CH367829A - Process for the production of new dibenzazepines - Google Patents
Process for the production of new dibenzazepinesInfo
- Publication number
- CH367829A CH367829A CH6192158A CH6192158A CH367829A CH 367829 A CH367829 A CH 367829A CH 6192158 A CH6192158 A CH 6192158A CH 6192158 A CH6192158 A CH 6192158A CH 367829 A CH367829 A CH 367829A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- dibenzazepines
- new
- acid
- bis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 7
- -1 allylthioethylamine Chemical compound 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- PGAOVVJJOXMLCQ-UHFFFAOYSA-N 2-methylsulfinylethanamine Chemical compound CS(=O)CCN PGAOVVJJOXMLCQ-UHFFFAOYSA-N 0.000 description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
- HJCTVUWPHAZTLI-UHFFFAOYSA-N 2-ethylsulfanylethanamine Chemical compound CCSCCN HJCTVUWPHAZTLI-UHFFFAOYSA-N 0.000 description 1
- IUMHWHARDIAQMZ-UHFFFAOYSA-N 2-ethylsulfinylethanamine Chemical compound CCS(=O)CCN IUMHWHARDIAQMZ-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- QDMWHNBXADHQCO-UHFFFAOYSA-N 2-propan-2-ylsulfanylethanamine Chemical compound CC(C)SCCN QDMWHNBXADHQCO-UHFFFAOYSA-N 0.000 description 1
- KHHKBTRFZTUVRD-UHFFFAOYSA-N 2-propylsulfanylethanamine Chemical compound CCCSCCN KHHKBTRFZTUVRD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- VNEOUFRVFBPYGL-UHFFFAOYSA-N BrCC1=C(C=CC(=C1)C)C1=C(C=C(C=C1)C)CBr Chemical group BrCC1=C(C=CC(=C1)C)C1=C(C=C(C=C1)C)CBr VNEOUFRVFBPYGL-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- URDSHYOWFGTOCY-UHFFFAOYSA-N n-methylsulfanylpropan-2-amine Chemical compound CSNC(C)C URDSHYOWFGTOCY-UHFFFAOYSA-N 0.000 description 1
- NDQGMKMWOPZABY-UHFFFAOYSA-N n-propoxyethanamine Chemical compound CCCONCC NDQGMKMWOPZABY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
Verfahren zur Herstellung von neuen Dibenzazepinen Die Erfindung betrifft ein Verfahren zur Her stellung von neuen Dibenzazepinen der Formel
EMI0001.0005
in welcher R1 einen niederen Alkylenrest, R2 einen niederen aliphatischen Rest, X Sauerstoff, Schwefel, SO oder S02, und die Symbole R3, R4, RS und R6 Wasserstoff, Halogen, Hydroxy, Alkyl,
Alkoxy oder Alkylmercapto darstellen.
Die neuen Azepine sollen bei Erkrankungen des vaskulären Systems, z. B. als Vasodilatoren usf., ver wendet werden.
Die neuen Dibenzazepine lassen sich in einfacher Weise herstellen, indem man erfindungsgemäss eine Verbindung der Formel
EMI0001.0024
in welcher Y einen abspaltbaren Rest, vorzugsweise Halogen, darstellt, mit einer Verbindung der Formel H,N-R,- X-R2 umsetzt. Die Umsetzung wird vorzugsweise in einem inerten Lösungsmittel, z. B. in Benzol, Toluol, Xylol, Dioxan usf., vorgenommen.
Erfindungsgemäss kann man beispielsweise fol gende Verbindungen miteinander umsetzen: o,o'-Bis-chlormethyl-biphenyl, o,o'-Bis-brommethyl-biphenyl, 2,2'-Bis-brommethyl-4,4'-dimethyl-biphenyl oder 2,2'-Bis-brommethyl-4,4'-methylmercapto-biphenyl mit Methylthioäthylamin, Äthylthioäthylamin, Propylthioäthylamin, Methylthioisopropylamin, Allylthioäthylamin, Isopropylthioäthylamin, Methoxyäthylamin, Äthoxyäthylamin,
Methoxypropylamin, Äthoxypropylamin, Alloxyäthylamin, Methylsulfinyläthylamin oder Athylsulfinyläthylamin.
Die erfindungsgemäss erhaltenen Dibenzazepine können gewünschtenfalls in ihre Säureadditionssalze übergeführt werden. Als zur Salzbildung geeignete Säuren lassen sich sowohl anorganische Säuren, wie z. B. Schwefelsäure, Chlorwasserstoffsäure, Brom wasserstoffsäure und Phosphorsäure, als auch orga nische Säuren, wie z. B.
Essigsäure, Glykolsäure, Citronensäure, Bernsteinsäure, Fumarsäure, Malein- säure, Dioxymaleinsäure, Methansulfonsäure und Oxyäthansulfonsäure, verwenden.
<I>Beispiel 1</I> 45 g o,o'-Bis-brommethyl-biphenyl werden mit 16,2 g Methylthioäthylamin in 500 cm3 Benzol während 20 Stunden bei Zimmertemperatur umge setzt. Nach Ausziehen mit verdünnter Salzsäure, Alkalisieren des sauren Extraktes und Extraktion mit Chloroform erhält man das Dibenzazepin der Formel
EMI0002.0004
als gelbes, dickflüssiges Öl, das unter 0,005 mm bei 150 C siedet. Es löst sich leicht in verdünnten orga nischen Säuren, wie Essigsäure, sowie in stark ver dünnter Salzsäure.
<I>Beispiel 2</I> 48,8 g o,o'-Bis-brommethyl-biphenyl und 16,6 g y-Methoxy propylamin werden in 500 cm3 Benzol 20 Stunden bei Zimmertemperatur umgesetzt. Nach dem Entfernen des Benzols im Vakuum wird der Rückstand mit 200 cm3 2n Natronlauge versetzt, die freigesetzte Base in 300 cm3 Chloroform aufgenom men und durch Destillation vorgereinigt (Kp. 0,1 mm: bis 175 C). Das Destillat wird in<B>100</B> cm3 Benzol warm gelöst und mit 2n Essigsäure extrahiert.
Die sauren Extrakte werden mit 2n Natronlauge alkali- siert, und das abgeschiedene Öl wird in Äther auf genommen. Nach dem Destillieren erhält man das Dibenzazepin der Formel
EMI0002.0021
als farbloses <B>öl;</B> Siedepunkt 0,1 mm: 147-150 C. Das in Äther hergestellte und aus Chloroform/Äther umkristallisierte Chlorhydrat dieser Verbindung schmilzt bei 158-159 C.
<I>Beispiel 3</I> In gleicher Weise, wie in den Beispielen 1 und 2 beschrieben, kann man o,o'-Bis-brommethyl-biphenyl in benzolischer Lösung mit Methylsulfinyläthylamin zur Reaktion bringen, wodurch man das Dibenzazepin der Formel
EMI0002.0030
erhält. Dieses kann gewünschtenfalls zum entspre chenden Sulfon oxydiert werden (z.
B. mit Hilfe von H202 in Eisessig usf.). <I>Beispiel 4</I> Durch Umsetzen von 2,2'-Bis-brommethyl-5-methylmercapto-biphenylmit Methylmercaptoäthyl- amin erhält man das Dibenzazepin der Formel
EMI0002.0041
<I>Beispiel 5</I> In gleicher Weise, wie im Beispiel 1 beschrieben, kann man 2,2'-Bis-brommethyl-5-chlor-biphenyl mit Methylmercaptoäthylamin umsetzen,
wodurch man das Dibenzazepin der Formel
EMI0002.0046
gewinnt. Setzt man anstelle des 2,2' Bis-brommethyl- 5-chlor-biphenyls das 2,2'-Bis-brommethyl-5,5'-di- chlor-biphenyl mit dem erwähnten Amin um, so er hält man das Dibenzazepin der Formel
EMI0002.0053
<I>Beispiel 6</I> Durch Umsetzen von o,
o'-Bis-brommethyl-bi- phenyl mit n-Propoxy-äthylamin in der im Beispiel 1 angegebenen Weise gewinnt man das Dibenzazepin der Formel
EMI0003.0005
Dieses kann als Hydrochlorid oder Fumarat iso liert werden.
Process for the production of new dibenzazepines The invention relates to a process for the production of new dibenzazepines of the formula
EMI0001.0005
in which R1 is a lower alkylene radical, R2 is a lower aliphatic radical, X is oxygen, sulfur, SO or S02, and the symbols R3, R4, RS and R6 are hydrogen, halogen, hydroxy, alkyl,
Represent alkoxy or alkyl mercapto.
The new azepines are intended to treat diseases of the vascular system, e.g. B. as vasodilators, etc., are used ver.
The new dibenzazepines can be produced in a simple manner by adding a compound of the formula according to the invention
EMI0001.0024
in which Y is a removable radical, preferably halogen, is reacted with a compound of the formula H, N-R, - X-R2. The reaction is preferably carried out in an inert solvent, e.g. B. in benzene, toluene, xylene, dioxane, etc., made.
According to the invention, for example, the following compounds can be reacted with one another: o, o'-bis-chloromethyl-biphenyl, o, o'-bis-bromomethyl-biphenyl, 2,2'-bis-bromomethyl-4,4'-dimethyl-biphenyl or 2,2'-bis-bromomethyl-4,4'-methylmercapto-biphenyl with methylthioethylamine, ethylthioethylamine, propylthioethylamine, methylthioisopropylamine, allylthioethylamine, isopropylthioethylamine, methoxyethylamine, ethoxyethylamine,
Methoxypropylamine, ethoxypropylamine, alloxyethylamine, methylsulfinylethylamine or ethylsulfinylethylamine.
The dibenzazepines obtained according to the invention can, if desired, be converted into their acid addition salts. Suitable acids for salt formation can be both inorganic acids, such as. B. sulfuric acid, hydrochloric acid, hydrobromic acid and phosphoric acid, as well as orga African acids such. B.
Use acetic acid, glycolic acid, citric acid, succinic acid, fumaric acid, maleic acid, dioxymaleic acid, methanesulphonic acid and oxyethanesulphonic acid.
<I> Example 1 </I> 45 g of o, o'-bis-bromomethyl-biphenyl are reacted with 16.2 g of methylthioethylamine in 500 cm3 of benzene for 20 hours at room temperature. After extraction with dilute hydrochloric acid, alkalization of the acidic extract and extraction with chloroform, the dibenzazepine of the formula is obtained
EMI0002.0004
as a yellow, viscous oil that boils below 0.005 mm at 150 C. It dissolves easily in dilute organic acids, such as acetic acid, and in very dilute hydrochloric acid.
<I> Example 2 </I> 48.8 g of o, o'-bis-bromomethyl-biphenyl and 16.6 g of γ-methoxypropylamine are reacted in 500 cm3 of benzene for 20 hours at room temperature. After the benzene has been removed in vacuo, the residue is treated with 200 cm3 of 2N sodium hydroxide solution, the released base is taken up in 300 cm3 of chloroform and pre-purified by distillation (boiling point 0.1 mm: up to 175 ° C.). The distillate is dissolved in <B> 100 </B> cm3 warm benzene and extracted with 2N acetic acid.
The acidic extracts are made alkaline with 2N sodium hydroxide solution and the separated oil is taken up in ether. After distilling, one obtains the dibenzazepine of the formula
EMI0002.0021
as a colorless <B> oil; </B> boiling point 0.1 mm: 147-150 C. The hydrochloride of this compound, which is produced in ether and recrystallized from chloroform / ether, melts at 158-159 C.
<I> Example 3 </I> In the same way as described in Examples 1 and 2, o, o'-bis-bromomethyl-biphenyl in a benzene solution can be reacted with methylsulfinylethylamine, whereby the dibenzazepine of the formula
EMI0002.0030
receives. If desired, this can be oxidized to the corresponding sulfone (e.g.
B. with the help of H202 in glacial acetic acid etc.). <I> Example 4 </I> By reacting 2,2'-bis-bromomethyl-5-methylmercapto-biphenyl with methylmercaptoethylamine, the dibenzazepine of the formula is obtained
EMI0002.0041
<I> Example 5 </I> In the same way as described in Example 1, 2,2'-bis-bromomethyl-5-chlorobiphenyl can be reacted with methylmercaptoethylamine,
which gives you the dibenzazepine of the formula
EMI0002.0046
wins. If, instead of the 2,2'-bis-bromomethyl-5-chlorobiphenyl, the 2,2'-bis-bromomethyl-5,5'-dichlorobiphenyl is reacted with the amine mentioned, then the dibenzazepine is obtained formula
EMI0002.0053
<I> Example 6 </I> By implementing o,
o'-Bis-bromomethyl-biphenyl with n-propoxy-ethylamine in the manner indicated in Example 1, the dibenzazepine of the formula is obtained
EMI0003.0005
This can be isolated as hydrochloride or fumarate.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6192158A CH367829A (en) | 1958-07-18 | 1958-07-18 | Process for the production of new dibenzazepines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6192158A CH367829A (en) | 1958-07-18 | 1958-07-18 | Process for the production of new dibenzazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH367829A true CH367829A (en) | 1963-03-15 |
Family
ID=4523983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6192158A CH367829A (en) | 1958-07-18 | 1958-07-18 | Process for the production of new dibenzazepines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH367829A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0192034A3 (en) * | 1985-01-10 | 1989-02-22 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Dibenzazepine derivatives, their preparation, starting materials for their preparation, and use of the dibenzazepine derivatives as pesticides |
-
1958
- 1958-07-18 CH CH6192158A patent/CH367829A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0192034A3 (en) * | 1985-01-10 | 1989-02-22 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Dibenzazepine derivatives, their preparation, starting materials for their preparation, and use of the dibenzazepine derivatives as pesticides |
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