Amino sugar derivatives

Details Amino sugar derivatives Amino sugar derivatives

1993-03-31

1995-07-11

Wityshyn, Michael G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 552, 536115, 536116, 536117, 536119, 536120, C07H 504, C07H 1104, C07H 1302

Patent

active

054322677

ABSTRACT:
A compound represented by formula (I): ##STR1## wherein R.sup.1 represents --CO--Z.sup.1 --N(Z.sup.11)--CO--Z.sup.2 --H or --CO--Z.sup.3 --H, wherein Z.sup.1, Z.sup.2, and Z.sup.3 each represent an alkylene group having from 1 to 20 carbon atoms, a phenylene group, or a combination thereof, and Z.sup.11 represents a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms which may be substituted with a phenyl group, a phenyl group which may be substituted with an alkyl group having from 1 to 20 carbon atoms, or an alkylene group having from 1 to 20 carbon atoms which may contain therein a phenylene group; R.sup.2 represents --CO--Z.sup.4 --N(Z.sup.12)--CO--Z.sup.5 --H, --CO--Z.sup.6 --H or a hydrogen atom, wherein Z.sup.4, Z.sup.5, and Z.sup.6 each have the same meaning as Z.sup.1, and Z.sup.12 has the same meaning as Z.sup.11 ; Q.sup.1 and Q.sup.2 each represent a carboxyl group or a phosphonoxy group; Q.sup.3 represents a hydrogen atom, a carboxyl group or a phosphonoxy group; m represents 0 or an integer of from 1 to 20; n represents 0 or an integer of from 1 to 20; Y.sup.1 represents an alkylene group having from 1 to 10 carbon atoms which may contain one or more substituents selected from --OCOR.sup.11 and --NHCOR.sup.12, wherein R.sup.11 represents --Z.sup.13 or --Z.sup.7 --N (Z.sup.14)--CO--Z.sup.8 --H (wherein Z.sup.7 and Z.sup.8 each have the same meaning as Z.sup.1, and Z.sup.13 and Z.sup.14 each have the same meaning as Z.sup.11) and R.sup.12 represents --Z.sup.15 or --Z.sup.9 --N(Z.sup.16)--CO--Z.sup.10 --H (wherein Z.sup.9 and Z.sup.10 each have the same meaning as Z.sup.1, and Z.sup.15 and Z.sup.16 each have the same meaning as Z.sup.11), and a salt thereof. The compound inhibits TNF derivation by endotoxin and is therefore useful for the treatment of multiorganic insufficiencies.

REFERENCES:
patent: 5278300 (1994-01-01), Hasegawa et al.
Proc. Natl. Acad. Sci., vol. 82, issued 1985, Teng et al, "Protection against Gram-Negative Bacteremia and Endotoxemia Wi Human Monoclonal IgM Antibodies", pp. 1790-1794.
Journal of Infectious Diseases, vol. 166, issued 1992, Wortel et al, "Effectiveness of a Human Monoclonal Anti-Endotoxin Antibody (HA-1A) in Gram-Negative Sepsis: Relationship to Endotoxin and Cytokine Levels", pp. 1367-1374.
The New England Journal of Medicine, vol. 324, No. 7, issued 14 Feb. 1991, Ziegler et al, "Treatment of Gram-Negative Bacteremia and Septic Shock with HA-1A Human Monoclonal Antibody Against Endotoxin-A Randomized, Double-Blind, Placebo-Controlled Trial", pp. 429-436.
JAMA vol. 266, No. 24, issued 25 Dec. 1991, Schulman et al, "Cost-Effectiness of HA-1A Monoclor Antibody for Gram-Negative Sepsis-Economic Assessment of a New Therapeutic Agent", pp. 3466-3471.
Nature, vol. 330, issued 17 Dec. 1987, Tracey et al, "Anti-Cachectin/TNF Monoclonal Antibodies Prevent Septic Shock during Lethal Bacteraemia" pp. 662-664.
The Lancet, vol. 335, issued 26 May 1990, Exley et al, "Monoclonal Antibody to TNF in Severe Septic Shock", pp. 1275-1277.
Cancer Research, vol. 49, issued 01 Aug. 1989, L. F. Tietze et al "Proton-mediated Liberation of Aldophosphamide from a Nontoxic Prodrug: A Strategy for Tumor-Selective Activation of Cytocidal Drugs" pp. 4179-4184.
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