133097-95-7

Usage

Uses

Used in Organic Synthesis:
(1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane is used as a chiral base and ligand in asymmetric catalysis for the formation of carbon-carbon and carbon-nitrogen bonds. Its unique stereochemistry allows for the selective formation of desired enantiomers in chemical reactions, which is crucial in the synthesis of biologically active compounds.
Used in Pharmaceutical Development:
(1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane has been investigated for its potential use in medicinal chemistry, particularly in the development of new pharmaceuticals. Its chiral nature and ability to act as a ligand in asymmetric catalysis make it a valuable tool in the synthesis of enantiomerically pure drug candidates, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane is used as a chiral ligand to induce enantioselectivity in various chemical reactions. Its presence can significantly improve the yield and selectivity of the desired enantiomer, making it an essential component in the synthesis of chiral compounds with potential applications in pharmaceuticals, agrochemicals, and other industries.
Used in Research and Development:
(1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane is also utilized in research and development for the exploration of new synthetic methods, catalysts, and reaction mechanisms. Its unique properties and applications in asymmetric catalysis make it an attractive candidate for studying the fundamental aspects of enantioselective synthesis and developing new strategies for the preparation of enantiomerically pure compounds.

Upstream product

• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 244768-98-7 2-tert-butoxycarbonyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 
• 179694-15-6 (1S,4S)-2-benzyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 

Downstream Products

• 1116571-76-6 C₁₆H₂₄N₂O₂S 
• 1235469-91-6 (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooctadec-9-en-7-yl phenylacetate 
• 1338705-94-4 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(((1S,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-yl)methyl)benzamide 
• 138808-76-1 danofloxacin mesylate 
• 1116571-79-9 C₁₃H₁₈N₂O₃S 
• 1116571-80-2 C₁₂H₁₅ClN₂O₂S 
• 1220095-03-3 C₁₇H₂₆N₂O₂S 
• 1116571-78-8 C₁₄H₂₀N₂O₂S 
• 767291-68-9 (1S,4S)-(+)-2,5-dimethyl-2,5-diazabicyclo[2.21]heptane 

Relevant academic research and scientific papers

Inhibitors of Bruton's Tyrosine Kinase

This application discloses 6-(2-Hydroxymethyl-phenyl)-2-methyl-2H-pyridazin-3-one derivatives according to generic Formula I: wherein, variables X, R, and Y4, are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation, such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.

Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid

Endocannabinoids (eCBs) are endogenous neuromodulators of synaptic transmission. Their dysfunction may cause debilitating disorders of diverse clinical manifestation. For example, drug addiction, lack of sex desire, eating disorders, such as anorexia or bulimia and dyssomnias. eCBs also participate in the regulation of core temperature and pain perception. In this context, it is important to recognize the utility of cannabinoid receptor 1 (CB1R) agonists, natural as Δ9-tetrahydrocannabinol (THC) or synthetic as Nabilone as useful drugs to alleviate this kind of patients' suffering. Therefore, we have developed a new drug, (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooct adec-9-en-7-yl phenylacetate (PhAR-DBH-Me), that appears to bind and activate the CB1R. This diazabicyclic amide was synthesized from phenylacetylricinoleic acid and (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. To test its cannabinergic properties we evaluated its effects on core temperature, pain perception, and the sleep-waking cycle of rats. Results indicate that 20 and 40 mg/kg of PhAR-DBH-Me readily reduced core temperature and increased pain perception threshold. In addition, 20 mg/kg increased REM sleep in otherwise normal rats. All these effects were prevented or attenuated by AM251, a CB1R antagonist. Place preference conditioning studies indicated that this molecule does not produce rewarding effects. These results strongly support that PhAR-DBH-Me possesses cannabinoid activity without the reinforcement effects.

Azabicyclic sulfonamides as potent 11β-HSD1 inhibitors

Inhibition of 11β-HSD1 has demonstrated potential in the treatment of various components of metabolic syndrome. We wish to report herein the discovery of novel azabicyclic sulfonamide based 11β-HSD1 inhibitors. Highly potent compounds exhibiting inhibitor

SUBSTITUTED BICYCLIC PIPERIDINYL-AND PIPERAZINYL- SULFONAMIDES USEFUL TO INHIBIT 11β-HYDROXYSTEROID DEHYDROGENASE TYPE-1

In its many embodiments, the present invention relates to a novel class of substituted bicyclic piperidinyl- and piperazinylsulfonamide compounds useful to inhibit 11β-hydroxysteroid dehydrogenase type-I, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more conditions associated with the expression of 11β-hydroxysteroid dehydrogenase type-I using such compounds or pharmaceutical compositions.

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

MUSCARINIC RECEPTOR LIGANDS

Described herein are D4 receptor-selective compounds of the general formula I: STR1 wherein: A and B are independently selected, optionally substituted, saturated or unsaturated 5-or 6-membered, homo-or heterocyclic rings;X 1 is selected from CH 2, O, NH, S, C=O, CH--OH, CH--NEt 2, C=CHCl, C=CHCN, N--C. sub.1-4 alkyl, N-acetyl, SO 2 and SO;X 2--is selected from N=, CH 2--, CH=, C(O)--, O--, and S--; n is 1 or 2; andZ is selected from C 1-6 alkyl optionally substituted with a substituent selected from OH, halo, C. sub.1-4 alkyl and C 1-4 alkoxy;and acid addition salts, solvates and hydrates thereof. Their use as ligands for dopamine receptor identification and in a drug screening program, and as pharmaceuticals to treat indications in which the M1/M2 receptor is implicated, such as schizophrenia, is also described.

Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates

(R,R)-2,5-Diazabicyclo[ 2.2.1]heptanes are prepared from a compound of the formula STR1 wherein X and R2 are as defined herein, by heating with tosylchloride in pyridine, reacting the formed compound of the formula STR2 with a C1 -C6 alkylamine or ammonia, and reducing or hydrolyzing the formed compound of the formula STR3 wherein R1 is hydrogen or C1 -C6 alkyl.