`
`Table 10: Fatty acid composition E. pacifica
`Solvent
`Saturated
`Unsaturated
`Mono
`22,54
`22,18
`22,11
`22,96
`22,98
`
`chio-meth
`acetone
`acetone
`ethanol
`
`26,18
`21,4
`19,09
`45,93
`45,96
`
`Di
`1,91
`1,75
`=2,03
`1,23
`1,24
`
`Unidentified
`
`Poly
`4,31
`4,67
`4,79
`2,72
`2,48
`
`H-Poly
`26,34
`24,52
`30,24
`11,11
`11,18
`
`18,72
`25,49
`21,72
`16,05 (500 pg/mL)
`16,15 (200 pg/mL)
`
`Data expressed in percentage of total fatty acids (%).
`
`\3
`
`0000020
`
`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0451
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`page 0451
`
`
`
`CA 02251265 1998-10-21
`
`TABLE 11. OPTIMAL CONDITIONS FORLIPID EXTRACTION OF
`AQUATIC ANIMAL TISSUES(suggested procedure)
`
`
`STEP
`
`CONDITIONS
`
`Grinding(if particles > 5mm)
`
`4°C
`
`Lipid extraction
`
`Filtration
`
`Washing
`
`Filtration
`
`Evaporation
`
`Oil-water separation
`
`Lipid extraction
`
`Filtration
`
`Evaporation
`
`sample-acetone ratio of 1:6 (w/v)
`2h (including swirling 20 min)
`4°C
`
`organic solvent resistantfilter
`under reduced pressure
`
`sample-acetone ratio of 1:2 (w/v)
`pure and cold acetone
`
`organic solvent resistantfilter
`under reduced pressure
`
`under reduced pressure
`
`4°C
`
`sample-ethano! ratio of 1:2 (w/v)
`pure ethanol
`30 min
`4°C
`
`organic solvent resistantfilter
`under reduced pressure
`
`.
`
`under reduced pressure
`
`20
`
`0000021
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0452
`
`page 0452
`
`
`
`CA 02251265 1998-10-21
`
`Bibliography
`
`Bowyer, D.E., Leat, W.M.F., Howard, A.N. and Gresham, G.A. 1962. The
`determination of the fatty acid composition of serum lipids separated by
`thin-layer chromatography; and a comparison with column chromatogra-
`phy. BBA. 70: 423-431
`
`Chandrasekar, B., Troyer, D.A., Venkatraman, J.T. and Fernandes, G. 1996.
`Tissue specific regulation of transforming growth factor beta by omega-3
`lipid-rich krill oi! in autoimmune murine lupus. Nutr Res. 16(3): 489-503
`
`Christensen, M.S., Hoy, C-E. and Redgrave, T.G. 1994. Lymphatic absorption
`of n-3 polyunsaturated fatty acids from marineoils with different intramole-
`cularfatty acid distributions. BBA. 1215: 198-204
`
`Difco laboratories. 1984. Difco Manual Dehydrated Culture Media and
`Reagents for Microbiology. 10™ ed. Detroit.
`
`Foich, J., Lees, M. and Sloane-Stanley, G.H. 1957. A simple method for the
`isolation and purification of totallipids from animaltissues. J. biol. Chem.
`226: 497-509
`
`Goodman Gilman, A., Goodman, L.L. and Gilman, A. 1980. The Pharmacological
`Basis of Therapeutics. 6" ed. Collier Macmillan Canada itd, Toronto.
`
`Heligren, L., Karistam, B., Mohr, V. and Vincent, J. 1991. Krill enzymes. A
`new concept forefficient debridement of necrotic ulcers. Int J Dermatol.
`30(2): 102-103
`
`Prawn Hatchery Food. 1997. http://Awww.kk-tech.com/Iillhtml
`
`Runge, J.A. and Joly, P. 1994. Rapport sur l'état des invertébrés en 1994-
`7:0 Zooplancton (Euphausiacés et Calanus) de|'Estuaire et du Golfe
`du Saint-Laurent.
`
`Sargent, J.R. 1997. Fish oils and humandiet. Br J Nutr.78 Supp! 1: S5-S13
`
`ZI
`
`0000022
`
`RIMFROST EXHIBIT 1024 page 0453
`
`RIMFROST EXHIBIT 1024
`
`
`page 0453
`
`
`
`CA 02251265 1998-10-21
`
`Although the present invention has been described herein
`
`above by way of preferred embodiments thereof, it can be modified, without
`
`departing from the spirit and nature of the subject invention as defined in the
`
`appendedclaims.
`
`0000023
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0454
`
`page 0454
`
`
`
`CA 02251265 1998-10-21
`
`WHAT.IS CLAIMED IS:
`
`1.
`
`A method for extracting lipids from an aquatic animal tissue
`
`comprising the stepsof:
`
`a) suspending said animal aquatic tissue in an organic solvent;
`
`b) extracting lipids by successive organic solvent treatment;
`
`and
`
`c)
`
`collecting said lipids in a first fraction and an organic
`
`insoluble fraction.
`
`2.
`
`The method of claim 1, wherein said organic solventof a)is
`
`acetone.
`
`3.
`
`The method of claim 1 or 2, wherein said organic solvent of b)
`
`is selected from at least one of acetone and alcohol.
`
`4.
`
`The method of claim 1, 2 or 3, wherein said organic insoluble
`
`fraction comprises a dry residue fraction which is enriched in protein.
`
`5.
`
`The method of claim 1, 2, 3 or 4, wherein said aquatic animal
`
`tissue is at least one tissue selected from the group consisting ofkrill tissue,
`
`Calanustissue andfish tissue.
`
`6.
`
`A lipid extract obtained by the methodofclaim 2, 3, 4 or 5.
`
`22
`
`0000024
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0455
`
`page 0455
`
`
`
`CA 02251265 1998-10-21
`
`7.
`
`8.
`
`A protein rich fraction obtained by the method of claim 4 or5.
`
`A lipid extract having the properties in accordance with the
`
`presentinvention.
`
`23
`
`0000025
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0456
`
`page 0456
`
`
`
`CA AAA TIAT 1998-10-21
`
`: 98-03-24 20:09:39
`Injection Date
`Sample Name a
`Acq. Operator
`: Chantal Beaudoin
`
`-
`Seq. Line :
`1
`Vial
`:
`1
`Inj
`:
`In} Volume : Manually
`
`Method
`Last changed
`
`|
`i
`|
`
`°
`5
`wo
`
`40 -
`-
`
`b
`
`<
`a
`
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`i
`
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`
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`l= =
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`
`—_844..™ °Ls
`
`: C:\HPCHEM\1\METHODS\ALAIN2 .M
`: 98-03-24 19:56:07
`by Chantal Beaudoin
`(modified after loading)
`Méthode corrigée lors de l'installation de la nouvelle colonne 12 septembre
`1997. Température du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la température a 175 degré C et
`le
`purge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`.
`
`FID1 A, of GEN00002.0
`i
`<3
`oo
`PAT
`Rae
`&
`| b
`|
`2
`:
`
`la
`|
`55 —
`i
`.
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`=
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`6
`
`[=22.606-20:4(6,10,14,18)
`
`tTaPOFi,.
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`an-_
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`)}56.373
`MA
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`
`ow
`oY
`ny
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`ie3Pe
`YLa
`
`24.103
`
`31.295
`
`49.721
`
`>°o
`
`3
`
`Figure 1: Gas-liquid chromatography of fatty acids from dry krill (chloroform-
`methanol).
`
`CONFIDENTIEL
`
`
`
`0000026
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0457
`
`page 0457
`
`
`
`.
`
`Injection Date
`Sample Name
`Acq. Operator
`
`
`CA 02251265 1998-10-21
`UNELUEN Lib
`: 98-03-25 20:00:46 -
`: 11
`: Chantal Beaudoin
`
`ao
`-
`Seq. Line :
`1
`Vial
`:
`1
`Inj
`:
`Inj Volume : Manually
`
`Method
`Last changed
`
`: C:\HPCHEM\1\METHODS\ALAIN2.M
`: 98-03-25 18:55:58
`by Chantal Beaudoin
`(modified after loading)
`Méthode corrigée lors de l'installation de la nouvelle colonne 12 septembre
`1997. Température du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la température a 175 degré C et
`le
`purge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`FID1 A, of GENO0005.0
`
`a
`
`50
`
`=BAAD1st
`
`~~wT
`x
`
`xw
`
`
`|
`
`45
`40
`
`20
`
`ii ' | |I|
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`3
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`:
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`o
`N
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`35
`|
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`os
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`8
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`+
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`
`nO
`-
`
`\
`
`Figure 2: Gas-liquid chromatographyoffatty acids from dry krill (acetone).
`
`CONFIDENTIEL
`
`
`
`0000027
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0458
`
`page 0458
`
`
`
`CA 02251265 1998-10-21
`
`Injection Date
`Sample Name
`Acq. Operator
`
`: 98-04-01 18:48:05
`: 26
`: Chantal Beaudoin
`
`-
`Seq. Line :
`1
`Vial
`:
`1
`Inj
`:
`Inj Volume : Manually
`
`Method
`: C:\HPCHEM\1\METHODS\ALAIN2.M
`Last changed
`: 98-04-01 18:45:50
`by Chantal Beaudoin
`(modified after loading)
`Méthode corrigée lors de l'installation de la nouvelle colonne 12 septembre
`1997. Température du four 170 degré C et purge flow = 150 ml/min. Flux dans
`ta colonne : 4,0 ml/min. Augmentation de la température a 175 degré C et
`le
`2urge flow est descendu a 140 ml/min,
`
`12.140-18:3
`
`&
`
`
`
`24.071
`
`
`
`le 13 IMars 1998. FID1 A, of GEN00008.D
`en, 22.575-20:4(6,10,14,18)
`
`
`>-====62.250
`F>26.215 NSo
`
`
`
`Figure 3: Gas-liquid chromatographyoffatty acids from frozen krill (acetone).
`
`CONFIDENTIEL
`
`
`
`0000028
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0459
`
`page 0459
`
`
`
`tr,
`
`CA 02251265 peg lot
`
`Injection Date
`Sample Name
`Acq. Operator
`
`: 98-04-02 17:35:45
`: 28
`: Chantal Beaudoin
`
`-
`Seq. Line :
`1
`Vial
`:
`1
`Inj
`:
`In} Volume : Manually
`
`Method
`Last changed
`
`: C:\HPCHEM\1\METHODS\ALAIN2 .M
`>: 98-04-02 17:28:39
`by Chantal Beaudoin
`(modified after loading)
`Méthode corrigée lors de l'installation de la nouvelle colonne 12 septembre
`1997. Température du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la température a 175 degré C et
`le
`. purge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`t
`FID? A, of GENO0009.D
`
`eoel48a
`
`oo
`™¢
`“=
`Oo=
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`-
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`¢net
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`
`aa. ,
`9
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`mw
`=™
`N
`
`= A
`
`Figure 4: Gas-liquid chromatography of fatty acids from frozen krill (ethanol).
`
`CONFIDENTIEL
`
`
`
`0000029
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0460
`
`page 0460
`
`
`
`0000030
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0461
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`page 0461
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`0000031
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`cholesterol 20
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`interest;Cai:
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0462
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0463
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`page 0463
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`page 0464
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0464
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`
`
`CA 02251265 1998-10-21
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`RIMFROST EXHIBIT 1024 page 0465
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`RIMFROST EXHIBIT 1024 page 0470
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`
`
`(19) Japan Patent Office (JP)
`(12) Patent Gazette (A)
`(11) Japanese Patent Application Publication
`Number HEI 8 — 231391
`
`(51) Int. Cl 4 Classification Symbol Internal No.
`A23L 1/42
`8412 — 4B
`A61K 9/48
`6742 —4C
`31/355
`7330 —4C
`
`ADL
`
`(43) Publication Date August 13, 1985
`
`(54) Title of Invention
`
`(72) Inventor
`(72) Inventor
`(71) Applicant
`
`Request for Review Unrequested Number of Claims 1 (Total 2 Pages)
`Nutritional Supplement
`(21) Application Number
`Sho 59 — 10625
`(22) Application Date
`January 24, 1984
`Motuski Kenji
`Tokyo-to, Nakano-ku, UenoMiya 4 Choume 9 Ban 6 Go
`Fukuoka Ryuu
`Tama-shi Nagayama 4 No 4 No 21 No 304
`Honen Seiyu Co. Ltd.
`Tokyo-to, Chiyoda-ku, Otemachi 1 Choume 2 Ban 3 Go
`
`Specification
`1. Title of Invention
`Nutritional supplement
`2. Scope of Claims
`(1) A nutritional supplement being contained inside
`a gelatin capsule and comprising a nutritional liquid
`being formed by melting vitamin E, soybean
`lecithin in an oil having high eicosapentaenoic acid
`content.
`(2) A nutritional supplement of claim 1 wherein the
`oil having high eicosapentaenoic acid contentis a
`sea animaloil such as pilchard oil, mackerel oil,
`cuttlefish oil, krill oil, or mink oil.
`3. Detailed Explanation of the Invention
`The present invention relates to a new nutritional
`supplementhavingas its primary ingredients
`vitamin E, soybean lecithin, and an oil having high
`eicosapentaenoic acid content. In recent years, the
`demand for nutritional supplements has greatly
`increased due to factors such as (1) lack of
`nutritional balance brought about by a rich food
`culture, (2) pickiness and lack of food diversity
`causedby a selective food palette, (3) lack of
`nutrition brought about by a breakdownin balance
`of nutrition and health, exercise, and energy, and (4)
`the necessity for supplementary nutrition to
`correspond to an aging population. In particular, the
`desire to stem adult disease by the improvementof
`food life is strong, so people enjoy eating nutritional
`supplements.
`
`The present invention arises out of the
`aforementioned nutritional needs andits object is to
`provide a new nutritional supplement from the
`combination of vitamin E, which (1) prevents the
`aging of cells, (2) lowers cholesterol and prevents
`the hardeningofarteries, (3) prevents the
`occurrence of liquid fatty deposits and encourages
`cell life, (4) cleans and washesbloodvessels and
`prevents brain or heart blood clots; soybean lecithin,
`which (1) encourages the absorption of vitamin E
`and eicosapentaenoic acid, (2) reduces cholesterol
`and prevents hardening of blood vessels and oil
`having high eicosapentaenoic acid content, whichis
`effective anti-platelet aggregation, making it an
`anti-coagulant and acts to prevent the hardening of
`blood vessels.
`In other words, the present invention is a
`nutritional supplement consisting of vitamin E and
`soybeanlecithin melted in an oil having high
`eicosapentaenoic acid content in liquid form
`inserted into a gelatin capsule.
`
`Asfor the vitamin E used in the present invention,
`items obtained by publicly known methods such as
`concentration by chromatography or molecular
`distillation of plant oils are appropriate, but the
`method of production thereofis not limited, and the
`source of energy is also not limited.
`Vitamin E is included in great amounts in
`saffloweroil, rice oil, corn oil, and other oil from
`water dwelling plants. However, the concentration
`
`AKBM 1014
`RIMFROST EXHIBIT 1024 page 0471
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`
`of the oil is at most 0.3%, so using any of these as-is is not desirable.
`
`‘The amount of vitamin E included in the present invention must be at
`least 1% of the liquid included in the capsule. If less than this
`concentration is achieved the activity of the vitamin in the body is
`reduced, and the benefits of vitamin E cannot be achieved.
`
`Also, soybean fatty substance containing soybeanoil obtained by
`dehydrating and drying gum produced by the production of soybean
`gumis generally acceptable for the soybeanlecithin used in
`conjunction with vitamin EF,butit is also acceptable to use lecithin
`that has been sugared and concentrated via acetone or alcohol, and it
`is also possible lo use separated lecithin that contains litle of no
`keratin.
`
`This soybean lecithin must be present in the liquid thatis inserted
`into the capsule in a concentration of at least 1%. As noted before,if
`the concentration falls bclow this level the effects of the substance
`will not be sufficient. In addition, for 011 with a high concentration of
`eicosapentaenoic acid (C20 : 5) that has vitamin E and soybean
`lecithin dissolved within it, an oil with a eicosapentaenoic acid
`content of 8% or higher may be used, such as that found in sea
`animaloils such as pilchard oil, mackerel oil, cuttlefish oil, krill oil,
`or mink oil, or an oil that was derived from oneof the above and had
`was concentrated with respect to eicosapentaenoic acid content.
`
`The concentration of oil having a high concentration of
`eicosapentaenoic acid in the present invention must be at least 10%
`of the volumeofliquid in the capsule. If this concentration 1s not
`achieved then the effect of the oil in the body will be lacking and as
`noted before the
`
`effects will not be sufficient. A nutritional supplement
`formed by melting vitamin F and soybean lecithin in oil
`with a high concentration of eicosapentaenoic acid, within
`the scope wherein it is possible to maintain the relative
`levels of the various substances, may be diluted with
`saffloweroil, rice oil, corn o11, soybean oil, or seaweed oil
`or other sea life oil. Mixed oil obtained in this way is
`inserted into a gelatin capsule under normal circumstances.
`As one example of the method of sealing the substance in
`a capsule, the mixed liquid will be sealed in a gelatin
`capsule in a certain amount, the gelatin formed by melting
`gelatin, glycerin, and water. After that, the entry hole will
`be heated and sealed to create the nutritional substance of
`the present invention.
`The form of the gelatin capsules may be spherical or in
`the form of a rugby ball.
`Because the nutritional supplement of the present
`invention obtained in this way contains vitamin E which
`prevents the aging of cells, lowers cholesterol numbers,
`prevents excess fat deposits, and has other positive side
`effects, as well as contains soybean lecithin, which acts to
`lower cholesterol and promote the absorption of
`eicosapentaenoic acid, and contains eicosapentaenoic acid,
`whichacts to prevent the hardening of blood vessels, the
`combined effects of the various ingredients act to reduce
`the cholesterol levels in the blood, prevent high blood
`pressure, reduce fat, and promote heart and brain function
`in brain and heart medical patients, and acts to treat and
`prevent adult circulatory diseases, and as such can besaid
`to functionas a nutritional supplement.
`
`Below, the embodiments of the present invention are explained.
`Embodiment 1.
`25 parts vitamin E and 25 parts soybean lecithin are dissolved into
`50 parts fish oil (containing 16% eicosapentaenoic acid), heated to
`around 60 degrees Celsius, and dried.
`Then 60 parts gelatin, 30 parts glycerin, and 10 parts water are
`uniformly mixed, arc made to take a film like form, are poured into a
`300 milligram capsule and put into a gelatin container. The
`aforementioned compound1s poured into this container, the entry
`point is heat scaled, and the nutritional supplement of the present
`invention is formed.
`
`[Embodiment 2
`30 parts vitamin F by weight and 30 parts soybean lecithin are
`dissolved into a 1:1 mixture of safflower oil and market concentrated
`
`eicosapentaenoic acid oil (produced by Nippon Yushi Co. Ltd., Sun
`Omega, and containing 25% eicosapentaenoic acid), the mixture
`being 40 parts. The liquid is heated to around 60 degrees Celsius and
`dried.
`Then 60 parts gelatin, 30 parts glycerin, and 10 parts water are
`uniformly mixed, are made to take a film like form, are poured into a
`300 milligram capsule and put into a gelatin container. The
`aforementioned compound is pouredinto this container, the entry
`point is heat sealed, and the nutritional supplement of the present
`invention is formed.
`
`-364-
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`RIMFROST EXHIBIT 1024 page 0472
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`000004
`
`RIMFROST EXHIBIT 1024 page 0476
`RIMFROST EXHTWR347 1PEM08O4517
`
`
`
`(19) Japan Patent Office (JP)
`
`(12) Patent Gazette (A)
`
`(51) Int. C16
`A61K 31/20
`
`Classification Symbol
`AAM
`
`Internal No.
`
`(11) Japanese Patent Application Publication Number
`Hei 8 — 231391
`(43) Publication Date September 10, 1996
`Technology Display Location
`FI
`A61K 31/20 AAM
`
`(21) Application Number
`(22) Application Date
`
`7 — 36362
`February 24, 1995
`
`
`
`Request for Review Unrequested Number of Claims 5 (Total 4 Pages)
`(71) Applicant
`392030380
`Kanagawa Kagaku Kenkyuujo Co. Ltd.
`Kanagawa-ken, Sumohara-shi, Nishi
`Onuma 4 Choume 4 Ban 1 Go
`000173762
`Sumo Central Chemical Research
`Location Foundation
`Kanagawa-ken, Sumohara-shi, Nishi
`Onuma 4 Choume 4 Ban | Go
`592197599
`Fuji Yakuhin Co. Ltd.
`Saitama-ken, Omiya-shi, Sakuragi Machi
`4 Choume 383 Banchi
`Ichira Yasawa
`Kanagawa_ken, Sumohara-shi, Kami-no-
`mori 1 — 28 —- 10
`Miyanaga Kazuo
`Gunma-ken, Macbashi-shi, Kanne Machi
`3-—5-29
`
`(71) Applicant
`
`(71) Applicant
`
`(72) Inventor
`
`(72) Inventor
`
`Continued onthe last page
`
`(54) [Title of the Invention] Medicine for Improvement of Dementia Symptoms
`
`(57) [Abstract]
`[Objective] To smoothly improve the symptoms of
`dementia and provide a medicine for said improvement
`without side effects.
`[Structure] A medicine for improvement of dementia
`symptomsthat has as a characteristic the inclusion of
`docosahexaenoic acid (DHA).
`[Effect] The medicine improves the following ailments
`caused by dementia: loss of will, delirium, worsening of
`human relationships, loitering, manic psychological
`episodes and/orthe reduction of powers of calculation,
`reduction ofjudgment, and reduction in the intellectual
`capacities and functioning of the higher functions.
`
`000001
`
`AKBM 1015
`RIMFROST EXHIBIT 1024 page 0477
`RIMFROST EXHIBE9347)pegos4518
`
`
`
`(2)
`
`[Scope of Claims]
`[Claim 1] A medicine for improvement of dementia symptoms
`being characterized by including as an active ingredient DHA.
`[Claim 2] A medicine for improvement of dementia symptoms
`of claim 1| that treats an adverse psychological state thatis
`dementia.
`[Claim 3] A medicine for improvement of dementia symptoms
`of claim 2 working to reduce will loss, delirium, worsening of
`humanrelationships, manic states, and/orloitering.
`[Claim 4] A medicine for improvement of dementia symptoms
`of claim 1 working to reduce the loss of higher functions and of
`judgment brought about by dementia.
`[Claim 5] A medicine for improvement of dementia symptoms
`of claim 1 working to reducethe loss of intellectual capacity,
`loss of facilities of calculation, loss of judgment, and/or loss of
`higher function due to dementia.
`
`[Detai