DD249268A5 - METHOD FOR THE PREPARATION OF 1- (ALPHA- (BIPHENYLYL) BENZYL) -IMIDAZOLE - Google Patents
METHOD FOR THE PREPARATION OF 1- (ALPHA- (BIPHENYLYL) BENZYL) -IMIDAZOLE Download PDFInfo
- Publication number
- DD249268A5 DD249268A5 DD29343886A DD29343886A DD249268A5 DD 249268 A5 DD249268 A5 DD 249268A5 DD 29343886 A DD29343886 A DD 29343886A DD 29343886 A DD29343886 A DD 29343886A DD 249268 A5 DD249268 A5 DD 249268A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- imidazole
- benzyl
- biphenylyl
- preparation
- reaction
- Prior art date
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- JWZINEXEXQUCNS-UHFFFAOYSA-N 1-[phenyl-(2-phenylphenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JWZINEXEXQUCNS-UHFFFAOYSA-N 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 21
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000019253 formic acid Nutrition 0.000 claims abstract description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 7
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims abstract description 5
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 abstract description 4
- 229960002206 bifonazole Drugs 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- XBECWGJPSXHFCS-UHFFFAOYSA-N imidazole-1-carbaldehyde Chemical compound O=CN1C=CN=C1 XBECWGJPSXHFCS-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 238000003833 Wallach reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 etc. Chemical compound 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WMFZVLIHQVUVGO-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)C1=CC=CC=C1 WMFZVLIHQVUVGO-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Die Erfindung betrifft ein neues Verfahren zur Darstellung von 1-(a-(Biphenylyl)benzyl)imidazol (Bifonazol). Erfindungsgemaess wird 1-(a-(Biphenylyl)benzyl)imidazol der Formel I, in der Weise hergestellt, dass p-Phenylbenzophenon durch Behandeln mit Imidazol und Ameisensaeure reduzierend aminiert wird. Formel IThe invention relates to a novel process for preparing 1- (α- (biphenylyl) benzyl) imidazole (bifonazole). According to the invention, 1- (α- (biphenylyl) benzyl) imidazole of the formula I is prepared in such a way that p-phenylbenzophenone is reduced in reduction by treatment with imidazole and formic acid. Formula I
Description
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß in Lösungsmitteln wie Ameisensäure, Chloroform, Tetrachlorkohlenstoff, Toluol, XiIoI; Säureester wie Essigsäurebutylester, Ameisensäurebutylester; Alkohole wie n-Butanol, Isobutanol, Amylalkohol u.a., oder 1-Formylimidazol selbst, gearbeitet wird.2. The method according to claim 1, characterized in that in solvents such as formic acid, chloroform, carbon tetrachloride, toluene, XiIoI; Acid esters such as butyl acetate, butyl formate; Alcohols such as n-butanol, isobutanol, amyl alcohol, etc., or 1-formylimidazole itself, is worked.
3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß es bei Temperaturen zwischen 60 und 2500C gearbeitet wird.3. The method according to claim 1, characterized in that it is carried out at temperatures between 60 and 250 0 C.
4. Verfahren nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß in Anwesenheit von Entwässerungsmitteln wie Natriumsulfat, Kaliumchlorid, Magnesiumsulfat gearbeitet wird.4. Process according to claims 1 to 3, characterized in that it is carried out in the presence of dehydrating agents such as sodium sulfate, potassium chloride, magnesium sulfate.
5. Verfahren nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß das Reaktionswasser durch azeotropische Destillation mit dem Reaktionslösungsmittel entfernt wird.5. Process according to claims 1 to 3, characterized in that the water of reaction is removed by azeotropic distillation with the reaction solvent.
Die vorliegende Erfindung betrifft ein neues Verfahren zur Darstellung von 1-(a-(Biphenyl)benzyl)imidazol (Bifonazol).The present invention relates to a novel process for the preparation of 1- (α- (biphenyl) benzyl) imidazole (bifonazole).
Bifonazol, d.h. 1-(a-(4-Biphenylyl)benzyl)imidazol, der Formel IBifonazole, i. 1- (α- (4-biphenylyl) benzyl) imidazole of the formula I.
ist ein Imidazolderivat mit antimikotischer Wirkung, das aus der Literatur bekannt ist (s. DE-OS No. 2.714.290 vom 5.10.1978). Diese Verbindung wird durch Reduktion des p-Phenylbenzophenons und Kondensation des so bereiteten p-Phenylbenzhydrois mit Imidazol in Anwesenheit von Thionylchlorid nach folgendem Schema 1 dargestellt.is an imidazole derivative with an antimicrobial effect, which is known from the literature (see DE-OS No. 2,714,290 of October 5, 1978). This compound is prepared by reduction of p-phenylbenzophenone and condensation of thus prepared p-phenylbenzhydrois with imidazole in the presence of thionyl chloride according to the following Scheme 1.
— Δ- ί.«+J7 - Δ- ί. "+ J7
SCHEMA 1SCHEMA 1
NaH4BNaH 4 B
SOCl2 ImidazolSOCl 2 imidazole
Die bedeutendsten Mängel dieser Herstellungsweise sind in der Anwendung von Thionylchlorid zu finden. Tatsächlich ist es wohl bekannt, daß diese Verbindung außerordentlich aggressiv und schwer zu handhaben ist. Ein weiterer Mangel ist die unbefriedigende Reinheit des Endproduktes.The most important deficiencies of this method of preparation can be found in the use of thionyl chloride. In fact, it is well known that this compound is extremely aggressive and difficult to handle. Another shortcoming is the unsatisfactory purity of the final product.
Ziel der Erfindung ist die Bereitstellung eines neuen und vorteilhaften Verfahrens zur Darstellung von Bifonazoi, mit dem die oben genannten Mangel des bekannten Verfahrens vermieden werden können.The aim of the invention is to provide a new and advantageous process for the preparation of bifonazoi, with which the abovementioned deficiencies of the known process can be avoided.
Der Erfindung liegt die Aufgabe zugrunde, eine neuartige Technologie für die Herstellung von Bifonazoi aufzufinden, insbesondere unter Vermeidung von Thionylchlorid.The invention has for its object to find a novel technology for the production of Bifonazoi, especially while avoiding thionyl chloride.
Das Verfahren gemäß der Erfindung ist durch die reduzierende Amination von p-Phenylbenzophenon durch Behandeln mit Imidazol und Ameisensäure nach der Methode von Leuckart-Wallach gekennzeichnet. Die Reaktionsfolge ist im folgenden Schema 2 erläutert:The process according to the invention is characterized by the reducing amination of p-phenylbenzophenone by treatment with imidazole and formic acid by the method of Leuckart-Wallach. The reaction sequence is explained in the following scheme 2:
SCHEMA 2 ' nr SCHEMA 2 ' no
HCOOHHCOOH
Gegenüber der in Schema 1 dargestellten Methode weist das Verfahren gemäß der Erfindung bedeutende Vorteile, d.h.Compared with the method shown in Scheme 1, the method according to the invention has significant advantages, i.
— Die Synthese wird in einziger Stufe/statt zwei, durchgeführt;- The synthesis is carried out in a single stage / instead of two;
— die Ausbeute der Kondensation ist besser;The yield of condensation is better;
— der Reaktionsablauf ist sehr eindeutig, und es werden praktisch keine Nebenprodukte gebildet, wobei nur eine untergeordnete Menge an p-Phenylbenzhydrol (das nach neueren Untersuchungen der Leuckart-Wallachschen Reaktion ein Reaktionszwischenprodukt ist) gebildet wird. Dadurch sind Gewinnung und Reinigung des Endproduktes erheblich erleichtert.The course of the reaction is very clear, and virtually no by-products are formed, with only a minor amount of p-phenylbenzhydrol (which according to recent studies of the Leuckart-Wallach reaction is a reaction intermediate) being formed. As a result, recovery and purification of the final product are greatly facilitated.
Die Umsetzung wird in Anwesenheit von Lösungsmitteln, deren Charakter unkritisch ist, vorgenommen. Es genügt, daß die Lösungsmittel keinen negativen Einfluß über die Reaktion ausüben.The reaction is carried out in the presence of solvents whose character is not critical. It is sufficient that the solvents exert no negative influence on the reaction.
Geeignete Lösungsmittel sind neben Ameisensäure selbst Chloroform, Tetrachlorkohlenstoff, Toluol, XiIoI; Säureester wie Essigsäurebutylester, Ameisensäurebutylester; Alkohole wie n-Butanol, Isobutanol, Amylalkohol und a.m.; oder 1-Formylimidazol selbst.Suitable solvents are not only formic acid itself chloroform, carbon tetrachloride, toluene, XiIoI; Acid esters such as butyl acetate, butyl formate; Alcohols such as n-butanol, isobutanol, amyl alcohol and a.m .; or 1-formylimidazole itself.
Es ist möglich, in An- oder Abwesenheit von Entwässerungsmitteln wie Natriumsulfat, Kalziumchlorid, Magnesiumsulfat zu arbeiten. Es ist auch geeignet, die Entwässerung durch azeotropische Destillation mit dem Umsetzungslösungsmittel durchzuführen.It is possible to work in the presence or absence of dehydrating agents such as sodium sulfate, calcium chloride, magnesium sulfate. It is also suitable to carry out the dehydration by azeotropic distillation with the reaction solvent.
Die Temperatur kann zwischen 60 und 250°C schwanken. Die Reaktionszeiten sind daran anzupassen.The temperature can vary between 60 and 250 ° C. The reaction times are to be adapted.
Die Erfindung wird nachstehend an einem Beispiel näher erläutertThe invention will be explained in more detail below by way of example
Das Beispiel soll keine Einschränkung der Erfindung sein. The example is not intended to be a limitation of the invention.
In einem Rundkolben von 100 ml werden 23,4g Imidazol und 12,8 ml Ameisensäure vorgelegt. Es wird mit einem Ölbad bei 2200C erhitzt, bis das der Bildung des Amids entsprechende Wasser freigesetzt wird.In a round bottom flask of 100 ml, 23.4 g of imidazole and 12.8 ml of formic acid are introduced. It is heated with an oil bath at 220 0 C until the formation of amide corresponding water is released.
Man kühlt auf 50°C, und weitere 12ml Ameisensäure und 5g p-Phenylbenzophenon werden zugesetzt. Die Mischung wird auf 200°Cfür20 Stunden erhitzt, dann auf 20°C abgekühlt. 30 g Natriumhydroxid, in 100 ml Wasser gelöst, und 100 ml Toluol werden zugefügt. Die Reaktionsmischung wird über Nacht auf Raumtemperatur gerührt.It is cooled to 50 ° C, and a further 12ml of formic acid and 5g of p-phenylbenzophenone are added. The mixture is heated to 200 ° C for 20 hours, then cooled to 20 ° C. 30 g of sodium hydroxide dissolved in 100 ml of water and 100 ml of toluene are added. The reaction mixture is stirred overnight at room temperature.
Der gebildete Niederschlag wird filtriert, mit Wasser und wenig Toluol gewaschen und getrocknet. Es werden 3,9g Rohprodukt erhalten, das aus Essigsäurenitril umgelöst wird.The precipitate formed is filtered, washed with water and a little toluene and dried. There are obtained 3.9 g of crude product which is redissolved from Essigsäurenitril.
Das erhaltene Produkt schmilzt bei 142°C. Die Elementaranalyse und das Infrarotspektrum stimmen mit denjenigen einer Probe des Produktes gemäß DE-OS 2.714.290 überein.The product obtained melts at 142.degree. The elemental analysis and the infrared spectrum are consistent with those of a sample of the product according to DE-OS 2,714,290.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22818/85A IT1201492B (en) | 1985-11-13 | 1985-11-13 | BIFONAZOLE SYNTHESIS METHOD |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD249268A5 true DD249268A5 (en) | 1987-09-02 |
Family
ID=11200796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD29343886A DD249268A5 (en) | 1985-11-13 | 1986-08-05 | METHOD FOR THE PREPARATION OF 1- (ALPHA- (BIPHENYLYL) BENZYL) -IMIDAZOLE |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT396931B (en) |
| DD (1) | DD249268A5 (en) |
| ES (1) | ES2001449A6 (en) |
| IT (1) | IT1201492B (en) |
| YU (1) | YU44292B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2808086A1 (en) * | 1978-02-24 | 1979-08-30 | Bayer Ag | SUBSTITUTED DIPHENYL-IMIDAZOLYL-METHANES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT |
| DE3538872A1 (en) * | 1985-11-02 | 1987-05-07 | Bayer Ag | O-Biphenylylimidazol-1-ylphenylmethane, process for its preparation and its use as an antimycotic |
-
1985
- 1985-11-13 IT IT22818/85A patent/IT1201492B/en active
-
1986
- 1986-07-02 YU YU116786A patent/YU44292B/en unknown
- 1986-08-05 DD DD29343886A patent/DD249268A5/en not_active IP Right Cessation
- 1986-11-11 ES ES8602982A patent/ES2001449A6/en not_active Expired
- 1986-11-11 AT AT299486A patent/AT396931B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1201492B (en) | 1989-02-02 |
| YU44292B (en) | 1990-04-30 |
| IT8522818A0 (en) | 1985-11-13 |
| YU116786A (en) | 1987-12-31 |
| ES2001449A6 (en) | 1988-05-16 |
| ATA299486A (en) | 1993-05-15 |
| AT396931B (en) | 1993-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A5 | Published as prov. exclusive patent | ||
| ENJ | Ceased due to non-payment of renewal fee |