CA2750230C - Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran - Google Patents
Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran Download PDFInfo
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- CA2750230C CA2750230C CA2750230A CA2750230A CA2750230C CA 2750230 C CA2750230 C CA 2750230C CA 2750230 A CA2750230 A CA 2750230A CA 2750230 A CA2750230 A CA 2750230A CA 2750230 C CA2750230 C CA 2750230C
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- CA
- Canada
- Prior art keywords
- composition
- dextran
- dtpa
- concentration
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 135
- 229920002307 Dextran Polymers 0.000 title claims abstract description 95
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229960003330 pentetic acid Drugs 0.000 title claims abstract description 42
- 238000000163 radioactive labelling Methods 0.000 title claims abstract description 27
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000004471 Glycine Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000003085 diluting agent Substances 0.000 claims abstract description 28
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 22
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 10
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 10
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 9
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 claims abstract description 7
- 229940056501 technetium 99m Drugs 0.000 claims abstract description 7
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 4
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical group [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 32
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 31
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 31
- 229960005055 sodium ascorbate Drugs 0.000 claims description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 26
- 239000006174 pH buffer Substances 0.000 claims description 19
- DPVHGFAJLZWDOC-PVXXTIHASA-N (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol;dihydrate Chemical group O.O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DPVHGFAJLZWDOC-PVXXTIHASA-N 0.000 claims description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 claims description 15
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 239000001488 sodium phosphate Substances 0.000 claims description 13
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 13
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 235000006708 antioxidants Nutrition 0.000 claims description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 238000001514 detection method Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- -1 salt dihydrate Chemical class 0.000 claims description 8
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 claims description 7
- 239000002953 phosphate buffered saline Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 6
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 6
- 235000011009 potassium phosphates Nutrition 0.000 claims description 6
- 230000003247 decreasing effect Effects 0.000 claims description 5
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 5
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 5
- 239000007975 buffered saline Substances 0.000 claims description 4
- 230000007774 longterm Effects 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 18
- 239000008215 water for injection Substances 0.000 claims 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 10
- 239000011261 inert gas Substances 0.000 claims 7
- 150000002840 non-reducing disaccharides Chemical class 0.000 claims 6
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N neotrehalose Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 229940074409 trehalose dihydrate Drugs 0.000 claims 2
- 238000002788 crimping Methods 0.000 claims 1
- 229940127043 diagnostic radiopharmaceutical Drugs 0.000 claims 1
- 150000004683 dihydrates Chemical group 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 210000005005 sentinel lymph node Anatomy 0.000 claims 1
- 229940033078 sodium pertechnetate tc 99m Drugs 0.000 claims 1
- PTIBVSAWRDGWAE-UHFFFAOYSA-K trisodium;phosphate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[O-]P([O-])([O-])=O PTIBVSAWRDGWAE-UHFFFAOYSA-K 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 abstract description 13
- 238000002347 injection Methods 0.000 abstract description 9
- 239000007924 injection Substances 0.000 abstract description 9
- 230000002452 interceptive effect Effects 0.000 abstract description 8
- 150000002500 ions Chemical class 0.000 abstract description 7
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract description 2
