Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1998-12-23
2000-12-12
Gorr, Rachel
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560160, 560184, 560167, 528 49, 528 69, 528 70, C08G 1871
Patent
active
061601616
DESCRIPTION:
BRIEF SUMMARY
The invention relates to the synthesis of new per(poly)fluorinated polyoxyethylated carbamates. These compounds can be used as surfactants or co-surfactants for phospholipids intended for the preparation or stabilisation of fluorocarbon emulsions, notably emulsions for biomedical applications.
Non-ionic fluorinated surfactants are currently used in various fields of application, such as fire-fighting, the plastics, rubber and petroleum industries, in the treatment of textiles, leather, paintings, pigments and coatings, mining and metallurgy, agriculture and silviculture, photography and the graphic arts, in biomedicine to deactivate coated viruses and thus in the preparation of blood products without substantial denaturation of the plasma proteins etc.
Although in some cases it is possible to content oneself with mixtures of polyoxyethylated surfactants [J. Am. Chem. Soc. 106 (1984) 6162], the finer applications (emulsions, microemulsions, gels etc.) occasionally demand homogeneous compounds with perfectly defined structure and of great purity, thus numerous monodisperse detergents have been developed despite their high cost. In particular may be cited: where p is generally less than 3, R.sub.F is a perfluorinated chain, W designates a chain of oxyethylene units (OC.sub.2 H.sub.4), where one or more oxygen atoms may be replaced by sulphur atoms, are described in FR-A-2,565,226; R.sub.F C.sub.2 H.sub.4 S(C.sub.2 H.sub.4 O).sub.m C.sub.2 H.sub.4 (C.sub.2 H.sub.4 O).sub.n H presenting oxyethylene and thioethyl groups which can be put together as desired and the number of which can be controlled accurately [Tenside Surf. Det. 31 51994) 124]; C.sub.n F.sub.2n+1 CH.sub.2 O(C.sub.2 H.sub.4 O).sub.m H which are excellent emulsifiers of fluorocarbons [EP-A-0051526; Tetrahedron, 39, (1983) 1313; J. Am. Chem. Soc., 106 (1984 6162; Langmuir, 10 (1994) 2131]. O).sub.m H [J. Fluorine Chem., 34 (1987) 385; R.sub.F (CH.sub.2).sub.n CONH(C.sub.2 H.sub.4 O).sub.M H [J. Chem. Research. (S), (1984) 292: J. Chem. Research (M), (1984) 2672], R.sub.F C.sub.2 H.sub.4 NHCOC(CH.sub.2 OH).sub.2 CH.sub.3 [J. Chem. Soc., Chem. Commun., (1991) 863], R.sub.F C.sub.2 H.sub.4 CH(CONH(C.sub.2 H.sub.4 O).sub.m H).sub.2 (MC Patent No 2334 1996)], the product sold under the trade mark XMO-10 with the formula C.sub.3 F.sub.7 O(CF.sub.2).sub.3 CONH(CH.sub.2).sub.3 N(O)(CH.sub.3).sub.2 [Prog. Clin. Biol. Res., 122 (1983) 169]; R.sub.F (CH.sub.2).sub.p C(O)N[OC.sub.2 H.sub.4).sub.n Me].sub.2 where p is generally less than 3. Products of this family where p=1 or 0 are described in French Patent Application No 87.06515. H.sub.4 O).sub.n Me where p is less than 5, in which R.sub.F is a perfluorinated chain and Q designates groups such as --O(CH.sub.2).sub.4 O--, --O(CH.sub.2).sub.3 C(O)O--, --CH(OEt)CH.sub.2 O-- [Biomat., Art. Cells, Biotech., 20 (1992) 115; J. Fluorine Chem., 68 (1994) 221]. H.sub.4 N[(C.sub.2 H.sub.4 O).sub.m R].sub.2 where m is 2 or 3, R.sub.F is a perfluorinated chain and R represents a hydrogen atom or a methyl group [J. Colloid Interface Sci., 177 (1996) 101]. purification of membrane proteins [New J. Chem., 1994, 18, 839] or in the preparation of organised systems [Carbohydrates as Organic Raw Materials, Verlagsgesellschaft. (Ed), Weinheim, (1993) 209-259: Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications R Filler et al (Eds), Elsevier, (1993) 339-380].
This invention relates to the use of per(poly)fluorinated polyoxyethylated carbamates as anti-thrombosis agents or as a surfactant or as a co-surfactant for, in particular, phospholipids, especially of egg yolk, to produce or stabilise emulsions, especially fluorocarbon emulsions intended, for example, for a biomedical application, for example as injectable oxygen transporters (called "blood substitutes"). The general formula for these carbamates is: ##STR1## in which R.sub.F represents a perfluorinated group containing between 1 and 18 carbon atoms, W represents an oxo group or nothing, n is an integer from 1 to 10, m is from 2 to 6, 80 or not define
REFERENCES:
patent: 4461717 (1984-07-01), Moore
patent: 4942164 (1990-07-01), Baum
Cambon Aime
Conte Lino
Edwards Carl Martin
Franke Ralf-Peter
Gambaretto Giampaolo
F2 Chemicals Limited
Gorr Rachel
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