KR960005707B1 - 벤조일페닐아세트산 유도체 약제 조성물 - Google Patents
벤조일페닐아세트산 유도체 약제 조성물 Download PDFInfo
- Publication number
- KR960005707B1 KR960005707B1 KR1019890000892A KR890000892A KR960005707B1 KR 960005707 B1 KR960005707 B1 KR 960005707B1 KR 1019890000892 A KR1019890000892 A KR 1019890000892A KR 890000892 A KR890000892 A KR 890000892A KR 960005707 B1 KR960005707 B1 KR 960005707B1
- Authority
- KR
- South Korea
- Prior art keywords
- pharmaceutical composition
- salt
- eye
- inflammatory
- ophthalmic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- YVKSMFUEDUPYIF-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanoic acid Chemical class C=1C=CC=CC=1C(C(=O)O)C(=O)C1=CC=CC=C1 YVKSMFUEDUPYIF-UHFFFAOYSA-N 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 229920003169 water-soluble polymer Polymers 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- -1 carboxypropyl Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 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 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 35
- 239000000203 mixture Substances 0.000 description 35
- 210000001508 eye Anatomy 0.000 description 25
- 239000003814 drug Substances 0.000 description 24
- 229940079593 drug Drugs 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000011200 topical administration Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 239000003889 eye drop Substances 0.000 description 15
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 14
- 230000002757 inflammatory effect Effects 0.000 description 14
- 208000030533 eye disease Diseases 0.000 description 13
- 229940012356 eye drops Drugs 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 206010061218 Inflammation Diseases 0.000 description 12
- 230000004054 inflammatory process Effects 0.000 description 12
- 239000002504 physiological saline solution Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 8
- 210000001331 nose Anatomy 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 229940098773 bovine serum albumin Drugs 0.000 description 7
- 229960000905 indomethacin Drugs 0.000 description 7
- 230000003637 steroidlike Effects 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 206010046851 Uveitis Diseases 0.000 description 5
- 239000002260 anti-inflammatory agent Substances 0.000 description 5
- 229940124599 anti-inflammatory drug Drugs 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 206010015943 Eye inflammation Diseases 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 241001420836 Ophthalmitis Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 description 4
- 210000001124 body fluid Anatomy 0.000 description 4
- 239000010839 body fluid Substances 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 208000010403 panophthalmitis Diseases 0.000 description 4
- 210000003462 vein Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 3
- 208000001860 Eye Infections Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000001746 atrial effect Effects 0.000 description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
- 229960000396 atropine Drugs 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 208000011323 eye infectious disease Diseases 0.000 description 3
- 239000003885 eye ointment Substances 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 229940069265 ophthalmic ointment Drugs 0.000 description 3
- 239000002997 ophthalmic solution Substances 0.000 description 3
- 229940054534 ophthalmic solution Drugs 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 210000004127 vitreous body Anatomy 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010027646 Miosis Diseases 0.000 description 2
- 208000030880 Nose disease Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000000692 Student's t-test Methods 0.000 description 2
- 239000003732 agents acting on the eye Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 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
