97664-58-9

Usage

General Description

1-Hexanamine, 6-(4-phenylbutoxy)-, also known as 4-Phenylbutylhexylamine, is a chemical compound commonly used as a precursor in the synthesis of pharmaceuticals and agrochemicals. It is classified as an aliphatic amine and is derived from hexane, a saturated hydrocarbon. 1-Hexanamine, 6-(4-phenylbutoxy)- has a six-carbon chain with a phenylbutyl group attached to the sixth carbon, making it a long-chain amine. It has a wide range of applications, including its use as an intermediate in the production of medicines, pesticides, and other organic compounds. Additionally, it may also be used in research and development activities for the synthesis of new chemical entities.

Upstream product

• 1205553-06-5 6-(4-phenylbutoxy)hexanenitrile 
• 928118-30-3 [6-(4-phenylbutoxy)hexyl]carbamic acid ter-butyl ester 
• 97664-55-6 N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine 
• 94749-73-2 6-bromohexyl 4-phenylbutyl ether 
• 3360-41-6 4-phenyl-butan-1-ol 
• 629-03-8 1 ,6-dibromohexane 
• 168412-89-3 1-azido-6-(4-phenylbutoxy)hexane 

Downstream Products

• 97664-55-6 N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine 
• 141474-14-8 1-(4-ethoxycarbonylamino-3-cyano-5-fluoro-phenyl)-2-[6-(4-phenyl-butoxy)hexylamino]-ethanol-hydrochloride 
• 928118-31-4 C₄₈H₅₃N₅O₃ 
• 1205553-07-6 6-(4-phenylbutoxy)hexyl isocyanate 
• 160889-19-0 2-Benzyloxy-5-((R)-2-{benzyl-[6-(4-phenyl-butoxy)-hexyl]-amino}-1-hydroxy-ethyl)-benzoic acid methyl ester 
• 135271-47-5 (S)-Salmeterol 
• 135271-47-5 (R)-(-)-salmeterol 
• 444809-33-0 (R)-1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-[6-(4-phenyl-butoxy)-hexylamino]-ethanol 

Relevant academic research and scientific papers

Structural isomers of saligenin-based β2-agonists: Synthesis and insight into the reaction mechanism

Salmeterol and albuterol are well-known β2-adenoreceptor agonists widely used in the treatment of inflammatory respiratory diseases, such as bronchial asthma and chronic obstructive pulmonary disease. Here we report the preparation of structural isomers of salmeterol and albuterol, which can be obtained from the same starting material as the corresponding β2-agonists, depending on the synthetic approach employed. Using 1D and various 2D NMR measurements, we determined that the structure of prepared isomers holds the β-aryl-β-aminoethanol moiety, in contrast to the α-aryl-β-aminoethanol moiety found in salmeterol and albuterol. We investigated the reaction of β-halohydrin and amines responsible for the formation of β-aryl-β-amino alcohol-both experimentally and using computational methods. The structure of β-halohydrin with the methyl salicylate moiety imposes the course of the reaction. The solvent plays a relevant, yet ambiguous role in the direction of the reaction, while the strength of the base influences the reaction yield and isomer ratio in a more evident way. Using computational methods, we have shown that the most probable reaction intermediate responsible for the formation of the unexpected isomer is the corresponding para-quinone methide, which can be formed due to phenol present in the methyl salicylate moiety. After successful preparation of albuterol and salmeterol isomers, we tested their inhibition potency to human acetylcholinesterase (AChE) and usual and atypical butyrylcholinesterase (BChE). Kinetic studies revealed that both isomers are low-potency reversible inhibitors of human cholinesterases.

ENZYME INHIBITORS AND THE USE THEREOF

The present invention provides compounds and methods for the treatment of diseases or disorders such as heart failure, hyperlipidemia, hypercholesterolemia, gonadotropin deficiency, diabetes mellitus, metabolic syndrome, hyperglycemia, insulin resistance,

Alpha2C adrenoreceptor agonists

In its many embodiments, the present invention relates to a novel class of phenylmorpholine and phenylthiomorpholine compounds useful as α2C adrenergic receptor agonists, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the α2C adrenergic receptor agonists using such compounds or pharmaceutical compositions.

SUBSTITUTED PHENYLPHOSPHATES AS MUTUAL PRODRUGS OF STEROIDS AND β -AGONISTS FOR THE TREATMENT OF PULMONARY INFLAMMATION AND BRONCHOCONSTRICTION

A mutual prodrug of a corticosteroid and a substituted phenylphosphate (β-agonist derivative) for formulation for delivery by aerosolization to inhibit pulmonary inflammation and bronchoconstriction is described. The mutual prodrug is preferably formulate

Derivatives of 6-(4-phenylbutoxy)hexylamine and process for producing Salmeterol

The present invention refers to new derivatives of the 6-(4-phenylbutoxy)hexylamine of the general formula (I): wherein: R1is CHO or CHOR3OR4, where R3and R4independently are C1-C6alkyl, aralkyl, or they form 5 or 6 membered cyclic acetals; and R2is H, benzyl or an alkyloxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl or acyl group; and to a process for its obtention. The invention also refers to a new process for obtaining Salmeterol or its pharmaceutically acceptable salts, characterized in that reaction of an organometallic compound of the general formula (13) is carried out in an inert solvent at low temperature with a synthetic intermediate of the general formula (I), wherein R1is CHO, and R2is an alkyloxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl or acyl group.

Phenylethanolamines, pharmaceutical compositions containing these compounds and process for preparing them

The invention relates to phenylethanolamines of general formula STR1 wherein R1 and R2 are defined as in claim 1, the enantiomers and the acid addition salts thereof, which have valuable pharmacological properties, not only analgesic, antiphlogistic, broncholytic, uterus-spasmolytic, lipolytic effects and an antispastic effect on the cross-striped muscle, but also β2 -mimetic and/or β1 -blocking effects, the use thereof as pharmaceuticals and as performance enhancers and processes for preparing them.

Synthesis of 1-amino-6-(4-phenylbutoxy)hexane: Arylalkylamino group in Salmeterol

An efficient preparation of the title arylalkyl amine (7) from 4-phenylbutanol and 1,6-dibromohexane (55percent overall yield in 3 steps) is reported.

Enantioselective synthesis of salmeterol via asymmetric borane reduction

Enantioselective syntheses of both enantiomers of salmeterol are accomplished using asymmetric borane reductions with chiral oxazaborolidines as catalysts.