Antimicrobial 2-deoxystreptamine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S039000

Reexamination Certificate

active

07943749

ABSTRACT:
The present invention is directed to analogs of paromomycin having a variety of chemical functional groups attached at the 2″-O-position as well as their preparation and use as prophylactic or therapeutics against microbial infection.

REFERENCES:
patent: 3808198 (1974-04-01), Naito et al.
patent: 3860574 (1975-01-01), Naito et al.
patent: 3896106 (1975-07-01), Naito et al.
patent: 3897412 (1975-07-01), Naito et al.
patent: 3956274 (1976-05-01), Umezawa et al.
patent: 4066753 (1978-01-01), Hanessian
patent: 4347354 (1982-08-01), Cron et al.
patent: 4424343 (1984-01-01), Cron et al.
patent: 5534408 (1996-07-01), Green et al.
patent: 5935776 (1999-08-01), Green et al.
patent: 2004/0229265 (2004-11-01), Lapidot et al.
patent: 2005/0148522 (2005-07-01), Baasov et al.
patent: 2008/0214845 (2008-09-01), Migawa et al.
patent: 2008/0293649 (2008-11-01), Swayze et al.
patent: 2008/0300199 (2008-12-01), Linsell et al.
patent: 1.361.393 (1964-04-01), None
patent: 2.183.236 (1973-12-01), None
patent: 1 400 676 (1975-07-01), None
patent: 1 456 674 (1976-11-01), None
patent: 1488420 (1977-10-01), None
patent: 2068366 (1981-08-01), None
patent: 49-101355 (1974-09-01), None
patent: 52-100464 (1977-08-01), None
patent: WO 92/02530 (1992-02-01), None
patent: WO 03/059246 (2003-07-01), None
patent: WO 2005/041984 (2005-05-01), None
patent: WO 2006/052930 (2006-05-01), None
patent: WO 2007/028012 (2007-03-01), None
patent: WO 2007/064954 (2007-06-01), None
Battistini et al., “Semisynthetic Aminoglycoside Antibiotics. IV 3′,4′-Dideoxyparomomycin and Analogues,”J. of Antibiotics 35(1): 98-101, Jan. 1982.
Greenberg et al., “Design and Synthesis of New Aminoglycoside Antibiotics Containing Neamine as an Optimal Core Structure: Correlation of Antibiotic Activity with in Vitro Inhibition of Translation,”J. Am. Chem. Soc. 121(28): 6527-6541, 1999.
Hanessian and Vatele, “Aminoglycoside Antibiotics 4′-Deoxyneomycin and 4′-Deoxyparomamine,”Journal of Antibiotics 33(6): 675-678, Jun. 1980.
Hermansky, “Neomycin N-methanesulfonate,” Database CAPLUS on STN, Accession No. 60:11121, 1962, 2 pages.
Kondo et al., “Crystal Structure of the Bacterial Ribosomal Decoding Site Complexed with a Synthetic Doubly Functionalized Paromomycin Derivative: a New Specific Binding Mode to an A-minor Motif Enhances in vitro Antibacterial Activity,”ChemMedChem 2: 1631-1638, 2007.
Li et al., “Investigation of the Regioselectivity for the Staudinger Reaction and Its Application for the Synthesis of Aminoglycosides with N-1 Modification,”J. Org. Chem. 72(11): 4055-4066, 2007.
Marrero-Ponce et al., “Non-stochastic and stochastic linear indices of the molecular pseudograph's atom-adjacency matrix: a novel approach for computational in silico screening and ‘rational’ selection of new lead antibacterial agents,”J. Mol. Model. 12: 255-271, 2006.
Marrero-Ponce et al., “Atom, atom-type, and total nonstochastic and stochastic quadratic fingerprints: a promising approach for modeling of antibacterial activity,”Biooorganic&Medicinal Chemistry 13: 2881-2899, 2005.
Narita et al., “Synthesis and Activity of Butirosin Derivatives with 5″-Amidino and 5″-Guanidino Substituents,”Journal of Antibiotics 44(1): 86-92, Jan. 1991.
Shier and Rinehart, Jr., “Chemistry and Biochemistry of the Neomycins. XVI Synthesis and Bioactivity of Hexa-N-Benzylneomycins,”Journal of Antibiotics 26(10): 547-550, Oct. 1973.
Scholl et al., “Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesity1-4,5-dihydroimidazol-2-ylidene Ligands,”Org. Lett. 1(6): 953-956, 1999.
Takamoto and Hanessian, “Aminoglycoside Antibiotics: Chemical Transformation of Paromomycin Into a Bioactive Pseudotrisaccharide,”Tetrahedron Letters 46: 4009-4012, 1974.
Takeda et al., “Mutational Biosynthesis of Butirosin Analogs II. 3′,4′-Dideoxy-6′-N-Methylbutirosins, New Semisynthetic Aminoglycosides,”Journal of Antibiotics 31(10): 1031-1038, Oct. 1978.
Takeda et al., “Mutational Biosynthesis of Butirosin Analogs III. 6′-N-Methylbutirosins and 3′,4′-Dideoxy-6′-C-Methylbutirosins, New Semisynthetic Aminoglycosides,”Journal of Antibiotics 31(10): 1039-1045, Oct. 1978.
Watanabe et al., “Synthesis of 6′-Amino-1-N-[(S)-4-Amino-2-Hydroxybutyryl]-6′-Deoxylividomycin A,”Bulletin of the Chemical Society of Japan 48(8): 2303-2305, 1975.
Watanabe et al., “Synthesis of 1-N-[(S)-4-Amino-2-hydroxybutyryl]lividomycin A,”Bulletin of the Chemical Society of Japan 48(7): 2124-2126, 1975.
Watanabe et al., “Synthesis of 1-N-((s)-4-Amino-2-Hydroxybutyryl) Lividomycin A,”Journal of Antibiotics 26(5): 310-312, May 1973.
The Merck Index, twelfth edition. Budavari (ed.), Whitehouse Station: Merck & Co., Inc., Compound 1559, 1996.
Alper et al., “Probing the Specificity of Aminoglycoside—Ribosomal RNA Interactions with Designed Synthetic Analogs”, Journal of American Chemical Society 120(9): 1965-1978, 1998.
Chow and Bogdan, “A Structural Basis for RNA-Ligand Interactions”, Chemical Reviews 97(5): 1489-1513, 1997.
Francois et al., “Antibacterial Aminoglycosides with a Modified Mode of Binding to the Ribosomal-RNA Decoding Site”, Angewandte Chemie Int. Ed. 43: 6735-6738, 2004.
Hanessian et al., “Aminoglycoside antibiotics: Chemical conversion of neomycin B, paromomycin, and lividomycin B into bioactive pseudosaccharides”, Canadian Journal of Chemistry 56(11): 1482-1491, Jun. 1, 1978.
Moazed and Noller, “Interaction of antibiotics with functional sites in 16S ribosomal RNA”, Nature 327: 389-394, Jun. 4, 1987.
Pénasse et al., “Sur quelques dérivés mono N-alcoylés de la néomycine et de la paromomycine”, Bulletin de la Societe chimique de France 7(415): 2391-2394, Jul. 1969.
Sunada et al., “Enzymatic 1-N-Acetylation of Paromomycin by an Actinomycete Strain #8 with Multiple Aminoglycoside Resistance and Paromomycin Sensitivity”, The Journal of Antibiotics 52(9): 809-814, Sep. 1999.
Taniyama et al., “Antibiotics Aminosidin. II. Some Amino Derivatives of Aminosidin and Their Biological Activity”, Chemical & Pharmaceutical Bulletin 21(3): 609-615, Mar. 1973.
Tok et al., “Binding of Aminoglycoside Antibiotics with Modified A-site 16S rRNA Construct Containing Non-Nucleotide Linkers”, Bioorganic & Medicinal Chemistry Letters 12: 365-370, 2002.
Wallis and Schroeder, “The Binding of Antibiotics to RNA”, Progress in Biophysics and Molecular Biology, 67 (2/3): 141-154, 1997.
Watanabe et al., “Synthesis of 6′-amino-6′-deoxylvidomycin B and 6′-deoxy-6′-methylamino- and 6′-deoxy-6′-(2-hydroxyethylamino)-lividomycin B”, The Journal of Antibiotics 26(12): 802-804, Dec. 1973.

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

Antimicrobial 2-deoxystreptamine compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Antimicrobial 2-deoxystreptamine compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antimicrobial 2-deoxystreptamine compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2701307

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