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Generated: June 27, 2017

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Details for Patent: 8,097,698

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Details for Patent: 8,097,698

Title:Derivatives of GLP-1 analogs
Abstract: The present invention relates to a pharmaceutical composition comprising a GLP-1 derivative having a lipophilic substituent; and a surfactant.
Inventor(s): Knudsen; Liselotte Bjerre (Valby, DK), Huusfeldt; Per Olaf (Copenhagen O, DK), Nielsen; Per Franklin (Vaerlose, DK), Kaarsholm; Niels C. (Vanlose, DK), Olsen; Helle Birk (Allerod, DK), Bjorn; Soren Erik (Lyngby, DK), Pedersen; Freddy Zimmerdahl (Vaerlose, DK), Madsen; Kjeld (Vaerlose, DK)
Assignee: Novo Nordisk A/S (Bagsvaerd, DK)
Filing Date:Nov 26, 2007
Application Number:11/944,757
Claims:1. A glucagon-like peptide 1 (GLP-1) derivative, said derivative containing a single lipophilic substituent of from 8 to 40 carbon atoms attached, optionally via a spacer, to the C-terminal amino acid residue of a parent polypeptide where i) the parent polypeptide is selected from the group consisting of GLP-1 (7-35), GLP-1 (7-36), GLP-1 (7-37), GLP-1 (7-38), GLP-1 (7-39), GLP-1 (7-40), GLP-1 (7-41) and an analogue of any of GLP-1 (7-35), GLP-1 (7-36), GLP-1 (7-37), GLP-1 (7-38), GLP-1 (7-39), GLP-1 (7-40) and GLP-1 (7-41) where the total number of different amino acids between said analogue and the corresponding native form of GLP-1 does not exceed five, and ii) the lipophilic substituent is selected from the group consisting of an acyl group of a straight-chain alkane .alpha.,.omega.-dicarboxylic acid, an acyl group of an alkyl group, and a straight chain alkyl group.

2. The GLP-1 derivative of claim 1, wherein the lipophilic substituent is an acyl group of a straight-chain alkane .alpha.,.omega.-dicarboxylic acid.

3. The GLP-1 derivative of claim 2, wherein the acyl group is from 8 to 25 carbons in length.

4. The GLP-1 derivative of claim 2, wherein the acyl group is HOOC(CH.sub.2).sub.mCO--, wherein m is 6-38.

5. The GLP-1 derivative of claim 4, wherein the acyl group is selected from the group consisting of HOOC(CH.sub.2).sub.14CO--, HOOC(CH.sub.2).sub.16CO--, HOOC(CH.sub.2).sub.18CO--, HOOC(CH.sub.2).sub.20CO--, and HOOC(CH.sub.2).sub.22CO--.

6. The GLP-1 derivative of claim 1, wherein the lipophilic substituent is a straight chain alkyl group.

7. The GLP-1 derivative of claim 6, wherein the alkyl group is from 8 to 25 carbon atoms.

8. The GLP-1 derivative of claim 1, wherein the parent polypeptide is selected from the group consisting of Arg.sup.26-GLP-1 (7-37); Arg.sup.34-GLP-1 (7-37); Lys.sup.36-GLP-1 (7-37); Arg.sup.26,34Lys.sup.36-GLP-1 (7-37); Arg.sup.26,34Lys.sup.39-GLP-1 (7-39); Arg.sup.26,34Lys.sup.40-GLP-1 (7-40); Arg.sup.26Lys.sup.36-GLP-1(7-37); Arg.sup.34Lys.sup.36-GLP-1 (7-37); Arg.sup.26Lys.sup.39-GLP-1 (7-39); Arg.sup.34Lys.sup.40-GLP-1 (7-40); Arg.sup.26,34Lys.sup.36,39-GLP-1 (7-39); Arg.sup.26,34Lys.sup.36,40-GLP-1 (7-40); Gly.sup.8Arg.sup.26-GLP-1(7-37); Gly.sup.8Arg.sup.34-GLP-1 (7-37); Gly.sup.8Lys.sup.36-GLP-1 (7-37); Gly.sup.8Arg.sup.26,34Lys.sup.36-GLP-1 (7-37); Gly.sup.8Arg.sup.26,34Lys.sup.39-GLP-1 (7-39); Gly.sup.8Arg.sup.26,34Lys.sup.40-GLP-1 (7-40); Gly.sup.8Arg.sup.26Lys.sup.36-GLP-1(7-37); Gly.sup.8Arg.sup.34Lys.sup.36-GLP-1 (7-37); Gly.sup.8Arg.sup.26Lys.sup.39-GLP-1 (7-39); Gly.sup.8Arg.sup.34Lys.sup.40-GLP-1 (7-40); Gly.sup.8Arg.sup.26,34Lys.sup.36,39-GLP-1 (7-39); and Gly.sup.8Arg.sup.26,34Lys.sup.36,40-GLP-1 (7-40).

9. The GLP-1 derivative of claim 8, wherein the lipophilic substituent is an acyl group of a straight-chain alkane .alpha.,.omega.-dicarboxylic acid.

10. The GLP-1 derivative of claim 9, wherein the acyl group is from 8 to 25 carbons in length.

11. The GLP-1 derivative of claim 9, wherein the acyl group is HOOC(CH.sub.2).sub.mCO--, wherein m is 6-38.

12. The GLP-1 derivative of claim 11, wherein the acyl group is selected from the group consisting of HOOC(CH.sub.2).sub.14CO--, HOOC(CH.sub.2).sub.16CO--, HOOC(CH.sub.2).sub.18CO--, HOOC(CH.sub.2).sub.20CO--, and HOOC(CH.sub.2).sub.22CO--.

13. The GLP-1 derivative of claim 8, wherein the lipophilic substituent is a straight chain alkyl group.

14. The GLP-1 derivative of claim 13, wherein the alkyl group is from 8 to 25 carbon atoms.

15. A GLP-1 derivative according to claim 1, wherein the spacer is an amino acid residue except Cys or a dipeptide.
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