4166-53-4

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLGLUTARIC ANHYDRIDE is used as a key intermediate in the synthesis of oxoeicosanoid receptor antagonists. These antagonists play a significant role in modulating the stimulatory effects on cell types involved in mediating immunity-based inflammatory reactions. By targeting these receptors, 3-METHYLGLUTARIC ANHYDRIDE contributes to the development of therapeutic agents that can potentially treat a range of inflammatory and immune-related disorders.

InChI:InChI=1/C6H8O3/c1-4-2-5(7)9-6(8)3-4/h4H,2-3H2,1H3

Upstream product

• 67-56-1 methanol 
• 626-51-7 3-methyl glutaric acid 
• 6280-15-5 3-methylpentanedial 
• 141-82-2 malonic acid 
• 123-63-7 paracetaldehyde 
• 4161-07-3 3-Methyl-glutarsaeure-mono--ester 
• 5832-70-2 diethyl 2-cyano-3-methylpentanedioate 

Downstream Products

• 106591-88-2 5-(3,4-dimethoxy-phenyl)-3-methyl-5-oxo-valeric acid 
• 27151-65-1 3-methyl-1,5-pentanedioic acid monomethyl ester 
• 500344-72-9 4-methyl-1-phenethyl-piperidine-2,6-dione 
• 858795-25-2 3-methyl-glutaric acid bis-phenethylamide 
• 100823-19-6 5-anilino-3-methyl-5-oxopentanoic acid 
• 56051-60-6 3-methyl-glutaric acid dibutyl ester 
• 2840-61-1 3-methyl-5-oxo-5-phenylpentanoic acid 
• 25883-04-9 3-(Acetyl-methyl-amino)-5-(4-carboxy-3-methyl-butyrylamino)-2,4,6-triiodo-benzoic acid 
• 4962-66-7 N-(3,4-Dimethoxyphenaethyl)-β-methylglutarsaeure monoamid) 
• 92864-22-7 5-(2,4-Dimethyl-phenyl)-3-methyl-5-oxo-pentanoic acid 
• 4457-71-0 3-methylpentane-1,5-diol 
• 71135-23-4 (R,S)-3-methyl-4-aminobutyric acid 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 

Relevant academic research and scientific papers

Total Synthesis of Huperzine R

A total synthesis of huperzine R was accomplished. Intramolecular cycloaddition of a nitrile oxide and reductive cleavage of the resulting isoxazoline induced sequential cleavage of the C-C and C-O bonds to form the characteristic bicyclic lactam core with an enone moiety. Construction of the butenolide moiety from the enone afforded huperzine R.

Development of novel phenoxyalkylpiperidines as high-affinity Sigma-1 (σ1) receptor ligands with potent anti-amnesic effect

The sigma-1 (σ1) receptor plays a significant role in many normal physiological functions and pathological disease states, and as such represents an attractive therapeutic target for both agonists and antagonists. Here, we describe a novel series of phenoxyalkylpiperidines based on the lead compound 1-[ω-(4-chlorophenoxy)ethyl]-4-methylpiperidine (1a) in which the degree of methylation at the carbon atoms alpha to the piperidine nitrogen was systematically varied. The affinity at σ1 and σ2 receptors and at Δ8-Δ7 sterol isomerase (SI) ranged from subnanomolar to micromolar Ki values. While the highest-affinity was displayed at the σ1, the increase of the degree of methylation in the piperidine ring progressively decreased the affinity. The subnanomolar affinity 1a and 1-[ω-(4-methoxyphenoxy)ethyl]-4-methylpiperidine (1b) displayed potent anti-amnesic effects associated with σ1 receptor agonism, in two memory tests. Automated receptor–small-molecule ligand docking provided a molecular structure-based rationale for the agonistic effects of 1a and 1b. Overall, the class of the phenoxyalkylpiperidines holds potential for the development of high affinity σ1 receptor agonists, and compound 1a, that appears as the best in class (exceeding by far the activity of the reference compound PRE-084) deserves further investigation.

LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

LIPID PRODRUGS OF BTK INHIBITORS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

LIPID PRODRUGS OF GLUCOCORTICOIDS AND USES THEREOF

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

MODULATORS OF INDOLEAMINE 2,3-DIOXYGENASE

Provided are IDO1 inhibitor compounds of Formula I and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and methods for their use in the prevention and/or treatment of diseases. Formula I Wherein R1 is a group having Formula II

LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS

The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

METHOD FOR PRODUCING CARBOXYLIC ANHYDRIDE AND ARYLBORONIC ACID COMPOUND

When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.