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 PDF

Info

Publication number: NO321523B1
Authority: NO; Norway
Prior art keywords: compound; formula; amorphous; derivatives; branched
Prior art date: 1999-06-24

Application number

NO20016232A

Other languages

English (en)

Norwegian (no)

Other versions

NO20016232L (no

NO20016232D0 (no

Inventor

Francesca Benedini

Patrizia Antognazza

Original Assignee

Nicox Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-06-24

Filing date

2001-12-19

Publication date

2006-05-15

2001-12-19 Application filed by Nicox Sa filed Critical Nicox Sa

2001-12-19 Publication of NO20016232L publication Critical patent/NO20016232L/no

2001-12-19 Publication of NO20016232D0 publication Critical patent/NO20016232D0/no

2006-05-15 Publication of NO321523B1 publication Critical patent/NO321523B1/no

Links

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
229920000168 Microcrystalline cellulose Polymers 0.000 description 9
239000008108 microcrystalline cellulose Substances 0.000 description 9
235000019813 microcrystalline cellulose Nutrition 0.000 description 9
229940016286 microcrystalline cellulose Drugs 0.000 description 9
238000012360 testing method Methods 0.000 description 9
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
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
230000000694 effects Effects 0.000 description 6
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
238000010521 absorption reaction Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
150000005419 hydroxybenzoic acid derivatives Chemical class 0.000 description 4
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
238000000889 atomisation Methods 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
238000001938 differential scanning calorimetry curve Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
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
229910052708 sodium Inorganic materials 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
238000007711 solidification Methods 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000000870 ultraviolet spectroscopy Methods 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
238000005303 weighing Methods 0.000 description 2
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
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000005792 cardiovascular activity Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
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
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1

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)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (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)

NO20016232A 1999-06-24 2001-12-19 Preparat omfattende et nitroksyderivat, farmasoytisk formulering inneholdende dette og fremgangsmate for fremstilling av preparatet. NO321523B1 (no)

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
NO20016232L NO20016232L (no)	2001-12-19
NO20016232D0 NO20016232D0 (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 (pl)
EP (1)	EP1187803B1 (pl)
JP (1)	JP2003503380A (pl)
KR (1)	KR100672001B1 (pl)
CN (1)	CN1187312C (pl)
AT (1)	ATE302746T1 (pl)
AU (1)	AU781479B2 (pl)
BR (1)	BR0011831A (pl)
CA (1)	CA2377132A1 (pl)
DE (1)	DE60022188T2 (pl)
DK (1)	DK1187803T3 (pl)
ES (1)	ES2246878T3 (pl)
HU (1)	HUP0201721A3 (pl)
IL (1)	IL146789A0 (pl)
IT (1)	IT1312115B1 (pl)
MX (1)	MXPA01013273A (pl)
NO (1)	NO321523B1 (pl)
NZ (1)	NZ515757A (pl)
PL (1)	PL195557B1 (pl)
RU (1)	RU2248963C2 (pl)
TR (1)	TR200103624T2 (pl)
WO (1)	WO2001000563A1 (pl)
ZA (1)	ZA200109862B (pl)

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JP5524851B2 (ja) *	2007-10-17	2014-06-18	エフ．オボカイティス，トッド	室温で安定な非結晶アスピリン
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TR201805216T4 (en)	2008-10-28	2018-06-21	Arena Pharm Inc	COMPOSITIONS OF A USEFUL 5-HT2A SEROTONINE RECEPTOR MODULATOR FOR THE TREATMENT OF RELATED DISORDERS
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WO2015187974A1 (en)	2014-06-06	2015-12-10	Ovokaitys Todd Frank	Methods and compositions for increasing the bioactivity of nutrients
HK1245660A1 (zh)	2015-06-12	2018-08-31	Axovant Sciences Gmbh	有用於预防和治疗rem睡眠行为障碍的二芳基脲和芳基脲衍生物
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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
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1999
- 1999-06-24 IT IT1999MI001402A patent/IT1312115B1/it active
2000
- 2000-06-21 MX MXPA01013273A patent/MXPA01013273A/es active IP Right Grant
- 2000-06-21 DE DE60022188T patent/DE60022188T2/de not_active Expired - Fee Related
- 2000-06-21 US US10/009,741 patent/US6753442B1/en not_active Expired - Fee Related
- 2000-06-21 DK DK00949202T patent/DK1187803T3/da active
- 2000-06-21 TR TR2001/03624T patent/TR200103624T2/xx unknown
- 2000-06-21 AT AT00949202T patent/ATE302746T1/de not_active IP Right Cessation
- 2000-06-21 CA CA002377132A patent/CA2377132A1/en not_active Abandoned
- 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 BR BR0011831-1A patent/BR0011831A/pt not_active Application Discontinuation
- 2000-06-21 CN CNB008091919A patent/CN1187312C/zh not_active Expired - Fee Related
- 2000-06-21 ES ES00949202T patent/ES2246878T3/es not_active Expired - Lifetime
- 2000-06-21 IL IL14678900A patent/IL146789A0/xx not_active IP Right Cessation
- 2000-06-21 HU HU0201721A patent/HUP0201721A3/hu unknown
- 2000-06-21 NZ NZ515757A patent/NZ515757A/xx unknown
- 2000-06-21 RU RU2001134613/04A patent/RU2248963C2/ru not_active IP Right Cessation
- 2000-06-21 WO PCT/EP2000/005723 patent/WO2001000563A1/en not_active Ceased
- 2000-06-21 KR KR1020017015729A patent/KR100672001B1/ko not_active Expired - Fee Related
- 2000-06-21 JP JP2001506976A patent/JP2003503380A/ja active Pending
- 2000-06-21 PL PL00352529A patent/PL195557B1/pl unknown
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
ITMI991402A1 (it)	2000-12-24
WO2001000563A1 (en)	2001-01-04
ES2246878T3 (es)	2006-03-01
ITMI991402A0 (it)	1999-06-24
EP1187803B1 (en)	2005-08-24
CA2377132A1 (en)	2001-01-04
EP1187803A1 (en)	2002-03-20
TR200103624T2 (tr)	2002-04-22
RU2248963C2 (ru)	2005-03-27
NO20016232L (no)	2001-12-19
DK1187803T3 (da)	2005-11-28
CN1187312C (zh)	2005-02-02
PL352529A1 (en)	2003-08-25
AU6264400A (en)	2001-01-31
MXPA01013273A (es)	2003-07-14
HUP0201721A2 (en)	2002-10-28
ZA200109862B (en)	2003-05-28
CN1356975A (zh)	2002-07-03
DE60022188D1 (de)	2005-09-29
NO20016232D0 (no)	2001-12-19
US6753442B1 (en)	2004-06-22
IT1312115B1 (it)	2002-04-04
BR0011831A (pt)	2002-03-19
ATE302746T1 (de)	2005-09-15
AU781479B2 (en)	2005-05-26
KR20020008220A (ko)	2002-01-29
PL195557B1 (pl)	2007-10-31
KR100672001B1 (ko)	2007-01-19
DE60022188T2 (de)	2006-06-08
NZ515757A (en)	2004-02-27
HUP0201721A3 (en)	2003-08-28
IL146789A0 (en)	2002-07-25
JP2003503380A (ja)	2003-01-28

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