Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-03-11
1996-12-10
Northington Davis, Zinna
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 22, C07D33908
Patent
active
055832350
ABSTRACT:
The present invention provides an improved procedure for the preparation of 3,6-disubstituted-1,2-dithiin derivatives, especially unsymmetrical 1,2-dithiins. In addition, the process offers significant process, scaleup, and safety advantages over the previously reported synthetic processes. The compounds synthesized by this new process and described herein are particularly effective in treating fungal infections, especially those caused by Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Trichophyton rubrum, Candida parapsilosis, Candida tropicalis, or Candida krusei.
REFERENCES:
patent: 4659733 (1987-04-01), DuPriest et al.
patent: 5202348 (1994-04-01), Towers et al.
Chemical Abstracts, vol. 77, No. 1, Abstract No. 4826n, p. 433, Jul. 3, 1972, Reid et al.
E. Block et al., "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 (1994).
T. W. Greene et al., "Protective Groups in Organic Synthesis", John Wiley & Sons, Inc., New York, 1991, p. 296.
Freeman and Kim, 1989, "The Chemistry of 1,2-Dithiins," Sulfur Reports 9(3):207-256.
Koreeda and Yang, Mar. 1994, "The Chemistry of 1,2-Dithiins: Synthesis of 1,2-Dithiin and 3,6-Disubstituted 1,2-Dithiins," Synlett 201-203.
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.
Mao et al., 1994, "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.
Yang and Koreeda, 1993, American Chemical Society, Division of Organic Chemistry, 206th National Meeting, Aug. 22-27 1993, Abstract 349.
Koreeda and Yang, 1994, "Chemistry of 1,2-Dithiins. Synthesis of the Potent Antibiotic Thiarubrine A", J Am Chem Soc 116:10793-10794.
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.
Ellis et al., 1993, "A Diathiacyclohexadiene 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.
Cimiraglia 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.
Aihara et al., 1990, "Chemical Evolution, Biosynthesis, and Aromaticity", J Bull Chem Soc Jpn, 63:2899-2903.
Balza et al., 1990, "Dithiacyclohexadiene 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.
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.
Fabian and Birner, 1988, "A Theoretical Study of the Disulfide/Dithione Valence Isomerism", Coll Czech Chem Comm 53:2096-2115.
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 Dithiacyclohexadiene Polyine", Planta Medica 51:225-229.
Rodriguez et al., 1985, "Thiarubrine A, a Bioactive Constituent of Aspilia (Asteraceae) Consumed by Wild Chimpanzees", 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 (S2Cl2 to Alkynes", Chemical Abstracts 77:433, Abstract 4826m.
Bohlmann and Kleine, 1965, "Uber rote Naturliche Schwefelacetylenverbindungen", M Chem Ber 98:3081-3086.
Mortensen et al., 1964, "Studies Related to Naturally Occurring 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", Izh. 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", Izh. Akad. Nauk SSSR, Ser. Khim. 8:1918.
Bierer Donald E.
Dener Jeffrey M.
Truong Thien V.
Davis Zinna Northington
Shaman Pharmaceuticals, Inc.
LandOfFree
Preparation of symmetrical and unsymmetrical 3,6-disubstituted-1 does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of symmetrical and unsymmetrical 3,6-disubstituted-1, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of symmetrical and unsymmetrical 3,6-disubstituted-1 will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-425053