`(10) Patent No.:
`US 9,034,388 B2
`
`Bruheim et al.
`(45) Date of Patent:
`May 19, 2015
`
`USOO9034388B2
`
`(54) BIOEFFECTIVE KRILL OIL COMPOSITIONS
`
`(75)
`
`Inventors:
`
`Inge Bruheim, Volda (NO); Mikko
`Griinari, Espoo (Fl); Snorre Tilseth,
`Bergen (NO); Sebastiano Banni,
`Cagliari (1T); Jeffrey Stuart Cohn,
`Camperdown (AU)’ Daniele Mancinelli
`Orsta (NO)
`’
`
`’
`
`(73) Assignee: AKER BIOMARINE ANTARTIC AS,
`Stamsund (NO)
`.
`.
`.
`.
`Subject to any d1scla1mer, the term ofth15
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 1181 days.
`
`.
`( * ) Not1ce:
`
`(21) Appl. No.: 12/057,775
`
`(22)
`
`Filed:
`
`Mar. 28, 2008
`
`(65)
`
`Prior Publication Data
`
`US 2008/0274203 A1
`
`NOV. 6, 2008
`
`4,505,936 A
`4,714,571 A
`4,749,522 A
`4314411 A
`5,006,281 A
`5’266’564 A
`5’434’183 A
`6,214,396 B1
`6,346,276 B1
`3:33:33; :1
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`7,666,447 B2
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`8,278,351 32
`8,383,675 B2
`8,697,138 B2
`2002/0076468 A1
`2003/0044495 A1
`2003/0113432 A1 *
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`2006/0078625 A1
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`Related US. Application Data
`
`2010/0143571 A1
`
`6/2010 Breivik
`
`(60) 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.
`
`(51)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 9/48
`A61K 31/23
`A61K 31/122
`A61K 31/202
`A 61K 31/683
`A61K 31/685
`CIIB 3/00
`A61K 45/06
`(52) US. Cl.
`CPC ............. A61K 35/612 (2013.01); A61K 9/4858
`(3213;:gzlg’lggifjg/Illzfagz/géggzlg’lgiggf
`A61K 31/685 (2013.01); A61K 45/06
`(2013.01); CIIB 3/006 (2013.01); A61K
`31/202 (2013.01)
`
`(58) Field Of Classification Search
`CPC - A61K 2300/00; A61K 31/122; A61K 31/23;
`A61K 31/683; A61K 31/685; A61K 35/612;
`A61K 31/2023 A61K 45/06; A61K 9/4858;
`A61K 9/2054; A61K 47/44; A61K 31/05 ;
`A61K 31/12; A61K 31/133; A61K 31/198;
`A61K 31/57; CUB 3/006
`See application file for complete search history.
`
`(56)
`
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`
`2 652 235 A
`4:036:993 A
`4,119,619 A
`4,133,077 A
`4,251,557 A
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`1
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`
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`$3
`
`2003332:
`
`$332;
`
`(Continued)
`
`OTHER PUBLICATIONS
`_
`_
`_
`‘I‘Isoilation 0f apolipoproteins from
`.1988,
`Ando and Hatano,
`caroten01d-carry1ng 11p0pr0te1n 1n the serum of chum salmon,
`Oncorhynchus keta”, J. Lipid Research, 29: 1264-1271.
`(Continued)
`
`Primary Examiner 7 Debbie K Ware
`(74) Attorney, Agent, or Firm 7 Casimir Jones S.C.
`
`ABSTRACT
`(57)
`This invention discloses new krill oil compositions charac-
`terizedby having high amounts ofphospholipids, 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 CO2 or CO2 plus approximately 5% of
`-
`l
`t Sta e 2 extracts the actual krill oils b usin
`g
`a CO SOYBH '
`g.
`.
`.
`.
`.
`y
`supercntlcal CO2 1n comb1natlon w1th approx1mately 20%
`ethanol. The krilloil materials obtained are compared with
`commerc1ally ava11able knll 011 and found to be more b1oef-
`fective in a number of areas such as anti-inflammation, anti-
`
`oxidant effects, improving insulin resistances and improving
`b1°°d hpld Pmfile‘
`
`4 Claims, 19 Drawing Sheets
`
`RIMFROST EXHIBIT 1047
`
`RIMFROST EXHIBIT 1047 page 0001
`
`page 0001
`
`
`
`US 9,034,388 B2
`
`Page 2
`
`(56)
`
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`CA
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`EP
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`EP
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`EP
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`JP
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`JP
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`JP
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`WO
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`WO
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`WO
`WO
`
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`
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`page 0005
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`Sheet 1 of 19
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`
`
`SZI'OW
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`page 0006
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`FIGURE 2
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0007
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`page 0007
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`Sheet 3 of 19
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`US 9,034,388 B2
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`FIGURE 3
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0008
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`page 0008
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`U.S. Patent
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`May 19, 2015
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`Sheet 4 of 19
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`US 9,034,388 B2
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`FIGURE 4
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0009
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`page 0009
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`US. Patent
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`May 19, 2015
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`Sheet 5 of 19
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`US 9,034,388 B2
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`FIGURE 5
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0010
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`page 0010
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`U.S. Patent
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`May 19, 2015
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`Sheet 6 of 19
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`US 9,034,388 B2
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0011
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`page 0011
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`US. Patent
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`Sheet 7 of 19
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`US 9,034,388 B2
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`RIMFROST EXHIBIT 1047
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`RIMFROST EXHIBIT 1047 page 0012
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`page 0012
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`U.S. Patent
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`May 19, 2015
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`Sheet 8 of 19
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`US 9,034,388 B2
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`FIGURE 8
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