Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV

The present invention is directed to pyrrolidinylaminoacetyl pyrrolidine boronic acid compounds that display selective, potent dipeptidyl peptidase IV (DPP-IV) inhibitory activity. These compounds are useful for the treatment of disorders that can be regulated or normalized via inhibition of DPP-IV...

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Main Authors Campbell, David Alan, Winn, David T, Betancort, Juan Manuel
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LanguageEnglish
Published 18.08.2009
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Abstract The present invention is directed to pyrrolidinylaminoacetyl pyrrolidine boronic acid compounds that display selective, potent dipeptidyl peptidase IV (DPP-IV) inhibitory activity. These compounds are useful for the treatment of disorders that can be regulated or normalized via inhibition of DPP-IV including those characterized by impaired glycemic control such as Diabetes Mellitus and related conditions. The compounds can be administered alone or with another medicament that displays pharmacological activity for treatment of these and other diseases.
AbstractList The present invention is directed to pyrrolidinylaminoacetyl pyrrolidine boronic acid compounds that display selective, potent dipeptidyl peptidase IV (DPP-IV) inhibitory activity. These compounds are useful for the treatment of disorders that can be regulated or normalized via inhibition of DPP-IV including those characterized by impaired glycemic control such as Diabetes Mellitus and related conditions. The compounds can be administered alone or with another medicament that displays pharmacological activity for treatment of these and other diseases.
Author Campbell, David Alan
Winn, David T
Betancort, Juan Manuel
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References Huber et al. (6040145) 20000300
Umemura, K., et al., "Pharmacokinetics and safety of Z-321, a novel specific orally active prolyl endopeptidase inhibitor, in healthy male volunteers.", J Clin Pharmacol., 39(5), (May 1999), 462-70.
Stout, D. M., et al., "Inhibitors of Acyl-CoA: Cholesterol O-Acyl Transferase (ACAT) as Hypocholesterolemic Agents. 6. The First Water-Soluble ACAT Inhibitor With Lipid-Regulating Activity", Chemtracts-Organic Chemistry, vol. 8, (1995), 359-362.
Hoffman et al. (4450171) 19840500
Bachovchin et al. (5462928) 19951000
Nicolosi, R. J., et al., "The ACAT Inhibitor, CI-1011 is Effective in the Prevention and Regression of Aortic Fatty Streak Area in Hamsters", Atherosclerosis 137, (1998),77-85.
Hara, S. , "Ileal Na+/blle Acid Cotransporter Inhibitors", Drugs of the Future, 24(4), (1999), 425-430.
"International Application Serial No. 04810839.3, Non-Final Office Action mailed Jul. 18, 2007", 4 pgs.
Sulsky (5962440) 19991000
Campbell et al. (2008/0182995) 20080700
Hoover et al. (5952322) 19990900
Drucker (5952301) 19990900
"International Application Serial No. 200603077-9, Non-Final Office Action mailed Mar. 24, 2008", 5 pgs.
Biller (4871721) 19891000
Mills et al. (5686104) 19971100
Grier et al. (4027009) 19770500
Villhauer (6432969) 20020800
"U.S. Appl. No. 11/381,085, Non-Final Office Action mailed Aug. 1, 2007", 9 pgs.
Cheng et al. (5770615) 19980600
"U.S. Appl. No. 11/556,944, Preliminary Amendment mailed Jul. 15, 2008", 9 pgs.
Holst, Jens J., et al., "Perspectives in Diabetes: Inhibition of the Activity of Dipeptidyl-Peptidase IV as a Treatment for Type 2 Diabetes", Diabetes, vol. 47, From the Department of Medical Physiology, University of Copenhagen, Copenhagen, Denmark, (Nov. 1998), 1663-1670.
Morissette et al. Advanced Drug Delivery Reviews 2004, 56, 275-300.
Campbell (2007/0185061) 20070800
(WO-2004/004661) 20040100
Biller, S. A., "Squalene Synthase Inhibitors", Current Pharmaceutical Design, 2(1), (1996), 1-40.
"Chilean Application Serial No. 1034-06, Office Action mailed Oct. 6, 2008", 10 pgs.
Biller et al. (5712279) 19980100
Dang, N. H, et al., "CD26: an expanding role in immune regulation and cancer.", Histol Histopathol., 17(4), (Oct. 2002), 1213-26.
Villhauer (6166063) 20001200
Hangeland et al. (6989402) 20060100
Campbell et al. (2007/0299036) 20071200
Habener (5614492) 19970300
Monaghan et al. (4231938) 19801100
(WO-00/38722) 20000700
Murakami, K., "A Novel Insulin Sensitizer Acts as a Coligand for Peroxisome Proliferation-Activated Receptor-α (PPAR-α) and PPAR-γ-Effect on PPAR-α Activation on Abnormal Lipid Metabolism in Liver of Zucker Fatty Rats", Diabetes, vol. 47, (Dec. 1998), 1841-1847.
Biller et al. (5739135) 19980400
Chen, W. T, "DPPIV and seprase in cancer invasion and angiogenesis.", Adv Exp Med Biol., 524, (2003), 197-203.
"U.S. Appl. No. 11/381,090, Response filed Sep. 23, 2008 to Non Final Office Action mailed Jun. 26, 2008", 25 pgs.
Creger (3674836) 19720700
(WO-91/16339) 19911000
McClard, R W., "Novel Phosphonylphosphinyl (P-C-P-C-) Analogues of Biochemically Interesting Diphosphates. Syntheses and Properties of P-C-P-C- Analogues of Isopentenyl Diphosphate and Dimethylallyl Diphosphate", J. Am. Chem. Soc., vol. 109, (1987), 5544-5545.
Terahara et al. (4346227) 19820800
(WO-93/10127) 19930500
(WO-03/045977) 20030600
Sedo, A., et al., "Dipeptidyl peptidase IV-like molecules: homologous proteins or homologous activities?", Biochim Biophys Acta., 1550(2), (Dec. 17, 2001), 107-16.
Sudre, B., et al., "Chronic inhibition of circulating dipeptidyl peptidase IV by FE 999011 delays the occurrence of diabetes in male zucker diabetic fatty rats.", Diabetes, 51(5), (May 2002), 1461-9.
Marighetto, A, et al., "Further evidence for a dissociation between different forms of mnemonic expressions in a mouse model of age-related cognitive decline: effects of tacrine and S 17092, a novel prolyl endopeptidase inhibitor.", Learn mem., 7(3), (May-Jun. 2000), 159-69.
Wetterau, II et al. (5595872) 19970100
(WO-2006040625) 20060400
Demuth, H.-U. , et al., "Rebuttal to Deacon and Holst: "Metformin Effects on Dipeptidyl Peptidase IV Degradation of Glucagon-like Peptide-1" Versus "Dipeptidyl Peptidase Inhibition as an Approach to the Treatment and Prevention of Type 2 Diabetes: a Historical Perspective"", Biochemical and Biophysical Research Communications 296, (2002), 229-232.
(WO-8903223) 19890400
(WO-98/00439) 19980100
(WO-98/50046) 19981100
Corey, E. J., "Application of Unreactive Analogs of Terpenoid Pyrophosphates to Studies of Multistep Biosynthesis. Demonstration That "Presqualene Pyrophosphate" Is An Essential Intermediate on the Path to Squalene", Journal of the American Chemical Society, 98(5), (1976), 1291-1293.
International Application Serial No. PCT/US04/37820, International Search Report mailed Mar. 10, 2005, 5 pgs.
U.S. Appl. No. 11/381,090, Response filed Mar. 20, 2009 to Final Office Action mailed Dec. 22, 2008, 13 pgs.
Conarello, S. L, et al., "Mice lacking dipeptidyl peptidase IV are protected against obesity and insulin resistance.", Proc Natl Acad Sci U S A., 100(11), (May 27, 2003), 6825-30.
Bachovchin, W. W., et al., "Inhibition of IgA1 Proteinases from Neisseria gonorrhoeae and Hemophilus influenzae by Peptide Prolyl Boronic Acids", Journal of Biological Chemistry. 265(7), (Mar. 5, 1990), 3738-3743.
"U.S. Appl. No. 10/514,575, Response filed Sep. 17, 2008 to Restriction Requirement mailed Aug. 19, 2008", 21 pgs.
"International Application Serial No. 200603077-9, Non-Final Office Action mailed May 29, 2007", 5 pgs.
Coutts, S. J., "Structure-Activity Relationships of Boronic Acid Inhibitors of Dipeptidyl Peptidase IV. 1. Variation of the P2 Position of Xaa-boroPro Dipeptides", J. Med. Chem. 39(10), (1996), 2087-2094.
Pospisilik, J. A, et al., "Dipeptidyl peptidase IV inhibitor treatment stimulates beta-cell survival and islet neogenesis in streptozotocin-induced diabetic rats.", Diabetes, 52(3), (Mar. 2003), 741-50.
(WO-2004044661) 20040500
(WO-2005075426) 20050800
Coutts, S. J., et al., "Two Efficient Methods for the Cleavage of Pinanediol boronate Esters Yielding the Free Boronic Acids", Tetrahedron Letters, 35(29), (1994),5109-5112.
Pederson, R. A, et al., "Improved glucose tolerance in Zucker fatty rats by oral administration of the dipeptidyl peptidase IV inhibitor isoleucine thiazolidide.", Diabetes, 47(8), (Aug. 1998), 1253-8.
(WO-89/03223) 19890400
"Point Therapeutics", http://www.pther.com, http://web.archive.org/web/20070827113729/http://www.pther.com/, Jun. 10, 2008.
Kirkpatrick, P. Nature Reviews Drug Discovery Jul. 2002, 1, 486-7.
"Avasimibe: Treatment of Lipoprotein Disorders, ACAT Inhibitor", Drugs of the Future 24(1), (1999), 9-15.
Ortiz De Montellano, P. R., "Inhibition of Squalene Synthetase by Farnesyl Pyrophosphate Analogues", Journal of Medicinal Chemistry, 20(2), (1977), 243-249.
Roth (4681893) 19870700
"Korean Application Serial No. 10-2006-7011419, OAR-MISC mailed May 16, 2008", 10 pgs.
Edmondson et al. (2003/0100563) 20030500
Villhauer (6107317) 20000800
(0896538) 19990200
"U.S. Appl. No. 11/381,090 Non-Final Office Action mailed Jun. 26, 2008", OARN, 18 Pgs.
Krause, B. R., "ACAT Inhibitors: Physiologic Mechanisms for Hypolipidemic and Anti-Atherosclerotic Activities in Experimental Animals", Inflammation: Mediators and Pathways, Ruffolo, Jr., et al., Editors, published by CRC Press, Boca Raton, FL, (1995), 173-198.
Balkan, B., et al., "Inhibition of dipeptidyl peptidase IV with NVP-DPP728 increases plasma GLP-1 (7-36 amide) concentrations and improves oral glucose tolerance in obese Zucker rats.", Diabetologia, 42(11), (Nov. 1999), 1324-31.
(WO-2005/047297) 20050500
(19616486) 19971000
(WO-03/045228) 20030600
"U.S. Appl. No. 11/381,085, Response filed Sep. 13, 2007 to Non-Final Office Action mailed Aug. 1, 2007", 9 pgs.
Hirai et al. (5260440) 19931100
Deacon, C. F., et al., "Both Subcutaneously and Intravenously Administered Glucagon-Like Peptide I are Rapidly Degraded From the NH2-Terminus in Type II Diabetic Patients and in Healthy Subjects", Diabetes, 44(9), Retrieved from the Internet: <http://gateway.ut.ovid.com.floyd.lib.umn.edu/gw2/ovidweb.cgi>, (1995), 1126-1131, (11 pgs.).
Glamkowski et al. (4448784) 19840500
Hinke, S. A., et al., "Metformin Effects on Dipeptidyl-Peptidase IV Degradation of Glucagon-like Peptide-1", Biochemical and Biophysical Research Communications 291, (2002), 1302-1308.
(WO-97/21993) 19970600
Smith, C., "RP 73163: A Bioavailable Alkysulphinyl-Diphenylimidazole ACAT Inhibitor", Bioorganic & Medicinal Chemistry Letters, 6(1), (1996), 47-50.
"International Application Serial No. 04810839.3, Supplemental European Search Report mailed Dec. 13, 2006", 3 pgs.
Fujikawa et al. (5011930) 19910400
Villhauer (6124305) 20000900
Tanaka, S., et al., "Suppression of Arthritis by the Inhibitors of Dipeptidyl PeptidaseIV", Ensho-Japanese Journal of Inflammation, 18(3), (1998), 199-202.
Lambeir, A M, et al., "Kinetic investigation of chemokine truncation by CD26/dipetidyl peptidase IV reveals a striking selectivity within the chemokine family", J Biol Chem., 276(32), (Aug. 10, 2001), 29839-45.
"International Application Serial No. 06015708.8-2177, Extended European Search Report mailed Dec. 13, 2006", 16 pgs.
Biller et al. (5760246) 19980600
Hulin et al. (5998463) 19991200
Yoshioka et al. (4572912) 19860200
(0818448) 19980100
Bachovchin et al. (2003/0153509) 20030800
(WO-93/08259) 19930400
"U.S. Appl. No. 11/381,085, Notice of Allowance mailed Oct. 11, 2007", 4 pgs.
Sliskovic, D. R., "ACAT Inhibitors: Potential Anti-atherosclerotic Agents", Current Medicinal Chemistry, 1(3), (1994), 204-225.
Angerbauer et al. (5006530) 19910400
Villhauer (6110949) 20000800
Demuth et al. (6303661) 20011000
Heiber et al. (5346701) 19940900
Bachovchin et al. (6258597) 20010700
Damon (6172081) 20010100
Kanstrup et al. (6380398) 20020400
Magnin et al. (5712396) 19980100
Bachovchin et al. (4935493) 19900600
Coutts, M. J., et al., "Structure-activity relationships of boronic acid inhibitors of dipeptidyl peptidase IV. 1. Variation of the P2 position of Xaa-bor
References_xml – year: 20000700
  ident: WO-00/38722
– year: 19980100
  ident: 5712279
  contributor:
    fullname: Biller et al.
– year: 19891000
  ident: 4871721
  contributor:
    fullname: Biller
– year: 20001200
  ident: 6166063
  contributor:
    fullname: Villhauer
– year: 20071200
  ident: 2007/0299036
  contributor:
    fullname: Campbell et al.
– year: 19801100
  ident: 4231938
  contributor:
    fullname: Monaghan et al.
– year: 19970400
  ident: WO-97/12613
– year: 20050800
  ident: WO-2005075426
– year: 20010100
  ident: 6172081
  contributor:
    fullname: Damon
– year: 19910400
  ident: 5011930
  contributor:
    fullname: Fujikawa et al.
– year: 19970100
  ident: 5595872
  contributor:
    fullname: Wetterau, II et al.
– year: 20061100
  ident: 20060121170
– year: 19930500
  ident: WO-93/10127
– year: 19950500
  ident: WO-95/11689
– year: 19991200
  ident: 5998463
  contributor:
    fullname: Hulin et al.
– year: 19770500
  ident: 4027009
  contributor:
    fullname: Grier et al.
– year: 19980100
  ident: 0818448
– year: 19900500
  ident: 4924024
  contributor:
    fullname: Biller
– year: 19990300
  ident: 5885983
  contributor:
    fullname: Biller et al.
– year: 20000800
  ident: 6107317
  contributor:
    fullname: Villhauer
– year: 19990100
  ident: WO-99/00353
– year: 19890400
  ident: WO-89/03223
– year: 19961200
  ident: WO-96/39385
– year: 19980600
  ident: 5770615
  contributor:
    fullname: Cheng et al.
– year: 20000200
  ident: 0978279
– year: 19960200
  ident: 5491134
  contributor:
    fullname: Sher et al.
– year: 19951000
  ident: 5462928
  contributor:
    fullname: Bachovchin et al.
– year: 19970500
  ident: 5631224
  contributor:
    fullname: Efendic et al.
– year: 20030600
  ident: WO-03/045977
– year: 19930100
  ident: 5177080
  contributor:
    fullname: Angerbauer et al.
– year: 19950900
  ident: 5447954
  contributor:
    fullname: Gribble et al.
– year: 19911000
  ident: WO-91/16339
– year: 19971100
  ident: 5686104
  contributor:
    fullname: Mills et al.
– year: 20010700
  ident: 6258597
  contributor:
    fullname: Bachovchin et al.
– year: 20061200
  ident: 2006/0276410
  contributor:
    fullname: Campbell et al.
– year: 20080700
  ident: 2008/0182995
  contributor:
    fullname: Campbell et al.
– year: 19990900
  ident: 5952301
  contributor:
    fullname: Drucker
– year: 20000900
  ident: 6124305
  contributor:
    fullname: Villhauer
– year: 19980500
  ident: WO-98/19998
– year: 20000800
  ident: WO-00/47206
– year: 19950100
  ident: 5385929
  contributor:
    fullname: Bjorge et al.
– year: 19980100
  ident: 5712396
  contributor:
    fullname: Magnin et al.
– year: 20011000
  ident: 6300314
  contributor:
    fullname: Wallner et al.
– year: 19870700
  ident: 4681893
  contributor:
    fullname: Roth
– year: 20030800
  ident: 2003/0153509
  contributor:
    fullname: Bachovchin et al.
– year: 19960700
  ident: 5541204
  contributor:
    fullname: Sher et al.
– year: 19840500
  ident: 4450171
  contributor:
    fullname: Hoffman et al.
– year: 19980700
  ident: 5776983
  contributor:
    fullname: Washburn et al.
– year: 19971000
  ident: 19616486
– year: 19890400
  ident: WO-8903223
– year: 19961100
  ident: 5574017
  contributor:
    fullname: Gutheil
– year: 19980400
  ident: 5739135
  contributor:
    fullname: Biller et al.
– year: 19970600
  ident: WO-97/21993
– year: 19940900
  ident: 5346701
  contributor:
    fullname: Heiber et al.
– year: 20020500
  ident: 6395767
  contributor:
    fullname: Robl et al.
– year: 20080100
  ident: 7317109
  contributor:
    fullname: Campbell et al.
– year: 19980100
  ident: WO-98/00439
– year: 20040500
  ident: WO-2004044661
– year: 19880700
  ident: 4759923
  contributor:
    fullname: Buntin et al.
– year: 19970400
  ident: WO-97/12615
– year: 20030500
  ident: 2003/0100563
  contributor:
    fullname: Edmondson et al.
– year: 19990100
  ident: WO-99/03850
– year: 19990600
  ident: WO-99/26659
– year: 20020800
  ident: 6432969
  contributor:
    fullname: Villhauer
– year: 19981100
  ident: WO-98/50046
– year: 20060100
  ident: 6989402
  contributor:
    fullname: Hangeland et al.
– year: 19840500
  ident: 4448784
  contributor:
    fullname: Glamkowski et al.
– year: 19941000
  ident: 5354772
  contributor:
    fullname: Kathawala
– year: 20061100
  ident: 2006/0264400
  contributor:
    fullname: Campbell et al.
– year: 20011000
  ident: 6303661
  contributor:
    fullname: Demuth et al.
– year: 19991000
  ident: 5965532
  contributor:
    fullname: Bachovchin
– year: 19820800
  ident: 4346227
  contributor:
    fullname: Terahara et al.
– year: 19970100
  ident: 5594016
  contributor:
    fullname: Ueno et al.
– year: 19900600
  ident: 4935493
  contributor:
    fullname: Bachovchin et al.
– year: 20030600
  ident: WO-03/045228
– year: 19931100
  ident: 5260440
  contributor:
    fullname: Hirai et al.
– year: 19950600
  ident: WO-95/15309
– year: 19970300
  ident: 5614492
  contributor:
    fullname: Habener
– year: 19991000
  ident: 5962440
  contributor:
    fullname: Sulsky
– year: 19980600
  ident: 5760246
  contributor:
    fullname: Biller et al.
– year: 19720700
  ident: 3674836
  contributor:
    fullname: Creger
– year: 19981000
  ident: 5827875
  contributor:
    fullname: Dickson, Jr. et al.
– year: 19990800
  ident: WO-99/38501
– year: 20050500
  ident: WO-2005/047297
– year: 19990900
  ident: WO-99/43663
– year: 20040100
  ident: WO-2004/004661
– year: 20070800
  ident: 2007/0185061
  contributor:
    fullname: Campbell
– year: 19910400
  ident: 5006530
  contributor:
    fullname: Angerbauer et al.
– year: 20040400
  ident: 1041068
– year: 19960100
  ident: 5488064
  contributor:
    fullname: Sher
– year: 19760900
  ident: 3983140
  contributor:
    fullname: Endo et al.
– year: 20000300
  ident: 6040145
  contributor:
    fullname: Huber et al.
– year: 20061100
  ident: 2006/0264401
  contributor:
    fullname: Campbell et al.
– year: 19990200
  ident: 0896538
– year: 19860200
  ident: 4572912
  contributor:
    fullname: Yoshioka et al.
– year: 19961200
  ident: WO-96/39384
– year: 20060400
  ident: WO-2006040625
– year: 20000800
  ident: 6110949
  contributor:
    fullname: Villhauer
– year: 19931200
  ident: 5273995
  contributor:
    fullname: Roth
– year: 20020400
  ident: 6380398
  contributor:
    fullname: Kanstrup et al.
– year: 20030900
  ident: 6617340
  contributor:
    fullname: Villhauer
– year: 20000600
  ident: WO-00/34241
– year: 20000100
  ident: 6011155
  contributor:
    fullname: Villhauer
– year: 19930400
  ident: WO-93/08259
– year: 19990900
  ident: 5952322
  contributor:
    fullname: Hoover et al.
– year: 20020300
  ident: 6355614
  contributor:
    fullname: Wallner
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Snippet The present invention is directed to pyrrolidinylaminoacetyl pyrrolidine boronic acid compounds that display selective, potent dipeptidyl peptidase IV (DPP-IV)...
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Title Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV
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