CH633284A5 - Process for preparing novel, N-substituted, N-2-(2-furylethyl)amines, their salts and optical antipodes - Google Patents
Process for preparing novel, N-substituted, N-2-(2-furylethyl)amines, their salts and optical antipodes Download PDFInfo
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- CH633284A5 CH633284A5 CH38181A CH38181A CH633284A5 CH 633284 A5 CH633284 A5 CH 633284A5 CH 38181 A CH38181 A CH 38181A CH 38181 A CH38181 A CH 38181A CH 633284 A5 CH633284 A5 CH 633284A5
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- A61P25/24—Antidepressants
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Abstract
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von neuen N-substituierten N-[2-(2-Furyl)-äthyl]-2-propinyl-aminen der allgemeinen Formel The invention relates to a process for the preparation of new N-substituted N- [2- (2-furyl) ethyl] -2-propynylamines of the general formula
1 1
r I r I
ch2-ch-n-ch2-csch ch2-ch-n-ch2-csch
Das erfmdungsgemässe Verfahren ist dadurch gekennzeichnet, dass man eine gegebenenfalls racemische oder optisch aktive Verbindung der allgemeinen Formel The process according to the invention is characterized in that an optionally racemic or optically active compound of the general formula
(I) (I)
(II) (II)
(I) (I)
worin wherein
R1 und R2 jeweils für Wasserstoff oder Ci- bis C<t-Alkyl stehen, sowie deren Salzen und optischen Antipoden. R1 and R2 each represent hydrogen or Ci to C <t-alkyl, and their salts and optical antipodes.
Die pharmakologische Wirkung der Verbindungen der allgemeinen Formel (I) ist der des Phenyläthylamins (J. Phar-macol. 72,265,1941) ähnlich. Die erfindungsgemäss erhältlichen N-substituierten 2-(2-Furyläthyl)-amine der allgemeinen Formel (I) haben jedoch keine unerwünschte Amphetamin-Wirkung, sondern hemmen in überraschender Weise selektiv die Monoaminoxydase. Eine derartige Hemmwirkung wurde schon für einige den erfindungsgemäss erhältlichen Verbindungen strukturell ähnliche Verbindungen nachgewiesen (Biochemical Pharmacology 18,1447,1969; Br. J. Pharmacology 45,490,1972). Die dort beschriebenen Verbindungen hemmen jedoch hauptsächlich die 5-Hydroxytryptaminoxidation, nur das den Gegenstand eines Patentes der Anmelderin bildende N-a-Dimethyl-N-ß-phenyläthyl-N-propinylamin (GB-PS 1031425) übt eine ähnliche Hemm Wirkung auf die Oxidation des Benzylamins (Br. J. Pharmacology 45,490,1972) aus. Die neuen Verbindungen der allgemeinen Formel (I) weisen eine vorteihaftere pharmakologische Wirkung auf. The pharmacological activity of the compounds of the general formula (I) is similar to that of phenylethylamine (J. Phar-macol. 72,265,1941). However, the N-substituted 2- (2-furylethyl) amines of the general formula (I) obtainable according to the invention have no undesirable amphetamine activity, but instead surprisingly selectively inhibit the monoamine oxidase. Such an inhibitory effect has already been demonstrated for some compounds structurally similar to the compounds obtainable according to the invention (Biochemical Pharmacology 18,1447,1969; Br. J. Pharmacology 45,490,1972). However, the compounds described therein mainly inhibit 5-hydroxytryptamine oxidation, only Na-dimethyl-N-β-phenylethyl-N-propynylamine (GB-PS 1031425), which is the subject of a patent by the applicant, has a similar inhibitory effect on the oxidation of benzylamine (Br. J. Pharmacology 45,490,1972). The new compounds of the general formula (I) have a more advantageous pharmacological action.
(II) (II)
io worin die Bedeutung von R1 und R2 die gleiche wie oben ist, in einem hochsiedenden Äther, wie Dibutyläther oder Dioxan, in Gegenwart von Kupferacetylid oder einer Kupferacetylid bildenden Verbindung mit Formaldehyd, welches in Form von Paraformaldehyd eingesetzt wird, und Acetylen ls kondensiert, ein gegebenenfalls erhaltenes racemisches Gemisch einer Verbindung der allgemeinen Formel (I) gewünschtenfalls in die optischen Antipoden aufspaltet und/ oder eine erhaltene Verbindung der allgemeinen Formel (I) in ein Salz überführt oder aus einem Salz freisetzt. 20 Die Reaktionstemperatur beträgt zweckmässig 80 bis 150°C. Die Reaktion kann z.B. so ausgeführt werden, dass man ein 2-(2-Furyl)-äthylamin der allgemeinen Formel (II) in Dioxan löst, der Lösung Paraformaldehyd sowie Kupferacetylid oder eine Kupferacetylid bildende Verbindung zusetzt 25 und unter Rühren und Erwärmen Acetylen in das Reaktionsgemisch einleitet. Die erhaltenen Verbindungen der allgemeinen Formel (I) werden in üblicher Weise isoliert. io in which the meaning of R1 and R2 is the same as above, in a high-boiling ether such as dibutyl ether or dioxane, in the presence of copper acetylide or a copper acetylide-forming compound with formaldehyde, which is used in the form of paraformaldehyde, and acetylene is condensed optionally obtained racemic mixture of a compound of the general formula (I) if desired split into the optical antipodes and / or a compound of the general formula (I) obtained is converted into a salt or released from a salt. 20 The reaction temperature is appropriately 80 to 150 ° C. The reaction can e.g. be carried out in such a way that a 2- (2-furyl) ethylamine of the general formula (II) is dissolved in dioxane, the solution is added paraformaldehyde and copper acetylide or a compound which forms copper acetylide 25 and acetylene is introduced into the reaction mixture with stirring and heating. The compounds of general formula (I) obtained are isolated in a conventional manner.
Ist die hergestellte Verbindung der allgemeinen Formel (I) eine tertiäre Base (R2 = Alkyl), so kann durch Acylieren des 30 Rückstandes gereinigt werden. Dabei wird die nicht umgesetzte sekundäre Base der allgemeinen Formel (II) acyliert, wodurch sie in verdünnten Säuren unlöslich wird. Die hergestellte tertiäre Base kann dann durch Extraktion mit einer verdünnten Säure rein isoliert werden. If the compound of general formula (I) produced is a tertiary base (R2 = alkyl), it can be purified by acylating the residue. The unreacted secondary base of the general formula (II) is acylated, which makes it insoluble in dilute acids. The tertiary base produced can then be isolated in pure form by extraction with a dilute acid.
35 Acyliert werden kann z.B. in der Wärme mit Essigsäureanhydrid oder mit Benzoylchlorid und Lauge. Das acylierte Reaktionsgemisch wird mit kalter verdünnter Salzsäure extrahiert, der salzsaure Extrakt alkalisch gemacht und die tertiäre Base mit einem Lösungsmittel extrahiert. Der Extrakt 40 wird eingedampft, der Rückstand destilliert und die Base gewünschtenfalls mit einer organischen oder anorganischen Säure in ein Salz übergeführt. 35 can be acylated e.g. while warm with acetic anhydride or with benzoyl chloride and lye. The acylated reaction mixture is extracted with cold, dilute hydrochloric acid, the hydrochloric acid extract is made alkaline and the tertiary base is extracted with a solvent. The extract 40 is evaporated, the residue is distilled and, if desired, the base is converted into a salt with an organic or inorganic acid.
Die erfindungsgemäss erhältlichen Verbindungen können mit biologisch vorteilhaften oder indifferenten Säuren zu 45 ihren Salzen umgesetzt werden bzw. in Fällen, wo die Reinigung der Verbindung über ein Salz erfolgt, aus ihren Salzen freigesetzt werden. Zur Salzbildung sind anorganische Säuren, z.B. Salzsäure, Schwefelsäure oder Phosphorsäure, und organische Säuren, z.B. Maleinsäure, Milchsäure, Citro-50 nensäure, Ascorbinsäure usw., geeignet. The compounds obtainable according to the invention can be reacted with biologically advantageous or indifferent acids to give their salts, or can be released from their salts in cases where the compound is purified using a salt. Inorganic acids, e.g. Hydrochloric acid, sulfuric acid or phosphoric acid, and organic acids, e.g. Maleic acid, lactic acid, citro-50-nenoic acid, ascorbic acid etc.
Diejenigen Verbindungen der allgemeinen Formel (I), in denen R1 für Alkyl steht, enthalten ein chirales Kohlenstoffatom und sind optisch aktiv. Die optisch aktiven Isomeren können erhalten werden, indem man racemische Verbin-55 düngen der allgemeinen Formel (I) in ihre optischen Antipoden zerlegt oder aber, indem man von optisch aktiven Verbindungen der allgemeinen Formel (II) ausgeht. Those compounds of the general formula (I) in which R1 represents alkyl contain a chiral carbon atom and are optically active. The optically active isomers can be obtained by decomposing racemic compound 55 of the general formula (I) into their optical antipodes or else by starting from optically active compounds of the general formula (II).
Die pharmakologische Wirkung erfindungsgemäss erhältlicher Verbindungen der Formel (I) wird nachstehend 60 demonstriert. The pharmacological action of compounds of the formula (I) obtainable according to the invention is demonstrated below.
Die Oxidation des Benzylamins in der Leber wird z.B. durch N-Methyl-N-[2-(2-furyl)-äthyl]-2-propinylamin in vivo in einer Dosis von 6,25 mg/kg um 79% gehemmt, während bei der gleichen Dosis die Hemmung der Tyraminoxida-65 tion nur 44%beträgt. Durch N-Methyl-N-[l-Methyl-2-(2-furyl)-äthyl]-2-propinylamin in einer Dosis von 5 mg/kg wird im Gehirn die Benzylaminoxidation um 53%, die des 5-Hydroxytryptamins nur um 2% gehemmt. Bei der gleichen The oxidation of benzylamine in the liver is e.g. inhibited by N-methyl-N- [2- (2-furyl) ethyl] -2-propynylamine in vivo in a dose of 6.25 mg / kg by 79%, while at the same dose the inhibition of tyramine oxida-65 tion is only 44%. N-methyl-N- [l-methyl-2- (2-furyl) ethyl] -2-propynylamine in a dose of 5 mg / kg reduces the benzylamine oxidation in the brain by 53%, that of 5-hydroxytryptamine only by 2% inhibited. At the same
633284 633284
Dosis zeigt das N-Methyl-N-[(l-methyl-2-phenyl)-äthyl]-2-propinylamin im Gehirn eine Hemmung der Benzylaminoxi-dation von 80%, die Hemmung der Oxidation des 5-Hydro-tryptamins beträgt 15%. In einer Dosis von 10 mg/kg angewendet, hemmt das Phenylderivat die Oxidation des Benzylamins in der Leber um 78%, die des 5-Hydroxytryptamins um 56%. Dose shows that N-methyl-N - [(l-methyl-2-phenyl) ethyl] -2-propynylamine inhibits benzylamine oxidation by 80% in the brain, and inhibits oxidation of 5-hydro-tryptamine by 15 %. Applied at a dose of 10 mg / kg, the phenyl derivative inhibits the oxidation of benzylamine in the liver by 78% and that of 5-hydroxytryptamine by 56%.
Aus diesen Daten ist ersichtlich, dass bei der Hemmung der Monoaminoxidase die Furanderivate eine selektivere Wirkung haben als die bekannten Phenylderivate. Die Selektivität ist bei In-vitro-Versuchen noch ausgeprägter. Auch die Reserpin-antagonistische antidepressive Wirkung der Furanderivate ist stärker als die der analogen Phenylverbin-dungen. Die Furanderivate weisen eine geringere Toxizität auf als die entsprechenden Phenylderivate. From these data it can be seen that the furan derivatives have a more selective effect than the known phenyl derivatives in the inhibition of monoamine oxidase. The selectivity is even more pronounced in in vitro experiments. The reserpine-antagonistic antidepressant effect of the furan derivatives is also stronger than that of the analog phenyl compounds. The furan derivatives have a lower toxicity than the corresponding phenyl derivatives.
Die erfindungsgemäss erhältlichen Verbindungen bzw. deren Salze können in an sich bekannter Weise zu Arzneimittelformulierungen verarbeitet werden. Zur Herstellung der Arzneimittelpräparate werden die erfindungsgemäss erhältlichen Verbindungen z.B. mit flüssigen oder festen Streckmitteln, Trägerstoffen und Hilfsstoffen wie Gleitmittel, Aromastoffen, Konservierungsmitteln usw. vermischt und in an sich bekannter Weise zu unmittelbar verwendbaren Arzneimitteln, wie Tabletten, Dragees, Kapseln, Mikrokapseln, Sup-positorien, Pulvermischungen, wässrigen Suspensionen, Lösungen usw. formuliert. Die Arzneimittelpräparate werden hauptsächlich peroral und parenteral angewendet. The compounds or their salts obtainable according to the invention can be processed to pharmaceutical formulations in a manner known per se. To prepare the pharmaceutical preparations, the compounds obtainable according to the invention are e.g. mixed with liquid or solid extenders, carriers and auxiliaries such as lubricants, flavors, preservatives etc. and in a manner known per se to form directly usable medicines, such as tablets, dragees, capsules, microcapsules, supositories, powder mixtures, aqueous suspensions, solutions, etc. formulated. The medicinal products are mainly used orally and parenterally.
Das erfindungsgemässe Verfahren wird durch folgende Beispiele näher erläutert: The process according to the invention is explained in more detail by the following examples:
Beispiel 1 example 1
13,9 g (0,1 Mol) N-Methyl-[l-methyl-2-(2-furyl)]-äthyl-amin werden in 80 ml Dioxan gelöst. Zu der Lösung werden 6 g Paraformaldehyd und 1 g Kupfer(I)-chlorid gegeben. Dann wird unter Rühren 30 Stunden lang Acetylen in die Lösung eingeleitet, danach filtriert und das Filtrat eingedampft. Der Rückstand wird in Benzol gelöst, die Lösung mit 13.9 g (0.1 mol) of N-methyl- [l-methyl-2- (2-furyl)] - ethylamine are dissolved in 80 ml of dioxane. 6 g of paraformaldehyde and 1 g of copper (I) chloride are added to the solution. Then acetylene is introduced into the solution with stirring for 30 hours, then filtered and the filtrate evaporated. The residue is dissolved in benzene, the solution with
Wasser gewaschen, über Kaliumcarbonat getrocknet und dann eingedampft. Der Rückstand wird im Vakuum destilliert. Es werden 6,8 g N-Methyl-N-[l-methyl-2-(2-furyl)-äthyl]-2-propinylamin erhalten. Kp.: 114-116°C/26,6 mbar; s no : 1,4910. Washed water, dried over potassium carbonate and then evaporated. The residue is distilled in vacuo. 6.8 g of N-methyl-N- [l-methyl-2- (2-furyl) ethyl] -2-propynylamine are obtained. Bp: 114-116 ° C / 26.6 mbar; s no: 1.4910.
Beispiel 2 Example 2
Das nach Beispiel 1 hergestellte N-Methyl-N-[l-methyl-2-(2-furyl)-äthyl]-2-propinylamin wird mit Dibenzoyl-D-wein-lo säure umgesetzt. Fp. des erhaltenen Salzes: 170-172°C (aus Chloroform). The N-methyl-N- [l-methyl-2- (2-furyl) ethyl] -2-propynylamine prepared according to Example 1 is reacted with dibenzoyl-D-wein-lo acid. Mp of the salt obtained: 170-172 ° C (from chloroform).
Beispiel 3 Example 3
D-(+)-N-Methyl-[l-methyl-2-(2-furyl)]-äthylamin wird auf ls die im Beispiel 1 beschriebene Weise mit Formaldehyd und Acetylen umgesetzt. Das (-)-N-Methyl-N-[l-methyl-2-(2-furyl)-äthyl]-2-propinylamin wird in gleicher Ausbeute erhalten. D - (+) - N-methyl- [l-methyl-2- (2-furyl)] - ethylamine is reacted in the manner described in Example 1 with formaldehyde and acetylene. The (-) - N-methyl-N- [l-methyl-2- (2-furyl) ethyl] -2-propynylamine is obtained in the same yield.
Md = —1,2° n2D°= 1,4892 20 Der (+)-Antipode wird analog erhalten. Md = —1.2 ° n2D ° = 1.4892 20 The (+) - antipode is obtained analogously.
[a]o = +1,2° n2D°= 1,4891 [a] o = + 1.2 ° n2D ° = 1.4891
Beispiel 4 Example 4
12,5 g (0,1 Mol) l-Methyl-2-(2-furyl)-äthylamin werden in 25 70 ml Dioxan gelöst. Zu der Lösung werden 6 g Paraformaldehyd und 1 g Kupfer(I)-chlorid zugegeben, wonach in die Lösung Acetylen — wie im Beispiel 1 beschrieben — eingeleitet und die erhaltene Lösung gemäss Beispiel 1 aufgearbeitet wird. 6,3 g N-[l-Methyl-2-(2-furyl)-äthyl]-2-propinyl-30 amin werden erhalten. 12.5 g (0.1 mol) of l-methyl-2- (2-furyl) ethylamine are dissolved in 25 70 ml of dioxane. 6 g of paraformaldehyde and 1 g of copper (I) chloride are added to the solution, after which acetylene - as described in Example 1 - is introduced and the solution obtained is worked up as in Example 1. 6.3 g of N- [l-methyl-2- (2-furyl) ethyl] -2-propynyl-30 amine are obtained.
Kp.: 55 bis 60°C/6,7 mbar Fp. (Hydrochlorid): 107 bis 111°C Kp .: 55 to 60 ° C / 6.7 mbar mp (hydrochloride): 107 to 111 ° C
np = 1,4895 np = 1.4895
Analyse: (CioHnNO - HCl) (%) Analysis: (CioHnNO - HCl) (%)
35 35
Ber.: Gef.: Calc .: Found .:
60,15 60,39 60.15 60.39
7,06 7,03 7.06 7.03
N 7,01 N 6,94 N 7.01 N 6.94
Cl Cl Cl Cl
17,75 18,27 17.75 18.27
B B
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75CI1632A HU174692B (en) | 1975-12-29 | 1975-12-29 | Process for preparing secondary and tertiary derivatives of 2-/2-furyl/-ethylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633284A5 true CH633284A5 (en) | 1982-11-30 |
Family
ID=10994595
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1640476A CH630620A5 (en) | 1975-12-29 | 1976-12-28 | Process for preparing novel N-2-(2-furylethyl)amines. |
| CH38181A CH633284A5 (en) | 1975-12-29 | 1981-01-21 | Process for preparing novel, N-substituted, N-2-(2-furylethyl)amines, their salts and optical antipodes |
| CH38281A CH633285A5 (en) | 1975-12-29 | 1981-01-21 | Process for preparing novel N-2-(2-furylethyl)amines, their salts and optical antipodes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1640476A CH630620A5 (en) | 1975-12-29 | 1976-12-28 | Process for preparing novel N-2-(2-furylethyl)amines. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH38281A CH633285A5 (en) | 1975-12-29 | 1981-01-21 | Process for preparing novel N-2-(2-furylethyl)amines, their salts and optical antipodes |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5283359A (en) |
| AR (4) | AR215610A1 (en) |
| AT (1) | AT361460B (en) |
| BE (1) | BE849892A (en) |
| CA (1) | CA1108163A (en) |
| CH (3) | CH630620A5 (en) |
| CS (2) | CS216166B2 (en) |
| DD (3) | DD131853A1 (en) |
| DE (1) | DE2658064A1 (en) |
| DK (1) | DK584376A (en) |
| EG (1) | EG12514A (en) |
| ES (1) | ES454581A1 (en) |
| FI (1) | FI63227C (en) |
| FR (1) | FR2336928A1 (en) |
| GB (1) | GB1570209A (en) |
| GR (1) | GR62443B (en) |
| HU (1) | HU174692B (en) |
| IL (1) | IL51145A (en) |
| IN (1) | IN145292B (en) |
| NL (1) | NL7614474A (en) |
| PL (3) | PL113903B1 (en) |
| SE (1) | SE429654B (en) |
| SU (5) | SU741796A3 (en) |
| YU (3) | YU314576A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1031425A (en) * | 1962-03-30 | 1966-06-02 | Chinoin Gyogyszer Es Vegyeszet | New aralkylamines and their preparation |
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1975
- 1975-12-29 HU HU75CI1632A patent/HU174692B/en not_active IP Right Cessation
-
1976
- 1976-12-22 IL IL51145A patent/IL51145A/en unknown
- 1976-12-22 DE DE19762658064 patent/DE2658064A1/en active Granted
- 1976-12-22 SE SE7614473A patent/SE429654B/en not_active IP Right Cessation
- 1976-12-23 AT AT957376A patent/AT361460B/en not_active IP Right Cessation
- 1976-12-23 GB GB53734/76A patent/GB1570209A/en not_active Expired
- 1976-12-24 ES ES454581A patent/ES454581A1/en not_active Expired
- 1976-12-24 FR FR7639108A patent/FR2336928A1/en active Granted
- 1976-12-25 EG EG790/76A patent/EG12514A/en active
- 1976-12-27 YU YU03145/76A patent/YU314576A/en unknown
- 1976-12-27 JP JP15666076A patent/JPS5283359A/en active Granted
- 1976-12-28 BE BE173664A patent/BE849892A/en not_active IP Right Cessation
- 1976-12-28 GR GR52486A patent/GR62443B/en unknown
- 1976-12-28 DD DD7600201731A patent/DD131853A1/en not_active IP Right Cessation
- 1976-12-28 DD DD7600201725A patent/DD131748A1/en unknown
- 1976-12-28 IN IN2269/CAL/1976A patent/IN145292B/en unknown
- 1976-12-28 SU SU762433999A patent/SU741796A3/en active
- 1976-12-28 FI FI763715A patent/FI63227C/en not_active IP Right Cessation
- 1976-12-28 DK DK584376A patent/DK584376A/en not_active Application Discontinuation
- 1976-12-28 CH CH1640476A patent/CH630620A5/en not_active IP Right Cessation
- 1976-12-28 NL NL7614474A patent/NL7614474A/en not_active Application Discontinuation
- 1976-12-28 DD DD7600196653A patent/DD129327A1/en not_active IP Right Cessation
- 1976-12-29 CS CS768751A patent/CS216166B2/en unknown
- 1976-12-29 PL PL1976216742A patent/PL113903B1/en unknown
- 1976-12-29 AR AR266039A patent/AR215610A1/en active
- 1976-12-29 CA CA268,811A patent/CA1108163A/en not_active Expired
- 1976-12-29 PL PL1976216741A patent/PL111945B1/en unknown
- 1976-12-29 CS CS775087A patent/CS216167B2/en unknown
- 1976-12-29 PL PL1976194802A patent/PL112123B1/en unknown
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1977
- 1977-01-01 AR AR269091D patent/AR221212A1/en active
- 1977-09-05 AR AR269092A patent/AR218263A1/en active
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1978
- 1978-01-11 SU SU782565049A patent/SU795473A3/en active
- 1978-01-11 SU SU782565000A patent/SU847918A3/en active
- 1978-08-23 AR AR273404A patent/AR217703A1/en active
- 1978-09-22 SU SU782665546A patent/SU845784A3/en active
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1979
- 1979-05-10 SU SU792764351A patent/SU932990A3/en active
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1981
- 1981-01-21 CH CH38181A patent/CH633284A5/en not_active IP Right Cessation
- 1981-01-21 CH CH38281A patent/CH633285A5/en not_active IP Right Cessation
-
1982
- 1982-07-08 YU YU01488/82A patent/YU148882A/en unknown
- 1982-07-08 YU YU01489/82A patent/YU148982A/en unknown
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