67459-50-1

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-AMINO-5-DIETHYLAMINOPENTANE is used as a reagent in organic synthesis, particularly in the pharmaceutical industry. It plays a crucial role in the production of various drugs and biologically active compounds, contributing to the development of novel therapeutic agents.
Used in Neuroprotection and Cognitive Enhancement:
(R)-2-AMINO-5-DIETHYLAMINOPENTANE has been studied for its potential as a neuroprotective and cognitive-enhancing agent. Its unique properties make it a promising candidate for the development of treatments aimed at improving brain function and protecting against neurodegenerative diseases.
Used in Metal-Catalyzed Reactions:
(R)-2-AMINO-5-DIETHYLAMINOPENTANE, has also been investigated for its potential as a ligand in metal-catalyzed reactions. Its ability to interact with metals could lead to the development of more efficient and selective catalytic processes in the chemical industry.
Used in Synthesis of Chiral Ligands:
(R)-2-AMINO-5-DIETHYLAMINOPENTANE has potential applications as a building block in the synthesis of chiral ligands. These ligands are essential in various asymmetric reactions, contributing to the production of enantiomerically pure compounds, which are vital in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C8H20N2/c1-4-10(5-2)7-6-8(3)9/h8H,4-7,9H2,1-3H3/p+2/t8-/m1/s1

Upstream product

• 105-14-6 5-diethylamino-2-pentanone 
• 140-80-7 5-diethylamino-2-pentylamine 
• 3852-09-3 methyl 3-methoxypropionate 
• 77529-81-8 N,N-diethyl-(S)-glutamine hydrochloride 
• 77529-85-2 (S)-2-amino-5-(diethylamino)pentan-1-ol 

Downstream Products

• 54-05-7 (R)-(-)-chloroquine 
• 69698-56-2 (R)-chloroquine phosphate 
• 69698-56-2 (R)-chloroquine phosphate 
• 140-80-7 5-diethylamino-2-pentylamine 

Relevant academic research and scientific papers

Optically active chloroquine and hydroxychloroquine and analogues thereof, and preparation method, composition and application of optically active chloroquine and hydroxychloroquine

The invention provides a rapid and simple method for preparing optically active chloroquine, hydroxychloroquine and analogues thereof, which comprises the following steps: reacting racemates of chloroquine, hydroxychloroquine and analogues thereof with an acidic chiral resolution reagent to generate corresponding salts, and separating and purifying to obtain optically pure salts of chloroquine, hydroxychloroquine and analogues thereof, and reacting with alkali to obtain (R)- or (S)- chloroquine with high optical purity and (R)- or (S)- hydroxychloroquine and analogues thereof. The method is simple and convenient to operate and low in cost, the enantiomer purity can reach 99.9% ee, and industrial production of chloroquine, hydroxychloroquine and analogues thereof with single chiral configuration is easy to realize. The invention also provides (R)- or (S)- chloroquine and (R)- or (S)- hydroxychloroquine and analogues thereof, pharmaceutical compositions and uses thereof, optically activechloroquine and hydroxychloroquine and analogues thereof reduce toxic and side effects, and have better treatment effects on coronavirus, influenza virus and autoimmune diseases.

Preparation method of enantiomer pure chloroquine and chloroquine phosphate

The invention discloses a preparation method of enantiomer pure chloroquine and chloroquine phosphate, which comprises the following steps of: salifying racemic 2-amino-5-diethylaminopentane under theaction of single-configuration acid to form diastereomer salt, separating out the diastereomer salt from the solution to obtain single-configuration 2-amino- 5-diethylaminopentane intermediate salt,and the like. According to the method, racemic 2-amino- 5-diethylaminopentane is salified under the action of single-configuration acid to form diastereomer salt. On the basis of synthesizing chloroquine/chloroquine phosphate in the prior art, 2-amino-5-diethylaminopentane is used as a raw material to form diastereomer salt to resolve chiral raw materials. The method is high in purity, green and suitable for large-scale production, hazardous chemicals do not need to be introduced, salifying resolution is achieved, reaction energy barriers are reduced through catalyst application, the reactionrate is increased, side reactions are reduced, the optical purity of the product is improved through HPLC determination, the resolution cost is reduced, and the method is suitable for large-scale production.

