CA1251453A - Bifunctional chelating agents - Google Patents
Bifunctional chelating agentsInfo
- Publication number
- CA1251453A CA1251453A CA000440522A CA440522A CA1251453A CA 1251453 A CA1251453 A CA 1251453A CA 000440522 A CA000440522 A CA 000440522A CA 440522 A CA440522 A CA 440522A CA 1251453 A CA1251453 A CA 1251453A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- mmoles
- hydrogen
- lower alkyl
- 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.)
- Expired
Links
- 239000002738 chelating agent Substances 0.000 title abstract description 6
- 230000001588 bifunctional effect Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000006239 protecting group Chemical group 0.000 claims abstract description 14
- 150000003573 thiols Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- -1 N-(2-mercaptoethyl)-glycyl homocysteine thiolactone Chemical compound 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 22
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- KIWQWJKWBHZMDT-UHFFFAOYSA-N homocysteine thiolactone Chemical compound NC1CCSC1=O KIWQWJKWBHZMDT-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000011503 in vivo imaging Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 230000002285 radioactive effect Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 210000000056 organ Anatomy 0.000 description 15
- 230000009467 reduction Effects 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 125000000129 anionic group Chemical group 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 11
- 238000002390 rotary evaporation Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000001962 electrophoresis Methods 0.000 description 8
- 210000003734 kidney Anatomy 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 229940090044 injection Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000012857 radioactive material Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 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 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 229910004878 Na2S2O4 Inorganic materials 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 239000001119 stannous chloride Substances 0.000 description 4
- 229910052713 technetium Inorganic materials 0.000 description 4
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 4
- CVKJXWOUXWRRJT-UHFFFAOYSA-N technetium dioxide Chemical compound O=[Tc]=O CVKJXWOUXWRRJT-UHFFFAOYSA-N 0.000 description 4
- 210000003462 vein Anatomy 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 239000007982 barbital buffer Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012217 radiopharmaceutical Substances 0.000 description 3
- 229940121896 radiopharmaceutical Drugs 0.000 description 3
- 230000002799 radiopharmaceutical effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940056501 technetium 99m Drugs 0.000 description 3
- PJMJFVQKDBRMIP-UHFFFAOYSA-N tetraphenylarsonium Chemical class C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PJMJFVQKDBRMIP-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000033368 Right sided atrial isomerism Diseases 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 238000010640 amide synthesis reaction Methods 0.000 description 2
- 210000003484 anatomy Anatomy 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000037396 body weight Effects 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000009850 completed effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical class 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 230000002633 protecting effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 125000005039 triarylmethyl group Chemical group 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- AZCRSQWHABNMIV-YFKPBYRVSA-N (2S)-2-amino-N-(2-aminoacetyl)-N-methyl-4-sulfanylbutanamide Chemical compound CN(C([C@@H](N)CCS)=O)C(CN)=O AZCRSQWHABNMIV-YFKPBYRVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 1
- 108010058907 Tiopronin Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical compound O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 125000005101 aryl methoxy carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960000796 barbital sodium Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
