4-(3,3-ethylenedioxo- cyclohexyl) acetophenone and derivatives t

Details 4-(3,3-ethylenedioxo- cyclohexyl) acetophenone and derivatives t 4-(3,3-ethylenedioxo- cyclohexyl) acetophenone and derivatives t

1989-11-20

1992-04-14

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549429, 549430, 562405, 562407, C07D31772, C07C 6306

Patent

active

051049953

DESCRIPTION:

BRIEF SUMMARY
The objects of the present invention are 4-(3,3-ethylenedioxo-cyclohexyl) acetophenone and derivatives of this compound, as well as methods for their preparation and the use of these compounds as starting product for the preparation of 2-[4-(3-oxo-cyclohexyl)phenyl] propionic acid and its derivatives.
2-[4-(3-oxo-cyclohexyl)phenyl] propionic acid and derivatives thereof are known as nonsteroid anti-inflammatories (NSAI) which have, over their homologues of the 2-aryl propionic type, the advantage of a greater activity and of a lesser toxicity. Such compounds and a method for their preparation are described in the French patent No. 7229436.
The known methods of preparation of these compounds comprise several steps of synthesis which require the separation of regioisomers. These methods have the disadvantage of being difficult to implement on an industrial scale and of having only relatively low yields.
The aim of the invention is to eliminate these disadvantages and to enable the obtention of 2-[4-(3-oxo-cyclohexyl)phenyl] propionic acid and derivatives thereof in an effective and a rapid manner, with a high yield.
For this purpose, according to the invention, the method of preparation of the 2-[4-(3-oxo-cyclohexyl)phenyl] propionic acid and of its derivatives having the formula ##STR6## in which A.sup.4 represents a group ##STR7## and R.sup.1, R.sup.2 R.sup.3, R.sup.4, R.sup.5, which can be identical or different, represent each a hydrogen or an alkyl group, is characterized in that a compound of the formula ##STR8## in which A.sup.1 represents a group ##STR9## and B represents a group ##STR10## is transformed into the compound of formula (I).
In a first version of this method, compounds of formula (IV) are transformed into compounds of formula (I), by forming successive intermediate compounds of the formula ##STR11## in which Y represents either the group B defined in clamin 1, or a group ##STR12## and A.sup.3 represents a group ##STR13## in which X represents OH, Cl or CN, the meaning of Y and X for each formula being that indicated in the following table:


______________________________________ Y = B ##STR14## ______________________________________ X = OH (IX) (XII) Cl (X) (XIII) CN (XI) (XIV) ______________________________________ OH, obtained by the reduction of the ketone function of the group A.sup.1 and, when required, the deacetalisation of the acetal function of the group B, a second intermediate compound (X) or (XIII) in which X represents Cl, obtained by a substitution of chlorine for the OH group of the first intermediate compound, and a third intermediate compound (XI) or (XIV) in which X represents CN, obtained by the substitution of the CN group for the chlorine of the second intermediate compound, then by transforming the third intermediate compound into a compound of formula (I), either directly in the case where Y is the group ##STR15## or, in the case where Y represents the group B, with deacetalisation of the latter group.
In a second version of this same method, the transformation of the compounds of formula (IV) into compounds of formula (I) is carried out by forming the successive intermediate compounds of the formula ##STR16## in which Y represents either the group B defined in claim 1 or the group ##STR17## and A.sup.3 represents a group ##STR18## in which X represents OH or Cl, the meaning of Y and X for each formula being that indicated in the following table:


______________________________________ Y = B ##STR19## ______________________________________ X = OH (IX) (XII) Cl (X) (XIII) ______________________________________ OH, obtained through the reduction of the ketone function of the group A.sup.1, and a second intermediate compound (X) or (XIII) in which X represents Cl, obtained through the substitution of the chlorine for the OH group of the first intermediate compound and afterwards by transforming, when required, the compound (XIII) into the compound (X) through the acetalisation of the ketone function Y, then by transform

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