156907-84-5 Usage
Uses
Used in Pharmaceutical Industry:
OSU6162hydrochloride is used as a pharmaceutical agent for its ability to act as a weak dopamine D2 receptor antagonist. This property makes it a promising candidate for the development of treatments targeting conditions related to dopamine receptor dysregulation, such as certain neurological and psychiatric disorders.
Used in Research Applications:
In the field of scientific research, OSU6162hydrochloride is used as a research tool to study the role of dopamine D2 receptors in various biological processes. Its weak antagonistic activity allows researchers to investigate the effects of modulating these receptors in a controlled manner, providing valuable insights into the underlying mechanisms of related diseases and potential therapeutic strategies.
Used in Drug Development:
OSU6162hydrochloride is used as a starting point for the development of new drugs targeting dopamine D2 receptors. Its weak antagonistic properties can be optimized and modified through chemical synthesis to create more potent and selective compounds with improved pharmacological profiles. This can lead to the discovery of novel therapeutic agents for the treatment of various diseases associated with dopamine receptor dysfunction.
Biological Activity
Dopamine stabilizer that lacks high in vitro affinity for various neuroreceptors (K i values are 447 and 1305 nM for D 2 and D 3 receptors respectively and > 1 μ M for other targets). In vivo, shows high D 2 receptor occupancy and is highly active on dopamine synthesis and turnover. Induces stabilizing effects on psychomotor function in behavioral tests without inducing hypolocomotion or catalepsy.
Check Digit Verification of cas no
The CAS Registry Mumber 156907-84-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,6,9,0 and 7 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 156907-84:
(8*1)+(7*5)+(6*6)+(5*9)+(4*0)+(3*7)+(2*8)+(1*4)=165
165 % 10 = 5
So 156907-84-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H23NO2S.ClH/c1-3-9-16-10-5-7-14(12-16)13-6-4-8-15(11-13)19(2,17)18;/h4,6,8,11,14H,3,5,7,9-10,12H2,1-2H3;1H/t14-;/m1./s1
156907-84-5Relevant academic research and scientific papers
Lipton, Michael F.,Mauragis, Michael A.,Maloney, Mark T.,Veley, Michael F.,VanderBor, Dale W.,Newby, John J.,Appell, Robert B.,Daugs, Edward D.
, p. 385 - 392 (2003)
The synthesis of the chiral, nonracemic 3-aryl piperidine, OSU 6162 (1), a potential CNS agent from Pharmacia Corporation, is presented. The key construction in the described synthesis is a palladium-catalyzed aryl cross-coupling reaction between bromosulfone (4) and pyridyl borane (14). Initially developed conditions for this Suzuki reaction, conducted in tetrahydrofuran/aqneous hydroxide, delivered free base (6) or hydrochloride salt (15a) in reproducible 80% yield. However, by changing the solvent to toluene and the base to carbonate, significant decreases in catalyst requirement were realized, and the methane sulfonate salt (15b) of the coupled product could be obtained in reproducible 92-94% yield on 200-kg input. The success of the Suzuki reaction was critically dependent on a bulk source of the pyridyl borane coupling partner. Cryogenic conditions were developed for its generation via lithium-halogen exchange to generate thermally labile 3-lithiopyridine followed by transmetalation with diethylmethoxy borane. This highly exothermic series of transformations yielded crystalline diethyl-3-pyridyl borane in reproducible 75-80% yield on scales ranging up to 200-kg input. Selective reduction of the biaryl, classical resolution and introduction of the propyl group via the Gribble reductive amination procedure completed the synthesis of OSU 6162 free base. This route was employed to deliver over 35 kg of clinical-quality bulk drug in short order.
