`US 9,078,905 B2
`(10) Patent No.:
`Bruheim et al.
`(45) Date of Patent:
`*Jul. 14, 2015
`
`US009078905B2
`
`(54) BIOEFFECTIVE KRILL OIL COMPOSITIONS
`
`(56)
`
`References Cited
`U.S. PATENT DOCUMENTS
`
`(71) Applicant: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`(72)
`
`Inventors:
`
`Inge Bruheim, Volda (NO); Snorre
`Tilseth, Bergen (NO); Daniele
`Mancinelli, Orsta (NO)
`
`(73) Assignee: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`( * ) Notice:
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`This patent is subject to a terminal dis-
`claimer.
`
`(21) Appl.No.: 14/490,221
`
`(22)
`
`Filed:
`
`Sep. 18, 2014
`
`(65)
`
`Prior Publication Data
`
`US 2015/0004227 A1
`
`Jan. 1, 2015
`
`Related US. Application Data
`
`(63) Continuation of application No. 12/057,775, filed on
`Mar. 28, 2008.
`
`(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)
`(2015.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 9/48
`A61K 31/23
`A61K 31/122
`A61K 35/612
`A61K 31/683
`A61K 31/685
`A61K 45/06
`CIIB 3/00
`A61K 31/202
`(52) us. Cl.
`CPC ............. A61K 35/612 (2013.01); A61K 9/4858
`(2013.01); A61K31/122 (2013.01); A61K
`31/202 (2013.01); A61K 31/23 (2013.01);
`A61K 31/683 (2013.01); A61K 31/685
`(2013.01); A61K45/06 (2013.01); CIIB 3/006
`(2013.01)
`
`(58) Field of Classification Search
`CPC ............ A61K 2300/00; A61K 31/122; A61K
`31/202; A61K 31/047; A61K 31/683; A61K
`31/685; A61K 31/23; A61K 35/612; A61K
`31/232; A61K 45/06; A61K 31/661; A61K
`9/4858; A61K 2800/522; A61K 31/045;
`A61K 31/07
`
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`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`AU
`BR
`
`2002322233
`8701265
`
`2/2003
`3/1987
`
`(Continued)
`OTHER PUBLICATIONS
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`
`(Continued)
`
`Primary Examiner 7 Debbie K Ware
`(74) Attorney, Agent, or Firm 7 Casimir Jones SC.
`
`ABSTRACT
`(57)
`This invention discloses new krill oil compositions charac-
`terized by 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
`a co-solvent. Stage 2 extracts the actual krill oils by using
`supercritical CO2 in combination with approximately 20%
`ethanol. The krill oil materials obtained are compared with
`commercially available krill oil and found to be more bioef-
`fective in a number of areas such as anti-inflammation, anti-
`oxidant effects, improving insulin resistances and improving
`blood lipid profile.
`
`See application file for complete search history.
`
`20 Claims, 19 Drawing Sheets
`
`RIMFROST EXHIBIT 1116 Page 0001
`RIMFROST EXHIBIT 1116 Page 0001
`
`
`
`US 9,078,905 B2
`
`Page 2
`
`(56)
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`Sheet 1 0f 19
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`Sheet 2 0f 19
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`Fig. 2
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`Sheet 3 0f 19
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`Fig. 3
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`Sheet 4 0f 19
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`Fig. 4
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`Sheet 5 0f 19
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`Fig. 5
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`Sheet 6 of 19
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`US 9,078,905 B2
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`RIMFROST EXHIBIT 1116 Page 0011
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`Sheet 7 0f 19
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`Fig. 7
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`Jul. 14,