799279-81-5

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)is used as a chiral resolving agent for the synthesis of enantiomerically pure pharmaceuticals. Its unique stereochemistry allows for the selective formation of desired enantiomers, improving the efficacy and safety of the resulting drugs.
Used in Organic Synthesis:
3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)is used as a chiral building block in the synthesis of various organic compounds, including natural products, agrochemicals, and other specialty chemicals. Its bicyclic structure and stereochemistry enable the formation of complex molecular architectures with high selectivity.
Used in Asymmetric Synthesis:
3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)is employed as a catalyst or ligand in asymmetric synthesis, facilitating the enantioselective formation of chiral centers in target molecules. Its unique stereochemistry enhances the efficiency and selectivity of asymmetric reactions, leading to the production of enantiomerically pure compounds with improved yields and reduced waste.
Used in Research and Development:
3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)serves as a valuable tool in academic and industrial research, where it is used to study the mechanisms of asymmetric reactions and develop new synthetic methodologies. Its unique properties and applications contribute to the advancement of organic chemistry and the discovery of novel chiral compounds with potential applications in various fields.

Upstream product

• 799279-84-8 (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate 
• 252770-03-9 Benzyl (4aS,7aS)-2,2-dimethylhexahydropyrrolo[3,4-d][1,3]oxazine-6(4H)-carboxylate (R)-mandelate 
• 799279-83-7 benzyl (3S,4S)-3-(amino)-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate trifluoroacetate 
• 252770-09-5 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 
• 246510-70-3 benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-methylsulfonyloxymethyl-pyrrolidine-1-carboxylate 
• 246510-69-0 benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-hydroxymethyl-pyrrolidine-1-carboxylate 
• 370881-43-9 benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate 

Downstream Products

• 956276-49-6 tert-butyl (1R,5S)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate 
• 799279-80-4 Sofinicline 
• 799279-93-9 5-[(1S,5S)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile 

Relevant academic research and scientific papers

QUINOLINE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE SEROTONIN 5-HT6 RECEPTOR

The present invention relates to novel quinoline compounds of the formula (I) and to the salts thereof. The compounds possess valuable therapeutic properties and are particularly suitable, for treating diseases that respond to modulation of the serotonin 5-HT6 receptor. In formula (I) R is a moiety of the formula (R) wherein * indicates the binding site to the quinolinyl radical and wherein A, B, X', Y, Q, R1, R2, R3, R4, R5, m, n, p, q, Ra, Rb, X and Ar are as defined in claim 1.

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 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, 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.

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.

(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.