CA2224060C - Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide - Google Patents
Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide Download PDFInfo
- Publication number
- CA2224060C CA2224060C CA002224060A CA2224060A CA2224060C CA 2224060 C CA2224060 C CA 2224060C CA 002224060 A CA002224060 A CA 002224060A CA 2224060 A CA2224060 A CA 2224060A CA 2224060 C CA2224060 C CA 2224060C
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- Prior art keywords
- alkyl
- group
- carbon atoms
- groups
- aryl
- Prior art date
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- Expired - Lifetime
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- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 title claims description 41
- 239000003446 ligand Substances 0.000 title claims description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 27
- 229910052748 manganese Inorganic materials 0.000 title claims description 16
- 239000011572 manganese Substances 0.000 title description 14
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 title description 12
- 239000003054 catalyst Substances 0.000 title description 11
- 150000002505 iron Chemical class 0.000 title description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 208000035475 disorder Diseases 0.000 claims abstract description 8
- 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 230000000302 ischemic effect Effects 0.000 claims abstract description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 6
- 230000006378 damage Effects 0.000 claims abstract description 6
- 208000006011 Stroke Diseases 0.000 claims abstract description 5
- 208000014674 injury Diseases 0.000 claims abstract description 5
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 4
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- -1 cycloalkenylalkyl Chemical group 0.000 claims description 224
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 66
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 12
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012990 dithiocarbamate Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 239000002552 dosage form Substances 0.000 claims description 5
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 claims description 4
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- LLYCMZGLHLKPPU-UHFFFAOYSA-M perbromate Chemical compound [O-]Br(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-M 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 150000001356 alkyl thiols Chemical class 0.000 claims description 3
- 150000001504 aryl thiols Chemical class 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000005623 Carcinogenesis Diseases 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 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 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 206010033647 Pancreatitis acute Diseases 0.000 claims description 2
- 206010038687 Respiratory distress Diseases 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000003229 acute pancreatitis Diseases 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000004789 alkyl aryl sulfoxides Chemical class 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims description 2
- 230000036952 cancer formation Effects 0.000 claims description 2
- 231100000504 carcinogenesis Toxicity 0.000 claims description 2
- 229910001919 chlorite Inorganic materials 0.000 claims description 2
- 229910052619 chlorite group Inorganic materials 0.000 claims description 2
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940001468 citrate Drugs 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical group O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 claims description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
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- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- 229940086735 succinate Drugs 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 2
- 208000037816 tissue injury Diseases 0.000 claims description 2
- 239000001226 triphosphate Substances 0.000 claims description 2
- 235000011178 triphosphate Nutrition 0.000 claims description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 2
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims description 2
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 102000019197 Superoxide Dismutase Human genes 0.000 abstract description 14
- 108010012715 Superoxide dismutase Proteins 0.000 abstract description 14
