Granted Patent
B2
US 12,239,739 · App. 16/361,971 · Granted Mar 4, 2025
Oral dosing of GLP-1 compounds
Assignee:
Novo Nordisk A/S
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Abstract
The present invention relates to improved uses of glucagon-like peptide-1 (GLP-1) peptides in oral therapy.
Claims (34)
1. A method for treating type 2 diabetes and/or reducing body weight in a subject in need of such treatment, the method comprising:
orally administering to the subject a therapeutically effective amount of a solid oral dosage form composition comprising a glucagon-like peptide-1 (GLP-1) peptide and an enhancer,
wherein:
(a) the GLP-1 peptide is N-epsilon26-[2-(2-{2-[2-(2-{2- [(S)-4-Carboxy-4-(17-carboxyheptadecanoyl-amino) butyrylamino] ethoxy} ethoxy) acetylamino] ethoxy} ethoxy) acetyl] [Aib8,Arg34] GLP-1-(7-37) (semaglutide); and
(b) the enhancer is sodium N-(8-(2-hydroxybenzoyl) amino) caprylate (SNAC);
wherein semaglutide is the only GLP-1 peptide administered;
wherein the composition is administered daily for a period of 70 days; and
wherein the variability in plasma exposure of said GLP-1 peptide is reduced when compared to a single dose of the GLP-1 peptide.
2. The method according to claim 1 , wherein the subject is in need of treatment for both type 2 diabetes and reducing body weight.
3. The method according to claim 2 , wherein the composition comprises 200-400 mg of the SNAC.
4. The method according to claim 2 , wherein the composition comprises 2-40 mg of the semaglutide.
5. The method according to claim 4 , wherein the composition comprises 300 mg of the SNAC.
6. The method according to claim 2 , wherein the composition comprises 5-50 mg of the semaglutide.
7. The method according to claim 6 , wherein the composition comprises 300 mg of the SNAC.
8. The method according to claim 2 , wherein the composition is in the form of a tablet.
9. The method according to claim 2 , wherein the subject suffers from obesity.
10. The method according to claim 1 , wherein the subject is in need of treatment for type 2 diabetes.
11. The method according to claim 10 , wherein the composition comprises 200-400 mg of the SNAC.
12. The method according to claim 10 , wherein the composition comprises 2-40 mg of the semaglutide.
13. The method according to claim 12 , wherein the composition comprises 300 mg of the SNAC.
14. The method according to claim 13 , wherein the composition is in the form of a tablet.
15. The method according to claim 10 , wherein the composition comprises 5-50 mg of the semaglutide.
16. The method according to claim 15 , wherein the composition comprises 300 mg of the SNAC.
17. The method according to claim 16 , wherein the composition is in the form of a tablet.
18. The method according to claim 1 , wherein the patient is in need of treatment for reducing body weight.
19. The method according to claim 18 , wherein the composition comprises 200-400 mg of the SNAC.
20. The method according to claim 18 , wherein the composition comprises 2-40 mg of the semaglutide.
21. The method according to claim 20 , wherein the composition comprises 300 mg of the SNAC.
22. The method according to claim 21 , wherein the subject suffers from obesity.
23. The method according to claim 21 , wherein the composition is in the form of a tablet.
24. The method according to claim 18 , wherein the composition comprises 5-50 mg of the semaglutide.
25. The method according to claim 24 , wherein the composition comprises 300 mg of the SNAC.
26. The method according to claim 25 , wherein the subject suffers from obesity.
27. The method according to claim 25 , wherein the composition is in the form of a tablet.
Priority Claims (1)
EP 13166205
· May 2, 2013
· regional
Continuity (3)
Continuation
14785493
References Cited (400)
US 5545618A
· Buckley et al.
· 1996
[cited by applicant]
US 5574010A
· McFadden
· 1996
[cited by applicant]
US 5604203A
· Balasubramaniam
· 1997
[cited by applicant]
US 5773647A
· Leone-Bay et al.
· 1998
[cited by applicant]
US 5866536A
· Leone-Bay et al.
· 1999
[cited by applicant]
US 5968899A
· Sekine et al.
· 1999
[cited by applicant]
US 6046167A
· Balasubramaniam
· 2000
[cited by applicant]
US 6071510A
· Leone-Bay et al.
· 2000
[cited by applicant]
US 6268343B1
· Knudsen et al.
· 2001
[cited by applicant]
US 6348447B1
· Hellstrom et al.
· 2002
[cited by applicant]
US 6458924B2
· Knudsen et al.
· 2002
[cited by applicant]
US 6514500B1
· Bridon et al.
· 2003
[cited by applicant]
US 7049283B2
· Ault et al.
· 2006
[cited by applicant]
US 7235627B2
· Knudson et al.
· 2007
[cited by applicant]
US 7271149B2
· Glaesner et al.
· 2007
[cited by applicant]
US 7417028B2
· Ewing et al.
· 2008
[cited by applicant]
US 7829123B2
· Sundholm et al.
· 2010
[cited by applicant]
US 8022035B2
· Schwartz et al.
· 2011
[cited by applicant]
US 8039018B2
· Majuru et al.
· 2011
[cited by applicant]
US 8053429B2
· Cumming et al.
· 2011
[cited by applicant]
US 8097698B2
· Knudsen et al.
· 2012
[cited by applicant]
US 8536122B2
· Lau et al.
· 2013
[cited by applicant]
US 8648041B2
· Garibay et al.
· 2014
[cited by applicant]
US 8895694B2
· Spetzler et al.
· 2014
[cited by applicant]
US 8901073B2
· Bloom
· 2014
[cited by applicant]
US 9067977B2
· Spetzler et al.
· 2015
[cited by applicant]
US 9085637B2
· Oestergaard et al.
· 2015
[cited by applicant]
US 9186392B2
· Klein et al.
· 2015
[cited by applicant]
US 9266940B2
· Wieczorek et al.
· 2016
[cited by applicant]
US 9278123B2
· Sauerberg
· 2016
[cited by examiner]
US 9527900B2
· Linderoth et al.
· 2016
[cited by applicant]
US 9993430B2
· Jensen
· 2018
[cited by examiner]
US 20010011071A1
· Knudsen et al.
· 2001
[cited by applicant]
US 20050009748A1
· Dinh et al.
· 2005
[cited by applicant]
US 20050148497A1
· Khan
· 2005
[cited by applicant]
US 20060078622A1
· Majuru et al.
· 2006
[cited by applicant]
US 20060078623A1
· Dhoot et al.
· 2006
[cited by applicant]
US 20060286129A1
· Sarubbi
· 2006
[cited by applicant]
US 20070049557A1
· Ahmed et al.
· 2007
[cited by applicant]
US 20070197445A1
· Balasubramaniam
· 2007
[cited by applicant]
US 20070203058A1
· Lau et al.
· 2007
[cited by applicant]
US 20080153779A1
· Liao et al.
· 2008
[cited by applicant]
US 20080269114A1
· Schwartz
· 2008
[cited by applicant]
US 20090088369A1
· Steiness
· 2009
[cited by applicant]
US 20090099074A1
· Bridon et al.
· 2009
[cited by applicant]
US 20090111730A1
· Dorwald et al.
· 2009
[cited by applicant]
US 20090124639A1
· Oyewumi et al.
· 2009
[cited by applicant]
US 20090186811A1
· Schwartz
· 2009
[cited by applicant]
US 20100069410A1
· Majuru et al.
· 2010
[cited by applicant]
US 20100292133A1
· Spetzler et al.
· 2010
[cited by applicant]
US 20100331245A1
· Dong
· 2010
[cited by applicant]
US 20110144008A1
· Larsen et al.
· 2011
[cited by applicant]
US 20110218148A1
· Azria et al.
· 2011
[cited by applicant]
US 20110275559A1
· Ostergaard et al.
· 2011
[cited by applicant]
US 20120040893A1
· Cowley et al.
· 2012
[cited by applicant]
US 20130040877A1
· Kofoed et al.
· 2013
[cited by applicant]
US 20130096055A1
· Kofoed et al.
· 2013
[cited by applicant]
US 20130240587A1
· Buchhalter
· 2013
[cited by applicant]
US 20150141336A1
· Joergensen et al.
· 2015
[cited by applicant]
US 20160067184A1
· Nielsen et al.
· 2016
[cited by applicant]
US 20180028622A1
· Burshtein et al.
· 2018
[cited by applicant]
US 20180036234A1
· Burshtein et al.
· 2018
[cited by applicant]
US 20180036382A1
· Burshtein et al.
· 2018
[cited by applicant]
US 20180050096A1
· Burshtein et al.
· 2018
[cited by applicant]
US 20190231876A1
· Pedersen et al.
· 2019
[cited by applicant]
CN 1190893A
· 1998
[cited by applicant]
CN 1487825A
· 2004
[cited by applicant]
CN 1867360A
· 2006
[cited by applicant]
CN 101005857A
· 2007
[cited by applicant]
CN 101010339A
· 2007
[cited by applicant]
CN 101133082A
· 2008
[cited by applicant]
CN 101268099A
· 2008
[cited by applicant]
CN 101463081A
· 2009
[cited by applicant]
CN 102946875A
· 2013
[cited by applicant]
EP 0708179A2
· 1996
[cited by applicant]
EP 0908515A2
· 1999
[cited by applicant]
EP 1364967A2
· 2003
[cited by applicant]
EP 2565202A1
· 2013
[cited by applicant]
EP 2651398A1
· 2013
[cited by applicant]
JP H05506427A
· 1993
[cited by applicant]
JP 2004131398A
· 2004
[cited by applicant]
JP 2004521093
· 2004
[cited by applicant]
JP 2006520818A
· 2006
[cited by applicant]
JP 2007536268A
· 2007
[cited by applicant]
JP 2008509933A
· 2008
[cited by applicant]
JP 2009542711A
· 2009
[cited by applicant]
JP 2010530962A
· 2010
[cited by applicant]
JP 4585037B2
· 2010
[cited by applicant]
JP 2011509077A
· 2011
[cited by applicant]
JP 2012121923A
· 2012
[cited by applicant]
JP 2013543814A
· 2013
[cited by applicant]
JP 2014503526A
· 2014
[cited by applicant]
JP 2015515459A
· 2015
[cited by applicant]
KR 20060100428A
· 2006
[cited by applicant]
KR 102072202
· 2020
[cited by applicant]
NZ 219575A
· 1990
[cited by applicant]
RU 2158138C2
· 2000
[cited by applicant]
RU 2275207C2
· 2006
[cited by applicant]
WO 9111457
· 1991
[cited by applicant]
WO 9111457A1
· 1991
[cited by applicant]
WO 9614854A1
· 1996
[cited by applicant]
WO 9629342
· 1996
[cited by applicant]
WO 9725064A1
· 1997
[cited by applicant]
WO 9808871A1
· 1998
[cited by applicant]
WO 9820895
· 1998
[cited by applicant]
WO 9820885A1
· 1998
[cited by applicant]
WO 9820895A1
· 1998
[cited by applicant]
WO 9943705A1
· 1999
[cited by applicant]
WO 9943706A1
· 1999
[cited by applicant]
WO 9943707A1
· 1999
[cited by applicant]
WO 9943708A1
· 1999
[cited by applicant]
WO 9964060
· 1999
[cited by applicant]
WO 9964394A1
· 1999
[cited by applicant]
WO 0007617A1
· 2000
[cited by applicant]
WO 0016797A2
· 2000
[cited by applicant]
WO 0034331
· 2000
[cited by applicant]
WO 200048589A1
· 2000
[cited by applicant]
WO 200050012A1
· 2000
[cited by applicant]
WO 0069911
· 2000
[cited by applicant]
WO 0066629A1
· 2000
[cited by applicant]
WO 0104156
· 2001
[cited by applicant]
WO 0124777A1
· 2001
[cited by applicant]
WO 200141737A2
· 2001
[cited by applicant]
WO 0246227A2
· 2002
[cited by applicant]
WO 0247716
· 2002
[cited by applicant]
WO 0248192A2
· 2002
[cited by applicant]
WO 03002158A1
· 2003
[cited by applicant]
WO 2003005944A1
· 2003
[cited by applicant]
WO 03011892A2
· 2003
[cited by applicant]
WO 03063838A1
· 2003
[cited by applicant]
WO 03072195A2
· 2003
[cited by applicant]
WO 2004067548A2
· 2004
[cited by applicant]
WO 04066966A2
· 2004
[cited by applicant]
WO 2004093823A2
· 2004
[cited by applicant]
WO 2004104018A2
· 2004
[cited by applicant]
WO 2005005667A2
· 2005
[cited by applicant]
WO 2005004900A1
· 2005
[cited by applicant]
WO 2005014035A2
· 2005
[cited by applicant]
WO 2005014049A2
· 2005
[cited by applicant]
WO 2005027978A2
· 2005
[cited by applicant]
WO 2005028516A2
· 2005
[cited by applicant]
WO 2005058954A1
· 2005
[cited by applicant]
WO 2005058958A2
· 2005
[cited by applicant]
WO 2005049061A2
· 2005
[cited by applicant]
WO 2005077072A2
· 2005
[cited by applicant]
WO 2005077094A2
· 2005
[cited by applicant]
WO 2005089786A2
· 2005
[cited by applicant]
WO 2005089789A2
· 2005
[cited by applicant]
WO 2005089790A2
· 2005
[cited by applicant]
WO 2005099672A1
· 2005
[cited by applicant]
WO 2005107462A2
· 2005
[cited by applicant]
WO 2005107773A2
· 2005
[cited by applicant]
WO 2005117984A2
· 2005
[cited by applicant]
WO 2005121090A1
· 2005
[cited by applicant]
WO 2006005667A2
· 2006
[cited by applicant]
WO 2006017251A2
· 2006
[cited by applicant]
WO 06020207A2
· 2006
[cited by applicant]
WO 2006037810
· 2006
[cited by applicant]
WO 06049681A2
· 2006
[cited by applicant]
WO 2006077035A1
· 2006
[cited by applicant]
WO 2006082204A1
· 2006
[cited by applicant]
WO 2006084164A2
· 2006
[cited by applicant]
WO 2006097535A2
· 2006
[cited by applicant]
WO 2006097536A2
· 2006
[cited by applicant]
WO 2006097538
· 2006
[cited by applicant]
WO 2006097538A1
· 2006
[cited by applicant]
WO 2006096515A2
· 2006
[cited by applicant]
WO 2006097537A2
· 2006
[cited by applicant]
WO 2006103661A2
· 2006
[cited by applicant]
WO 2006127948A2
· 2006
[cited by applicant]
WO 2006124047A2
· 2006
[cited by applicant]
WO 2006124047A3
· 2006
[cited by applicant]
WO 2007009894A2
· 2007
[cited by applicant]
WO 2007008778A2
· 2007
[cited by applicant]
WO 2007011958A2
· 2007
[cited by applicant]
WO 2007024700A2
· 2007
[cited by applicant]
WO 2007038943A1
· 2007
[cited by applicant]
WO 2007038942A1
· 2007
[cited by applicant]
WO 2007061434A2
· 2007
[cited by applicant]
WO 2007068718A1
· 2007
[cited by applicant]
WO 07065808A2
· 2007
[cited by applicant]
WO 2007067964A2
· 2007
[cited by applicant]
WO 2007093226A1
· 2007
[cited by applicant]
WO 07109354A2
· 2007
[cited by applicant]
WO 2007117706A2
· 2007
[cited by applicant]
WO 2007121318A2
· 2007
[cited by applicant]
WO 2007128817A2
· 2007
[cited by applicant]
WO 2007146234A2
· 2007
[cited by applicant]
WO 2008003947A1
· 2008
[cited by applicant]
WO 2008003050A2
· 2008
[cited by applicant]
WO 2008020096A1
· 2008
[cited by applicant]
WO 2008028859A1
· 2008
[cited by applicant]
WO 2008033888A2
· 2008
[cited by applicant]
WO 2008039351A2
· 2008
[cited by applicant]
WO 08053360A2
· 2008
[cited by applicant]
WO 2008087186A2
· 2008
[cited by applicant]
WO 2008087190A2
· 2008
[cited by applicant]
WO 2008109385A2
· 2008
[cited by applicant]
WO 2008132435A1
· 2008
[cited by applicant]
WO 2008154619A1
· 2008
[cited by applicant]
WO 2009007714A2
· 2009
[cited by applicant]
WO 2009030771A1
· 2009
[cited by applicant]
WO 2009030738A1
· 2009
[cited by applicant]
WO 2009032749A2
· 2009
[cited by applicant]
WO 2009033710A1
· 2009
[cited by applicant]
WO 2009050738A2
· 2009
[cited by applicant]
WO 09042922
· 2009
[cited by applicant]
WO 09042922A2
· 2009
[cited by applicant]
WO 2009059188A1
· 2009
[cited by applicant]
WO 2009083549A1
· 2009
[cited by applicant]
WO 2009138511A1
· 2009
[cited by applicant]
WO 2010020978A1
· 2010
[cited by applicant]
WO 2010029159A1
· 2010
[cited by applicant]
WO 10031707A1
· 2010
[cited by applicant]
WO 2010031521A2
· 2010
[cited by applicant]
WO 2010043319A1
· 2010
[cited by applicant]
WO 2010052144A2
· 2010
[cited by applicant]
WO 2010092163A2
· 2010
[cited by applicant]
WO 2010096175A1
· 2010
[cited by applicant]
WO 2011029551A2
· 2011
[cited by applicant]
WO 11033068A1
· 2011
[cited by applicant]
WO 2011033068A1
· 2011
[cited by applicant]
WO 11045232A2
· 2011
[cited by applicant]
WO 2011058165A1
· 2011
[cited by applicant]
WO 2011084618A2
· 2011
[cited by applicant]
WO 2011094531A1
· 2011
[cited by applicant]
WO 2011109787A1
· 2011
[cited by applicant]
WO 2011116139A2
· 2011
[cited by applicant]
WO 2011131646A1
· 2011
[cited by applicant]
WO 2011138421A1
· 2011
[cited by applicant]
WO 2012080471A1
· 2012
[cited by applicant]
WO 2012140117A1
· 2012
[cited by applicant]
WO 2013009545A1
· 2013
[cited by applicant]
WO 2013139694A1
· 2013
[cited by applicant]
WO 2013139695A1
· 2013
[cited by applicant]
WO 2013189988A1
· 2013
[cited by applicant]
WO 2014005858A1
· 2014
[cited by applicant]
WO 2014177683A1
· 2014
[cited by applicant]
WO 2014178018A1
· 2014
[cited by applicant]
WO 2015071355A1
· 2015
[cited by applicant]
WO 2016128970A1
· 2016
[cited by applicant]
WO 2016128971A1
· 2016
[cited by applicant]
WO 2016128972A1
· 2016
[cited by applicant]
WO 2016128973A1
· 2016
[cited by applicant]
WO 2016128974A1
· 2016
[cited by applicant]
WO 2016198682A1
· 2016
[cited by applicant]
WO 2017060500A1
· 2017
[cited by applicant]
GenScript, “Peptide YY (PYY) (3-36), human,” https://www.genscript.com/peptide/RP10354-Peptide_YY_PYY_3_36_human.html, accessed Jan. 27, 2020.
[cited by applicant]
National Institute of Diabetes and Digestive and Kidney Diseases,“Prescription Medications to Treat Overweight and Obesity,” Jul. 2016, 10 pages, retrieved on Apr. 13, 2020, URL: https://www.niddk.nih.gov/health-informa…
[cited by applicant]
W.K. Sietsema, “The absolute oral bioavailability of selected drugs.” Mar. 1989, International Journal of Clinical Pharmacology, Therapy and Toxicology, vol. 27, No. 4, pp. 179-211.
[cited by applicant]
Declaration of Doctor Peter Rue, for EP2827885 dated Jul. 29, 2020.
[cited by applicant]
Declaration of Professor Leon Aarons for EP2827885 dated Jul. 29, 2020.
[cited by applicant]
Shajahan et al., A flexible technology for modified-release drugs: Multiple-unit pellet system (MUPS) May 2009, Journal of Controlled Release, vol. 147, No. 1, pp. 2-16.
[cited by applicant]
Physicians' Desk Reference, 54th Edition, 2000, p. 1291.
[cited by applicant]
Physicians' Desk Reference, 63rd Edition, 2009, p. 1638.
[cited by applicant]
Arbit et al. “Oral heparin: status review”. Thrombosis J, May 2006, vol. 4, No. 6, pp. 1-7.
[cited by applicant]
Emisphere Announces License Agreement With Novo Nordisk to Develop Oral Formulation of GLP-1 Receptor Agonists for Diabetes, Jun. 23, 2008 retrieved from https://www.biospace.com/article/releases/emisphere-technologies-…
[cited by applicant]
European Medicines Agency, Rybelsus EPAR Public Assessment Report, Jan. 30, 2020, pp. 1-152, p. 72.
[cited by applicant]
Notice of Opposition by Galenicum, filed Dec. 9, 2020 in European Patent 3326620.
[cited by applicant]
Notice of Opposition by Hexal Ag, filed Dec. 8, 2020 in European Patent 3326620.
[cited by applicant]
Novo Nordisk starts phase 1 trial with long-acting oral GLP-1 analogue, Jan. 13, 2010, 2 pages retrieved from https://pipelinereview.com/index.php/2010011332046/Small-Molecules/Novo-Nordisk-starts-phase-1-trial-with-lon…
[cited by applicant]
Novo Nordisk, “Novo Nordisk to acquire Emisphere Technologies and obtain ownership of the Eligen® SNAC oral delivery technology”, Nov. 6, 2020 retrieved from <https://www.novonordisk.com/content/nncorp/global/en/news-an…
[cited by applicant]
Notice of Opposition by Teva filed Dec. 4, 2020 in European Patent 3326620.
[cited by applicant]
U.S. Appl. No. 61/425,087 P (priority of opposed patent), filed Dec. 20, 2010.
[cited by applicant]
Application No. 10195285.1 (priority of opposed patent), Dec. 16, 2010.
[cited by applicant]
Steinert et al., 2010, Am J Clin Nutr, vol. 92, pp. 810-817.
[cited by applicant]
Nauck et al., 2012, Abstracts of the 48th European Association for the Study of Diabetes Annual Meeting of the EASD, Oct. 1-5, 2012, Berlin, Germany, Diabetologia, 2012, vol. 55, Suppl, S7.
[cited by applicant]
Maher Sam et al., Overcoming poor permeability: translating permeation enhancers for oral peptide delivery, Journal: Drug Discovery Today:Technologies, Year: 2011, vol. 9, No. 2, pp. e113-e119.
[cited by applicant]
Maher Sam et al., Safety and efficacy of sodium caprate in promoting oral drug absorption: from in vitro to the clinic, Journal: Advanced Drug Delivery Reviews, Year: 2009, vol. 61, pp. 1427-1449.
[cited by applicant]
Michel Marre et al., GLP-1 receptor agonists today, Journal: Diabetes Research; and Clinical Practice, Year: 2011, vol. 93, No. 3, pp. 317-327.
[cited by applicant]
Walsch Edwin G et al., Oral delivery of macromolecules: rationale underpinning Gastrointestinal Permeation Enhancement Technology (GIPET®), Journal: Therapeutic Delivery, Year: 2011, vol. 2, No. 12, pp. 1595-1610. OTH.
[cited by applicant]
Makoto Otsuka, Chemoinformetrical evaluation of granule and tablet properties of pharmaceutical preparations by near-infrared spectroscopy, “Chemometrics and Intelligent Laboratory Systems” Year 2006, vol. 82, No. 1-2, …
[cited by applicant]
Shah R. B et al. Process Analytical Technology: Chemometric Analysis of Raman and Near Infra-red Spectroscopic Data for Predicting Physical Properties of Extended Release Matrix Tablets, “Journal of Pharmaceutical Scien…
[cited by applicant]
Aenugu H.P.R et al. Near Infra Red Spectroscopy—An Overview, “International Journal of ChemTech Research” Year 2011, vol. 3, No. 2, pp. 825-836.
[cited by applicant]
Donoso M et al. Prediction of Tablet Hardness and Porosity Using Near-Infrared Diffuse Reflectance Spectroscopy as a Nondestructive Method, “Pharmaceutical Development and Technology” Year 2003, vol. 8, No. 4, pp. 357-3…
[cited by applicant]
Jeckel et al. Importance of particle size knowledge for tablet porosity determination by NIRS, “Tablet Tech Seminar, FMC Biopolymer” Year 2007, retrieved from the Internet: URL:http://www.pharmtech.uni-bonn.de/forschung…
[cited by applicant]
Remington, The Science and Practice of Pharmacy, 22nd Edition, 2012.
[cited by applicant]
Felix Kratz “A Clinical Update of Using Albumin as a Drug Vehicle—A Commentary” Journal of Controlled Release 2014 vol. 190 pp. 331-336.
[cited by applicant]
Rivera et al. Oral Delivery of Heparin in Combination with Sodium N-[8-(2-Hydroxybenzoyl)amino]caprylate: Pharmacological Considerations. Pharmaceutical Research 1997 vol. 14 No. 12 pp. 1830-1834.
[cited by applicant]
Su Young Chae et al. “Preparation, Characterization and Application of Biotinylated and Biotin-PEGylated Glucagon-Like Peptide-1 Analogues for Enhanced Oral Delivery.” Bioconjugate Chemistry 2008 vol. 19 No. 1 pp. 334-3…
[cited by applicant]
Emisphere Technologies. “Carriers Enhance Drug Delivery” Manufacturing Chemistry 1999 vol. 70 No. 6 pp. 25-26.
[cited by applicant]
Adam W. G. Alani et al., “Mechanistic Understanding of Oral Drug Absorption Enhancement of Cromolyn Sodium by an Amino Acid Derivative,” Pharmaceutical Research, 2008, vol. 25, No. 1, pp. 48-54.
[cited by applicant]
Bhansali et al., “Historical Overview of Incretin Based Therapies,” Supplement to JAPI, 2010, vol. 58, pp. 10-14.
[cited by applicant]
Valentino et al., “Central and Peripheral Molecular Targets for Antiobesity Pharmacotherapy,” Clinical Pharmacology and Therapeutics, 2010, vol. 87, No. 6, pp. 652-662.
[cited by applicant]
Bastin et al., “Salt Selection and Optimisation Procedures for Pharmaceutical New Chemical Entities,” Org Proc Res & Devt, 2000, vol. 4, pp. 427-435.
[cited by applicant]
Drug Data Report, 2006, vol. 28, p. 933.
[cited by applicant]
Anonymous, “Eligen@ Technology. Summary and Value Proposition”, Emisphere, Feb. 24, 2017, pp. 1-10, URL: https://www.emisphere.com/wp-content/uploads/2017/02/Eligen-Technology-Presentation_2.15-Update.pdf, XP055520567.
[cited by applicant]
Keck et al., Moderne Pharmazeutische Technologie, 2009, pp. 8-14.
[cited by applicant]
Kidron et al., “A Novel Per-Oral Insulin Formulation: Proof of Concept Study in Non-Diabetic Subjects,” Diabetic Medicine, 2004, vol. 21, pp. 354-357.
[cited by applicant]
Letter to Sandoz International GmbH regarding English translation of claim of patent JP4585037, dated Aug. 29, 2018.
[cited by applicant]
Mullins, “Statistics for the Quality Control Chemistry Laboratory,” 2003, Chapter I, pp. 10-17.
[cited by applicant]
SNAC, Synchem, http://www.synchem.de/product/snac, accessed Aug. 16, 2018.
[cited by applicant]
Valentino et al., “Current Trends in Targeting the Hormonal Regulation of Appetite and Energy Balance to Treat Obesity,” Expert Rev Endocrinol Metab, 2010, vol. 5, pp. 765-783.
[cited by applicant]
WHO Drug Information, “International Nonproprietary Names for Pharmaceutical Substances,” 2009, vol. 23, No. 2, p. 164.
[cited by applicant]
U.S. Appl. No. 61/425,087, filed Dec. 20, 2010.
[cited by applicant]
EP Application No. 10195285.1, filed Dec. 16, 2010.
[cited by applicant]
Wang et al., “Non-peptidic glucose-like peptide-1 receptor agonists: aftermath of serendipitous discovery,” Acta Pharmacol. Sinica, 2010, vol. 31, pp. 1026-1030.
[cited by applicant]
Baynes, Kevin C. R., “The evolving world of GLP-1 agonist therapies for type 2 diabetes” Therapeutic Advances in Endocrinology and Metabolism, 2010,,vol. 1, No. 2, pp. 61-67.
[cited by applicant]
Buckley, Stephen T. et al., “Transcellular stomach absorption of a derivatized glucagon-like peptide-1 receptor agonist” Science Translational Medicine, Nov. 14, 2018, vol. 10, pp. 1-14.
[cited by applicant]
Christensen, Mikkel et al., “Once-Weekly GLP-1 Agonists: How Do They Differ from Exenatide and Liraglutide?” Curr Diab Rep, 2010, vol. 10, pp. 124-132.
[cited by applicant]
Davies, Melanie et al., “Effect of Oral Semaglutide Compared with Placebo and Subcutaneous Semaglutide on Glycemic Control in Patients with Type 2 Diabetes” JAMA, 2017, vol. 318, pp. 1460-1470.
[cited by applicant]
Declaration by the Inventor, Flemming S. Nielsen, dated Feb. 11, 2019.
[cited by applicant]
EMEA Assessment Report EMEA/379172/2009 for Victoza (liraglutide), 2009.
[cited by applicant]
Goldberg, Michael et al., “Challenges for the Oral Delivery of Macromolecules” Nature Reviews Drug Discovery, 2003, vol. 2, pp. 289-294.
[cited by applicant]
Granhall, Charlotte et al., “Safety and Pharmacokinetics of Single and Multiple Ascending Doses of the Novel Oral Human GLP-1 Analogue, Oral Semaglutide, in Healthy Subjects and Subjects with Type 2 Diabetes” Clinical P…
[cited by applicant]
Hellriegel, Edward T. et al., “Interpatient variability in bioavailability is related to the extent of absorption: Implications for bioavailability and bioequivalence studies” Clinical Pharmacology & Therapeutics, Dec. …
[cited by applicant]
King, Simon, “ViewPoints: Novo Nordisk R&D chief predicts an oral revolution for biologics” Nov. 14, 2018, Available from: [http://www.firstwordpharma.com/print/1604592?tsid=17].
[cited by applicant]
Lee, Hye J., “Protein Drug Oral Delivery: The Recent Progress” Archives of Pharmacal Research, 2002, vol. 25, No. 5, pp. 572-584.
[cited by applicant]
Madsen, Kjeld et al., “Structure—Activity and Protraction Relationship of Long-Acting Glucagon-like Peptide-1 Derivatives: Importance of Fatty Acid Lenght, Polarity, and Bulkiness” J. Med. Chem., 2007, vol. 50, pp. 6126…
[cited by applicant]
Morishita, Mariko et al., “Is the oral route possible for peptide and protein drug delivery?” Drug Discovery Today, Oct. 2006, vol. 11, No. 19/20, pp. 905-910.
[cited by applicant]
Novo Nordisk Company announcement No. 14/2015, Novo Nordisk announces positive results for phase 2 trial with oral semaglutide in people with type 2 diabetes, www.novonordisk.com CVR No. 24256790, dated Feb. 20, 2015, p…
[cited by applicant]
Novo Nordisk Company announcement No. 52/2015, Novo Nordisk to initiate phase 3a development of oral semaglutide, a once-daily oral GLP-1 analogue, www.novonordisk.com CVR No. 24256790, dated Aug. 26, 2015, p. 1-2.
[cited by applicant]
Novo Nordisk Company announcement No. 17/2018, Novo Nordisk successfully completes the first phase 3a trial, Pioneer 1, with oral semaglutide, www.novonordisk.com CVR No. 24256790, dated Feb. 22, 2018, p. 1-3.
[cited by applicant]
Novo Nordisk Company announcement No. 47/2018, Oral semaglutide shows superior improvement in HbA1C vs empagliflozin in the Pioneer 2 trial, www.novonordisk.com CVR No. 24256790, dated May 29, 2018, p. 1-3.
[cited by applicant]
Novo Nordisk Company announcement No. 51/2018, Oral semaglutide shows statiistically significantly greater reductions in HbA1c and weight compared to Victoza® and sitagliptin in the Pioneer 4 and 7 trials, www.novonordi…
[cited by applicant]
Study NCT02014259, version 1, published Dec. 18, 2013, accessed Jun. 5, 2019.
[cited by applicant]
“Drug Absorption, Distribution and Elimination; Pharmacokinetics” http://www.columbia.edu/itc/gsas/g9600/2004/GrazianoReadings/Drugabs.pdf, available since at least Apr. 24, 2006, accessed on Jun. 3, 2019.
[cited by applicant]
“Standards of Medical Care in Diabetes—2010”, Diabetes Care, vol. 33, supplement 1, Jan. 2010, pp. S11-S61.
[cited by applicant]
Andrew D. Morris, MD, “Addressing dosing frequency in diabetes: a simple approach to improving adherence to therapy and clinical outcomes,” The Diabetes Educator, 2003, vol. 29, No. 3, pp. 440-453.
[cited by applicant]
B.J. Aungst, “Absorption Enhancers: Applications and Advances,” The AAPS Journal, 2012, vol. 14, No. 1, pp. 10-18.
[cited by applicant]
ClinicalTrials.gov archive: History of Changes for Study NCT01686945, trackchange of version of Apr. 15, 2013 (published Apr. 16, 2013) as compared to version of Sep. 13, 2012 (published Sep. 18, 2012).
[cited by applicant]
Clinicaltrials.gov, NCT01686945, page as viewed in Apr. 2013, https://clinicaltrials.gov/ct2/history/NCT01686945?A=5&B=5&C=merged#StudyPageTop.
[cited by applicant]
Coskun et al., “LY3298176, a novel dual GIP and GLP-1 receptor agonist for the treatment of type 2 diabetes mellitus: From discovery to clinical proof of concept,” Molecular Metabolism, 2018, vol. 18, pp. 3-14.
[cited by applicant]
David J. Edmonds et al., “Oral GLP-1 Modulators for the Treatment of Diabetes”. Annual Reports in Medicinal Chemistry, 2013, 1st edition, vol. 48, Chapter 9, pp. 119-130.
[cited by applicant]
DJ. Birkett, “Pharmacokinetics made easy 11 Designing dose regimens,” Australian Prescriber, 1996, vol. 19, No. 3, pp. 76-88.
[cited by applicant]
E. Mutschler et al., Mutschler Arzneimittelwirkungen, Lehrbuch der Pharmakologie und Toxikologie, 8th edition 2001, pp. 48-51.
[cited by applicant]
Emisphere Annual Report and Proxy 2013, publicly available at the latest on Apr. 17, 2014.
[cited by applicant]
EU Clinical Trials Register Summary EudraCT No. 2012-004994-16 (NN9924-3790), published Jul. 30, 2013, accessed Jun. 7, 2019.
[cited by applicant]
EU Leaflet of Linagliptin, 1st authorization in EU: Aug. 24, 2011 (p. 2, 3 & 13).
[cited by applicant]
EU Leaflet of Linagliptin-Metformin, 1st authorization in EU:Jul. 20, 2012 (p. 2, 3 & 21).
[cited by applicant]
EU Leaflet of Metformin, 1st authorization in EU: Jul. 31, 2001 (p. 1, 2 & 11).
[cited by applicant]
EU Leaflet of Saxagliptin, 1st authorization in EU: Oct. 1, 2009 (p. 1 & 18).
[cited by applicant]
EU Leaflet of Sitagliptin, 1st authorization in EU: Mar. 21, 2007 (p. 2, 3 & 16).
[cited by applicant]
EU Leaflet of Sitagliptin-Metformin, 1st authorization in EU: Jul. 16, 2008 (p. 2, 3 & 20).
[cited by applicant]
EU Leaflet of Vildagliptin, 1st authorization in EU: Sep. 26, 2007(p. 2, 3 & 18).
[cited by applicant]
EU Leaflet of Vildagliptin-Metformin, 1st authorization in EU: Nov. 14, 2007 (p. 2, 3 & 21).
[cited by applicant]
European Patent Application 13166205, filed May 2, 2013.
[cited by applicant]
Geiser et al., “Clinical Pharmacokinetics of Dulaglutide in Patients with Type 2 Diabetes: Analyses of Data from Clinical Trials”. Clinical Pharmacokinetics, 2016, vol. 55, pp. 625-634.
[cited by applicant]
Granhall et al, Safety and Pharmacokinetics of Single and Multiple Ascending Doses of the Novel Oral Human GLP-1 Analogue, Oral Semaglutide, in Healthy Subjects and Subjects with Type 2 Diabetes, Clinical Pharmacokineti…
[cited by applicant]
Leon Shargel, Applied Biopharmaceutics and Pharmacokinetics, 6th edition, 2012, Chapter 8, Multiple-Dosage Regimens, pp. 153-175.
[cited by applicant]
Linda Felton, Remington, Essentials of Pharmaceutics, 2012, Chapter 37, pp. 708-709 and 712-713.
[cited by applicant]
M. Gonzalez Brao, “48th Annual Meeting of the European Association for the Study of Diabetes (EASD),” Drugs of the Future, 2012, vol. 37, No. 12, pp. 871-878.
[cited by applicant]
Malcolm Rowland et al., “Clinical Pharmacokinetics and Pharmacodynamics : Concepts and Applications,” Chapter 11—Multiple-Dose Regimens (pp. 293-329); 4th ed.; Philadelphia: Wolters Kluwer Health/Lippincott William & Wi…
[cited by applicant]
Product details regarding David J. Edmonds et al., “Oral GLP-1 Modulators for the Treatment of Diabetes”. Annual Reports in Medicinal Chemistry (2013), 1st edition, vol. 48, chapter 9, pp. 119-130, from amazon.com, acce…
[cited by applicant]
Prosecution file of EP2991671B1, available at the EPO Register, the pdf is not attached. https://register.epo.org/application?number=EP14721834&lng=en&tab=doclist, accessed Jun. 14, 2019.
[cited by applicant]
Quianzon et al., “Lixisenatide-Once daily glucagon-like peptide-1 receptor agonist in the management of type 2 diabetes,” 2011, US Endocrinology, Diabetes Management, vol. 7, No. 2, pp. 104-109.
[cited by applicant]
Rosenstock et al., “Potential of albiglutide, a long-acting GLP-1 receptor agonist, in type 2 diabetes: a randomized controlled trial exploring weekly, biweekly, and monthly dosing”. Diabetes Care, 2009, vol. 32, No. 10…
[cited by applicant]
S. Dhillon et al., “Basic Pharmacokinetics,” Clinical Pharmacokinetics, 2006, Pharmaceutical Press, London; Chapter 1, pp. 1-44.
[cited by applicant]
Sarfaraz K. Niazi, Handbook of Bioequivalence Testing, 2007, p. 13-15.
[cited by applicant]
Sisson, “Liraglutide: clinical pharmacology and considerations for therapy,” Pharmacotherapy, 2011, vol. 31, pp. 896-911.
[cited by applicant]
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