1,2-dithiins having antifungal activity

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

549 20, 549 22, C07D33908, A61K 31385

Patent

active

055808972

ABSTRACT:
Novel 1,2-dithiin compounds useful as antifungal or anti-infective agents, as well as methods for their use as such, are described. The 1,2-dithiin compounds are particularly effective in treating infections, especially those caused by Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Candida krusei, Candida parapsilosis, Candida tropicalis, Trichophyton rubrum, Epidermophyton species, Microsporum species, Sporothrix species, Blastomyces dermatitidis, Coccidiodes immiitis, Histoplasma capsulatum, Herpes virus, Influenza virus, Cytomegalovirus, human immunodeficiency virus, retrovirus, Adenovirus, Papillomavirus, Paravirus, Arenavirus, Bunyavirus, Coronavirus, Paramyxovirus, Picornavirus, Rhabdlovirus, Togavirus, Hepadnavirus, Staphylococcus aureus, Streptococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Enterobacter aerogenes, Klebsiella pneumoniae, Staphylococcus epidermis, Zanthomonus maltrophilia, Acinetobacter, Enterobacter cloacae, Serratia marscens, Listeria, Monocytogenes, Enterococcus faecalis, Streptococcus pyogenes; Straptococcus pneumonia, Viridans streptococci, Haemophilus influenzae, Proteus mirabilis, proteus vulgaris and Bacterioides fragilis.

REFERENCES:
patent: 4659733 (1987-04-01), DuPriest et al.
patent: 5202348 (1993-04-01), Towers et al.
patent: 5453500 (1995-09-01), Koreeda et al.
Mao et al., "In vitro Evaluation of a Series of Novel Substituted 1,2-Dithiins", XII Congress of the International Society for Human and Animal Mycology, Adelaide, South Australia, Mar. 13-18, 1994.
Koreeda and Yang, "Chemistry of 1,2-Dithiins. Synthesis of the Potent Antibiotic Thiarubrine A", J Am Chem Soc 116:10793-10794, 1994.
Koreeda and Yang, "The Chemistry of 1,2-Dithiins: Synthesis of the 1,2-Dithiin and and 3,6- Disubstituted 1,2-Dithiins", Synlett 201-203, Mar. 1994.
Block et al., 1994, "Total Synthesis of Thiarubrine B [3-(3-Buten-1-ynyl)-6-(1,3-pentadiynyl)-1,2-dithiin], the Antibiotic Principle of Giant Ragweed (Ambrosia trifida)", J Am Chem Soc 116:9403-9404.
Freeman et al., 1993, "Naturally Occurring 1,2-Dithiins" in Reviews on Heteroatom Chemistry; Oae, S., Ed., Tokyo pp. 1-19.
Hudson et al., 1993, "Light-Mediated Activities of Thiarubrines Against Human Immunodeficiency Virus", Photochemistry and Photobiology 57:675-680.
Yang and Koreeda, 1993, American Chemical Society, Division of Organic Chemistry, 206th National Meeting, Aug. 22-27 1993, Abstract 349.
Ellis et al., 1993, "A Diathiacyclohexadine Polyyne Alcohol from Ambrosia Chamissonis", Phytochemistry 33:224-228.
Gomez-Barrios et al., 1992, "Studies on the Biosynthesis of Thiarubrine A in Hairy Root Cultures of Ambrosia Artemisiifolia Using .sup.13 C-Labelled Acetates", Phytochemistry 31:2703-2707.
Cimiragilia et al., 1991, "An AB Initio Study of the Structure and Electronic Spectrum of 1,2-Dithiete and 1,2-Dithiin", J Mol Struct (Therochem). 230:287-293.
Greene and Wuts, "Protective Groups in Organic Synthesis", John Wiley & Sons, Inc., New York, 1991, P. 296.
Aihara et al., 1990, "Chemical Evolution, Biosynthesis, and Aromaticity", J Bull Chem Soc Jpn, 63:2899-2903.
Balza et al., 1990, "Dithiacyclohexadine Chlorohydrins and Related Sulphur Containing Polyynes from Ambrosia Chamissonis", Phytochemistry 29:2901-2904.
Balza et al., 1989, "Dithiacyclohexadienes and Thiophenes from Ambrosia Chamissonis", Phytochemistry 28(12):3523-3524.
Constabel et al., 1989, "Incorporation of .sup.35 S into Dithiacyclohexadiene and Thiophene Polyines in Hairy Root Cultures of Chaenactis Douglasii", Phytochemistry 28:93-95.
Freeman et al., 1989, "The Chemistry of 1,2-Dithiins", Sulfur Reports 9(3):207-256.
Constabel et al., 1989, "The Complex Nature of the Mechanism of Toxicity of Antibiotic Dithiacyclohexadiene Polyines (Thiarubrines) from the Asteraceae", Planta Med 55:35-37.
Hudson et al., 1986, "Comparison of the Antiviral Effects of Naturally Occurring Thiophenes and Polyacetylenes", N Planta Medica 52:453-457.
Hudson et al., 1986, "Antiviral Properties of Thiarubrine-A, a Naturally Occurring Polyine", Planta Med 52:51-54.
Cosio et al., 1986, "Production of Antibiotic Thiarubrines by a Crown gall Tumor Line of Chaenactis douglasii", J Plant Physiol 124:155-164.
Towers et al., 1985, "Antibiotic Properties of Thiarubrine A, a Naturally Occurring Dithiacyclohexadine Polyine", Planta Medica 51:225-229.
Rodriguez et al., 1985, "Thiarubrine A, a Bioactive Constituent of Aspilia (Asteraceae) Consumed by Wild Chimpazees", N Experimenta 41:419-420.
Kokwaro, 1976, Medicinal Plants of East Africa, East African Literature Bureau, pp. 58-76.
Ried and Ochs, 1972, "Electrophilic Addition of Disulfur Dichloride (S2C12 to Alkynes", Chemical Abstracts 77:433, Abstract 4826m.
Schroth et al., 1967, "1,2-Dithiins, a New Type of Heterocycle", Angew Chem, Int Ed Eng 6:698-699.
Schroth et al., 1966, "Stereoisomeric 1,4-dimercaptobutadiene", Chemical Abstracts vol. 64, Abstract 3339a.
Bohlmann and Kleine, 1965, "Uber rote Naturliche Schwefelacetylenverbindungen", M Chem Ber 98:3081-3086.
Mortensen et al., 1964, "Studies Related to Naturally Occuring Acetylene Compounds", Acta Chem Scand 18:2392-2394.
Dzhemilev et al., 1986, "A new catalytic reaction of elemental sulfur with acetylenes by the action of cobalt complexes", Izv. Akad. Nauk SSSR, Ser. Khim. 5:1211-1212.
Dzhemilev et al., 1987, "An original method for the preparation of sulfides and disulfides involving cobalt complexes", Izv. Akad. Nauk SSSR, Ser. Khim. 8:1918.
Koreeda et al, Syn Lett, Mar. 1994, pp. 201-203.
Fabian, Collection, Czechoslovak Chem. Communication, vol. 53, No. 9, Sep. 1988, pp. 2096-2115.

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

1,2-dithiins having antifungal activity does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 1,2-dithiins having antifungal activity, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 1,2-dithiins having antifungal activity will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-786032

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