CA 02251265 1998-10-21
`
`Table 10: Fatty acid composition E. pacifica
`Solvent
`Saturated
`Unsaturated
`Mono
`22.54
`22,18
`22.11
`22.96
`22.98
`
`chic-math
`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 pglmL)
`16.15 (200 ngmL)
`
`Data expressed in percentage of total fatty acids (96).
`
`\3
`
`0000020
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0451
`
`page 0451
`
`

`

`CA 02251265 1998-10-21
`
`TABLE 11. OPTIMAL CONDITIONS FOR LIPID EXTRACTION 0F
`AQUATIC ANIMAL TISSUES (suggested procedure)
`
`
`STEP
`
`C NDITIONS
`
`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 (wlv)
`2h (including swirling 20 min)
`4°C
`
`organic solvent resistant filter
`under reduced pressure
`
`sample-acetone ratio of 1:2 (wlv)
`pure and cold acetone
`
`organic solvent resistant filter
`under reduced pressure
`
`under reduced pressure
`
`4°C
`
`sample-ethanoi ratio of 1:2 (wlv)
`pure ethanol
`30 min
`
`4°C
`
`organic solvent resistant filter
`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., Leaf, W.M.F., Howard, AN. and Gresham. GA 1962. The
`determination of the fatty acid composition of serum lipids separated by
`thin-layer chromatography; and a comparison with column chromatogra-
`phy. BSA 70: 423-431
`
`Chandrasekar. B., Troyer, DA, Venkatraman, J.T. and Fernandes, G. 1996.
`Tissue specific regulation of transforming growth factor beta by omega-3
`lipid-rich krill oil 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 marine oils with different intramoie-
`cular fatty acid distributions. BBA 1215: 198—204
`
`Difco laboratories. 1984. Difco Manual Dehydrated Culture Media and
`Reagents for Microbiology. 10" ed. Detroit.
`
`Folch, J., Lees. M. and Sloane-Stanley. G.H. 1957. A simple method for the
`isolation and purification of total lipids from animal tissues. J. biol. Chem.
`226: 497-509
`
`Goodman Gilman, A, Goodman. LL. and Gilman, A 1980. The Pharmacological
`Basis of Therapeutics. 6" ed. Collier Macmillan Canada ltd. Toronto.
`
`Hellgren, L., Karlstam, B., Mohr, V. and Vincent, J. 1991. Kn'll enzymes. A
`new concept for efficient debridement of necrotic ulcers. Int J Dermatol.
`30(2): 102-103
`
`Prawn Hatchery Food. 1997. ht_tp://www.kk—techcom/lrrill.html
`
`Runge, JA and Joly, P. 1994. Rapport sur l'état des invertébrés en 1994:
`7:0 Zooplancton (Euphausiacés et Calanus) de I'Estuaire et du Gotfe
`du Saint-Laurent.
`
`Sargent, JR. 1997. Fish oils and human diet. Br J Nutr.78 Suppl 1: 85-813
`
`2|
`
`0000022
`
`RIMFROST EXHIBIT 1024 page 0453
`
`RIMFRO ST 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
`
`appended claims.
`
`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 steps of:
`
`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 solvent of 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 of krill tissue,
`
`Calanus tissue and fish tissue.
`
`6.
`
`A lipid extract obtained by the method of claim 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 or 5.
`
`A lipid extract having the properties in accordance with the
`
`present invention.
`
`23
`
`0000025
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0456
`
`page 0456
`
`

`

`CA 02251265 1998-10-21
`
`CUNFIDENTIEL
`
`Injection Date
`Sample Name
`Acq. Operator
`
`: 98-03-24 20:09:39
`:
`7
`»
`: Chantal Beaudoin
`
`—
`Seq. Line :
`1
`Vial
`:
`1
`Inj
`:
`Inj Volume : Manually
`
`Method
`Last changed
`
`: C:\HPCHEM\1\MBTHODS\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. Temperature du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la temperature a 175 degré C et
`le
`
`pur e flow est descendu a 140 ml/min,
`le 13 mars 1998.
`FlD1 A, arsenoooozo
`
`pAiiW-
`‘_'
`
`V
`
`I $1
`
`
`
`5.570
`
`13.458
`
`
`
`
`
`»-22.ooo20:4(d.1o.141a)
`
`31m.73(11§11c1u11)
`
`
`
`19.3442012
`
`28.287
`
`24.103
`
`r25.247
`
`31295
`
`D40.665
`
`49721
`
`D55373
`
`62.225
`
`~___
`
`fl...—
`
`Figure 1: Gas-liquid chromatography of fatty acids from dry krill (chloroform-
`methanol).
`
`CONFHJEM‘IEL
`
`
`
`0000026
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0457
`
`page 0457
`
`l 1
`
`I
`
`‘
`
`1 1 i i
`
`

`

`
`
`.'
`
`.
`
`Injection Date
`Sample Name
`Acq. Operator
`
`CA 02251265 l§§8110-21
`WM
`11M;
`-7
`_.
`98—03—25 20:00:46 -
`:
`: 11
`: Chantal Beaudoin
`
`_-i___-_
`—
`Seq. Line :
`1
`Vial
`2
`1
`Inj
`:
`In'j Volume : Manually
`
`Method
`
`: C:\HPCHEM\1\METHODS\ALAIN2.M
`
`Last changed
`
`by Chantal Beaudoin
`: 98-03—25 18:55:58
`(modified after loading)
`Méthode corrigée lors de l'installation de la nouvelle colonne 12 septembre
`1997. Temperature du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la temperature a 175 degré C et
`le
`purge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`FID1A. ofGENOOOOSD
`
`:1?
`
`
`
`-9.62?!116.3%
`
`I
`
`45
`
`‘°
`35
`
`304
`
`.
`2st _
`VA W
`
`20
`
`
`
`
`
`
`aa
`3
`'1
`
`A
`3-
`a:e
`
`§ «
`
`3
`{13
`N
`‘
`
`Figure 2: Gas-liquid chromatography of fatty acids from dry krill (acetone).
`
`CONFIDEme
`
`
`
`0000027
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0458
`
`page 0458
`
`

`

`'
`
`CA 02251265 1998-10-21
`
`CONFIDENTIEL
`
`Injection Date
`Sample Name
`Acq. Operator
`
`: 98-04—01 18:48:05
`: 26
`: Chantal Beaudoin
`
`—
`Seq. Line :
`l
`Vial
`:
`1
`Inj
`:
`Inj Volume : Manually
`
`Method
`Last changed
`
`: C:\HPCHEM\1\MEITHODS\ALAIN2.M
`: 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. Temperature du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la temperature a 175 degré C et
`le
`burge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`FI01 A oreeuoooow
`
`0|0
`
`
` U!0‘
`; aAng+hLAAJ4JJJ
`12.140-18:3
`
`
`
`V
`,
`J— r
`
`E
`8
`3'
`E‘
`A
`o.
`40
`[i
`9i
`3'
`§
`I
`3
`35'}
`z
`E
`“‘
`1
`i
`3
`3
`3
`3
`i
`l
`«2
`“'3
`J:
`fiv— 2
`l
`5
`,I
`"5' g
`-
`i
`25—);
`
`1
`~ .
`'
`20—:
`
`
`
`
`Figure 3: Gas-liquid chromatography of fatty acids from frozen krill (acetone).
`
`CONFHJENHEL
`
`
`
`0000028
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0459
`
`page 0459
`
`

`

`t
`
`‘
`
`"
`
`‘
`
`CA 02251265 1998-10-21
`
`UUNMHENTIEL
`
`Injection Date
`Sample Name
`Acq. Operator
`
`98—04—02 17:35:45
`:
`: 28
`: Chantal Beaudoin
`
`-
`Seq. Line :
`1
`Vial
`:
`l
`Inj
`:
`Inj 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. Temperature du four 170 degré C et purge flow = 150 ml/min. Flux dans
`la colonne : 4,0 ml/min. Augmentation de la temperature a 175 degré C e:
`le
`.purge flow est descendu a 140 ml/min,
`le 13 mars 1998.
`I
`FlmA 0152510000943
`.
`9229.
`
`5m .1s
`
`
` _
`
`21523-20:4(5,10,14,13)
`
`21.300-20:3
`
`Figure 4: Gas-liquid chromatography of fatty acids from frozen kn'll (ethanol).
`
`CONFIDENTIEL
`
`
`
`0000029
`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0460
`
`page 0460
`
`

`

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`220A
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`0000030
`
`RIMFROST EXHIBIT 1024
`
`page 0461
`
`RIMFROST EXHIBIT 1024 page 0461
`
`

`

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`RIMFROST EXHIBIT 1024
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`page 0462
`
`RIMFROST EXHIBIT 1024 page 0462
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`

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`
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`ano
`moleste'ml'zo
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`0000032
`
`RIMFROST EXHIBIT 1024
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`page 0463
`
`RIMFROST EXHIBIT 1024 page 0463
`
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`RIMFROST EXHIBIT 1024
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`page 0464
`
`RIMFROST EXHIBIT 1024 page 0464
`
`

`

`CA 02251265 1998-10-21
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`
`RIMFROST EXHIBIT 1024
`
`RIMFROST EXHIBIT 1024 page 0465
`
`page 0465
`
`

`

`CA 02251265 1998-10-21
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0466
`
`page 0466
`
`

`

`CA 02251265 1998- l0-21
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0467
`
`page 0467
`
`

`

`CA 02251265 1998-10-21
`
`
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`RIMFROST EXHIBIT 1024
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`RIMFROST EXHIBIT 1024 page 0468
`
`page 0468
`
`

`

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`RIMFROST EXHIBIT 1024 page 0470
`
`RIMFROST EXHIEF&%I1€6%QSZ%39
`
`

`

`(19) Japan Patent Office (JP)
`(12) Patent Gazette (A)
`(11) Japanese Patent Application Publication
`Number HE18 — 231391
`
`(51) Int. Cl 4 Classification Symbol Internal No.
`A23L 1/42
`8412—4B
`A61 K 9/48
`6742—4C
`
`31/355
`
`ADL
`
`7330—4C
`
`(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 4 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 content is a
`sea animal oil 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
`supplement having as 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
`caused by a selective food palette, (3) lack of
`nutrition brought about by a breakdown in 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 improvement of
`food life is strong, so people enjoy eating nutritional
`supplements.
`
`The present invention arises out of the
`aforementioned nutritional needs and its 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 hardening of arteries, (3) prevents the
`occurrence of liquid fatty deposits and encourages
`cell life, (4) cleans and washes blood vessels 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, which is
`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
`soybean lecithin melted in an oil having high
`eicosapentaenoic acid content in liquid form
`inserted into a gelatin capsule.
`
`As for 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 thereof is not limited, and the
`source of energy is also not limited.
`Vitamin E is included in great amounts in
`safflower oil, rice oil, corn oil, and other oil from
`water dwelling plants. However, the concentration
`
`-363-
`
`000001
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`AKBM 1014
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`RIMFROST EXHIBIT 1024 page 0471
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`RIMFROST EXHIWREIQé‘hn’mQ‘bZ’Mo
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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 soybean oil obtained by
`dehydrating and drying gum produced by the production of soybean
`gum is generally acceptable for the soybean lecithin used in
`conjunction with vitamin E, but it is also acceptable to use lecithin
`that has been sugared and concentrated via acetone or alcohol, and it
`is also possible to use separated lecithin that contains little of no
`keratin.
`
`This soybean lecithin must be present in the liquid that is inserted
`into the capsule in a concentration of at least 1%. As noted before, if
`the concentration falls below this level the effects of the substance
`
`will not be sufficient. In addition, for oil 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
`animal oils such as pilchard oil, mackerel oil, cuttlefish oil, krill oil,
`or mink oil, or an oil that was derived from one of 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 volume of liquid in the capsule. If this concentration is 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 E 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
`safflower oil, rice oil, corn oil, 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,
`which acts 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 be said
`to function as 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, 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 poured into this container, the entry
`point is heat sealed, and the nutritional supplement of the present
`invention is formed.
`
`Embodiment 2
`
`30 parts vitamin E 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 poured into this container, the entry
`point is heat sealed, and the nutritional supplement of the present
`invention is formed.
`
`-364-
`
`000002
`
`RIMFROST EXHIBIT 1024 page 0472
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`RIMFROST EXHIWRéIQé‘Mme‘bK‘m
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`

`

`(19) Japan Patent Office (JP)
`
`(12) Patent Gazette (A)
`
`(11) Japanese Patent Application Publication Number
`Hei 8 — 231391
`
`(43) Publication Date September 10, 1996
`
`(51) Int. Cl 6
`A61K 31/20
`
`Classification Symbol
`AAM
`
`Intemal No.
`
`Technology Display Location
`FI
`A61K31/20 AAM
`
`Request for Review Unrequested Number of Claims 5 (Total 4 Pages)
`
`(21) Application Number
`(22) Application Date
`
`7 — 36362
`February 24, 1995
`
`(71) Applicant
`
`(71) Applicant
`
`(71) Applicant
`
`(72) Inventor
`
`(72) Inventor
`
`
`
`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 1 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 i 28 i 10
`
`Miyanaga Kazuo
`Gunma-kcn, Macbashi-shi, Kannc Machi
`3 — 5 — 29
`
`Continued 011 the last page
`
`(54) [Title of the Invention] Medicine for Improvement of Dementia Symptoms
`
`(5 7) [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
`symptoms that 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/or the reduction of powers of calculation,
`reduction ofjudgment, and reduction in the intellectual
`capacities and fimctioning of the higher fun