WO2001028537A3 - Bissulfonamide derivatives as enzyme inhibitors - Google Patents

Bissulfonamide derivatives as enzyme inhibitors Download PDF

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Publication number
WO2001028537A3
WO2001028537A3 PCT/GB2000/003944 GB0003944W WO0128537A3 WO 2001028537 A3 WO2001028537 A3 WO 2001028537A3 GB 0003944 W GB0003944 W GB 0003944W WO 0128537 A3 WO0128537 A3 WO 0128537A3
Authority
WO
WIPO (PCT)
Prior art keywords
aryl
heteroaryl
alkyl
enzyme inhibitors
bissulfonamide
Prior art date
Application number
PCT/GB2000/003944
Other languages
French (fr)
Other versions
WO2001028537A2 (en
Inventor
David Madge
Grant Wishart
Mark Dolman
Peter Maunder
Original Assignee
Arrow Therapeutics Ltd
David Madge
Grant Wishart
Mark Dolman
Peter Maunder
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 Arrow Therapeutics Ltd, David Madge, Grant Wishart, Mark Dolman, Peter Maunder filed Critical Arrow Therapeutics Ltd
Priority to EP00968096A priority Critical patent/EP1239852A2/en
Priority to AU78054/00A priority patent/AU7805400A/en
Priority to KR1020027004720A priority patent/KR20020057973A/en
Priority to JP2001531367A priority patent/JP2003512319A/en
Priority to CA002387593A priority patent/CA2387593A1/en
Publication of WO2001028537A2 publication Critical patent/WO2001028537A2/en
Publication of WO2001028537A3 publication Critical patent/WO2001028537A3/en

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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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • 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
    • 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
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)

Abstract

Bissulfonamide derivatives of formula (I) are capable of inhibiting: a) the biosynthesis of aromatic amino acids via the shikimate pathway and b) the catabolism of quinic acid, wherein: Ar is an aryl or heteroaryl group; R1 and R2 are the same or different and each represent hydrogen or alkyl or R1 and R2 together form a C1-C3 alkylene group, -CO- or -CS-; and R3 and R4 are the same or different and each represent -alkyl-aryl, -alkyl-heteroaryl, -alkenyl-aryl, -alkenyl-heteroaryl, -alkynyl-aryl-alkynyl-heterorayl, aryl or heteroaryl.
PCT/GB2000/003944 1999-10-15 2000-10-13 Bissulfonamide derivatives as enzyme inhibitors WO2001028537A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP00968096A EP1239852A2 (en) 1999-10-15 2000-10-13 Bissulfonamide derivatives as enzyme inhibitors
AU78054/00A AU7805400A (en) 1999-10-15 2000-10-13 Enzyme inhibitors
KR1020027004720A KR20020057973A (en) 1999-10-15 2000-10-13 Enzyme inhibitors
JP2001531367A JP2003512319A (en) 1999-10-15 2000-10-13 Enzyme inhibitors
CA002387593A CA2387593A1 (en) 1999-10-15 2000-10-13 Enzyme inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9924522.7 1999-10-15
GBGB9924522.7A GB9924522D0 (en) 1999-10-15 1999-10-15 Enzyme inhibitors

Publications (2)

Publication Number Publication Date
WO2001028537A2 WO2001028537A2 (en) 2001-04-26
WO2001028537A3 true WO2001028537A3 (en) 2001-06-14

Family

ID=10862854

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/003944 WO2001028537A2 (en) 1999-10-15 2000-10-13 Bissulfonamide derivatives as enzyme inhibitors

Country Status (8)

Country Link
EP (1) EP1239852A2 (en)
JP (1) JP2003512319A (en)
KR (1) KR20020057973A (en)
AU (1) AU7805400A (en)
CA (1) CA2387593A1 (en)
GB (1) GB9924522D0 (en)
WO (1) WO2001028537A2 (en)
ZA (1) ZA200202897B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AUPR738301A0 (en) * 2001-08-30 2001-09-20 Starpharma Limited Chemotherapeutic agents
EP1534284B1 (en) * 2002-02-28 2011-07-27 Temple University - Of The Commonwealth System of Higher Education Amino-substituted sulfonanilides and derivatives thereof for treating proliferative disorders
WO2004091611A1 (en) * 2003-04-11 2004-10-28 Regents Of The University Of California A California Corporation Carbonic anhydrase inhibitors to eradicate helicobacter pylori
JP2008517930A (en) * 2004-10-21 2008-05-29 トランス テック ファーマ，インコーポレイテッド Bissulfonamide compounds, compositions, and methods of use as agonists of GalR1
GB0526255D0 (en) 2005-12-22 2006-02-01 Novartis Ag Organic compounds
CA2640304A1 (en) * 2006-02-13 2007-08-23 Laboratoires Serono S.A. Sulfonamide derivatives for the treatment of bacterial infections
WO2008114831A1 (en) * 2007-03-20 2008-09-25 National University Corporation Okayama University Antibacterial agent having sulfonamide group
EP2955173B1 (en) 2010-12-16 2017-10-04 Allergan, Inc. 1,2-bis-sulfonamide derivatives as chemokine receptor modulators
GB201223308D0 (en) * 2012-12-21 2013-02-06 Univ Sunderland Enzyme inhibitors
CN109042741A (en) * 2018-06-28 2018-12-21 贵州省松桃武陵源苗王茶业有限公司 A kind of microbial pesticide of the tealeaves prevention and control of plant diseases, pest control and its application
CN116283677B (en) * 2023-02-24 2024-05-17 中国科学院广州生物医药与健康研究院 Small molecular chemical cross-linking agent and preparation method and application thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ABDEL BARY, HAMED M. ET AL: "Reaction with coumarin. IV", AFINIDAD (1995), 52(459), 344-6, XP000984616 *
FRIEDRICHSEN, WILLY ET AL: "Cycloadditions with o-benzoquinone diimines, IV. Reactions of N,N'-diarylsulfonyl-o-benzoquinone diimines with fulvenes, I", JUSTUS LIEBIGS ANN. CHEM. (1978), (7), 1146-60, XP000984579 *
MARKOVSKII, L. N. ET AL: "Bis- and tris(crown ether) sulfonamides", ZH. ORG. KHIM. (1990), 26(9), 2014-18, XP000984582 *
MASSACRET, MAGALI ET AL: "Palladium(0)-catalyzed asymmetric synthesis of 1,2,3,4-tetrahydro-2- vinylquinoxalines", EUR. J. ORG. CHEM. (1999), (1), 129-134, XP000984502 *

Also Published As

Publication number Publication date
ZA200202897B (en) 2003-04-14
KR20020057973A (en) 2002-07-12
GB9924522D0 (en) 1999-12-15
JP2003512319A (en) 2003-04-02
WO2001028537A2 (en) 2001-04-26
EP1239852A2 (en) 2002-09-18
AU7805400A (en) 2001-04-30
CA2387593A1 (en) 2001-04-26

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