GB922585A - New hydrazine derivatives and processes for their manufacture - Google Patents
New hydrazine derivatives and processes for their manufactureInfo
- Publication number
- GB922585A GB922585A GB24662/59A GB2466259A GB922585A GB 922585 A GB922585 A GB 922585A GB 24662/59 A GB24662/59 A GB 24662/59A GB 2466259 A GB2466259 A GB 2466259A GB 922585 A GB922585 A GB 922585A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compound
- hydrogen
- denotes
- amino group
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises: (1) compounds of the general formula <FORM:0922585/IV(a)/1> (wherein A denotes a straight or branched alkylene chain, R1 denotes a free amino group, a monoacylated amino group, a secondary amino group or an alkylideneamino group, R2 denotes a hydrogen atom, or may also denote an acyl group if R1 is not a monoacylated amino group, R3 and R4 each denote a hydrogen atom or a C1-6 alkyl group or they jointly form with the adjacent nitrogen atom a 5- or 6-membered heterocyclic ring which may contain a further hetero atom, the total number of carbon atoms in R3, R4 and A being at least 3) and their addition salts with inorganic and organic acids; (2) 1-(11-dimethylaminobutyl-31) -1-acetyl-4-phenylthiosemicarbazide; (3) the preparation of compounds I by the following processes: (a) (when R1 is other than alkylideneamino, R2 is hydrogen and R3 and R4 are other than hydrogen) reacting a compound R11-NH2 (VII) (wherein R11 denotes a monoacylated or a secondary amino group) with an aliphatic oxo compound of the general formula <FORM:0922585/IV(a)/2> (wherein R13 and R14 have the meanings given for R3 and R4, except hydrogen, and <FORM:0922585/IV(a)/3> denotes A less a hydrogen atom) with subsequent reduction of the resulting hydrazone, or with an aminoalkyl halide of the general formula <FORM:0922585/IV(a)/4> (wherein hal denotes a chlorine, bromine or iodine atom), and in either case, if desired, splitting off the acyl group if R11 is a monoacylated amino group; (b) (when R1 is a free amino or alkylideneamino group, R2 is an acyl group and R3 and R4 are other than hydrogen) reacting an end product of (a) in which R1 is a free amino group, with an aliphatic oxo compound to convert R1 to an alkylideneamino group, or reacting a compound R11111-NH2 (XIII) wherein R11111 denotes an alkylideneamino group) with a compound of the general formula X above, and in either case treating the product with an acylating agent and, if desired, finally splitting off the alkylidene group; (c) (when R1 is other than alkylideneamino and R2, R3 and R4 are all hydrogen) reacting a compound VII above with a compound R7-CN (XVI) (wherein R7 is an alkenyl radical) to produce a compound of the general formula R11-NH-A1-CN XVII (wherein A1 denotes A less a methylene group) and reducing the cyano group to an aminomethyl group, and, if desired, splitting off the acyl group if R11 is a monoacylated amino group; (d) (when R1, R2, R3 and R4 are all hydrogen), reacting a compound XIII above with a compound XVI above to give a compound of the general formula R11111-NH-A1-CN XIX, splitting off the alkylidene group and reducing the cyano group to an aminomethyl group; (e) (when R1 is a secondary amino group and R3 and R4 are other than hydrogen) reducing a corresponding compound in which R1 is an alkylideneamino group and, if desired, splitting off R2 if it is an acyl group; (f) (as in (e) except that R2 must be hydrogen) reducing a corresponding compound in which R1 is a monoacylated amino group. The products are useful as monoamineoxidase inhibitors in pharmacy, as intermediates for the preparation of pharmaceutical agents, or as oxidation inhibitors in motor fuels. 1-(11- Dimethylaminobutyl- 31) - 1-acetyl-4-phenylthiosemicarbazide is prepared by reacting 1-(11-dimethylaminobutyl- 31)-1- acetylhydrazine with phenyl isothiocyanate. Phenylthiosemicarbazides are similarly prepared from 1-(dimethyl- and diethyl-aminoisopropyl)-1-acetylhydrazine also. N-Methyl-N- isopropylaminobutan-3-one is prepared by refluxing N-methyl-N-isopropylamine hydrochloride with acetone and paraformaldehyde in ethanol.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH6270158A CH370796A (en) | 1958-08-08 | 1958-08-08 | Process for the preparation of new hydrazine derivatives |
CH6433458 | 1958-09-25 | ||
CH7371559 | 1959-05-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB922585A true GB922585A (en) | 1963-04-03 |
Family
ID=27178501
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24662/59A Expired GB922585A (en) | 1958-08-08 | 1959-07-17 | New hydrazine derivatives and processes for their manufacture |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB922585A (en) |
-
1959
- 1959-07-17 GB GB24662/59A patent/GB922585A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR890003286A (en) | Methods and compositions for immunizing plants against disease | |
GB1466558A (en) | Additives for functional fluids | |
GB1184714A (en) | Di- and Tri-Phenylpropyl Piperazine Derivatives | |
GB787044A (en) | Fungicidal compositions | |
GB1291675A (en) | 0-(1,3,4-thiadiazol-2-yl)-imidazolidinone(2) derivatives, process for their production and their use as herbicidal agents | |
ES308210A1 (en) | 1, 3, 4, 9b-tetrahydro-2h-indeno(1, 2-c)pyridine derivatives | |
GB1061306A (en) | 4-substituted-2-benzhydryl-2-butanol derivatives | |
GB922585A (en) | New hydrazine derivatives and processes for their manufacture | |
GB919491A (en) | Pharmaceutical compositions | |
GB1073288A (en) | Aminoacetonitriles, their preparation and compositions containing them | |
GB822966A (en) | Manufacture of n,n-disubstituted amides of aryl acetic acids | |
GB1055221A (en) | Pyridobenzoxazepine derivatives | |
GB858792A (en) | New pyridazine derivatives and processes for their manufacture | |
ES311285A1 (en) | í -1,2,4-triazolone-(5) derivatives | |
US3641032A (en) | N n-disubstituted 2-alkyl-3-hydroxy-1(2h)-isoquinolonecarbamates | |
GB883219A (en) | Urazole derivatives and their preparation | |
US3436398A (en) | Benzhydrylidene thiazolidinones | |
ES352528A1 (en) | Phenazine derivatives | |
US3669986A (en) | Substituted dispiropentadecanes | |
GB1087840A (en) | 2,4,6-triiodoisophthalic acid derivatives and preparation thereof | |
ES363527A1 (en) | Novel Benzazocine Derivatives, the Preparation thereof and Compositions Containing the same | |
GB890725A (en) | Improvements in or relating to azetidine derivatives | |
GB1098879A (en) | 4-phenyl-ª‡-methylphenyl acetic acid amides | |
US3686408A (en) | Compositions with 5-nitro-2-furyl-isoxazoles and their use as antibacterial and antifungal agents | |
GB830223A (en) | Thianaphtheno-indoles |