- 238000000354 decomposition reaction Methods 0.000 description 2
- 208000032625 disorder of ear Diseases 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 210000000744 eyelid Anatomy 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003547 miosis Effects 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 239000003883 ointment base Substances 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012353 t test Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 206010011039 Corneal perforation Diseases 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
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- 208000010412 Glaucoma Diseases 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
- 206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000005856 abnormality Effects 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
- 230000001154 acute effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 210000001742 aqueous humor Anatomy 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- HZFGMQJYAFHESD-UHFFFAOYSA-M bromfenac sodium Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 HZFGMQJYAFHESD-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 201000007717 corneal ulcer Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 description 1
- 229960001048 fluorometholone Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940125702 ophthalmic agent Drugs 0.000 description 1
- 229940023490 ophthalmic product Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- PRGUDWLMFLCODA-UHFFFAOYSA-N oxybuprocaine hydrochloride Chemical compound [Cl-].CCCCOC1=CC(C(=O)OCC[NH+](CC)CC)=CC=C1N PRGUDWLMFLCODA-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- MJAQSCHBMPGJES-UHFFFAOYSA-M sodium (2-amino-3-benzoylphenyl)acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 MJAQSCHBMPGJES-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- BIYQNLJPABKADF-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-bromobenzoyl)phenyl]acetate;hydrate Chemical compound O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 BIYQNLJPABKADF-UHFFFAOYSA-M 0.000 description 1
- FVBKCOXGVZPEDP-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 FVBKCOXGVZPEDP-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 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
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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- 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
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Ophthalmology & Optometry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1668388 | 1988-01-27 | ||
| JP63-16683 | 1988-01-27 | ||
| JP88-16683 | 1988-01-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890011823A KR890011823A (ko) | 1989-08-22 |
| KR960005707B1 true KR960005707B1 (ko) | 1996-05-01 |
Family
ID=11923115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890000892A Expired - Lifetime KR960005707B1 (ko) | 1988-01-27 | 1989-01-27 | 벤조일페닐아세트산 유도체 약제 조성물 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4910225A (https=) |
| EP (1) | EP0326915B1 (https=) |
| JP (1) | JP2683676B2 (https=) |
| KR (1) | KR960005707B1 (https=) |
| AT (1) | ATE80043T1 (https=) |
| AU (1) | AU609932B2 (https=) |
| CA (1) | CA1325382C (https=) |
| DE (1) | DE68902649T2 (https=) |
| ES (1) | ES2052784T3 (https=) |
| GR (1) | GR3005586T3 (https=) |
| HK (1) | HK162895A (https=) |
| PH (1) | PH26827A (https=) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5897858A (en) | 1994-02-03 | 1999-04-27 | Schering-Plough Healthcare Products, Inc. | Nasal spray compositions exhibiting increased retention in the nasal cavity |
| US5475034A (en) * | 1994-06-06 | 1995-12-12 | Alcon Laboratories, Inc. | Topically administrable compositions containing 3-benzoylphenylacetic acid derivatives for treatment of ophthalmic inflammatory disorders |
