Modified peptide

Chemistry: natural resins or derivatives; peptides or proteins; – Proteins – i.e. – more than 100 amino acid residues – Chemical modification or the reaction product thereof – e.g.,...

Reexamination Certificate

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Details

C530S328000, C514S002600, C424S001690

Reexamination Certificate

active

07402663

ABSTRACT:
The invention provides a peptide based on biologically active CCK-8 having improved characteristics for the treatment of obesity and/or type 2 diabetes wherein the primary structure of CCK-8 is: Asp1Tyr2(SO3H)-Met3Gly4Trp5Met6Asp7Phe8amide (SEQ ID NO:1) and wherein the peptide has at least one amino add substitution and/or modification and is not Asp1-glucitol CCK-8. The invention also provides the use of the peptide in the preparation of a medicament to inhibit food intake, induce satiety, stimulate insulin secretion, moderate blood glucose excursions, enhance glucose disposal and/or exhibit enhanced stability in plasma compared to native CCK-8 and/or for treatment of obesity and/or type 2 diabetes.

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patent: 6924264 (2005-08-01), Prickett et al.
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patent: 276 482 (1990-02-01), None
M. Rodriguez et al., “Synthesis and biological activity of pseudopeptide analogues of the C-terminal heptapeptide of cholecystokinin. On the importance of the peptide bonds.”,Journal of Medicinal Chemistry30:8 (Aug. 1987) pp. 1366-1373, American Chemical Society. Washington.
M. Rodriguez et al., “Synthesis and biological activity of some partially modified retro-inverso analogues of cholecystokinin”, Journal of Medicinal Chemistry 32:10, pp. 2331-2339 (Oct. 1989) American Chemical Society, Washington.
R. Gonzalez-Muniz et al., “Solid phase synthesis of a fully active analogue of cholecystokinin using the acid-stable OC-Phe (p-CH2) SO3H as a substitute for Boc-Tyr (SO3H) in CCK8”,International Journal of Peptide and Protein Research, vol. 37, pp. 331-340 (1991) Munksgaard, Copenhagen, DK.
O'Harte, Finbarr P. M. et al., “Glycated cholecystokinin-8 has an enhanced satiating activity and is protected against enzymic degradation”,Diabetes47(10), 1619-1624 (1998).
M-C Galas et al., “Structure-Activity Relationship Studies On Cholecystokinin Analogues With Partial Agonist Activity”,American Journal of Physiology254:2 Part 1 (1988) pp. G176-G182.
Kuwahara A et al., “Effects Of Cholecystokinin Octapeptide On Gastric Motility Of Anesthetized Dogs”,American Journal of Physiology, 251:5 Part 1 (1986) pp. G678-G681.

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