DE1196207B - Process for the preparation of new quaternary ajmalinium salts - Google Patents
Process for the preparation of new quaternary ajmalinium saltsInfo
- Publication number
- DE1196207B DE1196207B DET24241A DET0024241A DE1196207B DE 1196207 B DE1196207 B DE 1196207B DE T24241 A DET24241 A DE T24241A DE T0024241 A DET0024241 A DE T0024241A DE 1196207 B DE1196207 B DE 1196207B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- ajmalinium
- salts
- preparation
- acid
- 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 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 ajmaline compound Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 claims description 2
- 244000061121 Rauvolfia serpentina Species 0.000 claims description 2
- 229960004332 ajmaline Drugs 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 description 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 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 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von neuen quartären Ajmaliniumsalzen Die Erfindung betrifft ein Verfahren zur Herstellung von neuen quartären Ajmaliniumsalzen, das dadurch gekennzeichnet ist, daß man eine Ajmalinverbindung der allgemeinen Formel in der R einen geradkettigen oder verzweigten Alkyl-, Alkenyl- oder Alkinylrest mit 3 bis 5 Kohlenstoff atomen und X(-) ein Halogenion oder das Anion einer aromatischen Sulfonsäure bedeutet, mit wäßrigen Alkalien behandelt, die erhaltene Base der allgemeinen Formel mit der äquimolaren Menge einer physiologisch verträglichen, mehrbasigen anorganischen oder organischen Säure der allgemeinen Formel HY umsetzt und das erhaltene quartäre Salz der allgemeinen Formel in der Y(-) das Anion einer einfach dissoziierten physiologisch verträglichen, mehrbasigen anorganischen oder organischen Säure bedeutet, isoliert.Process for the preparation of new quaternary ajmalinium salts The invention relates to a process for the preparation of new quaternary ajmalinium salts, which is characterized in that an ajmaline compound of the general formula is used in which R is a straight-chain or branched alkyl, alkenyl or alkynyl radical having 3 to 5 carbon atoms and X (-) is a halogen ion or the anion of an aromatic sulfonic acid, treated with aqueous alkalis, the base of the general formula obtained with the equimolar amount of a physiologically compatible, polybasic inorganic or organic acid of the general formula HY and the resulting quaternary salt of the general formula in which Y (-) denotes the anion of a simply dissociated, physiologically acceptable, polybasic inorganic or organic acid, isolated.
Die Aldehydbasen der allgemeinen Formel 11 werden zweckmäßig in der Weise erhalten, daß man eine Verbindung der allgemeinen Formel I in einer wäßrigen Alkalilösung, beispielsweise in einer Natriumhydrogencarbonat- oder einer Natriumcarbonat-Lösung, suspendiert und die in Freiheit gesetzte Aldehydbase mit einem inerten, mit Wasser nicht mischbaren Lösungsmittel, wie Äther, Chloroform oder Benzol, extrahiert und das Lösungsmittel anschließend abdestilliert. Die Aldehydbasen lassen sich mit Säuren wieder in quartäre Salze der allgemeinen Formel I überführen, es liegt also ein tautomeres Gleichgewicht zwischen den Verbindungen der Formeln I und II vor, dessen Lage vom pH-Wert abhängig ist. Die Struktur der Aldehydbasen ist durch ihr IR-Spektrum und Kernresonanzspektrum gesichert.The aldehyde bases of the general formula 11 are advantageously obtained by suspending a compound of the general formula I in an aqueous alkali solution, for example in a sodium hydrogen carbonate or a sodium carbonate solution, and the liberated aldehyde base with an inert one with water Immiscible solvents, such as ether, chloroform or benzene, extracted and the solvent is then distilled off. The aldehyde bases can be converted back into quaternary salts of the general formula I with acids, so there is a tautomeric equilibrium between the compounds of the formulas I and II, the position of which depends on the pH. The structure of the aldehyde bases is secured by their IR spectrum and nuclear magnetic resonance spectrum.
Die erhaltenen Aldehydbasen werden zweckmäßig ohne weitere Reinigung mit 1 Mol einer physiologisch verträglichen, mehrbasigen anorganischen oder organischen Säure der allgemeinen Formel HY versetzt, vorzugsweise in einem inerten Lösungsmittel, wie Methanol, Aceton oder Tetrahydrofuran. Die gewünschten quartären Salze kristallisieren aus der Lösung entweder gleich oder nach Abdampfen eines Teiles des Lösungsmittels aus. Als Säuren haben sich beispielsweise Schwefelsäure, Phosphorsäure, Weinsäure, Citronensäure, Oxalsäure, Maleinsäure, Bernsteinsäure, Glutarsäure, Fumarsäure undAdipinsäure als geeignet erwiesen.The aldehyde bases obtained are expediently without further purification with 1 mole of a physiologically compatible, polybasic inorganic or organic Acid of the general formula HY added, preferably in an inert solvent, such as methanol, acetone or tetrahydrofuran. The desired quaternary salts crystallize from the solution either immediately or after evaporation of part of the solvent the end. As acids, for example, sulfuric acid, phosphoric acid, tartaric acid, Citric acid, oxalic acid, maleic acid, succinic acid, glutaric acid, fumaric acid and adipic acid proved suitable.
Die neuen quartären Salze der allgemeinen Formel III sind wesentlich besser löslich als die Salze der allgemeinen Formel I; so ist das N-(n-Propyl)-ajmaliniumbromid weniger als 0,2% wasserlöslich, während sich beispielsweise vom N-(n-Propyl)-ajmalinium-hydrogentartrat ohne weiteres stabile wäßrige Lösungen mit 50% und mehr des Wirkstoffes herstellen lassen. Die neuen quartären Salze besitzen antiarrhythmische Wirksamkeit. Die nachstehenden Beispiele sollen die Erfindung näher erläutern.The new quaternary salts of the general formula III are essential more soluble than the salts of general formula I; so is the N- (n-propyl) -ajmalinium bromide less than 0.2% water-soluble, while for example from N- (n-propyl) -ajmalinium hydrogen tartrate readily produce stable aqueous solutions containing 50% or more of the active ingredient permit. The new quaternary salts have antiarrhythmic activity. the The following examples are intended to explain the invention in more detail.
Beispiel 1 75g N-(n-Propyl)-ajmaliniumbromid werden in 31 einer gesättigten Lösung von Natriumbicarbonat in Wasser suspendiert und mit 31 Chloroform versetzt. Anschließend wird 6 bis 8 Stunden kräftig durchgerührt, die Chloroformphase abgetrennt und zur Trockne eingeengt. Als Rückstand verbleiben 68 g der Aldehydbase (1I, gelber Sirup), deren IR-Spektrum eine Carbonylbande bei 5,83. aufweist. und in deren Kernresonanzspektrum ein Aldehydproton bei 9,5 ppm (Tetramethylsilan = 0 ppm) nachweisbar ist.Example 1 75 g of N- (n-propyl) -ajmalinium bromide are saturated in a 31 Solution of sodium bicarbonate suspended in water and treated with 31 chloroform. The mixture is then vigorously stirred for 6 to 8 hours and the chloroform phase is separated off and concentrated to dryness. 68 g of the aldehyde base (1I, yellower Syrup), the IR spectrum of which has a carbonyl band at 5.83. having. and in their nuclear magnetic resonance spectrum an aldehyde proton is detectable at 9.5 ppm (tetramethylsilane = 0 ppm).
Die Aldehydbase wird nun in etwa 150 ccm Aceton gelöst und unter Rühren und Eiskühlung langsam mit einer Lösung von 21 Aceton und 25 g Weinsäure versetzt. Der entstandene feine weiße _ Niederschlag wird abgesaugt, mit Äther nachgewaschen und getrocknet. Die Rohausbeute beträgt 80 g. Nach einmaliger Umkristallisation aus Athanol-Äther erhält man 50 g N-(n-Propyl)-ajmalinium-hydrogentartrat; F. 149 bis 152°C (Zersetzung).The aldehyde base is now dissolved in about 150 cc of acetone and a solution of 21% acetone and 25 g of tartaric acid is slowly added while stirring and while cooling with ice. The resulting fine white precipitate is filtered off, washed with ether and dried. The raw yield is 80 g. After a single recrystallization from ethanol-ether, 50 g of N- (n-propyl) -ajmalinium hydrogen tartrate are obtained; M.p. 149 to 152 ° C (decomposition).
Auf die gleiche Weise wurde auch das N-(n-Propyl)-ajmalinium-dihydrogenphosphat erhalten. Beispiel 2 Die Darstellung der Aldehydbase erfolgt wie im Beispiel 1 beschrieben.The N- (n-propyl) -ajmalinium dihydrogen phosphate was made in the same way obtain. Example 2 The aldehyde base is prepared as described in Example 1.
9 g Aldehydbase und 3,8 g Oxalsäure werden durch Erwärmen in etwa 70 ccm Äthanol gelöst und die Lösung anschließend bis zur beginnenden Trübung mit Äther versetzt. Im Verlauf von einigen Stunden kristallisieren etwa 9,5 g einer farblosen Substanz, die abgesaugt und getrocknet wird.9 g of aldehyde base and 3.8 g of oxalic acid are approx Dissolved 70 cc of ethanol and then added the solution to the onset of turbidity Ether shifted. Approximately 9.5 g crystallized in the course of a few hours colorless substance that is sucked off and dried.
Diese Kristalle werden zweimal aus Athanol-Äther umkristallisiert, wobei man 6,5 g farbloses N - (n - Propyl) - ajmalinium - hydrogenoxalat vom Schmelzpunkt 139 bis 143'C erhält.These crystals are recrystallized twice from ethanol-ether, 6.5 g of colorless N - (n - propyl) - ajmalinium hydrogen oxalate having a melting point 139 to 143'C.
Beispiel 3 Die Darstellung der Aldehydbase erfolgt wie im Biespiel 1 beschrieben.Example 3 The aldehyde base is prepared as in the example 1 described.
0,5 g Aldehydbase werden in etwa 10 ccm Äthanol gelöst und mit 2,72 ccm 1 n-Schwefelsäure versetzt. Diese Lösung wird kurze Zeit auf 50°C erhitzt, dann bis zur beginnenden Trübung mit Äther versetzt und zur Kristallisation in die Tiefkühltruhe gestellt. Die anfallenden Kristalle werden abgesaugt und getrocknet.0.5 g of aldehyde base are dissolved in about 10 ccm of ethanol and 2.72 ccm 1 n-sulfuric acid added. This solution is heated to 50 ° C for a short time, then Aether is added to the beginning of cloudiness and in the freezer to crystallize posed. The resulting crystals are suctioned off and dried.
Zur Reinigung wird aus Athanol-Ather umkristallisiert, wobei man 0,31 g farbloses N-(n-Propyl)-ajmalinium-hydrogensulfat vom Schmelzpunkt 279 bis 283'C (Zersetzung) erhält.For purification, it is recrystallized from ethanol ether, 0.31 g colorless N- (n-propyl) -ajmalinium hydrogen sulfate with a melting point of 279 to 283 ° C (Decomposition).
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR920678A FR2434M (en) | 1963-07-05 | 1963-01-07 | New derivatives of ajmaline. |
| FR980349A FR109F (en) | 1963-07-05 | 1964-07-01 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1196207XA | 1962-12-17 | 1962-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1196207B true DE1196207B (en) | 1965-07-08 |
Family
ID=22385379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET24241A Pending DE1196207B (en) | 1962-12-17 | 1963-07-05 | Process for the preparation of new quaternary ajmalinium salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1196207B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029115A1 (en) * | 1979-10-13 | 1981-05-27 | Kali-Chemie Pharma GmbH | N(b)-quaternary 10-bromo-ajmaline and 10-bromo-isoajmaline derivatives, process and intermediates for preparing the derivatives and medicaments containing the derivatives |
-
1963
- 1963-07-05 DE DET24241A patent/DE1196207B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029115A1 (en) * | 1979-10-13 | 1981-05-27 | Kali-Chemie Pharma GmbH | N(b)-quaternary 10-bromo-ajmaline and 10-bromo-isoajmaline derivatives, process and intermediates for preparing the derivatives and medicaments containing the derivatives |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1196207B (en) | Process for the preparation of new quaternary ajmalinium salts | |
| AT243997B (en) | Process for the production of new ajmaline derivatives | |
| DE1918253A1 (en) | 3-hydroxyisoxazoles (soil fungicides) prodn | |
| DE1912193A1 (en) | 1- (Phenylsulfonyl) -cyclopropanecarboxylic acids and derivatives | |
| DE969245C (en) | Process for the production of new spasmolytically effective basic esters of ª ‡ -alkylated phenylacetic acids | |
| DE641271C (en) | Process for the preparation of aromatically substituted pyridinium ethanols | |
| DE576712C (en) | Process for the preparation of a double salt of ª ‰ -Bromaethyltrimethylammonium | |
| DE965325C (en) | Process for the preparation of streptomycin isonicotinic acid hydrazone and its salts | |
| DE938249C (en) | Process for the preparation of dihydrocodeine hydrorhodanide | |
| AT346838B (en) | PROCESS FOR MANUFACTURING NEW OPTICALLY ACTIVE ANTHRACYCLINONES | |
| AT251580B (en) | Process for the preparation of new piperidine carboxylic acid esters | |
| AT113002B (en) | Process for the preparation of monoboric acid choline. | |
| DE613403C (en) | Process for the preparation of barbituric acids substituted on carbon and nitrogen | |
| AT260911B (en) | Process for the preparation of the optically active forms of α-methyl-β- (3,4-dihydroxyphenyl) alanine and their N, O, O-triacetyl derivatives | |
| DE974085C (en) | Process for the preparation of water-insoluble dipenicillin salts from diamines and penicillins | |
| DE527715C (en) | Process for the preparation of easily soluble salts of 3-acetylamino-4-oxybenzene-1-arsic acid | |
| DE931283C (en) | Process for the preparation of thiobarbituric acid derivatives | |
| AT165550B (en) | Process for the preparation of d (+) - pantothenic acid | |
| DE663586C (en) | Process for the preparation of novel derivatives of 8-oxyquinoline | |
| DE2032097C (en) | Process for the separation of (+) trans-chrysanthemum monocarboxylic acid from (+) - trans-chrysanthemum monocarboxylic acid | |
| DE3606665A1 (en) | Process for the preparation of vincamine | |
| DE2129991C3 (en) | Process for the preparation of 2- (4,5-dihydro-5-propyl-2 (3H) -furylidene) -1,3-cyclopentanedione | |
| DE1939056C (en) | Vintiamolester | |
| DE1113696B (en) | Process for the preparation of 1,3-disubstituted or 1,3,8-trisubstituted 9-methylisoxanthines | |
| AT219598B (en) | Process for the preparation of new 2- (p-aminobenzenesulfonamido) -5-alkoxypyrimidines |