Title:
HYDRAZONES AND THEIR THERAPEUTIC USE
Document Type and Number:
WIPO Patent Application WO2002070464
Kind Code:
A3
Abstract:
The invention relates to novel hydrazone derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as anti-infectives.
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Inventors:
BURRI KASPAR (CH)
HOFFNER JOHANNES (CH)
ISLAM KHALID (CH)
MUKHIJA SEEMA (CH)
HOFFNER JOHANNES (CH)
ISLAM KHALID (CH)
MUKHIJA SEEMA (CH)
Application Number:
PCT/EP2002/000474
Publication Date:
January 22, 2004
Filing Date:
January 18, 2002
Export Citation:
Assignee:
ARPIDA AG (CH)
BURRI KASPAR (CH)
HOFFNER JOHANNES (CH)
ISLAM KHALID (CH)
MUKHIJA SEEMA (CH)
BURRI KASPAR (CH)
HOFFNER JOHANNES (CH)
ISLAM KHALID (CH)
MUKHIJA SEEMA (CH)
International Classes:
C07D207/325; A61K31/166; A61K31/402; A61K31/4045; A61P31/04; A61P43/00; C07C243/38; C07C251/86; C07D207/327; C07D209/18; C07D207/32; (IPC1-7): C07C251/86; A61K31/15; A61P31/04; C07D207/325
Domestic Patent References:
| WO1999011262A1 | 1999-03-11 | |||
| WO2001070213A2 | 2001-09-27 | |||
| WO2003007955A2 | 2003-01-30 |
Foreign References:
| EP0866075A2 | 1998-09-23 |
Other References:
DUTTA, M. M. ET AL: "Studies on biologically active heterocycles. Part III. Synthesis and antibacterial activity of some 2-aryl/aralkyl-3-substituted-4- thiazolidinones", JOURNAL OF THE INDIAN CHEMICAL SOCIETY (1990), 67(4), 332-4, XP008017275
MOHSEN ISMAIL M: "NEW DERIVATIVES OF 3,5-DICHLOROSALICYLALDEHYDE AS ANTIMYCOTIC AGENTS", INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, XX, XX, vol. 48, no. 5, September 1986 (1986-09-01), pages 121 - 124, XP000926581, ISSN: 0250-474X
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CASCAVAL, ALEXANDRU ET AL: "Preparation of salicylic acid hydrazones from salicylic acid hydrazide an 2-hydroxyacetophenones", XP002241930, retrieved from STN Database accession no. 125:195202
BHAMARIA, R. P. ET AL: "In vitro effect of 1-acyl-4-alkyl-(or aryl)-thiosemicarbazides, 1-(5-chlorosalicylidine)-4-alkyl-(or aryl)-thiosemicarbazones, and some hydrazones of 5-chlorosalicylaldehyde against pathogenic bacteria, including Mycobacterium tuberculosis (H37Rv)", INDIAN JOURNAL OF EXPERIMENTAL BIOLOGY (1968), 6(1), 62-3, XP008017308
NAWAR. N. ET AL.: "SOME METAL(II) COMPLEXES OF O-AMINOACETOPHENONE BENZOYLHYDRAZONE (AABH): THEIR PREPARATION, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY", SYNTH. REACT. INORG. MET.-ORG. CHEM., vol. 29, no. 8, 1999, pages 1365 - 1384, XP008013882
HAKSAR C.N. ET AL.: "ANTIBACTERIAL ACTIVITY OF HYDRAZONES OF SOME SUBSTITUTED BENZOHYDRAZINES", LABDEV J. SCI. TECH., vol. 12B, no. 1, 1974, pages 13 - 16, XP008013852
NAWAR N ET AL: "SYNTHESIS, SPECTRAL AND ANTIMICROBIAL ACTIVITY STUDIES OF O-AMINOACETOPHENONE O-HYDROXYBENZOYLHYDRAZONE COMPLEXES", TRANSITION METAL CHEMISTRY, CHAPMAN & HALL, GB, vol. 25, no. 1, 2000, pages 1 - 8, XP008013873, ISSN: 0340-4285
CHAABAN, IBRAHIM ET AL: "Synthesis of substituted 2-acetylhydroquinone and 2-acetylbenzoquinone derivatives for an expected antibacterial activity", SCIENTIA PHARMACEUTICA (1984), 52(1), 59-65, XP008017341
MOHAN M ET AL: "SYNTHESIS, CHARACTERIZATION AND ANTITUMOR ACTIVITY OF IRON (II) ANDIRON (III) COMPLEXES OF 3- AND 5-SUBSTITUTED SALICYLALDEHYDE BENZOYL HYDRAZONES", INORGANICA CHIMICA ACTA, LAUSANNE, CH, vol. 135, 1 March 1987 (1987-03-01), pages 167 - 177, XP002067536, ISSN: 0020-1693
SYAMAL A ET AL: "BROMATE-BROMIDE MIXTURE AS A TITRIMETRIC REAGENT FOR THE DETERMINATION OF SOME ORTHO-HYDROXYALDEHYDES, ACIDS, HYDRAZIDES, SCHIFF BASES AND THEIR METAL COMPLEXES", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, THE INDIAN CHEMICAL SOCIETY, CALCUTTA, IN, vol. 65, 1 February 1988 (1988-02-01), pages 112 - 116, XP002067541, ISSN: 0019-4522
WANG, JITAO ET AL: "Synthesis and structure of pentacoordinate tin(IV) complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1989), 375(2), 173-81, XP001149038
AINSCOUGH, ERIC W. ET AL: "Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure-activity relationships", JOURNAL OF INORGANIC BIOCHEMISTRY (1999), 77(3-4), 125-133, XP002906285
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241931
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; INOUE, HITOSHI ET AL: "Preparation of acylhydrazone derivatives as Maillard reaction inhibitors and active oxygen scavengers", XP002241932, retrieved from STN Database accession no. 130:325088
AFONSO, A. M. ET AL: "Pyrocatechol-3-aldehyde salicyloylhydrazone as reagent for the fluorometric determination of zinc", MIKROCHIMICA ACTA (1984), 2(1-2), 53-60, XP008017272
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LAPIN, B. N. ET AL: "Synthesis and antiradiation activity of azomethines in a series of trihydroxybenzaldehydes", XP002241933, retrieved from STN Database accession no. 92:146370
PIETZSCH, W. ET AL: "Lipoxygenase-inhibitory azomethines and benzoylhydrazones. II. Effects of phenylsubstituted azomethines on the antigen-induced contractions of guinea pig lung parenchymal strips and jejunum segments", AGENTS AND ACTIONS (1991), 32(1-2), 142-3, XP008017307
OSMAN, MAHAR MOHAMED ET AL: "Complexes of cobalt(II), nickel(II), copper(II) and zinc(II) with 3-hydroxy-2-naphthoyl hydrazones of some aromatic aldehydes", ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICAE (1981), 108(1), 13-23, XP008017273
MAURYA, MANNAR R. ET AL: "New dioxouranium(VI) complexes of tridentate Schiff bases derived from o-cresotic acid hydrazide and various aldehydes/ketones", SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY (1989), 19(9), 923-30, XP001149015
PITT C G ET AL: "ESTERS AND LACTONES OF PHENOLIC AMINO CARBOXYLIC ACIDS: PRODRUGS FOR IRON CHELATION", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 29, no. 7, 1986, pages 1231 - 1237, XP002036485, ISSN: 0022-2623
DOUGLAS, S. PAUL ET AL: "Spectral studies of complexation reaction between copper(II) and 2,3,4-trihydroxyphenylethylidine benzoic acid hydrazide", JOURNAL OF THE INDIAN CHEMICAL SOCIETY (2000), 77(2), 81-82, XP008017274
PALACIOS, MARIA S. ET AL: "Spectroscopic properties and crystal structure of an oxovanadium(V) alkox complex with the ligand: 5-chloro-o-hydroxyacetophenone salicylhydrazide", POLYHEDRON (1997), 16(7), 1143-1147, XP002241929
KATROLIA, S. P. ET AL: "Studies on antifungal agents: aromatic acid hydrazones of vanillin, veratraldehyde, 5-bromo-vanillin and bourbonal", HINDUSTAN ANTIBIOTICS BULLETIN (1989), 31(3-4), 65-70, XP008017285
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241934
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241935
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241936
XIAN H ET AL: "PREPARATION OF 1,2-DIACYLBENZENES FROM O-HYDROXYARYL KETONE ACYLHYDRAZONES USING CROSS-LINKED POLYÄSTYRENE-(IODOSO DIACETATE)Ü", SYNTHETIC COMMUNICATIONS, MARCEL DEKKER, NEW YORK, NY, US, vol. 31, no. 16, 2001, pages 2413 - 2418, XP001102733, ISSN: 0039-7911
MOHSEN ISMAIL M: "NEW DERIVATIVES OF 3,5-DICHLOROSALICYLALDEHYDE AS ANTIMYCOTIC AGENTS", INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, XX, XX, vol. 48, no. 5, September 1986 (1986-09-01), pages 121 - 124, XP000926581, ISSN: 0250-474X
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CASCAVAL, ALEXANDRU ET AL: "Preparation of salicylic acid hydrazones from salicylic acid hydrazide an 2-hydroxyacetophenones", XP002241930, retrieved from STN Database accession no. 125:195202
BHAMARIA, R. P. ET AL: "In vitro effect of 1-acyl-4-alkyl-(or aryl)-thiosemicarbazides, 1-(5-chlorosalicylidine)-4-alkyl-(or aryl)-thiosemicarbazones, and some hydrazones of 5-chlorosalicylaldehyde against pathogenic bacteria, including Mycobacterium tuberculosis (H37Rv)", INDIAN JOURNAL OF EXPERIMENTAL BIOLOGY (1968), 6(1), 62-3, XP008017308
NAWAR. N. ET AL.: "SOME METAL(II) COMPLEXES OF O-AMINOACETOPHENONE BENZOYLHYDRAZONE (AABH): THEIR PREPARATION, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY", SYNTH. REACT. INORG. MET.-ORG. CHEM., vol. 29, no. 8, 1999, pages 1365 - 1384, XP008013882
HAKSAR C.N. ET AL.: "ANTIBACTERIAL ACTIVITY OF HYDRAZONES OF SOME SUBSTITUTED BENZOHYDRAZINES", LABDEV J. SCI. TECH., vol. 12B, no. 1, 1974, pages 13 - 16, XP008013852
NAWAR N ET AL: "SYNTHESIS, SPECTRAL AND ANTIMICROBIAL ACTIVITY STUDIES OF O-AMINOACETOPHENONE O-HYDROXYBENZOYLHYDRAZONE COMPLEXES", TRANSITION METAL CHEMISTRY, CHAPMAN & HALL, GB, vol. 25, no. 1, 2000, pages 1 - 8, XP008013873, ISSN: 0340-4285
CHAABAN, IBRAHIM ET AL: "Synthesis of substituted 2-acetylhydroquinone and 2-acetylbenzoquinone derivatives for an expected antibacterial activity", SCIENTIA PHARMACEUTICA (1984), 52(1), 59-65, XP008017341
MOHAN M ET AL: "SYNTHESIS, CHARACTERIZATION AND ANTITUMOR ACTIVITY OF IRON (II) ANDIRON (III) COMPLEXES OF 3- AND 5-SUBSTITUTED SALICYLALDEHYDE BENZOYL HYDRAZONES", INORGANICA CHIMICA ACTA, LAUSANNE, CH, vol. 135, 1 March 1987 (1987-03-01), pages 167 - 177, XP002067536, ISSN: 0020-1693
SYAMAL A ET AL: "BROMATE-BROMIDE MIXTURE AS A TITRIMETRIC REAGENT FOR THE DETERMINATION OF SOME ORTHO-HYDROXYALDEHYDES, ACIDS, HYDRAZIDES, SCHIFF BASES AND THEIR METAL COMPLEXES", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, THE INDIAN CHEMICAL SOCIETY, CALCUTTA, IN, vol. 65, 1 February 1988 (1988-02-01), pages 112 - 116, XP002067541, ISSN: 0019-4522
WANG, JITAO ET AL: "Synthesis and structure of pentacoordinate tin(IV) complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1989), 375(2), 173-81, XP001149038
AINSCOUGH, ERIC W. ET AL: "Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure-activity relationships", JOURNAL OF INORGANIC BIOCHEMISTRY (1999), 77(3-4), 125-133, XP002906285
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241931
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; INOUE, HITOSHI ET AL: "Preparation of acylhydrazone derivatives as Maillard reaction inhibitors and active oxygen scavengers", XP002241932, retrieved from STN Database accession no. 130:325088
AFONSO, A. M. ET AL: "Pyrocatechol-3-aldehyde salicyloylhydrazone as reagent for the fluorometric determination of zinc", MIKROCHIMICA ACTA (1984), 2(1-2), 53-60, XP008017272
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LAPIN, B. N. ET AL: "Synthesis and antiradiation activity of azomethines in a series of trihydroxybenzaldehydes", XP002241933, retrieved from STN Database accession no. 92:146370
PIETZSCH, W. ET AL: "Lipoxygenase-inhibitory azomethines and benzoylhydrazones. II. Effects of phenylsubstituted azomethines on the antigen-induced contractions of guinea pig lung parenchymal strips and jejunum segments", AGENTS AND ACTIONS (1991), 32(1-2), 142-3, XP008017307
OSMAN, MAHAR MOHAMED ET AL: "Complexes of cobalt(II), nickel(II), copper(II) and zinc(II) with 3-hydroxy-2-naphthoyl hydrazones of some aromatic aldehydes", ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICAE (1981), 108(1), 13-23, XP008017273
MAURYA, MANNAR R. ET AL: "New dioxouranium(VI) complexes of tridentate Schiff bases derived from o-cresotic acid hydrazide and various aldehydes/ketones", SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY (1989), 19(9), 923-30, XP001149015
PITT C G ET AL: "ESTERS AND LACTONES OF PHENOLIC AMINO CARBOXYLIC ACIDS: PRODRUGS FOR IRON CHELATION", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 29, no. 7, 1986, pages 1231 - 1237, XP002036485, ISSN: 0022-2623
DOUGLAS, S. PAUL ET AL: "Spectral studies of complexation reaction between copper(II) and 2,3,4-trihydroxyphenylethylidine benzoic acid hydrazide", JOURNAL OF THE INDIAN CHEMICAL SOCIETY (2000), 77(2), 81-82, XP008017274
PALACIOS, MARIA S. ET AL: "Spectroscopic properties and crystal structure of an oxovanadium(V) alkox complex with the ligand: 5-chloro-o-hydroxyacetophenone salicylhydrazide", POLYHEDRON (1997), 16(7), 1143-1147, XP002241929
KATROLIA, S. P. ET AL: "Studies on antifungal agents: aromatic acid hydrazones of vanillin, veratraldehyde, 5-bromo-vanillin and bourbonal", HINDUSTAN ANTIBIOTICS BULLETIN (1989), 31(3-4), 65-70, XP008017285
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241934
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241935
DATABASE CHEMCATS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002241936
XIAN H ET AL: "PREPARATION OF 1,2-DIACYLBENZENES FROM O-HYDROXYARYL KETONE ACYLHYDRAZONES USING CROSS-LINKED POLYÄSTYRENE-(IODOSO DIACETATE)Ü", SYNTHETIC COMMUNICATIONS, MARCEL DEKKER, NEW YORK, NY, US, vol. 31, no. 16, 2001, pages 2413 - 2418, XP001102733, ISSN: 0039-7911
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