WO1996002540A1 - Acides heterocyclyl-1-phenyl substitues quinolone-carboxyliques utilises comme agents antiviraux - Google Patents

Acides heterocyclyl-1-phenyl substitues quinolone-carboxyliques utilises comme agents antiviraux Download PDF

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Publication number
WO1996002540A1
WO1996002540A1 PCT/EP1995/002642 EP9502642W WO9602540A1 WO 1996002540 A1 WO1996002540 A1 WO 1996002540A1 EP 9502642 W EP9502642 W EP 9502642W WO 9602540 A1 WO9602540 A1 WO 9602540A1
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WO
WIPO (PCT)
Prior art keywords
compounds
phenyl
general formula
optionally
acid
Prior art date
Application number
PCT/EP1995/002642
Other languages
German (de)
English (en)
Inventor
Wolfgang Bender
Wolfgang RÖBEN
Arnold Paessens
Stephan Bartel
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU30762/95A priority Critical patent/AU3076295A/en
Publication of WO1996002540A1 publication Critical patent/WO1996002540A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to heterocyclyl-1-phenyl substituted quinolone carboxylic acids, processes for their preparation and their use as medicaments, in particular as antiviral agents.
  • the present invention now relates to heterocyclyl-1-phenyl substituted quinolonecarboxylic acids of the general formula (I),
  • A represents hydrogen or methyl
  • X represents a nitrogen atom or a group of the formula -CH, C-F or
  • T stands for an oxygen or sulfur atom or for the -CH -, - group
  • R represents phenyl, pyridyl, pyrimidyl or pyrazinyl, which may be up to 3 times the same or different by nitro, trifluoromethyl.
  • Halogen, cyano, hydroxy or by straight-chain or branched alkyl, acyl, Alkoxy or alkylthio are each substituted with up to 8 carbon atoms,
  • R 2 represents hydrogen or fluorine
  • Salts of the substances according to the invention with mineral acids, carboxylic acids or sulfonic acids are particularly preferred.
  • Physiologically acceptable salts can also be alkali, alkaline earth, silver and guanidinium salts of the compounds according to the invention.
  • A represents hydrogen or methyl
  • X represents a nitrogen atom or a group of the formula -CH, C-F or C-Cl,
  • T represents an oxygen atom
  • R 1 represents phenyl, pyridyl, py ⁇ midyl or pyrazinyl, which are optionally up to 3 times the same or different by nitro, trifluoromethyl, fluorine, chlorine, bromine, cyano, hydroxy or by straight-chain or branched alkyl, acyl, alkoxy or alkylthio with each up to 6 carbon atoms are substituted,
  • R 2 represents hydrogen or fluorine
  • A represents hydrogen or methyl
  • X represents a nitrogen atom or a group of the formula -CH, C-F or C-Cl,
  • T represents an oxygen atom
  • R 1 represents phenyl, pyridyl, pyrimidyl or pyrazinyl, which are optionally up to 3 times the same or different by nitro, trifluoromethyl, fluorine, chlorine, bromine, cyano, hydroxy or by straight-chain or branched alkyl, acyl, alkoxy or alkylthio with each up to 4 carbon atoms are substituted,
  • R 2 , X and T have the meaning given above and
  • R J represents halogen, preferably fluorine or chlorine
  • a and R 1 have the meaning given above,
  • Suitable solvents for all process steps are the customary inert solvents which do not change under the reaction conditions.
  • These preferably include organic solvents such as ethers, for example diethyl ether, dioxane or tetrahydrofuran, or hydrocarbons such as benzene, toluene, xylene, cyclohexane or petroleum fractions or halogenated hydrocarbons such as methylene chloride,
  • the usual basic compounds are suitable as bases for individual reaction steps. These include, for example, alkali or alkaline earth metal hydroxides, pyridine, triethylamine, diisopropylethylamine or N-methylpiperidine. or bicyclic amidines such as diazabicyclo [2,2,3] octane, 1,5-diazabicyclo [3,4,0] -nonene-5 (DBN) or 1,5-diazabicyclo [3,4,0] undecene- 5 (DBU). Diisopropylethylamine is preferred.
  • the bases are generally used in an amount of 1 to 3 mol, preferably 1 to 1.5 mol, based on 1 mol of the corresponding carboxylic acid.
  • the process is generally carried out in a temperature range from 0 ° C. to -60 ° C., preferably from 0 ° C. to + 140 ° C.
  • normal pressure In general, normal pressure is used. However, it is also possible to carry out the process under negative pressure or under positive pressure (e.g. in a range from 0.5 to 5 bar).
  • R 4 represents C r C 4 alkyl
  • R 5 represents C j -C 4 alkoxy or C j -C 4 dialkylamino
  • D represents halogen, preferably chlorine or fluorine
  • the process is generally carried out in a temperature range from 0 ° C. to -150 ° C., preferably from 0 ° C. to + 120 ° C.
  • the saponification is generally carried out in a mixture of glacial acetic acid / water and in the presence of an inorganic acid, preferably sulfuric acid or hydrochloric acid, in a temperature range from 50 to 100 ° C., preferably at 100 ° C.
  • an inorganic acid preferably sulfuric acid or hydrochloric acid
  • the compounds according to the invention showed activity in cell cultures infected with lentivirus. This could be shown using the example of the HIV virus.
  • the HIV test was carried out with minor modifications using the method of Pauwels et al. [see. Journal of Virological Methods 20, (1988), 309-321].
  • PBL Normal human blood lymphocytes
  • RPMI 1640 20% fetal calf serum with phythema agglutinin (90 ⁇ g / ml) and interleukin-2 (40U / ml).
  • phythema agglutinin 90 ⁇ g / ml
  • interleukin-2 40U / ml
  • PBLs were pelleted and the cell pellet was then suspended in 1 ml of HIV virus adsorption solution and incubated at 37 ° C. for 1 hour.
  • the virus adsorption solution was centrifuged and the infected cell pellet in
  • the remaining wells contained the compounds according to the invention in different combinations.
  • test batches were incubated at 37 ° C. until the untreated virus control showed the syncytia formation typical of HIN (between days 3 and 6 after infection), which was then evaluated microscopically.
  • the untreated virus control resulted in about 20 syncytia under these test conditions, while the untreated cell control showed no syncytia.
  • the IC 50 values were determined as the concentration of the treated and infected cells at which 50% (approx. 10 syncytia) of the virus-induced syncytia were suppressed by the treatment with the compound according to the invention.
  • the compounds according to the invention are valuable active substances for the treatment and prophylaxis of diseases caused by retroviruses in human and veterinary medicine.
  • Areas of indication in human medicine include: 1) The treatment and prophylaxis of human retrovirus infections
  • HIV I virus of human
  • AIDS AIDS related complex
  • LAS lymphadenopathy syndrome
  • Points 2, 3 and 4 above are preferred from the area of indications in human medicine
  • the present invention includes pharmaceutical preparations which, in addition to non-toxic, inert pharmaceutically suitable excipients, contain one or more compounds of the formula (I) or which consist of one or more
  • the active compounds of the formula (I) should be present in the pharmaceutical preparations listed above, preferably in a concentration of approximately 0.1 to 99.5, preferably approximately 0.5 to 95% by weight of the total mixture
  • the pharmaceutical preparations listed above can also contain other active pharmaceutical ingredients
  • the pharmaceutical preparations listed above are prepared in a customary manner by known methods, e.g. by mixing the active substance or substances with the carrier substance or substances.
  • the active compound (s) according to the invention in total amounts of from about 0.5 to about 500, preferably from 1 to 100 mg / kg of body weight per 24 hours , if necessary in the form of several single doses, to achieve the desired results.
  • a single dose contains the
  • Active ingredients preferably in amounts of about 1 to about 80, in particular 1 to 30 mg / kg body weight. However, it may be necessary to deviate from the doses mentioned, depending on the type and body weight of the object to be treated, the type and severity of the disease, the type of preparation and administration of the drug, and the period or Interval within which the administration takes place.
  • the retention indices relate to a series of homologous 2-alkanones
  • Example II The title compound is obtained analogously to Example III from the acrylic acid ester of Example IIIc and 3-morpholinoaniline (Example II).
  • DC system VI: R f 0.49
  • Example XI The title compound is prepared analogously to Example X by acidic saponification of the ester from Example XI.
  • Example XIII The title compound is prepared analogously to Example X by acidic saponification of the ester from Example XIII.
  • Example II The title compound is prepared analogously to Example XV from 2- (2,4-difluorobenzoyl) acrylic acid ethyl ester and 3-Mo ⁇ holinoanilin (Example II).
  • HPLC system I Rt 6.087 min.
  • Example II The title compound is prepared analogously to Example XV from 2- (2,4,5-trifluorobenzoyl) acrylic acid ethyl ester and 2-morpholinoaniline (Example II).
  • DC system I: R f 0.68
  • Example XV The title compound is prepared analogously to Example XV from 2- (2,3,4,5-tetrafluorobenzoyl) acrylic acid ethyl ester and 4-Mo ⁇ holinoanilin (Janssen Chimica).
  • Example XV The title compound is prepared analogously to Example XV from 2- (2,3,4,5-tetrafluorobenzoyl) acrylic acid ethyl ester and 2-Mo ⁇ holinoanilin (Lancaster).
  • Example II The title compound is prepared analogously to Example XV from 2- (3-chloro-2,4,5-trifluorobenzoyl) acrylic acid ethyl ester and 3-Mo ⁇ holinoanilin (Example II)
  • Example 1 The examples listed in Tables 1a and 1b below are prepared analogously to Example 1 by reacting the compound from Example IV and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl):
  • Example 2a and 2b are prepared analogously to Example 1 by reacting the compound from Example ⁇ T and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example VTH 7-chloro-1,4-dihydro-4-oxo-1 - [(4-moopholino) phenyl] -1, 8-naphthyridine-3- carboxylic acid hydrochloride
  • Example VTH 7-chloro-1,4-dihydro-4-oxo-1 - [(4-moopholino) phenyl] -1, 8-naphthyridine-3- carboxylic acid hydrochloride
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 4a and 4b are prepared analogously to Example 2 by reacting the compound from Example XII and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized using known methods (Houben-Weyl).
  • Example 2 The examples listed in Tables 5a and 5b below are prepared analogously to Example 2 by reacting the compound from Example X and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 6a and 6b are prepared analogously to Example 2 by reacting the compound from Example XIV and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 7a and 7b are prepared analogously to Example 3 by reacting the compound from Example XV and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 8a and 8b are prepared analogously to Example 4 by reacting the compound from Example XX and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl) .
  • Example 9a and 9b are prepared analogously to Example 4 by reacting the compound from Example XTX and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 10a and 10b are prepared analogously to Example 4 by reacting the compound from Example X ⁇ TII and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 11a and 11b are prepared analogously to Example 5 by reacting the compound from Example XXI and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 12a and 12b are prepared analogously to Example 6 by reacting the compound from Example XXVI and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 13a and 13b are prepared analogously to Example 6 by reacting the compound from Example XXV and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 14a and 14b are prepared analogously to Example 6 by reacting the compound from Example XXIV and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).
  • Example 15a and 15b are prepared analogously to Example 4 by reacting the compound from Example X ⁇ T and the corresponding piperazine derivatives.
  • the latter are commercially available (Aldrich, Janssen, Emka) or can be synthesized by known methods (Houben-Weyl).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention a pour objet des acides hétérocyclyl-1-phényl substitués quinolone-carboxyliques, de formule générale (I), dans laquelle les substituants ont les significations données dans la description, ainsi qu'un procédé de préparation de ces acides et leur utilisation comme médicaments, en particulier comme agents antiviraux.
PCT/EP1995/002642 1994-07-20 1995-07-07 Acides heterocyclyl-1-phenyl substitues quinolone-carboxyliques utilises comme agents antiviraux WO1996002540A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30762/95A AU3076295A (en) 1994-07-20 1995-07-07 Heterocyclyl-1-phenyl substituted quinolone carboxylic acids as antiviral agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4425647A DE4425647A1 (de) 1994-07-20 1994-07-20 Heterocyclyl-1-phenyl substituierte Chinoloncarbonsäuren
DEP4425647.7 1994-07-20

Publications (1)

Publication Number Publication Date
WO1996002540A1 true WO1996002540A1 (fr) 1996-02-01

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Application Number Title Priority Date Filing Date
PCT/EP1995/002642 WO1996002540A1 (fr) 1994-07-20 1995-07-07 Acides heterocyclyl-1-phenyl substitues quinolone-carboxyliques utilises comme agents antiviraux

Country Status (5)

Country Link
AU (1) AU3076295A (fr)
DE (1) DE4425647A1 (fr)
IL (1) IL114625A0 (fr)
WO (1) WO1996002540A1 (fr)
ZA (1) ZA956017B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997011068A1 (fr) * 1995-09-22 1997-03-27 Wakunaga Pharmaceutical Co., Ltd. Nouveaux derives de l'acide pyridone-carboxylique ou leurs sels et agent antibacterien les contenant comme ingredient actif
EP1927589A1 (fr) 2006-11-30 2008-06-04 Cadila Healthcare Ltd. Dérivés de quinoline

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6310211B1 (en) 1996-09-10 2001-10-30 Pharmacia & Upjohn Company 8-hydroxy-7-substituted quinolines as anti-viral agents
EP0935600A1 (fr) * 1996-10-30 1999-08-18 Bayer Ag Procede de fabrication de composes de naphtyridine et nouveaux produits intermediaires

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0422485A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Dérivés d'acide quinolone carboxylique, procédé pour leur préparation et leur utilisation
EP0572259A1 (fr) * 1992-05-27 1993-12-01 Ube Industries, Ltd. Dérivés d'aminoquinolones comme agents anti-HIV
DE4303657A1 (de) * 1993-02-09 1994-08-11 Bayer Ag Neue Chinolon- und Naphthyridoncarbonsäurederivate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0422485A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Dérivés d'acide quinolone carboxylique, procédé pour leur préparation et leur utilisation
EP0572259A1 (fr) * 1992-05-27 1993-12-01 Ube Industries, Ltd. Dérivés d'aminoquinolones comme agents anti-HIV
DE4303657A1 (de) * 1993-02-09 1994-08-11 Bayer Ag Neue Chinolon- und Naphthyridoncarbonsäurederivate

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997011068A1 (fr) * 1995-09-22 1997-03-27 Wakunaga Pharmaceutical Co., Ltd. Nouveaux derives de l'acide pyridone-carboxylique ou leurs sels et agent antibacterien les contenant comme ingredient actif
US5998436A (en) * 1995-09-22 1999-12-07 Wakunaga Pharmaceuticals Co., Ltd. Pyridonecarboxylic acid derivatives or their salts and antibacterial agent comprising the same as the active ingredient
US6133284A (en) * 1995-09-22 2000-10-17 Wakunaga Pharmaceutical Co., Ltd. Pyridonecarboxylic acid derivatives or their salts, and antibacterial agents containing the same as their effective components
US6156903A (en) * 1995-09-22 2000-12-05 Wakunaga Pharmaceutical Co., Ltd. Pyridonecarboxylic acid derivatives or their salts, and antibacterial agents containing the same as their effective components
EP1927589A1 (fr) 2006-11-30 2008-06-04 Cadila Healthcare Ltd. Dérivés de quinoline

Also Published As

Publication number Publication date
AU3076295A (en) 1996-02-16
ZA956017B (en) 1996-03-19
IL114625A0 (en) 1995-11-27
DE4425647A1 (de) 1996-01-25

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