# US 11,439,614 B2 · Fish egg extracts, omega-3 lipid-based compositions and uses thereof

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- Number: US 11,439,614 B2
- Document ID: US11439614B2
- Status: Granted
- Kind: B2
- Application number: 15/939,814
- Filed: 2018-03-29
- Published: 2018-10-04
- Granted: 2022-09-13
- Earliest claimed: 2017-03-29
- Assignees: Bioflash Inc.
- Applicants: Bioflash Inc.
- Inventors: Adrien Beaudoin; Luc Beaudoin
- Web page: https://patentgrep.com/patent/US11439614B2

## CPC

- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A23L 2/02: containing fruit or vegetable juices
- A23L 2/52: Adding ingredients (adding preservatives A23B70/10)
- A23L 17/30: Fish eggs, e.g. caviar; Fish-egg substitutes
- A23L 33/12: Fatty acids or derivatives thereof
- A23L 33/15: Vitamins
- A23L 33/16: Inorganic salts, minerals or trace elements
- A61K 8/361: {Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof}
- A61K 8/987: {of species other than mammals or birds}
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 33/06: Aluminium, calcium or magnesium; Compounds thereof {, e.g. clay}
- A61K 33/30: Zinc; Compounds thereof
- A61K 33/34: Copper; Compounds thereof
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61Q 17/00: Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q 19/00: Preparations for care of the skin
- A23C 9/1315: {Non-milk proteins or fats; Seeds, pulses, cereals or soja; Fatty acids, phospholipids, mono- or diglycerides or derivatives therefrom; Egg products}
- A23C 9/1322: {Inorganic compounds; Minerals, including organic salts thereof, oligo-elements; Amino-acids, peptides, protein-hydrolysates or derivatives; Nucleic acids or derivatives; Yeast extract or autolysate; Vitamins; Antibiotics; Bacteriocins}
- A23C 9/1522: {Inorganic additives, e.g. minerals, trace elements; Chlorination or fluoridation of milk; Organic salts or complexes of metals other than natrium or kalium; Calcium enrichment of milk}
- A23C 9/1528: {Fatty acids; Mono- or diglycerides; Petroleum jelly; Paraffine; Phospholipids; Derivatives thereof}
- A23C 9/154: containing thickening substances, eggs or cereal preparations; Milk gels
- A23C 9/156: Flavoured milk preparations {; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners}
- A23C 9/158: containing vitamins or antibiotics
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K 2800/10: General cosmetic use
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A23C: DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF (preservation thereof A23B11/00)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

Novel methods for isolating fish roe/egg extracts, notably a coagulum and a sediment extract, enriched in phospholipids and omega-3 fatty acids are described. Novel compositions comprising omega-3 polyunsaturated fatty acids and micronutrients, which may be used for the management of neurological conditions such as ADD-ADHD, autism, cognitive impairment, and mood disorders are also described. These compositions are homogenous compositions comprising effective amounts of omega-3 fatty acids in microencapsulated or emulsified form, and/or from the sediment extract from fish roe/egg, vitamin B6, magnesium, zinc and copper, and may further comprise additional ingredients such as folic acid (e.g., L-methyl folate) and gamma-linolenic acid (GLA).

## Claims

### Claim 1

A homogenous solid composition consisting of:
about 250 mg to about 5000 mg of omega-3 fatty acid ethyl esters in solid form, wherein said omega-3 fatty acid ethyl esters are in the form of microencapsulated omega-3 fatty acids ethyl esters, and wherein the docosahexaenoic acid (DHA) ethyl ester/eicosapentaenoic acid (EPA) ethyl ester ratio in said omega-3 fatty acid ethyl esters is from 1/4 to 4/1;
about 10 mg to about 100 mg of vitamin B6;
about 75 mg to about 500 mg of magnesium in the form of a pharmaceutically acceptable salt;
at least 3.5 mg of zinc in the form of a pharmaceutically acceptable salt;
optionally at least 100 μg of copper in the form of picolinate, glycinate, orotate or gluconate;
optionally about 20 mg to about 200 mg of a sediment obtained by a method comprising:
(a) grinding fish roe or eggs in the presence of an antioxidant;
(b) submitting said fish roe or eggs to an osmotic shock at a temperature of less than about 10° C. for at least 20 minutes to obtain a lysed fish roe or egg mixture;
(c) sedimenting the mixture obtained in (b) at a temperature of less than about 10° C., thereby obtaining a supernatant fraction enriched in vitellogenin and a sediment fraction enriched in phospholipids;
(d) separating the supernatant fraction and sediment fraction by filtration or decantation; and
(e) drying the sediment and coagulum at a temperature of about −30° C. to about 50° C.;
optionally about 50 mg to about 500 mg of gamma-linolenic acid (GLA);
optionally about 0.1 mg to about 1 mg of folic acid; and
one or more pharmaceutically acceptable excipients.

### Claim 2 (depends on 1)

The solid composition of claim 1, wherein the omega-3 fatty acid ethyl esters are present in an amount of about 250 mg.

### Claim 3 (depends on 1, 2)

The solid composition of claim 1 or 2, wherein said omega-3 fatty acid ethyl esters are in the form of microencapsulated omega-3 fatty acid ethyl esters obtained by complex coacervation.

### Claim 4 (depends on 1, 2)

The solid composition of claim 1 or 2, wherein said sediment is present in the composition.

### Claim 5 (depends on 1)

The solid composition of claim 1, wherein about 50 mg to about 600 mg of said omega-3 fatty acid ethyl esters in solid form are eicosapentaenoic acid (EPA) ethyl esters.

### Claim 6

A liquid composition consisting of:
about 250 mg to about 5000 mg of omega-3 fatty acid ethyl esters in liquid form, wherein said omega-3 fatty acids are microencapsulated omega-3 fatty acid ethyl esters, and wherein the docosahexaenoic acid (DHA) ethyl ester/eicosapentaenoic acid (EPA) ethyl ester ratio in said omega-3 fatty acids is from 1/4 to 4/1;
about 10 mg to about 100 mg of vitamin B6;
about 75 mg to about 500 mg of magnesium in the form of a pharmaceutically acceptable salt;
at least 3.5 mg of zinc in the form of a pharmaceutically acceptable salt;
optionally at least 100 μg of copper in the form of picolinate, glycinate, orotate or gluconate;
optionally about 20 mg to about 200 mg of a sediment obtained by a method comprising:
(a) grinding fish roe or eggs in the presence of an antioxidant;
(b) submitting said fish roe or eggs to an osmotic shock at a temperature of less than about 10° C. for at least 20 minutes to obtain a lysed fish roe or egg mixture;
(c) sedimenting the mixture obtained in (b) at a temperature of less than about 10° C., thereby obtaining a supernatant fraction enriched in vitellogenin and a sediment fraction enriched in phospholipids;
(d) separating the supernatant fraction and sediment fraction by filtration or decantation; and
(e) drying the sediment and coagulum at a temperature of about −30° C. to about 50° C.;
optionally about 50 mg to about 500 mg of gamma-linolenic acid (GLA);
optionally about 0.1 mg to about 1 mg of folic acid; and
one or more pharmaceutically acceptable excipients.

### Claim 7 (depends on 6)

The liquid composition of claim 6, where the omega-3 fatty acid ethyl esters are present in an amount of about 250 mg.

### Claim 8 (depends on 6, 7)

The liquid composition of claim 6 or 7, wherein said omega-3 fatty acids are microencapsulated omega-3 fatty acid ethyl esters obtained by complex coacervation.

### Claim 9 (depends on 8)

The liquid composition of claim 8, wherein about 50 mg to about 600 mg of said omega-3 fatty acid ethyl esters in solid form are eicosapentaenoic acid (EPA) ethyl esters.

### Claim 10 (depends on 1, 6)

A method for improving cognitive functions in a subject in need thereof, the method comprising administering to the subject an effective amount of the composition of claim 1 or 6.

### Claim 11 (depends on 10)

The method of claim 10, wherein said subject suffers from a cognitive impairment.

### Claim 12 (depends on 10)

The method of claim 10, wherein said subject suffers from attention-deficit/hyperactivity disorder (ADHD) or a neurodegenerative condition.

### Claim 13 (depends on 12)

The method of claim 12, wherein said neurodegenerative condition is mild cognitive impairment, Alzheimer's disease or Parkinson's disease.

### Claim 14 (depends on 1, 6)

The composition of claim 1 or 6, wherein said gamma-linolenic acid (GLA) and/or folic acid are present in the composition.

### Claim 15 (depends on 14)

A method for improving a symptom of a mood disorder in an adult subject comprising administering to said subject an effective amount of the composition defined in claim 14.

### Claim 16 (depends on 15)

The method of claim 15, wherein said mood disorder is depression or anxiety.

### Claim 17 (depends on 1)

The composition of claim 1, wherein the DHA/EPA ratio in said omega-3 fatty acids is from 2/3 to 3/2.

### Claim 18 (depends on 6)

The composition of claim 6, wherein the DHA/EPA ratio in said omega-3 fatty acids is from 2/3 to 3/2.

### Claim 19 (depends on 1)

The composition of claim 1, wherein the pharmaceutically acceptable salt of magnesium is magnesium picolinate, magnesium glycinate, or magnesium gluconate.

### Claim 20 (depends on 6)

The composition of claim 6, wherein the pharmaceutically acceptable salt of magnesium is magnesium picolinate, magnesium glycinate, or magnesium gluconate.

### Claim 21 (depends on 1)

The composition of claim 1, wherein the vitamin B6 is in the form of pyridoxine hydrochloride.

### Claim 22 (depends on 6)

The composition of claim 6, wherein the vitamin B6 is in the form of pyridoxine hydrochloride.

### Claim 23 (depends on 1)

The composition of claim 1, wherein the composition is for administration to a subject having one or more symptoms of a neurological condition.

### Claim 24 (depends on 6)

The composition of claim 6, wherein the composition is for administration to a subject having one or more symptoms of a neurological condition.

### Claim 25 (depends on 23)

The composition of claim 23, wherein the neurological condition is attention-deficit disorder (ADD), attention-deficit/hyperactivity disorder (ADHD), anxiety or depression.

### Claim 26 (depends on 24)

The composition of claim 24, wherein the neurological condition is attention-deficit disorder (ADD), attention-deficit/hyperactivity disorder (ADHD), anxiety or depression.