`
`PATENT
`
`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`In Re Application of:
`
`SAMPALIS, Fotini
`
`Confirmation No.:
`
`1767
`
`Serial No.:
`
`13/189,714
`
`Group Art Unit:
`
`1629
`
`Filed:
`
`July 25, 201 1
`
`Examiner:
`
`POLANSKY, Gregg
`
`FOR:
`
`NATURAL
`
`MARINE
`
`SOURCE
`
`PHOSPHOLIPIDS
`
`COMPRISING
`
`POLYUNSATURATED FATTY ACIDS AND THEIR APPLICATIONS
`
`Mail Stop Amendment
`Commissioner for Patents
`
`P.O. Box 1450
`
`Alexandria, VA 22313-1450
`
`AMENDMENT/RESPONSE TO OFFICE ACTION
`
`In response to the Non-Final Official Action dated January 5, 2012, please amend the
`
`above-identified patent application in the following manner:
`
`Amendments to the Claims begin on page 2 of this paper.
`
`Remarks begin on page 27 of this paper.
`
`89531 V4/BN
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`000001
`
`AKBM 1061
`
`000001
`
`
`
`IN THE CLAIMS:
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`Set forth below in ascending order, with status identifiers,
`
`is a complete listing of all
`
`claims currently under examination.
`
`Changes to any amended claims are indicated by
`
`strikethrough and underlining. This listing also reflects any cancellation and/or addition of
`
`claims.
`
`1. - 120. (Cancelled)
`
`121.
`
`(New) A phospholipid extract derived from marine or aquatic biomass,
`
`the extract
`
`comprising: a phospholipid of the formula (I),
`
`(1)
`
`if
`H2C—O—C—R1
`
`o
`
`fi
`
`I
`R2—C—O—CH
`
`H2C—O—P—O—X
`
`0.
`
`wherein R1 and R2, each together with the respective carboxyl groups to which each is attached,
`
`each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA)
`
`residue, and X is -CH2CH2NH3, -CH2CH2N(CH3)3, or
`
`89531v4/BN
`
`000002
`
`000002
`
`
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`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
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`wherein the extract is suitable for human consumption.
`
`122.
`
`(New) The extract according to claim 121, wherein the extract has a total phospholipid
`
`concentration in an amount of about 40% w/w, wherein about represents :: 10%.
`
`123.
`
`(New) The extract according to claim 121, wherein the extract has a total phospholipid
`
`concentration in an amount of about 45% w/w, wherein about represents :: 20%.
`
`124.
`
`(New) The extract according to claim 121, further comprising an additional lipid, wherein
`
`the additional
`
`lipid is selected from the group consisting of monoglycerides,
`
`triglycerides,
`
`cholesterols, mixtures thereof, and free fatty acids.
`
`125.
`
`(New) The extract according to claim 121, wherein the extract has a concentration of free
`
`fatty acids of about 5% w/w of the lipids in the extract.
`
`126.
`
`(New) The extract according to claim 121, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.
`
`127.
`
`(New) The extract according to claim 121, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.
`
`128.
`
`(New) The extract according to claim 121, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.
`
`129.
`
`(New) The extract according to claims 126, 127, or 128, wherein the polyunsaturated
`
`fatty acids are omega-3 fatty acids.
`
`130.
`
`(New) The extract according to claim 121, wherein DHA and EPA comprise at least 32%
`
`w/w of the lipids in the extract.
`
`131.
`
`(New) The extract according to claim 121, wherein DHA and EPA comprise at least 35%
`
`w/w of the lipids in the extract.
`
`132.
`
`(New) The extract according to claim 121, further comprising a metal.
`
`133.
`
`(New) The extract according to claim 132, wherein the metal is zinc, selenium or a
`
`mixture thereof
`
`134.
`
`(New) The extract according to claim 133, wherein the zinc comprises at least 0.005
`
`mg/ 100g of the extract and the selenium comprises less than 3 mg/ 100g of the extract.
`
`89531v4/BN
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`-3-
`
`000003
`
`000003
`
`
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`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
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`135.
`
`(New) The extract according to claim 124, wherein the fatty acid composition of the
`
`lipids in the extract is about:
`
`Total
`
`Phosphatidyl-
`
`Phosphatidyl-
`
`Phospholipid
`
`choline
`
`ethanolamine
`
`Fatty Acids
`
`Fatty Acid %
`
`Fatty Acid %
`
`Fatty Acid %
`
`2
`
`1
`
`0.2
`
`24
`
`2
`
`1
`
`9
`
`2
`
`1
`
`1
`
`2
`
`0.5
`
`0.6
`
`89531 V4/BN
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`-4-
`
`000004
`
`000004
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C20:3n3 Homo-y-
`
`LINOLENIC
`
`27
`
`1
`
`25
`
`wherein about represents :: 10%.
`
`136.
`
`(New) The extract according to claim 135, wherein the total fatty acid composition of all
`
`the lipids in the extract is:
`
`Sample
`
`Fatty Acid Composition
`
`C14 : 0
`
`C14 : 1
`
`C15 : 0
`
`%
`
`2300
`
`20.01
`
`>0.3
`
`89531v4/BN
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`-5-
`
`000005
`
`000005
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C16 :
`
`C16 :
`
`C18 :
`
`C18 :
`
`>—t©>—t©
`
`C18
`
`: 2n6
`
`C18
`
`: 3n6 GLA
`
`C18
`
`: 3n3 ALA
`
`C18
`
`: 4n3
`
`C20 :
`
`C20 :
`
`C20
`
`: 2n6
`
`C20
`
`: 3n6
`
`C20
`
`: 4n6
`
`C20
`
`: 3n3
`
`C20
`
`: 4n3
`
`C20
`
`: 5n3 EPA
`
`C22 :
`
`C22 :
`
`C22
`
`: 2n6
`
`C22
`
`: 4n6
`
`C22
`
`: 5n6
`
`C22
`
`: 5n3 DPA
`
`C22
`
`: 6n3 DHA
`
`C24 :
`
`C24 :
`
`E20.00
`
`E3.25
`
`E1.00
`
`E10.00
`
`E2.00
`
`E004
`
`E001
`
`E1.50
`
`E005
`
`E100
`
`E005
`
`E005
`
`E0.50
`
`E0.01
`
`E0.20
`
`E2500
`
`E0.01
`
`E1.50
`
`E003
`
`E0.01
`
`E0.01
`
`E0.50
`
`E1000
`
`>001
`
`E005.
`
`137.
`
`(New) The extract according to claim 136, wherein the total fatty acid composition of all
`
`the lipids is:
`
`Saturated (g/100g lipid)
`
`E2200
`
`89531 V4/BN
`
`-6-
`
`000006
`
`000006
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`Monounsaturated (g/100g lipid)
`
`Polyunsaturated (g/100g lipid)
`
`Omega-3 (g/ 100g lipid)
`
`Omega-6 (g/ 100g lipid)
`
`21 1.00
`
`235.00
`
`230.00
`
`21.00.
`
`138.
`
`(New) The extract according to claim 124, comprising:
`
`Monoglycerides (MG) (g/ 100g sample)
`
`Triglycerides (TG) (g/ 100g sample)
`
`Free Fatty Acids (FFA) (g/ 100g sample)
`
`Cholesterol (g/100g sample)
`
`Total Phospholipids (PL) (g/ 100g sample)
`
`Phosphatidyl Ethanolamine (PE) (g/ 100g sample)
`
`Phosphatidyl Inositol (PI) (g/ 100g sample)
`
`Phosphatidyl Serine (PS) (g/ 100g sample)
`
`Phosphatidyl Choline (PC) (g/ 100g sample)
`
`Sphingomyelin (g/ 100g sample)
`
`Vitamin A (ug/ 100 ml)
`
`Vitamin E (ug/100 ml)
`
`Beta-Carotene (ug/ 100 ml)
`
`Astaxanthin (mg/100 ml)
`
`Canthaxanthin (mg/100 ml)
`
`Flavonoid (mg/ 100 ml)
`
`20.7
`
`23.00
`
`25.00
`
`£2.00
`
`240.00
`
`22.50
`
`20.20
`
`20.20
`
`235.00
`
`20.50
`
`21,400
`
`215
`
`21,600
`
`210
`
`210
`
`27.0.
`
`139.
`
`(New) The extract of claim 121, wherein one of R1 and R2 is EPA and the other is DHA.
`
`140.
`
`(New) The extract of claim 121, wherein R1 and R2 is EPA.
`
`141.
`
`(New) The extract of claim 121, wherein R1 and R2 is DHA.
`
`142.
`
`(New) The extract of claim 121, further comprising an antioxidant.
`
`89531v4/BN
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`-7-
`
`000007
`
`000007
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`143.
`
`(New) The extract of claim 142, wherein the antioxidant is selected from the group
`
`consisting of Vitamin A, Vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin,
`
`flavonoids, and mixtures thereof.
`
`144.
`
`(New) A formulation for oral administration comprising a phospholipid extract derived
`
`from marine or aquatic biomass, the extract comprising: a phospholipid of the formula (I),
`
`(1)
`
`1:’
`H2C—O—C—R1
`
`o
`
`ii
`
`I
`R2—C—O—CH
`
`H2C—O—P—O—X
`
`wherein R1 and R2, each together with the respective carboxyl groups to which each is attached,
`
`each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA)
`
`residue, and X is -CH2CH2NH3, -CH2CH2N(CH3)3, or
`
`
`
`; and
`
`wherein the extract is suitable for human consumption.
`
`145.
`
`(New) The formulation according to claim 144, wherein the formulation for oral
`
`administration is in the form of one or more of a capsule, tablet, solution, syrup, and suspension.
`
`146.
`
`(New) The extract according to claim 144, wherein the extract has a total phospholipid
`
`concentration in an amount of about 40% w/w, wherein about represents :: 10%.
`
`89531v4/BN
`
`-8-
`
`000008
`
`000008
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`147.
`
`(New) The extract according to claim 144, wherein the extract has a total phospholipid
`
`concentration in an amount of about 45% w/w, wherein about represents :: 20%.
`
`148.
`
`(New) The formulation according to claim 144, further comprising an additional lipid,
`
`wherein the additional
`
`lipid is
`
`selected from the group consisting of monoglycerides,
`
`triglycerides, cholesterols, mixtures thereof, and free fatty acids.
`
`149.
`
`(New) The formulation according to claim 144, wherein the extract has a concentration of
`
`free fatty acids of about 5% w/w of the lipids in the extract.
`
`150.
`
`(New) The formulation according to claim 144, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.
`
`151.
`
`(New) The formulation according to claim 144, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.
`
`152.
`
`(New) The formulation according to claim 144, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.
`
`153.
`
`(New) The
`
`formulation according to claims
`
`150,
`
`151, or
`
`152, wherein the
`
`polyunsaturated fatty acids are omega-3 fatty acids.
`
`154.
`
`(New) The formulation according to claim 144, wherein DHA and EPA comprise at least
`
`32% w/w of the lipids in the extract.
`
`155.
`
`(New) The formulation according to claim 144, wherein DHA and EPA comprise at least
`
`35% w/w of the lipids in the extract.
`
`156.
`
`(New) The formulation according to claim 144, further comprising a metal.
`
`157.
`
`(New) The formulation according to claim 156, wherein the metal is zinc, selenium or a
`
`mixture thereof.
`
`158.
`
`(New) The formulation according to claim 157, wherein the zinc comprises at least 0.005
`
`mg/ 100g of the extract and the selenium comprises less than 3 mg/ 100g of the extract.
`
`159.
`
`(New) The formulation according to claim 144, wherein the fatty acid composition of the
`
`lipids in the extract is about:
`
`89531v4/BN
`
`-9-
`
`000009
`
`000009
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`Total
`
`Phosphatidy1-
`
`Phospholipid
`
`choline
`
`FattyAcid% FattyAcid%
`
`Phosphatidy1-
`
`cthanolarninc
`
`FattyAcid%
`
`O Q
`
`G DJ
`
`l\)-B
`
`O Q
`
`l\)-B
`
`G 00
`
`G OJ
`
`G
`
`G DJ
`
`[Q Q
`
`)—* l\)
`
`CCC
`
`1 1 1
`
`1
`
`1 1 1 1 1 1 1
`
`O Q
`
`G O\
`
`89531 V4/BN
`
`-10-
`
`0000010
`
`0000010
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`27
`
`1
`
`25
`
`wherein about represents :: 10%.
`
`160.
`
`(New) The formulation according to claim 159, wherein the total fatty acid composition
`
`of all the lipids in the extract is:
`
`Sample
`
`Fatty Acid Composition
`
`C14 : 0
`
`C14 : 1
`
`C15 : 0
`
`C16 : 0
`
`89531v4/BN
`
`-11-
`
`0000011
`
`%
`
`2300
`
`2001
`
`203
`
`220.00
`
`0000011
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C16 : 1
`
`C18 : 0
`
`C18 : 1
`
`C18 : 2n6
`
`C18 : 3n6 GLA
`
`C18 : 3n3 ALA
`
`C18 : 4n3
`
`C20 : 0
`
`C20 : 1
`
`C20 : 2n6
`
`C20 : 3n6
`
`C20 : 4n6
`
`C20 : 3n3
`
`C20 : 4n3
`
`C20 : 5n3 EPA
`
`C22 : 0
`
`C22 : 1
`
`C22 : 2n6
`
`C22 : 4n6
`
`C22 : 5n6
`
`C22 : 5n3 DPA
`
`C22 : 6n3 DHA
`
`C24 : 0
`
`C24 : 1
`
`23.25
`
`21.00
`
`210.00
`
`22.00
`
`20.04
`
`20.01
`
`21.50
`
`20.05
`
`21.00
`
`20.05
`
`20.05
`
`20.50
`
`20.01
`
`20.20
`
`225.00
`
`20.01
`
`21.50
`
`20.03
`
`20.01
`
`20.01
`
`20.50
`
`210.00
`
`20.01
`
`20.05.
`
`161.
`
`(New) The formulation according to claim 160, wherein the total fatty acid composition
`
`of all the lipids is:
`
`Saturated (g/100g lipid)
`
`Monounsaturated (g/100g lipid)
`
`222.00
`
`21 1.00
`
`89531v4/BN
`
`-12-
`
`0000012
`
`0000012
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`Polyunsaturated (g/100g lipid)
`
`Omega-3 (g/ 100g lipid)
`
`Omega-6 (g/ 100g lipid)
`
`235 .00
`
`230.00
`
`21.00.
`
`162.
`
`(New) The formulation according to claim 148, comprising:
`
`Monoglycerides (MG) (g/ 100g sample)
`
`Triglycerides (TG) (g/ 100g sample)
`
`Free Fatty Acids (FFA) (g/ 100g sample)
`
`Cholesterol (g/100g sample)
`
`Total Phospholipids (PL) (g/ 100g sample)
`
`Phosphatidyl Ethanolamine (PE) (g/ 100g sample)
`
`Phosphatidyl Inositol (PI) (g/ 100g sample)
`
`Phosphatidyl Serine (PS) (g/ 100g sample)
`
`Phosphatidyl Choline (PC) (g/ 100g sample)
`
`Sphingomyelin (g/ 100g sample)
`
`Vitamin A (ug/ 100 ml)
`
`Vitamin E (ug/100 ml)
`
`Beta-Carotene (ug/ 100 ml)
`
`Astaxanthin (mg/100 ml)
`
`Canthaxanthin (mg/100 ml)
`
`Flavonoid (mg/ 100 ml)
`
`20.7
`
`23.00
`
`25.00
`
`£2.00
`
`240.00
`
`22.50
`
`20.20
`
`20.20
`
`235.00
`
`20.50
`
`21,400
`
`215
`
`21,600
`
`210
`
`210
`
`27.0.
`
`163.
`
`(New) The formulation of claim 144, wherein one of R1 and R2 is EPA and the other is
`
`DHA.
`
`164.
`
`(New) The formulation of claim 144, wherein R1 and R2 is EPA.
`
`165.
`
`(New) The formulation of claim 144, wherein R1 and R2 is DHA.
`
`166.
`
`(New) The formulation of claim 144, further comprising an antioxidant.
`
`89531v4/BN
`
`-13-
`
`0000013
`
`0000013
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`167.
`
`(New) The formulation of claim 166, wherein the antioxidant is selected from the group
`
`consisting of vitamin A, vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin,
`
`flavonoids, and mixtures thereof.
`
`168.
`
`(New) A nutraceutical composition comprising a phospholipid extract derived from
`
`marine or aquatic biomass, the extract comprising: a phospholipid of the formula (I),
`
`(1)
`
`1:’
`H2C—O—C—R]
`
`o
`
`if
`
`I
`R2—C—O—CH
`
`H2C—O—P—O—X
`
`wherein R1 and R2, each together with the respective carboxyl groups to which each is attached,
`
`each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA)
`
`residue, and X is -CH2CH2NH3, -CH2CH2N(CH3)3, or
`
`; and
`
`wherein the extract is suitable for human consumption.
`
`169.
`
`(New) The nutraceutical composition of claim 168, wherein the nutraceutical is in the
`
`form of one or more of a food, beverage, energy bar, and supplement.
`
`89531v4/BN
`
`-14-
`
`0000014
`
`0000014
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`170.
`
`(New) The extract according to claim 168, wherein the extract has a total phospholipid
`
`concentration in an amount of about 40% w/w, wherein about represents :: 10%.
`
`171.
`
`(New) The extract according to claim 168, wherein the extract has a total phospholipid
`
`concentration in an amount of about 45% w/w, wherein about represents :: 20%.
`
`172.
`
`(New) The nutraceutical composition of claim 168, wherein the extract further comprises
`
`an additional
`
`lipid, wherein the additional
`
`lipid is selected from the group consisting of
`
`monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.
`
`173.
`
`(New) The nutraceutical composition of claim 168, wherein the extract has
`
`a
`
`concentration of free fatty acids of about 5% w/w of the lipids in the extract.
`
`174.
`
`(New) The nutraceutical composition of claim 168, wherein polyunsaturated fatty acids
`
`comprise at least 15% w/w of the lipids in the extract.
`
`175.
`
`(New) The nutraceutical composition of claim 168, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract
`
`176.
`
`(New) The nutraceutical composition of claim 168, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.
`
`177.
`
`(New) The nutraceutical composition of claim 174,
`
`175, or 176, wherein the
`
`polyunsaturated fatty acids are omega-3 fatty acids.
`
`178.
`
`(New) The nutraceutical composition of claim 168, wherein DHA and EPA comprise at
`
`least 32% w/w of the lipids in the extract.
`
`179.
`
`(New) The nutraceutical composition of claim 168, wherein DHA and EPA comprise at
`
`least 35% w/w of the lipids in the extract.
`
`180.
`
`(New) The nutraceutical composition of claim 168, wherein the extract further comprises
`
`a metal.
`
`181.
`
`(New) The nutraceutical composition of claim 180, wherein the metal is zinc, selenium or
`
`a mixture thereof
`
`182.
`
`(New) The nutraceutical composition of claim 181, wherein the zinc comprises at least
`
`0.005 mg/ 100g of the extract and the selenium comprises less than 3 mg/ 100g of the extract.
`
`89531v4/BN
`
`-15-
`
`0000015
`
`0000015
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`1 83.
`
`(New) The nutraceutical composition of claim 172, wherein the fatty acid composition of
`
`the lipids in the extract is about:
`
`Total
`
`Phosphatidy1-
`
`Phosphatidy1-
`
`Phospholipid
`
`choline
`
`ethanolarnine
`
`Fatty Acids
`
`Fatty Acid % Fatty Acid %
`
`Fatty Acid %
`
`C14:0 MYRISTIC
`
`C14:1 MYRISTOLEIC
`
`C15 :0 PENTADECANOIC
`
`C16:0 PALMITIC
`
`C16: 1 PALMITOLEIC
`
`C 1 8 :0 STEARIC
`
`C18:1OLEIC
`
`C18:2n6 LINOLEIC
`
`C18:3n6 GLA
`
`C 1 8 :3n3 ALA
`
`C18:4n3 OTA
`
`C20:0 ARACHIDIC
`
`2
`
`1
`
`0.2
`
`24
`
`2
`
`1
`
`9
`
`2
`
`1
`
`1
`
`2
`
`2
`
`0.7
`
`0.3
`
`27
`
`2
`
`1
`
`12
`
`2
`
`0.3
`
`1
`
`2
`
`0.3
`
`24
`
`0.7
`
`3
`
`24
`
`0.8
`
`0.3
`
`C20:1 cis-11-EICOSENOIC
`
`0.5
`
`0.6
`
`0.7
`
`C20 :2n6 EICOSADIENOIC
`
`C20:3n6 METHYL ETA
`
`C20:4n6 ARACHIDONIC
`
`0.6
`
`0.2
`
`0.7
`
`0.6
`
`89531 V4/BN
`
`-16-
`
`0000016
`
`0000016
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C20:3n3 Hon1o-y-
`
`LINOLENIC
`
`27
`
`1
`
`25
`
`wherein about represents :: 10%.
`
`184.
`
`(New) The nutraceutical composition of claim 183, wherein the total
`
`fatty acid
`
`composition of all the lipids in the extract is:
`
`Sample
`
`Fatty Acid Composition
`
`C14 : 0
`
`C14 : 1
`
`C15 : 0
`
`%
`
`2300
`
`20.01
`
`20.3
`
`89531v4/BN
`
`-17-
`
`0000017
`
`0000017
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C16 : 0
`
`C16 : 1
`
`C18 : 0
`
`C18 : 1
`
`C18 : 2n6
`
`C18 : 3n6 GLA
`
`C18 : 3n3 ALA
`
`C18 : 4n3
`
`C20 : 0
`
`C20 : 1
`
`C20 : 2n6
`
`C20 : 3n6
`
`C20 : 4n6
`
`C20 : 3n3
`
`C20 : 4n3
`
`C20 : 5n3 EPA
`
`C22 : 0
`
`C22 : 1
`
`C22 : 2n6
`
`C22 : 4n6
`
`C22 : 5n6
`
`C22 : 5n3 DPA
`
`C22 : 6n3 DHA
`
`C24 : 0
`
`C24 : 1
`
`E20.00
`
`E3.25
`
`E1.00
`
`E10.00
`
`E2.00
`
`E0.04
`
`E0.01
`
`E1.50
`
`E0.05
`
`E1.00
`
`E0.05
`
`E0.05
`
`E0.50
`
`E0.01
`
`E020
`
`E25.00
`
`E001
`
`E1.50
`
`E003
`
`E0.01
`
`E0.01
`
`E050
`
`E1000
`
`E0.01
`
`E005.
`
`185.
`
`(New) The nutraceutical composition of claim 184, wherein the total
`
`fatty acid
`
`composition of all the lipids is:
`
`Saturated (g/100g lipid)
`
`E22.00
`
`89531v4/BN
`
`-18-
`
`0000018
`
`0000018
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`Monounsaturated (g/100g lipid)
`
`Polyunsaturated (g/100g lipid)
`
`Omega-3 (g/ 100g lipid)
`
`Omega-6 (g/ 100g lipid)
`
`21 1.00
`
`235.00
`
`230.00
`
`21.00.
`
`186.
`
`(New) The nutraceutical composition of claim 172, comprising:
`
`Monoglycerides (MG) (g/ 100g sample)
`
`Triglycerides (TG) (g/ 100g sample)
`
`Free Fatty Acids (FFA) (g/ 100g sample)
`
`Cholesterol (g/100g sample)
`
`Total Phospholipids (PL) (g/ 100g sample)
`
`Phosphatidyl Ethanolamine (PE) (g/ 100g sample)
`
`Phosphatidyl Inositol (PI) (g/ 100g sample)
`
`Phosphatidyl Serine (PS) (g/ 100g sample)
`
`Phosphatidyl Choline (PC) (g/ 100g sample)
`
`Sphingomyelin (g/ 100g sample)
`
`Vitamin A (ug/ 100 ml)
`
`Vitamin E (ug/100 ml)
`
`Beta-Carotene (ug/ 100 ml)
`
`Astaxanthin (mg/100 ml)
`
`Canthaxanthin (mg/100 ml)
`
`Flavonoid (mg/ 100 ml)
`
`20.7
`
`23.00
`
`25.00
`
`£2.00
`
`240.00
`
`22.50
`
`20.20
`
`20.20
`
`235.00
`
`20.50
`
`21,400
`
`215
`
`21,600
`
`210
`
`210
`
`27.0.
`
`187.
`
`(New) The nutraceutical composition of claim 168, wherein one of R1 and R2 is EPA
`
`and the other is DHA.
`
`188.
`
`(New) The nutraceutical composition of claim 168, wherein R1 and R2 is EPA.
`
`189.
`
`(New) The nutraceutical composition of claim 168, wherein R1 and R2 is DHA.
`
`190.
`
`(New) The nutraceutical composition of claim 168, wherein the extract further comprises
`
`an antioxidant.
`
`89531v4/BN
`
`-19-
`
`0000019
`
`0000019
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`191.
`
`(New) The nutraceutical composition of claim 190, wherein the antioxidant is selected
`
`from the group consisting of Vitamin A, Vitamin E, carotenoid, beta-carotene, astaxanthin,
`
`canthaxanthin, flavonoids, and mixtures thereof.
`
`192.
`
`(New) A cosmetic preparation comprising a phospholipid extract derived from marine or
`
`aquatic biomass, the extract comprising: a phospholipid of the formula (I),
`
`(1)
`
`1:’
`H2C—O—C—R]
`
`o
`
`if
`
`I
`R2—C—O—CH
`
`H2C—O—P—O—X
`
`wherein R1 and R2, each together with the respective carboxyl groups to which each is attached,
`
`each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA)
`
`residue, and X is -CH2CH2NH3, -CH2CH2N(CH3)3, or
`
`; and
`
`wherein the extract is suitable for human consumption.
`
`193.
`
`(New) The cosmetic preparation of claim 192, wherein the cosmetic is in the form of a
`
`topical cosmetic product.
`
`89531v4/BN
`
`-20-
`
`0000020
`
`0000020
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`194.
`
`(New) The cosmetic preparation of claim 193, wherein the topical cosmetic product is
`
`one or more of a moisturizing cream and a sun-block product.
`
`195.
`
`(New) The extract according to claim 192, wherein the extract has a total phospholipid
`
`concentration in an amount of about 40% w/w, wherein about represents :: 10%.
`
`196.
`
`(New) The extract according to claim 192, wherein the extract has a total phospholipid
`
`concentration in an amount of about 45% w/w, wherein about represents :: 20%.
`
`197.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises an
`
`additional
`
`lipid, wherein the additional
`
`lipid is selected from the group consisting of
`
`monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.
`
`198.
`
`(New) The cosmetic preparation of claim 192, wherein the extract has a concentration of
`
`free fatty acids of about 5% w/w of the lipids in the extract.
`
`199.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.
`
`200.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.
`
`201.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises
`
`polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.
`
`202.
`
`(New) The cosmetic preparation of claim 199, 200, or 201, wherein the polyunsaturated
`
`fatty acids are omega-3 fatty acids.
`
`203.
`
`(New) The cosmetic preparation of claim 192, wherein DHA and EPA comprise at least
`
`32% w/w of the lipids in the extract.
`
`204.
`
`(New) The cosmetic preparation of claim 192, wherein DHA and EPA comprise at least
`
`35% w/w of the lipids in the extract.
`
`205.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises a
`
`metal.
`
`206.
`
`(New) The cosmetic preparation of claim 205, wherein the metal is zinc, selenium or a
`
`mixture thereof.
`
`89531v4/BN
`
`-21-
`
`0000021
`
`0000021
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`207.
`
`(New) The cosmetic preparation of claim 206, wherein the zinc comprises at least 0.005
`
`mg/ 100g of the extract and the selenium comprises less than 3 mg/ 100g of the extract.
`
`208.
`
`(New) The cosmetic preparation of claim 197, wherein the fatty acid composition of the
`
`lipids in the extract is about:
`
`Total
`
`Phosphatidyl-
`
`Phosphatidyl-
`
`Phospholipid
`
`choline
`
`ethanolamine
`
`Fatty Acids
`
`Fatty Acid %
`
`Fatty Acid %
`
`Fatty Acid %
`
`2
`
`1
`
`0.2
`
`24
`
`2
`
`1
`
`9
`
`2
`
`1
`
`1
`
`2
`
`0.5
`
`89531 V4/BN
`
`-22-
`
`0000022
`
`0000022
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C20:3n6 METHYL ETA
`
`C20:4n6 ARACHIDONIC
`
`0.6
`
`C20:3n3 Homo-y-
`
`LINOLENIC
`
`27
`
`1
`
`25
`
`wherein about represents :: 10%.
`
`209.
`
`(New) The cosmetic preparation of claim 208, wherein the total fatty acid composition of
`
`all the lipids in the extract is:
`
`Sample
`
`Fatty Acid Composition
`
`%
`
`89531v4/BN
`
`-23-
`
`0000023
`
`0000023
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`C14 :
`
`C14 :
`
`C15 :
`
`C16 :
`
`C16 :
`
`C18 :
`
`C18 :
`
`>—*©>—*©©>—‘©
`
`C18
`
`: 2n6
`
`C18
`
`: 3n6 GLA
`
`C18
`
`: 3n3 ALA
`
`C18
`
`: 4n3
`
`C20 :
`
`C20 :
`
`C20
`
`: 2n6
`
`C20
`
`: 3n6
`
`C20
`
`: 4n6
`
`C20
`
`: 3n3
`
`C20
`
`: 4n3
`
`C20
`
`: 5n3 EPA
`
`C22 :
`
`C22 :
`
`C22
`
`: 2n6
`
`C22
`
`: 4n6
`
`C22
`
`: 5n6
`
`C22
`
`: 5n3 DPA
`
`C22
`
`: 6n3 DHA
`
`C24 :
`
`C24 :
`
`E3.00
`
`E0.01
`
`E0.3
`
`E20.00
`
`E3.25
`
`E1.00
`
`E10.00
`
`E2.00
`
`E0.04
`
`E0.01
`
`E1.50
`
`E0.05
`
`E1.00
`
`E005
`
`E005
`
`E0.50
`
`E0.01
`
`E0.20
`
`E25.00
`
`E0.01
`
`E1.50
`
`E0.03
`
`>0.01
`
`E0.01
`
`E0.50
`
`E10.00
`
`>0.01
`
`E0.05.
`
`89531 V4/BN
`
`-24-
`
`0000024
`
`0000024
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`210.
`
`(New) The cosmetic preparation of claim 209, wherein the total fatty acid composition of
`
`all the lipids is:
`
`Saturated (g/100g lipid)
`
`Monounsaturated (g/100g lipid)
`
`Polyunsaturated (g/100g lipid)
`
`Omega-3 (g/ 100g lipid)
`
`Omega-6 (g/ 100g lipid)
`
`222.00
`
`21 1.00
`
`235.00
`
`230.00
`
`21.00.
`
`211.
`
`(New) The nutraceutical composition of claim 197, comprising:
`
`Monoglycerides (MG) (g/ 100g sample)
`
`Triglycerides (TG) (g/ 100g sample)
`
`Free Fatty Acids (FFA) (g/ 100g sample)
`
`Cholesterol (g/100g sample)
`
`Total Phospholipids (PL) (g/ 100g sample)
`
`Phosphatidyl Ethanolamine (PE) (g/ 100g sample)
`
`Phosphatidyl Inositol (PI) (g/ 100g sample)
`
`Phosphatidyl Serine (PS) (g/ 100g sample)
`
`Phosphatidyl Choline (PC) (g/ 100g sample)
`
`Sphingomyelin (g/ 100g sample)
`
`Vitamin A (ug/ 100 ml)
`
`Vitamin E (ug/100 ml)
`
`Beta-Carotene (ug/ 100 ml)
`
`Astaxanthin (mg/100 ml)
`
`Canthaxanthin (mg/100 ml)
`
`Flavonoid (mg/ 100 ml)
`
`20.7
`
`23.00
`
`25.00
`
`£2.00
`
`240.00
`
`22.50
`
`20.20
`
`20.20
`
`235.00
`
`20.50
`
`21,400
`
`215
`
`21,600
`
`210
`
`210
`
`27.0.
`
`212.
`
`(New) The cosmetic preparation of claim 192, wherein one of R1 and R2 is EPA and the
`
`other is DHA.
`
`213.
`
`(New) The cosmetic preparation of claim 192, wherein R1 and R2 is EPA.
`
`89531v4/BN
`
`-25-
`
`0000025
`
`0000025
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`214.
`
`(New) The cosmetic preparation of claim 192, wherein R1 and R2 is DHA.
`
`215.
`
`(New) The cosmetic preparation of claim 192, wherein the extract further comprises an
`
`antioxidant.
`
`216.
`
`(New) The cosmetic preparation of claim 215, wherein the antioxidant is selected from
`
`the group consisting of Vitamin A, Vitamin E, carotenoid, beta-carotene, astaxanthin,
`
`canthaxanthin, flavonoids, and mixtures thereof.
`
`89531 V4/BN
`
`-26-
`
`0000026
`
`0000026
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`REMARKS
`
`Status of the Claims
`
`Claims 1-20 are cancelled (claims 21-120 were previously cancelled). Claims 121-216
`
`are new. The new claims find basis in,
`
`inter alia,
`
`the claims as originally filed and the
`
`specification at, for example, 111] [0002], [0075]-[0077], [0088], [0095], [0096], [0097], and
`
`[0104]. No new matter has been added by way of these amendments.
`
`Rejections under 35 U.S.C. § 112
`
`On page 2,
`
`the Office Action rejects claims 12-15 under 35 U.S.C.
`
`§ 112, fourth
`
`paragraph as allegedly being indefinite for improper dependent form. Claims 12-15 have been
`
`cancelled, rendering this rejection moot. Applicant respectfully requests withdrawal of this
`
`rej ection.
`
`On page 4,
`
`the Office Action rejects claims 1-20 under 35 U.S.C.
`
`§ 112, second
`
`paragraph as allegedly being indefinite for failure to particularly point out and distinctly claim
`
`the subject matter which Applicant regards as the invention. Claims 1-20 have been cancelled,
`
`rendering this rejection moot. Applicant respectfully requests withdrawal of this rejection.
`
`Rejection under 35 U.S.C. § 102
`
`On page 7, the Office Action rejects claims 1-20 under 35 U.S.C. § 102(b) as allegedly
`
`being anticipated by Beaudoin (WO 00/23546).
`
`The Office Action argues that the extract disclosed and claimed in the instant application
`
`was “prepared using the same extraction methods disclosed in WO 00/23546” (Office Action
`
`dated 1/5/2012, page 7). The Office Action further states that “the summary of the extraction
`
`disclosed in the instant specification mirrors the extraction process taught by Beaudoin et al.”
`
`(Office Action dated 1/5/2012, page 7).
`
`Applicant
`
`respectfully disagrees with this
`
`characterization for the following reasons.
`
`89531v4/BN
`
`-27-
`
`0000027
`
`0000027
`
`
`
`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`The instant application claims extracts, formulations, nutraceutical compositions, and
`
`cosmetic compositions comprising phospholipids esterizzed with omega—3 fatty acids DHA
`
`and/or EPA (see claims 121, 144, 168, and 192 and claims dependent therefrom).
`
`In contrast,
`
`Beaudoin does Q disclose the types of fatty acids esterzfied on the phospholipids as recited in
`
`the instantly claimed extract. That omega-3 fatty acid carrying phosphates are not disclosed in
`
`Beaudoin is not surprising since Beaudoin explicitly discloses that fraction I and fraction II of
`
`the lipids are heated to remove traces of organic solventsl:
`
`“To get rid of traces of organic solvents, lipid fractions I and II are warmed to about 125°C for
`about 15 minutes under inert atmosphere.” Beaudoin, page 7, lines 18-19 (emphasis added).
`
`and
`
`Applicant also notes that Beaudoin reports either a single step extraction using acetone or a two-step
`1
`extraction of krill using successive acetone and alcohol treatments. The instant application discloses a three step
`process and a mixture of organic solvents used in the last step.
`Since different organic solvents dissolve
`biomolecules differently, the process of Beaudoin could not inherently produce the extracts claimed in the instant
`application as argued by the Office Action. For example, Beaudoin discloses a one step process of extracting with
`acetone:
`
`“The method of the invention comprises suspending freshly collected marine and aquatic material
`in acetone. Lipids are extracted with a ketone such as acetone.”
`
`and
`
`it is noted that extraction with acetone alone may be sufficient to allow a cost-effective
`“...
`recovery of lipid fractions...” Beaudoin, page 4, lines 29-31, Beaudoin, page 5, lines 18-19;
`
`and a two-step process:
`
`“In a preferred embodiment, the extraction is carried out by successive acetone and alcohol
`treatments. Preferred alcohols are isopropanol, and t-butanol. The alcohol may also be substituted
`with an ester of acetic acid such as ethyl acetate. The procedure produces two successive lipid
`fractions.” Beaudoin, page 5, lines 1-4. Beaudoin teaches a step-wise extraction using acetone
`first and then either alcohol or substitution of the alcohol with esters of acetic acid, i.e. ethyl
`acetate.
`
`In contrast, the present application discloses extracts made by a three step process: successive extractions
`with acetone followed by a mixture of organic solvents, preferably ethanol/ethyl acetate. For example, the instant
`specification teaches:
`
`“[0159] Preferably, freshly harvested and finely divided marine and aquatic animal material is
`subjected to acetone extraction
`agitated during extraction and a volume ratio of about 6:1 of
`acetone ....”
`
`“[0160] The solubilized lipid fraction is separated from the solid starting material by known
`techniques
`[t]he residue is optionally washed with acetone to recover more lipid and the
`acetone removed by flash evaporation
`”
`
`“ [0161] The solid residue left on the filter from the initial extraction is suspended and extracted
`with 95/5 ethyl acetate/ethanol, preferably two volumes (original volume of material).”
`
`Instant Application, Specification, paragraphs [0159]-[0161]. Even if one considered the successive extractions
`with acetone as one step, the mixture of ethyl acetate and ethanol is not taught or even suggested by Beaudoin.
`
`89531v4/BN
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`-28-
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`0000028
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`0000028
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`
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`Attorney Docket No. NEPN-001/02US 313663-2013
`Serial No. 13/189,714
`
`“To get rid of traces of solvents, it is important to briefly heat (to about 125°C, for about 15
`min) the oil under nitrogen.” Beaudoin, page 7, lines 19-20 (emphasis added).
`
`Not only is the fact that Beaudoin discloses heating at 125°C for 15 minutes supported by
`
`the Beaudoin reference itself, it is also consistent with other patent references. For example,
`
`U.S. Patent 7,572,464 to Chandler, a patent which cites Beaudoin’s WO 00/23546 on its face,
`
`states at Column 2, lines 13-22:
`
`“The extraction of essential fatty acids such as the polyunsaturated fatty acids ETA and EPA from
`raw material sources has been carried out routinely by simple solvent extraction, followed by
`evaporation and recovery of the solvent. Alternatively, supercritical carbon dioxide has been used
`as a solvent e. g. U.S. Pat. No. 6,083,536. The disadvantage of the former method is that heat
`must be used to evaporate the considerable guantities of solvent used and this leads to
`degradation of the active PUFA conten ” (emphasis added).
`
`and, at Column 3, lines 34-38:
`
`“One of the main advantages of the invention [z'.e., the contents of U.S. Patent 7,572,464] is that
`the extraction and filtration process can be operated at, or below, ambient temperature to ensure
`the best yield of active PUFAs. There is no need to evaporate large volumes of solvent from the
`extracted oil using heat” (emphasis added).
`
`Thus, Chandler states that a disadvantage of a process like that disclosed by Beaudoin is the
`
`necessity of removing the large amounts of solvents using elevated heat which “leads