Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1984-12-14
1986-04-15
Griffin, Ronald W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C08B 3716
Patent
active
045829004
ABSTRACT:
The invention relates to novel water-soluble mixed ethers of .beta.-cyclodextrin (.beta.-CD) with ether substituents comprising (C.sub.1 and C.sub.2) alkyl, hydroxy(C.sub.2 to C.sub.4)alkyl and carboxy(C.sub.1 and C.sub.2)alkyl such as methylhydroxyethyl-.beta.-CD or hydroxyethyl-carboxy-methyl-.beta.-CD; hydroxyethyl-hydroxy propyl ethers are excepted.
The process of the invention comprises reacting .beta.-cyclodextrin with at least two different alkylating, hydroxyalkylating and/or carboxyalkylating etherifying agents (for example, methyl chloride, ethylene oxide and/or chloroacetic acid) in a basic, liquid reaction medium containing an alkali-metal hydroxide, water and, optionally, at least one organic solvent (for example, dimethoxyethane or isopropanol).
REFERENCES:
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patent: 3453257 (1969-07-01), Parmerter et al.
patent: 3453258 (1969-07-01), Parmerter et al.
patent: 3459731 (1969-08-01), Gramera et al.
Chemical Abstracts, vol. 100, No. 26, Jun. 25, 1984, 100:211126s.
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Croft and Bartsch, "Synthesis fo Chemically Modified Cyclodextrins", Tetrahedron, vol. 39, No. 9, pp. 1417 to 1474 (Pergamon Press, GB, 1983); pp. 1427 to 1434.
Casu et al., "Conformation of O-Methylated Amylose and Cyclodextrins", Tetrahedron, vol. 24, pp. 803 to 821, (Pergamon Press, GB, 1968); pp. 803 to 813.
Bergeron et al., "Complex Formation between Mycobacterial Ploysaccharides or Cyclodextrins and Palmitoyl Coenzyme-A", J. Biological Chemistry, vol. 250, No. 4, pp. 1223 to 1230 (1975).
Weidenhoff et al., "Properties of Cyclodextrins, Part III, Cyclodextrin-Epichlorhydrin Resins: Preparation and Analysis", Die Starke, 21st year, No. 5, pp. 119 to 123 (1969); pp. 120-122.
Lammers et al., "Properties of Cyclodextrins, Part VI, Water Soluble Cyclodextrin-Derivatives, Preparation and Analysis", Die Starke, 23rd yr., No. 5, pp. 167 to 171 (1971).
Takeo et al., "Synthesis of Heptakis (2-O-methyl).beta.-Cycladextrin", Die Starke, 28th yr., No. 7, pp. 226, 227, (1976).
Szejtle et al., "Synthesis and .sup.13 C-NMR Spectroscopy of Methylated .beta.-Cyclodextrins", Starch/ Starke, 32 rd yr., No. 5, 165 to 169 (1980).
Szejtle et al.,"Method for the Preparation of Tablets which Rapidly Disintegrate in an Aqueous Medium", published PCT Application No. WO83/00809.
Brandt Lothar
Felcht Utz-Hellmuth
Griffin Ronald W.
Hoechst Aktiengesellschaft
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