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Title:
C-NITROSO COMPOUNDS AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO2002034705
Kind Code:
A3
Abstract:
A C-nitroso compound having a molecular weight ranging from 225 to 1,000 (from 225 to 600 for oral administration) on a monomeric basis wherein a nitroso group is attached to a tertiary carbon, which is obtained by nitrosylation of a carbon acid having a pKa less than about 25, is useful as an NO donor. When the compound is obtained from a carbon acid with a pKa less than about 10, it provides vascular relaxing effect when used at micromolar concentrations and this activity is potentiated by glutathione to be obtained at nanomolar concentrations. When the compound is obtained from a carbon acid with a pKa ranging from about 15 to 20, vascular relaxing effect is obtained at nanomolar concentrations without glutathione. In another embodiment, a biocompatible polymer incorporates a C-nitroso moiety.

Inventors:
STAMLER JONATHAN S (US)
TOONE ERIC J (US)
Application Number:
PCT/US2001/027734
Publication Date:
July 11, 2002
Filing Date:
September 27, 2001
Export Citation:
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Assignee:
UNIV DUKE (US)
STAMLER JONATHAN S (US)
TOONE ERIC J (US)
International Classes:
A61K31/00; A61K31/194; A61K31/195; A61K31/222; A61K31/553; A61K31/635; A61K38/00; A61L27/00; A61L31/00; A61P7/02; A61P9/10; A61P29/00; A61P31/04; A61P31/12; C07C207/00; C07C291/08; C07D231/12; C07D267/04; (IPC1-7): C07C207/00; C07C201/00; C07D207/46; A61P29/00; A61K31/00
Domestic Patent References:
WO1996016645A11996-06-06
WO1996017604A11996-06-13
Other References:
KLAUS REHSE ET AL.: "Azodioxides activated by electron acceptors in geminal or vicinal position", ARCH. PHARM. PHARM. MED. CHEM., vol. 331, 1998, pages 104 - 110, XP008001600
KLAUS REHSE ET AL.: "Pseudonitroles and their dimeric azodioxides", ARCH. PHARM. PHARM. MED. CHEM., vol. 331, 1998, pages 79 - 84, XP008001599
FEELISCH M ET AL: "DONORS OF NITROGEN OXIDES", METHODS IN NITRIC OXIDE RESEARCH, WILEY, CHICHESTER, GB, PAGE(S) 71-115, XP000609403
PETER H GROVES ET AL.: "Exogenous nitric oxide inhibits in vivo platelet adhesion following ballon angioplasty", CARDIOVASCULAR RESEARCH, vol. 26, 1992, pages 615 - 619, XP008001601
PETER H GROVES ET AL.: "SIN-1 reduces platelet adhesion and platelet thrombus formation in a porcine model of balloon angioplasty", CIRCULATION, vol. 87, no. 2, 1993, pages 590 - 597, XP001040370
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