AT401514B - Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden - Google Patents

Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden Download PDF

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Publication number
AT401514B
AT401514B AT0042192A AT42192A AT401514B AT 401514 B AT401514 B AT 401514B AT 0042192 A AT0042192 A AT 0042192A AT 42192 A AT42192 A AT 42192A AT 401514 B AT401514 B AT 401514B
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Prior art keywords
general formula
adamantyl
acid
radical
preparation
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AT0042192A
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English (en)
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ATA42192A (de
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Braham Shroot
Jacques Ing Eustache
Jean-Michel Bernardon
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Cird Galderma
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Furan Compounds (AREA)

Description


   <Desc/Clms Page number 1> 
 



   Gegenstand der vorliegenden Erfindung Ist ein Verfahren zur Herstellung von neuen Verbindungen der allgemeinen Formel 
 EMI1.1 
 wenn Ar einen Rest der allgemeinen Formel 
 EMI1.2 
 
 EMI1.3 
    in welcher R61-Methylcyclohexyl   oder 1-Adamantyl bedeutet und Q OH oder Cl ist, insbesondere von   3- (1-Adamantyl) -4-   decyloxybenzoesäure, 3-(1-Adamantyl)-4-methoxybenzoesäure und 3-(1,1-Dimethyldecyl)-4-methoxybenzoesäure und den entsprechenden Säurechloriden. 



   Diese Säuren bzw. Säurechloride können als Ausgangssubstanzen für die Herstellung neuer, therapeutisch wertvoller Stoffe verwendet werden. 



   Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass nach Bildung des   Magneslumderrva-   
 EMI1.4 
 entsprechende Säurechlorid zu erhalten. 



   Die erfindungsgemäss hergestellten Säuren bzw.   Säurechloride dienen vorzugsweise   zur Herstellung von neuen heterocyclischen Verbindungen der allgemeinen Formel 
 EMI1.5 
 In welcher   Ri-CHs.-CHzOH   oder 
 EMI1.6 
   wonn   R4 Wasserstoff, ein Alkylrest mit 1 bis 20 C-Atomen oder   ein Monohydroxyalkylrest ist,   oder einen Rest 
 EMI1.7 
 In welchem r'und r"Waserstoff oder einen nledngen Alkylrest bedeuten oder zusammen auch einen Heterocyclus bilden können, bedeutet, R2 Wasserstoff oder den Rest -CH3, Ar einen aromatischen Rest der allgemeinen Formel 

 <Desc/Clms Page number 2> 

 
 EMI2.1 
 
 EMI2.2 
 

 <Desc/Clms Page number 3> 

 mitBeispiel 3 :

   a) 3-   (1, 1-Dimethyldecyl) -4-methoxybenzoesäure   
28, 46 g (80 mMol)   4-Brom-2- (1, 1-dimethyldecyl)-anisol, gelöst In   80 ml trockenem Tetrahydrofuran, werden langsam zu 2, 34 g (96 m Grammatom) Magnesiumspänen und einem Jodkristall zugefügt. Bel Beginn der Zugabe erhitzt man, bis die Reaktion begonnen hat   (Rückflusseinrichtung).   Der Rückfluss wird sodann durch die Geschwindigkeit der Zugabe des Bromderivates aufrechterhalten. Nach beendeter Zugabe setzt man das Rühren 30 min bei   500C   fort,   kühlt   auf   OOC   ab und lässt 3 h einen   CO2-Gasstrom   durchströmen. 



   Das Tetrahydrofuran wird verdampft, man fügt 300 ml Wasser hinzu und säuert mit   6N-Chlorwasser-   stoffsäure auf einen pH-Wert = 1 an. Man extrahiert 3 x mit 100 ml Äthyläther. Die organische Phase wird mit einer gesättigten NaCI-Lösung gewaschen, über Magnesiumsulfat getrocknet und die Lösungsmittel verdampft. Der erhaltene Feststoff wird mit 50   ml   kaltem Hexan gewaschen und bel   80 C   im Trockenschrank getrocknet.

   Man erhält   15, 25 g 3- (1, 1-Dlmethyldecyl)-4-methoxybenzoesäure ;   Ausbeute 59 %, Fp =   112 C.   
 EMI3.1 
 (1. 1-Dimethy ! decy !)-4-methoxybenzoesäurech ! ortdIn analoger Welse wie In Beispiel 3 (b) beschneben erhält man, ausgehend von   14, 4 g (44, 8 mMol) der   nach   4 (a)   erhaltenen Säure und 9 ml (44, 8 mMol) Dicyclohexylamin das entsprechende Salz Dieses wird mit 3, 26 ml (44, 8 mMol) Thionylchlorid 16 h bel 200C behandelt, wodurch man das rohe Säurechlorid erhält.

Claims (2)

  1. Patentansprüche 1. Verfahren zur Herstellung von neuen Verbindungen der allgemeinen Formel EMI3.2 worin Ar einen Rest der allgemeinen Formel EMI3.3 darstellt, In welcher R6 Wasserstoff oder einen Alkylrest mit 1 bis 10 C-Atomen und R7 1, 1- Dtmethyidecyl, 1-Methylcyclohexyl oder 1-Adamantyl bedeutet und Q OH oder Cl ist, insbesondere von EMI3.4 -4-decyloxybenzoesäure, 3- (1-Adamantyl) -4-methoxybenzoesäuredecyl)-4-methoxybenzoesäure und den entsprechenden Säurechlonden, dadurch gekennzeichnet, dass nach Bildung des Magneslumdenvates einer Bromverbindung der allgemeinen Formel Ar-Br, wonn Ar wie vorher definiert ist, in einem wasserfreien organischen Lösungsmittel ein C02 Strom hindurchge- EMI3.5 gegebenenfalls direkt mit Thlonylchlo-nd reagieren gelassen wird, um das entsprechende Säurechlond zu erhalten.
  2. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass die Bromverbindung der allgemeinen Formel Ar-Br aus den folgenden ausgewählt ist-2- (1-Adamantyl)-4-brom- (decyloxybenzol), 2- (1-Ada- mantyl)-4-bromanisol.4-Brom-2- (1,1-dimthyldecyl)-anisol
AT0042192A 1984-09-19 1992-03-05 Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden AT401514B (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT0042192A AT401514B (de) 1984-09-19 1992-03-05 Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
LU85544A LU85544A1 (fr) 1984-09-19 1984-09-19 Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique
AT0271885A AT395714B (de) 1984-09-19 1985-09-18 Verfahren zur herstellung von neuen aromatischen heterocyclischen verbindungen
AT0042192A AT401514B (de) 1984-09-19 1992-03-05 Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden

Publications (2)

Publication Number Publication Date
ATA42192A ATA42192A (de) 1996-02-15
AT401514B true AT401514B (de) 1996-09-25

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Family Applications (2)

Application Number Title Priority Date Filing Date
AT0271885A AT395714B (de) 1984-09-19 1985-09-18 Verfahren zur herstellung von neuen aromatischen heterocyclischen verbindungen
AT0042192A AT401514B (de) 1984-09-19 1992-03-05 Verfahren zur herstellung von neuen organischen säuren bzw. säurechloriden

Family Applications Before (1)

Application Number Title Priority Date Filing Date
AT0271885A AT395714B (de) 1984-09-19 1985-09-18 Verfahren zur herstellung von neuen aromatischen heterocyclischen verbindungen

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US (3) US4740519A (de)
JP (1) JPH0784437B2 (de)
AR (1) AR243504A1 (de)
AT (2) AT395714B (de)
AU (2) AU578310B2 (de)
BE (2) BE903254A (de)
CA (2) CA1256804A (de)
CH (2) CH665841A5 (de)
DE (2) DE3533308C2 (de)
DK (1) DK169475B1 (de)
ES (1) ES8608487A1 (de)
FR (1) FR2570377B1 (de)
GB (3) GB2164648B (de)
GR (1) GR852270B (de)
IT (1) IT1209663B (de)
LU (1) LU85544A1 (de)
MX (1) MX166783B (de)
NL (1) NL192878C (de)
PT (1) PT81132B (de)
SE (2) SE461466B (de)
ZA (1) ZA857158B (de)

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US4920140A (en) 1990-04-24
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