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WO2002085841A3 - Derives de catechol substitues, derivant d'acides amines secondaires polybasiques, leur procede de production et leur utilisation - Google Patents

Derives de catechol substitues, derivant d'acides amines secondaires polybasiques, leur procede de production et leur utilisation Download PDF

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Publication number
WO2002085841A3
WO2002085841A3 PCT/EP2002/002071 EP0202071W WO02085841A3 WO 2002085841 A3 WO2002085841 A3 WO 2002085841A3 EP 0202071 W EP0202071 W EP 0202071W WO 02085841 A3 WO02085841 A3 WO 02085841A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
compounds
amino acids
secondary amino
aryl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2002/002071
Other languages
German (de)
English (en)
Other versions
WO2002085841A2 (fr
Inventor
Lothar Heinisch
Steffen Wittmann
Ina Scherlitz-Hofmann
Thomas Stoiber
Albrecht Berg
Ute Moellmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gruenenthal GmbH
Original Assignee
Gruenenthal GmbH
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 Gruenenthal GmbH filed Critical Gruenenthal GmbH
Publication of WO2002085841A2 publication Critical patent/WO2002085841A2/fr
Publication of WO2002085841A3 publication Critical patent/WO2002085841A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
    • C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne de nouveaux dérivés de catéchol substitués, dérivant d'acides aminés secondaires polybasiques, ainsi que des structures analogues de formule générale (I). Les composés selon cette invention sont efficaces en tant que sidérophores en cas de mycobactéries et de souches de bactéries de type Gram négatif, notamment de Pseudomonas et de souches E.coli et Salmonella. Ils peuvent servir de véhicules de transport pour introduire des substances actives, telles que des antibiotiques (sous forme de conjugués sidérophore-antibiotique), dans des cellules de bactéries et ainsi améliorer ou élargir leur efficacité antibactérienne dans une plus large mesure que les composés connus jusqu'à présent. De plus, lesdits composés sont, sous formes promédicamenteuses potentielles pour des chélateurs de fer, adaptés à un usage en cas de maladies basées sur un dysfonctionnement du métabolisme du fer. Dans la formule (I), R1 représente H, alkyle ou aryle, R2 et R3 représentent H ou acyle, R4 et R5 représentent H, alkyle ou aryle, R6 et R7 représentent H, alkyle ou des groupes catécholate, éventuellement sous forme acylée ou avec des groupes espaceurs, X et Z représentent des composés directs ou interrompus par des groupes espaceurs définis et Y représente OH (en tant qu'acides libres, sous forme de leurs sels ou de leurs esters facilement clivables).
PCT/EP2002/002071 2001-03-01 2002-02-27 Derives de catechol substitues, derivant d'acides amines secondaires polybasiques, leur procede de production et leur utilisation Ceased WO2002085841A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001111164 DE10111164A1 (de) 2001-03-01 2001-03-01 Neue substituierte Catecholderivate abgeleitet von mehrbasischen sekundären Aminosäuren, Verfahren zu ihrer Herstellung und ihre Anwendung
DE10111164.9 2001-03-01

Publications (2)

Publication Number Publication Date
WO2002085841A2 WO2002085841A2 (fr) 2002-10-31
WO2002085841A3 true WO2002085841A3 (fr) 2003-03-20

Family

ID=7676736

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/002071 Ceased WO2002085841A2 (fr) 2001-03-01 2002-02-27 Derives de catechol substitues, derivant d'acides amines secondaires polybasiques, leur procede de production et leur utilisation

Country Status (2)

Country Link
DE (1) DE10111164A1 (fr)
WO (1) WO2002085841A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004014844A2 (fr) 2002-08-09 2004-02-19 Transtech Pharma, Inc. Composes aryle et heteroaryle et procedes de modulation de la coagulation
WO2005014534A1 (fr) 2003-08-08 2005-02-17 Transtech Pharma, Inc. Composes aryle et heteroaryle, compositions, et methodes d'utilisation
US7208601B2 (en) 2003-08-08 2007-04-24 Mjalli Adnan M M Aryl and heteroaryl compounds, compositions, and methods of use
CN1832920A (zh) 2003-08-08 2006-09-13 特兰斯泰克制药公司 芳基和杂芳基化合物,组合物及其使用方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4240823A (en) * 1976-03-24 1980-12-23 Philagro S.A. New plant growth regulating compositions which contain derivatives of N-acyl methionine
DE19625524A1 (de) * 1996-06-26 1998-01-08 Gruenenthal Gmbh Neue synthetische Catecholderivate, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0863139A1 (fr) * 1997-03-05 1998-09-09 Grünenthal GmbH Dérivés de benzoxazine, leur procédé de préparation et leur application
WO2002070016A2 (fr) * 2001-03-01 2002-09-12 Grünenthal GmbH Conjugues catechol-beta-lactame, procedes de production et utilisations associes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4240823A (en) * 1976-03-24 1980-12-23 Philagro S.A. New plant growth regulating compositions which contain derivatives of N-acyl methionine
DE19625524A1 (de) * 1996-06-26 1998-01-08 Gruenenthal Gmbh Neue synthetische Catecholderivate, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0863139A1 (fr) * 1997-03-05 1998-09-09 Grünenthal GmbH Dérivés de benzoxazine, leur procédé de préparation et leur application
WO2002070016A2 (fr) * 2001-03-01 2002-09-12 Grünenthal GmbH Conjugues catechol-beta-lactame, procedes de production et utilisations associes

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
BIOVHIM. BIOPHYS. ACTA, vol. 177, no. 2, 1969, pages 321 - 328 *
CHEMICAL ABSTRACTS, vol. 129, no. 22, 30 November 1998, Columbus, Ohio, US; abstract no. 290321b, PORAS, HERVÉ ET AL.: "Synthesis and in vitro antibacterial activity of catechol-spiramycin conjugates." page 583; column 2; XP002209061 *
CHEMICAL ABSTRACTS, vol. 70, no. 21, 1969, Columbus, Ohio, US; abstract no. 97141c, O'BRIEN, I. G. ET AL.: "2,3-dihydroxy-N-benzoylserine" page 388; column 2; XP002209060 *
FREDERICK L. WEITL ET AL.: "Lipophilic enterobactin analogues.", JOURNAL OF ORGANIC CHEMISTRY., vol. 46, no. 25, 1981, EASTON US, pages 5234 - 5237, XP002222600 *
J. ANTIBIOT., vol. 51, no. 8, 1998, pages 786 - 794 *
LOTHAR HEINISCH ET AL.: "Highly antibacterial active aminoacyl penicillin conjugates with acylated bis-catecholate siderophores...", JOURNAL OF MEDICINAL CHEMISTRY., vol. 45, no. 14, 6 June 2002 (2002-06-06), WASHINGTON US, pages 3032 - 3040, XP002209059 *
TAKERU ITO ET AL.: "Products of "low-iron fermentation" with Bacillus subtilis:", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 80, no. 17, 1958, DC US, pages 4645 - 4647, XP002209058 *

Also Published As

Publication number Publication date
DE10111164A1 (de) 2002-09-05
WO2002085841A2 (fr) 2002-10-31

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