Preparation method of chiral aminochloroquinoline

The invention discloses a preparation method of chiral aminochloroquinoline, which comprises the following steps: splitting a chiral side chain, preparing enantiomer salt, splitting the side chain andchiral acid crystals to obtain chiral acid salt, neutralizing the chiral acid salt to obtain free basic groups, and reacting the free basic groups with 4, 7-dichloroquinoline to obtain chiral aminochloroquinoline. The yield of the chiral aminochloroquinoline obtained by the method is high, and the purity reaches 99.7%.

Chloroquine phosphate enantiomer crystal form and preparation method thereof

The invention discloses a chloroquine phosphate enantiomer crystal form and a preparation method thereof. The invention provides (R)/(S)-chloroquine phosphate and a preparation method thereof. According to the (S)-chloroquine phosphate provided by the invention, an X-ray powder diffraction pattern expressed by a 2theta angle has characteristic peaks at 10.4 degrees, 10.7 degrees, 15.6 degrees, 15.8 degrees, 17.8 degrees, 18.9 degrees, 21.3 degrees and 23.9 degrees +/-0.2 degrees. According to the (R)-chloroquine phosphate provided by the invention, an X-ray powder diffraction pattern expressedby a 2theta angle has characteristic peaks at 10.3 degrees, 15.5 degrees, 15.7 degrees, 17.8 degrees and 18.8 degrees +/-0.2 degrees.

Application of chiral chloroquine, hydroxychloroquine or salt of the chiral chloroquine and hydroxychloroquine as anti-coronavirus drug target 3CL hydrolase inhibitor for reducing cardiotoxicity

The invention discloses an application of chiral chloroquine, hydroxychloroquine or pharmaceutically acceptable salts of the chiral chloroquine and hydroxychloroquine in preparation of drugs used forpreventing and/or treating coronavirus pneumonia by using a coronavirus key drug target 3CL hydrolase (Mpro) as an action target. The chiral chloroquine and hydroxychloroquine have high bonding strength with the Mpro causing inflammation of the lung and the like; the activity of the Mpro can be significantly inhibited; and the chiral chloroquine and hydroxychloroquine are indicated to have the effect of preventing and treating pneumonia caused by coronaviruses and be able to be used as anti-pneumonia drugs. Through evaluation on the inhibitory activity of an hERG potassium ion channel, the concentration at which the chloroquine, hydroxychloroquine and enantiomers of the chloroquine and hydroxychloroquine are likely to generate cardiotoxicity to the hERG potassium ion channel is provided. The chiral chloroquine and hydroxychloroquine are prepared through chiral high-performance liquid chromatography and chiral synthesis; S-configuration chloroquine, hydroxychloroquine or salts of the chloroquine and hydroxychloroquine can be selected as a drug independently, or form a pharmaceutical composition for treating diseases caused by the coronaviruses; and due to higher activity and low cardiotoxicity of the chloroquine, hydroxychloroquine or salts of the chloroquine and hydroxychloroquine, the administration dosage range is greatly widened.

USE OF CHLOROQUINE AND CLEMIZOLE COMPOUNDS FOR TREATMENT OF INFLAMMATORY AND CANCEROUS CONDITIONS

Disclosed herein are methods for use of R-chloroquine or clemizole or combinations of R- chloroquine and clemizole for the treatment of a subject in need thereof. Uses include methods of treating inflammatory' conditions, treating liver cancer or reducing the risk of developing liver cancer in a subject. Uses also include methods of treating non-alcoholic steatohepatitis in a subject.

Chemoenzymatic dynamic kinetic resolution of primary amines catalyzed by CAL-B at 38-40°c

The (R)-selective chemoenzymatic dynamic kinetic resolution of primary amines was performed at 38-40 °C in MTBE, in good to high yields and with high enantiomeric excesses. These reactions associating CAL-B to octanethiol as radical racemizing agent were carried out in the presence of methyl β-methoxy propanoate as acyl donor, under photochemical irradiation at 350 nm in glassware.