I lllll llllllll Ill lllll lllll lllll lllll lllll 111111111111111111111111111111111
`US009644169B2
`
`c12) United States Patent
`Bruheim et al.
`
`(IO) Patent No.:
`(45) Date of Patent:
`
`US 9,644,169 B2
`*May 9, 2017
`
`(54) BIOEFFECTIVE KRILL OIL
`COMPOSITIONS
`
`(71) Applicant: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`(72)
`
`Inventors: Inge Bruheim, Valda (NO); Snorre
`Tilseth, Bergen (NO); Daniele
`Mancinelli, Orsta (NO)
`
`(73) Assignee: AKER BIOMARINE ANTARCTIC
`AS, Stamsund (NO)
`
`(58) Field of Classification Search
`None
`See application file for complete search history.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`2,652,235 A
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`
`9/1953 Samuelsen
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`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`( *) Notice:
`
`Subject to any disclaimer, the term ofthis
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`AU
`BR
`
`2002322233
`212003
`3/1987
`8701265
`(Continued)
`
`This patent is subject to a terminal dis(cid:173)
`claimer.
`
`OTHER PUBLICATIONS
`
`(21) Appl. No.: 15/180,431
`
`(22) Filed:
`
`Jun. 13, 2016
`
`(65)
`
`Prior Publication Data
`
`US 2016/0281026 Al
`
`Sep. 29, 2016
`
`(63)
`
`(51)
`
`(52)
`
`Related U.S. Application Data
`
`Continuation of application No. 14/020,162, filed on
`Sep. 6, 2013, now Pat. No. 9,375,453, which is a
`(Continued)
`
`Int. Cl.
`CJJB 3100
`A61K 9148
`
`(2006.01)
`(2006.01)
`(Continued)
`
`U.S. Cl.
`CPC ............ CJJB 31006 (2013.01); A61K 910053
`(2013.01); A61K 9148 (2013.01); A61K 914825
`(2013.01);
`
`(Continued)
`
`Takaichi et al., 2003, "Fatty Acids of astaxanthin esters in krill
`determined by mild mass spectrometry", Comparative Biochemistry
`and Physiology Part B, Biochemistry and Molecular Biology,
`Elsevier, Oxford, vol. 136, Jan. 1, 2003, p. 317-322.
`(Continued)
`
`Primary Examiner - Yate K Cutliff
`(74) Attorney, Agent, or Firm - Casimir Jones, S.C.
`ABSTRACT
`(57)
`This invention discloses new krill oil compositions charac(cid:173)
`terized by having high amounts of phospholipids, astaxan(cid:173)
`thin 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 approxi(cid:173)
`mately 5% of a co-solvent. Stage 2 extracts the actual krill
`oils by using supercritical co2 in combination with approxi(cid:173)
`mately 20% ethanol. The krill oil materials obtained are
`compared with commercially available krill oil and found to
`be more bioeffective in a number of areas such as anti(cid:173)
`inflammation, anti-oxidant effects, improving insulin resis(cid:173)
`tances and improving blood lipid profile.
`20 Claims, 19 Drawing Sheets
`
`RIMFROST EXHIBIT 1001 Page 0001
`
`

`

`US 9,644,169 B2
`Page 2
`
`Related U.S. Application Data
`
`continuation of application No. 12/057,775, filed on
`Mar. 28, 2008, now Pat. No. 9,034,388.
`
`(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)
`(2015.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 311122
`A61K 31123
`A61K 311683
`A61K 311685
`A61K 351612
`A61K 45106
`A61K 311202
`A61K 31120
`A61K 311235
`A61K 9100
`(52) U.S. Cl.
`CPC .......... 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
`351612 (2013.01); A61K 45106 (2013.01)
`
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`Declaration of Dr. Albert Lee in Support of Inter Partes Review of
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`Declaration of Dr. Albert Lee in Support of Inter Partes Review of
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`Declaration of Dr. Earl White submitted during prosecution of
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`Declaration of Dr. Ivar Storrn in support of Inter Partes Review of
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`Declaration of Dr. Ivar Storrn in support of Inter Partes Review of
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`Declaration of Dr. Jaczynski submitted during prosecution of parent
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`Declaration of Dr. Jeff Moore in Support of Inter Partes Review of
`U.S. Pat. No. 8,278,351 ("Moore").
`Declaration of Dr. Jeff Moore in Support of Inter Partes Review of
`U.S. Pat. No. 8,383,675 ("Moore").
`Declaration of Dr. Richard van Breemen in Support of Inter Partes
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`Declaration of Dr. Richard van Breemen in Support of Inter Partes
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`Declaration of Dr. Shahidi submitted during inter partes reexami(cid:173)
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`Declaration of Dr. Shahidi submitted during prosecution of parent
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`Declaration of Dr. Suzanne Budge in Support oflnter Partes Review
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`Declaration of Dr. Suzanne Budge in Support oflnter Partes Review
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`Declaration of Dr. Thomas Brenna in support oflnter Partes Review
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`Declaration of Dr. Thomas Brenna in support oflnter Partes Review
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`Declaration of Dr. Thomas Gundersen submitted during inter partes
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`Declaration of Dr. Tina Sampalis submitted during inter partes
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`Declaration of Dr. Van Breemen submitted during Ex parte Reex(cid:173)
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`Declaration of Dr. Van Breemen submitted during Inter partes
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`Declaration of Dr. Yeboah submitted during inter partes reexami(cid:173)
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`Declaration of Dr. Yeboah submitted during prosecution of parent
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