WO2007039749A3 - Antibacterial pyrrols - Google Patents

Antibacterial pyrrols Download PDF

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Publication number
WO2007039749A3
WO2007039749A3 PCT/GB2006/003713 GB2006003713W WO2007039749A3 WO 2007039749 A3 WO2007039749 A3 WO 2007039749A3 GB 2006003713 W GB2006003713 W GB 2006003713W WO 2007039749 A3 WO2007039749 A3 WO 2007039749A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkynylthiocarbonyl
alkenylthiocarbonyl
alkynylcarbonyl
alkylthiocarbonyl
alkenyloxycarbonyl
Prior art date
Application number
PCT/GB2006/003713
Other languages
French (fr)
Other versions
WO2007039749A2 (en
Inventor
Eric Lattmann
Simon Dunn
Nison Sattayasai
Suwanna Niamsit
Original Assignee
Univ Aston
Eric Lattmann
Simon Dunn
Nison Sattayasai
Suwanna Niamsit
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 Univ Aston, Eric Lattmann, Simon Dunn, Nison Sattayasai, Suwanna Niamsit filed Critical Univ Aston
Priority to EP06794664A priority Critical patent/EP1940390A2/en
Priority to CA002624501A priority patent/CA2624501A1/en
Publication of WO2007039749A2 publication Critical patent/WO2007039749A2/en
Publication of WO2007039749A3 publication Critical patent/WO2007039749A3/en

Links

Classifications

    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/456—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 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 other ring carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Use of a compound of formula (I), as shown in the description, or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of bacterial infection or disease: wherein, in formula (I), A is -NR1-, -O- or -S R1 is selected from hydrogen, a halogen or a substituted or unsubstituted heterocyclic, alkyl, alkyloxy, alkylthio, alkylcarbonyl, alkyloxycarbonyl, alkylthiocarbonyl, alkenyl, alkenylcarbony, alkenyloxycarbonyl, alkenylthiocarbonyl, alkynyl, alkynylcarbonyl, alkynyloxcarbonyl, alkynylthiocarbonyl, aryl, benzyl, arylcarbonyl or aryloxycarbonyl group; and Y and Z are not identical and are independently selected from hydrogen, a halogen, or a substituted or unsubstituted heterocyclic, alkyl, alkyloxy, alkylthio, alkylcarbonyl, alkyloxycarbonyl, alkylthiocarbonyl, alkenyl, alkenyloxy, alkenylthio, alkenylcarbonyl, alkenyloxycarbonyl, alkenylthiocarbonyl, alkynyl, alkynyloxy, alkynylthio, alkynylcarbonyl, alkynyloxycarbonyl, alkynylthiocarbonyl, aryl, benzyl, aryloxy, arylthio, arylcarbonyl, aryloxycarbonyl or arylthiocarbonyl, a NR1R2 group wherein R1' and R2 are as defined for R1 or NR1'R2 is NH2.
PCT/GB2006/003713 2005-10-06 2006-10-06 Antibacterial pyrrols WO2007039749A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP06794664A EP1940390A2 (en) 2005-10-06 2006-10-06 Antibacterial pyrrols
CA002624501A CA2624501A1 (en) 2005-10-06 2006-10-06 Antibacterial pyrrols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0520368.2 2005-10-06
GBGB0520368.2A GB0520368D0 (en) 2005-10-06 2005-10-06 Antibacterial pyrrols

Publications (2)

Publication Number Publication Date
WO2007039749A2 WO2007039749A2 (en) 2007-04-12
WO2007039749A3 true WO2007039749A3 (en) 2008-05-08

Family

ID=35429943

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2006/003713 WO2007039749A2 (en) 2005-10-06 2006-10-06 Antibacterial pyrrols

Country Status (4)

Country Link
EP (1) EP1940390A2 (en)
CA (1) CA2624501A1 (en)
GB (1) GB0520368D0 (en)
WO (1) WO2007039749A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100179214A1 (en) 2006-05-19 2010-07-15 Somaxon Pharmaceuticals, Inc. Doxepin trans isomers and isomeric mixtures and methods of using the same to treat sleep disorders
JP5210598B2 (en) * 2007-11-06 2013-06-12 花王株式会社 Autoinducer-2 inhibitor and preventive and / or therapeutic agent for infectious diseases

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337584A (en) * 1967-01-06 1967-08-22 Squibb & Sons Inc N-substituted maleimide compounds
FR1559600A (en) * 1966-04-23 1969-03-14 Fujisawa Pharm Co PROCESS FOR MANUFACTURING DERIVATIVES OF 2-PHENYL MALEIMIDE AND SUCCINIMIDE
DE1770042A1 (en) * 1968-03-23 1971-04-08 Basf Ag Process for the preparation of alpha, ss-dihalo-gamma-hydroxycrotone lactams
DE1770041A1 (en) * 1968-03-23 1971-09-16 Basf Ag Process for the preparation of alpha-amino-maleimides
US3816451A (en) * 1971-11-02 1974-06-11 Abbott Lab Maleimide derivatives as plant growth regulators
US3890270A (en) * 1974-04-10 1975-06-17 Tenneco Chem Polyvinyl halide resin compositions
US4353734A (en) * 1977-07-25 1982-10-12 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Maleimide and succinimide derivatives and herbicidal method of use thereof
EP0098953A2 (en) * 1982-06-12 1984-01-25 Bayer Ag Substituted maleic-acid imides, process for their preparation and their use as pesticides
JPS5931702A (en) * 1982-08-16 1984-02-20 Earth Chem Corp Ltd Repellent composition against noxious insect and acarid
JPH01221302A (en) * 1987-10-26 1989-09-04 Katayama Chem Works Co Ltd Bactericide for industry and sterilization
JPH01299280A (en) * 1988-05-24 1989-12-04 Takara Shuzo Co Ltd Novel antibiotic substance h9 and production thereof
JPH05294952A (en) * 1992-04-16 1993-11-09 Wakamoto Pharmaceut Co Ltd Antibiotic substance wap-4068, its derivative and production thereof
JPH10316510A (en) * 1997-05-14 1998-12-02 Nissan Chem Ind Ltd N-0194 and its production
WO1999065483A1 (en) * 1998-05-05 1999-12-23 Astrazeneca Ab Mycobacterial inhibitors
JP2003012413A (en) * 2001-07-03 2003-01-15 Takeda Chem Ind Ltd Industrial composition
JP2004238309A (en) * 2003-02-05 2004-08-26 Soda Aromatic Co Ltd Melanin production inhibitor
JP2005218320A (en) * 2004-02-03 2005-08-18 Ajinomoto Co Inc New antifungal agent fa424a(n), fa424a(o), fa424b and fa424d
US20050197384A1 (en) * 2004-03-08 2005-09-08 Masao Hattori Novel mixture and compounds from mycelia of Antrodia camphorata and use thereof

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1559600A (en) * 1966-04-23 1969-03-14 Fujisawa Pharm Co PROCESS FOR MANUFACTURING DERIVATIVES OF 2-PHENYL MALEIMIDE AND SUCCINIMIDE
US3337584A (en) * 1967-01-06 1967-08-22 Squibb & Sons Inc N-substituted maleimide compounds
DE1770042A1 (en) * 1968-03-23 1971-04-08 Basf Ag Process for the preparation of alpha, ss-dihalo-gamma-hydroxycrotone lactams
DE1770041A1 (en) * 1968-03-23 1971-09-16 Basf Ag Process for the preparation of alpha-amino-maleimides
US3816451A (en) * 1971-11-02 1974-06-11 Abbott Lab Maleimide derivatives as plant growth regulators
US3890270A (en) * 1974-04-10 1975-06-17 Tenneco Chem Polyvinyl halide resin compositions
US4353734A (en) * 1977-07-25 1982-10-12 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Maleimide and succinimide derivatives and herbicidal method of use thereof
EP0098953A2 (en) * 1982-06-12 1984-01-25 Bayer Ag Substituted maleic-acid imides, process for their preparation and their use as pesticides
JPS5931702A (en) * 1982-08-16 1984-02-20 Earth Chem Corp Ltd Repellent composition against noxious insect and acarid
JPH01221302A (en) * 1987-10-26 1989-09-04 Katayama Chem Works Co Ltd Bactericide for industry and sterilization
JPH01299280A (en) * 1988-05-24 1989-12-04 Takara Shuzo Co Ltd Novel antibiotic substance h9 and production thereof
JPH05294952A (en) * 1992-04-16 1993-11-09 Wakamoto Pharmaceut Co Ltd Antibiotic substance wap-4068, its derivative and production thereof
JPH10316510A (en) * 1997-05-14 1998-12-02 Nissan Chem Ind Ltd N-0194 and its production
WO1999065483A1 (en) * 1998-05-05 1999-12-23 Astrazeneca Ab Mycobacterial inhibitors
JP2003012413A (en) * 2001-07-03 2003-01-15 Takeda Chem Ind Ltd Industrial composition
JP2004238309A (en) * 2003-02-05 2004-08-26 Soda Aromatic Co Ltd Melanin production inhibitor
JP2005218320A (en) * 2004-02-03 2005-08-18 Ajinomoto Co Inc New antifungal agent fa424a(n), fa424a(o), fa424b and fa424d
US20050197384A1 (en) * 2004-03-08 2005-09-08 Masao Hattori Novel mixture and compounds from mycelia of Antrodia camphorata and use thereof

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
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CARDENAS ET AL: "Production of tricarboxylic acid anhydrides from fatty acids by a lipase-producing strain of Pseudomonas cepacia", BIOCATALYSIS AND BIOTRANSFORMATION, HARWOOD ACADEMIC PUBL., BASEL, CH, vol. 20, no. 2, 2002, pages 117 - 128, XP009095933, ISSN: 1024-2422 *
COONEY D A ET AL: "MALEIMIDE BIOCHEMICAL PHARMACOLOGIC AND TOXICOLOGIC STUDIES INTERACTION WITH L ASPARAGINASE METABOLISM", BIOCHEMICAL PHARMACOLOGY, vol. 27, no. 2, 1978, pages 151 - 166, XP002413425, ISSN: 0006-2952 *
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DAVIS P D ET AL: "INHIBITORS OF PROTEIN KINASE C 1. 2,3-BISARYLMALEIMIDES", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 35, no. 1, 1992, pages 177 - 184, XP000910195, ISSN: 0022-2623 *
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HENTZER M ET AL: "Pharmacological inhibition of quorum sensing for the treatment of chronic bacterial infections", JOURNAL OF CLINICAL INVESTIGATION, NEW YORK, NY, US, vol. 112, no. 9, November 2003 (2003-11-01), pages 1300 - 1307, XP002316251, ISSN: 0021-9738 *
JABBAR A ET AL: "Isolation and in vitro antibacterial screening of a tricarboxylic acid anhydride from Penicillium sp", PHARMAZIE, vol. 50, no. 10, 1995, pages 706 - 707, XP001538032, ISSN: 0031-7144 *
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OIKAWA HIDEAKI ET AL: "Synthetic study of tautomycetin: Synthesis of two large subunits", TETRAHEDRON LETTERS, vol. 38, no. 45, 10 November 1997 (1997-11-10), pages 7897 - 7900, XP004097200, ISSN: 0040-4039 *
ROTHHAAS, ALEXANDER: "Reaction of hydroxymaleic anhydride with ammonia and aliphatic amines. Preparation of substituted maleinimides", ANN. , 501, 295 -304, 1933, XP002413426 *
SAHOO M K ET AL: "Facile routes to alkoxymaleimides/maleic anhydrides", SYNTHESIS 2003 GERMANY, no. 3, 2003, pages 346 - 349, XP002469073, ISSN: 0039-7881 *
WATANABE S ET AL: "ANTIMICROBIAL ACTIVITY OF SOME N-(ARYLALKYL)MALEIMIDES", PESTICIDE SCIENCE, ELSEVIER APPLIED SCIENCE PUBLISHER. BARKING, GB, vol. 34, no. 2, January 1992 (1992-01-01), pages 99 - 104, XP000287971, ISSN: 0031-613X *
WINTERFELDT ET AL.: "Die Reaktionen von Mucochlorsäure-Derivate...", CHEM. BER., vol. 101, 1968, pages 3163 - 3171, XP002469071 *

Also Published As

Publication number Publication date
WO2007039749A2 (en) 2007-04-12
EP1940390A2 (en) 2008-07-09
GB0520368D0 (en) 2005-11-16
CA2624501A1 (en) 2007-04-12

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