DE1543522B2 - ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS - Google Patents

ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS

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Publication number
DE1543522B2
DE1543522B2 DE1966D0050562 DED0050562A DE1543522B2 DE 1543522 B2 DE1543522 B2 DE 1543522B2 DE 1966D0050562 DE1966D0050562 DE 1966D0050562 DE D0050562 A DED0050562 A DE D0050562A DE 1543522 B2 DE1543522 B2 DE 1543522B2
Authority
DE
Germany
Prior art keywords
acylaminophenol
alcanols
manufacturing
pharmaceutical agents
hydroxyphenyl
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.)
Granted
Application number
DE1966D0050562
Other languages
German (de)
Other versions
DE1543522A1 (en
Inventor
Gerhard Dr.-Ing.; Credner Karl Dr.med.;Kretzschmar Ulrich Dr.-Ing.; 1000 Berlin Renwanz
Original Assignee
Gödecke AG, 1000 Berlin
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 Gödecke AG, 1000 Berlin filed Critical Gödecke AG, 1000 Berlin
Priority to DE1966D0050562 priority Critical patent/DE1543522B2/en
Priority to DE19671593828 priority patent/DE1593828A1/en
Priority to DE19671593834 priority patent/DE1593834A1/en
Priority to CH829367A priority patent/CH523224A/en
Priority to AT560267A priority patent/AT273932B/en
Priority to SE904267A priority patent/SE335541B/xx
Priority to DK358267A priority patent/DK125198B/en
Priority to GB3211867A priority patent/GB1137596A/en
Priority to ES343008A priority patent/ES343008A1/en
Priority to FR114197A priority patent/FR1537803A/en
Priority to NL6709789A priority patent/NL6709789A/xx
Publication of DE1543522A1 publication Critical patent/DE1543522A1/en
Publication of DE1543522B2 publication Critical patent/DE1543522B2/en
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Description

in der R Wasserstoff oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen und .Ac den Acylrest einer aliphatischen, gesättigten Monocarbonsäure mit bis zu 4 Kohlenstoffatomen bedeutet.in which R is hydrogen or an alkyl group having 1 to 4 carbon atoms and .Ac is the acyl radical of a means aliphatic, saturated monocarboxylic acid with up to 4 carbon atoms.

2. Verfahren zur Herstellung der Acylaminophenolalkanole gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Amin der allgemeinen Formel2. Process for the preparation of the acylaminophenol alkanols according to Claim 1, characterized in that that one is an amine of the general formula

HOHO

CHOH-CH-NH2
R CHOH-CH-NH 2
R.

(H)(H)

wobei R die in Anspruch 1 angegebene Bedeutung hat, oder dessen Säureadditionssalz in an sich bekannter Weise mit einer aliphatischen, gesättigten Monocarbonsäure mit bis zu 4 Kohlenstoffatomen im Molekül oder einem reaktionsfähiges Derivat davon umsetzt.where R has the meaning given in claim 1, or its acid addition salt per se known way with an aliphatic, saturated monocarboxylic acid with up to 4 carbon atoms in the molecule or a reactive derivative thereof.

' 3. Pharmazeutisches Mittel, enthaltend eine Verbindung gemäß Anspruch 1 neben üblichem Fülloder Trägermaterial. '3. A pharmaceutical composition comprising a compound according to claim 1 in addition to customary fillers or carrier material.

Die Erfindung betrifft Acylaminophenolalkanole der allgemeinen FormelThe invention relates to acylaminophenol alkanols of the general formula

HOHO

CH-CH- NH-Ac (I)
OH RCH-CH- NH-Ac (I)
EAR

in der R Wasserstoff oder eine Alkylgruppe mit 1 bis Kohlenstoffatomen und Ac den Acylrest einer aliphatischen, gesättigten Monocarbonsäure mit bis zu Kohlenstoffatomen bedeutet.in which R is hydrogen or an alkyl group having 1 to carbon atoms and Ac is the acyl radical aliphatic, saturated monocarboxylic acid with up to carbon atoms means.

Es ist bekannt, daß therapeutisch wirksame Hydroxyphenylalkanolamine im Organismus ziemlich schnell zu unwirksamen Verbindungen abgebaut werden. In vielen Fällen ist der rasche Abbau erwünscht. Es gibt aber Kreislauferkrankungen, die einer Therapie mit weniger schnell abklingenden Pharmaka bedürfen.It is known that therapeutically effective hydroxyphenylalkanolamines are broken down into ineffective compounds fairly quickly in the organism. In many In some cases, rapid dismantling is desirable. But there are circulatory diseases that require therapy with less require rapidly decaying pharmaceuticals.

Es wurde nun gefunden, daß die Verbindungen gemäß Patentanspruch 1 für eine solche Therapie hervorragend geeignet sind. So ist z. B. das N-Acetyl-l-(3'-hydroxyphenyl)-2-aminoäthanol zwar im Tierversuch an der Katze oral und parenteral im Gegensatz zu l-(3'-Hydroxyphenyl)-2-aminoäthanol praktisch nicht pressorisch wirksam. Es war daher überraschend, daß N-Acetyl-1-(3'-hydroxyphenyl)-2-aminoäthanol im Schellongtest am Menschen nach oraler Gabe bestimmte hypotone Zustände sehr günstig beeinflußte; therapieresistende Hypotoniker ließen schon 24 bis 36 Stunden nach Beginn der Behandlung eine Kreislaufstabilisierung erkennen. ' . ■It has now been found that the compounds according to claim 1 are excellent for such a therapy are suitable. So is z. B. N-acetyl-1- (3'-hydroxyphenyl) -2-aminoethanol in animal experiments on cats orally and parenterally in contrast to l- (3'-hydroxyphenyl) -2-aminoethanol practically not effective in terms of pressure. It was therefore surprising that N-acetyl-1- (3'-hydroxyphenyl) -2-aminoethanol influenced certain hypotonic states very favorably in the Schellong test on humans after oral administration; therapy-resistant Hypotensive patients already had circulatory stabilization 24 to 36 hours after starting treatment recognize. '. ■

Von besonderem Vorteil ist, daß die Toxizität der Substanz wesentlich geringer ist als die der verwandten, nicht N-acylierten in der Therapie gebräuchlichen Sympathicomimetica.It is of particular advantage that the toxicity of the substance is significantly lower than that of the related, non-N-acylated sympathicomimetics commonly used in therapy.

Die bei hervorragender Wirkung auf den Kreislauf gegenüber bekannten Verbindungen erhöhte Vertrag-, lichkeit der erfindungsgemäßen Verbindungen bedeutet für die Therapie einen wesentlichen Fortschritt.The increased contract, Liability of the compounds according to the invention means a significant advance in therapy.

Diese Acylaminophenolalkanole der vorstehenden allgemeinen Formel (I) werden erfindungsgemäß dadurch hergestellt, daß man ein Amin der allgemeinen FormelThese acylaminophenol alkanols represented by the above general formula (I) are used in the present invention prepared by using an amine of the general formula

HOHO

CHOH-CH-NH2 (11)CHOH-CH-NH 2 (11)

wobei R die vorstehend angegebene Bedeutung hat oder dessen Säureadditionssalz in an sich bekannter Weise mit einer aliphatischen, gesättigten Monocarbonsäure mit bis zu 4 Kohlenstoffatomen im Molekül oder einem reaktionsfähigen Derivat davon umsetzt.where R has the meaning given above or its acid addition salt is known per se Way with an aliphatic, saturated monocarboxylic acid with up to 4 carbon atoms in the molecule or a reactive derivative thereof.

Zu den erfindungsgemäß umzusetzenden Aminen gehört beispielsweise l-(3'-Hydroxyphenyl)-2-aminoäthanol. Als reaktionsfähiges Derivat der aliphatischen, gesättigten Monocarbonsäure kann man beispielsweise ein Säurehalogenid, wie Acetyl-, Butyryl- oder Propionylbromid, ein Anhydrid, wie beispielsweise Essigsäureanhydrid, oder einen Ester, wie beispielsweise Propionsäuremethyl- bzw. -äthylester, verwenden.The amines to be reacted according to the invention include, for example, 1- (3'-hydroxyphenyl) -2-aminoethanol. As a reactive derivative of the aliphatic, saturated monocarboxylic acid, one can, for example an acid halide such as acetyl, butyryl or propionyl bromide, an anhydride such as acetic anhydride, or an ester such as methyl or ethyl propionate, for example.

Bei der Umsetzung von Säurehalogeniden oderWhen implementing acid halides or

Anhydriden mit einem Amin der Formel .(II) oderAnhydrides with an amine of the formula. (II) or

. seinem Säureadditionssalz, wie Hydrochlorid oder -bromid, in Pyridinlösung und in der Kälte geht man zweckmäßigerweise von 1 Mol Säurehalogenid oder Anhydrid pro Mol Amin oder Aminhydrochlorid oder -bromid aus. Bei der Umsetzung von Carbonsäureestern wird zur quantitativen Umsetzung vorzugsweise ein Überschuß an Ester eingesetzt, wobei unter Rückflußbedingungen erhitzt wird. Setzt man die Amine dagegen mit Säurehalogeniden um, so ist zur Erzielung einheitlicher Reaktionsprodukte das Arbeiten mit molaren Mengen in der Kälte zweckmäßig. Die Kondensation von Aminen mit Carbonsäuren führt man vorzugsweise in inerten Lösungsmitteln durch, die mit Wasser nicht mischbar sind, und führt das gebildete Reaktionswasser durch azeotrope Destillation ab. Die Kondensation mit Hilfe von wasserabspaltenden Mitteln, wie Carbonyldiimidazol oder Cyclohexylcarbodiimid, wird in Alkoholen, Methylenchlorid, Tetrahydrofuran, Pyridin oder anderen Lösungsmitteln, gegebenenfalls bei erhöhter Temperatur, vorgenommen.. Its acid addition salt, such as hydrochloride or bromide, in pyridine solution and in the cold you go expediently from 1 mole of acid halide or anhydride per mole of amine or amine hydrochloride or -bromide from. When converting carboxylic acid esters, a quantitative conversion is preferred Excess ester is used, the mixture being heated under reflux conditions. If you put the amines against it with acid halides, then working with to achieve uniform reaction products molar amounts in the cold appropriate. The condensation of amines with carboxylic acids is carried out preferably in inert solvents, which are immiscible with water, and carries out the formed Water of reaction from by azeotropic distillation. The condensation with the help of water-releasing agents, such as carbonyldiimidazole or cyclohexylcarbodiimide, is in alcohols, methylene chloride, tetrahydrofuran, Pyridine or other solvents, optionally at elevated temperature, made.

Die Herstellung der erfindungsgemäßen Verbindungen wird in den nachstehenden Beispielen im einzelnen erläutert.The preparation of the compounds according to the invention is detailed in the examples below explained.

Beispiel 1example 1

56,9 g l-(3'-Hydroxyphenyl)-2-aminoäthanol-hydrochlorid wurden in 150 ml Pyridin gelöst und unter Rühren bei 2O0C innerhalb 2 Stunden 30,6 g Essigsäureanhydrid zugetropft. Nach Stehen über Nacht wurde zur56.9 g of l- (3'-hydroxyphenyl) -2-aminoethanol hydrochloride was dissolved in 150 ml of pyridine and added dropwise with stirring at 2O 0 C in 2 hours 30.6 g of acetic anhydride. After standing overnight it became

Trockne eingeengt, der Rückstand mit 31,8 g wasserfreier Soda und 100 ml Wasser gelöst und erneut eingedampft. Der Rückstand wurde dreimal mit 250 ml Isopropanol extrahiert; die vereinigten Extrakte ergaben nach Eindampfen 52,4 g festen Rückstand. Dieser wurde zweimal aus Isopropanol umkristallisiert und ergab 31 g (52% der Theorie) dünnschichtchromatographisch einheitliches N-Acetyl-l-(3'-hydroxyphenyl)-2-aminoäthanol vom Schmelzpunkt 118 bis 119° C.
Ci0Hi3NO3 = 195,2:Concentrated to dryness, the residue was dissolved in 31.8 g of anhydrous soda and 100 ml of water and evaporated again. The residue was extracted three times with 250 ml of isopropanol; the combined extracts gave 52.4 g of solid residue after evaporation. This was recrystallized twice from isopropanol and gave 31 g (52% of theory) N-acetyl-1- (3'-hydroxyphenyl) -2-aminoethanol with a melting point of 118 to 119 ° C., which was uniform by thin layer chromatography.
Ci 0 Hi 3 NO 3 = 195.2:

Nberechnet = 7,18%;
Ngefunden = 7,08%.Ncalculated = 7.18%;
N found = 7.08%.

Beispiel 2Example 2

'5'5

16,4 g l-(3'-Hydroxyphenyl)-2-aminoäthanol-monohydrat wurden in 35 g Propionsäurepropylester 24 Stunden unter Rückflußbedingungen gerührt. Anschließend wurde im Vakuum zur Trockne eingeengt. Der Rückstand wurde aus Isopropanol-Essigester umkristallisiert. Man erhielt 12,1 g (58% der Theorie) N-Propionyl-1 -(3'-hydroxyphenyl)-2-aminoäthanol vom Schmelzpunkt 112 bis 114° C.16.4 g of 1- (3'-hydroxyphenyl) -2-aminoethanol monohydrate were stirred under reflux conditions in 35 g of propionate for 24 hours. Afterward was concentrated to dryness in vacuo. The residue was made from isopropanol / ethyl acetate recrystallized. 12.1 g (58% of theory) of N-propionyl-1 - (3'-hydroxyphenyl) -2-aminoethanol were obtained Melting point 112 to 114 ° C.

ChHi5NO3 = 209,25:ChHi 5 NO 3 = 209.25:

Nberechnet = 6,69%;
Ngefunden = 6,68%.Ncalculated = 6.69%;
N found = 6.68%.

Beispiel 3Example 3

1,67 g l-(3'-Hydroxyphenyl)-2-aminopropanol wurden mit 20 ml Essigsäure-n-butylester 12 Stunden unter Rückflußbedingungen erhitzt. Nach Einengen zur Trockne wurden an Kieselgel mit Benzol/Methanol (4 + 1) chromatographiert. Die Hauptfraktion ist dünnschichtchromatographisch einheitlich und ergab nach Kristallisation aus Aceton/Äther 0,88 g (42% der Theorie) N-Acetyl-1 -(3'-hydroxyphenyl)-2-aminopropanol vom Schmelzpunkt 115 bis 116° C.1.67 g of l- (3'-hydroxyphenyl) -2-aminopropanol were mixed with 20 ml of n-butyl acetate for 12 hours Heated to reflux conditions. After evaporation to dryness, on silica gel with benzene / methanol (4 + 1) chromatographed. The main fraction is uniform according to thin-layer chromatography and resulted after crystallization from acetone / ether, 0.88 g (42% of theory) of N-acetyl-1 - (3'-hydroxyphenyl) -2-aminopropanol from a melting point of 115 to 116 ° C.

ChHi5NO3 = 209,3:ChHi 5 NO 3 = 209.3:

Nberechnet = 6,69%;
Ngefunden = 6,52%.Ncalculated = 6.69%;
N found = 6.52%.

Claims (1)

Patentansprüche:Patent claims: 1. Acylaminophenolalkanole der allgemeinen Formel1. Acylaminophenolalkanols of the general formula HOHO CH-CH- NH-AcCH-CH-NH-Ac l I .l I. OH REAR
DE1966D0050562 1966-07-14 1966-07-14 ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS Granted DE1543522B2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
DE1966D0050562 DE1543522B2 (en) 1966-07-14 1966-07-14 ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS
DE19671593828 DE1593828A1 (en) 1966-07-14 1967-05-16 Process for the preparation of therapeutically active acylaminophenolalkanols
DE19671593834 DE1593834A1 (en) 1966-07-14 1967-05-26 Process for the preparation of therapeutically active acylaminophenolalkanols
CH829367A CH523224A (en) 1966-07-14 1967-06-12 Acylaminophenylalkanols - used to stabilize the blood circulation
AT560267A AT273932B (en) 1966-07-14 1967-06-16 Process for the preparation of new 1- (3'-hydroxyphenyl) -2-acylaminoalkanolen- (1) and their O <1> -mono- or O, O-diacyl derivatives
SE904267A SE335541B (en) 1966-07-14 1967-06-22
DK358267A DK125198B (en) 1966-07-14 1967-07-11 Analogous process for the preparation of therapeutically effective acylaminophenol alkanols.
GB3211867A GB1137596A (en) 1966-07-14 1967-07-12 Therapeutically active acylamino-phenol-alkanols
ES343008A ES343008A1 (en) 1966-07-14 1967-07-13 Procedure for preparing acilaninofenolalcanoles. (Machine-translation by Google Translate, not legally binding)
FR114197A FR1537803A (en) 1966-07-14 1967-07-13 Process for making acylaminophenolalkanols
NL6709789A NL6709789A (en) 1966-07-14 1967-07-14

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1966D0050562 DE1543522B2 (en) 1966-07-14 1966-07-14 ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS
DED0053088 1967-05-16
DED0053177 1967-05-26

Publications (2)

Publication Number Publication Date
DE1543522A1 DE1543522A1 (en) 1969-09-04
DE1543522B2 true DE1543522B2 (en) 1976-05-06

Family

ID=27209864

Family Applications (3)

Application Number Title Priority Date Filing Date
DE1966D0050562 Granted DE1543522B2 (en) 1966-07-14 1966-07-14 ACYLAMINOPHENOL ALCANOLS, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL AGENTS CONTAINING THESE ACYLAMINOPHENOL ALCANOLS
DE19671593828 Pending DE1593828A1 (en) 1966-07-14 1967-05-16 Process for the preparation of therapeutically active acylaminophenolalkanols
DE19671593834 Pending DE1593834A1 (en) 1966-07-14 1967-05-26 Process for the preparation of therapeutically active acylaminophenolalkanols

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE19671593828 Pending DE1593828A1 (en) 1966-07-14 1967-05-16 Process for the preparation of therapeutically active acylaminophenolalkanols
DE19671593834 Pending DE1593834A1 (en) 1966-07-14 1967-05-26 Process for the preparation of therapeutically active acylaminophenolalkanols

Country Status (7)

Country Link
AT (1) AT273932B (en)
CH (1) CH523224A (en)
DE (3) DE1543522B2 (en)
DK (1) DK125198B (en)
GB (1) GB1137596A (en)
NL (1) NL6709789A (en)
SE (1) SE335541B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6210048A (en) * 1985-07-04 1987-01-19 Microbial Chem Res Found Novel physiologically active substance mh435

Also Published As

Publication number Publication date
DK125198B (en) 1973-01-15
GB1137596A (en) 1968-12-27
DE1543522A1 (en) 1969-09-04
NL6709789A (en) 1968-01-15
DE1593828A1 (en) 1970-10-29
CH523224A (en) 1972-05-31
AT273932B (en) 1969-08-25
DE1593834A1 (en) 1971-02-25
SE335541B (en) 1971-06-01

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Date Code Title Description
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