Fluorinated organic compounds, ophthalmological applications the

Details Fluorinated organic compounds, ophthalmological applications the Fluorinated organic compounds, ophthalmological applications the

1998-02-26

2000-03-21

Wilson, James O.

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

Organic compounds

Halogen containing

570123, 570124, 570165, 570166, 570168, 570169, C07C 1702

Patent

active

06040485&

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field of the Invention
The present invention relates to novel fluorinated organic compounds having a fluorinated chain and a hydrogenated chain; the invention aims at applications of these novel compounds, particularly ophthalmological applications or as cell preservation medium, and relates to the method of making said compounds.
2. Background Art
Fluorinated compounds are known to have specific properties such as good stability, biocompatibility, and capacity to solubilize gases and specially oxygen, these properties being decisive in numerous applications.
Amoung these fluorinated compounds, specific compounds having a hydrogenated chain with a double bond: R.sub.F --CH.sub.2 --CH.dbd.CH--R.sub.H where R.sub.F is a fluorinated carbon chain and R.sub.H a saturated hydrogenated linear chain were recently prepared. Reference may be made to the following publications relating to this type of linear compounds and the applications thereof as blood substitutes or replacement of the vitrous humor in the eye: C. Cecutti et al., POTENTIAL BLOOD SUBSTITUTES SYNTHESIS AND MICROEMULSIFICATION OF MIXED HYDROGENATED AND FLUORINATED OILS, J. DISPERSION SCIENCE AND TECHNOLOGY, 7(3), 307-318 (1986); C. Cecutti et al., NEW FORMULTAION OF BLOOD SUBSTITUTES: OPTIMIZATION OF NOVEL FLUORINATED MICROEMULSIONS, Eur. J. Med. Chem. 24 (1989) 485-492 ; C. Cecutti et al., A NEW FORMULATION FOR BLOOD SUBSTITUTES, J. DISPERSION SCIENCE AND TECHNOLOGY, 11(2), 115-123 (1990). Anne NOVELLI, Thesis MICROEMULSIFICATION ET BIOCOMPATIBILITE D'UN RADIOPROTECTEUR HYDROPHILE ET D'UN TRANSPORTEUR D'OXYGENE HYDROPHOBE, I.N.P.T., presentation of May 18, 1990.
This family of linear fluorinated compounds has specific stability, density and oxygen solubilization properties which, in various applications, make the use thereof advantageous as compared to the other fluorinated compounds. Such properties result one the one hand from the central double bond and on the other hand from the hydrogenated chain located opposite to the fluorinated chain. The double bond reduces the volatility of the compound for a same number of carbons and increases their oxygen solubilization capacity. The presence of the hydrogenated chain leads to a density which is a function of the chain length, and which is lower than in the case of non hydrogenated fluorinated compounds having the same fluorinated chain. Accordingly, the combined choice of the fluorinated R.sub.F and hydrogenated R.sub.H chains allows to some extent to obtain liquid compounds with the desired density and number of fluorine atoms, i.e. a given oxygen solubilization capacity.
These linear fluorinated compounds are currently prepared by means of a method using the Wittig's reaction. However, the yield of this synthesis is low; for example, the average synthesis yields for fluorinated chains with eight carbon atoms are of the order of 50% (overall yield). Since the starting materials used in the Wittig's reaction are costly, the cost of the resulting linear fluorinated compounds is very high, which limits the possibility of their application considerably. To the knowledge of the inventors, these linear compounds were only synthesized in the laboratory for research purposes, and are not being used. Moreover, these linear compounds have good oxygen solubilization properties, provided that their fluorinated chain has a comparatively high number of carbon atoms, which is associated with high density compounds. For numerous applications, the density/oxygen solubilization compromise would therefore not be easy to obtain with such type of compounds.


DISCLOSURE OF THE INVENTION

The present invention aims at providing novel fluorinated organic compounds the properties thereof are at least as attractive as the above-mentioned linear fluorinated compounds, but with the benefit of higher synthesis yields, allowing a reduction in the preparation costs thereof in marked proportions, whereby the possibilities of application would be widened.
A further object of the invention is to provide flu

REFERENCES:
by C. Cecutti et al., "Potential Blood Substitutes Synthesis and Microemulsification of mixed Hydrogenated and Fluorinated Oils", J. Dispersion Science and Technology, vol. 7, No. 3, 1986, pp. 307-318.
by C. Cecutti et al., "New Formulation of Blood Substitutes; Optimization of Novel Fluorinated Microemulsions", Eur. J. Med. Chem., vol. 24, 1989, pp. 485-492.
by C. Cecutti et al., "A New Formulation for Blood Substitutes", J. Dispersion Science and Technology, vol. 11, No. 2, 1990, pp. 115-123.
by A. Novelli, "Microemulsification et Biocompatibilite d'un Radioprotecteur Hydrophile et d'un Transporteur d'Oxygene Hydrophobe", Le Titre De Docteur De L'Institut National Polytechnique De Toulouse, May 1990, pp. 9-10; 13-31 and 217-218.

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