NO321523B1 - Preparat omfattende et nitroksyderivat, farmasoytisk formulering inneholdende dette og fremgangsmate for fremstilling av preparatet. - Google Patents
Preparat omfattende et nitroksyderivat, farmasoytisk formulering inneholdende dette og fremgangsmate for fremstilling av preparatet. Download PDFInfo
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- NO321523B1 NO321523B1 NO20016232A NO20016232A NO321523B1 NO 321523 B1 NO321523 B1 NO 321523B1 NO 20016232 A NO20016232 A NO 20016232A NO 20016232 A NO20016232 A NO 20016232A NO 321523 B1 NO321523 B1 NO 321523B1
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 30
- 239000000203 mixture Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- -1 3-(nitro-oxymethyl)phenyl ester Chemical class 0.000 claims description 21
- 229920000858 Cyclodextrin Polymers 0.000 claims description 18
- 238000001694 spray drying Methods 0.000 claims description 15
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 12
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 150000002828 nitro derivatives Chemical class 0.000 claims description 8
- 238000000227 grinding Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229940097362 cyclodextrins Drugs 0.000 claims description 4
- 150000002016 disaccharides Chemical class 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000001116 FEMA 4028 Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 3
- 229960004853 betadex Drugs 0.000 claims description 3
- 150000001720 carbohydrates Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 238000004898 kneading Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 229920001542 oligosaccharide Polymers 0.000 claims description 3
- 150000002482 oligosaccharides Chemical class 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910004679 ONO2 Inorganic materials 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 23
- 238000004090 dissolution Methods 0.000 description 18
- 239000013543 active substance Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000007922 dissolution test Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 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 12
- 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 12
- 239000008101 lactose Substances 0.000 description 12
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- 238000012360 testing method Methods 0.000 description 9
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- 239000008367 deionised water Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
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- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-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 4
- 239000004570 mortar (masonry) Substances 0.000 description 4
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
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- 238000012512 characterization method Methods 0.000 description 2
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- VHVPQPYKVGDNFY-ZPGVKDDISA-N itraconazole Chemical compound O=C1N(C(C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-ZPGVKDDISA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- QEADDMRPIXYSTF-UHFFFAOYSA-N 2-[4-[bis(2-chloroethyl)amino]phenyl]ethyl acetate Chemical compound CC(=O)OCCC1=CC=C(N(CCCl)CCCl)C=C1 QEADDMRPIXYSTF-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 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 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
- 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 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 239000008119 colloidal silica Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
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- 238000003113 dilution method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 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
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999MI001402A IT1312115B1 (it) | 1999-06-24 | 1999-06-24 | Composti amorfi e relative composizioni farmaceutiche |
| PCT/EP2000/005723 WO2001000563A1 (en) | 1999-06-24 | 2000-06-21 | Amorphous nitric esters and their pharmaceutical compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20016232D0 NO20016232D0 (no) | 2001-12-19 |
| NO20016232L NO20016232L (no) | 2001-12-19 |
| NO321523B1 true NO321523B1 (no) | 2006-05-15 |
Family
ID=11383219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20016232A NO321523B1 (no) | 1999-06-24 | 2001-12-19 | Preparat omfattende et nitroksyderivat, farmasoytisk formulering inneholdende dette og fremgangsmate for fremstilling av preparatet. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6753442B1 (pt) |
| EP (1) | EP1187803B1 (pt) |
| JP (1) | JP2003503380A (pt) |
| KR (1) | KR100672001B1 (pt) |
| CN (1) | CN1187312C (pt) |
| AT (1) | ATE302746T1 (pt) |
| AU (1) | AU781479B2 (pt) |
| BR (1) | BR0011831A (pt) |
| CA (1) | CA2377132A1 (pt) |
| DE (1) | DE60022188T2 (pt) |
| DK (1) | DK1187803T3 (pt) |
| ES (1) | ES2246878T3 (pt) |
| HU (1) | HUP0201721A3 (pt) |
| IL (1) | IL146789A0 (pt) |
| IT (1) | IT1312115B1 (pt) |
| MX (1) | MXPA01013273A (pt) |
| NO (1) | NO321523B1 (pt) |
| NZ (1) | NZ515757A (pt) |
| PL (1) | PL195557B1 (pt) |
| RU (1) | RU2248963C2 (pt) |
| TR (1) | TR200103624T2 (pt) |
| WO (1) | WO2001000563A1 (pt) |
| ZA (1) | ZA200109862B (pt) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1319202B1 (it) | 2000-10-12 | 2003-09-26 | Nicox Sa | Farmaci per le malattie a base infiammatoria. |
| JP4092203B2 (ja) | 2000-12-21 | 2008-05-28 | ニトロメッド，インク． | 新規のシクロオキシゲナーゼ２選択的阻害剤としての置換アリール化合物、組成物、および使用方法 |
| EP1219306A1 (en) | 2000-12-29 | 2002-07-03 | Nicox S.A. | Compositions comprising cyclodextrins and NO- releasing drugs |
| EP1539134A4 (en) | 2002-06-11 | 2007-04-11 | Nitromed Inc | SELECTIVE INHIBITORS OF CYCLOOXIGENASE-2 NITROSIS AND / OR NITROSYLES, COMPOSITIONS AND METHODS OF USE |
| US7163958B2 (en) | 2002-07-03 | 2007-01-16 | Nitromed Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| US7244753B2 (en) | 2002-07-29 | 2007-07-17 | Nitromed, Inc. | Cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CN1826322B (zh) | 2003-07-22 | 2012-04-18 | 艾尼纳制药公司 | 用于预防和治疗相关病症而作为5-ht2a血清素受体调节剂的二芳基和芳基杂芳基脲衍生物 |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 |
| US9567327B2 (en) | 2007-08-15 | 2017-02-14 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| EA027333B1 (ru) * | 2007-10-17 | 2017-07-31 | Тодд Ф. Овокайтис | Стабильный при комнатной температуре некристаллический аспирин |
| BRPI0818575A2 (pt) * | 2007-10-17 | 2014-10-07 | Todd F Ovokaitys | Processo para a modificação do estado sólido de um composto e composições co-amorfas produzidas com o mesmo |
| ES2324007A1 (es) * | 2007-10-25 | 2009-07-28 | Ferrer Internacional, S.A. | Una forma amorfa de un compuesto antiinflamatorio. |
| US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
| EP2364142B1 (en) * | 2008-10-28 | 2018-01-17 | Arena Pharmaceuticals, Inc. | Compositions of a 5-ht2a serotonin receptor modulator useful for the treatment of disorders related thereto |
| EP2344592B1 (en) | 2008-11-04 | 2014-12-17 | DSM IP Assets B.V. | D 1413 ht radiation curable coatings for optical fiber |
| US10202598B2 (en) | 2014-05-30 | 2019-02-12 | Todd Frank Ovokaitys | Methods and systems for generation, use, and delivery of activated stem cells |
| WO2015187974A1 (en) | 2014-06-06 | 2015-12-10 | Ovokaitys Todd Frank | Methods and compositions for increasing the bioactivity of nutrients |
| US10384985B2 (en) | 2014-06-06 | 2019-08-20 | B.K. Consultants, Inc. | Methods and compositions for increasing the yield of, and beneficial chemical composition of, certain plants |
| AU2016276966A1 (en) | 2015-06-12 | 2018-01-18 | Axovant Sciences Gmbh | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of REM sleep behavior disorder |
| TW201720439A (zh) | 2015-07-15 | 2017-06-16 | Axovant Sciences Gmbh | 用於預防及治療與神經退化性疾病相關的幻覺之作為５－ｈｔ２ａ血清素受體的二芳基及芳基雜芳基脲衍生物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1243367B (it) * | 1990-07-26 | 1994-06-10 | Italfarmaco Spa | Derivati acidi benzoici sostituiti ad attivita' cardiovascolare |
| IT1256345B (it) * | 1992-08-20 | 1995-12-01 | Esteri nitrici di derivati dell'acido 2-(2,6-di-alo-fenilammino) fenilacetico e procedimento per la loro preparazione | |
| IT1256450B (it) | 1992-11-26 | 1995-12-05 | Soldato Piero Del | Esteri nitrici con attivita' farmacologica e procedimento per la loro preparazione |
| RU2145595C1 (ru) | 1994-05-10 | 2000-02-20 | Никокс С.А. | Нитроксисоединения и фармацевтическая композиция на их основе, имеющие противовоспалительную, анальгетическую и антитромбоцитарную активности |
| IT1276071B1 (it) * | 1995-10-31 | 1997-10-24 | Nicox Ltd | Compositi ad attivita' anti-infiammatoria |
| KR19990001564A (ko) | 1997-06-16 | 1999-01-15 | 유충식 | 용해도를 개선한 아졸계 항진균제 및 이를 함유하는 제제 |
| IT1307928B1 (it) | 1999-01-26 | 2001-11-29 | Nicox Sa | Metodo di sintesi di nitrossimetilfenil esteri di derivatidell'aspirina. |
-
1999
- 1999-06-24 IT IT1999MI001402A patent/IT1312115B1/it active
-
2000
- 2000-06-21 ES ES00949202T patent/ES2246878T3/es not_active Expired - Lifetime
- 2000-06-21 US US10/009,741 patent/US6753442B1/en not_active Expired - Fee Related
- 2000-06-21 RU RU2001134613/04A patent/RU2248963C2/ru not_active IP Right Cessation
- 2000-06-21 JP JP2001506976A patent/JP2003503380A/ja active Pending
- 2000-06-21 BR BR0011831-1A patent/BR0011831A/pt not_active Application Discontinuation
- 2000-06-21 DE DE60022188T patent/DE60022188T2/de not_active Expired - Fee Related
- 2000-06-21 KR KR1020017015729A patent/KR100672001B1/ko not_active IP Right Cessation
- 2000-06-21 EP EP00949202A patent/EP1187803B1/en not_active Expired - Lifetime
- 2000-06-21 AU AU62644/00A patent/AU781479B2/en not_active Ceased
- 2000-06-21 TR TR2001/03624T patent/TR200103624T2/xx unknown
- 2000-06-21 MX MXPA01013273A patent/MXPA01013273A/es active IP Right Grant
- 2000-06-21 CA CA002377132A patent/CA2377132A1/en not_active Abandoned
- 2000-06-21 PL PL00352529A patent/PL195557B1/pl unknown
- 2000-06-21 HU HU0201721A patent/HUP0201721A3/hu unknown
- 2000-06-21 DK DK00949202T patent/DK1187803T3/da active
- 2000-06-21 WO PCT/EP2000/005723 patent/WO2001000563A1/en active IP Right Grant
- 2000-06-21 IL IL14678900A patent/IL146789A0/xx not_active IP Right Cessation
- 2000-06-21 CN CNB008091919A patent/CN1187312C/zh not_active Expired - Fee Related
- 2000-06-21 NZ NZ515757A patent/NZ515757A/xx unknown
- 2000-06-21 AT AT00949202T patent/ATE302746T1/de not_active IP Right Cessation
-
2001
- 2001-11-29 ZA ZA200109862A patent/ZA200109862B/xx unknown
- 2001-12-19 NO NO20016232A patent/NO321523B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6753442B1 (en) | 2004-06-22 |
| NZ515757A (en) | 2004-02-27 |
| ATE302746T1 (de) | 2005-09-15 |
| IT1312115B1 (it) | 2002-04-04 |
| ITMI991402A0 (it) | 1999-06-24 |
| DK1187803T3 (da) | 2005-11-28 |
| AU6264400A (en) | 2001-01-31 |
| NO20016232D0 (no) | 2001-12-19 |
| JP2003503380A (ja) | 2003-01-28 |
| KR20020008220A (ko) | 2002-01-29 |
| NO20016232L (no) | 2001-12-19 |
| EP1187803A1 (en) | 2002-03-20 |
| MXPA01013273A (es) | 2003-07-14 |
| BR0011831A (pt) | 2002-03-19 |
| PL195557B1 (pl) | 2007-10-31 |
| WO2001000563A1 (en) | 2001-01-04 |
| ZA200109862B (en) | 2003-05-28 |
| CN1187312C (zh) | 2005-02-02 |
| HUP0201721A2 (en) | 2002-10-28 |
| CN1356975A (zh) | 2002-07-03 |
| IL146789A0 (en) | 2002-07-25 |
| ITMI991402A1 (it) | 2000-12-24 |
| AU781479B2 (en) | 2005-05-26 |
| TR200103624T2 (tr) | 2002-04-22 |
| EP1187803B1 (en) | 2005-08-24 |
| PL352529A1 (en) | 2003-08-25 |
| HUP0201721A3 (en) | 2003-08-28 |
| DE60022188D1 (de) | 2005-09-29 |
| RU2248963C2 (ru) | 2005-03-27 |
| CA2377132A1 (en) | 2001-01-04 |
| DE60022188T2 (de) | 2006-06-08 |
| KR100672001B1 (ko) | 2007-01-19 |
| ES2246878T3 (es) | 2006-03-01 |
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