220901-72-4

Upstream product

• 394-04-7 5-fluoro-2-methoxybenzoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 1207283-54-2 phenyl 3-fluoro-6-methoxy-2-methylbenzoate 
• 1207283-56-4 phenyl 6-{[(tert-butoxy)carbonyl]oxy}-3-fluoro-2-methylbenzoate 
• 1207283-57-5 (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-6-oxa-7-azapentacyclo[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5-⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaen-16-yl tert-butyl carbonate 
• 1207283-58-6 (1R,3S,4S,11S)-8-(benzyloxy)-4-(dimethylamino)-19-fluoro-11,12,16-trihydroxy-6-oxa-7-azapentacyclo-[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione 
• 1253799-57-3 C₄₈H₅₈FN₃O₇Si 
• 1253799-29-9 phenyl 2-(benzyloxy)-3-(dibenzylamino)-5-fluoro-6-methylbenzoate 

Relevant academic research and scientific papers

Tetracycline compounds

The present invention is directed to a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula I are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula I and its therapeutic use.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

Provided is a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity, and useful as a prophylactic or therapeutic drug for Alzheimer's disease, schizophrenia, pain, sleep disorder and the like. The present invention relates to a compound represented by the formula wherein ring A is a 4- to 7-membered ring optionally having substituent (s) ; L is -O-, -S-, -SO- or -SO2-; R1 is a C1-6 alkyl group optionally having substituent(s) (provided that when L is -O-, R1 is not a C1-6 alkyl group optionally substituted by halogen atom(s)), or a cyclic group optionally having substituent(s); X1 is -CRa= or -N=; X2 is -CRb= or -N=; X3 is-CRc= or -N=; Ra, Rb and Rc are each a C1-6 alkyl group, C2-6 alkenyl group, C1-6 alkoxy group, C3-6 cycloalkyl group, C3-6 cycloalkoxy group or C6-14 aryl group, each of which optionally having substituent(s), H or halogen, or a salt thereof.

TETRACYCLINE ANALOGS

The present invention is directed to a compound represented by Structural Formula (I), or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.

Fluorocyclines. 1. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6- deoxytetracycline: A potent, broad spectrum antibacterial agent

This and the accompanying report (DOI: 10.1021/jm201467r) describe the design, synthesis, and evaluation of a new generation of tetracycline antibacterial agents, 7-fluoro-9-substituted-6-demethyl-6-deoxytetracyclines ("fluorocyclines"), accessible through a recently developed total synthesis approach. These fluorocyclines possess potent antibacterial activities against multidrug resistant (MDR) Gram-positive and Gram-negative pathogens. One of the fluorocyclines, 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6- deoxytetracycline (17j, also known as TP-434, 50th Interscience Conference on Antimicrobial Agents and Chemotherapy Conference, Boston, MA, September 12-15, 2010, poster F1-2157), is currently undergoing phase 2 clinical trials in patients with complicated intra-abdominal infections (cIAI).

POLYCYCLIC TETRACYCLINE COMPOUNDS

The present invention is directed to a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.

C7-FLUORO SUBSTITUTED TETRACYCLINE COMPOUNDS

The present invention is directed to a compound represented by Structural Formula (A): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (A) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (A) and its therapeutic use.

SYNTHESIS OF TETRACYCLINES AND INTERMEDIATES THERETO

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides more efficient routes for preparing the enone intermediate and allows for substituents at positions 4a, 5, 5a, and 12a of the tetracycline ring system.