DE2641378A1 - NEW ORGANIC COMPOUNDS, THEIR USE AND PRODUCTION - Google Patents

NEW ORGANIC COMPOUNDS, THEIR USE AND PRODUCTION

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Publication number
DE2641378A1
DE2641378A1 DE19762641378 DE2641378A DE2641378A1 DE 2641378 A1 DE2641378 A1 DE 2641378A1 DE 19762641378 DE19762641378 DE 19762641378 DE 2641378 A DE2641378 A DE 2641378A DE 2641378 A1 DE2641378 A1 DE 2641378A1
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Germany
Prior art keywords
carbon atoms
compounds
formula
alkyl
hydroxyalkyl
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.)
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DE19762641378
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German (de)
Inventor
Fritz Dr Hunziker
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Sandoz AG
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Sandoz AG
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Filing date
Publication date
Priority claimed from CH1241375A external-priority patent/CH599196A5/en
Priority claimed from CH1241475A external-priority patent/CH602709A5/en
Priority claimed from CH725076A external-priority patent/CH602708A5/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of DE2641378A1 publication Critical patent/DE2641378A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, ***e

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroplating Methods And Accessories (AREA)

Description

SANDOZ-PATENT-GMBH 7850 LörrachSANDOZ-PATENT-GMBH 7850 Loerrach

Case SO0-5397Case SO0-5397

Neue organische Verbindungen, ihre Verwendung und ' Her.st.e.l.lun.g .New organic compounds, their uses and 'Her.st.e.l.lun.g.

Die vorliegende Erfindung betrifft Verbindungen der Formel I,The present invention relates to compounds of the formula I,

709814/1039709814/1039

500-5397500-5397

worin R für Wasserstoff, Alkyl mit 1-4 Kohlenstoffatomen, Hydroxyalkyl mit 2-4 Kohlenstoffatomen oder Alkoxyalkyl mit zusammen höchstens 5 Kohlenstoffatomen steht, R für Fluor oder Chlor und R für Alkyl mit 1-4 Kohlenstoffatomen, Hydroxyalkyl mit 2-4 Kohlenstoffatomen, Alkoxyalkyl mit zusammen höchstens 5 Kohlenstoffatomen oder Alkenyl mit 3-4 Kohlenstoffatomen stehen, mit der Massgabe, dass, falls R_ ' Methyl bedeutet, R-2 für Fluor steht, ihre Säureadditionssalze sowie ein Verfahren zu ihrer Herstellung.wherein R stands for hydrogen, alkyl with 1-4 carbon atoms, hydroxyalkyl with 2-4 carbon atoms or alkoxyalkyl with a maximum of 5 carbon atoms together, R for fluorine or chlorine and R for alkyl with 1-4 carbon atoms, hydroxyalkyl with 2-4 carbon atoms, alkoxyalkyl with a maximum of 5 carbon atoms or alkenyl with 3-4 carbon atoms, with the proviso that, if R_ 'denotes methyl, R -2 denotes fluorine, their acid addition salts and a process for their preparation.

Alkyl in R, besitzt vorzugsweise 1-2 Kohlenstoffatome.Alkyl in R, preferably has 1-2 carbon atoms.

,Der Alkoxyrest im Alkoxyalkyl und das Hydroxyl im Hydroxyalkyl befinden sich vorzugsweise in Endstellung der Alkylenkette und die Alkylenkette besitzt vorzugsweise 2 oder 3, insbesondere 2 Kohlenstoffatome. Der Alkoxyrest im Alkoxyalkyl bedeutet vorzugsweise Methoxy. Die Doppelbindung im Alkenyl befindet sich in 2-3 oder 3-4 Stellung. Alkenyl steht insbesondere für Allyl oder 2-Methyl-2-propenyl., The alkoxy radical in alkoxyalkyl and the hydroxyl in hydroxyalkyl are preferably in the end position of the alkylene chain and the alkylene chain preferably has 2 or 3, especially 2 carbon atoms. The alkoxy radical in alkoxyalkyl preferably means methoxy. The double bond in the alkenyl is in the 2-3 or 3-4 position. Alkenyl stands in particular for allyl or 2-methyl-2-propenyl.

R steht insbesondere für Methyl. R bedeutet vorzugsweise Alkyl oder Alkoxyalkyl, insbesondere Alkyl. Insbesondere bedeutet R_ Methyl, Aethyl oder n-Propyl.R stands in particular for methyl. R preferably denotes Alkyl or alkoxyalkyl, especially alkyl. In particular, R_ denotes methyl, ethyl or n-propyl.

Erfindungsgemäss gelangt man zu Verbindungen der Formel I und ihren Säureadditionssalzen, indem man Verbindungen der Formel II, ...-—--According to the invention, compounds of formula I and their acid addition salts by reacting compounds of formula II, ...----

70-9.814/103970-9.814 / 1039

500-5397500-5397

IIII

worin R? und R obige Bedeutung, besitzen, und X einen abspaltbaren Rest bedeutet, mit Verbindungen der Formel III,where R ? and R has the above meaning, and X is a removable radical, with compounds of the formula III,

HN N-R1 IIIHN NR 1 III

worin R, obige Bedeutung besitzt, umsetzt und die erhaltenen Verbindungen der Formel I gegebenenfallsin ihre Säureadditionssalze überführt.in which R, has the above meaning, and the compounds of the formula I obtained are optionally converted into their acid addition salts transferred.

Das Verfahren kann in einer für die Herstellung analoger Verbindungen bekannten Weise durchgeführt werden.The process can be carried out in a manner known for the preparation of analogous compounds.

In den Verbindungen der Formel II ist X an das Kohlenstoffatom kovalent oder ionisch gebunden und bedeutet zum Beispiel die Aminogruppe, die gegebenenfalls durch eine oder zwei Alkylgruppen mit 1-4 Kohlenstoffatomen, insbesondere Methylgruppen, substituiert sein kann, die Sulfhydrilgruppe, eine Alkoxy- oder Alkylthiogruppe mit 1-5 Kohlenstoffatomen, beispielsweise die Methoxy- oder die Methylthiogruppe, die p-Nitrobenzylthiogruppe oder die Tosyloxygruppe oder vorzugsweise Halogen, insbesondere Chlor.In the compounds of the formula II, X is covalently or ionically bonded to the carbon atom and means for Example the amino group, optionally replaced by one or two alkyl groups with 1-4 carbon atoms, in particular Methyl groups, the sulfhydril group, an alkoxy or alkylthio group with 1-5 carbon atoms, for example the methoxy or methylthio group, the p-nitrobenzylthio group or the tosyloxy group or, preferably, halogen, in particular chlorine.

709814/1039709814/1039

500-5397500-5397

Das Verfahren wird zweckmässigerweise bei Temperaturen zwischen 50 und 170° ,C in einem inerten organischen Lösungsmittel, beispielsweise Xylol oder Dioxan, durchgeführt. . . . . :The process is conveniently carried out at temperatures between 50 and 170 °, C in an inert organic Solvent, for example xylene or dioxane, carried out. . . . . :

Die Verbindungen der Formel I können in an sich bekannter Weise isoliert und gereinigt werden. ;The compounds of the formula I can be known per se Way to be isolated and purified. ;

Die Ausgangsverbindungen der Formel II können analog zu einem an sich bekannten Verfahren, z.B. des hier beschriebenen Verfahrens, z.B. aus dem entsprechenden Lactam, z.B. durch Umsetzung mit Phosphoroxychlorid, hergestellt werden.The starting compounds of the formula II can be analogous to a method known per se, for example that described here Process, e.g. from the corresponding lactam, e.g. by reaction with phosphorus oxychloride.

Die erfindungsgemäss hergestellten Verbindungen der Formel I zeichnen sich durch pharmakodynamische Eigenschaften aus. Sie können als Keuroleptika verwendet werden. Die Verbindungen der Formel I, worin FL Chlor und R3 Alkyl oder Alkenyl bedeuten,, zeichnen sich als Neuroleptika durch vorteilhafte Wirkungen, z.B. durch die weitgehende Abwesenheit von Nebenwirkungen beim Kreislauf aus:. Die Verbindungen der Formel I,worin R„ für Fluor steht, besitzen überdies eine antidepressive Wirkung.The compounds of the formula I prepared according to the invention are distinguished by pharmacodynamic properties. They can be used as keuroleptics. The compounds of the formula I, in which FL is chlorine and R 3 is alkyl or alkenyl, are distinguished as neuroleptics by advantageous effects, for example by the substantial absence of side effects in the circulatory system :. The compounds of the formula I in which R ″ stands for fluorine also have an antidepressant effect.

Die Verbindungen der Formel I können ebenfalls in Form von deren pharmazeutisch- verträglichen Säureadditionssalzen, beispielsweise als Hydrochlorid, Maleinat oder Fumarat, verabreicht werden, die den gleichen Grad an Aktivität besitzen wie die freien Basen.The compounds of the formula I can also be used in the form of their pharmaceutically acceptable acid addition salts, for example as hydrochloride, maleate or fumarate, administered that have the same level of activity as the free bases.

7098 U/10397098 U / 1039

- «β-- 500-5397- «β-- 500-5397

Die Verabreichung von Verbindungen der Formel I bzw. von deren Salzen kann entweder oral in Form von Tabletten, Granulaten, Kapseln oder Dragees, oder parenteral in Form von Injektionslösungen erfolgen.The administration of compounds of the formula I or their salts can either orally in the form of tablets, Granules, capsules or coated tablets, or parenterally in the form of injection solutions.

In den nachfolgenden Beispielen sind die Temperaturen in Grad-Celsius angegeben und sind unkorrigiert.In the following examples, the temperatures are given in degrees Celsius and are uncorrected.

70981 4/103970981 4/1039

500-5397500-5397

5,74 g 5~n~Propyl-8~chlor-10,ll-dihydro~5H-dibenzo[b,e][1,4] diazepin-ll-on, 30 ml Phosphoroxychlorid und 1 ml NfN-Dimethylanilin werden während 3 Stunden zum Sieden erhitzt. Die erhaltene Lösung des Imidchloride des Lactams wird im Vakuum zur Trockne eingedampft, der Rückstand zweimal mit Xylol nachgetrocknet und mit 20 ml Dioxan und 25 ml N-Methylpiperazin während 6 Stunden zum Sieden erhitzt« Die Lösung wird sodann möglichst weitgehend eingeengt und der Rückstand zwischen Ammoniakwasser und Aether verteilt. Die Aetherphase wird zweimal mit Wasser gewaschen und zur Abtrennung der basischen Anteile mit verdünnter Essigsäure erschöpfend extrahiert«, Die Base wird- aus den vereinigten Extrakten durch Zugabe von Natriumhydroxid freigesetzt, in· Chloroform aufgenommen, die Chloroformphase mit Wasser gewaschen, über wasserfreiem Natriumsulfat getrocknet und zur Trockne eingedampft.. Der Rückstand wird in Aether aufgenommen, über basischem Aluminiumoxid filtriert und aus Aether/Petroläther umkristallisiert, wobei man die Titelverbindung vom Smp. 120-122° erhält.5.74 g of 5-n-propyl-8-chloro-10, ll-dihydro-5H-dibenzo [b, e] [1,4] diazepin-II-one, 30 ml of phosphorus oxychloride and 1 ml of N f N-dimethylaniline are heated to boiling for 3 hours. The resulting solution of the imide chlorides of lactam is evaporated to dryness in vacuo, the residue is dried twice with xylene and heated to boiling with 20 ml of dioxane and 25 ml of N-methylpiperazine for 6 hours. The solution is then concentrated as much as possible and the residue between ammonia water and ether distributed. The ether phase is washed twice with water and exhaustively extracted with dilute acetic acid to separate the basic components. The base is released from the combined extracts by adding sodium hydroxide, taken up in chloroform, the chloroform phase is washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. The residue is taken up in ether, filtered through basic aluminum oxide and recrystallized from ether / petroleum ether, giving the title compound with a melting point of 120 ° -122 °.

Zu der Ausgangsverbindung kann man wie folgt gelangen:You can get to the starting compound as follows:

7098 U/10397098 U / 1039

INSPECTEDINSPECTED

- 500-5397- 500-5397

JOJO

2-Nitro-4-chlor-diphenylamin-2'-carbonsäure wird über das Säurechlorid in den 2-Nitro-4-chlor-diphenylainin-2 '-carbonsäuremethyiester vom Smp. 155-156° überführt, dieser wird mit n-Propyljodid in Gegenwart von Natriumhydrid in Hexamethylphosphorsäuretriamid zum N-n-Propyl-2-nitro--4-chlordiphenylamin-2'-carbonsäuremethylester umgesetzt, woraus man durch Reduktion mit Raney-Nickel in Essigester den N-n-Propyl-2-amino~4-chlor-diphenylamin-2 ä-carbonsäuremethylester erhält, den man einem Ringschluss durch mehrstündiges Erhitzen in Dioxan in Gegenwart von Natriumamid unterwirft, wobei man das 8-Chlor-5-n-propyl-10 f ll-dihydro-511-dibenzo [bfe][l,4]dlazepin~ll--on erhält.2-Nitro-4-chloro-diphenylamine-2'-carboxylic acid is converted via the acid chloride into the 2-nitro-4-chloro-diphenylamine-2'-carboxylic acid methyl ester of melting point 155 ° -156 °, which is converted into n-propyl iodide with n-propyl iodide The presence of sodium hydride in hexamethylphosphoric triamide is converted to Nn-propyl-2-nitro-4-chlorodiphenylamine-2'-carboxylic acid methyl ester, from which the Nn-propyl-2-amino-4-chloro-diphenylamine is obtained by reduction with Raney nickel in ethyl acetate 2 ä -carboxylic acid methyl ester is obtained, which is subjected to ring closure by heating for several hours in dioxane in the presence of sodium amide, the 8-chloro-5-n-propyl-10 f ll-dihydro-511-dibenzo [b f e] [l , 4] dlazepin ~ ll-on receives.

Analog Beispiel 1 und unter Verwendung entsprechender Ausgangsverbindungen gelangt man zu folgenden Verbindungen der Formel T:Analogously to Example 1 and using appropriate starting compounds the following compounds of the formula T are obtained:

Beispielexample VV ..8I.. 8 I. R3 R 3 Smp. ".M.p. ". ClCl CH3 CH 3 C2H5 C 2 H 5 22 ClCl CH3 CH 3 CH2CH2OCH3 CH 2 CH 2 OCH 3 145-146145-146 33 FF. CH3 CH 3 C2H5 C 2 H 5 160-161160-161 44th FF. CH3 CH 3 C3H7 C 3 H 7 133-135133-135 55 FF. CH3 CH 3 H-C4H9 HC 4 H 9 95-97 und 115-11795-97 and 115-117 66th ClCl CH3 CH 3 CH2-CH=CH2 CH 2 -CH = CH 2 124-125124-125 77th CiCi CH3 CH 3 CH2CH2OHCH 2 CH 2 OH 157-159157-159 88th ClCl CH3 CH 3 ISO-C3H7 ISO-C 3 H 7 157-159157-159 99 ClCl CH3 CH 3 ieo-CHieo-CH 152-154152-154 1010 128-131128-131

