361441-95-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Tricyclo[3.3.1.13,7]decane-1-acetonitrile,.alpha.S)is utilized as a key intermediate in the production of various organic compounds, particularly in the pharmaceutical industry. Its unique structure and stereochemistry make it an essential component in the synthesis of complex organic molecules, contributing to the development of novel drugs and therapeutic agents.
Used in Agrochemical Development:
In the agrochemical sector, Tricyclo[3.3.1.13,7]decane-1-acetonitrile,.alpha.S)is employed as a crucial building block for the synthesis of bioactive compounds. Its versatility and compatibility with various reaction conditions enable the creation of innovative agrochemicals with improved efficacy and selectivity, addressing the challenges of pest control and crop protection.
Used in Medicinal Chemistry Research:
Tricyclo[3.3.1.13,7]decane-1-acetonitrile,.alpha.S)-'s potential applications extend to medicinal chemistry research, where it serves as a valuable tool for exploring new chemical spaces and designing novel therapeutic agents. Its unique structural properties and reactivity provide researchers with opportunities to investigate its interactions with biological targets and develop new strategies for drug discovery and optimization.
Overall, Tricyclo[3.3.1.13,7]decane-1-acetonitrile,.alpha.S)is a versatile and essential chemical compound with a wide range of applications in various industries, particularly in the fields of pharmaceuticals, agrochemicals, and medicinal chemistry. Its unique structure, stereochemistry, and compatibility with diverse reaction conditions make it a promising building block for the development of innovative and effective compounds.

Upstream product

• 711-01-3 methyl adamantane-1-carboxylate 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 773837-37-9 sodium cyanide 
• 828-51-3 1-Adamantanecarboxylic acid 
• 770-71-8 1-adamantanemethanol 
• 151-50-8 potassium cyanide 

Downstream Products

• 102502-64-7 (S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride 
• 1564265-93-5 saxagliptin 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 709031-43-6 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester 
• 681282-72-4 (S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 

Relevant academic research and scientific papers

CFTR-MODULATING ARYLAMIDES

The present disclosure relates to heterocyclic compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

Catalytic Enantioselective Intermolecular Benzylic C(sp3)?H Amination

A practical general method for asymmetric intermolecular benzylic C(sp3)?H amination has been developed by combining the pentafluorobenzyl sulfamate PfbsNH2 with the chiral rhodium(II) catalyst Rh2(S-tfptad)4. Various substrates can be used as limiting components and converted to benzylic amines with excellent yields and high levels of enantioselectivity. Additional key features for the reaction are the low catalyst loading and the ability to remove the Pfbs group under mild conditions to give NH-free benzylic amines.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.

Protected amino hydroxy adamantane carboxylic acid and process for its preparation

Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided. The provided compounds can be used for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity agent and/or other therapeutic agent.

A PROCESS FOR INDUSTRIAL PREPARATION OF [(S)-N-TERT BUTOXYCARBONYL-3-HYDROXY]ADAMANTYLGLYCINE

A commercially viable process for industrial preparation of [(S)-n-tert butoxycarbonyl-3-hydroxy]adamantylglycine which is a key intermediate for saxagliptin synthesis and is represented by compound of Formula-VI. The compound-VI obtained by the process of present invention has more than 99.5% HPLC purity, not more than 0.15 % of dihydroxy impurity, not more than 0.05% of isomer impurity and not more than 0.1% of any unknown impurity. Formula (VI).

Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin

All eight stereoisomers of saxagliptin have been synthesized and evaluated for their inhibitory activity against DPP-IV. It was unambiguously confirmed that the configuration of saxagliptin was critical to potent inhibition of DPP-IV. Docking study was performed to elucidate the configuration-activity relationship of saxagliptin stereoisomers. Tyr662 and Tyr470 have been suggested as the key residues of DPP-IV interacting with the inhibitors. This work provides valuable information for further inhibitor design against DPP-IV.

Discovery and preclinical profile of saxagliptin (BMS-477118): A highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Efforts to further elucidate structure-activity relationships (SAR) within our previously disclosed series of β-quaternary amino acid linked L-cis-4,5-methanoprolinenitrile dipeptidyl peptidase IV (DPP-IV) inhibitors led to the investigation of vinyl substitution at the β-position of α-cycloalkyl-substituted glycines. Despite poor systemic exposure, vinyl-substituted compounds showed extended duration of action in acute rat ex vivo plasma DPP-IV inhibition models. Oxygenated putative metabolites were prepared and were shown to exhibit the potency and extended duration of action of their precursors in efficacy models measuring glucose clearance in Zuckerfa/fa rats. Extension of this approach to adamantylglycine- derived inhibitors led to the discovery of highly potent inhibitors, including hydroxyadamantyl compound BMS-477118 (saxagliptin), a highly efficacious, stable, and long-acting DPP-IV inhibitor, which is currently undergoing clinical trials for treatment of type 2 diabetes.

ADAMANTYGLYCINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS

Compounds are provided having the formula (I) [Chemical Structure] wherein: n is 0, 1 or 2; m is 0, 1 or 2; the sum of n + m less then or equal to 2; the dashed bonds forming a cyclopropyl ring can only be present when Y is CH; X is H or CN; Y is CH, CH2, CHF, CF2, O, S, SO, or SO2; and A is adamantyl. Further provided are methods of using such compounds for the treatment of diabetes and related diseases, and to pharmaceutical compositions containing such compounds.