DE1162846B - Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts. - Google Patents
Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts.Info
- Publication number
- DE1162846B DE1162846B DE1961B0063689 DEB0063689A DE1162846B DE 1162846 B DE1162846 B DE 1162846B DE 1961B0063689 DE1961B0063689 DE 1961B0063689 DE B0063689 A DEB0063689 A DE B0063689A DE 1162846 B DE1162846 B DE 1162846B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyalkyl
- esters
- nortropanes
- norgranatanes
- salts
- 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
- 150000002148 esters Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 inorganic acid halides Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AEIGUJIDYBREEB-UHFFFAOYSA-N 2-hydroxy-2-(2-methylphenyl)-2-phenylacetic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C1=CC=CC=C1 AEIGUJIDYBREEB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 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 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000001078 anti-cholinergic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- CINSFZZGMRTJKZ-UHFFFAOYSA-N 2-hydroxy-2-(4-methylphenyl)-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1C(O)(C(O)=O)C1=CC=CC=C1 CINSFZZGMRTJKZ-UHFFFAOYSA-N 0.000 description 1
- 229940087675 benzilic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LZVNPXGXPIHQTM-UHFFFAOYSA-N methyl 2-hydroxy-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=C(C)C=CC=1C(O)(C(=O)OC)C1=CC=CC=C1 LZVNPXGXPIHQTM-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND Internat. Kl.: C07d FEDERAL REPUBLIC OF GERMANY Internat. Class: C07d
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche KL: 12 ρ-13German KL: 12 ρ-13
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
B 63689 IVd/12 ρ
17. August 1961
13. Februar 1964B 63689 IVd / 12 ρ
17th August 1961
February 13, 1964
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Estern von N-(Hydroxyalkyl)-nortropanen bzw. -norgranatanen der FormelThe invention relates to a process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes of the formula
in der R Halogenatome oder Alkylgruppen, Y gegebenenfalls durch R einfach substituierte Phenyl-
oder Cycloalkylreste, X Wasserstoff- oder Halogenatome oder die Hydroxylgruppe, A Alkylgruppen
mit mindestens 2 C-Atomen bedeutet und η die Zahl 2 oder 3 darstellt, und ihren Salzen, die in
der Literatur bisher noch nicht beschrieben worden sind. Dieses Verfahren ist dadurch gekennzeichnet,
daß man in an sich bekannter Weise N-(Hydroxyalkyl)-nortropane bzw. -norgranatane der Formel
Verfahren zur Herstellung von Estern von
N-(Hydroxyalkyl)-nortropanen bzw.
-norgranatanen und ihren Salzenin which R is halogen atoms or alkyl groups, Y is phenyl or cycloalkyl radicals which are optionally monosubstituted by R, X is hydrogen or halogen atoms or the hydroxyl group, A is alkyl groups with at least 2 carbon atoms and η is the number 2 or 3, and their salts, which have not yet been described in the literature. This process is characterized in that, in a manner known per se, N- (hydroxyalkyl) -nortropanes or -norgranatanes of the formula processes for the preparation of esters of
N- (hydroxyalkyl) -nortropanes or
-norgranatans and their salts
Anmelder:Applicant:
C. F. Boehringer & Soehne G. m. b. H.,C. F. Boehringer & Soehne G. m. B. H.,
Mannheim-WaldhofMannheim-Waldhof
Als Erfinder benannt:Named as inventor:
Dr. rer. nat. Otto DoId, Lampertheim (Hess.),Dr. rer. nat. Otto DoId, Lampertheim (Hess.),
Dr.-Ing. Kurt Stach, Mannheim,Dr.-Ing. Kurt Stach, Mannheim,
Dr. med. Wolfgang Schaumann,Dr. med. Wolfgang Schaumann,
Mannheim-WaldhofMannheim-Waldhof
(CH2)*(CH 2 ) *
^A-OH^ A-OH
oder N-(Halogenalkyl)-nortropane bzw. -norgranatane mit substituierten Phenylessigsäuren der Formelor N- (haloalkyl) -nortropane or -norgranatane with substituted phenylacetic acids of the formula
R XR X
— COOH- COOH
oder ihren funktionellen Derivaten umsetzt, das erhaltene Reaktionsprodukt gegebenenfalls mit anorganischen Säurehalogeniden behandelt und die erhaltenen Ester gegebenenfalls mit Säuren umsetzt.or their functional derivatives, the reaction product obtained, optionally with inorganic ones Treated acid halides and optionally reacting the esters obtained with acids.
Die verfahrensgemäß hergestellten Verbindungen besitzen wertvolle anticholinergische Eigenschaften; sie sind dem z. B. aus dem Journal of the American Chemical Society, Bd. 64 (1942), S. 428 bis 433, bekannten Benzilsäureester des N-(Hydroxyäthyl)-piperidins hinsichtlich der zentralen und peripheren anticholinergischen Wirksamkeit bei zum Teil erheblich geringerer Toxizität deutlich überlegen und besitzen außerdem einen spezifischen zentralen Angriffspunkt. The compounds prepared according to the process have valuable anticholinergic properties; they are the z. From the Journal of the American Chemical Society, Vol. 64 (1942), pp. 428-433 Benzilic acid ester of N- (hydroxyethyl) piperidine with regard to the central and peripheral clearly superior to anticholinergic effectiveness and, in some cases, significantly lower toxicity also have a specific central point of attack.
In den nachstehenden Beispielen ist das erfindungsgemäße Verfahren erläutert.The process according to the invention is illustrated in the examples below.
1. p-Methylbenzilsäureester des
N-(/?-Hydroxyäthyl)-norgranatans1. p-methylbenzilic acid ester des
N - (/? - Hydroxyethyl) -norgranatans
23,2 g N-(/3-Hydroxyäthyl)-norgranatan, 35 g p-Methylbenzilsäure-methylester (F. 96 bis 980C) und 0,2 g Natrium werden 10 Stunden bei einem ©ruck von 25 mm auf 1200C erhitzt. Danach wird der Ansatz mit 6 η-Salzsäure und Äther aufgenommen, wobei sich eine ölige Substanz abscheidet.23.2 g of N - (/ 3-hydroxyethyl) -norgranatan, 35 g of p-methylbenzilic acid methyl ester (mp 96 to 98 0 C) and 0.2 g of sodium are 10 hours at a © jerk from 25 mm to 120 0 C heated. The batch is then taken up with 6η hydrochloric acid and ether, an oily substance separating out.
Diese Substanz wird kristallin erhalten, wenn man sie mit wenig Aceton versetzt und anreibt. Man saugt ab und erhält 34,6 g p-Methylbenzilsäureester des N-(/S-Hydroxyäthyl)-norgranatans in Form des Hydrochloride vom F. 195 bis 197°C (nach dem Umkristallisieren aus Isopropanol); die Ausbeute beträgt 58,6%.This substance is obtained in crystalline form if it is mixed with a little acetone and rubbed. Man sucks off and receives 34.6 g of p-methylbenzilic acid ester of N - (/ S-hydroxyethyl) -norgranatans in the form of the hydrochloride with a melting point of 195 ° to 197 ° C. (after recrystallization from isopropanol); the yield is 58.6%.
Eine wäßrige Lösung des Hydrochloride gibt beim Versetzen mit Sodalösung die ölige Base des N-(jS-Hydroxyäthyl)-norgranatan-(p-methyl)-benzilsäureesters. Aus einer ätherischen Lösung dieses Esters kann durch die Zugabe von Methansulfosäure in üblicher Weise das entsprechende Methansulfonat vom F. 149 bis 1510C (Isopropanol) gewonnen werden.An aqueous solution of the hydrochloride, when mixed with soda solution, gives the oily base of the N- (jS-hydroxyethyl) -norgranatan- (p-methyl) -benzilic acid ester. The corresponding methanesulfonate with a melting point of 149 to 151 ° C. (isopropanol) can be obtained in the usual way from an ethereal solution of this ester by adding methanesulfonic acid.
2. p-Chlorbenzilsäureester
des N-(/9-Hydroxyäthyl)-norgranatans2. p-chlorobenzilic acid ester
of N - (/ 9-hydroxyethyl) -norgranatane
33,9 g (0,2 Mol) N-(/9-Hydroxyäthyl)-norgranatan,33.9 g (0.2 mol) of N - (/ 9-hydroxyethyl) -norgranatane,
55,3 g (0,2 Mol) p-Chlorbenzilsäure-methylester (Kp.o,o8 174 bis 1800C) und 0,3 g Natrium werden55.3 g (0.2 mol) of p-Chlorbenzilsäure-methylester (Kp.o, o8 174-180 0 C) and 0.3 g of sodium are
8 Stunden bei einem Druck von 15 mm auf 1400C erhitzt. Nach dem Abkühlen wird der Ansatz mit Heated to 140 ° C. for 8 hours at a pressure of 15 mm. After cooling, the approach is with
409 508/436409 508/436
80 ml 6 η-Salzsäure und 40 ml Äther versetzt und 3 Stunden gerührt. Dabei fällt der p-Chlorbenzilsäureester des N-(/S-Hydroxyäthyl)-norgranatans in Form des Hydrochlorids kristallin aus und wird abgesaugt. Ausbeute 21,1 g (= 25,4%); F. 200 bis 2010C (nach dem Umkristallisieren aus Äthanol).80 ml of 6 η-hydrochloric acid and 40 ml of ether are added and the mixture is stirred for 3 hours. The p-chlorobenzilic acid ester of N - (/ S-hydroxyethyl) -norgranatans precipitates in crystalline form in the form of the hydrochloride and is filtered off with suction. Yield 21.1 g (= 25.4%); F. 200 to 201 0 C (after recrystallization from ethanol).
3. o-Methylbenzilsäureester
des N-(/?-Hydroxyäthyl)-norgranatans3. o-methylbenzilic acid ester
of N - (/? - Hydroxyethyl) -norgranatans
1010
24,2 g o-Methylbenzilsäure (F. 120 bis 122° C) und 5,6 g Kaliumhydroxyd werden in 150 ml absolutem Äthanol gelöst, kurze Zeit zum Sieden erhitzt und darauf bis zur Trockne eingeengt. Das erhaltene Kaliumsalz der o-Methylbenzilsäure wird 3 Stunden mit 22,4 g N-(jS-ChloräthyI)-norgranatan-Hydrochlorid (F. 237 bis 2380C) auf 140°C erhitzt. Darauf setzt man etwa 100 ml Isopropanol zu und erhitzt 3 Stunden am Rückfluß. Das ausgefallene Kaliumchlorid wird abgesaugt und das Isopropanol ab- ao destilliert. Man erhält 38,1 g o-Methylbenzilsäureester des N-(/J-Hydroxyäthyl)-norgranatans in Form des Hydrochlorids; die Ausbeute beträgt 88,6%; F. 197 bis 199°C (aus Isopropanol).24.2 g of o-methylbenzilic acid (melting point 120 to 122 ° C.) and 5.6 g of potassium hydroxide are dissolved in 150 ml of absolute ethanol, heated to the boil for a short time and then concentrated to dryness. The potassium salt of o-Methylbenzilsäure obtained is 3 hours, 22.4 g was heated to 140 ° C N- (jS-ChloräthyI) -norgranatan hydrochloride (F. 237-238 0 C). About 100 ml of isopropanol are then added and the mixture is refluxed for 3 hours. The precipitated potassium chloride is filtered off and the isopropanol off ao distilled. 38.1 g of o-methylbenzilic acid ester of N - (/ I-hydroxyethyl) -norgranatans are obtained in the form of the hydrochloride; the yield is 88.6%; 197 to 199 ° C (from isopropanol).
Aus der wäßrigen Lösung des Hydrochlorids erhält man nach Versetzen mit Sodalösung die Base vom F. 74 bis 750C (Petroläther).From the aqueous solution of the hydrochloride is obtained after treatment with sodium carbonate solution, the base mp 74-75 0 C (petroleum ether).
4. a-Chlor-p-methyldiphenylessigsäureester4. a-chloro-p-methyldiphenylacetic acid ester
des N-(^-Hydroxyäthyl)-norgranatansof N - (^ - hydroxyethyl) -norgranatane
10 g des nach dem Verfahren des Beispiels 1 hergestellten p-Methylbenzilsäureesters des N-(^-Hydroxyäthyl)-norgranatans werden in 200 ml Tetrachlorkohlenstoff und 20 ml Thionylchlorid etwa 3 Stunden am Rückfluß erhitzt; dabei löst sich das Salz allmählich vollständig auf. Dann wird bis zur Trockene eingeengt und der ölige Rückstand durch Verreiben mit Essigester zur Kristallisation gebracht. Das erhaltene Salz wird abgesaugt und dreimal aus Essigester umkristallisiert. Man erhält 5,7 g N-(/?-Hydroxyäthy^-norgranatan-a-chlor-p-methyldiphenylacetat als Hydrochlorid vom F. 140 bis 1410C; die Ausbeute beträgt 54,6%.10 g of the p-methylbenzilic acid ester of N - (^ - hydroxyethyl) -norgranatans prepared by the process of Example 1 are refluxed for about 3 hours in 200 ml of carbon tetrachloride and 20 ml of thionyl chloride; the salt gradually dissolves completely. It is then concentrated to dryness and the oily residue is crystallized by trituration with ethyl acetate. The salt obtained is filtered off with suction and recrystallized three times from ethyl acetate. To give 5.7 g of N - (/ - ^ Hydroxyäthy -norgranatan-a-chloro-p-methyldiphenylacetat as the hydrochloride, mp 140-141 0 C;?, The yield is 54.6%.
Claims (1)
(CHa)n N.
(CHa) n
Deutsche Patentschrift Nr. 680 662.Considered publications:
German patent specification No. 680 662.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961B0063689 DE1162846B (en) | 1961-08-17 | 1961-08-17 | Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts. |
| CH241066A CH423803A (en) | 1960-11-26 | 1961-10-13 | Process for the preparation of the hydrohalides of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes |
| CH1188261A CH423802A (en) | 1960-11-26 | 1961-10-13 | Process for the production of new esters of N - (- hydroxyalkyl) -nortropanes or -norgranatanes |
| GB3795661A GB920489A (en) | 1960-11-26 | 1961-10-23 | Nortropane and norgranatane derivatives |
| LU40856D LU40856A1 (en) | 1960-11-26 | 1961-11-23 | |
| BE610768A BE610768A (en) | 1960-11-26 | 1961-11-24 | New esters of n- (hydroxyalkyl) -nortropanes or - norgranatanes, their salts and quaternary ammonium compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961B0063689 DE1162846B (en) | 1961-08-17 | 1961-08-17 | Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1162846B true DE1162846B (en) | 1964-02-13 |
Family
ID=34398483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1961B0063689 Pending DE1162846B (en) | 1960-11-26 | 1961-08-17 | Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts. |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1162846B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219943B (en) * | 1964-06-30 | 1966-06-30 | Boehringer & Soehne Gmbh | Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE680662C (en) * | 1934-07-12 | 1939-09-06 | Chem Ind Basel | Process for the preparation of new basic esters of diphenyl acetic acid |
-
1961
- 1961-08-17 DE DE1961B0063689 patent/DE1162846B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE680662C (en) * | 1934-07-12 | 1939-09-06 | Chem Ind Basel | Process for the preparation of new basic esters of diphenyl acetic acid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219943B (en) * | 1964-06-30 | 1966-06-30 | Boehringer & Soehne Gmbh | Process for the preparation of esters of N- (hydroxyalkyl) -nortropanes or -norgranatanes and their salts |
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