- 235000011150 stannous chloride Nutrition 0.000 abstract description 2
- 239000001119 stannous chloride Substances 0.000 abstract description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 68
- 238000010828 elution Methods 0.000 description 44
- 239000008186 active pharmaceutical agent Substances 0.000 description 42
- 229940088679 drug related substance Drugs 0.000 description 42
- 229960002449 glycine Drugs 0.000 description 28
- 229940126534 drug product Drugs 0.000 description 24
- 239000000825 pharmaceutical preparation Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 20
- 239000000546 pharmaceutical excipient Substances 0.000 description 19
- 239000003446 ligand Substances 0.000 description 17
- 239000000902 placebo Substances 0.000 description 13
- 229940068196 placebo Drugs 0.000 description 13
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 10
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 239000007974 sodium acetate buffer Substances 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 7
- 238000012216 screening Methods 0.000 description 7
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 6
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 6
- 229960002442 glucosamine Drugs 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000001509 sodium citrate Substances 0.000 description 6
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
- 239000004067 bulking agent Substances 0.000 description 5
- 239000012216 imaging agent Substances 0.000 description 5
- 239000004201 L-cysteine Substances 0.000 description 4
- 235000013878 L-cysteine Nutrition 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000002738 chelating agent Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229940095064 tartrate Drugs 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
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000008351 acetate buffer Substances 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 235000021472 generally recognized as safe Nutrition 0.000 description 3
- 239000012931 lyophilized formulation Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012633 nuclear imaging Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229940072107 ascorbate Drugs 0.000 description 2
- 238000001574 biopsy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229960001269 glycine hydrochloride Drugs 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 210000002751 lymph Anatomy 0.000 description 2
- 210000001165 lymph node Anatomy 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000012217 radiopharmaceutical Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000011270 sentinel node biopsy Methods 0.000 description 2
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 2
- 239000001433 sodium tartrate Substances 0.000 description 2
- 229960002167 sodium tartrate Drugs 0.000 description 2
- 235000011004 sodium tartrates Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 235000001508 sulfur Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000007944 thiolates Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WTTKTIBMFBIUSE-RXSVEWSESA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;sodium Chemical compound [Na].OC[C@H](O)[C@H]1OC(=O)C(O)=C1O WTTKTIBMFBIUSE-RXSVEWSESA-N 0.000 description 1
- JALIROBOQHQXST-DKWTVANSSA-N (2r)-2-amino-3-sulfanylpropanoic acid;sodium Chemical compound [Na].SC[C@H](N)C(O)=O JALIROBOQHQXST-DKWTVANSSA-N 0.000 description 1
- UVKNREAAHQRBKA-IEOVAKBOSA-I 2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;technetium-99(4+) Chemical compound [99Tc+4].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O UVKNREAAHQRBKA-IEOVAKBOSA-I 0.000 description 1
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- 101100505076 Caenorhabditis elegans gly-2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
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- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/005—Sugars; Derivatives thereof; Nucleosides; Nucleotides; Nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/06—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules
- A61K51/065—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules conjugates with carriers being macromolecules
-
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- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0491—Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers
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- C—CHEMISTRY; METALLURGY
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- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
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- C—CHEMISTRY; METALLURGY
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- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/534—Production of labelled immunochemicals with radioactive label
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/60—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances involving radioactive labelled substances
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Molecular Biology (AREA)
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| US12/362,778 US20100196272A1 (en) | 2009-01-30 | 2009-01-30 | Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran |
| US12/362,778 | 2009-01-30 | ||
| PCT/US2010/000222 WO2010087959A1 (en) | 2009-01-30 | 2010-01-28 | Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran |
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| US20100196272A1 (en) | 2009-01-30 | 2010-08-05 | Neoprobe Corporation | Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran |
| JP6163698B2 (ja) * | 2013-03-21 | 2017-07-19 | 国立大学法人 千葉大学 | マクロファージマンノース受容体を認識する新規多糖金属錯体化合物、及び、その医薬組成物 |
| US20150023876A1 (en) | 2013-07-22 | 2015-01-22 | Navidea Biopharmaceuticals, Inc. | Compositions, methods and kits for diagnosing and treating cd206 expressing cell-related disorders |
| JP5924795B2 (ja) | 2014-06-13 | 2016-05-25 | テンボロン オイ | 複合体 |
| US10806803B2 (en) | 2014-07-17 | 2020-10-20 | Ohio State Innovation Foundation | Compositions for targeting macrophages and other CD206 high expressing cells and methods of treating and diagnosis |
| WO2016011415A2 (en) * | 2014-07-17 | 2016-01-21 | Ohio State Innovation Foundation | Compounds and compositions for targeting macrophages and other mannose-binding c-type lectin receptor high expressing cells and methods of treating and diagnosis using same |
| EP3218352B1 (en) * | 2014-11-13 | 2020-08-05 | Waters Technologies Corporation | Method for liquid chromatography calibration for labeled n-glycans, method for preparing a dextran ladder calibrant and calibrant |
| GB201504064D0 (en) | 2015-03-10 | 2015-04-22 | Accretion Biotechnology Ltd | Method and kits for preparing radionuclide complexes |
| CN106317237B (zh) * | 2015-07-03 | 2019-07-19 | 华中科技大学 | 一种用于spect成像的当归多糖衍生物及其合成方法 |
| CN106188226B (zh) * | 2016-07-04 | 2019-12-24 | 江苏省原子医学研究所 | 一种用于淋巴结检查的大分子显像剂及其制备方法 |
| FR3054445B1 (fr) * | 2016-07-26 | 2019-07-05 | Laboratoires Cyclopharma | Synthese d'une composition d'agent radioactif |
| US10695450B2 (en) | 2016-07-26 | 2020-06-30 | Laboratoires Cyclopharma | Synthesis of a radioactive agent composition |
| US11007272B1 (en) | 2016-10-07 | 2021-05-18 | Navidea Biopharmaceuticals, Inc. | Compounds and methods for diagnosis and treatment of viral infections |
| JP6329302B2 (ja) * | 2017-05-10 | 2018-05-23 | 国立大学法人千葉大学 | マクロファージマンノース受容体を認識する新規多糖金属錯体化合物、及び、その医薬組成物 |
| WO2020202831A1 (ja) * | 2019-03-29 | 2020-10-08 | 国立研究開発法人量子科学技術研究開発機構 | 放射性医薬の製造方法及び放射性医薬 |
| JP2023533405A (ja) | 2020-07-08 | 2023-08-03 | ナビディア、バイオファーマスーティカルズ、インコーポレイテッド | 均一に定められた分子量のマンノシル化デキストランおよびその誘導体の合成 |
| US12006339B2 (en) | 2022-05-20 | 2024-06-11 | Navidea Biopharmaceuticals, Inc. | CD206 targeted drug delivery vehicles carrying novel bisphosphonate drug payloads via a degradable linker |
| JP2025535006A (ja) | 2022-10-03 | 2025-10-22 | ナビディア、バイオファーマスーティカルズ、インコーポレイテッド | 炭水化物ポリマーに結合されたアミン終端リーシュへの糖部分のアミド結合 |
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| IT1053508B (it) * | 1970-07-06 | 1981-10-10 | Searle & Co | Procedimento per prepare composizioni marcate adatte a mettere in evidenza alterazioni della mucosa gastrointestinale prodotto ottenuto e relativo metodo di impiego |
| US4364920A (en) * | 1975-04-30 | 1982-12-21 | Medi-Physics, Inc. | Stable diagnostic reagents |
| US4048296A (en) * | 1975-05-27 | 1977-09-13 | Mallinckrodt, Inc. | Radiopharmaceutical scanning agents |
| JPS5569517A (en) * | 1978-11-20 | 1980-05-26 | Nippon Mejifuijitsukusu Kk | Labelling preparation for labelling of erythrocytes with radio-active technetium |
| SE465907B (sv) | 1984-11-01 | 1991-11-18 | Nyegaard & Co As | Diagnosticeringsmedel innehaallande en paramagnetisk metall |
| US5336762A (en) | 1985-11-18 | 1994-08-09 | Access Pharmaceuticals, Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| US4822594A (en) | 1987-01-27 | 1989-04-18 | Gibby Wendell A | Contrast enhancing agents for magnetic resonance images |
| CS263561B1 (en) | 1987-09-18 | 1989-04-14 | Kery Vladimir | Process for preparing water soluble allylderivatives of oligo and polysaccharides |
| GB8801646D0 (en) * | 1988-01-26 | 1988-02-24 | Nycomed As | Chemical compounds |
| US5328679A (en) * | 1988-04-01 | 1994-07-12 | Immunomedics, Inc. | Methods for technetium/rhenium labeling of proteins |
| DD286598A5 (de) | 1989-06-29 | 1991-01-31 | Adw Der Ddr,Zi F. Mulekularbiologie,De | Verfahren zur einfuehrung von primaeren aminogruppen in wasserloesliche polymere |
| EP0516873A1 (en) * | 1991-06-06 | 1992-12-09 | THE STATE of ISRAEL Atomic Energy Commission Soreq Nuclear Research Center | A method and kit for protein labelling with 99 mTC |
| US5789578A (en) | 1996-01-11 | 1998-08-04 | Massey University | Methods for the preparation of resins with ligands attached thereto through a linking group comprising sulfide, sulfoxide or sulfone functionality |
| US20010055563A1 (en) * | 1999-09-09 | 2001-12-27 | Rhomed Incorporated | Post-labeling stabilization of radiolabeled proteins and peptides |
| US6066309A (en) * | 1996-02-02 | 2000-05-23 | Rhomed Incorporated | Post-labeling stabilization of radiolabeled proteins and peptides |
| WO1997028181A2 (en) * | 1996-02-02 | 1997-08-07 | Rhomed Incorporated | Post-labeling stabilization of radiolabeled proteins and peptides |
| AU5135698A (en) | 1996-11-28 | 1998-06-22 | Nihon Schering K.K. | Contrast compound, contrast medium for mri, and method for mri |
| ES2228536T3 (es) | 1999-05-14 | 2005-04-16 | The Regents Of The University Of California | Soporte macromolecular a base de dextrano para un farmaco y suministro de un agente de diagnosotico. |
| US6887462B2 (en) * | 2001-04-09 | 2005-05-03 | Chiron Corporation | HSA-free formulations of interferon-beta |
| US7666979B2 (en) | 2002-03-01 | 2010-02-23 | Bracco International B.V. | Methods for preparing multivalent constructs for therapeutic and diagnostic applications and methods of preparing the same |
| MXPA04011624A (es) * | 2002-05-24 | 2005-03-07 | Schering Corp | Anticuerpo neutralizante humano anti-igfr. |
| CA2517939C (en) | 2003-03-03 | 2015-11-24 | Dyax Corp. | Peptides that specifically bind hgf receptor (cmet) and uses thereof |
| DE602005001833T2 (de) * | 2004-10-29 | 2008-04-17 | Pharma Mar S.A., Sociedad Unipersonal | Zusammensetzungen enthaltend Ecteinascidin und einen Disaccharide |
| TWI398272B (zh) * | 2005-03-08 | 2013-06-11 | Intervet Int Bv | 化學定義的安定劑 |
| US20090155351A1 (en) * | 2005-10-04 | 2009-06-18 | Alk-Abello A/S | Solid Vaccine Formulation |
| AU2007234612B2 (en) * | 2006-12-14 | 2013-06-27 | Johnson & Johnson Regenerative Therapeutics, Llc | Protein stabilization formulations |
| EA019345B1 (ru) * | 2007-03-05 | 2014-03-31 | Кадила Хелзкэр Лимитед | Композиции, содержащие конъюгаты пэг-интерферон-альфа и рафинозу в качестве криопротектора |
| US20100196272A1 (en) | 2009-01-30 | 2010-08-05 | Neoprobe Corporation | Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran |
| US20150023876A1 (en) | 2013-07-22 | 2015-01-22 | Navidea Biopharmaceuticals, Inc. | Compositions, methods and kits for diagnosing and treating cd206 expressing cell-related disorders |
| EP3169336A4 (en) | 2014-07-17 | 2018-04-04 | Ohio State Innovation Foundation | Compositions for targeting macrophages and other cd206 high expressing cells and methods of treating and diagnosis |
| WO2016011415A2 (en) | 2014-07-17 | 2016-01-21 | Ohio State Innovation Foundation | Compounds and compositions for targeting macrophages and other mannose-binding c-type lectin receptor high expressing cells and methods of treating and diagnosis using same |
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2009
- 2009-01-30 US US12/362,778 patent/US20100196272A1/en not_active Abandoned
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2010
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- 2010-01-28 EP EP21152405.3A patent/EP3884965A1/en not_active Withdrawn
- 2010-01-28 AU AU2010208624A patent/AU2010208624B2/en not_active Ceased
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2012
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2013
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2016
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| JP2012516328A (ja) | 2012-07-19 |
| US20160347679A1 (en) | 2016-12-01 |
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| JP2019178133A (ja) | 2019-10-17 |
| US20100196272A1 (en) | 2010-08-05 |
| US20140023586A1 (en) | 2014-01-23 |
| WO2010087959A1 (en) | 2010-08-05 |
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| AU2010208624A1 (en) | 2011-08-25 |
| EP2392012B1 (en) | 2021-01-20 |
| JP6833892B2 (ja) | 2021-02-24 |
| KR20110115148A (ko) | 2011-10-20 |
| JP2017066148A (ja) | 2017-04-06 |
| EP2392012A1 (en) | 2011-12-07 |
| US9439985B2 (en) | 2016-09-13 |
| JP6509796B2 (ja) | 2019-05-08 |
| JP2015164933A (ja) | 2015-09-17 |
| US20120213700A1 (en) | 2012-08-23 |
| KR20170027874A (ko) | 2017-03-10 |
| EP3884965A1 (en) | 2021-09-29 |
| KR101765717B1 (ko) | 2017-08-07 |
| BRPI1007487A2 (pt) | 2018-02-20 |
| JP6040276B2 (ja) | 2016-12-07 |
| JP5743905B2 (ja) | 2015-07-01 |
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