DK166757B1 - Flydende vandigt praeparat af en 2-amino-5-oxo-5h-(1)-benzopyran(2,3-b)-pyridin-3-karboxylsyre - Google Patents

Flydende vandigt praeparat af en 2-amino-5-oxo-5h-(1)-benzopyran(2,3-b)-pyridin-3-karboxylsyre Download PDF

Info

Publication number: DK166757B1
Authority: DK; Denmark
Prior art keywords: compound; solution; polyvinylpyrrolidone; aqueous liquid; preparation
Prior art date: 1985-08-19

Application number

DK379986A

Other languages

Danish (da)

English (en)

Other versions

DK379986A (da

DK379986D0 (da

Inventor

Hisayoshi Shimizu

Mitsuaki Oshima

Hideo Terayama

Original Assignee

Takeda Chemical Industries Ltd

Senju Pharma Co

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.)

1985-08-19

Filing date

1986-08-08

Publication date

1993-07-12

1986-08-08 Application filed by Takeda Chemical Industries Ltd, Senju Pharma Co filed Critical Takeda Chemical Industries Ltd

1986-08-08 Publication of DK379986D0 publication Critical patent/DK379986D0/da

1987-02-20 Publication of DK379986A publication Critical patent/DK379986A/da

1993-07-12 Application granted granted Critical

1993-07-12 Publication of DK166757B1 publication Critical patent/DK166757B1/da

Links

238000002360 preparation method Methods 0.000 title claims abstract description 49
239000007788 liquid Substances 0.000 title claims abstract description 35
239000011664 nicotinic acid Substances 0.000 title claims description 5
IARKXVVJPQZJJD-UHFFFAOYSA-N 2-aminochromen-5-one Chemical compound O1C(N)=CC=C2C1=CC=CC2=O IARKXVVJPQZJJD-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 45
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims abstract description 42
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 37
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 37
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 35
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 21
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims abstract description 21
229960001948 caffeine Drugs 0.000 claims abstract description 21
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims abstract description 21
239000002904 solvent Substances 0.000 claims abstract description 18
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 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 40
239000003889 eye drop Substances 0.000 claims description 24
229940126062 Compound A Drugs 0.000 claims description 15
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 15
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 15
239000004327 boric acid Substances 0.000 claims description 15
239000007923 nasal drop Substances 0.000 claims description 15
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
235000001968 nicotinic acid Nutrition 0.000 claims description 3
NJRNRSGIUZYMQH-UHFFFAOYSA-N chromen-5-one Chemical compound O1C=CC=C2C(=O)C=CC=C21 NJRNRSGIUZYMQH-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 36
206010015946 Eye irritation Diseases 0.000 abstract description 6
231100000013 eye irritation Toxicity 0.000 abstract description 6
239000000243 solution Substances 0.000 description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
239000008213 purified water Substances 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
235000010338 boric acid Nutrition 0.000 description 14
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 14
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 14
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 14
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
229940061607 dibasic sodium phosphate Drugs 0.000 description 11
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 11
229940012356 eye drops Drugs 0.000 description 11
229910021538 borax Inorganic materials 0.000 description 10
239000012528 membrane Substances 0.000 description 10
239000004328 sodium tetraborate Substances 0.000 description 10
235000010339 sodium tetraborate Nutrition 0.000 description 10
239000001116 FEMA 4028 Substances 0.000 description 9
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 9
235000011175 beta-cyclodextrine Nutrition 0.000 description 9
229960004853 betadex Drugs 0.000 description 9
235000011187 glycerol Nutrition 0.000 description 9
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 9
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 9
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 9
229960002216 methylparaben Drugs 0.000 description 9
239000013589 supplement Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 8
229940045641 monobasic sodium phosphate Drugs 0.000 description 8
229910000403 monosodium phosphate Inorganic materials 0.000 description 8
235000019799 monosodium phosphate Nutrition 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 8
239000008363 phosphate buffer Substances 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000007794 irritation Effects 0.000 description 5
229940100662 nasal drops Drugs 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 4
239000006172 buffering agent Substances 0.000 description 4
-1 hydroxytylcellulose Polymers 0.000 description 4
230000001954 sterilising effect Effects 0.000 description 4
238000004659 sterilization and disinfection Methods 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000000872 buffer Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229960003350 isoniazid Drugs 0.000 description 3
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 3
239000000865 liniment Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
239000004299 sodium benzoate Substances 0.000 description 3
235000010234 sodium benzoate Nutrition 0.000 description 3
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 3
229940033663 thimerosal Drugs 0.000 description 3
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000002738 chelating agent Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 2
239000006196 drop Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940040145 liniment Drugs 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000005152 nicotinamide Nutrition 0.000 description 2
239000011570 nicotinamide Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
229920002451 polyvinyl alcohol Polymers 0.000 description 2
229960004025 sodium salicylate Drugs 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
SZQWMYZNSVNSOI-UHFFFAOYSA-N 2-amino-7-propan-2-ylchromen-5-one Chemical compound O1C(N)=CC=C2C(=O)C=C(C(C)C)C=C21 SZQWMYZNSVNSOI-UHFFFAOYSA-N 0.000 description 1
WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 1
OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 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-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
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 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
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 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
239000002671 adjuvant Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 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
230000015572 biosynthetic process Effects 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000000463 material Substances 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
231100000286 mucous membrane, eye irritation or corrosion testing Toxicity 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
239000006179 pH buffering agent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000008569 process Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229940037001 sodium edetate Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
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235000011008 sodium phosphates Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
210000001835 viscera Anatomy 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
- A—HUMAN NECESSITIES
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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- A61K47/40—Cyclodextrins; Derivatives thereof
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
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DK379986A 1985-08-19 1986-08-08 Flydende vandigt praeparat af en 2-amino-5-oxo-5h-(1)-benzopyran(2,3-b)-pyridin-3-karboxylsyre DK166757B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP18238385		1985-08-19
JP18238385		1985-08-19

Publications (3)

Publication Number	Publication Date
DK379986D0 DK379986D0 (da)	1986-08-08
DK379986A DK379986A (da)	1987-02-20
DK166757B1 true DK166757B1 (da)	1993-07-12

Family

ID=16117350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK379986A DK166757B1 (da)	1985-08-19	1986-08-08	Flydende vandigt praeparat af en 2-amino-5-oxo-5h-(1)-benzopyran(2,3-b)-pyridin-3-karboxylsyre

Country Status (10)

Country	Link
US (1)	US4728509A (fr)
EP (1)	EP0213514B1 (fr)
JP (1)	JPS62123116A (fr)
AT (1)	ATE53944T1 (fr)
CA (1)	CA1269618A (fr)
DE (1)	DE3672097D1 (fr)
DK (1)	DK166757B1 (fr)
IE (1)	IE59425B1 (fr)
MY (1)	MY102075A (fr)
NO (1)	NO171005C (fr)

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PL2486942T3 (pl) *	2004-11-24	2019-05-31	Meda Pharmaceuticals Inc	Kompozycje zawierające azelastynę oraz sposoby ich stosowania
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WO2006099359A2 (fr)	2005-03-10	2006-09-21	3M Innovative Properties Company	Methodes de reduction d'une contamination microbienne
US20070009532A1 (en) *	2005-07-06	2007-01-11	Branimir Sikic	Treatment of patients with cancer using a calicheamicin-antibody conjugate in combination with zosuquidar
US20070010485A1 (en) *	2005-07-06	2007-01-11	Jeff Schwegman	Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins
US20070010487A1 (en) *	2005-07-06	2007-01-11	Jeff Schwegman	Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins
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1986
- 1986-08-05 US US06/893,161 patent/US4728509A/en not_active Expired - Lifetime
- 1986-08-08 DK DK379986A patent/DK166757B1/da not_active IP Right Cessation
- 1986-08-12 NO NO863253A patent/NO171005C/no unknown
- 1986-08-15 EP EP86111306A patent/EP0213514B1/fr not_active Expired - Lifetime
- 1986-08-15 DE DE8686111306T patent/DE3672097D1/de not_active Expired - Fee Related
- 1986-08-15 AT AT86111306T patent/ATE53944T1/de not_active IP Right Cessation
- 1986-08-18 IE IE221486A patent/IE59425B1/en not_active IP Right Cessation
- 1986-08-18 JP JP61193834A patent/JPS62123116A/ja active Granted
- 1986-08-18 CA CA000516160A patent/CA1269618A/fr not_active Expired - Lifetime
1987
- 1987-09-29 MY MYPI87002198A patent/MY102075A/en unknown

Also Published As

Publication number	Publication date
IE59425B1 (en)	1994-02-23
US4728509A (en)	1988-03-01
CA1269618A (fr)	1990-05-29
JPH0478614B2 (fr)	1992-12-11
NO171005C (no)	1993-01-13
DK379986A (da)	1987-02-20
MY102075A (en)	1992-03-31
JPS62123116A (ja)	1987-06-04
ATE53944T1 (de)	1990-07-15
NO171005B (no)	1992-10-05
IE862214L (en)	1987-02-19
EP0213514B1 (fr)	1990-06-20
DK379986D0 (da)	1986-08-08
EP0213514A2 (fr)	1987-03-11
NO863253D0 (no)	1986-08-12
NO863253L (no)	1987-02-20
DE3672097D1 (de)	1990-07-26
EP0213514A3 (en)	1987-07-22

Legal Events

Date	Code	Title	Description
1993-07-12	B1	Patent granted (law 1993)
1998-04-20	PBP	Patent lapsed

Publication	Publication Date	Title
US4728509A (en)	1988-03-01	Aqueous liquid preparation
KR920001461B1 (ko)	1992-02-14	안과 액제의 제조방법
JPH07116029B2 (ja)	1995-12-13	トラニラスト水溶液製剤
TWI495469B (zh)	2015-08-11	含有氟喹諾酮抗生素藥物之經改良藥學組成物
JP2003506416A (ja)	2003-02-18	モキシフロキサシン／塩化ナトリウム製剤
JPH1160505A (ja)	1999-03-02	防腐組成物
AU2014212274A1 (en)	2015-08-13	Aqueous ophthalmic solutions of phentolamine and medical uses thereof
JP3659801B2 (ja)	2005-06-15	トラニラスト水溶液製剤
EP0233615B1 (fr)	1992-03-04	Préparation aqueuse et son procédé de fabrication
JP2916340B2 (ja)	1999-07-05	ナトリウムクロモグリケートの水性医薬組成物
KR102444571B1 (ko)	2022-09-19	세티리진 및 토코페솔란을 포함하는 안과용 조성물
EP0348527B1 (fr)	1993-06-23	Collyre antiallergique
JPH03109326A (ja)	1991-05-09	フレロキサシン点眼液
JP2003192583A (ja)	2003-07-09	消炎点眼剤
JP2004238346A (ja)	2004-08-26	トラニラストの安定な水溶液製剤
WO1993003723A1 (fr)	1993-03-04	Complexe antagoniste de recepteur de leucotrienes-antihistamine
WO2005101982A2 (fr)	2005-11-03	Composition ophtalmique stable
JPH1029937A (ja)	1998-02-03	メフェナム酸水溶液製剤
BR112021001339A2 (pt)	2021-04-20	composições e métodos para tratar os olhos
JPWO2001087303A1 (ja)	2003-07-29	水性液剤
JPWO2002017932A1 (ja)	2003-10-14	Ｏｃｔ製剤
JP2822049B2 (ja)	1998-11-05	水性製剤組成物
WO2024225436A1 (fr)	2024-10-31	Composition ophtalmique
JPH08268892A (ja)	1996-10-15	水溶液製剤及びその製造方法
TWI907378B (zh)	2025-12-11	含有雷帕黴素的外用劑及其製造方法