DE1090672B - Process for the production of the locally anesthetically and antihistaminically active benzhydryl ether of nortropine and its salts - Google Patents
Process for the production of the locally anesthetically and antihistaminically active benzhydryl ether of nortropine and its saltsInfo
- Publication number
- DE1090672B DE1090672B DEB40763A DEB0040763A DE1090672B DE 1090672 B DE1090672 B DE 1090672B DE B40763 A DEB40763 A DE B40763A DE B0040763 A DEB0040763 A DE B0040763A DE 1090672 B DE1090672 B DE 1090672B
- Authority
- DE
- Germany
- Prior art keywords
- nortropine
- salts
- ether
- benzhydryl
- production
- 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
- YYMCYJLIYNNOMK-UHFFFAOYSA-N N-normethyltropine Natural products C1C(O)CC2CCC1N2 YYMCYJLIYNNOMK-UHFFFAOYSA-N 0.000 title claims description 21
- YYMCYJLIYNNOMK-MEKDEQNOSA-N (1r,5s)-8-azabicyclo[3.2.1]octan-3-ol Chemical compound C1C(O)C[C@@H]2CC[C@H]1N2 YYMCYJLIYNNOMK-MEKDEQNOSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 9
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 13
- 230000001387 anti-histamine Effects 0.000 claims description 11
- 150000002170 ethers Chemical class 0.000 claims description 4
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 3
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PCPKJCNOJKIDMG-UHFFFAOYSA-N C1=CC=C(C(C2=CC=CC=C2)OC(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.Br Chemical compound C1=CC=C(C(C2=CC=CC=C2)OC(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.Br PCPKJCNOJKIDMG-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000002921 anti-spasmodic effect Effects 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 salts diphenylmethyl ether Chemical class 0.000 description 3
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 2
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 229940088007 benadryl Drugs 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001459693 Dipterocarpus zeylanicus Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- JTBRUCSFYHKRFB-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 JTBRUCSFYHKRFB-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung des lokalanästhetisch und antihistaminisch wirksamen Benzhydryläthers des Nortropins und seiner Salze Diphenylmethyläther des Tropins und Pseudotropins sind bereits bekannt. Es ist ferner bekannt, daß diese Äther eine atropinähnliche krampflösende Wirkung sowie Antihistamineigenschaften besitzen. Bei diesen Verbindungen übersteigt die krampflösende Wirkung die anderen Eigenschaften so sehr, daß eine Verwendung als Antihistamin nicht in Frage kommt. Lediglich beim Tropin-p-chlor-b,enzhydryläther ist das Verhältnis von Antihistaminwirkung zur krampflösenden Wirkung so ausgeglichen, daß die Antihistaminwirkung ausgewertet werden kann.Process for the preparation of the local anesthetic and antihistaminic effective benzhydryl ether of nortropine and its salts diphenylmethyl ether of Tropins and pseudotropins are already known. It is also known that this Ether has an atropine-like antispasmodic effect as well as antihistamine properties own. With these compounds, the anticonvulsant effect outweighs the others Properties so much that it cannot be used as an antihistamine. Only in the case of tropine-p-chloro-beta-enzhydryl ether is the ratio of antihistamine effect so balanced for the antispasmodic effect that the antihistamine effect is evaluated can be.
Es wurde nun gefunden, daß durch eine Veränderung des Substituenten am Stickstoffatom des Tropingerüstes Verbindungen erhalten werden, deren Antihistaminwirkung die der bisher bekannten Verbindungen übertrifft und die darüber hinaus eine wesentlich gesteigerte Wirkungsdauer haben. Da es für die medizinische Anwendung günstig ist, wenn eine geringe krampflösende Wirkung mit einer starken Antihistaminwirkung verbunden ist, sind die neuen Äther besonders wertvoll.It has now been found that by changing the substituent on the nitrogen atom of the troping skeleton compounds are obtained whose antihistamine action that of the previously known compounds surpasses and, moreover, a substantial one have increased duration of action. Since it is favorable for medical use, when a low antispasmodic effect is combined with a strong antihistamine effect the new ethers are especially valuable.
Die Erfindung betrifft eine weitere Ausbildung des Verfahrens nach Patent 1077 223. Das Hauptpatent betrifft ein Verfahren zur Herstellung von lokalanästhetisch und antihistaminisch wirksamen N-substituierten Benzhydryläthern des Nortropins und deren Salzen der allgemeinen Formel in der R den Isopropyl- oder den Allylrest bedeutet, das dadurch gekennzeichnet ist, daß man die entsprechend substituiertenNortropine mit Benzhydrol oder seinen funktionellen Derivaten in an sich bekannter Weise veräthert und die erhaltenen Äther in ihre Salze überführt.The invention relates to a further development of the process according to patent 1077 223. The main patent relates to a process for the production of locally anesthetically and antihistaminically active N-substituted benzhydryl ethers of nortropine and their salts of the general formula in which R denotes the isopropyl or the allyl radical, which is characterized in that the appropriately substituted nortropines are etherified with benzhydrol or its functional derivatives in a manner known per se and the ethers obtained are converted into their salts.
Es wurde nun gefunden, daß der Benzhydryläther des Nortropins ebenso wie die nach dem Verfahren des Hauptpatents hergestellten Verbindungen den bereits bekannten Tropinäthern hinsichtlich ihrer Antihistaminwirkung überlegen ist.It has now been found that the benzhydryl ether of nortropine does the same like the connections produced according to the process of the main patent the already is superior to known tropine ethers with regard to their antihistamine effect.
Nach dem Verfahren der Erfindung werden der Benzhydryläther des Nortropins und seine Salze hergestellt.According to the process of the invention, the benzhydryl ethers of nortropine are obtained and made its salts.
Die Herstellung dieser Verbindung erfolgt durch Verätherung von Nortropin mit Benzhydrol oder seinen funktionellen Derivaten in an sich bekannter Weise. Wenn bei dieser Umsetzung der freie Äther erhalten wird, so kann dieser anschließend in die gewünschten Salze übergeführt werden.This connection is made through the etherification of nortropin with benzhydrol or its functional derivatives in a manner known per se. if in this implementation of the free ether is obtained, it can then be converted into the desired salts.
Die Herstellung des Äthers des Nortropins erfolgt in der im Hauptpatent angegebenen Weise. So besteht eine bevorzugte Ausführungsform des Verfahrens nach der Erfindung darin, daß man das Nortropin zusammen mit einem Benzhydrylhalogenid bei erhöhten Temperaturen in einem inerten, wasserfreien, organischen Lösungsmittel, das ein tertiäres Amin enthält, umsetzt. Bei dieser Arbeitsweise fällt sofort das halogenwasserstoffsaure Salz des Äthers aus.The production of the aether of Nortropin takes place in the main patent specified way. Thus, there is a preferred embodiment of the method according to of the invention is that the nortropine together with a benzhydryl halide at elevated temperatures in an inert, anhydrous, organic solvent, which contains a tertiary amine, reacts. With this way of working, that happens immediately Hydrogen halide salt of the ether.
Der nach dem Verfahren der Erfindung herstellbare Benzhydryläther
des Nortropins und seine Salze sind wertvolle Heilmittel, besonders Antihistaminica
und Lokalanästhetica. Wie aus der folgenden Tabelle hervorgeht, ist das Nortropinbenzhydryläther-hydrobromid
hinsichtlich der Antihistaminwirkungsdauer den in der Tabelle weiter angegebenen
bekannten Antihistaminen überlegen. Neben einer geringen Giftigkeit weist das Nortropinbenzhydryläther-hydrobromid
eine geringe krampflösende Wirkung auf, so daß mit Nebenwirkungen, wie sie beim
Atropin auftreten, nicht zu rechnen ist. Außerdem wirkt das Nortropinbenzhydryläther-hydrobromid
nicht beruhigend, was sowohl im Tierversuch als auch bei der Verabreichung dieser
Verbindung beim Menschen festgestellt wurde.
Auf dem Papierchromatogramm zeigt die Verbindung einen reinen scharfen Fleck.On the paper chromatogram, the compound shows a pure, sharp one Spot.
C20H23ON - HBr, Molekulargewicht 374,32. Berechnet C 64,17, H 6,46, N 3,74, Br 21,35%; gefunden C 64,15, H 6,64, N 3,74, Br 21,110/0. Das Methansulfonat des Nortropinbenzhydryläthers bildet weiße Kristalle vom F.=191 bis 193' C unter Zersetzung nach dem Umfällen aus Isopropanol-Isopropyläther.C20H23ON - HBr, molecular weight 374.32. Calculated C 64.17, H 6.46, N 3.74, Br 21.35%; Found C 64.15, H 6.64, N 3.74, Br 21.110 / 0. The methanesulfonate of nortropine benzhydryl ether forms white crystals with a temperature of 191 to 193 ° C. with decomposition after reprecipitation from isopropanol-isopropyl ether.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB40763A DE1090672B (en) | 1956-06-22 | 1956-06-22 | Process for the production of the locally anesthetically and antihistaminically active benzhydryl ether of nortropine and its salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB40763A DE1090672B (en) | 1956-06-22 | 1956-06-22 | Process for the production of the locally anesthetically and antihistaminically active benzhydryl ether of nortropine and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1090672B true DE1090672B (en) | 1960-10-13 |
Family
ID=6966183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB40763A Pending DE1090672B (en) | 1956-06-22 | 1956-06-22 | Process for the production of the locally anesthetically and antihistaminically active benzhydryl ether of nortropine and its salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1090672B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1289849B (en) * | 1963-02-15 | 1969-02-27 | Koninklijke Pharma Fab Nv | 3- (Dibenzo [a, d] -1, 4-cycloheptadien-5-yloxy) -nortropane and process for its preparation |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2678317A (en) * | 1954-05-11 | N - benzhydryltropylamine com | ||
| US2706198A (en) * | 1952-03-29 | 1955-04-12 | Merck & Co Inc | Benzhydryl ethers of tropine and processes of preparation |
-
1956
- 1956-06-22 DE DEB40763A patent/DE1090672B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2678317A (en) * | 1954-05-11 | N - benzhydryltropylamine com | ||
| US2706198A (en) * | 1952-03-29 | 1955-04-12 | Merck & Co Inc | Benzhydryl ethers of tropine and processes of preparation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1289849B (en) * | 1963-02-15 | 1969-02-27 | Koninklijke Pharma Fab Nv | 3- (Dibenzo [a, d] -1, 4-cycloheptadien-5-yloxy) -nortropane and process for its preparation |
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