ES2215305T3 - Metodos analgesicos usando los catalizadores sinteticos para la dismutacion de los radicales superoxido. - Google Patents
Metodos analgesicos usando los catalizadores sinteticos para la dismutacion de los radicales superoxido.Info
- Publication number
- ES2215305T3 ES2215305T3 ES98929022T ES98929022T ES2215305T3 ES 2215305 T3 ES2215305 T3 ES 2215305T3 ES 98929022 T ES98929022 T ES 98929022T ES 98929022 T ES98929022 T ES 98929022T ES 2215305 T3 ES2215305 T3 ES 2215305T3
- Authority
- ES
- Spain
- Prior art keywords
- heterocycle
- cycloalkyl
- attached
- independently
- carbon
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 63
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 22
- 238000007323 disproportionation reaction Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title description 9
- 239000003446 ligand Substances 0.000 claims abstract description 30
- -1 nitrogen-containing macrocycle Chemical class 0.000 claims abstract description 29
- 230000036592 analgesia Effects 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 10
- 239000011572 manganese Substances 0.000 claims abstract description 10
- 239000013110 organic ligand Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 102000019197 Superoxide Dismutase Human genes 0.000 claims description 16
- 108010012715 Superoxide dismutase Proteins 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 229960005181 morphine Drugs 0.000 claims description 13
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 11
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 230000002441 reversible effect Effects 0.000 claims description 8
- 229930194542 Keto Natural products 0.000 claims description 7
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 7
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 7
- 239000000014 opioid analgesic Substances 0.000 claims description 7
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 7
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229940035676 analgesics Drugs 0.000 claims description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- 230000003637 steroidlike Effects 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229910000085 borane Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 19
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 6
- 239000004202 carbamide Substances 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 5
- 239000003640 drug residue Substances 0.000 claims 2
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 claims 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 1
- 208000002193 Pain Diseases 0.000 description 30
- 230000036407 pain Effects 0.000 description 24
- 208000004454 Hyperalgesia Diseases 0.000 description 18
- 208000035154 Hyperesthesia Diseases 0.000 description 18
- 229940005483 opioid analgesics Drugs 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 239000000679 carrageenan Substances 0.000 description 12
- 229920001525 carrageenan Polymers 0.000 description 12
- 235000010418 carrageenan Nutrition 0.000 description 12
- 229940113118 carrageenan Drugs 0.000 description 12
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 12
- 208000000114 Pain Threshold Diseases 0.000 description 11
- 230000037040 pain threshold Effects 0.000 description 11
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 208000005298 acute pain Diseases 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000006186 oral dosage form Substances 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 206010048010 Withdrawal syndrome Diseases 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
- 210000000078 claw Anatomy 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 239000002840 nitric oxide donor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
- 229960002986 dinoprostone Drugs 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000007910 systemic administration Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 2
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229960002504 capsaicin Drugs 0.000 description 2
- 235000017663 capsaicin Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 229960002428 fentanyl Drugs 0.000 description 2
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 102000051367 mu Opioid Receptors Human genes 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 229940124641 pain reliever Drugs 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000001698 pyrogenic effect Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 230000009261 transgenic effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 108020001612 μ-opioid receptors Proteins 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 208000000187 Abnormal Reflex Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000010907 Cyclooxygenase 2 Human genes 0.000 description 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010049140 Endorphins Proteins 0.000 description 1
- 102000009025 Endorphins Human genes 0.000 description 1
- 108010092674 Enkephalins Proteins 0.000 description 1
- 206010015535 Euphoric mood Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 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
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 1
- URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 1
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 1
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 1
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 206010043220 Temporomandibular joint syndrome Diseases 0.000 description 1
- 108700019146 Transgenes Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000004727 amygdala Anatomy 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 1
- 229960001736 buprenorphine Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 108700023159 delta Opioid Receptors Proteins 0.000 description 1
- 102000048124 delta Opioid Receptors Human genes 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000002743 euphoric effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 210000004884 grey matter Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 206010020745 hyperreflexia Diseases 0.000 description 1
- 230000035859 hyperreflexia Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 102000048260 kappa Opioid Receptors Human genes 0.000 description 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
- 229960004752 ketorolac Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000008384 membrane barrier Effects 0.000 description 1
- 238000006241 metabolic reaction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 210000000929 nociceptor Anatomy 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 229940124583 pain medication Drugs 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 108020001588 κ-opioid receptors Proteins 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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 Table
- C07F13/005—Compounds without a metal-carbon linkage
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5040297P | 1997-06-20 | 1997-06-20 | |
| US50402P | 1997-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2215305T3 true ES2215305T3 (es) | 2004-10-01 |
Family
ID=21965044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98929022T Expired - Lifetime ES2215305T3 (es) | 1997-06-20 | 1998-06-15 | Metodos analgesicos usando los catalizadores sinteticos para la dismutacion de los radicales superoxido. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US6180620B1 (https=) |
| EP (1) | EP1001752B1 (https=) |
| JP (1) | JP2002506445A (https=) |
| AT (1) | ATE256467T1 (https=) |
| AU (1) | AU733415B2 (https=) |
| CA (1) | CA2294155A1 (https=) |
| DE (1) | DE69820633T2 (https=) |
| DK (1) | DK1001752T3 (https=) |
| ES (1) | ES2215305T3 (https=) |
| PT (1) | PT1001752E (https=) |
| WO (1) | WO1998058636A1 (https=) |
| ZA (1) | ZA985376B (https=) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127356A (en) | 1993-10-15 | 2000-10-03 | Duke University | Oxidant scavengers |
| US20060270639A1 (en) * | 1997-06-20 | 2006-11-30 | Daniela Salvemini | Combinations of superoxide dismutase mimetics and nonsteroidal analgesic/anti-inflammatory drugs |
| US6214817B1 (en) * | 1997-06-20 | 2001-04-10 | Monsanto Company | Substituted pyridino pentaazamacrocyle complexes having superoxide dismutase activity |
| US20050171198A1 (en) * | 1997-06-20 | 2005-08-04 | Metaphore Pharmaceuticals, Inc. | SODm therapy for treatment, prevention, inhibition and reversal of inflammatory disease |
| IL135949A0 (en) | 1997-11-03 | 2001-05-20 | Univ Duke | Substituted porphyrins |
| DK1616869T3 (da) | 1999-01-25 | 2012-05-07 | Nat Jewish Health | Substituerede porphyriner og deres terapeutiske anvendelse |
| DE60018925T2 (de) | 1999-05-27 | 2006-04-13 | Pharmacia Corp.(N.D.Ges.D.Staates Delaware) | Biomaterialien, modifiziert mit superoxid-dismutase imitatoren |
| US20030069281A1 (en) * | 2000-06-14 | 2003-04-10 | Irwin Fridovich | Tetrapyrroles |
| US20020072512A1 (en) * | 2000-12-08 | 2002-06-13 | Metaphore Pharmaceuticals, Inc | Method of preventing and treating HIV-mediated central nervous system damage |
| DE60235955D1 (de) * | 2001-01-05 | 2010-05-27 | Metaphore Pharmaceuticals Inc | Zusammensetzungen und verfahren zur erhöhung der zytokin-aktivität und zur behandlung der hypotension assoziiert mit der verabreichung von zytokinen |
| EP1392328B1 (en) | 2001-01-19 | 2009-08-12 | National Jewish Medical and Research Center | Medicament for protection in radiotherapy |
| WO2002058686A2 (en) * | 2001-01-26 | 2002-08-01 | Metaphore Pharmaceuticals, Inc. | Method of treatment of neurodegenerative disorders using pentaaza-macrocyclic ligand complexes |
| EP1405066B1 (en) * | 2001-03-02 | 2015-06-17 | Galera Therapeutics LLC | Chromatography of metal complexes |
| US20040137638A1 (en) | 2002-03-04 | 2004-07-15 | Slomczynska Urszula J. | Chromatography of metal complexes |
| AU2002312194B8 (en) * | 2001-06-01 | 2008-05-15 | Aeolus Sciences, Inc. | Oxidant scavengers for treatment of diabetes or use in transplantation or induction of immune tolerance |
| CA2449631A1 (en) * | 2001-06-08 | 2002-12-19 | Metaphore Pharmaceuticals, Inc. | Libraries of conformationally constrained peptides, chiral azacrowns, and peptidomimetics and methods of making the same |
| CA2451602A1 (en) * | 2001-06-26 | 2003-01-03 | Metaphore Pharmaceuticals, Inc. | Combination therapy of an sodm and a corticosteroid for prevention and/or treatment of inflammatory disease |
| EP1450824A4 (en) * | 2001-11-02 | 2005-09-28 | Elan Corp Plc | PHARMACEUTICAL COMPOSITION |
| SI1463563T1 (sl) * | 2001-12-14 | 2009-06-30 | Alcon Inc | Superoksidni dizmutazni mimetiki za zdravljenje očesnih motenj in bolezni |
| US6933275B2 (en) * | 2002-05-01 | 2005-08-23 | The Board Of Trustees Of The Leland Stanford Junior University | Protein kinase C peptides for use in withdrawal |
| AU2003237500A1 (en) * | 2002-06-07 | 2003-12-22 | Duke University | Substituted porphyrins |
| US20030232784A1 (en) * | 2002-06-14 | 2003-12-18 | Benedict James J. | Hyaluronic acid-associated superoxide dismutase mimics and their use in the treatment of joint pain |
| US6984636B2 (en) * | 2002-08-12 | 2006-01-10 | Medical Research Council | Mitochondrially targeted antioxidants |
| CA2499994C (en) * | 2002-09-23 | 2012-07-10 | Verion, Inc. | Abuse-resistant pharmaceutical compositions |
| US20060089343A1 (en) * | 2002-12-06 | 2006-04-27 | Alcon, Inc. | Superoxide dismutase mimics for the treatment of ocular disorders and diseases |
| MXPA05005937A (es) * | 2002-12-06 | 2005-08-18 | Alcon Inc | Imitaciones de superoxido de dismutasa para el tratamiento de trastornos y enfermedades oculares. |
| KR100648618B1 (ko) * | 2003-11-19 | 2006-11-23 | 주식회사 웰스킨 | 활성 산소 억제제 |
| US20070060557A1 (en) * | 2003-12-11 | 2007-03-15 | Klimko Peter G | Superoxide dismutase mimics for the treatment of optic nerve and retinal damage |
| WO2006069326A2 (en) * | 2004-12-21 | 2006-06-29 | Metaphore Pharmaceuticals, Inc. | Polyethylene glycolated superoxide dismutase mimetics |
| 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 |
| KR100724586B1 (ko) | 2005-12-09 | 2007-06-04 | 세종대학교산학협력단 | 수퍼옥사이드 디스뮤타아제 활성을 갖는 고리화합물 |
| US9855279B2 (en) | 2006-10-12 | 2018-01-02 | Galera Labs, Llc | Methods of treating oral mucositis |
| US8486928B2 (en) * | 2007-11-14 | 2013-07-16 | Galera Therapeutics | Super-oxide dismutase mimetics |
| EP2296645B1 (en) | 2008-05-22 | 2014-11-19 | Galera Therapeutics, LLC | Combination antitumor therapy |
| US11382895B2 (en) | 2008-05-23 | 2022-07-12 | National Jewish Health | Methods for treating injury associated with exposure to an alkylating species |
| 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 |
| IL297735B2 (en) | 2015-08-11 | 2024-08-01 | Galera Labs Llc | Macrocyclic ring pentase complexes with oral bioavailability |
| KR20230075528A (ko) | 2016-05-03 | 2023-05-31 | 갈레라 랩스, 엘엘씨 | 암 치료를 위한 조합 요법 |
| EP3506907B1 (en) | 2016-09-01 | 2023-06-07 | Galera Labs, LLC | Combination cancer therapy with a pentaaza macrocyclic ring complex and an ascorbate compound |
| CN110520107A (zh) | 2017-02-15 | 2019-11-29 | 加莱拉实验室有限责任公司 | 用于局部肠递送的五氮杂大环状环配合物 |
| EP3388082A1 (en) | 2017-04-13 | 2018-10-17 | Galera Labs, LLC | Combination cancer immunotherapy with pentaaza macrocyclic ring complex |
| IL295620B2 (en) | 2017-04-13 | 2024-01-01 | Galera Labs Llc | Combination cancer immunotherapy with pentaaza macrocyclic ring complex |
| MX2020008028A (es) | 2018-01-31 | 2020-12-11 | Galera Labs Llc | Terapia de combinacion para cancer con complejo de anillo macrociclico de pentaaza y agente anticancer basado en platino. |
| US20230071463A1 (en) * | 2020-02-13 | 2023-03-09 | Teva Pharmaceuticals International Gmbh | Solid state forms of avasopasem manganese and process for preparation thereof |
| AU2024300676A1 (en) * | 2023-07-21 | 2026-01-29 | Board Of Regents Of The University Of Texas System | Carcinogenesis reduction with pentaaza macrocyclic ring complex |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0751496B2 (ja) | 1986-04-02 | 1995-06-05 | 武田薬品工業株式会社 | リポソ−ムの製造法 |
| US5216021A (en) | 1986-08-28 | 1993-06-01 | Sorenson John R J | Analgesic method |
| US4999347A (en) | 1986-08-28 | 1991-03-12 | Sorenson John R J | Analgesic method |
| JPS63313581A (ja) * | 1987-06-16 | 1988-12-21 | Ube Ind Ltd | 修飾ス−パ−オキシドジスムタ−ゼ |
| CA2072934C (en) | 1991-07-19 | 2007-08-28 | Karl William Aston | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| ES2113952T3 (es) | 1991-07-19 | 1998-05-16 | Monsanto Co | Complejos de manganeso con ligandos macrociclicos nitrogenados eficaces como catalizadores para dismutar superoxidos. |
| CN1088086A (zh) * | 1992-12-14 | 1994-06-22 | 西北大学 | 一种新型的护肤保健品 |
| US6204259B1 (en) | 1993-01-14 | 2001-03-20 | Monsanto Company | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| US6525041B1 (en) | 1995-06-06 | 2003-02-25 | Pharmacia Corporation | Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| BR9708179A (pt) | 1996-03-13 | 1999-07-27 | Monsanto Co | Bioconjugados de complexos de manganês ou ferro de ligantes macrociclicos contendo nitrogênio eficazes como catalizadores para desmutar superoxidos |
-
1998
- 1998-04-09 US US09/057,831 patent/US6180620B1/en not_active Expired - Fee Related
- 1998-06-15 ES ES98929022T patent/ES2215305T3/es not_active Expired - Lifetime
- 1998-06-15 EP EP98929022A patent/EP1001752B1/en not_active Expired - Lifetime
