DE1643506B2 - N to the power of 1-acylphenylhydrazines, their salts, processes for their preparation and pharmaceuticals containing these compounds. Eliminated from: 1620441 - Google Patents
N to the power of 1-acylphenylhydrazines, their salts, processes for their preparation and pharmaceuticals containing these compounds. Eliminated from: 1620441Info
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- DE1643506B2 DE1643506B2 DE1643506A DE1643506A DE1643506B2 DE 1643506 B2 DE1643506 B2 DE 1643506B2 DE 1643506 A DE1643506 A DE 1643506A DE 1643506 A DE1643506 A DE 1643506A DE 1643506 B2 DE1643506 B2 DE 1643506B2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/02—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux
- C30B19/04—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux the solvent being a component of the crystal composition
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/06—Reaction chambers; Boats for supporting the melt; Substrate holders
- C30B19/061—Tipping system, e.g. by rotation
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/10—Inorganic compounds or compositions
- C30B29/40—AIIIBV compounds wherein A is B, Al, Ga, In or Tl and B is N, P, As, Sb or Bi
- C30B29/42—Gallium arsenide
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- Inorganic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Description
CH3OCH 3 O
NH-N=BNH-N = B
(H)(H)
in der B der Rest eines Aldehyds oder Ketons ist, mit einem Säurehalogenid der allgemeinen Formelin which B is the residue of an aldehyde or ketone, with an acid halide of the general formula
R—CO—YR-CO-Y
(HI)(HI)
in dei R—CO die vorstehende Bedeutung hat und Y ein Halogenatom ist, oder dem entsprechenden Säureanhydrid kondensiert und das erhaltene N'-Acylphenylhydrazon der allgemeinen Formelin dei R — CO has the above meaning and Y is a halogen atom, or the corresponding acid anhydride is condensed and the obtained N'-acylphenylhydrazone of the general formula
CH3O-^ V-N-CH 3 O- ^ VN-
=B= B
(IV)(IV)
C=OC = O
mit einer Säure spaltet und gegebenenfalls aus dem erhaltenen Salz des N'-Acylphenylhydrazins mit einer Base das N'-Acylphenylhydrazin in Freiheit setzt.cleaves with an acid and optionally from the resulting salt of N'-acylphenylhydrazine a base sets the N'-acylphenylhydrazine free.
3. Arzneimittel, gekennzeichnet durch einen Gehalt an einem N'-Acylphenylhydrazin oder dessen Salz mit einer Säure nach Anspruch 1 und üblichen TrägerstofFen und bzw. oder Verdünnungsmitteln. 3. Medicines, characterized by a content of an N'-acylphenylhydrazine or its salt with an acid according to claim 1 and customary carriers and / or diluents.
Die Erfindung betrifft N'-Acylphenylhydrazine der allgemeinen FormelThe invention relates to N'-acylphenylhydrazines general formula
CH3OCH 3 O
(D(D
in der R—CO die 2,4-Hexadienoyl-, a-Chloracetyl-, /5-Chlorpropionyl- oder y-Chlorbutyroylgruppe bedeutet, und ihre Salze mit Säuren.in the R — CO the 2,4-hexadienoyl, a-chloroacetyl, / Denotes 5-chloropropionyl or γ-chlorobutyroyl group, and their salts with acids.
Die Erfindung betrifft ferner ein Verfahren zur Herstellung der Nl-Acylphenylhydrazine der allgemeinen Formel I, das dadurch gekennzeichnet ist, daß man nach üblichen Methoden ein Phenylhydrazon der allgemeinen FormelThe invention also relates to a process for the preparation of the N 1 -acylphenylhydrazines of the general formula I, which is characterized in that a phenylhydrazone of the general formula is used by customary methods
CH3OCH 3 O
NH-N=BNH-N = B
in der B der Rest eines Aldehyds oder Ketons ist, mit einem Säurehalogenid der allgemeinen Formelin which B is the residue of an aldehyde or ketone, with an acid halide of the general formula
R-CO-YR-CO-Y
(IH)(IH)
in der R-CO die vorstehende Bedeutung hat und Y ein Halogenatom ist, oder dem entsprechenden Säureanhydrid kondensiert und das erhaltene hT-Acyiphenylhydrazon der allgemeinen Formelin which R-CO has the above meaning and Y is a halogen atom, or the corresponding acid anhydride condensed and the resulting hT-acyiphenylhydrazone of the general formula
CH3O-/ V-N-N=BCH 3 O- / VNN = B
mit einer Säure spaltet und gegebenenfalls aus dem erhaltenen Salz des N'-Acylphenylhydrazins mit einer Base das N'-Acylphenylhydrazin in Freiheit setzt.Cleaves with an acid and optionally from the resulting salt of N'-acylphenylhydrazine with a Base sets the N'-acylphenylhydrazine free.
Die Erfindung betrifft ferner Arzneimittel, die die vorstehenden Verbindungen enthalten.The invention also relates to medicaments which contain the above compounds.
Die vorstehend beschriebene Umsetzung verläuft über die StufenThe conversion described above takes place through the stages
[H] + [III]-[IV]-[I][H] + [III] - [IV] - [I]
Zur Herstellung der Verbindungen der Formeln IV und I werden die Phenylhydrazonverbindungen der Foimel II als Ausgangsverbindungen verwendet. Wenn das Stickstoffatom N2 acyliert wurde, ohne mit geeigneten Ketonen oder Aldehyden blockiert zu sein, kann man nicht selektiv die gewünschten Hydrazinverbindungen erhalten. In diesem Fall verläuft das Verfahren nach folgendem Reaktionsschema:To prepare the compounds of the formulas IV and I, the phenylhydrazone compounds of the Foimel II are used as starting compounds. If the nitrogen atom N 2 has been acylated without being blocked with suitable ketones or aldehydes, one cannot selectively obtain the desired hydrazine compounds. In this case, the process proceeds according to the following reaction scheme:
NH-NH2 + R-CO-YNH-NH 2 + R-CO-Y
CH1OCH 1 O
C = O
RC = O
R.
55 + CHi-/ 55 + CHi- /
C=OC = O
Ketone oder Aldehyde können allgemein zur Herstellung der Phenylhydrazone der allgemeinen Formel II verwendet werden. In der Praxis werden jedoch vorzugsweise solche Carbonylverbindungen verwendet, die keine Nebenreaktionen eingehen und die leicht erhältlich sind. Beispiele für solche Verbindungen sind Acetyldehyd, Chloral und Benzaldehyd. Bei der Umsetzung der Phenylhydrazone der all-Ketones or aldehydes can generally be used to prepare the phenylhydrazones of the general formula II can be used. In practice, however, such carbonyl compounds are preferably used which do not undergo side reactions and which are easily available. Examples of such compounds are acetyldehyde, chloral and benzaldehyde. In the implementation of the phenylhydrazones of the general
gemeinen Formel II mit dem Säurehalogenid der allgemeinen Formel III oder dem entsprechenden Säureanhydrid wird in einigen Fällen die N=C-Bindung durch den Rest B geschwächt. Man erhält im allgemeinen die N'-Acylphenylhydrazone der allgemeinen Formel IV, z. B. im Falle der Hydrazone von Acetaldehyd oder Lävulinsäuremethylester. Wird die Acylierung unter verhältnismäßig scharfen Bedingen durchgeführt, so wird die Hydrazonbindung nach der Acylierung leicht gespalten, und man erhält unmittelbar die N'-Acylphenylhydrazine der allgemeinen Formel I. Beispielsweise werden N*-(2,4-Hexadienoyl) - N1 - (p - methoxyphenyl) - hydrazin und N'-(Chloracety!)-phenylhydrazin unmittelbar aus den entsprechenden Hydrazonverbindungen erhalten.Common formula II with the acid halide of the general formula III or the corresponding acid anhydride, the N = C bond is weakened by the B radical in some cases. In general, the N'-acylphenylhydrazones of the general formula IV are obtained, e.g. B. in the case of the hydrazones of acetaldehyde or levulinic acid methyl ester. If the acylation is carried out under relatively severe conditions, the hydrazone bond is easily cleaved after the acylation, and the N'-acylphenylhydrazines of the general formula I are obtained immediately. For example, N * - (2,4-hexadienoyl) - N 1 - ( p - methoxyphenyl) - hydrazine and N '- (chloroacety!) - phenylhydrazine obtained directly from the corresponding hydrazone compounds.
Die neuen N'-Acylphenylhydrazinverbindungen der Formel \ und deren Salze werden im allgemeinen in hoher AusSute durch Spaltung der N'-Acylphenylhydrazone der allgemeinen Formel IV mit einer Säure erhalten. The novel N'-Acylphenylhydrazinverbindungen of formula \ and its salts are generally obtained in high AusSute with an acid by cleavage of the N'-Acylphenylhydrazone of the general formula IV.
Die N'-Acylphenylhydrazone der allgemeinen Formel IV leiten sich von verschiedenen Ketonen oder Aldehyden ab, wie Diäthylketon, Phenyläthylketon, Äthylbutylketon, Methoxyacnon, Benzaldehyd. Acetaldehyd, Chloral. Lävulinsäuremethylester und y-Methoxybutyraldehyd. Gewöhnlich wird eine Verbindung verwendet, die nach beendeter Umsetzung leicht gespalten werden kann und keine ausbeuteverminderndc Nebenreaktion eingeht und die leicht erhältlich ist. In dies.;r Hii icht ist Acetaldehyd als Carbonylverbindung besonders geeignet.The N'-acylphenylhydrazones of the general formula IV are derived from various ketones or Aldehydes, such as diethyl ketone, phenyl ethyl ketone, ethyl butyl ketone, methoxyacnone, benzaldehyde. Acetaldehyde, Chloral. Levulinic acid methyl ester and γ-methoxybutyraldehyde. Usually there will be a connection used, which can be easily split after completion of the reaction and does not reduce the yield Side reaction enters into and which is easily available. In this.; R hii icht is acetaldehyde as Carbonyl compound particularly suitable.
Die Spaltung wird Vorzugs* -ise in einem Lösungsmittel, z. B. einem Alkohol, durchgeführt. Wenn mehr als 1 Äquivalent Alkohol verwendet wird, kann man auch noch ein gevöhnliches inertes Lösungsmittel, wie Äther, Benzol oder Toluol, verwenden.The cleavage is preferably carried out in a solvent, z. B. an alcohol performed. If more than 1 equivalent of alcohol is used, one can also use a common inert solvent such as ether, benzene or toluene.
Zur Spaltung der N'-Acylphenylhydrazone können im allgemeinen anorganische Säuren, in einigen Fällen auch organische Säuren verwendet werden. Organische Säuren werden jedoch in den meisten Fällen nicht bevorzugt, weil bei ihrer Verwendung nicht nur die Ausbeute niedriger ist, sondern auch Nebenreaktionen ablaufen können. Die bevorzugten anorganischen Säuren sind Salzsäure, Schwefelsäure und Phosphorsäure. In diesem Fall können noch bessere Ergebnisse erhalten werden, je weniger Wasser die Säuren enthalten. In general, inorganic acids, in some cases, can be used to cleave the N'-acylphenylhydrazones organic acids can also be used. However, organic acids will not work in most cases preferred because when they are used, not only is the yield lower but also side reactions can expire. The preferred inorganic acids are hydrochloric acid, sulfuric acid and phosphoric acid. In this case, even better results can be obtained the less water the acids contain.
Die Umsetzung ist in kurzer Zeit selbst bei niedriger Temperatur beendet, und die Ausbeute ist überraschend hoch. Weiterhin werden die N'-Acylphenylhydrazine der allgemeinen Formel I in Form der Salze erhalten, die leicht in kristalliner Form entweder durch Einengen des Lösungsmittels oder durch Kühlung der Lösung erhalten werden können. Wenn diese Salze mit Basen behandelt werden, erhält man die freien Hydrazinverbindungen in quantitativer Ausbeute. The reaction is completed in a short time even at a low temperature, and the yield is surprising high. Furthermore, the N'-acylphenylhydrazines of the general formula I are in the form of Salts are easily obtained in crystalline form either by concentration of the solvent or by cooling the solution can be obtained. When these salts are treated with bases, one obtains the free hydrazine compounds in quantitative yield.
Die N'-Acylphenylhydrazine der allgemeinen Formel I haben bakterizide Wirkungen insbesondere gegenüber Mycobacterium tuberculosis. Sie sind ferner wichtige Zwischenprodukte zur Herstellung der verschiedensten Arzneimittel, z. B. mit antiphlogistischer, analgetischer oder antipyretischer Wirkung, sowie für Tranquilizer und gegen Arteriosklerose.The N'-acylphenylhydrazines of the general formula I have bactericidal effects in particular against Mycobacterium tuberculosis. They are also important intermediate products in the manufacture of a wide variety of products Drugs, e.g. B. with anti-inflammatory, analgesic or antipyretic effects, as well for tranquilizers and against arteriosclerosis.
Nachstehend ist die minimale Hemmkonzentration der Verbindungen der Erfindung dem bekannten Tuberkulostatikum p-Aminosalicylsäure gegenübereestellt. Below is the minimum inhibitory concentration of the compounds of the invention that is known Tuberculostatic p-aminosalicylic acid set against.
In-vitro-Aktivität gegen Mycobacterium tuberculosis var. bovisIn vitro activity against Mycobacterium tuberculosis var. bovis
MinimaleMinimal
Hennn-Hennn-
lconzcntrationConcentration
r/mlr / ml
1 2 21 2 2
phenyO-hydrazin-bydrocblorid phenyO-hydrazine-bydrocbloride
hydrazin-hydrochlorid hydrazine hydrochloride
phenyl)-hydrazin-hydrochlorid phenyl) hydrazine hydrochloride
phenyiy-hydrazin-hvdrochlorid ....phenyiy-hydrazine-hvdrochlorid ....
p-Aminosalicylsäure p-aminosalicylic acid
Die Erfindung wird durch die Beispiele erläutert.The invention is illustrated by the examples.
, 49 g Acetakiehyd-N1 -^'-chlorbutyroyD-N1 -{p-methoxyphenylHiydrazon werden in 200 ml Alkohol gelöst, und in die Lösung wird trockenes Chlorwasserstoffgas unter Eiskühlung eingeleitet. Danach wird überschüssiger Chlorwasserstoff unter vermindertem Druck abgetrennt. Es scheiden sich in großer Menge Kristalle ab, die abfiltriert und getrocknet werden. Man erhält das N1 - (4' - Chlorbutyroyl) - N1 - (p - methoxyphcnyl)-hydrazin-hydrochlorid vom Schmp. 159° C (Zersetzung) in 72%iger Ausbeute.49 g of Acetakiehyd-N 1 - ^ '- chlorbutyroyD-N 1 - {p-methoxyphenylHiydrazone are dissolved in 200 ml of alcohol, and dry hydrogen chloride gas is passed into the solution while cooling with ice. Excess hydrogen chloride is then separated off under reduced pressure. Large amounts of crystals separate out, which are filtered off and dried. The N 1 - (4 '- chlorobutyroyl) - N 1 - (p - methoxyphynyl) hydrazine hydrochloride of melting point 159 ° C. (decomposition) is obtained in 72% yield.
Gemäß Beispiel 1 wird Benzaldehyd-N'-(4'-chlorbutyroyi) - N1 - (p - methoxyphenyl) - hydrazon in das N1 - (4' - Chlorbutyroyl) N1 - (p - methoxyphenyl)-hydrazin umgewandelt.According to Example 1, benzaldehyde-N '- (4'-chlorobutyroyl) - N 1 - (p - methoxyphenyl) - hydrazone is converted into the N 1 - (4' - chlorobutyroyl) N 1 - (p - methoxyphenyl) hydrazine.
Gemäß Beispiel 1 wird Acel:.ldehyd-N'-(2',4'-hexadienoyl)-N'-(p-methoxyphenyl)-hydrazon der FormelAccording to Example 1, Acel becomes: .ldehyd-N '- (2', 4'-hexadienoyl) -N '- (p-methoxyphenyl) hydrazone the formula
CH3OCH 3 O
CH,CH,
N · IN · I
I coI. co
CH
CH
CHCH
CH
CH
IlIl
CH
CH3 CH
CH 3
in quantitativer Ausbeute in das N'-(2',4'-Hexadienoyl) - N1 - (p - methoxyphenyl) - hydrazin - hydrochlorid vom Schmp. 156 bis 1600C (Zersetzung) umgewandelt.in quantitative yield N '- (2', 4'-hexadienoyl) - N 1 - (p - methoxyphenyl) - hydrazine - hydrochloride of melting point 156-160 0 C. (decomposition) converted..
Gemäß Beispiel 1 wird Acetaldehyd-N'-(chloracetylj-l^-ip-methoxyphenyli-hydrazon in das N'-(ChloracetylJ-N'-ip-methoxyphenyO-hydrazin-hydrochlorid vom Schmp. 150 bis 151 ° C (Zersetzung) umgewandelt. Weiterhin wird dieses Hydrochlorid durch Behandlung mit 5%iger wäßriger Natriumcarbonatlösung in das freie N'-iChloracetylJ-N'-ip-methoxyphenylJ-hydrazin vom Schmp. 121 bis 122°C übergeführt.According to Example 1, acetaldehyde-N '- (chloroacetylj-l ^ -ip-methoxyphenyli-hydrazone into the N '- (chloroacetylJ-N'-ip-methoxyphenyO-hydrazine hydrochloride converted from m.p. 150 to 151 ° C (decomposition). Furthermore, this hydrochloride is by treatment with 5% aqueous sodium carbonate solution in the free N'-i-chloroacetylJ-N'-ip-methoxyphenylJ-hydrazine converted from melting point 121 to 122 ° C.
Eine gerührte Lösung von 4,9 g Acetaldehyd-(p-methoxyphenyi)-hydrazon und 3 g Triäthylamin in 120 ml Äther wird tropfenweise mit 4,6 g 3-Chlorpropionylchlorid bei einer Temperatur unterhalb' - 5°C versetzt. Danach wird die Lösung weitere 2 Stunden gerührt. Dann werden dem Reaktionsgemisch 40 ml Wasser zugegeben, die organische Schicht wird abgetrennt und zweimal mit je 50 ml Wasser gewaschen. Die erhaltene Ätherlösung wird auf 00C abgekühlt und tropfenweise mit 12 ml 6n-Lösung von Chlorwasserstoff in Äthanol versetzt. Das erhaltene Gemisch wird im Kühlschrank 16 bis 18 Stunden stehengelassen. Dann wird der kristalline Feststoff abfiltriert und mit Äther gewaschen. Man erhält N1 - (3 - Chlorpropionyl) - N- (p - methoxyphenyl)-hydrazin-hydrochlorid vom Schmp. 1400C (Zersetzung).A stirred solution of 4.9 g of acetaldehyde (p-methoxyphenyi) hydrazone and 3 g of triethylamine in 120 ml of ether is treated dropwise with 4.6 g of 3-chloropropionyl chloride at a temperature below -5 ° C. The solution is then stirred for a further 2 hours. Then 40 ml of water are added to the reaction mixture, the organic layer is separated off and washed twice with 50 ml of water each time. The ether solution is cooled to 0 0 C and treated dropwise with 12 ml of 6N solution of hydrogen chloride in ethanol. The resulting mixture is left to stand in the refrigerator for 16 to 18 hours. Then the crystalline solid is filtered off and washed with ether. Obtained N 1 - (3 - chloropropionyl) - N- (p - methoxyphenyl) hydrazine hydrochloride mp 140 0 C (decomposition)..
Claims (2)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP199966 | 1966-01-12 | ||
| JP2730066 | 1966-04-28 | ||
| JP2730066 | 1966-04-28 | ||
| JP2730166 | 1966-04-28 | ||
| JP2730166 | 1966-04-28 | ||
| JP2812566 | 1966-05-02 | ||
| JP2840066 | 1966-05-04 | ||
| JP4059166 | 1966-06-21 | ||
| JP4472466 | 1966-07-08 | ||
| JP4472366 | 1966-07-08 | ||
| JP5467466 | 1966-08-19 | ||
| JP5467566 | 1966-08-19 | ||
| DES0111292 | 1966-12-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1643506A1 DE1643506A1 (en) | 1972-03-30 |
| DE1643506B2 true DE1643506B2 (en) | 1973-01-04 |
| DE1643506C DE1643506C (en) | 1973-07-26 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| NL6700300A (en) | 1967-07-13 |
| CS155157B2 (en) | 1974-05-30 |
| DE1620441B2 (en) | 1974-09-19 |
| SE314985B (en) | 1969-09-22 |
| BR6786134D0 (en) | 1973-12-26 |
| DE1618933A1 (en) | 1972-03-16 |
| NL146804B (en) | 1975-08-15 |
| FI49162C (en) | 1975-04-10 |
| SU375847A3 (en) | 1973-03-23 |
| CS155158B2 (en) | 1974-05-30 |
| DK134715B (en) | 1977-01-03 |
| DE1620441A1 (en) | 1970-08-27 |
| BE692456A (en) | 1967-06-16 |
| AT283349B (en) | 1970-08-10 |
| NO126865B (en) | 1973-04-02 |
| DE1620441C3 (en) | 1975-05-22 |
| FR7844M (en) | 1970-06-01 |
| CS155156B2 (en) | 1974-05-30 |
| AT277995B (en) | 1970-01-12 |
| NO126862B (en) | 1973-04-02 |
| IL27173A (en) | 1972-08-30 |
| DK134715C (en) | 1977-05-31 |
| NO126864B (en) | 1973-04-02 |
| DE1643506A1 (en) | 1972-03-30 |
| AT277996B (en) | 1970-01-12 |
| SE307795B (en) | 1969-01-20 |
| AT280991B (en) | 1970-05-11 |
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| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |