Filed: March 19, 2021
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`MYLAN INSTITUTIONAL LLC and PFIZER INC.,
`Petitioners,
`
`v.
`
`NOVO NORDISK A/S,
`
`Patent Owner.
`
`
`Case No. IPR2020-003241
`U.S. Patent No. 8,114,833
`
`UPDATED LIST OF PETITIONERS’ EXHIBITS
`
`
`
`
`
`1
`IPR2020-01252 has been joined with this proceeding.
`
`
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`MYLAN INSTITUTIONAL LLC and PFIZER INC.,
`Petitioners,
`
`v.
`
`NOVO NORDISK A/S,
`
`Patent Owner.
`
`
`Case No. IPR2020-003241
`U.S. Patent No. 8,114,833
`
`UPDATED LIST OF PETITIONERS’ EXHIBITS
`
`
`
`
`
`1
`IPR2020-01252 has been joined with this proceeding.
`
`
`
`
`
`EXHIBIT
`NO.
`
`
`
`DESCRIPTION
`
`1001
`
`1002
`1003
`
`1004
`
`1005
`
`1006
`
`1007
`
`1008
`
`1009
`
`1010
`
`1011
`
`U.S. Patent No. 8,114,833, Propylene Glycol-Containing
`Peptide Formulations which Are Optimal for Production and
`for Use in Injection Devices (filed May 17, 2006) (issued Feb.
`14, 2012)
`
`Declaration of Laird Forrest, Ph.D.
`Prosecution history excerpts for U.S. Patent No. 8,114,833
`International Publication No. WO 03/002136, Stable
`Formulation of Modified GLP-1 (published Jan. 9, 2003)
`(“Flink”)
`International Publication No. WO 2004/004781, Liquid
`Formulations with High Concentration of Human Growth
`Hormone (hgh) Comprising 1,2-Propylene Glycol (published
`Jan. 15, 2004) (“Betz”)
`U.S. Patent No. 6,268,343, Derivatives of GLP-1 Analogs (filed
`Feb. 26, 1999) (issued July 31, 2001)
`EP 0 923 950, Liquid Agent for Contact Lens (issued June 23,
`1999)
`M. Powell et al., Parenteral Peptide Formulations: Chemical
`and Physical Properties of Native Luteinizing Hormone-
`Releasing Hormone (LHRH) and Hydrophobic Analogues in
`Aqueous Solution, 8(10) PHARM. RES. 1258 (1991)
`E. Epperson, Mannitol Crystallization in Plastic Containers, 35
`AM. J. HOSP. PHARM. 1337 (1978)
`W. Griffin et al., Polyhydric Alcohols, in CRC HANDBOOK OF
`FOOD ADDITIVES 431 (Thomas E. Furia ed., 2d ed. 1972)
`J. Jacobs, Factors Influencing Drug Stability in Intravenous
`Infusions, 27 J. HOSP. PHARM. 341 (Dec. 1969)
`
`
`
`
`
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1012
`
`1013
`
`1014
`
`1015
`1016
`1017
`
`1018
`
`1019
`
`1020
`
`1021
`
`1022
`1023
`
`1024
`
`MODERN PHARMACEUTICS (Gilbert S. Banker et al. eds., 3d ed.
`1996)
`REMINGTON’S PHARMACEUTICAL SCIENCES (18th ed. 1990)
`International Publication No. WO 03/072195, Method for
`Administering GLP-1 Molecules (published Sept. 4, 2003).
`INTENTIONALLY LEFT BLANK
`INTENTIONALLY LEFT BLANK
`U.S. Patent No. 8,759,291, Methods of Treatment using
`Exendin Peptides or GLP-1 Peptides (filed Apr. 5, 2011)
`(issued June 24, 2014)
`U.S. Patent Application Publication US 2005/0148497, Method
`for Administering GLP-1 Molecules (July 7, 2005)
`International Publication No. WO 95/22560 A1,
`Pharmaceutical Formulations of CNTF (published Aug. 24,
`1995)
`U.S. Patent No. 6,458,924, Derivatives of GLP-1 Analogs
`(filed Sept. 16, 1999) (issued Oct. 1, 2002)
`International Publication No. WO 00/37098 A1, Shelf-Stable
`Formulation of Glucagon-Like Peptide-1 (published June 29,
`2000)
`Handbook of Pharmaceutical Excipients (3d ed. 2000)
`Handbook of Pharmaceutical Excipients (4th ed. 2003)
`Akers, Formulation Development of Protein Dosage Forms in
`DEVELOPMENT AND MANUFACTURE OF PROTEIN
`PHARMACEUTICALS (2002)
`
`2
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1025
`
`1026
`
`1027
`
`1028
`
`1029
`
`1030
`
`1031
`
`1032
`
`1033
`
`1034
`
`1035
`
`1036
`
`International Patent Publication No. WO 1999/040788,
`Inotropic and Diuretic Effects of Exendin and GLP-1
`(published August 19, 1999)
`DEVELOPMENT OF BIOPHARMACEUTICAL PARENTERAL DOSAGE
`FORMS (John A. Bontempo ed., 1997)
`Gatlin, Formulation and Administration Techniques to
`Minimize Injection Pain and Tissue Damage Associated with
`Parenteral Products in INJECTABLE DRUG DEVELOPMENT
`(1999)
`A DICTIONARY OF CHEMISTRY (1996) (excerpts)
`FDA Guidance for Industry - Chemistry Manufacturing and
`Controls (2003)
`U.S. Patent No. 5,514,097, Self Administered Injection Pen
`Apparatus and Method (issued May 7, 1996)
`International Publication No. WO 93/19175, Receptor for the
`Glucagon-Like-Peptide-1 (GLP-1) (published Sept. 30, 1993)
`International Publication No. WO 99/43705, N-Terminally
`Truncated GLP-1 Derivatives (published Sept. 2, 1999)
`International Publication No. WO 99/43706, Derivatives of
`GLP-1 Analogs (published Sept. 2, 1999)
`International Publication No. WO 99/43707, N-Terminally
`Modified GLP-1 Derivatives (published Sept. 2, 1999)
`International Publication No. WO 98/08871, GLP-1
`Derivatives (published Mar. 5, 1998)
`International Publication No. WO 02/46227, GLP-1 Fusion
`Proteins (published June 13, 2002)
`
`3
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1037
`
`1038
`
`1039
`
`1040
`
`1041
`
`1042
`
`1043
`
`1044
`
`1045
`
`1046
`
`1047
`
`International Publication No. WO 99/43708, GLP-1
`Derivatives of GLP-1 and Exendin with Protracted Profile of
`Action (published Sep. 2, 1999)
`International Publication No. WO 99/43341, GLP-1
`Derivatives with Helix-Content Exceeding 25%, Forming
`Partially Structured Micellar-like Aggregates (published Sept.
`2, 1999)
`International Publication No. WO 87/06941, Insulinotropic
`Hormone (published Nov. 19, 1987)
`International Publication No. WO 90/11296, Insulinotropic
`Hormone (published Oct. 4, 1990)
`International Publication No. WO 91/11457, GLP-1 Analogs
`useful for Diabetes Treatment (published Aug. 8, 1991)
`International Publication No. WO 98/43658, Glucagon-Like
`Peptide-1 Analogs (published Oct. 8, 1998)
`International Publication No. EP 0 708 179, Glucagon-Like
`Insulinotropic Peptide Analogs, Compositions, and Methods of
`Use (published Dec. 22, 2004)
`International Publication No. EP 0 699 686, Biologically Active
`Fragments of Glucagon-Like Insulinotropic Peptide (published
`Oct. 8, 2003)
`International Publication No. WO 01/98331, Glucagon-Like
`Peptide-1 Analogs (published Dec. 27, 2001)
`J. Sturis et al., GLP-1 Derivative Liraglutide in Rats with β-cell
`Deficiencies: Influence of Metabolic State on β-cell Mass
`Dynamics, 140 BRIT. J. PHARMACOLOGY 123 (2003)
`J. Fransson et al., Local Tolerance of Subcutaneous Injections,
`48 J. PHARM. PHARMACOL. 1012 (1996)
`
`4
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1048
`
`1049
`
`1050
`
`1051
`
`1052
`
`1053
`
`1054
`
`1055
`
`1056
`
`1057
`
`L. Gerweck et al., Cellular pH Gradient in Tumor Versus
`Normal Tissue: Potential Exploitation for the Treatment of
`Cancer, 56 CANCER RESEARCH 1194 (1996)
`I. Madshus, Regulation of Intracellular pH in Eukaryotic Cells,
`250 BIOCHEM. J. 1 (1988)
`C. Fox et al., Ability to Handle, and Patient Preference for,
`Insulin Delivery Devices in Visually Impaired Patients with
`Type 2 Diabetes, 19(4) PRACTICAL DIABETES INT 104 (2002)
`A.M. Robinson et al., Subcutaneous Versus Intravenous
`Administration of Heparin in the Treatment of Deep Vein
`Thrombosis; Which do Patients Prefer? A Randomized Cross-
`Over Study, 69 POSTGRAD MED J. 115 (1993)
`D. Schade et al., The Intravenous, Intraperitoneal, and
`Subcutaneous Routes of Insulin Delivery in Diabetic Man, 28
`DIABETES 1069 (1979)
`X.H. Zhou et al., Peptide and Protein Drugs: I. Therapeutic
`Applications, Absorption and Parenteral Administration, 75
`INT’L J. PHARM. 97 (1991)
`J. Napaporn et al., Assessment of the Myotoxicity of
`Pharmaceutical Buffers Using an In vitro Muscle Model: Effect
`of pH, Capacity, Tonicity, and Buffer Type, 5(1) PHARM. DEV.
`& TECH. 123 (2000)
`
`C.M.B. Edwards et al., Peptides as Drugs, 92 Q J MED 1 (1999)
`C. Akiyama et al., Comparison of Behavior in Muscle Fiber
`Regeneration After Bupivacaine Hydrochloride- and Acid
`Anhydride-Induced Myonecrosis, 83 ACTA NEUROPATHOL 584
`(1992)
`Alfred Martin, PHYSICAL PHARMACY (4th ed. 1993)
`
`5
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1058
`
`1059
`
`1060
`
`1061
`
`1062
`
`1063
`
`1064
`
`1065
`
`1066
`
`1067
`
`1068
`
`S. Borchert et al., Particulate Matter in Parenteral Products: A
`Review, 40 J. PARENTERAL SCI. & TECH. 212 (1986)
`X. Chang et al., NMR Studies of the Aggregation of Glucagon-
`Like Peptide-1: Formation of a Symmetric Helical Dimer, 515
`FEBS LETTERS 165 (2002)
`M. Stranz et al., A Review of pH and Osmolarity, 6(3) INT’L J.
`PHARM. COMPOUNDING 216 (2002)
`PHARMACEUTICS THE SCIENCE OF DOSAGE FORM DESIGN
`(Michael E. Aulton ed., 2d ed. 2002)
`D. Dubost et al., Characterization of a Solid State Reaction
`Product from a Lyophilized Formulation of a Cyclic
`Heptapeptide. A Novel Example of an Excipient-Induced
`Oxidation, 13(12) PHARM. RESEARCH 1811 (1996)
`U.S. Patent No. 4,425,346, Pharmaceutical Compositions
`(issued Jan 10, 1984)
`U.S. Patent No. 6,207,684, Compounds with Combined
`Antihistaminic and Mast Cell Stabilizing Activities, Intended
`for Ophthalmic Use (issued Mar. 27, 2001)
`U.S. Patent No. 6,440,460, Pharmaceutical Compositions
`Containing Buffered Ortho Ester Polymers (issued Aug. 27,
`2002)
`J. Bothe et al., Peptide Oligomerization Memory Effects and
`Their Impact on the Physical Stability of the GLP-1 Agonist
`Liraglutide, 16 MOL. PHARMACEUTICS 2153 (2019)
`M.J. Akers, Excipient-Drug Interactions in Parenteral
`Formulations, J PHARM SCI 91(11) (2002)
`U.S. PHARMACOPEIA XXII, NATIONAL FORMULARY XVII
`(1990)
`
`6
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`1069
`
`1070
`
`1071
`
`1072
`
`1073
`
`1074
`
`1075
`
`1076
`
`1077
`
`1078
`
`1079
`
`DESCRIPTION
`
`R. Noel, Statistical Quality Control in the Manufacture of
`Pharmaceuticals, 4(4) QUALITY ENGINEERING 649 (1992)
`NOTE FOR GUIDANCE SPECIFICATIONS: TEST PROCEDURES AND
`ACCEPTANCE CRITERIA FOR NEW DRUG SUBSTANCES AND NEW
`DRUG PRODUCTS: CHEMICAL SUBSTANCES (CPMP/ICH/367/96)
`(2000)
`M. Gnanalingham et al., Accuracy and Reproducibility of Low
`Dose Insulin Administration Using Pen-Injectors and Syringes,
`79 ARCH. DIS. CHILD 59 (1998)
`C. Burke et al., The Adsorption of Proteins to Pharmaceutical
`Container Surfaces, 86 INT’L J. OF PHARMACEUTICS 89 (1992)
`T. Asakura et al., Occurrence of Coring in Insulin Vials and
`Possibility of Rubber Piece Contamination by Self-Injection,
`121(6) YAKUGAKU ZASSHI 459 (2001)
`M. Roe et al., Dose Accuracy Testing of the Humalog®
`Humulin® Insulin Pen Device, 3(4) DIABETES TECH. &
`THERAPEUTICS 623 (2001)
`Parenteral Drug Association, Points to Consider for Cleaning
`Validation. Technical Report No. 29, 52(6 suppl) PDA J
`PHARM SCI TECHNOL. 1 (1998)
`WIPO Patentscope PCT Bibliography Data for
`PCT/DK2004/000792
`Deposition transcript of Peter Tessier (Dec. 4, 2020)
`(Confidential – Protective Order Material)
`Deposition transcript of Dorthe Kot Engelund (Nov. 20, 2020)
`(Confidential – Protective Order Material)
`Deposition transcript of Tina B. Pedersen (Nov. 24, 2020)
`(Confidential – Protective Order Material)
`
`7
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`1080
`
`1081
`
`1082
`
`1083
`
`1084
`
`1085
`
`1086
`
`1087
`
`1088
`
`1089
`
`1090
`
`1091
`
`DESCRIPTION
`
`JAPANESE PHARMACEUTICAL EXCIPIENTS DIRECTORY (1996)
`EP 0 037 043, Stabilised ophthalmic formulation (issued
`November 21, 1984)
`U.S. Patent No. 5,686,411, Amylin agonist peptides and uses
`therefor (issued November 11, 1997)
`International Patent Publication No. WO 00/73331, Use of
`exendins [sic] and agonists thereof for the treatment of
`gestational diabetes mellitus (published December 7, 2000)
`Shirwaikar, Opthalmic Irritation Potential of Propylene Glycol,
`57(3) INDIAN J. PHARM. SCI. 109 (1993)
`Glasgow, Hyperosmolality in Small Infants Due to Propylene
`Glycol, 72 PEDIATRICS 353 (1983)
`Kakemi, Absorption of Drugs from the Skeletal Muscle of the
`Rats. Effect of Water-Soluble Adjuvants and Vehicles on the
`Intramuscular Absorption, 20(3) CHEM. PHARM. BULL. 443
`(1972)
`Caputo, Volume and Twitch Tension Changes in Single Muscle
`Fibers in Hypertonic Solutions, 52 J. GEN. PHYS. 793 (1968)
`Strickley, Parenteral Formulations of Small Molecules
`Therapeutics Marketed in the United States (1999) - Part I, 53
`PDA J. PHARM. SCI. & TECH. 324 (1999)
`Hedge, Anaphylaxis Caused by the Ingestion of Cultivated
`Mushroom (Agaricus bisporus): Identification of Allergen as
`Mannitol, 51 ALLERGOLOGY INT’L 121 (2002)
`Schmid, Peranesthetic Anaphylactoid Shock Due to Mannitol,
`47 ALLERGY 61 (1992)
`Lodish, Section 3.1 Hierarchical Structure of Proteins, in
`MOLECULAR CELL BIOLOGY (4th ed. 2000)
`
`8
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1092
`
`1093
`
`1094
`
`1095
`
`1096
`
`1097
`
`1098
`
`1099
`
`1100
`
`1101
`
`Andersen, Medium-Dependence of the Secondary Structure of
`Exendin-4 and Glucagon-like-peptide-1, 10 BIOORGANIC &
`MED. CHEM. 79 (2002)
`Costantino, Effect of Excipients on the Stability and Structure
`of Lyophilized Recombinant Human Growth Hormone, 87(11)
`J. PHARM. SCIS. 1412 (1998)
`Gomez-Orellana, Thermodynamic Characterization of an
`Intermediate State of Human Growth Hormone, 7 PROTEIN SCI.
`1352 (1998)
`Vekilov, The Physics of Protein Crystallization, 57 SOLID
`STATE PHYS. 1 (2002)
`Fink, Protein Aggregation: Folding Aggregates, Inclusion
`Bodies and Amyloid, 3 FOLDING & DESIGN R9 (1998)
`Schulga, Increased Stability of Human Growth Hormone with
`Reduced Lactogenic Potency, 528 FEBS LETTERS 257 (2002)
`Schreiber, Stability and Function: Two Constraints in the
`Evolution of Barstar and Other Proteins, 2 STRUCTURE 945
`(1994)
`Shaw, The Effect of Net Charge on the Solubility, Activity, and
`Stability of Ribonuclease Sa, 10 PROTEIN SCI. 1206 (2001)
`Gellerfors, Characterisation of a Secreted Form of
`Recombinant Derived Human Growth Hormone, Expressed in
`Escherichia coli Cells, 7(2) J. PHARM. & BIOMED. ANALYSIS
`173 (1989)
`Henriksson, Calculation of the Isoelectric Points of Native
`Proteins with Spreading of pKa Values, 16 ELECTROPHORESIS
`1377 (1995)
`
`9
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`
`DESCRIPTION
`
`1102
`
`1103
`1104
`1105
`
`1106
`
`1107
`
`1108
`
`1109
`
`1110
`
`1111
`
`1112
`
`1113
`
`1114
`
`1115
`
`HANDBOOK OF CHEMISTRY AND PHYSICS (David R. Lide ed.,
`84th ed. 2003)
`U.S. Provisional Patent Application 60/394,699
`U.S. Provisional Patent Application 60/394,612
`U.S. Provisional Patent Application 60/394,611
`Reply Declaration of Dr. Laird Forrest
`(Confidential – Protective Order Material)
`U.S. Patent No. 8,846,618, Stable formulation of modified
`GLP-1 (Issued September 30, 2014)
`Danish Patent Application No. PA 2001 01010, filed June 28,
`2001
`Danish Patent Application No. PA 2001 01011, filed June 28,
`2001
`Danish Patent Application No. PA 2001 01052, filed July 4,
`2001
`Danish Patent Application No. PA 2001 01053, filed July 4,
`2001
`Danish Patent Application No. PA 2002 00092, filed January
`18, 2002
`Danish Patent Application No. PA 2001 00093, filed January
`18, 2002
`Robblee, Hypoxemia after Intraluminal Oxygen Line
`Obstruction During Cardiopulmonary Bypass, 48 ANN.
`THORAC. SURG. 575 (1989)
`Jeffrey, The Preparation of a Sterile Solution of Mannitol, 20
`AM. J. HOSP. PHARM. 255 (1963)
`
`10
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`1116
`
`1117
`
`1118
`
`1119
`1120
`
`1121
`
`1122
`
`1123
`
`1124
`
`1125
`
`1126
`
`1127
`
`DESCRIPTION
`
`Markman Hearing Transcript, Novo Nordisk Inc. v. Mylan
`Institutional LLC, No. 19-1551 (D. Del. Sept. 9, 2020)
`APPROVED DRUG PRODUCT WITH THERAPEUTIC EQUIVALENCE
`EVALUATIONS, ADA 165 (40th ed. 2020)
`Complaint, Novo Nordisk Inc. v. Mylan Institutional LLC, No.
`19-1551 (D. Del. Aug. 20, 2019), ECF No. 1
`Zumdahl, CHEMISTRY (3rd ed. 1993)
`Shah, Effect of pH, Chlorobutanol, Cysteine Hydrochloride,
`Ethylenediaminetetraacetic Acid, Propylene Glycol, Sodium
`Metabisulfite, and Sodium Sulfite on Furosemide Stability in
`Aqueous Solutions, 69(5) J. PHARM. SCIS. 594 (1980)
`Hribar, How Ions Affect the Structure of Water, 124(41) J. AM.
`CHEM. SOC. 12302 (2002)
`Smith, Behavior of Erythrocytes in Various Solvent Systems III,
`56 J. PHARM. SCIS. 351 (1967)
`FDA, Draft Guidance for Industry on Drug Product:
`Chemistry, Manufacturing, and Controls Information (Jan.
`2003)
`U.S. PHARMACOPEIA & NATIONAL FORMULARY (USP 24 NF 19,
`2000)
`U.S. PATENT NO. 6,284,727, Prolonged delivery of peptides
`(issued September 4, 2001)
`International Patent Publication No. WO 00/15224, Protein
`formulations (published March 23, 2000)
`THE MERCK INDEX (12th ed. 1996)
`
`11
`
`
`
`
`
`
`
`EXHIBIT
`NO.
`1128
`
`1129
`
`1130
`
`1131
`
`1132
`
`DESCRIPTION
`
`FDA, Draft Guidance for Industry on Sterile Drug Products
`Produced by Aseptic Processing—Current Good
`Manufacturing Practice (Aug. 2003)
`Maryott, TABLE OF DIELECTRIC CONSTANTS OF PURE LIQUIDS
`(1951)
`Corrected Reply Declaration of Laird Forrest, Ph.D.
`(Confidential – Protective Order Material)
`(subject to Board permission (see email dated Jan. 20, 2021))
`Email from Patent Trial and Appeal Board End to End System
`dated Friday, March 5, 2021 and having Subject line
`“IPR2020-00324: Motion Filed - Mylan Institutional LLC v.
`Novo Nordisk A/S”
`Email from Patent Trial and Appeal Board End to End System
`dated Friday, March 5, 2021 and having Subject line
`“IPR2020-00324: Document(s) Filed - Mylan Institutional LLC
`v. Novo Nordisk A/S”
`
`1133
`
`Declaration of Lara J. Dueppen
`
`Dated: March 19, 2021
`
`
`
`
`
`
`
`/s/ Lara J. Dueppen
`Lara J. Dueppen
`Reg. No. 65,002
`Counsel for Petitioner Mylan
`Institutional LLC
`
`12
`
`
`
`
`
`
`
`
`CERTIFICATE OF SERVICE
`
`Pursuant to 37 C.F.R. § 42.6(e), I certify that I caused to be served a true and
`
`correct copy of the foregoing: Updated List of Petitioners’ Exhibits by email to the
`
`electronic service addresses for Patent Owner and Petitioner Pfizer Inc.:
`
`Jeffrey Oelke
`Laura T. Moran
`Ryan P. Johnson
`FENWICK & WEST LLP
`joelke@fenwick.com
`laura.moran@fenwick.com
`ryan.johnson@fenwick.com
`Novo833IPR@fenwick.com
`
`Counsel for Patent Owner
`
`Thomas J. Meloro
`Michael W. Johnson
`WILLKIE FARR & GALLAGHER LLP
`tmeloro@willkie.com
`mjohnson1@willkie.com
`
`Counsel for Petitioner Pfizer Inc.
`
`
`
`
`
`/s/ Lara J. Dueppen
`Lara J. Dueppen
`Reg. No. 65,002
`Counsel for Petitioner Mylan Institutional LLC
`
`
`Dated: March 19, 2021
`
`
`
`
`
`
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