| US5895645A (en) * | 1995-01-31 | 1999-04-20 | Bausch & Lomb Incorporated | Opthalmic solution for artificial tears |
| RU2116070C1 (ru) * | 1996-07-08 | 1998-07-27 | Севиньдж Исмаил кызы Акберова | Фармацевтическая композиция |
| AR020661A1 (es) * | 1998-09-30 | 2002-05-22 | Alcon Lab Inc | Una composicion farmaceutica topica oftalmica, otica o nasal y el uso de la misma para la manufactura de un medicamento |
| DE19961307A1 (de) * | 1999-12-18 | 2001-07-12 | Krewel Meuselbach Gmbh | Medizinprodukt zur Befeuchtung und Reinigung der Nasenschleimhaut |
| AR030345A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes relacionados con angiogenesis |
| AR030346A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes neurodegenerativos de la retina y cabeza de nervio optico |
| AU2002247284A1 (en) | 2001-04-02 | 2002-10-15 | Alcon, Inc. | Method of treating ocular inflammatory and angiogenesis-related disorders using an amide derivative of flubiprofen or ketorolac |
| US7030149B2 (en) | 2002-04-19 | 2006-04-18 | Allergan, Inc. | Combination of brimonidine timolol for topical ophthalmic use |
| PL373787A1 (en) * | 2002-05-03 | 2005-09-19 | Alcon Inc. | Method of treating vascular endothelial growth factor mediated vascular disorders using amfenac or nepafenac |
| PT1586316E (pt) | 2003-01-21 | 2008-05-28 | Senju Pharma Co | Preparação líquida aquosa contendo ácido 2-amino-3-(4- bromobenzoil)fenilacético |
| US20030187072A1 (en) * | 2003-02-14 | 2003-10-02 | Kapin Michael A. | Method of treating angiogenesis-related disorders |
| US20070043006A1 (en) * | 2003-06-13 | 2007-02-22 | Bingaman David P | Formulations of non-steroidal anti-inflammatory agents to treat pathologic ocular angiogenesis |
| EP1683526B1 (en) * | 2003-11-14 | 2012-04-11 | Senju Pharmaceutical Co., Ltd. | Aqueous solution preparation containing aminoglycoside antibiotic and bromfenac |
| FR2876581B1 (fr) * | 2004-10-20 | 2007-05-18 | Interpharm Dev | Composition bioadhesive a liberation programmee |
| JP4933897B2 (ja) | 2004-11-05 | 2012-05-16 | 千寿製薬株式会社 | 眼内移行性促進水性点眼剤 |
| TWI358290B (en) * | 2004-12-02 | 2012-02-21 | Alcon Inc | Topical nepafenac formulations |
| DK1906916T3 (da) * | 2005-05-10 | 2009-01-19 | Alcon Inc | Oftalmisk suspension, der omfatter et oftalmisk lægemiddel, en poloxamin og et tonicitetsregulerende glycolbaseret middel, anvendelse af sammensætningen til fremstilling af et medikament til behandling af oftalmiske lidelser |
| BRPI0609227A2 (pt) * | 2005-05-10 | 2010-03-09 | Alcon Inc | composições de suspensão de nepafenac e outros fármacos oftálmicos, bem como uso das referidas composições no tratamento tópico de distúrbios oftálmicos |
| US20100130580A1 (en) * | 2006-01-25 | 2010-05-27 | Aciex Therapeutics, Inc. | Formulations and Methods for Treating Dry Eye |
| US20070254841A1 (en) * | 2006-01-25 | 2007-11-01 | Ophthalmic Research Associates, Inc. | Formulations and methods for treating dry eye |
| TW200812575A (en) * | 2006-04-28 | 2008-03-16 | Alcon Inc | Formulations containing amide derivatives of carboxylic acid NSAIDs for topical administration to the eye |
| US20090105245A1 (en) * | 2006-12-21 | 2009-04-23 | Bingaman David P | Methods for treating macular edema and ocular angiogenesis using an anti-inflammatory agent and a receptor tyrosine kinase inhibitor |
| US20080153819A1 (en) * | 2006-12-21 | 2008-06-26 | Bingaman David P | Methods for treating macular edema and pathologic ocular angiogenesis using a neuroprotective agent and a receptor tyrosine kinase inhibitor |
| US20080153818A1 (en) * | 2006-12-21 | 2008-06-26 | Bingaman David P | Methods for preventing inflammation during surgery |
| UY31058A1 (es) * | 2007-05-01 | 2008-10-31 | Alcon Res Ltd | Formulaciones de aminoacido n-halogenado con compuestos antiinflamatorios |
| WO2008153746A1 (en) * | 2007-05-24 | 2008-12-18 | Aciex Therapeutics, Inc. | Formulations and methods for treating dry eye |
| EP2247289A4 (en) * | 2008-02-21 | 2011-05-04 | Ista Pharmaceuticals | OPHTHALMIC NSAIDS AS ADJUVANTIES |
