ES2401128T3 - Derivados de xantina como agonistas selectivos de HM74A - Google Patents
Derivados de xantina como agonistas selectivos de HM74A Download PDFInfo
- Publication number
- ES2401128T3 ES2401128T3 ES10172674T ES10172674T ES2401128T3 ES 2401128 T3 ES2401128 T3 ES 2401128T3 ES 10172674 T ES10172674 T ES 10172674T ES 10172674 T ES10172674 T ES 10172674T ES 2401128 T3 ES2401128 T3 ES 2401128T3
- Authority
- ES
- Spain
- Prior art keywords
- chloro
- mmol
- butyl
- dihydro
- purine
- Prior art date
- 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.)
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- 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
- 238000002360 preparation method Methods 0.000 description 28
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 125000003373 pyrazinyl group Chemical group 0.000 description 24
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 24
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
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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
- 125000002496 methyl group Chemical group [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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- 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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- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
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- 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
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- 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
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- 238000012360 testing method Methods 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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- 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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Classifications
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- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
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- 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
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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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 |
| GB0607736A GB0607736D0 (en) | 2006-04-19 | 2006-04-19 | Novel compounds |
| GB0607736 | 2006-04-19 | ||
| GB0614569 | 2006-07-21 | ||
| GB0614569A GB0614569D0 (en) | 2006-07-21 | 2006-07-21 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2401128T3 true ES2401128T3 (es) | 2013-04-17 |
Family
ID=37189397
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10172674T Active ES2401128T3 (es) | 2005-08-10 | 2006-08-08 | Derivados de xantina como agonistas selectivos de HM74A |
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| KR (2) | KR20080038396A (enExample) |
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| AT (1) | ATE487719T1 (enExample) |
| AU (2) | AU2006278215A1 (enExample) |
| BR (2) | BRPI0615145A2 (enExample) |
| CA (2) | CA2618963A1 (enExample) |
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| EA (2) | EA014556B1 (enExample) |
| ES (1) | ES2401128T3 (enExample) |
| HR (1) | HRP20100725T1 (enExample) |
| IL (2) | IL189083A0 (enExample) |
| MA (2) | MA29692B1 (enExample) |
| MX (2) | MX2008001931A (enExample) |
| MY (1) | MY142067A (enExample) |
| NO (2) | NO20081212L (enExample) |
| NZ (1) | NZ565494A (enExample) |
| PE (1) | PE20070405A1 (enExample) |
| PL (1) | PL1912991T3 (enExample) |
| PT (1) | PT1912991E (enExample) |
| SI (1) | SI1912991T1 (enExample) |
| TW (1) | TW200800217A (enExample) |
| WO (2) | WO2007017262A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7495005B2 (en) * | 2002-08-22 | 2009-02-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, their preparation and their use in pharmaceutical compositions |
| SI1781657T1 (sl) * | 2004-02-14 | 2013-07-31 | Glaxosmithkline Intellectual Property Development Limited | Zdravila z aktivnostjo na receptor hm74a |
| DE102004030502A1 (de) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
| EP1912992A1 (en) * | 2005-08-10 | 2008-04-23 | SmithKline Beecham Corporation | Xanthine derivatives as selective hm74a agonists |
| CA2656039A1 (en) | 2006-06-23 | 2007-12-27 | Incyte Corporation | Purinone derivatives as hm74a agonists |
| AR061626A1 (es) | 2006-06-23 | 2008-09-10 | Incyte Corp | Derivados de purinona como agonistas de hm74a |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| PL2370440T3 (pl) | 2008-12-08 | 2015-05-29 | Glaxosmithkline Llc | Bezwodnik 2-amino-2-(hydroksymetylo)-1,3-propanodiolu 8-chloru-3-pentylo-3,7-dihydro-1H-puryno-2,6-dionu do leczenia chorób |
| JP2013503135A (ja) | 2009-08-26 | 2013-01-31 | サノフイ | 新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| KR101799429B1 (ko) | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| PH12013500301A1 (en) * | 2010-08-16 | 2013-03-25 | Boehringer Ingelheim Int | Oxadiazole inhibitors of leukotriene production |
| US8580825B2 (en) * | 2010-09-23 | 2013-11-12 | Boehringer Ingelheim International Gmbh | Oxadiazole inhibitors of leukotriene production |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2855455B1 (en) * | 2012-05-30 | 2017-11-08 | F. Hoffmann-La Roche AG | Triazolo compounds as pde10 inhibitors |
| DK2970303T6 (en) * | 2013-03-15 | 2018-10-08 | Hydra Biosciences Inc | SUBSTITUTED XANTHINES AND PROCEDURES FOR USING IT |
| JP6417403B2 (ja) | 2013-05-10 | 2018-11-07 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| EP2994139B1 (en) | 2013-05-10 | 2019-04-10 | Gilead Apollo, LLC | Acc inhibitors and uses thereof |
| EP2994138A4 (en) * | 2013-05-10 | 2016-12-28 | Nimbus Apollo Inc | ACC-HEMMER AND USES THEREOF |
| BR112015028173A2 (pt) | 2013-05-10 | 2017-07-25 | Nimbus Apollo Inc | inibidores de acc e usos dos mesmos |
| CN105646492B (zh) * | 2014-11-14 | 2019-04-09 | 中国医学科学院药物研究所 | 含五元芳杂环的取代黄嘌呤类化合物及其制备方法和用途 |
| DE102017000359A1 (de) | 2016-08-26 | 2018-03-01 | Bihl+Wiedemann Gmbh | Diagnose-Repeater für AS-Interface Netze |
| CN110461838B (zh) * | 2017-03-07 | 2022-05-06 | 豪夫迈·罗氏有限公司 | 噁二唑瞬时受体电位通道抑制剂 |
| CN112724141A (zh) * | 2021-01-21 | 2021-04-30 | 南京艾美斐生物医药科技有限公司 | 一种gpr109a蛋白受体抑制剂及其制备和应用 |
| TW202342465A (zh) * | 2022-02-03 | 2023-11-01 | 美商Ｄ Ｅ 蕭爾研究有限公司 | 作為trpa1抑制劑之n3經取代脲嘧啶化合物 |
| CN120835783A (zh) * | 2023-01-30 | 2025-10-24 | D·E·萧尔研究有限责任公司 | 作为trpa1抑制剂的双环酰亚胺化合物 |
| AR133217A1 (es) * | 2023-07-10 | 2025-09-10 | De Shaw Res Llc | Inhibidores de trpa1 bicíclicos y monocíclicos |
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| US2797220A (en) * | 1954-12-02 | 1957-06-25 | Univ Michigan | Substituted paraxanthines |
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| WO1993016699A1 (en) | 1992-02-21 | 1993-09-02 | Smithkline Beecham Corporation | Tnf inhibitors |
| ATE230990T1 (de) | 1992-03-04 | 2003-02-15 | Cell Therapeutics Inc | Enantiomere hydroxylierte xanthinverbindungen |
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| US6323201B1 (en) * | 1994-12-29 | 2001-11-27 | The Regents Of The University Of California | Compounds for inhibition of ceramide-mediated signal transduction |
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| HU230384B1 (hu) * | 2001-02-24 | 2016-03-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xantinszármazékok, előállításuk és alkalmazásuk gyógyszerként |
| US20040254224A1 (en) | 2001-04-11 | 2004-12-16 | Foord Steven Michael | Medicaments |
| EP1404675B1 (en) * | 2001-07-03 | 2008-03-12 | Novo Nordisk A/S | Dpp-iv-inhibiting purine derivatives for the treatment of diabetes |
| EP1338595B1 (en) * | 2002-02-25 | 2006-05-03 | Eisai Co., Ltd. | Xanthine derivatives as DPP-IV inhibitors |
| US7482337B2 (en) * | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
| CN1227492C (zh) * | 2003-03-11 | 2005-11-16 | 张跃 | 一种吸收式空调主体 |
| GB0319124D0 (en) * | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| SI1781657T1 (sl) * | 2004-02-14 | 2013-07-31 | Glaxosmithkline Intellectual Property Development Limited | Zdravila z aktivnostjo na receptor hm74a |
| WO2006045564A1 (en) | 2004-10-22 | 2006-05-04 | Smithkline Beecham Corporation | Xanthine derivatives with hm74a receptor activity |
| BRPI0517458A (pt) * | 2004-10-22 | 2008-10-07 | Smithkline Beecham Corp | derivados da xantina com atividade para o receptor hm74a |
| US20090209561A1 (en) * | 2004-10-22 | 2009-08-20 | Richard Jonathan Daniel Hatley | Xanthine Derivatives with HM74A Receptor Activity |
| JP2008530074A (ja) * | 2005-02-14 | 2008-08-07 | スミスクライン・ビーチャム・コーポレイション | Ｈｍ７４ａ受容体アゴニストとしてのアントラニル酸誘導体 |
| GB0516462D0 (en) * | 2005-08-10 | 2005-09-14 | Smithkline Beecham Corp | Novel compounds |
| EP1912992A1 (en) * | 2005-08-10 | 2008-04-23 | SmithKline Beecham Corporation | Xanthine derivatives as selective hm74a agonists |
| DE102008009758A1 (de) * | 2008-02-18 | 2009-08-20 | Beiersdorf Ag | Verwendung von 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-on zur verbesserten Hautkonturierung bzw. gegen Cellulite |
| PL2370440T3 (pl) | 2008-12-08 | 2015-05-29 | Glaxosmithkline Llc | Bezwodnik 2-amino-2-(hydroksymetylo)-1,3-propanodiolu 8-chloru-3-pentylo-3,7-dihydro-1H-puryno-2,6-dionu do leczenia chorób |
-
2006
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- 2006-08-08 CA CA002618963A patent/CA2618963A1/en not_active Abandoned
- 2006-08-08 HR HR20100725T patent/HRP20100725T1/hr unknown
- 2006-08-08 ES ES10172674T patent/ES2401128T3/es active Active
- 2006-08-08 DE DE602006018151T patent/DE602006018151D1/de active Active
- 2006-08-08 EA EA200800555A patent/EA014556B1/ru not_active IP Right Cessation
- 2006-08-08 NZ NZ565494A patent/NZ565494A/en not_active IP Right Cessation
- 2006-08-08 TW TW095128952A patent/TW200800217A/zh unknown
- 2006-08-08 CA CA002626723A patent/CA2626723A1/en not_active Abandoned
- 2006-08-08 EP EP10172674A patent/EP2272848B1/en active Active
- 2006-08-08 MY MYPI20063833A patent/MY142067A/en unknown
- 2006-08-08 WO PCT/EP2006/007869 patent/WO2007017262A1/en not_active Ceased
- 2006-08-08 BR BRPI0615145-0A patent/BRPI0615145A2/pt not_active Application Discontinuation
- 2006-08-08 MX MX2008001931A patent/MX2008001931A/es active IP Right Grant
- 2006-08-08 MX MX2008001929A patent/MX2008001929A/es not_active Application Discontinuation
- 2006-08-08 KR KR1020087005724A patent/KR20080038396A/ko not_active Withdrawn
- 2006-08-08 US US12/063,434 patent/US8143264B2/en not_active Expired - Fee Related
- 2006-08-08 US US12/063,432 patent/US20100179128A1/en not_active Abandoned
- 2006-08-08 SI SI200630916T patent/SI1912991T1/sl unknown
- 2006-08-08 WO PCT/EP2006/007865 patent/WO2007017261A1/en not_active Ceased
- 2006-08-08 AU AU2006278215A patent/AU2006278215A1/en not_active Abandoned
- 2006-08-08 DK DK06763016.0T patent/DK1912991T3/da active
- 2006-08-08 EA EA200800564A patent/EA200800564A1/ru unknown
- 2006-08-08 BR BRPI0614270-2A patent/BRPI0614270A2/pt not_active IP Right Cessation
- 2006-08-08 KR KR1020087005717A patent/KR20080034993A/ko not_active Ceased
- 2006-08-08 JP JP2008525475A patent/JP2009504592A/ja not_active Withdrawn
- 2006-08-08 PT PT06763016T patent/PT1912991E/pt unknown
- 2006-08-08 PL PL06763016T patent/PL1912991T3/pl unknown
- 2006-08-08 AR ARP060103459A patent/AR055369A1/es unknown
- 2006-08-08 AT AT06763016T patent/ATE487719T1/de active
- 2006-08-08 JP JP2008525474A patent/JP5112316B2/ja not_active Expired - Fee Related
- 2006-08-08 AU AU2006278216A patent/AU2006278216A1/en not_active Abandoned
- 2006-08-08 PE PE2006000963A patent/PE20070405A1/es not_active Application Discontinuation
- 2006-08-08 EP EP06763016A patent/EP1912991B1/en active Active
-
2008
- 2008-01-28 IL IL189083A patent/IL189083A0/en unknown
- 2008-01-28 IL IL189081A patent/IL189081A0/en unknown
- 2008-02-08 MA MA30628A patent/MA29692B1/fr unknown
- 2008-02-08 MA MA30629A patent/MA29693B1/fr unknown
- 2008-02-21 CR CR9748A patent/CR9748A/es not_active Application Discontinuation
- 2008-02-21 CR CR9749A patent/CR9749A/es not_active Application Discontinuation
- 2008-03-07 NO NO20081212A patent/NO20081212L/no not_active Application Discontinuation
- 2008-03-07 NO NO20081211A patent/NO20081211L/no not_active Application Discontinuation
-
2011
- 2011-01-12 CY CY20111100033T patent/CY1111757T1/el unknown
- 2011-04-18 US US13/088,962 patent/US20110257205A1/en not_active Abandoned
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