CH490321A - Process for the preparation of dibenzocycloheptenes - Google Patents
Process for the preparation of dibenzocycloheptenesInfo
- Publication number
- CH490321A CH490321A CH1882868A CH1882868A CH490321A CH 490321 A CH490321 A CH 490321A CH 1882868 A CH1882868 A CH 1882868A CH 1882868 A CH1882868 A CH 1882868A CH 490321 A CH490321 A CH 490321A
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- sep
- sulfamoyl
- formula
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 150000008508 dibenzocycloheptenes Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- -1 halogen formate Chemical class 0.000 claims description 5
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 239000000284 extract Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Dibenzocycloheptenen Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Dibenzocycloheptenen der Formel
EMI0001.0000
worin R Niederalkyl ist und X und X' für Wasserstoff, Niederalkyl, Niederalkenyl, Halogen, Trifluormethyl, Oxy, Niederalkoxy, Mercapto, Niederalkyl-mercapto, Niederalkyl-sulfonyl, Sulfamoyl, Niederalkyl-sulfamoyl oder Diniederalkyl-sulfamoyl stehen.
Dieses erfindungsgemässe Verfahren zur Herstellung obiger Verbindungen I oder II ist dadurch gekennzeich net, dass man eine Verbindung der Formel
EMI0001.0002
entalkyliert, nämlich, dass man die Verbindung Ia mit einem Halogenformiat der Formel - HalCOOR3 worin Hal Halogen und R' Alkyl, Aralkyl oder Aryl bedeutet, behandelt und das erhaltene Urethanzwischen- produkt hydrolysiert.
Im allgemeinen kann die Behandlung mit Halogenfor- miat in Abwesenheit eines Lösungsmittels durchgeführt werden, doch es ist von Vorteil ein Lösungsmittel zu ver wenden. Als geeignete Lösungsmittel können die aromati schen Kohlenwasserstoffe, wie Benzol und Toluol, ali phatische Kohlenwasserstoffe wie Heptan und Hexan, und die Halogen-Kohlenwasserstoffe, wie Chloroform und Kohlenstofftetrachlorid, genannt werden. Die Reak tion kann bei Zimmertemperatur durchgeführt werden, obschon eine erhöhte Temperatur von Vorteil ist. Nach Beendigung dieser Reaktion wird das Urethan, nach Ent fernen der Verunreinigungen, durch Abdampfen des Lö- sungsmittels gewonnen.
Das auf diese Weise erzeugte Urethan-Zwischenpro- dukt wird dann der Hydrolyse unterworfen. Nach Beendi gung der Hydrolyse wird das gewünschte Produkt auf übliche Weise, wie durch Extrahieren in ein geeignetes Lösungsmittel und Abdampfen dieses Lösungsmittels, gewonnen.
Die durch die oben angeführte Strukturformel I ver anschaulichte erfindungsgemäss erzeugte Verbindung können mit Vorteil als Heilmittel zur Bekämpfung depres siver Zustände verwendet werden, nachdem sie eine aus gesprochene antidepressive Wirksamkeit aufweisen.
Als antidepressives Mittel können sie oral in Form von Tabletten Pulvern, in verstärkter Stosseinzeldosis- form und ähnl. verabreicht werden, oder sie können oral oder parenteral in Form von wässrigen Lösungen oder Suspensionen dargetan werden. Bei oraler oder parente- raler Verabreichung gelangt man zu zufriedenstellenden Ergebnissen bei einer täglichen Dosiskonzentration von etwa 60 mg bis etwa etwa 60 mg bis etwa 1000mg, die vortcilhafterweise in aufgeteilten Dosen während dem Tag in Form von ver stärkten Stosseinzeldosen gegeben wird.
Diese Verbin dungen werden zweckmässigerweise in Form ihrer nicht toxischen sauren Additionssalze verabreicht, wobei diese Salze gleichfalls gemäss dem vorliegenden erfindungsge- mässen Verfahren erzeugt werden. Die durch die oben angeführte Strukturformel ver anschaulichten, erfindungsgemäss erzeugten Verbindungen bestehen als geometrische Isomere, welche durch die ste- rische Beziehung der Hydroxylgruppen zueinander be stimmt werden. Zwecks Herstellung eines der genannten Isomere ist es notwendig ein geeignetes Ausgangsmaterial derselben Isomerenform, die auch als Endprodukt ge wünscht wird, zu verwenden.
<I>Beispiel</I> cis-5-[3-(N-Carbäthoxy-N-methylamino)-propyliden]- -10, I l -diacetoxy- l0, l I -dihydro-5H-dibenzo[a,d]- cyclohepten Eine Lösung bestehend aus 7,86 g, das sind 0,02 Mo le, cis-10,11-Diacetoxy-10,11-dihydro-5-(3-dimethylami- no-propyliden)-5H-dibenzo[a,d]cyclohepten in 40 ml trok- kenem Benzol wird innerhalb von 90 Minuten zu einer gerührten Lösung von 8 ml Äthylchlorformiat in 20 m1 trockenem Benzol zutropfen gelassen. Das Gemisch wird dann bei Rückfluss während 2¸ Stunden erhitzt.
Nach Kühlung und Verdünnen mit 50 ml Benzol, wird die Lö sung mit 3 N Chlorwasserstoffsäure und dann mit Was ser gewaschen. Nach Abdestillieren des Benzols unter ver mindertem Druck bleiben 7,85 g, das ist 87%, cis-5-[3- -(N-Carbäthoxy- N - methylamino)-propyliden] - 10,11 - di- acetoxy-10,11-dihydro-5H-dibenzo-[a,d]-cyclohepten, in Form eines öligen Rückstandes.
cis-10, l l -Dihydro-10,11 -dioxy-5-(3-methylaminopropyl)- -5H-dibenzo[a,d]cyclohepten Eine Lösung von 2,8 g, das sind 0,0076 Mole, des oben erhaltenen öligen Urethans und 2,5 g, das sind 0,04 Mole, Kaliumhydroxyd in 25 ml n-Butyl-alkohol wird gerührt und bei Rückfluss in einer Stickstoffatmosphäre während 6 Stunden erhitzt. Das Lösungsmittel wird unter vermindertem Druck abdestilliert und der Rückstand zwischen Benzol und Wasser aufgeteilt. Nach Reextrak- tion der wässrigen Phase werden die vereinigten Benzol .xtrakte mit Wasser gewaschen und dann mit 15 ml- und 10 ml-Portionen einer 0,5 M Zitronensäure extrahiert.
Der Säureextrakt wird mit Natrium-hydroxyd alkalisiert und die sich ausgeschiedene ölige Base in Benzol extra- liert. Der gewaschene und getrocknete Benzolextrakt wird dann auf ein kleines Volumen eingeengt. Die sich abgeschiedenen Produkte in Form weisser Kristalle wer- [en gesammelt, mit Benzol gewaschen und getrocknet; man erhält 1,05 g, das ist 47%, mit F = 140-143 C. Das eine Produkt aus einem anderen Experiment und nach wiederholtem Kristallisieren aus Benzol und aus Gemi schen von Äthanol und Wasser hat ein F = 143-145 C.
EMI0002.0027
Analyse <SEP> für <SEP> C19H21NO2:
<tb> Berechnet: <SEP> C <SEP> 77,26 <SEP> H <SEP> 7,17 <SEP> N <SEP> 4,74
<tb> Gefunden: <SEP> C <SEP> 77,34 <SEP> H <SEP> 7,18 <SEP> N <SEP> 4,59
Process for the preparation of dibenzocycloheptenes The present invention relates to a process for the preparation of dibenzocycloheptenes of the formula
EMI0001.0000
wherein R is lower alkyl and X and X 'are hydrogen, lower alkyl, lower alkenyl, halogen, trifluoromethyl, oxy, lower alkoxy, mercapto, lower alkyl-mercapto, lower alkyl-sulfonyl, sulfamoyl, lower alkyl-sulfamoyl or di-lower alkyl-sulfamoyl.
This inventive method for the preparation of the above compounds I or II is characterized in that a compound of the formula
EMI0001.0002
dealkylated, namely that the compound Ia is treated with a haloformate of the formula - HalCOOR3 in which Hal is halogen and R 'is alkyl, aralkyl or aryl, and the urethane intermediate product obtained is hydrolyzed.
In general, the treatment with halogen formate can be carried out in the absence of a solvent, but it is advantageous to use a solvent. Suitable solvents are the aromatic hydrocarbons such as benzene and toluene, aliphatic hydrocarbons such as heptane and hexane, and the halogen hydrocarbons such as chloroform and carbon tetrachloride. The reaction can be carried out at room temperature, although an elevated temperature is advantageous. After this reaction has ended, the urethane, after removing the impurities, is recovered by evaporating the solvent.
The urethane intermediate produced in this way is then subjected to hydrolysis. After completion of the hydrolysis, the desired product is obtained in a conventional manner, such as by extracting into a suitable solvent and evaporating this solvent.
The compounds produced according to the invention and illustrated by the structural formula I listed above can be used with advantage as remedies for combating depressive states, since they have a pronounced antidepressant activity.
As an antidepressant they can be administered orally in the form of tablets, powders, in increased single dose form and the like. or they can be presented orally or parenterally in the form of aqueous solutions or suspensions. In the case of oral or parenteral administration, satisfactory results are obtained at a daily dose concentration of from about 60 mg to about 60 mg to about 1000 mg, which is advantageously given in divided doses during the day in the form of reinforced burst single doses.
These compounds are expediently administered in the form of their non-toxic acidic addition salts, these salts also being produced in accordance with the present inventive method. The compounds produced according to the invention and illustrated by the structural formula given above exist as geometric isomers which are determined by the steric relationship of the hydroxyl groups to one another. For the production of one of the isomers mentioned, it is necessary to use a suitable starting material of the same isomeric form that is also desired as the end product.
<I> Example </I> cis-5- [3- (N-Carbethoxy-N-methylamino) -propylidene] - -10, I l -diacetoxy- l0, l I -dihydro-5H-dibenzo [a, d ] - cycloheptene A solution consisting of 7.86 g, that is 0.02 moles, cis-10,11-diacetoxy-10,11-dihydro-5- (3-dimethylamino-propylidene) -5H-dibenzo [ a, d] cycloheptene in 40 ml of dry benzene is added dropwise within 90 minutes to a stirred solution of 8 ml of ethyl chloroformate in 20 ml of dry benzene. The mixture is then heated at reflux for 2¸ hours.
After cooling and diluting with 50 ml of benzene, the solution is washed with 3N hydrochloric acid and then with water. After distilling off the benzene under reduced pressure, 7.85 g, that is 87%, remain cis-5- [3- - (N-Carbethoxy- N - methylamino) propylidene] - 10.11 - di- acetoxy-10, 11-dihydro-5H-dibenzo- [a, d] -cycloheptene, in the form of an oily residue.
cis -10,11 -Dihydro-10,11 -dioxy-5- (3-methylaminopropyl) -5H-dibenzo [a, d] cycloheptene A solution of 2.8 g, that is 0.0076 moles, of the above obtained Oily urethane and 2.5 g, that is 0.04 moles, of potassium hydroxide in 25 ml of n-butyl alcohol is stirred and heated at reflux in a nitrogen atmosphere for 6 hours. The solvent is distilled off under reduced pressure and the residue is partitioned between benzene and water. After re-extraction of the aqueous phase, the combined benzene extracts are washed with water and then extracted with 15 ml and 10 ml portions of 0.5 M citric acid.
The acid extract is made alkaline with sodium hydroxide and the oily base which has separated out is extracted in benzene. The washed and dried benzene extract is then concentrated to a small volume. The deposited products in the form of white crystals are collected, washed with benzene and dried; 1.05 g, that is 47%, with F = 140-143 C. One product from another experiment and after repeated crystallization from benzene and from mixtures of ethanol and water has an F = 143-145 C.
EMI0002.0027
Analysis <SEP> for <SEP> C19H21NO2:
<tb> Calculated: <SEP> C <SEP> 77.26 <SEP> H <SEP> 7.17 <SEP> N <SEP> 4.74
<tb> Found: <SEP> C <SEP> 77.34 <SEP> H <SEP> 7.18 <SEP> N <SEP> 4.59
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US296463A US3390179A (en) | 1963-07-22 | 1963-07-22 | Novel 10, 11-dihydro-10, 11-dihydroxy-(3-substituted aminopropylidene)-5h-dibenzo [a, d] cycloheptenes |
| CH953364A CH494731A (en) | 1963-07-22 | 1964-07-21 | Process for the preparation of derivatives of dibenzocyclo-heptene |
| US4847870A | 1970-06-22 | 1970-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH490321A true CH490321A (en) | 1970-05-15 |
Family
ID=27176254
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1882868A CH490321A (en) | 1963-07-22 | 1964-07-21 | Process for the preparation of dibenzocycloheptenes |
| CH1882968A CH476677A (en) | 1963-07-22 | 1964-07-21 | Process for the preparation of 5-hydroxy-5- (3-tertiary-aminopropyl) derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1882968A CH476677A (en) | 1963-07-22 | 1964-07-21 | Process for the preparation of 5-hydroxy-5- (3-tertiary-aminopropyl) derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH490321A (en) |
-
1964
- 1964-07-21 CH CH1882868A patent/CH490321A/en not_active IP Right Cessation
- 1964-07-21 CH CH1882968A patent/CH476677A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH476677A (en) | 1969-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |