CH579077A5 - Antiallergic benzo(4,5) cyclohepta(1,2-b)-thiophene derivs - prepd by reacting 4-(4-piperidinylidene)-4 H-benzo(4,5)6 cyclohepta(1,2-b)thiophen-9(10H)-one with a benz(hydr)yl halide - Google Patents
Antiallergic benzo(4,5) cyclohepta(1,2-b)-thiophene derivs - prepd by reacting 4-(4-piperidinylidene)-4 H-benzo(4,5)6 cyclohepta(1,2-b)thiophen-9(10H)-one with a benz(hydr)yl halideInfo
- Publication number
- CH579077A5 CH579077A5 CH1219172A CH1219172A CH579077A5 CH 579077 A5 CH579077 A5 CH 579077A5 CH 1219172 A CH1219172 A CH 1219172A CH 1219172 A CH1219172 A CH 1219172A CH 579077 A5 CH579077 A5 CH 579077A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- formula
- cyclohepta
- benzo
- halogen
- Prior art date
Links
- BQYAIXRTUQAHCK-UHFFFAOYSA-N 2h-benzo[1,2]cyclohepta[3,6-b]thiophene Chemical compound C1=C2C=CC=CC2=CC2=CCSC2=C1 BQYAIXRTUQAHCK-UHFFFAOYSA-N 0.000 title 1
- 230000003266 anti-allergic effect Effects 0.000 title 1
- 150000004820 halides Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 230000001558 histaminolytic effect Effects 0.000 claims abstract description 9
- 230000003042 antagnostic effect Effects 0.000 claims abstract description 5
- 230000001078 anti-cholinergic effect Effects 0.000 claims abstract description 5
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- -1 benzyl halides Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 231100000820 toxicity test Toxicity 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 241000700198 Cavia Species 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- BPJWPQMWJVBHKC-UHFFFAOYSA-N O=C(CC1=C2C=CS1)C(C=CC=C1)=C1C2=C1CCN(CC(C=C2)=CC=C2Cl)CC1 Chemical compound O=C(CC1=C2C=CS1)C(C=CC=C1)=C1C2=C1CCN(CC(C=C2)=CC=C2Cl)CC1 BPJWPQMWJVBHKC-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 206010040108 Serotonin syndrome Diseases 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 2
- 229960004373 acetylcholine Drugs 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001340 histamine Drugs 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003285 pharmacodynamic effect Effects 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000012730 sustained-release form Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- LJRKFCOGIJPEHN-UHFFFAOYSA-N 10-piperidin-4-ylidene-4h-benzo[1,2]cyclohepta[3,4-b]thiophen-5-one Chemical compound C12=CC=CC=C2C(=O)CC=2SC=CC=2C1=C1CCNCC1 LJRKFCOGIJPEHN-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 description 1
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
- C07D409/08—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Process for preparing new thiophene derivs of formula (I) comprises reacting corresp. N-unsubstd. cpds. of formula (II) with benzyl halides (III), then opt. converting (I) to an acid addition salt. (R1 = H or a halo or lower alkoxy substit. at 6 or 7 posn.; R2 = H or halo; R3 = H, phenyl or halophenyl) (I) have histaminolytic, serotonin-antagonistic and anticholinergic activities so are useful in treating various sorts of allergies.
Description
unter den Reaktionsbedingungen inerten organischen Lösungsmittel und vorzugsweise in Gegenwart eines alka lischen Kondensationsmittels wie Natrium- oder Kaliumcarbo nat. Die Anwendung eines stark polaren Lösungsmittels wie Hexamethylphosphorsäuretriamid, Dimethylsulfoxid, Dimethylformamid usw. ist von Vorteil.
Praktisch werden die Verbindungen der Formel III als
Chlorid oder Bromid eingesetzt. Die Reaktionstemperatur wird vorteilhafterweise niedrig, zwischen Raumtemperatur und etwa 600, gehalten.
Die Verbindungen der Formel I und ihre pharmakologisch verträglichen Säureadditionssalze sind in der Literatur bisher noch nicht beschrieben worden. Sie zweichnen sich durch phar makodynamische Eigenschaften aus und können daher als
Heilmittel verwendet werden.
So zeichnen sie sich durch histaminolytische Eigenschaften aus, wie aus den Resultaten im Histamin-Toxizitätstest am Meerschweinchen hervorgeht. Die histaminolytische Wirkung der 10-Keto-Verbindungen der Formel list spezifisch, da bei diesen 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 9-Keto-Verbindungen der Formel I weisen über ihre histaminolytischen Eigenschaften hinaus auch noch serotoninantagonistische und anticholinerge Eigenschaften auf. Sie sind aufgrund dieser Eigenschaften als Antaminika zu bewerten.
Die erfindungsgemässen Verbindungen können bei allergischen Affektionen verschiedenster Genese eingesetzt werden.
Die zu verwendenden Dosen variieren naturgemäss je nach der Art der verwendeten Substanz, der Administration und des zu behanelnden Zustandes. Sie 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 flüssigen Trägersubstanzen oder Verdünnungsmitteln.
Als Heilmittel können die Verbindungen der Formel I bzw.
ihre physiologisch verträglichen Säureadditionssalze allein oder in geeigneter Arzneiform 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, das die Erfindung näher erläutert, erfolgen alle Temperaturangaben in Celsiusgraden und sind unkorrigiert.
Beispiel
4-(1-p-Chlorbenzyl-4-piperidyliden)-4H-benzo [4,5]cyclohepta[1 ,2-b]thiophen-9( 10H)-on
Zum Gemisch von 1,8 g wasserfreiem Natriumcarbonat und 3,0 g 4-(4-Piperidinyliden)-4H-benzo[4,5]cyclohepta- [1,2-b]thiophen-10(9H)-on in 15 ml N,N-Dimethylformamid lässt man 2,8 ml p-Chlorbenzylchlorid bei Raumtemperatur zutropfen, rührt das Reaktionsgemisch 4,5 Stunden bei 70 , kühlt es auf Raumtemperatur ab und giesst es auf 200 ml Wasser. Das erhaltenen Produkt wird in üblicher Weise aufgearbeitet und als Öl erhalten. Physikalische Charakterisierung: CO-Band bei 1660 mll (Nujol); Rf 0,7 (auf neutralem Aluminiumoxyd; Methylenchlorid; Rf 0,77 (auf basischem Kieselgel; Benzol/Äthanol/Ammoniak 84/15/1).
PATENTANSPRUCH
Verfahren zur Herstellung neuer 4H-Benzo[4,5]cyclohepta [1,2-b]thiophen-Derivate der Formel I
Die Erfindung betrifft ein Verfahren zur Herstellung neuer 4H-Benzo-[4,5] cyclohepta[l,2-b]thiophen-Derivate der Formel I,
EMI1.1
worin Rl für Wasserstoff oder einen in 6- oder 7-Stellung ständigen Halogen- oder niederen Alkoxyrest steht, R2 für Wasserstoff oder Halogen steht und R3 Wasserstoff, Phenyl oder Halogenphenyl bedeutet, und ihrer Säureadditionssalze.
Stellt das Symbol Rl Halogen dar, so steht es insbesondere für Chlor oder Brom.
Stellt Rl eine niedere Alkoxygruppe dar, so enthält diese insbesondere 1 bis 4 Kohlenstoffatome.
Stellt R2 Halogen dar, so steht es insbesondere für Fluor, Chlor oder Brom.
Als Halogensubstituente für den Phenylrest R3 sind auch insbesondere Fluor, Chlor und Brom geeignet.
Erfindungsgemäss gelangt man zu den Verbindungen der Formel I und ihren Säureadditionssalzen, indem man Verbindungen der Formel II,
EMI1.2
worin Ri obige Bedeutung besitzt mit Verbindungen der Formel III
EMI1.3
worin R2 und R3 obige Bedeutung besitzen und Hal für Halogen steht, umsetzt und gewünschtenfalls die so erhaltenen Verbindungen der Formel I in ihre Säureadditionssalze überführt.
Aus den freien Basen lassen sich in bekannter Weise Säureadditionssalze herstellen und umgekehrt.
Die Umsetzung der Verbindungen der Formel II mit den Verbindungen der Formel III erfolgt beispielsweise in einem
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Organic solvents which are inert under the reaction conditions and preferably in the presence of an alkaline condensing agent such as sodium or potassium carbonate. The use of a strongly polar solvent such as hexamethylphosphoric triamide, dimethyl sulfoxide, dimethylformamide, etc. is advantageous.
In practice, the compounds of formula III as
Chloride or bromide used. The reaction temperature is advantageously kept low, between room temperature and about 600 °.
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 called
Remedies are used.
They are characterized by histaminolytic properties, as can be seen from the results of the histamine toxicity test on guinea pigs. The histaminolytic effect of the 10-keto compounds of the formula list is specific, since no significant serotonin-antagonistic or anticholinergic properties can be determined in these using the serotonin toxicity test and the acetylcholine toxicity test on guinea pigs. These compounds can be characterized as specific histaminolytics.
In addition to their histaminolytic properties, the 9-keto compounds of the formula I also have serotonin-antagonistic and anticholinergic properties. Due to these properties, they are to be assessed as antaminics.
The compounds according to the invention can be used in allergic diseases of the most varied of origins.
The doses to be used naturally vary depending on the type of substance used, the administration and the condition to be treated. If necessary, they 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 applications, the partial doses contain about 0.15 to 10 mg of the new compounds in addition to solid or liquid carriers or diluents.
The compounds of the formula I or
their physiologically acceptable acid addition salts are administered alone or in a suitable pharmaceutical form.
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, all temperatures are given in degrees Celsius and are uncorrected.
example
4- (1-p-Chlorobenzyl-4-piperidylidene) -4H-benzo [4,5] cyclohepta [1,2-b] thiophen-9 (10H) -one
To the mixture of 1.8 g of anhydrous sodium carbonate and 3.0 g of 4- (4-piperidinylidene) -4H-benzo [4.5] cyclohepta- [1,2-b] thiophen-10 (9H) -one in 15 ml N, N-dimethylformamide is allowed to drop in 2.8 ml of p-chlorobenzyl chloride at room temperature, the reaction mixture is stirred for 4.5 hours at 70, cooled to room temperature and poured into 200 ml of water. The product obtained is worked up in a customary manner and obtained as an oil. Physical characterization: CO band at 1660 ml (Nujol); Rf 0.7 (on neutral aluminum oxide; methylene chloride; Rf 0.77 (on basic silica gel; benzene / ethanol / ammonia 84/15/1).
PATENT CLAIM
Process for the preparation of new 4H-benzo [4,5] cyclohepta [1,2-b] thiophene derivatives of the formula I.
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,
EMI1.1
where Rl is hydrogen or a halogen or lower alkoxy radical in the 6- or 7-position, R2 is hydrogen or halogen and R3 is hydrogen, phenyl or halophenyl, and their acid addition salts.
If the symbol R1 represents halogen, it stands in particular for chlorine or bromine.
If Rl represents a lower alkoxy group, it contains in particular 1 to 4 carbon atoms.
If R2 represents halogen, it particularly represents fluorine, chlorine or bromine.
Fluorine, chlorine and bromine are also particularly suitable as halogen substituents for the phenyl radical R3.
According to the invention, the compounds of the formula I and their acid addition salts are obtained by adding compounds of the formula II,
EMI1.2
wherein Ri has the above meaning with compounds of the formula III
EMI1.3
in which R2 and R3 have the above meanings and Hal stands for halogen, and, if desired, converts the compounds of the formula I thus obtained into their acid addition salts.
Acid addition salts can be prepared from the free bases in a known manner and vice versa.
The reaction of the compounds of the formula II with the compounds of the formula III takes place, for example, in one
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1219172A CH579077A5 (en) | 1972-08-17 | 1972-08-17 | Antiallergic benzo(4,5) cyclohepta(1,2-b)-thiophene derivs - prepd by reacting 4-(4-piperidinylidene)-4 H-benzo(4,5)6 cyclohepta(1,2-b)thiophen-9(10H)-one with a benz(hydr)yl halide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1219172A CH579077A5 (en) | 1972-08-17 | 1972-08-17 | Antiallergic benzo(4,5) cyclohepta(1,2-b)-thiophene derivs - prepd by reacting 4-(4-piperidinylidene)-4 H-benzo(4,5)6 cyclohepta(1,2-b)thiophen-9(10H)-one with a benz(hydr)yl halide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH579077A5 true CH579077A5 (en) | 1976-08-31 |
Family
ID=4380741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1219172A CH579077A5 (en) | 1972-08-17 | 1972-08-17 | Antiallergic benzo(4,5) cyclohepta(1,2-b)-thiophene derivs - prepd by reacting 4-(4-piperidinylidene)-4 H-benzo(4,5)6 cyclohepta(1,2-b)thiophen-9(10H)-one with a benz(hydr)yl halide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH579077A5 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5393753A (en) * | 1990-10-10 | 1995-02-28 | Schering Corporation | Substituted imidazobenzazepines |
-
1972
- 1972-08-17 CH CH1219172A patent/CH579077A5/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5393753A (en) * | 1990-10-10 | 1995-02-28 | Schering Corporation | Substituted imidazobenzazepines |
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