Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1993-07-02
1994-04-26
Cintins, Marianne M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
558155, 558156, 558179, 558180, 558194, 558208, 558214, C07F 9117, C07F 9144, C07F 940, A61K 3166
Patent
active
053068416
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INVENTION
The present invention relates to novel derivatives of different phosphorus-containing isomers of inositol and compositions containing the same.
BACKGROUND OF THE INVENTION
The family of hexahydroxy derivatives of cyclohexane is known as inositols. There exist nine different isomers and one of these, myo-inositol, is of biological importance. Chiro-inositols and scyllo-inositols are also naturally occurring but very little is known about their biological role.
Myo-inositol is an essential nutrient for microorganisms and under special dietary conditions for different animals.
There are some known derivatives of myo-inositol such as phosphates and phospholipids.
Myo-inositol is found in plants primarily as its hexaphosphate ester, i.e. phytic acid.
Different specific isomers of myo-inositol phosphates such as D-myo-inositol1,4,5-trisphosphate has been reported in Biochem. Biophys. Res. Commun. 120.2 (1984) p. 481. This compound is known as an intracelluar calcium mobilizer in mammalian cells. Other specific isomers of myo-inositol trisphosphate have been disclosed in the U.S. Pat. No. 4,797,390. Compounds described in the above mentioned patent are used for example in pharmaceutical preparation.
Despite the ionic structure of the compounds the pharmacological effect of these compounds is very significant also after oral administration. However, in order to improve the penetration through biological membranes different lipophilic derivatives of inositol phosphates have been disclosed in the European Patent Application No. 269105. Examples of these are acyloxyalkylesters of inositol phosphates where the phosphate substituents are further esterified with acyloxyalkyl moities.
In certain biological systems it is desirable that the substituents on the inositol phosphate compounds are removed after the penetration of cellular membranes. For example after oral administration of an inositol phosphate derivative it is in many cases important to design the derivative in such a way that the original compound is formed in the blood stream. After the penetration of cell membranes for example esterified inositol phosphates are degraded enzymatically by different forms of esterases. However, in many cases the degradation process is quite slow and thus the formation of the requested compound is retarded.
SUMMARY OF THE INVENTION
According to the present invention it has quite unexpectedly been possible to produce novel derivatives of inositol in pure form.
A compound having the formula ##STR5## has been produced with high purity wherein X is a radical of myo-inositol or a radical of a configuration isomer thereof ##STR6## wherein Y is (1) oxygen ##STR7## where A.sup.1 and A.sup.2 are the same or different and are hydrogen, alkyl, aryl, aralkyl, alkenyl, cycloalkyl or cycloalkenyl and n is 3-10 ##STR8## where A.sup.1 and A.sup.2 are as described above and where m is 1-5 ##STR9## where A.sup.1 and A.sup.2 are as described above wherein R.sup.1 is hydrogen, straight or branched alkyl, alkenyl, aryl, alkaryl, alkoxy or aryloxy, wherein R.sup.2 is
In the above definition alkyl means a straight or branched chain preferably containing 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl or octyl. Alkenyl designates a straight or branched chain preferably containing 2 to 6 carbon atoms such as propenyl, butenyl or pentenyl. Aryl means radicals such as phenyl and naphtyl while cycloalkyl means a structure containing preferably 4 to 7 carbon atoms such as cyclohexyl. Alkoxy means a straight or branched chain containing 1 to 10 carbon atoms such as methoxy, ethoxy, propyloxy, butyloxy and hexyloxy whereas aryloxy contains 6-12 carbon atoms and means phenyloxy or naphtyloxy.
The above mentioned radicals are unsubstituted or substituted with substituents such as alkyl, alkoxy, alkylthio, halogen, amino or hydroxyl.
The described compounds of formula (I) are inositol phosphates and inositol phosphonates substituted with specific forms of acyloxyalkyl moities. After
REFERENCES:
patent: 4515722 (1985-05-01), Yang et al.
patent: 4585762 (1986-04-01), Teraji et al.
patent: 4797390 (1989-01-01), Siren
patent: 5157140 (1992-10-01), Siren
Biochem. Biophys. Res. Commun., vol. 120; 2, pp. 481-485 (1984); Suematsu et al.
Bundgaard, deceased Hans
Bundgaard, legal representative by Charlotte
Cintins Marianne M.
Hydorn Michael B.
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