CA2989115C - Nicotinamide riboside and pterostilbene compositions and methods for treatment of skin disorders - Google Patents
Nicotinamide riboside and pterostilbene compositions and methods for treatment of skin disorders Download PDFInfo
- Publication number
- CA2989115C CA2989115C CA2989115A CA2989115A CA2989115C CA 2989115 C CA2989115 C CA 2989115C CA 2989115 A CA2989115 A CA 2989115A CA 2989115 A CA2989115 A CA 2989115A CA 2989115 C CA2989115 C CA 2989115C
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- CA
- Canada
- Prior art keywords
- substituted
- therapeutically effective
- effective amount
- pterostilbene
- nicotinamide riboside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- JLEBZPBDRKPWTD-TURQNECASA-O N-ribosylnicotinamide Chemical compound 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 59
- 235000020956 nicotinamide riboside Nutrition 0.000 title claims abstract description 54
- 239000011618 nicotinamide riboside Substances 0.000 title claims abstract description 54
- 208000017520 skin disease Diseases 0.000 title claims abstract description 54
- VLEUZFDZJKSGMX-ONEGZZNKSA-N pterostilbene Chemical compound COC1=CC(OC)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 VLEUZFDZJKSGMX-ONEGZZNKSA-N 0.000 title claims abstract description 50
- VLEUZFDZJKSGMX-UHFFFAOYSA-N pterostilbene Natural products COC1=CC(OC)=CC(C=CC=2C=CC(O)=CC=2)=C1 VLEUZFDZJKSGMX-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000011282 treatment Methods 0.000 title claims description 31
- 238000000034 method Methods 0.000 title abstract description 40
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
- 208000000453 Skin Neoplasms Diseases 0.000 claims abstract description 3
- 201000000849 skin cancer Diseases 0.000 claims abstract description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 12
- 235000011187 glycerol Nutrition 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 201000004700 rosacea Diseases 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 6
- 235000019359 magnesium stearate Nutrition 0.000 claims description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 6
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- 235000013311 vegetables Nutrition 0.000 claims description 6
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- 229960003943 hypromellose Drugs 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
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- 235000013871 bee wax Nutrition 0.000 claims description 4
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- 235000012745 brilliant blue FCF Nutrition 0.000 claims description 4
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 claims description 4
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- 206010061218 Inflammation Diseases 0.000 claims description 3
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- 230000004054 inflammatory process Effects 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 206010068388 Actinic elastosis Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 206010012455 Dermatitis exfoliative Diseases 0.000 claims description 2
- 208000019872 Drug Eruptions Diseases 0.000 claims description 2
- 208000010975 Dystrophic epidermolysis bullosa Diseases 0.000 claims description 2
- 206010014190 Eczema asteatotic Diseases 0.000 claims description 2
- 206010014954 Eosinophilic fasciitis Diseases 0.000 claims description 2
- 206010014970 Ephelides Diseases 0.000 claims description 2
- 206010015218 Erythema multiforme Diseases 0.000 claims description 2
- 206010020649 Hyperkeratosis Diseases 0.000 claims description 2
- 208000001126 Keratosis Diseases 0.000 claims description 2
- 206010066945 Lichen striatus Diseases 0.000 claims description 2
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- 201000009053 Neurodermatitis Diseases 0.000 claims description 2
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- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 2
- 208000000766 Pityriasis Lichenoides Diseases 0.000 claims description 2
- 206010036087 Polymorphic light eruption Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 2
- 206010040954 Skin wrinkling Diseases 0.000 claims description 2
- 206010042496 Sunburn Diseases 0.000 claims description 2
- 206010044223 Toxic epidermal necrolysis Diseases 0.000 claims description 2
- 231100000087 Toxic epidermal necrolysis Toxicity 0.000 claims description 2
- 206010047115 Vasculitis Diseases 0.000 claims description 2
- 206010047642 Vitiligo Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 208000009621 actinic keratosis Diseases 0.000 claims description 2
- 208000004631 alopecia areata Diseases 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 208000000594 bullous pemphigoid Diseases 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 201000001981 dermatomyositis Diseases 0.000 claims description 2
- 208000004298 epidermolysis bullosa dystrophica Diseases 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 206010024217 lentigo Diseases 0.000 claims description 2
- 206010024428 lichen nitidus Diseases 0.000 claims description 2
- 201000011486 lichen planus Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 201000005962 mycosis fungoides Diseases 0.000 claims description 2
- 206010033898 parapsoriasis Diseases 0.000 claims description 2
- 201000001976 pemphigus vulgaris Diseases 0.000 claims description 2
- 230000036211 photosensitivity Effects 0.000 claims description 2
- 208000009954 pyoderma gangrenosum Diseases 0.000 claims description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 2
- 201000003385 seborrheic keratosis Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 230000037303 wrinkles Effects 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 231100000168 Stevens-Johnson syndrome Toxicity 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 22
- 230000036561 sun exposure Effects 0.000 abstract description 5
- 230000002757 inflammatory effect Effects 0.000 abstract description 3
- -1 nicotinoyl ribosides Chemical class 0.000 description 44
- 125000003118 aryl group Chemical group 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 25
- 125000001072 heteroaryl group Chemical group 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- FQWLMRXWKZGLFI-YVYUXZJTSA-N (-)-trans-epsilon-viniferin Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC2=C1[C@@H](C=1C=C(O)C=C(O)C=1)[C@H](C=1C=CC(O)=CC=1)O2 FQWLMRXWKZGLFI-YVYUXZJTSA-N 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000003368 amide group Chemical group 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
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- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 235000001968 nicotinic acid Nutrition 0.000 description 9
- 229960003512 nicotinic acid Drugs 0.000 description 9
- 239000011664 nicotinic acid Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- DAYLJWODMCOQEW-TURQNECASA-N NMN zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)([O-])=O)O2)O)=C1 DAYLJWODMCOQEW-TURQNECASA-N 0.000 description 8
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- 239000013543 active substance Substances 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- FQWLMRXWKZGLFI-UHFFFAOYSA-N cis epsilon-viniferine Natural products C1=CC(O)=CC=C1C=CC1=CC(O)=CC2=C1C(C=1C=C(O)C=C(O)C=1)C(C=1C=CC(O)=CC=1)O2 FQWLMRXWKZGLFI-UHFFFAOYSA-N 0.000 description 8
- SXRAUGAFMDOHKN-UHFFFAOYSA-N epsilon-viniferin Natural products CC1(Oc2cc(O)cc(C=Cc3ccc(O)cc3)c2C1(C)c4cc(O)cc(O)c4)c5ccc(O)cc5 SXRAUGAFMDOHKN-UHFFFAOYSA-N 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000013265 extended release Methods 0.000 description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 7
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
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- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
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| US201562173733P | 2015-06-10 | 2015-06-10 | |
| US62/173,733 | 2015-06-10 | ||
| PCT/US2016/019653 WO2016200447A1 (en) | 2015-06-10 | 2016-02-25 | Nicotinamide riboside and pterostilbene compositions and methods for treatment of skin disorders |
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| CA2989115A1 CA2989115A1 (en) | 2016-12-15 |
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| CA2989115A Active CA2989115C (en) | 2015-06-10 | 2016-02-25 | Nicotinamide riboside and pterostilbene compositions and methods for treatment of skin disorders |
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| US20180325931A1 (en) | 2017-01-21 | 2018-11-15 | Ningbo Zhiming Biotechnology Co., Ltd. | Use of paeoniflorin-6'-o-benzenesulfonate in treatment of sjögren's syndrome |
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| JP2020517736A (ja) * | 2017-04-24 | 2020-06-18 | エリシウム ヘルス，インコーポレーテッド | 腎臓損傷の治療及び予防 |
| JP7143402B2 (ja) * | 2017-05-17 | 2022-09-28 | ウニベルシタ デ バレンシア－エストゥディ ヘネラル | ニコチンアミドリボシドを使用する運動ニューロン疾患の治療及び予防 |
| WO2018213715A1 (en) * | 2017-05-18 | 2018-11-22 | Elysium Health, Inc. | Methods and compositions for improving sleep |
| CN111542312A (zh) * | 2017-07-28 | 2020-08-14 | 老龄化控制中心股份公司 | 预防和逆转衰老方面的组合物和方法 |
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| US20210186996A1 (en) * | 2017-12-01 | 2021-06-24 | Elysium Health, Inc. | Methods and compositions for treating multiple sclerosis |
| WO2019108875A1 (en) * | 2017-12-01 | 2019-06-06 | Elysium Health, Inc. | Methods and compositions for treating glaucoma |
| GB201811312D0 (en) * | 2018-07-10 | 2018-08-29 | Nuchido Ltd | Compositions |
| SG11202102204PA (en) | 2018-09-25 | 2021-04-29 | Ponce De Leon Health Designated Activity Company | Process of making calcium alpha-ketoglutarate |
| CN111569084B (zh) * | 2019-02-19 | 2021-07-13 | 中国科学院上海药物研究所 | 基于柳胺酚和紫檀芪的成环偶联分子dcz0801类化合物、其制备方法及用途 |
| WO2020176445A1 (en) * | 2019-02-26 | 2020-09-03 | Universitat De Valencia-Estudi General | Methods and compositions for treating motor neuron diseases |
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| CN113768946A (zh) * | 2020-05-25 | 2021-12-10 | 南京帝昌医药科技有限公司 | 一种治疗糖尿病皮肤并发症的软膏及其制备方法 |
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| EP2322159A1 (en) | 2009-10-30 | 2011-05-18 | Green Molecular, S.L. | Use of pterostilbene (pter) as medicament for prevention and/or treatment of skin diseases, damages or injures or as cosmetic |
| CN103547256A (zh) | 2011-03-23 | 2014-01-29 | 加利福尼亚大学校务委员会 | 炎性和传染性皮肤病的治疗 |
| US8841350B2 (en) | 2011-05-11 | 2014-09-23 | ChromaDex Inc. | Method for inducing UDP-glucuronosyltransferase activity using pterostilbene |
| US20130296440A1 (en) | 2012-05-01 | 2013-11-07 | ChromaDex Inc. | Pterostilbene and curcumin combination for treatment of oxidative stress and inflammation |
| CA2928656C (en) * | 2013-10-30 | 2020-07-28 | ChromaDex Inc. | Nicotinamide riboside compositions for topical use in treating skin conditions |
| CN106715455A (zh) * | 2014-06-06 | 2017-05-24 | 葛兰素史密斯克莱知识产权（第2 号）有限公司 | 烟酰胺核苷类似物及其药物组合物和用途 |
| EP3271370B1 (en) | 2015-03-16 | 2023-06-21 | Chromadex Inc. | Nicotinic acid riboside or nicotinamide riboside compositions, reduced derivatives thereof, and the use thereof |
| US20180071273A1 (en) * | 2015-03-17 | 2018-03-15 | Speccialty Nutrition Group, Inc. | Nutritional compositions to enhance mitochondrial energy production |
| AU2016274126A1 (en) | 2015-06-10 | 2018-01-18 | Elysium Health, Inc. | Nicotinamide riboside and pterostilbene compositions and methods for treatment of skin disorders |
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| US11426398B2 (en) | 2022-08-30 |
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| TWI725033B (zh) | 2021-04-21 |
| US20220362233A1 (en) | 2022-11-17 |
| ZA201800056B (en) | 2023-10-25 |
| AU2020286208B2 (en) | 2022-11-10 |
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