NO321028B1 - Tiazolinsyrederivater, anvendelse av disse for fremstilling av medikamenter, samt anvendelse av disse for forebygging eller behandling av en patologisk tilstand mottagelig for chelatering eller sekvesttrasjon av trivalente metaller. - Google Patents
Tiazolinsyrederivater, anvendelse av disse for fremstilling av medikamenter, samt anvendelse av disse for forebygging eller behandling av en patologisk tilstand mottagelig for chelatering eller sekvesttrasjon av trivalente metaller. Download PDFInfo
- Publication number
- NO321028B1 NO321028B1 NO20011003A NO20011003A NO321028B1 NO 321028 B1 NO321028 B1 NO 321028B1 NO 20011003 A NO20011003 A NO 20011003A NO 20011003 A NO20011003 A NO 20011003A NO 321028 B1 NO321028 B1 NO 321028B1
- Authority
- NO
- Norway
- Prior art keywords
- pharmaceutically acceptable
- compound according
- alkyl
- salts
- carbon atoms
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 34
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 15
- 239000002184 metal Substances 0.000 title claims abstract description 15
- 230000001575 pathological effect Effects 0.000 title claims abstract description 13
- 150000002739 metals Chemical class 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000009920 chelation Effects 0.000 title claims description 5
- 230000002265 prevention Effects 0.000 title claims description 5
- 230000009919 sequestration Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 208000018565 Hemochromatosis Diseases 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- 208000031856 Haemosiderosis Diseases 0.000 claims description 3
- 230000007882 cirrhosis Effects 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 3
- 150000003549 thiazolines Chemical class 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 35
- -1 pyridoxyl isonicotinoyl hydrazone Chemical class 0.000 description 24
- 229910052742 iron Inorganic materials 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000797 iron chelating agent Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 239000000589 Siderophore Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000010438 iron metabolism Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000287227 Fringillidae Species 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical compound CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 229940014259 gelatin Drugs 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 229940075525 iron chelating agent Drugs 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JFZAJWBGISKERI-UHFFFAOYSA-N 2,4-dihydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(O)=C1 JFZAJWBGISKERI-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 108010061075 Enterobactin Proteins 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- 102000008857 Ferritin Human genes 0.000 description 2
- 108050000784 Ferritin Proteins 0.000 description 2
- 238000008416 Ferritin Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 208000002903 Thalassemia Diseases 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000002655 chelation therapy Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SERBHKJMVBATSJ-BZSNNMDCSA-N enterobactin Chemical compound OC1=CC=CC(C(=O)N[C@@H]2C(OC[C@@H](C(=O)OC[C@@H](C(=O)OC2)NC(=O)C=2C(=C(O)C=CC=2)O)NC(=O)C=2C(=C(O)C=CC=2)O)=O)=C1O SERBHKJMVBATSJ-BZSNNMDCSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 230000012953 feeding on blood of other organism Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229960003299 ketamine Drugs 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000003859 lipid peroxidation Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000032258 transport Effects 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- PUWVNTVQJFSBDH-UHFFFAOYSA-N (2S-cis)-N,N'-[(3,6-dioxopiperazine-2,5-diyl)di-3,1-propanediyl]bis[N-hydroxyacetamide] Natural products CC(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(C)=O)NC1=O PUWVNTVQJFSBDH-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- QIJRTFXNRTXDIP-YBBRRFGFSA-N (2s)-2-amino-3-sulfanylpropanoic acid;hydrate;hydrochloride Chemical compound O.Cl.SC[C@@H](N)C(O)=O QIJRTFXNRTXDIP-YBBRRFGFSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GRUVVLWKPGIYEG-UHFFFAOYSA-N 2-[2-[carboxymethyl-[(2-hydroxyphenyl)methyl]amino]ethyl-[(2-hydroxyphenyl)methyl]amino]acetic acid Chemical compound C=1C=CC=C(O)C=1CN(CC(=O)O)CCN(CC(O)=O)CC1=CC=CC=C1O GRUVVLWKPGIYEG-UHFFFAOYSA-N 0.000 description 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 229930195710 D‐cysteine Natural products 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- SERBHKJMVBATSJ-UHFFFAOYSA-N Enterobactin Natural products OC1=CC=CC(C(=O)NC2C(OCC(C(=O)OCC(C(=O)OC2)NC(=O)C=2C(=C(O)C=CC=2)O)NC(=O)C=2C(=C(O)C=CC=2)O)=O)=C1O SERBHKJMVBATSJ-UHFFFAOYSA-N 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- TZXKOCQBRNJULO-UHFFFAOYSA-N Ferriprox Chemical compound CC1=C(O)C(=O)C=CN1C TZXKOCQBRNJULO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- 206010065973 Iron Overload Diseases 0.000 description 1
- 206010022979 Iron excess Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- GYMWSBVKAPVTPI-UHFFFAOYSA-N N1N=[C-]N=C1 Chemical class N1N=[C-]N=C1 GYMWSBVKAPVTPI-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102000004338 Transferrin Human genes 0.000 description 1
- 108090000901 Transferrin Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000004656 cell transport Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- BQYIXOPJPLGCRZ-REZTVBANSA-N chembl103111 Chemical compound CC1=NC=C(CO)C(\C=N\NC(=O)C=2C=CN=CC=2)=C1O BQYIXOPJPLGCRZ-REZTVBANSA-N 0.000 description 1
- PWRDYSVMTCDMOD-SSDOTTSWSA-N chembl11300 Chemical compound OC(=O)[C@H]1CSC(C=2C(=CC(O)=CC=2)O)=N1 PWRDYSVMTCDMOD-SSDOTTSWSA-N 0.000 description 1
- OEUUFNIKLCFNLN-LLVKDONJSA-N chembl432481 Chemical compound OC(=O)[C@@]1(C)CSC(C=2C(=CC(O)=CC=2)O)=N1 OEUUFNIKLCFNLN-LLVKDONJSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical class *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001944 cysteine derivatives Chemical class 0.000 description 1
- 229960000958 deferoxamine Drugs 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- SRMBQCVUAVULDJ-UHFFFAOYSA-N ferrioxamine b Chemical compound [Fe+3].CC(=O)N([O-])CCCCCNC(=O)CCC(=O)N([O-])CCCCCNC(=O)CCC(=O)N([O-])CCCCCN SRMBQCVUAVULDJ-UHFFFAOYSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 230000003617 peroxidasic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011809 primate model Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 210000001995 reticulocyte Anatomy 0.000 description 1
- PUWVNTVQJFSBDH-RYUDHWBXSA-N rhodotorulic acid Chemical compound CC(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(C)=O)NC1=O PUWVNTVQJFSBDH-RYUDHWBXSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 208000004003 siderosis Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 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
- 238000012360 testing method Methods 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 231100000402 unacceptable toxicity Toxicity 0.000 description 1
- 238000010518 undesired secondary reaction Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229940100445 wheat starch Drugs 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P25/28—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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/04—Chelating agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Toxicology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Game Rules And Presentations Of Slot Machines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/144,103 US6083966A (en) | 1998-08-31 | 1998-08-31 | Thiazoline acid derivatives |
| PCT/US1999/019691 WO2000012493A1 (en) | 1998-08-31 | 1999-08-31 | Thiazoline acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011003L NO20011003L (no) | 2001-02-27 |
| NO20011003D0 NO20011003D0 (no) | 2001-02-27 |
| NO321028B1 true NO321028B1 (no) | 2006-02-27 |
Family
ID=22507049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011003A NO321028B1 (no) | 1998-08-31 | 2001-02-27 | Tiazolinsyrederivater, anvendelse av disse for fremstilling av medikamenter, samt anvendelse av disse for forebygging eller behandling av en patologisk tilstand mottagelig for chelatering eller sekvesttrasjon av trivalente metaller. |
Country Status (24)
| Country | Link |
|---|---|
| US (9) | US6083966A (zh) |
| EP (1) | EP1109795B1 (zh) |
| JP (3) | JP4817498B2 (zh) |
| KR (1) | KR20010074907A (zh) |
| CN (1) | CN100455574C (zh) |
| AT (1) | ATE317392T1 (zh) |
| AU (1) | AU759851B2 (zh) |
| BR (1) | BR9913441B1 (zh) |
| CA (1) | CA2342210C (zh) |
| CZ (1) | CZ2001711A3 (zh) |
| DE (1) | DE69929807T2 (zh) |
| EA (1) | EA200100261A1 (zh) |
| ES (1) | ES2260933T3 (zh) |
| HK (1) | HK1035720A1 (zh) |
| HU (1) | HUP0103165A3 (zh) |
| IL (2) | IL141611A0 (zh) |
| NO (1) | NO321028B1 (zh) |
| NZ (1) | NZ509899A (zh) |
| PL (1) | PL346852A1 (zh) |
| PT (1) | PT1109795E (zh) |
| TR (1) | TR200100541T2 (zh) |
| UA (1) | UA57161C2 (zh) |
| WO (1) | WO2000012493A1 (zh) |
| YU (1) | YU21801A (zh) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083966A (en) * | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| NZ526880A (en) * | 1998-09-21 | 2005-05-27 | Univ Florida | Antimalarial agents |
| EP1488791A3 (en) * | 1998-09-21 | 2005-04-06 | University Of Florida Research Foundation, Inc. | Antimalarial agents |
| US6806363B1 (en) * | 1999-04-16 | 2004-10-19 | Mayo Foundation For Medical Education & Research | Cobalamin conjugates useful as antitumor agents |
| CA2387767A1 (en) | 1999-10-15 | 2001-04-26 | Henricus P. C. Hogenkamp | Cobalamin conjugates useful as imaging and therapeutic agents |
| US6689788B1 (en) * | 2000-08-25 | 2004-02-10 | University Of Florida | Method and composition for treatment of inflammatory bowel disease |
| WO2002055530A2 (en) * | 2000-10-25 | 2002-07-18 | Mayo Foundation | Transcobalamin binding conjugates useful for treating abnormal cellular proliferation |
| AU2003247374A1 (en) * | 2002-05-15 | 2003-12-02 | Genzyme Corporation | Synthesis of 2-alkylcysteines, 2-(hydroxylated phenyl)-4-alkylthiazoline-4-carboxylic acids and derivatives thereof |
| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| AU2003263948A1 (en) * | 2002-08-22 | 2004-03-11 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| US20060069134A1 (en) * | 2002-10-01 | 2006-03-30 | Kaneka Corporation | Process for producing optically active alpha-substituted cysteine or salt thereof, intermediate therefor, and process for producing the same |
| US20040185028A1 (en) * | 2003-03-19 | 2004-09-23 | Zhenze Hu | Antimicrobial compositions containing ethanolamine buffer and biguanide disinfectant |
| DE602004014949D1 (de) * | 2003-09-09 | 2008-08-21 | Univ Florida | Polyamin-metallchelatbildner-konjugate |
| AU2003270473A1 (en) * | 2003-09-09 | 2005-04-27 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| US20120095058A1 (en) * | 2003-12-03 | 2012-04-19 | Hanauske-Abel H M | Method of preventing survival of retrovirally cells and of inhibiting formation of infectious retroviruses |
| US7919623B2 (en) * | 2004-02-04 | 2011-04-05 | Shionogi & Co., Ltd. | Naphthyridine derivatives having inhibitory activity against HIV integrase |
| CN101189216B (zh) * | 2005-04-04 | 2011-10-19 | 佛罗里达大学研究基金会 | Desferrithiocin聚醚类似物 |
| US7365371B2 (en) | 2005-08-04 | 2008-04-29 | Cree, Inc. | Packages for semiconductor light emitting devices utilizing dispensed encapsulants |
| AU2007351826A1 (en) * | 2006-12-12 | 2008-10-30 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogue actinide decorporation agents |
| AU2008229472B2 (en) * | 2007-03-15 | 2013-03-14 | University Of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
| US8063227B2 (en) * | 2008-07-14 | 2011-11-22 | Ferrokin Biosciences, Inc. | Salts and polymorphs of desazadesferrithiocin polyether analogues as metal chelation agents |
| US20130053387A1 (en) | 2010-05-04 | 2013-02-28 | FerroKin BioScience, Inc. | Desazadesferrothiocin and desazadesferrothiocin polyether analogues as metal chelation agents |
| CN103562379A (zh) * | 2011-05-19 | 2014-02-05 | 国立大学法人德岛大学 | 细胞分化诱导剂以及分化诱导方法 |
| KR102111176B1 (ko) | 2011-12-16 | 2020-05-15 | 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 | 4'-데스페리티오신 유사체의 용도 |
| JP6353751B2 (ja) * | 2013-09-25 | 2018-07-04 | 国立大学法人電気通信大学 | 新規複素環式化合物及びその塩、並びに、発光基質組成物 |
| EP3071201A4 (en) * | 2013-11-22 | 2017-04-26 | University of Florida Research Foundation, Inc. | Desferrithiocin analogs and uses thereof |
| AU2016255770A1 (en) | 2015-04-27 | 2017-11-16 | University Of Florida Research Foundation, Incorporated | Metabolically programmed metal chelators and uses thereof |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274207A (en) | 1966-09-20 | Processes for preparing thiazole carboxylic acids | ||
| US3809754A (en) | 1968-12-31 | 1974-05-07 | Medial De Toledo & Cie | Method of treating diseases of the mucous membrane using compounds of a thiazolidine carboxylic acid and pharmaceutical preparations thereof |
| US3882110A (en) | 1969-06-11 | 1975-05-06 | Roussel Uclaf | Novel 2-alkyl-5-thiazole-carboxylic acid derivatives |
| DE2045818A1 (de) | 1969-09-17 | 1971-04-08 | Godo Shusei Kabushiki Kaisha, Tokio | Aeruginoinsäure und Verfahren zu ihrer Herstellung |
| FR2062120A5 (zh) | 1969-10-10 | 1971-06-25 | Messier Fa | |
| FR2141526B1 (zh) | 1971-06-14 | 1975-05-30 | Roussel Uclaf | |
| DE2245560A1 (de) | 1972-09-16 | 1974-03-21 | Basf Ag | Verfahren zur herstellung von 4alkoxycarbonyl-2-thiazolinen |
| US4430344A (en) | 1978-04-08 | 1984-02-07 | Santen Pharmaceutical Co., Ltd. | Antihypertensive 4-thiazolidinecarboxylic acids |
| CS205217B1 (cs) | 1979-04-05 | 1981-05-29 | Zdenek Vitamvas | Dozimetr ionizujícího záření |
| DE3002989A1 (de) | 1980-01-29 | 1981-07-30 | Hoechst Ag, 6000 Frankfurt | Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels |
| JPS5758682A (en) * | 1980-07-28 | 1982-04-08 | Ciba Geigy Ag | Thiazoline derivatives, manufacture and medicinal composition containing same |
| DE3170401D1 (en) * | 1980-07-28 | 1985-06-13 | Ciba Geigy Ag | Triazoline derivatives and processes for their preparation |
| JPS5772975A (en) | 1980-10-24 | 1982-05-07 | Kureha Chem Ind Co Ltd | 2-substituted phenylthiazole derviative, and medicine for peptic ulcer containing said derivative as active component |
| US4367233A (en) | 1981-10-02 | 1983-01-04 | American Home Products Corporation | Inhibitors of mammalian collagenase |
| WO1986003677A1 (en) | 1984-12-18 | 1986-07-03 | David Rubin | Anti-tumor compositions containing the reaction product of a cytotoxic aldehyde with penicillamine and method of use thereof |
| HU200177B (en) | 1985-06-18 | 1990-04-28 | Biogal Gyogyszergyar | Process for producing thiazolidinecarboxylic acids and pharmaceutical compositions comprising such compounds |
| US4736060A (en) | 1985-08-06 | 1988-04-05 | Nippon Rikagakuyakuhin Co., Ltd. | Method for optical resolution of DL-cysteine and (R,S)-1-(1-naphthyl) ethylamine |
