103505-49-3

Usage

Uses

Used in Pharmaceutical Research and Development:
6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is used as a research chemical for the development of new pharmaceuticals due to its potential biological activity and its role in the treatment of various diseases.
Used in Drug Discovery:
In the field of drug discovery, 6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is used as a lead compound for the identification and optimization of new therapeutic agents, given its unique chemical structure and properties.
Used in Medicinal Chemistry:
6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is employed as a key intermediate in the synthesis of various medicinal compounds, contributing to the advancement of novel drug candidates.
Used in Chemical Synthesis:
6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is utilized as a reagent or building block in the synthesis of complex organic molecules, particularly in the pharmaceutical and chemical industries, for the creation of new chemical entities with potential therapeutic applications.
Used in Biological Studies:
6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is used in biological assays and screenings to evaluate its interactions with biological targets, which can provide insights into its mechanism of action and potential therapeutic uses.
Used in Toxicological Studies:
In the field of toxicology, 6-CHLORO-N4-(4-CHLOROPHENYL)-4,5-PYRIMIDINEDIAMINE is used to assess its safety profile and potential side effects, which is crucial for the development of safe and effective pharmaceuticals.

InChI:InChI=1/C10H8Cl2N4/c11-6-1-3-7(4-2-6)16-10-8(13)9(12)14-5-15-10/h1-5H,13H2,(H,14,15,16)

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 205753-24-8 7-Chloro-3-(4-chloro-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 875925-98-7 (4-chloro-phenyl)-(8-fluoro-5-oxa-2,4,11-triaza-dibenzo[a,d]cyclohepten-1-yl)-amine 
• 686344-48-9 2-chloro-N-[4-chloro-6-(4-chlorophenylamino)pyrimidin-5-yl]benzamide 
• 103566-04-7 6-chloro-9-(p-chlorophenyl)-9H-purine 
• 1408075-33-1 tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate 
• 1408075-34-2 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-piperidin-4-amine 
• 686344-50-3 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine 
• 1307786-04-4 6-chloro-9-(4-chlorophenyl)-8-ethyl-9H-purine 
• 686344-49-0 9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-ol 

Relevant academic research and scientific papers

Functionalized 6-(Piperidin-1-yl)-8,9-Diphenyl Purines as Peripherally Restricted Inverse Agonists of the CB1 Receptor

Peripherally restricted CB1 receptor antagonists may be useful in treating metabolic syndrome, diabetes, liver diseases, and gastrointestinal disorders. Clinical development of the centrally acting CB1 inverse agonist otenabant (1) was halted due to its p

Functionalized 6-(piperidin-1-yl)-8,9-diphenyl purines as inverse agonists of the CB1 receptor – SAR efforts towards selectivity and peripheralization

Antagonists of type 1 cannabinoid receptors (CB1) may be useful in treating diabetes, hepatic disorders, and fibrosis. Otenabant (1) is a potent and selective CB1 inverse agonist that was under investigation as an anti-obesity agent, but its development was halted once adverse effects associated with another marketed inverse agonist rimonabant (2) became known. Non-tissue selective antagonists of CB1 that have high levels of brain penetration produce adverse effects in a small subset of patients including anxiety, depression and suicidal ideation. Currently, efforts are underway to produce compounds that have limited brain penetration. In this report, novel analogs of 1 are explored to develop and test strategies for peripheralization. The piperidine of 1 is studied as a linker, which is functionalized with alkyl, heteroalkyl, aryl and heteroaryl groups using a connector in the form of an amine, amide, sulfonamide, sulfamide, carbamate, oxime, amidine, or guanidine. We also report more polar replacements for the 4-chlorophenyl group in the 9-position of the purine core, which improve calculated physical properties of the molecules. These studies resulted in compounds such as 75 that are potent inverse agonists of hCB1 with exceptional selectivity for hCB1 over hCB2. SAR studies revealed ways to adjust physical properties to limit brain exposure.

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

An efficient synthesis of 4,6-substituted pyrrolo[3,2-d]pyrimidines by silver-catalyzed cyclization of acetylene amine

A silver catalyzed cyclization of acetylene amine was developed to synthesize 4,6-substituted pyrrolo[3,2-d]pyrimidine, a bioactive isosteric scaffold of purine. Starting from simple commercially available acetylenes and pyrimidines, the method was found

ARYLPIPERAZINE-CONTAINING PURINE DERIVATIVES AND USES THEREOF

A novel arylpiperazine-containing purine derivatives and a pharmaceutical composition comprising the same as an active ingredient, which are useful for preventing or treating depressive disorders, are provided.

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.

Microwave-assisted three component one-pot synthesis of pyrimido-oxazepines

A synthetic approach toward pyrimido-oxazepine analogs was developed through the use of microwave heating. Certain analogs can be made in one step, which make this a valuable tool in the investigation of this therapeutically relevant scaffold.

PROCESS FOR PREPARING PURINE COMPOUNDS

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

New bicyclic cannabinoid receptor-1 (CB1-R) antagonists

A series of conformationally constrained bicyclic derivatives derived from SR141716 was prepared and evaluated as hCB1-R antagonists and inverse agonists. Optimization of the structure-activity relationships around the 2,6-dihydro-pyrazolo[4,3-

Tricyclic azepine derivatives: Pyrimido[4,5-b]-1,4-benzoxazepines as a novel class of epidermal growth factor receptor kinase inhibitors

A novel class of pyrimido[4,5-b]-1,4-benzoxazepines is described as inhibitors of epidermal growth factor receptor (EGFR) tyrosine kinase. Two compounds display potent EGFR inhibitory activity of less than 1 μM in cellular phosphorylation assays (IC50 0.47-0.69 μM) and are highly selective against a small kinase panel. Such compounds demonstrate anti-EGFR activity within a class that is different from any known EGFR inhibitor scaffolds. They also provide a basis for the design of kinase inhibitors with the desired selectivity profile.