DE1966821A1 - ACYLHYDRASIDE AND ITS ACID ADDITION SALT - Google Patents

ACYLHYDRASIDE AND ITS ACID ADDITION SALT

Info

Publication number
DE1966821A1
DE1966821A1 DE19691966821 DE1966821A DE1966821A1 DE 1966821 A1 DE1966821 A1 DE 1966821A1 DE 19691966821 DE19691966821 DE 19691966821 DE 1966821 A DE1966821 A DE 1966821A DE 1966821 A1 DE1966821 A1 DE 1966821A1
Authority
DE
Germany
Prior art keywords
acid addition
acylhydraside
addition salt
hydrazide
addition salts
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
DE19691966821
Other languages
German (de)
Other versions
DE1966821C3 (en
DE1966821B2 (en
Inventor
Giuseppe Dr Bartholini
Balthasar Dr Hegedues
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of DE1966821A1 publication Critical patent/DE1966821A1/en
Publication of DE1966821B2 publication Critical patent/DE1966821B2/en
Application granted granted Critical
Publication of DE1966821C3 publication Critical patent/DE1966821C3/en
Expired 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
    • 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
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/34—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a carbon skeleton further substituted by nitrogen atoms

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

Μ 28. Jan. 197* ■ Μ Jan. 28, 197 * ■

RAN 4007/14-001RAN 4007 / 14-001

F. HoiFmann-La Roche & Co. Aktiengesellschaft, Basel/SchweizF. HoiFmann-La Roche & Co. Aktiengesellschaft, Basel / Switzerland

Acylhydrazid und dessen SäureadditionssalzeAcyl hydrazide and its acid addition salts

Die Erfindung betrifft ein neues, von L-Serin abgeleitetes Hydrazid der Formel :The invention relates to a new hydrazide derived from L-serine of the formula:

CH=N-NH-CO-CH-CH OHCH = N-NH-CO-CH-CH OH

HO OH
sowie Saureadditionssalze hiervon.HO OH
and acid addition salts thereof.

Die erfindungsgemässen Verbindungen sind Zwischenverbindungen zur Herstellung von Ν-,-L-Seryl-Np- (2,3,4-trihydroxybenzyl)-hydrazid sowie dessen Säureadditionssalzen. Die letztgenannte Verbindung weist pharmakoiogische Wirkung auf, und .zwar besitzt sie eine Decarboxylase-hernmende Wirkung, wobei von besonderem Interesse ist, dass sie in Kombination mit L-Dopa hervorragende Mittel zur Behandlung von Parkinsonismus darstellt und antidepressiv wirkt. Pur weitere Angaben hin-The compounds of the invention are intermediate compounds for the production of Ν -, - L-Seryl-Np- (2,3,4-trihydroxybenzyl) -hydrazide as well as its acid addition salts. The latter compound has a pharmacological effect, and .Although it has a decarboxylase-inhibiting effect, where Of particular interest, when combined with L-Dopa, they are excellent agents for treating Parkinsonism and has an antidepressant effect. For further information

409828/1056409828/1056

BAD OHiGiNALBAD OHiGiNAL

sichtlich der Brauchbarkeit des aus den erfindungsgemässen Zwischenverbindungen hergestellten N,-L-Seryl-N-(2,3,4-trihydroxybenzyl)-hydrazide sowie dessen Säureadditionssalzen wird auf die Patentanmeldung P 19 4l 284.1-42 verwiesen.With regard to the usefulness of the N, -L-seryl-N- (2,3,4-trihydroxybenzyl) hydrazide and its acid addition salts prepared from the intermediate compounds according to the invention, reference is made to patent application P 19 41 284.1-42.

Die erfindungsgemässe Verbindung der Formel I und deren Salze können nach an sich bekannten Methoden erhalten werden, beispielsweise durch Umsetzung eines Säureadditionssalzes-von L-Serinhydrazid mit 2,j5,4-Trihydroxy-benzaldehyd.The compound of the formula I according to the invention and their Salts can be obtained by methods known per se, for example by reacting an acid addition salt of L-serine hydrazide with 2, j5,4-trihydroxy-benzaldehyde.

Beispielexample

Herstellung von Ν,-L-Seryl-Np-(2,3,4-trihydroxy-benzyliden)-hydrazid-hyarochlorid Production of Ν, -L-Seryl-Np- (2,3,4-trihydroxy- benzylidene) -hydrazide-hyarochloride

15,4 g 2,3,4-Trihydroxybenzaldehyd werden in 200 ml siedendem Wasser gelöst und auf einmal mit 15,2 g L-Serin-hydrazidhydrpchlorid versetzt. Man erhält eine klare Lösung. Diese wird unter vermindertem Druck eingeengt und durch portionenweise Zugabe von Aethanol wird das Wasser allmählich verdrängt. Hierbei entsteht ein Kristallbrei. Dieser wird genutscht und mit Aethanol und Aether gewaschen. Man erhält das N..-L-Seryl-Np-(2,3,4-trihydroxy-benzyliden)-hydrazid-hydrochlorid vom F. = 260 - 265°C. ία] = +23° (c = 1; H2O). 15.4 g of 2,3,4-trihydroxybenzaldehyde are dissolved in 200 ml of boiling water, and 15.2 g of L-serine hydrazide hydrochloride are added all at once. A clear solution is obtained. This is concentrated under reduced pressure and the water is gradually displaced by adding ethanol in portions. This creates a crystal pulp. This is sucked and washed with ethanol and ether. The N ..- L-Seryl-N p - (2,3,4-trihydroxy-benzylidene) hydrazide hydrochloride with a melting point of 260-265 ° C. is obtained. ία] = + 23 ° (c = 1; H 2 O).

409828/ 1056409828/1056

Claims (1)

PatentanspruchClaim Vom L-Serin abgeleitetes Hydrazid der FormelHydrazide derived from L-serine of the formula HOHO -TV-TV CH=N-NH-Co-CH-CH2OH NCH = N-NH-Co-CH-CH 2 OH N HO OHHO OH sowie Säureadditionssalze hiervon.and acid addition salts thereof. 409828/1056409828/1056
DE1966821A 1968-08-16 1969-08-13 Ni.i ^ »> i-N2 - (23.4-trihydroxy-benzylidene) hydrazide and its acid addition salts Expired DE1966821C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1240368A CH554844A (en) 1968-08-16 1968-08-16 METHOD OF MANUFACTURING A HYDRAZIDE.

Publications (3)

Publication Number Publication Date
DE1966821A1 true DE1966821A1 (en) 1974-07-11
DE1966821B2 DE1966821B2 (en) 1978-03-16
DE1966821C3 DE1966821C3 (en) 1978-11-23

Family

ID=4382677

Family Applications (2)

Application Number Title Priority Date Filing Date
DE1966821A Expired DE1966821C3 (en) 1968-08-16 1969-08-13 Ni.i ^ »> i-N2 - (23.4-trihydroxy-benzylidene) hydrazide and its acid addition salts
DE1941284A Expired DE1941284C3 (en) 1968-08-16 1969-08-13 N to the power of 1-L-Seryl-N to the power of 2- (2,3,4trihydroxybenzyl) hydrazide, process for its preparation and its acid addition salts and pharmaceuticals containing them

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE1941284A Expired DE1941284C3 (en) 1968-08-16 1969-08-13 N to the power of 1-L-Seryl-N to the power of 2- (2,3,4trihydroxybenzyl) hydrazide, process for its preparation and its acid addition salts and pharmaceuticals containing them

Country Status (16)

Country Link
JP (1) JPS5114501B1 (en)
AT (2) AT299158B (en)
BE (1) BE737420A (en)
CA (1) CA958418A (en)
CH (1) CH554844A (en)
CS (1) CS162689B2 (en)
DE (2) DE1966821C3 (en)
DK (1) DK126776B (en)
ES (1) ES370500A1 (en)
FR (2) FR2015792B1 (en)
GB (1) GB1250279A (en)
IE (1) IE33519B1 (en)
IL (1) IL32767A (en)
MY (1) MY7300018A (en)
NL (1) NL6912320A (en)
SE (1) SE378242B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103951587A (en) * 2014-04-11 2014-07-30 浙江耐司康药业有限公司 Synthetic method for intermediate of benserazide hydrochloride
WO2015197909A1 (en) 2014-06-27 2015-12-30 Fermion Oy Process for the preparation of a crystalline polymorph of 2-amino-3-hydroxy-n'-(2,3,4-trihydroxybenzyl)propanehydrazide (benserazide) hydrochloride

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065265A (en) * 1957-07-04 1962-11-20 Hoffmann La Roche Amino acid hydrazides

Also Published As

Publication number Publication date
CH554844A (en) 1974-10-15
GB1250279A (en) 1971-10-20
IL32767A0 (en) 1969-11-12
IL32767A (en) 1973-01-30
AT299160B (en) 1972-06-12
DE1941284A1 (en) 1970-02-19
DE1941284B2 (en) 1974-05-30
FR2015792B1 (en) 1973-08-10
AT299158B (en) 1972-06-12
SE378242B (en) 1975-08-25
BE737420A (en) 1970-02-13
NL6912320A (en) 1970-02-18
DK126776B (en) 1973-08-20
JPS5114501B1 (en) 1976-05-10
DE1941284C3 (en) 1975-01-30
ES370500A1 (en) 1971-04-16
CS162689B2 (en) 1975-07-15
FR2104722A1 (en) 1972-04-21
IE33519L (en) 1970-02-16
DE1966821C3 (en) 1978-11-23
MY7300018A (en) 1973-12-31
IE33519B1 (en) 1974-07-24
FR2015792A1 (en) 1970-04-30
FR2104722B1 (en) 1974-03-22
DE1966821B2 (en) 1978-03-16
CA958418A (en) 1974-11-26

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Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)
8339 Ceased/non-payment of the annual fee