686344-29-6

Basic information

• Product Name: Otenabant
• Synonyms: otenabant;1-[9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylaminopiperidine-4-carboxamide;Otenabant (CP-945,598);Otenabant, >=98%;CP945598 free base
• CAS NO: 686344-29-6
• Molecular Formula: C25H25Cl2N7O
• Molecular Weight: 510.42
• Mol File: 686344-29-6.mol

Chemical Properties

• Boiling Point: 757.891 °C at 760 mmHg
• Flash Point: 412.158 °C
• Appearance: /
• Density: 1.46
• PKA: 16.30±0.20(Predicted)
• CAS DataBase Reference: Otenabant(CAS DataBase Reference)
• NIST Chemistry Reference: Otenabant(686344-29-6)
• EPA Substance Registry System: Otenabant(686344-29-6)

Safety Data

• Hazardous Substances Data: 686344-29-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Otenabant is used as a potential anti-obesity drug for its ability to block CB1 receptors, thereby reducing appetite and promoting weight loss. However, its development was discontinued due to safety concerns, including adverse effects on the liver and cardiovascular system.
Used in Clinical Research:
Otenabant was used in clinical trials to evaluate its potential as a weight-loss medication. The trials aimed to assess its efficacy in reducing food intake and body weight, as well as to monitor any potential side effects and safety issues.
Despite its promising potential as an anti-obesity drug, Otenabant's use was ultimately not pursued due to the identified safety issues, highlighting the importance of thorough research and evaluation in drug development.

Upstream product

• 84100-54-9 4-ethylaminopiperidine-4-carboxylic acid amide 
• 686344-50-3 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine 

Relevant articles and documents

Development of a Practical and Efficient Synthesis of CP-945, 598-01, a CBi Antagonist for the Treatment of Obesity

Development of an efficient bond-forming sequence and optimization of reaction conditions are described for the synthesis of CP-945, 598-01 (1-HC1), a CB, antagonist in clinical studies for the treatment of obesity. Reordering of the bond-forming sequence

Discovery of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4- ethylamino-piperidine-4-carboxylic Acid Amide Hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist

We report the structure-activity relationships, design, and synthesis of the novel cannabinoid type 1 (CB1) receptor antagonist 3a (CP-945,598). Compound 3a showed subnanomolar potency at human CB1 receptors in binding (Ki= 0.7 nM) and functional assays (K i = 0.12 nM). In vivo, compound 3a reversed cannabinoid agonist-mediated responses, reduced food intake, and increased energy expenditure and fat oxidation in rodents. The endocannabinoid system (ECS a), and speci?cally the cannabinoid type 1 (CB1) receptor, plays a pivotal role in energy homeostasis.1-3 As such, stimulation of the ECS promotes food intake and energy storage and may be chronically overactive in obese subjects.4-7 In contrast, blockade of the CB 1 receptor decreases food intake and increases energy expenditure, leading to a reduction in body weight.8-11 It was hoped that CB 1 ceptor antagonists might provide effective therapy options for the management of metabolic disorders, such as obesity. Unfortunately, several CB1 receptor inverse agonists/antagonists were recently withdrawn from clinical development including the diarylpyrazole rimonabant12 1 (SR141716A) and the acyclic amide taranabant132 (MK-0364). Herein, we describe the design strategies that led to the identi?cation of a series of purine derivatives as CB1 receptor antagonists, and the optimization of PK properties that resulted in the discovery of the orally active 3a (CP-945,598), a novel, potent, and selective CB1 receptor antagonist, recently evaluated in phase 3 clinical trials for weight management.

PROCESS FOR PREPARING PURINE COMPOUNDS

A process for preparing compounds of Formula (I) are described herein as well as key intermediates.

PURINE COMPOUNDS AND USES THEREOF AS CANNABINOID RECEPTOR LIGANDS

Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals are described herein.