| US8778999B2 (en) * | 2009-03-05 | 2014-07-15 | Insite Vision Incorporated | Non-steroidal anti-inflammatory ophthalmic compositions |
| GB0919757D0 (en) | 2009-11-12 | 2009-12-30 | Johnson Matthey Plc | Polymorphs of bromfenac sodium and methods for preparing bromfenac sodium polymorphs |
| US8299295B2 (en) * | 2009-10-15 | 2012-10-30 | Johnson Matthey Public Limited Company | Polymorphs of bromfenac sodium and methods for preparing bromfenac sodium polymorphs |
| US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
| CA2824433C (en) | 2011-01-18 | 2019-11-12 | Senju Pharmaceutical Co., Ltd. | Aqueous liquid bromfenac composition having preservative efficacy |
| US9827191B2 (en) | 2012-05-03 | 2017-11-28 | The Johns Hopkins University | Compositions and methods for ophthalmic and/or other applications |
| ES3055223T3 (en) | 2012-05-03 | 2026-02-10 | Alcon Inc | Pharmaceutical nanoparticles showing improved mucosal transport |
| JP6360039B2 (ja) | 2012-05-03 | 2018-07-18 | カラ ファーマシューティカルズ インコーポレイテッド | 複数の被覆された粒子を含む組成物、医薬組成物、医薬製剤、及び当該粒子の形成方法 |
| US11596599B2 (en) | 2012-05-03 | 2023-03-07 | The Johns Hopkins University | Compositions and methods for ophthalmic and/or other applications |
| PL2919755T3 (pl) | 2012-11-19 | 2018-07-31 | Bausch & Lomb Incorporated | Wodna ciekła kompozycja zawierająca kwas 2-amino-3-(4-bromobenzoilo)fenylooctowy |
| EP2956138B1 (en) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
| US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
| MX368903B (es) | 2013-02-20 | 2019-10-21 | Kala Pharmaceuticals Inc | Compuestos terapéuticos y sus usos en el tratamiento de enfermedades proliferativas. |
| CA2911983A1 (en) | 2013-06-19 | 2014-12-24 | Sentiss Research Center | Stable bromfenac solution |
| US9458169B2 (en) | 2013-11-01 | 2016-10-04 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| US20170000889A1 (en) | 2013-12-12 | 2017-01-05 | Sentiss Pharma Private Limited | Stable bromfenac ophthalmic solution |
| CN106404952B (zh) * | 2016-08-31 | 2019-06-11 | 辰欣佛都药业（汶上）有限公司 | 一种溴芬酸钠滴眼液有关物质的测定方法 |
| AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| US10336767B2 (en) | 2016-09-08 | 2019-07-02 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| EP3509423A4 (en) | 2016-09-08 | 2020-05-13 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
| JPWO2019117252A1 (ja) * | 2017-12-14 | 2020-12-17 | 参天製薬株式会社 | ２−アミノ−３−（４−ブロモベンゾイル）フェニル酢酸またはその塩を含有する点眼剤 |
| EP4238552A1 (en) | 2020-10-29 | 2023-09-06 | Taejoon Pharmaceutical Co., Ltd. | Ophthalmic composition |
| WO2022158893A2 (ko) | 2021-01-21 | 2022-07-28 | 주식회사태준제약 | 점안 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU512570B2 (en) * | 1975-08-13 | 1980-10-16 | A.H. Robins Company, Incorporated | Amino benzophenones |
| CH577461A5 (https=) * | 1975-08-13 | 1976-07-15 | Robins Co Inc A H | |
| JPS58201710A (ja) * | 1982-05-18 | 1983-11-24 | Meiji Seika Kaisha Ltd | 口腔内用抗炎症ペ−スト剤 |
| US4568695A (en) * | 1983-12-07 | 1986-02-04 | A. H. Robins Company, Incorporated | 2-Amino-3-benzoyl-phenethylalcohols and intermediates therefor |
| US4683242A (en) | 1985-10-28 | 1987-07-28 | A. H. Robins Company, Incorporated | Transdermal treatment for pain and inflammation with 2-amino-3-aroylbenzeneacetic acids, salts and esters |
-
1989
- 1989-01-24 US US07/301,033 patent/US4910225A/en not_active Expired - Lifetime
- 1989-01-24 CA CA000589025A patent/CA1325382C/en not_active Expired - Lifetime
- 1989-01-25 AU AU28786/89A patent/AU609932B2/en not_active Expired
- 1989-01-25 AT AT89101237T patent/ATE80043T1/de not_active IP Right Cessation
- 1989-01-25 ES ES89101237T patent/ES2052784T3/es not_active Expired - Lifetime
- 1989-01-25 EP EP89101237A patent/EP0326915B1/en not_active Expired - Lifetime
- 1989-01-25 DE DE8989101237T patent/DE68902649T2/de not_active Expired - Lifetime
- 1989-01-26 PH PH38108A patent/PH26827A/en unknown
