ES2401128T3 - Derivados de xantina como agonistas selectivos de HM74A - Google Patents

Derivados de xantina como agonistas selectivos de HM74A Download PDF

Info

Publication number: ES2401128T3
Authority: ES; Spain
Prior art keywords: chloro; mmol; butyl; dihydro; purine
Prior art date: 2005-08-10
Legal status (The legal status 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 status listed.): Active

Application number

ES10172674T

Other languages

English (en)

Spanish (es)

Inventor

Richard Jonathan Daniel Hatley

Andrew Mcmurtrie Mason

Ivan Leo Pinto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GlaxoSmithKline LLC

Original Assignee

GlaxoSmithKline LLC

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.)

2005-08-10

Filing date

2006-08-08

Publication date

2013-04-17

2005-08-10 Priority claimed from GB0516464A external-priority patent/GB0516464D0/en

2006-04-19 Priority claimed from GB0607736A external-priority patent/GB0607736D0/en

2006-07-21 Priority claimed from GB0614569A external-priority patent/GB0614569D0/en

2006-08-08 Application filed by GlaxoSmithKline LLC filed Critical GlaxoSmithKline LLC

2013-04-17 Application granted granted Critical

2013-04-17 Publication of ES2401128T3 publication Critical patent/ES2401128T3/es

Status Active legal-status Critical Current

2026-08-08 Anticipated expiration legal-status Critical

Links

101000843809 Homo sapiens Hydroxycarboxylic acid receptor 2 Proteins 0.000 title claims description 29
102100030643 Hydroxycarboxylic acid receptor 2 Human genes 0.000 title claims description 28
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title description 27
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 7
239000000556 agonist Substances 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 289
150000003839 salts Chemical class 0.000 claims abstract description 45
125000003118 aryl group Chemical group 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 19
150000002367 halogens Chemical class 0.000 claims abstract description 18
125000002947 alkylene group Chemical group 0.000 claims abstract description 17
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
125000005647 linker group Chemical group 0.000 claims abstract description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 143
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 72
229910052757 nitrogen Inorganic materials 0.000 claims description 70
238000011282 treatment Methods 0.000 claims description 42
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 37
208000017170 Lipid metabolism disease Diseases 0.000 claims description 30
201000010099 disease Diseases 0.000 claims description 26
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
208000032928 Dyslipidaemia Diseases 0.000 claims description 22
208000031226 Hyperlipidaemia Diseases 0.000 claims description 19
229960003512 nicotinic acid Drugs 0.000 claims description 19
235000001968 nicotinic acid Nutrition 0.000 claims description 19
239000011664 nicotinic acid Substances 0.000 claims description 19
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
238000000634 powder X-ray diffraction Methods 0.000 claims description 17
CGNXDNSPHUBQDH-UHFFFAOYSA-N 3-butyl-8-chloro-1-[4-(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)butyl]-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C=2N=C(Cl)NC=2C(=O)N1CCCCC(N=1)=NOC=1C1=CC=CC=N1 CGNXDNSPHUBQDH-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
201000001320 Atherosclerosis Diseases 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
206010003210 Arteriosclerosis Diseases 0.000 claims description 10
208000024172 Cardiovascular disease Diseases 0.000 claims description 10
208000008589 Obesity Diseases 0.000 claims description 10
208000011775 arteriosclerosis disease Diseases 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
208000020346 hyperlipoproteinemia Diseases 0.000 claims description 10
208000006575 hypertriglyceridemia Diseases 0.000 claims description 10
125000002950 monocyclic group Chemical group 0.000 claims description 10
235000020824 obesity Nutrition 0.000 claims description 10
208000000103 Anorexia Nervosa Diseases 0.000 claims description 9
206010070901 Diabetic dyslipidaemia Diseases 0.000 claims description 9
206010019280 Heart failures Diseases 0.000 claims description 9
208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 9
230000004913 activation Effects 0.000 claims description 9
230000009286 beneficial effect Effects 0.000 claims description 9
206010002383 Angina Pectoris Diseases 0.000 claims description 8
206010022489 Insulin Resistance Diseases 0.000 claims description 8
208000006011 Stroke Diseases 0.000 claims description 8
208000007536 Thrombosis Diseases 0.000 claims description 8
208000020832 chronic kidney disease Diseases 0.000 claims description 8
208000022831 chronic renal failure syndrome Diseases 0.000 claims description 8
208000029078 coronary artery disease Diseases 0.000 claims description 8
125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
208000018262 Peripheral vascular disease Diseases 0.000 claims description 7
125000002619 bicyclic group Chemical group 0.000 claims description 7
239000003981 vehicle Substances 0.000 claims description 7
239000013543 active substance Substances 0.000 claims description 6
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229920000080 bile acid sequestrant Polymers 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
229940125753 fibrate Drugs 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
208000027866 inflammatory disease Diseases 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
150000003536 tetrazoles Chemical group 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 2
-1 for example Chemical group 0.000 description 371
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 309
239000000203 mixture Substances 0.000 description 269
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 264
238000001819 mass spectrum Methods 0.000 description 208
239000000243 solution Substances 0.000 description 133
235000019439 ethyl acetate Nutrition 0.000 description 123
239000007787 solid Substances 0.000 description 119
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
238000000034 method Methods 0.000 description 107
239000000047 product Substances 0.000 description 104
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 94
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 87
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 82
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 76
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 75
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 74
UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 68
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
238000002414 normal-phase solid-phase extraction Methods 0.000 description 62
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
238000005160 1H NMR spectroscopy Methods 0.000 description 47
239000012044 organic layer Substances 0.000 description 47
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
239000012267 brine Substances 0.000 description 44
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
229910052943 magnesium sulfate Inorganic materials 0.000 description 41
235000019341 magnesium sulphate Nutrition 0.000 description 41
238000000746 purification Methods 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
238000003756 stirring Methods 0.000 description 37
239000012074 organic phase Substances 0.000 description 36
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 30
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
239000000377 silicon dioxide Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 28
239000012043 crude product Substances 0.000 description 28
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FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 25
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238000009472 formulation Methods 0.000 description 21
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
238000004519 manufacturing process Methods 0.000 description 18
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229910000024 caesium carbonate Inorganic materials 0.000 description 16
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UEHBSOZKEHODBZ-UHFFFAOYSA-N 3-butyl-8-chloro-7-prop-2-enylpurine-2,6-dione Chemical compound O=C1NC(=O)N(CCCC)C2=C1N(CC=C)C(Cl)=N2 UEHBSOZKEHODBZ-UHFFFAOYSA-N 0.000 description 14
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239000012535 impurity Substances 0.000 description 14
239000000463 material Substances 0.000 description 14
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 13
235000011181 potassium carbonates Nutrition 0.000 description 13
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
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239000000284 extract Substances 0.000 description 11
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GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 11
239000000523 sample Substances 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
239000000725 suspension Substances 0.000 description 11
WTUVPERXQXSPFE-UHFFFAOYSA-N 8-chloro-3-pentyl-7-prop-2-enylpurine-2,6-dione Chemical compound O=C1NC(=O)N(CCCCC)C2=C1N(CC=C)C(Cl)=N2 WTUVPERXQXSPFE-UHFFFAOYSA-N 0.000 description 10
ZXSNABHDRKDSMU-UHFFFAOYSA-N ethyl 4-(3-butyl-8-chloro-2,6-dioxo-7h-purin-1-yl)butanoate Chemical compound O=C1N(CCCC(=O)OCC)C(=O)N(CCCC)C2=C1NC(Cl)=N2 ZXSNABHDRKDSMU-UHFFFAOYSA-N 0.000 description 10
229910000029 sodium carbonate Inorganic materials 0.000 description 10
235000017550 sodium carbonate Nutrition 0.000 description 10
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206010061218 Inflammation Diseases 0.000 description 8
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239000007788 liquid Substances 0.000 description 8
239000002243 precursor Substances 0.000 description 8
229940075420 xanthine Drugs 0.000 description 8
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239000002253 acid Substances 0.000 description 7
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239000000706 filtrate Substances 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
235000021588 free fatty acids Nutrition 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
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229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WPTWHVQNBTXLFA-UHFFFAOYSA-N 2-(3-chloropropyl)-5-[(2,4-difluorophenyl)methyl]-1,3,4-oxadiazole Chemical compound FC1=CC(F)=CC=C1CC1=NN=C(CCCCl)O1 WPTWHVQNBTXLFA-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
102100039356 Hydroxycarboxylic acid receptor 3 Human genes 0.000 description 6
239000002168 alkylating agent Substances 0.000 description 6
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230000000052 comparative effect Effects 0.000 description 6
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
239000012453 solvate Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
238000005406 washing Methods 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
KULPEMIOTUCHSD-UHFFFAOYSA-N 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propan-1-ol Chemical compound O1C(CCCO)=NC(CC=2C=CC=CC=2)=N1 KULPEMIOTUCHSD-UHFFFAOYSA-N 0.000 description 5
JYSUEVTYUOMXFW-UHFFFAOYSA-N 3-butyl-8-chloro-1-[3-[3-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]-1,2,4-oxadiazol-5-yl]propyl]-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C=2N=C(Cl)NC=2C(=O)N1CCCC(ON=1)=NC=1CN1C=CC(C(F)(F)F)=N1 JYSUEVTYUOMXFW-UHFFFAOYSA-N 0.000 description 5
BAXZLWYKDFEHAS-UHFFFAOYSA-N 5-(3-butyl-8-chloro-2,6-dioxo-7h-purin-1-yl)-n'-hydroxypentanimidamide Chemical compound O=C1N(CCCCC(=N)NO)C(=O)N(CCCC)C2=C1NC(Cl)=N2 BAXZLWYKDFEHAS-UHFFFAOYSA-N 0.000 description 5
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LGPSLLXIJLFLIW-UHFFFAOYSA-N n'-hydroxy-2-thiophen-3-ylethanimidamide Chemical compound ON=C(N)CC=1C=CSC=1 LGPSLLXIJLFLIW-UHFFFAOYSA-N 0.000 description 1
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COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 description 1
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JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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239000008109 sodium starch glycolate Substances 0.000 description 1
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GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
239000012265 solid product Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
229960002920 sorbitol Drugs 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
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230000008719 thickening Effects 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
230000017423 tissue regeneration Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000003146 transient transfection Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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239000007762 w/o emulsion Substances 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Cardiology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Nutrition Science (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

ES10172674T 2005-08-10 2006-08-08 Derivados de xantina como agonistas selectivos de HM74A Active ES2401128T3 (es)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB0516464		2005-08-10
GB0516464A GB0516464D0 (en)	2005-08-10	2005-08-10	Novel compounds
GB0607736		2006-04-19
GB0607736A GB0607736D0 (en)	2006-04-19	2006-04-19	Novel compounds
GB0614569A GB0614569D0 (en)	2006-07-21	2006-07-21	Novel compounds
GB0614569		2006-07-21

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ES2401128T3 true ES2401128T3 (es)	2013-04-17

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ES10172674T Active ES2401128T3 (es)	2005-08-10	2006-08-08	Derivados de xantina como agonistas selectivos de HM74A

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US (3)	US20100179128A1 (2)
EP (3)	EP1912992A1 (2)
JP (2)	JP2009504592A (2)
KR (2)	KR20080038396A (2)
AR (1)	AR055369A1 (2)
AT (1)	ATE487719T1 (2)
AU (2)	AU2006278215A1 (2)
BR (2)	BRPI0615145A2 (2)
CA (2)	CA2618963A1 (2)
CR (2)	CR9749A (2)
CY (1)	CY1111757T1 (2)
DE (1)	DE602006018151D1 (2)
DK (1)	DK1912991T3 (2)
EA (2)	EA014556B1 (2)
ES (1)	ES2401128T3 (2)
HR (1)	HRP20100725T1 (2)
IL (2)	IL189081A0 (2)
MA (2)	MA29692B1 (2)
MX (2)	MX2008001931A (2)
MY (1)	MY142067A (2)
NO (2)	NO20081211L (2)
NZ (1)	NZ565494A (2)
PE (1)	PE20070405A1 (2)
PL (1)	PL1912991T3 (2)
PT (1)	PT1912991E (2)
SI (1)	SI1912991T1 (2)
TW (1)	TW200800217A (2)
WO (2)	WO2007017262A1 (2)

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2006
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Publication number	Publication date
BRPI0614270A2 (pt)	2011-03-22
EA200800555A1 (ru)	2008-08-29
NO20081212L (no)	2008-05-06
NZ565494A (en)	2011-06-30
HRP20100725T1 (hr)	2011-01-31
WO2007017261A1 (en)	2007-02-15
DE602006018151D1 (de)	2010-12-23
CR9749A (es)	2008-05-22
AR055369A1 (es)	2007-08-22
US20100168122A1 (en)	2010-07-01
ATE487719T1 (de)	2010-11-15
PT1912991E (pt)	2011-01-17
PE20070405A1 (es)	2007-05-06
JP2009504591A (ja)	2009-02-05
MX2008001929A (es)	2008-03-24
EP1912991B1 (en)	2010-11-10
EA200800564A1 (ru)	2008-08-29
HK1116779A1 (en)	2009-01-02
BRPI0615145A2 (pt)	2009-11-03
EA014556B1 (ru)	2010-12-30
IL189083A0 (en)	2008-08-07
CY1111757T1 (el)	2015-10-07
US20110257205A1 (en)	2011-10-20
KR20080038396A (ko)	2008-05-06
PL1912991T3 (pl)	2011-04-29
US20100179128A1 (en)	2010-07-15
US8143264B2 (en)	2012-03-27
EP2272848A1 (en)	2011-01-12
JP5112316B2 (ja)	2013-01-09
MX2008001931A (es)	2008-03-24
JP2009504592A (ja)	2009-02-05
NO20081211L (no)	2008-05-08
WO2007017262A1 (en)	2007-02-15
MA29692B1 (fr)	2008-08-01
AU2006278215A1 (en)	2007-02-15
CA2626723A1 (en)	2007-02-15
TW200800217A (en)	2008-01-01
KR20080034993A (ko)	2008-04-22
DK1912991T3 (da)	2011-02-21
CR9748A (es)	2008-05-05
AU2006278216A1 (en)	2007-02-15
SI1912991T1 (sl)	2011-03-31
IL189081A0 (en)	2008-08-07
EP1912992A1 (en)	2008-04-23
EP2272848B1 (en)	2012-12-26
MA29693B1 (fr)	2008-08-01
CA2618963A1 (en)	2007-02-15
MY142067A (en)	2010-08-30
EP1912991A1 (en)	2008-04-23

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