246510-69-0

Usage

Uses

Used in Organic Synthesis:
(3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE is used as a building block for creating complex molecules with specific stereochemical arrangements. Its unique structure allows for the synthesis of a variety of compounds with tailored properties.
Used in Asymmetric Catalysis:
In the field of catalysis, (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE serves as a chiral ligand, playing a crucial role in asymmetric catalysis. This application is vital for the production of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals.
Used in Pharmaceutical Synthesis:
As a precursor in the synthesis of pharmaceuticals and natural products, (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE contributes to the development of new drugs and medicines. Its presence in the synthesis process can influence the effectiveness and selectivity of the final product.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE has potential applications in the development of new drugs. Its unique properties and reactivity make it a valuable component in the design and synthesis of novel therapeutic agents.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 252770-03-9 Benzyl (4aS,7aS)-2,2-dimethylhexahydropyrrolo[3,4-d][1,3]oxazine-6(4H)-carboxylate (R)-mandelate 
• 370881-76-8 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate (S)-mandelate 
• 569682-60-6 benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate 
• 114790-39-5 benzyl N-(2,2-dimethoxyethyl)carbamate 
• 501-53-1 benzyl chloroformate 
• 252770-09-5 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 
• 370880-76-5 benzyl N-[2-(hydroxyimino)ethyl]-N-(prop-2-en-1-yl)carbamate 
• 370880-75-4 benzyl N-(2-oxoethyl)-N-(prop-2-en-1-yl)carbamate 
• 252770-08-4 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 

Downstream Products

• 246510-70-3 benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-methylsulfonyloxymethyl-pyrrolidine-1-carboxylate 
• 869956-05-8 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine 
• 869956-21-8 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(phenylsulfanil)methylpyrrolidine 
• 869956-08-1 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-formylpyrrolidine 
• 799279-83-7 benzyl (3S,4S)-3-(amino)-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate trifluoroacetate 
• 799279-80-4 Sofinicline 
• 799279-84-8 (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate 
• 799279-81-5 (1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate 
• 370881-43-9 benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel α4β2 nicotinic acetylcholine receptor selective agonists

A series of novel, potent neuronal nicotinic acetylcholine receptor (nAChR) ligands derived from 3,6-diazabicyclo[3.2.0]heptane have been synthesized and evaluated for binding affinity and agonist activity at the α4β2 nAChR subtype. Structure-activity relationship studies of these novel nAChR ligands focused on substitution effects on the pyridine ring, as well as stereo- and regiochemical influences of the 3,6-diazabicyclo[3.2.0]heptane core. Small 5-substituents on the pyridine ring had a modest impact on the binding affinities and functional activities. 6-Bromo, 6-chloro, and 6-methyl substituents on the pyridine ring led to increased binding affinities and improved functional activities. Most of the 6-N-pyridinyl-substituted 3,6-diazabicyclo[3.2.0]heptanes are selective for the α4β2 nAChR subtype. Compounds (1R,5S)-25, (1R,5S)-55, and (1R,5S)-56 were virtually inactive as agonists at the hα3β4 nAChR but retained potency and efficacy at the hα4β2 nAChR subtype. 3-N-Pyridinyl-substituted series demonstrated more complex SAR. (1R,5R)-39, (1R,5R)-41, and (1R,5R)-42 were found to be much more potent at the hα3β4 nAChR subtype, whereas (1R,5R)-38 and (1R,5R)-40 were very selective at the hα4β2 nAChR subtype. The SAR studies of these novel ligands led to the discovery of several compounds with interesting in vitro pharmacological profiles.

(1S,5S)-3-(5,6-dichloropyridin-3-YL)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate

The present invention relates to the salt (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate and to methods of preparing the salt.

(1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent

The present invention discloses (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane, salts thereof, and its use to treat pain and other disorders associated with the nicotinic acetylcholine receptor.

Substituted diazabicycloakane derivatives

Compounds of formula (I) Z-Ar1—Ar2??(I) wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from an unsubstituted or substituted 5-membered heteroaryl ring; an unsubstituted or substituted 6-membered heteroaryl ring; 3,4-(methylenedioxy)phenyl; and phenyl substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.

Substituted diazabicycloalkane derivatives

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.

Amino-substituted tricyclic derivatives and methods of use

Compounds of formula (I) wherein A and B are amine-substituted sidechains, Y1 and Y2 form various tricyclic cores, Xa and Xb are C, CH, or N, as defined herein, and Rx is an optional substituent. Compounds and compositions of formula (I) are contemplated as well as methods for treating conditions or disorders prevented by or ameliorated by α7nAChR ligands that encompass compounds of formula (I) and other tricyclic derivatives. Methods of using amino-substituted tricyclic derivatives also are described herein.

Amino-substituted tricyclic derivatives and methods of use

Compounds of formula (I) wherein A and B are amine-substituted sidechains, Y1 and Y2 form various tricyclic cores, and Rx is an optional substituent. Compounds and compositions of formula (I) are contemplated as well as methods for treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands that encompass compounds of formula (I) and other tricyclic derivatives.

(1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent

The present invention discloses (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane and its use to treat pain and other disorders associated with the nicotinic acetylcholine receptor.

(IS-5S)-3-(5,6-dichloro-3-pyridinyl-)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent

The present invention discloses (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane and its use to treat pain and other disorders associated with the nicotinic acetylcholine receptor.

Diazabicyclic central nervous system active agents

Compounds of formula I pharmaceutical compositions of these compounds, and use of said compositions to control synaptic transmission in mammals.