- 208000027866 inflammatory disease Diseases 0.000 abstract description 5
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- 229940032362 superoxide dismutase Drugs 0.000 abstract 2
- 208000037906 ischaemic injury Diseases 0.000 abstract 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 29
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- 229910001868 water Inorganic materials 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
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- 238000000034 method Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 150000004985 diamines Chemical class 0.000 description 13
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
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- 125000002877 alkyl aryl group Chemical group 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 7
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D259/00—Heterocyclic compounds containing rings having more than four nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/915—Therapeutic or pharmaceutical composition
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46885495A | 1995-06-06 | 1995-06-06 | |
| US08/468,854 | 1995-06-06 | ||
| US08/596,887 | 1996-03-14 | ||
| US08/596,887 US6525041B1 (en) | 1995-06-06 | 1996-03-14 | Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| PCT/US1996/007552 WO1996039396A1 (en) | 1995-06-06 | 1996-05-31 | Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
Publications (2)
| Publication Number | Publication Date |
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| CA2224060A1 CA2224060A1 (en) | 1996-12-12 |
| CA2224060C true CA2224060C (en) | 2009-03-24 |
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| CA002224060A Expired - Lifetime CA2224060C (en) | 1995-06-06 | 1996-05-31 | Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
Country Status (7)
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| KR19990037647A (ko) * | 1995-08-17 | 1999-05-25 | 죤 에이치. 뷰센 | 망간 착체의 바이오콘쥬게이트 및 촉매로서의 그 사용 |
| BR9610241A (pt) * | 1995-08-17 | 1999-06-29 | Monsanto Co | Processos para análise de imagem de diagnóstico utilizando bioconjgados de complexos de metal de ligandos macrocíclicos contendo nitrogênio |
| US5976498A (en) * | 1995-08-17 | 1999-11-02 | Neumann; William L. | Methods of diagnostic image analysis using metal complexes of nitrogen-containing macrocyclic ligands |
| CZ271198A3 (cs) * | 1996-03-13 | 1999-01-13 | Monsanto Company | Biokonjugáty manganu nebo komplexy železa makrocyklických ligandů obsahujících dusík, působící jako katalyzátory pro dismutaci superoxidu |
| EP0888115A1 (en) * | 1996-03-13 | 1999-01-07 | Monsanto Company | Iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| US6180620B1 (en) * | 1997-06-20 | 2001-01-30 | G.D. Searle & Co. | Analgesic methods using synthetic catalysts for the dismutation of superoxide radicals |
| US20050171198A1 (en) * | 1997-06-20 | 2005-08-04 | Metaphore Pharmaceuticals, Inc. | SODm therapy for treatment, prevention, inhibition and reversal of inflammatory disease |
| US6214817B1 (en) | 1997-06-20 | 2001-04-10 | Monsanto Company | Substituted pyridino pentaazamacrocyle complexes having superoxide dismutase activity |
| GB9817845D0 (en) | 1998-08-17 | 1998-10-14 | Glaxo Group Ltd | Chemical compounds |
| EP1185312B1 (en) | 1999-05-27 | 2005-03-23 | Monsanto Company | Biomaterials modified with superoxide dismutase mimics |
| US6264966B1 (en) * | 2000-02-22 | 2001-07-24 | Concat, Ltd. | Compounds with chelation affinity and selectivity for first transition elements and their use in cosmetics and personal care products, inhibition of metalloenzymes, and inhibition of reperfusion injury |
| WO2002071054A1 (en) * | 2001-03-02 | 2002-09-12 | Metaphore Pharmaceuticals, Inc. | Chromatography of metal complexes |
| WO2005042718A2 (en) * | 2003-10-31 | 2005-05-12 | Metaphore Pharmaceuticals, Inc. | Compositions and methods for treating, preventing, reversing and inhibiting pain |
| US7299082B2 (en) * | 2003-10-31 | 2007-11-20 | Abbott Diabetes Care, Inc. | Method of calibrating an analyte-measurement device, and associated methods, devices and systems |
| US7699964B2 (en) | 2004-02-09 | 2010-04-20 | Abbott Diabetes Care Inc. | Membrane suitable for use in an analyte sensor, analyte sensor, and associated method |
| US8165651B2 (en) * | 2004-02-09 | 2012-04-24 | Abbott Diabetes Care Inc. | Analyte sensor, and associated system and method employing a catalytic agent |
| US8217166B2 (en) * | 2005-05-05 | 2012-07-10 | Galera Therapeutics, Llc | Polyethylene glycolated superoxide dismutase mimetics |
| US20120301403A1 (en) | 2007-06-21 | 2012-11-29 | Galera Therapeutics, Llc | Polyethylene glycolated superoxide dismutase mimetics |
| US7885698B2 (en) | 2006-02-28 | 2011-02-08 | Abbott Diabetes Care Inc. | Method and system for providing continuous calibration of implantable analyte sensors |
| EP2056675B1 (en) | 2006-10-12 | 2019-01-09 | Galera Labs, LLC | Methods of treating oral mucositis |
| US20080161666A1 (en) * | 2006-12-29 | 2008-07-03 | Abbott Diabetes Care, Inc. | Analyte devices and methods |
| WO2009124095A1 (en) * | 2008-03-31 | 2009-10-08 | Abbott Diabetes Care Inc. | Shallow implantable analyte sensor with rapid physiological response |
| WO2009143454A2 (en) | 2008-05-22 | 2009-11-26 | Kereos, Inc. | Combination antitumor therapy |
| JP6267638B2 (ja) | 2011-09-26 | 2018-01-24 | ガレラ・ラブス・リミテッド・ライアビリティ・カンパニーＧａｌｅｒａ Ｌａｂｓ， Ｌｌｃ | 疾患の治療方法 |
| CN102634241B (zh) * | 2012-05-30 | 2014-01-29 | 沈阳化工大学 | 一种复合改性氧化铁红染料及其制备方法 |
| WO2015102745A1 (en) | 2013-12-31 | 2015-07-09 | Abbott Diabetes Care Inc. | Self-powered analyte sensor and devices using the same |
| SG10202002859QA (en) | 2015-08-11 | 2020-05-28 | Galera Labs Llc | Pentaaza macrocyclic ring complexes possessing oral bioavailability |
| IL269915B (en) | 2017-04-13 | 2022-09-01 | Galera Labs Llc | Cancer immunotherapy combined with a macrocyclic ring pentase complex |
| CN111902147A (zh) | 2018-01-31 | 2020-11-06 | 加莱拉实验室有限责任公司 | 五氮杂大环状环配合物和基于铂的抗癌剂的组合癌症治疗 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001212A (en) | 1973-10-03 | 1977-01-04 | E. I. Du Pont De Nemours And Company | Macrocyclic polyamines |
| US3930867A (en) | 1974-01-07 | 1976-01-06 | E. I. Du Pont De Nemours And Company | Macrocyclic polyamines as sensitizers for silver halide emulsions |
| JPS5998074A (ja) | 1982-11-27 | 1984-06-06 | Nippon Redarii Kk | 大環状ジオキソテトラミン−銅錯体 |
| JPS59193824A (ja) | 1983-04-20 | 1984-11-02 | Ajinomoto Co Inc | 尿結石溶解剤 |
| JPS61226751A (ja) | 1985-03-30 | 1986-10-08 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料用処理液及びその処理方法 |
| US4885363A (en) | 1987-04-24 | 1989-12-05 | E. R. Squibb & Sons, Inc. | 1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs |
| US5223538A (en) | 1987-03-31 | 1993-06-29 | Duke University | Superoxide dismutase mimic |
| US5096724A (en) | 1988-06-03 | 1992-03-17 | Aquanautics Corporation | Methods, compositions, and systems for ligand extraction |
| JP2930709B2 (ja) | 1988-12-22 | 1999-08-03 | ザ ダウ ケミカル カンパニー | モノ―ｎ―アルキル化ポリアザ大員環の製造方法 |
| FR2644785B1 (fr) | 1989-03-24 | 1991-07-05 | Guerbet Sa | Nouveaux ligands macrocycliques azotes, procede de preparation, complexes metalliques formes par ces ligands et composition de diagnostic les contenant |
| US5914095A (en) | 1989-04-07 | 1999-06-22 | Salutar, Inc. | Polychelants containg amide bonds |
| CA2032559C (en) | 1989-12-28 | 2001-11-06 | Kiyofumi Ishikawa | Endothelin antagonistic cyclic pentapeptides |
| GB9001245D0 (en) | 1990-01-19 | 1990-03-21 | Salutar Inc | Compounds |
| CA2072934C (en) * | 1991-07-19 | 2007-08-28 | Karl William Aston | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| KR0145953B1 (ko) | 1991-07-19 | 1998-08-17 | 제임스 클리프튼 보올딩 | 슈퍼옥사이드의 불균화촉매로서 효과적인 질소를 포함하는 마크로사이클 릭리간드의 망간착물 |
| US6204259B1 (en) | 1993-01-14 | 2001-03-20 | Monsanto Company | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| EP0756495A1 (en) * | 1994-04-22 | 1997-02-05 | Monsanto Company | Diagnostic image analysis with metal complexes |
| JPH11507621A (ja) * | 1995-06-07 | 1999-07-06 | モンサント カンパニー | 置換ポリアザ大環状化合物の製造法 |
-
1996
- 1996-03-14 US US08/596,887 patent/US6525041B1/en not_active Expired - Lifetime
- 1996-05-31 WO PCT/US1996/007552 patent/WO1996039396A1/en not_active Application Discontinuation
- 1996-05-31 CN CN96195778A patent/CN1191530A/zh active Pending
- 1996-05-31 CA CA002224060A patent/CA2224060C/en not_active Expired - Lifetime
- 1996-05-31 AU AU60237/96A patent/AU6023796A/en not_active Abandoned
- 1996-05-31 EP EP96917823A patent/EP0830352A1/en not_active Withdrawn
- 1996-05-31 JP JP9500693A patent/JPH11506734A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11506734A (ja) | 1999-06-15 |
| AU6023796A (en) | 1996-12-24 |
| WO1996039396A1 (en) | 1996-12-12 |
| CA2224060A1 (en) | 1996-12-12 |
| CN1191530A (zh) | 1998-08-26 |
| EP0830352A1 (en) | 1998-03-25 |
| US6525041B1 (en) | 2003-02-25 |
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