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

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 AS RADIOLIGANDS FOR THE DIAGNOSIS OF DISEASE

Radiolabeled ligands useful as probes for determining the relative abundance, receptor occupancy, and/or function of nicotinic acetylcholine receptors. The compounds of Formula I as described herein are labeled with a radioactive isotopic moiety such as 11C, 18F, 76Br, 123I or 125I. Disorders are diagnosed by administering to a mammal a detectably labeled compound and detecting the binding of that compound to the nAChR. The compounds that have been administered are detected using methods including, but not limited to, position emission topography and single-photon to emission computed tomography. The present invention is useful in diagnosing a wide variety of diseases and disorders as discussed herein.