JP5586117B2 - ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 - Google Patents
ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 Download PDFInfo
- Publication number
- JP5586117B2 JP5586117B2 JP2002518950A JP2002518950A JP5586117B2 JP 5586117 B2 JP5586117 B2 JP 5586117B2 JP 2002518950 A JP2002518950 A JP 2002518950A JP 2002518950 A JP2002518950 A JP 2002518950A JP 5586117 B2 JP5586117 B2 JP 5586117B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- composition
- branched alkyl
- alkyl
- straight chain
- 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 - Fee Related
Links
- 230000033115 angiogenesis Effects 0.000 title claims description 15
- 238000000034 method Methods 0.000 title description 4
- YVKSMFUEDUPYIF-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)C1=CC=CC=C1 YVKSMFUEDUPYIF-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 14
- ALDSXDRDRWDASQ-UHFFFAOYSA-N 2-(3-benzoylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 ALDSXDRDRWDASQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- QEFAQIPZVLVERP-UHFFFAOYSA-N nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 238000002054 transplantation Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 4
- 238000011200 topical administration Methods 0.000 claims description 4
- XAARRDGAECXQPW-UHFFFAOYSA-N 2-[2-amino-3-(4-fluorobenzoyl)phenyl]acetamide Chemical group NC(=O)CC1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1N XAARRDGAECXQPW-UHFFFAOYSA-N 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 208000002780 macular degeneration Diseases 0.000 claims description 3
- 201000007914 proliferative diabetic retinopathy Diseases 0.000 claims description 3
- VOUHFMUNVVHZNG-UHFFFAOYSA-N 2-amino-2-[3-(4-chlorobenzoyl)phenyl]acetamide Chemical compound NC(=O)C(N)C1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1 VOUHFMUNVVHZNG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 229940113601 irrigation solution Drugs 0.000 claims 2
- QYWOBAQCODTFCM-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1N QYWOBAQCODTFCM-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- -1 2-amino-3-benzoylphenylethyl alcohol Chemical compound 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- 238000002513 implantation Methods 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 229960001002 nepafenac Drugs 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SOYCMDCMZDHQFP-UHFFFAOYSA-N amfenac Chemical class NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 SOYCMDCMZDHQFP-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000010412 Glaucoma Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010038935 Retinopathy sickle cell Diseases 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 210000001927 retinal artery Anatomy 0.000 description 2
- 210000001957 retinal vein Anatomy 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GTMSVJVBRIPWOZ-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 GTMSVJVBRIPWOZ-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 206010055665 Corneal neovascularisation Diseases 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
- 206010015958 Eye pain Diseases 0.000 description 1
- 101000585663 Homo sapiens Myocilin Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102100029839 Myocilin Human genes 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 201000002154 Pterygium Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 206010039705 Scleritis Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229950008930 amfenac Drugs 0.000 description 1
- 230000002491 angiogenic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 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
- 239000006172 buffering agent Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 201000000159 corneal neovascularization Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 201000004514 liver lymphoma Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000010997 liver sarcoma Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 201000003142 neovascular glaucoma Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 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
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
- 229960004224 tyloxapol Drugs 0.000 description 1
- 229920001664 tyloxapol Polymers 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
-
- 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
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明は、血管形成疾患を処置または予防するための特定の3−ベンゾイルフェニル酢酸および誘導体の使用に関する。
3−ベンゾイルフェニル酢酸およびその特定の誘導体は、抗炎症活性を有することが公知である。米国特許第4,254,146号、同第4,045,576号、同第4,126,635号および同第4,503,073号、ならびに英国特許出願番号2,071,086Aおよび同2,093,027Aは、抗炎症活性を有する種々の3−ベンゾイルフェニル酢酸、その塩およびエステル、ならびにその水和物を開示する。米国特許第4,568,695号は、抗炎症活性を有する2−アミノ−3−ベンゾイルフェニルエチルアルコールを開示する。米国特許第4,313,949号は、抗炎症活性を有する2−アミノ−3−ベンゾイル−フェニルアセトアミドを開示する。
特定の3−ベンゾイルフェニル酢酸および誘導体(ナパフェナク(2−アミノ,3−ベンゾイル−フェニルアセトアミド)を含む)が、血管形成に関連する障害の処置に有用であることが、今回見出された。
本発明の方法に有用な3−ベンゾイルフェニル酢酸および誘導体は、以下の式(I)のものである。
Y=OR’、NR”R’;
R’=H、C1〜10分枝アルキル、C1〜10直鎖アルキル、非置換、置換(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nZ(CH2)n’A;
n=2〜6;
n’=1〜6;
Z=なし、O、C=O、OC(=O)、C(=O)O、C(=O)NR3、NR3C(=O)、
n2=0〜2;
R3=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換);
A=H、OH、必要に応じて、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nOR3;
R”=H、OH、OR’;
独立して、XおよびX’=H、F、Cl、Br、I、OR’、CN、OH、
R=H、C1〜2アルキル;
Y=NR’R”;
R’=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、−(CH2)nZ(CH2)n’A;
Z=なし、O、CHOR3、NR3;
R3=H;
A=H、OH、非置換アリール、置換アリール(以下のXによって規定されるような置換);
XおよびX’(独立して)=H、F、Cl、Br、CN、CF3、OR’、SR4、R4;
R”=H;
R4=C1〜4直鎖アルキル、C1〜4分枝アルキル;
m=0〜2;
m’=0〜2;
W=H;
n=2〜4;
n’=0〜3
である。
以下の処方物は、本発明において有用な局所的組成物の代表である。
式(1)の化合物 0.01〜0.5%
ポリソルベート80 0.01%
塩化ベンザルコニウム 0.01%+10%過剰
EDTA二ナトリウム 0.1%
リン酸ナトリウム 0.03%
リン酸二ナトリウム 0.1%
塩化ナトリウム 290〜300mOsm/Kgまで
NaOHおよび/またはHClで pH4.2〜7.4
pHを調整する
水 100%まで
(処方物2)
式(1)の化合物 0.01〜0.5%
ヒドロキシプロピルメチルセルロース 0.5%
ポリソルベート80 0.01%
塩化ベンザルコニウム 0.01%+5%過剰
EDTA二ナトリウム 0.01%
リン酸二ナトリウム 0.2%
塩化ナトリウム 290〜300mOsm/Kgまで
NaOHおよび/またはHClで pH4.2〜7.4
pHを調整する
水 100%まで
(処方物3)
ネパフェナク 0.1+6%過剰
カーボポール(carbopol)974P 0.08%
チロキサポール 0.01%
グリセリン 2.4%
EDTA二ナトリウム 0.01%
塩化ベンザルコニウム 0.01%
NaOHおよび/またはHClでpHを調整する pH7.5±0.2
水 100%まで。
Claims (12)
- 血管形成に関連する障害に罹患しているか、または該障害の素因を有する患者の該血管形成に関連する障害を処置もしくは予防するための組成物であって、該組成物は、治療的有効量の以下の式の3−ベンゾイルフェニル酢酸もしくは誘導体を含有する、組成物であって、以下:
【化1】
ここで、
R=H、C1〜4分枝アルキル、C1〜4直鎖アルキル、CF3、SR4;
Y=OR’、NR”R’;
R’=H、C1〜10分枝アルキル、C1〜10直鎖アルキル、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nZ(CH2)n’A;
n=2〜6;
n’=1〜6;
Z=なし、O、C=O、OC(=O)、C(=O)O、C(=O)NR3、NR3C(=O)、
【化2】
CHOR3、NR3;
n2=0〜2;
R3=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換);
A=H、OH、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nOR3;
R”=H、OH、OR’;
独立して、XおよびX’=H、F、Cl、Br、I、OR’、CN、OH、
【化3】
CF3、R4、NO2;
R4=C1〜6分枝アルキル、C1〜6直鎖アルキル;
m=0〜3;
m’=0〜5;ならびに
W=O、H
であり、ここで、該血管形成に関連する障害が、眼の血管形成に関連する障害であり;
該血管形成に関連する障害が、滲出性黄斑変性;増殖性糖尿病性網膜症;虚血性網膜症;および未熟児網膜症からなる群より選択される、組成物。
- 請求項1に記載の組成物であって、ここで:
R=H、C1〜2アルキル;
Y=NR’R”;
R’=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、−(CH2)nZ(CH2)n’A;
Z=なし、O、CHOR3、NR3;
R3=H;
A=H、OH、非置換アリール、置換アリール(以下のXによって規定されるような置換);
独立して、XおよびX’=H、F、Cl、Br、CN、CF3、OR’、SR4、R4;
R”=H;
R4=C1〜4分枝アルキル、C1〜4直鎖アルキル;
m=0〜2;
m’=0〜2;
W=H;
n=2〜4;ならびに
n’=0〜3
である、組成物。
- 請求項2に記載の組成物であって、前記3−ベンゾイルフェニル酢酸または誘導体が、2−アミノ−3−(4−フルオロベンゾイル)−フェニルアセトアミド;2−アミノ−3−ベンゾイル−フェニルアセトアミド;および2−アミノ−3−(4−クロロベンゾイル)−フェニルアセトアミドからなる群より選択される、組成物。
- 前記3−ベンゾイルフェニル酢酸または誘導体が、眼に局所的に投与されるのに適している、請求項1に記載の組成物。
- 前記治療的有効量の3−ベンゾイルフェニル酢酸または誘導体が、0.001〜4.0%(w/v)である、請求項4に記載の組成物。
- 前記3−ベンゾイルフェニル酢酸または誘導体が、経口投与、静脈内投与、結膜下への注入もしくは移植、テノン下への注入もしくは移植、硝子体への注入もしくは移植、または外科的な灌注溶液の組み込みによって、投与されるのに適している、請求項1に記載の組成物。
- 血管形成に関連する障害に罹患しているか、または該障害の素因を有する患者の該血管形成に関連する障害を処置もしくは予防するための医薬の製造における、以下の式の3−ベンゾイルフェニル酢酸もしくは誘導体の使用であって、以下:
【化4】
ここで、
R=H、C1〜4分枝アルキル、C1〜4直鎖アルキル、CF3、SR4;
Y=OR’、NR”R’;
R’=H、C1〜10分枝アルキル、C1〜10直鎖アルキル、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nZ(CH2)n’A;
n=2〜6;
n’=1〜6;
Z=なし、O、C=O、OC(=O)、C(=O)O、C(=O)NR3、NR3C(=O)、
【化5】
CHOR3、NR3;
n2=0〜2;
R3=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換);
A=H、OH、非置換アリール、置換アリール(以下のXによって規定されるような置換)、非置換複素環、置換複素環(以下のXによって規定されるような置換)、−(CH2)nOR3;
R”=H、OH、OR’;
独立して、XおよびX’=H、F、Cl、Br、I、OR’、CN、OH、
【化6】
CF3、R4、NO2;
R4=C1〜6分枝アルキル、C1〜6直鎖アルキル;
m=0〜3;
m’=0〜5;ならびに
W=O、H
であり、ここで、該血管形成に関連する障害が、眼の血管形成に関連する障害であり;
該血管形成に関連する障害が、滲出性黄斑変性;増殖性糖尿病性網膜症;虚血性網膜症;および未熟児網膜症からなる群より選択される、使用。
- 請求項7に記載の使用であって、ここで:
R=H、C1〜2アルキル;
Y=NR’R”;
R’=H、C1〜6分枝アルキル、C1〜6直鎖アルキル、−(CH2)nZ(CH2)n’A;
Z=なし、O、CHOR3、NR3;
R3=H;
A=H、OH、非置換アリール、置換アリール(以下のXによって規定されるような置換);
独立して、XおよびX’=H、F、Cl、Br、CN、CF3、OR’、SR4、R4;
R”=H;
R4=C1〜4分枝アルキル、C1〜4直鎖アルキル;
m=0〜2;
m’=0〜2;
W=H;
n=2〜4;ならびに
n’=0〜3
である、使用。
- 請求項8に記載の使用であって、前記3−ベンゾイルフェニル酢酸または誘導体が、2−アミノ−3−(4−フルオロベンゾイル)−フェニルアセトアミド;2−アミノ−3−ベンゾイル−フェニルアセトアミド;および2−アミノ−3−(4−クロロベンゾイル)−フェニルアセトアミドからなる群より選択される、使用。
- 前記医薬が、眼に局所的に投与されるのに適している、請求項7に記載の使用。
- 前記3−ベンゾイルフェニル酢酸または誘導体が、0.001〜4.0%(w/v)である、請求項10に記載の使用。
- 前記医薬が、経口投与、静脈内投与、結膜下への注入もしくは移植、テノン下への注入もしくは移植、硝子体への注入もしくは移植、または外科的な灌注溶液の組み込みによって、投与されるのに適している、請求項7に記載の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22513300P | 2000-08-14 | 2000-08-14 | |
US60/225,133 | 2000-08-14 | ||
PCT/US2001/025318 WO2002013804A2 (en) | 2000-08-14 | 2001-08-13 | Method of treating angiogenesis-related disorders using benzoyl phenylacetic acid |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012158552A Division JP2012193214A (ja) | 2000-08-14 | 2012-07-17 | ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004520267A JP2004520267A (ja) | 2004-07-08 |
JP2004520267A5 JP2004520267A5 (ja) | 2008-08-14 |
JP5586117B2 true JP5586117B2 (ja) | 2014-09-10 |
Family
ID=22843668
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002518950A Expired - Fee Related JP5586117B2 (ja) | 2000-08-14 | 2001-08-13 | ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 |
JP2012158552A Pending JP2012193214A (ja) | 2000-08-14 | 2012-07-17 | ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012158552A Pending JP2012193214A (ja) | 2000-08-14 | 2012-07-17 | ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US20020037929A1 (ja) |
EP (1) | EP1309323B1 (ja) |
JP (2) | JP5586117B2 (ja) |
KR (1) | KR20030017653A (ja) |
CN (1) | CN1447688A (ja) |
AR (1) | AR030345A1 (ja) |
AT (1) | ATE345123T1 (ja) |
AU (2) | AU2001283337B2 (ja) |
BR (1) | BR0113204A (ja) |
CA (1) | CA2417282C (ja) |
DE (1) | DE60124560T2 (ja) |
DK (1) | DK1309323T3 (ja) |
ES (1) | ES2275710T3 (ja) |
HK (1) | HK1057331A1 (ja) |
MX (1) | MXPA03001057A (ja) |
PL (1) | PL366220A1 (ja) |
PT (1) | PT1309323E (ja) |
WO (1) | WO2002013804A2 (ja) |
ZA (1) | ZA200300782B (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1507522A2 (en) * | 2002-05-03 | 2005-02-23 | Alcon, Inc. | Method of treating vascular endothelial growth factor mediated vascular disorders using amfenac or nepafenac |
CN1681510A (zh) * | 2002-09-16 | 2005-10-12 | 爱尔康制造有限公司 | Pde ⅳ抑制剂治疗血管生成的用途 |
CA2504460A1 (en) * | 2002-11-12 | 2004-05-27 | Peter G. Klimko | Histone deacetylase inhibitors for the treatment of ocular neovascular or edematous disorders and diseases |
DE602004013420T2 (de) | 2003-01-21 | 2009-06-04 | Senju Pharmaceutical Co., Ltd. | Wässrige flüssige zubereitung mit 2-amino-3-(4-bromobenzoyl)phenylessigsäure |
CA2584286C (en) * | 2004-11-09 | 2014-01-14 | Alcon, Inc. | 5,6,7-trihydroxyheptanoic acid and analogs for the treatment of ocular diseases and diseases associated with hyperproliferative and angiogenic responses |
TWI358290B (en) * | 2004-12-02 | 2012-02-21 | Alcon Inc | Topical nepafenac formulations |
FR2909876A1 (fr) * | 2006-12-19 | 2008-06-20 | Galderma Res & Dev S N C Snc | Utilisation du nepafenac ou ses derives pour le traitement de desordres dermatologiques |
US20100292289A1 (en) * | 2007-11-30 | 2010-11-18 | Ampla Pharmaceuticals Inc. | Treatment of metabolic syndrome with novel amides |
JP2011513229A (ja) * | 2008-02-21 | 2011-04-28 | イスタ・ファーマスーティカルズ・インコーポレイテッド | 補助剤としての眼科用nsaid |
US8962686B2 (en) * | 2010-04-28 | 2015-02-24 | The Chinese University Of Hong Kong | Method and medication for prevention and treatment of ocular hypertension and glaucoma |
EP3013790A1 (en) | 2013-06-27 | 2016-05-04 | Mylan Laboratories Ltd. | Process for the preparation of nepafenac |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
US4313949A (en) * | 1979-09-26 | 1982-02-02 | A. H. Robins Company, Inc. | Method of producing an inhibitory effect on blood platelet aggregation |
ZA805476B (en) * | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
US4254146A (en) * | 1979-10-18 | 1981-03-03 | A. H. Robins Company, Inc. | 3-Benzoyl-2-nitrophenylacetic acids, metal salts, amides and esters |
IL61945A (en) * | 1980-02-19 | 1984-09-30 | Robins Co Inc A H | 2-amino-3-(hydroxy(phenyl)methyl)phenylacetic acids,esters and amides and pharmaceutical compositions containing them |
DE3026402A1 (de) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Die verwendung analgetischer und nicht-hormonaler, entzuendungshemmender mittel bei der behandlung von mikrovaskulaeren erkrankungen |
US4503073A (en) * | 1981-01-07 | 1985-03-05 | A. H. Robins Company, Incorporated | 2-Amino-3-(alkylthiobenzoyl)-phenylacetic acids |
IL64724A0 (en) * | 1981-02-17 | 1982-03-31 | Robins Co Inc A H | 2-amino-3-(halobenzoyl)-methylphenylacetic acids and esters and salts thereof and pharmaceutical compositions containing them |
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 |
US4910225A (en) * | 1988-01-27 | 1990-03-20 | Senju Pharmaceutical Co., Ltd. | Locally administrable therapeutic composition for inflammatory disease |
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 |
US5811446A (en) * | 1997-04-18 | 1998-09-22 | Cytos Pharmaceuticals Llc | Prophylactic and therapeutic methods for ocular degenerative diseases and inflammations and histidine compositions therefor |
US6066671A (en) * | 1997-12-19 | 2000-05-23 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with 3-benzoyl-phenylacetic acids, esters, or amides |
US5994379A (en) * | 1998-02-13 | 1999-11-30 | Merck Frosst Canada, Inc. | Bisaryl COX-2 inhibiting compounds, compositions and methods of use |
US6207700B1 (en) * | 1999-01-07 | 2001-03-27 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
EP1221917B1 (en) * | 1999-10-21 | 2004-11-24 | Alcon Inc. | Drug delivery device |
US6416777B1 (en) * | 1999-10-21 | 2002-07-09 | Alcon Universal Ltd. | Ophthalmic drug delivery device |
AU1051201A (en) * | 1999-11-11 | 2001-06-06 | Wireless Methods Ltd. | Remote switching and actuation of electrical devices |
-
2001
- 2001-08-10 AR ARP010103846A patent/AR030345A1/es not_active Application Discontinuation
- 2001-08-13 WO PCT/US2001/025318 patent/WO2002013804A2/en active IP Right Grant
- 2001-08-13 DK DK01962132T patent/DK1309323T3/da active
- 2001-08-13 CN CN01814168A patent/CN1447688A/zh active Pending
- 2001-08-13 AT AT01962132T patent/ATE345123T1/de active
- 2001-08-13 KR KR10-2003-7001087A patent/KR20030017653A/ko not_active Application Discontinuation
- 2001-08-13 AU AU2001283337A patent/AU2001283337B2/en not_active Ceased
- 2001-08-13 EP EP01962132A patent/EP1309323B1/en not_active Expired - Lifetime
- 2001-08-13 BR BRPI0113204-0A patent/BR0113204A/pt not_active Application Discontinuation
- 2001-08-13 PT PT01962132T patent/PT1309323E/pt unknown
- 2001-08-13 JP JP2002518950A patent/JP5586117B2/ja not_active Expired - Fee Related
- 2001-08-13 DE DE60124560T patent/DE60124560T2/de not_active Expired - Lifetime
- 2001-08-13 CA CA002417282A patent/CA2417282C/en not_active Expired - Fee Related
- 2001-08-13 US US09/929,381 patent/US20020037929A1/en not_active Abandoned
- 2001-08-13 MX MXPA03001057A patent/MXPA03001057A/es active IP Right Grant
- 2001-08-13 ES ES01962132T patent/ES2275710T3/es not_active Expired - Lifetime
- 2001-08-13 AU AU8333701A patent/AU8333701A/xx active Pending
- 2001-08-13 PL PL01366220A patent/PL366220A1/xx not_active Application Discontinuation
-
2003
- 2003-01-29 ZA ZA200300782A patent/ZA200300782B/en unknown
- 2003-11-14 HK HK03108333A patent/HK1057331A1/xx not_active IP Right Cessation
-
2012
- 2012-07-17 JP JP2012158552A patent/JP2012193214A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
HK1057331A1 (en) | 2004-04-02 |
DE60124560T2 (de) | 2007-09-06 |
JP2004520267A (ja) | 2004-07-08 |
JP2012193214A (ja) | 2012-10-11 |
AU8333701A (en) | 2002-02-25 |
MXPA03001057A (es) | 2004-09-10 |
DK1309323T3 (da) | 2007-03-19 |
DE60124560D1 (de) | 2006-12-28 |
ES2275710T3 (es) | 2007-06-16 |
PT1309323E (pt) | 2007-01-31 |
ATE345123T1 (de) | 2006-12-15 |
US20020037929A1 (en) | 2002-03-28 |
BR0113204A (pt) | 2006-02-21 |
AU2001283337B2 (en) | 2006-06-15 |
PL366220A1 (en) | 2005-01-24 |
ZA200300782B (en) | 2004-08-27 |
EP1309323B1 (en) | 2006-11-15 |
CN1447688A (zh) | 2003-10-08 |
KR20030017653A (ko) | 2003-03-03 |
CA2417282A1 (en) | 2002-02-21 |
AR030345A1 (es) | 2003-08-20 |
EP1309323A2 (en) | 2003-05-14 |
CA2417282C (en) | 2009-12-22 |
WO2002013804A2 (en) | 2002-02-21 |
WO2002013804A3 (en) | 2002-06-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2012193214A (ja) | ベンゾイルフェニル酢酸を使用して、血管形成関連障害を処置するための方法 | |
KR101237534B1 (ko) | 안질환, 및 과잉증식 및 혈관형성 반응과 관련된 질환치료용 5,6,7-트리하이드록시헵탄산 및 유사체 | |
EP1309322B1 (en) | Use of 3-benzoylphenylacetic acid derivatives for the treatment of retinal disorders | |
AU2001283337A1 (en) | Method of treating angiogenesis-related disorders using benzoyl phenylacetic acid | |
US6646003B2 (en) | Method of treating ocular inflammatory and angiogenesis-related disorders of the posterior segment of the eye using an amide derivative of flurbiprofen or ketorolac | |
US6455567B1 (en) | Method of treatment | |
JP2004506010A5 (ja) | ||
JP2004520267A5 (ja) | ||
US20030207941A1 (en) | Method of treating vascular endothelial growth factor mediated vascular disorders | |
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 | |
US20040132773A1 (en) | Method of treating neurodgenerative disorders of the retina and optic nerve head | |
AU2001281258B2 (en) | Method of treating neurodegenerative disorders of the retina and optic nerve head | |
US20030187072A1 (en) | Method of treating angiogenesis-related disorders | |
AU2001281258A1 (en) | Method of treating neurodegenerative disorders of the retina and optic nerve head | |
AU2006217547A1 (en) | Method of treating angiogenesis-related disorders | |
EP0607697A2 (en) | DILAZEP for reduction of elevated intraocular pressure |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080627 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080627 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110809 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111109 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20111109 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120316 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120717 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20120830 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120921 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20121012 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140603 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140722 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5586117 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |