DE858401C - Process for the production of nicotinic acid esters - Google Patents
Process for the production of nicotinic acid estersInfo
- Publication number
- DE858401C DE858401C DET3384A DET0003384A DE858401C DE 858401 C DE858401 C DE 858401C DE T3384 A DET3384 A DE T3384A DE T0003384 A DET0003384 A DE T0003384A DE 858401 C DE858401 C DE 858401C
- Authority
- DE
- Germany
- Prior art keywords
- nicotinic acid
- ethylene glycol
- acid
- production
- nicotinic
- 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.)
- Expired
Links
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 7
- 239000011664 nicotinic acid Substances 0.000 claims description 19
- 229960003512 nicotinic acid Drugs 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 235000001968 nicotinic acid Nutrition 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 6
- -1 nicotinic acid halides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IZJRISIINLJVBU-UHFFFAOYSA-N beta-Butoxyethyl nicotinate Chemical compound CCCCOCCOC(=O)C1=CC=CN=C1 IZJRISIINLJVBU-UHFFFAOYSA-N 0.000 description 3
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940064982 ethylnicotinate Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 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
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Nicotinsäureestern Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von hyperämisierend wirkenden Estern der Nicotinsäure.Process for the preparation of nicotinic acid esters The present invention relates to a process for the preparation of esters with a hyperaemia Nicotinic acid.
Es -ist bekannt, daß der Nicotinsäureester des Tetrahydrofurfurylalköhols ebenso wie Nicotinsäurealkylester, die q. bis 8 Kohlenstoffatome im Alkylrest enthalten, hyperämisierend auf die Haut wirken. Dagegen ist die kapillarerweiternde Wirkung von Estern der Nicotinsäure mit niedermolekularen Alkoholen nur kurz dauernd.It is known that the nicotinic acid ester of tetrahydrofurfuryl alcohol as well as nicotinic acid alkyl esters, the q. contain up to 8 carbon atoms in the alkyl radical, have a hyperaemic effect on the skin. On the other hand, there is the capillary-expanding effect of esters of nicotinic acid with low molecular weight alcohols only lasts for a short time.
Gemäß der vorliegenden Erfindung erhält man hyperämisierend wirkende Ester der Nicotinsäure von langer Wirkungsdauer, indem man Nicotinsäure, Nicotinsäureanhydrid oder Nicotinsäurehalogenide in Gegenwart von wasserentziehenden oder säurebindenden Mitteln mit den Monoalkyl-, -aryl- oder -aralkyläthern des Äthylenglykols, gegebenenfalls bei Anwesenheit von .Lösungsmitteln, umsetzt. Man kann selbstverständlich auch so arbeiten, daß man Alkylester der Nicotinsäure mit den Monoalkyl-, -aryl- oder -aralkyläthern.._ des Äthylenglykolls umestert.According to the present invention, hyperaemic effects are obtained Nicotinic acid esters of long duration of action by adding nicotinic acid, nicotinic anhydride or nicotinic acid halides in the presence of dehydrating or acid-binding agents Agents with the monoalkyl, -aryl- or -aralkyl ethers of ethylene glycol, if appropriate in the presence of solvents. Of course you can do that too work that one alkyl esters of nicotinic acid with the monoalkyl, -aryl or -aralkyl ethers .._ of the ethylene glycol is transesterified.
Wie festgestellt wurde, zeigen die Halbester von Nicotinsäure mit Äthylenglykol, dessen zweite Hydroxylgruppe alkyliert, aryliert oder aralkyliert ist, eine ausgezeichnete und lang andauernde hyperämisierende Wirkung auf die Haut und können daher pharmazeutische Verwendung finden.As has been found, the half esters of nicotinic acid show with Ethylene glycol, the second hydroxyl group of which is alkylated, arylated or aralkylated is, an excellent and long-lasting hyperaemic effect on the skin and can therefore find pharmaceutical use.
Wird die Umsetzung der Ausgangsstoffe in Gegenwart von organischen Lösungsmitteln vorgenommen, so können beispielsweise Benzol, Toluol, Tetrachlorkohlenstoff u. ä. Verwendung finden. Als wasserentziehende Mittel zur Durchführung des erfindungsgemäßen Verfahrens sind u. a. Salzsäure und Schwefelsäure geeignet.If the implementation of the starting materials in the presence of organic Solvents made, for example, benzene, toluene, carbon tetrachloride and the like. As a dehydrating agent to carry out of the method according to the invention are inter alia. Hydrochloric acid and sulfuric acid are suitable.
Bei Verwendung von Nicotinsäurehalogeniden als Ausgangsmaterial kommen zur Bindung des frei werdenden Halogenwasserstoffs Pyridin, Dimethylanilin u. ä. in Betracht.When using nicotinic acid halides as starting material come to bind the released hydrogen halide pyridine, dimethylaniline and the like. into consideration.
Die Durchführung des erfindungsgemäßen Verfahrens soll im folgenden an Hand einiger Ausführungsbeispiele näher erläutert werden. Beispiel 1 61,5g N icotinsäure werden mit 26o g reinem Thionylchlorid versetzt und 30 Minuten am Rückflußkühler erhitzt. Die Hauptmenge des Thionylchloridswird dann bei gewöhnlichem Druck und der Rest im Vakuum bei einer 70° nicht übersteigenden Außentemperatur abdestilliert. Zu dem Kristallkuchen von Nicotinsäurechloridhydrochlorid gibt man, nachdem ein Rückfluß'kühler aufgesetzt wurde, ein Gemisch von 83 g Äthy lenglykolmonopropyläther und 64g wasserfreiem Pyridin zii und schüttelt kräftig, wobei starke Erwärmung eintritt, bis zur völligen Lösung. Nach mehrstündigem Stehen wird Wasser zugegeben und so viel Natriumcarbonat, bis sich keine Kohlensäure mehr entwickelt.' Die abgeschiedene, ölige Flüssigkeit wird der Vakuumdestillation unterworfen. I`Ticotinsäure-ß-propoxyäthylester, Kp" 165°, ölige, gelbliche Flüssigkeit. Beispiel e Eine Mischung von 61,5 g Nicotinsäure und 125 g Äthylenglykolmonopropyläther wird unter Durchleitung eines Salzsäuregasstromes d. Stunden im Ölbad von etwa i4o° erhitzt und, wie in Beispiel i angegeben, aufgearbeitet. hTicotinsäure-ß-propoxyäthylester, Kp17 165o. Beispiel 3 Das aus 61,5- Nicotinsäure erhaltene Nicotinsäurechloridhydrochlorid wird unter Riickflußkiiiilung und Feuchtigkeitsausschluß mit einem Gemisch -R von i i8 g Äthylenglykolmonobutyläther und ioo g wasserfreiem Pyridin unter kräftigem Umschütteln versetzt, wobei unter starker Wärmeentwicklung Lösung eintritt. Das Reaktionsgemisch wird wie in Beispiel i aufgearbeitet. Nicotinsäure-ß-butoxyäthylester, Kp" 166 bis 167°, ölige, gelbliche Flüssigkeit. 36 g N icotinsäurechloridhydrochlorid werden unter Rückflußkühlung mit einer Lösung von 3c >g Äthylenglykolmonophenvläther, 40 9 wasserfreiem Pyridin und 30g, Benzol versetzt. Das Gemisch wie i Stunde im Dampfbad erhitzt und nach dem Abkühlen wie in Beispiel i aufgearbeitet. Nicotinsäure-ß-1>lienoxyäthylester, Kl>zi i95 bis 196°. gelbliche, ölige Flüssigkeit. Beispiel 36 g Nicotinsäurechlori,dhydrochlorid werden unter Rückflußkühlung mit einer Mischung von 30 g Äthylenglykolmonobenzyläther, 2o ccm wasserfreiem Benzol und 40 ccm wasserfreiem Pyridin versetzt. Zur Vervollständigung der Reaktion erwärmt man 2 Stunden auf dem Dampfbad. Die Aufarbeitung erfolgt wie in Beispiel i. Man erhält Nicotinsäu,re-ß-benzyloxy.äthylester, Kps 2o5° (unter Stickstoff), ölige, gelbliche Flüssigkeit. Beispie16 ioo g Nicotinsäureäthylester und 3009 Äthylenglykolmonobutyläther werden, zweckmäßig unter Zusatz von i g Nicotinsäure als Katalysator und unter Durchleiten eines Stickstoffstromes 6 Stunden am Luftkühler im Ölbad in kräftigem Sieden gehalten. Danach wird die Flüssigkeit der Vakuumdestillation unterworfen und das nach der Entfernung des überschüssigen Butylglykols übergegangene Gemisch von Nicotinsäureäthylester und Nicotinsäure-ß-butoxy äthylester mit Wasser ausgeschüttelt. Die wasserunlösliche Schicht wird nochmals im Vakuum destilliert. Der erhaltene Nicotinsäure-ß-butoxyäthylester 'hat bei i i mm einen Kp. von 166 bis 16j°.The implementation of the method according to the invention will be explained in more detail below with the aid of a few exemplary embodiments. Example 1 To 61.5 g of nicotinic acid, 260 g of pure thionyl chloride are added and the mixture is heated in a reflux condenser for 30 minutes. Most of the thionyl chloride is then distilled off at normal pressure and the remainder in vacuo at an external temperature not exceeding 70 °. To the crystal cake of nicotinic acid chloride hydrochloride, after a reflux condenser has been attached, a mixture of 83 g of ethylene glycol monopropyl ether and 64 g of anhydrous pyridine is added and shaken vigorously, with intense heating, until complete solution. After standing for several hours, water is added and enough sodium carbonate until no more carbonic acid develops. ' The separated, oily liquid is subjected to vacuum distillation. I`Ticotinic acid-ß-propoxyethyl ester, bp "165 °, oily, yellowish liquid. Example e A mixture of 61.5 g of nicotinic acid and 125 g of ethylene glycol monopropyl ether is heated for hours in an oil bath at about 14o ° while passing through a stream of hydrochloric acid gas given in Example I. hTicotinic acid-β-propoxyethyl ester, boiling point 17 165o. Example 3 The nicotinic acid chloride hydrochloride obtained from 61,5-nicotinic acid is refluxed and with exclusion of moisture with a mixture -R of 18 g of ethylene glycol monobutyl ether and 100 g of anhydrous pyridine shaking vigorously The reaction mixture is worked up as in Example I. β-butoxyethyl nicotinate, boiling point 166 ° to 167 °, oily, yellowish liquid. 36 g of nicotinic acid chloride hydrochloride are refluxed with a solution of 3 g> g of ethylene glycol monophene ether, 40 g of anhydrous pyridine and 30 g of benzene. The mixture was heated in the steam bath for 1 hour and, after cooling, worked up as in Example 1. Β-1 nicotinic acid lienoxyethyl ester, Kl> zi i95 to 196 °. yellowish, oily liquid. EXAMPLE 36 g of nicotinic acid chloride are added under reflux cooling with a mixture of 30 g of ethylene glycol monobenzyl ether, 20 cc of anhydrous benzene and 40 cc of anhydrous pyridine. To complete the reaction, the mixture is heated on the steam bath for 2 hours. The work-up is carried out as in Example i. Nicotinic acid, re-ß-benzyloxyethyl ester, Kps 2o5 ° (under nitrogen), an oily, yellowish liquid, is obtained. Beispie16 100 g of ethyl nicotinate and 3009 g of ethylene glycol monobutyl ether are kept vigorously boiling for 6 hours in an air cooler in an oil bath, expediently with the addition of ig nicotinic acid as a catalyst and while a stream of nitrogen is passed through. The liquid is then subjected to vacuum distillation and the mixture of ethyl nicotinate and ß-butoxy ethyl nicotinate which has passed over after the removal of the excess butyl glycol is extracted with water. The water-insoluble layer is distilled again in vacuo. The β-butoxyethyl nicotinate obtained has a boiling point of 166 to 16 ° at i mm.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET3384A DE858401C (en) | 1950-10-10 | 1950-10-10 | Process for the production of nicotinic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET3384A DE858401C (en) | 1950-10-10 | 1950-10-10 | Process for the production of nicotinic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE858401C true DE858401C (en) | 1952-12-08 |
Family
ID=7544234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET3384A Expired DE858401C (en) | 1950-10-10 | 1950-10-10 | Process for the production of nicotinic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE858401C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1157624B (en) * | 1958-04-14 | 1963-11-21 | Eprova Ag | Process for the preparation of the new 1, 3, 4, 6- and 1, 3, 4, 5-tetranicotinoyl-fructose |
| DE1172678B (en) * | 1958-03-28 | 1964-06-25 | Donau Pharmazie Ges M B H | Process for the production of the new nicotinic acid ester of methyl- (p-tolyl) -carbinol |
| DE1205541B (en) * | 1963-07-18 | 1965-11-25 | Krewel Leuffen Gmbh | Process for the production of basic nicotinic acid esters |
-
1950
- 1950-10-10 DE DET3384A patent/DE858401C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1172678B (en) * | 1958-03-28 | 1964-06-25 | Donau Pharmazie Ges M B H | Process for the production of the new nicotinic acid ester of methyl- (p-tolyl) -carbinol |
| DE1157624B (en) * | 1958-04-14 | 1963-11-21 | Eprova Ag | Process for the preparation of the new 1, 3, 4, 6- and 1, 3, 4, 5-tetranicotinoyl-fructose |
| DE1205541B (en) * | 1963-07-18 | 1965-11-25 | Krewel Leuffen Gmbh | Process for the production of basic nicotinic acid esters |
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