HK25892A - Aromatic compounds - Google Patents

Aromatic compounds

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Publication number
HK25892A
HK25892A HK258/92A HK25892A HK25892A HK 25892 A HK25892 A HK 25892A HK 258/92 A HK258/92 A HK 258/92A HK 25892 A HK25892 A HK 25892A HK 25892 A HK25892 A HK 25892A
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HK
Hong Kong
Prior art keywords
formula
compound
enyl
pyrrolidino
prop
Prior art date
Application number
HK258/92A
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English (en)
French (fr)
Inventor
Geoffrey George Coker
John William Addison Findlay
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The Wellcome Foundation Limited
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Publication date
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Publication of HK25892A publication Critical patent/HK25892A/en

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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
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Emergency Medicine (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Superconductors And Manufacturing Methods Therefor (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (17)

1. Verfahren zur Herstellung einer Verbindung der Formel (I): oder deren Salz, Ester oder Amid, worin
R1 eine C1-7 bivalente aliphatische Kohlenwasserstoffgruppe oder eine Einfachbindung bedeutet;
R2 und R3 gleich oder verschieden sind und jedes Wasserstoff, und C1-4-Alkyl repräsentiert oder zusammen mit dem Stickstoff einen 4- bis 6-gliedrigen, Stickstoff enthaltenden heterocyclischen Ring bedeuten;
R4 Wasserstoff, Halogen, Hydroxy, Cyano, C1-4-Acyloxy, C1-4-Alkoxy oder C1-4-Alkyl bedeutet, gegebenenfalls substituiert durch 1 bis 3 Halogenatome;
X -N= oder -CH= bedeutet; und
A und B jedes Wasserstoffatome darstellt oder ―CA―CB -C=C- darstellt; umfassend:
a) Reaktion einer Verbindung der Formel (VI) oder deren Ester mit einem Amin HNR2R3, worin X, A, B und R1 bis R4 die in Anspruch 1 genannte Bedeutung haben, und L eine Austrittsgruppe bedeutet;
b) falls eine Verbindung gemäß Formel (I) hergestellt werden soll, worin R1 (CH2)0 und A und B Wasserstoff sind, Reaktion einer Verbindung der Formel (VII) worin X, R2, R3, R4 die in Anspruch 1 genannte Bedeutung haben und R5 ein Halogenatom bedeutet, mit einer C1-16-Alkyllithiumverbindung und nachfolgender Behandlung mit Kohlendioxid;
c) falle eine Verbindung nach Formel (I) hergestellt werden soll, worin R1 (CH2)a CH=CH(CH2)b und a 0 ist, Reaktion einer Verbindung der Formel (VIII) worin X, A, B, R2, R3 und R4 die in Anspruch 1 genannte Bedeutung haben mit einem geeigneten Wittig-Reagens zum Verknüpfen der Seitenkette CH=CH(CH2)bCOR6, worin COR6 eine vorstehend definierte Säure, Ester- oder Amidgruppe ist, mit - falls gewünscht - nachfolgender Deprotektion der Carboxygruppe;
d) falls eine Verbindung nach Formel (I) hergestellt werden soll, worin CA-CB eine Doppelbindung bedeutet:
i) Reaktion eines Esters, Amids oder Carbonsäuresalzes einer Verbindung nach Formel (IX): mit einem geeigneten Wittig-Reagens für die Verknüpfung der Seitenkette =CHCH2NR2R3, worin X und R1 bis R4 die in Anspruch 1 gegebene Bedeutung haben, mit-falls gewünscht- nachfolgender Deprotektion der Carboxygruppe;
ii) Eliminierung von R7OH aus einer Verbindung nach Formel (X): oder deren Ester oder Amid, worin X, R1 bis R4 die in Anspruch 1 genannte Bedeutung haben und R7 Wasserstoff oder C1-4-Acyl bedeutet;
iii) Reaktion einer Verbindung gemäß Formel (XI): mit einem Amin HNR2R3, worin X, R1 bis R4 die in Anspruch 1 genannte Bedeutung haben und R8 eine C1-4-Acyloxygruppe bedeutet;
e) gegebenenfalls anschließendes Umwandeln einer Verbindung nach Formel (I) in eine andere Verbindung der Formel (I) durch Isomerisierung einer Doppelbindung, Reduzierung einer oder mehrerer Doppelbindungen oder Entesterung der Estergruppe.
2. Verfahren nach Anspruch 1 zur Herstellung einer Verbindung nach Formel (II) oder deren Salz, Ester oder Amid, worin R1 bis R4, X, A und B die in Anspruch 1 genannte Bedeutung haben.
3. Verfahren nach einem der Ansprüche 1 oder 2 zur Herstellung einer Verbindung, worin R1 eine Gruppe (CH2)n bedeutet, worin n eine ganze Zahl von 0 bis 7 ist, oder eine Gruppe (CH2)a CH=CH(CH2)b bedeutet, worin a und b unabhängig voneinander 0 bis 5 sind und die Summe von a und b 5 nicht übersteigt.
4. Verfahren nach einem der Ansprüche 1 bis 3 zur Herstellung einer Verbindung nach Formel (Illa) oder (Illb) oder deren Salz, Ester oder Amid, worin R1 (CH2)n ist, wobei n eine ganze Zahl zwischen 1 bis 7 ist, oder (CH2)aCH=CH-(CH2)b' bedeutet, wobei a und b unabhängig voneinander 0 bis 5 sind und die Summe von a und b 5 nicht übersteigt; R2 und R3 sind gleich oder verschieden und sind Wasserstoff, Niedrigalkyl (1 bis 4 Kohlenstoffatome) oder bilden zusammen mit dem Stickstoffatom einen Stickstoff enthaltenden heterocyclischen Ring (4- bis 6-gliedrig) und R4A bedeutet Wasserstoff, Halogen, Niederalkyl (1 bis 4 Kohlenstoffatome) oder Niederalkoxy (1 bis 4 Kohlenstoffatome).
5. Verfahren nach einem der Ansprüche 1 bis 4 zur Herstellung einer Verbindung, worin R2 und R3 zusammen mit dem Stickstoff eine Pyrrolidino-, Piperidino- oder Morpholinogruppe bilden.
6. Verfahren nach einem der Ansprüche 1 bis 5 zur Herstellung einer Verbindung, worin R1 (CH2)2 oder CH=CH bedeutet, NR2R3 eine Pyrrolidinogruppe oder eine Dimethylaminogruppe bedeutet und R4 Methyl, Trifluormethyl, Methoxy, Brom oder Chlor bedeutet.
7. Verfahren nach einem der Ansprüche 1 bis 6 zur Herstellung einer Verbindung nach Formel (IV): oder deren Salz, Ester oder Amid, worin R1 bis R4 die in Anspruch 1 genannte Bedeutung haben.
8. Verfahren nach Anspruch 7, worin R1 in Formel (IV) eine Einfachbindung, CH=CH oder CH2CH2 bedeutet; NR2R3 bedeutet Pyrrolidino und R4 bedeutet Methyl oder Trifluormethyl.
9. Verfahren nach einem der Ansprüche 1 bis 8, worin CA-CB eine Doppelbindung darstellt und die Gruppe CH2NR2R3 in trans-Stellung zum X enthaltenden Ring steht.
10. Verfahren nach einem der Ansprüche 1 bis 6 zur Herstellung einer Verbindung der Formel (V) oder deren Salz, Ester oder Amid, worin R1 bis R4 die in Anspruch 1 gegebene Bedeutung haben.
11. Verfahren nach Anspruch 10, worin R1 in Formel (V) eine Einfachbindung, CH=CH oder CH2CH2 bedeutet, NR2R3 bedeutet Dimethylamino und R4 bedeutet Chlor oder Brom.
12. Verfahren nach Anspruch 1 zur Herstellung einer Verbindung, ausgewählt aus:
(E)-3-(6-(3-Pyrrolidino-1-(4-tolyl)-prop-1E-enyl)-2-pyridyl)-acrylsäure,
3-(6-(3-Pyrrolidino-1-(4-tolyl)-prop-1 E-enyl)-2-pyridyl)-propionsäure,
(E)-3-(6-(3-Dimethylamino-1-(4-tolyl)-prop-1E-enyl)-2-pyridyl)-acrylsäure,
(E)-3-(6-(3-Pyrrolidino-1-(4-trifluormethylphenyl)-prop-1 E-enyl)-2-pyridyl)-acrylsäure,
(E)-3-(6-(3-Pyrrolidino-1-(4-methoxyphenyl)-prop-1 E-enyl)-2-pyridyl)-acrylsäure,
(E)-3-(6-(1-Phenyl-3-pyrrolidinoprop-1-E-enyl)-2-pyridyl)-acrylsäure,
(E)-3-(6-(1-(4-Chlorphenyl)-3-pyrrolidinoprop-1 E-enyl)-2-pyridyl)-acrylsäure 6-(3-Pyrrolidino-1-(4-tolyl)-prop-1 E-enyl)-pyridin-2-carbonsäure
(E)-3-(3-Pyrrolidino-1-(4-tolyl)-prop-1-enyl)-benzoesäure,
(E)-3-(3-Pyrrolidino-1-(4-tolyl)-prop-1-enyl)-zimtsäure,
(E)-3-((E)-3-Pyrrolidino-1-(4-methoxyphenyl)-prop-1-enyl)-zimtsäure,
(E)-3-((E)-3-Dimethylamino-1-(4-tolyl)-prop-1-enyl))-zimtsäure,
(E)-3-(3-(3-Pyrrolidino-1-(4-tolyl)-prop-1-enyl)-phenyl)-propionsäure,
oder deren Salz, Ester oder Amid.
13. Pharmazeutische Zubereitung, umfassend eine Verbindung der Formel (I) zusammen mit einem oder mehreren pharmazeutisch annehmbaren Trägern und gegebenenfalls anderen therapeutischen Bestandteilen.
14. Verfahren zur Herstellung einer pharmazeutischen Zubereitung nach Anspruch 13, bei dem die aktive Verbindung mit einem Träger zusammengebracht wird, der einen oder mehrere Nebenbestandteil(e) darstellt.
15. Verfahren zur Herstellung einer Verbindung der Formel (X): worin R1, R2, R3, R4 und X die in Anspruch 1 definierte Bedeutung haben und R7 Wasserstoff oder C1-4-Acyl bedeutet, bei dem entweder
(i) für den Fall, daß R7 Wasserstoff ist, eine Verbindung der Formel XX worin R2, R3, R4 und X die in Formel (X) gegebene Bedeutung haben, umgesetzt wird mit einer Verbindung CH=CHCOR13' worin COR13 eine Ester- oder Amidgruppe ist; oder
(ii) eine Verbindung der Formel XXII worin R2, R3, R4, R7 und X die in Formel (X) gegebene Bedeutung haben, umgesetzt wird mit Malonsäure.
16. Verfahren zur Herstellung einer Verbindung der Formel (XI) worin
R1 eine C1-7-bivalente aliphatische Kohlenwasserstoffgruppe oder eine Einfachbindung bedeutet;
R4 Wasserstoff, Halogen, Hydroxy, Cyano, C1-4-Acyloxy, C1-4-Alkoxy oder C1-4-Alkyl bedeutet, gegebenenfalls substituiert durch 1 bis 3 Halogenatome;
X -N= oder -CH= bedeutet; und
R8 eine C1-4-Acyloxygruppe bedeutet;
die entsprechende Verbindung, worin R8 eine Hydroxygruppe bedeutet, mit einem C1-4-Acylierungsmittel acyliert wird.
17. Verfahren nach Anspruch 1, Verfahrensschritt (e), worin die Verbindung der Formel (I) eine Verbindung nach Formel (XII) ist, worin R1, R2, R3, R4 und X die in Formel (I) gegebene Bedeutung haben.
HK258/92A 1982-02-04 1992-04-09 Aromatic compounds HK25892A (en)

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GB8203261 1982-02-04
GB8229705 1982-10-18

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GB8707416D0 (en) * 1987-03-27 1987-04-29 Wellcome Found Pharmaceutical formulations
DE3711866A1 (de) * 1987-04-08 1988-10-27 Hoechst Ag Synthese von peptidamiden mittels festphasenmethode unter verwendung von saeurelabilen ankergruppen
GB8914040D0 (en) * 1989-06-19 1989-08-09 Wellcome Found Agents for potentiating the effects of antitumour agents and combating multiple drug resistance
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