Use of amygdalin analogues for the treatment of psoriasis

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S004100, C536S018400

Reexamination Certificate

active

07956039

ABSTRACT:
The compounds of formula (I), wherein n is an integer from 0 to 4; R1 is a radical selected from the group consisting of H, CH3, CH2-CH3, C(CH3)3, COOH, CONH2and C≡CH; R2, R3, R4 and R5 are radicals independently selected from the group consisting of H, F, Cl, Br, (C1-C3)-alkoxyl and (C1-C4)-alkyl; and R6 is a radical selected from the group consisting of H, F, Cl, Br, (C1-C3)-alkoxyl, (C1-C4)-alkyl, R7, CH═CH—R7 and O—CH2—R7; wherein R7 is phenyl or phenyl mono- or independently di-substituted with F, Cl, Br, (C1-C3)-alkoxyl or (C1-C4)-alkyl, exhibit a similar chemotactic index to that of amygdalin (natural product whose chemotaxis profile is similar to that of peptide T) and, consequently, are useful for treating inflammatory and/or allergic dermatophathies, such as psoriasis, and are especially much less toxic than amygdalin.

REFERENCES:
patent: 54098339 (1979-08-01), None
patent: 2003113088 (2003-04-01), None
Fukuda et al., “Anti-tumor Promoting Effect of Glycosides fromPrunus persicaSeeds” Biol. Pharm. Bull. (2003) vol. 26 No. 2, pp. 271-273.
Prieto et al., “Pharmacological approach to the pro- and anti-inflammatory effects ofRanunculus sceleratusL.” Journal of Ethnopharmacology (2003) vol. 89 pp. 131-137.
Yamazaki et al., “XPA Gene-Deficient, SCF-Transgenic Mice with Epidermal Melanin Are Resistant to UV-Induced Carcinogenesis” Journal of Investigative Dermatology (2004) vol. 123, pp. 220-228.
Giner et al., “Anti-inflammatory glycoterpenoids fromScrophularia auriculata” European Journal of Pharmacology (2000) vol. 389, pp. 243-252.
Baroni et al., “Immunomodulatory effects of a set of amygdalin analogues on human keratinocyte cells” Experimental Dermatology (2005) vol. 14 No. 11 pp. 854-859.
Yoon et al., “Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol withBacillus maceranscyclomaltodextrin glucanyltransferase andLeuconostoc mesenteroidesB-742CB dextransucrase” Carbohydrate Research (2004) vol. 339 pp. 1517-1529.
Heilman et al., “Radical Scavenger Activity of Phenylethanoid Glycosides in FMLP Stimulated Human Polymorphonuclear Leukocytes: Structure-Activity Relationships” Planta Medica (2000) vol. 66 pp. 746-748.
E. M. Faber et al., “Peptide T Improves Psoriasis when Infused into Lesions in Nanogram Amounts”, Proc. Natl. Acad. Sci., J Am Acad Dermatol 1991, vol. 25, p. 658.
T. Talme et al., “Histopathological and Immunohistochemical Changes in Psoriatic Skin during Peptide T Treatment”, Proc. Natl. Acad. Sci., Arch Dermatol 1995, vol. 287, p. 553.
M. Marastoni et al., “Structure-Activity Relationships of Cyclics and Linear Peptide T Analogues”, Int. J. Pept. Protein Res. 1993, vol. 41, pp. 447-454.
N.B. Centeno et al., “A Proposed Bioactive Conformation of Peptide T”, J. Comp.-Aided Mol. Design 1998, vol. 12, p. 7-14.
O. Llorens et al., “A Proposed Bioactive Form of Peptide T and the Design of Peptidomimetics”, Lett. Pept. Sci. 1998, vol. 5, pp. 179-182.
O. Llorens et al., “Amygdalin Binds to the CD4 Receptor as Suggested From Molecular Modeling Studies”, Bioorg. Med. Chem. Lett. 1998, vol. 8, pp. 781-786.
C. Bliard et al., “Amygdalin as Building Block in Oligosaccharide Synthesis”, Tetrahedron Lett. 1993, vol. 34., No. 32, 5083-5084.
H. Gross et al., “Dichloromethyl-Methylether as a Reagent for Organic Synthesis and Carbohydrate Chemistry”, Zeitschrit für Chemie, 18 (1978) 201-210.
I. Farkas et al., “Selective Cleavage of Glycosides .5. Cleavage of Hepta-O-Acetylamygdalin by Means of Dichloromethyl Methyl-Ether”, Annalen der Chemie-Justus Liebig (3): 440-449 1976.
M. Bergmann et al., Gentiobial and the Ring Structure of Glucans (Part 13, on the Reduction Products of Unsaturated Sugars), Chem. Ber., 62 (1929) 2783-2788.
T. Ziegler et al., “Preparation of Some Amygdalin-Derived Gentiobiosyl Donors and Acceptors for Oligosaccharide Synthesis”, Institut fur Organische Chemie and Isotopenforschung der Universitat Stuttgart, Pfaffenwaldring 55., J. Carbohydrate Chem., 10(5), 313-631 (1991).
MA, Seung-Jin et al., “Substrate Specificity of β-Primeverosidase, A key Enzyme in Aroma Formation during Oolong Tea and Black Tea Manufacturing”, Institute for Chemical Research, Kyoto University., Bioscience, Biotechnology and Biochemistry, 2001, vol. 65, No. 12, 2719-2729.
Hirata, Toshifumi et al., “Diastereoselective Formation of Disaccharides from (RS)-1-phenylethanol by Cultured Cells ofCatharanthus roseus”., Bulletin of the Chemical Society of Japan, 2001, vol. 74, No. 3 (Abstract).
Smith D. et al., “Preparative and Analytical Separation of Amygdalin and Related Compounds in Injectables and Tablets by Reversed-phase HPLC and the Effect of Temperature on the Separation”, Journal of Chromatographic Science, 1984, vol. 22, No. 3 (Abstract).
Araya, E. et al., “Sythesis and Evaluation of Diverse Analogs of Amygdalin as Potential Peptidomimetics of Peptide T”, Bioorganic & Medicinal Chemistry Letters, vol. 15, No. 5., 2005.
International Search Report and the Written Opinion corresponding to PCT/ES2005/000641, (2005).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Use of amygdalin analogues for the treatment of psoriasis does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Use of amygdalin analogues for the treatment of psoriasis, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of amygdalin analogues for the treatment of psoriasis will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2730864

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.