160145-83-5

Usage

Uses

Used in Pharmaceutical Industry:
Telithromycin intermediate (7A) is used as a crucial intermediate in the synthesis of telithromycin, an antibiotic medication, for its role in treating respiratory tract infections. Its importance lies in its contribution to the final formulation of the antibiotic, ensuring the effectiveness of the medication in combating bacterial infections in the respiratory system.

Upstream product

• 198782-60-4 (2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,4S,5S,6R,7R,9R,13S,14R,E)-14-ethyl-4,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradec-11-en-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate 
• 198782-59-1 10,11-anhydro-6-O-methyldescladinosylerythromycin A 
• 144604-03-5 (10E)-10,11-didehydro-11-deoxy-6-O-methylerythromycin 
• 143353-81-5 3-Ode-[(2,6-dideoxy-3-methyl-3-O-methyl-α-L-ribohexopyranosyl)oxy]-6-O-methylerythromycin 2￠-acetate 
• 118058-74-5 3-O-descladinosylclarithromycin 
• 81103-11-9 clarithromycin 
• 530-62-1 1,1'-carbonyldiimidazole 
• 214694-76-5 2'-O-acetyl-10,11-didehydro-11-deoxy-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A 
• 160145-81-3 Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((3R,5R,6R,7R,9R,11R,12R,13R,14R)-14-ethyl-13-hydroxy-12-methanesulfonyloxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 143353-82-6 Acetic acid (2S,3R,4S,6R)-4-dimethylamino-2-((3R,5R,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-oxacyclotetradec-6-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 

Downstream Products

• 143353-30-4 (3aS,4R,7R,9R,10R,11R,13R,15aR)-10-((2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-(4-phenyl-butyl)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone 
• 191114-48-4 telithromycin 

Relevant academic research and scientific papers

An Approach to Modify 14-Membered Lactone Macrolide Antibiotic Scaffolds

A ketolide derivative with (12R)-configuration was obtained via a novel ketene acetal in acidic conditions. The structure of this atypical β-keto ketene acetal intermediate within the macrocyclic system has been determined by NMR and X-ray methods. The use of basic conditions at an elevated temperature yielded new, doubly α,β-unsaturated ketone macrolide derivatives with (4E)-configuration as two conformational isomers of folded-in or folded-out conformations.

Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity

In an effort to find new antibiotics, a novel series of 14-membered macrolides with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains has been synthesized based on commercially available clarithromycin. Chemical transformation of hydroxy group at position C-3 afforded range of ketolides and acylides. Compared to telithromycin, compound 15a demonstrated improved in vitro activity against erythromycin-susceptible and -resistant strains.

PROCESS FOR THE PRODUCTION OF TELITHROMYCIN

The present invention relates to a process for the preparation of erythromysin derivatives, in particular telithromycin of formula (I) and its pharmaceutically acceptable salts, providing the isolated intermediates in crystalline form of superior stability and purity.

Synthesis and antibacterial activity of ketolides (6-O-methyl-3- oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens

In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo- 6-O-methylerythromycin derivatives, so-called 'ketolides'. A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12- carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,-12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.