JPH10502931A - ペプチド誘導の放射性核種キレート化剤 - Google Patents
ペプチド誘導の放射性核種キレート化剤Info
- Publication number
- JPH10502931A JPH10502931A JP8505323A JP50532396A JPH10502931A JP H10502931 A JPH10502931 A JP H10502931A JP 8505323 A JP8505323 A JP 8505323A JP 50532396 A JP50532396 A JP 50532396A JP H10502931 A JPH10502931 A JP H10502931A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- carboxyl
- compound
- compound according
- 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.)
- Granted
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 41
- 239000002738 chelating agent Substances 0.000 title abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 27
- 239000002184 metal Substances 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
- -1 amino, carboxyl Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 238000003384 imaging method Methods 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 150000008575 L-amino acids Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000539 amino acid group Chemical group 0.000 claims description 12
- 150000004767 nitrides Chemical class 0.000 claims description 10
- 230000008685 targeting Effects 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000562 conjugate Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 15
- 238000002372 labelling Methods 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 10
- 235000018102 proteins Nutrition 0.000 description 10
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- 102000004169 proteins and genes Human genes 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 238000002059 diagnostic imaging Methods 0.000 description 5
- 229910052713 technetium Inorganic materials 0.000 description 5
- QDWVRVNMKUFQJL-UHFFFAOYSA-N 2-(dibenzylamino)acetic acid Chemical compound C=1C=CC=CC=1CN(CC(=O)O)CC1=CC=CC=C1 QDWVRVNMKUFQJL-UHFFFAOYSA-N 0.000 description 4
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 108010053993 N-terminal tetrapeptide cystatin C Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 108010077895 Sarcosine Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 108700003601 dimethylglycine Proteins 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 238000010647 peptide synthesis reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052702 rhenium Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229940043230 sarcosine Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 230000009920 chelation Effects 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
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- 229940078490 n,n-dimethylglycine Drugs 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 150000003573 thiols Chemical group 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- WGJUFIXHTBAMBX-BYPYZUCNSA-N (2s)-2,6,6-triaminohexanoic acid Chemical compound NC(N)CCC[C@H](N)C(O)=O WGJUFIXHTBAMBX-BYPYZUCNSA-N 0.000 description 1
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 1
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- PZUPAGRIHCRVKN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]-5-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol Chemical class OCC1OC(O)C(O)C(O)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(COC4C(C(O)C(O)CO4)O)O3)O)C(COC3C(C(O)C(O)CO3)O)O2)O)C(COC2C(C(O)C(O)CO2)O)O1 PZUPAGRIHCRVKN-UHFFFAOYSA-N 0.000 description 1
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- OLIFSFOFKGKIRH-WUJLRWPWSA-N Gly-Thr Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)CN OLIFSFOFKGKIRH-WUJLRWPWSA-N 0.000 description 1
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- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003495 technetium Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 101150002091 tfa1 gene Proteins 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- PQGFRBOHUKOXQZ-FSCNPAMSSA-J tris[[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoyl]oxy]stannyl (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Sn+4].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O PQGFRBOHUKOXQZ-FSCNPAMSSA-J 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- 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
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.下記式(I): (式中、 Xは、直鎖又は分岐の、飽和又は不飽和の、C1-4アルキル鎖(これは、場合 により、N、O及びSから選択される1個又は2個の複素原子により中断されて いてもよく、かつ場合により、ハロゲン、ヒドロキシル、アミノ、カルボキシル 、C1-4アルキル、アリール及び(CO)Zから選択される少なくとも一つの基 により置換されていてもよい)であり; Yは、H又はXと同義の置換基であり; X及びYは、一緒になって、5−員〜8−員の、飽和又は不飽和複素環(これ らは、場合により、ハロゲン、ヒドロキシル、アミノ、カルボキシル、オキソ、 C1-4アルキル、アリール及び(CO)Zから選択される少なくとも一つの基に より置換されていてもよい)を形成してもよく; R1〜R4は、独立して、H;カルボキシル;C1-4アルキル;C1-4アルキル( これは、ヒドロキシル、アミノ、スルフヒドリル、ハロゲン、カルボキシル、C1-4 アルコキシカルボニル及びアミノカルボニルから選択される基により置換さ れている);プロリン以外のD−又はL−アミノ酸のα炭素側鎖;及びC(O) Zから選択され; R5及びR6は、独立して、H;カルボキシル;アミノ;C1-4アルキ ル;C1-4アルキル(これは、ヒドロキシル、カルボキシル又はアミノにより置 換されている);及びC(O)Zから選択され; R7は、H及び硫黄保護基から選択され;そして Zは、ヒドロキシル、C1-4アルコキシ及び標的分子から選択される)で示さ れる化合物。 2.R1、R2、R4、R5及びR6が、水素である、請求項1記載の化合物。 3.X及びYが、独立して、C1-4アルキル及びアリール置換C1-4アルキルから 選択される、請求項1記載の化合物。 4.R3が、ヒドロキシメチル及び1−ヒドロキシエチルから選択される、請求 項1記載の化合物。 5.Yが、独立して、Xと同義の置換基である、請求項1記載の化合物。 6.X及びYが、メチル、エチル及びベンジルから選択される同一の基である、 請求項5記載の化合物。 7.R3が、ヒドロキシメチル及び1−ヒドロキシエチルから選択される、請求 項5記載の化合物。 8.R1、R2、R4、R5及びR6が、水素である、請求項5記載の化合物。 9.Zが、標的分子である、請求項1記載の化合物。 10.標的分子が、ペプチドである、請求項9記載の化合物。 11.該ペプチドが、3個又はそれ以上のアミノ酸残基を含む、請求項10記載 の化合物。 12.該ペプチドが、配列TKPPRを含む、請求項11記載の化合物。 13.該ペプチドが、配列Gly−Thr−Lys−Pro−Pro−Arg− OHを含む、請求項12記載の化合物。 14.金属放射性核種又はそのオキシド若しくはニトリドとの錯体形態である、 請求項1〜13いずれか1項記載の化合物。 15.該金属放射性核種が、99mTc、64Cu、67Cu、97Ru、105Rh、109 Pd、186Re、188Re、198Au、199Au、203Pb、212Pb及び212Biか ら選択される、請求項14記載の化合物。 16.該金属放射性核種が、99mTc、186Re及び188Reから選択される、請 求項14記載の化合物。 17.該金属放射性核種が、99mTcである、請求項14記載の化合物。 18.一般式(II): (式中、 Xは、直鎖又は分岐の、飽和又は不飽和の、C1-4アルキル鎖(これは、場合 により、N、O及びSから選択される1個又は2個の複素原子により中断されて いてもよく、かつ場合により、ハロゲン、ヒドロキシル、アミノ、カルボキシル 、C1-4アルキル、アリール及び(CO)Zにより選択される少なくとも一つの 基により置換されていてもよい)であり; Yは、H又はXと同義の置換基であり; X及びYは、一緒になって、5−員〜8−員の、飽和又は不飽和複素環(これ らは、場合により、ハロゲン、ヒドロキシル、アミノ、カルボキシル、オキソ、 C1-4アルキル、アリール及び(CO)Zから選択される少なくとも一つの基に より置換されていてもよい)を形成してもよく; R1〜R4は、独立して、H;カルボキシル;C1-4アルキル;C1-4アルキル( これは、ヒドロキシル、アミノ、スルフヒドリル、ハロゲン、カルボキシル、C1-4 アルコキシカルボニル及びアミノカルボニルから選択される基により置換さ れている);プロリン以外のD−又はL−アミノ酸のα炭素側鎖;及びC(O) Zから選択され; R5及びR6は、独立して、H;カルボキシル;アミノ;C1-4アルキル;C1-4 アルキル(これは、ヒドロキシル、カルボキシル又はアミノにより置換されてい る);及びC(O)Zから選択され; Zは、ヒドロキシル、C1-4アルコキシ及び標的化分子から選択され; そして Mは、金属放射性核種又はそのオキシド若しくはそのニトリドである)で示さ れる化合物。 19.Mが、99mTc、64Cu、67Cu、97Ru、105Rh、109Pd、186Re、188 Re、198Au、199Au、203Pb、212Pb及び212Bi、並びにそのオキシ ド又はニトリドから選択される、請求項18記載の化合物。 20.Mが、99mTc、186Re及び188Re、並びにそのオキシド又はニトリド から選択される、請求項18記載の化合物。 21.Mが、99mTc又はそのオキシド若しくはニトリドである請求項18記載 の化合物。 22.哺乳動物中の標的分子の存在部位を検出するための方法であって、 請求項14記載の化合物(ここで、Zは、標的分子である)の診断に有効な量 を投与する工程を含むことを特徴とする方法。 23.該金属放射性核種が、99mTcである、請求項22記載の方法。 24.哺乳動物中の病巣炎症部位を造影するための方法であって、 請求項10記載の化合物(これは、金属放射性核種又はそのオキシド若しくは ニトリドとの錯体の形態である)の診断に有効な量を投与する工程を含むことを 特徴とする方法。 25.該金属放射性核種が、99mTcである、請求項24記載の方法。 26.哺乳動物中の病巣炎症部位を造影するための方法であって、 請求項12記載の化合物(これは、金属放射性核種又はそのオキシド若しくは ニトリドとの錯体の形態である)の診断に有効な量を投与する工程を含むことを 特徴とする方法。 27.該金属放射性核種が、99mTcである、請求項26記載の方法。 28.N,N−ジメチルGly−Ser−Cys(Acm)−Gly−Thr− Lys−Pro−Pro−Arg−OH; N,N−ジメチルGly−Thr−Cys(Acm)−Gly−Thr−Ly s−Pro−Pro−Arg−OH; N,N−ジエチルGly−Ser−Cys(Acm)−Gly−Thr−Ly s−Pro−Pro−Arg−OH;及び N,N−ジベンジルGly−Ser−Cys(Acm)Gly−Thr−Ly s−Pro−Pro−Arg−OHから選択される、請求項1記載の化合物。 29.金属放射性核種又はそのオキシド若しくはニトリドとの錯体の形態 である、請求項28記載の化合物。 30.該金属放射性核種が、99mTcである、請求項29記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/279,155 US5662885A (en) | 1994-07-22 | 1994-07-22 | Peptide derived radionuclide chelators |
US08/279,155 | 1994-07-22 | ||
PCT/CA1995/000249 WO1996003427A1 (en) | 1994-07-22 | 1995-04-28 | Peptide derived radionuclide chelators |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10502931A true JPH10502931A (ja) | 1998-03-17 |
JP3753734B2 JP3753734B2 (ja) | 2006-03-08 |
Family
ID=23067872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50532396A Expired - Fee Related JP3753734B2 (ja) | 1994-07-22 | 1995-04-28 | ペプチド誘導の放射性核種キレート化剤 |
Country Status (11)
Country | Link |
---|---|
US (3) | US5662885A (ja) |
EP (1) | EP0772628B1 (ja) |
JP (1) | JP3753734B2 (ja) |
CN (1) | CN1158133A (ja) |
AT (1) | ATE194845T1 (ja) |
AU (1) | AU700772B2 (ja) |
CA (1) | CA2194551A1 (ja) |
DE (1) | DE69518083T2 (ja) |
HU (1) | HUT77137A (ja) |
NO (1) | NO970273L (ja) |
WO (1) | WO1996003427A1 (ja) |
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-
1994
- 1994-07-22 US US08/279,155 patent/US5662885A/en not_active Expired - Lifetime
-
1995
- 1995-04-28 CA CA002194551A patent/CA2194551A1/en not_active Abandoned
- 1995-04-28 HU HU9700196A patent/HUT77137A/hu unknown
- 1995-04-28 AT AT95916539T patent/ATE194845T1/de not_active IP Right Cessation
- 1995-04-28 DE DE69518083T patent/DE69518083T2/de not_active Expired - Lifetime
- 1995-04-28 CN CN95195127A patent/CN1158133A/zh active Pending
- 1995-04-28 US US08/612,842 patent/US5976495A/en not_active Expired - Lifetime
- 1995-04-28 WO PCT/CA1995/000249 patent/WO1996003427A1/en not_active Application Discontinuation
- 1995-04-28 EP EP95916539A patent/EP0772628B1/en not_active Expired - Lifetime
- 1995-04-28 JP JP50532396A patent/JP3753734B2/ja not_active Expired - Fee Related
- 1995-04-28 AU AU23011/95A patent/AU700772B2/en not_active Ceased
-
1996
- 1996-08-28 US US08/703,988 patent/US5780006A/en not_active Expired - Lifetime
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1997
- 1997-01-21 NO NO970273A patent/NO970273L/no unknown
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---|---|
EP0772628B1 (en) | 2000-07-19 |
DE69518083T2 (de) | 2001-03-22 |
NO970273D0 (no) | 1997-01-21 |
JP3753734B2 (ja) | 2006-03-08 |
AU2301195A (en) | 1996-02-22 |
EP0772628A1 (en) | 1997-05-14 |
NO970273L (no) | 1997-03-12 |
ATE194845T1 (de) | 2000-08-15 |
CN1158133A (zh) | 1997-08-27 |
US5780006A (en) | 1998-07-14 |
CA2194551A1 (en) | 1996-02-08 |
DE69518083D1 (de) | 2000-08-24 |
WO1996003427A1 (en) | 1996-02-08 |
US5976495A (en) | 1999-11-02 |
AU700772B2 (en) | 1999-01-14 |
US5662885A (en) | 1997-09-02 |
HUT77137A (hu) | 1998-03-02 |
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