(12) Unlted States Patent
`(10) Patent No.:
`US 9,072,752 B1
`
`Bruheim et a].
`(45) Date of Patent:
`*Jul. 7, 2015
`
`USOO9072752B1
`
`(54) BIOEFFECTIVE KRILL OIL COMPOSITIONS
`
`-
`.
`(71) Appl1cant.
`
`(72)
`
`Inventors:
`
`:ISGESR BIOlélARgNE ANTARCTIC
`,
`tamsun (N )
`
`Inge Bruheim, Volde (NO); Snorre
`Tilseth3 Bergen (NO); Daniele
`Mancinelli Orsta (NO)
`’
`
`.
`.
`(73) Ass1gnee. AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`( * ) Notice:
`
`'
`'
`Subject to any disclaimer, the term of this
`31:13 1155:);Slbtil) (Eyegldluswd under 35
`’
`’
`’
`’
`~
`~
`~
`~
`~
`_
`Tlhrs patent 1s subject to a terminal d1s
`C almer-
`
`(21) Appl. No.: 14/620,784
`
`(22)
`
`Filed:
`
`Feb. 12, 2015
`
`Related US. Application Data
`(63) Continuation of application No. 12/057,775, filed on
`Mar. 28, 2008.
`
`AU
`Ei
`
`5,006,281 A
`5,266,564 A
`5,434,183 A
`6,214,396 B1
`6,346,276 B1
`6,537,787 B1
`6,800,299 B1
`7,488,503 B1
`7,666,447 B2
`8,030,348 B2
`8,278,351 B2
`8,383,675 B2
`8,697,138 B2
`2002/0076468 A1
`3883;89411431212; :1
`2004/0241249 A1
`2006/0078625 A1
`2006/0193962 A1
`2008/0166419 A1
`2008/0166420 A1
`2010/0143571 A1
`2010/0160659 A1
`2011/0130458 A1
`
`4/1991 Rubin et a1.
`11/1993 Modolell
`7/1995 Larsson-Backstrom
`4/2001 Barrier
`2/2002 Tanouchi et 31.
`3/2003 Breton
`10/2004 Beaudoin et a1.
`2/2009 Porzio et a1.
`2/2010 Rockway
`10/2011 Sampalis
`10/2012 Sampalis
`2/2013 Sampalis
`4/2014 Bruheim et a1.
`6/2002 Saxby
`0s 1t0m1 eta .
`33883 $381211? et €11~
`1
`12/2004 Sampalis
`4/2006 Rockway
`8/2006 Kamiya et a1.
`7/2008 Sones
`7/2008 Sones
`6/2010 Breivik
`6/2010 Catchpole
`6/2011 Breivik
`
`............
`
`426/643
`
`................ 426/615
`
`FOREIGN PATENT DOCUMENTS
`
`2002322233
`figgéggg
`
`2/2003
`431/1981
`,
`(Continued)
`
`(60) Provisional application No. 60/920,483, filed on Mar.
`28, 2007, provisional application No. 60/975,058,
`filed on Sep. 25’ 2007’ prov1s1onal applicat1on NO'
`60/983,446,
`filed on Oct. 29, 2007, prov1s1onal
`1‘
`tion No 61/024 072 filed on Jan 28 2008
`app lea
`’
`’
`’
`’
`’
`’
`
`(51)
`
`(2015.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int- Cl-
`A61K 35/612
`A61K 31/122
`A61K 31/20
`A61K 9/48
`A61K 31/235
`(52) U'S' Cl'
`CPC """"""" A61K 35/612 (201301); A61K 31/122
`(2013.01); A61K 31/20 (2013.01); A61K 9/48
`.
`(2013.01); A61K31/235 (2013.01)
`.
`(58) Fleld of Class1ficat10n Search
`CPC ............ A61K 2300/00; A61K 31/122; A61K
`31/685; A61K 35/612; A61K 31/683; A61K
`31/23; A61K 31/202; A61K 45/06; A61K
`9/4858; A61K 31/133; A61K 31/198; A61K
`31/201; A61K 31/232; A61K 31/575; A61K
`31/661; A61K 38/1767; A61K 9/2009;
`A61K 9/2054
`See application file for complete search history.
`
`(56)
`
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`A 1.
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`pp ”3 “.m 0'.
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`.
`Brzust0w1cz, Mlchael R., et a1., “Controlllng Membrane Cholesterol
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`.
`.”, Journal of Chro-
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`(Continued)
`
`,
`.
`.
`.
`Primary hammer * Debl’le K Ware:
`(74) Attorney, Agent, or Flrm 7 Cas1m1r Jones S.C.
`
`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
`
`20 Claims, 19 Drawing Sheets
`
`RIMFROST EXHIBIT 1118 Page 0001
`RIMFROST EXHIBIT 1118 Page 0001
`
`

`

`US 9,072,752 B1
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`RIMFROST EXHIBIT 1118 Page 0002
`RIMFROST EXHIBIT 1118 Page 0002
`
`

`

`US 9,072,752 B1
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`
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`
`

`

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`Fig. 2
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`HDL
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`LDL
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`Fig. 4
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`US 9,072,752 B1
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