- 1989-01-27 KR KR1019890000892A patent/KR960005707B1/ko not_active Expired - Lifetime
- 1989-01-27 JP JP1018549A patent/JP2683676B2/ja not_active Expired - Lifetime
-
1992
- 1992-09-03 GR GR920401848T patent/GR3005586T3/el unknown
-
1995
- 1995-10-19 HK HK162895A patent/HK162895A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR890011823A (ko) | 1989-08-22 |
| ES2052784T3 (es) | 1994-07-16 |
| DE68902649D1 (de) | 1992-10-08 |
| AU2878689A (en) | 1989-07-27 |
| EP0326915A1 (en) | 1989-08-09 |
| JP2683676B2 (ja) | 1997-12-03 |
| GR3005586T3 (https=) | 1993-06-07 |
| AU609932B2 (en) | 1991-05-09 |
| DE68902649T2 (de) | 1993-02-11 |
| ATE80043T1 (de) | 1992-09-15 |
| US4910225A (en) | 1990-03-20 |
| PH26827A (en) | 1992-11-05 |
| EP0326915B1 (en) | 1992-09-02 |
| JPH02124817A (ja) | 1990-05-14 |
| HK162895A (en) | 1995-10-27 |
| CA1325382C (en) | 1993-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR960005707B1 (ko) | 벤조일페닐아세트산 유도체 약제 조성물 | |
| KR100276743B1 (ko) | 눈 또는 코에 사용하기 위한 항알레르기 조성물 | |
| US4599360A (en) | Ophthalmic anti-inflammatory agents | |
| EP0642789A1 (en) | Remedy for glaucoma | |
| HU199072B (en) | Antimicrobal conserving composition and process for production of compositions for oculist purpuses | |
| JPH0216728B2 (https=) | ||
| JPH0696521B2 (ja) | 眼局所投与用眼圧降下剤 | |
| US5198454A (en) | Use of OB-104 to treat ocular inflammation | |
| JPH06316519A (ja) | 薬剤で誘導される瞳孔拡大を抑制し又は拡大された瞳孔を 縮小するための、一定のスルファモイル置換フェネチルア ミン誘導体の使用、及びそれに用いる局部的投与組成物 | |
| WO2019024433A1 (zh) | 氨基金刚烷胺单硝酸酯类化合物眼用组合物及其制剂和应用 | |
| KR100193406B1 (ko) | 근시의 예방 및 치료용 조성물 | |
| JP2020514347A (ja) | チオトロピウムを有効成分として含有する近視予防、近視治療および／または近視進行抑制剤 | |
| JPS5810517A (ja) | 非ステロイド系消炎剤を主成分とする点眼剤 | |
| US5093348A (en) | Pharmaceutical composition for topical ophthalmic use having improved local tolerability | |
| JPH10500130A (ja) | テラゾシンを含有する緑内障治療用医薬組成物 | |
| JPH0330571B2 (https=) | ||
| JPH06172176A (ja) | アジマリンを必須成分とする眼圧降下剤 | |
| JPH10203979A (ja) | チアプロフェン酸を含有する抗眼炎症剤 | |
| KR960013437B1 (ko) | 산화형 글루타티온 점안제 | |
| JP2741285B2 (ja) | 緑内障治療剤 | |
| EP0607697A2 (en) | DILAZEP for reduction of elevated intraocular pressure | |
| WO2004069822A1 (ja) | ステロイド副作用抑制組成物 | |
| JPS60136516A (ja) | 抗炎症眼科用液剤およびその製法 | |
| JPH09295935A (ja) | 抗眼炎症剤 | |
| JPH04134029A (ja) | 緑内障治療剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19890127 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19930311 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19890127 Comment text: Patent Application |
|
| G160 | Decision to publish patent application | ||
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19960406 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19960723 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19960729 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 19960729 End annual number: 3 Start annual number: 1 |
|
| PR1001 | Payment of annual fee |
Payment date: 19990413 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20000426 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20010425 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20020424 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20030422 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20040423 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20050422 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20060502 Start annual number: 11 End annual number: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20070424 Start annual number: 12 End annual number: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20080425 Start annual number: 13 End annual number: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090424 Start annual number: 14 End annual number: 14 |
|
| FPAY | Annual fee payment |
Payment date: 20100427 Year of fee payment: 15 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100427 Start annual number: 15 End annual number: 15 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |