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FR2359110A1 - Salicylic acid acyloxy-methyl ester derivs. - with analgesic, antiinflammatory and antipyretic activity with reduced gastric irritation - Google Patents

Salicylic acid acyloxy-methyl ester derivs. - with analgesic, antiinflammatory and antipyretic activity with reduced gastric irritation

Info

Publication number
FR2359110A1
FR2359110A1 FR7722248A FR7722248A FR2359110A1 FR 2359110 A1 FR2359110 A1 FR 2359110A1 FR 7722248 A FR7722248 A FR 7722248A FR 7722248 A FR7722248 A FR 7722248A FR 2359110 A1 FR2359110 A1 FR 2359110A1
Authority
FR
France
Prior art keywords
alkyl
analgesic
gastric irritation
salicylic acid
antiinflammatory
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.)
Withdrawn
Application number
FR7722248A
Other languages
French (fr)
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of FR2359110A1 publication Critical patent/FR2359110A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

New salicylic acid ester derivs. are of formula (I). In the formula R is H or a hydrolytically labile gp. R1 is H or 1-5C alkyl, R2 is 4-12 C alkyl, 1-(1-5C alkyl)-(4-6C cycloalkyl) or (4-6C cycloalkyl) or (4-6C cycloalkyl)-(1-5C alkyl), and X is H, halogen, 1-5C alkyl, 1-5C alkoxy, NO2, amino or acetamido. (I) have analgesic, anti-inflammatory and antipyretic activity, and in addition they give rise to a reduction in Zimmermann particles, which reduces gastric irritation. (I) thus have all he favourable properties of aspirin without the undesirable gastric irritation caused by aspirin. Specific cpds. (I) include pivaloyloxymethyl salicylate. In an example, this was prepd. by refluxing Na salicylate with chloromethyl pivalate, KI and acetonitrile.
FR7722248A 1976-07-21 1977-07-20 Salicylic acid acyloxy-methyl ester derivs. - with analgesic, antiinflammatory and antipyretic activity with reduced gastric irritation Withdrawn FR2359110A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US70716976A 1976-07-21 1976-07-21

Publications (1)

Publication Number Publication Date
FR2359110A1 true FR2359110A1 (en) 1978-02-17

Family

ID=24840632

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7722248A Withdrawn FR2359110A1 (en) 1976-07-21 1977-07-20 Salicylic acid acyloxy-methyl ester derivs. - with analgesic, antiinflammatory and antipyretic activity with reduced gastric irritation

Country Status (5)

Country Link
JP (1) JPS5331640A (en)
DE (1) DE2732144A1 (en)
FR (1) FR2359110A1 (en)
IL (1) IL52494A0 (en)
SE (1) SE7708340L (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0002872A1 (en) * 1977-12-23 1979-07-11 THE PROCTER & GAMBLE COMPANY Process for preparing acylated esters of hydroxy carboxylates
WO2009049961A3 (en) * 2007-10-19 2009-06-25 Nicox Sa New no-donor aspirin derivatives
WO2010118968A1 (en) * 2009-04-16 2010-10-21 Nicox S.A. No-donor aspirin derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2518922A (en) * 1946-06-19 1950-08-15 Monsanto Chemicals Salicylic acid derivatives and method for making same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2518922A (en) * 1946-06-19 1950-08-15 Monsanto Chemicals Salicylic acid derivatives and method for making same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0002872A1 (en) * 1977-12-23 1979-07-11 THE PROCTER & GAMBLE COMPANY Process for preparing acylated esters of hydroxy carboxylates
WO2009049961A3 (en) * 2007-10-19 2009-06-25 Nicox Sa New no-donor aspirin derivatives
WO2010118968A1 (en) * 2009-04-16 2010-10-21 Nicox S.A. No-donor aspirin derivatives

Also Published As

Publication number Publication date
IL52494A0 (en) 1977-10-31
DE2732144A1 (en) 1978-02-02
JPS5331640A (en) 1978-03-25
SE7708340L (en) 1978-01-22

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Legal Events

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ST Notification of lapse