Amino-cyclodextrin syntheses
First Claim
1. A compound of the formula ##STR35## wherein C is cyclodextrin, A is amino, azido or aralkoxycarbonyl-substituted amino, wherein said aralkoxy has 7 to 10 carbon atoms and n is 0, 1, 2 or 3, B is hydroxyl, or one of A and B is azido and the other is aralkoxycarbonyl-substituted amino, R is alkenyl of 2 to 6 carbon atoms, aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl of 1 to 6 carbon atoms, wherein the OR group is in at least one of the -2 and -3 positions and with the proviso that when n is 0, R is aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl;
- and where A and when B is not hydroxyl, B are attached at the cyclodextrin deoxy primary hydroxyl sites, and R forms an etherified secondary hydroxyl group wherein the A, B groups are present exclusively at the primary hydroxyl side and the R group is present exclusively at the secondary hydroxyl side of the cyclodextrin.
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Abstract
There are disclosed certain amino or azido cyclodextrin ethers, which have similar or improved properties to known cyclodextrins. The novel compounds are substituted cyclodextrins having substituents comprising amino, azido, aralkoxycarbonylamino and certain ether-linked aminoalkyl, azidoalkyl, or alkenyl groups. Also disclosed are processes for preparing such compounds.
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Citations
19 Claims
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1. A compound of the formula ##STR35## wherein C is cyclodextrin, A is amino, azido or aralkoxycarbonyl-substituted amino, wherein said aralkoxy has 7 to 10 carbon atoms and n is 0, 1, 2 or 3, B is hydroxyl, or one of A and B is azido and the other is aralkoxycarbonyl-substituted amino, R is alkenyl of 2 to 6 carbon atoms, aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl of 1 to 6 carbon atoms, wherein the OR group is in at least one of the -2 and -3 positions and with the proviso that when n is 0, R is aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl;
- and where A and when B is not hydroxyl, B are attached at the cyclodextrin deoxy primary hydroxyl sites, and R forms an etherified secondary hydroxyl group wherein the A, B groups are present exclusively at the primary hydroxyl side and the R group is present exclusively at the secondary hydroxyl side of the cyclodextrin.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
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12. A process of preparation of a compound of the formula ##STR36## wherein C is cyclodextrin, A is amino, azido or aralkoxy carbonylamino, wherein said aralkoxy has 7 to 10 carbon atoms and n is 0, 1, 2 or 3, B is hydroxyl, or one of A and B is azido and the other is aralkoxy carbonylanino, R is alkenyl of 2 to 6 carbon atoms, aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl of 1 to 6 carbon atoms, wherein the OR group is in at least one of the -2 and -3 positions, and with the proviso that when n is 0, R is aminoalkyl of 3 to 6 carbon atoms, or azidoalkyl;
- and wherein A and when B is not hydroxyl, B are attached at the cyclodextrin deoxy primary hydroxyl sites, and R forms an etherified secondary hydroxyl group wherein the A, B groups are present exclusively at the primary hydroxyl side and the R group is present exclusively at the secondary hydroxyl side of the cyclodextrin
(a) when A is azido, B is hydroxyl, n is 1,2, or 3 reacting a cyclodextrin of formula I, wherein C is cyclodextrin, B is hydroxyl, R is alkenyl of 2 to 6 carbon atoms, with alkali metal azide, triphenyl phosphine, and carbon tetrabromide, (b) when A is azido, B is aralkoxy carbonylamino, wherein said aralkoxy has 7 to 10 carbon atoms, n is 1, 2, or 3, reacting a cyclodextrin of formula I, wherein C is cyclodextrin, A is aralkoxy carbonylamino, wherein said aralkoxy has 7 to 10 carbon atoms, B is hydroxyl, R is alkenyl of 2 to 6 carbon atoms, with alkali metal azide, triphenyl phosphine, and carbon tetrabromide, (c) when A is amino, B is hydroxyl, n is 1, 2, or 3, reacting a cyclodextrin of formula I, wherein C is cyclodextrin, A is azido, B is hydroxyl, R is alkenyl of 2 to 6 carbon atoms, with hydrogen in the presence of palladium on charcoal, (d) when A is aralkoxy carbonylamino, B is hydroxyl, n is 1, 2, or 3, reacting a cyclodextrin of formula I wherein C is cyclodextrin, A is azido, B is hydroxyl, R is alkenyl of 2 to 6 carbon atoms, with sodium bicarbonate and aralkyl chloroformate, wherein said aralkyl has 7 to 10 carbon atoms, (e) when n is 0, B is hydroxyl, R is azidoalkyl of 1 to 6 carbon atoms reacting cyclodextrin with alkali metal hydride in a first step, and the product thereof with halo-, azido-alkane in a second step, and (f) when n is 0, B is hydroxyl, R is aminoalkyl of 3 to 6 carbon atoms, reacting a cyclodextrin of formula I, wherein n is 0, B is hydroxyl, R is azidoalkyl of 3 to 6 carbon atoms with triphenylphosphine in the presence of ammonia. - View Dependent Claims (13, 14, 15, 16, 17, 18, 19)
- and wherein A and when B is not hydroxyl, B are attached at the cyclodextrin deoxy primary hydroxyl sites, and R forms an etherified secondary hydroxyl group wherein the A, B groups are present exclusively at the primary hydroxyl side and the R group is present exclusively at the secondary hydroxyl side of the cyclodextrin
Specification