CA2156618A1 - Bifunctional chelators and their use in radiopharmaceuticals - Google Patents
Bifunctional chelators and their use in radiopharmaceuticalsInfo
- Publication number
- CA2156618A1 CA2156618A1 CA002156618A CA2156618A CA2156618A1 CA 2156618 A1 CA2156618 A1 CA 2156618A1 CA 002156618 A CA002156618 A CA 002156618A CA 2156618 A CA2156618 A CA 2156618A CA 2156618 A1 CA2156618 A1 CA 2156618A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- amino
- carbon atoms
- hydrogen atom
- hydroxy
- 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.)
- Abandoned
Links
- 239000012217 radiopharmaceutical Substances 0.000 title claims abstract description 21
- 229940121896 radiopharmaceutical Drugs 0.000 title claims abstract description 21
- 230000002799 radiopharmaceutical effect Effects 0.000 title claims abstract description 21
- 239000002738 chelating agent Substances 0.000 title description 7
- 230000001588 bifunctional effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 10
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 9
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 8
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 8
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 8
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 hydroxy, carboxy Chemical group 0.000 claims description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 claims description 31
- 229940056501 technetium 99m Drugs 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229920002521 macromolecule Polymers 0.000 claims description 18
- 150000003431 steroids Chemical class 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 239000012634 fragment Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 239000002502 liposome Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NUAGCEFLVCODRQ-KETPNHLCSA-N (3S)-3-[[(2S)-2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-[[(2S)-6-amino-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-3-carboxy-1-[[(2S,3S)-1-[[(2S,3S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1-oxohexan-2-yl]amino]-4-oxobutanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(C)=O)C(C)C)C1=CN=CN1 NUAGCEFLVCODRQ-KETPNHLCSA-N 0.000 claims description 2
- 108010092219 BQ 3020 Proteins 0.000 claims description 2
- NTSBFTNRWQVBCA-IVGDYKFASA-N His-leu-asp-ile-ile-trp Chemical compound C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)[C@@H](C)CC)C1=CN=CN1 NTSBFTNRWQVBCA-IVGDYKFASA-N 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 108010002990 endothelin (16-21) Proteins 0.000 claims description 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000002191 fatty alcohols Chemical class 0.000 claims 1
- 238000012800 visualization Methods 0.000 claims 1
- 229910052713 technetium Inorganic materials 0.000 abstract description 6
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 97
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
- 239000008363 phosphate buffer Substances 0.000 description 39
- 229910000397 disodium phosphate Inorganic materials 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000003480 eluent Substances 0.000 description 36
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 35
- 235000019800 disodium phosphate Nutrition 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- 230000002829 reductive effect Effects 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 238000002372 labelling Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- 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 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 18
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- 230000003637 steroidlike Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- ADHPSJYHXQTWNZ-UHFFFAOYSA-N 2-amino-N-[2-oxo-2-(prop-2-ynylamino)ethyl]acetamide Chemical compound NCC(=O)NCC(=O)NCC#C ADHPSJYHXQTWNZ-UHFFFAOYSA-N 0.000 description 7
- QYAWAUVNEUGIMK-UHFFFAOYSA-N CC(=O)SC(CC(=O)O)C(=O)N(C)CC(=O)NCC(=O)NCC#C Chemical compound CC(=O)SC(CC(=O)O)C(=O)N(C)CC(=O)NCC(=O)NCC#C QYAWAUVNEUGIMK-UHFFFAOYSA-N 0.000 description 7
- OKNWWUOVZULEJA-UHFFFAOYSA-N CC(NCC(NCC([N-]CC#C)=O)=O)=[S+]C(C1=CC=CC=C1)=O Chemical compound CC(NCC(NCC([N-]CC#C)=O)=O)=[S+]C(C1=CC=CC=C1)=O OKNWWUOVZULEJA-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229940086542 triethylamine Drugs 0.000 description 6
- CQPVFZGYSUJWEG-NSHDSACASA-N CC(N[C@@H](CCC(N)=O)C(NCC([N-]CC#C)=O)=O)=[S+]C(C)=O Chemical compound CC(N[C@@H](CCC(N)=O)C(NCC([N-]CC#C)=O)=O)=[S+]C(C)=O CQPVFZGYSUJWEG-NSHDSACASA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ULCAVETZPRCWII-UHFFFAOYSA-N N-hexadecyl-4-oxo-3-[[2-oxo-2-[[2-oxo-2-(prop-2-ynylamino)ethyl]amino]ethyl]carbamothioyl]pentanamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)CC(C(=O)C)C(=S)NCC(=O)NCC(=O)NCC#C ULCAVETZPRCWII-UHFFFAOYSA-N 0.000 description 4
- 230000003143 atherosclerotic effect Effects 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
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- VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
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- 150000004032 porphyrins Chemical class 0.000 description 1
- LKFCPWBGBPJDRC-UHFFFAOYSA-M potassium;thiobenzate Chemical compound [K+].[O-]C(=S)C1=CC=CC=C1 LKFCPWBGBPJDRC-UHFFFAOYSA-M 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
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- 230000003439 radiotherapeutic effect Effects 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- WUAPFZMCVAUBPE-IGMARMGPSA-N rhenium-186 Chemical compound [186Re] WUAPFZMCVAUBPE-IGMARMGPSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 230000008685 targeting Effects 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
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- QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
-
- 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/57536—Endothelin, vasoactive intestinal contractor [VIC]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Toxicology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4311021A DE4311021A1 (de) | 1993-03-31 | 1993-03-31 | Bifunktionelle Chelatbildner, deren Technetium- und Rhenium-Komplexe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende radiopharmazeutische Mittel |
| DEP4311021.5 | 1993-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2156618A1 true CA2156618A1 (en) | 1994-10-13 |
Family
ID=6484685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002156618A Abandoned CA2156618A1 (en) | 1993-03-31 | 1994-03-29 | Bifunctional chelators and their use in radiopharmaceuticals |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0692979A1 (ko) |
| JP (1) | JPH08508261A (ko) |
| KR (1) | KR960701667A (ko) |
| AU (1) | AU6501594A (ko) |
| CA (1) | CA2156618A1 (ko) |
| DE (1) | DE4311021A1 (ko) |
| HU (1) | HUT72733A (ko) |
| NO (1) | NO953865L (ko) |
| NZ (1) | NZ263792A (ko) |
| WO (1) | WO1994022491A1 (ko) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981490A (en) * | 1995-10-05 | 1999-11-09 | Darwin Discovery, Ltd. | Peptidyl compounds |
| WO2002092631A1 (en) * | 2001-05-14 | 2002-11-21 | The Horticulture And Food Research Institute Of New Zealand Limited | Kinetic assay |
| US7153822B2 (en) | 2002-01-29 | 2006-12-26 | Wyeth | Compositions and methods for modulating connexin hemichannels |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4310999C2 (de) * | 1993-03-31 | 1996-07-18 | Diagnostikforschung Inst | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner vom Typ XN¶1¶S¶1¶X' für radioaktive Isotope und deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DE4311022C2 (de) * | 1993-03-31 | 1996-07-11 | Diagnostikforschung Inst | Bifunktionelle chalkogenatom-unterbrochene Chelatbildner vom Typ S¶3¶N¶2¶ für radioaktive Isotope und deren Metallkomplexe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DE4337600A1 (de) * | 1993-11-01 | 1995-05-04 | Diagnostikforschung Inst | N-Alkyl-Peptidchelatbildner, deren Metallkomplexe mit Radionukliden, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende radiopharmazeutische Zusammesetzungen |
| US5632969A (en) * | 1994-10-13 | 1997-05-27 | Merck & Co., Inc. | N3 S2 chelating ligands optionally radiolabelled with Tc or Re, useful for diagnostic or therapeutic applications |
| EP0826000B1 (en) * | 1995-05-10 | 2002-10-23 | Darwin Discovery Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation and their therapeutic uses |
| DE19652374A1 (de) * | 1996-12-04 | 1998-06-10 | Schering Ag | Verwendung von Endothelin-Konjugaten in der Therapie, neue Endothelin-Konjugate, diese enthaltende Mittel, sowie Verfahren zu deren Herstellung |
| CN101648028B (zh) * | 2002-05-06 | 2012-11-21 | 恩多塞特公司 | 维生素-定向的显象剂 |
| WO2014007632A1 (en) * | 2012-07-06 | 2014-01-09 | Stichting Het Nederlands Kanker Instituut | Cysteine protease capturing agents |
| CN116731101A (zh) | 2016-06-01 | 2023-09-12 | 雅斯娜 | 用于治疗多种疾病的n-己酸-l-酪氨酸-l-异亮氨酸-(6)-氨基己酰胺的衍生物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3855239T2 (de) * | 1987-07-16 | 1996-10-31 | Nycomed Imaging As | Aminocarbonsäure und Derivate |
| WO1992019274A1 (en) * | 1991-05-08 | 1992-11-12 | Mallinckrodt Medical, Inc. | Technetium chelates to be used for determining the renal function |
| JPH0570484A (ja) * | 1991-09-12 | 1993-03-23 | Hitachi Chem Co Ltd | ペプチドおよびその塩 |
| DE69332470D1 (de) * | 1992-02-06 | 2002-12-12 | Biosynthema Inc | Liganden zur verbesserung der metallchelatbildungskinetik |
-
1993
- 1993-03-31 DE DE4311021A patent/DE4311021A1/de not_active Withdrawn
-
1994
- 1994-03-29 EP EP94912439A patent/EP0692979A1/de not_active Withdrawn
- 1994-03-29 CA CA002156618A patent/CA2156618A1/en not_active Abandoned
- 1994-03-29 KR KR1019950704236A patent/KR960701667A/ko not_active Application Discontinuation
- 1994-03-29 JP JP6521540A patent/JPH08508261A/ja active Pending
- 1994-03-29 NZ NZ263792A patent/NZ263792A/en unknown
- 1994-03-29 WO PCT/DE1994/000369 patent/WO1994022491A1/de not_active Application Discontinuation
- 1994-03-29 AU AU65015/94A patent/AU6501594A/en not_active Abandoned
- 1994-03-29 HU HU9502858A patent/HUT72733A/hu unknown
-
1995
- 1995-09-29 NO NO953865A patent/NO953865L/no unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981490A (en) * | 1995-10-05 | 1999-11-09 | Darwin Discovery, Ltd. | Peptidyl compounds |
| WO2002092631A1 (en) * | 2001-05-14 | 2002-11-21 | The Horticulture And Food Research Institute Of New Zealand Limited | Kinetic assay |
| US7153822B2 (en) | 2002-01-29 | 2006-12-26 | Wyeth | Compositions and methods for modulating connexin hemichannels |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6501594A (en) | 1994-10-24 |
| KR960701667A (ko) | 1996-03-28 |
| NO953865L (no) | 1995-11-23 |
| HU9502858D0 (en) | 1995-11-28 |
| NO953865D0 (no) | 1995-09-29 |
| HUT72733A (en) | 1996-05-28 |
| EP0692979A1 (de) | 1996-01-24 |
| DE4311021A1 (de) | 1994-10-27 |
| JPH08508261A (ja) | 1996-09-03 |
| NZ263792A (en) | 1997-02-24 |
| WO1994022491A1 (de) | 1994-10-13 |
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