CH387010A - Process for the preparation of benzamide derivatives which are optionally substituted in the core - Google Patents

Process for the preparation of benzamide derivatives which are optionally substituted in the core

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Publication number
CH387010A
CH387010A CH650160A CH650160A CH387010A CH 387010 A CH387010 A CH 387010A CH 650160 A CH650160 A CH 650160A CH 650160 A CH650160 A CH 650160A CH 387010 A CH387010 A CH 387010A
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CH
Switzerland
Prior art keywords
preparation
compound
optionally substituted
amide
formula
Prior art date
Application number
CH650160A
Other languages
German (de)
Inventor
Takahashi Torizo
Ogiu Kikuo
Fujimura Hajime
Satoda Isao
Fukui Tomijiro
Yamamoto Yasuo
Original Assignee
Nippon Shinyaku Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd
Publication of CH387010A publication Critical patent/CH387010A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

  

  
 



  Verfahren zur Herstellung von   Benzamid-Abkömmlingen,    die gegebenenfalls im Kern substituiert sind
Die Erfindung betrifft ein Verfahren zur Herstellung von Benzamid-Abkömmlingen, die gegebenenfalls im Kern substituiert sind, und die Formel
EMI1.1     
 aufweisen, in der   Rj    Wasserstoff, einen Alkyl- oder Alkoxyrest, R2 einen Alkylenrest und R3 einen mono- oder dialkylsubstituierten Aminrest oder ein cyclisches Amin, welches über das Stickstoffatom an die Carbonylgruppe gebunden ist, bedeuten.



  Diese Verbindungen sind neu und bisher noch nicht in der Literatur beschrieben worden. Diese Verbindungen sind zweckmässig, da sie ausgezeichnete antipyretische, analgetische, antiphlogistische undloder krampflösende Wirkungen besitzen. Einige dieser Verbindungen sind sehr wasserlöslich und für Injektionslösungen geeignet.



   Gemäss der Erfindung werden die Verbindungen der obigen Formel hergestellt durch Umsetzung von Verbindungen der Formel
EMI1.2     
 mit Verbindungen, die durch die Formel XR2COR3 dargestellt werden, in der X Halogen ist.



   Bei der Durchführung des erfindungsgemässen Verfahrens ist es bevorzugt, das als Ausgangsverbindung dienende Amid mit Natriumalkoholat, metallischem Natrium oder Natriumalkoholat in Gegenwart eines nicht polaren Lösungsmittels, wie Benzol, Toluol, Xylol usw., umzusetzen, und sodann zusammen mit der Verbindung der Formel   XR2COR3    zu erwärmen. Die sich ergebende Verbindung kann sodann aus einem entsprechenden Lösungsmittel, wie Benzol, Xylol, n-Hexan oder Methyläthylketon, umkristallisiert werden.



   Beispiel 1
Herstellung von   N-(2-Methoxy-benzoyl)-N',N'-    dimethylglycinamid
Es wird ein Gemisch aus 15 g 2-Methoxybenzamid und 4,5 g pulverisiertem Natriumamid in wasserfreiem Benzol oder Xylol mehrere Stunden am Rückfluss gekocht, und sodann eine Lösung von 15 g Chloressigsäuredimethylamid in Benzol oder Xylol eingetropft, und unter Erwärmen mehrere Stunden gerührt. Die Lösung wird sodann abgekühlt, filtriert und das Filtrat eingeengt. Der Rückstand wird sodann aus Xylol, geringen Mengen an Benzol oder Benzol-n-Hexan oder Methyläthylketon umkristallisiert, wodurch die obige Verbindung in Form farbloser Nadeln mit einem Fp. =   117-1184 C    in 650/oiger Ausbeute erhalten wird.



  Analyse: berechnet für   C12H16O0N2      (236,26):   
C   61,000/o    H   6,830/o    N   11,860/o    gefunden: C   61, 30 /o    H   6,740/o    N   11,880/o   
Bei Anwendung metallischen Natriums anstelle von Natriumamid kann die gewünschte Verbindung in   600/oiger    Ausbeute erhalten werden. Anderseits kann es auch bevorzugt sein, Natriumalkoholat anzuwenden. Es werden z. B. 15 g 2-Methoxybenzamid in 200 ml Benzol suspendiert und mit 5,5 g Natriummethylat unter Erwämen gerührt. Es werden sodann etwa 100   ml    Benzol abdestilliert, um so das Methanol zu entfernen. Unter Kühlen und Rühren  werden 12,5 g Chloressigsäuredimethylamid eingetropft und weitere 2 Stunden erwärmt.

   Die Lösung wird filtriert und sodann in der gleichen Weise weiterverarbeitet, wie weiter oben angegeben. Die gewünschte Verbindung, mit einem Fp. = 117 bis   118     C, wird in 63%iger Ausbeute erhalten.



   Beispiel   2   
Herstellung von N-B   enzoyl-N',N'-dimethyl-    glycinamid
Unter Anwendung von Benzamid und Chloressigsäuredimethylamid kann die obige Verbindung erhalten werden, wenn, wie im Beispiel 1 angegeben, verfahren wird. Man erhält farblose Säulen mit einem Fp.   =      112-113     C, die Ausbeute beträgt   52/o.   



  Analyse: berechnet für C11H14O2N2   (206,24):   
C   64,06o    H 6,84% N   13,580/o    gefunden: C   64,320/o    H   7, 05 /o    N   13,640/o   
Beispiel 3
Herstellung von   N-(2-Methyl-benzoyl)-N',N'-    dimethylglycinamid
Diese Verbindung in Form farbloser Nadeln mit einem Fp. =   137-138 C    (Methyläthylketon) kann erhalten werden, wenn 2-Methylbenzamid und Chloressigsäuredimethylamid angewandt und in der in Beispiel angegebenen Weise verarbeitet werden.



  Die Ausbeute beträgt   550/o.   



  Analyse: berechnet für C12H16O2N2   (220,26):    N   12,720/o    gefunden: N   12,780/o   
Beispiel 4
Herstellung von N-(2-Äthoxy-benzoyl)-N',N' dimethylglycinamid
Diese Verbindung in Form farbloser Nadeln mit einem Fp. =   125-126  C    (Alkohol-Hexan) kann erhalten werden, wenn 2-Äthoxybenzamid und Natriumamid angewandt wird, und anschliessend mit Chloressigsäuredimethylamid in Toluol umgesetzt wird. Die Ausbeute beträgt   600/o.   



  Analyse: berechnet für C13H18O3N2 (250,29):
C 62,38% H   7,250/o    N 11,190/0 gefunden: C 62,15% H 7,21% N 11,37%
Beispiel 5
Herstellung von   N-(4-Methoxy-benzoyl)-N',N'-    dimethylglycinamid
Es wird ein Gemisch aus 5 g 4-Methoxybenzamid und 1,4 g Natriumamid in 50 ml Toluol am Rückfluss gekocht und sodann eine Lösung von Chloressigsäuredimethylamid in Toluol eingetropft.



  Man kocht 5 Stunden am Rückfluss, kühlt ab, filtriert, und das Filtrat wird anschliessend eingeengt.



  Der Rückstand wird aus Aceton-Äther umkristallisiert, wobei die obige Verbindung in 470/oiger Ausbeute mit einem Fp. =   103-104  C    erhalten wird.



  Analyse: berechnet für C12H16O3N2   (236,26):   
C 61,00% H 6,85% N 11,86 gefunden: C 60,97% H   6,650/o    N   ll,850/o   
Beispiel 6
Herstellung von   N-(4-Methyl-benzoyl)-N',N'-    dimethylglycinamid
Ein Gemisch aus 5 g 4-Methylbenzamid, 1,6 g Natriumamid und 50 ml Toluol wird 2 Stunden am Rückfluss gekocht. Sodann wird bei Raumtemperatur eine Lösung von 4,5 g Chloressigsäuredimethylamid in Toluol eingetropft, weitere 5 Stunden am Rückfluss gekocht, abgekühlt und filtriert. Das Filtrat wird eingeengt und der Rückstand aus Aceton Äther umkristallisiert, wodurch die obige Verbindung in 53%iger Ausbeute mit einem Fp.   =    1190 C erhalten wird.



  Analyse: berechnet für   C1 H16O2N.      (220,26):   
C 65,43% H 7,32% N 12,72% gefunden: C 65,67% H 7,24% N 12,69%
Beispiel 7
Herstellung von   N-(2-Methoxy-benzoyl)-N',N'-    diäthylglycinamid
Es wird ein Gemisch aus 10 g 2-Methoxybenzamid, 3,0 g Natriumamid und 150 ml Benzol am Rückfluss gekocht, sodann mit 1,2 g Chloressigsäurediäthylamid erwärmt, filtriert und das Filtrat eingeengt. Die sich ergebende, nicht kristallisierende Substanz wird unter verringertem Druck destilliert, wodurch 12 g   (690/o)    der gewünschten Verbindung mit einem Sp.   =    204-206  C/1,0 mm Hg erhalten werden.



  Analyse: berechnet für   C14H20O3N2      (264,32):   
C 63,61% H 7,63% N 10,60% gefunden: C   63,110/o    H 7,660/0 N 10,56%
Beispiel 8
Herstellung von N-(2-Methoxy-benzoyl)-N' methylglycinamid
Diese Verbindung kann aus 2-Methoxybenzamid und Chloressigsäuremethylamid erhalten werden. Das in 640/oiger Ausbeute erhaltene Produkt weist einen Fp. = 98-99  C auf. Wenn diese Verbindung sich selbst überlassen wird, wandelt sich dieselbe in eine polymorphe Form mit einem Fp. = 113-114  C um.  



  Analyse: berechnet für   CllHl403N2      (222,24):   
C 59,45% H 6,35% N 12,60% gefunden: C 59,59% H 6,49% N 12,45%
Beispiel 9
Herstellung von N-(2-Methoxy-benzoyl) glycinpiperidid
Diese Verbindung, mit einem Fp. =   97-98  C,    (Benzol-n-Hexan) kann aus 2-Methoxybenzamid und Chloressigsäurepiperidid erhalten werden.



  Analyse: berechnet für   C15H20O3N2      (276,33):   
C 65,19% H 7,30% N 10,14% gefunden: C 65,25% H 7,41% N 9,95%
Beispiel 10
Herstellung von N-(2-Methoxy-benzoyl) glycinmorpholid
Diese Verbindung, mit einem Fp. =   114-1166    C (die Verbindung enthält 1 Mol Kristallwasser), kann aus 2-Methoxy-benzamid und Chloressigsäuremorpholid erhalten werden.



  Analyse: berechnet für   C14H16O4N2#H2O      (296,32):   
C 56,74% H 6,80% N 9,45% gefunden: C 56,95% H 6,79% N 9,74%
Beispiel 11
Herstellung von N-(2-Methoxy-benzoyl)-N',N' dimethylalaninamid
Diese Verbindung, mit einem Fp. =   75-77O C    (die Verbindung enthält 1 Mol Kristallwasser), kann aus 2-Methoxybenzamid und a-Brompropionsäuredimethylamid erhalten werden.   



  
 



  Process for the preparation of benzamide derivatives which are optionally substituted in the core
The invention relates to a process for the preparation of benzamide derivatives, which are optionally substituted in the core, and the formula
EMI1.1
 in which Rj is hydrogen, an alkyl or alkoxy radical, R2 is an alkylene radical and R3 is a mono- or dialkyl-substituted amine radical or a cyclic amine which is bonded to the carbonyl group via the nitrogen atom.



  These compounds are new and have not yet been described in the literature. These compounds are useful because they have excellent antipyretic, analgesic, anti-inflammatory and / or antispasmodic effects. Some of these compounds are very soluble in water and suitable for injection solutions.



   According to the invention, the compounds of the above formula are prepared by reacting compounds of the formula
EMI1.2
 with compounds represented by the formula XR2COR3 in which X is halogen.



   When carrying out the process according to the invention, it is preferred to react the starting amide with sodium alcoholate, metallic sodium or sodium alcoholate in the presence of a non-polar solvent such as benzene, toluene, xylene, etc., and then to react together with the compound of the formula XR2COR3 heat. The resulting compound can then be recrystallized from an appropriate solvent such as benzene, xylene, n-hexane or methyl ethyl ketone.



   example 1
Preparation of N- (2-methoxy-benzoyl) -N ', N'-dimethylglycine amide
A mixture of 15 g of 2-methoxybenzamide and 4.5 g of powdered sodium amide in anhydrous benzene or xylene is refluxed for several hours, and then a solution of 15 g of chloroacetic acid dimethylamide in benzene or xylene is added dropwise and the mixture is stirred while warming for several hours. The solution is then cooled, filtered and the filtrate concentrated. The residue is then recrystallized from xylene, small amounts of benzene or benzene-n-hexane or methyl ethyl ketone, whereby the above compound is obtained in the form of colorless needles with a melting point = 117-1184 ° C. in a yield of 650%.



  Analysis: calculated for C12H16O0N2 (236.26):
C 61.000 / o H 6.830 / o N 11.860 / o found: C 61. 30 / o H 6.740 / o N 11.880 / o
If metallic sodium is used instead of sodium amide, the desired compound can be obtained in 600% yield. On the other hand, it can also be preferred to use sodium alcoholate. There are z. B. 15 g of 2-methoxybenzamide suspended in 200 ml of benzene and stirred with 5.5 g of sodium methylate while warming. About 100 ml of benzene are then distilled off in order to remove the methanol. With cooling and stirring, 12.5 g of chloroacetic acid dimethylamide are added dropwise and the mixture is heated for a further 2 hours.

   The solution is filtered and then processed in the same way as indicated above. The desired compound, with a melting point = 117 to 118 ° C., is obtained in 63% yield.



   Example 2
Production of N-B enzoyl-N ', N'-dimethylglycine amide
Using benzamide and chloroacetic acid dimethylamide, the above compound can be obtained if the procedure given in Example 1 is followed. Colorless columns with a melting point = 112-113 ° C. are obtained; the yield is 52%.



  Analysis: calculated for C11H14O2N2 (206.24):
C 64.06o H 6.84% N 13.580 / o found: C 64.320 / o H 7.05 / o N 13.640 / o
Example 3
Preparation of N- (2-methyl-benzoyl) -N ', N'-dimethylglycine amide
This compound in the form of colorless needles with a melting point = 137-138 ° C. (methyl ethyl ketone) can be obtained if 2-methylbenzamide and chloroacetic acid dimethylamide are used and processed in the manner indicated in the example.



  The yield is 550%.



  Analysis: calculated for C12H16O2N2 (220.26): N 12.720 / o found: N 12.780 / o
Example 4
Preparation of N- (2-ethoxy-benzoyl) -N ', N' dimethylglycine amide
This compound in the form of colorless needles with a melting point = 125-126 ° C. (alcohol-hexane) can be obtained when 2-ethoxybenzamide and sodium amide are used and then reacted with chloroacetic acid dimethylamide in toluene. The yield is 600 / o.



  Analysis: calculated for C13H18O3N2 (250.29):
C 62.38% H 7.250 / o N 11.190 / 0 found: C 62.15% H 7.21% N 11.37%
Example 5
Preparation of N- (4-methoxy-benzoyl) -N ', N'-dimethylglycine amide
A mixture of 5 g of 4-methoxybenzamide and 1.4 g of sodium amide in 50 ml of toluene is refluxed and a solution of chloroacetic acid dimethylamide in toluene is then added dropwise.



  The mixture is refluxed for 5 hours, cooled, filtered, and the filtrate is then concentrated.



  The residue is recrystallized from acetone-ether, the above compound being obtained in 470% yield with a melting point = 103-104 ° C.



  Analysis: calculated for C12H16O3N2 (236.26):
C 61.00% H 6.85% N 11.86 found: C 60.97% H 6.650 / o N II, 850 / o
Example 6
Preparation of N- (4-methyl-benzoyl) -N ', N'-dimethylglycine amide
A mixture of 5 g of 4-methylbenzamide, 1.6 g of sodium amide and 50 ml of toluene is refluxed for 2 hours. A solution of 4.5 g of chloroacetic acid dimethylamide in toluene is then added dropwise at room temperature, the mixture is refluxed for a further 5 hours, cooled and filtered. The filtrate is concentrated and the residue is recrystallized from acetone / ether, whereby the above compound is obtained in 53% yield with a melting point = 1190.degree.



  Analysis: calculated for C1 H16O2N. (220.26):
C 65.43% H 7.32% N 12.72% found: C 65.67% H 7.24% N 12.69%
Example 7
Production of N- (2-methoxy-benzoyl) -N ', N'-diethylglycine amide
A mixture of 10 g of 2-methoxybenzamide, 3.0 g of sodium amide and 150 ml of benzene is refluxed, then heated with 1.2 g of chloroacetic acid diethylamide, filtered and the filtrate is concentrated. The resulting non-crystallizing substance is distilled under reduced pressure, whereby 12 g (690 / o) of the desired compound having a b.p. = 204-206 C / 1.0 mmHg are obtained.



  Analysis: calculated for C14H20O3N2 (264.32):
C 63.61% H 7.63% N 10.60% found: C 63.110 / o H 7.660 / 0 N 10.56%
Example 8
Preparation of N- (2-methoxy-benzoyl) -N 'methylglycine amide
This compound can be obtained from 2-methoxybenzamide and chloroacetic acid methylamide. The product obtained in 640% yield has a melting point = 98-99 ° C. When this compound is left to its own devices, it transforms into a polymorphic form with a m.p. = 113-114C.



  Analysis: calculated for CllHl403N2 (222.24):
C 59.45% H 6.35% N 12.60% found: C 59.59% H 6.49% N 12.45%
Example 9
Preparation of N- (2-methoxy-benzoyl) glycine piperidide
This compound, with a melting point = 97-98 ° C., (benzene-n-hexane) can be obtained from 2-methoxybenzamide and chloroacetic acid piperidide.



  Analysis: calculated for C15H20O3N2 (276.33):
C 65.19% H 7.30% N 10.14% found: C 65.25% H 7.41% N 9.95%
Example 10
Preparation of N- (2-methoxy-benzoyl) glycine morpholide
This compound, with a melting point = 114-1166 C (the compound contains 1 mol of water of crystallization), can be obtained from 2-methoxy-benzamide and chloroacetic acid morpholide.



  Analysis: calculated for C14H16O4N2 # H2O (296.32):
C 56.74% H 6.80% N 9.45% found: C 56.95% H 6.79% N 9.74%
Example 11
Preparation of N- (2-methoxy-benzoyl) -N ', N' dimethylalanine amide
This compound, with a melting point = 75-770 ° C. (the compound contains 1 mol of water of crystallization), can be obtained from 2-methoxybenzamide and a-bromopropionic acid dimethylamide.

Claims (1)

Analyse: berechnet für C13C18O5N2#H2O (268,31): C 58,19% H 7,51% N 10,44% gefunden: C 58,23% H 7,49% N 10,38% PATENTANSPRUCH Verfahren zur Herstellung von Benzamid-Abkömmlingen, die gegebenenfalls im Kern substituiert sind, und die Formel EMI3.1 aufweisen, in der R1 Wasserstoff, einen Alkyl- oder Alkoxyrest, R2 einen Alkylenrest und R3 einen mono- oder dialkylsubstituierten Aminrest oder ein cyclisches Amin, welches über das Stickstoffatom an die Carbonylgruppe gebunden ist, bedeuten, dadurch gekennzeichnet, dass die durch die Formel EMI3.2 dargestellte Verbindung mit einer Verbindung umgesetzt wird, die durch die Formel XROCOR, dargestellt wird, in der X Halogen bedeutet. Analysis: calculated for C13C18O5N2 # H2O (268.31): C 58.19% H 7.51% N 10.44% found: C 58.23% H 7.49% N 10.38% PATENT CLAIM Process for the preparation of benzamide derivatives, which are optionally substituted in the nucleus, and the formula EMI3.1 have in which R1 is hydrogen, an alkyl or alkoxy radical, R2 is an alkylene radical and R3 is a mono- or dialkyl-substituted amine radical or a cyclic amine which is bonded to the carbonyl group via the nitrogen atom, characterized in that the by the formula EMI3.2 is reacted with a compound represented by the formula XROCOR, in which X is halogen.
CH650160A 1959-06-11 1960-06-08 Process for the preparation of benzamide derivatives which are optionally substituted in the core CH387010A (en)

Applications Claiming Priority (4)

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JP1898359 1959-06-11
JP2805459 1959-09-01
JP3011259 1959-09-19
JP273660 1960-01-29

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CH650360A CH387011A (en) 1959-06-11 1960-06-08 Process for the production of salicylic acid derivatives
CH650160A CH387010A (en) 1959-06-11 1960-06-08 Process for the preparation of benzamide derivatives which are optionally substituted in the core
CH659060A CH393355A (en) 1959-06-11 1960-06-09 Process for the preparation of derivatives of benzamide

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011845A2 (en) * 1978-11-30 1980-06-11 Henkel Kommanditgesellschaft auf Aktien Antiseborrhoeic hair treatment composition

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5378729A (en) * 1985-02-15 1995-01-03 Research Corporation Technologies, Inc. Amino acid derivative anticonvulsant
US5654301A (en) * 1985-02-15 1997-08-05 Research Corporation Technologies, Inc. Amino acid derivative anticonvulsant
US4672059A (en) * 1985-06-10 1987-06-09 American Home Products Corporation N-[[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]-thioxomethyl and carbonyl]-N-methylglycinamides
JP4799794B2 (en) * 2000-03-21 2011-10-26 エミスフェアー・テクノロジーズ・インク A process for preparing alkylated salicylamides via dicarboxylated intermediates.
WO2005077122A2 (en) * 2004-02-11 2005-08-25 Irm Llc Compounds and compositions as lxr modulators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900576C (en) * 1942-12-18 1953-12-28 Geigy Ag J R Process for the preparation of acylated aliphatic aminocarboxamides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011845A2 (en) * 1978-11-30 1980-06-11 Henkel Kommanditgesellschaft auf Aktien Antiseborrhoeic hair treatment composition
EP0011845A3 (en) * 1978-11-30 1981-05-06 Henkel Kommanditgesellschaft auf Aktien Antiseborrhoeic hair treatment composition

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GB950281A (en) 1964-02-26
CH393355A (en) 1965-06-15
CH387011A (en) 1965-01-31
DE1185194B (en) 1965-01-14

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