CH531509A - Imidazo (2,1-a) isoindoles useful as anorexige - nics and cns stimulants - Google Patents
Imidazo (2,1-a) isoindoles useful as anorexige - nics and cns stimulantsInfo
- Publication number
- CH531509A CH531509A CH1572372A CH1572372A CH531509A CH 531509 A CH531509 A CH 531509A CH 1572372 A CH1572372 A CH 1572372A CH 1572372 A CH1572372 A CH 1572372A CH 531509 A CH531509 A CH 531509A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- imidazo
- isoindoles
- useful
- anorexige
- Prior art date
Links
- YNFXWRMIKILVHC-UHFFFAOYSA-N 3h-imidazo[2,1-a]isoindole Chemical class C1=CC=CC2=C3N=CCN3C=C21 YNFXWRMIKILVHC-UHFFFAOYSA-N 0.000 title claims description 3
- 239000002269 analeptic agent Substances 0.000 title abstract 2
- 229940124332 anorexigenic agent Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 150000002518 isoindoles Chemical class 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 230000002891 anorexigenic effect Effects 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
- JWWLTRDKVHXMRA-UHFFFAOYSA-N 5-(3-fluorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=CC(F)=C1 JWWLTRDKVHXMRA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- -1 Hexane or heptane Chemical class 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000578 anorexic effect Effects 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- QAFJIJWLEBLXHH-UHFFFAOYSA-N methyl 2-fluorobenzoate Chemical class COC(=O)C1=CC=CC=C1F QAFJIJWLEBLXHH-UHFFFAOYSA-N 0.000 description 1
- WICGATIORFSOJL-UHFFFAOYSA-N methyl 3,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(Cl)=C1 WICGATIORFSOJL-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Imidazo 2,1-a isoindoles useful as anorexigenics and CNS stimulants. Processes for the preparation of title cpds. of formula (I) (where R and R1 are H, F or Cl) are claimed. Also claimed are cpds. of formula (II) (where R3 is H or phenyl) and their salts with mineral and organic acids, which have anorexigenic activity. (II; R3 = H) are intermediates for (I). Other intermediates in the prepn. of (I) are also claimed.
Description
Verfahren zur Herstellung von Imidazot2,1-a]isoindolen
Die Erfindung betrifft ein Verfahren zur Herstellung von Imidazo[2,1-a]isoindolen der Formel I
EMI1.1
worin R und R1 Wasserstoff, Fluor oder Chlor bedeuten.
Die Verbindungen der Formel I kommen bekanntlich in verschiedenen ionischen und tautomeren Formen vor, die von der Formel I ebenfalls umfasst werden sollen.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man die Verbindung der Formel II
EMI1.2
mit Verbindungen der Formel III
EMI1.3
worin R und R1 obige Bedeutung besitzen und X für
Chlor, Brom oder einen Rest -OR2 steht, in welchem R ein geradkettiges Alkyl mit 1-4 Kohlenstoffatomen bedeutet, unter inerter Atmosphäre und in einem inerten organischen Lösungsmittel umsetzt und das erhaltene
Addukt hydrolysiert.
Die erste Stufe des Verfahrens kann beispielsweise unter Stickstoff und in einem Kohlenwasserstoff, wie
Hexan oder Heptan, oder einem Äther, wie Diäthyläther oder Tetrahydrofuran, als Lösungsmittel durchgeführt werden. Man arbeitet zweckmässigerweise bei Temperaturen zwischen etwa 0 und 100 C, vorzugsweise Raumtemperatur und Rückflusstemperatur des Reaktionsgemisches, und die Reaktionszeit kann beispielsweise zwischen etwa 0,5 und 48 Stunden liegen. Die nachfolgende Hydrolyse kann in an sich bekannter Weise durchgeführt werden, beispielsweise mittels Wasser, verdünnter Mineralsäure oder Ammoniumchlorid-Lösung.
Die Verbindungen der Formel I können gegebenen falls in an sich bekannter Weise in Säureadditionssalze umgewandelt werden und umgekehrt. Als Ausgangspro dukte kann man gegebenenfalls ebenso Säureadditionssalze verwenden, so dass man direkt zu Säureadditionssalzen gelangt.
Die Isolierung und Reinigung der erfindungsgemässen Verbindungen erfolgt ebenfalls in an sich bekannter Weise.
Die Ausgangsprodukte der Formel II sind neu.
Sie können hergestellt werden durch Umsetzung der Verbindung der Formel IV
EMI2.1
mit Verbindungen der Formel V R2Li V worin R2 obige Bedeutung besitzt, unter inerter Atmosphäre und in einem inerten organischen Lösungsmittel.
Das Verfahren wird zweckmässigerweise bei Temperaturen zwischen etwa Raumtemperatur und 1000C, vorzugsweise bei Rückflusstemperatur des Reaktionsgemisches, durchgeführt, und die Reaktionszeit kann beispielsweise 0,5 bis 24 Stunden betragen. Ansonsten kann das Verfahren analog zur ersten Stufe des erfindungsgemässen Verfahrens durchgeführt werden.
Die Verbindung der Formel IV ist bekannt
Es ist bekannt, dass die Verbindungen der Formel I appetitzügelnde und ZNS-stimulierende Wirkung zeigen und sich als Anorexika sowie Psychopharmaka verwenden lassen (s. z.B. belgische Patentschrift Nr. 712 596).
Beispiel I
S-f4Chlorphenyl)-5-hydroxy-2,3SdihysSro-5H- -im idazo [2,1 -a]isoindol a) N,o-Dilithium-Derivat von 2-Phenyl-2-imidazolin
Ein mit Rührer, Kühler und Tropftrichter versehener, unter Stickstoff gehaltener Kolben wird mit 7,3 g (0,05 Mol) 2-Phenylimidazolin und 100 ml trockenem Di äthyläther beschickt. Unter Rühren fügt man innerhalb 15 Minuten 94 ml einer 1,6molaren Lösung von n-Butyllithium in Hexan (0,15 Mol n-Butyllithium) zu. Die Suspension wird etwa 24 Stunden bei Raumtemperatur gerührt, und man erhält so das N,o-Dilithium-Derivat von 2-Phenylimidazolin.
b) 5-(4-Chlorphenyl)-5-hydroxy-2,3-dihydro-SH- -imidazo[2, 1 -a]isoindol
Die gemäss Verfahrensstufe a) erhaltene Suspension wird, weiterhin unter Stickstoffatmosphäre, in einem Eisbad auf eine Innentemperatur von 10 + 50C gekühlt und tropfenweise mit einer Lösung von 19,1 g (0,11 Mol) 4-Chlorbenzoylchlorid in 75 ml Diäthyläther versetzt. Das Gemisch wird 6 Stunden bei Raumtemperatur gerührt, in einem Eisbad gekühlt und mit 25 ml gesättigter Ammoniumchlorid-Lösung behandelt. Die Ätherschicht wird abgetrennt, mit 50 ml 2N Kaliumhydroxid-Lösung gewaschen, mit Magnesiumsulfat getrocknet, filtriert und im Vakuum eingeengt. Nach Umkristallisieren des Rückstandes aus Methanol-Tetrahydrofuran (1:1) erhält man das 5-(4-Chlorphenyl)-5-hy droxy-2,3-dihydro-5H-imidazo[2, 1 -ajisoindol vom Smp.
1980 -2000C.
Beispiel 2
5-(3,4-Dchlorphenyl)-5-kydroxy-2,3-dikydro-5H- -zmidazo[2,1 -ajisoindol
Gemäss Beispiel 1 jedoch unter Verwendung von 3,4 Dichlorbenzoesäuremethylester anstelle von 4-Chlorbenzoylchlorid, gelangt man zur Titelverbindung vom Smp.
2000 - 201OC.
Beispiel 3
5-(3-Fluorphenyl)-5-hydroxy-2 ,3-dihydro -5H- -imidazo[2,1-a]isoindol
Gemäss Beispiel 1 jedoch unter Verwendung von 3 Fluorbenzoesäuremethylester anstelle von 4-Chlorben- zoylchlorid, gelangt man zur Titelverbindung vom Smp.
200 - 203 C.
Beispiel 4
5-Hydroxy-5-phenyl-2, 3-dlliydro-5H- -imidazo[Z1-d\isoipidol
Analog den vorhergehenden Beispielen und unter Verwendung entsprechender Ausgangsprodukte in geeigneten Mengen gelangt man zur Titelverbindung vom Smp. 197- 199ob.
Process for the preparation of imidazot2,1-a] isoindoles
The invention relates to a process for the preparation of imidazo [2,1-a] isoindoles of the formula I.
EMI1.1
wherein R and R1 are hydrogen, fluorine or chlorine.
The compounds of the formula I are known to occur in various ionic and tautomeric forms, which are also intended to be encompassed by the formula I.
The inventive method is characterized in that the compound of formula II
EMI1.2
with compounds of the formula III
EMI1.3
wherein R and R1 have the above meaning and X is
Chlorine, bromine or a radical -OR2, in which R is a straight-chain alkyl with 1-4 carbon atoms, is reacted under an inert atmosphere and in an inert organic solvent and the resultant
Hydrolyzed adduct.
The first stage of the process can, for example, under nitrogen and in a hydrocarbon such as
Hexane or heptane, or an ether such as diethyl ether or tetrahydrofuran, can be carried out as a solvent. It is expedient to work at temperatures between about 0 and 100 ° C., preferably room temperature and the reflux temperature of the reaction mixture, and the reaction time can be, for example, between about 0.5 and 48 hours. The subsequent hydrolysis can be carried out in a manner known per se, for example using water, dilute mineral acid or ammonium chloride solution.
The compounds of the formula I can optionally be converted into acid addition salts and vice versa in a manner known per se. Acid addition salts can optionally also be used as starting products, so that acid addition salts are obtained directly.
The compounds according to the invention are likewise isolated and purified in a manner known per se.
The starting products of Formula II are new.
They can be prepared by reacting the compound of the formula IV
EMI2.1
with compounds of the formula V R2Li V in which R2 has the above meaning, under an inert atmosphere and in an inert organic solvent.
The process is expediently carried out at temperatures between about room temperature and 1000 ° C., preferably at the reflux temperature of the reaction mixture, and the reaction time can be, for example, 0.5 to 24 hours. Otherwise, the process can be carried out analogously to the first stage of the process according to the invention.
The compound of the formula IV is known
It is known that the compounds of the formula I have an appetite suppressant and CNS-stimulating effect and can be used as anorexics and psychotropic drugs (see, for example, Belgian patent specification No. 712 596).
Example I.
S-f4Chlorophenyl) -5-hydroxy-2,3SdihysSro-5H- -imidazo [2,1 -a] isoindole a) N, o-dilithium derivative of 2-phenyl-2-imidazoline
A flask kept under nitrogen and equipped with a stirrer, condenser and dropping funnel is charged with 7.3 g (0.05 mol) of 2-phenylimidazoline and 100 ml of dry diethyl ether. 94 ml of a 1.6 molar solution of n-butyllithium in hexane (0.15 mol of n-butyllithium) are added over 15 minutes with stirring. The suspension is stirred for about 24 hours at room temperature, and the N, o-dilithium derivative of 2-phenylimidazoline is obtained in this way.
b) 5- (4-chlorophenyl) -5-hydroxy-2,3-dihydro-SH- -imidazo [2, 1 -a] isoindole
The suspension obtained according to process step a) is cooled in an ice bath to an internal temperature of 10 + 50 ° C., still under a nitrogen atmosphere, and a solution of 19.1 g (0.11 mol) of 4-chlorobenzoyl chloride in 75 ml of diethyl ether is added dropwise. The mixture is stirred for 6 hours at room temperature, cooled in an ice bath and treated with 25 ml of saturated ammonium chloride solution. The ether layer is separated off, washed with 50 ml of 2N potassium hydroxide solution, dried with magnesium sulfate, filtered and concentrated in vacuo. After recrystallization of the residue from methanol-tetrahydrofuran (1: 1), 5- (4-chlorophenyl) -5-hy droxy-2,3-dihydro-5H-imidazo [2,1-ajisoindole of mp.
1980-2000C.
Example 2
5- (3,4-Dchlorophenyl) -5-kydroxy-2,3-dikydro-5H- -zmidazo [2,1 -ajisoindole
According to Example 1, however, using methyl 3,4 dichlorobenzoate instead of 4-chlorobenzoyl chloride, the title compound has a melting point of.
2000 - 201OC.
Example 3
5- (3-fluorophenyl) -5-hydroxy-2,3-dihydro -5H-imidazo [2,1-a] isoindole
According to Example 1, however, using 3 methyl fluorobenzoates instead of 4-chlorobenzoyl chloride, the title compound has a melting point of.
200 - 203 C.
Example 4
5-Hydroxy-5-phenyl-2,3-dihydro-5H -imidazo [Z1-d \ isoipidol
The title compound with a melting point of 197-199ob is obtained analogously to the preceding examples and using appropriate starting materials in suitable amounts.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82595469A | 1969-05-19 | 1969-05-19 | |
| US85617969A | 1969-10-09 | 1969-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH531509A true CH531509A (en) | 1972-12-15 |
Family
ID=27124961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1572372A CH531509A (en) | 1969-05-19 | 1970-02-20 | Imidazo (2,1-a) isoindoles useful as anorexige - nics and cns stimulants |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH531509A (en) |
-
1970
- 1970-02-20 CH CH1572372A patent/CH531509A/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH649980A5 (en) | PHENOXYBENZYL ALCOHOLS AND METHOD FOR THE PRODUCTION THEREOF. | |
| DE2614242C3 (en) | Process for the production of acyl cyanides | |
| CH597199A5 (en) | 3-Phenyl pyridaz-6-ones prodn. | |
| DE2009780C2 (en) | N, o-Dilithium derivative of 2-phenyl-2-imidazoline, a process for the production thereof and a process for the production of imidazo [2, l-a] isoindoles | |
| DE69902071T2 (en) | Process for the preparation of 2-substituted pyridines | |
| CH531509A (en) | Imidazo (2,1-a) isoindoles useful as anorexige - nics and cns stimulants | |
| DE19858594A1 (en) | Cyanobenzene-boronic acid or ester preparation in high yield comprises treating halo-benzonitrile and trialkyl borate with alkyl lithium, used as intermediate e.g. for liquid crystals, pesticides or drugs | |
| DE2758624A1 (en) | PROCESS FOR THE PREPARATION OF LOW ALKYLESTERS OF THE RACEMIC 2,2-DISUBSTITUTED TRANS-CYCLOPROPANE-1,3-DICARBONIC ACIDS AND NEW ESTERS OF THESE ACIDS | |
| DE2642608A1 (en) | 4-HYDROXYMETHYL-2-PYRROLIDINONE AND THE METHOD FOR THEIR PRODUCTION | |
| EP0063740B1 (en) | Process for the preparation of tertiary alkyl cyanides | |
| EP0132681B1 (en) | Process for the preparation of fluorocarboxylic acids | |
| DE2225545A1 (en) | Phosphinic acid halides prodn - from phosphinic acids or their salts and inorg acid halides | |
| DE1083261B (en) | Process for the preparation of tertiary alkylcyclopentadienes | |
| DE2125229A1 (en) | Process for the production of china zolinen | |
| DE2649856A1 (en) | PROCESS FOR THE MANUFACTURING OF DIHALOGUE VINYLCYCLOPROPANCARBON ACID ESTERS | |
| DE1121060B (en) | Process for the preparation of N-alkyl-amidosulfonyl chlorides | |
| AT236394B (en) | Process for the preparation of new N-substituted heterocyclic compounds | |
| DE1470379C (en) | 11 (1 methyl 4 piperidyhden) morphan thridin its acid salts and manufacturing process | |
| DE952084C (en) | Process for the production of organic isothiocyanates | |
| DD150895A1 (en) | METHOD FOR PRODUCING SUBSTITUTED NITROBENZO-ETHERCYCLES | |
| AT273966B (en) | Process for the preparation of new 1- (polyhaloalkylthio) indazoles | |
| DD153841A5 (en) | PROCESS FOR THE PREPARATION OF DIAZONIUM TETRAFLUOROBORATES | |
| DE2836085A1 (en) | SULFAMOYLBENZENE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF | |
| DE1081471B (en) | Process for the preparation of N- [4, 5, 6, 7, 10, 10-hexachloro-4, 7-endomethylene-4, 7, 8, 9-tetrahydro-phthalanyl- (1)] - ª ‡ -aminocarboxylic acid esters | |
| DE1231714B (en) | Process for the production of bis-2- (1, 3, 2-dioxaborolane), bis-2- (1, 3, 2-dioxaborinane) or bis-2- (1, 3, 2-dioxabenzoborol) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |