500556-90-1

Basic information

• Synonyms: tert-butyl (1R,3R,4S)-3-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate;ert-butyl (1R,3R,4S)-3-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate;(1S,2R,4R)-tert-butyl 2-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate;tert-butyl (1S,2R,4R)-2-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate
• CAS NO: 500556-90-1
• Molecular Formula: C₁₁H₂₀N₂O₂
• Molecular Weight: 212.2887
• EINECS: -0
• Mol File: 500556-90-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N/A(CAS DataBase Reference)
• NIST Chemistry Reference: N/A(500556-90-1)
• EPA Substance Registry System: N/A(500556-90-1)

Safety Data

• Hazardous Substances Data: 500556-90-1(Hazardous Substances Data)

Upstream product

• 500556-94-5 exo-tert-butyl (1S,2R,4R)-(+)-2{[(benzyloxy)carbonyl]amino}-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 500556-94-5 exo-tert-butyl (1S,2R,4R)-(+)-2-{[(benzyloxy)carbonyl]amino}-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 1221818-81-0 (1S,2R,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 
• 1250884-79-7 tert-butyl exo-2-{[(benzyloxy)carbonyl]amino}-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 500556-94-5 tert-butyl (1S,2R,4R)-2-{[(benzyloxy)carbonyl]amino}-7-azabicyclo[2.2.1]heptane-7-carboxylate 

Downstream Products

• 139120-69-7 5-(4-chlorophenylsulfanyl)-thiophene-2-carboxaldehyde 

Relevant articles and documents

Substituted Azabicyclo[2.2.1]heptanes as Selective Orexin-1 Antagonists: Discovery of JNJ-54717793

The orexin system consists of two neuropeptides (orexin-A and orexin-B) that exert their mode of action on two receptors (orexin-1 and orexin-2). While the role of the orexin-2 receptor is established as an important modulator of sleep wake states, the role of the orexin-1 receptor is believed to play a role in addiction, panic, or anxiety. In this manuscript, we describe the optimization of a nonselective substituted azabicyclo[2.2.1]heptane dual orexin receptor antagonist (DORA) into orally bioavailable, brain penetrating, selective orexin-1 receptor (OX1R) antagonists. This resulted in the discovery of our first candidate for clinical development, JNJ-54717793.

Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists

A novel set of azabicyclic aryl amides have been identified as potent and selective agonists of the α7 nAChR. A two-pronged approach was taken to improve the potential hERG liability of previously disclosed α7 nAChR agonist, PNU-282,987, while maintaining the compound's other desirable pharmacological properties. The first approach involved further exploration of the aryl carboxylic acid fragment of PNU-282,987, while the second approach focused on modification of the azabicyclic amine portion of PNU-282,987. The best compounds from each series are characterized by rapid brain penetration, good oral bioavailability in rat, and demonstrate in vivo efficacy in a rat P50 auditory sensory gating assay. At least one analog from each series (1h, 1o, 2a, 9a, and 18a) shows an improved hERG safety profile over PNU-282,987.

COMPOUNDS HAVING BOTH α7 NICOTINIC AGONIST ACTIVITY AND 5HT3 ANTAGONIST ACTIVITY FOR TREATMENT OF CNS DISEASES

The invention discloses compounds that are selective α7 nAChR agonists and 5-HT3 antagonists. The compounds are useful for treating many CNS diseases.