JP2004175790A - ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT - Google Patents
ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT Download PDFInfo
- Publication number
- JP2004175790A JP2004175790A JP2003374551A JP2003374551A JP2004175790A JP 2004175790 A JP2004175790 A JP 2004175790A JP 2003374551 A JP2003374551 A JP 2003374551A JP 2003374551 A JP2003374551 A JP 2003374551A JP 2004175790 A JP2004175790 A JP 2004175790A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- zinc
- complex
- vitamins
- food
- 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.)
- Pending
Links
Images
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本発明は、生体物質であるアミノ酸類、ビタミン類、ピコリン酸類、カルボン酸類、オリゴペプチド類、食品添加物であるマルトール類、及びそれらの誘導体からなる化合物を配位子として有する亜鉛(II)有機錯体に、生体物質であるアミノ酸類、ビタミン類、カルボン酸類などを含んでなる特定保健用食品、健康(機能)食品、栄養(機能)食品等の食品及び薬剤に関する。 The present invention relates to a zinc (II) organic compound having, as a ligand, a compound consisting of biological substances such as amino acids, vitamins, picolinic acids, carboxylic acids, oligopeptides, maltols as food additives, and derivatives thereof. The present invention relates to foods and drugs such as foods for specified health use, health (functional) foods, nutritional (functional) foods, and the like, which contain amino acids, vitamins, carboxylic acids, and the like as biological substances in the complex.
亜鉛イオンを用いたα−グルコシダーゼ阻害作用に関しては研究報告がなされている(非特許文献1)。しかし、亜鉛(II)イオン(硫酸亜鉛、酢酸亜鉛、塩化亜鉛)は無機塩であるため、生体膜の通過が難しく、生体内へ取り込まれにくい。そのような課題を克服するために、ほど良い安定性をもち、ほど良い脂溶性をもつa−グルコシダーゼ阻害作用を有する亜鉛(II)錯体としては、トラネキサム酸亜鉛化合物のみが知られている(特許文献1)。 Research reports have been made on the α-glucosidase inhibitory action using zinc ions (Non-Patent Document 1). However, since zinc (II) ions (zinc sulfate, zinc acetate, zinc chloride) are inorganic salts, they are difficult to pass through a biological membrane and are hardly taken into a living body. In order to overcome such problems, only zinc tranexamate compounds are known as zinc (II) complexes having moderate stability and moderate lipophilicity and having a-glucosidase inhibitory action (Patent Reference 1).
この発明に関する先行技術文献情報としては次のものがある。
亜鉛(II)イオン(硫酸亜鉛、酢酸亜鉛、塩化亜鉛など)は無機塩であるため、生体膜の通過が難しく、生体内へ取り込まれにくい。その為、α−グルコシダーゼ阻害剤としての生理作用が発現しにくい。 Since zinc (II) ions (zinc sulfate, zinc acetate, zinc chloride, etc.) are inorganic salts, they are difficult to pass through a biological membrane and are hardly taken into a living body. Therefore, a physiological action as an α-glucosidase inhibitor is hardly exhibited.
そのような課題を克服するために、本発明は、亜鉛(II)イオンよりも毒性が低く、ほど良い安定性をもち、ほど良い脂溶性をもち、かつヒトにやさしい亜鉛(II)錯体として、生体物質であるアミノ酸類、ピコリン酸類、ビタミン類、カルボン酸類、オリゴペプチド類、食品添加物であるマルトール類、及びそれらの誘導体である化合物からなる配位子と亜鉛源とを含んでなるα−グルコシダーゼを阻害する亜鉛(II)錯体を用いる。
この発明が解決しようとしている課題は、前記、亜鉛(II)錯体を有効成分として含有する食品及び薬剤であり、α−グルコシダーゼ阻害作用を有する組成物に関する。
本発明の食品及び薬剤は、前記した亜鉛(II)錯体のほかに、さらに食品上及び薬剤上、許容される単体及びそれらの混合物を含有してなる食品及び薬剤が好ましい。
In order to overcome such a problem, the present invention provides a zinc (II) complex that is less toxic than zinc (II) ion, has good stability, has good lipophilicity, and is human-friendly. Α- comprising a ligand consisting of amino acids, picolinic acids, vitamins, carboxylic acids, oligopeptides, maltols as food additives, and derivatives thereof, which are biological substances, and a zinc source. A zinc (II) complex that inhibits glucosidase is used.
The problem to be solved by the present invention is a food and a drug containing the zinc (II) complex as an active ingredient, and relates to a composition having an α-glucosidase inhibitory action.
The food and drug of the present invention are preferably foods and drugs which further contain, in addition to the above-mentioned zinc (II) complex, an acceptable single substance and a mixture thereof on food and medicine.
本発明で用いられる亜鉛源としては、ヒト及び他の動物への投与に好適な亜鉛源であればどのようなものでもよいが、例えば、亜鉛の鉱産塩や亜鉛有機錯体などが好ましいものとして挙げられる。
亜鉛の鉱産塩としては、例えば、酢酸亜鉛、塩化亜鉛、硫酸亜鉛、硝酸亜鉛等が挙げられる。なお、亜鉛源として亜鉛の鉱産塩を使用した場合には、pH調整剤として、例えば、水酸化カリウム、水酸化ナトリウム、水酸化リチウム、水酸化バリウム等の塩基性水溶液や、クエン酸緩衝液、リン酸緩衝液等の緩衝液を併用してもよい。亜鉛(II)有機錯体としては、例えば、アミノ酸類、ピコリン酸類、ビタミン類、マルトール類、カルボン酸類、オリゴペプチド類、及びそれらの誘導体である化合物群より選ばれた配位子を有する亜鉛(II)有機錯体が好ましいものとして挙げられる。
本発明にかかる食品及び薬剤の形状は、粉末状、顆粒状、錠剤型、カプセル、液状、ゲル状、その他いずれのものでもよい。
As the zinc source used in the present invention, any zinc source suitable for administration to humans and other animals may be used.Examples include zinc mineral salts and zinc organic complexes. Can be
Examples of mineral salts of zinc include zinc acetate, zinc chloride, zinc sulfate, zinc nitrate and the like. In addition, when a mineral salt of zinc is used as a zinc source, as a pH adjuster, for example, a basic aqueous solution such as potassium hydroxide, sodium hydroxide, lithium hydroxide, barium hydroxide, a citrate buffer, A buffer such as a phosphate buffer may be used in combination. Examples of the zinc (II) organic complex include zinc (II) having a ligand selected from the group consisting of amino acids, picolinic acids, vitamins, maltols, carboxylic acids, oligopeptides, and compounds thereof. ) Organic complexes are preferred.
The shape of the food and drug according to the present invention may be powder, granule, tablet, capsule, liquid, gel, or any other form.
本発明に係る、亜鉛と錯体を形成し得る有機化合物と亜鉛源とを含んでなる食品及び薬剤は、亜鉛(II)イオンよりも毒性が低く、ほど良い安定性をもち、ほど良い脂溶性をもち、かつα−グルコシダーゼ阻害作用をもつ亜鉛(II)錯体を含んでなる食品及び薬剤として大いに期待されるものである。さらに、生活習慣病やその予備群などの健康状態を改善する食品及び薬剤として大いに期待される。 The food and drug according to the present invention comprising an organic compound capable of forming a complex with zinc and a zinc source are less toxic than zinc (II) ion, have good stability, and have good fat solubility. It is highly expected as a food and drug containing a zinc (II) complex having an α-glucosidase inhibitory action. Furthermore, it is expected as a food and a drug for improving health conditions such as lifestyle-related diseases and their spare groups.
本発明の亜鉛(II)錯体は、ほど良い安定性とほど良い脂溶性をもち、かつα−グルコシダーゼ阻害作用を有する。従って、本発明の亜鉛含有物は、食後に起こる高血糖を改善してインスリン需要を低減させ、糖代謝を改善し、糖尿病状態の改善が期待される。
また、本発明の錯体は、生体物質や食品添加物を配位子として用いており、長期間の摂取においても、実質的な副作用を伴わず安全である。
The zinc (II) complex of the present invention has good stability and good lipophilicity and has an α-glucosidase inhibitory action. Therefore, the zinc-containing substance of the present invention is expected to improve postprandial hyperglycemia, reduce insulin demand, improve glucose metabolism, and improve diabetes.
Further, the complex of the present invention uses a biological substance or a food additive as a ligand, and is safe without substantial side effects even during long-term ingestion.
以下の実施例は、この発明を説明するために示したものであり、本発明はこれらの実施例や試験例に限定されるものではない。 The following examples are provided for illustrating the present invention, and the present invention is not limited to these examples and test examples.
(薬理試験例1)
亜鉛(II)錯体の溶液(マウス体重1kg当たり5mg Znもしくは10mg Znとなるような溶液)、それら亜鉛(II)錯体に対応する配位子の溶液、およびイオン交換水を調整し、実験日前日の深夜から約12〜14時間絶食させた2型糖尿病モデル動物であるKK-Ayマウスに投与した(−60分と定義)。上記、溶液投与60分後に、しょ糖溶液をマウス体重1kg当たり2gとなるように調整し、ゾンデを用いて投与した(0分と定義)。血糖値は、−60分から測定をはじめ、0、15、30、60、90、120分(120分は測定していないものもある)まで測定した。
(Pharmacological test example 1)
A zinc (II) complex solution (solution of 5 mg Zn or 10 mg Zn per kg of mouse body weight), a ligand solution corresponding to the zinc (II) complex, and ion-exchanged water were prepared. Was administered to KK- Ay mice, a type 2 diabetes model animal that was fasted for about 12 to 14 hours from midnight (defined as -60 minutes). 60 minutes after the administration of the solution, the sucrose solution was adjusted to 2 g per 1 kg of mouse body weight, and administered using a sonde (defined as 0 minutes). The blood glucose level was measured from -60 minutes to 0, 15, 30, 60, 90, and 120 minutes (some 120 minutes were not measured).
上記、薬理試験例1に則り、被験物質である亜鉛(II)錯体、比較物質としてマルトール(mal)、グルタミン(Gln)、アルギニン(Arg)、カルニチン(Car)、ビタミンC(Vc)およびイオン交換水(コントロール群)をKK-Ayマウスに投与し、しょ糖負荷試験を行ったところ、コントロール群と比較して亜鉛(II)錯体投与群では血糖値の上昇が抑えられた(図1〜5)。また、マルトール、グルタミン酸、アルギニン、カルニチン、およびビタミンCなどの配位子を投与した群では、コントロール群と比較すると若干の血糖値上昇抑制効果は観測されたが、特記すべきほどの変化は見られなかった。
これらのことから、亜鉛(II)錯体はα−グルコシダーゼ阻害作用を有しており、それらの効果は、配位子のみを投与したときと比較して、高いα−グルコシダーゼ阻害作用を有していることが証明された。
以上の結果から、亜鉛(II)錯体は、亜鉛の補給とα−グルコシダーゼ阻害作用との両方を兼ね備えた化合物であり、糖尿病状態を改善させる効果が期待される。
According to the above pharmacological test example 1, a zinc (II) complex as a test substance, maltol (mal), glutamine (Gln), arginine (Arg), carnitine (Car), vitamin C (Vc), and ion exchange as comparative substances When water (control group) was administered to KK- Ay mice and a sucrose tolerance test was performed, an increase in blood glucose level was suppressed in the zinc (II) complex-administered group as compared to the control group (FIGS. 1 to 5). ). In the group to which ligands such as maltol, glutamic acid, arginine, carnitine, and vitamin C were administered, the effect of suppressing a slight increase in blood glucose level was observed as compared with the control group, but a remarkable change was not observed. I couldn't.
From these facts, the zinc (II) complex has an α-glucosidase inhibitory effect, and the effect of the zinc (II) complex is higher than when only the ligand is administered. Proven to be.
From the above results, the zinc (II) complex is a compound having both zinc supplementation and α-glucosidase inhibitory activity, and is expected to have an effect of improving the diabetic state.
(薬理試験例2)
α―グルコシダーゼ阻害活性の検討は、特開2002-316939に記載の、Dehiqvistの方法を改良して行った。
0.1 M基質(マルトース、スクロースを0.15M HEPES緩衝液pH 6.8に溶解したもの)溶液、または4%デンプン溶液(0.15M HEPES緩衝液pH 6.8に溶解したもの)0.1 mlに、被験物質溶液0.1 ml、および酵素液0.1 mlを加え、37℃ 60分間反応させたあと、煮沸させ、反応を停止した。生じたグルコース量は、グルコースオキシダーゼ法(グルコースCIIテストワコー)により測定した。空試験として、基質溶液の代わりに、0.15 M HEPES緩衝液(pH=6.8)を加えて、同様の試験を行った時の吸光度をブランク値とし、この値を差し引き、試験液Asを求めた。なお、酵素液は市販のα―グルコシダーゼ(和光純薬工業社製)を、0.015 M HEPES緩衝液(pH=6.8)で5 units/mlに調整したものを用いた。また、対照としては、被験物質の代わりに、溶媒を加えた時の吸光度Acを測定し、下式によって、αグルコシダーゼ阻害活性を測定した(図6と7)。
α−グルコシダーゼ阻害活性(%)=[(Ac―As)/Ac]×100
(Pharmacological test example 2)
The α-glucosidase inhibitory activity was examined by improving the Dehiqvist method described in JP-A-2002-316939.
0.1 ml of a 0.1 M substrate (maltose, sucrose dissolved in 0.15 M HEPES buffer pH 6.8) solution or 0.1 ml of 4% starch solution (dissolved in 0.15 M HEPES buffer pH 6.8), 0.1 ml of the test substance solution, After adding 0.1 ml of the enzyme solution and reacting at 37 ° C. for 60 minutes, the mixture was boiled to stop the reaction. The amount of generated glucose was measured by a glucose oxidase method (Glucose CII Test Wako). As a blank test, a 0.15 M HEPES buffer (pH = 6.8) was added instead of the substrate solution, and the absorbance at the time of performing the same test was used as a blank value, and this value was subtracted to obtain a test solution As. As the enzyme solution, a commercially available α-glucosidase (manufactured by Wako Pure Chemical Industries, Ltd.) adjusted to 5 units / ml with 0.015 M HEPES buffer (pH = 6.8) was used. As a control, the absorbance Ac when a solvent was added instead of the test substance was measured, and the α-glucosidase inhibitory activity was measured by the following formula (FIGS. 6 and 7).
α-Glucosidase inhibitory activity (%) = [(Ac-As) / Ac] × 100
上記、薬理試験例2に則り、被験物質である亜鉛(II)錯体のα−グルコシダーゼ阻害活性を測定し、IC50値を求めると、表1および表2に示す濃度が得られた。
図6と7に示すように、ビス(ビタミンC)/亜鉛(II)錯体、Zn(Vc)2、は、濃度依存的にα−グルコシダーゼ阻害活性を有することが明らかになった。
Above, pursuant to Pharmacological Test Example 2, by measuring the α- glucosidase inhibitory activity of zinc (II) complex of the test substance, when determining an IC 50 value, the concentration shown in Table 1 and Table 2 were obtained.
As shown in FIGS. 6 and 7, it was revealed that the bis (vitamin C) / zinc (II) complex, Zn (Vc) 2 , had an α-glucosidase inhibitory activity in a concentration-dependent manner.
Claims (12)
Further, a drug which can be safely treated and prevented as an α-glucosidase inhibitor comprising other foods, food additives, vitamins and minerals.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003374551A JP2004175790A (en) | 2002-11-12 | 2003-11-04 | ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002327684 | 2002-11-12 | ||
JP2003374551A JP2004175790A (en) | 2002-11-12 | 2003-11-04 | ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2004175790A true JP2004175790A (en) | 2004-06-24 |
Family
ID=32716133
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003374551A Pending JP2004175790A (en) | 2002-11-12 | 2003-11-04 | ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2004175790A (en) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007043606A1 (en) * | 2005-10-12 | 2007-04-19 | Genolac Bl Corporation | Antidiabetic agent comprising anionic polyamino acid-metal complex |
WO2009123364A1 (en) * | 2008-04-03 | 2009-10-08 | Fujifilm Corporation | Mineral absorption accelerator and iron deficiency anemia improver or food composition |
CN103156170A (en) * | 2011-12-12 | 2013-06-19 | 朱兵 | Blood sugar-reducing tablet and preparation method thereof |
CN103156171A (en) * | 2011-12-12 | 2013-06-19 | 朱兵 | Slimming tablet and preparation method thereof |
WO2014098822A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Zinc amino acid halide mouthwashes |
WO2014098813A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Zinc amino acid/trimethylglycine halide |
WO2014098824A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral gel comprising zinc - amino acid complex |
WO2014098826A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
WO2014098814A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Composition with zinc amino acid/trimethylglycine halide precursors |
WO2014098828A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor|comprising zinc amino acid halides |
WO2014099226A3 (en) * | 2012-12-19 | 2014-09-25 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
WO2014204439A1 (en) * | 2013-06-18 | 2014-12-24 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
JP2015117212A (en) * | 2013-12-19 | 2015-06-25 | 二村 芳弘 | Uronic acid derivative which shows longevity gene sirt1 activating action adapting health care culture, and production method thereof |
WO2015195491A1 (en) * | 2014-06-18 | 2015-12-23 | Thetis Pharmaceuticals Llc | Mineral amino-acid complexes of active agents |
US9498421B2 (en) | 2012-12-19 | 2016-11-22 | Colgate-Palmolive Company | Two component compositions containing tetrabasic zinc-amino acid halide complexes and cysteine |
US9504858B2 (en) | 2012-12-19 | 2016-11-29 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
US9675823B2 (en) | 2012-12-19 | 2017-06-13 | Colgate-Palmolive Company | Two component compositions containing zinc amino acid halide complexes and cysteine |
US9750670B2 (en) | 2012-12-19 | 2017-09-05 | Colgate-Palmolive Company | Zinc amino acid complex with cysteine |
US9757316B2 (en) | 2012-12-19 | 2017-09-12 | Colgate-Palmolive Company | Zinc-lysine complex |
US9775792B2 (en) | 2012-12-19 | 2017-10-03 | Colgate-Palmolive Company | Oral care products comprising a tetrabasic zinc-amino acid-halide complex |
US9827177B2 (en) | 2012-12-19 | 2017-11-28 | Colgate-Palmolive Company | Antiperspirant products with protein and antiperspirant salts |
US9861563B2 (en) | 2012-12-19 | 2018-01-09 | Colgate-Palmolive Company | Oral care products comprising tetrabasic zinc chloride and trimethylglycine |
US9901523B2 (en) | 2012-12-19 | 2018-02-27 | Colgate-Palmolive Company | Oral care products comprising zinc oxide and trimethylglycine |
US10130719B2 (en) | 2016-06-03 | 2018-11-20 | Thetis Pharmaceuticals Llc | Compositions and methods relating to salts of specialized pro-resolving mediators |
US10188112B2 (en) | 2012-12-19 | 2019-01-29 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
WO2020131665A1 (en) * | 2018-12-21 | 2020-06-25 | Colgate-Palmolive Company | Zinc-arginine-halide complex |
-
2003
- 2003-11-04 JP JP2003374551A patent/JP2004175790A/en active Pending
Cited By (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007043606A1 (en) * | 2005-10-12 | 2007-04-19 | Genolac Bl Corporation | Antidiabetic agent comprising anionic polyamino acid-metal complex |
WO2009123364A1 (en) * | 2008-04-03 | 2009-10-08 | Fujifilm Corporation | Mineral absorption accelerator and iron deficiency anemia improver or food composition |
CN103156170A (en) * | 2011-12-12 | 2013-06-19 | 朱兵 | Blood sugar-reducing tablet and preparation method thereof |
CN103156171A (en) * | 2011-12-12 | 2013-06-19 | 朱兵 | Slimming tablet and preparation method thereof |
US9757316B2 (en) | 2012-12-19 | 2017-09-12 | Colgate-Palmolive Company | Zinc-lysine complex |
WO2014098814A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Composition with zinc amino acid/trimethylglycine halide precursors |
US9763865B2 (en) | 2012-12-19 | 2017-09-19 | Colgate-Palmolive Company | Oral gel comprising zinc-amino acid complex |
WO2014098826A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
RU2636226C2 (en) * | 2012-12-19 | 2017-11-21 | Колгейт-Палмолив Компани | Gel for oral care, containing zinc complex and amino acids |
WO2014098828A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor|comprising zinc amino acid halides |
WO2014099226A3 (en) * | 2012-12-19 | 2014-09-25 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
WO2014099166A3 (en) * | 2012-12-19 | 2014-10-16 | Colgate-Palmolive Company | Two component compositions containing zinc amino acid halide complexes and cysteine |
US11197811B2 (en) | 2012-12-19 | 2021-12-14 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor |
US9775792B2 (en) | 2012-12-19 | 2017-10-03 | Colgate-Palmolive Company | Oral care products comprising a tetrabasic zinc-amino acid-halide complex |
CN104853721A (en) * | 2012-12-19 | 2015-08-19 | 高露洁-棕榄公司 | Zinc amino acid/trimethylglycine halide |
CN104853723A (en) * | 2012-12-19 | 2015-08-19 | 高露洁-棕榄公司 | Oral gel comprising zinc - amino acid complex |
CN104853724A (en) * | 2012-12-19 | 2015-08-19 | 高露洁-棕榄公司 | Zinc amino acid halide mouthwashes |
KR20150097491A (en) * | 2012-12-19 | 2015-08-26 | 콜게이트-파아므올리브캄파니 | Zinc amino acid complex with cysteine |
KR20150097505A (en) * | 2012-12-19 | 2015-08-26 | 콜게이트-파아므올리브캄파니 | Zinc amino acid halide complex with cysteine |
AU2012397254B2 (en) * | 2012-12-19 | 2015-09-17 | Colgate-Palmolive Company | Zinc amino acid/trimethylglycine halide |
AU2012397263B2 (en) * | 2012-12-19 | 2015-09-24 | Colgate-Palmolive Company | Zinc amino acid halide mouthwashes |
AU2012397267B2 (en) * | 2012-12-19 | 2015-10-08 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
AU2012397269B2 (en) * | 2012-12-19 | 2015-10-29 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor|comprising zinc amino acid halides |
KR102161832B1 (en) | 2012-12-19 | 2020-10-06 | 콜게이트-파아므올리브캄파니 | Zinc amino acid complex with cysteine |
JP2016504996A (en) * | 2012-12-19 | 2016-02-18 | コルゲート・パーモリブ・カンパニーColgate−Palmolive Company | Zinc amino acid halide complexes with cysteine |
AU2012397265B2 (en) * | 2012-12-19 | 2016-02-25 | Colgate-Palmolive Company | Oral gel comprising zinc - amino acid complex |
US9498421B2 (en) | 2012-12-19 | 2016-11-22 | Colgate-Palmolive Company | Two component compositions containing tetrabasic zinc-amino acid halide complexes and cysteine |
US9504858B2 (en) | 2012-12-19 | 2016-11-29 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
US9572756B2 (en) | 2012-12-19 | 2017-02-21 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor |
US9675823B2 (en) | 2012-12-19 | 2017-06-13 | Colgate-Palmolive Company | Two component compositions containing zinc amino acid halide complexes and cysteine |
RU2625757C2 (en) * | 2012-12-19 | 2017-07-18 | Колгейт-Палмолив Компани | Cleansing compositions for personal use which consist of amino acid halogenide/trimethylglycine zinc |
US10792236B2 (en) | 2012-12-19 | 2020-10-06 | Colgate-Palmolive Company | Dentifrice comprising zinc-amino acid complex |
US9750670B2 (en) | 2012-12-19 | 2017-09-05 | Colgate-Palmolive Company | Zinc amino acid complex with cysteine |
WO2014098822A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Zinc amino acid halide mouthwashes |
WO2014098824A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral gel comprising zinc - amino acid complex |
US10610470B2 (en) | 2012-12-19 | 2020-04-07 | Colgate-Palmolive Company | Oral care composition zinc-lysine complex |
WO2014098813A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Zinc amino acid/trimethylglycine halide |
US9827177B2 (en) | 2012-12-19 | 2017-11-28 | Colgate-Palmolive Company | Antiperspirant products with protein and antiperspirant salts |
US9861563B2 (en) | 2012-12-19 | 2018-01-09 | Colgate-Palmolive Company | Oral care products comprising tetrabasic zinc chloride and trimethylglycine |
US9901523B2 (en) | 2012-12-19 | 2018-02-27 | Colgate-Palmolive Company | Oral care products comprising zinc oxide and trimethylglycine |
RU2648513C2 (en) * | 2012-12-19 | 2018-03-26 | Колгейт-Палмолив Компани | Zinc amino acid halide mouthwash |
US9925130B2 (en) | 2012-12-19 | 2018-03-27 | Colgate-Palmolive Company | Composition with zinc amino acid/trimethylglycine halide precursors |
US9943473B2 (en) | 2012-12-19 | 2018-04-17 | Colgate-Palmolive Company | Zinc lysine halide complex |
US9980890B2 (en) | 2012-12-19 | 2018-05-29 | Colgate-Palmolive Company | Zinc amino acid halide mouthwashes |
US9993407B2 (en) | 2012-12-19 | 2018-06-12 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor |
US10610475B2 (en) | 2012-12-19 | 2020-04-07 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor |
CN104853724B (en) * | 2012-12-19 | 2018-07-24 | 高露洁-棕榄公司 | Zinc and amino-acids halide collutory |
US10105303B2 (en) | 2012-12-19 | 2018-10-23 | Colgate-Palmolive Company | Oral care composition comprising zinc amino acid halides |
US10588841B2 (en) | 2012-12-19 | 2020-03-17 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
US10188112B2 (en) | 2012-12-19 | 2019-01-29 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
US10195125B2 (en) | 2012-12-19 | 2019-02-05 | Colgate-Palmolive Company | Oral care composition comprising zinc-lysine complex |
US10245222B2 (en) | 2012-12-19 | 2019-04-02 | Colgate-Palmolive Company | Dentifrice comprising zinc-amino acid complex |
KR102030761B1 (en) * | 2012-12-19 | 2019-10-10 | 콜게이트-파아므올리브캄파니 | Zinc amino acid halide complex with cysteine |
US10524995B2 (en) | 2012-12-19 | 2020-01-07 | Colgate-Palmolive Company | Zinc amino acid halide mouthwashes |
WO2014204439A1 (en) * | 2013-06-18 | 2014-12-24 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
JP2015117212A (en) * | 2013-12-19 | 2015-06-25 | 二村 芳弘 | Uronic acid derivative which shows longevity gene sirt1 activating action adapting health care culture, and production method thereof |
US9999626B2 (en) | 2014-06-18 | 2018-06-19 | Thetis Pharmaceuticals Llc | Mineral amino-acid complexes of active agents |
CN107074884A (en) * | 2014-06-18 | 2017-08-18 | 西蒂斯制药有限责任公司 | The mineral amino acid compound of activating agent |
WO2015195491A1 (en) * | 2014-06-18 | 2015-12-23 | Thetis Pharmaceuticals Llc | Mineral amino-acid complexes of active agents |
US10130719B2 (en) | 2016-06-03 | 2018-11-20 | Thetis Pharmaceuticals Llc | Compositions and methods relating to salts of specialized pro-resolving mediators |
US11135298B2 (en) | 2016-06-03 | 2021-10-05 | Thetis Pharmaceuticals Llc | Compositions and methods relating to salts of specialized pro-resolving mediators |
US11191840B2 (en) | 2016-06-03 | 2021-12-07 | Thetis Pharmaceuticals Llc | Compositions and methods relating to salts of specialized pro-resolving mediators |
US11925688B2 (en) | 2016-06-03 | 2024-03-12 | Thetis Pharmaceuticals Llc | Compositions and methods relating to salts of specialized pro-resolving mediators |
WO2020131665A1 (en) * | 2018-12-21 | 2020-06-25 | Colgate-Palmolive Company | Zinc-arginine-halide complex |
US10952943B2 (en) | 2018-12-21 | 2021-03-23 | Colgate-Palmolive Company | Zinc-arginine-chloride complex |
US11826448B2 (en) | 2018-12-21 | 2023-11-28 | Colgate-Palmolive Company | Zinc-arginine-chloride complex |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2004175790A (en) | ZINC-CONTAINING MATERIAL HAVING alpha-GLUCOSIDASE INHIBITORY EFFECT | |
KR100613037B1 (en) | Novel chromium? alpha amino acid complexes | |
RU2007136761A (en) | SALTS, ADDITIVE PRODUCTS AND COMPLEX COMPOUNDS OF GUANIDINE ACID ACID | |
MX2010009075A (en) | Folates, compositions and uses thereof. | |
JP5290975B2 (en) | Calcium L-carnitine fumarate and production method and use thereof | |
Abakumova et al. | Anticancer activity of oxovanadium compounds | |
JPS62270522A (en) | Nutrient enhancer for treating uremia | |
US7354953B2 (en) | Time-release compositions for delivery of [Cr3O(carboxylate)6(H2O)3]+ | |
US5366723A (en) | Method of alleviating toxicity originating from treatment with anticancer platinum compounds | |
JP2003319760A (en) | Zinc-containing substance having anti-obesity function | |
CA2391844A1 (en) | Method and formula for tumor remission and suppression of cancer | |
JP2011529904A (en) | Accelerated therapy | |
US20060153897A1 (en) | Zinc-containing foods | |
US5665385A (en) | Dietary metal supplements | |
JP3824604B2 (en) | Zinc-containing substance having antioxidative action | |
JP3769267B2 (en) | Zinc-enhanced food and method for producing the same | |
JP2004099573A (en) | Zinc-containing material having blood flow promoting action | |
WO2004052123A1 (en) | Zinc-rich foods having effect of preventing diabetes | |
US7572832B2 (en) | Non-hygroscopic L-carnitine salts | |
Eliason et al. | The anti‐tumor arotinoid RO 40‐8757 protects bone marrow from the toxic effects of cyclophosphamide | |
JP2007137857A (en) | Zinc organic complex having adiponectin increase action | |
JP2003335665A (en) | Composition for regulating in vivo vitamin c level | |
RU2262868C2 (en) | Food biologically active additive | |
JP2024500539A (en) | Method of treating pain using vanadium compounds | |
Hayakawa et al. | Effects of pH and ligands on the metals-catalyzed hydrolysis of clioquinol conjugates |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070508 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070709 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20071029 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20080108 |