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CH462136A - Procédé de préparation de dérivés de l'acide a-phényl-propionique - Google Patents

Procédé de préparation de dérivés de l'acide a-phényl-propionique

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Publication number
CH462136A
CH462136A CH1646367A CH1646367A CH462136A CH 462136 A CH462136 A CH 462136A CH 1646367 A CH1646367 A CH 1646367A CH 1646367 A CH1646367 A CH 1646367A CH 462136 A CH462136 A CH 462136A
Authority
CH
Switzerland
Prior art keywords
phenyl
propionic acid
acid
calculated
found
Prior art date
Application number
CH1646367A
Other languages
English (en)
Inventor
Stuart Nicholson John
Sanders Adams Stewart
Original Assignee
Boots Pure Drug 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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Publication of CH462136A publication Critical patent/CH462136A/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
    • C07C33/22—Benzylalcohol; phenethyl alcohol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/28—Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings
    • C07C33/30—Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/38—Alcohols containing six-membered aromatic rings and other rings and having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
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    • C07—ORGANIC CHEMISTRY
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    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
    • F16L3/00—Supports for pipes, cables or protective tubing, e.g. hangers, holders, clamps, cleats, clips, brackets
    • F16L3/14—Hangers in the form of bands or chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T24/00—Buckles, buttons, clasps, etc.
    • Y10T24/40—Buckles
    • Y10T24/4079—Sliding part of wedge
    • Y10T24/4084—Looped strap
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T24/00—Buckles, buttons, clasps, etc.
    • Y10T24/47—Strap-end-attaching devices

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description


  
 



  Procédé de préparation de dérivés de l'acide a-phényl-propionique
 La présente invention, qui est un développement de l'invention faisant l'objet du brevet principal, a pour objet un procédé de préparation de nouveaux dérivés de l'acide a-phényl-propionique, possédant des propriétés anti-inflammatoires, analgésiques et antipyrétiques.



   Ces nouveaux dérivés de l'acide a-phényl-propionique sont de formule:
EMI1.1     
 dans laquelle R représente un radical éthyle, n-propyle, isopropyle, n-butyle, n-pentyle, alcoyle ramifié   (C6-C7),    cycloalcoyle (C3-C5), alcoyloxy   (Ca-C4),    alcényloxy (C3
C4), alcoylthio   (C1-C5),    alcénylthio   (C3-CÏ),    cycloalcoyloxy (C3-C7), cycloalcoylthio (C3-C7), phénoxy, phénylthio ou alcényle   (C2. -C4).   



   Le procédé selon l'invention est caractérisé en ce que   l'on    transforme un ester d'un acide de formule générale:
EMI1.2     
 en le malonate correspondant par réaction avec du carbonate d'éthyle, en ce qu'on isole le malonate, en ce qu'on le méthyle, en ce qu'on isole l'ester méthylé, en ce qu'on hydrolyse les groupes ester au moyen d'un alcali, en ce qu'on décarboxyle l'acide malonique à environ   200OC,    et en ce qu'on cristallise l'acide phénylpropionique obtenu. Si désiré, on transforme l'acide libre en un sel.



   Ce procédé peut être mis en oeuvre de la manière décrite dans le brevet principal.



   Exemple
 On estérifie 59 g d'acide 4-n-propyl-phénylacétique avec 200   ml    d'alcool absolu et 6   ml    d'acide sulfurique concentré. On obtient 41 g d'ester, que   l'on    traite par 60   ml    de carbonate d'éthyle et de l'éthylate de sodium formé à partir de 5,7 g de sodium dans 117   ml    d'éthanol, et on chauffe. Lorsque l'alcool et le carbonate d'éthyle en excès ont distillé, on interrompt le chauffage et on ajoute de l'acide acétique glacial et de l'eau au mélange réactionnel agité et glacé. L'ester se sépare et on l'extrait à l'éther, on lave l'extrait avec une solution de carbonate de sodium et avec de l'eau et on le distille, obtenant ainsi le 4-n-propyl-phénylmalonate d'éthyle, p. éb. 1521540 C/2 mm.



   Trouvé: C   69,1;    H 7,5. Calculé pour   C,,H-,O,:   
C   69,0;    H 7,9    /o.   



   On ajoute 25 g de 4-n-propyl-phénylmalonate d'éthyle à une solution d'éthylate de sodium formée à partir de 2,1 g de sodium dans 80   ml    d'éthanol. On ajoute 14   ml    d'iodure de méthyle, on chauffe le mélange à reflux pendant deux heures et on chasse l'alcool par distillation
On extrait l'ester du mélange réactionnel refroidi au moyen d'éther, on lave l'extrait éthéré avec une solution de bisulfite de sodium, une solution de carbonate de sodium et avec de l'eau, on le sèche et on l'évapore. On chauffe à reflux l'huile résiduelle avec 60   ml    d'éthanol et   120ml    d'hydroxyde de sodium,   2,5 N    pendant une heure, on distille l'alcool, on recueille le sel de sodium résiduel, on le dissout dans de l'eau chaude et on acidule la solution.

   On recueille l'acide malonique substitué qui s'est séparé, on le lave à l'eau et on le sèche sous vide.



  On le chauffe à   180-200     C pendant 20 minutes pour le décarboxyler et on cristallise le résidu dans de l'éther de pétrole (p. éb.   40-600C)    glacé, obtenant ainsi l'acide 2-(4'-n-propyl-phényl)-propionique (p. f. 39-400C).  



   Trouvé: C   74,7;    H 8,6. Calculé pour C12H16O2 :
C   75,0;    H 8,3    /o.   



   Les composés suivants ont été préparés de manière semblable :
 Acide 2-(4'-isopropyl-phényl)-propionique, p. f. 67,569,50 C.



   Trouvé: C   75,2;    H 8,4. Calculé pour C12H16O2 :
C   75,0;    H 8,3    /o.   



   Acide 2- (4'-n-butyl-phényl) -propionique, p. éb.



  143 C/0,5 mm :
 Trouvé: C   76,6;    H 8,7. Calculé pour C13H18O2 :
C   75,8;    H 8,7    /o.   



   Acide 2-(4'-n-pentyl-phényl)-propionique, p. éb. 154155 C/1 mm :
 Trouvé: C   76,0;    H 9,15. Calculé pour C14H20O2 :
C 76,4 ; H 9,1 %.



   Acide 2- (4'-cyclopentyl-phényl)-propionique, p. f.



  103-104 C.



   Trouvé: C   77,0;    H 8,3. Calculé pour C14H18O2 :
C   77,0;    H 8,3 %.



   Acide 2-(4'-éthyl-phényl)-pripionique, p. f. 34,537,50 C.



   Trouvé: C   74,2;    H 8,0. Calculé pour C11H14O2 :
C   74,2;    H 7,9    /o.   



   Acide 2-(4'-phénoxy-phényl)-propionique, p. f. 69700 C.



   Trouvé: C   74,4;    H 5,8. Calculé pour C15H14O3 :
C   74,4;    H 5,8    /o.   



   Acide 2-[4'-(1",1"-diéthyl-éhyl)-phényl]-propionique, p. éb. 157-158 C/1,5 mm.



   Trouvé: C   76,8;    H 9,3. Calculé pour C15H22O2 :
C   77,0;    H 9,4    /o.   



   Acide   2-[4'-(1",1"- diéthyl-propyl)-phényl] -propioni-    que, p. éb. 1800 C/0,05 mm.



   Trouvé: C   77,8;    H 10,1. Calculé pour C16H24O2 :
C   77,4;    H 9,7    /o.   



   Acide 2-(4'-phénylthio-phényl)-propionique, p. f. 9091 C.



   Trouvé: C   69,2;    H 5,6. Calculé pour C15H14O2S :
C 69,8 ; H 5,4 %.



   Acide 2-[4'-(1",1"-diméthyl-butyl)-phényl]-propionique, p. f. 82-84,5  C.



   Trouvé: C   77,1;    H 9,5. Calculé pour C15H22O2 :
C 76,9 ; H 9,4 %.



   Acide 2-(4'-allyloxy-phényl)-propionique, p. f. 47,5490 C.



   Trouvé: C   70,4;    H 7,0. Calculé pour C12H14O8 :
C 69,9 ; H 6,8 %.



   Acide 2-[4'-but-2"-ényloxy)-phényl]-propionique, p. f. 61,5-65  C.



   Trouvé: C   70,9;    H 7,4. Calculé pour C13H16O3 :
C 70,9 ; H 7,3 %.



   Acide 2-(4'-isopropoxy-phényl)-propionique. p. f.



  73,5-76,5 C.



   Trouvé: C 69,3 ; H 7,8. Calculé pour C12H16O2 :
C   69,25;    H 7,7 %.



   Acide 2-(4'-propylthio-phényl)-pripionique, p. éb.



  158-1600   C/0,2mm.   



   Trouvé: C   64,4;    H   7,3;    S 14,1. Calculé pour
C12H10O2S : C 64,3 ; H 7,1 ; S 14,3 %.



   Acide 2-(4'-n.propoxy-phényl)-propionique, p. f. 5859,50 C.



   Acide 2-(4'-n.butoxy-phényl)-propionique, p. éb.



  143 C/0,15 mm.

Claims (1)

  1. REVENDICATION Procédé de préparation des composés de formule: EMI2.1 dans laquelle R représente un radical éthyle, n-propyle, isopropyle, n-butyle, n-pentyle, alcoyle ramifié (C6-C7), cycloalcoyle (C3-C5), alcoyloxy (C3-C4), alcényloxy (C3 C4), alcoylthio (C1-C5), alcénylthio (C3-C5), cycloalcoyloxy (Cs-C7), cycloalcoylthio (C3-C7), phénoxy, phénylthio ou alcényle (C2-C4), caractérisé en ce que l'on transforme un ester d'un acide de formule générale: EMI2.2 en le malonate correspondant par réaction avec du carbonate d'éthyle, en ce qu'on isole le malonate, en ce qu'on le méthyle, en ce qu'on isole l'ester méthylé, en ce qu'on hydrolyse les groupes ester au moyen d'un alcali, en ce qu'on décarboxyle l'acide malonique à environ 2000 C, et en ce qu'on cristallise l'acide phénylpropionique obtenu.
    SOUS-REVENDICATION Procédé selon la revendication, caractérisé en ce que l'on transforme l'acide obtenu en un sel en le faisant réagir avec une base inorganique ou organique.
CH1646367A 1961-02-02 1963-07-26 Procédé de préparation de dérivés de l'acide a-phényl-propionique CH462136A (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB399961A GB971700A (en) 1961-02-02 1961-02-02 Anti-Inflammatory Agents

Publications (1)

Publication Number Publication Date
CH462136A true CH462136A (fr) 1968-09-15

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Family Applications (3)

Application Number Title Priority Date Filing Date
CH21266A CH444137A (fr) 1961-02-02 1962-02-02 Procédé de préparation de dérivés de l'acide a-phényl-propinoique
CH132762A CH425755A (fr) 1961-02-02 1962-02-02 Procédé de préparation d'agents anti-inflammatoires
CH1646367A CH462136A (fr) 1961-02-02 1963-07-26 Procédé de préparation de dérivés de l'acide a-phényl-propionique

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Application Number Title Priority Date Filing Date
CH21266A CH444137A (fr) 1961-02-02 1962-02-02 Procédé de préparation de dérivés de l'acide a-phényl-propinoique
CH132762A CH425755A (fr) 1961-02-02 1962-02-02 Procédé de préparation d'agents anti-inflammatoires

Country Status (7)

Country Link
US (2) US3228831A (fr)
CH (3) CH444137A (fr)
DE (1) DE1443429C3 (fr)
DK (2) DK116277B (fr)
FR (1) FR1512834A (fr)
GB (1) GB971700A (fr)
SE (2) SE305208B (fr)

Families Citing this family (173)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053639A (en) * 1964-01-24 1977-10-11 The Boots Company Limited Therapeutically active phenylalkane derivatives
US3526653A (en) * 1964-06-15 1970-09-01 Merck & Co Inc Phenylacetamides
US3457300A (en) * 1965-06-11 1969-07-22 Merck & Co Inc Acetic acid type compounds
SE363818B (fr) * 1968-08-15 1974-02-04 Lilly Co Eli
US3919304A (en) * 1968-10-25 1975-11-11 Ciba Geigy Corp {62 -Hydroxy-{62 -(cycloalkenylphenyl)alkanoic acids, esters and salts
GB1245711A (en) * 1969-01-13 1971-09-08 Allen & Hanburys Ltd Phenethyl alcohols
US3876800A (en) * 1969-05-12 1975-04-08 Clin Midy Pharmaceutical compositions and methods for treating inflammation and pain
US4062895A (en) * 1969-05-28 1977-12-13 Eli Lilly And Company 2-(3-Phenoxyphenyl) propanol
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US3228831A (en) 1966-01-11
CH444137A (fr) 1967-09-30
DK116277B (da) 1969-12-29
SE305208B (fr) 1968-10-21
DE1443429A1 (de) 1968-10-24
DK115394B (da) 1969-10-06
SE305214B (fr) 1968-10-21
DE1443429C3 (de) 1975-07-31
FR1512834A (fr) 1968-02-09
DE1443429B2 (de) 1974-11-07
GB971700A (en) 1964-09-30
CH425755A (fr) 1966-12-15
FR3124M (fr) 1965-02-15
US3385886A (en) 1968-05-28

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