DE833817C - Process for the preparation of nicotinic acid amides - Google Patents
Process for the preparation of nicotinic acid amidesInfo
- Publication number
- DE833817C DE833817C DEP25542A DEP0025542A DE833817C DE 833817 C DE833817 C DE 833817C DE P25542 A DEP25542 A DE P25542A DE P0025542 A DEP0025542 A DE P0025542A DE 833817 C DE833817 C DE 833817C
- Authority
- DE
- Germany
- Prior art keywords
- nicotinic acid
- preparation
- acid amides
- phenyl radical
- denotes
- 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
- 238000000034 method Methods 0.000 title claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 3
- 235000005152 nicotinamide Nutrition 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 15
- 235000001968 nicotinic acid Nutrition 0.000 claims description 8
- 239000011664 nicotinic acid Substances 0.000 claims description 8
- 229960003512 nicotinic acid Drugs 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- -1 nicotinic acid halide Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- YZDOCZIVQJMSSL-UHFFFAOYSA-N hypochlorous acid pyridine-3-carbonyl chloride Chemical compound ClO.ClC(=O)C1=CC=CN=C1 YZDOCZIVQJMSSL-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001114 myogenic effect Effects 0.000 description 1
- IYJLJJIRPLWNTG-UHFFFAOYSA-N n-benzhydrylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 IYJLJJIRPLWNTG-UHFFFAOYSA-N 0.000 description 1
- JIAOUYONZMRJJD-UHFFFAOYSA-N n-benzylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCC1=CC=CC=C1 JIAOUYONZMRJJD-UHFFFAOYSA-N 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 125000000627 niacin group Chemical group 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 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
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Nicotinsäureamiden Es ist bekannt, daß das Benzylamid der Nicotinsäure eine deutliche spasmolytische Aktivität besitzt. Die Wirksamkeit dieser Verbindung ist aber derart schwach, daß ihre praktische Verwendung als Spasmolytikum kaum in Frage kommt. Außerdem steht die Toxizität der therapeutischen Verwendung dieser Verbindung hinderlich im Wege. Ferner sind in der Patentschrift 54o 697 eine größere Anzahl Verbindungen beschrieben, von denen die meisten spasmolytisch wirken sollen. Unter diesen 1)efindet sich ein Derivat der N icotinsäure, nämlich das Hydrobromid des Pyridin-3-carbonsäurepiperidyl-N-äthylamids. Eigene Versuche haben ergeben, daß die spasmolvtische Wirkung dieser Verbindung unbefriedigend ist.Process for the preparation of nicotinic acid amides It is known that the benzylamide of nicotinic acid has a marked spasmolytic activity. However, the effectiveness of this compound is so weak that its practical use as a spasmolytic is hardly an option. Besides, the toxicity is the therapeutic one Use of this connection obstructive in the way. Furthermore, in the patent 54o 697 a large number of compounds are described, most of which are spasmolytic should work. Among these 1) there is a derivative of nicotinic acid, viz the hydrobromide of pyridine-3-carboxylic acid piperidyl-N-ethylamide. Own attempts have shown that the spasmolvtische effect of this compound is unsatisfactory.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung einer Reihe neuer, therapeutisch wertvoller N-substituierter Nicotinsäureamide, welche sowohl das Nicotinsäurebenzylamid als auch das Nicotinsäurepiperidyl-N-äthylamid an Wirksamkeit um das Vielfache übertreffen und die namentlich zur Behebung neurogener und myogener Spasmen verwendet werden sollen.The invention relates to a method for producing a series new, therapeutically valuable N-substituted nicotinic acid amides, which both the nicotinic acid benzylamide as well as the nicotinic acid piperidyl-N-ethylamide in effectiveness many times over, and in particular for the elimination of neurogenic and myogenic Spasms should be used.
Zur Herstellung der neuen 'Verbindungen nach dem erfindungsgemäßen Verfahren setzt man eine zur Einführung des Nicotinsäurtrestes geeignete Verbindung, z. B. Nicotinsäure, ihr Anhydrid, ein N icotinsäurehalogenid oder -ester, mit einem Amin um von der allgemeinen Formel worin R1 den Phenylrest und R2 den Phenylrest oder einen mit einem Phen_vlrest verbundenen ah= phatischen Rest, der eine Oxygruppe enthalten kann, bedeuten oder worin das mit dem Stickstoff-und dem Wasserstoffatom verbundene Kohlenstoffatom Bestandteil eines Ringes ist, an welchem zwei aromatische 6-Ringe ankondensiert sind. Beispiel i Zu 32,7 g Nicotinsäurechloridchlorhydrat und 42 g Aminodiphenylmethan in 250 ccm absolutem Benzol werden langsam unter Rühren 5i,1 g frisch geglühtes Kaliumcarbonat gegeben. Das Gemisch wird 9 Stunden unter Rückflußkiihlung gekocht, das Ungelöste abfiltriert und aus Äthanol umkristallisiert. Ausbeute 57,3 g = 86,4% der Theorie. Das so erhaltene Nicotinsäurediphenylmethylamid kristallisiert in farblosen, bei 175 bis 18o° schmelzenden Nadeln. Es ist leicht löslich in Chloroform, Aceton und Methanol, mäßig gut in Äthanol, wenig löslich in Benzol und Äther, unlöslich in Wasser. Beispiel e Eine Mischung von 36 g Nicotinsäurie und 57,5 g 1. 2-Diphenyläth#-lamin in 300 ccm Cumol wird auf ihren Kochpunkt erhitzt, so daß Cumol und das bei -der Reaktion sich bildende Wasser langsam in eine Vorlage destillieren, die eine Messung des Volumens des Destillates gestattet. Sobald die untere, wässerige Schicht 5,2 ccm beträgt, wird das restliche Cumol im Vakuum abdestilliert und der aus Nicotitisäure-(a-, ß-diphenyl)-äthylamid bestehende Rückstand aus Äthanol umkristallisiert. Die neue Verbindung bildet farblose Drusen nadelförmiger Kristalle vom Schmelzpunkt 159°. Sie ist leicht löslich in 5 n-Salzsäure, mäßig gut löslich in Methanol, Aceton, Äther und Benzol, wenig löslich in Äthanol und unlöslich in Wasser und in Alkalien. Beispiel 3 Einem Gemisch von 28,44 g N icotinsäurechloridchlorhvdrat, 34,23 g 2-Oxv-1. 2-diphenyläthylamin und 200 ccm absolutem Alkohol werden 44,35 g frisch geglühtes Kaliumcarbonat zugefügt. Das Ganze wird i t Stunden am Rückflußkühler gekocht, dann, nach dem Erkalten, das Ungelöste abfiltriert und aus Äthanol umkristallisiert. Man erhält so 37,8 g Nicot1nsäure-(a-hhen_vl-@-oxy-ß-phenyl)-äthylamid in farblosen Nadeln vom Schmelzpunkt 2ä3°. Die neue Verbindung ist leicht löslich in Aceton und Pvridiri, wenig löslich in Äther, Benzol. Eisessig und Äthanol. unlöslich in Wasser.To prepare the new 'compounds by the process according to the invention, a compound suitable for introducing the nicotinic acid residue is used, e.g. B. nicotinic acid, its anhydride, a nicotinic acid halide or ester, with an amine around of the general formula where R1 denotes the phenyl radical and R2 denotes the phenyl radical or a phatic radical connected to a phenyl radical, which may contain an oxy group, or in which the carbon atom connected to the nitrogen and hydrogen atom is part of a ring on which two aromatic 6-membered rings are condensed. EXAMPLE i To 32.7 g of nicotinic acid chloride chlorohydrate and 42 g of aminodiphenylmethane in 250 cc of absolute benzene are slowly added 51.1 g of freshly calcined potassium carbonate with stirring. The mixture is refluxed for 9 hours, the undissolved material is filtered off and recrystallized from ethanol. Yield 57.3 g = 86.4% of theory. The nicotinic acid diphenylmethylamide thus obtained crystallizes in colorless needles melting at 175 to 180 °. It is easily soluble in chloroform, acetone and methanol, moderately well in ethanol, little soluble in benzene and ether, insoluble in water. EXAMPLE e A mixture of 36 g of nicotinic acid and 57.5 g of 1,2-diphenylethelamine in 300 cc of cumene is heated to its boiling point so that cumene and the water formed during the reaction slowly distill into a receiver which a measurement of the volume of the distillate is allowed. As soon as the lower, aqueous layer is 5.2 ccm, the remaining cumene is distilled off in vacuo and the residue consisting of nicotitic acid (α-, ß-diphenyl) ethylamide is recrystallized from ethanol. The new compound forms colorless drusen of needle-shaped crystals with a melting point of 159 °. It is easily soluble in 5N hydrochloric acid, moderately soluble in methanol, acetone, ether and benzene, slightly soluble in ethanol and insoluble in water and in alkalis. Example 3 A mixture of 28.44 g of nicotinic acid chloride chlorohydrate, 34.23 g of 2-Oxv-1. 2-diphenylethylamine and 200 cc of absolute alcohol are added to 44.35 g of freshly calcined potassium carbonate. The whole thing is refluxed for hours, then, after cooling, the undissolved material is filtered off and recrystallized from ethanol. 37.8 g of nicotinic acid (a-hhen_vl - @ - oxy-ß-phenyl) ethylamide are obtained in colorless needles with a melting point of 2-3 °. The new compound is easily soluble in acetone and pvridiri, not very soluble in ether and benzene. Glacial acetic acid and ethanol. insoluble in water.
In ähnlicher Weise kann auch hergestellt werden das Nicotinsäure-[-fluorenvl-9-]-amid (farblos Kristalle vom Schmelzpunkt 287 bis 288°).Nicotinic acid - [- fluorenvl-9 -] - amide can also be prepared in a similar manner (colorless crystals with a melting point of 287 to 288 °).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH833817X | 1945-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE833817C true DE833817C (en) | 1952-03-13 |
Family
ID=4540523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP25542A Expired DE833817C (en) | 1945-09-15 | 1948-12-19 | Process for the preparation of nicotinic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE833817C (en) |
-
1948
- 1948-12-19 DE DEP25542A patent/DE833817C/en not_active Expired
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