PT91501B - Processo para a preparacao de uma composicao que inclui complexos hospedeiros/ hospedes que formam cavitatos ou clatratos como agentes de contraste - Google Patents
Processo para a preparacao de uma composicao que inclui complexos hospedeiros/ hospedes que formam cavitatos ou clatratos como agentes de contraste Download PDFInfo
- Publication number
- PT91501B PT91501B PT91501A PT9150189A PT91501B PT 91501 B PT91501 B PT 91501B PT 91501 A PT91501 A PT 91501A PT 9150189 A PT9150189 A PT 9150189A PT 91501 B PT91501 B PT 91501B
- Authority
- PT
- Portugal
- Prior art keywords
- derivatives
- host
- solution
- phenyl
- acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 230000008602 contraction Effects 0.000 title 1
- 239000002872 contrast media Substances 0.000 claims abstract description 5
- 238000011835 investigation Methods 0.000 claims abstract description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 19
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- -1 (2,2,4-tri-methylchroman-4-yl) -phenyl Chemical group 0.000 claims description 11
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 claims description 8
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910001868 water Inorganic materials 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- YECHEDVCXXVLIY-UHFFFAOYSA-N cyclotriveratrylene Chemical group C1C2=CC(OC)=C(OC)C=C2CC2=CC(OC)=C(OC)C=C2CC2=C1C=C(OC)C(OC)=C2 YECHEDVCXXVLIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- BDLNCFCZHNKBGI-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)benzene Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=C([N+]([O-])=O)C=C1 BDLNCFCZHNKBGI-UHFFFAOYSA-N 0.000 claims description 2
- NRZSTQWBQJYRAN-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-thiochromen-4-yl)phenol Chemical compound C12=CC=CC=C2SC(C)(C)CC1(C)C1=CC=C(O)C=C1 NRZSTQWBQJYRAN-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 2
- 241000234282 Allium Species 0.000 claims description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- KVDANDXXMLZEGA-UHFFFAOYSA-N N[Ni]C#N Chemical compound N[Ni]C#N KVDANDXXMLZEGA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 2
- 229960003964 deoxycholic acid Drugs 0.000 claims description 2
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002211 flavins Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052815 sulfur oxide Inorganic materials 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- XPGUQALNGZNWRM-UHFFFAOYSA-L 4-methylpyridine;nickel(2+);dithiocyanate Chemical class CC1=CC=NC=C1.CC1=CC=NC=C1.CC1=CC=NC=C1.CC1=CC=NC=C1.N#CS[Ni]SC#N XPGUQALNGZNWRM-UHFFFAOYSA-L 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims 1
- 229940039231 contrast media Drugs 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 55
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000001035 drying Methods 0.000 description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
- 239000005968 1-Decanol Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 229960004337 hydroquinone Drugs 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052724 xenon Inorganic materials 0.000 description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000001282 iso-butane Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002604 ultrasonography Methods 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910018503 SF6 Inorganic materials 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229950011148 cyclopropane Drugs 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 3
- 229960000909 sulfur hexafluoride Drugs 0.000 description 3
- ZIKHLMVJGCYVAC-UHFFFAOYSA-N tri-o-thymotide Chemical compound O1C(=O)C2=C(C)C=CC(C(C)C)=C2OC(=O)C2=C(C)C=CC(C(C)C)=C2OC(=O)C2=C1C(C(C)C)=CC=C2C ZIKHLMVJGCYVAC-UHFFFAOYSA-N 0.000 description 3
- RCHBEKYABIIBAT-UHFFFAOYSA-N 2,4,4-trimethyl-2,3-dihydrochromene Chemical compound C1=CC=C2OC(C)CC(C)(C)C2=C1 RCHBEKYABIIBAT-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- BLIQUJLAJXRXSG-UHFFFAOYSA-N 1-benzyl-3-(trifluoromethyl)pyrrolidin-1-ium-3-carboxylate Chemical compound C1C(C(=O)O)(C(F)(F)F)CCN1CC1=CC=CC=C1 BLIQUJLAJXRXSG-UHFFFAOYSA-N 0.000 description 1
- VTZDWVXUYPHSKJ-UHFFFAOYSA-N 4-(2,2,4,7-tetramethyl-3h-thiochromen-4-yl)phenol Chemical compound C=1C(C)=CC=C2C=1SC(C)(C)CC2(C)C1=CC=C(O)C=C1 VTZDWVXUYPHSKJ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000386115 Coras Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BMYPQOLESFVQPA-UHFFFAOYSA-N O=[Xe]=O Chemical compound O=[Xe]=O BMYPQOLESFVQPA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 101000916532 Rattus norvegicus Zinc finger and BTB domain-containing protein 38 Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 229910000070 arsenic hydride Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 210000001214 frontal sinus Anatomy 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GJPZDZHEZDANAG-UHFFFAOYSA-N methyl n-(1h-benzimidazol-2-yl)carbamate;propan-2-yl n-(3,4-diethoxyphenyl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.CCOC1=CC=C(NC(=O)OC(C)C)C=C1OCC GJPZDZHEZDANAG-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 210000004165 myocardium Anatomy 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
- ALYMILAYQDOMFU-UHFFFAOYSA-L nickel(2+);dithiocyanate Chemical class [Ni+2].[S-]C#N.[S-]C#N ALYMILAYQDOMFU-UHFFFAOYSA-L 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- ARUUTJKURHLAMI-UHFFFAOYSA-N xenon hexafluoride Chemical compound F[Xe](F)(F)(F)(F)F ARUUTJKURHLAMI-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
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/189—Host-guest complexes, e.g. cyclodextrins
-
- 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
- A61K49/228—Host-guest complexes, clathrates, chelates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Medicinal Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Acoustics & Sound (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3828905A DE3828905A1 (de) | 1988-08-23 | 1988-08-23 | Mittel bestehend aus cavitate oder clathrate bildenden wirt/gast-komplexen als kontrastmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT91501A PT91501A (pt) | 1990-03-08 |
| PT91501B true PT91501B (pt) | 1995-05-31 |
Family
ID=6361599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT91501A PT91501B (pt) | 1988-08-23 | 1989-08-22 | Processo para a preparacao de uma composicao que inclui complexos hospedeiros/ hospedes que formam cavitatos ou clatratos como agentes de contraste |
Country Status (12)
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922304A (en) | 1989-12-22 | 1999-07-13 | Imarx Pharmaceutical Corp. | Gaseous precursor filled microspheres as magnetic resonance imaging contrast agents |
| US6001335A (en) | 1989-12-22 | 1999-12-14 | Imarx Pharmaceutical Corp. | Contrasting agents for ultrasonic imaging and methods for preparing the same |
| US6551576B1 (en) | 1989-12-22 | 2003-04-22 | Bristol-Myers Squibb Medical Imaging, Inc. | Container with multi-phase composition for use in diagnostic and therapeutic applications |
| US6146657A (en) | 1989-12-22 | 2000-11-14 | Imarx Pharmaceutical Corp. | Gas-filled lipid spheres for use in diagnostic and therapeutic applications |
| US5542935A (en) | 1989-12-22 | 1996-08-06 | Imarx Pharmaceutical Corp. | Therapeutic delivery systems related applications |
| US5776429A (en) | 1989-12-22 | 1998-07-07 | Imarx Pharmaceutical Corp. | Method of preparing gas-filled microspheres using a lyophilized lipids |
| US20020150539A1 (en) | 1989-12-22 | 2002-10-17 | Unger Evan C. | Ultrasound imaging and treatment |
| US5580575A (en) | 1989-12-22 | 1996-12-03 | Imarx Pharmaceutical Corp. | Therapeutic drug delivery systems |
| US5469854A (en) | 1989-12-22 | 1995-11-28 | Imarx Pharmaceutical Corp. | Methods of preparing gas-filled liposomes |
| US6088613A (en) | 1989-12-22 | 2000-07-11 | Imarx Pharmaceutical Corp. | Method of magnetic resonance focused surgical and therapeutic ultrasound |
| US5585112A (en) | 1989-12-22 | 1996-12-17 | Imarx Pharmaceutical Corp. | Method of preparing gas and gaseous precursor-filled microspheres |
| IN172208B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 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 |
| US5445813A (en) * | 1992-11-02 | 1995-08-29 | Bracco International B.V. | Stable microbubble suspensions as enhancement agents for ultrasound echography |
| US5205290A (en) | 1991-04-05 | 1993-04-27 | Unger Evan C | Low density microspheres and their use as contrast agents for computed tomography |
| US5874062A (en) | 1991-04-05 | 1999-02-23 | Imarx Pharmaceutical Corp. | Methods of computed tomography using perfluorocarbon gaseous filled microspheres as contrast agents |
| JPH06510758A (ja) * | 1991-07-05 | 1994-12-01 | ニユコメド・イメージング・アクシエセルカペト | 造影剤におけるまたは造影剤に関する改良 |
| US5409688A (en) * | 1991-09-17 | 1995-04-25 | Sonus Pharmaceuticals, Inc. | Gaseous ultrasound contrast media |
| US6723303B1 (en) | 1991-09-17 | 2004-04-20 | Amersham Health, As | Ultrasound contrast agents including protein stabilized microspheres of perfluoropropane, perfluorobutane or perfluoropentane |
| KR100191303B1 (ko) * | 1991-09-17 | 1999-06-15 | 씨. 큐웨이 스티븐 | 기체상의 초음파 조영제 및 초음파 조영제로서 사용하기 위한 기체를 선택하는 방법 |
| MX9205298A (es) | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
| IL104084A (en) * | 1992-01-24 | 1996-09-12 | Bracco Int Bv | Long-lasting aqueous suspensions of pressure-resistant gas-filled microvesicles their preparation and contrast agents consisting of them |
| US5558855A (en) * | 1993-01-25 | 1996-09-24 | Sonus Pharmaceuticals | Phase shift colloids as ultrasound contrast agents |
| NZ262237A (en) * | 1993-01-25 | 1997-06-24 | Sonus Pharma Inc | Ultrasound contrast agents comprising phase shift colloids having a boiling point below the body temperature of the animal it is used in |
| IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
| CN1061893C (zh) * | 1993-03-08 | 2001-02-14 | 柯铭清 | 声学造影剂 |
| US5716597A (en) * | 1993-06-04 | 1998-02-10 | Molecular Biosystems, Inc. | Emulsions as contrast agents and method of use |
| CA2164813C (en) * | 1993-07-30 | 2009-11-24 | Ernest G. Schutt | Stabilized microbubble compositions for ultrasound |
| US5798091A (en) | 1993-07-30 | 1998-08-25 | Alliance Pharmaceutical Corp. | Stabilized gas emulsion containing phospholipid for ultrasound contrast enhancement |
| US7083572B2 (en) | 1993-11-30 | 2006-08-01 | Bristol-Myers Squibb Medical Imaging, Inc. | Therapeutic delivery systems |
| DK0682530T3 (da) | 1993-12-15 | 2003-07-14 | Bracco Research Sa | Gasblandinger, der kan anvendes som ultralydkontrastmidler |
| US5545396A (en) | 1994-04-08 | 1996-08-13 | The Research Foundation Of State University Of New York | Magnetic resonance imaging using hyperpolarized noble gases |
| US5622687A (en) * | 1994-11-15 | 1997-04-22 | Molecular Biosystems, Inc. | Calixarene conjugates useful as MRI and CT diagnostic imaging agents |
| US6743779B1 (en) | 1994-11-29 | 2004-06-01 | Imarx Pharmaceutical Corp. | Methods for delivering compounds into a cell |
| US5830430A (en) | 1995-02-21 | 1998-11-03 | Imarx Pharmaceutical Corp. | Cationic lipids and the use thereof |
| US6139819A (en) | 1995-06-07 | 2000-10-31 | Imarx Pharmaceutical Corp. | Targeted contrast agents for diagnostic and therapeutic use |
| US6521211B1 (en) | 1995-06-07 | 2003-02-18 | Bristol-Myers Squibb Medical Imaging, Inc. | Methods of imaging and treatment with targeted compositions |
| US6033645A (en) | 1996-06-19 | 2000-03-07 | Unger; Evan C. | Methods for diagnostic imaging by regulating the administration rate of a contrast agent |
| US6231834B1 (en) | 1995-06-07 | 2001-05-15 | Imarx Pharmaceutical Corp. | Methods for ultrasound imaging involving the use of a contrast agent and multiple images and processing of same |
| EP0766968B1 (en) * | 1995-10-06 | 2001-01-17 | Nihon Medi-Physics Co., Ltd. | Diagnostic imaging agent |
| DE19543077C2 (de) * | 1995-11-13 | 1997-10-16 | Schering Ag | Verwendung von gashaltigen Metallkomplexen als Ultraschallkontrastmittel |
| PT904113E (pt) * | 1996-03-05 | 2004-09-30 | Acusphere Inc | Gases fluorados microencapsulados para utilizacao como agentes de aquisicao de imagem |
| US5611344A (en) * | 1996-03-05 | 1997-03-18 | Acusphere, Inc. | Microencapsulated fluorinated gases for use as imaging agents |
| JP2001507207A (ja) | 1996-05-01 | 2001-06-05 | イマアーレクス・フアーマシユーチカル・コーポレーシヨン | 化合物を細胞に送達する方法 |
| US6414139B1 (en) | 1996-09-03 | 2002-07-02 | Imarx Therapeutics, Inc. | Silicon amphiphilic compounds and the use thereof |
| US5846517A (en) | 1996-09-11 | 1998-12-08 | Imarx Pharmaceutical Corp. | Methods for diagnostic imaging using a renal contrast agent and a vasodilator |
| DE19709704C2 (de) * | 1997-03-10 | 1999-11-04 | Michael Georgieff | Verwendung einer flüssigen Präparation von Xenon zur intravenösen Verabreichung bei Einleitung und/oder Aufrechterhaltung der Anaesthesie |
| US6143276A (en) | 1997-03-21 | 2000-11-07 | Imarx Pharmaceutical Corp. | Methods for delivering bioactive agents to regions of elevated temperatures |
| US6120751A (en) | 1997-03-21 | 2000-09-19 | Imarx Pharmaceutical Corp. | Charged lipids and uses for the same |
| US6090800A (en) | 1997-05-06 | 2000-07-18 | Imarx Pharmaceutical Corp. | Lipid soluble steroid prodrugs |
| US6537246B1 (en) | 1997-06-18 | 2003-03-25 | Imarx Therapeutics, Inc. | Oxygen delivery agents and uses for the same |
| US7452551B1 (en) | 2000-10-30 | 2008-11-18 | Imarx Therapeutics, Inc. | Targeted compositions for diagnostic and therapeutic use |
| US6416740B1 (en) | 1997-05-13 | 2002-07-09 | Bristol-Myers Squibb Medical Imaging, Inc. | Acoustically active drug delivery systems |
| US6548047B1 (en) | 1997-09-15 | 2003-04-15 | Bristol-Myers Squibb Medical Imaging, Inc. | Thermal preactivation of gaseous precursor filled compositions |
| US6123923A (en) | 1997-12-18 | 2000-09-26 | Imarx Pharmaceutical Corp. | Optoacoustic contrast agents and methods for their use |
| US20010003580A1 (en) | 1998-01-14 | 2001-06-14 | Poh K. Hui | Preparation of a lipid blend and a phospholipid suspension containing the lipid blend |
| US6284222B1 (en) | 1998-11-03 | 2001-09-04 | Medi--Physics, Inc. | Hyperpolarized helium-3 microbubble gas entrapment methods |
| DE19851605A1 (de) * | 1998-11-09 | 2000-05-11 | Messer Griesheim Gmbh | Mikropartikel enthaltendes Injektionsanästhesiemittel |
| JP4544551B2 (ja) * | 1999-07-28 | 2010-09-15 | 日本曹達株式会社 | トリ−ｏ−チモチド類を成分化合物とする分子化合物 |
| WO2002045721A1 (en) * | 2000-12-04 | 2002-06-13 | Uws Ventures Limited | Noble gas complexes |
| US8012457B2 (en) | 2004-06-04 | 2011-09-06 | Acusphere, Inc. | Ultrasound contrast agent dosage formulation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4276885A (en) * | 1979-05-04 | 1981-07-07 | Rasor Associates, Inc | Ultrasonic image enhancement |
| US4718433A (en) * | 1983-01-27 | 1988-01-12 | Feinstein Steven B | Contrast agents for ultrasonic imaging |
| DE3637926C1 (de) * | 1986-11-05 | 1987-11-26 | Schering Ag | Ultraschall-Manometrieverfahren in einer Fluessigkeit mittels Mikroblaeschen |
-
1988
- 1988-08-23 DE DE3828905A patent/DE3828905A1/de not_active Ceased
-
1989
- 1989-08-18 WO PCT/DE1989/000548 patent/WO1990001952A1/de unknown
- 1989-08-18 IE IE268589A patent/IE65168B1/en not_active IP Right Cessation
- 1989-08-18 ES ES89250016T patent/ES2042986T3/es not_active Expired - Lifetime
- 1989-08-18 DE DE8989250016T patent/DE58901585D1/de not_active Expired - Lifetime
- 1989-08-18 EP EP89250016A patent/EP0357163B1/de not_active Expired - Lifetime
- 1989-08-18 JP JP01508694A patent/JP3142539B2/ja not_active Expired - Fee Related
- 1989-08-18 AT AT89250016T patent/ATE76758T1/de not_active IP Right Cessation
- 1989-08-18 AU AU40651/89A patent/AU641363B2/en not_active Ceased
- 1989-08-22 PT PT91501A patent/PT91501B/pt not_active IP Right Cessation
-
1991
- 1991-02-21 DK DK030391A patent/DK30391A/da not_active Application Discontinuation
- 1991-02-22 NO NO910711A patent/NO302101B1/no not_active IP Right Cessation
-
1992
- 1992-08-20 GR GR920401406T patent/GR3005457T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO910711L (no) | 1991-02-22 |
| DK30391D0 (da) | 1991-02-21 |
| GR3005457T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-24 |
| DK30391A (da) | 1991-02-21 |
| JP3142539B2 (ja) | 2001-03-07 |
| ATE76758T1 (de) | 1992-06-15 |
| IE892685L (en) | 1990-02-23 |
| DE3828905A1 (de) | 1990-03-15 |
| IE65168B1 (en) | 1995-10-04 |
| DE58901585D1 (de) | 1992-07-09 |
| WO1990001952A1 (de) | 1990-03-08 |
| EP0357163B1 (de) | 1992-06-03 |
| AU641363B2 (en) | 1993-09-23 |
| AU4065189A (en) | 1990-03-23 |
| NO910711D0 (no) | 1991-02-22 |
| NO302101B1 (no) | 1998-01-26 |
| PT91501A (pt) | 1990-03-08 |
| JPH04501559A (ja) | 1992-03-19 |
| EP0357163A1 (de) | 1990-03-07 |
| ES2042986T3 (es) | 1993-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PT91501B (pt) | Processo para a preparacao de uma composicao que inclui complexos hospedeiros/ hospedes que formam cavitatos ou clatratos como agentes de contraste | |
| AU627456B2 (en) | Ultrasonic contrast medium made up of small gas bubbles and fatty-acid-containing microparticles | |
| JPS62155224A (ja) | 超音波検査用造影剤及びその製造方法 | |
| Wang et al. | High‐Performance Upconversion Nanoprobes for Multimodal MR Imaging of Acute Ischemic Stroke | |
| Langheinrich et al. | Acute rat lung injury: feasibility of assessment with micro-CT | |
| JPS59205328A (ja) | 微粒子及び気泡を含有する超音波診断用造影剤及びその製法 | |
| JPS62501070A (ja) | Ｎｍｒ造影剤としてのガドリニウムキレ−ト類 | |
| JPS61155338A (ja) | 診断用組成物 | |
| PT96691B (pt) | Processo para a preparacao de microparticulas de polimeros biodegradaveis e de composicoes farmaceuticas que os contem | |
| Wolters et al. | Clinical perspectives of hybrid proton-fluorine magnetic resonance imaging and spectroscopy | |
| CN116099011B (zh) | 一种irmof-8或irmof-10在常温条件下在超灵敏磁共振成像中的应用 | |
| Holman et al. | Perfluorocarbon emulsion contrast agents: A mini review | |
| CN115400229B (zh) | 一种金属有机骨架纳米造影剂在超灵敏磁共振成像中的应用 | |
| Vaccaro et al. | Supramolecular aggregates of amphiphilic gadolinium complexes as blood pool MRI/MRA contrast agents: physicochemical characterization | |
| Matsumoto et al. | Proton hyperpolarization relay from nanocrystals to liquid water | |
| CN115558000B (zh) | 一种钌-钆异核杂金属配合物及其制备方法和应用 | |
| JP5015606B2 (ja) | モレキュラーイメージング用の超音波造影剤 | |
| JP2007517858A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| Vollett et al. | A Manganese Porphyrin Platform for the Design and Synthesis of Molecular and Targeted MRI Contrast Agents | |
| Noel et al. | New approaches to acute kidney injury | |
| Melone et al. | Cyclodextrin‐Based Organic Radical Contrast Agents for in vivo Imaging of Gliomas | |
| CN115073726B (zh) | 一种靶向m2型巨噬细胞甘露糖受体的超声分子探针及其制备方法与应用 | |
| US10814022B2 (en) | Oxamide nanogel, a preparation method of the same, and use thereof | |
| CN110772649A (zh) | 一种多孔高分子超声造影剂及其制备方法 | |
| Seitenfus et al. | Aerosol Distribution Pattern of a Single-port Device: New Perspective Treatment for Peritoneal Carcinomatosis in Brazil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG3A | Patent granted, date of granting |
Effective date: 19941123 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20000531 |