157341-41-8

Usage

Uses

Used in Respiratory Conditions:
DMP 777 is used as a therapeutic agent for managing respiratory conditions such as emphysema, cystic fibrosis, and adult respiratory distress syndrome. Its role in modulating immune responses is crucial in these applications, as it helps in controlling the inflammation and damage caused by these diseases.
Used in Alzheimer's Disease Research:
DMP 777 is used as a potential treatment option in Alzheimer's disease research. Its immune-modulating properties are being explored for their potential to slow down the progression of the disease or improve the symptoms associated with it.
Used in Medical and Scientific Research:
DMP 777 is used as a research tool in the field of medical and scientific research. Its ability to modulate immune responses makes it a valuable compound for studying the underlying mechanisms of various diseases and conditions, as well as for developing new therapeutic strategies. The full extent of its implications in therapeutic treatment is still under investigation, indicating that DMP 777 holds promise for future advancements in medicine.

InChI:InChI=1/C31H40N4O6/c1-5-8-24(22-11-14-25-26(19-22)40-20-39-25)32-30(38)35-28(37)31(6-2,7-3)29(35)41-23-12-9-21(10-13-23)27(36)34-17-15-33(4)16-18-34/h9-14,19,24,29H,5-8,15-18,20H2,1-4H3,(H,32,38)/t24-,29+/m1/s1

Upstream product

• 63740-97-6 1-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)butan-1-one 
• 179930-11-1 (R)-E-β-((1, 3-benzodioxol-5-ylmethylene)amino)benzene-ethanol 
• 120-57-0 piperonal 
• 85858-94-2 1-(4-hydroxybenzoyl)-4-methyl-piperazine 
• 99-96-7 4-hydroxy-benzoic acid 
• 197508-43-3 (R)-N-[1-(1,3-Benzodioxol-5-yl)butylidene]-α-methylbenzene-methanamine 
• 178946-02-6 3.3-Diethyl-4S-(4'-carboxyphenoxy)-2-azetidinone 
• 181481-61-8 (S)-α-propylpiperonyl alcohol 
• 181481-62-9 1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-(1R)-butylamine 
• 178946-03-7 (R,S)-2-[4-(benzyloxycarbonyl)phenoxy]-3,3-diethylazetidin-4-one 
• 181481-64-1 (R)-α-Propylpiperonylazide 
• 142935-44-2 4-Propionyloxy-3,3-diethylazetidin-2-one 
• 94-18-8 Benzyl 4-hydroxybenzoate 
• 109-01-3 1-methyl-piperazine 

Downstream Products

• 6890-31-9 1-(1,3-benzodioxol-5-yl)butan-1-ol 
• 85858-94-2 1-(4-hydroxybenzoyl)-4-methyl-piperazine 

Relevant academic research and scientific papers

An efficient large-scale process for the human leukocyte elastase inhibitor, DMP 777

This report describes a new convergent, selective, and economical synthesis of DMP 777, ending with the coupling of the chiral β-lactam half of the molecule (1) to the chiral amine as the isocyanate (2). Other steps involve the coupling of the β-lactam 3 to the phenolic moiety under phase-transfer conditions, followed by resolution of the resulting piperazine derivative using a chiral acid, and recycling of the undesired enantiomer also under phase-transfer conditions. The chiral amine 4 was produced efficiently starting from (R)-α-methylbenzylamine and the corresponding butyrophenone.

An asymmetric synthesis of L-694,458, a human leukocyte elastase inhibitor, via novel enzyme resolution of β-lactam esters

A convergent synthesis of [S-(R*,S*)]-2-[4-[(4-methylpiperazin-1-yl)carbonyl]phenoxy]-3,3-diet hyl-N-[1-[3,4-(methylenedioxy)phenyl]butyl]-4-oxo-1-azetidinecarboxami de (L-694,458, 1), a potent human leukocyte elastase inhibitor, was achieved via chiral synthesis of key intermediates: (S)-3,3-diethyl-4-[4'-[(N-methylpiperazin-1-yl)carbonylphenoxy]-2-azet idinone (2) and (R)-α-propylpiperonyl isocyanate (3). Synthesis of β-lactam 2 was achieved by a novel enantioselective lipase hydrolysis of ester 5 to produce (S)-3,3-diethyl-4-(4'-carboxyphenoxy)-2-azetidinone (6) (60% yield, three cycles, 93% ee) with isolation, epimerization, and recycling of the undesired (R)-ester 5. Isocyanate 3 was prepared by chiral addition of Zn(n-Pr)2 to piperonal (98% yield, 99.2% ee), azide displacement and reduction to (R)-α-propylpiperonylamine (11) (58% yield, 85% ee), crystallization as the D-pyroglutamic acid salt (92% yield, 98.2% ee), and isocyanate formation (98% yield) with phosgene.