WO2002022137A1 - Analogues de $g(b)-lactamine et utilisations de ceux-ci - Google Patents

Analogues de $g(b)-lactamine et utilisations de ceux-ci Download PDF

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Publication number
WO2002022137A1
WO2002022137A1 PCT/US2001/029108 US0129108W WO0222137A1 WO 2002022137 A1 WO2002022137 A1 WO 2002022137A1 US 0129108 W US0129108 W US 0129108W WO 0222137 A1 WO0222137 A1 WO 0222137A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkene
heteroalkyl
cyclic
heterocyclic
Prior art date
Application number
PCT/US2001/029108
Other languages
English (en)
Inventor
Brian K. Shoichet
Larry C. Blasczcak
Fabio Prati
Emilia Caselli
Original Assignee
Shoichet Brian K
Blasczcak Larry C
Fabio Prati
Emilia Caselli
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 Shoichet Brian K, Blasczcak Larry C, Fabio Prati, Emilia Caselli filed Critical Shoichet Brian K
Priority to AU2001292732A priority Critical patent/AU2001292732A1/en
Publication of WO2002022137A1 publication Critical patent/WO2002022137A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • 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
    • A61K31/69—Boron compounds

Definitions

  • R 7 is H or R 7 is alkyl or heteroalkyl, each of which may be unsubstituted or substituted with one or more R 4 groups; m is 1-4; and n is 0-2; or a pharmaceutically-acceptable salt thereof.
  • Cyclic alkene means a structure containing from 1 to 3 rings, each ring containing from 4 to 7 carbon atoms, and at least one double bond. One, two or all three of the rings may be aromatic.
  • Representative cyclic alkenes include -C 6 H 5 and
  • ⁇ -lactam antibiotics are known (see above), ⁇ -lactam antibiotics are effective (in the absence of resistance) against a wide range of bacterial infections. These include those caused by both gram-positive and gram-negative bacteria, for example, bacteria of the genus Staphylococcus (such as Staphylococcus aureus and Staphylococcus epidermidis), Streptococcus (such as Streptococcus agalactine, Streptococcus penumoniae and Streptococcus faecalis), Micrococcus (such as Micrococcus luteus), Bacillus (such as Bacillus subtilis), Listerella (such as Listerella monocytogenes), Escherichia (such as Escherichia coli), Klebsiella (such as Klebsiella pneumoniae), Proteus (such as Proteus mirab ⁇ lis and Proteus vulgaris), Salmonella (such as Salmonella typhosa), Shig
  • a tablet may be made by compression or molding, optionally with one or more accessory ingredients.
  • Compressed tablets may be prepared using binder (for example, gelatin or hydroxypropylmethyl cellulose), lubricant, inert diluent, preservative, disintegrant (for example, sodium starch glycolate or cross-linked sodium carboxymethyl cellulose), surface-active or dispersing agent.
  • Molded tablets may be made by molding in a suitable machine a mixture of the powdered active ingredient(s) moistened with an inert liquid diluent.
  • compositions may also contain adjuvants such as wetting agents, emulsifying agents and dispersing agents. It may also be desirable to include isotonic agents, such as sugars, sodium chloride, and the like in the compositions, h addition, prolonged absorption of the injectable pharmaceutical form maybe brought about by the inclusion of agents which delay absorption such as aluminum monostearate and gelatin.
  • Extemporaneous injection solutions and suspensions maybe prepared from sterile powders, granules and tablets of the type described above.
  • compositions of the present invention may also be used in the form of veterinary formulations, including those adapted for the following: (1) oral administration, for example, drenches (aqueous or non-aqueous solutions or suspensions), tablets, boluses, powders, granules or pellets for admixture with feed stuffs, pastes for application to the tongue; (2) parenteral administration, for example, by subcutaneous, intramuscular or intravenous injection as, for example, a sterile solution or suspension or, when appropriate, by intramammary injection where a suspension or solution is introduced into the udder of the animal via its teat; (3) topical application, for example, as a cream, ointment or spray applied to the skin; or (4) mtravaginally, for example, as a pessary, cream or foam.
  • oral administration for example, drenches (aqueous or non-aqueous solutions or suspensions), tablets, boluses, powders, granules or pellets for admixture

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé permettant de traiter une infection bactérienne résistante à la β-lactamine à l'aide d'une combinaison d'une β-lactamine et d'un analogue de β-lactamine. L'invention concerne également un procédé permettant l'inhibition d'une β-lactamase comprenant la mise en contact de la β-lactamase avec un analogue de β-lactamine. Enfin, l'invention concerne des composés qui sont des analogues de β-lactamine et des compositions contenant des analogues de β-lactamine. Les analogues de β-lactamine correspondent à la formule (I) dans laquelle R2 correspond à la définition donnée dans la description.
PCT/US2001/029108 2000-09-12 2001-09-12 Analogues de $g(b)-lactamine et utilisations de ceux-ci WO2002022137A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001292732A AU2001292732A1 (en) 2000-09-12 2001-09-12 Beta-lactam analogs and uses therefor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23205500P 2000-09-12 2000-09-12
US60/232,055 2000-09-12

Publications (1)

Publication Number Publication Date
WO2002022137A1 true WO2002022137A1 (fr) 2002-03-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/029108 WO2002022137A1 (fr) 2000-09-12 2001-09-12 Analogues de $g(b)-lactamine et utilisations de ceux-ci

Country Status (2)

Country Link
AU (1) AU2001292732A1 (fr)
WO (1) WO2002022137A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7541381B2 (en) 2002-02-19 2009-06-02 Northwestern University Non-covalent inhibitors of AmpC β-lactamase
US9012491B2 (en) 2011-08-31 2015-04-21 Rempex Pharmaceuticals, Inc. Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
US9101638B2 (en) 2013-01-04 2015-08-11 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9132140B2 (en) 2013-01-04 2015-09-15 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9156858B2 (en) 2012-05-23 2015-10-13 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9296763B2 (en) 2010-08-10 2016-03-29 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US9642869B2 (en) 2013-01-04 2017-05-09 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9687497B1 (en) 2014-05-05 2017-06-27 Rempex Pharmaceuticals, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
US9963467B2 (en) 2014-05-19 2018-05-08 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US10206937B2 (en) 2014-07-01 2019-02-19 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US10294249B2 (en) 2016-06-30 2019-05-21 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US10385074B2 (en) 2014-05-05 2019-08-20 Rempex Pharmaceuticals, Inc. Synthesis of boronate salts and uses thereof
US10561675B2 (en) 2012-06-06 2020-02-18 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US10618918B2 (en) 2015-03-17 2020-04-14 Qpex Biopharma, Inc. Substituted boronic acids as antimicrobials
US10662205B2 (en) 2014-11-18 2020-05-26 Qpex Biopharma, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US11286270B2 (en) 2017-10-11 2022-03-29 Qpex Biopharma, Inc. Boronic acid derivatives and synthesis thereof
US11999759B2 (en) 2021-11-05 2024-06-04 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015473A (en) * 1984-01-30 1991-05-14 Pfizer Inc. 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
US5494666A (en) * 1994-03-11 1996-02-27 Hoffmann-La Roche Inc. β-lactam compounds
US5637579A (en) * 1993-08-24 1997-06-10 Hoffmann-La Roche Inc. Penam derivatives
US6075014A (en) * 1997-06-13 2000-06-13 Northwestern University Inhibitors of β-lactamases and uses therefor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015473A (en) * 1984-01-30 1991-05-14 Pfizer Inc. 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
US5637579A (en) * 1993-08-24 1997-06-10 Hoffmann-La Roche Inc. Penam derivatives
US5494666A (en) * 1994-03-11 1996-02-27 Hoffmann-La Roche Inc. β-lactam compounds
US6075014A (en) * 1997-06-13 2000-06-13 Northwestern University Inhibitors of β-lactamases and uses therefor

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7541381B2 (en) 2002-02-19 2009-06-02 Northwestern University Non-covalent inhibitors of AmpC β-lactamase
US9694025B2 (en) 2010-08-10 2017-07-04 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US10639318B2 (en) 2010-08-10 2020-05-05 Rempex Pharmaceuticals, Inc. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives
US11090319B2 (en) 2010-08-10 2021-08-17 Melinta Subsidiary Corp. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives
US9296763B2 (en) 2010-08-10 2016-03-29 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US11684629B2 (en) 2010-08-10 2023-06-27 Melinta Subsidiary Corp. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives
US10183034B2 (en) 2010-08-10 2019-01-22 Rempex Pharmaceuticals, Inc. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives
US10004758B2 (en) 2010-08-10 2018-06-26 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and methods of making the same
US10172874B2 (en) 2010-08-10 2019-01-08 Rempex Pharmaceuticals, Inc. Pharmaceutical compositions comprising cyclic boronic acid ester derivatives
US9012491B2 (en) 2011-08-31 2015-04-21 Rempex Pharmaceuticals, Inc. Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
US9156858B2 (en) 2012-05-23 2015-10-13 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US11007206B2 (en) 2012-06-06 2021-05-18 Melinta Subsidiary Corp. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US10561675B2 (en) 2012-06-06 2020-02-18 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9642869B2 (en) 2013-01-04 2017-05-09 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9132140B2 (en) 2013-01-04 2015-09-15 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9101638B2 (en) 2013-01-04 2015-08-11 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9687497B1 (en) 2014-05-05 2017-06-27 Rempex Pharmaceuticals, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
US10385074B2 (en) 2014-05-05 2019-08-20 Rempex Pharmaceuticals, Inc. Synthesis of boronate salts and uses thereof
US10669292B2 (en) 2014-05-05 2020-06-02 Rempex Pharmaceuticals, Inc. Synthesis of boronate salts and uses thereof
US9963467B2 (en) 2014-05-19 2018-05-08 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US10206937B2 (en) 2014-07-01 2019-02-19 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US10662205B2 (en) 2014-11-18 2020-05-26 Qpex Biopharma, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US10618918B2 (en) 2015-03-17 2020-04-14 Qpex Biopharma, Inc. Substituted boronic acids as antimicrobials
US10570159B2 (en) 2016-06-30 2020-02-25 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US11180512B2 (en) 2016-06-30 2021-11-23 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US10294249B2 (en) 2016-06-30 2019-05-21 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US11286270B2 (en) 2017-10-11 2022-03-29 Qpex Biopharma, Inc. Boronic acid derivatives and synthesis thereof
US11999759B2 (en) 2021-11-05 2024-06-04 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof

Also Published As

Publication number Publication date
AU2001292732A1 (en) 2002-03-26

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