GB974744A - 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 sameInfo
- Publication number
- GB974744A GB974744A GB2419664A GB2419664A GB974744A GB 974744 A GB974744 A GB 974744A GB 2419664 A GB2419664 A GB 2419664A GB 2419664 A GB2419664 A GB 2419664A GB 974744 A GB974744 A GB 974744A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- radical
- hydroxy
- malonic acid
- 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
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 general formula <FORM:0974744/C1/1> in which R1 represents an alkyl (1-6C) radical or a halogen atom, their tautomers, and their salts with inorganic or organic bases; and their preparation by: (1) converting a mercapto compound of formula <FORM:0974744/C1/2> wherein R3 represents an acyl radical which easily split off or an a -alkoxy-alkyl radical in which the alkoxy group and the alkyl group may also be bound together to form a ring, into a compound I by hydrolysis, the mercapto compound optionally being prepared by (A) reacting in the presence of an alkaline condensing agent a malonic acid diester of formula <FORM:0974744/C1/3> wherein Y1 represents a hydrocarbon radical, with a hydroxy-hydrazo-benzene derivative of formula <FORM:0974744/C1/4> wherein R2 represents an a -alkoxy-alkyl radical in which the alkoxy group and the alkyl group may 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:0974744/C1/5> wherein Y2 represents chlorine, bromine or an acetoxy radical with a hydroxy-hydrazobenzene derivative of formula <FORM:0974744/C1/6> or (C) reacting in the presence of an acid binding agent a malonic acid derivative of formula <FORM:0974744/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:0974744/C1/8> with a hydrazo compound of formula <FORM:0974744/C1/9> wherein R4 represents hydrogen or R3, by means of an N,N-disubstituted carbodiimide and if necessary hydrolysing the condensation product. The description also refers 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 yields malonic acids VIII which on treatment with inorganic acid halides or acetic anhydride yield malonic acid 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.
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 |
|---|---|
| GB974744A true GB974744A (en) | 1964-11-11 |
Family
ID=4219283
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB593261A Expired GB974743A (en) | 1960-02-18 | 1961-02-17 | New 4-substituted 1,2-diaryl-3,5-dioxopyrazolidines and processes for preparing same |
| GB2419664A Expired GB974744A (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 |
|---|---|---|---|
| GB593261A Expired GB974743A (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) | ES264968A1 (en) |
| GB (2) | GB974743A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR67999B (en) | 1979-05-11 | 1981-10-26 | Ciba Geigy Ag |
-
1960
- 1960-02-18 CH CH181760A patent/CH381695A/en unknown
-
1961
- 1961-02-17 BE BE600340A patent/BE600340A/en unknown
- 1961-02-17 GB GB593261A patent/GB974743A/en not_active Expired
- 1961-02-17 GB GB2419664A patent/GB974744A/en not_active Expired
- 1961-02-17 ES ES0264968A patent/ES264968A1/en not_active Expired
- 1961-02-17 ES ES0264967A patent/ES264967A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE600340A (en) | 1961-08-17 |
| ES264968A1 (en) | 1961-08-01 |
| CH381695A (en) | 1964-09-15 |
| GB974743A (en) | 1964-11-11 |
| ES264967A1 (en) | 1961-08-01 |
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