Process for preparing amino-functional cyclodextrin derivative
First Claim
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1. A process for preparing cyclodextrin (CD) derivatives having an amino function which is linked to the CD via a spacer, comprisingreacting α
- -cyclodextrin, a partially substituted α
-cyclodextrin derivative, β
-cyclodextrin, a partially substituted β
-cyclodextrin derivative, γ
-cyclodextrin, a partially substituted γ
-cyclodextrin derivative, or mixtures thereof, in the presence of a catalyst,with at least one cyclic carbamic ester;
and utilizing at least one base or at least one basic ion exchanger as said catalyst.
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Abstract
A process for preparing amino-functional cyclodextrin derivatives has an amino function which is linked to the cyclodextrin (CD) via a spacer. Compositions containing CD derivatives are prepared by this process. In this process, α-cyclodextrin, β-cyclodextrin or γ-cyclodextrin, or their partially substituted derivatives, is reacted individually or in arbitrary mixture with at least one cyclic carbamic ester. The CD derivatives, as regards the listed amino substituents, have an average degree of molar substitution per anhydroglucose unit (MS) of 0.01-0.2 and a proportion of monoamino-substituted CD derivatives which is greater than 70%.
17 Citations
10 Claims
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1. A process for preparing cyclodextrin (CD) derivatives having an amino function which is linked to the CD via a spacer, comprising
reacting α - -cyclodextrin, a partially substituted α
-cyclodextrin derivative, β
-cyclodextrin, a partially substituted β
-cyclodextrin derivative, γ
-cyclodextrin, a partially substituted γ
-cyclodextrin derivative, or mixtures thereof, in the presence of a catalyst,with at least one cyclic carbamic ester; and utilizing at least one base or at least one basic ion exchanger as said catalyst. - View Dependent Claims (2, 3, 4, 5)
- -cyclodextrin, a partially substituted α
- 6. A cyclodextrin derivative of the formula I
- space="preserve" listing-type="equation">CD--[O--(CR.sup.1 R.sup.2).sub.n --(CR.sup.3 R.sup.4).sub.m --NHR.sup.5 ].sub.k (I)
wherein CD denotes alpha-cyclodextrin, beta-cyclodextrin or gamma-cyclodextrin, or a derivative of alpha-cyclodextrin, a derivative of beta-cyclodextrin or a derivative of gamma-cyclodextrin, having at least one free OH group, wherein R1, R2, R3 and R4 are either identical or different and denote hydrogen, C1 to C4 alkyl, aryl, or aryl which is substituted by hydroxyl, C1 to C4 alkoxy, halogen or C1 to C4 alkylamine, or, when two of the radicals R1 to R4 are linked, C1 to C4 cycloalkyl, or C1 to C4 cycloalkyl- which is substituted by hydrogen, C1 to C4 alkoxy, halogen or C1 to C4 alkylamine; R5 has the same meaning as mentioned for R1 to R4, or denotes carboxyl, n and m are either identical or different and denote 1, 2 or 3. and, if CD is α
-cyclodextrin, k denotes an integer from 1 to 18,or, if CD is β
-cyclodextrin, k denotes an integer from 1 to 21,or, if CD is β
-cyclodextrin, k denotes an integer from 1 to 24,or, if CD is one of the said CD derivatives, k denotes an integer from 1 up to the number of free OH groups on the CD derivative, which has, as regards the listed amino substituents, an average degree of molar substitution per anhydroglucose unit (MS) of 0.01-0.2 and a proportion of monoamino-substituted CD derivatives which is greater than 70%. - View Dependent Claims (7)
- 8. A cyclodextrin derivative of the formula I
- space="preserve" listing-type="equation">CD--[O--(CR.sup.1 R.sup.2).sub.n --(CR.sup.3 R.sup.4).sub.m --NHR.sup.5 ].sub.k (I)
wherein CD denotes alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, or a derivative of alpha-cyclodextrin, a derivative of beta-cyclodextrin or a derivative of gamma-cyclodextrin, having at least one free OH group, R1, R2, R3 and R4 are either identical or different and denote hydrogen, or C1 to C4 alkyl, aryl, aryl- which is substituted by hydroxyl, C1 to C4 alkoxy, halogen, C1 to C4 alkylamine, or, when two of the radicals R1 to R4 are linked, C1 to C4 cycloalkyl, or C1 to C4 cycloalkyl- which is substituted by hydroxyl, C1 to C4 alkoxy, halogen or C1 to C4 alkylamine, R5 has the same meaning as mentioned for R1 to R4, or denotes carboxyl-, n and m are either identical or different and denote 1, 2 or 3, and k denotes the number 1.
- 9. A cyclodextrin derivative of the formula I
- space="preserve" listing-type="equation">CD--[O--(CR.sup.1 R.sup.2).sub.n --(CR.sup.3 R.sup.4).sub.m --NHR.sup.5 ].sub.k (I)
wherein CD denotes alpha-cyclodextrin, beta-cyclodextrin or gamma-cyclodextrin, or a derivative of alpha-cyclodextrin, a derivative of beta-cyclodextrin or a derivative of gamma-cyclodextrin, having at least one free OH group, wherein R1, R2, R3 and R4 are either identical or different and denote hydrogen, C1 to C4 alkyl, or aryl, R5 has the same meaning as mentioned for R1 to R4, or denotes carboxyl, n and m are either identical or different and denote 1, 2 or 3. and, if CD is α
-cyclodextrin, k denotes an integer from 1 to 18,or, if CD is β
-cyclodextrin, k denotes an integer from 1 to 21,or, if CD is γ
-cyclodextrin, k denotes an integer from 1 to 24,or, if CD is one of the said CD derivatives, k denotes an integer from 1 up to the number of free OH groups on the CD derivative, which has, as regards the listed amino substituents, an average degree of molar substitution per anhydroglucose unit (MS) of 0.01-0.2 and a proportion of monoamino-substituted CD derivatives which is greater than 70%.
- 10. A cyclodextrin derivative of the formula I
- space="preserve" listing-type="equation">CD--[O--(CR.sup.1 R.sup.2).sub.n --(CR.sup.3 R.sup.4).sub.m --NHR.sup.5 ].sub.k (I)
wherein CD denotes alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, or a derivative of alpha-cyclodextrin, a derivative of beta-cyclodextrin or a derivative of gamma-cyclodextrin, having at least one free OH group, R1, R2, R3 and R4 are either identical or different and denote hydrogen, or C1 to C4 alkyl, or aryl, R5 has the same meaning as mentioned for R1 to R4 or denotes carboxyl-, n and m are either identical or different and denote 1, 2 or 3, and k denotes the number 1.
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Current AssigneeConsortium Fur Elektrochemische Industrie GmbH
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Original AssigneeConsortium Fur Elektrochemische Industrie GmbH
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InventorsHirsenkorn, Rolf
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Primary Examiner(s)Nutter, Nathan M.
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Application NumberUS08/354,637Time in Patent Office581 DaysField of Search536/103, 536/107, 536/115, 536/124US Class Current536/103CPC Class CodesB01J 20/3092 Packing of a container, e.g...B01J 20/321 consisting of a polymer obt...B01J 20/3217 Resulting in a chemical bon...B01J 20/3221 the chemical bond being an ...B01J 20/3251 comprising at least two dif...B01J 20/3255 comprising a cyclic structu...B01J 2220/58 Use in a single columnC08B 37/0012 Cyclodextrin [CD], e.g. cyc...
