GB1307284A - 2-substituted phenyl propionic acids - Google Patents

2-substituted phenyl propionic acids

Info

Publication number
GB1307284A
GB1307284A GB1257070A GB1307284DA GB1307284A GB 1307284 A GB1307284 A GB 1307284A GB 1257070 A GB1257070 A GB 1257070A GB 1307284D A GB1307284D A GB 1307284DA GB 1307284 A GB1307284 A GB 1307284A
Authority
GB
United Kingdom
Prior art keywords
acids
fluorophenoxy
phenyl
compounds
acetophenone
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
GB1257070A
Inventor
S Adams
J Tantum
B Armitage
J Nicholson
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.)
Boots Co PLC
Original Assignee
Boots Co PLC
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 Boots Co PLC filed Critical Boots Co PLC
Publication of GB1307284A publication Critical patent/GB1307284A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1307284 2 - Phenylpropionic acid derivatives BOOTS CO Ltd 19 April 1971 [16 March 1970] 12570/70 Heading C2C The invention comprises novel 2-phenylpropionic acids of the formula wherein X is O or NH; R 1 is halogen; R 2 and R 3 are H or halogen, at least one of them being H; Y is COOH, CONH 2 or CH 2 OH; together with pharmaceutically acceptable esters, and salts with inorganic and organic bases of those compounds in which Y is COOH, and their preparation. The free acids of the above formula are prepared by the decarboxylation of the corresponding 2 - [3 - R3 - 4 - (4 - R 1 - 2 - R 2 - phenoxy)phenyl] - 2 - methyl - malonic acids or 2 - [3 - R 3 - 4 - (4 - R 1 - 2 - R 2 - anilino)phenyl]- 2-methylmalonic acids. Acids in which X is O may also be obtained by the Ullmann reaction between either 4 - R 1 - 2 - R2 - phenols and 2- (3 - R 3 - 4 - halophenyl) - propionic acids or 4 - R 1 - 2 - R 2 - halobenzenes and 2 - (3 - R 1 - 4- hydroxyphenyl)propionic acids. Acids in which X is NH may be made by hydrolysing compounds of the formula wherein R 5 is an acyl group. The acids thus obtained may be reduced to the corresponding compounds in which Y is CH 2 OH or converted to esters, amides or salts. Other methods of preparation are described in general terms. The following intermediates and starting materials are also prepared: diethyl 2-[4-(4- fluorophenoxy)phenyl]- 2 - methyl - malonate, 4<SP>1 </SP>- (4 - fluorophenoxy)acetophenone, 4 - (4- fluorophenoxy)phenylacetic acid and its ethyl ester, 2 - [4 - (4 - fluorophenoxy)phenyl]- 2- methylmalonic acid, diethyl 2 - [4 - (4 - chlorophenoxy)phenyl] - 2 - methylmalonate, ethyl 4 - (4 - chlorophenoxy)phenylacetate, 41 - (4 fluorophenoxy) - 3<SP>1</SP>- nitroacetophenone, 31- amino - 4<SP>1</SP> - (4 - fluorophenoxy)acetophenone, 3<SP>1</SP> - chloro - 4<SP>1</SP> - (4 - fluorophenoxy)acetophenone, ethyl 3 - chloro - 4 - (4 - fluorophenoxy)phenylacetate, diethyl 3 - chloro - 4 - (4 - fluorophenoxyl)phenyl - 2 - methylmalonate, 4<SP>1</SP>- bromo - 31 - nitroacetophenone, and 2 - [4- (2,4 - difluorophenoxy)- phenyl]propionyl chloride. Pharmaceutical compositions suitable for oral, topical, parenteral and rectal administration, contain the above novel compounds in association with pharmaceutical excipients. The compounds possess anti-inflammatory, analgesic and antipyretic properties.
GB1257070A 1970-03-16 1970-03-16 2-substituted phenyl propionic acids Expired GB1307284A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1257070 1970-03-16

Publications (1)

Publication Number Publication Date
GB1307284A true GB1307284A (en) 1973-02-14

Family

ID=10007088

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1257070A Expired GB1307284A (en) 1970-03-16 1970-03-16 2-substituted phenyl propionic acids

Country Status (18)

Country Link
AT (4) AT318577B (en)
BE (2) BE764258A (en)
CA (2) CA925878A (en)
CH (2) CH530363A (en)
CS (4) CS170543B2 (en)
DE (2) DE2112322A1 (en)
DK (1) DK139673B (en)
ES (4) ES389253A1 (en)
FR (2) FR2085712B1 (en)
GB (1) GB1307284A (en)
IE (2) IE35234B1 (en)
IL (2) IL36394A (en)
NL (2) NL7103404A (en)
NO (2) NO131507C (en)
PL (4) PL72430B1 (en)
RO (4) RO61058A (en)
SE (2) SE366732B (en)
ZA (2) ZA711643B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2163986A1 (en) * 1999-07-13 2002-02-01 Menarini Lab Set of inflammation and pain inhibitors for e.g. cyclooxygenase activity inhibitors comprises alpha aryl propionic acids and aryl acetic acids
WO2005051888A2 (en) * 2003-11-27 2005-06-09 Merk Patent Gmbh Diphenylamine derivatives

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2837525A1 (en) * 1978-08-28 1980-03-20 Bayer Ag PROCESS FOR THE PRODUCTION OF 4-FLUORO-3-PHENOXY-TOLUENE
SE8400239D0 (en) * 1984-01-19 1984-01-19 Pharmacia Ab NEW ARYLETIC ACID DERIVATIVES
WO1989006227A1 (en) * 1987-12-28 1989-07-13 The Dow Chemical Company Phenoxyphenoxypropionates, intermediates thereof and methods of preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE363818B (en) * 1968-08-15 1974-02-04 Lilly Co Eli

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2163986A1 (en) * 1999-07-13 2002-02-01 Menarini Lab Set of inflammation and pain inhibitors for e.g. cyclooxygenase activity inhibitors comprises alpha aryl propionic acids and aryl acetic acids
WO2005051888A2 (en) * 2003-11-27 2005-06-09 Merk Patent Gmbh Diphenylamine derivatives
WO2005051888A3 (en) * 2003-11-27 2005-08-11 Merck Patent Gmbh Diphenylamine derivatives

Also Published As

Publication number Publication date
IE35109L (en) 1971-09-16
NL7103404A (en) 1971-09-20
ES398803A1 (en) 1974-08-16
FR2085713A1 (en) 1971-12-31
SE366733B (en) 1974-05-06
AT318577B (en) 1974-10-25
IL36395A (en) 1975-02-10
NO132989C (en) 1976-02-18
DE2112323A1 (en) 1971-11-25
IL36394A (en) 1974-11-29
NO131507C (en) 1975-06-11
AT318575B (en) 1974-10-25
DK139673B (en) 1979-03-26
CS169814B2 (en) 1976-07-29
FR2085713B1 (en) 1974-08-23
ZA711643B (en) 1971-12-29
IL36395A0 (en) 1971-05-26
PL94402B1 (en) 1977-08-31
ES398802A1 (en) 1974-08-16
CH532010A (en) 1972-12-31
RO61065A (en) 1976-08-15
NL7103403A (en) 1971-09-20
RO61093A (en) 1976-08-15
FR2085712A1 (en) 1971-12-31
CH530363A (en) 1972-11-15
CS170542B2 (en) 1976-08-27
IE35234B1 (en) 1975-12-24
AT318576B (en) 1974-10-25
RO61058A (en) 1976-08-15
NO132989B (en) 1975-11-10
FR2085712B1 (en) 1974-09-27
IL36394A0 (en) 1971-05-26
CA925878A (en) 1973-05-08
AT318574B (en) 1974-10-25
ES389252A1 (en) 1974-04-16
NO131507B (en) 1975-03-03
CA925520A (en) 1973-05-01
SE366732B (en) 1974-05-06
PL94403B1 (en) 1977-08-31
BE764258A (en) 1971-09-15
BE764257A (en) 1971-09-15
RO62254A (en) 1977-08-15
DE2112322A1 (en) 1971-10-14
PL70292B1 (en) 1974-02-28
ES389253A1 (en) 1973-06-16
IE35109B1 (en) 1975-11-12
ZA711644B (en) 1971-12-29
CS169813B2 (en) 1976-07-29
IE35234L (en) 1971-09-16
CS170543B2 (en) 1976-08-27
PL72430B1 (en) 1974-06-29
DK139673C (en) 1979-09-10

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee