Title:
COMPOUND; TAUTOMER AND GEOMETRIC ISOMER THEREOF; SALT OF SAID COMPOUND, TAUTOMER, OR GEOMETRIC ISOMER; METHOD FOR MANUFACTURING SAID COMPOUND, TAUTOMER, ISOMER, OR SALT; ANTIMICROBIAL AGENT; AND ANTI-INFECTIVE DRUG
Document Type and Number:
WIPO Patent Application WO/2014/061752
Kind Code:
A1
Abstract:
A compound characterized in being represented by any of general formulae (1) to (5); a tautomer or a geometric isomer thereof; a salt of the compound, tautomer, or geometric isomer; and the like. (In the formulae, X1 represents a single bond or a C1-8 alkylene group; Y1 represents a single bond, -O-, -NHCO-, etc.; Z1 represents a C8-30 alkyl group optionally having a halogen atom; X2 represents a single bond, -CO-, etc.; Y2 represents a hydrogen atom or an optionally-substituted C1-30 hydrocarbon group; Z2 represents a C5-30 hydrocarbon group optionally having a halogen atom; X3 represents a single bond, or -NH-; Y3 represents -O-, -NH-, etc.; X4 represents a C1-8 alkylene group; Z represents a hydrogen atom, a halogen atom, a C1-6 alkoxy group, or a C1-20 hydrocarbon group; R1 represents an optionally-substituted C1-30 hydrocarbon group; and Z3 represents a halogen atom, a C1-6 alkoxy group, or a C1-20 hydrocarbon group).
Inventors:
ISHIKAWA TERUHIKO (JP)
KITAOKA TATSUYA (JP)
KATAYAMA SHYOTA (JP)
ITOH YOSHIKUNI (JP)
UTSUMI RYUTARO (JP)
IGARASHI MASAYUKI (JP)
KITAOKA TATSUYA (JP)
KATAYAMA SHYOTA (JP)
ITOH YOSHIKUNI (JP)
UTSUMI RYUTARO (JP)
IGARASHI MASAYUKI (JP)
Application Number:
PCT/JP2013/078233
Publication Date:
April 24, 2014
Filing Date:
October 17, 2013
Export Citation:
Assignee:
UNIV OKAYAMA (JP)
MICROBIAL CHEM RES FOUND (JP)
YUIMEDIC INC (JP)
UNIV KINKI (JP)
MICROBIAL CHEM RES FOUND (JP)
YUIMEDIC INC (JP)
UNIV KINKI (JP)
International Classes:
C07D209/34; A61K31/353; A61K31/404; A61P31/04; C07D311/56
Foreign References:
| JP2006515012A | 2006-05-18 | |||
| JPH11349568A | 1999-12-21 | |||
| JP2005533841A | 2005-11-10 | |||
| JPH06340649A | 1994-12-13 | |||
| JPH07509488A | 1995-10-19 | |||
| US3122557A | 1964-02-25 | |||
| JPS5242881A | 1977-04-04 | |||
| JPH06501248A | 1994-02-10 | |||
| JP2000500490A | 2000-01-18 | |||
| CN102217597A | 2011-10-19 |
Other References:
SHTRIGOL, S. YU. ET AL.: "The nootropic properties of new 2-oxoindolin-3-glyoxylic acid derivates.", VISNIK FARMATSII, vol. 4, 2008, pages 75 - 77, XP008178899
AGARWAL, S. K. ET AL.: "Synthesis, characterization and screening of antibacterial activity of some new Mannich bases", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 57, no. 12, 1980, pages 1240 - 1241, XP008178893
UKITA, TYUNOSHIN ET AL.: "Antibacterial properties of compounds containing the tricarbonylmethane group. IX. Effects of nitrogenous radicals in the side-chains of 3-acyl-4-hydroxycoumarins and their derivatives", PHARMACEUTICAL BULLETIN, vol. 1, 1953, pages 255 - 260, XP055247034
PATONAY, T. ET AL.: "Synthesis, antibacterial and antifungal activity of 4-hydroxycoumarin derivatives, analogs of novobiocin", PHARMAZIE, vol. 39, no. 2, 1984, pages 86 - 91, XP001526727
LEE, BYUNG H. ET AL.: "Anthelmintic p-hydroxyketoamides (BKAS)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 23, 1998, pages 3317 - 3320, XP004143750
FONTAINE, LOUIS ET AL.: "Antinflammatory activity of coumarins, indandiones, and acylindandiones related to oral anticoagulants", MEDICINA ET PHARMACOLOGIA EXPERIMENTALIS, vol. 17, no. 6, 1967, pages 497 - 507, XP008178895
FONTAINE, LOUIS ET AL.: "Choleretic activities of coumarins, indandiones, and acylindandiones related to roal anticoagulants", CHIMICA THERAPEUTICA, vol. 2, no. 6, 1967, pages 430 - 440
LIN, PEN-YUAN ET AL.: "Synthesis and antibacterial activities of novel 4-hydroxy, 7-hydroxy- and 3-carboxycoumarin derivatives", MOLECULES, vol. 17, no. 9, 2012, pages 10846 - 10863, XP055247092
BALUJA, SHIPRA ET AL.: "Antibacterial studies of some metal complexes of coumarin chalcones: part - II", JOURNAL OF THE INSTITUTION OF CHEMISTS, vol. 81, no. 4, 2009, pages 102 - 109, XP008178896
KLOSA, JOSEF: "Synthesis of 6-methyl-4- hydroxycoumarin derivatives", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 289, 1956, pages 156 - 161, XP008178891
KLOSA, JOSEF: "Synthesis of 4-hydroxy-6- chlorocoumarin derivatives", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 289, 1956, pages 143 - 150, XP008178897
TRKOVNIK, M. ET AL.: "Synthesis of 4-hydroxycoumarins with hogher monobasic carboxylic acids", CROATICA CHEMICA ACTA, vol. 40, 1968, pages 91 - 92, XP008178892
MULWAD, V. V. ET AL.: "Synthesis of some antibacterial compounds from 4-hydroxycoumarin", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 42B, no. 9, 2003, pages 2091 - 2096, XP055247137
See also references of EP 2910547A4
"Frontiers in Antimicrobial Resistance", 2005, ASM PRESS AMERICAN SOCIETY FOR MICROBIOLOGY
JEVONS, M.P., BR. MED. J., 1961, pages 124 - 125
SIEVERT, D.M. ET AL.: "Staphylococcus aureus Resistant to Vancomycin-United States", MMWR, vol. 51, 2002, pages 565 - 567
AGARWAL, S. K. ET AL.: "Synthesis, characterization and screening of antibacterial activity of some new Mannich bases", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 57, no. 12, 1980, pages 1240 - 1241, XP008178893
UKITA, TYUNOSHIN ET AL.: "Antibacterial properties of compounds containing the tricarbonylmethane group. IX. Effects of nitrogenous radicals in the side-chains of 3-acyl-4-hydroxycoumarins and their derivatives", PHARMACEUTICAL BULLETIN, vol. 1, 1953, pages 255 - 260, XP055247034
PATONAY, T. ET AL.: "Synthesis, antibacterial and antifungal activity of 4-hydroxycoumarin derivatives, analogs of novobiocin", PHARMAZIE, vol. 39, no. 2, 1984, pages 86 - 91, XP001526727
LEE, BYUNG H. ET AL.: "Anthelmintic p-hydroxyketoamides (BKAS)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 23, 1998, pages 3317 - 3320, XP004143750
FONTAINE, LOUIS ET AL.: "Antinflammatory activity of coumarins, indandiones, and acylindandiones related to oral anticoagulants", MEDICINA ET PHARMACOLOGIA EXPERIMENTALIS, vol. 17, no. 6, 1967, pages 497 - 507, XP008178895
FONTAINE, LOUIS ET AL.: "Choleretic activities of coumarins, indandiones, and acylindandiones related to roal anticoagulants", CHIMICA THERAPEUTICA, vol. 2, no. 6, 1967, pages 430 - 440
LIN, PEN-YUAN ET AL.: "Synthesis and antibacterial activities of novel 4-hydroxy, 7-hydroxy- and 3-carboxycoumarin derivatives", MOLECULES, vol. 17, no. 9, 2012, pages 10846 - 10863, XP055247092
BALUJA, SHIPRA ET AL.: "Antibacterial studies of some metal complexes of coumarin chalcones: part - II", JOURNAL OF THE INSTITUTION OF CHEMISTS, vol. 81, no. 4, 2009, pages 102 - 109, XP008178896
KLOSA, JOSEF: "Synthesis of 6-methyl-4- hydroxycoumarin derivatives", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 289, 1956, pages 156 - 161, XP008178891
KLOSA, JOSEF: "Synthesis of 4-hydroxy-6- chlorocoumarin derivatives", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 289, 1956, pages 143 - 150, XP008178897
TRKOVNIK, M. ET AL.: "Synthesis of 4-hydroxycoumarins with hogher monobasic carboxylic acids", CROATICA CHEMICA ACTA, vol. 40, 1968, pages 91 - 92, XP008178892
MULWAD, V. V. ET AL.: "Synthesis of some antibacterial compounds from 4-hydroxycoumarin", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 42B, no. 9, 2003, pages 2091 - 2096, XP055247137
See also references of EP 2910547A4
"Frontiers in Antimicrobial Resistance", 2005, ASM PRESS AMERICAN SOCIETY FOR MICROBIOLOGY
JEVONS, M.P., BR. MED. J., 1961, pages 124 - 125
SIEVERT, D.M. ET AL.: "Staphylococcus aureus Resistant to Vancomycin-United States", MMWR, vol. 51, 2002, pages 565 - 567
Attorney, Agent or Firm:
HIROTA, Koichi et al. (JP)
Koichi Hirota (JP)
Koichi Hirota (JP)
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