ZA200006313B - Labelled glutamine and lysine analogues. - Google Patents
Labelled glutamine and lysine analogues. Download PDFInfo
- Publication number
- ZA200006313B ZA200006313B ZA200006313A ZA200006313A ZA200006313B ZA 200006313 B ZA200006313 B ZA 200006313B ZA 200006313 A ZA200006313 A ZA 200006313A ZA 200006313 A ZA200006313 A ZA 200006313A ZA 200006313 B ZA200006313 B ZA 200006313B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- group
- metal
- value
- amino acid
- Prior art date
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- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 title claims description 6
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 title description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 77
- 229910052751 metal Inorganic materials 0.000 claims description 53
- 239000002184 metal Substances 0.000 claims description 53
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 27
- 150000001413 amino acids Chemical class 0.000 claims description 23
- 239000008139 complexing agent Substances 0.000 claims description 19
- 208000007536 Thrombosis Diseases 0.000 claims description 17
- 108010033276 Peptide Fragments Proteins 0.000 claims description 16
- 102000007079 Peptide Fragments Human genes 0.000 claims description 16
- 150000004696 coordination complex Chemical class 0.000 claims description 16
- 125000000539 amino acid group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 238000003745 diagnosis Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 208000005189 Embolism Diseases 0.000 claims description 9
- 102000011632 Caseins Human genes 0.000 claims description 8
- 108010076119 Caseins Proteins 0.000 claims description 8
- 108010069514 Cyclic Peptides Proteins 0.000 claims description 7
- 102000001189 Cyclic Peptides Human genes 0.000 claims description 7
- 102000016359 Fibronectins Human genes 0.000 claims description 7
- 108010067306 Fibronectins Proteins 0.000 claims description 7
- 230000000536 complexating effect Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 235000021247 β-casein Nutrition 0.000 claims description 6
- 229920000954 Polyglycolide Polymers 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 239000004633 polyglycolic acid Substances 0.000 claims description 5
- 239000004626 polylactic acid Substances 0.000 claims description 5
- 206010043376 Tetanus Diseases 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 108010040003 polyglutamine Proteins 0.000 claims description 3
- 229920000155 polyglutamine Polymers 0.000 claims description 3
- 239000005018 casein Substances 0.000 claims description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 2
- 235000021240 caseins Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 239000003446 ligand Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 235000001014 amino acid Nutrition 0.000 description 19
- 239000000758 substrate Substances 0.000 description 15
- 102000009123 Fibrin Human genes 0.000 description 14
- 108010073385 Fibrin Proteins 0.000 description 14
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 14
- 229950003499 fibrin Drugs 0.000 description 14
- 238000003384 imaging method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002738 chelating agent Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229910021645 metal ion Inorganic materials 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- -1 1,5-disubstituted tetrazoles Chemical class 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 108090000190 Thrombin Proteins 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
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- 239000011541 reaction mixture Substances 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 238000002372 labelling Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 210000002216 heart Anatomy 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 235000018102 proteins Nutrition 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 239000012217 radiopharmaceutical Substances 0.000 description 5
- 229940121896 radiopharmaceutical Drugs 0.000 description 5
- 230000002799 radiopharmaceutical effect Effects 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- 238000004007 reversed phase HPLC Methods 0.000 description 5
- 229910052713 technetium Inorganic materials 0.000 description 5
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 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 description 4
- 108010049003 Fibrinogen Proteins 0.000 description 4
- 102000008946 Fibrinogen Human genes 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940012952 fibrinogen Drugs 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 4
- 238000002595 magnetic resonance imaging Methods 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000005298 paramagnetic effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 238000011552 rat model Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 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 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 229910052688 Gadolinium Inorganic materials 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 101001068640 Nicotiana tabacum Basic form of pathogenesis-related protein 1 Proteins 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 239000007975 buffered saline Substances 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
- 238000010265 fast atom bombardment Methods 0.000 description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 3
- 125000000404 glutamine group Chemical class N[C@@H](CCC(N)=O)C(=O)* 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- WTKQMHWYSBWUBE-UHFFFAOYSA-N (3-nitropyridin-2-yl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CN=C1SCl WTKQMHWYSBWUBE-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 108010000196 Factor XIIIa Proteins 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 108060003393 Granulin Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
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- UMRUUWFGLGNQLI-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 UMRUUWFGLGNQLI-QFIPXVFZSA-N 0.000 description 1
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- HHCPAKJHIFSCSD-UHFFFAOYSA-N 1,4,8,11-tetrazacyclotetradecan-5-one Chemical compound O=C1CCNCCNCCCNCCN1 HHCPAKJHIFSCSD-UHFFFAOYSA-N 0.000 description 1
- BGVLBVASHIQNIO-UHFFFAOYSA-N 1,4,8,11-tetrazacyclotetradecane-5,7-dione Chemical compound O=C1CC(=O)NCCNCCCNCCN1 BGVLBVASHIQNIO-UHFFFAOYSA-N 0.000 description 1
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 1
- DLKBRTKDSDXWNA-UHFFFAOYSA-N 1-methyl-3-(4-nitrophenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 DLKBRTKDSDXWNA-UHFFFAOYSA-N 0.000 description 1
- UFJRJAOQYVMWEZ-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1C(F)(F)F UFJRJAOQYVMWEZ-UHFFFAOYSA-N 0.000 description 1
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
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- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
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- A—HUMAN NECESSITIES
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- 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
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- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Radiology & Medical Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Genetics & Genomics (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98303872 | 1998-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006313B true ZA200006313B (en) | 2002-07-17 |
Family
ID=8234827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006313A ZA200006313B (en) | 1998-05-15 | 2000-11-03 | Labelled glutamine and lysine analogues. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7049289B1 (zh) |
| EP (1) | EP1077998B1 (zh) |
| JP (2) | JP4199420B2 (zh) |
| KR (1) | KR100660509B1 (zh) |
| CN (2) | CN101407543A (zh) |
| AT (1) | ATE384075T1 (zh) |
| AU (1) | AU762736B2 (zh) |
| BR (1) | BR9910468A (zh) |
| CA (1) | CA2332277A1 (zh) |
| DE (1) | DE69937996T2 (zh) |
| ES (1) | ES2299245T3 (zh) |
| HU (1) | HUP0102154A3 (zh) |
| IL (1) | IL139385A (zh) |
| NO (1) | NO20005751L (zh) |
| RU (1) | RU2205186C2 (zh) |
| WO (1) | WO1999060018A1 (zh) |
| ZA (1) | ZA200006313B (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1379885A4 (en) * | 2001-01-05 | 2005-07-06 | Univ Duke | CONTRAST REINFORCING AGENT FOR MAGNETIC RESONANCE IMAGING |
| GB0116815D0 (en) | 2001-07-10 | 2001-08-29 | Nycomed Amersham Plc | Improved chelator conjugates |
| IL159310A0 (en) * | 2001-07-10 | 2004-06-01 | Amersham Health As | Peptide-based compounds |
| GB0223249D0 (en) * | 2002-10-08 | 2002-11-13 | Amersham Plc | Improved imaging agents |
| GB0224799D0 (en) * | 2002-10-25 | 2002-12-04 | Amersham Plc | Improved complex compositions |
| WO2004106939A2 (en) * | 2003-06-03 | 2004-12-09 | Paul Scherrer Institut | Method for the linkage of bifunctional chelating agents and (radioactive) transition metal complexes to proteins and peptides |
| GB0515974D0 (en) * | 2005-08-03 | 2005-09-07 | Ge Healthcare Ltd | Compounds and imaging methods |
| PT1978015T (pt) | 2005-11-29 | 2018-03-26 | Nihon Mediphysics Co Ltd | Composto precursor de composto orgânico marcado com halogéneo radioativo |
| WO2008060368A2 (en) * | 2006-10-02 | 2008-05-22 | Duke University | Transglutaminase-binding peptides and methods of use |
| US20130195756A1 (en) * | 2012-01-31 | 2013-08-01 | General Electric Company | 99mTc IMAGING AGENTS AND METHODS OF USE |
| WO2015017815A1 (en) | 2013-08-01 | 2015-02-05 | Rochester Institute Of Technology | Modular imaging agents containing amino acids and peptides |
| GB201610176D0 (en) * | 2016-06-10 | 2016-07-27 | Edinburgh Molecular Imaging Ltd | Imaging agents and methods of use |
| EP3538093B1 (en) * | 2016-11-09 | 2023-10-25 | Qiagen Sciences, LLC | Photoprotective mixtures as imaging reagents in sequencing-by-synthesis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59186947A (ja) * | 1983-03-09 | 1984-10-23 | Kowa Co | 新規ペプチド |
| WO1989000051A1 (en) * | 1987-07-07 | 1989-01-12 | Cytrx Biopool Ltd. | Fibrin-binding compound and method |
| US5270030A (en) * | 1988-12-29 | 1993-12-14 | Bio-Technology General Corp. | Fibrin binding domain polypeptide and method of producing |
| WO1993012819A1 (en) * | 1992-01-03 | 1993-07-08 | Rhomed Incorporated | Protein- and peptide-metal ion pharmaceutical applications |
| US5608110A (en) * | 1993-06-15 | 1997-03-04 | Bracco International B.V. | Heteroatom-bearing ligands and metal complexes thereof |
| AU5570898A (en) * | 1997-01-21 | 1998-08-07 | Nycomed Amersham Plc | Labelled factor xiiia substrates |
-
1999
- 1999-05-14 JP JP2000549636A patent/JP4199420B2/ja not_active Expired - Fee Related
- 1999-05-14 BR BR9910468-7A patent/BR9910468A/pt not_active IP Right Cessation
- 1999-05-14 DE DE69937996T patent/DE69937996T2/de not_active Expired - Lifetime
- 1999-05-14 US US09/674,616 patent/US7049289B1/en not_active Expired - Fee Related
- 1999-05-14 WO PCT/GB1999/001550 patent/WO1999060018A1/en not_active Application Discontinuation
- 1999-05-14 CN CNA2008101666071A patent/CN101407543A/zh active Pending
- 1999-05-14 HU HU0102154A patent/HUP0102154A3/hu unknown
- 1999-05-14 KR KR1020007012755A patent/KR100660509B1/ko not_active IP Right Cessation
- 1999-05-14 AU AU39428/99A patent/AU762736B2/en not_active Ceased
- 1999-05-14 CA CA002332277A patent/CA2332277A1/en not_active Abandoned
- 1999-05-14 AT AT99922325T patent/ATE384075T1/de not_active IP Right Cessation
- 1999-05-14 RU RU2000131699/04A patent/RU2205186C2/ru not_active IP Right Cessation
- 1999-05-14 CN CN99808609A patent/CN1309661A/zh active Pending
- 1999-05-14 ES ES99922325T patent/ES2299245T3/es not_active Expired - Lifetime
- 1999-05-14 EP EP99922325A patent/EP1077998B1/en not_active Expired - Lifetime
- 1999-05-14 IL IL13938599A patent/IL139385A/xx not_active IP Right Cessation
-
2000
- 2000-11-03 ZA ZA200006313A patent/ZA200006313B/en unknown
- 2000-11-14 NO NO20005751A patent/NO20005751L/no unknown
-
2005
- 2005-11-02 JP JP2005319889A patent/JP2006137751A/ja active Pending
-
2006
- 2006-04-24 US US11/410,177 patent/US20060292075A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010043608A (ko) | 2001-05-25 |
| CN1309661A (zh) | 2001-08-22 |
| NO20005751L (no) | 2001-01-08 |
| JP4199420B2 (ja) | 2008-12-17 |
| AU3942899A (en) | 1999-12-06 |
| IL139385A (en) | 2005-09-25 |
| WO1999060018A1 (en) | 1999-11-25 |
| HUP0102154A2 (hu) | 2001-09-28 |
| RU2205186C2 (ru) | 2003-05-27 |
| ATE384075T1 (de) | 2008-02-15 |
| DE69937996D1 (de) | 2008-03-06 |
| ES2299245T3 (es) | 2008-05-16 |
| BR9910468A (pt) | 2001-01-09 |
| HUP0102154A3 (en) | 2009-01-28 |
| CN101407543A (zh) | 2009-04-15 |
| JP2002515510A (ja) | 2002-05-28 |
| US7049289B1 (en) | 2006-05-23 |
| EP1077998B1 (en) | 2008-01-16 |
| EP1077998A1 (en) | 2001-02-28 |
| US20060292075A1 (en) | 2006-12-28 |
| DE69937996T2 (de) | 2009-01-02 |
| AU762736B2 (en) | 2003-07-03 |
| IL139385A0 (en) | 2001-11-25 |
| KR100660509B1 (ko) | 2006-12-22 |
| NO20005751D0 (no) | 2000-11-14 |
| JP2006137751A (ja) | 2006-06-01 |
| CA2332277A1 (en) | 1999-11-25 |
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