28049-61-8

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile is used as an intermediate in the preparation of Sibutramine and its respective metabolites. Sibutramine is an anti-obesity drug that has been used to aid in weight loss and maintenance.
Additionally, 1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile can be used in the synthesis of pharmacologically active metabolites of Sibutramine, which may have potential applications in the treatment of obesity and related health conditions.

InChI:InChI=1/C11H10ClN/c12-10-4-2-9(3-5-10)11(8-13)6-1-7-11/h2-5H,1,6-7H2

Upstream product

• 106-39-8 bromochlorobenzene 
• 4426-11-3 cyclobutanecarbonitrile 
• 109-64-8 1,3-dibromo-propane 
• 140-53-4 p-chlorobenzyl cyanide 
• 84467-19-6 1-(3,4-dichlorophenyl)-1-cyclobutanecarbonitrile 
• 352-33-0 1-Chloro-4-fluorobenzene 

Downstream Products

• 186521-85-7 1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one 
• 106650-56-0 didesmethylsibutramine 
• 895159-96-3 (Z)-N-{1-[1-(4-chlorophenyl)-phenyl]-1,3-dienyl}-acetamide 
• 84467-20-9 1-[1-(4-chlorophenyl)cyclobutyl]ethanone 
• 63010-09-3 C-[1-(4-chlorophenyl)cyclobutyl]methylamine 
• 84485-00-7 sibutramine hydrochloride 
• 1064700-79-3 {3-[1-(4-chloro-phenyl)-cyclobutyl]-[1,2,4]oxadiazol-5-ylmethyl}-{2-[4-(2-methoxy-phenyl)-piperidin-1-yl]-ethyl}-amine hydrochloride 
• 1064701-90-1 {3-[1-(4-chloro-phenyl)-cyclobutyl]-[1,2,4]oxadiazol-5-ylmethyl}-{2-[4-(2-methoxy-phenyl)-piperidin-1-yl]-ethyl}-amine 
• 1021436-69-0 5-chloromethyl-3-[1-(4-chloro-phenyl)-cyclobutyl]-[1,2,4]oxadiazole 

Relevant academic research and scientific papers

Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes

We herein report the first example of iridium-catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

Oxadiazole Amine Derivative Compounds as Histone Deacetylase 6 Inhibitor, and the Pharmaceutical Composition Comprising the same

The present invention relates to a novel compound having an activity of inhibiting histone deacetylase 6 (HDAC6), an optical isomer thereof or a pharmaceutically acceptable salt thereof, a use thereof for preparation of a drug for treatment, a pharmaceutical composition comprising the same, a treatment method using the composition, and a method for preparing the same. The novel compound, an optical isomer thereof or a pharmaceutically acceptable salt thereof according to the present invention has an activity of inhibiting histone deacetylase 6 (HDAC6), and is effective for preventing or treating HDAC6-related diseases, including infectious diseases; neoplasm; endocrine, nutritional and metabolic diseases; mental and behavior disorders; nerve disorders; eye and adnexa diseases; cardiovascular diseases; respiratory diseases; digestive organ diseases; skin and subcutaneous tissue diseases; musculoskeletal and connective tissue diseases; or congenital malformation, deformation and chromosomal abnormality.COPYRIGHT KIPO 2017

Identification of A Novel Small-Molecule Binding Site of the Fat Mass and Obesity Associated Protein (FTO)

N-(5-Chloro-2,4-dihydroxyphenyl)-1-phenylcyclobutanecarboxamide (N-CDPCB, 1a) is found to be an inhibitor of the fat mass and obesity associated protein (FTO). The crystal structure of human FTO with 1a reveals a novel binding site for the FTO inhibitor and defines the molecular basis for recognition by FTO of the inhibitor. The identification of the new binding site offers new opportunities for further development of selective and potent inhibitors of FTO, which is expected to provide information concerning novel therapeutic targets for treatment of obesity or obesity-associated diseases.

Development of a palladium-catalyzed α-arylation of cyclopropyl nitriles

1,1-Disubstituted aryl cyclopropyl nitriles are useful moieties in biologically active compounds and provide access to a range of cyclopropyl derivatives. Herein, we describe the development of a palladium-catalyzed α-arylation of cyclopropyl, cyclobutyl, and cyclopentyl nitriles that affords these functional groups in one step from a variety of aryl bromides in good to excellent yields. Furthermore, we demonstrate the transformation of aryl cyclopropyl nitriles into aryl trifluoromethyl cyclopropanes.

SYNTHESIS, METHODS OF USING, AND COMPOSITIONS OF CYCLOALKYLMETHYLAMINES

The present invention provides novel cycloalkylmethylamine analogs, and methods of preparing cycloalkylmethylamine analogs. The present invention also provides methods of using cycloalkylmethylamine analogs and compositions of cycloalkylmethylamine analogs. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications.

Phase transfer alkylation of arylacetonitriles revisited

Phase transfer alkylations of phenylacetonitrile derivatives carried out in the presence of 60-75% aqueous KOH, instead of the typical 50% NaOH, provide substantial improvements in the overall yields and purity of products. Reactions with simple secondary alkyl halides, as well as cycloalkylations with 1,2- and 1,3-dihaloalkanes proceed with good yields. Increasing the concentration of base diminishes the formation of by-products from competitive β-elimination processes.

Method of treating addiction or dependence using a ligand for a monoamine receptor or transporter

One aspect of the present invention relates to a method of treating of drug addiction or drug dependence in a mammal, comprising the step of administering to a mammal in need thereof a therapuetically effective amount of a heterocyclic compound, e.g., a 3-substituted piperidine. In a preferred embodiment, the method of the present invention treats cocaine addiction or methamphetamine addiction.

Ligands for monoamine receptors and transporters, and methods of use thereof

One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, schizophrenia, Parkinson's disease, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.

Thiazole and other heterocyclic ligands for mammalian dopamine, muscarinic and serotonin receptors and transporters, and methods of use thereof

One aspect of the present invention relates to novel heterocyclic compounds. A second aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for various mammalian cellular receptors, including G-protein coupled receptors. A third aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for mammalian dopamine, muscarinic or serotonin receptors or transporters. Another aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for mammalian dopamine, muscarinic or serotonin receptors. The compounds of the present invention will also find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, analgesia, schizophrenia, Parkinson's disease, restless leg syndrome, sleeping disorders, attention deficit hyperactivity disorder, irritable bowel syndrome, premature ejaculation, menstrual dysphoria syndrome, urinary incontinence, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, Tourette's syndrome, psychiatric disorders, stroke, senile dementia, peptic ulcers, pulmonary obstruction disorders, and asthma.

First asymmetric synthesis of (R)-desmethylsibutramine

A catalytic enantioselective addition of iBuLi to aldimine 3 derived from methyl amine and 1-(4-chlorophenyl) cyclobutanecarboxaldehyde is used as the key step in the asymmetric synthesis of (R)-desmethylsibutramine, a single enantiomer version of a pharmacologically active metabolite of anti-obesity drug sibutramine (Meridia).