ES237614A1 - Substituted 3, 5-diketo-pyrazolidines - Google Patents
Substituted 3, 5-diketo-pyrazolidinesInfo
- Publication number
- ES237614A1 ES237614A1 ES0237614A ES237614A ES237614A1 ES 237614 A1 ES237614 A1 ES 237614A1 ES 0237614 A ES0237614 A ES 0237614A ES 237614 A ES237614 A ES 237614A ES 237614 A1 ES237614 A1 ES 237614A1
- Authority
- ES
- Spain
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic 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 |
---|---|
ES237614A1 true ES237614A1 (en) | 1958-03-01 |
Family
ID=4513680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES0237614A Expired ES237614A1 (en) | 1956-10-04 | 1957-08-16 | 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 |
---|---|
GB843691A (en) | 1960-08-10 |
FR1196847A (en) | 1959-11-26 |
DE1058518B (en) | 1959-06-04 |
NL99967C (en) | |
CH364509A (en) | 1962-09-30 |
BE561351A (en) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO164335B (en) | MIXING, BINDING AND USING THE BINDING ON COLLAGENT MATERIAL. | |
DE1445751A1 (en) | Process for the preparation of 2-hydroxylaminobenzoxazinones | |
Ardakani et al. | 1 H-and 2 H-indazoles by thermal and photolytic decomposition of o-azidobenzoic acid and o-azidobenzaldehyde derivatives | |
GB804761A (en) | Thiophosphoric acid esters | |
ES237614A1 (en) | Substituted 3, 5-diketo-pyrazolidines | |
US3336326A (en) | Novel imidazole carboxamides | |
GB815279A (en) | Novel benzomorpholone derivatives and a process for the manufacture thereof | |
US2762805A (en) | 3-ethyl-3-phenyl-2, 6-piperazinedione and derivatives thereof | |
Sheremetev | One-pot synthesis of 3-amino-4-aryl-and 3-amino-4-hetarylfurazans | |
US2543764A (en) | Diaralkyl carbinyl esters of dialkylamino alkanoates and the production thereof | |
Alami et al. | Synthesis of Some New N-protected 2-(Substituted-1H-1, 2, 3-Triazol-1-yl) glycine Derivatives | |
GB836332A (en) | Novel amino-acid hydrazides and a process for the manufacture of same | |
GB843688A (en) | Substituted 3,5-diketo-pyrazolidines | |
US2489354A (en) | Benzotriazines | |
GB811780A (en) | Hydrazides and thiosemicarbazones | |
Besgubenko et al. | Complexes of silicon and phosphorus chlorides with nitrogen-containing bases as the condensing agents in the synthesis of amides | |
GB769261A (en) | Novel thiamorpholone compounds and the manufacture of same | |
JPS5944312B2 (en) | Production method of indazole derivatives | |
Figurka et al. | Synthesis and biological evaluation of new amino derivatives of 1, 4-naphthoquinone | |
GB770498A (en) | -a-acylamino--ß-amino-propio-nitrophenones and derivatives and process for their preparation | |
Esikov et al. | Synthesis and Acidity of 5-Phenyltetrazol-2-ylalkanoic Acids and the Corresponding 5-(5-Phenyltetrazol-2-ylalkyl) tetrazoles | |
GB664550A (en) | Stabilizers for photographic emulsions | |
GB789696A (en) | Process for producing acridine compounds | |
GB847205A (en) | A process for the manufacture of ethylenimine derivatives and novel ethylenimine derivatives | |
GB735454A (en) | Improvements in or relating to threo-aminodiols and intermediates therefor |