6038-49-9

Usage

Uses

Used in Pharmaceutical Industry:
9beta-(4-Chlorophenyl)-1,2,3,9beta-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one is used as an active pharmaceutical ingredient for the development of imidazoisoindole-based antiviral agents. It is specifically designed for the treatment of respiratory syncytial virus (RSV) infections, targeting the virus's replication process and alleviating symptoms associated with the infection.

Upstream product

• 107-15-3 ethylenediamine 
• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 

Downstream Products

• 477886-50-3 9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one 
• 22590-16-5 9b-(4-chloro-phenyl)-1-(toluene-4-sulfonyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one 
• 477886-54-7 C₂₄H₁₉ClN₂O₃ 
• 22232-71-9 Mazindol 
• 23864-93-9 4'-chloro-2-(imidazolin-2-yl)benzophenone hydrochloride 
• 477886-49-0 C₂₄H₁₉ClN₂O₂ 

Relevant academic research and scientific papers

The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1

Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R1) and benzoyl (R2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and log D) and excellent rat pharmacokinetics (e.g., rat oral bioavailability of 89% for compound 17).

Further optimization of the M5 NAM MLPCN probe ML375: Tactics and challenges

This Letter describes the continued optimization of the MLPCN probe ML375, a highly selective M5 negative allosteric modulator (NAM), through a combination of matrix libraries and iterative parallel synthesis. True to certain allosteric ligands, SAR was shallow, and the matrix library approach highlighted the challenges with M5 NAM SAR within in this chemotype. Once again, enantiospecific activity was noted, and potency at rat and human M5 were improved over ML375, along with slight enhancement in physiochemical properties, certain in vitro DMPK parameters and CNS distribution. Attempts to further enhance pharmacokinetics with deuterium incorporation afforded mixed results, but pretreatment with a pan-P450 inhibitor (1-aminobenzotriazole; ABT) provided increased plasma exposure.

Discovery of the first M5-selective and CNS penetrant negative allosteric modulator (NAM) of a muscarinic acetylcholine receptor: (S)-9b-(4-chlorophenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydro-1 H -imidazo[2,1- a ]isoindol-5(9b H)-one (ML375)

A functional high throughput screen and subsequent multidimensional, iterative parallel synthesis effort identified the first muscarinic acetylcholine receptor (mAChR) negative allosteric modulator (NAM) selective for the M5 subtype. ML375 is a

POLYCYCLIC AGENTS FOR THE TREATMENT OF RESPIRATORY SYNCYTIAL VIRUS INFECTIONS

Compounds of formula (I), and their use as in the treatment of infections involving viruses of the Pneumovirinae sub-family (RSV) are disclosed. In the formula ring (A) may be phenyl, pyridyl etc., (B-C) may be CH2-CH2etc., (R1) may be phenyl and substituted forms thereof, (R2) may be assorted substituents.

Polycyclic amino derivatives of pyrrolidone and piperidone

A series of compounds of the formula STR1 have been found to exhibit useful pharmacological properties, e.g. antiinflammatory and analgetic activity.

5H-imidazo[2,1-a]isoindol-5-one compounds

A new class of chemical compounds whose members exert an appetite suppressant and mood elevating effect in man has been invented. This class is defined as being composed of those compounds having the 1-substituted-2,5-benzodiazocine structure, fully saturated in the nonbenzenoid portion, and whose nitrogens are tervalent. Members of this class are prepared by condensing an orthobenzoylbenzoic acid or ester thereof with an ethylenediamine and reducing with a metallic alkaline hydride the product thus obtained.