DE1189549B - Process for the preparation of the fungistatically active 5, 7-dibromo-8-benzoyloxyquinoline - Google Patents
Process for the preparation of the fungistatically active 5, 7-dibromo-8-benzoyloxyquinolineInfo
- Publication number
- DE1189549B DE1189549B DES73190A DES0073190A DE1189549B DE 1189549 B DE1189549 B DE 1189549B DE S73190 A DES73190 A DE S73190A DE S0073190 A DES0073190 A DE S0073190A DE 1189549 B DE1189549 B DE 1189549B
- Authority
- DE
- Germany
- Prior art keywords
- dibromo
- benzoyloxyquinoline
- preparation
- benzoyl chloride
- benzoic anhydride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- GCMOMWMDHKAGKT-UHFFFAOYSA-N (5,7-dibromoquinolin-8-yl) benzoate Chemical compound BrC1=CC(Br)=C2C=CC=NC2=C1OC(=O)C1=CC=CC=C1 GCMOMWMDHKAGKT-UHFFFAOYSA-N 0.000 title description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 7
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N 8-Hydroxyquinoline Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- GLRLAIQRBWDBGX-UHFFFAOYSA-N 5,7-dibromo-8-phenylmethoxyquinoline Chemical compound BrC1=CC(Br)=C2C=CC=NC2=C1OCC1=CC=CC=C1 GLRLAIQRBWDBGX-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000001408 fungistatic Effects 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000001717 pathogenic Effects 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MUIOQQIOJYTXPZ-UHFFFAOYSA-N (5,7-dibromoquinolin-8-yl) acetate Chemical compound C1=CN=C2C(OC(=O)C)=C(Br)C=C(Br)C2=C1 MUIOQQIOJYTXPZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- ZDASUJMDVPTNTF-UHFFFAOYSA-N Broxyquinoline Chemical compound C1=CN=C2C(O)=C(Br)C=C(Br)C2=C1 ZDASUJMDVPTNTF-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 235000019749 Dry matter Nutrition 0.000 description 1
- 210000003608 Feces Anatomy 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- -1 benzoyl ester Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000249 desinfective Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 244000052769 pathogens Species 0.000 description 1
- 230000003285 pharmacodynamic Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche Kl.: 12 ρ-1/10German class: 12 ρ-1/10
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
1189 549
S73190IVd/12p
28. März 1961
25. März 19651189 549
S73190IVd / 12p
March 28, 1961
March 25, 1965
Das erfindungsgemäße Verfahren zur Herstellung der fungistatisch wirksamen Verbindung 5,7-Dibrom-8-benzoyloxychinolin ist dadurch gekennzeichnet, daß man in an sich bekannter Weise 5,7-Dibrom-8-hydroxychinolin The inventive method for production the fungistatically active compound 5,7-dibromo-8-benzoyloxyquinoline is characterized in that 5,7-dibromo-8-hydroxyquinoline is used in a manner known per se
a) mit Benzoesäureanhydrid bei erhöhter Temperatur in Gegenwart von Pyridin oder Schwefelsäure odera) with benzoic anhydride at elevated temperature in the presence of pyridine or sulfuric acid or
b) mit Benzoylchlorid oder einer Mischung von Benzoylchlorid und Benzoesäureanhydrid in Gegenwart eines inerten organischen Lösungsmittels und eines tertiären Aminsb) with benzoyl chloride or a mixture of benzoyl chloride and benzoic anhydride in Presence of an inert organic solvent and a tertiary amine
umsetzt.implements.
Das Verfahren wird beispielsweise so ausgeführt, daß S^-Dibrom-S-oxychinolin mit Benzoesäureanhydrid in Gegenwart von konzentrierter Schwefelsäure oder Pyridin auf höhere Temperatur, vorzugsweise 130 bis 1600C, erhitzt wird. Die Reaktionslösung wird sodann direkt oder nach Abdestillieren des überschüssigen Acylierungsmittels auf Eis gegossen. Nach Abnutschen und Nachwaschen mit Wasser erhält man den entsprechenden Ester. Verwendet man Benzoylchlorid oder eine Mischung von Benzoylchlorid und Benzoesäureanhydrid, dann werden das 5,7-Dibrom-8-oxychinolin und das Acylierungsmittel in einem inerten organischen Lösungsmittel, z. B. Benzol, Toluol, Xylol, Methylenchlorid, Äthylenchlorid, Tetrachlorkohlenstoff und Pyridin oder Triäthylamin oder Dimethylanilin, gelöst oder aufgeschlämmt. Die Lösung bzw. Mischung der Reaktionspartner wird bei Zimmertemperatur oder erhöhter Temperatur, vorzugsweise bei der Siedepunktstemperatur des verwendeten Lösungsmittels, gerührt. Schließlich wird der gebildete Ester nach bekannten Methoden isoliert und gereinigt.The process is for example performed so that S ^ S-dibromo-oxyquinoline with benzoic anhydride in the presence of concentrated sulfuric acid or pyridine to a higher temperature is preferably 130, heated to 160 0 C. The reaction solution is then poured onto ice either directly or after the excess acylating agent has been distilled off. After filtering off with suction and washing with water, the corresponding ester is obtained. If benzoyl chloride or a mixture of benzoyl chloride and benzoic anhydride is used, then the 5,7-dibromo-8-oxyquinoline and the acylating agent are dissolved in an inert organic solvent, e.g. B. benzene, toluene, xylene, methylene chloride, ethylene chloride, carbon tetrachloride and pyridine or triethylamine or dimethylaniline, dissolved or slurried. The solution or mixture of the reactants is stirred at room temperature or at an elevated temperature, preferably at the boiling point temperature of the solvent used. Finally, the ester formed is isolated and purified by known methods.
Der nach dem Verfahren hergestellte Benzoylester des 5,7-Dibrom-8-oxychinolins ist eine feste Base. Er zeichnet sich durch therapeutisch verwertbare pharmakodynamische Eigenschaften aus, indem er eine erhöhte Wirksamkeit gegen pathogene Pilze und auch andere Krankheitserreger aufweist. Die neue Verbindung soll als Desinfektionsmittel verwendet werden. Sie dient ferner als Zwischenprodukt für die Herstellung von Fungiziden und Medikamenten. Im nachfolgenden Beispiel ist der Schmelzpunkt in Celsiusgraden und unkorrigiert angegeben.The benzoyl ester of 5,7-dibromo-8-oxyquinoline prepared by the process is a solid base. He is characterized by therapeutically utilizable pharmacodynamic properties in that it has an increased Has effectiveness against pathogenic fungi and other pathogens. The new connection should be used as a disinfectant. It also serves as an intermediate product for manufacture of fungicides and medicines. In the example below, the melting point is in degrees Celsius and given uncorrected.
5,7-Dibrom-8-benzoxychinolin5,7-dibromo-8-benzoxyquinoline
Zu einer Suspension von 60,6 g 5,7-Dibrom-8-oxychinolin (Schmp. 195 bis 197°), 16,0 g Pyridin und
Verfahren zur Herstellung des fungistatisch
wirksamen 5,7-Dibrom-8-benzoyloxychinolinsTo a suspension of 60.6 g of 5,7-dibromo-8-oxyquinoline (melting point 195 ° to 197 °), 16.0 g of pyridine and a method for producing the fungistatic
effective 5,7-dibromo-8-benzoyloxyquinoline
Anmelder:Applicant:
SANDOZ Aktiengesellschaft, Basel (Schweiz)SANDOZ Aktiengesellschaft, Basel (Switzerland)
Vertreter:Representative:
Dr. W. Schalk, Dipl.-Ing. P. Wirth,Dr. W. Schalk, Dipl.-Ing. P. Wirth,
Dipl.-Ing. G. E. M. DannenbergDipl.-Ing. G. E. M. Dannenberg
und Dr. V. Schmied-Kowarzik,and Dr. V. Schmied-Kowarzik,
Frankfurt/M., Große Eschenheimer Str. 39Frankfurt / M., Große Eschenheimer Str. 39
Als Erfinder benannt:Named as inventor:
Dr. Jany Renz,Dr. Jany Renz,
Dr. Jean-Pierre Bourquin,Dr. Jean-Pierre Bourquin,
Dr. Erhard Schenker, Basel (Schweiz)Dr. Erhard Schenker, Basel (Switzerland)
Beanspruchte Priorität:
Schweiz vom 29. März 1960 (3542),
vom 11. Mai 1960 (5398)Claimed priority:
Switzerland of March 29, 1960 (3542),
dated May 11, 1960 (5398)
ecm Xylol läßt man bei Raumtemperatur unter Rühren 29,4 g Benzoylchlorid (Sdp. 194 bis 196°) hinzutropfen. Der Ansatz wird hierauf bei einer Badtemperatur von 140° unter Rühren während 4 Stunden zum Sieden am Rückfluß erhitzt. Nach dem Abkühlen auf Raumtemperatur wird das gebildete Pyridinhydrochlorid abgenutscht, mit 100 ecm Benzol nachgewaschen und das Filtrat im Vakuum zur Trockne eingeengt. Das rohe 5,7-Dibrom-8-benzoxychinolin hat einen Schmp. von 131 bis 139°. Nach wiederholtem Umkristallisieren der Substanz aus Tetrachlorkohlenstoff erhält man das analysenreine 5,7-Dibrom-8-benzoxychinolin vom konstanten Schmp. 140 bis 142°.29.4 g of benzoyl chloride (boiling point 194 ° to 196 °) are added dropwise at room temperature with stirring ecm xylene. The batch is then carried out at a bath temperature of 140 ° with stirring for 4 hours heated to reflux. After cooling to room temperature, the pyridine hydrochloride formed is suction filtered, washed with 100 ecm benzene and the filtrate concentrated to dryness in vacuo. The crude 5,7-dibromo-8-benzoxyquinoline has a melting point of 131 ° to 139 °. After repeated Recrystallization of the substance from carbon tetrachloride gives the analytically pure 5,7-dibromo-8-benzoxyquinoline from the constant melting point 140 to 142 °.
VergleichsversucheComparative experiments
In den folgenden Vergleichsversuchen wurde die fungistatische Wirkung der beiden bekannten Verbindungen In the following comparative tests, the fungistatic effect of the two known compounds
(I) 5,7-Dibrom-8-oxychinaldin (deutsche Patentschrift 852 953) und(I) 5,7-dibromo-8-oxychinaldine (German patent specification 852 953) and
(II) 5,7-Dibrom-8-acetoxychinolin (belgische Patentschrift 544 024)(II) 5,7-dibromo-8-acetoxyquinoline (Belgian patent 544 024)
mit 5,7-Dibrom-8-benzoyloxychinolin (III) verglichen.compared to 5,7-dibromo-8-benzoyloxyquinoline (III).
509 520/415509 520/415
Als Testorganismen wurden verwendet:The test organisms used were:
Aspergillus niger,Aspergillus niger,
Trichophyton interdigitalis,Trichophyton interdigitalis,
Trichophyton rubrum,Trichophyton rubrum,
Trichophyton mentagrophytes, Trichophyton gallinae.Trichophyton mentagrophytes, Trichophyton gallinae.
Die Prüfung wurde mit allen Pilzen in Verdünnungsreihen der Substanzen durchgeführt. Als Nährlösung diente helle, ungehopfte Bierwürze, die mit Leitungswasser 1: 8 verdünnt wurde (Trockensubstanzgehalt der verdünnten Bierwürze: 2%) mit einem Zusatz von 1% Glucose. Das pH beträgt 6,4. Die Substanzverdünnungen wurden in Doppelreihen in Röhrchen je 5 ml angesetzt und die Verdünnungsreihen mit Suspensionen der Stämme beimpft, so daß l^Konidien je 5 ecm resultierten. Die Bebrütung wurde bei 22°, die Kontrolle des Wachstums jede Woche, endgültig nach 3 Wochen durchgeführt. Die Verdünnungen sind in molaren Konzentrationen angegeben.The test was carried out with all fungi in dilution series of the substances. As a nutrient solution served light, unhopped wort made with tap water 1: 8 was diluted (dry matter content of the diluted wort: 2%) with an addition of 1% glucose. The pH is 6.4. The substance dilutions were made in double rows in tubes 5 ml each and inoculated the dilution series with suspensions of the strains, so that l ^ conidia 5 ecm each resulted. Incubation became final at 22 °, control of growth every week carried out after 3 weeks. The dilutions are given in molar concentrations.
binam
dungmanure
nigerNiger
inter-inter-
digit.digit.
rubrumrubrum
menta-
groph.Trichoph.
menta-
groph.
gallinaeTrichoph.
gallinae
II
in I.
II
in
400 000
50000050,000
400,000
500000
250 000
400 000100,000
250,000
400,000
640 000
1600 000160,000
640,000
1,600,000
400 000
500 000125,000
400,000
500,000
400 000
1000 000125,000
400,000
1,000,000
Aus den Daten der vorstehenden Tabelle ist deutlich ersichtlich, daß die Verbindungen I und II wesentlich schwächer wirksam sind als die Verbindung III.From the data in the table above it can be clearly seen that compounds I and II are essential are less effective than the compound III.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH354260A CH383970A (en) | 1960-03-29 | 1960-03-29 | Process for the preparation of new esters of 5,7-dibromo-8-oxyquinolines |
| CH539860A CH397680A (en) | 1960-03-29 | 1960-05-11 | Process for the production of novel esters of 5,7-chloro-8-oxyquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1189549B true DE1189549B (en) | 1965-03-25 |
Family
ID=25693274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES73190A Pending DE1189549B (en) | 1960-03-29 | 1961-03-28 | Process for the preparation of the fungistatically active 5, 7-dibromo-8-benzoyloxyquinoline |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE601859A (en) |
| CH (1) | CH397680A (en) |
| DE (1) | DE1189549B (en) |
| ES (1) | ES266124A1 (en) |
| GB (1) | GB974981A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984417A (en) * | 1971-12-27 | 1976-10-05 | Ajinomoto Co., Inc. | Method of producing active amino acid esters |
| CH732174A4 (en) * | 1974-05-29 | 1975-10-31 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE14971C (en) * | A. WOENIGER in Quaritz | Horizontal wind motor with regulation of the wing position by the wind pressure | ||
| DE891257C (en) * | 1950-05-16 | 1953-09-28 | Ciba Geigy | Process for the preparation of new esters of oxyquinolines |
-
1960
- 1960-05-11 CH CH539860A patent/CH397680A/en unknown
-
1961
- 1961-02-20 GB GB615461A patent/GB974981A/en not_active Expired
- 1961-03-27 BE BE601859A patent/BE601859A/en unknown
- 1961-03-28 ES ES0266124A patent/ES266124A1/en not_active Expired
- 1961-03-28 DE DES73190A patent/DE1189549B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE14971C (en) * | A. WOENIGER in Quaritz | Horizontal wind motor with regulation of the wing position by the wind pressure | ||
| DE891257C (en) * | 1950-05-16 | 1953-09-28 | Ciba Geigy | Process for the preparation of new esters of oxyquinolines |
Also Published As
| Publication number | Publication date |
|---|---|
| BE601859A (en) | 1961-09-27 |
| CH397680A (en) | 1965-08-31 |
| ES266124A1 (en) | 1961-11-01 |
| GB974981A (en) | 1964-11-11 |
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