NZ738457B2 - Metal ion complexes - Google Patents

Metal ion complexes Download PDF

Info

Publication number
NZ738457B2
NZ738457B2 NZ738457A NZ73845716A NZ738457B2 NZ 738457 B2 NZ738457 B2 NZ 738457B2 NZ 738457 A NZ738457 A NZ 738457A NZ 73845716 A NZ73845716 A NZ 73845716A NZ 738457 B2 NZ738457 B2 NZ 738457B2
Authority
NZ
New Zealand
Prior art keywords
process according
copper
salt
copper ion
tautomer
Prior art date
Application number
NZ738457A
Other versions
NZ738457A (en
Inventor
Llewellyn Stephen Frank Casbolt
William John Simpson
Original Assignee
Rr Medsciences Pty Ltd
Filing date
Publication date
Application filed by Rr Medsciences Pty Ltd filed Critical Rr Medsciences Pty Ltd
Priority claimed from PCT/AU2016/050518 external-priority patent/WO2016201524A1/en
Publication of NZ738457A publication Critical patent/NZ738457A/en
Publication of NZ738457B2 publication Critical patent/NZ738457B2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/34—Copper; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/76—Metal complexes of amino carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Abstract

The present invention provides a process for the preparation of metal ion complexes, the process comprising contacting a metal in the form of particles with a chelating agent in solid form and, while the metal is in contact with the chelating agent, contacting the metal and chelating agent with an oxidising agent. The present invention also provides novel metal ion complexes. The invention further provides uses of the metal ion complexes.

Claims (33)

CLAIMS :
1. A process for the preparation of a copper ion complex, the process comprising: (a) contacting copper in the form of particles having a bulk 5 density of between about 0.2 and about 8.0 g/cm with a chelating agent in solid form; and (b) while the copper is in contact with the chelating agent, contacting the copper and chelating agent with an oxidising agent, to form at least one copper ion complex, 10 wherein the chelating agent is ethylenediaminetetraacetic acid (EDTA) or a salt thereof.
2. The process according to claim 1, comprising the further step of allowing the oxidising agent, copper and chelating agent to react until completion. 15
3. The process according to claim 1 or 2, wherein the bulk density of the copper is between about 0.3 and about 4.0 g/cm .
4. The process according to any one of claims 1 to 3, wherein the bulk density of the copper is between about 0.8 and about 2.5 g/cm .
5. The process according to any one of claims 1 to 4, wherein the 20 copper and chelating agent are above ambient temperature when the copper and chelating agent are contacted with the oxidising agent.
6. The process according to any one of claims 1 to 5, wherein the oxidising agent is above ambient temperature when the copper and chelating agent are contacted with the oxidising agent. 25
7. The process according to any one of claims 1 to 6, wherein the ratio of copper:chelating agent in moles is within the range of about 1:1 to about 50:1.
8. The process according to any one of claims 1 to 7, wherein the ratio of chelating agent:oxidising agent in moles is within the 30 range of about 1:1 to about 1:20.
9. The process according to any one of claims 1 to 8, wherein the chelating agent is ethylenediaminetetraacetic acid (EDTA) disodium salt.
10. The process according to any one of claims 1 to 9, wherein the 5 oxidising agent is selected from the group consisting of peroxides, peracids, ozone and oxidising salts.
11. The process according to any one of claims 1 to 10, wherein the oxidising agent is in solution.
12. The process according to claim 11, wherein the oxidising agent 10 is in aqueous solution.
13. The process according to claim 10, wherein the peroxide is hydrogen peroxide.
14. The process according to claim 13, wherein the hydrogen peroxide is in aqueous solution.
15. 15 15. The process according to claim 14, wherein the aqueous solution of hydrogen peroxide has a concentration in the range of about 5 wt.% to about 60 wt.%.
16. The process according to claim 15, wherein the aqueous solution of hydrogen peroxide has a concentration of about 50 wt.%. 20
17. The process according to any one of claims 1 to 16, wherein the chelating agent is ethylenediaminetetraacetic acid (EDTA) disodium salt and the oxidising agent is hydrogen peroxide.
18. The process according to claim 17, wherein the hydrogen peroxide is in an aqueous solution, and the ratio of 25 Cu:ethylenediaminetetraacetic acid (EDTA) disodium salt in moles is about 1:1 to about 50:1 and the ratio of Cu:hydrogen peroxide in moles is about 1:1 to about 1:20.
19. The process according to claim 17 or 18, wherein the Cu in contact with ethylenediaminetetraacetic acid (EDTA) disodium salt is 30 maintained at above about 75 ?C when the Cu and EDTA are contacted with the hydrogen peroxide, the hydrogen peroxide also being at above about 75 ?C.
20. The process according to any one of claims 1 to 19, further comprising a step of removing unreacted copper and/or unreacted chelating agent and/or unreacted oxidising agent.
21. A copper ion complex obtained by the process according to any 5 one of claims 1 to 20, or a salt thereof, or tautomer thereof.
22. A composition comprising a copper ion complex or a mixture of copper ion complexes obtained by the process according to any one of claims 1 to 20, or a salt thereof, or tautomer thereof.
23. A formulation for topical administration comprising a copper 10 ion complex or a mixture of copper ion complexes obtained by the process according to any one of claims 1 to 20, or a salt thereof, or tautomer thereof.
24. A copper ion complex comprising a ligand of Formula (I) or Formula (II) wherein 1 2 1 2 R is H and R is H or OH, or R and R together with the carbon atom to which they are attached form a carbonyl (C=O); 3 4 3 4 R is H and R is H or OH, or R and R together with the carbon atom to 20 which they are attached form a carbonyl (C=O); 5 7 7 7 6 5 6 R is -CH(OR )CH OR or -CH CO R and R is absent or H, or R is H and R 2 2 2 7 7 7 is -CH(OR )CH OR or -CH CO R ; and 2 2 2 each R is independently absent or H; or a salt thereof, or tautomer thereof.
25. The copper ion complex according to claim 24, wherein the ligand is of Formula (I), or a salt thereof, or tautomer thereof. 5 26. The copper ion complex according to claim 25, wherein 5 7 7 7 6
26. R is -CH(OR )CH OR or -CH CO R and R is absent or H, or a salt 2 2 2 thereof, or tautomer thereof.
27. The copper ion complex according to claim 26, wherein the ligand is of Formula (Ia) wherein 1 2 1 2 R is H and R is OH, or R and R together with the carbon atom to which they are attached form a carbonyl (C=O); 3 4 3 4 R is H and R is OH, or R and R together with the carbon atom to 15 which they are attached form a carbonyl (C=O); R is absent or H; and each R is independently absent or H; or a salt thereof, or tautomer thereof.
28. The copper ion complex according to claim 27, wherein the ligand is of Formula (Ib) 5 wherein R is absent or H; and each R is independently absent or H; or a salt thereof, or tautomer thereof.
29. The copper ion complex according to claim 24, wherein 10 the ligand is of Formula (II), or a salt thereof, or tautomer thereof.
30. The copper ion complex according to claim 29, wherein the ligand is of Formula (IIa) wherein each R is independently absent or H; or a salt thereof, or tautomer thereof. 5
31. The copper ion complex according to any one of claims 24 to 2+ 3+ 2+ 3+ 30, comprising Cu , Cu or a mixture of Cu and Cu .
32. A composition comprising a copper ion complex or a mixture of copper ion complexes according to any one of claims 24 to 31, or a salt thereof, or tautomer thereof. 10
33. A formulation for topical administration comprising a copper ion complex or a mixture of copper ion complexes according to any one of claims 24 to 31, or a salt thereof, or tautomer thereof. -
NZ738457A 2016-06-17 Metal ion complexes NZ738457B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2015902374A AU2015902374A0 (en) 2015-06-19 Process for Preparing Metal Ion Complexes
PCT/AU2016/050518 WO2016201524A1 (en) 2015-06-19 2016-06-17 Metal ion complexes

Publications (2)

Publication Number Publication Date
NZ738457A NZ738457A (en) 2024-10-25
NZ738457B2 true NZ738457B2 (en) 2025-01-28

Family

ID=

Similar Documents

Publication Publication Date Title
Truong et al. Iron ions chelation-based antioxidant potential vs. pro-oxidant risk of ferulic acid: A DFT study in aqueous phase
MY151233A (en) Production of iron orthophosphate
Sanchez-Eguia et al. Side-on cupric–superoxo triplet complexes as competent agents for H-abstraction relevant to the active site of PHM
Weitl et al. Sulfonated catecholamide analogs of enterobactin as iron sequestering agents
EP2572580A4 (en) Disinfectant composition for hard article, and method for disinfection of surface of hard article
JP2012514580A5 (en)
Shainyan et al. Carbenes and nitrenes. An overview
JP2018537854A (en) Copper etching composition and hydrogen peroxide-based metal etching composition
FI3310789T3 (en) Metal ion complexes
Petillon et al. Recent advances in the chemistry of tris (thiolato) bridged cyclopentadienyl dimolybdenum complexes
NZ738457B2 (en) Metal ion complexes
KR20160138477A (en) Enhancement of recombinant protein expression with copper
WO2007099450A3 (en) Process for the preparation of 2-nitro substituted benzoic acids
Einstein et al. Synthesis and structure of some novel transition metal arylazo complexes involving metal-o-carbon bonds
Mukherjee et al. In vitro kinetic based adduct formation mechanism of a cytotoxic Pt (II) complex with sulfur containing bio-relevant molecules and a theoretical approach
Shoukry et al. Coordination properties of N, O-carboxymethyl chitosan (NOCC). Synthesis and equilibrium studies of some metal ion complexes. Ternary complexes involving Cu (II) with (NOCC) and some biorelevant ligand
Chahal et al. Binding enabled catalytic activation of SO 2 by copper koneramine complexes under ambient conditions
WO2007142804A3 (en) Preparation of complexing agents and metal ion complexes in aqueous media
Rzączyńska et al. Thermal and spectroscopic properties of light lanthanides (III) and sodium complexes of 2, 5-pyridinedicarboxylic acid
JPH04193704A (en) Method for stabilizing acidic aqueous hydrogen peroxide solution containing copper
JP2013142082A (en) Metal complex and anion-removing material comprising the same
Suh et al. Catalysis by binuclear zinc ions in ester hydrolysis
Nguyen et al. Solution equilibrium study of divalent metal ions with phenylpropanoid derivatives and acetylcysteine ligands
EP3393246B1 (en) Process for the preparation of a quelating agent
Wu et al. Transition Metal Complexes of N‐(4, 6‐Dimethoxypyrimidin‐2‐Ylcarbamothioyl) Benzamide: Design, Synthesis and Herbicidal Activity