CA2761335A1

CA2761335A1 - Compounds, compositions and methods for modulating uric acid levels

Compounds, compositions and methods for modulating uric acid levels Download PDF

Info

Publication number: CA2761335A1
Authority: CA; Canada
Prior art keywords: compound; uric acid; methyl; naphthalen; formula
Prior art date: 2009-05-20
Legal status : Abandoned

Application number

CA2761335A

Other languages

English (en)

French (fr)

Inventor

Martha De La Rosa

Jean-Luc Girardet

Current Assignee

Ardea Biociences Inc

Original Assignee

Ardea Biociences Inc

Priority date

2009-05-20

Filing date

2010-05-20

Publication date

2010-11-25

2010-05-20 Application filed by Ardea Biociences Inc filed Critical Ardea Biociences Inc

2010-11-25 Publication of CA2761335A1 publication Critical patent/CA2761335A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 300
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 title claims abstract description 160
229940116269 uric acid Drugs 0.000 title claims abstract description 136
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 title claims abstract description 135
238000000034 method Methods 0.000 title claims abstract description 106
239000000203 mixture Substances 0.000 title abstract description 170
238000011282 treatment Methods 0.000 claims abstract description 35
210000004369 blood Anatomy 0.000 claims abstract description 11
239000008280 blood Substances 0.000 claims abstract description 11
230000009467 reduction Effects 0.000 claims abstract description 8
-1 CF2H Chemical group 0.000 claims description 167
201000005569 Gout Diseases 0.000 claims description 82
125000004432 carbon atom Chemical group C* 0.000 claims description 79
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 67
239000000651 prodrug Chemical group 0.000 claims description 67
229940002612 prodrug Drugs 0.000 claims description 67
150000003839 salts Chemical class 0.000 claims description 58
125000005842 heteroatom Chemical group 0.000 claims description 42
150000002148 esters Chemical class 0.000 claims description 41
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 38
125000003118 aryl group Chemical group 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 34
239000012453 solvate Substances 0.000 claims description 34
239000003795 chemical substances by application Substances 0.000 claims description 33
206010003246 arthritis Diseases 0.000 claims description 31
239000002207 metabolite Substances 0.000 claims description 31
229910052794 bromium Inorganic materials 0.000 claims description 30
239000008194 pharmaceutical composition Substances 0.000 claims description 29
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
210000001519 tissue Anatomy 0.000 claims description 27
201000001431 Hyperuricemia Diseases 0.000 claims description 25
230000003247 decreasing effect Effects 0.000 claims description 25
208000035475 disorder Diseases 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 21
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
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206010020772 Hypertension Diseases 0.000 claims description 17
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
210000000056 organ Anatomy 0.000 claims description 16
206010007027 Calculus urinary Diseases 0.000 claims description 15
206010029148 Nephrolithiasis Diseases 0.000 claims description 15
OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims description 15
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IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 12
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MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 12
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
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208000035317 Total hypoxanthine-guanine phosphoribosyl transferase deficiency Diseases 0.000 claims description 11
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 11
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208000008127 lead poisoning Diseases 0.000 claims description 11
DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 claims description 11
229960003081 probenecid Drugs 0.000 claims description 11
125000000168 pyrrolyl group Chemical group 0.000 claims description 11
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208000035318 Partial hypoxanthine-guanine phosphoribosyl transferase deficiency Diseases 0.000 claims description 10
101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 10
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
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125000002971 oxazolyl group Chemical group 0.000 claims description 9
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239000000275 Adrenocorticotropic Hormone Substances 0.000 claims description 8
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102100039259 Cytochrome c oxidase subunit 8A, mitochondrial Human genes 0.000 claims description 8
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IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 claims description 8
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101100347612 Arabidopsis thaliana VIII-B gene Proteins 0.000 claims description 7
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210000002966 serum Anatomy 0.000 claims description 7
MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 claims description 7
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VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 7
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229960001338 colchicine Drugs 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
150000003536 tetrazoles Chemical class 0.000 claims description 6
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208000014951 hematologic disease Diseases 0.000 claims description 4
208000018706 hematopoietic system disease Diseases 0.000 claims description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
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HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
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