NO305685B2 - Ekkogene partikler, fremgangsmate for fremstilling av slike, anvendelser derav, diagnostikum eller terapeutikum inneholdende partiklene samt fremstilling derav. - Google Patents
Ekkogene partikler, fremgangsmate for fremstilling av slike, anvendelser derav, diagnostikum eller terapeutikum inneholdende partiklene samt fremstilling derav. Download PDFInfo
- Publication number
- NO305685B2 NO305685B2 NO19923424A NO923424A NO305685B2 NO 305685 B2 NO305685 B2 NO 305685B2 NO 19923424 A NO19923424 A NO 19923424A NO 923424 A NO923424 A NO 923424A NO 305685 B2 NO305685 B2 NO 305685B2
- Authority
- NO
- Norway
- Prior art keywords
- echogenic particles
- echogenic
- acid
- particles
- particles according
- Prior art date
Links
- 239000002245 particle Substances 0.000 title claims abstract description 149
- 238000000034 method Methods 0.000 title claims description 18
- 239000003814 drug Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000001694 spray drying Methods 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 210000004072 lung Anatomy 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- DSLBDPPHINVUID-REOHCLBHSA-N (2s)-2-aminobutanediamide Chemical compound NC(=O)[C@@H](N)CC(N)=O DSLBDPPHINVUID-REOHCLBHSA-N 0.000 claims description 10
- 238000007493 shaping process Methods 0.000 claims description 9
- 239000008280 blood Substances 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 229920002307 Dextran Polymers 0.000 claims description 5
- 108010010803 Gelatin Proteins 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 230000017531 blood circulation Effects 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 108010039918 Polylysine Proteins 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000656 polylysine Polymers 0.000 claims description 4
- -1 polymethylene malonate Polymers 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- 108010088751 Albumins Proteins 0.000 claims description 3
- 102000009027 Albumins Human genes 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 229920002732 Polyanhydride Polymers 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 229930182830 galactose Natural products 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- LFPLRGMCQXEYDO-UHFFFAOYSA-N 4-[1-(4-carboxyphenoxy)propoxy]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1OC(CC)OC1=CC=C(C(O)=O)C=C1 LFPLRGMCQXEYDO-UHFFFAOYSA-N 0.000 claims description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 229920000805 Polyaspartic acid Polymers 0.000 claims description 2
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 229920001710 Polyorthoester Polymers 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229940098773 bovine serum albumin Drugs 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 229910052756 noble gas Inorganic materials 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 108010064470 polyaspartate Proteins 0.000 claims description 2
- 229920002643 polyglutamic acid Polymers 0.000 claims description 2
- 239000004633 polyglycolic acid Substances 0.000 claims description 2
- 239000004626 polylactic acid Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 238000002604 ultrasonography Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000007921 spray Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000005242 cardiac chamber Anatomy 0.000 description 6
- 239000002872 contrast media Substances 0.000 description 6
- 239000002961 echo contrast media Substances 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- 210000003932 urinary bladder Anatomy 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- KPNBUPJZFJCCIQ-LURJTMIESA-N methyl L-lysinate Chemical compound COC(=O)[C@@H](N)CCCCN KPNBUPJZFJCCIQ-LURJTMIESA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000004891 diazines Chemical class 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000004626 scanning electron microscopy Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000012800 visualization Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YSAVZVORKRDODB-UHFFFAOYSA-N Diethyl tartrate Chemical compound CCOC(=O)C(O)C(O)C(=O)OCC YSAVZVORKRDODB-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000007373 indentation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 210000001147 pulmonary artery Anatomy 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 210000005245 right atrium Anatomy 0.000 description 2
- 210000005241 right ventricle Anatomy 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- JODXKZAUFHEYGO-JCYAYHJZSA-N (2R,3R)-2,3-dihydroxybutanedioyl dichloride Chemical class O[C@H]([C@@H](O)C(Cl)=O)C(Cl)=O JODXKZAUFHEYGO-JCYAYHJZSA-N 0.000 description 1
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- QPBGNSFASPVGTP-UHFFFAOYSA-N 2-bromoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Br)=C1 QPBGNSFASPVGTP-UHFFFAOYSA-N 0.000 description 1
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 description 1
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VLQJIOWOXQANRZ-RGMNGODLSA-N C(C=CC(=O)O)(=O)O.COC([C@@H](N)CCCCN)=O Chemical compound C(C=CC(=O)O)(=O)O.COC([C@@H](N)CCCCN)=O VLQJIOWOXQANRZ-RGMNGODLSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 108010002885 Polygeline Proteins 0.000 description 1
- INVRLGIKFANLFP-WDSKDSINSA-N [(4s,5s)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)O[C@@H](CO)[C@H](CO)O1 INVRLGIKFANLFP-WDSKDSINSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940119744 dextran 40 Drugs 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- OMPDFDUBCHJQKW-UHFFFAOYSA-N dichloromethane;furan Chemical compound ClCCl.C=1C=COC=1 OMPDFDUBCHJQKW-UHFFFAOYSA-N 0.000 description 1
- XEBCWEDRGPSHQH-UHFFFAOYSA-N diisopropyl tartrate Chemical compound CC(C)OC(=O)C(O)C(O)C(=O)OC(C)C XEBCWEDRGPSHQH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- BMBDJILYIZBBMQ-UHFFFAOYSA-N furan-2,3-dicarbonyl chloride Chemical class ClC(=O)C=1C=COC=1C(Cl)=O BMBDJILYIZBBMQ-UHFFFAOYSA-N 0.000 description 1
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 description 1
- OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000003058 plasma substitute Substances 0.000 description 1
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 1
- 239000002745 poly(ortho ester) Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/225—Microparticles, microcapsules
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4129187 | 1991-09-03 | ||
| DE4209488A DE4209488A1 (de) | 1992-03-24 | 1992-03-24 | Echogene Partikel, Verfahren zu deren Herstellung und deren Verwendung |
| DE4209487 | 1992-03-24 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO923424D0 NO923424D0 (no) | 1992-09-02 |
| NO923424L NO923424L (no) | 1993-03-04 |
| NO305685B1 NO305685B1 (no) | 1999-07-12 |
| NO305685B2 true NO305685B2 (no) | 1999-07-12 |
Family
ID=27202878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19923424A NO305685B2 (no) | 1991-09-03 | 1992-09-02 | Ekkogene partikler, fremgangsmate for fremstilling av slike, anvendelser derav, diagnostikum eller terapeutikum inneholdende partiklene samt fremstilling derav. |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0535387B2 (fr) |
| JP (1) | JPH05194276A (fr) |
| KR (1) | KR100267164B1 (fr) |
| AT (1) | ATE141518T1 (fr) |
| AU (1) | AU660039B2 (fr) |
| CA (1) | CA2077383A1 (fr) |
| DE (1) | DE59206943D1 (fr) |
| DK (1) | DK0535387T3 (fr) |
| ES (1) | ES2093160T5 (fr) |
| GR (1) | GR3021038T3 (fr) |
| NO (1) | NO305685B2 (fr) |
| NZ (1) | NZ244147A (fr) |
| TW (1) | TW222236B (fr) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7083778B2 (en) | 1991-05-03 | 2006-08-01 | Bracco International B.V. | Ultrasound contrast agents and methods of making and using them |
| US6989141B2 (en) | 1990-05-18 | 2006-01-24 | Bracco International B.V. | Ultrasound contrast agents and methods of making and using them |
| US6613306B1 (en) | 1990-04-02 | 2003-09-02 | Bracco International B.V. | Ultrasound contrast agents and methods of making and using them |
| USRE39146E1 (en) | 1990-04-02 | 2006-06-27 | Bracco International B.V. | Long-lasting aqueous dispersions or suspensions of pressure-resistant gas-filled microvesicles and methods for the preparation thereof |
| IN172208B (fr) | 1990-04-02 | 1993-05-01 | Sint Sa | |
| US5578292A (en) | 1991-11-20 | 1996-11-26 | Bracco International B.V. | Long-lasting aqueous dispersions or suspensions of pressure-resistant gas-filled microvesicles and methods for the preparation thereof |
| IL104084A (en) | 1992-01-24 | 1996-09-12 | Bracco Int Bv | Sustainable aqueous suspensions of pressure-resistant and gas-filled blisters, their preparation, and contrast agents containing them |
| DE4219723A1 (de) * | 1992-06-13 | 1993-12-16 | Schering Ag | Mikropartikel, Verfahren zu deren Herstellung, sowie die Verwendung dieser in der Diagnostik |
| WO1995003835A1 (fr) | 1993-07-30 | 1995-02-09 | Alliance Pharmaceutical Corp. | Compositions a mocrobulles stabilisees pour applications mettant en ×uvre des ultrasons |
| US5798091A (en) | 1993-07-30 | 1998-08-25 | Alliance Pharmaceutical Corp. | Stabilized gas emulsion containing phospholipid for ultrasound contrast enhancement |
| US6333021B1 (en) * | 1994-11-22 | 2001-12-25 | Bracco Research S.A. | Microcapsules, method of making and their use |
| AU6378096A (en) * | 1995-06-07 | 1996-12-30 | Brown University Research Foundation | Spray dried polymeric microparticles containing imaging agen ts |
| HU226714B1 (en) * | 1996-03-05 | 2009-07-28 | Acusphere | Microencapsulated fluorinated gases for use as imaging agents |
| US5611344A (en) * | 1996-03-05 | 1997-03-18 | Acusphere, Inc. | Microencapsulated fluorinated gases for use as imaging agents |
| US5837221A (en) | 1996-07-29 | 1998-11-17 | Acusphere, Inc. | Polymer-lipid microencapsulated gases for use as imaging agents |
| US8012457B2 (en) | 2004-06-04 | 2011-09-06 | Acusphere, Inc. | Ultrasound contrast agent dosage formulation |
| US20090148385A1 (en) * | 2004-11-19 | 2009-06-11 | Koninklijke Philips Electronics, N.V. | Ultrasound Contrast Agents For Molecular Imaging |
| EP1741968A1 (fr) * | 2005-07-08 | 2007-01-10 | Uponor Innovation Ab | Bague de serrage |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107288A (en) † | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| US4265251A (en) * | 1979-06-28 | 1981-05-05 | Rasor Associates, Inc. | Method of determining pressure within liquid containing vessel |
| US4718433A (en) † | 1983-01-27 | 1988-01-12 | Feinstein Steven B | Contrast agents for ultrasonic imaging |
| US4900540A (en) † | 1983-06-20 | 1990-02-13 | Trustees Of The University Of Massachusetts | Lipisomes containing gas for ultrasound detection |
| SE8701479L (sv) † | 1987-04-09 | 1988-10-10 | Carbomatrix Ab | Metod foer inneslutning av biologiskt verksamma preparat samt anvaendning daerav |
| IE61591B1 (en) † | 1987-12-29 | 1994-11-16 | Molecular Biosystems Inc | Concentrated stabilized microbubble-type ultrasonic imaging agent and method of production |
| SE465910B (sv) * | 1988-01-28 | 1991-11-18 | Jan Axel Svensson | Anordning foer sammankoppling av katetrar i en hudgenomgaang |
| JP2907911B2 (ja) * | 1988-02-05 | 1999-06-21 | シエーリング アクチエンゲゼルシヤフト | 超音波造影剤、その製造方法及び該超音波造影剤からなる診断又は治療用製剤 |
| US4957656A (en) † | 1988-09-14 | 1990-09-18 | Molecular Biosystems, Inc. | Continuous sonication method for preparing protein encapsulated microbubbles |
| FR2660864A1 (fr) * | 1990-04-13 | 1991-10-18 | Guerbet Sa | Composition de contraste, procede de preparation de cette composition et application a l'imagerie. |
| US5137928A (en) * | 1990-04-26 | 1992-08-11 | Hoechst Aktiengesellschaft | Ultrasonic contrast agents, processes for their preparation and the use thereof as diagnostic and therapeutic agents |
| AU636481B2 (en) † | 1990-05-18 | 1993-04-29 | Bracco International B.V. | Polymeric gas or air filled microballoons usable as suspensions in liquid carriers for ultrasonic echography |
| US5236693A (en) * | 1990-11-14 | 1993-08-17 | Brigham And Women's Hospital | Medical ultrasound contrast agent and method of using same |
| DE4219723A1 (de) † | 1992-06-13 | 1993-12-16 | Schering Ag | Mikropartikel, Verfahren zu deren Herstellung, sowie die Verwendung dieser in der Diagnostik |
-
1992
- 1992-08-31 NZ NZ244147A patent/NZ244147A/en unknown
- 1992-09-02 DE DE59206943T patent/DE59206943D1/de not_active Expired - Lifetime
- 1992-09-02 ES ES92114981T patent/ES2093160T5/es not_active Expired - Lifetime
- 1992-09-02 CA CA002077383A patent/CA2077383A1/fr not_active Abandoned
- 1992-09-02 DK DK92114981.1T patent/DK0535387T3/da active
- 1992-09-02 AT AT92114981T patent/ATE141518T1/de not_active IP Right Cessation
- 1992-09-02 EP EP92114981A patent/EP0535387B2/fr not_active Expired - Lifetime
- 1992-09-02 NO NO19923424A patent/NO305685B2/no not_active IP Right Cessation
- 1992-09-02 JP JP4234020A patent/JPH05194276A/ja not_active Abandoned
- 1992-09-02 KR KR1019920015887A patent/KR100267164B1/ko not_active IP Right Cessation
- 1992-09-02 AU AU22039/92A patent/AU660039B2/en not_active Ceased
- 1992-09-05 TW TW081107034A patent/TW222236B/zh active
-
1996
- 1996-09-13 GR GR960402397T patent/GR3021038T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2203992A (en) | 1993-03-11 |
| TW222236B (fr) | 1994-04-11 |
| NO305685B1 (no) | 1999-07-12 |
| DE59206943D1 (de) | 1996-09-26 |
| EP0535387A1 (fr) | 1993-04-07 |
| NO923424D0 (no) | 1992-09-02 |
| ATE141518T1 (de) | 1996-09-15 |
| NZ244147A (en) | 1994-09-27 |
| CA2077383A1 (fr) | 1993-03-04 |
| EP0535387B2 (fr) | 2001-10-04 |
| KR100267164B1 (ko) | 2000-10-16 |
| DK0535387T3 (da) | 1996-12-09 |
| GR3021038T3 (en) | 1996-12-31 |
| JPH05194276A (ja) | 1993-08-03 |
| EP0535387B1 (fr) | 1996-08-21 |
| ES2093160T5 (es) | 2002-03-16 |
| NO923424L (no) | 1993-03-04 |
| ES2093160T3 (es) | 1996-12-16 |
| KR930005618A (ko) | 1993-04-20 |
| AU660039B2 (en) | 1995-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO305685B2 (no) | Ekkogene partikler, fremgangsmate for fremstilling av slike, anvendelser derav, diagnostikum eller terapeutikum inneholdende partiklene samt fremstilling derav. | |
| US5205287A (en) | Ultrasonic contrast agents, processes for their preparation and the use thereof as diagnostic and therapeutic agents | |
| US5190982A (en) | Ultrasonic contrast agents, processes for their preparation and the use thereof as diagnostic and therapeutic agents | |
| JP3381930B2 (ja) | 超音波造影剤 | |
| US5674468A (en) | Contrast agents comprising gas-containing or gas-generating polymer microparticles or microballoons | |
| AU703652B2 (en) | Gas-filled microspheres with fluorine-containing shells | |
| US5562099A (en) | Polymeric microparticles containing agents for imaging | |
| AU740728B2 (en) | Method for enhancing the echogenicity and decreasing the attenuation of microencapsulated gases | |
| KR100477857B1 (ko) | 이미지형성제로사용되는마이크로캡슐화된불소첨가가스 | |
| US20060235193A1 (en) | Biocompatible materials and probes | |
| OA10096A (en) | Improvements in or relating to contrast agents | |
| JP2001527547A (ja) | 超音波コントラスト剤として、および、血流への薬剤デリバリーのために有用な微小パーティクル | |
| EP0707474A1 (fr) | Utilisation medicale d'aerogels organiques et d'aerogels organiques biodegradables | |
| Min et al. | Gas-generating polymeric microspheres for long-term and continuous in vivo ultrasound imaging | |
| US5613494A (en) | Polycondensates which contain tartaric acid derivatives, processes for their preparation and use thereof | |
| NO312940B1 (no) | Mikroinnkapslede fluorerte gasser for anvendelse som avbildningsmidler | |
| JP2007517858A (ja) | モレキュラーイメージング用の超音波造影剤 | |
| Qu et al. | Stepwise dual pH and redox-responsive cross-linked polypeptide nanoparticles for enhanced cellular uptake and effective cancer therapy | |
| JP2010138137A (ja) | パーフルオロカーボンエマルション及びそれから成る超音波造影剤 | |
| DE4209488A1 (de) | Echogene Partikel, Verfahren zu deren Herstellung und deren Verwendung | |
| CN101637613A (zh) | 一种脂质靶向超声造影剂及其制备方法 | |
| CN113929740B (zh) | 两亲性聚多肽及其制备方法和应用 | |
| US20040022732A1 (en) | Microparticles based on aspartic acid and use thereof as mri contrast agents | |
| CN116355048A (zh) | 一种靶向治疗角膜新生血管的多肽纳米材料及其制备方法和应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |