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DE2643303A1 - HYPOGLYKAEMICALLY ACTIVE DRUG - Google Patents

HYPOGLYKAEMICALLY ACTIVE DRUG

Info

Publication number
DE2643303A1
DE2643303A1 DE19762643303 DE2643303A DE2643303A1 DE 2643303 A1 DE2643303 A1 DE 2643303A1 DE 19762643303 DE19762643303 DE 19762643303 DE 2643303 A DE2643303 A DE 2643303A DE 2643303 A1 DE2643303 A1 DE 2643303A1
Authority
DE
Germany
Prior art keywords
pehp
pyruvic acid
compound
hypoglykaemically
active drug
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.)
Withdrawn
Application number
DE19762643303
Other languages
German (de)
Inventor
Rainer Prof Dr Haeckel
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.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
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 Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Priority to DE19762643303 priority Critical patent/DE2643303A1/en
Priority to CA285,770A priority patent/CA1106389A/en
Priority to PH20220A priority patent/PH14931A/en
Priority to GB38889/77A priority patent/GB1530848A/en
Priority to FI772743A priority patent/FI66844C/en
Priority to HU77BO1682A priority patent/HU176064B/en
Priority to BG037375A priority patent/BG28044A3/en
Priority to CS776087A priority patent/CS194185B2/en
Priority to YU02224/77A priority patent/YU222477A/en
Priority to NLAANVRAGE7710292,A priority patent/NL180661C/en
Priority to IL52966A priority patent/IL52966A/en
Priority to AR269262A priority patent/AR214338A1/en
Priority to PL1977200962A priority patent/PL106525B1/en
Priority to CH1156377A priority patent/CH635314A5/en
Priority to ZA00775641A priority patent/ZA775641B/en
Priority to SE7710577A priority patent/SE440904B/en
Priority to NZ185234A priority patent/NZ185234A/en
Priority to IT27853/77A priority patent/IT1086373B/en
Priority to US05/835,939 priority patent/US4136196A/en
Priority to PT67068A priority patent/PT67068B/en
Priority to JP11449677A priority patent/JPS5340727A/en
Priority to LU78161A priority patent/LU78161A1/xx
Priority to DK419377A priority patent/DK146719C/en
Priority to IE1947/77A priority patent/IE45693B1/en
Priority to SU772524850A priority patent/SU719493A3/en
Priority to DD7700201181A priority patent/DD132784A5/en
Priority to AT682677A priority patent/AT351015B/en
Priority to BE181144A priority patent/BE858987A/en
Priority to ES462599A priority patent/ES462599A1/en
Priority to FR7728698A priority patent/FR2365555A1/en
Publication of DE2643303A1 publication Critical patent/DE2643303A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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

Landscapes

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

Description

Die vorliegende Erfindung betrifft ein neues Arzneimittel mit blutzuckersenkender Wirkung.The present invention relates to a new medicament having a blood sugar lowering effect.

Aus der Literatur (1, 2) ist bekannt, dass Phenyläthylhydrazin (Phenelzin) die blutzuckersenkende Wirkung von Insulin unterstützt. Es wurde vorgeschlagen, diese Substanz zur Behandlung des Diabetes mellitus in der Humanmedizin einzusetzen. Phenelzin ist außerdem ein Inhibitor der Monoaminooxidase und wurde als solcher ursprünglich in die Therapie von psychiatrischen Erkrankungen (3) eingeführt.It is known from literature (1, 2) that phenylethylhydrazine (phenelzine) supports the blood sugar-lowering effect of insulin. It has been proposed to use this substance for the treatment of diabetes mellitus in human medicine. Phenelzine is also an inhibitor of monoamine oxidase and was originally introduced as such in the treatment of psychiatric diseases (3).

Die vorliegende Erfindung betrifft nun das Hydrazon von Phenyläthylhydrazin mit Brenztraubensäure. Die Phenyläthylhydrazono-brenztraubensäure (im folgenden als PEHP bezeichnet) wurde bisher noch nicht beschrieben.The present invention now relates to the hydrazone of phenylethylhydrazine with pyruvic acid. Phenylethylhydrazono-pyruvic acid (hereinafter referred to as PEHP) has not yet been described.

Darstellung von PEHP:Representation of PEHP:

1. Phenelzin, 4 mmol/l in 10 ml bidest. Wasser lösen.1. Phenelzine, 4 mmol / l in 10 ml redist. Dissolve water.

2. Natriumpyruvat, 4 mmol in 10 ml bidest. Wasser lösen.2. Sodium pyruvate, 4 mmol in 10 ml redist. Dissolve water.

3. Beide Lösungen zusammengießen. Im Kühlschrank etwa 4 Stunden stehen lassen bis sich weiße Kristalle gebildet haben. Zentrifugieren und Überstand abgießen.3. Pour both solutions together. Let stand in the refrigerator for about 4 hours until white crystals have formed. Centrifuge and pour off the supernatant.

4. Kristalle in etwa 20 ml Äthylalkohol aufnehmen. Es entsteht eine kolloidale Lösung. 15 ml bidest. Wasser hinzugeben und mit einem Glasstab kräftig an der Glaswand reiben bis sich Kristalle bilden. Lösung noch etwa 4 Stunden stehen lassen und danach filtrieren (Selecta-Faltenfilter).4. Absorb the crystals in about 20 ml of ethyl alcohol. A colloidal solution is created. 15 ml redist. Add water and rub vigorously on the glass wall with a glass rod until crystals form. Let the solution stand for another 4 hours and then filter (Selecta folded filter).

5. Substanz auf dem Faltenfilter an der Luft trocknen lassen.5. Let the substance air dry on the folded filter.

6. Punkt 4 und 5 wiederholen.6. Repeat points 4 and 5.

Charakterisierung von PEHP:Characterization of PEHP:

Weiße Kristalle, nadelförmigWhite crystals, needle-shaped

im leicht alkalischen Milieu gut wasserlöslichEasily soluble in water in a slightly alkaline medium

Infrarot-Spektrum: charakteristische Banden bei 3,0, 6,0, 6,9, 7,3, 7,4, 8,5, 11,8, 12,0, 13,4, 14,2, 20,0 micron.Infrared spectrum: characteristic bands at 3.0, 6.0, 6.9, 7.3, 7.4, 8.5, 11.8, 12.0, 13.4, 14.2, 20.0 micron.

Schmelzpunkt: 65,5°CMelting point: 65.5 ° C

Pharmakologische Wirkungen:Pharmacological effects:

PEHP hat folgende pharmakologische Wirkungen beim Meerschweinchen gezeigt:PEHP has shown the following pharmacological effects in guinea pigs:

1. PEHP senkt den Blutzuckerspiegel bei 48 Stunden gefasteten Meerschweinchen von 5,29 mmol/l (= Mittelwert aus 14 Beobachtungen, Standardabweichung = 0,47) nach etwa 3 Stunden signifikant auf 2,81 mmol/l (= Mittelwert aus 11 Beobachtungen, Standardabweichung = 0,98) mit einer Konzentration von 30 mg/kg Körpergewicht intraperitoneal injiziert.1. PEHP significantly reduces the blood sugar level in guinea pigs fasted for 48 hours from 5.29 mmol / l (= mean value from 14 observations, standard deviation = 0.47) after about 3 hours to 2.81 mmol / l (= mean value from 11 observations, Standard deviation = 0.98) with a concentration of 30 mg / kg body weight injected intraperitoneally.

2. PEHP wirkt auch per oral.2. PEHP also works orally.

3. PEHP hemmt die Glucosebildung der Leber, ähnlich wie Phenelzin, jedoch mit einer 10-fach niedrigeren Konzentration. Versuche mit der isoliert perfundierten Meerschweinchenleber zeigten, dass die Glucoseneubildung aus Lactat und Pyruvat gehemmt werden. Ein toxischer Effekt auf den Leberstoffwechsel konnte dabei nicht beobachtet werden. Der ATP/ADP Quotient, ein empfindlicher Indikator für die oxidative Phosphorylierung, d.h. für den Energiestoffwechsel der Zelle, wird nicht beeinflusst.3. PEHP inhibits glucose production in the liver, similar to phenelzine, but at a 10-fold lower concentration. Experiments with the isolated perfused guinea pig liver showed that the formation of new glucose from lactate and pyruvate is inhibited. A toxic effect on the liver metabolism could not be observed. The ATP / ADP quotient, a sensitive indicator for oxidative phosphorylation, i.e. for the energy metabolism of the cell, is not influenced.

4. Der Lactat/Pyruvat- und 3-Hydroxybutyrat/Acetoacetat Quotient werden weder in der Leberzelle noch im Blut erhöht. Ein Anstieg dieser Quotienten würde eine Hemmung der Zellatmung bedeuten.4. The lactate / pyruvate and 3-hydroxybutyrate / acetoacetate quotient are neither increased in the liver cells nor in the blood. An increase in these quotients would mean an inhibition of cell respiration.

5. Die Aktivitäten der hepotischen Monoaminooxidase wird bis zu einer Konzentration von 50 µmol/l PEHP nicht beeinflusst.5. The activity of the hepotic monoamine oxidase is not influenced up to a concentration of 50 µmol / l PEHP.

Phenelzin bewirkt bei dieser Konzentration bereits eine vollständige Hemmung des Enzyms. Testprinzip nach Ref. 4.Phenelzine already causes complete inhibition of the enzyme at this concentration. Test principle according to Ref. 4.

6. Phenelzin senkt die Konzentration von 3-Hydroxybutyrat und Acetoacetat (Ketonkörper) im Blut.6. Phenelzine lowers the levels of 3-hydroxybutyrate and acetoacetate (ketone bodies) in the blood.

Andere Derivate der Brenztraubensäure, die zur Hydrazonbildung mit Phenyläthylhydrazin fähig sind, wie Amide, Methylester und Äthylester entfalten die gleichen pharmakologischen Wirkungen wie PEHP.Other derivatives of pyruvic acid which are capable of hydrazone formation with phenylethylhydrazine, such as amides, methyl esters and ethyl esters, display the same pharmacological effects as PEHP.

Vorteile von PEHP gegenüber vergleichbaren Substanzen:Advantages of PEHP compared to comparable substances:

1. Gegenüber Phenelzin hat PEHP folgende Vorteile bezüglich der Verwendung als Diabetestherapeutikum:1. Compared to phenelzine, PEHP has the following advantages in terms of its use as a diabetes therapeutic:

1.1 Etwa 5-mal empfindlicher inbezug auf die blutzuckersenkende Wirkung,1.1 About 5 times more sensitive to the blood sugar lowering effect,

1.2 Geringere Hemmwirkung auf die Monoaminooxidase. Phenelzin ist ein sehr empfindlicher Hemmstoff der Monoaminooxidase, was zu unerwünschten Nebenwirkungen bei der Diabetestherapie führt. Daher hat sich diese Substanz auch nicht in der Diabetestherapie durchsetzen können.1.2 Less inhibitory effect on monoamine oxidase. Phenelzine is a very sensitive inhibitor of monoamine oxidase, which leads to undesirable side effects in diabetes therapy. Therefore, this substance has not been able to establish itself in diabetes therapy.

1.3 Senkung der Ketonkörperkonzentration im Blut. Diese Eigenschaft des PEHP ist insofern von Vorteil, als diese Substanzen beim Diabetes mellitus oft ansteigen und zur sogenannten Ketoazidose führen.1.3 Lowering the concentration of ketone bodies in the blood. This property of PEHP is advantageous insofar as these substances often increase in diabetes mellitus and lead to so-called ketoacidosis.

2. Vorteile gegenüber Insulin: PEHP ist oral anwendbar.2. Advantages over insulin: PEHP can be used orally.

3. Vorteile gegenüber Sulfonylharnstoff-Derivaten, die in der oralen Diabetestherapie eingesetzt werden: PEHP ist unabhängig von der Insulinsekretion der Bauchspeicheldrüse.3. Advantages over sulfonylurea derivatives, which are used in oral diabetes therapy: PEHP is independent of the insulin secretion of the pancreas.

4. Vorteile gegenüber Biguaniden, die ebenfalls in der oralen Diabetestherapie eingesetzt werden:4. Advantages over biguanides, which are also used in oral diabetes therapy:

4.1 wie 1.34.1 like 1.3

4.2 Biguanide können unter bestimmten Umständen (z.B. bei Niereninsuffizienz) zu einer Hemmung der oxidativen Phosphorylierung und der intracellulären Atmung führen. Dadurch werden schwere Lactacidosen mit einem Anstieg des Lactat/Pyruvat-Quotienten hervorgerufen, die meistens tödlich verlaufen. Diese Effekte haben die Biguanidtherapie in letzter Zeit zunehmend in Misskredit gebracht.4.2 Biguanides can, under certain circumstances (e.g. renal insufficiency), inhibit oxidative phosphorylation and intracellular respiration. This causes severe lactic acidoses with an increase in the lactate / pyruvate ratio, which are usually fatal. These effects have recently brought biguanide therapy into disrepute.

PEHP kann zwar wegen der Hemmung der Glucoseneubildung in der Leber ebenfalls zu einem leichten Lactatanstieg im Blut führen. Dieser ist aber ungefährlich, da gleichzeitig die oxidativen Prozesse nicht beeinflusst werden. Nach Huckabee (5) ist nämlich nur der Lactatanstieg gefährlich, der gleichzeitig mit einem Abfall der Pyruvatkonzentration verbunden ist (daher: Anstieg des Lactat/Pyruvat Quotienten). Bei PEHP steigen Lactat und Pyruvat an, sodass der Lactat/Pyruvat Quotient konstant bleibt.PEHP can also lead to a slight increase in lactate in the blood because of the inhibition of the formation of new glucose in the liver. However, this is not dangerous because the oxidative processes are not influenced at the same time. According to Huckabee (5), only the increase in lactate is dangerous, which is also associated with a decrease in the pyruvate concentration (hence: an increase in the lactate / pyruvate quotient). With PEHP, lactate and pyruvate increase so that the lactate / pyruvate quotient remains constant.

Literaturliterature

1. Adnitt, P.I.: Hypoglycemic action of monoamino oxidase inhibitors. Diabetes 17: 628 - 633 (1968).1. Adnitt, P.I .: Hypoglycemic action of monoamino oxidase inhibitors. Diabetes 17: 628-633 (1968).

2. Wickström, L., Petterson, K.: Treatment of diabetes with monoamino oxidase inhibitors. Lancet 2: 995 - 997 (1964).2. Wickström, L., Petterson, K .: Treatment of diabetes with monoamino oxidase inhibitors. Lancet 2: 995-997 (1964).

3. Van Praag, H.H., Leijnse, B.: The influence of some antidepressant drugs of the hydrazine type on the glucose metabolism in depressed patients. Clin.Chim.Acta S: 466 - 475 (1963).3. Van Praag, H.H., Leijnse, B .: The influence of some antidepressant drugs of the hydrazine type on the glucose metabolism in depressed patients. Clin. Chim. Acta S: 466-475 (1963).

4.4th


<NichtLesbar>
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5. Huckabee, W.E.: Hyperlactatemia. Helvetica Medica Acta 35: 363 - 376 (1969).5. Huckabee, W.E .: Hyperlactatemia. Helvetica Medica Acta 35: 363-376 (1969).

Claims (3)

1. Beansprucht wird der Patentschutz für ein neues Arzneimittel, bestehend aus einer Verbindung mit der allgemeinen Formel: 1. Patent protection is claimed for a new drug consisting of a compound with the general formula: 2. Arzneimittel nach Anspruch 1, dadurch gekennzeichnet, dass es sich um eine Phenyläthylhydrazonverbindung der Brenztraubensäure oder deren Salze handelt mit der Formel oder um eine Phenyläthylhydrazinverbindung mit folgenden Derivaten der Brenztraubensäure handelt: Amide, Methylester oder Äthylester der Brenztraubensäure.2. Medicament according to claim 1, characterized in that it is a phenylethylhydrazone compound of pyruvic acid or its salts with the formula or a phenylethylhydrazine compound with the following derivatives of pyruvic acid: amides, methyl esters or ethyl esters of pyruvic acid. 3. Arzneimittel nach Anspruch 1, dadurch gekennzeichnet, dass es zur Blutzuckersenkung verwendet werden kann, entweder intraperitoneal als Lösung injiziert mit einer Dosierung von 5-30 mg/kg Körpergewicht oder per oral verabreicht in Tabletten-, Kapsel- oder gelöster Form mit einer Dosierung von 10-50 mg/kg Körpergewicht.3. Medicament according to claim 1, characterized in that it can be used to lower blood sugar, either injected intraperitoneally as a solution with a dosage of 5-30 mg / kg body weight or administered orally in tablet, capsule or dissolved form with a dosage from 10-50 mg / kg body weight.
DE19762643303 1976-09-25 1976-09-25 HYPOGLYKAEMICALLY ACTIVE DRUG Withdrawn DE2643303A1 (en)

Priority Applications (30)

Application Number Priority Date Filing Date Title
DE19762643303 DE2643303A1 (en) 1976-09-25 1976-09-25 HYPOGLYKAEMICALLY ACTIVE DRUG
CA285,770A CA1106389A (en) 1976-09-25 1977-08-30 2-(phenylalkylhydrazono)-propionic acid derivatives and the preparation thereof
PH20220A PH14931A (en) 1976-09-25 1977-09-12 2-(phenylaleylhydrazono)-propionic acid derivatives
GB38889/77A GB1530848A (en) 1976-09-25 1977-09-19 2-(phenylalkylhydrazono)-propionic acid derivatives
FI772743A FI66844C (en) 1976-09-25 1977-09-19 FOERFARANDE FOER FRAMSTAELLNING AV SAOSOM LAEKEMEDEL ANVAENDBARA 2- (PHENYLALKYLHYDRAZONO) -PROPIONSYRADERIVAT
HU77BO1682A HU176064B (en) 1976-09-25 1977-09-19 Process for preparing 2-/phenyl-alkyl-hydrazono/-propionic acid derivatives
BG037375A BG28044A3 (en) 1976-09-25 1977-09-20 Method of obtaining of derivatives of 2- (phenylalkylhidrazono)- propionic acid
CS776087A CS194185B2 (en) 1976-09-25 1977-09-20 Method of producing derivatives of 2-/phenylalkylhydrazono/propionic acid
YU02224/77A YU222477A (en) 1976-09-25 1977-09-20 Process for preparing 2-(phenyl-alkylhydrazino)-propionic acid derivatives
NLAANVRAGE7710292,A NL180661C (en) 1976-09-25 1977-09-20 METHOD FOR THE PREPARATION OF MEDICINAL PRODUCTS, OBJECTS AND HYDRAZINE DERIVATIVES WITH BLOOD SUGAR MIRROR-LOWERING ACTION
IL52966A IL52966A (en) 1976-09-25 1977-09-20 2-(phenylalkylhydrazono)-propionic acid derivatives,process for their preparation and pharmaceutical compositions containing the same
AR269262A AR214338A1 (en) 1976-09-25 1977-09-20 A PROCEDURE FOR PREPARING DERIVATIVES OF 2- (PHENYLALKYL HYDRAZONE) -PROPIONIC ACID
PL1977200962A PL106525B1 (en) 1976-09-25 1977-09-20 METHOD OF PRODUCTION OF NEW DERIVATIVES OF 2- / PHENYLALKYLHYDRAGONO / PROPIONIC ACID
CH1156377A CH635314A5 (en) 1976-09-25 1977-09-21 METHOD FOR PRODUCING 2- (PHENYLALKYLHYDRAZONO) PROPIONIC ACID DERIVATIVES.
ZA00775641A ZA775641B (en) 1976-09-25 1977-09-21 New 2-(phenylalkylhydrazono)-propionic acid derivatives and the preparation thereof
SE7710577A SE440904B (en) 1976-09-25 1977-09-21 PROCEDURE FOR THE PREPARATION OF 2- (PHENYLALKYL HYDRAZONO) -PROPIONIC ACID DERIVATIVES
NZ185234A NZ185234A (en) 1976-09-25 1977-09-22 (phenylalkylhydrazono)-propionic acid derivatives, and pharmaceutical compositions
IT27853/77A IT1086373B (en) 1976-09-25 1977-09-22 ACID DERIVATIVES 2- (PHENYLALKYL HYDRAZONE) -PROPIONICS, PROCESS FOR THEIR PREPARATION AND DRUGS THAT CONTAIN THEM
US05/835,939 US4136196A (en) 1976-09-25 1977-09-22 Hypoglycaemically active 2-(phenylalkyl- or -alkenyl hydrazono)-propionic acid derivatives
PT67068A PT67068B (en) 1976-09-25 1977-09-22 2- (PHENYL ALKYLHYDRAZONO) -PROPIONSAUREDERIVATE PROCESS FOR PREPARING THE SAME AND MEDICAMENTS CONTAINING THEM
JP11449677A JPS5340727A (en) 1976-09-25 1977-09-22 22*phenylalkylhydrazono**propionic acid derivative* preparation thereof and blood sugar depressant
LU78161A LU78161A1 (en) 1976-09-25 1977-09-22
DK419377A DK146719C (en) 1976-09-25 1977-09-22 ANALOGY PROCEDURE FOR PREPARING 2- (PHENYLALKYL HYDRAZONE) -PROPIONIC ACID DERIVATIVES
IE1947/77A IE45693B1 (en) 1976-09-25 1977-09-23 2-(phenylalkylhydrazono)-propionic acid derivatives
SU772524850A SU719493A3 (en) 1976-09-25 1977-09-23 Method of preparing 2-(arylalkylhydrazono)-propionic acid or its derivatives
DD7700201181A DD132784A5 (en) 1976-09-25 1977-09-23 PROCESS FOR THE PREPARATION OF 2- (PHENYL ALKYLHYDRAZONO) -PROPIONSAEUREDERIVATES
AT682677A AT351015B (en) 1976-09-25 1977-09-23 PROCESS FOR THE PREPARATION OF NEW 2- (PHENYL- ALKYL- OR -ALKENYLHYDRAZONO) -PROPIONIC ACIDS AND OF THEIR SALT, ESTERS AND AMIDES
BE181144A BE858987A (en) 1976-09-25 1977-09-23 2- (PHENYL-ALCOYL-HYDRAZONO) -PROPIONIC ACID DERIVATIVES WITH HYPOGLYCEMATING ACTION AND PROCESS FOR THEIR PREPARATION
ES462599A ES462599A1 (en) 1976-09-25 1977-09-23 Hypoglycaemically active 2-(phenylalkyl- or -alkenyl hydrazono)-propionic acid derivatives
FR7728698A FR2365555A1 (en) 1976-09-25 1977-09-23 2- (PHENYLALKYLHYDRAZONO) -PROPIONIC ACID DERIVATIVES, PROCESS FOR THEIR PREPARATION AND MEDICINAL PRODUCTS CONTAINING SUCH BODIES

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762643303 DE2643303A1 (en) 1976-09-25 1976-09-25 HYPOGLYKAEMICALLY ACTIVE DRUG

Publications (1)

Publication Number Publication Date
DE2643303A1 true DE2643303A1 (en) 1978-03-30

Family

ID=5988884

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19762643303 Withdrawn DE2643303A1 (en) 1976-09-25 1976-09-25 HYPOGLYKAEMICALLY ACTIVE DRUG

Country Status (4)

Country Link
BE (1) BE858987A (en)
DE (1) DE2643303A1 (en)
GB (1) GB1530848A (en)
ZA (1) ZA775641B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2726210A1 (en) * 1977-06-10 1978-12-21 Boehringer Mannheim Gmbh Hypoglycaemic 2-phenylalkyl-hydrazono-propionic acid derivs. - with minimal mono:amine oxidase inhibitory activity
EP0001144A1 (en) * 1977-09-01 1979-03-21 Roche Diagnostics GmbH N-substituted 2-hydrazono-propionic acid derivatives, process for their preparation and pharmaceutical compositions containing them
EP0046554A1 (en) * 1980-08-23 1982-03-03 Roche Diagnostics GmbH N-Substituted pyruvic-acid hydrazones, processes for their preparation and medicaments containing these compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2726210A1 (en) * 1977-06-10 1978-12-21 Boehringer Mannheim Gmbh Hypoglycaemic 2-phenylalkyl-hydrazono-propionic acid derivs. - with minimal mono:amine oxidase inhibitory activity
EP0001144A1 (en) * 1977-09-01 1979-03-21 Roche Diagnostics GmbH N-substituted 2-hydrazono-propionic acid derivatives, process for their preparation and pharmaceutical compositions containing them
EP0046554A1 (en) * 1980-08-23 1982-03-03 Roche Diagnostics GmbH N-Substituted pyruvic-acid hydrazones, processes for their preparation and medicaments containing these compounds

Also Published As

Publication number Publication date
ZA775641B (en) 1978-09-27
BE858987A (en) 1978-03-23
GB1530848A (en) 1978-11-01

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