DE1146495B - Process for the preparation of tri- [ª ‰ -theophyllinyl- (7) -aethyl] -orthophosphoric acid ester - Google Patents
Process for the preparation of tri- [ª ‰ -theophyllinyl- (7) -aethyl] -orthophosphoric acid esterInfo
- Publication number
- DE1146495B DE1146495B DEH39159A DEH0039159A DE1146495B DE 1146495 B DE1146495 B DE 1146495B DE H39159 A DEH39159 A DE H39159A DE H0039159 A DEH0039159 A DE H0039159A DE 1146495 B DE1146495 B DE 1146495B
- Authority
- DE
- Germany
- Prior art keywords
- orthophosphoric acid
- tri
- acid ester
- theophyllinyl
- preparation
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 235000011007 phosphoric acid Nutrition 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 229960005387 etofylline Drugs 0.000 description 4
- 229960000278 theophylline Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWPRCRWQMGIBOT-UHFFFAOYSA-N 7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCO)C=N2 NWPRCRWQMGIBOT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 210000003205 muscle Anatomy 0.000 description 1
- -1 orthophosphoric acid ester Chemical class 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
H39159IVd/12pH39159IVd / 12p
BEKANNTMACHUNG DER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT:NOTIFICATION OF THE NOTIFICATION AND ISSUE OF THE EDITORIAL:
4. A P RIL 19634. A P RIL 1963
Zahlreiche Verbindungen mit therapeutischen Eigenschaften werden aus Theophyllin hergestellt. Die meisten dieser Theophyllinderivate entstehen durch Substitution des in 7-Stellung befindlichen Wasserstoffatoms durch einen organischen Rest, der insbesondere aus einem Aminoalkyl-, Carboxyalkyl- oder Oxyalkylrest bestehen kann. In dem unter der Bezeichnung Oxyphyllin bekannten Derivat besteht der in 7-Stellung befindliche Rest aus dem /?-Oxyäthylrest; es handelt sich also um das 7-ß-Oxyäthyltheophyllin.Numerous compounds with therapeutic properties are made from theophylline. the Most of these theophylline derivatives result from substitution of the 7-position hydrogen by an organic radical, which in particular consists of an aminoalkyl, carboxyalkyl or oxyalkyl radical can exist. In the derivative known under the name oxyphylline, it is in the 7-position the remainder from the /? - Oxyäthylrest; it deals So it is about 7-ß-oxyethyltheophylline.
Die Erfindung soll ein neues, therapeutisch wertvolles Theophyllinderivat bereitstellen, dessen Eigenschaften sich von denen der 7-^-Oxyäthyltheophyllinderivate unterscheiden und das in mancher Hinsicht insbesondere spezifischer und intensiver wirkt.The invention is intended to provide a new, therapeutically useful theophylline derivative, the properties of which from those of the 7 - ^ - Oxyäthyltheophylinderivate and which in some respects has a more specific and intense effect.
Die Erfindung betrifft ein Verfahren zur Herstellung des Tri - [ß - theophyllinyl - (7) - äthyl] - orthophosphorsäureesters, also der Verbindung der FormelThe invention relates to a process for the preparation of the tri - [ß - theophyllinyl - (7) - ethyl] - orthophosphoric acid ester, that is to say the compound of the formula
Th-CH2-CH2-O.Th-CH 2 -CH 2 -O.
Th — CH2 — CH2 — O -~ P = O
Th — CH2 — CH2 — OTh - CH 2 - CH 2 - O - ~ P = O
Th - CH 2 - CH 2 - O
wobei jedes Symbol »Th« einen Theophyllinyl-(7)-rest bedeutet.where each symbol "Th" means a theophyllinyl (7) radical.
Nach diesem Verfahren werden 3 Mol 7-^-Oxyäthyltheophyllin mit 1 Mol eines Trihalogenids der Orthophosphorsäure, insbesondere Phosphoroxychlorid, phosphoryliert. Die Umsetzung geschieht in Gegenwart eines Chlorwasserstoff aufnehmenden Mittels. Insbesondere kann man eine Lösung von Phosphoroxychlorid in überschüssigem wasserfreiem Pyridin langsam einem wannen Gemisch aus 7-/S-0xyäthyltheophyllin und Pyridin zugeben und das Ganze dann auf Rückflußtemperatur erhitzen.According to this procedure 3 moles of 7 - ^ - Oxyäthyltheophyllin with 1 mole of a trihalide of orthophosphoric acid, in particular phosphorus oxychloride, phosphorylated. The reaction takes place in the presence of an agent which absorbs hydrogen chloride. In particular, one can use a solution of phosphorus oxychloride in excess anhydrous pyridine slowly add a tub mixture of 7- / S-0xyäthyltheophyllin and pyridine and then the whole thing heat to reflux temperature.
Das Verfahrensprodukt eignet sich in pharmakologischer Hinsicht besser zu klinischen Zwecken als das Theophyllin und erst recht als das 7-jS-Oxyäthyltheophyllin, von dem es abstammt. Der Tri-rjJ-theo-Verfahren zur HerstellungFrom a pharmacological point of view, the product of the process is better suited for clinical purposes than that Theophylline and even more so than the 7-jS-Oxyäthyltheophylline, from which it is derived. The tri-rjJ-theo-procedure for the production
vonTri-[ß-theophyllinyl-(7)-äthyl]-of tri- [ß-theophyllinyl- (7) -ethyl] -
orthophosphorsäureesterorthophosphoric acid ester
Anmelder:Applicant:
Rene Jules Paul Hazard,Rene Jules Paul Hazard,
Jean Marie Cheymol,Jean Marie Cheymol,
Pierre Eugene Chabrier de Lassauniere, Avigeel Carayon-Gentil, geb. Kramers, und Marcelle Jeanne Beauvallet, ParisPierre Eugene Chabrier de Lassauniere, Avigeel Carayon-Gentil, née Kramers, and Marcelle Jeanne Beauvallet, Paris
Vertreter: Dr. W. Beil, A. Hoeppener und Dr. H. J. Wolff, Rechtsanwälte, Frankfurt/M.-Höchst, Antoniterstr. 36Representative: Dr. W. Beil, A. Hoeppener and Dr. H. J. Wolff, lawyers, Frankfurt / M.-Höchst, Antoniterstr. 36
Beanspruchte Priorität: Frankreich vom 14. April 1959 (Nr. 792 055)Claimed priority: France of April 14, 1959 (No. 792 055)
Rene Jules Paul Hazard, Jean Marie Cheymol, Pierre Eugene Chabrier de Lassauniere, Avigael Carayon-Gentil, geb. Kramers, und Marcelle Jeanne Beauvallet, Paris, sind als Erfinder genannt wordenRene Jules Paul Hazard, Jean Marie Cheymol, Pierre Eugene Chabrier de Lassauniere, Avigael Carayon-Gentil, née Kramers, and Marcelle Jeanne Beauvallet, Paris, have been named as inventors
phyllinyl - (7) - äthyl] - orthophosphorsäureester besitzt eine krampflösende und eine kardiovaskuläre Wirkung, die beide intensiver sind als die des Theophylline, dem dieser Ester pharmakologisch nähersteht als dem 7-iS-Oxyäthyltheophyllin.phyllinyl - (7) - ethyl] - orthophosphoric acid ester has an antispasmodic and cardiovascular effect, both of which are more intense than those of theophylline, to which this ester is pharmacologically closer than that 7-iS-oxyethyltheophylline.
Von der bekannten Verbindung der FormelFrom the known compound of the formula
Jl ΓΙ V_-Jl1o ν.-JrIo ' \J ' is. Jl ΓΙ V_-Jl1o ν.-JrIo ' \ J ' is.
,0CH1=, 0CH 1 =
'OCH.'OCH.
sind keine pharmakologischen Eigenschaften von 5° Unlöslichkeit außerordentlich schwierig. Diese Unlös-Bedeutung zu erwarten. Wollte man die Substanz lichkeit verbietet die Verabreichung der Verbindung daraufhin untersuchen, so wäre dies auf Grund ihrer auf parenteralem Wege.No pharmacological properties of 5 ° insolubility are extremely difficult. This unsolvable meaning expected. If one wanted the substance, the administration of the compound was forbidden then examine it, so this would be due to their parenteral route.
309 548/336309 548/336
1 l461 l46
Die Ergebnisse der pharmakologischen Versuche sind in nachstehender Tabelle zusammengefaßt:The results of the pharmacological tests are summarized in the table below:
■ Verbindungen■ Connections
Toxizität
DL50 in-Milligramm je,
Kilogramm Tiergewicht
(weiße Maus);toxicity
DL 50 in-milligrams each,
Kilograms of animal weight
(white mouse);
intravenöse
Verabreichungintravenous
administration
Kardiovaskuläre WirkungCardiovascular effect
isoliertesisolated
FroschherzFrog heart
(inotrope(inotropic
Wirkung) in situ ·■' '
chloralosiertesEffect) in situ · ■ ''
chlorinated
Hundeherz
Rhythmus undDog heart
Rhythm and
Amplitudeamplitude
arteriellerarterial
Druckpressure
(chloralosierter
Hund)(chloralized
Dog)
Wirkung auf die glattenEffect on the smooth
Muskeln; Hemmung derMuscles; Inhibition of
durch das Acetylcholinby the acetylcholine
verursachten Kontraktioncaused contraction
TheophyllinTheophylline
7-/3-Oxyäthyltheophyllin. 7- / 3-oxyethyltheophylline.
VerfahrensproduktProcess product
■ 150■ 150
500
150500
150
In einen 100 ecm fassenden Dreihalskolben, der mit einem mechanischen Rührwerk mit Quecksilberdichtung, einem Tropftrichter, einem Thermometer und einem Rückflußkühler, auf dem sich ein Calciumchloridrohr befindet, versehen ist, bringt man 30 g 7-/S-Oxyäthylthophylline und 90 cm3 wasserfreies Pyridin. In dieses auf etwa 50° C erwärmte Gemisch führt man tropfenweise 6,7 g Phosphoroxychlorid, das in 15 cm3 Pyridin gelöst ist, ein. Allmählich geht alles in Lösung. Nach beendetem Zusatz hält man das· Ganze 8 Stunden auf annähernd 50° C. Das überschüssige Pyridin wird im Vakuum abdestilliert. Der Rückstand wird mit kaltem Methanol aufgenommen. Ein in der Kälte schlecht löslicher Niederschlag scheidet sich ab. Dieser Niederschlag wird gesammelt, mit Wasser gewaschen und dann aus warmem Methylalkohol umkristalh'siert. Auf diese Weise gewinnt man in etwa 60%iger Ausbeute Tri-fjS-thiiöphyllinyl-(7)-äthyl]-orthophosphorsäureester mit einem Schmelzpunkt von 170° C. In Wasser, Aceton, kaltem Äthanol (Wirksamkeit = 1) 30 g of 7- / S-oxyethylthophylline and 90 cm 3 of anhydrous pyridine are placed in a 100 ecm three-necked flask equipped with a mechanical stirrer with a mercury seal, a dropping funnel, a thermometer and a reflux condenser on which there is a calcium chloride tube . 6.7 g of phosphorus oxychloride dissolved in 15 cm 3 of pyridine are introduced dropwise into this mixture, which has been heated to about 50 ° C. Gradually everything goes into solution. When the addition is complete, the whole is kept at approximately 50 ° C. for 8 hours. The excess pyridine is distilled off in vacuo. The residue is taken up in cold methanol. A precipitate, which is poorly soluble in the cold, separates out. This precipitate is collected, washed with water and then recrystallized from warm methyl alcohol. In this way, tri-fjS-thiiöphyllinyl- (7) -ethyl] -orthophosphoric acid ester with a melting point of 170 ° C. is obtained in about 60% yield. In water, acetone, cold ethanol (effectiveness = 1)
(Wirksamkeit = 0,5) (Wirksamkeit = 25)(Effectiveness = 0.5) (effectiveness = 25)
und Äther ist er sehr schlecht löslich, in warmem Methanol jedoch ist er löslich.and ether it is very poorly soluble, but it is soluble in warm methanol.
Analyse:Analysis:
Berechnet
gefundenCalculated
found
N 23,46%, P 4,32%; N 23,40%, P 4,23%.N 23.46%, P 4.32%; N 23.40%, P 4.23%.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR792055A FR1343459A (en) | 1959-04-14 | 1959-04-14 | Theophylline derivatives and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1146495B true DE1146495B (en) | 1963-04-04 |
Family
ID=8713632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH39159A Pending DE1146495B (en) | 1959-04-14 | 1960-04-13 | Process for the preparation of tri- [ª ‰ -theophyllinyl- (7) -aethyl] -orthophosphoric acid ester |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1146495B (en) |
| FR (1) | FR1343459A (en) |
| LU (1) | LU38510A1 (en) |
| NL (2) | NL121068C (en) |
-
0
- NL NL250531D patent/NL250531A/xx unknown
- LU LU38510D patent/LU38510A1/xx unknown
- NL NL121068D patent/NL121068C/xx active
-
1959
- 1959-04-14 FR FR792055A patent/FR1343459A/en not_active Expired
-
1960
- 1960-04-13 DE DEH39159A patent/DE1146495B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| LU38510A1 (en) | |
| FR1343459A (en) | 1963-11-22 |
| NL250531A (en) | |
| NL121068C (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT395853B (en) | NEW IMIDAZOLE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
| DE68912263T2 (en) | 4-Methyl-5 [2- (4-phenyl-1-piperazinyl) ethyl] thiazole derivatives, their preparation and compositions containing them. | |
| CH632759A5 (en) | METHOD FOR PRODUCING NEW SUBSTITUTED PURINES. | |
| DE2702092A1 (en) | CHROMAN DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING THESE COMPOUNDS | |
| EP0521353B1 (en) | Antineoplastic medicament containing octadecyl-[2-(N-methylpiperidino)-ethyl] phosphate and synthesis thereof | |
| DE1146495B (en) | Process for the preparation of tri- [ª ‰ -theophyllinyl- (7) -aethyl] -orthophosphoric acid ester | |
| DD143611A5 (en) | METHOD FOR PRODUCING DILIGNOLE-RELATED COMPOUNDS | |
| DE2403786A1 (en) | NEW DERIVATIVES OF CUMARINE | |
| DE1242619B (en) | Process for the production of new nicotionic acid esters | |
| CH497413A (en) | Proscillaridin a derivs | |
| DE1817861C3 (en) | N-alkylated 3,4-methylenedioxymandelic acid amidines and their pharmacologically non-toxic acid addition salts and pharmaceutical compositions containing them. Eliminated from: 1811804 | |
| DE2159679C3 (en) | Isonipecotic acid derivatives | |
| AT343139B (en) | PROCESS FOR PRODUCING NEW PHOSPHINYL DERIVATIVES | |
| AT288390B (en) | Process for the preparation of a new cinnamic acid amide | |
| AT277474B (en) | Process for the preparation of new derivatives of bufadienolide glycosides | |
| AT251585B (en) | Process for the preparation of new 6,7-dihydro-5H-pyrrolo- [3,4-d] -pyrimidines | |
| AT280263B (en) | PROCESS FOR PRODUCING NEW FURAZANDERIVATIVES | |
| AT329022B (en) | PROCESS FOR THE PRODUCTION OF NEW HALOGENATED HYDROXYBENZYLAMINES AND THEIR ACID ADDITION SALTS | |
| AT288395B (en) | Process for the preparation of new cinnamic acid amides | |
| DE2016057C3 (en) | Square brackets on (thenylidene (2) -amino) -oxy] -alkylcarboxylic acids, their salts and alkyl esters, processes for their production and pharmaceutical preparations containing them | |
| AT371440B (en) | METHOD FOR PRODUCING NEW N-SUBSTITUTED MORANOLINE DERIVATIVES AND THEIR ACID ADDITION SALTS | |
| DE1944758C3 (en) | 1 -Cinnamoyl ^ -methyl-S-methoxy-Sindolylessigsäureester, process for their preparation and medicinal products | |
| AT288398B (en) | Process for the preparation of new cinnamic acid amides | |
| DE2003840A1 (en) | 3-Phenyl-4-acyloxycarbostyrile, process for their preparation and their use in medicaments | |
| AT334885B (en) | PROCESS FOR THE PREPARATION OF NEW BASIC ESTERS OR AMIDES OF 3,5-DIMETHYLBENZOIC ACID AND THEIR SALT |