CA2568304A1 - Composes de furanopyrimidine efficaces comme inhibiteurs des canaux potassiques - Google Patents
Composes de furanopyrimidine efficaces comme inhibiteurs des canaux potassiques Download PDFInfo
- Publication number
- CA2568304A1 CA2568304A1 CA002568304A CA2568304A CA2568304A1 CA 2568304 A1 CA2568304 A1 CA 2568304A1 CA 002568304 A CA002568304 A CA 002568304A CA 2568304 A CA2568304 A CA 2568304A CA 2568304 A1 CA2568304 A1 CA 2568304A1
- Authority
- CA
- Canada
- Prior art keywords
- furo
- compound
- phenyl
- alkyl
- ylmethyl
- 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.)
- Abandoned
Links
- 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 23
- 108020001213 potassium channel Proteins 0.000 title claims abstract description 23
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- JUQAECQBUNODQP-UHFFFAOYSA-N furo[3,2-d]pyrimidine Chemical class C1=NC=C2OC=CC2=N1 JUQAECQBUNODQP-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
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- JPIPZNJBXFDXHH-UHFFFAOYSA-N furo[2,3-d]pyrimidin-4-amine Chemical compound NC1=NC=NC2=C1C=CO2 JPIPZNJBXFDXHH-UHFFFAOYSA-N 0.000 claims description 13
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000012038 nucleophile Substances 0.000 claims description 5
- OVSXQHNSAWRCHB-UHFFFAOYSA-N 2-(2-methoxyethoxy)-5-phenyl-n-(pyridin-2-ylmethyl)furo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=COC2=NC(OCCOC)=NC=1NCC1=CC=CC=N1 OVSXQHNSAWRCHB-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- LAIWYHUYKKVRBT-UHFFFAOYSA-N 2-n,2-n-dimethyl-4-n-[(6-methylpyridin-2-yl)methyl]-5-phenylfuro[2,3-d]pyrimidine-2,4-diamine Chemical compound C=12C(C=3C=CC=CC=3)=COC2=NC(N(C)C)=NC=1NCC1=CC=CC(C)=N1 LAIWYHUYKKVRBT-UHFFFAOYSA-N 0.000 claims description 2
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- TVLQJKBIMWJDQJ-UHFFFAOYSA-N 2-[[5-phenyl-4-(pyridin-2-ylmethylamino)furo[2,3-d]pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C=12C(C=3C=CC=CC=3)=COC2=NC(NC(CO)CO)=NC=1NCC1=CC=CC=N1 TVLQJKBIMWJDQJ-UHFFFAOYSA-N 0.000 claims 1
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- WMLVBIYXJAFIFR-UHFFFAOYSA-N ethyl 3-cyano-4-(3,4-dimethoxyphenyl)furan-2-carboximidate Chemical compound N#CC1=C(C(=N)OCC)OC=C1C1=CC=C(OC)C(OC)=C1 WMLVBIYXJAFIFR-UHFFFAOYSA-N 0.000 description 1
- DDLDCOWLZFFCON-UHFFFAOYSA-N ethyl 4-(1,3-benzodioxol-5-yl)-3-cyanofuran-2-carboximidate Chemical compound N#CC1=C(C(=N)OCC)OC=C1C1=CC=C(OCO2)C2=C1 DDLDCOWLZFFCON-UHFFFAOYSA-N 0.000 description 1
- GBBODERVKZXOAS-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-3-cyanofuran-2-carboximidate Chemical compound N#CC1=C(C(=N)OCC)OC=C1C1=CC=C(Cl)C=C1 GBBODERVKZXOAS-UHFFFAOYSA-N 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
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- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- KQGXYVJZOMKLSA-UHFFFAOYSA-N furo[2,3-d]pyrimidine Chemical class N1=CN=C2OC=CC2=C1 KQGXYVJZOMKLSA-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 102000046526 human KCNA5 Human genes 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 229960004053 ibutilide Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 208000004731 long QT syndrome Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- JDNIKJPVCBJUHY-UHFFFAOYSA-N n-(furan-2-ylmethyl)-2-methylsulfonyl-5-phenylfuro[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C=3C=CC=CC=3)=COC2=NC(S(=O)(=O)C)=NC=1NCC1=CC=CO1 JDNIKJPVCBJUHY-UHFFFAOYSA-N 0.000 description 1
- HYLVIWZFJNNKJH-UHFFFAOYSA-N n-[(6-methylpyridin-2-yl)methyl]-2-methylsulfonyl-5-phenylfuro[2,3-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(CNC=2C=3C(C=4C=CC=CC=4)=COC=3N=C(N=2)S(C)(=O)=O)=N1 HYLVIWZFJNNKJH-UHFFFAOYSA-N 0.000 description 1
- ZBMZVLHSJCTVON-GFCCVEGCSA-N n-[4-[(1s)-1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide Chemical compound CC(C)NC[C@@H](O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-GFCCVEGCSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229940046166 oligodeoxynucleotide Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 239000004224 potassium gluconate Substances 0.000 description 1
- 235000013926 potassium gluconate Nutrition 0.000 description 1
- 229960003189 potassium gluconate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical group CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57835004P | 2004-06-10 | 2004-06-10 | |
| US60/578,350 | 2004-06-10 | ||
| GBGB0412986.2A GB0412986D0 (en) | 2004-06-10 | 2004-06-10 | Compounds |
| GB0412986.2 | 2004-06-10 | ||
| PCT/GB2005/002318 WO2005121149A1 (fr) | 2004-06-10 | 2005-06-10 | Composes de furanopyrimidine efficaces comme inhibiteurs des canaux potassiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2568304A1 true CA2568304A1 (fr) | 2005-12-22 |
Family
ID=35094157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002568304A Abandoned CA2568304A1 (fr) | 2004-06-10 | 2005-06-10 | Composes de furanopyrimidine efficaces comme inhibiteurs des canaux potassiques |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1758909A1 (fr) |
| JP (1) | JP4955557B2 (fr) |
| KR (1) | KR20070055486A (fr) |
| AU (1) | AU2005252440A1 (fr) |
| BR (1) | BRPI0511917A (fr) |
| CA (1) | CA2568304A1 (fr) |
| MX (1) | MXPA06014256A (fr) |
| WO (1) | WO2005121149A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005061170A1 (de) * | 2005-12-21 | 2007-07-05 | Bayer Healthcare Ag | Neue, acyclisch substituierte Furopyrimidin-Derivate und ihre Verwendung |
| DE102005061171A1 (de) | 2005-12-21 | 2007-07-05 | Bayer Healthcare Ag | Neue, cyclisch substituierte Furopyrimidin-Derivate und ihre Verwendung |
| DE102007019690A1 (de) * | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von cyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007019691A1 (de) * | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von acyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007027799A1 (de) | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte Furopyrimidine und ihre Verwendung |
| DE102007027800A1 (de) * | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte bicyclische Heteroaryl-Verbindungen und ihre Verwendung |
| DE102007054786A1 (de) | 2007-11-16 | 2009-05-20 | Bayer Healthcare Ag | Trisubstituierte Furopyrimidine und ihre Verwendung |
| EP3124475B1 (fr) | 2009-09-03 | 2019-08-07 | Bristol-Myers Squibb Company | Quinazolines en tant qu'inhibiteurs du canal ionique du potassium |
| NO3175985T3 (fr) | 2011-07-01 | 2018-04-28 | ||
| AR090037A1 (es) | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
| NZ627942A (en) | 2012-01-27 | 2016-03-31 | Gilead Sciences Inc | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| WO2014134419A1 (fr) | 2013-03-01 | 2014-09-04 | Gilead Sciences, Inc. | Utilisation de bloqueurs ikach pour le traitement de maladies cardiaques |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199584A (en) * | 1977-05-27 | 1980-04-22 | Imperial Chemical Industries Limited | Pesticidal active furo[2,3-d] pyrimidine derivatives, compositions containing the same and use thereof |
| US5137879A (en) * | 1990-03-30 | 1992-08-11 | Dowelanco | Furopyrimidin-4-imine derivatives |
| CA2341678C (fr) * | 1998-09-01 | 2009-10-13 | Bristol-Myers Squibb Company | Inhibiteurs de canaux potassium et leur methode d'utilisation |
| JP2003518101A (ja) * | 1999-12-21 | 2003-06-03 | アイカゲン インコーポレイテッド | カリウムチャネル阻害剤 |
| DE10141212A1 (de) * | 2001-08-22 | 2003-03-06 | Bayer Ag | Neue 4-Aminofuropyrimidine und ihre Verwendung |
-
2005
- 2005-06-10 EP EP05751879A patent/EP1758909A1/fr not_active Withdrawn
- 2005-06-10 AU AU2005252440A patent/AU2005252440A1/en not_active Abandoned
- 2005-06-10 CA CA002568304A patent/CA2568304A1/fr not_active Abandoned
- 2005-06-10 MX MXPA06014256A patent/MXPA06014256A/es not_active Application Discontinuation
- 2005-06-10 JP JP2007526555A patent/JP4955557B2/ja not_active Expired - Fee Related
- 2005-06-10 KR KR1020077000590A patent/KR20070055486A/ko not_active Application Discontinuation
- 2005-06-10 BR BRPI0511917-0A patent/BRPI0511917A/pt not_active IP Right Cessation
- 2005-06-10 WO PCT/GB2005/002318 patent/WO2005121149A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008501773A (ja) | 2008-01-24 |
| BRPI0511917A (pt) | 2008-01-15 |
| MXPA06014256A (es) | 2007-03-12 |
| WO2005121149A1 (fr) | 2005-12-22 |
| EP1758909A1 (fr) | 2007-03-07 |
| AU2005252440A1 (en) | 2005-12-22 |
| JP4955557B2 (ja) | 2012-06-20 |
| KR20070055486A (ko) | 2007-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |