GB974743A - New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same - Google Patents

New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same

Info

Publication number
GB974743A
GB974743A GB593261A GB593261A GB974743A GB 974743 A GB974743 A GB 974743A GB 593261 A GB593261 A GB 593261A GB 593261 A GB593261 A GB 593261A GB 974743 A GB974743 A GB 974743A
Authority
GB
United Kingdom
Prior art keywords
formula
radical
hydroxy
compounds
derivative
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
GB593261A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB974743A publication Critical patent/GB974743A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C07D231/36—Oxygen atoms with hydrocarbon radicals, substituted by hetero atoms, attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of formula <FORM:0974743/C1/1> wherein R1 represents hydrogen, an alkyl (1-6C) radical or a halogen atom and X represents SO or SO2, their tautomers, and their salts with inorganic or organic bases: and their preparation by; (1) converting a mercapto compound of formula <FORM:0974743/C1/2> wherein R3 represents an acyl radical which is easily split off or an a -alkoxy-alkyl radical in which the alkoxy groups and the alkyl group can also be bound together to form a ring, by hydrolysis and previous or subsequent oxidation into a compound I, the mercapto compound optionally being prepared by (A) reacting in the presence of an alkaline condensing agent a malonic acid diester of formula <FORM:0974743/C1/3> wherein Y1 represents a hydrocarbon radical, with a hydroxy-hydrazobenzene derivative of formula <FORM:0974743/C1/4> wherein R2 represents an a -alkoxy-alkyl radical in which the alkoxy group and the alkyl group can also be bound together to form a ring and one of the symbols Z1 and Z2 represents hydrogen and the other represents hydrogen or an acyl radical which is easily split off, or (B) reacting in the presence of an acid binding agent a malonic acid derivative of formula <FORM:0974743/C1/5> wherein Y2 represents chlorine, bromine or an acetoxy radical with a hydroxy-hydrazobenzene derivative of formula <FORM:0974743/C1/6> or (C) reacting in the presence of an acid binding agent a malonic acid derivative of formula <FORM:0974743/C1/7> with a hydroxy-hydrazobenzene derivative of Formula III and treating the reaction product so obtained with an alkaline condensing agent; or (2) condensing a substituted malonic acid of formula <FORM:0974743/C1/8> with a hydrazo compound of formula <FORM:0974743/C1/9> wherein R4 represents hydrogen or R3, by means of an N1N1-di-substituted carbodiimide and if necessary hydrolysing the condensation product; or (3) performing the previous condensation (2) with a starting material wherein X is s and oxidising the product; or (4) oxidising a compound of formula <FORM:0974743/C1/100> The description refers also to process (1) (B) performed without an acid binding agent by using as starting materials metal derivatives of compounds V wherein the N-hydrogen atoms have been replaced. Malonic acid diesters II can be prepared by condensing C-unsubstituted diesters with phenylthioalkyl-halides; hydrolysis, and possibly oxidation, yields the malonic acids VIII and analogous compounds wherein X is S which on treatment with inorganic acid halides or acetic anhydride yield malonic qcid derivatives IV. Hydroxy-hydrazobenzene derivatives III, V and IX are made by reducing hydroxy-azobenzenes, first forming the acetal or acylated derivatives if appropriate. Pharmaceutical compositions are mentioned comprising compounds I and their salts with bases together with carriers for oral (tablets, powders, capsules), parenteral (solutions) and rectal (suppositories) administration. The compounds have uricosuric, antiphlogistic and analgesic properties. Specification 974,744 is referred to.
GB593261A 1960-02-18 1961-02-17 New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same Expired GB974743A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH181760A CH381695A (en) 1960-02-18 1960-02-18 Process for the preparation of new 4-substituted 1,2-diaryl-3,5-dioxo-pyrazolidines

Publications (1)

Publication Number Publication Date
GB974743A true GB974743A (en) 1964-11-11

Family

ID=4219283

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2419664A Expired GB974744A (en) 1960-02-18 1961-02-17 New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same
GB593261A Expired GB974743A (en) 1960-02-18 1961-02-17 New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2419664A Expired GB974744A (en) 1960-02-18 1961-02-17 New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same

Country Status (4)

Country Link
BE (1) BE600340A (en)
CH (1) CH381695A (en)
ES (2) ES264967A1 (en)
GB (2) GB974744A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4296128A (en) 1979-05-11 1981-10-20 Ciba-Geigy Corporation Carboxylic acid hydrazides and processes for their manufacture

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4296128A (en) 1979-05-11 1981-10-20 Ciba-Geigy Corporation Carboxylic acid hydrazides and processes for their manufacture

Also Published As

Publication number Publication date
BE600340A (en) 1961-08-17
ES264967A1 (en) 1961-08-01
GB974744A (en) 1964-11-11
CH381695A (en) 1964-09-15
ES264968A1 (en) 1961-08-01

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