DE1545869A1 - Process for the preparation of 3-phenyl-3-pyridyl (2 ') -propylamine derivatives - Google Patents
Process for the preparation of 3-phenyl-3-pyridyl (2 ') -propylamine derivativesInfo
- Publication number
- DE1545869A1 DE1545869A1 DE19651545869 DE1545869A DE1545869A1 DE 1545869 A1 DE1545869 A1 DE 1545869A1 DE 19651545869 DE19651545869 DE 19651545869 DE 1545869 A DE1545869 A DE 1545869A DE 1545869 A1 DE1545869 A1 DE 1545869A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- above meanings
- phenyl
- pyridyl
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 3-Phenyl-3-pyridyl(2') propylamin-derivatenProcess for the preparation of 3-phenyl-3-pyridyl (2 ') propylamine derivatives
Zuscitz zu PatentZuscitz to patent
= Fw '1794)= Fw '1794)
(Patentanmeldung F 46 262 IVb/12 q(Patent application F 46 262 IVb / 12 q
Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung von Diphenylpropylamin-derivaten der allgemeinen Formel I The main patent relates to a process for the preparation of diphenylpropylamine derivatives of the general formula I.
CII-CH0 -CHn -NII-CH-CHCII-CH 0 -CH n -NII-CH-CH
R,R,
(I)(I)
11.11.
in- der R1 und R0 Wasserstoff oder eine Alkoxygruppe mit höchstens k Kohlenstoffatomen, R Wasserstoff oder die Mothylgruppe, U1 und Rr Alkylgruppen mit höchstens 4 Kohlenstoffatomen bedeuten und deren Salzen, das dadurch gekennzeichnet ist, daß manin which R 1 and R 0 denote hydrogen or an alkoxy group with at most k carbon atoms, R denotes hydrogen or the methyl group, U 1 and R r denote alkyl groups with at most 4 carbon atoms and their salts, which is characterized in that one
n) Verbindungen der ,allgemeinen Formel IIn) compounds of the general formula II
909849/1529909849/1529
Fvr 479^ aFvr 479 ^ a
-N-CH-C-N-CH-C
R,R,
R.R.
(II)(II)
in der R Wasserstoff, oder die Benzylgruppe bedeutet und R1 bis Rr die obigen Bedeutungen besitzen, reduziert in which R is hydrogen or the benzyl group and R 1 to R r have the above meanings, reduced
b) Verbindungen der allgemeinen Formel IIIb) compounds of the general formula III
Bl>-v Bl > -v
0R<
-N-OH-CH-/0R <
-N-OH-CH- /
(III Ir(III Ir
in der R bis R- die obigen Bedeutungen besitzen und R>- einen Alkyl- oder.den.Benzylrest bedeutet mit ätherspaltenden Mitteln behandelt oder katalytisch hydriert,in which R to R- have the above meanings and R> - means an alkyl or den.benzyl radical treated with ether-splitting agents or catalytically hydrogenated,
c) Verbindungen der allgemeinen Formel IVc) compounds of the general formula IV
Y T3 ?A%Y T3? A %
CH2-CH2-N-CH-CH-//CH 2 -CH 2 -N-CH-CH - //
(IV)(IV)
in der R, bis.R_-die obigen Bedeutungen besitzen und Ac einen Acylrest bedeutet, alkalisch oder sauer verseift,in which R, bis.R_-have the above meanings and Ac is an acyl radical, saponified in alkaline or acidic conditions,
d) Verbindungen der allgemeinen Formel Vd) Compounds of the general formula V
(V)(V)
R.R.
9O9849/I5i99O9849 / I5i9
ORIGINAL INSPECTEDORIGINAL INSPECTED
- 3 - Fw fr79fr a - 3 - Fw fr79fr a
in der R bis R die obigen Bedeutungen besitzen und X ein Sauerstoffatom oder die Gruppe ^ bedeutet, katalytisch hydriertin which R to R have the above meanings and X is an oxygen atom or the group ^ means catalytically hydrogenated
e) Verbindungen der allgemeinen Formel VIe) Compounds of the general formula VI
CH-CH0-CH0-NH (VI) RCH-CH 0 -CH 0 -NH (VI) R
in der R bis R0 die obigen Bedeutungen besitzen, entweder mit Äthylenoxyden der allgemeinen Formel VIIin which R to R 0 have the above meanings, either with ethylene oxides of the general formula VII
!3 fv"'! 3 fv "'
HC - CH-^ *> (VII)HC - CH- ^ *> (VII)
^b R5 ^ b R 5
in der R- bis R- die obigen Bedeutungen besitzen, um setzt oder mit Verbindungen der allgemeinen Formel VIIIin which R- to R- have the above meanings to sets or with compounds of the general formula VIII
X ^RX ^ R
(VIII)(VIII)
in der R- bis R- die obigen Bedeutungen besitzen, kondensiert und gleichzeitig oder anschließend reduziert ,in which R- to R- have the above meanings, condensed and reduced at the same time or afterwards,
f) Diphenylpropionaldehyde der allgemeinen Formel IX R ' CH-CHn-CHO (IX) ■ f) Diphenylpropionaldehydes of the general formula IX R 'CH-CH n -CHO (IX) ■
»2 ^»2 ^
. . _ 909849/1529. . _ 909849/1529
xn der R1 und R0 die obigen Bedeutungen besitzen,xn where R 1 and R 0 have the above meanings,
Fw 479fr aFw 479fr a
mit Verbindungen der allgemeinen Formel Xwith compounds of the general formula X
(X)(X)
Il \-)CIl \ -) C
in der X, R und R bis R- die obigen Bedeutungen besitzen, kondensiert und gleichzeitig oder anschließend reduziert .in which X, R and R to R- have the above meanings, condensed and reduced at the same time or subsequently.
g) Verbindungen der allgemeinen Formel XIg) compounds of the general formula XI
(XI)(XI)
in der X und R bis R- die obigen Bedeutungen besitzen mit komplexen Metallhydriden reduziert oderin which X and R to R- have the above meanings reduced or with complex metal hydrides
h) Verbindungen der allgemeinen Formel I, in der R, und/oder R Hydroxygruppen bedeutet, mit Alkylierungsmitteln behandelt und bei allen Verfahrensweisenh) Compounds of the general formula I in which R, and / or R is hydroxy groups treated with alkylating agents and in all procedures
anschließend eine gegebenenfalls vorhandene N-Benzylgruppe abspaltet und die erhaltenen basischen Verbindungen gegebenenfalls durch Behandlung mit anorganischen oder organischen Säuren in ihre Salze überführt.subsequently splitting off any N-benzyl group which may be present and the basic compounds obtained, optionally by treatment with inorganic or organic Acids converted into their salts.
In weiterer Ausgestaltung des erfindungsgemäßen Verfahrens wurde nun gefunden, daß man herz- und blutdruckwirksame Verbindungen erhält, wenn man nach dem Verfahren der Hauptanmeldung solche Verbindungen herstellt, in denen anstelle des einen Phenylrestes in der Dxphenylpropylgruppe ein Pyridyl(2)-rest enthalten ist.In a further embodiment of the method according to the invention it has now been found that compounds which act on the heart and blood pressure are obtained if one follows the procedure of the main application produces compounds in which instead of a phenyl radical in the Dxphenylpropylgruppe a pyridyl (2) radical is included.
Gegenstand der Erfindung ist somit ein Verfahren zur HerstellungThe invention thus relates to a method for production
909849/1529909849/1529
/5/ 5
Fw 4794 aFw 4794 a
von 3-Phenyl-3-pyridyl(2')-propylamin-derivaten der allgemeinen Formel Iof 3-phenyl-3-pyridyl (2 ') propylamine derivatives der general formula I.
1 CH-CH0-CH,1 CH-CH 0 -CH,
-NH -CII -CII-NH -CII -CII
(D(D
in der R1 Wasserstoff oder eine Alkoxygruppe mit höchstens k Kohlenstoffatomen, R_ Wasserstoff oder die Methy1gruppe, R. und R_ Alkylgruppen mit höchstens k Kohlenstoffatomen bedeuten und deren Salzen, das dadurch gekennzeichnet ist, daß manin which R 1 is hydrogen or an alkoxy group with at most k carbon atoms, R_ is hydrogen or the Methy1gruppe, R. and R_ are alkyl groups with at most k carbon atoms and their salts, which is characterized in that one
a) Verbindungen der allgemeinen Formel IIa) Compounds of the general formula II
(II)(II)
H-CH0-CH0-N-CH-C-/H-CH 0 -CH 0 -N-CH-C- /
in der R Wasserstoff oder die Benzylgruppe bedeutet und R bis R die obigen Bedeutungen besitzen, reduziertin which R is hydrogen or the benzyl group and R to R have the above meanings, reduced
b) Verbindungen der allgemeinen Formel IIIb) compounds of the general formula III
CH-CH0-CH9 CH-CH 0 -CH 9
(III)(III)
in der R bis R1. die obigen Bedeutungen besitzen und R, einen Alkyl- oder den Benzyl-rest bedeutet, mit ätherspaltenden Mitteln behandelt oder katalytisch hydriert,in R to R 1 . have the above meanings and R is an alkyl or benzyl radical, treated with ether-splitting agents or catalytically hydrogenated,
c) Verbindungen der allgemeinen Formel IVc) compounds of the general formula IV
/6/ 6
903849/1529903849/1529
Fw 4794 aFw 4794 a
H-CH0-CH1 H-CH 0 -CH 1
R R- OAc -N-CH-CHhR R- OAc -N-CH-CHh
(IV)(IV)
in der R bis R die obigen Bedeutungen besitzen und Ac einen Acylrest bedeutet, alkalisch oder sauer verseift,in which R to R have the above meanings and Ac means an acyl radical, saponified alkaline or acidic,
d) Verbindungen der allgemeinen Formel Vd) Compounds of the general formula V
=CH-CH.= CH-CH.
Ms fMs f
. -N-CH-C. -N-CH-C
(V)(V)
R.R.
\=lN\ = lN
in der R bis R die obigen Bedeutungen besitzen und Xin which R to R have the above meanings and X
H ein Sauerstoffatom oder die Gruppe <^" bedeutet,H denotes an oxygen atom or the group <^ ",
katalytisch hydriert H catalytically hydrogenated H
e) Verbindungen der allgemeinen Formel VIe) Compounds of the general formula VI
CH-CH2-CH2-NH RCH-CH 2 -CH 2 -NH R
(VI)(VI)
in der R und R die obigen Bedeutungen besitzen, entweder mit Äthylenoxyden der allgemeinen Formel VIIin which R and R have the above meanings, either with ethylene oxides of the general formula VII
?3 ? 3
HC - Z VHC - Z V
(VII)(VII)
in der R bis R. die obigen Bedeutungen besitzen, umsetzt oder mit Verbindungen der allgemeinen Formel VIIIin which R to R have the above meanings, reacts or with compounds of the general formula VIII
909849/1529909849/1529
/7/ 7
15458B915458B9
- 7 - Fvf k79lt a - 7 - Fvf k79 l ta
O=C-C-/ \ (VIII)O = CC- / \ (VIII)
in der R- bis R_ die obigen Bedeutungen besitzen, kondensiert und gleichzeitig oder anschließend reduziert, in which R- to R_ have the above meanings, condensed and reduced at the same time or subsequently,
f) Phenyl-pyridyl(2)-propionaldehyde der allgemeinen Formel IXf) Phenyl-pyridyl (2) -propionaldehyde of the general Formula IX
(IX)(IX)
in der R1 die obige Bedeutung besitzt, mit Verbindungen der alIgen«inen Formel Xin which R 1 has the above meaning, with compounds of the al Igen "inen formula X
HN-C-C·/' R XHN-C-C · / 'R X
in der X, und R1 R. bis R_ die obigen Bedeutungen besitzen, kondensiert und gleichzeitig oder anschließend reduziertin which X, and R 1 R. to R_ have the above meanings, condensed and reduced simultaneously or subsequently
g) Verbindungen der allgemeinen Formel XIg) compounds of the general formula XI
H-CH2-CO-N-C-H-CH 2 -CO-NC-
R5 R 5
in der X und R bis R_ die obigen Bedeutungen besitzen, mit komplexen Metallhydriden reduziert oderin which X and R to R_ have the above meanings, reduced with complex metal hydrides or
h) Verbindungen der allgemeinen Formel I, in der R1 eineh) Compounds of the general formula I in which R 1 is a
909849/1529909849/1529
Hydroxygruppe bedeutet, mit Alkylierungsmitteln behandelt und bei allen VerfahrensweisenHydroxy group means treated with alkylating agents and in all procedures
anschließend eine gegebenenfalls vorhandene N-Benzylgruppe abspaltet und die erhaltenen basischen Verbindungen gegebenenfalls durch Behandlung mit anorganischen oder organischen Säuren in ihre Salze überführt.then an optionally present N-benzyl group split off and the basic compounds obtained, if appropriate by treatment with inorganic or organic Acids converted into their salts.
Die unter a) -g) aufgeführten Verfahrensweisen werden, wie im Hauptpatent beschrieben, durchgeführt. Die Herstellung der Ausgangsverbindungen der allgemeinen Formeln II, III und-IV erfolgt in der im Hauptpatent beschriebenen Weise, wobei je-, doch anstelle von 1,l-Diphenylpropyl-3-amin das 1-Phenyl-lpyridyl-(2' ) -propyl/Sinin eingesetzt wird. Dieses Amin kann auch für die unter e) beschriebenen Verfahrensweise verwendet werden, während für die unter f) aufgeführten Verfahrensweisen als Ausgangsstoffe die den Verbindungen der Formel IX entsprechenden Phenyl-pyridyl(2)-propionaldehyde und für die unter g) aufgeführte Verfahrensweise die entsprechenden Phenyl-pyridyl(2)-propionsäur«amide verwendet werden.The procedures listed under a) -g) are how described in the main patent. The preparation of the starting compounds of the general formulas II, III and IV takes place in the manner described in the main patent, but 1-phenyl-lpyridyl- (2 ') -propyl / sinine is used instead of 1,1-diphenylpropyl-3-amine. This amine can can also be used for the procedure described under e), while for the procedures listed under f) the starting materials used are the compounds of the formula IX corresponding phenyl-pyridyl (2) -propionaldehyde and for the The procedure listed under g) the corresponding phenyl-pyridyl (2) -propionic acid amides are used.
Die Verfahrensprodukte sind wertvolle Arzneimittel und weisen neben einer sehr guten Herz- und Kreislaufwirkung zusätzlich eine günstige Blutdrucksenkung auf.The products of the process are valuable pharmaceuticals and, in addition to having a very good cardiovascular effect, also have a favorable lowering of blood pressure.
So senkt z.B. das 1-t3',4'-Dimethylphenyl)-2-^phenyl-pyridyl(2")-propylamino7-px*opanol-( 1) -hydrochlorid bei Ratten, die einen Nierenhochdruck haben, den Blutdruck stark und langanhaltend:For example, the 1-t3 ', 4'-dimethylphenyl) -2- ^ phenyl-pyridyl (2 ") -propylamino7-px * opanol- (1) -hydrochloride in rats that have a Have high kidney pressure, high and persistent blood pressure:
Der mittlere Blutdruck betrug bei 11 Hochdruckratten durchschnittlich 192 nun Hg. 2 Stunden nach der subcutanen Gabe von 40 mg/kg des Verfahrensproduktes war der Blutdruck auf I36 mm Hg abgesunken und 24 Stunden nach der Injektion betrugt er I68 mm Hg, hatte also den Auegangswert noch nicht wieder erreicht.The mean blood pressure in 11 hypertensive rats averaged 192 now Hg. 2 hours after the subcutaneous administration of 40 mg / kg of the product of the process was the blood pressure of 136 mm Hg dropped and 24 hours after the injection it was 168 mm Hg, so had not yet reached the initial value again.
Das genannte Verfahrensprodukt zeigt außerdem «ine starke ßsympathicolytische Wirkung. Es zeigt z.B. an der Trachealkette nach Castillo mit nur 2,5f auf 50 ecm Tyrodelösung eineThe above-mentioned product also shows a strong sympathicolytic effect. For example, it shows a Tyrode solution on the tracheal chain according to Castillo with only 2.5f to 50 ecm
909849/1529909849/1529
/9/ 9
Verminderung der Wirkung von 5 V Isopropylnoradrenalin um ca. 50 %. Reduction of the effect of 5 V isopropyl noradrenaline by approx. 50 %.
Am isolierten Meerschweinchenherzen nach Langendorff verminderte das Verfahrensprodukt bei Dauer infusion von 0,1-qt pro Minute die durch 0,1^f Isopropylnoradrenalin bewirkte Zunahme der Herzfrequenz um ein Drittel. Am Meerschweinchenherzen nach Langendorff wurde durch 15 $ des Verfahrensproduktes die Coronardurchströmung deutlich erhöht. In the isolated guinea pig heart according to Langendorff, the product of the process decreased with continuous infusion of 0.1 qt per minute caused by 0.1 ^ f isopropyl noradrenaline Increase in heart rate by a third. On the guinea pig heart According to Langendorff, the coronary flow was significantly increased by $ 15 of the process product.
Durch die Kombination der 3 erwähnten Wirkungen zeichnen sich die Verfahrensprodukte durch besondere Vorteile gegenüber bisher bekannten Verbindungen aus. Die Verfahrensprodukte sind zur Behandlung der Hypertonie besonders günstig, denn gerade bei Hypertonikern ist eine Herzkranzgefäß- erweiternde Wirkung von Vorteil, da das Herz des Hochdruckkranken eine stark erhöhte Muskelmasse aufweist, die ernährt werden muß. Außerdem neigt der Hypertoniker zu Atheroskleroee der Herzkranzgefäße, deren Folgen evtl. durch eine Erweiterung der kleinen, nicht verkalkenden Gefäße kompensiert werden kann.Due to the combination of the 3 mentioned effects, the process products have particular advantages over them previously known compounds. The products of the process are particularly favorable for the treatment of hypertension, because especially in hypertensive patients there is a coronary artery dilatation This is beneficial because the heart of the hypertensive patient has a greatly increased muscle mass that needs to be nourished got to. In addition, the hypertensive person is prone to atherosclerosis Coronary arteries, the consequences of which may be due to an enlargement the small, non-calcifying vessels can be compensated.
/10/ 10
909849/1529909849/1529
Fw fr79fr aFw fr79fr a
- 10- 10
l-( 3 ' »4 ' -Dimethylphenyl) -2-^phenyl-pyridyl-( 2" ) propylamine^- propanol-(1)-hydrochloridl- (3 '»4' -Dimethylphenyl) -2- ^ phenyl-pyridyl- (2") propylamine ^ - propanol (1) hydrochloride
'CH.'CH.
7,1 g ß-Phenyl-ß-pyridyl-(2)-propionaldehyd und 6,0 g 1-(3',V-Dimethylphenyl)-2-aminopropanol-(1) (Schmp. 90 ), (hergestellt durch Bromierung von 3,4-Dimethylpropiopfenon, Umsetzung der erhaltenen Bronnrerbindung mit Benzylamin und anschließender katalytisch Hydrierung), werdem zusammen in 30 ecm Benzol gelöst, wobei sich die Lösung leicht erwärmt. Das Benzol wird im Vakuum abdestilliert, der Rückstand in Methanol gelöst und 1 g Natriumborhydrid in kleinen Portionen eingetragen, wobei eine lebhafte Reaktion eintritt. Man läßt ca. 15 Minuten stehen, säuert mit verdünnter Salzsäure an und destilliert das Methanol im Vakuum ab. Der Rückstand wird mit verdünnter Natronlauge und Äther geschüttelt. Die ätherische Phase wird abgetrennt, mit Kaliumcarbonat getrocknet und der Äther abdestilULert. Der Rückstand wird mit wenig Methanol gelöst und In Salzsäure zugegeben* Nach Abdestillieren des Lösungsmittels wird der Rückstand aus Aceton/Äther umkristallisiert. Es werden 9,5 g 1-(3',V-Dimethylphenyl) -2^/phenyl-pyridyl( 2" ) -propylamino/'-propanol (I)-hydrochlorid vom Schmp. I96 - 197 erhalten.7.1 g of ß-phenyl-ß-pyridyl- (2) -propionaldehyde and 6.0 g of 1- (3 ', V-dimethylphenyl) -2-aminopropanol- (1) (melting point 90), (prepared by bromination of 3,4-dimethylpropiopfenone, reaction of the bromine compound obtained with benzylamine and then catalytic hydrogenation), are dissolved together in 30 ecm benzene, the solution warms up slightly. The benzene is distilled off in vacuo, the residue is dissolved in methanol and 1 g of sodium borohydride entered in small portions, with one vigorous reaction occurs. It is left to stand for about 15 minutes, acidified with dilute hydrochloric acid and the methanol is distilled off in vacuo. The residue is diluted with sodium hydroxide and Ether shaken. The ethereal phase is separated off, dried with potassium carbonate and the ether is distilled off. Of the The residue is dissolved with a little methanol and hydrochloric acid is added. * After the solvent has been distilled off, the residue is recrystallized from acetone / ether. 9.5 g of 1- (3 ', V-dimethylphenyl) -2 ^ / phenyl-pyridyl (2 ") -propylamino /' -propanol (I) hydrochloride of melting point 196-197 are obtained.
1111
909849/1529909849/1529
Claims (1)
=CH-CH2-N-CH-C-</ ^ (V) I | 3 H r — χ k
= CH-CH 2 -N-CH-C - </ ^ (V)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0046262 | 1965-06-05 | ||
DEF0047601 | 1965-11-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1545869A1 true DE1545869A1 (en) | 1969-12-04 |
Family
ID=25976808
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19651493715 Pending DE1493715A1 (en) | 1965-06-05 | 1965-06-05 | Process for the preparation of diphenylpropylamine derivatives |
DE19651545869 Pending DE1545869A1 (en) | 1965-06-05 | 1965-11-05 | Process for the preparation of 3-phenyl-3-pyridyl (2 ') -propylamine derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19651493715 Pending DE1493715A1 (en) | 1965-06-05 | 1965-06-05 | Process for the preparation of diphenylpropylamine derivatives |
Country Status (14)
Country | Link |
---|---|
US (1) | US3414578A (en) |
AT (8) | AT277980B (en) |
BE (1) | BE682140A (en) |
BR (1) | BR6680181D0 (en) |
CH (4) | CH465645A (en) |
DE (2) | DE1493715A1 (en) |
DK (1) | DK118407B (en) |
ES (1) | ES327479A1 (en) |
FI (1) | FI45184C (en) |
GB (1) | GB1124838A (en) |
IL (1) | IL25875A (en) |
NL (1) | NL6607736A (en) |
NO (1) | NO117860B (en) |
SE (1) | SE348457B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4275198A (en) * | 1980-07-18 | 1981-06-23 | Carter-Wallace Inc. | Method for preparing basic dithienyl compounds |
-
1965
- 1965-06-05 DE DE19651493715 patent/DE1493715A1/en active Pending
- 1965-11-05 DE DE19651545869 patent/DE1545869A1/en active Pending
-
1966
- 1966-05-30 IL IL25875A patent/IL25875A/en unknown
- 1966-06-02 CH CH797366A patent/CH465645A/en unknown
- 1966-06-02 FI FI661451A patent/FI45184C/en active
- 1966-06-02 CH CH1468468A patent/CH464962A/en unknown
- 1966-06-02 CH CH1468168A patent/CH464961A/en unknown
- 1966-06-02 CH CH1468068A patent/CH464960A/en unknown
- 1966-06-02 SE SE07542/66A patent/SE348457B/xx unknown
- 1966-06-02 ES ES0327479A patent/ES327479A1/en not_active Expired
- 1966-06-03 DK DK288666AA patent/DK118407B/en unknown
- 1966-06-03 BR BR180181/66A patent/BR6680181D0/en unknown
- 1966-06-03 AT AT01690/68A patent/AT277980B/en active
- 1966-06-03 AT AT529166A patent/AT272310B/en active
- 1966-06-03 AT AT169468A patent/AT272314B/en active
- 1966-06-03 AT AT169368A patent/AT275501B/en active
- 1966-06-03 AT AT169268A patent/AT272313B/en active
- 1966-06-03 AT AT168968A patent/AT272312B/en active
- 1966-06-03 NL NL6607736A patent/NL6607736A/xx unknown
- 1966-06-03 AT AT169168A patent/AT275500B/en active
- 1966-06-03 AT AT168868A patent/AT272311B/en active
- 1966-06-04 NO NO163304A patent/NO117860B/no unknown
- 1966-06-06 BE BE682140D patent/BE682140A/xx unknown
- 1966-06-06 GB GB25044/66A patent/GB1124838A/en not_active Expired
- 1966-10-27 US US589816A patent/US3414578A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AT275500B (en) | 1969-10-27 |
IL25875A (en) | 1970-04-20 |
DE1493715A1 (en) | 1969-06-19 |
AT272312B (en) | 1969-07-10 |
FI45184C (en) | 1972-04-10 |
AT272311B (en) | 1969-07-10 |
CH464962A (en) | 1968-11-15 |
AT277980B (en) | 1970-01-12 |
CH464960A (en) | 1968-11-15 |
AT275501B (en) | 1969-10-27 |
BE682140A (en) | 1966-12-06 |
NL6607736A (en) | 1966-12-06 |
CH465645A (en) | 1968-11-30 |
AT272313B (en) | 1969-07-10 |
US3414578A (en) | 1968-12-03 |
CH464961A (en) | 1968-11-15 |
SE348457B (en) | 1972-09-04 |
AT272310B (en) | 1969-07-10 |
FI45184B (en) | 1971-12-31 |
BR6680181D0 (en) | 1973-12-26 |
NO117860B (en) | 1969-10-06 |
DK118407B (en) | 1970-08-17 |
GB1124838A (en) | 1968-08-21 |
ES327479A1 (en) | 1967-10-16 |
AT272314B (en) | 1969-07-10 |
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