I lllll llllllll Ill lllll lllll lllll lllll lllll 111111111111111111111111111111111
`US009320765B2
`
`c12) United States Patent
`Bruheim et al.
`
`(IO) Patent No.:
`(45) Date of Patent:
`
`US 9,320,765 B2
`*Apr. 26, 2016
`
`(54) BIOEFFECTIVE KRILL OIL COMPOSITIONS
`
`(71) Applicant: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`A61K 31/198; A61K 31/575; A61K 35/60;
`CllB 3/006
`See application file for complete search history.
`
`(72)
`
`Inventors: Inge Bruheim, Valda (NO); Snorre
`Tilseth, Bergen (NO); Daniele
`Mancinelli, Orsta (NO)
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`(73) Assignee: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`( *) Notice:
`
`Subject to any disclaimer, the term ofthis
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 204 days.
`
`This patent is subject to a terminal dis(cid:173)
`claimer.
`
`(21) Appl. No.: 14/020,155
`
`(22) Filed:
`
`Sep. 6, 2013
`
`(65)
`
`Prior Publication Data
`
`US 2014/0010888 Al
`
`Jan. 9, 2014
`
`Related U.S. Application Data
`
`(63) Continuation of application No. 12/057,775, filed on
`Mar. 28, 2008, now Pat. No. 9,034,388.
`
`(60)
`
`(51)
`
`(52)
`
`(58)
`
`Provisional application No. 60/920,483, filed on Mar.
`28, 2007, provisional application No. 60/975,058,
`filed on Sep. 25, 2007, provisional application No.
`60/983,446, filed on Oct. 29, 2007, provisional
`application No. 61/024,072, filed on Jan. 28, 2008.
`
`(2015.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 351612
`A61K9/48
`A61K 311122
`CllB 3100
`A61K 31123
`A61K 311683
`A61K 311685
`A61K 45106
`A61K 311202
`A61K 31120
`A61K 311235
`U.S. Cl.
`CPC ................. A61K 351612 (2013.01); A61K 9148
`(2013.01); A61K 914858 (2013.01); A61K
`311122 (2013.01); A61K 31120 (2013.01);
`A61K 311202 (2013.01); A61K 31123
`(2013.01); A61K 311235 (2013.01); A61K
`311683 (2013.01); A61K 311685 (2013.01);
`A61K 45106 (2013.01); CllB 31006 (2013.01)
`Field of Classification Search
`CPC ............ A61K 2300/00; A61K 31/122; A61K
`35/612; A61K 31/685; A61K 31/23; A61K
`31/683; A61K 31/202; A61K 45/06; A61K
`31/6615; A61K 8/553; A61K 2800/70;
`A61K 31/047; A61K 35/63; A61K 35/64;
`A61K 8/925; A61K 9/48; A61K 9/4858;
`A61K 31/20; A61K 31/235; A61K 31/133;
`
`2,652,235 A
`4,036,993 A
`4,038,722 A
`4,119,619 A
`4,133,077 A
`4,251,557 A
`4,505,936 A
`4,714,571 A
`4,749,522 A
`4,814,111 A
`5,006,281 A
`5,266,564 A
`5,434,183 A
`6,214,396 Bl
`6,346,276 Bl
`6,537,787 Bl
`6,800,299 Bl
`7,488,503 Bl
`
`9/1953 Samuelsen
`7/1977 Ikeda
`8/1977 Terase et al.
`10/1978 Rogozhin et al.
`1/1979 Jasniewicz
`2/1981 Shimose et al.
`3/1985 Meyers et al.
`12/1987 Kearns et al.
`6/1988 Kamarei
`3/1989 Kearns et al.
`4/1991 Rubin et al.
`1111993 Modolell
`7/1995 Larsson-Backstrom
`4/2001 Barrier
`212002 Tanouchi et al.
`3/2003 Breton
`10/2004 Beaudoin et al.
`212009 Porzio et al.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`AU
`BR
`
`2002322233
`212003
`3/1987
`8701265
`(Continued)
`
`OTHER PUBLICATIONS
`
`EPOppositionfiledFeb. 13, 2014 by Olympic SeafoodAS, EPPatent
`Application No. EP0871891016.
`(Continued)
`
`Primary Examiner - Debbie K Ware
`(74) Attorney, Agent, or Firm - Casimir Jones, S.C.
`
`(57)
`
`ABSTRACT
`
`This invention discloses new krill oil compositions charac(cid:173)
`terized by having high amounts of phospholipids, astaxanthin
`esters and/or omega-3 contents. The krill oils are obtained
`from krill meal using supercritical fluid extraction in a two
`stage process. Stage 1 removes the neutral lipid by extracting
`with neat supercritical C02 or C02 plus approximately 5% of
`a co-solvent. Stage 2 extracts the actual krill oils by using
`supercritical C02 in combination with approximately 20%
`ethanol. The krill oil materials obtained are compared with
`commercially available krill oil and found to be more bioef(cid:173)
`fective in a number of areas such as anti-inflammation, anti(cid:173)
`oxidant effects, improving insulin resistances and improving
`blood lipid profile.
`
`48 Claims, 19 Drawing Sheets
`RIMFROST EXHIBIT 1117 Page 0001
`
`

`

`US 9,320,765 B2
`Page 2
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`7,666,447 B2
`8,030,348 B2
`8,278,351 B2
`8,383,675 B2
`8,586,567 B2
`8,697,138 B2
`2002/0076468 Al
`2003/0044495 Al
`2003/0113432 Al
`2004/0241249 Al *
`2005/0003073 Al
`2006/0078625 Al
`2006/0193962 Al
`2008/0166419 Al
`2008/0166420 Al
`2010/0143571 Al
`2010/0160659 Al
`201110130458 Al
`201110160161 Al
`201110256216 Al
`
`2/2010 Rockway
`10/2011 Sampalis
`10/2012 Sampalis
`212013 Sampalis
`1112013 Sampalis
`412014 Bruheim et al.
`612002 Saxby
`3/2003 Kagan et al.
`6/2003 Yoshitomi et al ............. 426/643
`12/2004 Sampalis ...................... 424/520
`112005 Pivovarov et al.
`412006 Rockway
`8/2006 Kamiya et al. ................ 426/615
`7 /2008 Sones
`7 /2008 Sones
`612010 Breivik
`612010 Catchpole
`612011 Breivik
`612011 Sampalis
`10/2011 Lefkowitz
`
`FOREIGN PATENT DOCUMENTS
`
`CA
`CA
`CL
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`GB
`GB
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`
`1098900
`2251265
`40348
`0609078
`670306
`1127497
`1392623
`1406641
`1542670
`0973532
`1660071
`1689413
`1743531
`1631280
`1123368
`1406641
`1419768
`1292294
`1706106
`1385500
`2097014
`921537
`A-S51-125774
`A-S52-114046
`60-153779
`61281159
`S6323819
`02049091
`2215351
`4012665
`2963152
`04057853
`3081692
`2524217
`H08-231391
`3344887
`3611222
`2001-158736 A
`2003-003192 A
`2003-048831 A
`2003-146883 A
`3467794
`2003-530448
`2003-531857 A
`3486778
`2004-525180 A
`2004-534800
`2004-536059 A
`3678317
`2005-245379 A
`2006-502196 A
`
`4/1981
`412000
`7 /1997
`8/1994
`6/1995
`8/2001
`3/2004
`412004
`6/2005
`912005
`512006
`8/2006
`112007
`3/2008
`4/2008
`112009
`112009
`3/2009
`712009
`7/2010
`10/1982
`6/1999
`1111976
`9/1977
`8/1985
`12/1986
`2/1988
`2/1990
`8/1990
`111992
`2/1992
`2/1992
`7 /1994
`8/1996
`9/1996
`7 /1997
`8/1997
`6/2001
`112003
`212003
`5/2003
`9/2003
`10/2003
`10/2003
`10/2003
`8/2004
`1112004
`12/2004
`512005
`912005
`112006
`
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`JP
`SU
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`
`2006-069948 A
`2006-083136 A
`2006-290784 A
`2006-316073 A
`2006-328014 A
`2006-528233 A
`2007-502805 A
`2007-509131 A
`2007-126455 A
`2007-518764 A
`2007-246404 A
`220741
`86/06082
`89/01031
`89/10960
`90/05765
`93/24142
`97/38585
`97/39759
`98/34498
`99/39589
`00/23546
`00/25608
`00/38708
`01128526
`01/76385
`01182928
`02/083122
`02/092540
`02/102394
`03/011873
`03/13497
`2004/028529
`2004/047554
`2004/100943
`2004/112767
`2005/004393
`2005/018632
`2005/037848
`2005/038037
`2005/070411
`2006/030552
`2006/111633
`2007/080514
`2007/080515
`2007 /108702
`2007 /123424
`2008/006607
`2008/072563
`2008/117062
`2009/027692
`2012/139588
`
`3/2006
`3/2006
`10/2006
`1112006
`12/2006
`12/2006
`212007
`4/2007
`5/2007
`7/2007
`9/2007
`111971
`10/1986
`2/1989
`1111989
`5/1990
`12/1993
`10/1997
`10/1997
`8/1998
`8/1999
`412000
`512000
`712000
`4/2001
`10/2001
`1112001
`10/2002
`1112002
`12/2002
`212003
`212003
`412004
`6/2004
`1112004
`12/2004
`1/2005
`3/2005
`412005
`412005
`8/2005
`3/2006
`10/2006
`7/2007
`7/2007
`9/2007
`1112007
`1/2008
`6/2008
`10/2008
`3/2009
`10/2012
`
`OTHER PUBLICATIONS
`
`Brzustowicz, Michael R., et al., "Controlling Membrane Cholesterol
`Content. A Role
`for Polyunsaturated
`(Docosahexaenoate)
`Phospholipids," Biochemistry (2002), 41, pp. 12509-12519.
`Jong-Ho Lee, "A Review: Antioxygenic and Peroxide-decomposing
`Activities of Antarctic Krill Lipids," J. Korean Soc. Food Mutr. 13(3)
`pp. 326-333 (1984).
`Ki Woong Cho, et al., "Lipid and Fatty Acid Composition of the
`Antarctic Krill Euphausia superba," Ocean Research 21(2): 109-116
`(1999).
`Hvattum, Erlend, et al., "Effect of soybean oil and fish oil on indi(cid:173)
`vidual molecular species of Atlantic salmon ... ",Journal of Chro(cid:173)
`matography B, 748 (2000) 137-149.
`Igarashi, Daisuke, et al., "Positional Distribution ofDHA and EPA in
`Phosphatidylcholine and Phosphatidylethanolamine from Different
`Tissues of Squids," J. Oleo Sci. vol. 50, No. 9 (2001).
`Tochizawa, Kaoru, et al., "Effects of Phospholipds Containing
`Docosahexaenoic Acid on Differentiation and Growth of HL-60
`Human Promyelocytic Leukemia Cells," J. Jpn. Oil Chem. Soc. vol.
`46, No. 4 (1997).
`Zerouga, Mustapha, et al., "Comparison of phosphatidylcholines
`containing one or two docosahexaenoic acyl chains on properties of
`phospholipid monolayers and bilayers," Biochimica et Biophysica
`Acta 1236 (1995) 266-272.
`
`RIMFROST EXHIBIT 1117 Page 0002
`
`

`

`US 9,320,765 B2
`Page 3
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Eung-Ho Lee, et al., "Studies on the Processing of Krill Sauce," J.
`Korean Soc. Food Nutr. 13(1) 97-106 (1984).
`Hyun-Ku Kim, et al., "Effects of Cooking and Drying Methods on the
`Polar Lipds Composition of Shrimp," Korean J. Food Sci. Technol.
`vol. 21, No. 1, pp. 25-30 (1989).
`Shon, Mi-Yae, et al., "Effects of Krill and Cadmium on Lipid Com(cid:173)
`position of Plasma in Cholesterol-Fed Rats," J. Korean Soc. Food
`Nutr. 23(1), 38-43 (1994).
`Summons MaterialsdownloadedfromESPACE on Dec. 16, 2014 for
`EP Patent Application No. 08 718 910.6.
`"Neptune Technologies & Bioressources Soon to Obtain a Major
`Patent in Over 30 Countries" ("2001 Press Release,").
`Action Closing Prosecution, '348 patent, Oct. 21, 2011.
`Apr. 2, 2012 Response to Office Action, '351 patent.
`Balassa et al., Microencapsulation in the Food Industry, Critical
`Reviews in Food Technology, 2:2, 245-265 (1971) ("Balassa").
`Bell and Dick, Molecular Species Composition of the Major Diacyl
`Glycerophospholipids from Muscle, Liver, Retina and Brain of Cod
`(Gadus morhua), Lipids, vol. 26, No. 8, pp. 565-573 (1991) ("Bell
`and Dick").
`Bell, Molecular Species Analysis of Phosphoglycerides from the
`Ripe Roes of Cod, Lipids, vol. 24, No. 7 (1989).
`Bell, Molecular Species Composition of Phosphatidylcholine from
`Crypthecodinium cohnii in Relation to Growth Temperature Lipids
`25, 115-118 (1990).
`Bergelson (ed.), Lipid Biochemical Preparations, Chapter I.l, pp.
`1-13 (1980) ("Bergelson").
`Bottino, N.R., "Lipid Composition of Two Species of Antarctic Krill:
`Euphausia superba and E. crystallorophias," Comp. Biochem.
`Physiol., 1975, vol. SOB, pp. 479-484 ("Bottino").
`Buchi R-220 Rotovapor® Manual, Nov. 16, 2009.
`Buda, Structural order of membranes and compos1tJon of
`phospholipids in fish brain cells during thermal acclimatization,
`Proc. Natl. Acad. Sci. USA vol. 91, pp. 8234-8238, Aug. 1994.
`Certificate of translation of Ex. 1072: Fisheries Agency, General
`Report on Research and Development of Techniques in Processing
`and Utilization of Marine Products, Chapter 6, Development of tech(cid:173)
`nology for recovery of valuable substances (astaxanthin) from krill,
`by Takao Fujita, pp. 273-307 (Mar. 1985); Japanese language docu(cid:173)
`ment.
`Certificate of translation of Ex. 1074: Japanese Patent No.
`60-153779, entitled "Nutritional Supplement", 2013.
`Certificate of translation of Ex. 1076: Japanese Patent Publication
`No. H08-23139 l, entitled "Medicine for Improvement of Dementia
`Symptoms", 2013.
`Certification of translation of Ex. 1070: Japanese Unexamined Patent
`Application Publication No. 02-215351, 2013.
`Certified translation of Ex. 1070: Japanese Unexamined Patent
`Application Publication No. 02-215351, titled Krill Phospholipids
`Fractioning Method ("Maruyama,"); Certificate of Translation pro(cid:173)
`vided as Ex. 1071, Aug. 28, 1990.
`Certified translation of Ex. 1072: Fisheries Agency, General Report
`on Research and Development of Techniques in Processing and Uti(cid:173)
`lization of Marine Products, Chapter 6, Development of technology
`for recovery of valuable substances ( astaxanthin) from krill, by Takao
`Fujita, pp. 273-307 (Mar. 1985) ("Fujita"); Certificate ofTranslation
`provided as Ex. 1073.
`Certified translation of Ex. 1074: Japanese Patent No. 60-153779,
`entitled "Nutritional Supplement" ("Fukuoka"); Certificate ofTrans(cid:173)
`lation provided as Ex. 1075, Aug. 13, 1985.
`Certified translation of Ex. 1076: Japanese Patent Publication No.
`H08-231391, entitled "Medicine for Improvement of Dementia
`Symptoms" ("Yasawa"); Certificate of Translation provided as Ex.
`1077,Sep. 10, 1996.
`Declaration of Bjorn Ole Haugsgjerd in support of Inter Partes
`Review of U.S. Pat. No. 8,278,351 ("Haugsgjerd"), Oct. 4, 2011.
`Declaration of Bjorn Ole Haugsgjerd submitted during inter partes
`reexamination of parent U.S. Pat. No. 8,030,348 ("Haugsgjerd '348
`Deel."), Oct. 4, 2011.
`
`Declaration of Dr. Albert Lee in Support of Inter Partes Review of
`U.S. Pat. No. 8,278,351 ("Lee"), Oct. 14, 2013.
`Declaration of Dr. Albert Lee in Support of Inter Partes Review of
`U.S. Pat. No. 8,383,675 ("Lee"), Oct. 14, 2013.
`Declaration of Dr. Chong Lee submitted during inter partes reexami(cid:173)
`nation of parent U.S. Pat. No. 8,030,348 ("Yeboah Reexam Deel."),
`Mar. 16, 2011.
`Declaration of Dr. Earl White submitted during prosecution of parent
`U.S. Pat. No. 8,030,348 ("2011 White Deel."), May31, 2011.
`Declaration of Dr. Ivar Storf0 in support of Inter Partes Review of
`U.S. Pat. No. 8,278,351 ("Storf0"), 2013.
`Declaration of Dr. Ivar Storf0 in support of Inter Partes Review of
`U.S. Pat. No. 8,383,675 ("Storf0"), 2013.
`Declaration of Dr. Jacek Jaczynski from interpartes reexamination of
`the parent U.S. Pat. No. 8,030,348 ("Jaczynski Reexam. Deel."), Mar.
`16, 2012.
`Declaration of Dr. Jaczynski submitted during prosecution of parent
`U.S. Pat. No. 8,278,351 (Jaczynski '351 Deel.), Mar. 29, 2012.
`Declaration of Dr. Jeff Moore in Support of Inter Partes Review of
`U.S. Pat. No. 8,278,351 ("Moore"), 2013.
`Declaration of Dr. Jeff Moore in Support of Inter Partes Review of
`U.S. Pat. No. 8,383,675 ("Moore"), Oct. 2013.
`Declaration of Dr. Richard van Breemen in Support of Inter Partes
`Review of U.S. Pat. No. 8,278,351 ("Van Breemen"), 2013.
`Declaration of Dr. Richard van Breemen in Support of Inter Partes
`Review of U.S. Pat. No. 8,383,675 ("Van Breemen"), 2012.
`Declaration of Dr. Shahidi submitted during inter partes reexamina(cid:173)
`tion of parent U.S. Pat. No. 8,030,348 (Shahidi Reexam. Deel.), Mar.
`16, 2012.
`Declaration of Dr. Shahidi submitted during prosecution of parent
`U.S. Pat. No. 8,278,351 (Shahidi '351 Deel.), Mar. 29, 2012.
`Declaration of Dr. Suzanne Budge in Support oflnter Partes Review
`of U.S. Pat. No. 8,278,351 ("Budge"), 2013.
`Declaration of Dr. Suzanne Budge in Support oflnter Partes Review
`of U.S. Pat. No. 8,383,675 ("Budge"), 2013.
`Declaration of Dr. Thomas Brenna in support of Inter Partes Review
`of U.S. Pat. No. 8,278,351, 2013.
`Declaration of Dr. Thomas Brenna in support of Inter Partes Review
`of U.S. Pat. No. 8,383,675, Oct. 17, 2013.
`Declaration of Dr. Thomas Gundersen submitted during inter partes
`reexamination of parent U.S. Pat. No. 8,030,348 ("Gundersen
`Deel."), Oct. 4, 2011.
`Declaration of Dr. Tina Sampalis submitted during inter partes reex(cid:173)
`amination of parent U.S. Pat. No. 8,030,348 (Sampalis), Mar. 16,
`2012.
`Declaration of Dr. Van Breemen submitted during Ex parte Reexami(cid:173)
`nation of the '351 patent (Van Breemen '351 Reexam. Deel., Oct. 1,
`2012.
`Declaration of Dr. Van Breemen submitted during Inter partes Reex(cid:173)
`amination of the '348 patent (Van Breemen '348 Reexam Deel., Apr.
`17,2012.
`Declaration of Dr. Yeboah submitted during inter partes reexamina(cid:173)
`tion of parent U.S. Pat. No. 8,030,348 ("Yeboah Reexam Deel."),
`Mar. 16, 2012.
`Declaration of Dr. Yeboah submitted during prosecution of parent
`U.S. Pat. No. 8,278,351 ("Yeboah '351 Deel."), Mar. 16, 2012.
`Eichberg, "Lecithin-It Manufacture and Use in the Fat and Oil
`Industry," Oils and Soap 51-54, 1939 ("Eichberg").
`Expert Witness Report of Dr. Theodore Welch submitted in relation to
`ITC Investigation No. 337-TA-877 ("Welch"), Sep. 16, 2013.
`Farkas, Composition and Physical State of Phospholipids in Calanoid
`Copepods from India and Norway, Lipids, vol. 23, No. 6 (1988).
`Final Prospectus dated May 11, 2001 ("Final Prospectus").
`Fisheries Agency, General Report on Research and Development of
`Techniques in Processing and Utilization of Marine Products, Chap(cid:173)
`ter 6, Development of technology for recovery of valuable substances
`(astaxanthin) from krill, by Takao Fujita, pp. 273-307 (Mar. 1985);
`Japanese language document.
`Folch, et al., A Simple Method for the Isolation and Purification of
`Total Lipids from Animal Tissues. J. Biol. Chem., 226, 497-509
`(1957).
`Grant of Request for Ex parte Reexamination of the '351 patent, Dec.
`21, 2012.
`
`RIMFROST EXHIBIT 1117 Page 0003
`
`

`

`US 9,320,765 B2
`Page 4
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Grit et al., Hydrolysis ofphosphatidylcholine in aqueous liposome
`dispersions, Int. J. Pharmaceutics 50:1-6 (1989).
`Henderson et al., Lipid Composition of the Pineal Organ from Rain(cid:173)
`bow Trout (Oncorhynchus mykiss), Lipids, vol. 29, No. 5, pp. 311-
`317 (1994) ("Henderson").
`Herman and Groves, The Influence of Free Fatty Acid Formation on
`the pH of Phospholipid-Stabilized Triglyceride Emulsions, Pharma(cid:173)
`ceutical Research 10(5):774-776 (1993).
`Itano Refrigerated Food Co., Ltd., Bio & High Technology
`Announcement and Natural Astaxanthin & Krill Lecithin, pp. 1-16
`(on or before Dec. 28, 1994) ("Itano").
`Johnson and Lucas, Comparison of Alternative Solvents for Oils
`Extraction, JAOCS 60(2):229-242 (1983).
`Le Grandois et al., Investigation of Natural Phosphatidylholine
`Sources: Separation and Identification by Liquid Chromatography(cid:173)
`Electrospray Ionization-Tandem Mass Spectrometry (LC-ESI(cid:173)
`MS2) of Molecular Species, J. Agric. Food Chem., 57, 6014-20
`(2009) ("Le Grandois").
`the
`Lin et al., Effect of Dietary N-3 Fatty Acids Upon
`PhospholipidMolecular Species of the Monkey Retina, Invest
`Ophthalmol Vis Sci. 1994;35:794-803.
`Medina et al., C Nuclear Magnetic Resonance Monitoring of Free
`Fatty Acid Release After Fish Thermal Processing, J. Amer. Oil
`Chem. Soc. 71(5):479-82 (1994).
`Oct. 24, 2012 Office Action, '675 patent.
`Office Action dated Jan. 5, 2012, '351 patent.
`U.S. Appl. No. 60/307,842 (Priority document for the '351 patent),
`Jul. 27, 2001.
`Supplemental Declaration of Bjorn Ole Haugsgjerd submitted during
`inter partes reexamination of parent U.S. Pat. No. 8,030,348
`("Haugsgjerd '348 Supp. Deel."), Apr. 16, 2012.
`Supplemental Declaration of Dr. Earl White submitted during inter
`partes reexamination of parent U.S. Pat. No. 8,030,348 ("White
`Supp. Reexam. Deel."), Mar. 16, 2012.
`Supplemental Declaration of Dr. Earl White submitted during pros(cid:173)
`ecution of parent U.S. Pat. No. 8,278,351 ("White Supp. Deel."),
`Mar. 29, 2012.
`Supplemental Declaration of Dr. Thomas Gundersen submitted dur(cid:173)
`ing inter partes reexamination of parent U.S. Pat. No. 8,030,348
`("Gundersen Supp. Deel."), Apr. 18, 2012.
`Suzuki, T. and Shibata, N., "The utilization of Antarctic krill for
`human food," Food Rev. Int'!, 6: 1, 119-147 (1990) ("Suzuki").
`Takahashi et al., Compositional Changes in Molecular Species of
`Fish Muscle Phosphatidylcholine During Storage, Bull. Fae. Fish.
`Hokkaido Univ. 37(1), 80-84 1986.
`Takahashi et al., Molecular Species of Fish Muscle Lecithin, Bulletin
`of the Japanese Society of Scientific Fisheries 48 (12), 1803-1814
`(1982).
`Takahashi et al., Prediction of Relative Retention Value of the Indi(cid:173)
`vidual Molecular Species of Diacyl Glycerolipid on High Perfor(cid:173)
`mance Liquid Chromatography, Bull. Fae. Fish. Hokkaido Univ.
`38(4), 398-404. 1987.
`Tanaka, Biosynthesis of
`l,2-dieicosapentaenoyl-sn-glycero-3-
`phosphocholine in Caenorhabditis elegans, Eur. J. Biochem. 263,
`189±194 (1999).
`Tocher, Chapter 6, Glycerophospholipid metabolism, Biochemistry
`and molecular biology of fishes, vol. 4, Hochachka and Mommsen
`(eds.)(1995).
`Watanabe et al., Effective Components in Cuttlefish Meal and Raw
`Krill for Improvement of Quality of Red Seabream Pagrus major
`Eggs, Nippon Suisan Gakkaishi 57(4):681-694 (199l)("Watanabe").
`WHO News and Activities, Bulletin of the World Health Organiza(cid:173)
`tion, 73(4), pp. 547-551 (1995) ("WHO Bulletin").
`Valeri, D., et al., "Visocities of Fatty acids, triglycerides and their
`binary mixtures," JAOCS 74 (1997) pp. 1221-1226.
`CRC 2013-2014, 94th ed., pp. 6-231-6-235.
`European Search Report, EP Patent Application No. EP12187516,
`mailed Jun. 10, 2013.
`
`CN Office Action mailed Apr. 27, 2012, JP Patent Application No.
`200880112125.6 (and English translation).
`Fricke, et al., Lipid, Sterol and Fatty Acid Composition of Antarctic
`Krill (Euphausia superba Dana), Lipids (1984) 19 (11): 821-827.
`Fricke, et al., 1-0-Alkylglycerolipids in Antarctic Krill (Euphausia
`superba Dana), Comp. Biochem. Physiol. (1986) 85B(l): 131-134.
`Gordeev, K.Y., et al. "Fatty Acid Composition of the Main
`Phospholipids of the Antarctic Krill, Euphausia superba," Chem.
`Nat. Cmpds. (1990) 26(2), pp. 143-147.
`Grantham (1977) Southern Ocean Fisheries Survey Progranune,
`FAO Rome, GLO/S0/77/3: 1-61.
`Raventos et al., Application and Posssibilities of Supercritical C02
`Extraction in Food Processing Industry: An Overview, Food Science
`and Technology International (2002) 8: 269-284.
`Tanaka, T.,
`(PAF)-like
`et
`al., Platelet-activating Factor
`Phospholoipds Formed during Peroxidation of Phosphatidylcholines
`from Different Foodstuffs, Biosci. Biotech. Biochem. (1995) 59 (8),
`pp. 1389-1393.
`Winther, et al., Elucidation of Phosphatidylcholine Composition in
`Krill Oil Extracted from Euphausia superba, Lipids (2011) 46: 25-36.
`JP Office Action mailed Feb. 23, 2012, JP Patent Application No.
`2010-522444 (and English translation).
`Dec. 8, 2011 Office Action, KR Patent Application No. 10-2010-
`7006897 and its English translation.
`Sikorski, E., "The Utilization of Krill for Food," Food Process Eng.,
`1:845-855 (1980).
`Budzinskli, E., et al., "Possibilities of processing and marketing of
`products made from Antarctic Krill", FAO Fish. Tech. Pap. (268) 46
`pages (1985).
`Bunea R., et al.., "Evaluation of the Effects of Neptune Krill Oil on
`the Clinical Course of Hyperlipidemia," Alternative Medicine
`Review, Thorne Research Inc., Sandpoint, US, vol. 9, No. 4, Jan. 1,
`2004.
`Gordeev, K.Y., et al. "Fatty Acid Composition of the Main
`Phospholipids of the Antarctic Krill, Euphausia superba," Khim.
`Prirod. Soed. 2 (1990), pp. 181-187.
`Takaichi et al., 2003, "Fatty Acids of astaxanthin esters in krill deter(cid:173)
`mined by mild mass spectrometry", Comparative Biochemistry and
`Physiology Part B, Biochemistry and Molecular Biology, Elsevier,
`Oxford, vol. 136, Jan. 1, 2003, p. 317-322.
`Tanaka et al., 2004, "Extraction of Phospholipids from Salmon Roe
`with Supercritical Carbon Dioxide and an Entrainer", J. Oleo Sci,
`53(9): 417-424.
`Tanaka et al., 2005, "Extraction of Phospholipids from Unused
`Natrual Resources with Supercritical Carbon Dioxide and an
`Entrainer", Journal of Oleo Science, vol. 54(11): 569-576.
`Todoric et al., 2006, "Adipose tissue inflanunation induced by high(cid:173)
`fat diet in obese diabetic mice is prevented by n-3 polyunsaturated
`fatty acids", Diabetologia, 49(9): 2109-2119.
`Tou et al., 2007, "Krill for human consumption: nutritional value and
`potential health benefits.", Nutrition Rev 65 (2):63-77.
`Trayhurn et al., 2004, "Adipokines: inflanunation and the pleiotropic
`role of white adipose tissue", Br. J. Nutrition, 92(3): 347-355.
`Trebble et al., 2003, "Inhibition of tumour necrosis factor-alpha and
`interleukin 6 production by mononuclear cells following dietary
`fish-oil supplementation in healthy men and response to antioxidant
`co-supplementation", Br. J. Nutrition, 90(2): 405-412.
`Ukkola et al., 2002, "Adiponectin: a link between excess adiposity
`and associated comorbidities?", J. Mo!. Med., 80 (11): 696-702.
`Van Der Veen et al., 1971 "The Lipids of Krill (Euphausia Species)
`and Red Crab (Pleuroncodes planipes)", Lipids, 6(7): 481-485.
`Virtue, et al. 1996, Reproductive trade-off in male Antarctic krill,
`Euphausia superba, Marine Biology, vol. 126, No. 3, pp. 521-527.
`Yamaguchi eta!., 1983, "The Composition ofCarotenoidPigments in
`the Antarctic Krill Euphausia superba", Bulletin of the Japanese
`Society of Scientific Fisheries, 49(9): 1411-1415.
`Yamaguchi et al., 1986, "Supercritical Carbon Dioxide Extraction of
`Oils From Antarctic Krill," Journal of Agricultural and Food Chem(cid:173)
`istry, vol. 34, pp. 904-907.
`Yanase M; 1974, "Modification ofa Russian method for separation of
`heat-coagulated protein from Antarctic krill", Database FSTA
`( online ); International Food Information Service (IFIS); Frankfurt(cid:173)
`Main, DE.
`
`RIMFROST EXHIBIT 1117 Page 0004
`
`

`

`US 9,320,765 B2
`Page 5
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Yen et al., 1994, "Effect of dietary omega-3 and omega-6 fatty acid
`sources on PUVA-induced cutaneous toxicity and tumorogenesis in
`the hairless mouse", Arch. Dermatol. Res., 286(6): 331-6.
`Database WPI Week 200682, Thomson Scientific, London, GB,
`2006.
`English Abstract; JP 2003-531857; See abstract from corresponding
`WO 2001/082928.
`English Abstract; JP 2004-5 25180; See abstract from corresponding
`WO 2002/083122.
`English Abstract; JP 2006-528233; See abstract from corresponding
`WO 2004/100943.
`English Abstract; JP 2007-502805; See abstract from corresponding
`WO 2005/018632.
`English Abstract; JP 2007-509131; See abstract from corresponding
`WO 2005/037848.
`English Abstract; JP 2007-5187 64; See abstract from corresponding
`WO 2005/070411.
`English Abstract; JP 2004-536059; See abstract from corresponding
`WO 2002/09254.
`English Abstract; JP 2006-502196; See abstract from corresponding
`WO 2004/028529.
`Ando and Hatano, 1988, "Isolation of apolipoproteins from
`carotenoid-carrying lipoprotein in the serum of chum salmon,
`Oncorhynchus keta", J. Lipid Research, 29: 1264-1271.
`Aoi et al., 2003, "Astaxanthin limits exercise-induced skeletal and
`cardiac muscle damage in mice", Antioxidants & Redox Signaling,
`5(1): 139-44.
`Britton, 1985, "General CarotenoidMethods", Methods in Enzymol(cid:173)
`ogy, vol. 111, pp. 113-149.
`Calder, 2006, "n-3 polyunsaturated fatty acids, inflanunation, and
`inflanunatory diseases", Am. J. Clin. Nutr., 83: 1505S.
`Charest et al., 2001, "Astaxanthin Extraction from Crawfish Shells by
`Supercritical C02 with Ethanol as Cosolvent", J. Aquatic Food Prod(cid:173)
`uct Technology, 10(3): 79-93.
`Chen and Meyers, 1982, "Extraction of Astaxanthin Pigment from
`Crawfish Waste Using a Soy Oil Process", J. Food Sci., 47: 892-896.
`Clarke, 1980, "The Biochemical Composition of Krill, Euphausia
`superba dana,from South Georgia", J. Exp. Mar. Biol. Ecol., 43:
`221-236.
`Czeczuga, 1974, "Comparative Studies ofCarotenoids in the Fauna
`of the Gullmar Fjord (Bohuslan, Sweden). II. Crustacea: Eupagurus
`bernhardus, Hyas coarctatus and Upogebia deltaura", Marine Biol(cid:173)
`ogy, 28: 95-98.
`De Ritter and Purcell, 1981, "Carotenoid Analytical Methods",
`Carotenoids as Colorants and Vitamin A Precursors: Technological
`and Nutritional Applications, pp. 815-882.
`Deutch, 1995, "Menstrual pain in Danish women correlated with low
`n-3 polyunsaturated fatty acid intake", Eur. J. Clin. Nutr., 49(7):
`508-16.
`Diez et al., 2003, "The role of the novel adipocyte-derived hormone
`adiponectin in human disease", Eur. J. Endocrinol., 148(3): 293-300.
`Ellingsen et al., 1987, "Biochemistry of the autolytic processes in
`Antarctic krill post mortem. Autoproteolysis." Biochem. J. 246, 295-
`305.
`Emodi, 1978, "Carotenoids: Properties and Applications", Food
`Technology, 32(5): 38.
`Felix-Valenzuela et al., 2001, "Supercritical C02/Ethanol Extraction
`of Astaxanthin from Blue Crab (Callinectes sapidus) Shell Waste",
`Journal of Food Process Engineering, 24: 101-112.
`Fox and Scheer, 1941, "Comparative Studies of the Pigments of
`Some Pacific Coast Echinoderms", The Biological Bulletin, 441-
`455.
`Fricke, et al., 1984, "Lipid, Sterol and Fatty Acid Composition of
`Antarctic Krill (Euphausia superba Dana)", Lipids, 19 (11): 821-
`827.
`Geusens et al., 1994, "Long-term effect of omega-3 fatty acid supple(cid:173)
`mentation in active rheumatoid arthritis. A 12-month, double-blind,
`controlled study", Arthritis Rheum., 37(6): 824-9.
`
`Gilchrist and Green, 1960, "The Pigments of Artemia", Proceedings
`of the Royal Society, Series B Biological Sciences, vol. 152 No. 946,
`pp. 118-136.
`Goodwin and Srisukh, 1949, "Some Observations on Astaxanthin
`Distribution in Marine Crustacea", Department of Biochemistry,
`University of Liverpool, pp. 268-270.
`Gulyaev and Bugrova, 1976 "Removing fats from the protein paste
`Okean". Konservnaya I Ovoshchesushil'naya Promyshlennost, (4),
`37-8.
`Hardardottir and Kinsella, 1988, "Extraction of Lipid and Choles(cid:173)
`terol from Fish Muscle with Supercritical Fluids" Journal of Food
`Science, 53(6): 1656-1658.
`International Aqua Feed, 2006, vol. 9.
`International Search Report and Written Opinion for PCT/GB2008/
`002934, Dated Mar. 11, 2009.
`International Search Report and Written Opinion for PCT/IB2010/
`000512; dated Jun. 24, 2010.
`International Search Report for PCT /IB2007 /000098, dated: Jun. 26,
`2007.
`Itoh et al., 2007; "Increased adiponectin secretion by highly purified
`eicosapentaenoic acid in rodent models of obesity and human obese
`subjects", Arteriosclerosis, Thrombosis, and Vascular Biology;
`27(9): 1918-1925.
`Johnson et al., 1978, "Simple Method for the Isolation of Astaxanthin
`from the Basidiomycetous Yeast Phaffia rhodozyrna", Applied and
`Environmental Microbiology, 35(6): 1155-1159.
`Kolakowska, 1989, "Krill lipids after frozen storage of about one year
`in relation to storage time before freezing", Die N aluung Food, 33(3 ):
`241-244.
`Kris-Etherton et al., 2002, "Fish Consumption, Fish Oil, Omega-3
`Fatty Acids, and Cardiovascular Disease", Circulation, 106:2747-
`2757.
`Kristensen et al., 1989, "Dietary supplementation with n-3 polyun(cid:173)
`saturated fatty acids and human platelet function: a review with
`particular emphasis on implications for cardiovascular disease", J.
`Intern. Med. Suppl. 731:141-50.
`Kunesova et al., 2006, "The influence of n-3 polyunsaturated fatty
`acids and very low calorie diet during a short-term weight reducing
`regimen on weight loss and serum fatty acid composition in severely
`obese women", Physiol Res.; 55 (1):63-72.
`Laight et al., 1999, "F2-isoprostane evidence of oxidant stress in the
`insulin resistant, obese Zucker rat: effects of vitamin E", Eur. J.
`Pharmacol. 377(1): 89-92.
`Lambertson and Braekkan, 1971, "Method of Analysis of
`Astaxanthin and its Occurrence in some Marine Products," J. Sci.
`Food. Agr., vol. 22(2): 99-101.
`Libby et al., 2006, "Inflammation and Atherothrombosis: From
`Population Biology and Bench Research to Clinical Practice" J.
`Amer. Coll. Card. 48 (9 Suppl. A): A33-A46.
`Lopez et al., 2004, "Selective extraction of astaxanthin from crusta(cid:173)
`ceans by use of supercritical carbon dioxide", Talanta, 64: 726-731.
`Mandeville, 1991, "Isolation and Identification of Carotenoid Pig(cid:173)
`ments, Lipids and Flavor Active Components from Raw Commercial
`Shrimp Waste", Food Biotechnology, 5(2): 185-195.
`Meyers and Bligh, 1981, "Characterization of Astaxanthin Pigments
`from Heat-Processed Crawfish Waste", J. Agric. Food Chem., 29:
`505-508.
`Meyers, 1977, "Using Crustacean Meals and Carotenoid-Fortified
`Diets", Feedstuffs, vol. 49(19).
`Meyers, 1994, "Developments in world aquaculture, feed formula(cid:173)
`tions, and role of carotenoids", Pure & Appl. Chem, vol. 66(5):
`1069-1076.
`Mills et al., 1989, "DietaryN-6 and N-3 fatty acids and salt-induced
`hypertension in the borderline hypertensive rat", Lipids, 24(1):
`17-24.
`Moates and Van Bentem, 1990, "Separating out the value", Food
`Science and Technology Today, 4(4): 213-214.
`Nikolaeva, 1967 "Amino acid composition of protein-coagulate in
`krill", VNIRO, 63:161-4.
`Phleger, et al. (2002) "Interannual and between species comparison
`in the lipids, fatty acids, and sterols of Antarctic krill from the US
`
`RIMFROST EXHIBIT 1117 Page 0005
`
`

`

`US 9,320,765 B2
`Page 6
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`AMLR Elephant Island survey area: 1997 and 1998''. Comp
`Biochem Physiol 131B:733-747.
`Popp-Snijders et al., 1987, "Dietary supplementation of omega-3
`polyunsaturated fatty acids improves insulin sensitivity in non-insu(cid