HRP970381A2 - Furan nitrone compounds - Google Patents
Furan nitrone compoundsInfo
- Publication number
- HRP970381A2 HRP970381A2 HR60/022,169A HRP970381A HRP970381A2 HR P970381 A2 HRP970381 A2 HR P970381A2 HR P970381 A HRP970381 A HR P970381A HR P970381 A2 HRP970381 A2 HR P970381A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- alkyl
- cycloalkyl
- aryl
- alkaryl
- Prior art date
Links
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims description 136
- -1 Furan nitrone compounds Chemical class 0.000 title claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 158
- 125000000217 alkyl group Chemical group 0.000 claims description 148
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 131
- 125000003118 aryl group Chemical group 0.000 claims description 124
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 110
- 125000003342 alkenyl group Chemical group 0.000 claims description 107
- 125000000304 alkynyl group Chemical group 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 104
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 103
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 102
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 102
- 239000001257 hydrogen Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 230000001154 acute effect Effects 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 150000001768 cations Chemical class 0.000 claims description 22
- 239000003937 drug carrier Substances 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 208000027866 inflammatory disease Diseases 0.000 claims description 18
- 230000004770 neurodegeneration Effects 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- 208000023275 Autoimmune disease Diseases 0.000 claims description 15
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 238000011161 development Methods 0.000 claims description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- 206010012289 Dementia Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 5
- 206010015226 Erythema nodosum Diseases 0.000 claims description 4
- 206010024229 Leprosy Diseases 0.000 claims description 4
- 206010040070 Septic Shock Diseases 0.000 claims description 4
- 206010046851 Uveitis Diseases 0.000 claims description 4
- HCFOIMKMIBDXBF-UHFFFAOYSA-N furan;sulfuryl dichloride Chemical class C=1C=COC=1.ClS(Cl)(=O)=O HCFOIMKMIBDXBF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000036303 septic shock Effects 0.000 claims description 4
- 230000009885 systemic effect Effects 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000013223 septicemia Diseases 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- RHBMVXBGYGIDJN-UHFFFAOYSA-N furan-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CO1 RHBMVXBGYGIDJN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- WCSYSXNCNHIGRB-UHFFFAOYSA-N n-cyclohexyl-1-(5-sulfofuran-2-yl)methanimine oxide Chemical compound O1C(S(=O)(=O)O)=CC=C1C=[N+]([O-])C1CCCCC1 WCSYSXNCNHIGRB-UHFFFAOYSA-N 0.000 claims description 2
- GCJGLGAMQZFNIF-UHFFFAOYSA-N n-propan-2-yl-1-(5-sulfofuran-2-yl)methanimine oxide Chemical compound CC(C)[N+]([O-])=CC1=CC=C(S(O)(=O)=O)O1 GCJGLGAMQZFNIF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 150000002431 hydrogen Chemical class 0.000 claims 45
- 150000003254 radicals Chemical class 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000002474 experimental method Methods 0.000 description 29
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 241000700159 Rattus Species 0.000 description 18
- 238000004611 spectroscopical analysis Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 208000006011 Stroke Diseases 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 201000010099 disease Diseases 0.000 description 15
- STHCVXSOPOLWFU-UHFFFAOYSA-M sodium;5-[[oxido(propan-2-yl)azaniumylidene]methyl]furan-2-sulfonate Chemical compound [Na+].CC(C)[N+]([O-])=CC1=CC=C(S([O-])(=O)=O)O1 STHCVXSOPOLWFU-UHFFFAOYSA-M 0.000 description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- 230000001363 autoimmune Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 13
- 238000004435 EPR spectroscopy Methods 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 102000047918 Myelin Basic Human genes 0.000 description 11
- 101710107068 Myelin basic protein Proteins 0.000 description 11
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- 239000002158 endotoxin Substances 0.000 description 11
- 229920006008 lipopolysaccharide Polymers 0.000 description 11
- 230000000626 neurodegenerative effect Effects 0.000 description 11
- 210000002569 neuron Anatomy 0.000 description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 11
- URIMPWMBVPNFDM-UHFFFAOYSA-N 5-formylfuran-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)O1 URIMPWMBVPNFDM-UHFFFAOYSA-N 0.000 description 10
- 102000004127 Cytokines Human genes 0.000 description 10
- 108090000695 Cytokines Proteins 0.000 description 10
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 150000002443 hydroxylamines Chemical class 0.000 description 9
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
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- 230000004968 inflammatory condition Effects 0.000 description 8
- IYSYLWYGCWTJSG-UHFFFAOYSA-N n-tert-butyl-1-phenylmethanimine oxide Chemical compound CC(C)(C)[N+]([O-])=CC1=CC=CC=C1 IYSYLWYGCWTJSG-UHFFFAOYSA-N 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
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- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
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- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 6
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- VCUVETGKTILCLC-UHFFFAOYSA-N 5,5-dimethyl-1-pyrroline N-oxide Chemical compound CC1(C)CCC=[N+]1[O-] VCUVETGKTILCLC-UHFFFAOYSA-N 0.000 description 3
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
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- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ZTJAVDOZUQPVAV-UHFFFAOYSA-M sodium;5-formylfuran-2-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=O)O1 ZTJAVDOZUQPVAV-UHFFFAOYSA-M 0.000 description 1
- ATHQLWIRLNAEKR-UHFFFAOYSA-M sodium;benzoic acid;hydroxide Chemical compound O.[Na+].[O-]C(=O)C1=CC=CC=C1 ATHQLWIRLNAEKR-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/64—Sulfur atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2216996P | 1996-07-19 | 1996-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP970381A2 true HRP970381A2 (en) | 1998-08-31 |
Family
ID=21808169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR60/022,169A HRP970381A2 (en) | 1996-07-19 | 1997-07-15 | Furan nitrone compounds |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US6376540B1 (fr) |
| EP (1) | EP1021430A1 (fr) |
| JP (1) | JP2000514822A (fr) |
| KR (1) | KR20000067915A (fr) |
| AR (1) | AR008781A1 (fr) |
| AU (1) | AU715226B2 (fr) |
| CA (1) | CA2260825A1 (fr) |
| CO (1) | CO4910142A1 (fr) |
| HR (1) | HRP970381A2 (fr) |
| ID (1) | ID19679A (fr) |
| IL (1) | IL128070A0 (fr) |
| MA (1) | MA26434A1 (fr) |
| NZ (1) | NZ333705A (fr) |
| TN (1) | TNSN97125A1 (fr) |
| WO (1) | WO1998003496A1 (fr) |
| ZA (1) | ZA976388B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW429241B (en) * | 1996-09-26 | 2001-04-11 | Sumitomo Pharma | Nitrone derivatives |
| AU2226999A (en) * | 1998-01-16 | 1999-08-02 | Renovis, Inc. | Thiophene nitrone compounds |
| JP2002509143A (ja) * | 1998-01-16 | 2002-03-26 | センター ファーマシューティカルズ， インコーポレイテッド | チオエーテルフランニトロン化合物 |
| AU3985799A (en) * | 1998-05-19 | 1999-12-06 | Centaur Pharmaceuticals, Inc. | Furan nitrone therapeutics for the treatment of inflammatory bowel disease |
| DE69917643T2 (de) | 1998-07-17 | 2004-10-07 | Renovis Inc | Alpha-(2-hydroxyphenyl)nitrone, diese enthaltenden pharmazeutische zubereitungen sowie deren verwendung zur behandlung von entzündungen |
| US6730700B2 (en) * | 1998-12-02 | 2004-05-04 | Renovis, Inc. | 3,4,5,-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same |
| UA66401C2 (en) | 1998-12-02 | 2004-05-17 | Sentor Pharmaceuticals Inc | 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same |
| EP1562975A2 (fr) * | 2002-10-25 | 2005-08-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Composes steroides comprenant des groupes mimetiques de la superoxyde dismutase et des groupes donneurs d'oxyde nitrique, et leur utilisation dans la preparation de medicaments |
| US20060166894A1 (en) * | 2002-11-29 | 2006-07-27 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Ace-inhibitors having antioxidant and no-donor activity |
| US20050059638A1 (en) * | 2003-08-04 | 2005-03-17 | Kelly Michael G. | Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders |
| US20050182060A1 (en) * | 2004-02-13 | 2005-08-18 | Kelly Michael G. | 2-Substituted and 4-substituted aryl nitrone compounds |
| US9034926B2 (en) | 2010-12-30 | 2015-05-19 | Nicholas V. Perricone | Topical nitrone spin trap compositions for psoriasis |
| US8986739B2 (en) | 2011-02-28 | 2015-03-24 | Nicholas V. Perricone | Treatment of urinary incontinence using nitrone spin traps |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666754A (en) | 1965-11-06 | 1972-05-30 | Dainippon Pharmaceutical Co | 2-(5-nitrofuryl) nitrone derivatives |
| US3988159A (en) | 1967-07-28 | 1976-10-26 | American Can Company | Light-sensitive material containing nitrone for forming heat-fixed images |
| US3834073A (en) | 1971-05-03 | 1974-09-10 | Scm Corp | Phenyl nitrone derivatives useful as seed protectants |
| US3849934A (en) | 1971-05-03 | 1974-11-26 | Scm Corp | Alpha-aryl-n-lower alkyl nitrone-containing compositions useful as anti-fungal agents |
| US3950327A (en) | 1972-09-19 | 1976-04-13 | Ciba-Geigy Corporation | New nitrones, their manufacture and their use for the manufacture of n-substituted araliphatic aldehyde-nitrones |
| US3903049A (en) | 1974-01-30 | 1975-09-02 | Goodyear Tire & Rubber | Oxidation resistant sulfur curable rubbery polymers |
| US3917700A (en) | 1974-01-30 | 1975-11-04 | Goodyear Tire & Rubber | Nitrone compounds |
| GB1588417A (en) | 1977-03-15 | 1981-04-23 | Agfa Gevaert | Photoresist materials |
| US4153722A (en) | 1977-10-06 | 1979-05-08 | William H. Rorer, Inc. | Method of treatment |
| GB2137619A (en) | 1983-03-30 | 1984-10-10 | Gerald Scott | Nitrone compounds and stabilised rubber compositions containing them |
| US5723502A (en) | 1985-07-18 | 1998-03-03 | Proctor; Peter H. | Topical spin trap composition and method |
| US5352442A (en) | 1985-07-18 | 1994-10-04 | Proctor Peter H | Topical tempo |
| US4871862A (en) | 1986-08-27 | 1989-10-03 | Fisons Corporation | α-Substituted ketonitrone derivatives |
| US4803282A (en) | 1986-08-27 | 1989-02-07 | Pennwalt Corporation | Alpha-substituted ketonitrone derivatives |
| DE68917946T2 (de) | 1988-01-29 | 1995-01-05 | Peter H Proctor | Haarwachstumanregung mit Nitroxyd und anderen Radikalen. |
| CA2069961C (fr) * | 1989-10-17 | 2000-05-02 | John M. Carney | Methode et compositions pour l'inhibition des troubles associes a des lesions dues a l'oxydation |
| WO1992022290A1 (fr) * | 1991-06-18 | 1992-12-23 | Oklahoma Medical Research Foundation | Emploi du blocage par spin pour le traitement de maladies associees a l'oxydation des lipides et des proteines |
| US5292746A (en) | 1991-09-12 | 1994-03-08 | Merrell Dow Pharmaceuticals Inc. | Cyclic nitrones, pharmaceutical compositions thereof and their use in treating shock |
| GB9300894D0 (en) | 1992-02-07 | 1993-03-10 | Zeneca Ltd | Oxime derivatives |
| US5455272A (en) | 1993-10-22 | 1995-10-03 | Oklahoma Medical Research Foundation | Spin trap nitronyl hindered phenols |
| US5488145A (en) * | 1993-12-23 | 1996-01-30 | Oklahoma Medical Research Foundation | 2,4-disulfonyl phenyl butyl nitrone, its salts, and their use as pharmaceutical free radical traps |
| CA2235765C (fr) | 1995-11-17 | 2006-04-04 | David A. Becker | Agents de piegeage de spin a base d'azulenyl-nitrones, et leurs procedes de fabrication et d'utilisation |
| TW429241B (en) | 1996-09-26 | 2001-04-11 | Sumitomo Pharma | Nitrone derivatives |
-
1997
- 1997-07-14 US US09/230,065 patent/US6376540B1/en not_active Expired - Fee Related
- 1997-07-14 IL IL12807097A patent/IL128070A0/xx unknown
- 1997-07-14 CA CA002260825A patent/CA2260825A1/fr not_active Abandoned
- 1997-07-14 AU AU36555/97A patent/AU715226B2/en not_active Ceased
- 1997-07-14 NZ NZ333705A patent/NZ333705A/xx unknown
- 1997-07-14 KR KR1019997000372A patent/KR20000067915A/ko not_active Withdrawn
- 1997-07-14 EP EP97933350A patent/EP1021430A1/fr not_active Withdrawn
- 1997-07-14 WO PCT/US1997/011960 patent/WO1998003496A1/fr not_active Ceased
- 1997-07-14 JP JP10506980A patent/JP2000514822A/ja active Pending
- 1997-07-15 HR HR60/022,169A patent/HRP970381A2/hr not_active Application Discontinuation
- 1997-07-16 MA MA24719A patent/MA26434A1/fr unknown
- 1997-07-17 US US08/895,968 patent/US5942507A/en not_active Expired - Fee Related
- 1997-07-18 AR ARP970103231A patent/AR008781A1/es unknown
- 1997-07-18 ID IDP972489A patent/ID19679A/id unknown
- 1997-07-18 CO CO97040897A patent/CO4910142A1/es unknown
- 1997-07-18 ZA ZA9706388A patent/ZA976388B/xx unknown
- 1997-07-18 TN TNTNSN97125A patent/TNSN97125A1/fr unknown
-
1999
- 1999-05-24 US US09/317,267 patent/US6040444A/en not_active Expired - Fee Related
- 1999-05-24 US US09/317,266 patent/US6051571A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000067915A (ko) | 2000-11-25 |
| TNSN97125A1 (fr) | 2005-03-15 |
| US6051571A (en) | 2000-04-18 |
| ID19679A (id) | 1998-07-30 |
| MA26434A1 (fr) | 2004-12-20 |
| US6376540B1 (en) | 2002-04-23 |
| AU3655597A (en) | 1998-02-10 |
| US5942507A (en) | 1999-08-24 |
| AU715226B2 (en) | 2000-01-20 |
| JP2000514822A (ja) | 2000-11-07 |
| AR008781A1 (es) | 2000-02-23 |
| WO1998003496A1 (fr) | 1998-01-29 |
| ZA976388B (en) | 1998-02-19 |
| NZ333705A (en) | 2000-09-29 |
| US6040444A (en) | 2000-03-21 |
| CA2260825A1 (fr) | 1998-01-29 |
| EP1021430A1 (fr) | 2000-07-26 |
| CO4910142A1 (es) | 2000-04-24 |
| IL128070A0 (en) | 1999-11-30 |
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| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20000715 Year of fee payment: 4 |
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| ODBC | Application rejected |