LU84530A1 - Procede de preparation d'acide p-butoxyphenylacethydroxamique a l'etat finement divise et composition contenant cet acide - Google Patents
Procede de preparation d'acide p-butoxyphenylacethydroxamique a l'etat finement divise et composition contenant cet acide Download PDFInfo
- Publication number
- LU84530A1 LU84530A1 LU84530A LU84530A LU84530A1 LU 84530 A1 LU84530 A1 LU 84530A1 LU 84530 A LU84530 A LU 84530A LU 84530 A LU84530 A LU 84530A LU 84530 A1 LU84530 A1 LU 84530A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- acid
- solution
- butoxyphenylacethydroxamic
- preparation
- precipitating
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title description 8
- 239000000243 solution Substances 0.000 claims abstract description 45
- 239000004094 surface-active agent Substances 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 230000001376 precipitating effect Effects 0.000 claims abstract description 6
- 239000003637 basic solution Substances 0.000 claims abstract 2
- MXJWRABVEGLYDG-UHFFFAOYSA-N bufexamac Chemical compound CCCCOC1=CC=C(CC(=O)NO)C=C1 MXJWRABVEGLYDG-UHFFFAOYSA-N 0.000 claims description 29
- 229960000962 bufexamac Drugs 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- -1 sorbitan ester Chemical class 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000012154 double-distilled water Substances 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 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
- 239000003889 eye drop Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000007901 soft capsule Substances 0.000 description 2
- 238000007614 solvation Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001887 cortisones Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K9/08—Solutions
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU84530A LU84530A1 (fr) | 1982-12-13 | 1982-12-13 | Procede de preparation d'acide p-butoxyphenylacethydroxamique a l'etat finement divise et composition contenant cet acide |
| JP58010017A JPS59110655A (ja) | 1982-12-13 | 1983-01-26 | ｐ−ブトキシフェニルアセチルヒドロキサム酸の製造方法 |
| DE8383201719T DE3365914D1 (en) | 1982-12-13 | 1983-12-05 | Process for the preparation of finely divided p-butoxyphenyl acethydroxamic acid, and compositions containing them |
| EP83201719A EP0116182B2 (de) | 1982-12-13 | 1983-12-05 | Verfahren zur Herstellung von fein zerteilter p-Butoxyphenylacethydroxamsäure |
| AT83201719T ATE21889T1 (de) | 1982-12-13 | 1983-12-05 | Verfahren zur herstellung von fein zerteilter p- butoxyphenylacethydroxamsaeure und die sie enthaltenden zusammensetzungen. |
| US06/558,885 US4534911A (en) | 1982-12-13 | 1983-12-07 | Method for the preparation of p-butoxyphenylacetyl-hydroxamic acid in the finely divided state and a composition containing this acid |
| CA000443104A CA1218675A (en) | 1982-12-13 | 1983-12-12 | Method for the preparation of p- butoxyphenylacetylhydroxamic acid in the finely divided state and a composition containing this acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU84530 | 1982-12-13 | ||
| LU84530A LU84530A1 (fr) | 1982-12-13 | 1982-12-13 | Procede de preparation d'acide p-butoxyphenylacethydroxamique a l'etat finement divise et composition contenant cet acide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84530A1 true LU84530A1 (fr) | 1984-10-22 |
Family
ID=19730000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84530A LU84530A1 (fr) | 1982-12-13 | 1982-12-13 | Procede de preparation d'acide p-butoxyphenylacethydroxamique a l'etat finement divise et composition contenant cet acide |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4534911A (de) |
| EP (1) | EP0116182B2 (de) |
| JP (1) | JPS59110655A (de) |
| AT (1) | ATE21889T1 (de) |
| CA (1) | CA1218675A (de) |
| DE (1) | DE3365914D1 (de) |
| LU (1) | LU84530A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3468336D1 (en) * | 1983-06-22 | 1988-02-11 | Univ Ohio State Res Found | Small particle formation |
| DE3604050A1 (de) * | 1986-02-08 | 1987-08-13 | Boehringer Mannheim Gmbh | Thioether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| EP0885609A1 (de) * | 1997-06-17 | 1998-12-23 | Continental Pharma Incorporated | Verwendung einer pharmazeutischen Zusammensetzung zur Behandlung traumatischer Arthritis in Pferden |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE600278A (fr) * | 1960-02-18 | 1961-08-16 | Basf Ag | Procédé pour la production de N-aryl-N'-hydroxy-urées. |
| SU390074A1 (ru) * | 1970-08-04 | 1973-07-11 | Всесоюзный научно исследовательский , проектный институт механической обработки полезных ископаемых | Способ получения алкилгидроксамовых |
| SU632690A1 (ru) * | 1977-06-08 | 1978-11-15 | Предприятие П/Я М-5245 | Способ получени с7-с9-алкилгидроксамовых кислот |
| JPS5777646A (en) * | 1980-10-31 | 1982-05-15 | Kanto Kagaku Kk | Preparation of hydroxamic acid |
-
1982
- 1982-12-13 LU LU84530A patent/LU84530A1/fr unknown
-
1983
- 1983-01-26 JP JP58010017A patent/JPS59110655A/ja active Granted
- 1983-12-05 AT AT83201719T patent/ATE21889T1/de not_active IP Right Cessation
- 1983-12-05 EP EP83201719A patent/EP0116182B2/de not_active Expired
- 1983-12-05 DE DE8383201719T patent/DE3365914D1/de not_active Expired
- 1983-12-07 US US06/558,885 patent/US4534911A/en not_active Expired - Lifetime
- 1983-12-12 CA CA000443104A patent/CA1218675A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0116182B1 (de) | 1986-09-03 |
| JPS6121618B2 (de) | 1986-05-28 |
| CA1218675A (en) | 1987-03-03 |
| DE3365914D1 (en) | 1986-10-09 |
| JPS59110655A (ja) | 1984-06-26 |
| US4534911A (en) | 1985-08-13 |
| EP0116182B2 (de) | 1989-12-27 |
| EP0116182A1 (de) | 1984-08-22 |
| ATE21889T1 (de) | 1986-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transfer of rights |
Free format text: 860109 CONTINENTAL PHARMA INC. BRUXELLES |