DE1035140B - Process for the preparation of N-aminoacylated iminodibenzyls and their salts - Google Patents
Process for the preparation of N-aminoacylated iminodibenzyls and their saltsInfo
- Publication number
- DE1035140B DE1035140B DEG18012A DEG0018012A DE1035140B DE 1035140 B DE1035140 B DE 1035140B DE G18012 A DEG18012 A DE G18012A DE G0018012 A DEG0018012 A DE G0018012A DE 1035140 B DE1035140 B DE 1035140B
- Authority
- DE
- Germany
- Prior art keywords
- iminodibenzyls
- iminodibenzyl
- propionyl
- dichloro
- aminoacylated
- 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
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- -1 α - piperidino - propionyl Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003589 local anesthetic agent Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 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 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
DEUTSCHESGERMAN
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von basisch acylierten, substituierten Iminodibenzylen und deren Salzen mit wertvollen pharmakologischen Eigenschaften.The invention relates to a process for the preparation of basic acylated, substituted iminodibenzyls and their salts with valuable pharmacological properties.
Kernsubstituierte Iminodibenzyle, z. B. 3,7-Dichloriminodibenzyl [3,7-Dichlor-10,ll-dihydro-5-dibenzo-(b,f)-azepin] oder 2,8-Dimethyl-iminodibenzyl, sind bisher nicht bekanntgeworden. Es wurde nun gefunden, daß solche Verbindungen der allgemeinen FormelNuclear substituted iminodibenzyls, e.g. B. 3,7-dichloroiminodibenzyl [3,7-dichloro-10, ll-dihydro-5-dibenzo- (b, f) -azepine] or 2,8-dimethyl-iminodibenzyl, are so far not known. It has now been found that such compounds of the general formula
V^ Χίο ' Ks XXn V ^ Χίο ' Ks XXn
CO-CnH2n-AmCO-C n H 2n -Am
in der η eine niedrige Zahl, Am einen niedermolekularen Dialkylaminorest oder einen Alkyleniminorest mit 5 bis 6 Ringgliedern und X ein Halogenatom oder eine Methylgruppe bedeutet, sowie auch deren Salze starke lokalanästhetische und teilweise auch spasmolytische Wirksamkeit besitzen.in which η denotes a low number, Am denotes a low molecular weight dialkylamino group or an alkylenimino group with 5 to 6 ring members and X denotes a halogen atom or a methyl group, and the salts thereof also have strong local anesthetic and sometimes also spasmolytic activity.
Es ist bekannt, N-aminoacylierte Iminodibenzyle durch Umsetzung von N-(Halogenalkanoyl)-iminodibenzylen mit niedermolekularen Dialkylaminen oder Alkyleniminen mit 5 bis 6 Ringgliedern herzustellen und die erhaltenen Basen gegebenenfalls in ihre Salze überzuführen. Diese Verbindungen zeigen lokalanästhetische Wirkung (Helvetica Chimica Acta, Bd. 37 [1954], S. 472 bis 483).It is known to use N-aminoacylated iminodibenzyls Reaction of N- (haloalkanoyl) -iminodibenzylene with low molecular weight dialkylamines or alkyleneimines with 5 to 6 ring members and optionally converting the bases obtained into their salts. These Compounds show a local anesthetic effect (Helvetica Chimica Acta, Vol. 37 [1954], pp. 472 to 483).
Die neuen kernsubstituierten N-aminoacylierten Iminodibenzyle und deren Salze werden erhalten, wenn man bei dem Verfahren zur Herstellung von N-aminoacylierten Iminodibenzylen und deren Salzen durch Umsetzung von N-(Halogenalkanoyl)-iminodibenzylen mit niedermolekularen Dialkylaminen oder Alkyleniminen mit 5 bis 6 Ringgliedern sowie gegebenenfalls Behandlung der erhaltenen Basen mit anorganischen oder organischen Säuren substituierte N-(Halogenalkanoyl)-iminodibenzyle der allgemeinen FormelThe new nuclear-substituted N-aminoacylated iminodibenzyls and their salts are obtained when in the process for the preparation of N-aminoacylated Iminodibenzylene and its salts by reacting N- (haloalkanoyl) -iminodibenzylene with low molecular weight Dialkylamines or alkylenimines with 5 to 6 ring members and, if appropriate, treatment of the obtained bases with inorganic or organic acids substituted N- (haloalkanoyl) -iminodibenzyls the general formula
CH9 CH 9
CO-C„H2K —HaiCO-C “H 2K — Shark
Verfahren zur HerstellungMethod of manufacture
von N-aminoacylierten Iminodibenzylenof N-aminoacylated iminodibenzyls
und deren Salzenand their salts
Anmelder:
J. R. Geigy A.-G., Basel (Schweiz)Applicant:
JR Geigy A.-G., Basel (Switzerland)
Vertreter: Dr. F. Zumstein, Patentanwalt,
München 2, Bräuhausstr. 4Representative: Dr. F. Zumstein, patent attorney,
Munich 2, Bräuhausstr. 4th
Beanspruchte Priorität:
Schweiz vom 22. September 1954Claimed priority:
Switzerland from September 22, 1954
Dr. Walter Schindler, Riehen,Dr. Walter Schindler, Riehen,
und Dr. Franz Häfliger, Basel (Schweiz),and Dr. Franz Häfliger, Basel (Switzerland),
sind als Erfinder genannt wordenhave been named as inventors
in der η eine niedrige Zahl, Hai ein Halogenatom und X ein Halogenatom oder eine Methylgruppe bedeutet, umsetzt.in which η is a low number, Hal is a halogen atom and X is a halogen atom or a methyl group.
Die Umsetzung kann in einem inerten Lösungsmittel,The reaction can be carried out in an inert solvent,
z. B. Benzol oder dessen Homologen, vorgenommen werden. Zur Bindung der bei der Reaktion frei werdenden Halogenwasserstoffsäure kann ein Überschuß des zur Umsetzung gelangenden Amins dienen; man kann dazu aber auch eine organische tertiäre Base, wie Dimethylanilin oder Pyridin, oder anorganische säurebindende Stoffe, z. B. Natrium- oder Kaliumcarbonat, verwenden.z. B. benzene or its homologues can be made. To bind the released during the reaction Hydrohalic acid can be used in an excess of the amine which is reacted; one can do this but also an organic tertiary base, such as dimethylaniline or pyridine, or inorganic acid-binding bases Substances, e.g. B. sodium or potassium carbonate, use.
Als 5 - (Halogenalkanoyl) - 3,7 - dichlor - iminodibenzyle seien beispielsweise genannt: Chloracetyl-, Bromacetyl-, a-Chlor-propionyl-, a-Brom-propionyl-, a-Brom-butyryl-, a-Brom-isobutyryl-, a-Brom-valeryl-, a-Brom-isovaleryl-, a-Brom-caproyl-3,7-dichlorimino-dibenzyl, ^-Chlor-propionyl-, /9-Brom-propionyl-, /J-Chlor-butyryl-, /?-Brombutyryl-.ß-Chlor-isobutyryl-.jS-Brom-isobutyryl-.ß-Brorn- valeryl-, /J-Brom-isovaleryl-, y-Chlor-butyryl-, y-Chlorvaleryl- und o-Chlor-valeryl-S^-dichlor-iminodibenzyl. Ebensogut können die entsprechenden Derivate des 1,9- oder 2,8-Dichlor- oder des 1,9-, 2,8- oder 3,7-Dibromiminodibenzyls, 2,8-Dimethyl- oder 3,7-Dimethyl-iminodibenzyls verwendet werden.Examples of 5 - (haloalkanoyl) - 3,7 - dichloro - iminodibenzyls are: chloroacetyl, bromoacetyl, a-chloro-propionyl-, a-bromo-propionyl-, a-bromo-butyryl-, a-bromo-isobutyryl-, a-bromo-valeryl-, a-bromo-isovaleryl-, a-bromo-caproyl-3,7-dichloroimino-dibenzyl, ^ -chloropropionyl-, / 9-bromo-propionyl-, / J-chloro-butyryl-, /?-bromobutyryl-.ß-chlorine-isobutyryl-.jS-bromo-isobutyryl-.ß-brorn- valeryl-, / J-bromo-isovaleryl-, y-chloro-butyryl-, y-chlorovaleryl- and o-chloro-valeryl-S ^ -dichloro-iminodibenzyl. The corresponding derivatives of 1,9- or 2,8-dichloro- or 1,9-, 2,8- or 3,7-dibromiminodibenzyl, 2,8-dimethyl- or 3,7-dimethyl-iminodibenzyls can be used.
Die genannten N-(Halogenalkanoyl)-3,7-dichlor-iminodibenzyle können beispielsweise mit Dimethylamin, Methyl-äthylamin, Diäthylamin, Dipropylamin, Diisopropylamin, Dibutyl- und Diamylaminen, Methylallylamin, Diallylamin, Pyrrolidin, Piperidin oder C-alkylierten Pyrrolidinen oder Piperidinen umgesetzt werden.The N- (haloalkanoyl) -3,7-dichloro-iminodibenzyls mentioned can, for example, with dimethylamine, methylethylamine, diethylamine, dipropylamine, diisopropylamine, Dibutyl and diamyl amines, methylallylamine, diallylamine, pyrrolidine, piperidine or C-alkylated Pyrrolidines or piperidines are implemented.
Mit anorganischen und organischen Säuren, z. B. Salzsäure, Schwefelsäure, Phosphorsäure, Weinsäure, Citronen-With inorganic and organic acids, e.g. B. hydrochloric acid, sulfuric acid, phosphoric acid, tartaric acid, citric
. . . 809 579/447. . . 809 579/447
säure und Salicylsäure, bilden die neuen Verbindungen Salze, welche teilweise in Wasser mit annähernd neutraler Reaktion löslich sind.acid and salicylic acid, the new compounds form salts, some of which in water with approximately neutral salts Reaction are soluble.
DieerfindungsgemäßenN-aminoacyliertensubstituierten Iminodibenzyle sind in der lokalanästhetischen Wirksamkeit den in den Benzolkernen unsubstituierten N-acylierten Iminodibenzylen, welche in Helvetica Chimica Acta, Bd. 37 (1954), S. 472 bis 483, beschrieben sind, überlegen. So erwies sich im Vergleichsversuch nach der Methode von Regnier an der Kaninchencornea das N-a-Diäthylaminopropionyl-3,7-dimethyl-iminodibenzyl und das N-a-Diäthylamino - propionyl -2,8 - dimethyl - iminodibenzyl 2,3- bzw. 7,3mal wirksamer als das bekannte N-a-Diäthylamino-propionyl-iminodibenzyl und das N-Diäthylaminoacetyl-3,7-dichlor-iminodibenzyl 11 mal wirksamer als das bekannte N-Diäthylamino-acetyl-iminobenzyl bei etwas geringerer Toxizität.The N-aminoacylated substituted iminodibenzyls of the invention are in local anesthetic effectiveness the N-acylated iminodibenzylene unsubstituted in the benzene nuclei, which in Helvetica Chimica Acta, Vol. 37 (1954), pp. 472 to 483, are superior. This proved to be the case in a comparative test using the method of Regnate the N-α-diethylaminopropionyl-3,7-dimethyl-iminodibenzyl on the rabbit cornea and the N-a-diethylamino - propionyl -2,8 - dimethyl - iminodibenzyl 2,3- or 7.3 times more effective than the known N-a-diethylamino-propionyl-iminodibenzyl and the N-diethylaminoacetyl-3,7-dichloro-iminodibenzyl 11 times more effective than that known N-diethylamino-acetyl-iminobenzyl for something lower toxicity.
Die nachfolgenden Beispiele sollen die Herstellung der neuen Verbindungen näher erläutern. Teile bedeuten Gewichtsteile.The following examples are intended to explain the preparation of the new compounds in more detail. Parts mean Parts by weight.
CHCH
Beispiel 1
CH,example 1
CH,
C Ho C HoC Ho C Ho
CH9-CH,CH 9 -CH,
XH9 XH 9
CH9-CHCH 9 -CH
CoH1 CoH 1
Sn5S n 5
CO-CH9-N:CO-CH 9 -N:
15Teile5-Chloracetyl-3,7-dichlor-iminodibenzyl(F.142°C) werden mit 50 Volumteilen reinem Diäthylamin 16 Stunden unter Rückfluß gekocht. Dann gießt man in Wasser und schüttelt mit Äther aus. Den Ätherlösungen wird die Base durch Schütteln mit verdünnter Salzsäure entzogen. Die vereinigten salzsauren Auszüge werden mit konzentriertem Ammoniak alkalisch gestellt und das ausgefallene 5-Diäthylaminoacetyl-S^-dichlor-iminodibenzyl [5-Diäthylaminoacetyl-3,7-dichlor-10,ll-dihydro-5-dibenzo-(b,f)- azepin] aus Alkohol umkristallisiert, worauf es einen Schmelzpunkt von 99 bis 100° C besitzt.15 parts 5-chloroacetyl-3,7-dichloro-iminodibenzyl (M.p. 142 ° C) are refluxed for 16 hours with 50 parts by volume of pure diethylamine. Then you pour in water and shakes out with ether. The base is removed from the ether solutions by shaking with dilute hydrochloric acid. the combined hydrochloric acid extracts are made alkaline with concentrated ammonia and the precipitated 5-diethylaminoacetyl-S ^ -dichloro-iminodibenzyl [5-Diethylaminoacetyl-3,7-dichloro-10, ll-dihydro-5-dibenzo- (b, f) - azepine] recrystallized from alcohol, whereupon a Has a melting point of 99 to 100 ° C.
In analoger Weise erhält man das 5-Piperidino-acetyl-3,7-dichlor-iminodibenzyl [S-Piperidinoacetyl-S^-dichlor-10,ll-dihydro-dibenzo-(b,f)-azepin] vom F. 1050C, das S-(a- Piperidino - propionyl) - 3,7 - dimethyl - iminodibenzyl vom F. 124 bis 125° C sowie das 5-(cc-Diäthylaminopropionyl)-3,7-dimethyl-iminodibenzyl vom F. 265 bis 2670C.In an analogous manner there is obtained 5-Piperidinoacetyl-3,7-dichloro-iminodibenzyl [S-Piperidinoacetyl-S ^ Dichloro-10, ll-dihydro-dibenzo (b, f) azepine], mp 105 0 C, the S- (a- piperidino-propionyl) -3,7-dimethyl-iminodibenzyl from mp 124 to 125 ° C and the 5- (cc-diethylaminopropionyl) -3,7-dimethyl-iminodibenzyl from mp 265 to 267 0 C.
Claims (1)
Helvetica Chimica Acta, Bd. 37 (1954), S. 472 bis 483.Considered publications:
Helvetica Chimica Acta, 37: 472-483 (1954).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1035140X | 1954-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1035140B true DE1035140B (en) | 1958-07-31 |
Family
ID=4553932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG18012A Pending DE1035140B (en) | 1954-09-22 | 1955-09-21 | Process for the preparation of N-aminoacylated iminodibenzyls and their salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1035140B (en) |
-
1955
- 1955-09-21 DE DEG18012A patent/DE1035140B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
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