GB1495488A - Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids - Google Patents
Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acidsInfo
- Publication number
- GB1495488A GB1495488A GB2609676A GB2609676A GB1495488A GB 1495488 A GB1495488 A GB 1495488A GB 2609676 A GB2609676 A GB 2609676A GB 2609676 A GB2609676 A GB 2609676A GB 1495488 A GB1495488 A GB 1495488A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzoxazolyl
- optically active
- propionitrile
- phenyl
- hydroxy
- 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
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1495488 Optically active 2 - (2 - phenyl- 5-benzoxazolyl)propionic acids IPPCO INTERNATIONAL PHARMACEUTICAL PATENTS CO ESTABLISHMENT 23 June 1976 26096/76 Heading C2C Novel optically active compounds of the Formula I in which X is F or Cl and therapeutically acceptable salts with bases, may be prepared by the sucessive steps of (a) resolving 2-(4- hydroxy - 3 - nitrophenyl) - propionitrile into its optical isomers (b) reducing the nitro group of the laevorotatory isomer to (-)2-(4-hydroxy- 3 - aminophenyl)propionitrile, (c) cyclizing this product with p-fluoro or p-chloro-benzoylhalide to form the (-)2-(2-p-halophenyl-5- benzoxazolyl)-propionitrile and (b) hydrolysing the nitrile group, with an accompanying inversion of configuration. Step (a) is preferably effected via the lephedrine salt and the residual isomer is racemized and reused. Pharmaceutical compositions of the compound I with the usual excipients show antiinflammatory activity when administered orally, parenterally or rectally.
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2609676A GB1495488A (en) | 1976-06-23 | 1976-06-23 | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
IE125977A IE45148B1 (en) | 1976-06-23 | 1977-06-20 | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
DK276377A DK145418C (en) | 1976-06-23 | 1977-06-22 | PROCEDURE FOR PREPARING AN OPTICAL ACTIVE DERIVATIVE OF 2- (2-P-HALOGENPHENYL-5-BENZOXAZOLYL) -PROPIONIC ACID |
IT2494677A IT1080779B (en) | 1976-06-23 | 1977-06-22 | OPTICALLY ACTIVE BENZOXAZOLYL-PROPIONIC ACID DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THERAPEUTIC COMPOSITIONS CONTAINING THEM |
LU77593A LU77593A1 (en) | 1976-06-23 | 1977-06-22 | |
BE178724A BE856044A (en) | 1976-06-23 | 1977-06-23 | OPTICALLY ACTIVE DERIVATIVES OF BENZOXAZOLYLPROPIONIC ACID, THEIR METHOD OF PREPARATION AND THEIR USE |
CH773477A CH605865A5 (en) | 1976-06-23 | 1977-06-23 | |
JP7392477A JPS5331661A (en) | 1976-06-23 | 1977-06-23 | Optical active compound* its preparation and medical composition containing same as active ingredient |
NL7706959A NL189352C (en) | 1976-06-23 | 1977-06-23 | METHOD FOR PREPARING OPTICALLY ACTIVE BENZOXAZOLYL-PROPIONIC ACID DERIVATIVES, AND PREPARATIONS WITH THESE COMPOUNDS AS AN ACTIVE SUBSTANCE. |
DE19772728323 DE2728323A1 (en) | 1976-06-23 | 1977-06-23 | OPTICALLY ACTIVE DERIVATIVES OF BENZOXAZOLYLPROPIONIC ACID, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS |
FR7719236A FR2355839A1 (en) | 1976-06-23 | 1977-06-23 | OPTICALLY ACTIVE DERIVATIVES OF BENZOXAZOLYL-PROPIONIC ACID, PROCESS FOR THEIR PREPARATION AND THERAPEUTIC COMPOSITIONS CONTAINING THEM |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2609676A GB1495488A (en) | 1976-06-23 | 1976-06-23 | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1495488A true GB1495488A (en) | 1977-12-21 |
Family
ID=10238311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2609676A Expired GB1495488A (en) | 1976-06-23 | 1976-06-23 | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS5331661A (en) |
BE (1) | BE856044A (en) |
CH (1) | CH605865A5 (en) |
DE (1) | DE2728323A1 (en) |
DK (1) | DK145418C (en) |
FR (1) | FR2355839A1 (en) |
GB (1) | GB1495488A (en) |
IE (1) | IE45148B1 (en) |
IT (1) | IT1080779B (en) |
LU (1) | LU77593A1 (en) |
NL (1) | NL189352C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2432512A1 (en) * | 1978-08-04 | 1980-02-29 | Ravizza Spa | PROCESS FOR THE PREPARATION OF BENZOXAZOLYL-PROPIONIC ACID DERIVATIVES |
EP0169302A1 (en) * | 1984-07-23 | 1986-01-29 | RAVIZZA S.p.A. | Process for the resolution of (+) 2-/2'-(p-fluorophenyl)-5'-benzoxazolyl/-propionic acid |
EP0324402A1 (en) * | 1988-01-13 | 1989-07-19 | EURORESEARCH S.r.L. | Water-soluble salts of (+)2-(4-fluorophenyl)-alpha-methyl-5-benzoxazole acetic acid and their preparation process |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3888864A (en) | 1973-06-29 | 1975-06-10 | Hoffmann La Roche | Amino lower alkyl ether derivatives of opium alkaloids |
IT1157295B (en) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | PROCESS PERFECTED FOR THE PREPARATION OF DERIVATIVES OF BENZOXAZOLYL PROPIONIC ACID |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL37633A (en) * | 1970-09-10 | 1975-08-31 | Merck & Co Inc | 2-(4-(2-benzoxazolyl)phenyl)alkanoic acid derivatives |
GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
GB1590587A (en) * | 1977-06-28 | 1981-06-03 | Lilly Industries Ltd | Benoxaprofen |
-
1976
- 1976-06-23 GB GB2609676A patent/GB1495488A/en not_active Expired
-
1977
- 1977-06-20 IE IE125977A patent/IE45148B1/en not_active IP Right Cessation
- 1977-06-22 IT IT2494677A patent/IT1080779B/en active
- 1977-06-22 DK DK276377A patent/DK145418C/en not_active IP Right Cessation
- 1977-06-22 LU LU77593A patent/LU77593A1/xx unknown
- 1977-06-23 DE DE19772728323 patent/DE2728323A1/en active Granted
- 1977-06-23 BE BE178724A patent/BE856044A/en not_active IP Right Cessation
- 1977-06-23 CH CH773477A patent/CH605865A5/xx not_active IP Right Cessation
- 1977-06-23 FR FR7719236A patent/FR2355839A1/en active Granted
- 1977-06-23 JP JP7392477A patent/JPS5331661A/en active Pending
- 1977-06-23 NL NL7706959A patent/NL189352C/en not_active IP Right Cessation
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2432512A1 (en) * | 1978-08-04 | 1980-02-29 | Ravizza Spa | PROCESS FOR THE PREPARATION OF BENZOXAZOLYL-PROPIONIC ACID DERIVATIVES |
EP0169302A1 (en) * | 1984-07-23 | 1986-01-29 | RAVIZZA S.p.A. | Process for the resolution of (+) 2-/2'-(p-fluorophenyl)-5'-benzoxazolyl/-propionic acid |
US4698432A (en) * | 1984-07-23 | 1987-10-06 | Ravizza Spa | Process for the resolution of (±) 2-[2'-(p-fluorophenyl)-5'-benzoxazolyl]-propionic acid |
EP0324402A1 (en) * | 1988-01-13 | 1989-07-19 | EURORESEARCH S.r.L. | Water-soluble salts of (+)2-(4-fluorophenyl)-alpha-methyl-5-benzoxazole acetic acid and their preparation process |
Also Published As
Publication number | Publication date |
---|---|
FR2355839A1 (en) | 1978-01-20 |
DE2728323A1 (en) | 1978-01-19 |
LU77593A1 (en) | 1977-09-29 |
NL7706959A (en) | 1977-12-28 |
CH605865A5 (en) | 1978-10-13 |
DK145418C (en) | 1983-04-11 |
IE45148L (en) | 1977-12-23 |
DK145418B (en) | 1982-11-15 |
FR2355839B1 (en) | 1980-09-26 |
NL189352B (en) | 1992-10-16 |
NL189352C (en) | 1993-03-16 |
IT1080779B (en) | 1985-05-16 |
BE856044A (en) | 1977-10-17 |
DK276377A (en) | 1977-12-24 |
JPS5331661A (en) | 1978-03-25 |
IE45148B1 (en) | 1982-06-30 |
DE2728323C2 (en) | 1989-10-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19960622 |