867308-86-9

Usage

Chemical structure

A complex organic compound with a long and specific chemical structure.

Functional groups

Contains various functional groups including an imidazole ring, a carboxylic acid group, and a benzyl amide moiety.

Fluorine-substituted phenyl group

The presence of a fluorine atom in the phenyl group can influence the compound's reactivity and physical properties.

Isopropyl group

The presence of an isopropyl group can affect the compound's steric properties and reactivity.

tert-Butoxycarbonylmethyl group

The presence of a tert-butoxycarbonylmethyl group can influence the compound's reactivity and stability.

Stereochemistry

The compound has a specific stereochemistry, with the 4R,6R configuration at the [1,3]dioxan-4-yl group.

Potential applications

The compound's chemical properties and potential applications can be inferred from its structural features, but a detailed study would be necessary to fully understand its properties and potential uses.

Reactivity

The compound's reactivity can be influenced by the presence of various functional groups and the specific stereochemistry.

Physical properties

The compound's physical properties, such as solubility and melting point, can be influenced by the presence of various functional groups and the specific stereochemistry.

Stability

The compound's stability can be influenced by the presence of various functional groups and the specific stereochemistry.

Upstream product

• 867309-02-2 N-(1-benzylcarbamoyl-3-methyl-2-oxobutyl)-4-fluorobenzamide 
• 125971-86-0 tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 845280-58-2 {[2-((4R,6R)-6-tert-Butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-isobutyryl-amino}-(4-fluoro-phenyl)-acetic acid 
• 403-43-0 4-fluorobenzoyl chloride 
• 867304-09-4 1-[2-((4R,6R)-6-tert-Butoxycarbonylmethyl-2,2-dimethyl[1,3]dioxan-4-yl)-ethyl]-2-(4-fluoro-phenyl)-5-isopropyl-1H-imidazole-4-carboxylic acid 
• 100-46-9 benzylamine 
• 867308-77-8 1-[2-((4R,6R)-6-tert-butoxycarbonylmethyl-2,2-dimethyl[1,3]dioxan-4-yl)-ethyl]-2-(4-fluoro-phenyl)-5-isopropyl-1H-imidazole-4-carboxylic acid benzyl ester 
• 867308-78-9 2-(4-fluorobenzoylamino)-4-methyl-3-oxopentanoic acid benzyl ester 
• 1319747-40-4 C₂₆H₂₅NO₃ 

Downstream Products

• 1071147-05-1 C₃₁H₄₀FN₃O₅ 

Relevant academic research and scientific papers

Discovery of novel hepatoselective HMG-CoA reductase inhibitors for treating hypercholesterolemia: A bench-to-bedside case study on tissue selective drug distribution

The design of drugs with selective tissue distribution can be an effective strategy for enhancing efficacy and safety, but understanding the translation of preclinical tissue distribution data to the clinic remains an important challenge. As part of a discovery program to identify next generation liver selective HMG-CoA reductase inhibitors we report the identification of (3R,5R)-7-(4-((3-fluorobenzyl)carbamoyl)-5-cyclopropyl-2-(4-fluorophenyl) -1H-imidazol-1-yl)-3,5-dihydroxyheptanoic acid (26) as a candidate for treating hypercholesterlemia. Clinical evaluation of 26 (PF-03491165), as well as the previously reported 2 (PF-03052334), provided an opportunity for a case study comparison of the preclinical and clinical pharmacokinetics as well as pharmacodynamics of tissue targeted HMG-CoA reductase inhibitors.

Preparation of a HMG-CoA reductase inhibitor via an optimized imidazole-forming condensation reaction

Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.

CRYSTAL FORM OF SODIUM; (3R,5R)-7-[4-BENZYLCARBAMOYL-2-(4-FLUOROPHENYL)-5-ISOPROPYL-IMIDAZOL-1-YL]-3,5-DIHYDROXY-HEPTANOATE

A crystal form A of sodium; (3R, 5R)-7-[4-benzylcarbamoyl-2-(4-fluoropheynl)-5-isopropyl- imidazol-1-yl]-3,5-dihydroxy-heptanoate is provided.