| EP0214933A3 (de) | 1985-09-03 | 1989-05-24 | Ciba-Geigy Ag | Kombinationspräparate zur Behandlung von Malaria |
| EP0214101A3 (de) | 1985-09-03 | 1989-05-31 | Ciba-Geigy Ag | Verwendung von Eisen(III)-Chelatoren vom Typ Desferrioxamin B und Desferriferrithiocin zur Behandlung von Malaria |
| JPS62142168A (ja) | 1985-10-16 | 1987-06-25 | Mitsubishi Chem Ind Ltd | チアゾ−ル誘導体及びそれを有効成分とするロイコトリエンきつ抗剤 |
| DE3735757A1 (de) | 1987-10-22 | 1989-05-03 | Degussa | Optisch aktive salze aus einem substituierten thiazolidin-4-carboxylat und 3-chlor-2-hydroxypropyltrimethylammonium, deren herstellung und verwendung |
| ATE98631T1 (de) | 1988-01-20 | 1994-01-15 | Ciba Geigy Ag | Verfahren zur herstellung von komplexverbindungen. |
| GB8826035D0 (en) | 1988-11-07 | 1988-12-14 | Ici Plc | Herbicidal compositions |
| US5182402A (en) | 1988-11-07 | 1993-01-26 | Imperial Chemical Industries Plc | Herbicidal compositions |
| US5106992A (en) | 1989-07-28 | 1992-04-21 | E. R. Squibb & Sons, Inc. | 3,5-dihydroxypentanoic acid derivatives useful as antihypercholesterolemic agents and method for preparing same |
| NL9001955A (nl) | 1990-09-05 | 1992-04-01 | Cedona Pharm Bv | Nieuwe thiazolidinederivaten. |
| US5393777A (en) | 1990-11-15 | 1995-02-28 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon Health Sciences University | Deferration using anguibactin siderophore |
| SG86971A1 (en) | 1990-11-30 | 2002-03-19 | Teijin Ltd | 2-arylthiazole derivatives and pharmaceutical composition thereof |
| DK0934937T3 (da) | 1990-11-30 | 2002-04-02 | Otsuka Pharma Co Ltd | Azolderivater som superoxidradikalinhibitor |
| FR2677021B1 (fr) | 1991-05-31 | 1993-10-01 | Upsa Laboratoires | Nouveaux derives de thiazole antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| US5840739A (en) * | 1992-11-16 | 1998-11-24 | University Of Florida Research Foundation, Inc. | Thiazoline acid derivatives |
| AU5602594A (en) * | 1992-11-16 | 1994-06-08 | University Of Florida Research Foundation, Inc. | 2-(pyrid-2'-yl)-2-thiazoline-4(s)-carboxylic acid derivatives |
| DE4301356A1 (de) | 1993-01-20 | 1994-07-21 | Basf Ag | Verfahren zur Herstellung von 2-Alkyl-4-fluormethyl-thiazolcarbonsäure-alkylestern |
| FR2749583B1 (fr) | 1996-06-07 | 1998-08-21 | Lipha | Nouveaux derives de thiazolidine -2,4- dione substitues, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| US20020049316A1 (en) | 1997-04-29 | 2002-04-25 | Halbert Stacie Marie | Protease inhibitors |
| US6373912B1 (en) * | 1997-06-16 | 2002-04-16 | Legerity, Inc. | Phase-locked loop arrangement with fast lock mode |
| US6174070B1 (en) * | 1998-03-02 | 2001-01-16 | Elna Kabushiki Kaisha | Portable lighting instrument having a light emitting diode assembly |
| MA26618A1 (fr) | 1998-04-09 | 2004-12-20 | Smithkline Beecham Corp | Composes et compositions pharmaceutiques pour le traitement du paludisme |
| US6147070A (en) | 1998-06-05 | 2000-11-14 | Facchini; Francesco | Methods and compositions for controlling iron stores to treat and cure disease states |
| US6083966A (en) | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| US6159983A (en) | 1998-09-18 | 2000-12-12 | University Of Florida | Method and composition for treatment of inflammatory bowel disease |
| NZ526880A (en) * | 1998-09-21 | 2005-05-27 | Univ Florida | Antimalarial agents |
| US6251927B1 (en) * | 1999-04-20 | 2001-06-26 | Medinox, Inc. | Methods for treatment of sickle cell anemia |
| DE19919336A1 (de) | 1999-04-27 | 2000-11-16 | Consortium Elektrochem Ind | Verfahren zur Ringspaltung von Thiazolidinderivaten |
| DE19948434A1 (de) | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| AU2003263948A1 (en) | 2002-08-22 | 2004-03-11 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| DE602004014949D1 (de) | 2003-09-09 | 2008-08-21 | Univ Florida | Polyamin-metallchelatbildner-konjugate |
