CH510018A - Antiphlogistic, antipyretic halo-cinnamamides - Google Patents

Antiphlogistic, antipyretic halo-cinnamamides

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Publication number
CH510018A
CH510018A CH342771A CH342771A CH510018A CH 510018 A CH510018 A CH 510018A CH 342771 A CH342771 A CH 342771A CH 342771 A CH342771 A CH 342771A CH 510018 A CH510018 A CH 510018A
Authority
CH
Switzerland
Prior art keywords
acid
formula
piperidide
antiphlogistic
cinnamic acid
Prior art date
Application number
CH342771A
Other languages
German (de)
Inventor
Manfred Dr Kleemann
Wolfgang Dr Grell
Gerhard Dr Dahms
Hans Dr Machleidt
Albrecht Dr Eckenfels
Original Assignee
Thomae Gmbh Dr K
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
Priority claimed from AT1091167A external-priority patent/AT280283B/en
Priority claimed from AT1075568A external-priority patent/AT281821B/en
Priority claimed from AT1075768A external-priority patent/AT285606B/en
Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K
Priority claimed from CH1780868A external-priority patent/CH510662A/en
Publication of CH510018A publication Critical patent/CH510018A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/72—Acyl halides containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/224—Phosphorus triamides
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4056—Esters of arylalkanephosphonic acids
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/535—Organo-phosphoranes
    • C07F9/5352—Phosphoranes containing the structure P=C-
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5456—Arylalkanephosphonium compounds
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings

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  • 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)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Title amides of formula (I): (where R1 is Br or I and R2 is piperidino or morpholino), which have antiphlogistic and antipyretic activity, are prepd. by reacting an R1 substd. benzaldehyde with a cpd. of formula (II): (where Y is alkoxy, alkylthio or R2) and subsequently with an acid.

Description

  

  
 



  Verfahren zur Herstellung neuer Zimtsäureamide
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Zimtsäureamide der Formel I
EMI1.1     
 worin R1 ein Brom- oder Jodatom und    R5    einen Piperidino- oder Morpholinorest bedeuten, das dadurch gekennzeichnet ist, dass man einen Aldehyd der Formel II
II
EMI1.2     
 mit einer Verbindung der Formel III
EMI1.3     
 worin Y eine Alkoxy- oder Alkylthiogruppe darstellt oder die gleiche Bedeutung wie der Rest R2 besitzt und anschliessend mit einer Säure umsetzt.



   Die Umsetzung erfolgt vorteilhafterweise in einem   Lö    sungsmittel, z.B. Benzol oder Toluol, unter Erwärmen, z.B. auf die Siedetemperatur des verwendeten Lösungsmittels. Anschliessend wird das Kondensationsprodukt mittels einer Säure, z.B. Eisessig oder Schwefelsäure, zweckmässigerweise bei 50 bis   1100C,    in eine Verbindung der Formel I überführt.



   Die bei dem Verfahren verwendeten Ausgangsstoffe sind teilweise neu und lassen sich nach bekannten Methoden darstellen. So lässt sich beispielsweise ein Ketenacetal der Formel III durch Umsetzung eines entsprechenden Essigsäureamids mit Dimethylsulfat und anschliessender Behandlung mit Alkoholat und Calcium, durch Umsetzung eines Orthoessigsäureesters mit einem entsprechenden Amin oder durch Methylierung eines entsprechenden Thioessigsäureamids mit Methyljodid und anschliessende Umsetzung mit Alkoholat herstellen.



   Die erfindungsgemäss hergestellten neuen Zimtsäureamide der Formel I besitzen wertvolle pharmakologische Eigenschaften, insbesondere eine antiphlogistische und antipyretische Wirkung.



   Im Kaolin- und Carrageenin-ödem-Test an der Ratte sind die Verbindungen der Formel I dem Phenylbutazon bezüglich der therapeutischen Breite überlegen.



   Die nachstehenden Beispiele dienen zur näheren Erläuterung der Erfindung:
Beispiel I
4-Brom-zimtsäurepiperidid
10,3 g (0,065   Mol) -l-Piperidino-l-methylmercapto-    -äthylen (Kp.:   ,      91-920C,    hergestellt aus Thioessigsäurepiperidid, Methyljodid und Kalium-tert.-butylat) und
11,8 g (0,064 Mol) 4-Brombenzaldehyd werden getrennt in je 30 ml Benzol gelöst. Man gibt die Lösungen zusammen, dampft i. Vak. ein und erhitzt das öl 2 Stunden auf    100 C.    Anschliessend wird das Kondensationsprodukt in 40 ml Eisessig 2 Stunden zum Sieden erhitzt. Man entfernt das Lösungsmittel i. Vak., behandelt den Rückstand mit Äther und erhält 2,0 g (11% d. Th.) 4-Brom-zimtsäurepiperidid vom Fp.   132-1340C.    Als Säure kann auch konzentrierte Schwefelsäure bei 20 - 500C verwendet werden.  



   Beispiel 2    4-Broii-zitiitsättrepiperidid   
Zu einer ösung von 10,0 g (0,054 Mol) 4-Brombenzaldehyd in 150 ml absolutem Toluol werden bei 200C 10,5 g (0,054 Mol)   1,1 -Dipiperidino.äthylen    (Kp.: 10   120-1220C,    hergestellt aus Orthoessigsäureäthylester und Piperidin) getropft. Man erhitzt 1 Stunde zum Sieden, dampft i. Vak.



  ein, löst den Rückstand in 180 ml Eisessig und erhitzt erneut 3 Stunden unter Rückfluss. Der Eisessig wird i.



  Vak. entfernt. Man löst das zurückbleibende öl in Essigester und extrahiert mit verd. Salzsäure, verd. Natronlauge und Wasser. Aus der Essigester-Lösung werden 2,2 g   14thC    d. Th.) 4-Brom-zimtsäurepiperidid vom Fp. 133 1340C (aus Methanol) erhalten.



   Beispiel 3    4-Brotn-zimtsäurepiperidid   
2,0 g   (1,3    m Mol)   1-PiDeridino-1-äthoxy-äthylen    (Kp.:   86-900C,    hergestellt aus Essigsäurepiperidid, Dimethyl sulfat, Natriumäthylat und nachfolgender Behandlung mit Calcium) und 2,4 g (1,3 m Mol) 4-Brombenzaldehyd werden in 30 ml absolutem Toluol 3 Stunden unter Rückfluss erhitzt. Man dampft i. Vak. ein und löst den Rückstand in 40 ml Eisessig. Nach 4stündigem Erhitzen auf   1100C    wird wieder i. Vak. eingedampft. Das zurückbleibende Reaktionsrohprodukt wird in Methylenchlorid aufgenommen. Man schüttelt die Lösung mit Wasser, verd.



  Natronlauge und verd. Salzsäure, trocknet über Natriumsulfat und engt i. Vak. ein. Säulenschromatographie an Kieselgel (Benzol/Aceton = 9 . 1) liefert 110 mg   (3qfO    d. Th.) 4-Brom-zimtsäurepiperidid vom   Fp.    131 - 1330C.



   Analog wurden folgende Verbindungen hergestellt:
3-Brom-zimtsäurepiperidid, Fp. 95 - 990C
4-Brom-zimtsäuremorpholid,   Fp.      142 - l440C   
3-Brom-zimtsäuremorpholid, Fp. 80 - 810C
4-Jod-zimtsäurepiperidid, Fp.   134 - 1350C   
3-Jod-zimtsäurepiperidid, Fp.   109 - 1 100C   
4-Jod-zimtsäuremorpholid, Fp. 175 -   177ob   
3-Jod-zimtsäuremorpholid, Fp.   100 - 101 oC   
Die erfindungsgemäss hergestellten Verbindungen der Formel I lassen sich nach an sich bekannten Methoden in übliche pharmazeutische Anwendungsformen, gegebenenfalls in Kombination mit anderen Wirksubstanzen, einarbeiten. 

  Die Einzeldosis beträgt bei Erwachsenen 200,00 mg -   60G,00    mg, bevorzugt 300,00 mg - 400,00 mg und die Tagesdosis 400,00 mg -   1 200,00    mg, bevorzugt 600,00 mg - 800,00 mg. 



  
 



  Process for the production of new cinnamic acid amides
The invention relates to a process for the preparation of new cinnamic acid amides of the formula I.
EMI1.1
 wherein R1 is a bromine or iodine atom and R5 is a piperidino or morpholino radical, which is characterized in that an aldehyde of the formula II
II
EMI1.2
 with a compound of the formula III
EMI1.3
 wherein Y represents an alkoxy or alkylthio group or has the same meaning as the radical R2 and then reacts with an acid.



   The reaction is advantageously carried out in a solvent, e.g. Benzene or toluene, with heating, e.g. on the boiling point of the solvent used. The condensation product is then removed by means of an acid, e.g. Glacial acetic acid or sulfuric acid, conveniently at 50 to 110C, converted into a compound of the formula I.



   Some of the starting materials used in the process are new and can be prepared using known methods. For example, a ketene acetal of the formula III can be prepared by reacting a corresponding acetic acid amide with dimethyl sulfate and subsequent treatment with alcoholate and calcium, by reacting an orthoacetic acid ester with a corresponding amine or by methylating a corresponding thioacetic acid amide with methyl iodide and subsequent reaction with alcoholate.



   The new cinnamic acid amides of the formula I prepared according to the invention have valuable pharmacological properties, in particular an anti-inflammatory and anti-pyretic effect.



   In the kaolin and carrageenin edema test on rats, the compounds of the formula I are superior to phenylbutazone with regard to the therapeutic range.



   The following examples serve to explain the invention in more detail:
Example I.
4-bromo-cinnamic acid piperidide
10.3 g (0.065 mol) -l-piperidino-l-methylmercapto-ethylene (bp .: 91-920C, prepared from thioacetic acid piperidide, methyl iodide and potassium tert-butoxide) and
11.8 g (0.064 mol) of 4-bromobenzaldehyde are dissolved separately in 30 ml of benzene each time. The solutions are combined, i evaporated. Vac. and the oil is heated to 100 ° C. for 2 hours. The condensation product is then heated to boiling for 2 hours in 40 ml of glacial acetic acid. The solvent is removed i. Vac., Treats the residue with ether and receives 2.0 g (11% of theory) of 4-bromocinnamic acid piperidide of melting point 132-1340C. Concentrated sulfuric acid at 20 - 500C can also be used as the acid.



   Example 2 4-Broii Citiitsaturate Repiperidide
To a solution of 10.0 g (0.054 mol) of 4-bromobenzaldehyde in 150 ml of absolute toluene, 10.5 g (0.054 mol) of 1,1-Dipiperidino.äthylen (boiling point: 10 120-1220C, prepared from ethyl orthoacetate) are added at 200C and piperidine). The mixture is heated to boiling for 1 hour, evaporated i. Vac.



  a, dissolve the residue in 180 ml of glacial acetic acid and reflux for 3 hours. The glacial acetic acid is i.



  Vac. away. The oil that remains is dissolved in ethyl acetate and extracted with dilute hydrochloric acid, dilute sodium hydroxide solution and water. From the ethyl acetate solution, 2.2 g of 14thC d. Th.) 4-Bromo-cinnamic acid piperidide of melting point 133 1340C (from methanol).



   Example 3 4-Bread Cinnamic Acid Piperidide
2.0 g (1.3 m mol) of 1-PiDeridino-1-ethoxy-ethylene (Kp .: 86-900C, made from acetic acid piperidide, dimethyl sulfate, sodium ethylate and subsequent treatment with calcium) and 2.4 g (1, 3 m mol) of 4-bromobenzaldehyde are heated under reflux for 3 hours in 30 ml of absolute toluene. One steams i. Vac. and dissolve the residue in 40 ml of glacial acetic acid. After 4 hours of heating at 1100C again i. Vac. evaporated. The remaining crude reaction product is taken up in methylene chloride. The solution is shaken with water, dil.



  Sodium hydroxide solution and dilute hydrochloric acid, dried over sodium sulfate and concentrated i. Vac. one. Column chromatography on silica gel (benzene / acetone = 9.1) gives 110 mg (3% of theory) of 4-bromocinnamic acid piperidide with a melting point of 131-1330C.



   The following connections were made in the same way:
3-Bromo-cinnamic acid piperidide, m.p. 95-990C
4-Bromo-cinnamic acid morpholide, m.p. 142-1440C
3-Bromo-cinnamic acid morpholide, m.p. 80-810C
4-iodo-cinnamic acid piperidide, m.p. 134-1350C
3-iodo-cinnamic acid piperidide, m.p. 109-1100C
4-iodo-cinnamic acid morpholide, m.p. 175-177ob
3-iodo-cinnamic acid morpholide, melting point 100-101 oC
The compounds of the formula I prepared according to the invention can be incorporated into customary pharmaceutical application forms by methods known per se, optionally in combination with other active substances.

  The single dose for adults is 200.00 mg - 60G.00 mg, preferably 300.00 mg - 400.00 mg and the daily dose 400.00 mg - 1200.00 mg, preferably 600.00 mg - 800.00 mg.

Claims (1)

PATENTANSPRUCH PATENT CLAIM Verfahren zur Herstellung neuer Zimtsäureamide der Formel 1 (1) EMI2.1 worin R1 ein Brom- oder Jodatom und R einen Piperidino- oder Morpholinorest bedeuten, dadurch gekennzeichnet, dass man einen Aldehyd der Formel II (11) EMI2.2 mit einer Verbindung der Formel III EMI2.3 worin Y eine Alkoxy- oder Alkylthiogruppe darstellt oder die gleiche Bedeutung wie der Rest R besitzt und anschliessend mit einer Säure umsetzt. Process for the preparation of new cinnamic acid amides of the formula 1 (1) EMI2.1 wherein R1 is a bromine or iodine atom and R is a piperidino or morpholino radical, characterized in that an aldehyde of the formula II (11) EMI2.2 with a compound of the formula III EMI2.3 wherein Y represents an alkoxy or alkylthio group or has the same meaning as the radical R and then reacts with an acid. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in einem Lösungsmittel durchführt. SUBCLAIMS 1. The method according to claim, characterized in that the reaction is carried out in a solvent. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 4-Bromzimtsäurepiperidid herstellt. 2. The method according to claim, characterized in that 4-bromocinnamic acid piperidide is produced. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 3-Bromzimtsäurepiperidid herstellt. 3. The method according to claim, characterized in that 3-bromocinnamic acid piperidide is produced. 4. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 4-Jodzimtsäurepiperidid herstellt. 4. The method according to claim, characterized in that 4-iodocinnamic acid piperidide is produced. 5. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 4-Jodzimtsäuremorpholid herstellt. 5. The method according to claim, characterized in that 4-iodocinnamic acid morpholide is prepared.
CH342771A 1967-12-01 1968-11-29 Antiphlogistic, antipyretic halo-cinnamamides CH510018A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AT1091167A AT280283B (en) 1967-12-01 1967-12-01 Process for the preparation of new cinnamic acid amides
AT1075568A AT281821B (en) 1968-11-05 1968-11-05 Process for the production of new cinnamic acid amides
AT1075768A AT285606B (en) 1968-11-05 1968-11-05 Process for the production of new cinnamic acid amides
CH1780868A CH510662A (en) 1967-12-01 1968-11-29 Cinnamic acid amides antiinflammatory antipyretic

Publications (1)

Publication Number Publication Date
CH510018A true CH510018A (en) 1971-07-15

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CH342771A CH510018A (en) 1967-12-01 1968-11-29 Antiphlogistic, antipyretic halo-cinnamamides

Country Status (1)

Country Link
CH (1) CH510018A (en)

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