DE2250327C2 - Phenoxyibuttersäurederivate, ihre Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutische Mittel - Google Patents

Phenoxyibuttersäurederivate, ihre Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutische Mittel

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Publication number
DE2250327C2
DE2250327C2 DE2250327A DE2250327A DE2250327C2 DE 2250327 C2 DE2250327 C2 DE 2250327C2 DE 2250327 A DE2250327 A DE 2250327A DE 2250327 A DE2250327 A DE 2250327A DE 2250327 C2 DE2250327 C2 DE 2250327C2
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Germany
Prior art keywords
acid
addition salts
preparation
phenoxyibutyric
processes
Prior art date
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Expired
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DE2250327A
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DE2250327A1 (de
Inventor
Andre Lausanne Mieville
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Innophar Gesellschaft fur Pharmaforschung und Inn
Original Assignee
Caf Chemischer Arzneimittelvertrieb 6600 Saarbruecken De GmbH
Caf Chemischer Arzneimittelvertrieb 6600 Saarbruecken GmbH
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Priority claimed from CH151769A external-priority patent/CH515873A/fr
Priority claimed from CH1302269A external-priority patent/CH543472A/fr
Priority claimed from GB4792771A external-priority patent/GB1415295A/en
Application filed by Caf Chemischer Arzneimittelvertrieb 6600 Saarbruecken De GmbH, Caf Chemischer Arzneimittelvertrieb 6600 Saarbruecken GmbH filed Critical Caf Chemischer Arzneimittelvertrieb 6600 Saarbruecken De GmbH
Publication of DE2250327A1 publication Critical patent/DE2250327A1/de
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Publication of DE2250327C2 publication Critical patent/DE2250327C2/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • 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
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • 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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • 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
    • 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
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
    • 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
    • C07C59/74—Unsaturated compounds containing —CHO groups
    • 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
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • 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
    • 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
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C8/00—Solid state diffusion of only non-metal elements into metallic material surfaces; Chemical surface treatment of metallic material by reaction of the surface with a reactive gas, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C8/06—Solid state diffusion of only non-metal elements into metallic material surfaces; Chemical surface treatment of metallic material by reaction of the surface with a reactive gas, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using gases
    • C23C8/08—Solid state diffusion of only non-metal elements into metallic material surfaces; Chemical surface treatment of metallic material by reaction of the surface with a reactive gas, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using gases only one element being applied
    • C23C8/10—Oxidising
    • C23C8/12—Oxidising using elemental oxygen or ozone
    • C23C8/14—Oxidising of ferrous surfaces
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C8/00—Solid state diffusion of only non-metal elements into metallic material surfaces; Chemical surface treatment of metallic material by reaction of the surface with a reactive gas, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C8/80—After-treatment

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

mit R = H, Methyl, Äthyl, Isoprcpyl, Diäthylaminoäthyl, Piperidinoäthyl, Morpholinoäthyl, to
-CH2-CH2-N J
oder
-CH2
und ihre Säureadditionssalze.
2. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß in an sich bekannter Weise 4-Hydroxy-4'-chIorbenzo-
mit einer a-Halogenisobuttersäure der allgemeinen Formel
X-C(CHj)2-COOH
in der X ein Halogenatom bedeutet,
oder einem entsprechenden Ester in alkalischem Medium umgesetzt und die Carboxylgruppe gegebenenfalls verestert wird und die so erhaltenen Verbindungen ggfs. in ihre Säureadditionssalze übergeführt werden.
3. Pharmazeutische Mittel, gekennzeichnet durch eine Verbindung nach Anspruch 1 zusammen mit pharmazeutisch üblichen Hilfs- und/oder Trägerstoffen.
Die Erfindung betrifft den Gegenstand der Ansprüche.
Die erfindungsgemäßen Verbindungen sind pharmazeutisch wirksam und lassen sich in der Humantherapie vorteilhaft zur Senkung des Cholesterinspiegels im Serum einsetzen.
Die erfindungsgemäßen pharmazeutischen Mittel enthalten eine wirksame Menge einer Verbindung der allgemeinen Formel I oder eines ihrer nichttoxischen j 5 Säureadditionssalze neben pharmazeutisch geeigneten Hilfs- und Trägerstoffen.
Die folgenden Beispiele erläutern die Herstellung der erfindungsgemäßen Verbindungen.
Cl-
Beispiel 1
4-ip-Chlorbenzoyl)-phenoxyisobuttersäure (Verbindung 1)
O V-0 — C(CH3),
CO
1 Mol 4-Hydroxy-4'-chlorbenzophenon wird in wasserfreiem Aceton gelöst. Zu der Lösung werden 5 Mol gepulvertes Natriumhydroxid hinzugegeben, worauf das Phenolat ausfällt. Man erhitzt am Rückfluß und gibt !,5 Mol CHCIj, verdünnt in wasserfreiem Aceton, hinzu. Nach Beendigung der Zugabe wird 10 Stunden lang am Rückfluß erhitzt; nach dem Abkühlen wird Wasser zugesetzt und das Aceton i>,rdampft. Die mit Äther gewaschene wässerige Phase wird angesäuert; d.is erhaltene Öl wird in Äther aufgenommen und mit einer Hydrogencarbonatlösung extrahiert. Durch Ansäuern wird die gewünschte Säure erhalten.
Ausbeute: 75%.
Cl-
Beispiel 2
4-(p-Chlorbenzoyl)-phenoxyisobuttersäureiso-
propylester — lsopropyl-4-(p-Chlorbenzoyl)-
phenoxyisobutyrat (Verbindung 4)
O V-O-C(CHjJ2-CO-O-CH(CHj)2
CO
Die nach Beispiel 1 erhaltene Säure (1 Mol) wird mit 65 einem inerten Lösungsmittel wie Benzol kondensiert. Thionylchlorid (2,5 Mol) in das Säurechlorid umgewan- In der nachstehenden Tabelle 1 sind Verbindungen
delt. I Mol des Säurechlorids wird dann mit 1,05 Mol angeführt, die nach Beispiel I bzw. 2 erhalten wurden. Isopropanol in Gegenwart von 0,98 Mol Pyridin in
Tabelle 1 Eigenschaften erfindungsgemäßer Verbindungen der Formel
-CO
O V-O-C(CHj)2-CO-O-R
Ver- R bindung
Nr.
(0C)
IR-Spektrum
i'co
(Keto) i'co
(Carboxy)
UV-Spektrum (nm)
Pharmakolngrche Wirkung
1 H
CH,
•ä.
1 		3 C2H5
4 i-C,H7
5 CH2-CH2-N
1640 1710
1660 1740
79 1665 1735
78 1650 1730
120 1650 1745
C2H,
6 CH2-CH2-N 104 1650 1730
\
C2H5
7 CH2-CH2-N J 116 1645 1730 (Fumarat) ^—'
(Hydrochlorid)
CH2-CH2-N (Hydrochlorid)
144
O 145
1660
1645
1740
1740
259
294
207
284
208
2S5
207
286
207
285
206
286
259
285
208
286
13 000
17 000
13 000 12 000
19 000
18 000
19 500 18 000
33 000 16000
22 000 17500
208 26 000 284 14 000
20000 19000
20 000 16 000
Senkung des Cholesteringehalts im Serum
desgl.
desgl. desgl. desgl.
desgl.
01,SgI.
desgl. desgl.
Da bei der Herstellung des Säurechlorids mit Thionylchlorid bisweilen SO2-Spuren im Produkt verbleiben, die zu einem schlechten Geruch führen, kann zur Vermeidung dieses Nachteils auch direkt verestert werden.
Pharmakologische Untersuchungen
Die pharmakologische Wirksamkeit der erfindungsgemäßen Verbindungen 1 bis 9 gegenüber Vergleichsverbindungen wurde im Hinblick auf die Senkung des Cholesterinspiegels im Serum an Ratten untersucht, wobei nach Sornay et al. Arzneimittel-Forschung, 26 (1976), 885 - 889, verfahren wurde.
Als Vergleichsverbindungen dienten
60 2-(4-BenzoyIphenoxy)-2-methylpropionsäure = 2-(4-Benzoylphenoxy)-isobuttersäure, nach der DE-PS 20 03 430 (Vergleichsverbindung A),
2-(4-Benzoylphenoxy)-2-methylpropionsäuremethylester = 2-(4-Benzoylphenoxy)-isobuttersäure, nach der DE-PS 20 03 430 (Vergleichsverbindung B) und
^-^-ChlorphenoxyJ^-methylpropionsäureäthylester = 2-(4-Chlorphenoxy)-isobuttersäureäthylester, Clofibrat (Vergleichsverbindung C).
Die Verbindungen wurden oral verabreicht. Die erhaltenen Ergebnisse sind in Tabelle zusammengefaßt.
22 50 327 Therapeu
Tabelle 2 tischer Index
Verbindung LD;,, EDt1, U-D511ZED;,,,)
(mg/kg) (mg/kg)
Erfindungsgemüße 96
Verbindung 43
1 2400 25 58
2 3200 75 64
3 3200 55 35
4 3200 50 30
5 2250 65 34
6 2400 80 28
7 2350 70 51
8 1800 65
9 3200 63
Vergleichsverbindung
A >32OO 180 >18
B > 3200 > 300 -11
C 3200 165 19
* Dosis, die ötn Che'.esterinspiegel um 30% senkt.
Die Ergebnisse zeigen, daß die erfindungsgemäßen Verbindungen einen günstigeren therapeutischen Index als die Vergleichsverbindungen besitzen.

Claims (1)

  1. Patentansprüche: . 4-(p-Chlorbenzoyl)-phenoxyisobuttersäure und ihre Ester der allgemeinen Formel
    O —C(CHj)2-CO-O-R
    phenon der Formel
    ei—<T ο >—co
    CO-
DE2250327A 1969-01-31 1972-10-13 Phenoxyibuttersäurederivate, ihre Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutische Mittel Expired DE2250327C2 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH151769A CH515873A (fr) 1969-01-31 1969-01-31 Procédé de préparation de composés dérivés de l'acide phénoxy-alkyl-carboxylique
CH1302269A CH543472A (fr) 1969-01-31 1969-08-28 Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques
GB4792771A GB1415295A (en) 1971-10-14 1971-10-14 Substituted phenoxy-alkyl-carboxylic acids and derivatives thereof
GB4792671 1971-10-14

Publications (2)

Publication Number Publication Date
DE2250327A1 DE2250327A1 (de) 1973-04-26
DE2250327C2 true DE2250327C2 (de) 1982-07-01

Family

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DE2003430A Expired DE2003430C3 (de) 1969-01-31 1970-01-27 p-Benzoylphenoxyisobuttersäureester, ihre Herstellung und diese enthaltende Arzneimittel
DE2250327A Expired DE2250327C2 (de) 1969-01-31 1972-10-13 Phenoxyibuttersäurederivate, ihre Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutische Mittel

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DE2003430A Expired DE2003430C3 (de) 1969-01-31 1970-01-27 p-Benzoylphenoxyisobuttersäureester, ihre Herstellung und diese enthaltende Arzneimittel

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DE (2) DE2003430C3 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
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JPS5195049A (en) * 1975-02-12 1976-08-20 * **********so*****no***tsu*****************************************ni*no
GB1563195A (en) * 1975-08-20 1980-03-19 Sori Soc Rech Ind Derivating of phenoxy-alkylcarboxylic acids
GB1548777A (en) 1976-12-27 1979-07-18 Kaken Chemical Co Benzoyl phenoxy acetic acid derivatives
NL7903434A (nl) * 1978-05-09 1979-11-13 Alfa Farmaceutici Spa Derivaten van benzoylfenoxyalkaancarbonzuren met anti- lipemische en anticholesterolemische werking, alsmede farmaceutische preparaten die zo'n verbinding bevatten.
US4661505A (en) * 1982-11-03 1987-04-28 Eli Lilly And Company Leukotriene antagonists
US4782176A (en) * 1983-01-24 1988-11-01 Hoffmann-La Roche Inc. Phenoxycarboxylic acids
US4537984A (en) * 1983-05-19 1985-08-27 Nissan Chemical Industries Ltd. Process for producing 2-(4-hydroxyphenoxy) propionate derivatives
US5008439A (en) * 1988-03-21 1991-04-16 Hoechst Celanese Corporation Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters
US4935522A (en) * 1988-03-21 1990-06-19 Hoechst Celanese Corporation Process for producing ethyl 2-[4'-(6"-chloro-2"-benzoxazolyloxy)phenoxy]propionate
US4908476A (en) * 1988-03-21 1990-03-13 Hoechst Celanese Corporation Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids
GB9603127D0 (en) * 1996-02-15 1996-04-17 Rhone Poulenc Agriculture New process for preparing intermediates
US6083497A (en) 1997-11-05 2000-07-04 Geltex Pharmaceuticals, Inc. Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers
TW200637803A (en) 2005-01-13 2006-11-01 Wyeth Corp Processes for the preparation of aminoethoxybenzyl alcohols
WO2008035359A2 (en) * 2006-06-12 2008-03-27 Cadila Healthcare Limited Oximinophenoxyalkanoic acid and phenylalkanoic acid derivatives
WO2009024685A1 (fr) * 2007-07-05 2009-02-26 Finorga Procede de preparation du fenofibrate
EP2864309A1 (de) * 2012-06-25 2015-04-29 Cadila Healthcare Limited Verbindungen zur behandlung von dyslipidämie und anderen erkrankungen
US20200190043A1 (en) * 2017-06-19 2020-06-18 Basf Se 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi

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DE2003430A1 (de) 1970-09-03
DE2003430B2 (de) 1978-03-16
BE790026R (fr) 1973-02-01
DE2250327A1 (de) 1973-04-26
DE2003430C3 (de) 1978-12-07

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