52 results about "2-Azetidinone" patented technology

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

The invention encompasses (3R,4S)-4-((4-benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-2-azetidinone (Compound 2a) having an enantiomeric purity of at least about 97.5%. The invention also encompasses Compound 2a having a chemical purity of at least about 97%. The invention further encompasses processes for preparing Compound 2a from Compound 1 having the following formula:The invention also encompasses processes for preparing a compound having the following formula:from a compound having the following formula:wherein R is selected from the group consisting of: H or a hydroxyl protecting group. The invention also encompasses processes for preparing Compound 2a, preferably to form Compound 2a-Form 01. Also included are processes for preparing ezetimibe from Compound 2a-Form 01 or Compound 2a prepared according to the invention, compositions containing such ezetimibe, and methods for reducing cholesterol using such compositions

The instant invention provides novel cholesterol absorption inhibitors of Formula I and the pharmaceutically acceptable salts and esters thereof. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating and preventing atherosclerosis and atherosclerotic disease events.

A process for the production of 1-(4-3(R)-[3(S)-(4-fluorophenyl)-3-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) according to the following reaction scheme: (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI) where the substances of the general Formulas II, IV, VI, VIII, IX, X and XI are new, Formula III is a non-isolated intermediate, R1, R2 and R3 are represented by the compounds of Formulas Va-Vd, (Va), (Vb), (Vc), (Vd) and R4 is a silyl, e.g., tert-butyl-dimethyl-silyl, tert-butyl-diphenyl-silyl group.

A synthesis method of 4-acetoxyl-2-azetidinone comprises the following steps of: (1) taking N-p-methoxypheny-N-(acetyl) methyleneimine as a raw material and carrying out cyclization reaction with (R)3-tert-butyldimethylsilyloxy-sulfo-butyrate-S-2-pyridinyl ester to obtain (3S,4S)-3-[(1'R)-tert-butyldimethylsilyloxyethyl]-4-acetyl-1-p-methoxyphenyl-2-azetidinone; (2) preparing (3R,4R)-3-[(1'R)-tert-butyldimethylsilyloxyethyl]-4-acetoxyl -1-p-methoxyphenyl-2-azetidinone from peroxyacetic acid through oxidization in the presence of Na3PO4 and a phase transfer catalyst; and (3) removing protective groups to obtain a final product (3R,4R)-3-[(1'R)-tert-butyldimethylsilyloxyethyl]-4-acetoxyl-2-azetidinone. The invention has the advantages of shortening reaction period, improving reaction total yield, and improving reaction yield and product purity by introducing the phase transfer catalyst in the step (2). The method is simple, causes small pollution and has great application value and economic benefit.

The invention relates to a preparation method of 4-acetyloxy-2-azetidinone compounds, and is used for solving the problem that the large-scale industrial production cannot be favorably realized because of defects such as severe reaction condition, complex treatment process, high cost, serious environment pollution and the like in the prior art. The method provided by the invention comprises the step of carrying out oxidization deacidification in the existence of a dehydrating agent N, N'-dicyclohexylcarbodiimide and an oxidizing agent peroxyacetic acid by taking 4-carboxyl-2-azetidinone compounds I as raw materials to obtain the 4-acetyloxy-2-azetidinone compounds II. A heavy metal oxidizing agent or catalyst is prevented from being used in the oxidization deacidification process, so that the residue and discharge of heavy metals and environmental pollution caused by the heavy metals are greatly reduced. Byproducts generated in a reaction process can be conveniently recycled, so that the production cost is reduced to the great extent, and the preparation method is more excellent on the aspect of economical efficiency. The method is mild in reaction condition, simple and convenient to operate and suitable for large-scale production; the 4-acetyloxy-2-azetidinone compounds are easy to separate and purify and high in yield.