CH565172A5 - 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors - Google Patents
4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitorsInfo
- Publication number
- CH565172A5 CH565172A5 CH98872A CH98872A CH565172A5 CH 565172 A5 CH565172 A5 CH 565172A5 CH 98872 A CH98872 A CH 98872A CH 98872 A CH98872 A CH 98872A CH 565172 A5 CH565172 A5 CH 565172A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperidylidene
- cyclohepta
- formula
- benzo
- methyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cpds. of formula (I): (where R1, at posns. 6 or 7, = H, halo or lower alkoxy; A and B are either (a) both carbonyl; (b) one is hydroxy- or hydroxyimino-methylene and other is methylene in which case R2 is lower alkyl, benzyl or diphenylmethyl opt. ring substd. by halo, or (c) one is carbonyl and the other methylene in which case R2 is benzyl or diphenylmethyl opt. ring substd. by halo) and their acid salts.
Description
Die Erfindung betrifft ein Verfahren zur Herstellung neuer 4H-Benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate der Formel I, worin Rl für Wasserstoff oder einen in 6- oder 7-Stellung ständigen Halogen- oder niederen Alkoxyrest steht, R2 niederes Alkyl, eine Benzylgruppe, die gegebenenfalls im Phe nylrest durch Halogen substituiert sein kann, oder eine Diphenylmethylgruppe, die gegebenenfalls in einem oder in beiden Phenylresten durch Halogen substituiert sein kann, und X fir eine in 9- oder l0-Stellung ständige Oximgruppe steht.
und ihrer Säureadditionssalze.
Stellt das Symbol R1 Halogen dar, so steht es insbesondere für Chlor oder Brom.
Stellt R, eine niedere Alkoxygruppe dar, so enthält diese insbesondere 1 bis 4 Kohlenstoffatome.
Stellt R2 eine niedere Alkylgruppe dar, so enthält diese vorzugsweise 1 bis 4 Kohlenstoffatome.
Als ailfallige Halogensubstituenten der Phenylreste, die in R.. enthalten sein können, sind insbesondere Fluor, Chlor und Brom geeignet.
Erfindungsgemäss gelangt man zu den Verbindungen der Formel I und ihren Säureadditionssalzen, indem man Verbindungen der Formel II, worin R1 und R2 obige Bedeutung besitzen und Y eine in 9- oder 10-Stellung stiindige Oxogruppe bedeutet, mit Hydroxylamin umsetzt und gewtinschten- falls die so erhaltenen Verbindungen der Formel I in ihre Säureadditionssalze tiberftihrt.
Aus den freien Basen lassen sich auf an sich bekannte Weise Säureadditionssalze herstellen und umgekehrt.
Praktisch wird Hydroxylamin als Salz eingesetzt, beispielsweise als Hydrochlorid.
Die Umsetzung erfolgt beispielsweise in einem unter den Reaktionsbedingungen inerten Lösungsmittel, z.B. in einem niederen Alkanol wie Athanol oder in Wasser. Falls mit einem Salz von Hydroxylamin gearbeitet wird, fallt die erhaltene Verbindung der Formel I als Salz an.
Die Reaktionstemperatur kann zwischen Raumtemperatur und Rückflusstemperatur variieren. Die Reaktionsdauer ist von der Reaktionstemperatur abhängig.
Die Verbindungen der Formel I und ihre pharmakologisch verträglichen Säureadditionssalze sind in der Literatur bisher noch nicht beschrieben worden. Sie zeichnen sich durch phar- makodynamische Eigenschaften aus und können daher als Heilmittel verwendet werden. Sie zeichnen sich durch histaminolytische Eigenschaften aus, wie aus den Resultaten im Histamin-Toxizitatstest am Meerschweinchen hervorgeht, und können aufgrund dieser Eigenschaften bei allergischen Affektionen verschiedenster Genese eingesetzt werden.
Die histaminolytische Wirkung der 9-Oxime der Formel list spezifisch, da mit Hilfe des Serotonin-Toxizitätstests und des Acetylcholin-Toxizitätstests am Meerschweinchen keine signifikanten serotoninantagonistischen und anticholinergen Eigenschaften festgestellt werden können. Diese Verbindungen sind als spezifische Histaminolytika zu charakterisieren.
Die 10-Oxime der Formel I weisen tiber ihre histaminolytischen Eigenschaften hinaus, auch noch serotoninantagonistische und anticholinerge Eigenschaften aus. Sie sind aufgrund dieser Eigenschaften als Antaminika zu bewerten.
Die zu verwendenden Dosen variieren naturgemass je nach der Art der verwendeten Substahz, der Administration und des zu behandelnden Zustandes. Diese Dosen können nötigenfalls in 2 bis 3 Anteilen oder auch als Retardform verabreicht werden. Die Tagesdosis liegt bei etwa 0,5 bis 20 mg. Für orale Applikationen enthalten die Teildosen etwa 0,15 bis 10 mg der neuen Verbindungen neben festen oder fltissigen Trägersubstanzen oder Verdunnungsmitteln.
Als Heilmittel können die Verbindungen der Formel I bzw.
ihre physiologisch vertraglichen Säureadditionssalze allein oder in geeigneter Arzneiform mit pharmakologisch indifferenten Hilfsstoffen verabreicht werden.
Soweit die Herstellung der Ausgangsverbindungen nicht beschrieben wird, sind diese bekannt oder nach an sich bekannten Verfahren bzw. analog zu den hier beschriebenen oder analog zu an sich bekannten Verfahren herstellbar.
Im nachfolgenden Beispiel, welches die Erfindung naher erlautert, ihren Umfang aber in keiner Weise einschränken soll, erfolgen alle Temperaturangaben in Celsiusgraden und sind unkorrigiert.
Beispiel I
9,10-Dihydro-9-hydroxyimino-4-(1-methyl-4-piperidyliden)- -4H-benzo[4,5jcyclohepta[1.2-bjthiophen
Ein Gemisch von 13,5 g Hydroxylaminohydrochlorid, 200 ccm absolutem ethanol und 20 g 4-(1 -Methyl-4-piperidy- liden)-4H-benzo[4,5]cyclohepta[1 ,2-b]thiophen-9(1 OH)-on -Base wird während 1 Stunde am Rückfluss gekocht. Darauf wird auf 0-5 abgektihlt und das ausgefallene Kristallisat abfiltriert. Nach dem Umkristallisieren aus Methanol wird das reine 9,1 0-Dihydro-9-hydroxyimino-4-(1 -methyl-4-piperidyli- den)-4H-benzo[4,5]cyclohepta[1,2-b]thiophenhydrochlorid erhalter, welches einen Zersetzungsbereich von 290-3000 aufweist.
Die Mikroanalyse stimmt auf die Formel Cl9H20N2OS HCI. Die Struktur wurde mit Hilfe der IR- und NMR-Spektren ermittelt.
Beispiel 2
9,10-Dihydro-10-hydroxyimino-4-(1 -methyl -4-piperidylid en)- -4H-benzo[4,5]cycThhepia[1,2-blthiophen
Ein Gemisch von 15 g 4-(1-Methyl-4-piperidyliden)-4H- -benzo[4,5]cyclohepta[1 ,2-b]thiophen-1 0(9H)-on-Base, 10,1 g Hydroxylaminhydrochlorid und 120 ccm Wasser wird 1 Stunde bei 90 Innentemperatur gerührt. Anschliessend wird die heisse Reaktionslösung mit 3 N Natronlauge alkalisiert und die auskristallisierte Base abfiltriert. Zur Reinigung wird die Rohbase in 25 ccm Eisessig und 50 ccm Wasser gelöst, mit wenig Kohle filtriert und das Filtrat zu einer Lösung von 80 ccm konzentriertem Ammoniak und 500 ccm Wasser gegossen.
Die ausgefallene Base wird abfiltriert, mit Wasser gewaschen und im Vakuum getrocknet. Auf diese Weise wird die reine 9,1 0-Dihydro-l0-hydroxyimino-4-(1 -methyl-4-piperidyliden)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-Base erhalten, welche bei 239-241" unter Zersetzung schmilzt. Die Mi- kroanalyse stimmt auf die Formel C1jH20N2OS. Nach NMR Spektrum handelt es sich um ein Isomeren-Gemisch von syn/ anti-Oxim im Verhältnis 6: 4.
EMI1.1
EMI2.1
The invention relates to a process for the preparation of new 4H-benzo [4,5] cyclohepta [1,2-b] thiophene derivatives of the formula I in which Rl is hydrogen or a halogen or lower alkoxy radical in the 6- or 7-position R2 is lower alkyl, a benzyl group which may optionally be substituted in the phenyl radical by halogen, or a diphenylmethyl group which may optionally be substituted in one or both phenyl radicals by halogen, and X is a 9- or 10-position Oxime group.
and their acid addition salts.
If the symbol R1 represents halogen, it stands in particular for chlorine or bromine.
If R 1 represents a lower alkoxy group, it contains in particular 1 to 4 carbon atoms.
If R2 represents a lower alkyl group, this preferably contains 1 to 4 carbon atoms.
Fluorine, chlorine and bromine, in particular, are suitable as possible halogen substituents of the phenyl radicals which may be contained in R ...
According to the invention, the compounds of the formula I and their acid addition salts are obtained by reacting compounds of the formula II in which R1 and R2 have the above meaning and Y is an oxo group in the 9 or 10 position with hydroxylamine, and if so desired The resulting compounds of the formula I are converted into their acid addition salts.
Acid addition salts can be prepared from the free bases in a manner known per se, and vice versa.
In practice, hydroxylamine is used as a salt, for example as the hydrochloride.
The reaction takes place, for example, in a solvent which is inert under the reaction conditions, e.g. in a lower alkanol such as ethanol or in water. If a salt of hydroxylamine is used, the compound of the formula I obtained is obtained as a salt.
The reaction temperature can vary between room temperature and reflux temperature. The reaction time depends on the reaction temperature.
The compounds of the formula I and their pharmacologically acceptable acid addition salts have not yet been described in the literature. They are characterized by pharmacodynamic properties and can therefore be used as remedies. They are characterized by histaminolytic properties, as can be seen from the results of the histamine toxicity test on guinea pigs, and because of these properties they can be used in allergic diseases of the most varied of origins.
The histaminolytic effect of the 9-oximes of the formula is specific, since the serotonin toxicity test and the acetylcholine toxicity test on guinea pigs do not reveal any significant serotonin-antagonistic or anticholinergic properties. These compounds can be characterized as specific histaminolytics.
In addition to their histaminolytic properties, the 10-oximes of the formula I also have serotonin-antagonistic and anticholinergic properties. Due to these properties, they are to be assessed as antaminics.
The doses to be used naturally vary depending on the type of substance used, the administration and the condition to be treated. If necessary, these doses can be administered in 2 to 3 portions or as a sustained release form. The daily dose is around 0.5 to 20 mg. For oral administration, the partial doses contain about 0.15 to 10 mg of the new compounds in addition to solid or liquid carrier substances or diluents.
The compounds of the formula I or
their physiologically acceptable acid addition salts are administered alone or in a suitable pharmaceutical form with pharmacologically inert adjuvants.
If the preparation of the starting compounds is not described, they are known or can be prepared by processes known per se or analogously to those described here or analogously to processes known per se.
In the following example, which explains the invention in more detail but is not intended to limit its scope in any way, all temperatures are given in degrees Celsius and are uncorrected.
Example I.
9,10-Dihydro-9-hydroxyimino-4- (1-methyl-4-piperidylidene) -4H-benzo [4,5jcyclohepta [1,2-bjthiophene
A mixture of 13.5 g of hydroxylamino hydrochloride, 200 cc of absolute ethanol and 20 g of 4- (1-methyl-4-piperidylidene) -4H-benzo [4,5] cyclohepta [1,2-b] thiophene-9 ( 1 OH) -one base is refluxed for 1 hour. It is then cooled to 0-5 and the precipitated crystals are filtered off. After recrystallization from methanol, the pure 9.1 0-dihydro-9-hydroxyimino-4- (1-methyl-4-piperidylidene) -4H-benzo [4.5] cyclohepta [1,2-b] thiophene hydrochloride is obtained obtained, which has a decomposition range of 290-3000.
The microanalysis agrees with the formula Cl9H20N2OS HCI. The structure was determined with the help of the IR and NMR spectra.
Example 2
9,10-dihydro-10-hydroxyimino-4- (1 -methyl -4-piperidylidene) -4H -benzo [4,5] cycThhepia [1,2-thiophene
A mixture of 15 g of 4- (1-methyl-4-piperidylidene) -4H- -benzo [4.5] cyclohepta [1,2-b] thiophene-10 (9H) -one base, 10.1 g Hydroxylamine hydrochloride and 120 ccm of water are stirred at an internal temperature of 90 for 1 hour. The hot reaction solution is then made alkaline with 3N sodium hydroxide solution and the base which has crystallized out is filtered off. For cleaning, the raw base is dissolved in 25 cc of glacial acetic acid and 50 cc of water, filtered with a little charcoal and the filtrate is poured into a solution of 80 cc of concentrated ammonia and 500 cc of water.
The precipitated base is filtered off, washed with water and dried in vacuo. In this way, the pure 9.1 0-dihydro-10-hydroxyimino-4- (1-methyl-4-piperidylidene) -4H-benzo [4,5] cyclohepta [1,2-b] thiophene base is obtained, which melts at 239-241 "with decomposition. The microanalysis agrees with the formula C1jH20N2OS. According to the NMR spectrum, it is an isomer mixture of syn / anti-oxime in the ratio 6: 4.
EMI1.1
EMI2.1
Claims (1)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE794377D BE794377A (en) | 1972-01-24 | NEW DERIVATIVES OF BENZO-CYCLOHEPTA-THIOPHENE | |
CH98872A CH565172A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
US286281A US3862156A (en) | 1972-01-24 | 1972-09-05 | 4h-benzo{8 4,5{9 cyclohepta{8 1,2-6{9 thiophenes |
JP47117590A JPS5760351B2 (en) | 1972-01-24 | 1972-11-22 | |
DD167577A DD102701A5 (en) | 1972-01-24 | 1972-12-15 | |
SE7300501A SE383347B (en) | 1972-01-24 | 1973-01-15 | PROCEDURE FOR PREPARING NEW 4 H-BENZO (4,5) CYCLOHEPTA (1,2-B) THIOFENE DERIVATIVES |
DK22573A DK134405B (en) | 1972-01-24 | 1973-01-15 | Analogous process for the preparation of benzo / 4,5 / cyclohepta / 1,2-b / thiophene derivatives or acid addition salts thereof. |
FI110/73A FI55843C (en) | 1972-01-24 | 1973-01-16 | PROCEDURE FOR THE FRAMEWORK OF THERAPEUTIC ANVAENDBARA 9,10-DIHYDRO-9-ELLER -10-HYDROXY-IMINO-4- (1-ALKYL-4-PIPERIDYLIDENE) -4H-BENZO (4,5) CYCLOHEPTA ) TIOFENDERIVAT OCH DERAS SYRAADDITIONSSALTER |
NL7300796A NL7300796A (en) | 1972-01-24 | 1973-01-19 | |
PL16037373A PL83920B1 (en) | 1972-01-24 | 1973-01-22 | |
CY992A CY992A (en) | 1972-01-24 | 1973-01-22 | Benzocycloheptathiophene derivatives |
GB311873A GB1415591A (en) | 1972-01-24 | 1973-01-22 | Benzocycloheptathiophene derivatives |
DE2302944A DE2302944C2 (en) | 1972-01-24 | 1973-01-22 | 9,10-Dihydro-4- (1-substituted-4-piperidylidene) -4H-benzene [4,5] cyclohepta [1,2-b] thiophenes, processes for their preparation and pharmaceuticals containing them |
HUSA2447A HU165130B (en) | 1972-01-24 | 1973-01-22 | |
PL18205073A PL92124B1 (en) | 1972-01-24 | 1973-01-22 | |
CS415273A CS180000B2 (en) | 1972-01-24 | 1973-01-23 | Method for production of novel benzocycloheptathiophenone derivatives |
FR7302444A FR2183663B2 (en) | 1972-01-24 | 1973-01-24 | |
SU2027852A SU505364A3 (en) | 1972-01-24 | 1974-05-28 | The method of obtaining derivatives of 4n-benzo (4,5) c of clogpeta (1,2-v) triofen |
ES438596A ES438596A1 (en) | 1972-01-24 | 1975-06-16 | Procedure for obtaining derivatives of benzocicloheptatiofeno. (Machine-translation by Google Translate, not legally binding) |
AT685775A AT337182B (en) | 1972-01-24 | 1975-09-05 | PROCESS FOR THE PREPARATION OF NEW 4- (4-PIPERIDYLIDEN) -4H-BENZO (4,5) CYCLOHEPTA (1,2-B) THIOPHEN DERIVATES AND THEIR ACID ADDITIONAL SALTS |
FI790145A FI59591C (en) | 1972-01-24 | 1979-01-17 | REFERENCE FOR THERAPEUTIC TREATMENT OF THERAPEUTIC ACID 4H-BENZO (4,5) CYCLOHEPTA (1,2-B) THIOPHENE DERIVATIVES |
HK112/79A HK11279A (en) | 1972-01-24 | 1979-03-08 | Benzocycloheptathiophene derivatives |
MY114/79A MY7900114A (en) | 1972-01-24 | 1979-12-30 | Benzocycloheptathiophene derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH98872A CH565172A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
CH565172A5 true CH565172A5 (en) | 1975-08-15 |
Family
ID=4199855
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH98872A CH565172A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Country Status (6)
Country | Link |
---|---|
CH (1) | CH565172A5 (en) |
CS (1) | CS180000B2 (en) |
DK (1) | DK134405B (en) |
ES (1) | ES438596A1 (en) |
PL (1) | PL92124B1 (en) |
SU (1) | SU505364A3 (en) |
-
1972
- 1972-01-24 CH CH98872A patent/CH565172A5/en not_active IP Right Cessation
-
1973
- 1973-01-15 DK DK22573A patent/DK134405B/en not_active IP Right Cessation
- 1973-01-22 PL PL18205073A patent/PL92124B1/pl unknown
- 1973-01-23 CS CS415273A patent/CS180000B2/en unknown
-
1974
- 1974-05-28 SU SU2027852A patent/SU505364A3/en active
-
1975
- 1975-06-16 ES ES438596A patent/ES438596A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK134405C (en) | 1977-03-28 |
PL92124B1 (en) | 1977-03-31 |
SU505364A3 (en) | 1976-02-28 |
ES438596A1 (en) | 1977-09-01 |
DK134405B (en) | 1976-11-01 |
CS180000B2 (en) | 1977-12-30 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |