CH631449A5 - Forme cristalline nouvelle de l'agent antiinflammatoire : acide 2-(4-chlorophenyl-alpha-methyl-5-benzoxazolylacetique, procede pour sa preparation et application comme medicaments. - Google Patents
Forme cristalline nouvelle de l'agent antiinflammatoire : acide 2-(4-chlorophenyl-alpha-methyl-5-benzoxazolylacetique, procede pour sa preparation et application comme medicaments. Download PDFInfo
- Publication number
- CH631449A5 CH631449A5 CH691778A CH691778A CH631449A5 CH 631449 A5 CH631449 A5 CH 631449A5 CH 691778 A CH691778 A CH 691778A CH 691778 A CH691778 A CH 691778A CH 631449 A5 CH631449 A5 CH 631449A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- chlorophenyl
- acid
- benzoxazolylacetic
- benoxaprofen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title description 2
- 239000003814 drug Substances 0.000 title description 2
- VSIWFWMESDLVCO-UHFFFAOYSA-N 2-(1,3-benzoxazol-5-yl)-2-(4-chlorophenyl)propanoic acid Chemical compound C=1C=C2OC=NC2=CC=1C(C(O)=O)(C)C1=CC=C(Cl)C=C1 VSIWFWMESDLVCO-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 36
- 229960005430 benoxaprofen Drugs 0.000 description 14
- 150000003863 ammonium salts Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CTLLPMGXBURFMU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-methyl-3H-1,3-benzoxazol-5-yl]acetonitrile Chemical compound ClC1=CC=C(C=C1)C1(OC2=C(N1)C=C(C=C2)CC#N)C CTLLPMGXBURFMU-UHFFFAOYSA-N 0.000 description 1
- 229910000570 Cupronickel Inorganic materials 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26907/77A GB1590587A (en) | 1977-06-28 | 1977-06-28 | Benoxaprofen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH631449A5 true CH631449A5 (fr) | 1982-08-13 |
Family
ID=10251100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH691778A CH631449A5 (fr) | 1977-06-28 | 1978-06-26 | Forme cristalline nouvelle de l'agent antiinflammatoire : acide 2-(4-chlorophenyl-alpha-methyl-5-benzoxazolylacetique, procede pour sa preparation et application comme medicaments. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0000276B1 (cs) |
| JP (1) | JPS5411224A (cs) |
| AT (1) | AT360008B (cs) |
| AU (1) | AU518403B2 (cs) |
| BE (1) | BE868522A (cs) |
| CH (1) | CH631449A5 (cs) |
| DE (2) | DE2828074A1 (cs) |
| DK (1) | DK145419C (cs) |
| FI (1) | FI69453C (cs) |
| FR (1) | FR2396004A1 (cs) |
| GB (1) | GB1590587A (cs) |
| IE (1) | IE47009B1 (cs) |
| IL (1) | IL55015A (cs) |
| IT (1) | IT1105065B (cs) |
| LU (1) | LU79879A1 (cs) |
| NZ (1) | NZ187674A (cs) |
| ZA (1) | ZA783660B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11981645B1 (en) | 2023-10-10 | 2024-05-14 | King Faisal University | N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as antimicrobial compound |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| US3888864A (en) | 1973-06-29 | 1975-06-10 | Hoffmann La Roche | Amino lower alkyl ether derivatives of opium alkaloids |
| GB1495488A (en) * | 1976-06-23 | 1977-12-21 | Ippco Int Pharma Patents Co Es | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
| IT1099589B (it) * | 1978-08-04 | 1985-09-18 | Ravizza Spa | Processo per la preparazione di derivati dell'acido benzoxazolil propionico |
| IT1157295B (it) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | Processo perfezionato per la preparazione di derivati dell'acido benzoxazolil propionico |
| UA83620C2 (ru) | 2001-12-05 | 2008-08-11 | Уайт | Замещенные бензоксазолы и их аналоги как эстрогенные агенты |
| WO2021116820A1 (en) * | 2019-12-10 | 2021-06-17 | Aurobindo Pharma Limited | An improved process for the preparation of benoxaprofen |
| DE102022117931A1 (de) | 2022-07-18 | 2024-01-18 | HUECK System GmbH & Co. KG | Profilanordnung mit wärmedämmung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| GB1488003A (en) * | 1973-10-23 | 1977-10-05 | Lilly Industries Ltd | 1,2-benzisoxazole derivatives processes for their preparation and their use as pharmaceuticals |
| US4087437A (en) * | 1976-09-07 | 1978-05-02 | Eli Lilly And Company | 2-Phenyl-5-benzoxazolylalkanoic acid purification process |
-
1977
- 1977-06-28 GB GB26907/77A patent/GB1590587A/en not_active Expired
-
1978
- 1978-06-26 DK DK287578A patent/DK145419C/da not_active IP Right Cessation
- 1978-06-26 CH CH691778A patent/CH631449A5/fr not_active IP Right Cessation
- 1978-06-26 NZ NZ187674A patent/NZ187674A/xx unknown
- 1978-06-27 FR FR7819091A patent/FR2396004A1/fr active Granted
- 1978-06-27 AT AT466178A patent/AT360008B/de not_active IP Right Cessation
- 1978-06-27 EP EP78300082A patent/EP0000276B1/en not_active Expired
- 1978-06-27 DE DE19782828074 patent/DE2828074A1/de not_active Ceased
- 1978-06-27 IT IT50048/78A patent/IT1105065B/it active
- 1978-06-27 ZA ZA00783660A patent/ZA783660B/xx unknown
- 1978-06-27 LU LU79879A patent/LU79879A1/xx unknown
- 1978-06-27 BE BE6046515A patent/BE868522A/xx not_active IP Right Cessation
- 1978-06-27 JP JP7795178A patent/JPS5411224A/ja active Granted
- 1978-06-27 DE DE7878300082T patent/DE2862013D1/de not_active Expired
- 1978-06-27 AU AU37501/78A patent/AU518403B2/en not_active Expired
- 1978-06-27 IL IL55015A patent/IL55015A/xx unknown
- 1978-06-27 FI FI782043A patent/FI69453C/fi not_active IP Right Cessation
- 1978-06-27 IE IE1277/78A patent/IE47009B1/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11981645B1 (en) | 2023-10-10 | 2024-05-14 | King Faisal University | N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as antimicrobial compound |
Also Published As
| Publication number | Publication date |
|---|---|
| FI782043A7 (fi) | 1978-12-29 |
| IT7850048A0 (it) | 1978-06-27 |
| EP0000276A1 (en) | 1979-01-10 |
| EP0000276B1 (en) | 1982-09-01 |
| IE47009B1 (en) | 1983-11-30 |
| GB1590587A (en) | 1981-06-03 |
| ZA783660B (en) | 1979-06-27 |
| DK145419B (da) | 1982-11-15 |
| LU79879A1 (cs) | 1978-12-07 |
| AT360008B (de) | 1980-12-10 |
| DE2862013D1 (en) | 1982-10-28 |
| DK145419C (da) | 1983-04-18 |
| FI69453B (fi) | 1985-10-31 |
| DK287578A (da) | 1978-12-29 |
| IE781277L (en) | 1978-12-28 |
| JPS6231714B2 (cs) | 1987-07-09 |
| NZ187674A (en) | 1980-11-14 |
| IT1105065B (it) | 1985-10-28 |
| FR2396004A1 (fr) | 1979-01-26 |
| IL55015A0 (en) | 1978-08-31 |
| ATA466178A (de) | 1980-05-15 |
| IL55015A (en) | 1981-11-30 |
| FI69453C (fi) | 1986-02-10 |
| JPS5411224A (en) | 1979-01-27 |
| DE2828074A1 (de) | 1979-01-11 |
| AU3750178A (en) | 1980-01-03 |
| AU518403B2 (en) | 1981-10-01 |
| BE868522A (fr) | 1978-12-27 |
| FR2396004B1 (cs) | 1981-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |