1. A method for treating an aqueous solution containing cadmium, comprising the steps of:
contacting the aqueous solution with a thiourea based resin to form a cadmium-loaded resin and a cadmium-depleted solution;
separating the cadmium-loaded resin from the cadmium-depleted solution;
contacting the cadmium-loaded resin with an acidic chloride solution; and
eluting the cadmium-loaded resin with water to obtain a cadmium eluate solution and a cadmium-depleted resin.
2. The method of claim 1, wherein the aqueous solution is obtained from a pressure oxidative leaching process.
3. The method of claim 1, wherein the aqueous solution is a sulfate solution or a mixed sulfatechloride solution.
4. The method of claim 3, wherein the aqueous solution is a Voisey’s Bay Nickel pressure oxidative leach solution.
5. The method of claim 3, wherein the aqueous solution further comprises at least one metal selected from the group consisting of nickel, cobalt, zinc, manganese, calcium and magnesium.
6. The method of claim 1, wherein the aqueous solution comprises about 0.5-50 mgL of cadmium.
7. The method of claim 1, wherein the thiourea based resin is Lewatit\xae TP 214.
8. The method of claim 3, wherein the sulfate solution or a mixed sulfatechloride solution comprises up to about 25 gL of chlorides.
9. The method of claim 1, wherein the acidic chloride solution is a hydrochloric acid solution or a mixture of hydrochloric or sulfuric acid and chloride salt of an alkali or alkali-earth metal.
10. The method of claim 8, wherein the cadmium-loaded resin is contacted with the hydrochloric acid solution at a concentration of between about 5-50 gL.
11. The method of claim 9, wherein the cadmium-loaded resin is contacted with the hydrochloric acid solution at a concentration of between about 5-50 gL.
12. The method of claim 9, wherein the acidic chloride solution comprises sulfuric acid at a concentration between 0 and 20 gL and chlorides at concentrations between 10 and 100 gL Cl provided from the chloride salt of an alkali or alkali-earth metal.
13. The method of claim 1, wherein the amount of the acidic chloride solution used is up to about 4 times an amount of thiourea based resin used.
14. The method of claim 1, wherein the step of contacting the cadmium-loaded resin with an acidic chloride solution does not elute any significant amount of cadmium from the cadmium-loaded resin.
15. The method of claim 13, wherein an amount of water used is up to about 30 times the amount of thiourea based resin used.
16. The method of claim 1, wherein the contacting of the cadmium-loaded resin with the acidic chloride solution is performed in a stirred reactor.
17. The method of claim 1, further comprising:
separating the cadmium-depleted resin from the cadmium eluate solution; and
recycling the cadmium-depleted for adsorption of cadmium from the aqueous solution.
18. The method of claim 1, further comprising neutralizing the cadmium eluate solution to precipitate cadmium in a suitable form for disposal.
19. The method of claim 1, wherein the contacting of the cadmium-loaded resin and the acidic chloride solution is performed in a column.
20. The method of claim 1, further comprising transferring the cadmium-depleted solution to a nickel or a cobalt electro-winning circuit.
21. The method of claim 20, wherein nickel or cobalt metal obtained from electrowinning of the cadmium-depleted solution comprises less than about 5 ppm of cadmium.
22. A method for eluting a cadmium-loaded resin, comprising the steps of:
contacting the cadmium-loaded resin with an acidic chloride solution; and
eluting the cadmium-loaded resin with water to obtain a cadmium eluate solution and a cadmium depleted resin,
wherein the cadmium-loaded resin is obtained by contacting an aqueous solution containing cadmium with a thiourea based resin.
23. (canceled)
24. (canceled)
25. (canceled)
26. (canceled)
27. (canceled)
28. The method of claim 22, wherein the acidic chloride solution is a hydrochloric acid solution or a mixture of hydrochloric or sulfuric acid and chloride salt of an alkali or alkali-earth metal.
29. (canceled)
30. The method of claim 28, wherein the cadmium-loaded resin is contacted with the hydrochloric acid solution at a concentration of between about 5-50 gL, wherein an amount of hydrochloric acid solution used is about 4 times an amount of thiourea based resin used, wherein an amount of water used is about 30 times the amount of thiourea based resin used.
31. (canceled)
32. (canceled)
33. (canceled)
34. The method of claim 22, further comprising:
separating the cadmium-depleted resin from the cadmium eluate solution; and recycling the cadmium-depleted resin for use in adsorption of cadmium from the aqueous solution.
35. (canceled)
36. (canceled)
37. (canceled)
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
What is claimed is:
1. A compound of the formula
6
and to pharmaceutically acceptable salts thereof, wherein:
R1 is H, C(O)(CR3R4)mR2, C(O)O(CR3R4)mR2, C(O)N(R )(CR3R4)mR2, or (CR3R4)mR2, wherein m is an integer ranging from 0 to 6 and both R3 and R4 may vary for each iteration where m is greater than 1;
each R3 and R4 is independently selected from H, halogen, or C1-C6 alkyl, or R3 and R4 toegether with the carbon to which they are attached form a 3-10 membered cycloalkyl group, wherein 1 to 3 carbons of said alkyl or cycloalkyl are optionally replaced by a heteroatom selected from O, S and N and said cycloalkyl group is optionally substituted by 1 to 3 substituents independently selected from the group consisting of C(O)O(C1-C10)alkyl, O(C1-C10)alkyl, C1-C10 alkanoyl, halo, nitro, cyano, C1C10 alkyl, N(C1-C10)alkyl, S(C1-C10)alkyl, SO(C1-C10)alkyl, SO2(C1-C10)alkyl, SO2N(C1-C10)alkyl, NHC(O)C1-C10alkyl and NHC(O)N(C1-C10)alkyl;
R2 is a C1-C18 alkyl, a 4-10 membered heterocyclic group or C6-C10aryl, wherein 1 to 3 carbons of said alkyl are optionally replaced by a heteroatom selected from O, S and N and said heterocyclic and aryl groups are optionally substituted by 1 to 3 substituents independently selected from the group consisting of C(O)O(C1-C10)alkyl, O(C1-C10)alkyl, C1-C10 alkanoyl, halo, nitro, cyano, C1-C10 alkyl, N(C1-C10)alkyl, S(C1-C10)alkyl, SO(C1-C10)alkyl, SO2(C1-C10)alkyl, SO2N(C1-C10)alkyl, NHC(O)C1-C10alkyl and NHC(O)N(C1-C10)alkyl; and
R5 is H, C(O)O(C1-C18)alkyl, or C1-C18 alkanoyl wherein 1 to 3 carbons of said alkyl are optionally replaced by a heteroatom selected from O, S and N and wherein in the alkyl portion of said alkanoyl one or two carbons optionally may be replaced by a heteroatom selected from O, S and N.
2. The compound of claim 1 wherein R5 is H.
3. The compound of claim 1 wherein R1 is (CH2)mR2, wherein m is as defined in claim 1.
4. The compound of claim 3 wherein R1 is 4-10 membered heterocyclic group or C6-C10 aryl.
5. The compound of claim 4, wherein R2 is quinolin-4-yl, 4-phenyl-imidazol-1-yl, imidazo(4,5-b)pyridin-3-yl, and 4-pyridin-3-yl-imidazol-1-yl.
6. The compound of claim 3 wherein m is 3.
7. The compound of claim 6 wherein R2 is quinolin-4-yl, 4-phenyl-imidazol-1-yl, imidazo(4,5-b)pyridin-3-yl, and 4-pyridin-3-yl-imidazol-1-yl.
8. The compound of claim 1 wherein said compound is selected from the group consisting of:
the compound of formula 1 wherein R5H, R13-quinolin-4-yl-propyl;
the compound of formula 1 wherein R5H, R17-methoxy-quinolin-4-yl-propyl;
the compound of formula 1 wherein R5H, R13-benzoimidazol-1-yl-propyl;
the compound of formula 1 wherein R5H, R13-indol-1-yl-propyl;
the compound of formula 1 wherein R5H, R13-indazol-1-yl-propyl;
the compound of formula 1 wherein R5H, R13-carbazol-1-yl-propyl;
the compound of formula 1 wherein R5H, Rl3-(5-phenyl-1 H-pyrrol-2-yi)-propyl;
the compound of formula 1 wherein R5H, Rl3-(4-phenyi-imidazol-1-yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(4-pyridin-3-yl-imidazol-1-yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(4-pyndin4-yl-imidazol-1 -yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(4-pyridin-2-yl-imidazol-1-yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(imidazo(4,5-b)pyridin-3-yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(3-(4-chlorophenyl)-(1,2,4)oxadizol-5- yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(3-(4-methoxyphenyl)- (1 ,2,4)oxadizol-5-yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-(3-(4-pyridin-4-yl)-(1,2,4)oxadizol-5- yl)-propyl;
the compound of formula 1 wherein R5H, Rl3-benzotrizol-1-yl-propyl;
the compound of formula 1 wherein R5H, Rl3-benzotrizol-2-yl-propyl;
the compound of formula 1 wherein R5H, Rl3-(1 H-indol-3-yl)-propyl;
the compound of formula 1 wherein R5H, R13-pyridin-4-yl-propyl;
the compound of formula 1 wherein R5H, R13-pyridin-3-yl-propyl;
the compound of formula 1 wherein R5H, R13-pyridin-2-yl-propyl;
the compound of formula 1 wherein R5H, R13-phenylpropyl;
the compound of formula 1 wherein R5H, R13-(2-methoxyphenyl)-propyl;
the compound of formula 1 wherein R5H, R13-furan-2-yl-propyl;
the compound of formula 1 wherein R5H, R13-thiophen-2-yl-propyl;
the compound of formula 1 wherein R5H, R13-thiophen-2-yl-propyl;
the compound of formula 1 wherein R5H, R13-pyrrol-1-yl-propyl;
the compound of formula 1 wherein R5H, R1-(3-(2-pyridin-3-yl-thiazol-4-yl)-propyl;
the compound of formula 1 wherein R5H, R13-(2-phenyl-thiazol-5-yl)-propyl;
the compound of formula 1 wherein R5H, R1-(3-(2-phenyl-thiazol-5-yl)-propyl;
the compound of formula 1 wherein R5H, R13-(4-phenyl-1H-imidazol-2-yl)-propyl; and
the pharmaceutically acceptable salts of the foregoing compounds.
9. A pharmaceutical composition for the treatment of a bacterial infection or a protozoa infection in a mammal, fish, or bird which comprises a therapeutically effective amount of a compound of formula 1 and a pharmaceutically acceptable carrier.
10. A method of treating a bacterial infection or a protozoa infection in a mammal, fish, or bird which comprises administering to said mammal, fish or bird a therapeutically effective amount of a compound of formula 1.
11. A method of preparing a compound of the formula
7
and to pharmaceutically acceptable salts thereof, wherein:
R is H, C(O)(CR3R4)mR2, C(O)O(CR3R4)mR2, C(O)N(R3)(CR3R4)mR2 or (CR3R4)mR2, wherein m is an integer ranging from 0 to 6 and both R3 and R4 may vary for each iteration where m is greater than 1;
each R3 and R4 is independently selected from H, halogen, or C1-C6 alkyl, or R3 and R4 toegether with the carbon to which they are attached form a 3-10 membered cycloalkyl group, wherein 1 to 3 carbons of said alkyl or cycloalkyl are optionally replaced by a heteroatom selected from O, S and N and said cycloalkyl group is optionally substituted by 1 to 3 substituents independently selected from the group consisting of C(O)O(C1-C10)alkyl, O(C1-C10)alkyl, C1-C10 alkanoyl, halo, nitro, cyano, C1-C10 alkyl, N(C1-C10)alkyl, S(C1-C10)alkyl, SO(C1-C10)alkyl, SO2(C1-C10)alkyl, SO2N(C1-C10)alkyl, NHC(O)C1-C10alkyl and NHC(O)N(C1-C10)alkyl;
R2 is a C1-C18 alkyl, a 4-10 membered heterocyclic group or C6-C10aryl, wherein 1 to 3 carbons of said alkyl are optionally replaced by a heteroatom selected from O, S and N and said heterocyclic and aryl groups are optionally substituted by 1 to 3 substituents independently selected from the group consisting of C(O)O(C1-C10)alkyl, O(C1-C10)alkyl, C1-C10alkanoyl, halo, nitro, cyano, C1-C10 alkyl, N(C1-C10)alkyl, S(C1-C10)alkyl, SO(C1-C10)alkyl, SO2(C1-C10)alkyl, SO2N(C1-C10)alkyl, NHC(O)C1-C10alkyl and NHC(O)N(C1-C10)alkyl; and
R5 is H, C(O)O(C1-C18)alkyl, or C1-C18 alkanoyl wherein 1 to 3 carbons of said alkyl are optionally replaced by a heteroatom selected from O, S and N and wherein in the alkyl portion of said alkanoyl one or two carbons optionally may be replaced by a heteroatom selected from O, S and N, which comprises treating a compound of the formula
8
wherein R1 and R5 are as defined for said compound of formula 1, with a compound of the formula R6SO2Cl wherein Re is methyl, ethyl, propyl, phenyl or para-methylphenyl, in the presence of a base to form the compound of formula 1.
12. The method of claim 11 wherein the base is selected from the group consisting of pyridine, sodium bicarbonate, triethylamine, 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) and diisopropylethylamine.
13. The method of claim 11 wherein Re is methyl and the compound of the formula R6SO2Cl is methanesulfonyl chloride.
14. The method of claim 11 wherein R is para-tolyl and the compound of the formula R6SO2Cl is para-toluenesulfonyl chloride.