Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Patent
1990-12-10
1992-01-21
Lone, Warren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
568 27, 568 37, 568 38, C07C31714, C07C31722
Patent
active
050829742
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel 3-halogeno-2,3-diphenylacrylaldehyde derivatives, a process for preparing the derivatives and a pharmaceutical composition containing such derivative for treating hyperlipidemia. The derivatives are also useful as synthetic intermediates for diphenylthiophene derivatives usable as an anti-inflammatory agent.
PRIOR ART AND PROBLEMS THEREOF
An object of the present invention is to provide novel compounds useful not only as synthetic intermediates for an anti-inflammatory agent, but as a medicament such as an agent for treating hyperlipidemia.
Another object of the invention is to provide a process for mass production of the compounds.
A further object of the invention is to provide a novel medicament for treating hyperlipidemia and a method of treating and preventing hyperlipidemia.
DISCLOSURE OF THE INVENTION
According to the present invention, there are provided 3-halogeno-2,3-diphenylacrylaldehyde derivatives represented by the following general formula [1] ##STR2## wherein R is an alkyl group having 1 to 6 carbon atoms, X and Y each represent a halogen atom, and n is 0, 1 or 2, and a process for preparing the derivatives.
We conducted extensive research and successfully prepared the compounds of the general formula [1]. Our findings were that the compounds are useful as intermediates for synthesizing diphenylthiophene derivatives represented by the formula [7] given hereinafter and usable as an anti-inflammatory agent, and that the compounds per se have an activity of lowering the concentration of lipids and are thus useful for treating or preventing, e.g., hyperlipidemia such as hypercholesterolemia, hypertriglyceridemia, hyperphospholipidemia, hyper-free fatty acidemia and the like. The present invention has been accomplished based on these novel findings.
Specific examples of the alkyl groups of 1 to 6 carbon atoms represented by R are methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and like straight- or branched-chain alkyl groups. Examples of the halogen atoms represented by X, Y or Z include fluorine, chlorine, bromine and iodine.
The compounds represented by the formula [1] wherein X is a fluorine atom and Y is a chlorine atom are more preferable.
The derivatives of the present invention can be prepared by various processes, more specifically by the process as illustrated below in Reaction Scheme-1. ##STR3##
In the foregoing formulae, R, X, Y and n are as defined above, and Z is a halogen atom.
The phenylacetyl halide derivative [2] used as the starting material in Reaction Scheme-1 can be prepared substantially quantitatively by reacting the corresponding phenylacetic acid derivative with a nucleophilic halogenating agent such as thionyl chloride, thionyl bromide, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride or the like.
In Reaction Scheme-1, the reaction of the phenylacetyl halide derivative [2] with the halogenobenzene derivative [3] can be conducted usually with an ordinary Lewis acid in the presence or absence of a suitable solvent. In particular, the halogenobenzene derivative [3] used in the reaction can also serve as a solvent and can be readily recovered after the reaction. In this case, it is preferable to effect the reaction without addition of a solvent. However, the reaction may be carried out using common inert organic solvents such as dichloromethane, 1,2-dichloroethane, carbon disulfide and the like. Illustrative of useful Lewis acids are various kinds of those commonly used, such as aluminum chloride, titanium tetrachloride, ferric chloride, zinc chloride, boron trifluoride etherate and the like. The kind and the amount of the Lewis acid used can be suitably determined depending on the reactivity, selectivity and the like. The Lewis acid is usually used in an amount of about 1 to about 5 moles, preferably about 1 to about 2 moles, per mole of the phenylacetyl halide derivative [2]. A suitable reaction temperature is in the range of about -10.degree. to about 100.degree. C. The reacti
REFERENCES:
patent: 4324628 (1982-04-01), Avar et al.
Hashimoto Kinji
Inoue Makoto
Minamikawa Jun-ichi
Lone Warren B.
Otsuka Pharaceutical Factory, Inc.
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