DE1228262B - Process for the production of new pyrrolidine derivatives and their salts - Google Patents
Process for the production of new pyrrolidine derivatives and their saltsInfo
- Publication number
- DE1228262B DE1228262B DES72107A DES0072107A DE1228262B DE 1228262 B DE1228262 B DE 1228262B DE S72107 A DES72107 A DE S72107A DE S0072107 A DES0072107 A DE S0072107A DE 1228262 B DE1228262 B DE 1228262B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- salts
- general formula
- iii
- pyrrolidine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. α.:Int. α .:
C07dC07d
Deutsche Kl.: 12p-2German class: 12p-2
Nummer: 1228262Number: 1228262
Aktenzeichen: S72107IVd/12pFile number: S72107IVd / 12p
Anmeldetag: 18. Januar 1961 Filing date: January 18, 1961
Auslegetag: 10. November 1966Opening day: November 10, 1966
Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Pyrrolidinderivaten der allgemeinen Formel IThe invention relates to a process for the preparation of new pyrrolidine derivatives of the general Formula I.
CH2 CH2 CH 2 CH 2
worin Ri ein Wasserstoffatom, ein Halogenatom oder eine niedere Alkylgruppe und R2 eine niedere Alkylgruppe bedeutet, und ihren Salzen, welches dadurch gekennzeichnet ist, daß man in an sich bekannter Weise ein Diphenylmethanderivat der allgemeinen Formel IIwherein Ri is a hydrogen atom, a halogen atom or a lower alkyl group and R 2 is a lower alkyl group, and its salts, which is characterized in that a diphenylmethane derivative of the general formula II
IIII
Verfahren zur Herstellung von neuen
Pyrrolidinderivaten und ihren SalzenMethod of making new
Pyrrolidine derivatives and their salts
Anmelder:Applicant:
SANDOZ A. G., Basel (Schweiz)SANDOZ A. G., 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, Patentanwälte,and Dr. V. Schmied-Kowarzik, patent attorneys,
Frankfurt/M., Große Eschenheimer Str. 39Frankfurt / M., Große Eschenheimer Str. 39
Als Erfinder benannt:Named as inventor:
Dr. Ernst Jucker, Binningen;Dr. Ernst Jucker, Binningen;
Dr. Anton Ebnöther, Basel (Schweiz)Dr. Anton Ebnöther, Basel (Switzerland)
Beanspruchte Priorität:Claimed priority:
Schweiz vom 19. Januar 1960(537),
vom 3. August 1960 (8807),
vom 27. September 1960 (10 897)Switzerland of January 19, 1960 (537),
dated August 3, 1960 (8807),
of September 27, 1960 (10 897)
mit einer Pyrrolidinverbindung der allgemeinen Formel IIIwith a pyrrolidine compound of the general formula III
H2C CH2 H 2 C CH 2
X-CH2- CH2 — HC CH2 X-CH 2 - CH 2 - HC CH 2
\N/\ N /
R2 R 2
IIIIII
worin Ri und R2 in den Formeln II und III die obenstehende Bedeutung besitzen und ein X die Hydroxylgruppe und das andere ein Chlor- oder Bromatom bedeutet, umsetzt und gegebenenfalls die erhaltenen Basen mit Säuren behandelt.in which Ri and R 2 in formulas II and III have the above meaning and one X is the hydroxyl group and the other is a chlorine or bromine atom, and, if appropriate, the bases obtained are treated with acids.
Das Verfahren wird beispielsweise wie folgt ausgeführt: Man kondensiert ein Diphenylmethanderivat der Formel II, in dem X für die Hydroxylgruppe steht, in Gegenwart von Natriumamid mit einer Verbindung der Formel III, in dem X für ein Chlor- oder Bromatom steht, in einem indifferenten organischen Lösungsmittel, wie z. B. Benzol. Zur Vervollständigung der Reaktion erhitzt man noch mehrere Stunden zum Sieden. Das Endprodukt der Formel I wird aus dem Reaktionsgemisch nach bekannten Methoden isoliert, durch Destillation im Hochvakuum gereinigt und gewünschtenfalls mit anorganischen oder organischen Säuren in Säureadditionssalze übergeführt.The process is carried out, for example, as follows: A diphenylmethane derivative is condensed of formula II, in which X stands for the hydroxyl group, in the presence of sodium amide with a compound of the formula III in which X is a chlorine or bromine atom, in an indifferent one organic solvents, such as. B. benzene. The mixture is heated to complete the reaction several hours to simmer. The end product of formula I is made from the reaction mixture according to known methods isolated, purified by distillation in a high vacuum and, if desired, converted into acid addition salts with inorganic or organic acids.
Das Verfahren kann auch so durchgeführt werden, daß man während mehrerer Stunden 1-Methylpyrrolidinyl-(2)-äthanol in Gegenwart eines halogenwasserstoffbindenden Mittels, wie z. B. wasserfreies Natriumcarbonat, mit p-Chlorphenyl-phenylmethylchlormethan bei erhöhter Temperatur kondensiert. Das Reaktionsgemisch wird anschließend mit einem indifferenten organischen Lösungsmittel, beispielsweise Benzol, versetzt, anorganische Salze durch Filtration entfernt, und das Filtrat im Vakuum eingedampft.The process can also be carried out in such a way that 1-methylpyrrolidinyl- (2) -ethanol for several hours in the presence of a hydrogen halide binding agent, such as. B. anhydrous sodium carbonate, with p-chlorophenyl-phenylmethylchloromethane condensed at elevated temperature. The reaction mixture is then with a Indifferent organic solvents, for example benzene, added, inorganic salts through Filtration removed and the filtrate evaporated in vacuo.
Die verfahrensgemäß hergestellten, bisher unbekannten Äther sind auf Grund ihrer interessanten pharmakodynamischen Eigenschaften zur Verwendung als Heilmittel in hohem Maße geeignet.The so far unknown ethers produced according to the process are interesting because of their pharmacodynamic properties are highly suitable for use as medicaments.
609 710/302609 710/302
Sie zeichnen sich bei geringer Toxizität durch eine bemerkenswerte histaminhemmende Wirkung bei schwacher acetylcholinhemmender (atropinähnlicher) Wirkung aus. Die neuen Verbindungen sollen deshalb in der Therapie als Antihistaminika Verwendung finden.They are characterized by a remarkable histamine-inhibiting effect with low toxicity weak acetylcholine-inhibiting (atropine-like) effect. The new connections should therefore find use in therapy as antihistamines.
In den nachfolgenden Beispielen, die die Ausführung des Verfahrens erläutern sollen, erfolgen alle Temperaturangaben in Celsiusgraden. Die Schmelz- und Siedepunkte sind nicht korrigiert.In the following examples, which are intended to explain the implementation of the process, take place all temperature data in degrees Celsius. The melting and boiling points are not corrected.
N-Methyl-2-[2'-(a-methyl-benzhydryloxy)-äthyl]-N-methyl-2- [2 '- (a-methyl-benzhydryloxy) -ethyl] -
pyrrolidin .pyrrolidine.
Man versetzt die Suspension von 2,3g pulverisiertem Natriumamid in 30 ecm Benzol mit 9,9 g a-Methylbenzhydrol. Anschließend werden 7,4 g N-Methyl-pyrrolidinyl-(2)'äthylchlorid zugesetzt und die Lösung 20 Stunden am Rückfluß zum Sieden erhitzt. Dann schüttelt man zuerst mit Wasser und darauf viermal mit je 25 ecm 2 η-Salzsäure aus, stellt die sauren Auszüge unter guter Kühlung alkalisch und nimmt das ausgefallene öl in Äther auf. Nach Trocknen' der' ätherischen Lösung über Kaliumcarbonat ,wird das Lösungsmittel eingedampft und der Rückstand im Hochvakuum fraktioniert destilliert, wobei das N-Methyl-2-[2'-(a-methylbenzhydryloxy)-äthyl]-pyrrolidin bei 143° unter einem Druck von 0,02 mm Hg übergeht. n2i = 1,5510.The suspension of 2.3 g of powdered sodium amide in 30 ecm of benzene is mixed with 9.9 g of α-methylbenzhydrol. 7.4 g of N-methyl-pyrrolidinyl- (2) 'ethyl chloride are then added and the solution is refluxed for 20 hours. Then it is shaken out first with water and then four times with 25 ecm 2 η-hydrochloric acid each time, the acidic extracts are rendered alkaline with good cooling and the precipitated oil is taken up in ether. After drying 'the' ethereal solution over potassium carbonate, the solvent is evaporated and the residue is fractionally distilled in a high vacuum, the N-methyl-2- [2 '- (a-methylbenzhydryloxy) ethyl] pyrrolidine at 143 ° under one pressure of 0.02 mm Hg. n 2 i = 1.5510.
Das neutrale Naphthalin-l,5-disulfonat schmilzt nach Kristallisation aus Äthanol bei 175 bis 176° (Zersetzung).The neutral naphthalene-1,5-disulfonate melts after crystallization from ethanol at 175 to 176 ° (Decomposition).
Analog wie oben beschrieben werden aus N-Methyl-pyrrolidinyl-(2)-äthylchlorid und einem Diphenylcarbinol der Formel II folgende Verbindungen erhalten: ' 'Analogously to that described above, N-methyl-pyrrolidinyl- (2) -ethyl chloride is obtained and a diphenylcarbinol of the formula II, the following compounds are obtained: ''
BrechungsindexBp / mm Hg
Refractive index
(Formel II)Starting substance
(Formula II)
pyrrolidin
N-Methyl-2-[2'-(a-methyl-p-brom-benzhydryloxy)-äthyI]-
pyrrolidin
N-Methyl-2-[2'-(a-methyl-p-methyl-benzhydryloxy)-äthyl]-
pyrrolidinN-methyl-2- [2 '- (a-methyl-p-chloro-benzhydryloxy) -ethyl] -
pyrrolidine
N-methyl-2- [2 '- (a-methyl-p-bromo-benzhydryloxy) -ethyI] -
pyrrolidine
N-methyl-2- [2 '- (a-methyl-p-methyl-benzhydryloxy) -ethyl] -
pyrrolidine
nf = 1,5582
162°/0,02
n2i = 1,5698
15270,02
«F = 1,5480154 o / 0.02
nf = 1.5582
162 ° / 0.02
n 2 i = 1.5698
15270.02
«F = 1.5480
phenylcarbinol
Methyl-p-bromphenyl-
phenylcarbinol
Methyl-p-tolyl-
phenylcarbinolMethyl-p-chlorophenyl-
phenylcarbinol
Methyl-p-bromophenyl-
phenylcarbinol
Methyl-p-tolyl-
phenylcarbinol
N-Methyl-2-[2'-(2-methyl-p-chlorbenzhydryloxy)-äthyl]-pyrrolidin N-methyl-2- [2 '- (2-methyl-p-chlorobenzhydryloxy) ethyl] pyrrolidine
ρ - Chlorphenyl - phenyl - methyl - chlormethan, das durch Versetzen einer Lösung von 11,6 g a-Methylp-chlorbenzhydrol in 100 ecm Pentan mit 5 g Calciumchlorid, Sättigen derselben bei 0° mit Chlorwasserstoff, anschließendes Stehenlassen des Gemisches 2 Stunden lang bei 0°, wobei ein leichter Chlorwasserstoffstrom eingeleitet wird, Abfiltrieren des Calciumchlorids und Entfernung des Lösungsmittels durch Einblasen von Stickstoff bei 0° erhalten worden ist, wird bei 0° mit 13,0 g l-Methyl-2-pyrrolidinyl-äthanol versetzt und das Reaktionsgemisch während 18 Stunden bei Raumtemperatur stehengelassen. Nach Zusatz von Äther und mehrmaligem Waschen mit Wasser (bis pH 7), wird die ätherische Phase abgetrennt und dreimal mit 5%iger Essigsäure extrahiert. Die vereinigten Extrakte macht man anschließend unter Eiskühlung mit Kaliumhydroxyd alkalisch und nimmt das ausgeschiedene öl wieder in Äther auf. Nach Trocknen der ätherischen Lösung über Kaliumcarbonat wird das Lösungsmittel eingedampft und der Rückstand im Kugelrohr destilliert, wobei dasN-Methyl-2-[2'-(2-methyl - ρ - chlorbenzhydryloxy) - äthyl] - pyrrolidin als gelbes öl bei 125 bis 140° unter einem Druck von 0,1 mm Hg übergeht.ρ - chlorophenyl - phenyl - methyl - chloromethane, which is obtained by adding a solution of 11.6 g of a-methylp-chlorobenzhydrol in 100 ecm pentane with 5 g calcium chloride, saturate the same at 0 ° with hydrogen chloride, then allowing the mixture to stand for 2 hours at 0 °, with a slight A stream of hydrogen chloride is passed in, the calcium chloride is filtered off and the solvent is removed has been obtained by blowing nitrogen at 0 ° is obtained at 0 ° with 13.0 g of l-methyl-2-pyrrolidinyl-ethanol added and the reaction mixture allowed to stand for 18 hours at room temperature. After adding ether and washing several times with water (up to pH 7), the essential Phase separated and extracted three times with 5% acetic acid. The combined extracts makes one then alkaline with potassium hydroxide while cooling with ice and takes the precipitated oil again in ether. After drying the essential solution over potassium carbonate, the The solvent was evaporated and the residue was distilled in a bulb tube, the N-methyl-2- [2 '- (2-methyl - ρ - chlorobenzhydryloxy) - ethyl] - pyrrolidine as a yellow oil at 125 to 140 ° under a pressure of 0.1 mm Hg passes.
Das aus der Base hergestellte saure Fumarat schmilzt nach der Kristallisation aus Isopropanol und Methanol bei 158 bis 160° (Sintern ab 156°).The acidic fumarate produced from the base melts after crystallization from isopropanol and methanol at 158 to 160 ° (sintering from 156 °).
In analoger Weise wird das N-Methyl-2-[2'-(a-methyl - benzhydryloxy) - äthyl] - pyrrolidin hergestellt; Sdp. 130 bis 14070,1 mm Hg (gelbes öl).N-methyl-2- [2 '- (a-methyl-benzhydryloxy) -ethyl] -pyrrolidine is prepared in an analogous manner; Bp 130 to 14070.1 mm Hg (yellow oil).
Claims (1)
R2 I.
R 2
X-CH2-CH2-HC CH2 H 2 C - ^ - CH 2
X-CH 2 -CH 2 -HC CH 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH53760A CH382164A (en) | 1960-01-19 | 1960-01-19 | Process for the production of new ethers |
| CH880760A CH389608A (en) | 1960-01-19 | 1960-08-03 | Process for the production of new ethers |
| CH1089760 | 1960-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1228262B true DE1228262B (en) | 1966-11-10 |
Family
ID=27172192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES72107A Pending DE1228262B (en) | 1960-01-19 | 1961-01-18 | Process for the production of new pyrrolidine derivatives and their salts |
Country Status (8)
| Country | Link |
|---|---|
| BR (1) | BR6125965D0 (en) |
| CH (1) | CH389608A (en) |
| CY (1) | CY379A (en) |
| DE (1) | DE1228262B (en) |
| ES (1) | ES264077A1 (en) |
| FR (1) | FR1279691A (en) |
| GB (1) | GB942152A (en) |
| OA (1) | OA00698A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0279707A2 (en) * | 1987-02-20 | 1988-08-24 | A.H. Robins Company, Incorporated | Aryloxymethyl derivatives of nitrogenous heterocyclic methanols and ethers thereof having cardiovascular activity |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1307255A (en) * | 1970-09-12 | 1973-02-14 | Pfizer Ltd | Substituted basic benzhydryl ethers |
| JPS5223068A (en) * | 1975-08-13 | 1977-02-21 | Nippon Kayaku Co Ltd | Preparation of optically active 1-methyl -2-(2'-(alpha-methyl-p-chlorobenz hydryloxy) ethtyl) pyrrolidine fumarates |
| CA2512319A1 (en) | 2003-01-14 | 2004-08-05 | Gilead Sciences, Inc. | Compositions and methods for combination antiviral therapy |
| TWI471145B (en) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | Unitary pharmaceutical dosage form |
| TWI375560B (en) | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
| CN107011228B (en) * | 2017-05-24 | 2019-08-09 | 浙江诚意药业股份有限公司 | A kind of preparation method of clemastine fumarate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE934890C (en) * | 1951-10-07 | 1955-11-10 | Chem Fab Promonta Ges Mit Besc | Process for the preparation of basic benzhydryl ethers |
-
1960
- 1960-08-03 CH CH880760A patent/CH389608A/en unknown
- 1960-12-14 GB GB43068/60A patent/GB942152A/en not_active Expired
-
1961
- 1961-01-17 FR FR849932A patent/FR1279691A/en not_active Expired
- 1961-01-18 ES ES0264077A patent/ES264077A1/en not_active Expired
- 1961-01-18 BR BR125965/61A patent/BR6125965D0/en unknown
- 1961-01-18 DE DES72107A patent/DE1228262B/en active Pending
-
1964
- 1964-12-08 OA OA50776A patent/OA00698A/en unknown
-
1967
- 1967-03-04 CY CY37967A patent/CY379A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE934890C (en) * | 1951-10-07 | 1955-11-10 | Chem Fab Promonta Ges Mit Besc | Process for the preparation of basic benzhydryl ethers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0279707A2 (en) * | 1987-02-20 | 1988-08-24 | A.H. Robins Company, Incorporated | Aryloxymethyl derivatives of nitrogenous heterocyclic methanols and ethers thereof having cardiovascular activity |
| EP0279707A3 (en) * | 1987-02-20 | 1989-07-19 | A.H. Robins Company, Incorporated | Aryloxymethyl derivatives of nitrogenous heterocyclic methanols and ethers thereof having cardiovascular activity |
Also Published As
| Publication number | Publication date |
|---|---|
| OA00698A (en) | 1967-07-15 |
| GB942152A (en) | 1963-11-20 |
| BR6125965D0 (en) | 1973-06-28 |
| ES264077A1 (en) | 1961-07-16 |
| CH389608A (en) | 1965-03-31 |
| FR1279691A (en) | 1961-12-22 |
| CY379A (en) | 1967-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1228262B (en) | Process for the production of new pyrrolidine derivatives and their salts | |
| DE1200831B (en) | Process for the preparation of thioxanthene derivatives | |
| DE2724478C2 (en) | 5,11-Dihydro-6H-pyrido [2,3-b] [1,4] benzodiazepin-6-one derivatives, processes for their preparation and pharmaceuticals containing these compounds | |
| DE1090667B (en) | Process for the preparation of basic phenthiazine derivatives | |
| US2838516A (en) | 2-(thienyl methyl) piperidines | |
| DE1059460B (en) | Process for the preparation of phenthiazine derivatives | |
| DE1931487C3 (en) | 5,10-Dihydro-11H-dibenzo substituted in the 5-position, square brackets on b, square brackets on square brackets on 1,4 square brackets on diazepin-11-one and process for their preparation | |
| AT356665B (en) | METHOD FOR PRODUCING NEW CHINUCLIDINE DERIVATIVES, THEIR STEREOISOMERS, OPTICAL ISOMERS AND SALTS | |
| AT371448B (en) | METHOD FOR PRODUCING NEW CIS-4A-PHENYL-ISOCHINOLINE DERIVATIVES AND THEIR ACID ADDITION SALTS | |
| AT222650B (en) | Process for the production of new ethers | |
| AT221503B (en) | Process for the production of new basic phenol ethers and their salts | |
| DE1153378B (en) | Process for the preparation of piperidinoalkyl-iminodibenzylenes and their salts | |
| AT222649B (en) | Process for the preparation of new piperidine derivatives | |
| AT253131B (en) | Process for the preparation of enantiomeric compounds from the dehydroemetin series | |
| AT361493B (en) | METHOD FOR PRODUCING NEW 5,11- DIHYDRO-6H-PYRIDO (2,3-B) (1,4) -BENZODIAZEPINE-6-ON DERIVATIVES AND THEIR SALTS | |
| AT235280B (en) | Process for the production of new indole derivatives | |
| AT361933B (en) | METHOD FOR PRODUCING NEW 5,11- DIHYDRO-6H-PYRIDO (2,3-B) (1,4) - BENZODIAZEPINE-6-ON DERIVATIVES AND THEIR SALTS | |
| DE1227461B (en) | Process for the production of new thioxanthene derivatives | |
| DE1252209B (en) | ||
| DE1182237B (en) | Process for the preparation of 10- [4'-hydroxy-4'-hydroxyalkylpiperidinoalkyl] -phenthiazine derivatives | |
| AT237603B (en) | Process for the production of new o-toluidides | |
| DE964048C (en) | Process for the production of new, antihistamine active piperazine offshoots | |
| AT330176B (en) | METHOD FOR MANUFACTURING ARYL KETONES | |
| AT319916B (en) | Process for the production of new basic ethers | |
| AT211836B (en) | Process for the production of new phenthiazine derivatives |