-(4-bromobenzylamino)acetamide 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1228660-43-2 1-(4-bromobenzyl)-3-propylimidazolidine-2,4-dione 
• 1228660-41-0 1-(4-bromobenzyl)-3-methylimidazolidine-2,4-dione 
• 1228660-45-4 1-(4-Bromo-benzyl)-3-(2-methoxyethyl)imidazolidine-2,4-dione 
• 1228594-59-9 1-(4-bromobenzyl)-3-isobutylimidazolidine-2,4-dione 
• 1228660-42-1 1-(4-bromobenzyl)-3-ethylimidazolidine-2,4-dione 
• 1228594-48-6 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione 
• 1338056-02-2 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-isobutylimidazolidine-2,4-dione 
• 1228659-57-1 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-propylimidazolidine-2,4-dione 
• 1228659-71-9 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-(2-methoxy-ethyl)imidazolidine-2,4-dione 
• 1228659-50-4 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-methylimidazolidine-2,4-dione 

Relevant academic research and scientific papers

Structure-kinetic relationship studies of cannabinoid CB2 receptor agonists reveal substituent-specific lipophilic effects on residence time

A decade ago, the drug-target residence time model has been (re-)introduced, which describes the importance of binding kinetics of ligands on their protein targets. Since then, it has been applied successfully for multiple protein targets, including GPCRs, for the development of lead compounds with slow dissociation kinetics (i.e. long target residence time) to increase in vivo efficacy or with short residence time to prevent on-target associated side effects. To date, this model has not been applied in the design and pharmacological evaluation of novel selective ligands for the cannabinoid CB2 receptor (CB2R), a GPCR with therapeutic potential in the treatment of tissue injury and inflammatory diseases. Here, we have investigated the relationships between physicochemical properties, binding kinetics and functional activity in two different signal transduction pathways, G protein activation and β-arrestin recruitment. We synthesized 24 analogues of 3-cyclopropyl-1-(4-(6-((1,1-dioxidothiomorpholino)methyl)-5-fluoropyridin-2-yl)benzyl)imidazoleidine-2,4-dione (LEI101), our previously reported in vivo active and CB2R-selective agonist, with varying basicity and lipophilicity. We identified a positive correlation between target residence time and functional potency due to an increase in lipophilicity on the alkyl substituents, which was not the case for the amine substituents. Basicity of the agonists did not show a relationship with affinity, residence time or functional activity. Our findings provide important insights about the effects of physicochemical properties of the specific substituents of this scaffold on the binding kinetics of agonists and their CB2R pharmacology. This work therefore shows how CB2R agonists can be designed to have optimal kinetic profiles, which could aid the lead optimization process in drug discovery for the study or treatment of inflammatory diseases.

HETEROCYCLIC DERIVATIVES

The present invention relates to a heterocyclic derivative of formula (I) wherein the variables are as defined in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention further relates to pharmaceutical compositions comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of disorders mediated by glutamate dysfunction, such as schizophrenia and generalised anxiety disorder.

Discovery and optimization of 1-(4-(Pyridin-2-yl)benzyl)imidazolidine-2,4- dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists

Here, we report the identification and optimization of 1-(4-(pyridin-2-yl) benzyl)imidazolidine-2,4-dione derivatives as a novel chemotype with selective cannabinoid CB2 receptor agonist activity. 1 is a potent and selective cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.6). The compound was found to be metabolically unstable, which resulted in low oral bioavailability in rat (Fpo = 4%) and possessed off-target activity at the hERG ion channel (pKi = 5.5). Systematic modification of physicochemical properties, such as lipophilicity and basicity, was used to optimize the pharmacokinetic profile and hERG affinity of this novel class of cannabinoid CB2 receptor agonists. This led to the identification of 44 as a potent, selective, and orally bioavailable cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.0; hERG pKi po = 100%), which was active in a rat spinal nerve ligation model of neuropathic pain.

1-(4-(PYRIDIN-2-YL)BENZYL)IMIDAZOLIDINE-2,4-DIONE DERIVATIVES

The invention relates to 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivative having the general Formula I wherein R1 is H, (C1-6)alkyl (optionally substituted with oxo, (C1-3)alkyloxy, (C1-3)alkyloxycar

1-(BIPHENYL-4-YLMETHYL)IMIDAZOLIDINE-2,4-DIONE

The invention relates to A 1-(biphenyl-4-ylmethyl)imidazolidine-2,4-dione derivative having the general Formula I wherein R1 is H, (C1-6)alkyl (optionally substituted with oxo, OR4, COOR5, halogen or CN), (C2-6)alkenyl, (C2-6)alkynyl, (C3-6)cycloalkyl or (C3-6)cycloalkyl(C1-3)alkyl; R2 and R2′ are independently H or (C1-3)alkyl; or R2 and R2′ form together with the carbon atom to which they are bound a (C3-5)cycloalkyl group; R3 represents H or 1 to 4 F substituents; Y represents or NR8R9; X represents CHR6, CF2, O, S, SO or SO2; R4 and R5 are (C1-6)alkyl; R6 is H, OR7 or CN; R7 is (C1-3)alkyl; R8 is (C5-7)cycloalkyl comprising a heteroatom selected from O, S, SO and SO2; R9 is H or (C1-4)alkyl; o and m represent the ortho or meta position of the substituent Y—CH2; or a pharmaceutically acceptable salt thereof; as well as to the use of said 1-(biphenyl-4-ylmethyl)imidazolidine-2,4-dione derivatives in the treatment of pain such as for example peri-operative pain, chronic pain, neuropathic pain, cancer pain and pain and spasticity associated with multiple sclerosis.

Process for producing 1-substituted-hydantoins

The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: STR1 wherein R1 represents d hydrocarbon group which may be substituted and others, cheracterized by reacting N-sustituted-N-alkcycarbonylamnilo-acetonitrile of Formula II: STR2 wherein R2 represents an alkyl group and others, with an alkali metal hydroxides or the like and then treating with an acid.

Process for producing 1-substituted-hydantoins

The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: wherein R1represents a hydrocarbon group which may be substituted and others,characterized by reacting N-substituted-N-alkoxycarbonylamino-acetonitrile of Formula II: wherein R2represents an alkyl group and others,with an alkali metal hydroxides or the like and then treating with an acid.