| AU2003270473A1 (en) * | 2003-09-09 | 2005-04-27 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| CA2587558A1 (en) | 2004-11-19 | 2006-05-26 | Shiva Biomedical, Llc | Methods of treating erythropoietin-resistance |
| CN101189216B (zh) * | 2005-04-04 | 2011-10-19 | 佛罗里达大学研究基金会 | Desferrithiocin聚醚类似物 |
| AU2007351826A1 (en) * | 2006-12-12 | 2008-10-30 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogue actinide decorporation agents |
| AU2008229472B2 (en) * | 2007-03-15 | 2013-03-14 | University Of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
-
1998
- 1998-08-31 US US09/144,103 patent/US6083966A/en not_active Ceased
-
1999
- 1999-08-31 JP JP2000567521A patent/JP4817498B2/ja not_active Expired - Fee Related
- 1999-08-31 PL PL99346852A patent/PL346852A1/xx not_active Application Discontinuation
- 1999-08-31 EP EP99945267A patent/EP1109795B1/en not_active Expired - Lifetime
- 1999-08-31 DE DE69929807T patent/DE69929807T2/de not_active Expired - Lifetime
- 1999-08-31 EA EA200100261A patent/EA200100261A1/ru unknown
- 1999-08-31 CZ CZ2001711A patent/CZ2001711A3/cs unknown
- 1999-08-31 ES ES99945267T patent/ES2260933T3/es not_active Expired - Lifetime
- 1999-08-31 YU YU21801A patent/YU21801A/sh unknown
- 1999-08-31 BR BRPI9913441-1B1A patent/BR9913441B1/pt not_active IP Right Cessation
- 1999-08-31 CN CNB998099899A patent/CN100455574C/zh not_active Expired - Fee Related
- 1999-08-31 PT PT99945267T patent/PT1109795E/pt unknown
- 1999-08-31 HU HU0103165A patent/HUP0103165A3/hu unknown
- 1999-08-31 CA CA002342210A patent/CA2342210C/en not_active Expired - Fee Related
- 1999-08-31 TR TR2001/00541T patent/TR200100541T2/xx unknown
- 1999-08-31 AT AT99945267T patent/ATE317392T1/de not_active IP Right Cessation
- 1999-08-31 IL IL14161199A patent/IL141611A0/xx active IP Right Grant
- 1999-08-31 NZ NZ509899A patent/NZ509899A/en not_active IP Right Cessation
- 1999-08-31 WO PCT/US1999/019691 patent/WO2000012493A1/en not_active Application Discontinuation
- 1999-08-31 KR KR1020017002702A patent/KR20010074907A/ko not_active Application Discontinuation
- 1999-08-31 UA UA2001032117A patent/UA57161C2/uk unknown
- 1999-08-31 AU AU57897/99A patent/AU759851B2/en not_active Ceased
-
2000
- 2000-03-20 US US09/531,755 patent/US6525080B1/en not_active Expired - Lifetime
- 2000-03-20 US US09/531,753 patent/US6559315B1/en not_active Expired - Lifetime
- 2000-03-20 US US09/531,754 patent/US6521652B1/en not_active Expired - Lifetime
-
2001
- 2001-02-22 IL IL141611A patent/IL141611A/en not_active IP Right Cessation
- 2001-02-27 NO NO20011003A patent/NO321028B1/no not_active IP Right Cessation
- 2001-09-04 HK HK01106220A patent/HK1035720A1/xx not_active IP Right Cessation
- 2001-10-17 US US09/981,586 patent/USRE39132E1/en not_active Expired - Lifetime
-
2002
- 2002-11-20 US US10/300,071 patent/US20030236417A1/en not_active Abandoned
-
2004
- 2004-09-17 US US10/944,150 patent/US7126004B2/en not_active Expired - Fee Related
-
2006
- 2006-09-15 US US11/522,299 patent/US7531563B2/en not_active Expired - Fee Related
-
2009
- 2009-03-27 US US12/383,854 patent/US8008502B2/en not_active Expired - Fee Related
-
2011
- 2011-04-22 JP JP2011095879A patent/JP5520875B2/ja not_active Expired - Fee Related
-
2013
- 2013-12-12 JP JP2013257270A patent/JP2014065730A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7531563B2 (en) | Thiazoline acid derivatives | |
| EP1380577B1 (en) | Thiazoline acid derivatives | |
| Bergeron et al. | The desferrithiocin pharmacophore | |
| AU774956B2 (en) | Antimalarial agents | |
| MXPA01001968A (en) | Thiazoline acid derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |