GB843691A - Substituted 3, 5-diketo-pyrazolidines - Google Patents
Substituted 3, 5-diketo-pyrazolidinesInfo
- Publication number
- GB843691A GB843691A GB3087057A GB3087057A GB843691A GB 843691 A GB843691 A GB 843691A GB 3087057 A GB3087057 A GB 3087057A GB 3087057 A GB3087057 A GB 3087057A GB 843691 A GB843691 A GB 843691A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylpiperidyl
- isopropyl
- ethyl
- dioxopyrazolidine
- phenyl
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises 3:5-dioxopyrazolidines having in one tautomeric form the general formula: <FORM:0843691/IV(b)/1> (wherein R1 represents an alkyl, alkenyl, aryl, cycloalkyl or aralkyl radical, R2 represents hydrogen or an alkyl, aralkyl or acyl radical, and R3 represents an alkyl radical of up to 4 carbon atoms, with the proviso that R1, R2 and R3 need not be dissimilar), and their salts with hydrochloric, hydrobromic, sulphuric, citric, tartaric, succinic, maleic, acetic, benzoic and hexahydrobenzoic acids, and the production thereof by condensing a piperidyl-4-hydrazine of the general formula: <FORM:0843691/IV(b)/2> with a reactive derivative of malonic acid, of the general formula: <FORM:0843691/IV(b)/3> (wherein X and Y may be similar or dissimilar, and each represents bromine, chlorine or an azide, amino or alkoxy group), R2 when an acyl group being optionally split off during or after the condensation, and the products being, if desired, converted into acid addition salts. The condensation is advantageously carried out in the absence of a solvent at 150-200 DEG C. or in an anhydrous inert organic solvent in the neighbourhood of the boiling temperature. The products are useful as antipyretics and analgesics for the treatment of rheumatism. In examples: (1) N-methylpiperidyl-4-hydrazine is refluxed with ethylmalonic acid diethyl ester in benzonitrile to produce 1-(N-methylpiperidyl-41) - 4 - ethyl - 3:5 - dioxopyrazolidine;(2)-(9) similarly prepared are the corresponding 4-isopropyl-, 4-n-butyl-, 4-phenyl-, 4-benzyl-, 2-methyl-4-phenyl-, 2-methyl-4-n-butyl-, 2-isopropyl-4-n-butyl- and 4-methyl-compounds; (10) ethylmalonyl dichloride is reacted with 1 - (N - methylpiperidyl - 41) - 2 - acetylhydrazine in chloroform in the presence of triethylamine to form 1 - (N - methylpiperidyl-41) - 2 - acetyl-4 - ethyl - 3:5 - dioxopyrazolidine; (11) ethyl-malonic and dihydrazide is treated with hydrochloric acid and sodium nitrite and the resulting diazide is reacted with N - methylpiperidyl - 4-hydrazine to give 1-(N-methylpiperidyl-41)-4-ethyl-3:5-dioxopyrazolidine; (12) n-propyl-malonic acid diethyl ester is heated with N-methylpiperidyl-4-hydrazine to produce 1-(N - methylpiperidyl - 41) - 4 - n - propyl - 3:5 - dioxopyrazolidine; (13) n-butylmalonyl dichloride is reacted as in (10) to give 1-(N-methylpiperidyl - 41) - 2 - acetyl - 4 - m - butyl - 3:5 - dioxopyrazolidine, from which (14) the acetyl group is removed by heating with aqueous methanol; (15) the product of (14) is prepared by heating 1 - (N - methylpiperidyl - 41) - 2 - acetylhydrazine with n-butylmalonic acid diethyl ester, the acetyl group being split off during the condensation; (16) N - methylpiperidyl - 4 - hydrazine is reacted as in (13) to produce 1-(N-methylpiperidyl - 41) - 4 - n - butyl - 3:5 - dioxopyrazolidine; (17) phenylmalonyl dichloride is reacted as in (10) to form 1-(N-methylpiperidyl-41) - 2 - acetyl - 4 - phenyl - 3:5 - dioxopyrazolidine, from which (18) the acety group is split off as in (14) or by heating with dilute hydrochloric acid (the product in the latter clase being in the form of its hydrochloride): (19) the product of (18) is prepared by a process analogous to that of (15); (20) and (21) N-methylpiperidyl-4-hydrazine is heated with phenylmalonic acid diamide or ethyl ester-amide to produce 1-(N-methylpiperidyl - 41) - 4 - phenyl - 3:5 -dioxopyrazolidine; (22) 1 - (N - methylpiperidyl - 41) - 2 - methylhydrazine is heated with ethylmalonic acid diethyl ester to give 1-(N-methylpiperidyl-41)-2-methyl - 4 - ethyl - 3:5 - dioxopyrazolidine; (23)-(35) similarly prepared are the corresponding 2 - methyl - 4 - isopropyl-, 2 - methyl - 4 - benzyl-, 2 - ethyl - 4 - phenyl-, 2 - ethyl - 4 - n - butyl-, 2 - ethyl - 4 - alkyl -, 2 - isopropyl - 4 - phenyl-, 2 - isopropyl - 4 - methyl-, 2 - isopropyl - 4-ethyl-, 2 - isopropyl - 4 - n - propyl-, 2:4 - diisopropyl-, 2 - isopropyl - 4 - hexyl-, 2 - isopropyl - 4 - cyclohexyl- and 2-benzyl-4-phenylcompounds; (36)-(45) by methods analogous to one or other of the foregoing are prepared 1-(N-methylpiperidyl-41)-2-isopropyl-4-phenyl, -2-methy-4 - benzyl-, - 2 - ethyl - 4 - phenyl, - 2 - isopropyl-4 - phenyl-, - 2 - isopropyl - 4 - ethyl-, - 2 - ethyl-4 - n - butyl-, - 2 - isopropyl - 4 - n - butyl-, - 4 - n - butyl-, and - 2:4 - dimethyl - 3:5 - dioxopyrazolidine and 1-(N-n-butylpiperidyl-41)-4 - phenyl - 3:5 - dioxopyrazolidine. Salts of some of the products are described. Specifications 843,688 and 843,689 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH3817256A CH364509A (en) | 1956-10-04 | 1956-10-04 | Process for the preparation of new 3,5-diketopyrazolidines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB843691A true GB843691A (en) | 1960-08-10 |
Family
ID=4513680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3087057A Expired GB843691A (en) | 1956-10-04 | 1957-10-02 | Substituted 3, 5-diketo-pyrazolidines |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE561351A (en) |
CH (1) | CH364509A (en) |
DE (1) | DE1058518B (en) |
ES (1) | ES237614A1 (en) |
FR (1) | FR1196847A (en) |
GB (1) | GB843691A (en) |
NL (1) | NL99967C (en) |
-
0
- NL NL99967D patent/NL99967C/xx active
- BE BE561351D patent/BE561351A/xx unknown
-
1956
- 1956-10-04 CH CH3817256A patent/CH364509A/en unknown
-
1957
- 1957-08-16 ES ES0237614A patent/ES237614A1/en not_active Expired
- 1957-09-24 DE DES55244A patent/DE1058518B/en active Pending
- 1957-10-02 FR FR1196847D patent/FR1196847A/en not_active Expired
- 1957-10-02 GB GB3087057A patent/GB843691A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES237614A1 (en) | 1958-03-01 |
DE1058518B (en) | 1959-06-04 |
CH364509A (en) | 1962-09-30 |
NL99967C (en) | |
FR1196847A (en) | 1959-11-26 |
BE561351A (en) |
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