GB1495488A - Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids - Google Patents

Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids

Info

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
Application number
GB2609676A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IPPCO INT PHARMA PATENTS CO ES
Original Assignee
IPPCO INT PHARMA PATENTS CO ES
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IPPCO INT PHARMA PATENTS CO ES filed Critical IPPCO INT PHARMA PATENTS CO ES
Priority to GB2609676A priority Critical patent/GB1495488A/en
Priority to IE125977A priority patent/IE45148B1/en
Priority to DK276377A priority patent/DK145418C/en
Priority to IT2494677A priority patent/IT1080779B/en
Priority to LU77593A priority patent/LU77593A1/xx
Priority to BE178724A priority patent/BE856044A/en
Priority to CH773477A priority patent/CH605865A5/xx
Priority to JP7392477A priority patent/JPS5331661A/en
Priority to NL7706959A priority patent/NL189352C/en
Priority to DE19772728323 priority patent/DE2728323A1/en
Priority to FR7719236A priority patent/FR2355839A1/en
Publication of GB1495488A publication Critical patent/GB1495488A/en
Expired legal-status Critical Current

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.
GB2609676A 1976-06-23 1976-06-23 Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids Expired GB1495488A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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