CH374990A - Process for the production of new, spasmolytic compounds - Google Patents
Process for the production of new, spasmolytic compoundsInfo
- Publication number
- CH374990A CH374990A CH876163A CH876163A CH374990A CH 374990 A CH374990 A CH 374990A CH 876163 A CH876163 A CH 876163A CH 876163 A CH876163 A CH 876163A CH 374990 A CH374990 A CH 374990A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- new
- atoms
- compounds
- production
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 title description 3
- 230000002048 spasmolytic effect Effects 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- -1 alkyl radicals Chemical class 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 8
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229960001789 papaverine Drugs 0.000 description 4
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- XTMWXULZPRKUTG-UHFFFAOYSA-N n-iodo-n-methylmethanamine Chemical compound CN(C)I XTMWXULZPRKUTG-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000000956 myotropic effect Effects 0.000 description 1
- PHNJOCFERRWJLI-UHFFFAOYSA-N n-ethyl-n-iodoethanamine Chemical compound CCN(I)CC PHNJOCFERRWJLI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/28—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung neuer, spasmolytisch wirksamer Verbindungen
Die vorliegende Erfindung betrifft ein Verfahren zur r Herstellung neuer, spasmolytisch wirksamer Verbindungen.
Im Schweizer Patent Nr. 371112 sind basische Ather entsprechend der Formel I beschrieben :
EMI1.1
worin Ri für Wasserstoff oder ein Halogen, vorzwgs- weise Chlor, steht, R2 und R3 f r Wasserstoff oder niede, re Alkylreste mit 1-2 C-Atomen sttehen, woKi mindestens einer dieser beiden Reste jedoch einem Alkylrest der erwÏhnten Art bedeutet, R4 f r -CH=CH-oder-CH2-CH2-steht und R5 f r eine Dialkylaminogruppe, deren Alkylreste je 1-2 C Atome enthalten, oder f r einen 5- oder 6gliedrigen, ein Stickstoffatom enthaltenden und über das Stick stoffatom gebundenen heterocyclischen Rest steht.
Es wurde nunmehr gefunden, dass quatemäre Ammoniumverbindungen dieser basischen ¯ther ebenfalls eine hohe. spasmolytische Wirksamkeit besitzen. Die gemäss der Erfindung herzustellenden quaternÏren Ammoniumverbindungen entsprechen der allgemeinen Formel II :
EMI1.2
worin R6 f r Wasserstoff oder ein Halogen, vorzugs- weise Chlor, steht, R7 und R8 f r Wasserstoff oder niedere Alkylreste mit 1-2 C-Atomen stehen, wobei mindestens einer dieser beiden Reste jedoch einen Alkylrest der erwÏhnten Art bedeutet, R9 f r -CH=CH- oder -CH2-CH2- steht, R10 und R11 Alkylreste mit 1-2 C-Atomen oder zusammen mit t dem Stickstoffatom, an das sie gebunden sind, einen 5-oder 6gliedrigen, ein Stickstoffatom enthaltenden heterocyclischen Rest darstellen, R12 Alkylreste mit 1-4 C-Atomen und X ein Halogenatom sind.
Als 5-oder 6gliedriger, ein Stickstoffatom ent- haltender heterocyclischer Rest kommt bevorzugt dex Piperidisno-, Morpholino-und Pyrrolidinorest in B. e tracht. R12 ist bevorzugt Methyl oder Äthyl.
Die neuen Verbindungen der Formel II werden erfindungsgemäss hergestellt, indem ein basischer ¯ther der obigen Formel I vorzugsweise in Gegen- wart eines organischen Lösungsmittels mit einem Halogenalkyl mit 1-4 C-Atomen, vorzugsweise unter Erhitzen, umgesetzt wird und die gebildete quater- näne Ammoniumverbindung aus dem Reaktions gemasch isoliert wird.
Die neuen Produkte besitzen eine ausgeprägte e Papaverinwirkung, verbunden mit einer guten anti cholinergischen Wirkung. Die folgende Tabelle zeigt einen Vergleich mit quaternären Verbindungen be kannter Produkte ähnlicher Konstitution. Die in der Tabelle angeführten, erfindu. ngsgemäss hergestellten Produkte entsprechen der Formel III
EMI2.1
Die jeweilige Bedeutung R6, R7, R8 und R13 ist in den ersten vier Reihen der Tabelle angegeben.
Die Reihe V der Tabelle zeigt den anticholinergischen Aktivitätsindex im Vergleich zu Atropin (= 1), gemessen am Carbaminoylcholinchlorid-Krampf unter Verwendung einer Konzentration von 10-7 g/ml. Die Reihe VI der Tabelle zeigt die myotrope Wirkung im Vergleich zu Papaverin (= 1), gemessen unter Verwendung einer Konzentration von 4 . 10-4 BaCl2 g/ml.
Die Reihe VII, der Tabelle zeigt die Histamin-antago- nistische Wirkung im Vergleich zu Diphenhydramin (= 1), gemessen in einer Konzentration von 1 . 10-6 Histamn g/ml.
Tabelle
EMI2.2
<SEP> R8 <SEP> R13 <SEP> V <SEP> VI <SEP> VII
<tb> H <SEP> H <SEP> CH3 <SEP> Dimethylamino-brom-Ïthylat <SEP> 1,2 <SEP> 1,1 <SEP> 0, <SEP> 04
<tb> H <SEP> H <SEP> CH9 <SEP> Dimethylamino-jod-Ïthylat <SEP> 1,2 <SEP> 0,5 <SEP> 0, <SEP> 03
<tb> Cl <SEP> CH3 <SEP> H <SEP> Dimethylamino-jod-methylat <SEP> 0,8 <SEP> 0,7 <SEP> 0, <SEP> 4
<tb> H <SEP> CH3 <SEP> H <SEP> Pipfrldino-brommethylat <SEP> 1, <SEP> 0 <SEP> 1, <SEP> 4 <SEP> 0, <SEP> 03
<tb> H <SEP> H <SEP> H <SEP> Dimethylamino-jod-methylat <SEP> 1,0 <SEP> 0,1 <SEP> 0, <SEP> 05
<tb> H <SEP> H <SEP> H <SEP> DiÏthylamino-jod-methylat <SEP> 3,0 <SEP> 0,06 <SEP> 0, <SEP> 008
<tb>
Alle Versuche wurden am isolierten Meerschwein chendarm ausgeführt.
Die Tabelle zeigt, dass die neuen Produkte eine Papaverinwirkung besitzen, die 10-bis 20fach grösser ist als die Papaverinwirkung der vorbekannten Produkte, bei denen R7 und R8 für Wasserstoff stehen.
Die anticholinergische Wirkung der neuen Produkte ist etwa gleich gross wie die des Atropins.
Beispiel 1 ¯-Dimethylamino-Ïthyl-(6-methyl-2,5-endomethylen ?3-tetrahydrobenzhydryl)-Ïther-jod-methylat
28, 5 g (0, 1 Mol) ¯-DimethylaminoÏthyl-(6-methyl2, 5-endomethylen-?3-tetrahydrobenzhydryl)-Ïther werdenin 75 ml Essigsäureäthylester gelöst und mit
14, 2 g (0, 1 Mol) Methyljodid versetzt. Nach 24 Stunden werden 250 ml absoluter Ather zugegeben, das ausgefallene Salz abgesaugt und aus Aceton oder
EssigsÏureÏthylester umkristallisiert. Fp 175-184¯C.
Ausbeute : 50-60 11/o, der Theorie.
Beispiet 2 ¯-Piperidino-Ïthyl-(α-methyl-2,5-endomethylen-?3- tetrahydrobenzhydryl)-Ïther-brom-methylat
32, 5 g ¯-Piperidino-Ïthyl-(α-methyl-2,5-endo- methylen-ds-tetrahydro-benzhydxyl)-äther werden in 100 mlEssigsäuTeäfhylestergelöst, mit 19 g Methyl- bromid versetzt und 5 Minuten zum Sieden erhitzt.
Nach dem Erkalten wird das ausgefallene Salz abge saugt und aus Aceton unter Zusatz von etwas Alkohol umkristallisiert.
Fp 220-222 C.
Analog den Beispielenlund 2 wurden aus den entsprechenden tertiären Basen die folgenden Quar- tärsalze hergestellt :
EMI3.1
EMI4.1
Process for the production of new, spasmolytic compounds
The present invention relates to a process for the production of new, spasmolytically active compounds.
Basic ethers according to formula I are described in Swiss patent No. 371112:
EMI1.1
where Ri stands for hydrogen or a halogen, preferably chlorine, R2 and R3 stand for hydrogen or lower, more alkyl radicals with 1-2 C atoms, whereKi stands for at least one of these two radicals, however, an alkyl radical of the type mentioned, R4 for -CH = CH- or -CH2-CH2- and R5 represents a dialkylamino group, the alkyl radicals of which each contain 1-2 C atoms, or a 5- or 6-membered heterocyclic radical containing a nitrogen atom and bonded via the nitrogen atom.
It has now been found that quaternary ammonium compounds of these basic ethers also have a high. Have spasmolytic effectiveness. The quaternary ammonium compounds to be prepared according to the invention correspond to the general formula II:
EMI1.2
in which R6 stands for hydrogen or a halogen, preferably chlorine, R7 and R8 stand for hydrogen or lower alkyl radicals having 1-2 C atoms, but at least one of these two radicals is an alkyl radical of the type mentioned, R9 for -CH = CH- or -CH2-CH2-, R10 and R11 represent alkyl radicals with 1-2 C atoms or, together with the nitrogen atom to which they are bonded, a 5- or 6-membered heterocyclic radical containing a nitrogen atom, R12 represents alkyl radicals with 1-4 carbon atoms and X is a halogen atom.
The 5- or 6-membered heterocyclic radical containing a nitrogen atom is preferably the piperidisno, morpholino and pyrrolidino radical in B. e. R12 is preferably methyl or ethyl.
The new compounds of the formula II are prepared according to the invention by reacting a basic ether of the above formula I, preferably in the presence of an organic solvent, with a haloalkyl having 1-4 C atoms, preferably with heating, and the quaternene formed Ammonium compound is isolated from the reaction gemasch.
The new products have a pronounced papaverine effect, combined with a good anti-cholinergic effect. The following table shows a comparison with quaternary compounds of known products of similar constitution. The listed in the table, inventu. Products manufactured in accordance with the formula III
EMI2.1
The respective meaning of R6, R7, R8 and R13 is given in the first four rows of the table.
Row V of the table shows the anticholinergic activity index in comparison to atropine (= 1), measured on carbaminoylcholine chloride spasm using a concentration of 10-7 g / ml. Row VI of the table shows the myotropic effect compared to papaverine (= 1), measured using a concentration of 4. 10-4 BaCl2 g / ml.
Row VII of the table shows the histamine-antagonistic effect in comparison with diphenhydramine (= 1), measured at a concentration of 1. 10-6 histamn g / ml.
table
EMI2.2
<SEP> R8 <SEP> R13 <SEP> V <SEP> VI <SEP> VII
<tb> H <SEP> H <SEP> CH3 <SEP> dimethylamino-bromo-ethylate <SEP> 1,2 <SEP> 1,1 <SEP> 0, <SEP> 04
<tb> H <SEP> H <SEP> CH9 <SEP> Dimethylamino-iodine-ethylate <SEP> 1.2 <SEP> 0.5 <SEP> 0, <SEP> 03
<tb> Cl <SEP> CH3 <SEP> H <SEP> dimethylamino iodine methylate <SEP> 0.8 <SEP> 0.7 <SEP> 0, <SEP> 4
<tb> H <SEP> CH3 <SEP> H <SEP> Pipfrldino-bromomethylate <SEP> 1, <SEP> 0 <SEP> 1, <SEP> 4 <SEP> 0, <SEP> 03
<tb> H <SEP> H <SEP> H <SEP> dimethylamino iodine methylate <SEP> 1.0 <SEP> 0.1 <SEP> 0, <SEP> 05
<tb> H <SEP> H <SEP> H <SEP> diethylamino iodine methylate <SEP> 3.0 <SEP> 0.06 <SEP> 0, <SEP> 008
<tb>
All experiments were carried out on the isolated guinea pig.
The table shows that the new products have a papaverine effect that is 10 to 20 times greater than the papaverine effect of the previously known products in which R7 and R8 stand for hydrogen.
The anticholinergic effect of the new products is about the same as that of atropine.
Example 1 ¯-Dimethylamino-ethyl- (6-methyl-2,5-endomethylene-3-tetrahydrobenzhydryl) -ether-iodo-methylate
28.5 g (0.1 mol) of ¯-dimethylaminoethyl (6-methyl2, 5-endomethylene-3-tetrahydrobenzhydryl) ether are dissolved in 75 ml of ethyl acetate and mixed with
14.2 g (0.1 mol) of methyl iodide were added. After 24 hours, 250 ml of absolute ether are added, the precipitated salt is suctioned off and extracted from acetone or
Recrystallized ethyl acetate. 175-184¯C.
Yield: 50-60 11 / o, of theory.
For example, 2¯-piperidino-ethyl- (α-methyl-2,5-endomethylene-? 3-tetrahydrobenzhydryl) -ether-bromomethylate
32.5 g of ¯-piperidino-ethyl (α-methyl-2,5-endomethylene-ds-tetrahydrobenzhydxyl) ether are dissolved in 100 ml of ethyl acetate, mixed with 19 g of methyl bromide and heated to the boil for 5 minutes .
After cooling, the precipitated salt is filtered off with suction and recrystallized from acetone with the addition of a little alcohol.
Mp 220-222 C.
Analogously to Examples 1 and 2, the following quarternary salts were prepared from the corresponding tertiary bases:
EMI3.1
EMI4.1
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA27439A DE1052982B (en) | 1957-06-29 | 1957-06-29 | Process for the production of new, spasmolytically effective, basic ethers, their salts or quaternary ammonium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH374990A true CH374990A (en) | 1964-02-15 |
Family
ID=6926391
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6113858A CH371112A (en) | 1957-06-29 | 1958-06-27 | Process for the production of new, spasmolytic compounds |
| CH876163A CH374990A (en) | 1957-06-29 | 1958-06-27 | Process for the production of new, spasmolytic compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6113858A CH371112A (en) | 1957-06-29 | 1958-06-27 | Process for the production of new, spasmolytic compounds |
Country Status (2)
| Country | Link |
|---|---|
| CH (2) | CH371112A (en) |
| DE (1) | DE1052982B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152410B (en) * | 1959-04-01 | 1963-08-08 | Koninklijke Pharma Fab Nv | Process for the preparation of dibenzocycloheptane derivatives with spasmolytic and central effects |
| NL246462A (en) | 1959-08-06 | |||
| DE1108684B (en) * | 1960-01-29 | 1961-06-15 | Boehringer & Soehne Gmbh | Process for the production of new basic ethers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955895C (en) * | 1953-08-05 | 1957-01-10 | Gross Berliner Eisenmoebel Fab | Safety device for the support frame of the headboard of a bed, in particular a hospital bed |
-
1957
- 1957-06-29 DE DEA27439A patent/DE1052982B/en active Pending
-
1958
- 1958-06-27 CH CH6113858A patent/CH371112A/en unknown
- 1958-06-27 CH CH876163A patent/CH374990A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1052982B (en) | 1959-03-19 |
| CH371112A (en) | 1963-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH374990A (en) | Process for the production of new, spasmolytic compounds | |
| DE814294C (en) | Process for the preparation of insecticidal phosphorus compounds | |
| DE1088481B (en) | Process for the preparation of new compounds of the tetracycline series | |
| DE1668550C (en) | ||
| CH396870A (en) | Process for the preparation of N-substituted carbamic acid derivatives | |
| CH369759A (en) | Process for the preparation of N-alkylpiperidine-α-carboxylic acid anilides | |
| AT254868B (en) | Process for the preparation of new disubstituted isoxazole compounds | |
| DE1158510B (en) | Process for the preparation of metal carbonyls partially substituted by cyclopentadienyl or indenyl radicals | |
| AT221520B (en) | Process for the preparation of new N, N'-tetrasubstituted 3-amino-2-azaprop-2-en-1-ylidene ammonium halides | |
| AT255409B (en) | Process for the preparation of new substituted benzimidazole derivatives and their salts | |
| AT258936B (en) | Process for the production of new basic substituted cyclic ureas and their salts | |
| AT204554B (en) | Process for the preparation of N-alkyl-α-piperidinecarboxylic acid anilides | |
| AT226240B (en) | Process for the preparation of new N-substituted carbamic acid esters | |
| AT229873B (en) | Process for the preparation of 1,4-disubstituted piperazine derivatives | |
| AT238186B (en) | Process for the preparation of new pyrrolidine compounds | |
| AT243445B (en) | Process for the preparation of new 3- (dibenzo- [a, d] -1, 4-cycloheptadien-5-yloxy) -nortropanes substituted on the nitrogen and of salts of these compounds | |
| AT211823B (en) | Process for the preparation of new aryloxyacetic acid amides | |
| AT231452B (en) | Process for the preparation of new, racemic or optically active 1- (p-chlorophenyl- [pyridyl- (2 ')] -methyl) -4-hydroxyethoxyethyl-piperazine | |
| AT259542B (en) | Process for the preparation of new 2-amino-5-halobenzylamines and their addition salts with acids | |
| AT272353B (en) | Process for the production of basic substituted phthalazones and their salts and quaternary ammonium compounds | |
| CH390920A (en) | Process for the preparation of alkyleneiminoquinones | |
| AT208879B (en) | Process for the preparation of new theophylline bases | |
| AT273967B (en) | Process for the preparation of new salts of substituted s-triazines | |
| AT267075B (en) | Process for the preparation of new 3- (dibenzo- [a, d] -1,4-cycloheptadien-5-yloxy) -nortropanes substituted on the nitrogen and of salts of these compounds | |
| AT268243B (en) | Process for the preparation of new 2-amino-benzylamines and their acid addition salts |