1306763-71-2

Basic information

• Product Name: (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate
• Synonyms: (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate;(S)-tert-butyl (4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate;tert-butyl (S)-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate
• CAS NO: 1306763-71-2
• Molecular Formula: C23H22N4O3
• Molecular Weight: 402.44578
• EINECS: -0
• Mol File: 1306763-71-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate(1306763-71-2)
• EPA Substance Registry System: (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate(1306763-71-2)

Safety Data

• Hazardous Substances Data: 1306763-71-2(Hazardous Substances Data)

Usage

General Description

This chemical, also known as BI 99179, is a potent and selective phosphodiesterase 9A (PDE9A) inhibitor. PDE9A is an enzyme that plays a role in the regulation of cellular signaling pathways in the brain, and inhibition of this enzyme has been suggested as a potential treatment for cognitive impairments associated with neurodegenerative diseases such as Alzheimer's. The compound specifically targets PDE9A and has shown promising results in preclinical studies as a potential therapeutic agent for cognitive dysfunction. Its structure includes a carbamate group and an oxadiazole ring, which are important for its PDE9A inhibitory activity. (R)-tert-butyl (4-(5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate holds potential for the development of novel treatments for cognitive impairment and neurodegenerative diseases.

Upstream product

• 1306763-28-9 (R)-N-((R)-4-cyano-2,3-dihydro-1H-inden-1-yl)-2-methylpropane-2-sulfinamide 
• 1306763-29-0 (R)-(1-amino-2,3-dihydro-1H-indene-1-yl)-4-carbonitrile hydrochloride 
• 60899-34-5 4-cyano-2,3-dihydro-1H-inden-1-one 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 
• 1306763-27-8 (R)-N-(4-cyano-2,3-dihydro-1H-indene-1-ylidene)-2-methylpropane-2-sulfinamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1306763-24-5 (R)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile 
• 1306763-32-5 (R)-tert-butyl 4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-ylcarbamate 
• 1306763-30-3 (R)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate 

Relevant articles and documents

Enantioselective Synthesis of Ozanimod, the Active Pharmaceutical Ingredient of a New Drug for Multiple Sclerosis

We report here a short enantioselective synthesis of Ozanimod, a potent modulator of the enzyme Sphingosine-1-phosphate receptor (S1PR), recently approved by FDA and EMA for the treatment of relapsing-remitting multiple sclerosis. Amongst different synthetic approaches explored, we achieved the best result introducing the stereogenic centre in the last step through imine asymmetric transfer hydrogenation (ATH) using Wills’ catalysts. Besides the reduced numbers of enantiomeric purity controls required, this process culminates in an exceptionally high enantioselective reductive amination obtained with commercially available tethered Ru catalysts. Starting from commercially available 4-cyano-indanone, enantiomerically pure Ozanimod was obtained in 5 steps in 62 % overall yield and 99 % ee.

SELECTIVE SPHINGOSINE 1 PHOSPHATE RECEPTOR MODULATORS AND COMBINATION THERAPY THEREWITH

Compounds that selectively modulate the sphingosine 1 phosphate receptor are provided, including compounds which modulate subtype 1 of the S1P receptor, and methods of their therapeutic and/or prophylactic use in combination with at least one other medicament adapted for treatement of a malcondition for which activation of S1P1 is medically indicated, such as multiple sclerosis.