Derivatives of gamma-cyclodextrin

• US 4,764,604 A
• Filed: 02/27/1986
• Issued: 08/16/1988
• Est. Priority Date: 03/15/1985
• Status: Expired due to Term

• Current Assignee: Janssen Pharmaceutica NV (Johnson & Johnson)
• Original Assignee: Janssen Pharmaceutica NV (Johnson & Johnson)
• Inventors: Muller, Bernd W. W.
• Primary Examiner(s): GRIFFIN, RONALD
• Application Number:
  US06/833,622
• Time in Patent Office: 901 Days
• Field of Search: 536/103
• US Class Current: 536/103
• CPC Class Codes: A61K 47/6951 using cyclodextrin cyclodextrins used as simple excipients A61K47/40
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C08B 37/0012 Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof

Abstract

This invention relates to γ-cyclodextrin ethers and mixed ethers wherein the ether substituents are C₁ -C₆ alkyl, hydroxy C₁ -C₆ alkyl, carboxy C₁ -C₆ alkyl or (C₁ -C₆ alkyloxycarbonyl) C₁ -C₆ alkyl; provided that hydroxypropyl is not a sole substituent.

Claims

1. A γ

-cyclodextrin ether or mixed ether wherein the ether substituents are C₁ -C₆ alkyl, hydroxy C₁ -C₆ alkyl, carboxy C₁ -C₆ -alkyl or (C₁ -C₆ alkyloxycarbonyl) C₁ -C₆ alkyl;

provided that hydroxypropyl is not a sole substituent.

2. A γ

-cyclodextrin ether or mixed ether according to claim 1 wherein the ether substituents are C₁ -C₃ alkyl, hydroxy C₂ -C₄ alkyl or carboxy C₁ -C₂ alkyl.

3. A γ

-cyclodextrin derivative according to claim 1, wherein the ether substituents are methyl, ethyl, isopropyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, carboxymethyl or carboxyethyl.

8. A process for preparing a compound as defined in claim 1, characterized by reacting γ

-cyclodextrin with an O-alkylating agent.

9. A process for preparing a compound as defined in claim 2, characterized by reacting γ

-cyclodextrin with an O-alkylating agent.

10. A process for preparing a compound as defined in claim 3, characterized by reacting γ

-cyclodextrin with an O-alkylating agent.

11. A process according to claim 9, wherein the process is conducted in a reaction-inert solvent in the presence of a base.

12. A process according to claim 9, wherein the process is conducted at a temperature in the range from 30°

C. to 200°

C.

13. A process according to claim 10, wherein the process is conducted in a reaction-inert solvent in the presence of a base.

14. A process according to claim 10, wherein the process is conducted at a temperature in the range from 30°

C. to 200°

C.

4. A γ

-cyclodextrin ether or mixed ether wherein the ether substituents are C₁ -C₃ alkyl, hydroxy C₂ -C₄ alkyl or carboxy C₁ -C₂ alkyl and wherein the degree of substitution is in the range of 0.125 to 3 and the average molar substitution is in the range of 0.125 to 10.

5. A γ

-cyclodextrin derivative according to claim 4, wherein the degree of substitution is in the range of 0.3 to 2 and the average molar substitution is in the range of 0.3 to 3.

6. A γ

-cyclodextrin ether or mixed ether wherein the ether substituents are methyl, ethyl, isopropyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, carboxymethyl or carboxyethyl and wherein the degree of substitution is in the range of 0.125 to 3 and the average molar substitution is in the range of 0.125 to 10.

7. A γ

-cyclodextrin derivative according to claim 6, wherein the degree of substitution is in the range of 0.3 to 2 and the average molar substitution is in the range of 0.3 to 3.

15. A γ

-cyclodextrin ether or mixed ether wherein the ether substituents are C₁ -C₆ alkyl, hydroxy C₁ -C₂ alkyl, hydroxy C₄ -C₆ alkyl, carboxy C₁ -C₆ alkyl or (C₁ -C₆ alkoxy carbonyl) C₁ -C₆ alkyl.

16. A γ

-cyclodextrin ether or mixed ether according to claim 15 wherein the ether substituents are C₁ -C₃ alkyl, hydroxy C₂ alkyl, hydroxy C₄ alkyl, or carboxy C₁ -C₂ alkyl.

17. A γ

-cyclodextrin derivative according to claim 15 wherein the either substituents are methyl, ethyl, isopropyl, hydroxyethyl, hydroxybutyl, carboxymethyl, or carboxyethyl.