- HWJHZLJIIWOTGZ-UHFFFAOYSA-N n-(hydroxymethyl)acetamide Chemical compound CC(=O)NCO HWJHZLJIIWOTGZ-UHFFFAOYSA-N 0.000 description 1
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- 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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Optics & Photonics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US439,960 | 1982-11-08 | ||
| US06/439,960 US4434151A (en) | 1982-11-08 | 1982-11-08 | Bifunctional chelating agents |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524036A Division CA1281499C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
| CA000524035A Division CA1281500C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1251453A true CA1251453A (en) | 1989-03-21 |
Family
ID=23746836
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000440522A Expired CA1251453A (en) | 1982-11-08 | 1983-11-04 | Bifunctional chelating agents |
| CA000524035A Expired - Lifetime CA1281500C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
| CA000524036A Expired - Lifetime CA1281499C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524035A Expired - Lifetime CA1281500C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
| CA000524036A Expired - Lifetime CA1281499C (en) | 1982-11-08 | 1986-11-27 | Bifunctional chelating agents |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4434151A (enExample) |
| EP (1) | EP0108406B1 (enExample) |
| JP (1) | JPS59104377A (enExample) |
| AT (1) | ATE27282T1 (enExample) |
| CA (3) | CA1251453A (enExample) |
| DE (1) | DE3371635D1 (enExample) |
| DK (1) | DK507183A (enExample) |
| NO (1) | NO834063L (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4575556A (en) * | 1982-11-08 | 1986-03-11 | Medi-Physics, Inc. | Bifunctional chelating agents |
| US4673562A (en) * | 1983-08-19 | 1987-06-16 | The Children's Medical Center Corporation | Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents |
| US4670406A (en) * | 1984-01-06 | 1987-06-02 | Becton Dickinson And Company | Tracers for use in assays |
| US4638051A (en) * | 1984-04-30 | 1987-01-20 | The Johns Hopkins University | Brain imaging radiopharmaceuticals |
| US4670545A (en) * | 1984-05-11 | 1987-06-02 | University Patents, Inc. | Chelating agents for technetium-99M |
| US4980147A (en) * | 1984-06-25 | 1990-12-25 | University Of Utah Research Foundation | Radiolabeled technetium chelates for use in renal function determinations |
| US5242679A (en) * | 1985-01-14 | 1993-09-07 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US5175343A (en) * | 1985-01-14 | 1992-12-29 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4897255A (en) * | 1985-01-14 | 1990-01-30 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4746505A (en) * | 1985-04-26 | 1988-05-24 | President And Fellows Of Harvard College | Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands |
| EP0200211A1 (en) * | 1985-05-01 | 1986-11-05 | The Research Foundation Of State University Of New York | Diagnostic radiopharmaceutical compounds |
| US4861869A (en) * | 1986-05-29 | 1989-08-29 | Mallinckrodt, Inc. | Coupling agents for joining radionuclide metal ions with biologically useful proteins |
| US5279811A (en) * | 1987-02-18 | 1994-01-18 | The Du Pont Merck Pharmaceutical Company | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
| US4965392A (en) * | 1987-03-26 | 1990-10-23 | Neorx Corporation | Chelating compounds for metal-radionuclide labeled proteins |
| US5091514A (en) * | 1987-03-26 | 1992-02-25 | Neorx Corporation | Metal-radionuclide-labeled proteins and glycoproteins for diagnosis and therapy |
| US5021556A (en) * | 1987-07-22 | 1991-06-04 | Neorx Corporation | Method of radiolabeling chelating compounds comprising sulfur atoms with metal radionuclides |
| US4871836A (en) * | 1987-10-13 | 1989-10-03 | E. R. Squibb & Sons, Inc. | Boronic acid adducts of rhenium and radioactive isotopes of rhenium dioxime complexes |
| US5202451A (en) * | 1988-02-17 | 1993-04-13 | Neorx Corporation | Anchimeric radiometal chelating compounds |
| US4917878A (en) * | 1988-05-02 | 1990-04-17 | Thomas Jefferson University | Novel use of a radiolabelled antibody against stage specific embryonic antigen for the detection of occult abscesses in mammals |
| US4988496A (en) * | 1988-05-31 | 1991-01-29 | Neorx Corporation | Metal radionuclide chelating compounds for improved chelation kinetics |
| US5218128A (en) * | 1988-06-15 | 1993-06-08 | Centocor, Inc. | Bifunctional coupling agents and radionuclide labeled compositions prepared therefrom |
| US5443816A (en) * | 1990-08-08 | 1995-08-22 | Rhomed Incorporated | Peptide-metal ion pharmaceutical preparation and method |
| EP0489061A4 (en) * | 1989-08-24 | 1992-10-14 | Australian Nuclear Science And Technology Organisation | Radio-labelled antibodies for imaging |
| US6019958A (en) * | 1991-02-08 | 2000-02-01 | Diatide, Inc. | Technetium-99m labeled peptides for imaging inflammation |
| US5965107A (en) * | 1992-03-13 | 1999-10-12 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US5997844A (en) * | 1991-02-08 | 1999-12-07 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US5849261A (en) * | 1991-02-08 | 1998-12-15 | Diatide, Inc. | Radiolabeled vasoactive intestinal peptides for diagnosis and therapy |
| US5736122A (en) * | 1991-02-08 | 1998-04-07 | Diatide, Inc. | Technetium-99m labeled peptides for thrombus imaging |
| US5645815A (en) | 1991-02-08 | 1997-07-08 | Diatide, Inc. | Radiolabled compounds for thrombus imaging |
| US7238340B1 (en) | 1991-11-27 | 2007-07-03 | Cis Bio International | Monoamine, diamide, thiol-containing metal chelating agents |
| US5443815A (en) * | 1991-11-27 | 1995-08-22 | Diatech, Inc. | Technetium-99m labeled peptides for imaging |
| US6107459A (en) * | 1991-02-08 | 2000-08-22 | Diatide, Inc. | Technetium-99m labeled peptides for diagnostic imaging |
| JP2774378B2 (ja) * | 1991-02-08 | 1998-07-09 | ダイアテク，インコーポレイテッド | 映像用テクネチウム−９９ｍ標識化ポリペプチド |
| US5561220A (en) * | 1991-02-08 | 1996-10-01 | Diatech, Inc. | Technetium-99m labeled peptides for imaging inflammation |
| US5225180A (en) * | 1991-09-10 | 1993-07-06 | Diatech, Inc. | Technetium-99m labeled somatostatin-derived peptides for imaging |
| US5783170A (en) * | 1991-11-27 | 1998-07-21 | Diatide, Inc. | Peptide-metal chelate conjugates |
| US5508020A (en) * | 1992-06-05 | 1996-04-16 | Diatech, Inc. | Technetium-99M labeled peptides for imaging |
| US5968476A (en) * | 1992-05-21 | 1999-10-19 | Diatide, Inc. | Technetium-99m labeled peptides for thrombus imaging |
| US5951964A (en) * | 1993-06-04 | 1999-09-14 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US6171576B1 (en) | 1995-11-03 | 2001-01-09 | Organix Inc. | Dopamine transporter imaging agent |
| US5948933A (en) | 1997-07-11 | 1999-09-07 | Organix, Inc. | Tropane analogs and methods for inhibition of monoamine transport |
| US7105678B2 (en) | 1995-11-03 | 2006-09-12 | Organix, Inc. | Boat tropanes |
| CA2285516C (en) | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| DE20120708U1 (de) | 2001-10-09 | 2002-08-01 | Blundell, Paul, Sommerville, Mass. | Tropan-Analoga zur Inhibierung des Monoamin-Transports |
| JP2006515630A (ja) * | 2003-01-22 | 2006-06-01 | ザ ジェネラル ホスピタル コーポレイション | アミロイド結合性金属キレート剤 |
| SE526214C2 (sv) | 2003-02-28 | 2005-07-26 | Amersham Biosciences Ab | Ett sätt att generera metallkelaterande affinitetsligander |
| JP4629660B2 (ja) * | 2003-03-05 | 2011-02-09 | ジーイー・ヘルスケア・バイオサイエンス・アクチボラグ | マルチモードアニオン交換リガンドの製造法 |
| SE0300612D0 (sv) * | 2003-03-05 | 2003-03-05 | Amersham Biosciences Ab | A method of preparing ligands for hydrophobic interaction chromatography |
| SE0300624D0 (sv) * | 2003-03-05 | 2003-03-05 | Amersham Biosciences Ab | A method of preparing affinity ligands |
| US20080269065A1 (en) * | 2007-04-30 | 2008-10-30 | Syntrix Biosystems, Inc. | Conformationally Constrained Analytical Probes |
| GB2482739A (en) * | 2010-08-13 | 2012-02-15 | Univ Reading | Processes and compounds useful in peptide synthesis |
| EP2886550A1 (en) * | 2013-12-23 | 2015-06-24 | Centre National de la Recherche Scientifique (C.N.R.S.) | Dynamic molecules and dynamic combinatorial library |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2551480C3 (de) | 1975-11-15 | 1982-04-22 | Hoechst Ag, 6000 Frankfurt | Technetium-99m-markiertes Nierendiagnostikum und Verfahren zu seiner Herstellung |
| AU537592B2 (en) * | 1979-04-02 | 1984-07-05 | E.R. Squibb & Sons, Inc. | Mercaptoacyldipeptides |
| US4255443A (en) | 1979-11-16 | 1981-03-10 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Homocysteine thiolactone perchlorate as a tumor promotor |
-
1982
- 1982-11-08 US US06/439,960 patent/US4434151A/en not_active Expired - Lifetime
-
1983
- 1983-11-04 DK DK507183A patent/DK507183A/da not_active Application Discontinuation
- 1983-11-04 AT AT83111043T patent/ATE27282T1/de active
- 1983-11-04 EP EP83111043A patent/EP0108406B1/en not_active Expired
- 1983-11-04 CA CA000440522A patent/CA1251453A/en not_active Expired
- 1983-11-04 DE DE8383111043T patent/DE3371635D1/de not_active Expired
- 1983-11-07 JP JP58208909A patent/JPS59104377A/ja active Granted
- 1983-11-07 NO NO834063A patent/NO834063L/no unknown
-
1986
- 1986-11-27 CA CA000524035A patent/CA1281500C/en not_active Expired - Lifetime
- 1986-11-27 CA CA000524036A patent/CA1281499C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1281500C (en) | 1991-03-12 |
| JPH0421671B2 (enExample) | 1992-04-13 |
| JPS59104377A (ja) | 1984-06-16 |
| EP0108406A3 (en) | 1985-10-23 |
| EP0108406A2 (en) | 1984-05-16 |
| EP0108406B1 (en) | 1987-05-20 |
| CA1281499C (en) | 1991-03-12 |
| NO834063L (no) | 1984-05-09 |
| US4434151A (en) | 1984-02-28 |
| DE3371635D1 (en) | 1987-06-25 |
| ATE27282T1 (de) | 1987-06-15 |
| DK507183D0 (da) | 1983-11-04 |
| DK507183A (da) | 1984-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1251453A (en) | Bifunctional chelating agents | |
| US4575556A (en) | Bifunctional chelating agents | |
| US4571430A (en) | Homocysteine and homocysteinamide derivatives | |
| US4673562A (en) | Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents | |
| US4746505A (en) | Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands | |
| DK175089B1 (da) | Estersubstituerede diamindithioler eller farmaceutisek egnede salte deraf, især i steril, farmaceutisk acceptabel form, samt deres anvendelse i forbindelse med radionuclidkomplekser | |
| CA1316296C (en) | Technetium chelates to be used for determining the renal function | |
| US5817776A (en) | Amino acid analogs for tumor imaging | |
| US4279887A (en) | Amides useful as brain imaging agents | |
| CA2040204C (en) | Chelating compounds and their use | |
| CA2046654C (en) | Radiolabeled proteins for diagnostic or therapeutic use | |
| EP0642357B1 (en) | Radiolabelled somatostatin | |
| CN118126024B (zh) | 一种全新骨架99mTc-FAPI诊断探针及其在制备诊断肿瘤的药物或试剂中的应用 | |
| US5187264A (en) | Technetium chelates to be used for determining the renal function | |
| CA2232391A1 (en) | Bifunctional sulfide-containing sulfonamide-chelating agents such as xsns for radioactive isotypes | |
| JPS6026099B2 (ja) | ペプチド、その酸附加塩およびその製造法 | |
| US5534497A (en) | Technetium chelates to be used for determining the renal function | |
| CA2232315A1 (en) | Bifunctional sulfide-containing sulfonamide-chelating agents such as s2 ny for radioactive isotopes | |
| CA2031528C (en) | Radionuclide metal chelates for the radiolabeling of proteins | |
| CA2173844A1 (en) | N-alkyl peptide chelate formers, their metal complexes with radionuclides, processes for producing them and radio-pharmaceutical compositions containing these compounds | |
| Tang et al. | Synthesis of small peptides and their use as bifunctional chelating agents in diagnostic radiopharmaceuticals | |
| WO2003044031A1 (en) | Technetium or rhenium complexes, radiopharmaceutical products comprising them | |
| JPH05221958A (ja) | 核医学に使用することができる核種のための錯化剤としてのジアミノメルカプト（チオ）エーテル | |
| JPS5946264A (ja) | 分子中にキレ−ト形成基とアミノ基またはアルキルアミノ基を有する新規化合物 | |
| KR20020093404A (ko) | 심근 및 암 영상용 방사성 동위원소 착화합물과 리간드 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |