IE59229B1 - Transdermal treatment of pain and inflammation with 2-amino-3-aroylbenzeneacetic acids, salts and esters - Google Patents
Transdermal treatment of pain and inflammation with 2-amino-3-aroylbenzeneacetic acids, salts and estersInfo
- Publication number
- IE59229B1 IE59229B1 IE281186A IE281186A IE59229B1 IE 59229 B1 IE59229 B1 IE 59229B1 IE 281186 A IE281186 A IE 281186A IE 281186 A IE281186 A IE 281186A IE 59229 B1 IE59229 B1 IE 59229B1
- Authority
- IE
- Ireland
- Prior art keywords
- amino
- acid
- benzoyl
- bromobenzoyl
- benzeneacetic
- Prior art date
Links
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 24
- 230000004054 inflammatory process Effects 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 239000002253 acid Substances 0.000 title claims description 108
- 150000002148 esters Chemical class 0.000 title abstract description 10
- 150000007513 acids Chemical class 0.000 title description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 24
- SOYCMDCMZDHQFP-UHFFFAOYSA-N amfenac Chemical class NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 SOYCMDCMZDHQFP-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 loweralkyl Chemical group 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 83
- 159000000000 sodium salts Chemical class 0.000 claims description 64
- 239000006071 cream Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 229910001868 water Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 150000004682 monohydrates Chemical class 0.000 claims description 29
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 229960003424 phenylacetic acid Drugs 0.000 claims description 13
- 241000282412 Homo Species 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- KASVLKJSQYEVBJ-UHFFFAOYSA-N 2-[2-amino-3-(4-bromobenzoyl)-5-chlorophenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1C(=O)C1=CC=C(Br)C=C1 KASVLKJSQYEVBJ-UHFFFAOYSA-N 0.000 claims description 9
- ZBPLOVFIXSTCRZ-UHFFFAOYSA-N bromfenac Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 ZBPLOVFIXSTCRZ-UHFFFAOYSA-N 0.000 claims description 8
- HZOREEUASZHZBI-UHFFFAOYSA-M sodium;2-phenylacetate Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1 HZOREEUASZHZBI-UHFFFAOYSA-M 0.000 claims description 8
- 150000004683 dihydrates Chemical class 0.000 claims description 7
- 239000000017 hydrogel Substances 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 150000003751 zinc Chemical class 0.000 claims description 6
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- KWWGUYKWKFVFLY-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1C(=O)C1=CC=CC=C1 KWWGUYKWKFVFLY-UHFFFAOYSA-N 0.000 claims description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 4
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 4
- QXXLWWRWJAXJNE-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-4-chlorophenyl)acetic acid Chemical compound NC1=C(CC(O)=O)C=CC(Cl)=C1C(=O)C1=CC=CC=C1 QXXLWWRWJAXJNE-UHFFFAOYSA-N 0.000 claims description 3
- YGZBDEDBFYZFIJ-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)-5-methylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 YGZBDEDBFYZFIJ-UHFFFAOYSA-N 0.000 claims description 3
- NAOMGJHIWJUPAX-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)-5-fluorophenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(F)C=C1C(=O)C1=CC=C(Cl)C=C1 NAOMGJHIWJUPAX-UHFFFAOYSA-N 0.000 claims description 3
- LJPBYWHKMWBFMQ-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)-5-methylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 LJPBYWHKMWBFMQ-UHFFFAOYSA-N 0.000 claims description 3
- RSTMBQVADWZPHX-UHFFFAOYSA-N 2-[2-amino-3-(4-methoxybenzoyl)phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC(CC(O)=O)=C1N RSTMBQVADWZPHX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- HDVDLQFPDLTOSI-UHFFFAOYSA-L O[AlH]O Chemical compound O[AlH]O HDVDLQFPDLTOSI-UHFFFAOYSA-L 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000008309 hydrophilic cream Substances 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 150000004684 trihydrates Chemical class 0.000 claims description 3
- ZYACJBUZANJOSR-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-methoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C=CC=CC=2)=C1 ZYACJBUZANJOSR-UHFFFAOYSA-N 0.000 claims description 2
- HRCFKMKHWZWLOA-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)-5-fluorophenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(F)C=C1C(=O)C1=CC=C(Cl)C=C1Cl HRCFKMKHWZWLOA-UHFFFAOYSA-N 0.000 claims description 2
- XGPCBYFVNCLKKQ-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl XGPCBYFVNCLKKQ-UHFFFAOYSA-N 0.000 claims description 2
- XACINTMLMWIYOE-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dimethylbenzoyl)phenyl]acetic acid Chemical compound CC1=CC(C)=CC=C1C(=O)C1=CC=CC(CC(O)=O)=C1N XACINTMLMWIYOE-UHFFFAOYSA-N 0.000 claims description 2
- WBLCAEKAKAWBKQ-UHFFFAOYSA-N 2-[2-amino-3-(4-bromo-2-chlorobenzoyl)-5-chlorophenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1C(=O)C1=CC=C(Br)C=C1Cl WBLCAEKAKAWBKQ-UHFFFAOYSA-N 0.000 claims description 2
- JZJHAOGTBRHZPB-UHFFFAOYSA-N 2-[2-amino-3-(4-bromobenzoyl)-5-methylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C=CC(Br)=CC=2)=C1 JZJHAOGTBRHZPB-UHFFFAOYSA-N 0.000 claims description 2
- KRBPPWORXFPTOL-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)-5-methoxyphenyl]acetic acid Chemical compound COC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 KRBPPWORXFPTOL-UHFFFAOYSA-N 0.000 claims description 2
- UJHCATOJRKRCLV-UHFFFAOYSA-N 2-[2-amino-3-(4-fluorobenzoyl)-5-methylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=C(N)C(C(=O)C=2C=CC(F)=CC=2)=C1 UJHCATOJRKRCLV-UHFFFAOYSA-N 0.000 claims description 2
- BJHJMEKWXKIIDE-UHFFFAOYSA-N 2-[2-amino-5-bromo-3-(4-chlorobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Br)C=C1C(=O)C1=CC=C(Cl)C=C1 BJHJMEKWXKIIDE-UHFFFAOYSA-N 0.000 claims description 2
- MNFMLKDTODVPEC-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-(4-hydroxybenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1C(=O)C1=CC=C(O)C=C1 MNFMLKDTODVPEC-UHFFFAOYSA-N 0.000 claims description 2
- RDDKWPSSKOTLAY-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-(4-methylbenzoyl)phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(Cl)=CC(CC(O)=O)=C1N RDDKWPSSKOTLAY-UHFFFAOYSA-N 0.000 claims description 2
- JINFAKSUGHCKFJ-UHFFFAOYSA-N 2-[2-amino-5-fluoro-3-(4-methylbenzoyl)phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(F)=CC(CC(O)=O)=C1N JINFAKSUGHCKFJ-UHFFFAOYSA-N 0.000 claims description 2
- OWKJWCLQIUAOSS-UHFFFAOYSA-N 2-[2-amino-5-methyl-3-(4-methylbenzoyl)phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(C)=CC(CC(O)=O)=C1N OWKJWCLQIUAOSS-UHFFFAOYSA-N 0.000 claims description 2
- YWLBYZXTJKMZPN-UHFFFAOYSA-N 2-[3-benzoyl-2-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 YWLBYZXTJKMZPN-UHFFFAOYSA-N 0.000 claims description 2
- MLBAFRHKOXZRGK-UHFFFAOYSA-N ethyl 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C(=O)C=2C=CC(Br)=CC=2)=C1N MLBAFRHKOXZRGK-UHFFFAOYSA-N 0.000 claims description 2
- IGDMGNPJPXBDAN-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)phenyl]propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1N IGDMGNPJPXBDAN-UHFFFAOYSA-N 0.000 claims 1
- NFMLUVYWNKTOPN-UHFFFAOYSA-N 2-[2-amino-3-(4-bromobenzoyl)phenyl]propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC(Br)=CC=2)=C1N NFMLUVYWNKTOPN-UHFFFAOYSA-N 0.000 claims 1
- IZULUALBZMPWKX-UHFFFAOYSA-N 2-[2-amino-3-(4-iodobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(I)C=C1 IZULUALBZMPWKX-UHFFFAOYSA-N 0.000 claims 1
- MMZATVKTLKAZAS-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-(4-chlorobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1C(=O)C1=CC=C(Cl)C=C1 MMZATVKTLKAZAS-UHFFFAOYSA-N 0.000 claims 1
- PACSXJGHXHPLEP-UHFFFAOYSA-N 2-[2-amino-5-fluoro-3-(4-fluorobenzoyl)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(F)C=C1C(=O)C1=CC=C(F)C=C1 PACSXJGHXHPLEP-UHFFFAOYSA-N 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- UPYCUTQRBSCGMS-UHFFFAOYSA-L copper;2-(2-amino-3-benzoylphenyl)acetate Chemical compound [Cu+2].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1.NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 UPYCUTQRBSCGMS-UHFFFAOYSA-L 0.000 claims 1
- DFPBOQPTKIKFFP-UHFFFAOYSA-N ethyl 2-(2-amino-3-benzoyl-5-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1N DFPBOQPTKIKFFP-UHFFFAOYSA-N 0.000 claims 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 claims 1
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- 239000013543 active substance Substances 0.000 description 29
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- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
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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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/792,269 US4683242A (en) | 1985-10-28 | 1985-10-28 | Transdermal treatment for pain and inflammation with 2-amino-3-aroylbenzeneacetic acids, salts and esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE862811L IE862811L (en) | 1987-04-28 |
| IE59229B1 true IE59229B1 (en) | 1994-01-26 |
Family
ID=25156312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE281186A IE59229B1 (en) | 1985-10-28 | 1986-10-24 | Transdermal treatment of pain and inflammation with 2-amino-3-aroylbenzeneacetic acids, salts and esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4683242A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0221753B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH07116027B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE71358T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU596813B2 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3683350D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2039354T3 (cg-RX-API-DMAC7.html) |
| GR (1) | GR3004278T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HU197210B (cg-RX-API-DMAC7.html) |
| IE (1) | IE59229B1 (cg-RX-API-DMAC7.html) |
| PH (1) | PH22410A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA867988B (cg-RX-API-DMAC7.html) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3620674A1 (de) * | 1986-06-20 | 1987-12-23 | Nattermann A & Cie | Salbe zur behandlung von hauterkrankungen |
| US4782089A (en) * | 1986-08-26 | 1988-11-01 | A. H. Robins Company, Incorporated | 2-amino-3-aroyl-gamma-oxobenzenebutanoic acids and esters |
| US4910225A (en) * | 1988-01-27 | 1990-03-20 | Senju Pharmaceutical Co., Ltd. | Locally administrable therapeutic composition for inflammatory disease |
| US5016615A (en) * | 1990-02-20 | 1991-05-21 | Riverside Research Institute | Local application of medication with ultrasound |
| DK0719145T3 (da) | 1994-05-27 | 2001-01-02 | Cellegy Pharma Inc | Nitrogenoxiddonorpræparat til behandling af anale lidelser |
| 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 |
| DE19631220C2 (de) * | 1996-08-02 | 2000-03-23 | Beiersdorf Ag | Schaumförmige oder schäumbare Zubereitungen mit einem Gehalt an grenzflächenaktiven Substanzen und Elektrolyten |
| US6066671A (en) * | 1997-12-19 | 2000-05-23 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with 3-benzoyl-phenylacetic acids, esters, or amides |
| US6646001B2 (en) | 1997-12-19 | 2003-11-11 | Alcon Manufacturing, Ltd. | Use of non-steroidal anti-inflammatory agents in combination with prostaglandin FP receptor agonists to treat glaucoma and ocular hypertension |
| US7066884B2 (en) * | 1998-01-08 | 2006-06-27 | Sontra Medical, Inc. | System, method, and device for non-invasive body fluid sampling and analysis |
| US8287483B2 (en) * | 1998-01-08 | 2012-10-16 | Echo Therapeutics, Inc. | Method and apparatus for enhancement of transdermal transport |
| US20060015058A1 (en) * | 1998-01-08 | 2006-01-19 | Kellogg Scott C | Agents and methods for enhancement of transdermal transport |
| US20040171980A1 (en) | 1998-12-18 | 2004-09-02 | Sontra Medical, Inc. | Method and apparatus for enhancement of transdermal transport |
| AR030346A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes neurodegenerativos de la retina y cabeza de nervio optico |
| AR030345A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes relacionados con angiogenesis |
| US6503894B1 (en) | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US7186745B2 (en) | 2001-03-06 | 2007-03-06 | Astrazeneca Ab | Indolone derivatives having vascular damaging activity |
| 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 |
| US20030207941A1 (en) * | 2002-05-03 | 2003-11-06 | Bingaman David P. | Method of treating vascular endothelial growth factor mediated vascular disorders |
| KR101059711B1 (ko) | 2003-01-21 | 2011-08-29 | 센주 세이야꾸 가부시키가이샤 | 2-아미노-3-(4-브로모벤조일)페닐아세트산 함유 수성액제 |
| US20030187072A1 (en) * | 2003-02-14 | 2003-10-02 | Kapin Michael A. | Method of treating angiogenesis-related disorders |
| US20060094944A1 (en) * | 2004-10-28 | 2006-05-04 | Sontra Medical Corporation | System and method for analyte sampling and analysis with error correction |
| TWI358290B (en) * | 2004-12-02 | 2012-02-21 | Alcon Inc | Topical nepafenac formulations |
| PL2450041T3 (pl) | 2005-10-12 | 2019-02-28 | Unimed Pharmaceuticals, Llc | Ulepszony żel zawierający testosteron do zastosowania do leczenia hipogonadyzmu |
| US7432069B2 (en) * | 2005-12-05 | 2008-10-07 | Sontra Medical Corporation | Biocompatible chemically crosslinked hydrogels for glucose sensing |
| TW200812575A (en) * | 2006-04-28 | 2008-03-16 | Alcon Inc | Formulations containing amide derivatives of carboxylic acid NSAIDs for topical administration to the eye |
| 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 |
| 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 |
| 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 |
| RU2444980C2 (ru) * | 2007-03-07 | 2012-03-20 | Эко Терапьютикс, Инк. | Трансдермальная система мониторинга аналита и способы детекции аналита |
| KR101211252B1 (ko) | 2007-04-27 | 2012-12-12 | 에코 테라퓨틱스, 인크. | 경피 피분석물 감지 또는 경피 약제 전달용 피부 침투장치 |
| GB0919757D0 (en) * | 2009-11-12 | 2009-12-30 | Johnson Matthey Plc | Polymorphs of bromfenac sodium and methods for preparing bromfenac sodium polymorphs |
| GB2484843A (en) * | 2009-10-15 | 2012-04-25 | Johnson Matthey Plc | Polymorphs of Bromfenac sodium |
| US8299295B2 (en) | 2009-10-15 | 2012-10-30 | Johnson Matthey Public Limited Company | Polymorphs of bromfenac sodium and methods for preparing bromfenac sodium polymorphs |
| CN104177272B (zh) * | 2014-06-16 | 2016-04-06 | 广东众生药业股份有限公司 | 一种溴芬酸钠的制备方法 |
| CN104151182B (zh) * | 2014-06-16 | 2016-03-30 | 广东众生药业股份有限公司 | 一种溴芬酸钠倍半水合物的制备方法 |
| 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 |
| CN115093340B (zh) * | 2022-06-27 | 2024-05-03 | 辰欣药业股份有限公司 | 一种溴芬酸钠倍半水合物的制备方法 |
Family Cites Families (7)
| 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 |
| JPS53130634A (en) * | 1977-04-20 | 1978-11-14 | Hisamitsu Pharmaceut Co Inc | Novel 2-(3-phenoxyphenyl) propionic acid ester derivatives |
| JPS596287B2 (ja) * | 1980-11-28 | 1984-02-10 | 日東電工株式会社 | 医薬製剤 |
| 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 |
| JPS5883622A (ja) * | 1981-11-10 | 1983-05-19 | Hisamitsu Pharmaceut Co Inc | 消炎鎮痛ゲル状クリーム剤 |
| WO1986002636A1 (fr) * | 1984-10-30 | 1986-05-09 | Takeda Chemical Industries, Ltd. | Derives de l'acide benzoique et procede de preparation |
-
1985
- 1985-10-28 US US06/792,269 patent/US4683242A/en not_active Expired - Lifetime
-
1986
- 1986-10-21 ZA ZA867988A patent/ZA867988B/xx unknown
- 1986-10-24 IE IE281186A patent/IE59229B1/en not_active IP Right Cessation
- 1986-10-24 PH PH34409A patent/PH22410A/en unknown
- 1986-10-27 HU HU864499A patent/HU197210B/hu not_active IP Right Cessation
- 1986-10-27 AU AU64447/86A patent/AU596813B2/en not_active Ceased
- 1986-10-28 EP EP86308373A patent/EP0221753B1/en not_active Expired - Lifetime
- 1986-10-28 ES ES86308373T patent/ES2039354T3/es not_active Expired - Lifetime
- 1986-10-28 DE DE8686308373T patent/DE3683350D1/de not_active Expired - Fee Related
- 1986-10-28 AT AT86308373T patent/ATE71358T1/de not_active IP Right Cessation
- 1986-10-28 JP JP61256712A patent/JPH07116027B2/ja not_active Expired - Lifetime
-
1992
- 1992-04-06 GR GR920400633T patent/GR3004278T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0221753A2 (en) | 1987-05-13 |
| JPS62126124A (ja) | 1987-06-08 |
| US4683242A (en) | 1987-07-28 |
| AU6444786A (en) | 1987-04-30 |
| EP0221753A3 (en) | 1988-04-27 |
| PH22410A (en) | 1988-08-26 |
| HU197210B (en) | 1989-03-28 |
| DE3683350D1 (de) | 1992-02-20 |
| HUT42948A (en) | 1987-09-28 |
| EP0221753B1 (en) | 1992-01-08 |
| IE862811L (en) | 1987-04-28 |
| GR3004278T3 (cg-RX-API-DMAC7.html) | 1993-03-31 |
| ATE71358T1 (de) | 1992-01-15 |
| ZA867988B (en) | 1987-06-24 |
| JPH07116027B2 (ja) | 1995-12-13 |
| AU596813B2 (en) | 1990-05-17 |
| ES2039354T3 (es) | 1996-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |