WO2021125708A1 - Nicotinamide riboside derivative conjugated to fatty amine - Google Patents
Nicotinamide riboside derivative conjugated to fatty amine Download PDFInfo
- Publication number
- WO2021125708A1 WO2021125708A1 PCT/KR2020/018182 KR2020018182W WO2021125708A1 WO 2021125708 A1 WO2021125708 A1 WO 2021125708A1 KR 2020018182 W KR2020018182 W KR 2020018182W WO 2021125708 A1 WO2021125708 A1 WO 2021125708A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nicotinamide riboside
- formula
- whitening
- present
- group
- Prior art date
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- JLEBZPBDRKPWTD-TURQNECASA-O N-ribosylnicotinamide Chemical class NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=C1 JLEBZPBDRKPWTD-TURQNECASA-O 0.000 title claims abstract description 71
- 150000001412 amines Chemical class 0.000 title abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 32
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- 230000002087 whitening effect Effects 0.000 claims abstract description 17
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- 125000001931 aliphatic group Chemical group 0.000 claims description 6
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- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
Definitions
- the present invention relates to a fatty amine-conjugated nicotinamide riboside derivative, and more particularly, to nicotinamide riboside (nicotinamide riboside) that is a precursor of nicotinamide adenine dinucleotide (NAD) through increased stability and bioabsorption and hydrolysis in the body ( It relates to a fatty amine-conjugated nicotinamide riboside derivative capable of supplying NR) and a composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory composition comprising the same.
- nicotinamide riboside that is a precursor of nicotinamide adenine dinucleotide (NAD) through increased stability and bioabsorption and hydrolysis in the body
- NAD nicotinamide adenine dinucleotide
- Nicotinamide adenine dinucleotide is a key molecule that regulates the activity between the nucleus and mitochondria, and is a chemical substance that allows signals to be transmitted.
- NAD may exist in the form of NADH and NAD + depending on the reaction in the body, where NADH is the reduced form of NAD and NAD + is the oxidized form of NAD.
- NAD is an essential compound for cellular respiration, a key molecule that generates energy, and activates the SIRT1 protein, which is known to promote healthy metabolism throughout the body.
- Korean Patent Application Laid-Open No. 10-2016-0047914 discloses a cosmetic composition for anti-aging containing a precursor of NAD
- Korean Patent Publication No. 10-2016-0067195 discloses topical administration of NR or a salt thereof.
- NR NAD
- precursors of NAD such as NR have very poor stability.
- NRs contain labile glycosidic bonds, yielding nicotinamide and ribose degradation products spontaneously in aqueous solution. This decomposition reaction takes place over hours or days, depending on the ambient conditions. Accordingly, it is difficult to apply NR to products while ensuring stability. Therefore, there is an urgent need for development of NR derivatives with increased stability.
- the NAD precursor in order to apply the NAD precursor as a functional material such as wrinkle improvement, it is necessary to improve the bioabsorption rate.
- Another object of the present invention is to provide a composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory composition comprising the fatty amine-conjugated nicotinamide riboside derivative.
- the present invention relates to a nicotinamide riboside derivative represented by the following formula (1).
- R is a C 8 -C 34 saturated or unsaturated aliphatic hydrocarbon group
- R 1 , R 2 and R 3 are each independently a hydrogen atom or an acyl group
- X is a sulfonate group or a halogen atom.
- the C 8 -C 34 saturated or unsaturated aliphatic hydrocarbon group refers to a linear or branched saturated or unsaturated hydrocarbon group composed of 8 to 34 carbon atoms, for example, a C 8 -C 34 alkyl group, C 8 -C It may be a 34 alkenyl group or a C 8 -C 34 alkynyl group.
- the C 8 -C 34 saturated or unsaturated aliphatic hydrocarbon group includes, but is not limited to, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, cetyl, stearyl, octenyl, nonenyl, and the like.
- acyl group as used herein represents a group of the formula -COR a (where R a is hydrogen, a C 1 -C 5 alkyl group, or an aryl group), for example, an acetyl group, a benzoyl group, etc. are included, but are limited thereto it is not
- R may be a C 12 -C 22 saturated aliphatic hydrocarbon group.
- X may be a methylsulfonate group, a trifluoromethylsulfonate group, chloride or bromide.
- the nicotinamide riboside derivative of Formula 1 may be a compound of Formula 1-1 below.
- X is a sulfonate group or a halogen atom
- n is an integer from 6 to 32;
- n may be an integer from 10 to 20.
- the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 according to the present invention may be prepared according to the method shown in Scheme 1 below.
- the method described in the following scheme is merely an example of the method typically used in the present invention, and the order of unit operations, reaction reagents, reaction conditions, and the like may be changed in any case.
- X and n are as defined in Formula 1-1.
- the nicotinamide riboside derivative of Formula 1 is obtained by condensation reaction of nicotinic acid and fatty amine to obtain alkyl nicotinamide, followed by condensation reaction of the alkyl nicotinamide and tetraacetyl furanose, followed by deprotection reaction. can be manufactured.
- the condensation reaction of nicotinic acid and fatty amine is preferably performed in the presence of a condensing agent and an organic amine catalyst in a solvent.
- the condensing agent includes N,N,N',N'-tetramethyl-(benzotriazol-1-yl)-uroniumtetrafluoroborate (TBTU), N-(3-dimethylaminopropyl)-N' -Ethyl-carbodiimide (EDC), N,N'-diisopropylcarbodiimide (DIC), or N,N'-dicyclohexylcarbodiimide (DCC) may be used, but is not limited thereto.
- the condensing agent may be used in an amount of 1.0 to 5.0 equivalents based on nicotinic acid.
- the organic amine catalyst for accelerating the condensation reaction may be triethylamine (TEA), diisopropylethylamine (DIPEA), or 4-dimethylaminopyridine (DMAP), but is not limited thereto.
- the organic amine catalyst may be used in an amount of 1.0 to 5.0 equivalents based on nicotinic acid.
- an anhydrous organic solvent for example, one or more selected from dichloromethane, chloroform, benzene, toluene, tetrahydrofuran and diethyl ether may be used, but is not limited thereto.
- the condensation reaction may be carried out at room temperature or in a heated state.
- a silyl compound such as trimethylsilyltrifluoromethanesulfonate, trimethylsilylmethanesulfonate, trimethylsilyltoluenesulfonate, etc. may be used as a condensation agent, but is not limited thereto.
- the condensing agent may be used in an amount of 1.0 to 5.0 equivalents based on the alkyl nicotinamide.
- At least one selected from dichloromethane, tetrahydrofuran, and acetonitrile may be used, but is not limited thereto.
- the condensation reaction may proceed in a cooled or heated state.
- the deprotection reaction is preferably performed in the presence of a base.
- a base sodium ethoxide (NaOEt), sodium methoxide (NaOMe), ammonia, or the like may be used, but is not limited thereto.
- the base may be used in an amount of 1.0 to 10.0 equivalents.
- At least one selected from ethanol and methanol may be used as a solvent for the deprotection reaction, but is not limited thereto.
- the deprotection vaporization reaction may be carried out in a cooling to room temperature state.
- the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 according to the present invention has significantly improved stability and increased bioabsorption compared to nicotinamide riboside ( FIGS. 1 to 3 ).
- the nicotinamide riboside derivative of Formula 1 according to the present invention is hydrolyzed in the body to supply nicotinamide riboside (NR), a precursor of nicotinamide adenine dinucleotide (NAD), as a source of NAD precursor, and wrinkles It can be effectively used in cosmetic compositions, pharmaceutical compositions and health functional foods for improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory.
- NR nicotinamide riboside
- NAD nicotinamide adenine dinucleotide
- One embodiment of the present invention relates to a cosmetic composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory treatment comprising the nicotinamide riboside derivative of Formula 1 above.
- the cosmetic composition according to the present invention contains the nicotinamide riboside derivative of Formula 1 as an active ingredient in an amount of about 0.001 to 10% by weight, preferably 0.01 to 5% by weight.
- the content of the active ingredient may be appropriately determined according to the purpose of its use.
- the cosmetic composition of the present invention may further include a penetration enhancer in addition to the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 as an active ingredient.
- a penetration enhancer in addition to the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 as an active ingredient.
- permeation enhancer various surfactants known in the art may be used without limitation.
- saturated or unsaturated fatty acids and derivatives thereof, saturated or unsaturated fatty alcohols and derivatives thereof, etc. may be used, for example, fatty acid sorbitan esters, polyoxyethylene alkyl ethers, etc.
- fatty acid sorbitan esters for example, fatty acid sorbitan esters, polyoxyethylene alkyl ethers, etc.
- These commercially available products include Span 60, Span 65, Span 80, Tween 20, Tween 60, Tween 80, Brij 30, Brij 35, Brij 58, Brij 78, Brij 93, Brij 98, Brij 700, Triton X-100, etc. There is this. These can be used individually or in combination of 2 or more types.
- the penetration enhancer may be included in an amount of 0.01 to 20% by weight based on 100% by weight of the total cosmetic composition. When the penetration enhancer is included in the above range, it is advantageous not only for skin penetration but also for stabilization of the formulation.
- the cosmetic composition of the present invention includes components commonly used in cosmetic compositions in addition to the above components, for example, conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments and fragrances, and carriers.
- conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments and fragrances, and carriers.
- the cosmetic composition of the present invention may be prepared in any formulation commonly used in the art, for example, it may be formulated as a solution, suspension, emulsion, paste, gel, cream, powder, spray, and the like.
- the formulation of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide, etc. may be used as a carrier component.
- lactose When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, etc. may be used as a carrier component.
- additional chlorofluorohydrocarbon In particular, in the case of a spray, additional chlorofluorohydrocarbon, It may contain propellants such as propane/butane or dimethyl ether.
- a solvent for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylglycol oil, glycerol fatty acid ester, polyethylene glycol, fatty acid ester of sorbitan, etc.
- solubilizer or emulsifier for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylglycol oil, glycerol fatty acid ester, polyethylene glycol, fatty acid ester of sorbitan, etc.
- the formulation of the present invention is a suspension
- a liquid diluent such as water, ethanol or propylene glycol
- a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester or polyoxyethylene sorbitan ester, microcrystals
- the cosmetic composition of the present invention includes skin, lotion, cream, essence, pack, foundation, color cosmetics, sun cream, two-way cake, face powder, compact, makeup base, skin cover, eye shadow, lipstick, lip gloss, lip fix, eyebrow pencil It can be applied to cosmetics such as
- Another embodiment of the present invention relates to a wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory pharmaceutical composition
- a wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory pharmaceutical composition comprising the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 above.
- the pharmaceutical composition according to the present invention may be administered orally (eg, taking or inhalation) or parenterally (eg, injection, transdermal absorption, rectal administration), and injection is, for example, intravenous injection , subcutaneous injection, intramuscular injection or intraperitoneal injection.
- the pharmaceutical composition according to the present invention may be administered as a tablet, capsule, granule, fine subtilae, powder, sublingual tablet, suppository, ointment, injection, emulsion, suspension, syrup, spray, etc., depending on the route of administration. can be formulated.
- the various types of the pharmaceutical composition according to the present invention can be prepared by known techniques using a pharmaceutically acceptable carrier commonly used for each formulation.
- Examples of pharmaceutically acceptable carriers include excipients, binders, disintegrating agents, lubricants, preservatives, antioxidants, isotonic agents, buffers, coating agents, sweetening agents, solubilizing agents, bases, dispersing agents, wetting agents , suspending agents, stabilizing agents, coloring agents, and the like.
- the pharmaceutical composition according to the present invention varies depending on the form of the drug, but contains about 0.001 to 10% by weight, preferably 0.01 to 2% by weight of the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 above.
- the specific dosage of the pharmaceutical composition of the present invention may vary depending on the type of mammal, including the person to be treated, body weight, sex, degree of disease, judgment of a doctor, and the like.
- 10 to 200 mg of the active ingredient per 1 kg of body weight is administered per day.
- the total daily dose may be administered at one time or divided into several doses depending on the severity of the disease, the judgment of the doctor, and the like.
- the pharmaceutical composition of the present invention may further include a permeation enhancer in addition to the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 as an active ingredient.
- a permeation enhancer in addition to the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 as an active ingredient.
- the type and content of the permeation promoter are the same as those described in the cosmetic composition.
- Another embodiment of the present invention relates to a health functional food for wrinkle improvement, whitening, cell regeneration, hair loss treatment, or anti-inflammatory, comprising the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 above.
- the type of health functional food according to the present invention is not particularly limited, and is in the form of oral preparations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, or candies, confectionery, gum, ice cream, noodles, bread, It can be added to general foods such as beverages.
- the health functional food of the present invention can be prepared by appropriately using a food-logically acceptable carrier such as a filler, an extender, a binder, a wetting agent, a disintegrant, a sweetener, a fragrance, a preservative, a surfactant, a lubricant, and an excipient in a conventional manner depending on the form.
- a food-logically acceptable carrier such as a filler, an extender, a binder, a wetting agent, a disintegrant, a sweetener, a fragrance, a preservative, a surfactant, a lubricant, and an excipient in a conventional manner depending on the form.
- the content of the fatty amine-conjugated nicotinamide riboside derivative of Formula 1 varies depending on the type of health functional food, but is about 0.001 to 10% by weight, preferably 0.1 to 5% by weight. .
- the fatty amine-conjugated nicotinamide riboside derivative according to the present invention has the effects of increasing solubility in organic solvents, improving stability, reducing toxicity and improving bioabsorption.
- the fatty amine-conjugated nicotinamide riboside derivative according to the present invention is hydrolyzed under in vivo pH conditions to gradually release the precursor of nicotinamide adenine dinucleotide (NAD), thereby continuously improving physiological activities such as wrinkle improvement.
- NAD nicotinamide adenine dinucleotide
- the fatty amine-conjugated nicotinamide riboside derivative according to the present invention is an excellent source of NAD precursor, and can be effectively used for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory cosmetic composition, pharmaceutical composition, health functional food, etc. can
- 1 is a graph showing the stability test results of nicotinamide riboside derivatives conjugated with fatty amines according to the present invention.
- FIG. 2 is a graph showing the skin absorption test results of the fatty amine-conjugated nicotinamide riboside derivative according to the present invention.
- FIG. 3 is a graph showing the skin absorption test results when the fatty amine-conjugated nicotinamide riboside derivative according to the present invention is used together with a permeation enhancer.
- the collagen synthesis ability of the fatty amine-conjugated nicotinamide riboside derivative according to the present invention was evaluated.
- Human skin fibroblasts were cultured at a concentration of 1x10 4 /well. Each sample was treated in the cells, and collagen synthesis ability was evaluated by measuring the amount of collagen synthesis. As a positive control, adenosine was treated at a concentration of 50 ppm, and the remaining samples were treated at a concentration of 10 ppm. Collagen quantification was performed using a Type I Procollagen C-Peptide EIA kit (Takara, Japan). A case in which the sample was not treated was used as a control (CON). The results are shown in Table 1 below.
- the fatty amine-conjugated nicotinamide riboside derivative according to the present invention showed an increase in collagen synthesis compared to the control (CON).
- the fatty amine-conjugated nicotinamide riboside derivative according to the present invention exhibited an increase in collagen synthesis at the same level as when adenosine, a positive control, was treated at a concentration of 50 ppm at a concentration of 10 ppm.
- the whitening efficacy of the fatty amine-conjugated nicotinamide riboside derivative according to the present invention was evaluated.
- the compound of Example 3 showed tyrosinase activity inhibitory effects of 21.7% and 41.6% at concentrations of 10 ppm and 100 ppm, respectively, and showed superior whitening effect compared to arbutin.
- the cell regeneration effect of the fatty amine-conjugated nicotinamide riboside derivative according to the present invention was evaluated.
- HDF Human Dermal Fibroblasts
- HDP Human Hair Follicle Dermal Papilla cell
- the compound of Example 3 showed an HDP cell proliferation efficacy of 16.0% compared to the control at a concentration of 1 ppm and 17% at a concentration of 10 ppm, and it was confirmed that it had excellent hair loss efficacy compared to minoxidil.
- HaCaT cells were seeded in a 12-well plate by 1X10 5 cells/well, and after 24 hours, they were replaced with a basal medium and starvated for 6 hours. After that, it was replaced with the basal medium containing the sample and cultured for 24 hours. After the medium was removed, stimulation with UVB was applied, and the basal medium was added and incubated for 24 hours. The medium was completely removed and washed twice with PBS. Cells were disrupted using TRIsure to recover RNA, and then RT-PCR was performed to amplify TNF- ⁇ . Electrophoresis was performed on an agarose gel and the expression rate was measured using the Gel Documentation system. 200 ⁇ M dexamethasone was used as a positive control. The results are shown in Table 5 below.
- Example 3 inhibits the expression of TNF- ⁇ , an inflammatory gene, in HaCaT cells.
- the compound of Example 3 was shown to reduce the expression of TNF- ⁇ by 35% compared to the control at a treatment concentration of 5 ppm.
- Example 3 The compound of Example 3 was dissolved in purified water, sealed and stored at room temperature for 4 weeks, taken at regular intervals and analyzed by HPLC to evaluate stability.
- Skin permeation was evaluated using a Franz diffusion cell.
- the skin used Strat-M® membrane, a synthetic model for in vitro transdermal diffusion evaluation.
- the membrane was clamped between the donor and receptor phases with the smooth side facing up.
- the area of the surface in contact with the receptor phase was 1.093 cm 2 , and purified water was used as the receptor phase.
- the receptor face was stirred at 140 rpm using a magnetic bar.
- Nicotinamide riboside as a compound of Example 3 and a comparative compound was added to the surface of the donor's membrane, and then taken at regular intervals up to 24 hours and analyzed.
- the compound of Example 3 and nicotinamide riboside were each dissolved in the same solvent as the receptor face at a concentration of 10 mg/ml and used. Each time 0.5 mL of the receptor face was taken with a syringe through the sampling port, and HPLC measurement was performed.
- the receptor face was filled with purified water, and a permeation test of nicotinamide riboside and the compound of Example 3 was performed. The results are shown in FIG. 2 .
- each receptor face was filled with purified water prepared at a concentration of 0.5% Brij®98 (permeation enhancer, Aldrich), and a permeation experiment of the comparative compound nicotinamide riboside and the compound of Example 3 was performed. The results are shown in FIG. 3 .
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Abstract
Description
구분division | 타입 1 프로콜라겐 유전자 발현 (% of control)Type 1 procollagen gene expression (% of control) | |
농도(ppm)Concentration (ppm) |
CON |
1010 |
니코틴아미드 리보사이드 |
100100 | 102.4102.4 |
실시예 3의 화합물compound of example 3 | 118.5118.5 | |
Adenosine(50 ppm)Adenosine (50 ppm) | 119.3119.3 |
구분division | 티로시나제 활성 (% of control)Tyrosinase activity (% of control) | ||
농도(ppm)Concentration (ppm) |
CON |
1010 | 100100 |
니코틴아미드 리보사이드 |
100100 | 81.681.6 | 76.376.3 |
실시예 3의 화합물compound of example 3 | 78.378.3 | 58.458.4 | |
알부틴arbutin | 92.692.6 | 76.776.7 |
구분division | 증식(Proliferation) (% of control)Proliferation (% of control) | |
농도(ppm)Concentration (ppm) |
CON |
1010 |
니코틴아미드 리보사이드 |
100100 | 108.3108.3 |
실시예 3의 화합물compound of example 3 | 116.0116.0 | |
EGFEGF | 183.0183.0 |
구분division | 증식(Proliferation) (% of control)Proliferation (% of control) | ||
농도(ppm)Concentration (ppm) | CONCON | 1One | 1010 |
니코틴아미드 리보사이드 |
100100 | 103.2103.2 | 104.9104.9 |
실시예 3의 화합물compound of example 3 | 116.0116.0 | 117.0117.0 | |
미녹시딜 (100 ppm)Minoxidil (100 ppm) | 109.2109.2 |
구분division | TNF-α 유전자 발현 (% of control)TNF-α gene expression (% of control) | ||
농도(ppm)Concentration (ppm) | CONCON | 1One | 55 |
니코틴아미드 리보사이드 |
100100 | 69.169.1 | 66.266.2 |
실시예 3의 화합물compound of example 3 | 64.864.8 | 65.065.0 | |
덱사메타손 (200 μM)Dexamethasone (200 μM) | 69.669.6 |
Claims (9)
- 하기 화학식 1의 니코틴아미드 리보사이드 유도체:Nicotinamide riboside derivatives of the formula (1):[화학식 1] [Formula 1]상기 식에서,In the above formula,R은 C8-C34의 포화 또는 불포화 지방족 탄화수소기이고,R is a C 8 -C 34 saturated or unsaturated aliphatic hydrocarbon group,R1, R2 및 R3는 각각 독립적으로 수소 원자 또는 아실기이고, R 1 , R 2 and R 3 are each independently a hydrogen atom or an acyl group,X는 술포네이트기 또는 할로겐 원자이다.X is a sulfonate group or a halogen atom.
- 제1항에 있어서, R은 C12-C22의 포화 지방족 탄화수소기인 니코틴아미드 리보사이드 유도체.The nicotinamide riboside derivative according to claim 1, wherein R is a C 12 -C 22 saturated aliphatic hydrocarbon group.
- 제1항에 있어서, X는 메틸술포네이트기, 트리플루오로메틸술포네이트기, 클로라이드 또는 브로마이드인 니코틴아미드 리보사이드 유도체.The nicotinamide riboside derivative according to claim 1, wherein X is a methylsulfonate group, a trifluoromethylsulfonate group, chloride or bromide.
- 제1항에 있어서, 하기 화학식 1-1의 화합물인 니코틴아미드 리보사이드 유도체:The nicotinamide riboside derivative according to claim 1, which is a compound of Formula 1-1:[화학식 1-1][Formula 1-1]상기 식에서,In the above formula,X는 술포네이트기 또는 할로겐 원자이고, X is a sulfonate group or a halogen atom,n은 6 내지 32의 정수이다.n is an integer from 6 to 32;
- 제1항 내지 제4항 중 어느 한 항에 따른 니코틴아미드 리보사이드 유도체를 포함하는 주름개선, 미백, 세포재생, 탈모 치료 또는 항염용 화장료 조성물.A cosmetic composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory treatment comprising the nicotinamide riboside derivative according to any one of claims 1 to 4.
- 제5항에 있어서, 투과촉진제를 추가로 포함하는 주름개선, 미백, 세포재생, 탈모 치료 또는 항염용 화장료 조성물.[Claim 6] The cosmetic composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory treatment according to claim 5, further comprising a penetration enhancer.
- 제1항 내지 제4항 중 어느 한 항에 따른 니코틴아미드 리보사이드 유도체를 포함하는 주름개선, 미백, 세포재생, 탈모 치료 또는 항염용 약제학적 조성물.A pharmaceutical composition for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory treatment comprising the nicotinamide riboside derivative according to any one of claims 1 to 4.
- 제7항에 있어서, 투과촉진제를 추가로 포함하는 주름개선, 미백, 세포재생, 탈모 치료 또는 항염용 약제학적 조성물.The pharmaceutical composition according to claim 7, further comprising a permeation promoter for wrinkle improvement, whitening, cell regeneration, hair loss treatment or anti-inflammatory.
- 제1항 내지 제4항 중 어느 한 항에 따른 니코틴아미드 리보사이드 유도체를 포함하는 주름개선, 미백, 세포재생, 탈모 치료 또는 항염용 건강기능식품.A health functional food for wrinkle improvement, whitening, cell regeneration, hair loss treatment, or anti-inflammatory, comprising the nicotinamide riboside derivative according to any one of claims 1 to 4.
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Application Number | Priority Date | Filing Date | Title |
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KR10-2019-0168485 | 2019-12-17 | ||
KR1020190168485A KR102315139B1 (en) | 2019-12-17 | 2019-12-17 | Nicotinamide Riboside Derivatives Conjugated with Fatty Amine |
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WO2023119230A1 (en) | 2021-12-22 | 2023-06-29 | L'oreal | Coagulation pathway and nicotinamide-adenine dinucleotide pathway modulating compositions and methods of their use |
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WO2023119230A1 (en) | 2021-12-22 | 2023-06-29 | L'oreal | Coagulation pathway and nicotinamide-adenine dinucleotide pathway modulating compositions and methods of their use |
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