DERIVATIVES OF MONOSACCHARIDES AS 5-LIPOXYGENASE INHIBITORS
Field of Invention
The present invention relates to the use of derivatives of monosaccharides as 5-lipoxygenase inhibitor.
Background of Invention
5- Lipoxygenase is a key enzyme that oxidizes arachidonic acid into biologically active leukotrienes, namely cysteinyl leukotrienes and leukotriene B4 (Clin. Exp. Allergy Rev., \_ 196, 2001). Leukotrienes play important role in the pathophysiology of inflammatory / allergic diseases including bronchial asthma (Clin, Exp. Allergy Rev., ]_, 264, 2001), allergic rhinitis (Clin. Exp. Allergy Rev. ]_, 235, 2001), urticaria, atopic dermatitis (Clin. Exp. Allergy Rev. ]_, 305, 2001), chronic obstructive pulmonary disease (Eur. Respir. J., 22, 926, 2003) etc. Incidence of allergic / inflammatory diseases are on the rise globally (Emerging Therapeutic Targets, 3, 229, 1999; Expert Opin. Investigation^ Drugs, K), 1361,2000).
A variety of stimuli namely antigen-antibody reaction, cold or hyperosmotic shock etc, that elevates intracellular calcium level, can evoke arachidonic acid release from cell membrane under the influence of cytosolic phospholipase A2. Arachidonic acid is transferred to nuclear membrane by 5-lipoxygenase binding protein (FLAP) and acted upon by 5-lipoxygenase enzyme to generate 5-hydroperoxyeicosatetraenoic acid (HPETE). HPETE is converted to LTA4 by 5-lipoxygenase. Depending upon cell type, LTA4 is converted to either cysteinyl leukotrienes and/or leukotriene B4 (Clin. Exp. Allergy Rev. ]_, 196, 2001; Curr. Drug Targets - Inflammation & Allergy, ]_, 23, 2002; Drug Safety, 26, 484, 2003).
Leukotrienes are generated by a variety of inflammatory cell types. Neutrophils and monocytes generate LTB4 whereas mast cells, basophils, eosinophils and bronchial epithelial cells produce cysteinyl leukotrienes. LTB4 acts as a chemoattractant for neutrophils through specific cell surface receptors. Cysteinyl leukotrienes, which include LTC4, LTD4 and LTE4, act on CysLTl and CysLT2 receptors and increase bronchial smooth muscle contractility, promote mucosal secretion, increase vascular permeability and encourage eosinophils recruitment. (Am. J. Respir. Critic Care
Med. 157. S210, 1998; Thorax 55, S32, 2000; Clin. Exp. Allergy Rev., I, 196, 2001; Clin. Exp.
Allergy Rev. \, 220, 2001; Drug Safety, 26, 484, 2003).
There is evidence suggesting that cysteinyl leukotrienes can increase airway smooth muscle contractility in preclinical (Am. J. Respir Crit. Care Med,. 157 S214, 1998) and clinical studies (Clin. Exp. Allergy Rev. ]_, 220, 2001). Inhalation of leukotrienes also increase influx of inflammatory cells in the airway of animals (Clin. Exp. Allergy Rev. 1, 220, 2001) and humans (Am. J. Respir Crit. Care Med., 157, S210, 1998). In patients with asthma, urinary excretion of LTE4 correlates with exercise or cold air induced bronchoconstriction (Lancet, ]_, 584, 1989) allergen induced early and late phase response (Clin. Exp Aller. 28, 1332, 1998; Am. J. Respir. Crit. Care Med J_57, S210, 1998), as well as with reduction of FEV1 in patients with nocturnal asthma (Am. J. Respir. Crit. Care Med. 157. S233, 1998). Efficacy of leukotriene biosynthesis inhibitors and leukotriene receptor antagonists have been tested in numerous trials involving asthma patients (Clin. Exp. Aller. Review ]_, 254, 2001; Drug Safety, 26, 483, 20Q3-NEJM, 340, 197, \999\Am. J. Respir. Crit. Care Med. 157. S233, 1998).
Evidence is emerging that leukotrienes also contribute towards pathophysiology of COPD. Two major cell types, neutrophils and macrophages, that generate LTB4 and are modulated by the same in turn are believed to participate in the pathogenesis of COPD (Am. J. Respir. Crit. Care Med. 157. S210, 1998). Patients with COPD exhibit elevated sputum neutrophilia and LTB4 levels (Chest, 121. 197S, 2002). Elevated levels of LTB4 were shown to be present in the exhaled breath condensate of COPD patients (Thorax., 58, 585 2003) as well as in patients experiencing exacerbation of COPD (Thorax., 58, 294, 2003). Inhibitors of leukotriene biosynthesis as well as LTB4 receptor antagonists have shown to reduce airway reactivity, airway inflammation and airway neutrophilia in animals (J. Clin. Exp. Aller. 91_, 917, 1992; JPharmacol. Exp. Ther. 297. 458, 2000) as well as in human subjects (Thorax 5J_, 1178, 1996; Chest,. 122, 289, 2002). Cysteinyl leukotriene antagonists like Montelukast have shown protective effect in hypertonic saline induced bronchoconstriction in COPD patients (Eur. Respir. J. 22:926, 2003).
Similarly, evidence is emerging based on animal and human data that leukotriene pathway
modulators can play role in arthritis (J. Pharmacol. Exp. Ther. 285, 946, 1998) allergic rhinitis and urticaria (Clin. Exp. Aller. Review, J_, 235, 2001)
Several leukotriene receptor antagonists, Montelukast, Zafirlukast, and Pranlukast, and one 5-lipoxygenase inhibitor, Zileuton, have been launched in the market. Both categories of molecules have shown efficacy in clinical trials of bronchial asthma. Inhibitors of 5-lipoxygenase exhibit greater potential to exhibit efficacy in COPD as well because of their inhibitory effect on LTB4 mediated processes. However, commercially available 5-lipoxygenase inhibitor is associated with poor pharmacokinetic properties and adverse events, like elevation of hepatic transaminase levels. This has prompted the search for novel inhibitors of 5-lipoxygenase with improved pharmacokinetic profiles and reduced adverse effects.
WO2004/071515 discloses preparation of monosaccharides derivatives for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies.
U.S. Patent No. 6,329,344 discloses several derivatives of monosaccharides as cell adhesion inhibitors. U.S. Patent No. 6,329,344 discloses classes of monosaccharides compounds useful for inhibition and prevention of cell adhesion and cell adhesion mediated pathologies. U.S. Patent No. 6,590,085 discloses further derivatives of monosaccharides similarly useful.
Summary of the Invention
According to one aspect a method for inhibiting the 5-Lipoxygenase enzyme is provided, comprising the administration to a patient in need of such treatment, a therapeutically effective amount of a compound, having the structure of Formula I,
(Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, amides, prodrugs
or metabolites
wherein,
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkylaryl;
R' is SO2C6H5, SO2C6l-UCI-h-p or SO2C6H4-Cl, phenyl or substituted phenyl, represented as C6H4-R'"-p R'" being CI, NO2, OCH3, CH3, CH2COOH, CH2COOCH3, CH2COLDVP, CH2CODVP,
CH2COVP, wherein LDVP DVP and VP represent tetrapeptide (Leucyl-aspartyl-alyl-prolyl),
tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl) respectively;
R" is H or CH3 and
(w ) represents idofuranose, talofuranose, xylofuranose or ribofuranose configurations.
According to another aspect a method for inhibiting the 5-Lipoxygenase enzyme is provided, comprising the administration to a patient in need of such treatment, a therapeutically effective amount of a compound, having the structure of Formula II
(Formula Removed)
its pharmaceutically acceptable salts, esterf,°ewdtiomers, diastereomers, N-oxides, amides, prodrugs or metabolites, wherein
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkyl aryl;
R' is SO2C6H5, SO2C6H5CH3-p, S02 C6H4Cl-p, phenyl or substitutd phenyl, represented as C6H4-R'"-p, wherein R'" being Cl, NO2, OCH3, CH3, CH2COOH, CH2COOCH3, CH2COLDVP, CH2CODVP, CH2COVP, wherein LDVP, DVP and VP represent tetrapeptide (Leucyl-aspartyl-valyl-prolyl), tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl), respectively; and
R" is H or CH3
According to a further aspect a method for inhibiting the 5 Lipoxygenase enzyme is provided, comprising the administration to a patient in need of such treatment a therapeutically effective amount of a compound, having the structure of Formula III,
(Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, amides, prodrugs
or metabolites
wherein
R' is COLDVP, CODVP, COVP or CH2NHCONHR" wherein LDVP, DVP and VP represent
tetrapeptide (Leucyl-aspartyl-valyl-prolyl), tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl), respectively; R" is C6H4R"'-p ( R'" is Cl, NO2, OCH3, CH3, CH2COOH, CH2CO-LDVP,
CH2CO-DVP or CH2CO-VP wherein LDVP, DVP and VP are the same as defined earlier).
(Formula Removed)
According to yet another aspect, a method for inhibiting the 5-Lipoxygenase enzyme is provided, comprising the administration to a patient in need of such treatment a therapeutically effective amount of a compound, having the structure of Formula IV.
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, amides, prodrugs or metabolites, wherein
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkylaryl; RI is phenyl, o-m- or p-chlorophenyl, tolyl, methoxyphenyl or nitrophenyl; and
(Formula Removed)
R2 is H, pyrrolidinyl, piperidinyl, morphilinyl or hexamethyleneimino or a radical of the Formula-
NHRa wherein RS is C1 to C15 alkyl, alkene or alkyne (straight chain or branched) or a radical of the
Formula
in which n is a whole number between 2 and 5 and
is a five, six or seven - membered, heterocyclic ring, For (Formula Removed)
example,
(Formula Removed)
can be pyrrolidinyl, piperidinyl, morpholinyl or hexamethyleneimino moieties.
It is another further aspect to provide novel methods for 5-lipoxygenase enzyme inhibition comprising the administration to a patient in need of such treatment a therapeutically effective amount of a compound or pharmaceutically acceptable salt of a compound of Formulae I, II, III and IV.
Detailed Description of the Invention
An illustrative list of particular compounds according to Formula I includes:
l,2-0-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β-L-idofuranose (Compound No. 1),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β -L-idofuranose (Compound No. 2),
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β -L-idofuranose (Compound No. 3),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-p -L-idofuranose (Compound No. 4),
1,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} -β -L-idofuranose (Compound No. 5),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β -L-idofuranose (Compound No. 6),
l,2-0-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β -L-idofuranose (Compound No. 7),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β -L-idofuranose (Compound No. 8),
1,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose (Compound No. 9),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β -L-idofuranose (Compound No. 10),
1,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose (Compound No. 11),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino}-β -L-idofuranose (Compound No. 12),
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose (Compound No. 13),
l,2-0-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose (Compound No. 14),
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose (Compound No. 15),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose (Compound No. 16),
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] amino
carbonylamino}-β-L-taIofuranose (Compound No. 17),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenylamino carbonylamino}-β-L-talofuranose (Compound No. 18),
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β-L-talofuranose (Compound No. 19),
l,2-0-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β-L-talofuranose (Compound No. 20),
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} -β-L-talofuranose (Compound No. 21),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-5-epiallofuranose (Compound No. 22),
l,2-0-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β-L-talofuranose (Compound No. 23),
l,2-0-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β-L-talofuranose (Compound No.24),
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β-L-talofuranose (Compound No. 25),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β-L-talofuranose (Compound No. 26),
l,2-O-isopropylidene-3-O-heptyI-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β-L-talofuranose (Compound No. 27),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β-L-talofuranose (Compound No. 28),
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-talofuranose (Compound No. 29),
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-talofuranose (Compound No. 30),
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-taIofuranose (Compound No. 31),
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-taIofuranose (Compound No. 32),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose (Compound No. 33),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose (Compound No. 34),
l,2-O-isopropylidene-3-O-hexyI-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose (Compound No. 35),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose (Compound No. 36),
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose (Compound No. 37),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-
xylofuranose (Compound No. 38),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose (Compound No. 39),
l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose (Compound No. 40),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}a,D-xylofuranose (Compound No. 41),
l,2-0-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}a,D-xylofuranose (Compound No. 42),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} a,D-xylofuranose (Compound No. 43),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} a,D-
xylofuranose (Compound No. 44),
l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} a,D-
xylofuranose (Compound No. 45),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} a,D-
xylofuranose (Compound No. 46),
l,2-0-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} a,D-xylofuranose (Compound No. 47),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-xylofuranose (Compound No. 48),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-xylo-furanose (Compound No. 49),
l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-xylo-furanose (Compound No. 50),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-xylo-furanose (Compound No. 51),
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-xylo-furanose (Compound No. 52),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-L-Leucyl-a,L-Aspartyl-L-Valyl-L-Proline}- a,D-xylofuranose (Compound No. 53),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-a,L-Aspartyl-L-Valyl-L-Proline}- a,D-xy!ofuranose (Compound No. 54),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-alyl-L-Proline}- a,D-xylofuranose (Compound No. 55)
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-a,D-ribofuranose (Compound No. 56),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-a,D-ribofuranose (Compound No. 57),
l,2-0-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-a,D-ribofuranose (Compound No. 58),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-a,D-ribofuranose (Compound No. 59),
l,2-0-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-ribofuranose (Compound No. 60),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-
ribofuranose(Compound No. 61),
l,2-0-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose (Compound No. 62),
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose (Compound No.63),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose (Compound No. 64),
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose (Compound No. 65),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose (Compound No. 66),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
ribofuranose (Compound No. 67),
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose (Compound No. 68),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
ribofuranose (Compound No. 69),
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose (Compound No. 70),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribo-furanose (Compound No. 71),
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribo-furanose (Compound No. 72),
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribo-furanose (Compound No. 73),
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribo-furanose (Compound No. 74),
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribo-furanose (Compound No. 75),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylaminophenyl]acetyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Prollne }-α,D-ribofuranose (Compound No. 76),
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylaminophenyl]acetyl-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-ribofuranose (Compound No. 77), and
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylaminophenyl]acetyl-L-Valyl-L-Proline }-α,D-ribofuranose (Compound No.78).
An illustrative list of particular compounds according to Formula II includes:
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β, L-gulofuranoside (Compound No. 79),
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β, L-gulofuranoside (Compound No. 80),
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β, L-gulofuranoside (Compound No. 81),
2,3-0-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β, L-gulofuranoside (Compound No. 82),
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β, L-gulofuranoside (Compound No. 83),
Tris salt of 2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl) phenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 84)
Sodium salt of 2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxo-ethyl)phenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 85)
2,3-O-isopropyIidene-l-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 86),
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-chIorophenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 87),
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 88),
2,3-O-isopropyIidene-l-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 89),
2,3-O-isopropylidene-l -O-dodecyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} -β, L-gulofuranoside (Compound No. 90),
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β, L-gulofuranoside (Compound No. 91),
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β, L-gulofuranoside (Compound No. 92),
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β, L-gulofuranoside (Compound No. 93),
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β, L-gulofuranoside (Compound No. 94),
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β, L-gulofuranoside (Compound No. 95),
2,3-0-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 96),
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 97),
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 98),
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 99),
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside (Compound No. 100),
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside (Compound No. 101),
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside (Compound No. 102),
2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside (Compound No. 103),
2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranose (Compound No. 104),
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside (Compound No. 105),
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside (Compound No. 106),
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonyIamino}α,D-lyxofuranoside (Compound No. 107),
2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside (Compound No. 108),
2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside (Compound No. 109),
2,3-O-isopropylidene-l-O-dodecyI-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-
lyxofuranoside (Compound No. 110),
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside (Compound No. Ill),
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
lyxofuranoside (Compound No. 112),
2,3-0-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside (Compound No. 113),
2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
lyxofuranoside (Compound No. 114),
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} αD-lyxofuranoside (Compound No. 115),
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}a,D-lyxo-furanoside (Compound No. 116),
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxo-furanoside (Compound No. 117),
2,3-0-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxo-furanoside (Compound No. 118),
2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxo-furanoside (Compound No. 119),
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxo-furanoside (Compound No. 120),
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Proline}-a,D-lyxofuranoside (Compound No. 121),
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-lyxofuranoside (Compound No. 122), and
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-L-Valyl-L-Proline}-α,D-lyxofuranoside (Compound No. 123).
An illustrative list of particular compounds according to Formula III includes:
2,3;4,6-Di-O-isopropylidene-l-carbonyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Proline-α,L-xy!o-2-hexulofuranosonic acid (Compound No. 124),
2,3;4,6-Di-O-isopropylidene-l-carbonyl-a,L-Aspartyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid (Compound No. 125),
2,3-O-isopropylidene-l-carbonyl-L-Leucyl-a,L-Aspartyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid (Compound No. 126),
2,3-O-isopropylidene-l-carbonyl-α,L-Aspartyl-L-Valyl-L-Proline-a,L-xylo-2-hexulofuranosonic acid (Compound No. 127),
2,3-O-isopropylidene-l-carbonyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid (Compound No. 128),
2,3;4,6-Di-O-isopropylidene-l-deoxy-l-N-{[4-chlorophenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose (Compound No. 129),
2,3;4,6-Di-0-isopropylidene-l-deoxy-l-N-{[4-methoxyphenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose (Compound No. 130),
2,3;4,6-Di-O-isopropylidene-l-deoxy-l-N-{[4-tolyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose (Compound No. 131),
2,3-O-isopropylidene-l-deoxy-l-N-{[4-(2-hydroxy-2oxoethyl))phenylaminocarbonylamino}-α,L-xylo- 2-hexulofuranose (Compound No. 132),
2,3-O-isopropylidene-l-deoxy-l-N-{[4-chlorophenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose (Compound No. 133),
2,3-0-isopropylidene-l-deoxy-l-N-{[4-methoxyphenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose (Compound No. 134),
2,3-O-isopropylidene-l-deoxy-l-N-{[4-tolyl]aminocarbonylamino}-α,L-xylo-2-hexuIo furanose(Compound No. 135),
2,3-O-isopropylidene-ldeoxy-l-N-{[aminocarbonylaminophenylacetyl-L-LeucyI-α,L-Aspartyl-L-Valyl-L-Proline)}-α,L-xylo-2-hexulofuranose(Compound No. 136),
2,3-O-isopropylidene-l-deoxy-l-N-{[aminocarbonylaminophenylacetyl-α,L-Aspartyl-L-Valyl-L-Proline)}-α,L-xylo-2-hexulofuranose (Compound No. 137), 2,3-O-isopropylidene-ldeoxy-l-N-{[aminocarbonylaminophenylacetyl-L-Valyl-L-
Proline)}-α,L-xylo-2-hexulofuranose (Compound No. 138).
An illustrative list of particular compounds according to Formula IV include:
2,3-O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl) -6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 139),
2,3-O-Isopropylidene-l-O-dodecyl-4-0-(methylaminocarbonyl) -6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 140),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 141),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 142),
2,3-O-IsopropyIidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yi-α-L-xylo-2-hexulofuranose (Compound No. 143),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 144)
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 145),
2,3-O-lsopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 146),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 147),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 148),
2,3-O-lsopropyIidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 149),
2,3-0-lsopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 150),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenyIaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yI-α-L-xylo-2-hexulofuranose (Compound No. 151),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 152),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolyIaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 153),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 154),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 155),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 156),
2,3-0-Isopropyiidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyI)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 157),
2,3-O-Isopropylidene-l-O-dodecyl-4-0-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 158),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 159),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 160),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 161),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 162),
2,3-0-Isopropylidene-l-O-decyl-4-0-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 163),
2,3-0-IsopropyIidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 164),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 165),
2,3-0-Isopropylidene-l-O-heptyl-4-0-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 166),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chIorophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 167),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 168),
2,3-0-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 169),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 170),
2,3-O-Isopropyl idene-1 -O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-1 -yl-α-L-xylo-2-hexulofuranose (Compound No. 171),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 172),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 173),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 174),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nltrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 175),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 176),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xyIo-2-hexulofuranose (Compound No. 177),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 178),
2,3-0-lsopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 179),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yI-α-L-xylo-2-hexulofuranose (Compound No. 180),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 181),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-a-L-xylo-2-hexuIofuranose (Compound No. 182),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 183),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-a-L-xylo-2-hexulofuranose (Compound No. 184),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 185),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 186),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 187),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 188),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -a-L-xylo-2-hexulofuranose (Compound No. 189),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 190),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 191),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose(Compound No. 192),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 193),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 194),
2,3-O-Isopropylidene-1 -O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1 -yl -α-L-xylo-2-hexulofuranose (Compound No. 195),
2,3-O-lsopropylidene-1 -O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6- azepan-1 -yl -α-L-xylo-2-hexulofuranose (Compound No. 196),
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 197),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 198),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 199),
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 200),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 201),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose (Compound No. 202),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose (Compound No. 203),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyljamino -α-L-xylo-2-hexulofuranose (Compound No 204),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 205),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-1-yl) ethyljamino -α-L-xylo-2-hexulofuranose (Compound No. 206),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl]amino -α-L-xylo-2-hexulofuranose (Compound No. 207),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yI) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 208),
2,3-0-lsopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose(Compound No. 209),
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 210),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 211),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 212),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 213),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 214),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 215),
2,3-0-lsopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 216),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 217),
2,3-O-Isopropylidene-1 -O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-1 -yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 218),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 219),
2,3-O-lsopropyiidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 220),
2,3-O-Isopropylidene-l-O-dodecyl-4-0-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-1-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 221),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 222),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 223),
2,3-0-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 224),
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 225),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 226),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 227),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 228),
2,3-0-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 229),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 230),
2,3-0-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 231),
2,3-0-lsopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 232),
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino-α-L-xylo-2-hexulofuranose (Compound No. 233),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-(2-ethylmorphilin-4-yl)-α-L-xylo-2-hexulofuranose (Compound No. 234),
2,3-O-IsopropyIidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No.235),
2,3-O-lsopropylidene-l-O-dodecyl-4-0-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 236),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexu!ofuranose (Compound No. 237),
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 238),
2,3-0-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino-α-L-xylo-2-hexulofuranose (Compound No. 239),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 240),
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose(CompoundNo. 241),
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 242),
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 243),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 244),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No.245),
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 246),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 247),
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 248),
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose (Compound No.249),
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 250),
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 251),
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-( pyrrolidin-1-yl)
ethyl] amino-α-L-xylo-2-hexulofuranose (Compound No. 252),
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 253),
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 254),
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 255),
2,3,O-lsopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 256),
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 257),
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 258),
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 259),
2,3,O-lsopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose (Compound No. 260),
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 261),
2,3,O-Isopropylidene-l-O-heptyl-4-O- (methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose (Compound No. 262),
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No. 263), and
2,3,O-lsopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose (Compound No.264).
Pharmacological activity
The compounds of Formulae I, II, III and IV showed inhibitory activity on A23187-induced LTB4 release from human neutrophils. Standard assays were performed on particular illustrative compounds of Formulae I, II, III and Formula IV, and are mentioned below.
A23187 Induced LTB4 Release from Human Neutrophils
Neutrophils were isolated from freshly drawn human blood after dextran sedimentation and ficoll separation (EurJ Biochem., 169, 175, 1987). 180 µl of the neutrophil suspension (0.2 x 106 cells/ml) were taken, and added 19ul of Hank's Buffer salt solution along with 1 µl of the test drug (200 times concentrated) in a 24-well plate and incubated at 37°C for 1 hr. 3 min before the end of test compound incubation, 0.25 mM Ca++/Mg++ was added. Then, 0.3 µg/ml A23187 was added and incubated for 10 min further. The reaction was stopped by adding 80 µl of cold methanol and spun at 3500 rpm for 10 min. to remove cell debris. The samples were analysed for LTB4 assay (J. Pharmacol. Exp. Ther. 297:267, 2001) using LTB4ELISA kits (Assay Design Inc., USA). The amount of LTB4was quantified and percent inhibition in LTB4 release was calculated with respect to negative and positive controls to compute IC50 values.
Compound Nos. 1,2, 6, 10, 14,33,36, 79,80,83-85,87,92,99, 101, 102, 105, 110, 115, 120, 168, 177, 193, 194, 197, 200, 210, and 241 were tested, giving IC50 value of between about 2.5
µm and about 30µm, or between about 2.5 µm and about 10 µm, or between about 2.5 µm and about
5 µm.

WE CLAIM:
1. Use of a compound for the manufacture of a medicament for inhibiting the 5-lipoxygenase
enzyme or related processes in a mammal, wherein the compounds are having the structure of
Formula I,
(Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, or amides, wherein
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkyl aryl; R' is SO2C6H5, SO2C6H4CH3-p, or SO2C6H4-Cl-p, phenyl or substituted phenyl, represented as C6H4-R'"-p, wherein R'" is Cl, NO2, OCH3, CH3, CH2COOH, CH2COOCH3, CH2COLDVP, CH2CODVP, or CH2COVP, wherein LDVP DVP and VP represent tetra peptide (Leucyl-aspartyl-alyl-prolyl), tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl) respectively; and R" is H or CH3; wherein
(^^^) represents idofuranose, talofuranose, xylofuranose or ribofuranose configurations.
2. Use of a compound for the manufacture of a medicament for inhibiting the 5-lipoxygenase
enzyme or related processes in a mammal, wherein the compounds are having the structure of
Formula 11, (Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, or amides,
wherein;
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkyl aryl; R' is SO2C6H5, SO2C6H5CH3-p, SO2 C6H4CI-p, phenyl or substitutd phenyl, represented as C6H4-
R'"-p, wherein R'" is Cl, NO2, OCH3, CH3, CH2COOH, CH2COOCH3, CH2COLDVP, CH2CODVP, or CH2COVP, wherein LDVP, DVP and VP represent tetra peptide (Leucyl-aspartyl-valyl-prolyl), tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl), respectively; and R" is H or CH3
3. Use of a compound for the manufacture of a medicament for inhibiting the 5-lipoxygenase
enzyme or related processes in a mammal, wherein the compounds are having the structure of
Formula III,
(Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides,or amides,
wherein
R' is CO-LDVP, CO-DVP, CO-VP or CH2NHCONHR" wherein LDVP, DVP and VP represent tetra
peptide (Leucyl-aspartyl-valyl-prolyl), tripeptide (aspartyl-valyl-prolyl) and dipeptide (valyl-prolyl),
respectively; wherein R" is C6H4R'"-p ( R'" is Cl, NO2, OCH3, CH3, CH2COOH, CH2COLDVP,
CH2CODVP or CH2COVP wherein LDVP, DVP and VP are the same as defined earlier).
4. Use of a compound for the manufacture of a medicament for inhibiting the 5-lipoxygenase
enzyme or related processes in a mammal, wherein the compounds are having the structure of
Formula IV,
(Formula Removed)
its pharmaceutically acceptable salts, esters, enantiomers, diastereomers, N-oxides, or amides,
wherein
R is C1 to C15 alkyl, alkene, alkyne (straight chain or branched), aryl, substituted aryl or alkyl aryl;
RI is methoyl phenyl, o-m- or p-chlorophenyl, tolyl, methoxyphenyl or nitrophenyl; and
R2 is H, pyrrolidinyl, piperidinyl, morphilinyl or hexamethyleneimino or a radical of the Formula-
NHR3 wherein R3, is C1 to C15 alkyl, alkene or alkyne (straight chain or branched) or a radical of the Formula
(Formula Removed)
in which n is a whole number in the range of 2-5 and
(Formula Removed)
is a five, six- or seven-membered heterocyclic ring containing one or more hetero atoms.
5. Use of a compound for the manufacture of a medicament for inhibiting the 5-lipoxygenase enzyme or related processes in a mammal, wherein the compounds are:
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonyi amino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl) phenyl]amino-
carbonylamino} -β -L-idofuranose,
1,2-O-isopropylidene-3-O-dodecy!-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonyl-amino}-β -L-idofuranose ,
l,2-O-isopropy!idene-3-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β -L-idofuranose,
1,2-0-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β -L-idofuranose,
l,2-0-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose,
1,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β -L-idofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose,
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose,
l,2-0-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-idofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] amino
carbonyl amino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β-L-talofuranose,
l,2-0-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β-L-talofuranose,
l,2-0-isopropylidene-3-O-butyl-5,6-didep;oxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-dodecy!-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} -β-L-talofuranose,
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-5-epiallofuranose,
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β-L-talofuranose,
l,2-0-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β-L-talofuranose,
l,2-0-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β-L-talofuranose,
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]amino carbonylamino} -β-L-talofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonyIamino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β-L-talofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino} -α,D-xylofuranose,
l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose,
l,2-0-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-
xylofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose,
l,2-0-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose,
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}α,D-xylofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
xylofuranose,
l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
xylofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-
xylofuranose,
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-xylofuranose, l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-xylofuranose, l,2-O-isopropylidene-3-O-hexyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-xylofuranose, l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-xylofuranose, 1,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-tolyl] aminocarbonylamino} α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino] phenylacetyl-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-xylofuranose,
l,2-0-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino] phenylacetyl-alyl-L-Proline}-α,D-xylofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl) phenyl]amino carbonylamino}-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-ribofuranose,
l,2-0-isopropy!idene-3-O-dodecyl-5-deoxy-5-N-{[4-chlorophenyl]amino carbonylamino} α,D-ribofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose,
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose,
l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-ribofuranose,
l,2-O-isopropylidene-3-O-dodecyI-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose,
l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose,
l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose,
l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose,
1,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-ribofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribofuranose, l,2-O-isopropylidene-3-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-ribofuranose, l,2-O-isopropylidene-3-O-heptyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-ribofuranose, l,2-O-isopropylidene-3-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino} α,D-ribofuranose, l,2-O-isopropylidene-3-O-methyl-5-deoxy-5-N-{[4-olyl]aminocarbonylamino}α,D-ribofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylaminophenyl]acetyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Proline }-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-{[aminocarbonylaminophenyl]acetyI-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-ribofuranose,
l,2-O-isopropylidene-3-O-dodecyl-5-deoxy-5-N-[aminocarbonylamino phenyl]acetyl-L-Valyl-L-Proline }-α,D-ribofuranose.
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonyl amino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-dodecyI-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonylamino}-β, L-gulofuranoside,
Ditris salt of 2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]aminocarbonylamino}-β, L-gulofuranoside,
Sodium salt of 2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-chlorophenyl] aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-0-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-chlorophenyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-chlorophenyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} -β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} -β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-methoxyphenyl]aminocarbonyl amino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-butyl-5,6-dideoxy-5-N-{[4-tolyl]amino carbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-hexyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-decyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5,6-dideoxy-5-N-{[4-tolyl]aminocarbonylamino}-β, L-gulofuranoside,
2,3-0-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyI)phenyl]amino carbonylamino}-α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranoside,
2,3-0-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl]amino carbonylamino}-α,D-lyxofuranose,
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[4-(2-hydroxy-2-oxoethyl)phenyl] aminocarbonyl amino}-α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonyIamino}α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino}α,D-lyxofuranoside,
2,3-O-isopropyiidene-l-O-dodecyl-5-deoxy-5-N-{[4-chlorophenyl]aminocarbonylamino} α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside,
2,3-0-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[4-methoxyphenyl]aminocarbonylamino} αD-lyxofuranoside,
2,3-O-isopropylidene-l-O-methyl-5-deoxy-5-N-{[4-tolyl]amino carbonylamino}α,D-lyxo-furanoside,
2,3-O-isopropylidene-l-O-butyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-Iyxo furanoside, 2,3-O-isopropylidene-l-O-heptyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxofuranoside, 2,3-O-isopropylidene-l-O-decyl-5-deoxy-5-N-{[4-tolyl]aminocarbonylamino}α,D-lyxofuranoside,
2,3-0-isopropyIidene-l-O-dodecyl-5-deoxy-5-N-{[4-tolyl]amino carbonylamino}α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino] phenylacetyl-L-Leucyl-a,L-Aspartyl-L-Valyl-L-Proline}-α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-α,L-Aspartyl-L-Valyl-L-Proline}-α,D-lyxofuranoside,
2,3-O-isopropylidene-l-O-dodecyl-5-deoxy-5-N-{[aminocarbonylamino]phenylacetyl-L-Valyl-L-Proline}-α,D-lyxofuranoside.
2,3;4,6-Di-O-isopropylidene-l-carbonyl-L-Leucyl-a,L-Aspartyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid,
2,3;4,6-Di-0-isopropyIidene-l-carbonyl-a,L-Aspartyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid,
2,3-O-isopropylidene-l-carbonyl-L-Leucyl-a,L-Aspartyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid,
2,3-O-isopropylidene-l-carbonyl-α,L-Aspartyl-L-Valyl-L-Proline-a,L-xylo-2-hexulo furanosonic
acid,
2,3-O-isopropylidene-l-carbonyl-L-Valyl-L-Proline-α,L-xylo-2-hexulofuranosonic acid,
2,3;4,6-Di-O-isopropylidene-l-deoxy-l-N-{[4-chlorophenyl]aminocarbonylamino}-α,L-xyIo-2-hexulofuranose,
2,3;4,6-Di-0-isopropylidene-l-deoxy-l-N-{[4-methoxyphenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose,,
2,3;4,6-Di-O-isopropylidene-l-deoxy-l-N-{[4-tolyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose,
2,3-O-isopropylidene-l-deoxy-l-N-{[4-(2-hydroxy-2oxoethyl)phenyl]aminocarbonylamino}-α,L-xylo- 2-hexulofuranose,
2,3-O-isopropylidene-l-deoxy-l-N-{[4-chlorophenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose,
2,3-0-isopropylidene-l-deoxy-l-N-{[4-methoxyphenyl]aminocarbonylamino}-α,L-xylo-2-hexulofuranose,
2,3-O-isopropylidene-l-deoxy-l-N-{[4-tolyl]aminocarbonylamino}-α,L-xylo-2-hexulo-furanose,
2,3-O-isopropylidene-ldeoxy-l-N-{[aminocarbonylaminophenylacetyl-L-Leucyl-α,L-Aspartyl-L-Valyl-L-Proline)}-α,L-xylo-2-hexulofuranose,
2,3-O-isopropylidene-l-deoxy-l-N-{[aminocarbonylaminophenylacetyl-a,L-Aspartyl-L-Valyl-L-Proline)}-α,L-xylo-2-hexulofuranose, and
2,3-O-isopropylidene-ldeoxy-l-N-{[aminocarbonylaminophenylacetyl-L-Valyl-L-Proline)}-α,L-xylo-2-hexulofuranose.
2,3-O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-0-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-1 -O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-1 -yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yI-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-to!ylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyI)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yI-α-L-xylo-2-hexulofuranose,
2,3-0-lsopropylidene-l-O-decyl-4-O-(4-methoxyphenyIaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-toIylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yI-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xyIo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-l -yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-0-lsopropylidene-l-O-decyI-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-1 -O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-1 -yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-a-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-a-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-a-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -a-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-azepan-1-yl -a-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -a-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l -O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose ,
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-azepan-1 -yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-azepan-1 -y 1 -α-L-xylo-2-hexulofuranose,
2,3-O-IsopropyIidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6- azepan-1-yl -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyljamino -α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrroIidin-l-yI)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-0-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-1-yl) ethyl]amino -α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl]amino -α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-1-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-1-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl]amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-1-yl) ethyl]amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yI) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-0-lsopropylidene-l-O-decyl-4-0-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl]amino -α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-methoxyphenyIaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(piperidin-l-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropyIidene-l-O-dodecyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-(2-ethylmorphilin-4-yl)-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl]amino-α-L-xy!o-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(morphiIin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
Hydrochloride salt of 2,3-O-Isopropylidene-l-O-decyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-decyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-dodecyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-O-Isopropylidene-l-O-heptyl-4-O-(phenylaminocarbonyl)-6-deoxy-6-[2-(morphiIin-4-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3-0-lsopropylidene-l-O-heptyl-4-O-(4-chlorophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-tolylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-O-lsopropylidene-l-O-heptyl-4-O-(4-methoxyphenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3-0-Isopropylidene-l-O-heptyl-4-O-(4-nitrophenylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-y!)ethyl]amino-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-dodecyI-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(pyrroiidin-l-yl) ethyl] amino-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-dodecyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3,O-lsopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morpholin-4-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl)ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-decyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl) ethyl] amino -α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-pyrrolidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-morphoIin-4-yl-α-L-xylo-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-azepan-l-yl-α-L-xy!o-2-hexulofuranose,
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-piperidin-l-yl-α-L-xylo-2-hexulofuranose,
2,3,0-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(pyrrolidin-l-yl) ethyl] amino -a-L-xylo-2-hexulofuranose, and
2,3,O-Isopropylidene-l-O-heptyl-4-O-(methylaminocarbonyl)-6-deoxy-6-[2-(morphilin-4-yl)ethyl] amino -α-L-xylo-2-hexulofuranose.
6. Use of a compound for the manufacture of a medicament for inhibiting, preventing or
suppressing the generation of leukotrienes and related substances, wherein the compounds are
selected from a compound claimed in any of the claims 1-5.
7. The method according to claim 6, wherein the related substances are selected from the group
comprising of cytokines, chemokine gene expressions and proteolytic enzymes.

8. Use of a compound for the manufacture of a medicament for the treatment of a pathology
wherein 5-lipoxygenase activation is implicated and activation of 5-lipoxygenase is accomplished by
administering a compound claimed in any of the claims 1-5 into a mammal in the need of such
therapy.
9. The method according to claim 8, wherein the treatment comprises the prophylaxis or direct
treatment of a mammal suffering from allergic rhinitis.
10. The method according to claim 8, wherein the treatment comprising the prophylaxis or direct
treatment of an animal suffering from chronic obstructive pulmonary disease (COPD).