WO2020237117A1 - Composés réagissant avec une espèce réactive pour contrôler des sous-produits - Google Patents

Composés réagissant avec une espèce réactive pour contrôler des sous-produits Download PDF

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Publication number
WO2020237117A1
WO2020237117A1 PCT/US2020/034133 US2020034133W WO2020237117A1 WO 2020237117 A1 WO2020237117 A1 WO 2020237117A1 US 2020034133 W US2020034133 W US 2020034133W WO 2020237117 A1 WO2020237117 A1 WO 2020237117A1
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WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
compound
electron
conjugated
Prior art date
Application number
PCT/US2020/034133
Other languages
English (en)
Inventor
Christopher Duke
Original Assignee
Christopher Duke
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Christopher Duke filed Critical Christopher Duke
Publication of WO2020237117A1 publication Critical patent/WO2020237117A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
    • C07C225/06—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/46—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Definitions

  • Various polymers and terpenoid compounds have also been used to control ozone levels.
  • a rubber olefin polymer containing double bond groups has been used for decomposing ozone generated from an electrophotographic copying machine.
  • Terpenoid compounds capable of decomposing ozone such as linalool, linalool ester, citral and the like, in various solutions and gels have also been used.
  • paints containing a variety of organic materials have been proposed.
  • the decomposition efficiency is not high enough for use in practice.
  • the by-products formed after decomposition of the ozone has not been fully characterized in these cases. Therefore, it is unclear whether exposure to these by-products affect a person’s health, and whether there are any negative environmental impacts.
  • Methods of generating a reactive carbonyl using these compounds is also provided.
  • Methods of using the above compounds to decompose a free radical, a reactive oxygen species (ROS) or another reactive species are also provided.
  • the methods comprise contacting the free radical or the ROS with the above compounds.
  • Ri, R2, R3, and R4 are each independently a lone pair of electrons, hydrogen, a substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted heteroarylalkyl, polymer, nanoparticle, activated carbon, or cellulose, an electron- donating or electron-withdrawing group, conjugated or unconjuted, a carbonyl, or a cationic, anionic, or delocalized lipophilic cation, Any of the electron-withdrawing groups can be directly adjacent to the carbonyl, on the alpha, beta, or further carbons, can be an oxygen, sulfur, amine, or another electronegative c
  • Compound LIV shows a polymer that already has been activated, or already contains reactive carbonyls, that will bind directly to the pathogen upon exposure, but also contains an alkene that is activated upon exposure to ozone. It is a lipophilic polymer so it will form a permanent coating unless removed through a lipophilic solvent.
  • the reactive carbonyl that will come off it will be a lipophilic aldehyde, that can bind to pathogenic proteins and help denature the protein.
  • the pathway on the top shows a lipid peroxyl radical reacting with an enol ether, and upon reaction, followed by attack by water, the newly formed lipid alkoxyl radical will have to compete for the hydrogen atom from the water molecule, with the vinyl ether. If the hydrogen atom goes to the molecule, rather than the lipid, this can cause further lipid peroxidation.
  • the lipid alkoxyl radical will be more reactive than the newly formed conjugated alkoxyl radical, so we can form an alcohol on the lipid, and help prevent further lipid peroxidation.
  • Ri, R 2 , R 3 , R 4 are each independently A 3 -R 5 , a lone pair of electrons, hydrogen, a substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, electron-donating or electron- withdrawing, conjugated or unconjugated, cationic, anionic, substituted or unsubstituted arylalkyl, or substituted or unsubstituted heteroarylalkyl;
  • Compound XXXV and XXXVI will react with peroxyl radicals and lipid peroxyl radicals, remove an oxygen atom from the peroxyl radical, then have a more stable alkoxyl resonating radical compared to the lipid or reactive species alkoxyl radical, so the water molecule that attacks the epoxide will donate the hydrogen atom to the reactive lipid alkoxyl species or reactive alkoxyl species while the above compounds will stabilize the radical.
  • This method allows the formation of functional lipids, such as cardiolipin alcohol, versus traditional antioxidants which would want to donate a hydrogen atom to the peroxyl radical, forming dysfunctional hydrogen peroxide cardiolipin.
  • the compound comprises the structure
  • PCT Patent Publication WO 2016/023015 PCT Patent Publication WO 2017/049305.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés qui génèrent un peroxyde et un tensioactif lorsqu'ils réagissent avec de l'ozone en présence d'eau. L'invention concerne également des procédés d'utilisation des composés susmentionnés pour décomposer un radical libre, une espèce réactive de l'oxygène (ROS) ou une autre espèce réactive. L'invention concerne en outre une peinture, un spray, un matériau solide, un article vêtimentaire, un tissu, un tapis, une peinture, un agent d'étanchéité, un apprêt, un filtre à air, un filtre à eau, un masque facial, un produit cosmétique, une crème, une lotion, une lingette, un tissu, un enduit, un nettoyant, un assainisseur d'air, un nettoie-vitre, un produit pharmaceutique, un aliment, un aliment pour animaux, un sac ou un emballage de produit comprenant les composés susmentionnés. L'invention concerne en outre un composé qui réagit avec des amines, des thiols et des nucléophiles. L'invention concerne également des composés qui se lient à des amines, des thiols, des protéines, des acides aminés et des microbes. L'invention concerne en outre un composé qui stabilise les radicaux libres sur un système conjugué. L'invention concerne en outre la formation d'alpha-hydroxyaldéhydes et d'alpha-hydroxycétones spécifiques et non toxiques lors de réactions avec une espèce réactive. L'invention concerne également la formation de lactaldéhyde lors d'une réaction avec une espèce réactive.
PCT/US2020/034133 2019-05-23 2020-05-22 Composés réagissant avec une espèce réactive pour contrôler des sous-produits WO2020237117A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US201962851813P 2019-05-23 2019-05-23
US62/851,813 2019-05-23
US201962856950P 2019-06-04 2019-06-04
US62/856,950 2019-06-04
US202063011111P 2020-04-16 2020-04-16
US63/011,111 2020-04-16

Publications (1)

Publication Number Publication Date
WO2020237117A1 true WO2020237117A1 (fr) 2020-11-26

Family

ID=73458692

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2020/034133 WO2020237117A1 (fr) 2019-05-23 2020-05-22 Composés réagissant avec une espèce réactive pour contrôler des sous-produits

Country Status (1)

Country Link
WO (1) WO2020237117A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113368282A (zh) * 2021-03-18 2021-09-10 郑州圣华药物食品技术开发有限公司 用氙准分子光源制备臭氧的脉动消毒方法及其装备

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040059107A1 (en) * 2000-11-28 2004-03-25 Bernard Malfroy-Camine Cyclic salen-metal compounds as scavengers for oxygen radicals and useful as antioxidants in the treatment and prevention of diseases
WO2018102463A1 (fr) * 2016-11-30 2018-06-07 Christopher Duke Composés réactifs avec des radicaux libres et des dérivés réactifs de l'oxygène
US20180371376A1 (en) * 2017-06-21 2018-12-27 The Procter & Gamble Company Solvent containing anitmicrobial hard surface cleaning compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040059107A1 (en) * 2000-11-28 2004-03-25 Bernard Malfroy-Camine Cyclic salen-metal compounds as scavengers for oxygen radicals and useful as antioxidants in the treatment and prevention of diseases
WO2018102463A1 (fr) * 2016-11-30 2018-06-07 Christopher Duke Composés réactifs avec des radicaux libres et des dérivés réactifs de l'oxygène
US20180371376A1 (en) * 2017-06-21 2018-12-27 The Procter & Gamble Company Solvent containing anitmicrobial hard surface cleaning compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113368282A (zh) * 2021-03-18 2021-09-10 郑州圣华药物食品技术开发有限公司 用氙准分子光源制备臭氧的脉动消毒方法及其装备
CN113368282B (zh) * 2021-03-18 2023-08-08 郑州圣华药物食品技术开发有限公司 用氙准分子光源制备臭氧的脉动消毒方法及其装备

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