GB1067575A - Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same - Google Patents

Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same

Info

Publication number
GB1067575A
GB1067575A GB25773/63A GB2577363A GB1067575A GB 1067575 A GB1067575 A GB 1067575A GB 25773/63 A GB25773/63 A GB 25773/63A GB 2577363 A GB2577363 A GB 2577363A GB 1067575 A GB1067575 A GB 1067575A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
formula
acetyl
compound
lower alkyl
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
GB25773/63A
Inventor
Jacques Maillard
Michel Vincent
Pierre Delaunay
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.)
JACQUES LOGEAIS SOC D EXPL DES
Laboratoires Jacques Logeais SA
Original Assignee
JACQUES LOGEAIS SOC D EXPL DES
Laboratoires Jacques Logeais SA
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 JACQUES LOGEAIS SOC D EXPL DES, Laboratoires Jacques Logeais SA filed Critical JACQUES LOGEAIS SOC D EXPL DES
Priority to GB25773/63A priority Critical patent/GB1067575A/en
Priority to BE649628D priority patent/BE649628A/xx
Priority to FR979422A priority patent/FR3580M/en
Publication of GB1067575A publication Critical patent/GB1067575A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel compounds of Formula I <FORM:1067575/C2/1> in which R1 and R2 are lower alkyl groups, R6 is hydrogen, or an acetyl or ethoxycarbonyl group, R3 is a group of the formula -OH, -OH.A, -OMe or -NR4R5, where A is an amine, Me a monovalent equivalent of a metal, and R4 and R5 are hydrogen, lower alkyl or acetyl, or, when R6 is an acetyl or ethoxycarbonyl group, R3 may be an -OCOCH3 or -OCOOC2H5 group, and X and Y are hydrogen or halogen, but excluding compounds in which X and Y are each hydrogen or chlorine, R1 and R2 are methyl, R3 is hydroxy and R6 is hydrogen, and the preparation thereof by carbonating with carbon dioxide under pressure a compound of Formula II. <FORM:1067575/C2/2> to produce a compound of Formula I in which R3 is -OMe and X and Y are hydrogen, and, if desired, treating the product with a solution of halogen in a solvent to produce a compound of Formula I in which X and/or Y is halogen and R3 is -OMe, or acidifying the product to produce a compound of Formula I in which X and Y are hydrogen, and R3 is -OH, followed, if desired, by treating this compound with a solution of sulphuryl halide in a halogenated solvent to produce a compound of Formula I in which X and/or Y are halogen and R3 is -OH, these acids then being treated with two molecules of acetic anhydride or ethyl chlorocarbonate per molecule to give compounds of Formula I in which R3 is -OCOCH3 and R6 is acetyl or R3 is -OCOOC2H5 and R6 is ethoxycarbonyl respectively, these products then being treated with a solution of compound HNR4R5 in an organic solvent to give a compound of Formula I in which R3 is -NR4R5, where R4 and/or R5 are hydrogen and/or lower alkyl and R6 is hydrogen, the amides then being transformed into compounds of Formula I in which R3 is -NR4R5, where R4 and/or R5 are hydrogen, lower alkyl or acetyl, and R6 is acetyl by acylation with acetic anhydride, or into compounds of Formula I in which R3 is -NR4R5, where R4 and/or R5 are hydrogen o lower alkyl groups, and R6 is an ethoxycarbonyl group, by treatment with ethyl chlorocarbonate.ALSO:Therapeutic compositions having analgesic and anti-inflammatory activity, and which may be administered orally, parenterally or rectally, comprise as active ingredient a compound of formula <FORM:1067575/A5-A6/1> in which R1 and R2 are lower alkyl groups, and R3 is a group of formula -OH, -OH.A, -OMe, or -NR4R5, A being an amine, Me a monovalent equivalent of a metal, and R4 and R5 being hydrogen, lower alkyl or acetyl, or when R6 is an acetyl or ethoxycarbonyl group R3 may be a -OCOCH3 or -OCOOC2H5 group respectively, R6 is hydrogen, or an acetyl or ethoxycarbonyl group, and X and Y are hydrogen or halogen.
GB25773/63A 1963-06-28 1963-06-28 Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same Expired GB1067575A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB25773/63A GB1067575A (en) 1963-06-28 1963-06-28 Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same
BE649628D BE649628A (en) 1963-06-28 1964-06-23
FR979422A FR3580M (en) 1963-06-28 1964-06-24 Medicinal product which can be used in particular as an analgesic and anti-inflammatory drug, based on a phloroglucinol derivative.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB25773/63A GB1067575A (en) 1963-06-28 1963-06-28 Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same

Publications (1)

Publication Number Publication Date
GB1067575A true GB1067575A (en) 1967-05-03

Family

ID=10233052

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25773/63A Expired GB1067575A (en) 1963-06-28 1963-06-28 Therapeutic compositions containing phloroglucinol derivatives, new derivatives of phloroglucinol and process for preparing the same

Country Status (3)

Country Link
BE (1) BE649628A (en)
FR (1) FR3580M (en)
GB (1) GB1067575A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT401514B (en) * 1984-09-19 1996-09-25 Cird Galderma Process for the preparation of novel organic acids and acid chlorides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT401514B (en) * 1984-09-19 1996-09-25 Cird Galderma Process for the preparation of novel organic acids and acid chlorides

Also Published As

Publication number Publication date
FR3580M (en) 1965-10-04
BE649628A (en) 1964-12-23

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