709814/1039709814/1039

500-5397500-5397

Beispielexample VV Ri. -■ R i. - ■ .R3 . . ..R 3 . . . Smp. °M.p. ° 1111 ClCl CH3 CH 3 n"C4H9 n " C 4 H 9 122-124122-124 12;12; FF. CH3 CH 3 CH3 CH 3 172-174172-174 1313th FF. CH2CH2OHCH 2 CH 2 OH CH3 CH 3 122-124122-124 1414th FF. C2H5 C 2 H 5 CH3 CH 3 146-147146-147 1515th FF. HH CH3 CH 3 147-149147-149 1616 FF. i-C3H7 iC 3 H 7 CH3 CH 3 136-137136-137 17 ;■""-:.17; ■ "" - :. FF. H-C3H7 HC 3 H 7 CH3 CH 3 136-138136-138 1818th FF. CH0CH-OCH0 CH 0 CH-OCH 0 CK3 CK 3 107-109107-109 1919th FF. t-C4H9 tC 4 H 9 CH3 'CH 3 ' 170-171170-171 2020th FF. CH3 CH 3 CH2-CH=CHCH 2 -CH = CH 139-140139-140

7098 14/10397098 14/1039

Claims (3)

500-5397500-5397 Patervtans^ruchPatervtans ^ ruch \1λ Verfahren zur Herstellung von Verbindungen der
Formel I, \ 1λ Process for the production of compounds of the
Formula I, worin R. für Wasserstoff, Alkyl mit 1-4 Kohlenstoffatomen, Hydroxyalkyl mit 2-4 Kohlenstoffatomen oder Alkoxyalkyl mit zusammen höchstens 5 Kohlenstoffatomen steht, R für Fluor oder Chlor und R für Alkyl mit 1-4 Kohlenstoffatomen,
Hydroxyalkyl mit 2-4 Kohlenstoffatomen, Alkoxyalkyl mit
zusammen höchstens 5 Kohlenstoffatomen oder Alkenyl mit 3-4 Kohlenstoffatomen stehen, mit der Massgabe, dass, falls R, Methyl bedeutet, R_ für Fluor steht, und ihren Säureadditionssalzen, dadurch gekennzeichnet, dass man Verbindungen der Formel II,where R. for hydrogen, alkyl with 1-4 carbon atoms, hydroxyalkyl with 2-4 carbon atoms or alkoxyalkyl with a maximum of 5 carbon atoms together, R for fluorine or chlorine and R for alkyl with 1-4 carbon atoms,
Hydroxyalkyl with 2-4 carbon atoms, alkoxyalkyl with
together are at most 5 carbon atoms or alkenyl with 3-4 carbon atoms, with the proviso that, if R is methyl, R_ is fluorine, and their acid addition salts, characterized in that compounds of the formula II, 7098 U /10397098 U / 1039 Ie--Ie-- 500-5397500-5397 IIII worin R_ und R obige Bedeutung besitzen, und X einen abspaltbaren Rest bedeutet, mit Verbindungen der Formel III,wherein R_ and R have the above meaning, and X one means that can be split off, with compounds of the formula III, HNHN N-R,NO, IIIIII worin R, obige Bedeutung besitzt, umsetzt und die erhaltenen Verbindungen der Formel I gegebenenfalls in ihre Säureadditionssalze überführt.in which R, has the above meaning, and the compounds of the formula I obtained are optionally converted converted into their acid addition salts. 37OO/IG/RR/SE37OO / IG / RR / SE 70981 A/ 103970981 A / 1039 500-5397 Deutschland500-5397 Germany 2. Verbindungen der Formel I,2. Compounds of the formula I, worin R für Wasserstoff, Alkyl mit 1-4 Kohlenstoffatomen, Hydroxyalkyl mit 2-4 Kohlenstoffatomen oder Alkoxyälkyl mit zusammen höchstens 5 Kohlenstoff atomen Steht.,-R.-für. Fluor oder Chlor und-R für Alkyl mit 1-4 Kohlenstoffatomen, Hydroxyalkyl mit 2-4 Kohlenstoffatomen, Alkoxyälkyl mit zusammen höchstens 5-Kohlenstoffatomen oder Alkenyl mit 3-4 Kohlenstoffatomen stehen, mit der Massgabe, dass, falls R Methyl bedeutet, R_ für Fluor steht, und ihre Säureadditionssalze» . """-_""."where R is hydrogen, alkyl with 1-4 carbon atoms, Hydroxyalkyl with 2-4 carbon atoms or Alkoxyälkyl with together not more than 5 carbon atoms., - R.- for. fluorine or chlorine and -R for alkyl with 1-4 carbon atoms, Hydroxyalkyl with 2-4 carbon atoms, alkoxyalkyl with together not more than 5 carbon atoms or alkenyl with 3-4 Carbon atoms, with the proviso that if R Methyl means, R_ stands for fluorine, and its acid addition salts » . "" "-_" "." 3. Therapeutische Zusammensetzung, gekennzeichnet durch. den Gehalt an Verbindungen der Formel I.3. Therapeutic composition, characterized by. the content of compounds of the formula I. 3700/IG/SE3700 / IG / SE 709814/ 10 39709814/10 39
DE19762641378 1975-09-24 1976-09-15 NEW ORGANIC COMPOUNDS, THEIR USE AND PRODUCTION Withdrawn DE2641378A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1241375A CH599196A5 (en) 1975-09-24 1975-09-24 (11)-Piperazinyl dibenzo-(b,e) (1,4)-diazepine derivs.
CH1241475A CH602709A5 (en) 1975-09-24 1975-09-24 (11)-Piperazinyl dibenzo-(b,e) (1,4)-diazepine derivs.
CH725076A CH602708A5 (en) 1976-06-09 1976-06-09 (11)-Piperazinyl dibenzo-(b,e) (1,4)-diazepine derivs.

Publications (1)

Publication Number Publication Date
DE2641378A1 true DE2641378A1 (en) 1977-04-07

Family

ID=27175741

Family Applications (1)

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DE19762641378 Withdrawn DE2641378A1 (en) 1975-09-24 1976-09-15 NEW ORGANIC COMPOUNDS, THEIR USE AND PRODUCTION

Country Status (16)

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JP (1) JPS5239689A (en)
AU (1) AU1808576A (en)
DE (1) DE2641378A1 (en)
DK (1) DK416476A (en)
ES (1) ES451772A1 (en)
FI (1) FI762646A (en)
FR (1) FR2325381A1 (en)
GB (1) GB1554275A (en)
IE (1) IE43727B1 (en)
IL (1) IL50531A0 (en)
NL (1) NL7610420A (en)
NO (1) NO763172L (en)
NZ (1) NZ182137A (en)
PT (1) PT65629B (en)
SE (1) SE7610219L (en)
SU (1) SU668602A3 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991010661A1 (en) * 1990-01-11 1991-07-25 Novokuznetsky Nauchno-Issledovatelsky Khimiko-Farmatsevtichesky Institut DERIVATIVES OF 5-AMINO-8-CHLORINE-DIBENZO[b,e][1,4]-DIAZEPINE AND A PHARMACEUTICAL PREPARATION FOR TREATMENT OF EPILEPSY AND EPILEPTIC STATUS BASED THEREON
US6034078A (en) * 1992-05-29 2000-03-07 Eli Lilly And Company Limited Thienobenzodiazepine compounds
TW268005B (en) * 1992-05-29 1996-01-11 Lilly Industries Ltd
US7550454B2 (en) 2003-12-22 2009-06-23 Acadia Pharmaceuticals, Inc. Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders
WO2013070107A1 (en) * 2011-11-09 2013-05-16 Общество С Ограниченной Ответственностью "Валентек" 5h-dibenzo[b,e][1,4]diazepine derivatives and use thereof

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IE43727L (en) 1977-03-24
NZ182137A (en) 1978-12-18
NL7610420A (en) 1977-03-28
FR2325381A1 (en) 1977-04-22
AU1808576A (en) 1978-04-06
PT65629B (en) 1978-05-10
SU668602A3 (en) 1979-06-15
PT65629A (en) 1976-10-01
IL50531A0 (en) 1976-11-30
IE43727B1 (en) 1981-05-06
SE7610219L (en) 1977-03-25
ES451772A1 (en) 1978-01-01
FI762646A (en) 1977-03-25
JPS5239689A (en) 1977-03-28
FR2325381B1 (en) 1978-11-17
GB1554275A (en) 1979-10-17
DK416476A (en) 1977-03-25
NO763172L (en) 1977-03-25

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