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US3989843A Expired / Lapsed US ⏱️ 0.0 years remaining

Emulsification of fluorocarbon compounds for biological application as oxygen transporters

Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1974-10-22
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Granted: 1976-11-02
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Expires: 1994-10-22
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Abstract

Abstract Aqueous emulsions of polyfluorinated organic compounds useful as physiological transporters of oxygen, particularly in saline solutions isotonic with blood, are prepared by a method which comprises mixing a polyfluorinated compound with water or aqueous saline solution in the presence of at least one predominantly lipophilic polyfluorinated emulsifier and also at least one predominantly hydrophilic polyfluorinated emulsifier.

Inventors

  • 👤 Pierre Chabert
  • 👤 Louis Foulletier
  • 👤 Andre Lantz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-22 16:22
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/0012; A61K9/0019; A61K9/0026; A61K31/00; A61K31/02

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 232 words
A method of preparing an aqueous oxygen-transporting emulsion suitable for injection into the bloodstream which comprises i. combining water with from about 5 to 35% by volume base on the water of a polyfluorinated carbon compound which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluoronaphthalane, perfluoromethylnaphthalene, 1,1,2-trihydroperfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane or a substance having the formula C.sub.p F.sub.2p.sub.+1 --CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8; and a mixture of polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40, and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub. 2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 1 to 5; the weight ratio of hydrophilic surfactants to lipophilic surfactants is from about 1/1 to 2.5/1, ii. heating said emulsifiable composition, with stirring, to at least about 70° C and iii. cooling the heated composition with continued stirring until a
Claim 2
Independent Claim 232 words
A method of preparing an aqueous oxygen-transporting emulsion suitable for injection into the bloodstream which comprises i. combining water with from about 5 to 35% by volume base on the water of a polyfluorinated carbon compound which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluoronaphthalane, perfluoromethylnaphthalene, 1,1,2-trihydroperfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane or a substance having the formula C.sub.p F.sub.2p.sub.+1 --CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8; and a mixture of polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40, and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub. 2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 1 to 5; the weight ratio of hydrophilic surfactants to lipophilic surfactants is from about 1/1 to 2.5/1, ii. heating said emulsifiable composition, with stirring, to at least about 70° C and iii. cooling the heated composition with continued stirring until a
Claim 3
Dependent Claim 21 words
The method of claim 1 wherein each of the emulsifiers has the formula C.sub.6 F.sub.13 --C.sub.2 H.sub.4 --O(C.sub.2 H.sub.4 O).sub.n H.
Claim 4
Dependent Claim 11 words
the method of claim 1 wherein the emulsified polyfluorinated compound is
Claim 5
Dependent Claim 11 words
The method of claim 1 wherein the emulsified polyfluorinated compound is
Claim 6
Dependent Claim 11 words
The method of claim 1 wherein the emulsifiable composition also contains
Claim 7
Dependent Claim 195 words
An aqueous oxygen-transportation emulsion suitable for injection into the bloodstream which comprises water, a polyfluorinated carbon compound in an amount of from about 5 to 35% by volume of the water which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluoronaphthalane, perfluoromethylnaphthalane, 1,1,2-trihydro-perfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane, or a substance having the formula C.sub.p F.sub.2p.sub.+1 -CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8, and a mixture of nonionic polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40 and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4 and n is 1 to 5; the weight ratio of the hydrophilic surfactants
Claim 8
Dependent Claim 195 words
An aqueous oxygen-transportation emulsion suitable for injection into the bloodstream which comprises water, a polyfluorinated carbon compound in an amount of from about 5 to 35% by volume of the water which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluoronaphthalane, perfluoromethylnaphthalane, 1,1,2-trihydro-perfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane, or a substance having the formula C.sub.p F.sub.2p.sub.+1 -CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8, and a mixture of nonionic polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40 and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4 and n is 1 to 5; the weight ratio of the hydrophilic surfactants
Claim 9
Independent Claim 214 words
The method of promoting the transport of oxygen in the bloodstream which comprises injecting into said bloodstream an effective amount of an aqueous emulsion which contains water, from about 5 to 35% by volume of the water of a polyfluorinated carbon compound which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluronaphthalane, perfluoromethylnaphthalane, 1,1,2-trihydro-perfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane, or a substance having the formula: C.sub.p F.sub.2p.sub.+1 --CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8, and a mixture of nonionic polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40, and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4 and n is 1 to 5; the weight ratio of hydrophilic surfactants to lipophilic surfactants is from about 1/1 to 2.5/1.
Claim 10
Independent Claim 214 words
The method of promoting the transport of oxygen in the bloodstream which comprises injecting into said bloodstream an effective amount of an aqueous emulsion which contains water, from about 5 to 35% by volume of the water of a polyfluorinated carbon compound which is perfluorobutylamine, perfluorotributylamine, perfluorinated butyltetrahydrofuran, perfluorooctane, perfluronaphthalane, perfluoromethylnaphthalane, 1,1,2-trihydro-perfluoro-1-decane, 1,1,1,2,2-pentahydroperfluorodecane, or a substance having the formula: C.sub.p F.sub.2p.sub.+1 --CH=CH--C.sub.q F.sub.2q.sub.+1 wherein p and q are identical or different whole numbers from 2 to 10 and wherein their sum (p+q) is equal to or greater than 8, and a mixture of nonionic polyfluorinated surfactants whose total weight is from about 5 to 20% of the weight of the water, said mixture containing (1) predominantly hydrophilic surfactants (H) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4, and n is 6 to 40, and (2) predominantly lipophilic surfactants (L) of the formula: C.sub.m F.sub.2m.sub.+1 --(CH.sub.2).sub.a --O(CH.sub.2 CH.sub.2 O).sub.n H wherein m is 4 to 10, C m F 2m +1 -- is linear or branched, a is 1 to 4 and n is 1 to 5; the weight ratio of hydrophilic surfactants to lipophilic surfactants is from about 1/1 to 2.5/1.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-11-02 1980-05-03 1980-11-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-11-02 1984-05-03 1984-11-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-11-02 1988-05-03 1988-11-02 $7700.00 Window Closed / Lapsed

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