DE1908047A1 - Continuous fine rolling - Google Patents

Continuous fine rolling

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Publication number
DE1908047A1
DE1908047A1 DE19691908047 DE1908047A DE1908047A1 DE 1908047 A1 DE1908047 A1 DE 1908047A1 DE 19691908047 DE19691908047 DE 19691908047 DE 1908047 A DE1908047 A DE 1908047A DE 1908047 A1 DE1908047 A1 DE 1908047A1
Authority
DE
Germany
Prior art keywords
mono
urea
methyl
heptyl
amines
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.)
Pending
Application number
DE19691908047
Other languages
German (de)
Inventor
Dr Willy Herbrand
Dr Karl-Heinz Jaeger
Dr Hermann Kasparek
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
HERBRAND KG DR
Original Assignee
HERBRAND KG DR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by HERBRAND KG DR filed Critical HERBRAND KG DR
Priority to DE19691908047 priority Critical patent/DE1908047A1/en
Publication of DE1908047A1 publication Critical patent/DE1908047A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
    • C07C273/1827—X being H
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Assembly has several cages set one behind the other. One cage is set in the bulge of the loop, between two other cages. The first cage may be displaced vertically or laterally until all the cages are aligned on the same rolling line, after which the first cage is returned to the working position. Used to compensate rolled products for length.

Description

Therapeutisch wirksame, N-mono-substituierte Harnstoffe.Therapeutically effective, N-mono-substituted ureas.

BESCHREIBUNG Die Erfindung betrifft bisher unbekannte N-mono-substituierte Harnstoffe der allgemeinen Formel: in der R Wasserstoff oder eine Hydroxyl- bzw. Sulfhydryl-Gruppe bedeutet und R1 Wasserstoff oder einen niederen Alkylrest darstellt und n eine Größe zwischen 1 und 4 ist.DESCRIPTION The invention relates to previously unknown N-mono-substituted ureas of the general formula: in which R is hydrogen or a hydroxyl or sulfhydryl group and R1 is hydrogen or a lower alkyl radical and n is between 1 and 4.

Es ist bekannt, daß niedere aliphatische Amine symphaticomimetische Eigenschaften besitzen und z.B. eine Steigerung des Blutdruckes verursachen. Diese pressorische Wirkung hat ihre Ursache weniger in einer Tonisierung des Gefäßapparates, vielmehr liegt ihr vor allem eine Verbesserung der Herztätigkeit von strophantinähnlichem Charakter zu Grunde. Im allgemeinen ist jedoch die Wirkungsdauer dieser Stoffe relativ kurz, sodaß häufigere Applikationen erforderlich sind, um einen ausreichenden therapeutischen Effekt zu erzielen.It is known that lower aliphatic amines are symphaticomimetic Have properties and e.g. cause an increase in blood pressure. These the pressor effect is less due to a toning of the vascular system, rather, it is primarily an improvement in the heart's activity similar to that of strophantine Basic character. In general, however, the duration of action of these substances is relative short, so that more frequent applications are required to achieve a sufficient therapeutic To achieve effect.

Es wurde nun gefunden, daß man durch Überführung der therapeutisch wirksamen, primären oder sekundären Amine in Harnstoff-Derivate Verbindungen erhält, in denen teilweise die cardiotonische Wirkung noch verstärkt ist. Die Wirkungsdauer der Harnstoffe ist gegenüber den Aminen wesentlich verlängert.It has now been found that by transferring the therapeutic contains effective primary or secondary amines in urea derivatives compounds, in which the cardiotonic effect is partially increased. The duration of action the urea is considerably longer than the amines.

Die neuen Verbindungen zeichnen sich außerdem durch sehr gute Verträglichkeit aus.The new compounds are also characterized by very good compatibility the end.

Die Darstellung der mono-substituierten Harnstoffe erfolgt am besten durch umsetzung geeigneter primärer oder sekundärer Amine mit Cyansäure. The monosubstituted ureas are best prepared by reacting suitable primary or secondary amines with cyanic acid.

Zweckmäßigerweise erhitzt man die Hydrochloride der Amine mit einem Alkali-oder Erdalkali-Salz der Cyansäure in wässriger Lösung auf Temperaturen zwischen 50 und 900. Meist scheiden sich die Reaktionsprodukte zunächst als Öle ab, die beim Kühlen kristallisieren.The hydrochloride of the amines is expediently heated with a Alkali or alkaline earth salt of cyanic acid in aqueous solution at temperatures between 50 and 900. Most of the time, the reaction products are initially separated as oils, which in the Crystallize cooling.

Therapeutisch wirksame, N-mono-subsituierte Harnstoffe.Therapeutically effective, N-mono-substituted ureas.

BEISPIEI;E 1.) Darstellung von N-[6-Methyl-6-hydroxy-heptyl(2)]-harnstoff In einem 500 ml Dreihalskolben, versehen mit Rührer, Tropftrichter und Thermometer werden 127 g (0,7 M) 6-Methyl-6-hydroxy-2-amino-heptan-hydrochlorid in 150 ml Wasser gelöst und auf 70-750 C erhitzt. Unter kräftigem Rühren tropft man innerhalb weniger Minuten eine Lösung von 58,4 g (0,721 M) Kaliumcyanat in 70 ml Wasser zu. Das Reaktionsgemisch wird dann 3 Stunden auf 70-75° erhitzt und kräftig gerührt. Während dieser Zeit scheidet sich ein farbloses Öl ab. Nach beendigter Reaktion gießt man das noch heiße Reaktionsgut in ein Becherglas und rührt bei gleichzeitiger Außenkühlung mit Eiswasser bis Kristallisation eintritt und das Gemisch sich auf 100 C abgekühlt hat. Durch scharfes Absaugen oder besser Zentrifugieren entfernt man möglichst große Anteile der Mutterlauge aus dem Kristallkuchen. Danach trocknet man das Produkt bei 70° im Vakuumtrockenschrank bis zur Gewichtskonstanz. Die Masse wird fein pulverisiert und 20 Minuten in 700 ml siedendem Essigsäureäthylester erhitzt. Man saugt rasch vom ungelösten Kaliumchlorid ab. EXAMPLE; E 1.) Preparation of N- [6-methyl-6-hydroxy-heptyl (2)] - urea In a 500 ml three-necked flask equipped with a stirrer, dropping funnel and thermometer 127 g (0.7 M) 6-methyl-6-hydroxy-2-amino-heptane hydrochloride in 150 ml of water dissolved and heated to 70-750 C. While stirring vigorously, one drips within a few Minutes to a solution of 58.4 g (0.721 M) potassium cyanate in 70 ml of water. The reaction mixture is then heated to 70-75 ° for 3 hours and stirred vigorously. During this time a colorless oil separates. When the reaction is complete, the still hot one is poured Place the reaction mixture in a beaker and stir it with ice water while cooling the outside at the same time until crystallization occurs and the mixture has cooled to 100.degree. By Sharp suction or, better still, centrifugation removes the largest possible amount the mother liquor from the crystal cake. The product is then dried at 70 ° in the vacuum drying cabinet until the weight is constant. The mass is finely pulverized and heated in 700 ml of boiling ethyl acetate for 20 minutes. You suck quickly from undissolved potassium chloride.

Aus dem Filtrat scheidet sich beim Abkühlen - eventuell durch Anreiben - das Reaktionsprodukt in Form farbloser, kleiner Kristalle ab. The filtrate separates out on cooling - possibly by rubbing - the reaction product in the form of colorless, small crystals.

Fpi 107 - 1090 C Ausbeute: 129 g (98% der Theorie) Fpi 107-1090 C Yield: 129 g (98% of theory)

Claims (1)

Therapeutisch wirksame, N-mono-substituierte Harnstoffe. Therapeutically effective, N-mono-substituted ureas. P A T E N T A N S P R Ü C H E 1.) N- b -Methyl-6-hydroxy-heptyl(2)-] -Harnstofi 2.) N- [6-Methyl-6-merkapto-heptyl(2)-] -Harnstoff 3.) N- [6-Methyl-heptyl(2)-] -Harnstoff 4.) Verfahren zur Herstellung von N-mono-substituierten # Harnstoffen der allgemeinen Formel: i@ er zu R Wasserstoff oder eine Hydroxyl- bzw. Sulfhy dryl-Gruppe be@eutet und R1 Wasserstoff oder einen niederen Alk@r@st darstellt und n eine Größe zwischen 1 und 4 ist, @adurch gekennzeichnet, daß man Amine der allgemeinen @@rmel: mit Cyansaure in wässri@en @e@ium bei höheren Temperaturen, @i@ v@r@@ swel@e z@is @en @0 @is 90°C liegen, umsetzt.PATENT CLAIMS 1.) N- b -Methyl-6-hydroxy-heptyl (2) -] -urea 2.) N- [6-methyl-6-mercapto-heptyl (2) -] -urea 3.) N - [6-Methyl-heptyl (2) -] -urea 4.) Process for the preparation of N-mono-substituted # ureas of the general formula: i @ er to R is hydrogen or a hydroxyl or sulfhydryl group and R1 is hydrogen or a lower alk @ r @ st and n is a size between 1 and 4, @ characterized in that amines of the general @@ rmel: with cyanoic acid in aqueous @ en @ e @ ium at higher temperatures, @ i @ v @ r @@ swel @ ez @ is @en @ 0 @is 90 ° C. 5.) Verfahren zur Herstellung von N-mono-substituierten Harnstoffen gemäß Anspruch 4.), dadurch gekennzeichnet, daß man @ie Hydrochloride der Amine mit Alkali- oder Erdalkali-Salzen der Cyansäure behandelt,5.) Process for the production of N-mono-substituted ureas according to claim 4), characterized in that @ie hydrochlorides of amines treated with alkali or alkaline earth salts of cyanic acid,
DE19691908047 1969-02-18 1969-02-18 Continuous fine rolling Pending DE1908047A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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Application Number Priority Date Filing Date Title
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Publications (1)

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DE1908047A1 true DE1908047A1 (en) 1970-09-10

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3928566A1 (en) * 1989-08-29 1991-03-07 Chemie Linz Deutschland Unsymmetrically-substd. urea(s) prepn. - by reaction of prim. or sec. amine with substd. ammonium isocyanate in inert diluent
DE3928595A1 (en) * 1989-08-29 1991-03-07 Chemie Linz Deutschland Asymmetrically substd. urea(s) prodn. - by passing prim. or sec. amine into hot gaseous mixt. of isocyanic acid and ammonia and cooling reaction mixt. to condense prod.
US5043444A (en) * 1989-07-28 1991-08-27 Chemie Linz Gesellschaft M.B.H. Process for the preparation of asymmetrically substituted ureas
US5248755A (en) * 1989-07-28 1993-09-28 Chemie Linz Gesellschaft M.B.H. Process for the preparation of asymmetrically substituted ureas, carbamates or thiocarbamates

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5043444A (en) * 1989-07-28 1991-08-27 Chemie Linz Gesellschaft M.B.H. Process for the preparation of asymmetrically substituted ureas
US5248755A (en) * 1989-07-28 1993-09-28 Chemie Linz Gesellschaft M.B.H. Process for the preparation of asymmetrically substituted ureas, carbamates or thiocarbamates
US5481035A (en) * 1989-07-28 1996-01-02 Chemie Linz Gesellschaft M.B.H. Process for the preparation of asymmetrically substituted ureas, carbamates, thiocarbamates and substituted isocyanates
DE3928566A1 (en) * 1989-08-29 1991-03-07 Chemie Linz Deutschland Unsymmetrically-substd. urea(s) prepn. - by reaction of prim. or sec. amine with substd. ammonium isocyanate in inert diluent
DE3928595A1 (en) * 1989-08-29 1991-03-07 Chemie Linz Deutschland Asymmetrically substd. urea(s) prodn. - by passing prim. or sec. amine into hot gaseous mixt. of isocyanic acid and ammonia and cooling reaction mixt. to condense prod.

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