DE2901362A1 - GUANIDE DERIVATIVES, THEIR PRODUCTION AND USE - Google Patents
GUANIDE DERIVATIVES, THEIR PRODUCTION AND USEInfo
- Publication number
- DE2901362A1 DE2901362A1 DE19792901362 DE2901362A DE2901362A1 DE 2901362 A1 DE2901362 A1 DE 2901362A1 DE 19792901362 DE19792901362 DE 19792901362 DE 2901362 A DE2901362 A DE 2901362A DE 2901362 A1 DE2901362 A1 DE 2901362A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- compounds
- alkyl
- hydrogen
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/28—Halogen atoms
Description
- 3 » 100-5467- 3 »100-5467
Die Erfindung betrifft Guanidinderivate der Formel IThe invention relates to guanidine derivatives of the formula I
-R,-R,
worin R , R und R gleich oder verschieden sind und jeweils für Viasserstoff, Halogen oder Alkyl mit 1-4 Kohlenstoffatomen stehen, und entweder R4 und R unabhängig voneinander Wasserstoff,wherein R, R and R are the same or different and each represent hydrogen, halogen or alkyl with 1-4 carbon atoms, and either R 4 and R independently of one another are hydrogen,
Alkyl oder Hydroxyalkyl mit jeweils 1-4 Kohlenstoffatomen oder Alkoxyalkyl mit höchstens 6 Kohlenstoffatomen bedeuten, oder R. und R zusammen für Dimethylen oder Trimethylen stehen,Alkyl or hydroxyalkyl each with 1-4 carbon atoms or alkoxyalkyl with are at most 6 carbon atoms, or R. and R together for dimethylene or trimethylene stand,
R_ und R7 unabhängig voneinander WasserstoffR_ and R 7 independently of one another are hydrogen
oder Alkyl mit 1-4 Kohlenstoffatomen bedeuten, undor alkyl with 1-4 carbon atoms, and
X Schwefel, Sauerstoff, Imino oder Alkyliiaino mit 1-4 Kohlenstoffatomen bedeutet,X sulfur, oxygen, imino or alkyliiaino with 1-4 carbon atoms means
ihre Säureadditionssalze sowie ein Verfahren zu deren Herstellung.their acid addition salts and a process for their preparation.
Halogen bedeutet jeweils Fluor, Chlor, Brom oder Jod, vorzugsweise Chlor oder Brom. Alkyl besitzt vorzugsweise 1-3 Kohlenstoffatome, insbesondere 1 oder 2 Kohlenstoff atome. Hydroxyalkyl enthält vorzugsweise 2 oder 3 Kohlenstoffatome. Die Hydroxylgruppe steht vorzugsweise nicht an dem an das Stickstoffatom gebundeneHalogen in each case denotes fluorine, chlorine, bromine or iodine, preferably chlorine or bromine. Alkyl preferably has 1-3 carbon atoms, especially 1 or 2 carbon atoms. Hydroxyalkyl preferably contains 2 or 3 carbon atoms. The hydroxyl group preferably stands not bound to the nitrogen atom
909830/0668909830/0668
- 4 - 500-5467- 4 - 500-5467
Kohlenstoffatom. Der Alkoxyrest im Alkoxyalkyl befindet sich vorzugsweise in Endstellung der Alkylenkette, die vorzugsweise 2 oder 3 Kohlenstoffatome, insbesondere Kohlenstoffatome besitzt. Der Alkoxyrest im Alkoxyalkyl steht vorzugsweise für Methoxy.Carbon atom. The alkoxy radical is located in the alkoxyalkyl preferably in the end position of the alkylene chain, which preferably has 2 or 3 carbon atoms, in particular Has carbon atoms. The alkoxy radical in alkoxyalkyl is preferably methoxy.
R steht vorzugsweise für Halogen. R_ steht vorzugsweise für Halogen. X bedeutet zweckmässigerweise Schwefel oder Sauerstoff, vorzugsweise Schwefel.R preferably represents halogen. R_ is preferably for halogen. X is conveniently sulfur or Oxygen, preferably sulfur.
Erfindungsgemäss gelangt man zu Verbindungen der Fortnel I, indem man Verbindungen der Formel II,According to the invention one arrives at compounds of the Fortnel I by adding compounds of the formula II,
CH_COYCH_COY
λ II λ II
worin R1, R , R_ und X obige Bedeutung besitzen, und Ywherein R 1 , R, R_ and X have the above meaning, and Y
X £m «JX £ m «J
einen abspaltbaren Rest bedeutet, mit Verbindungen der Formel III,denotes a removable radical, with compounds of the formula III,
/ 5/ 5
HN=C ° IIIHN = C ° III
worin R., R5, R und R_ obige Bedeutung besitzen, umsetzt, und die erhaltenen Verbindungen der Formel Iin which R., R 5 , R and R_ have the above meaning, reacted, and the compounds of the formula I obtained
gegebenenfalls in ihre Säureadditionssalze überführt.optionally converted into their acid addition salts.
Das Verfahren kann in einer für die Herstellung analoger Ν,Ν,Ν-substituierter Guanidinderivate bekannten Weise durchgeführt werden. Y steht z.B. für Hydroxy, Alkoxy mit 1-4 Kohlenstoffatomen, Chlor oder Brom.The process can be carried out in a manner known for the preparation of analogous Ν, Ν, Ν-substituted guanidine derivatives be performed. Y stands for example for hydroxy, alkoxy with 1-4 carbon atoms, chlorine or bromine.
909830/0 668909830/0 668
BADBATH
- 5 - 100-5467- 5 - 100-5467
23013622301362
Die Ausgangsverbindungen der Formel II sind entweder bekannt oder nach an sich bekannten Verfahren herstellbar. Die Thienylessigsäuren können erhalten werden, indem man z.B. 2- bzw. 3-Methy!thiophene in 2- bzw. 3-Brommethylthiophene überführt und aus diesen über die 2- bzw. 3-Thienylacetonitrile die 2- bzw. 3-Thienylessigsäuren herstellt.The starting compounds of the formula II are either known or can be prepared by processes known per se. The thienylacetic acids can be obtained by converting, for example, 2- or 3-methylthiophenes into 2- or 3-bromomethylthiophenes and using the 2- or 3-thienylacetonitriles to prepare the 2- or 3-thienylacetic acids.
Die Verbindungen der Formel I können in an sich bekannter Weise in ihre Säureadditionssalze übergeführt werden und umgekehrt. Als Säuren sind z.B. Maleinsäure, Oxalsäure oder Chlorwasserstoffsäure geeignet.The compounds of the formula I can be known per se Way to be converted into their acid addition salts and vice versa. The acids are e.g. maleic acid, Oxalic acid or hydrochloric acid are suitable.
Die Verbindungen der Formel I zeichnen sich durch günstige pharmakodynamische Eigenschaften aus. Sie wirken insbesondere antihypertensiv.The compounds of the formula I are distinguished by favorable pharmacodynamic properties. they seem especially antihypertensive.
Die Verbindungen der Formel I können ebenfalls in Form ihrer pharmazeutisch verträglichen Säureadditionssalze 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 administered that have the same level of activity as the free bases.
Die Erfindung umfasst pharmazeutische Zubereitungen, die Verbindungen der Formel I in Form der freien Basen oder in Form pharmazeutisch verträglicher Säureaddi™ tionssalze zusammen mit pharmazeutisch verwendbaren Träger- oder Verdünnungsmitteln enthalten. Sie können in an sich bekannter Weise hergestellt werden und liegen z„B» als Tabletten oder Kapseln vor.The invention encompasses pharmaceutical preparations, the compounds of the formula I in the form of the free bases or in the form of pharmaceutically acceptable acid addition salts together with pharmaceutically acceptable ones Contain carriers or diluents. They can be produced and located in a manner known per se z “B” as tablets or capsules.
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 "
9098 30/06689098 30/0668
~ 6 - 500-5467~ 6 - 500-5467
In der Tabelle werden folgende Bezeichnungen verwendet:The following terms are used in the table:
1) freie Base, falls nicht anders angegeben1) free base, unless otherwise stated
2) Zersetzung2) decomposition
3) Hydrochlorid3) hydrochloride
4) R4 + R6 = -CH2-CH2-4) R 4 + R 6 = -CH 2 -CH 2 -
Beispiel 1: (2,4-Dichlor-3-thienyl)acetyl-guanidin Example 1: (2,4- dichloro-3- thienyl) acetylguanidine
Eine Lösung von 3 g Guanidin in 80 ml Isopropanol wird mit einer Lösung von 10 g (2,4-Dichlor-3-thienyl)essigsUuremethylester in 10 ml Isopropanol versetzt und 15 Stunden bei Zimmertemperatur gerührt. Das Reaktionsgemisch wird daraufhin eingedampft. Der Rückstand wird zwischen 2N wässeriger Chlorwasserstoffsäure und Aether verteilt, die wässerige Phase mit wässeriger Ammoniaklösung basisch gestellt und anschliessend mit Essigester extrahiert. Die Essigesterlösung wird weitgehend eingeengt, bis die Titelverbindung vom Smp. 215-223° (Zers.) auskristallisiert.A solution of 3 g of guanidine in 80 ml of isopropanol becomes with a solution of 10 g (2,4-dichloro-3-thienyl) ethyl acetate added in 10 ml of isopropanol and stirred for 15 hours at room temperature. The reaction mixture is then evaporated. The residue is between 2N aqueous hydrochloric acid and ether distributed, the aqueous phase made basic with aqueous ammonia solution and then with ethyl acetate extracted. The ethyl acetate solution is largely concentrated until the title compound has a melting point of 215-223 ° (decomp.) crystallized out.
Zu dem als Ausgangsverbindung verwendeten (2,4-Dichlor-3-thienyl)essigsäuremethylester kann man wie folgt gelangen: To the (2,4-dichloro-3-thienyl) acetic acid methyl ester used as the starting compound can be reached as follows:
a)a)
Ein Gemisch von 25 g 2,4-Dibrom-3-methylthiophen, 29 g Kupfer(I) Chlorid und 75 ml Dimethylformamid wird 20 Stunden lang unter Stickstoff zum Rückfluss erhitzt. Das erkaltete Gemisch wird in 750 ml Wasser gegossenA mixture of 25 g of 2, 4-dibromo-3-methylthiophene, 29 g of copper (I) chloride and 75 ml of dimethylformamide is heated for 20 hours under nitrogen to reflux. The cooled mixture is poured into 750 ml of water
909830/0668909830/0668
- 7 - 500-5467- 7 - 500-5467
und einer Wasserdampfdestillation unterworfen. Die organische Phase wird abgetrennt, getrocknet und destilliert, wobei man die Titelverbindung als farbloses OeI erhält.and subjected to steam distillation. The organic Phase is separated off, dried and distilled, the title compound being obtained as a colorless oil.
b)b)
9,4 g 2,4-Dichlor-3-methylthiophen, 10 g N-Bromsuccinimid und 50 rag α,α'-Azoisobutyronitril und 100 ml Tetrachlorkohlenstoff werden zusammen 15 Stunden land zum Rückfluss erhitzt. Das Gemisch wird filtriert, das Filtrat wird ein gedampft. Der ölige Rückstand wird destilliert, wobei man die Titelverbindung erhält.9.4 g of 2,4-dichloro-3-methylthiophene, 10 g of N-bromosuccinimide and 50 ml of α, α'-azoisobutyronitrile and 100 ml of carbon tetrachloride are refluxed together for 15 hours. The mixture is filtered, the filtrate is concentrated steamed. The oily residue is distilled to give the title compound.
c) (2jt4-Dichlor-3-thienYl]^acetonitrilc) (2 jt 4-dichloro-3-thienYl] ^ acetonitrile
9,6 g 2,4-Dichlor-3-brommethylthiophen werden in 160 ml Aethanol gelöst und mit einer Lösung von 5,8 g Kaliumcyanid in 50 ml Wasser versetzt. Das Gemisch wird 30 Minuten lang auf 65° erhitzt und gerührt. Danach wird rasch abgekühlt, 50 ml Wasser dazugegeben und mit Methylenchlorid extrahiert. Die organische Phase wird mit Aktivkohle behandelt, getrocknet und eingedampft. Der Rückstand wird destilliert, wobei man (2,4-Dichlor-3-thienyl)acetonitril erhält.9.6 g of 2,4-dichloro-3-bromomethylthiophene are added to 160 ml Dissolved ethanol and a solution of 5.8 g of potassium cyanide added in 50 ml of water. The mixture is heated to 65 ° for 30 minutes and stirred. After that, will cooled rapidly, added 50 ml of water and extracted with methylene chloride. The organic phase is with Treated activated charcoal, dried and evaporated. The residue is distilled, using (2,4-dichloro-3-thienyl) acetonitrile receives.
5,4 g (2,4-Dichlor-3-thienyl)acetonitril, 8 ml Eisessig, 5 ml Wasser und 5 ml konz. Schwefelsäure werden zusammen 3 Stunden lang zum Rückfluss erhitzt. Das Reaktionsgemisch wird mit etwas Eiswasser verdünnt. Der entstandene Niederschlag wird abfiltriert und in verdünnter wässriger Ammoniaklösung gelöst. Die Lösung wird mit Aktiv-Kohle behandelt, filtriert und mit verdünnter Schwefelsäure angesäuert, wobei man die Titelverbindung erhält.5.4 g (2,4-dichloro-3-thienyl) acetonitrile, 8 ml glacial acetic acid, 5 ml water and 5 ml conc. Sulfuric acid are refluxed together for 3 hours. The reaction mixture is diluted with a little ice water. The resulting precipitate is filtered off and dissolved in dilute aqueous ammonia solution. The solution is treated with activated charcoal , filtered and acidified with dilute sulfuric acid to give the title compound.
909830/0668909830/0668
- 8 - 500-5467- 8 - 500-5467
5,2 g (2f4-Dichlor-3-thienyl)essigsäure, 40 ml Methanol und 0,8 ml konz. Schwefelsäure werden zusammen 5 Stunden lang zürn Rückfluss erhitzt. Das Re akt ions gemisch wird dann eingedampft und der Rückstand mit 25 g Eis versetzt. Dieses Gemisch wird mit Methylenchlorid extrahiert. Die organische Phase wird mit wässriger Ammoniaklösung gewaschen, getrocknet und eingedampft, wobei man den (2,4-Dichlor-3-thienyl)essigsäuremethylester erhält.5.2 g (2 f 4-dichloro-3-thienyl) acetic acid, 40 ml of methanol and 0.8 ml of conc. Sulfuric acid are refluxed together for 5 hours. The reaction mixture is then evaporated and 25 g of ice are added to the residue. This mixture is extracted with methylene chloride. The organic phase is washed with aqueous ammonia solution, dried and evaporated to give methyl (2,4-dichloro-3-thienyl) acetic acid.
Analog Beispiel 1 gelangt man zu folgenden Verbindungen der Formel I, worin X Schwefel bedeutet und der Acetylguanidinrest in der durch "y" angegebenen Stellung steht;Analogously to Example 1, the following compounds of the formula I are obtained, in which X is sulfur and the acetylguanidine radical is in the position indicated by "y";
909830/0668 BAD O909830/0668 BAD O
- 9 - 500-5467- 9 - 500-5467
3700/IG/SE SANDOZ-PATENT-GMBH3700 / IG / SE SANDOZ-PATENT-GMBH
909830/0668909830/0668
Claims (1)
LorrachSandoz Patent GribH
Lorrach
X Schwefel, Sauerstoff, Imino oder Alkyliminoth, and
X sulfur, oxygen, imino or alkylimino
HN=C III R 5
HN = C III
BAD ORIGINAL909830/0668
BATH ORIGINAL
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH79978 | 1978-01-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2901362A1 true DE2901362A1 (en) | 1979-07-26 |
Family
ID=4195448
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792901362 Withdrawn DE2901362A1 (en) | 1978-01-25 | 1979-01-15 | GUANIDE DERIVATIVES, THEIR PRODUCTION AND USE |
Country Status (12)
Country | Link |
---|---|
JP (1) | JPS54112859A (en) |
AU (1) | AU4359279A (en) |
BE (1) | BE873658A (en) |
DE (1) | DE2901362A1 (en) |
FR (1) | FR2415636A1 (en) |
GB (1) | GB2013192A (en) |
IE (1) | IE790126L (en) |
IL (1) | IL56486A0 (en) |
IT (1) | IT7947732A0 (en) |
NL (1) | NL7900444A (en) |
SE (1) | SE7900459L (en) |
ZA (1) | ZA79315B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200602045A (en) | 2004-06-16 | 2006-01-16 | Wyeth Corp | Amino-5, 5-diphenylimidazolone derivatives for the inhibition of β-secretase |
JP2008503460A (en) | 2004-06-16 | 2008-02-07 | ワイス | Diphenylimidazopyrimidine and imidazolamine as inhibitors of β-secretase |
CN101103034A (en) | 2005-01-14 | 2008-01-09 | 惠氏公司 | Amino-imidazolones for the inhibition of beta-secretase |
KR20070107062A (en) | 2005-02-01 | 2007-11-06 | 와이어쓰 | AMINO-PYRIDINES AS INHIBITORS OF beta;-SECRETASE |
WO2006088694A1 (en) | 2005-02-14 | 2006-08-24 | Wyeth | SUBSTITUTED THIENYL AND FURYL ACYLGUANIDINES AS β-SECRETASE MODULATORS |
AU2006214627A1 (en) | 2005-02-14 | 2006-08-24 | Wyeth | Azolylacylguanidines as beta-secretase inhibitors |
TW200738683A (en) | 2005-06-30 | 2007-10-16 | Wyeth Corp | Amino-5-(5-membered)heteroarylimidazolone compounds and the use thereof for β-secretase modulation |
MX2008000212A (en) | 2005-06-30 | 2008-03-24 | Wyeth Corp | Amino-5-(6-membered)heteroarylimidazolone compounds and the use thereof for beta-secretase modulation. |
KR20080050430A (en) | 2005-09-26 | 2008-06-05 | 와이어쓰 | Amino-5-[4-(difluoromethoxy)phenyl]-5-phenylimidazolone compounds as inhibitors of the beta-secretase (bace) |
WO2007100536A1 (en) | 2006-02-24 | 2007-09-07 | Wyeth | DIHYDROSPIRO[DIBENZO[A,D][7]ANNULENE-5,4'-IMIDAZOL] COMPOUNDS FOR THE INHIBITION OF β-SECRETASE |
US7700606B2 (en) | 2006-08-17 | 2010-04-20 | Wyeth Llc | Imidazole amines as inhibitors of β-secretase |
PE20090617A1 (en) | 2007-03-23 | 2009-05-08 | Wyeth Corp | AMINO-5 - [- 4- (DIFLUOROMETOXI) PHENYL] -5-PHENYLIMIDAZOLONE COMPOUNDS FOR THE INHIBITION OF -SECRETASE |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1298112A (en) * | 1969-02-20 | 1972-11-29 | Wander Ag Dr A | Phenyl acetyl guanidine derivatives |
-
1979
- 1979-01-15 DE DE19792901362 patent/DE2901362A1/en not_active Withdrawn
- 1979-01-18 SE SE7900459A patent/SE7900459L/en unknown
- 1979-01-19 NL NL7900444A patent/NL7900444A/en not_active Application Discontinuation
- 1979-01-22 GB GB7902149A patent/GB2013192A/en not_active Withdrawn
- 1979-01-23 BE BE0/193042A patent/BE873658A/en unknown
- 1979-01-23 AU AU43592/79A patent/AU4359279A/en not_active Abandoned
- 1979-01-23 FR FR7901657A patent/FR2415636A1/en not_active Withdrawn
- 1979-01-23 IT IT7947732A patent/IT7947732A0/en unknown
- 1979-01-23 IL IL56486A patent/IL56486A0/en unknown
- 1979-01-24 JP JP621579A patent/JPS54112859A/en active Pending
- 1979-01-25 ZA ZA79315A patent/ZA79315B/en unknown
- 1979-01-30 IE IE790126A patent/IE790126L/en unknown
Also Published As
Publication number | Publication date |
---|---|
SE7900459L (en) | 1979-07-26 |
JPS54112859A (en) | 1979-09-04 |
IT7947732A0 (en) | 1979-01-23 |
IE790126L (en) | 1979-07-25 |
BE873658A (en) | 1979-07-23 |
FR2415636A1 (en) | 1979-08-24 |
ZA79315B (en) | 1980-09-24 |
AU4359279A (en) | 1979-08-02 |
IL56486A0 (en) | 1979-03-12 |
GB2013192A (en) | 1979-08-08 |
NL7900444A (en) | 1979-07-27 |
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Legal Events
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8139 | Disposal/non-payment of the annual fee |