1. A process for cleaning a gas stream containing carbon dioxide, comprising
a) removing a part of the carbon dioxide contained in the gas stream by bringing the gas stream into contact with a first ammoniated liquid, to form a liquid enriched in carbon dioxide and a gas stream partly depleted in carbon dioxide;
b) removing, at least a part of, the carbon dioxide contained in the gas stream by bringing the gas stream partly depleted in carbon dioxide leaving step a) into contact with at least a second ammoniated liquid, to form a carbon dioxide depleted gas stream enriched in ammonia; and
c) removing, at least a part of, the ammonia of the gas stream by bringing the carbon dioxide depleted gas stream enriched in ammonia leaving step b) into contact with the liquid enriched in carbon dioxide formed in step a), to absorb into the liquid ammonia from the gas stream, such that a carbon dioxide depleted gas stream at least partly depleted in ammonia and a liquid enriched in ammonia are formed, wherein the liquid enriched in ammonia is the first ammoniated liquid used in step a).
2. The process according to claim 1, wherein the gas stream enriched in ammonia formed in step b) is passed directly to step c) without being subjected to intermediate washing.
3. The process according to claim 1, wherein the first ammoniated liquid formed in step c) has a R-value of 2.0 to 3.0.
4. The process according to claim 1, wherein step a) provides a partial removal of carbon dioxide from the gas stream of between 1 and 10%.
5. The process according to claim 4, wherein the liquid enriched in carbon dioxide formed in step a) has a R-value of 1.5 to 1.9.
6. The process according to claim 1, further comprising, prior to step a), adjusting the temperature of the gas stream containing carbon dioxide to a temperature of 0-20\xb0 C.
7. The process according to claim 6, wherein temperature of the gas stream is adjusted to below 5\xb0 C.
8. The process according to claim 1, further comprising
d) removing, at least a part of, the ammonia of the gas stream by bringing the gas stream at least partly depleted in ammonia from step c) into contact with a post-conditioning liquid, to absorb into the liquid ammonia from the gas stream, such that a gas stream depleted in ammonia and a liquid enriched in ammonia are formed.
9. A gas cleaning system for cleaning a gas stream containing carbon dioxide, comprising
a pre-conditioning stage arranged to receive and clean the gas stream;
a carbon dioxide removal stage, located downstream of the pre-conditioning stage with respect to the flow direction of the gas stream, which is arranged to remove carbon dioxide from the gas stream;
a post-conditioning stage, located downstream of the carbon dioxide removal stage with respect to the flow direction of the gas stream, which is arranged to clean the gas stream;
the pre-conditioning stage comprises at least a first gas-liquid contacting device which is arranged upstream of the carbon dioxide removal stage, with respect to the flow direction of the gas stream, wherein the first gas-liquid contacting device is arranged to partly remove carbon dioxide from the gas stream by bringing it into contact with a first ammoniated liquid, such that a liquid enriched in carbon dioxide is formed;
the carbon dioxide removal stage comprises a carbon dioxide absorber vessel arranged to receive the gas stream from the gas-liquid contacting device of the pre-conditioning stage arranged upstream of the carbon dioxide removal stage, and to remove carbon dioxide from the gas stream by bringing the gas stream into contact with at least a second ammoniated liquid, such that a carbon dioxide depleted gas stream enriched in ammonia is formed;
the post-conditioning stage comprises at least a first gas-liquid contacting device which is arranged downstream of the carbon dioxide removal stage, with respect to the flow direction of the gas stream, wherein the first gas-liquid contacting device is arranged to receive the carbon dioxide depleted gas stream enriched in ammonia from the absorber vessel and to partly remove ammonia from the gas stream by bringing the gas stream into contact with the liquid enriched in carbon dioxide, such that the first ammoniated liquid is formed;
wherein the first gas-liquid contacting device of the pre-conditioning stage is arranged in liquid connection with the first gas-liquid contacting device of the post-conditioning stage, such that at least a portion of the liquid used in the first gas-liquid contacting device of the pre-conditioning stage is directed for use in the first gas-liquid contacting device of the post-conditioning stage and at least a portion of the liquid used in the first gas-liquid contacting device of the post-conditioning stage is directed for use in the first gas-liquid contacting device of the pre-conditioning stage.
10. The gas cleaning system according to claim 9, wherein the carbon dioxide absorber vessel is arranged to feed the carbon dioxide depleted gas stream enriched in ammonia directly to the first gas-liquid contacting device of the post-conditioning stage.
11. The gas cleaning system according to claim 9, wherein the first gas-liquid contacting device of the pre-conditioning stage is adapted for handling of solids.
12. The gas cleaning system according to claim 11, wherein the first gas-liquid contacting device consists of an open spray tower or sieve trays.
13. The gas cleaning system according to claim 9, wherein the first gas-liquid contacting device of the post-conditioning stage is adapted for handling of solids.
14. The gas cleaning system according to claim 13, wherein the first gas-liquid contacting device consists of an open spray tower or sieve trays.
15. The gas cleaning system according to claim 9, wherein the pre-conditioning stage comprises a second gas-liquid contacting device which is arranged upstream of the first gas-liquid contacting device of the pre-conditioning stage, wherein the second gas-liquid contacting device is arranged to cool the gas stream by bringing it into contact with a cooling liquid.
16. The gas cleaning system according to claim 9, wherein the post-conditioning stage comprises a second gas-liquid contacting device which is arranged downstream of the first gas-liquid contacting device of the post-conditioning stage, wherein the second gas-liquid contacting device is arranged to receive the gas stream from the first gas-liquid contacting device of the post-conditioning stage and to further remove, at least a part of, the ammonia from the gas stream by bringing it into contact with a post-conditioning liquid.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A compound of formula (III):
wherein:
A is \u2014R1, \u2014OR1, \u2014C(O)N(R1)R2, \u2014P(O)N(R1)R22, \u2014N(R1)C(O)R2, \u2014N(R16)C(O)OR2, \u2014N(R1)R21, \u2014N(R16)C(O)N(R1)R16, \u2014S(O)tR1, \u2014SO2NHC(O)R1, \u2014N(R1)SO2R22, \u2014SO2N(R1)H, \u2014C(O)NHSO2R22, or \u2014CH\u2550NOR1;
X and Y are both N, U is C(R5) and Z is C(R19)
or X and Z are both N, U is C(R5) and Y is C(R19)
or U and X are both N, and Z and Y are both C(R19)
or Y and Z are both N, U is C(R5) and X is C(R19);
V is S, O or C(R4)H;
each W is N or CH;
n is zero or an integer from 1 to 3;
q is zero or one;
r is zero or one;
t is zero, one or two;
is an optionally substituted carbocyclyl or optionally substituted N-heterocyclyl;
each R1 and R2 are independently chosen from the group consisting of hydrogen, optionally substituted C1-C20 alkyl, optionally substituted cycloalkyl, \u2014C0-C8 alkyl\u2014R9, \u2014C2-C8 alkenyl\u2014R9, \u2014C2-C8 alkynyl\u2014R9, \u2014C2-C8 alkyl\u2014R10 (optionally substituted by hydroxy), \u2014C1-C8\u2014R11 (optionally substituted by hydroxy), optionally substituted heterocyclyl;
or R1 and R2 together with the nitrogen atom to which they are attached is an optionally substituted N-heterocyclyl;
R4 is chosen from the group consisting of hydrogen, alkyl, aryl, aralkyl and cycloalkyl; provided that when A is \u2014R1 or \u2014OR1, R4 cannot be hydrogen, and when V is CH, R4 may additionally be hydroxy;
R5 is chosen from the group consisting of hydrogen, halo, alkyl, haloalkyl, optionally substituted aralkyl, optionally substituted aryl, \u2014OR16, \u2014S(O)t\u2014R16, \u2014N(R16)R21, \u2014N(R16)C(O)N(R1)R16, \u2014N(R16)C(O)OR16, \u2014N(R16)C(O)R16, \u2014C0-C8 alkyl\u2014C(O)OR16, \u2014C0-C8 alkyl\u2014C(H)C(O)OR162, and \u2014C0-C8 alkyl\u2014C(O)N(R1)R16;
each R9 is independently chosen from the group consisting of haloalkyl, cycloalkyl (optionally substituted with halo, cyano, alkyl or alkoxy), carbocyclyl (optionally substituted with one or more substituents selected from the group consisting of halo, alkyl and alkoxy), and heterocyclyl (optionally substituted with alkyl, aralkyl or alkoxy);
each R10 is independently chosen from the group consisting of halo, alkoxy, optionally substituted aryloxy, optionally substituted aralkoxy, optionally substituted \u2014S(O)t\u2014R22, acylamino, amino, monoalkylamino, dialkylamino, (triphenylmethyl)amino, hydroxy, mercapto, alkylsulfonamido;
each R11 is independently chosen from the group consisting of cyano, di(alkoxy)alkyl, carboxy, alkoxycarbonyl, aminocarbonyl, monoalkylaminocarbonyl and dialkylaminocarbonyl;
each R12, R13, R14 and R20 is independently hydrogen or alkyl;
each R16 is independently hydrogen, alkyl, optionally substituted aryl, optionally substituted aralkyl or cycloalkyl;
each R19 is independently hydrogen, alkyl (optionally substituted with hydroxy), cyclopropyl, halo or haloalkyl;
each R21 is independently hydrogen, alkyl, cyclopropyl, optionally substituted aryl, optionally substituted aralkyl, \u2014C(O)R22 or \u2014SO2R22;
or R21 taken together with R1 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl;
or R21 taken together with R16 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl; and
each R22 is independently alkyl, cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
as a single stereoisomer or mixture thereof, or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 having the formula (IIIa), formula (IIIb) or formula (IIIc):
3. The compound of claim 2 wherein
is an optionally substituted phenyl or optionally substituted naphthyl.
4. The compound of claim 3 selected from the group consisting of:
4-chloro-2-(1H-imidazol-1-yl)-6-(2-methoxyphenyl)aminopyrimidine; and
N-(1,3-benzodioxol-5-yl)methyl-3-2-(1H-imidazol-1-yl)pyrimidin-4-yloxy-4-methoxybenzamide.
5. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of formula (III):
wherein:
A is \u2014R1, \u2014OR1, \u2014C(O)N(R1)R2, \u2014P(O)N(R1)R22, \u2014N(R1)C(O)R2, \u2014N(R16)C(O)OR2, \u2014N(R1)R21, \u2014N(R16)C(O)N(R1)R16, \u2014S(O)tR1, \u2014SO2NHC(O)R1, \u2014N(R1)SO2R22, \u2014SO2N(R1)H, \u2014C(O)NHSO2R22, or \u2014CH\u2550NOR1;
X and Y are both N, U is C(R5) and Z is C(R19)
or X and Z are both N, U is C(R5) and Y is C(R19)
or U and X are both N, and Z and Y are both C(R19)
or Y and Z are both N, U is C(R5) and X is C(R19);
V is S, O or C(R4)H;
each W is N or CH;
n is zero or an integer from 1 to 3;
q is zero or one;
r is zero or one;
t is zero, one or two;
is an optionally substituted carbocyclyl or optionally substituted N-heterocyclyl;
each R1 and R2 are independently chosen from the group consisting of hydrogen, optionally substituted C1-C20 alkyl, optionally substituted cycloalkyl, \u2014C0-C8 alkyl\u2014R9, \u2014C2-C8 alkenyl\u2014R9, \u2014C2-C8 alkynyl\u2014R9, \u2014C2-C8 alkyl\u2014R10 (optionally substituted by hydroxy), \u2014C1-C8\u2014R11 (optionally substituted by hydroxy), and optionally substituted heterocyclyl;
or R1 and R2 together with the nitrogen atom to which they are attached is an optionally substituted N-heterocyclyl;
R4 is chosen from the group consisting of hydrogen, alkyl, aryl, aralkyl and cycloalkyl; provided that when A is \u2014R1 or \u2014OR1, R4 cannot be hydrogen, and when V is CH, R4 may additionally be hydroxy;
R5 is chosen from the group consisting of hydrogen, halo, alkyl, haloalkyl, optionally substituted aralkyl, optionally substituted aryl, \u2014OR16, \u2014S(O)t\u2014R16, \u2014N(R16)R21, \u2014N(R16)C(O)N(R1)R16, \u2014N(R16)C(O)OR16, \u2014N(R16)C(O)R16, \u2014C0-C8 alkyl\u2014C(O)OR16, \u2014C0-C8 alkyl\u2014C(H)C(O)OR162, and \u2014C0-C8 alkyl\u2014C(O)N(R1)R16;
each R9 is independently chosen from the group consisting of haloalkyl, cycloalkyl (optionally substituted with halo, cyano, alkyl or alkoxy), carbocyclyl (optionally substituted with one or more substituents selected from the group consisting of halo, alkyl and alkoxy), and heterocyclyl (optionally substituted with alkyl, aralkyl or alkoxy);
each R10 is independently chosen from the group consisting of halo, alkoxy, optionally substituted aryloxy, optionally substituted aralkoxy, optionally substituted \u2014S(O)t\u2014R22, acylamino, amino, monoalkylamino, dialkylamino, (triphenylmethyl)amino, hydroxy, mercapto, and alkylsulfonamido;
each R11 is independently chosen from the group consisting of cyano, di(alkoxy)alkyl, carboxy, alkoxycarbonyl, aminocarbonyl, monoalkylaminocarbonyl and dialkylaminocarbonyl;
each R12, R13, R14 and R20 are independently hydrogen or alkyl;
each R16 is independently hydrogen, alkyl, optionally substituted aryl, optionally substituted aralkyl or cycloalkyl;
each R19 is independently hydrogen, alkyl (optionally substituted with hydroxy), cyclopropyl, halo or haloalkyl;
each R21 is independently hydrogen, alkyl, cyclopropyl, optionally substituted aryl, optionally substituted aralkyl, \u2014C(O)R22 or \u2014SO2R22;
or R21 taken together with R1 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl;
or R21 taken together with R16 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl; and
each R22 is independently alkyl, cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
as a single stereoisomer or mixture thereof, or a pharmaceutically acceptable salt thereof.
6. A method of treating a condition resulting from an abnormality in nitric oxide production which comprises administering to a mammal having a condition resulting from an abnormality in nitric oxide production a therapeutically effective amount of a compound of formula (III):
wherein:
A is \u2014R1, \u2014OR1, \u2014C(O)N(R1)R2, \u2014P(O)N(R1)R22, \u2014N(R1)C(O)R2, \u2014N(R10)C(O)OR21, \u2014N(R1)R21, \u2014N(R16)C(O)N(R1)R16, \u2014S(O)tR1, \u2014SO2NHC(O)R1, \u2014N(R1)SO2R22, \u2014SO2N(R1)H, \u2014C(O)NHSO2R22, or \u2014CH\u2550NOR1;
X and Y are both N, U is C(R5) and Z is C(R19)
or X and Z are both N, U is C(R5) and Y is C(R19)
or U and X are both N, and Z and Y are both C(R19)
or Y and Z are both N, U is C(R5) and X is C(R19);
V is S, O or C(R4)H;
each W is N or CH;
n is zero or an integer from 1 to 3;
q is zero or one;
r is zero or one;
t is zero, one or two;
is an optionally substituted carbocyclyl or optionally substituted N-heterocyclyl;
each R1 and R2 are independently chosen from the group consisting of hydrogen, optionally substituted C1-C20 alkyl, optionally substituted cycloalkyl, \u2014C0-C8 alkyl\u2014R9, \u2014C2-C8 alkenyl\u2014R9, \u2014C2-C8 alkynyl\u2014R9, \u2014C2-C8 alkyl\u2014R10 (optionally substituted by hydroxy), \u2014C1-C8\u2014R11 (optionally substituted by hydroxy), and optionally substituted heterocyclyl;
or R1 and R2 together with the nitrogen atom to which they are attached is an optionally substituted N-heterocyclyl;
R4 is chosen from the group consisting of hydrogen, alkyl, aryl, aralkyl and cycloalkyl; provided that when A is \u2014R1 or \u2014OR1, R4 cannot be hydrogen, and when V is CH, R4 may additionally be hydroxy;
R5 is chosen from the group consisting of hydrogen, halo, alkyl, haloalkyl, optionally substituted aralkyl, optionally substituted aryl, \u2014OR16, \u2014S(O)t\u2014R16, \u2014N(R16)R21, \u2014N(R16)C(O)N(R1)R6, \u2014N(R16)C(O)OR16, \u2014N(R16)C(O)R16, \u2014C0-C8 alkyl\u2014C(O)OR16, \u2014C0-C8 alkyl\u2014C(H)C(O)OR162, and \u2014C0-C8 alkyl\u2014C(O)N(R1)R16;
each R9 is independently chosen from the group consisting of haloalkyl, cycloalkyl (optionally substituted with halo, cyano, alkyl or alkoxy), carbocyclyl (optionally substituted with one or more substituents selected from the group consisting of halo, alkyl and alkoxy), and heterocyclyl (optionally substituted with alkyl, aralkyl or alkoxy);
each R10 is independently chosen from the group consisting of halo, alkoxy, optionally substituted aryloxy, optionally substituted aralkoxy, optionally substituted \u2014S(O)t\u2014R22, acylamino, amino, monoalkylamino, dialkylamino, (triphenylmethyl)amino, hydroxy, mercapto, and alkylsulfonamido;
each R11 is independently chosen from the group consisting of cyano, di(alkoxy)alkyl, carboxy, alkoxycarbonyl, aminocarbonyl, monoalkylaminocarbonyl and dialkylaminocarbonyl;
each R12, R13, R14 and R20 are independently hydrogen or alkyl;
each R16 is independently hydrogen, alkyl, optionally substituted aryl, optionally substituted aralkyl or cycloalkyl;
each R19 is independently hydrogen, alkyl (optionally substituted with hydroxy), cyclopropyl, halo or haloalkyl;
each R21 is independently hydrogen, alkyl, cyclopropyl, optionally substituted aryl, optionally substituted aralkyl, \u2014C(O)R22 or \u2014SO2R22;
or R21 taken together with R1 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl;
or R21 taken together with R16 and the nitrogen to which they are attached is an optionally substituted N-heterocyclyl; and
each R22 is independently alkyl, cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
as a single stereoisomer or mixture thereof, or a pharmaceutically acceptable salt thereof.
7. The method according to claim 6 wherein said condition resulting from an abnormality in nitric oxide production is chosen from the group consisting of multiple sclerosis, stroke or cerebral ischemia, Alzheimer’s disease, HIV dementia, Parkinson’s disease, meningitis, dilated cardiomyopathy and congestive heart failure, atherosclerosis, restenosis or graft stenosis, septic shock and hypotension, hemorrhagic shock, asthma, adult respiratory distress syndrome, smoke or particulate-mediated lung injury, pathogen-mediated pneumonias, trauma of various etiologies, rheumatoid arthritis and osteoarthritis, glomerulonephritis, systemic lupus erythematosus, inflammatory bowel diseases such as ulcerative colitis and Crohn’s disease, insulin dependent diabetes mellitus, diabetic neuropathy or nephropathy, acute and chronic organ transplant rejection, transplant vasculopathies, graft-versus-host disease, psoriasis and other inflammatory skin diseases, and cancer.
8. The method of claim 7 wherein the condition is multiple sclerosis.
9. The method of claim 7 wherein the condition is rheumatoid arthritis.
10. The method of claim 7 wherein the condition is dilated cardiomyopathy.
11. The method of claim 7 wherein the condition is congestive heart failure.