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FR2392951A2 - Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity - Google Patents

Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity

Info

Publication number
FR2392951A2
FR2392951A2 FR7716654A FR7716654A FR2392951A2 FR 2392951 A2 FR2392951 A2 FR 2392951A2 FR 7716654 A FR7716654 A FR 7716654A FR 7716654 A FR7716654 A FR 7716654A FR 2392951 A2 FR2392951 A2 FR 2392951A2
Authority
FR
France
Prior art keywords
ninhydrin
phenol
condensation products
spasmolytic
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.)
Granted
Application number
FR7716654A
Other languages
French (fr)
Other versions
FR2392951B2 (en
Inventor
Jean-Pierre Poupelin
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.)
CREAT LAB
Original Assignee
CREAT LAB
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
Priority claimed from GB527475A external-priority patent/GB1533388A/en
Application filed by CREAT LAB filed Critical CREAT LAB
Priority to FR7716654A priority Critical patent/FR2392951A2/en
Publication of FR2392951A2 publication Critical patent/FR2392951A2/en
Application granted granted Critical
Publication of FR2392951B2 publication Critical patent/FR2392951B2/fr
Granted 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
    • C07C65/32—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 keto groups
    • C07C65/40—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 keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • 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
    • C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups

Landscapes

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

Abstract

Condensation products of ninhydrin with phenols, polyphenols, and their derivatives, and having the formula (I), are new: In (I) n = 1-3; R1 and R2 = H, alkyl, acyl, aryl or heteroaryl; R3, R4, R5 and R6 = H, halogen, alkyl alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, aryl, formyl, acyl, acyloxy, carboxy, carboxyalkyl, sulphonyl, which may be substd.; or R3 and/or R4 may form an aromatic, alicyclic, polycyclic, or heterocyclic group which may be substd.). (I) are antiinflammatories, analgesics, spasmolytics, and uricosurics. Very low toxicity (Ld50 >1000 mg/kg i.p. mouse) and good gastric toleration are obtd. This is an addition to FR 76.02461. The compounds are prepared as described in the parent patent from ninhydrin and the phenol, preferably in acetic acid containing 0.2-1% HCl. The product is precipitated by addition of a mixture of heptane and ethyl acetate in the ratio 20:80 to 80:20.
FR7716654A 1975-02-07 1977-06-01 Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity Granted FR2392951A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7716654A FR2392951A2 (en) 1975-02-07 1977-06-01 Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB527475A GB1533388A (en) 1975-02-07 1975-02-07 Ninhydrin-phenol condensation products their preparation and use as therapeutic agents
FR7716654A FR2392951A2 (en) 1975-02-07 1977-06-01 Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity

Publications (2)

Publication Number Publication Date
FR2392951A2 true FR2392951A2 (en) 1978-12-29
FR2392951B2 FR2392951B2 (en) 1980-02-08

Family

ID=26220051

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7716654A Granted FR2392951A2 (en) 1975-02-07 1977-06-01 Condensation products of ninhydrin and phenol(s) - having antiinflammatory, analgesic, spasmolytic and uricosuric activity

Country Status (1)

Country Link
FR (1) FR2392951A2 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138272A1 (en) * 1983-10-14 1985-04-24 Akzo N.V. Diarylindane-1,3-diones, their preparation and use
EP0398258A1 (en) * 1989-05-16 1990-11-22 Mitsubishi Kasei Corporation Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient
US9346749B2 (en) 2011-06-16 2016-05-24 Korea Research Institute Of Chemical Technology 1,3-di-oxo-indene derivative, pharmaceutically acceptable salt or optical isomer thereof, preparation method thereof, and pharmaceutical composition containing same as an antiviral, active ingredient
US9951058B2 (en) 2012-12-14 2018-04-24 Katholieke Universiteit Leuven K.U. Leuven R & D Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing the same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
US12083092B2 (en) 2020-04-20 2024-09-10 Novartis Ag Antiviral 1,3-di-oxo-indene compounds
US12286423B2 (en) 2020-04-20 2025-04-29 Novartis Ag Antiviral 1,3-di-oxo-indene compounds

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138272A1 (en) * 1983-10-14 1985-04-24 Akzo N.V. Diarylindane-1,3-diones, their preparation and use
EP0398258A1 (en) * 1989-05-16 1990-11-22 Mitsubishi Kasei Corporation Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient
US5076830A (en) * 1989-05-16 1991-12-31 Mitsubishi Kasei Corporation Indan-1,3-dione derivative and herbicidal composition containing the same as active ingredient
US9346749B2 (en) 2011-06-16 2016-05-24 Korea Research Institute Of Chemical Technology 1,3-di-oxo-indene derivative, pharmaceutically acceptable salt or optical isomer thereof, preparation method thereof, and pharmaceutical composition containing same as an antiviral, active ingredient
US9951058B2 (en) 2012-12-14 2018-04-24 Katholieke Universiteit Leuven K.U. Leuven R & D Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing the same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
US12083092B2 (en) 2020-04-20 2024-09-10 Novartis Ag Antiviral 1,3-di-oxo-indene compounds
US12286423B2 (en) 2020-04-20 2025-04-29 Novartis Ag Antiviral 1,3-di-oxo-indene compounds

Also Published As

Publication number Publication date
FR2392951B2 (en) 1980-02-08

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