Lincomycin derivatives possessing antibacterial activity

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

Reexamination Certificate

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C536S016200, C536S016300

Reexamination Certificate

active

10777455

ABSTRACT:
Novel lincomycin derivatives are disclosed. These lincomycin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against bacteria, including gram positive organisms, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

REFERENCES:
patent: 2851463 (1958-09-01), Hinman et al.
patent: 2928844 (1960-03-01), De Boer et al.
patent: 3086912 (1963-04-01), Bergy et al.
patent: 3255174 (1966-06-01), Bannister et al.
patent: 3268556 (1966-08-01), Hoeksema
patent: 3282917 (1966-11-01), Magerlein
patent: 3361739 (1968-01-01), Argoudelis et al.
patent: 3364197 (1968-01-01), Hoeksema
patent: 3380992 (1968-04-01), Argoudelis et al.
patent: 3435025 (1969-03-01), Birkenmeyer
patent: 3475407 (1969-10-01), Birkenmeyer
patent: 3496163 (1970-02-01), Birkenmeyer et al.
patent: 3502648 (1970-03-01), Birkenmeyer et al.
patent: 3509127 (1970-04-01), Kagan et al.
patent: 3539689 (1970-11-01), Birkenmeyer et al.
patent: 3544551 (1970-12-01), Kagan et al.
patent: 3549615 (1970-12-01), Birkenmeyer
patent: 3555007 (1971-01-01), Magerlein
patent: 3671647 (1972-06-01), Argoudelis et al.
patent: 3674647 (1972-07-01), Visser
patent: 3692767 (1972-09-01), Magerlein
patent: 3702322 (1972-11-01), Bannister
patent: 3714141 (1973-01-01), Shephard
patent: 3715346 (1973-02-01), Magerlein
patent: 3764672 (1973-10-01), Argoudelis et al.
patent: 3787390 (1974-01-01), Birkenmeyer
patent: 3817979 (1974-06-01), Argoudelis et al.
patent: 3833475 (1974-09-01), Reusser et al.
patent: 3849396 (1974-11-01), Birkenmeyer et al.
patent: 3853843 (1974-12-01), Morozwich
patent: 3856943 (1974-12-01), Birkenmeyer
patent: 3870699 (1975-03-01), Bannister
patent: 3892729 (1975-07-01), Birkenmeyer
patent: 3892730 (1975-07-01), Birkenmeyer
patent: 3915954 (1975-10-01), Bannister
patent: 4031304 (1977-06-01), Bannister
patent: RE29558 (1978-02-01), Bannister
patent: 4271266 (1981-06-01), Bergy et al.
patent: 4278789 (1981-07-01), Birkenmeyer
patent: 4293547 (1981-10-01), Lewis et al.
patent: 4309533 (1982-01-01), Birkenmeyer
patent: 4310660 (1982-01-01), Birkenmeyer
patent: 4317903 (1982-03-01), Hofstetter
patent: 4383109 (1983-05-01), Argoudelis et al.
patent: 4430495 (1984-02-01), Patt et al.
patent: 4464466 (1984-08-01), Argoudelis et al.
patent: 4568741 (1986-02-01), Livingston
patent: 4710565 (1987-12-01), Livingston et al.
patent: 2004/0116690 (2004-06-01), Lewis et al.
patent: 0161 794 (1985-11-01), None
patent: 1 298 295 (1972-11-01), None
patent: 1 347 598 (1974-02-01), None
patent: WO 89/04672 (1989-06-01), None
patent: WO 99/63937 (1999-12-01), None
patent: WO 2004/016632 (2004-02-01), None
patent: WO 2005/007665 (2005-01-01), None
patent: WO 2005/012320 (2005-02-01), None
Bannister, B. et al. (1989). “The S-Alkylation of Sulphides by an Activated Carbohydrate Epimine Under Acidic Catalysis: The Formation of α-Acetamido-Sulphides. Part 5. The Introduction of Functionality into the Sulphide Substituent,”J. Chem. Res. 4:701-794.
Corrected version of an International Search Report mailed on Jul. 26, 2004, for PCT Patent Application PCT/US03/25820 filed on Aug. 15, 2003, 2 pages.
Spizek, J. et al. (2004). “Lincomycin, Cultivation of Producing Strains and Biosynthesis,”Appl. Microbiol. Biotechnol. 63:510-519.
Sztaricskai, F. et al. (Nov. 1999). “Structural Modification of the Lincomycin Antibiotic,”The Journal of Antibiotics52(11):1050-1055.
Sztaricskai, F. et al. (Oct. 1997). “Chemical Synthesis and Structural Study of Lincomycin Sulfoxides and a Sulfone,”The Journal of Antibiotics50(10):866-873.
Sztaricskai, F. et al. (Sep. 1996). “Semisynthetic Modification of Antibiotic Lincomycin,”The Journal of Antibiotics49(9):941-943.
Anonymous (2001). “The Merck Index: Clindamycin,”Merck&Co.Monograph No. 2377, XP-002271008, one page.
Anonymous (2001). “The Merck Index: Lincomycin,”Merck&Co.Monograph No. 5522, XP-002271009, one page.
International Search Report mailed on May 18, 2004, for PCT Patent Application PCT/US03/25820 filed on Aug. 15, 2003, six pages.
Alexander, J. et al. (1988). “(Acyloxy)alkyl Carbamates as Novel Bioreversible Prodrugs for Amines: Increased Permeation through Biological Membranes,”Journal of Medicinal Chemistry31(2):318-322.
Alexander, J. et al. (1996). “Investigation of (Oxodioxolenyl)methyl Carbanates as Nonchiral Bioreversible Prodrug Moietes for Chiral Amines,”J. Med. Chem. 39(2):480-486.
Baldwin, J. E. et. al. (1990). “Stereoppecific Synthesis of Dealanylalahopcin,”Tetrahedron46(13/14):4733-4748.
Baldwin, J. E. et al. (1989). “Amino Acid Synthesis Using (L)-Pyroglutamic Acid As A Chiral Starting Material,”Tetrahedron. 45(23):7459-7468.
Birkenmeyer, R. D. et al. (1984). “Synthesis and Antimicrobial Activity of Clindamycin Analogues: A Potent Antibacterial Agent,”Journal of Medicinal Chemistry27(2):216-223.
Bousquet, Y. et al. (1997). “Preparation of Enantiopure 4-Oxygenated Pipeolic Acid Derivatives,”Tetrahedron53(46):15671-15680.
Bundgaard, H. et al. (1980). “Prodrugs as Drug Delivery Systems IV: N-Mannich bases as Potential Novel Prodrugs for Amides, Ureide, Amines, and Other NH-Acidic Compounds,”Journal of Pharmaceutical Sciences69(1):44-46.
Demange, L. et al. (1998). “Practical Synthesis of the Boc and Fmoc Protected 4-Fluoro and 4-Difluoroprolines fromTrans-4-Hydroxyproline,”Tetrahedron Letters39:1169-1172.
Del Valle, J. R. et al. (2003), “Asymmetric Hydrogenations for the Synthesis of Boc-Protected 4-Alkylprolinols and Prolines,”Journal of Organic Chemistry68(10):3923-3931.
Flaherty, P. et al. (1996). “Synthesis and Selective Monoamine Oxidase B-Inhibiting Properties of 1-Methyl-2,3,6-Tetrahydropyrid-4yl Carbomate Derivatives: Potential Prodrugs of (R)- and (S)- Nordeprenyl,”Journal of Medicinal Chemistry39(24):4756-4761.
Goldstein, B. P. et al. (1995). “Antimicrobial Activity of MDL 63,246, a New Semisynthetic Glycopeptide Antibiotic,”Antimicrob. Agents&Chemother. 39(7):1580-1588.
Jensen, N.P. et al. (1980). “Use of Aceylacetone to Prepare A Prodrug of Cycloserine,”Journal of Medicinal Chemistry23(1):6-8.
Magerlein, B. J. (1972). “Lincomycin. 14. An Improved Synthesis and Resolution of the Antimalarial Agent, 1′-Demethyl-4′-Depropyle-4′(R)-(S)-Pentyclindamycin Hydrochloride (U-24, 729A),”Journal of Medicinal Chemistry15(12):1255-1259.
Osuch, C. et al. (1956). “The Use of Organolithium Compounds to Effect the Alkylation of 2- and 4- Picoline,”Journal of American Chemical Society78:1723-1725.
Sakamoto, F. et al. (1984). “Studies on Prodrugs. II. Preparation and Characterization of (5-Substited 2-Oxo-1,3-Dioxolen-4-yl)methyl Esters of Ampicillin,”Chem, Pharm. Bull. 36(6):2241-2448.
Schroeder, W. et al. (1967). “Lincomycin. III. The Structure and Steroechemistry of the Carbohydrate Moiety,”Journal of the American Chemical Society89(10):2448-2453.
Shek, E. et al. (1976). “Improved Delivery through Biological Membranes. 2. Distribution, Excretion , and Metabolism of N-Methyl-1,6-dihyropyrident-2-Carbaldoxime Hydrochloride, A Pro-Drug of N-Methylpyridinium-2Carbalkdoxime Chloride ,”Journal of Medicinal Chemistry19(1):108-112.
Shuman, R. T. et al. (1990). “An Improved Synthesis of Homoproline and Derivatives,”Journal of Organic Chemistry55:738-741.
Weiss, W. J. et al. (1999). “In Vivo Activities of Peptidic Prodrugs of Novel Aminomethyl Tetrahydrofuranyl-lβ-Methylcarbapenems ,”Antimicrobial Agents and Chemotherapy43(3):460-464.
Yong, K. et al. (2001). “Studies on the Alkylation of 3-Methyl-3-buten-1-ol Dianion: An Efficient Synthesis of 3-Methylene-lalkanols Including A San Jose Scale Sex Pheromone,”Journal of Organic Chemistry66(24):8248-8251.
Zhang, R. et al. (1998). “Pseudo

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