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WO1996030336A1 - 1,3,9,11-tetraoxa-4,5,7,8-tetraazaundecadiene-4,7-dioxydes-5,7 substitues, leur preparation et leur application - Google Patents

1,3,9,11-tetraoxa-4,5,7,8-tetraazaundecadiene-4,7-dioxydes-5,7 substitues, leur preparation et leur application Download PDF

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Publication number
WO1996030336A1
WO1996030336A1 PCT/LV1996/000001 LV9600001W WO9630336A1 WO 1996030336 A1 WO1996030336 A1 WO 1996030336A1 LV 9600001 W LV9600001 W LV 9600001W WO 9630336 A1 WO9630336 A1 WO 9630336A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
tetraazaundecadiene
tetraoxa
substituted
dioxides
Prior art date
Application number
PCT/LV1996/000001
Other languages
English (en)
Inventor
Janis Kuzmanis
Ivars Kalvinsh
Original Assignee
Latvian Institute Of Organic Synthesis
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 Latvian Institute Of Organic Synthesis filed Critical Latvian Institute Of Organic Synthesis
Publication of WO1996030336A1 publication Critical patent/WO1996030336A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/08—Azoxy compounds

Definitions

  • the present invention relates to new chemical compounds - substituted 1,3,9, 1 1 - tetraoxa-4,5,7,8-tetraazaundecadiene-4,7-dioxides-5,7 with general structure Fl , to methods of their preparation, and to pharmaceutical compositions, containing these compounds.
  • such compounds can act as potential donors of nitric oxide NO in living organisms, and as strong cytostatic agents they can be employed in cancer chemotherapy
  • Second group of known related compounds are by F2 alkylation obtained substituted alkoxydialkyltriazene-N-oxides with general structure F3, where Ri - R . . are different organic residues (Keefer L. K. et. al., WO 93/071 14, publ. 15.04. 1993 ).
  • A represents oxygen or nitrogen containing substituent, but B is photolytically unstable group
  • Compounds F2 show cytostatic activity (WO 93/20806), they inhibit 3 H- thymidine incorporation in DNA of human melanoma A-375-C6 cells to 50% at concentrations 24 - 280 ⁇ M.
  • Aerosols comprising compounds Fl in therapeutically active amounts, which are sprayed by pulverizator or pressurized propellant, as freon, propane, etc
  • Galenic forms for parenteral use include sterile injection solutions of compounds Fl in therapeutically active amounts in water or other solvents, as well as microcrystalline compounds Fl suspensions, which additionally may contain conserving, bacteriostatic, buffering agents, antioxidants, salts, as well as other pharmaceutically acceptable ingredients for galenic drug preparation This includes also ex tempore prepared injection solutions and suspensions
  • Mouse lympholeucosis P-388 (mouse line DBA/2) cell suspension was made in RPMI-1640 medium with 5% serum, cell concentration 10 5 cells/ml. Incubation with compounds 2 hr, incubation with ⁇ -thymidine ( l ⁇ Ci/ml medium) - 1 hr
  • NMU N-methyl-N-nitrosourea

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Nouveaux composés chimiques dits 1,3,9,11-tétraoxa-4,5,7,8-tétraazaundécadiène-4,7-dioxydes-5,7 substitués ayant la structure générale F1, leurs procédés de préparation, et compositions pharmaceutiques les contenant. Plus précisément, ces composés peuvent servir de donneurs potentiels d'oxyde nitrique NO dans les organismes vivants, et d'agents cytostatiques puissants dans la chimiothérapie du cancer.
PCT/LV1996/000001 1995-03-30 1996-03-19 1,3,9,11-tetraoxa-4,5,7,8-tetraazaundecadiene-4,7-dioxydes-5,7 substitues, leur preparation et leur application WO1996030336A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LVP-95-84 1995-03-30
LVP-95-84A LV11542B (en) 1995-03-30 1995-03-30 Substituted 1,3,9,11-tetraoxa-4,5,7,8-tetraazaundecadien-4,7-dioxides-5,7, preparation and use thereof

Publications (1)

Publication Number Publication Date
WO1996030336A1 true WO1996030336A1 (fr) 1996-10-03

Family

ID=19735911

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/LV1996/000001 WO1996030336A1 (fr) 1995-03-30 1996-03-19 1,3,9,11-tetraoxa-4,5,7,8-tetraazaundecadiene-4,7-dioxydes-5,7 substitues, leur preparation et leur application

Country Status (2)

Country Link
LV (1) LV11542B (fr)
WO (1) WO1996030336A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003074082A1 (fr) * 2002-03-06 2003-09-12 Cellegy Pharmaceuticals, Inc. Formulations et procedes d'utilisation de substances mimetiques de l'oxyde nitrique dans le traitement du cancer
EP1502604A1 (fr) * 2000-04-26 2005-02-02 Cellegy Pharmaceuticals, Inc Utilisation de substances mimetiques de l'oxide nitrique dans le traitement du cancer
WO2005056048A1 (fr) * 2003-12-10 2005-06-23 Georg Bauer Procede pour accroitre de maniere specifique la sensibilite de cellules tumorales
US6946484B2 (en) 2000-04-26 2005-09-20 Cellegy Pharmaceuticals, Inc. Formulations and methods of using nitric oxide mimetics against a malignant cell phenotype
US7678391B2 (en) 2000-04-26 2010-03-16 Queen's University At Kingston Formulations and methods of using nitric oxide mimetics against a malignant cell phenotype

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993020806A1 (fr) * 1992-04-13 1993-10-28 The United States Of America, Represented By The Secretary, Department Of Health And Human Services Utilisation de complexes d'oxyde nitrique/nucleophile dans le traitement du cancer
WO1994027957A1 (fr) * 1993-05-26 1994-12-08 The Regents Of The University Of California Composes degageant de l'oxyde nitrique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993020806A1 (fr) * 1992-04-13 1993-10-28 The United States Of America, Represented By The Secretary, Department Of Health And Human Services Utilisation de complexes d'oxyde nitrique/nucleophile dans le traitement du cancer
WO1994027957A1 (fr) * 1993-05-26 1994-12-08 The Regents Of The University Of California Composes degageant de l'oxyde nitrique

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 093, no. 17, 27 October 1980, Columbus, Ohio, US; abstract no. 167536, YANDOVSKII V N ET AL: "Azo- and azoxy compounds. V. Alkylation of bis(nitrosohydroxylamino)methane salts. Synthesis of 1,7-dialkyl-1,7-dioxa-2,3,5,6-tetraaza-2,5-heptadiene 3,5-dioxides" XP002005358 *
CHEMICAL ABSTRACTS, vol. 104, no. 25, 23 June 1986, Columbus, Ohio, US; abstract no. 224533, MARCHENKO G A ET AL: "Derivatives of N'-alkoxydiazene N-oxides. II. Reaction of 2,2-bis(2-methoxy-1-oxodiazenyl)ethanol esters with nucleophiles" XP002005359 *
CHEMICAL ABSTRACTS, vol. 113, no. 11, 10 September 1990, Columbus, Ohio, US; abstract no. 096995, MARCHENKO G A ET AL: "N'-alkoxydiazene N-oxides. VI. Ethers of N'-alkoxydiazene N-oxides" XP002005651 *
WOODWARD R B ET AL: "Methoxazonyl group", TETRAHEDRON LETT. (TELEAY);69; (32); PP.2689-92, 1969, HARVARD UNIV.;CAMBRIDGE; MASS., XP002005357 *
ZH. ORG. KHIM. (ZORKAE,05147492);80; VOL.16 (5); PP.933-6, LENINGR. GOS. UNIV.;LENINGRAD; USSR *
ZH. ORG. KHIM. (ZORKAE,05147492);85; VOL.21 (7); PP.1429-31, USSR (SU) *
ZH. ORG. KHIM. (ZORKAE,05147492);90; VOL.26 (2); PP.276-9, USSR (SU) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1502604A1 (fr) * 2000-04-26 2005-02-02 Cellegy Pharmaceuticals, Inc Utilisation de substances mimetiques de l'oxide nitrique dans le traitement du cancer
US6946484B2 (en) 2000-04-26 2005-09-20 Cellegy Pharmaceuticals, Inc. Formulations and methods of using nitric oxide mimetics against a malignant cell phenotype
US7678391B2 (en) 2000-04-26 2010-03-16 Queen's University At Kingston Formulations and methods of using nitric oxide mimetics against a malignant cell phenotype
US8168232B2 (en) 2000-04-26 2012-05-01 Queen's University At Kingston Formulations and methods of using nitric oxide mimetics in cancer treatment
WO2003074082A1 (fr) * 2002-03-06 2003-09-12 Cellegy Pharmaceuticals, Inc. Formulations et procedes d'utilisation de substances mimetiques de l'oxyde nitrique dans le traitement du cancer
WO2005056048A1 (fr) * 2003-12-10 2005-06-23 Georg Bauer Procede pour accroitre de maniere specifique la sensibilite de cellules tumorales

Also Published As

Publication number Publication date
LV11542B (en) 1997-02-20
LV11542A (lv) 1996-10-20

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