- 1998-06-15 DE DE69820633T patent/DE69820633T2/de not_active Expired - Fee Related
- 1998-06-15 JP JP50459399A patent/JP2002506445A/ja not_active Ceased
- 1998-06-15 AU AU80685/98A patent/AU733415B2/en not_active Ceased
- 1998-06-15 CA CA002294155A patent/CA2294155A1/en not_active Abandoned
- 1998-06-15 PT PT98929022T patent/PT1001752E/pt unknown
- 1998-06-15 DK DK98929022T patent/DK1001752T3/da active
- 1998-06-15 WO PCT/US1998/012231 patent/WO1998058636A1/en not_active Ceased
- 1998-06-15 AT AT98929022T patent/ATE256467T1/de not_active IP Right Cessation
- 1998-06-19 ZA ZA985376A patent/ZA985376B/xx unknown
-
2000
- 2000-08-09 US US09/634,152 patent/US6395725B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6180620B1 (en) | 2001-01-30 |
| ATE256467T1 (de) | 2004-01-15 |
| DK1001752T3 (da) | 2004-04-19 |
| DE69820633T2 (de) | 2004-09-23 |
| DE69820633D1 (de) | 2004-01-29 |
| JP2002506445A (ja) | 2002-02-26 |
| ZA985376B (en) | 1999-06-21 |
| WO1998058636A1 (en) | 1998-12-30 |
| AU733415B2 (en) | 2001-05-17 |
| CA2294155A1 (en) | 1998-12-30 |
| AU8068598A (en) | 1999-01-04 |
| EP1001752A1 (en) | 2000-05-24 |
| EP1001752B1 (en) | 2003-12-17 |
| US6395725B1 (en) | 2002-05-28 |
| PT1001752E (pt) | 2004-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2215305T3 (es) | Metodos analgesicos usando los catalizadores sinteticos para la dismutacion de los radicales superoxido. | |
| RU2000102359A (ru) | Фармацевтическая композиция, обладающая улучшенным противораковым действием и/или сниженными побочными эффектами, содержащая противораковый агент и производное гидроксамовой кислоты | |
| ES2251097T3 (es) | Tratamiento con cromo/biotina de la diabetes tipo ii. | |
| ES2356986T3 (es) | Agentes antitumorales. | |
| ES2381968T3 (es) | 2,2'-ditio-bis(etanosulfonato) para su uso en la inhibición de la termoestesia anómala inducida por paclitaxel | |
| BRPI0608716A2 (pt) | composição, uso de uma composição, e, kit para inibir crescimento de célula anormal | |
| US20040219138A1 (en) | Combinations of superoxide dismutase mimetics and opioids | |
| KR20130118981A (ko) | 다형 교모세포종의 치료를 위한 마시텐탄 포함 조합물 | |
| US20090131377A1 (en) | Combinations of Superoxide Dismutase Mimetics and Nonsteroidal Analgesic/Anti-Inflammatory Drugs | |
| EP3740215A1 (en) | Combination therapy for treatment of leukemia | |
| FR2556216A1 (fr) | Nouveau medicament analgesique contenant du proglumide, eventuellement en association avec des medicaments analgesiques-narcotiques | |
| JP2018172419A (ja) | メタロポルフィリン神経学処置 | |
| WO2005041886A2 (en) | Methods for generating or increasing revenues related to pain inhibitor commerce | |
| ES2249616T3 (es) | Citidina-fosfocolina para el tratamiento de la neuropatia diabetica. | |
| WO2005042718A2 (en) | Compositions and methods for treating, preventing, reversing and inhibiting pain | |
| JP2004536076A (ja) | Ｐ−ｇｐインヒビターおよび抗癲癇薬を含んでなる組合せ剤 | |
| US20130096068A1 (en) | Combination therapy with a proteasome inhibitor and a gallium complex | |
| RU2005132175A (ru) | Комбинированное лечение опухолей, включающее неморубицин и лучевую терапию | |
| ES2214548T3 (es) | Combinacion de un bloqueante de los beta-receptores y un opioide. | |
| US20080255238A1 (en) | Composition containing a thiourea derivative for preventing or treating pruritic or irritant skin diseases | |
| RU2823100C2 (ru) | Анальгетическая субстанция эндогенной природы, фармацевтическая композиция на ее основе и способы их применения | |
| RU2303450C2 (ru) | Нестероидное противовоспалительное анальгетическое средство | |
| WO2005060437A2 (en) | Composition combinations and methods for treating, preventing, reversing and inhibiting pain | |
| WO2005041894A2 (en) | Compositions and methods for treating, preventing, reversing and inhibiting pain | |
| WO2007083985A1 (es) | Composición farmacéutica sinergística de diclofenaco y clonixinato de lisina |