NO325873B1 - 2-aminopyridinforbindelser, deres anvendelse samt farmasoytisk preparat - Google Patents
2-aminopyridinforbindelser, deres anvendelse samt farmasoytisk preparat Download PDFInfo
- Publication number
- NO325873B1 NO325873B1 NO20030637A NO20030637A NO325873B1 NO 325873 B1 NO325873 B1 NO 325873B1 NO 20030637 A NO20030637 A NO 20030637A NO 20030637 A NO20030637 A NO 20030637A NO 325873 B1 NO325873 B1 NO 325873B1
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- Prior art keywords
- group
- amino
- furyl
- agent
- oxo
- Prior art date
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- 150000003930 2-aminopyridines Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 2-aminopyridine compound Chemical class 0.000 claims abstract description 104
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 21
- 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 155
- 239000003795 chemical substances by application Substances 0.000 claims description 59
- 206010010774 Constipation Diseases 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 229940124597 therapeutic agent Drugs 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 208000008384 ileus Diseases 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 102000000506 Adenosine A2 Receptors Human genes 0.000 claims description 9
- 108010041368 Adenosine A2 Receptors Proteins 0.000 claims description 9
- 208000002249 Diabetes Complications Diseases 0.000 claims description 7
- 206010012655 Diabetic complications Diseases 0.000 claims description 7
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
- 206010022489 Insulin Resistance Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 208000001132 Osteoporosis Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 239000002220 antihypertensive agent Substances 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 210000002249 digestive system Anatomy 0.000 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- 230000001882 diuretic effect Effects 0.000 claims description 7
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 206010010356 Congenital anomaly Diseases 0.000 claims description 6
- 239000003472 antidiabetic agent Substances 0.000 claims description 6
- 230000004064 dysfunction Effects 0.000 claims description 6
- BNAIEOPFNARKGS-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)NC=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CC(F)=C1 BNAIEOPFNARKGS-UHFFFAOYSA-N 0.000 claims description 5
- 102000007470 Adenosine A2B Receptor Human genes 0.000 claims description 5
- 108010085273 Adenosine A2B receptor Proteins 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000003389 potentiating effect Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- HXVMSFNFURRFAM-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)NC=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 HXVMSFNFURRFAM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- DRVWWLAUEASFQH-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 DRVWWLAUEASFQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
- 230000013872 defecation Effects 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- IHYJDSLHUCKBPI-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-(1-methyl-6-oxopyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CC(F)=C1 IHYJDSLHUCKBPI-UHFFFAOYSA-N 0.000 claims description 2
- 229940124049 Adenosine A2 receptor antagonist Drugs 0.000 claims description 2
- 229940123053 Adenosine A2b receptor antagonist Drugs 0.000 claims description 2
- 239000003449 adenosine A2 receptor antagonist Substances 0.000 claims description 2
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- ZDYCXPYXHMPLCB-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(1-methyl-6-oxopyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 ZDYCXPYXHMPLCB-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 101150078577 Adora2b gene Proteins 0.000 abstract description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 13
- 230000008485 antagonism Effects 0.000 abstract description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 140
- 239000007858 starting material Substances 0.000 description 95
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- 239000002904 solvent Substances 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 44
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000002585 base Substances 0.000 description 38
- 239000003153 chemical reaction reagent Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- 238000004519 manufacturing process Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 22
- 229910000027 potassium carbonate Inorganic materials 0.000 description 22
- 235000011181 potassium carbonates Nutrition 0.000 description 22
- 102000005962 receptors Human genes 0.000 description 22
- 108020003175 receptors Proteins 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 150000001298 alcohols Chemical class 0.000 description 21
- 238000001914 filtration Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 150000002170 ethers Chemical class 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 239000012047 saturated solution Substances 0.000 description 15
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 14
- 235000019270 ammonium chloride Nutrition 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 11
- 229960005305 adenosine Drugs 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000002140 halogenating effect Effects 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
- 235000011118 potassium hydroxide Nutrition 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 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 8
- 239000000843 powder Substances 0.000 description 8
- JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
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- 238000002474 experimental method Methods 0.000 description 6
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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- 235000014113 dietary fatty acids Nutrition 0.000 description 5
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- RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 4
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- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
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- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 150000001412 amines Chemical class 0.000 description 4
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
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- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 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
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Endocrinology (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
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- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000245056 | 2000-08-11 | ||
PCT/JP2001/006870 WO2002014282A1 (fr) | 2000-08-11 | 2001-08-09 | Composes 2-aminopyridine et leur utilisation comme medicaments |
Publications (3)
Publication Number | Publication Date |
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NO20030637D0 NO20030637D0 (no) | 2003-02-07 |
NO20030637L NO20030637L (no) | 2003-04-10 |
NO325873B1 true NO325873B1 (no) | 2008-08-11 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20030637A NO325873B1 (no) | 2000-08-11 | 2003-02-07 | 2-aminopyridinforbindelser, deres anvendelse samt farmasoytisk preparat |
Country Status (18)
Country | Link |
---|---|
US (1) | US6750232B2 (fr) |
EP (1) | EP1308441B1 (fr) |
JP (1) | JP4251868B2 (fr) |
KR (1) | KR100804111B1 (fr) |
CN (1) | CN1446202A (fr) |
AT (1) | ATE444752T1 (fr) |
AU (2) | AU7774101A (fr) |
CA (1) | CA2417846A1 (fr) |
DE (1) | DE60140126D1 (fr) |
HU (1) | HUP0700086A2 (fr) |
IL (2) | IL153995A0 (fr) |
MX (1) | MXPA03001136A (fr) |
NO (1) | NO325873B1 (fr) |
NZ (1) | NZ523998A (fr) |
RU (1) | RU2250898C2 (fr) |
TW (1) | TWI298064B (fr) |
WO (1) | WO2002014282A1 (fr) |
ZA (1) | ZA200300482B (fr) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI330183B (fr) | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
PT2942082T (pt) | 2002-01-28 | 2019-06-06 | Kyowa Hakko Kogyo Kk | Antagonistas do recetor de a2a para utilização no tratamento de distúrbios de movimento |
AU2002950853A0 (en) * | 2002-08-19 | 2002-09-12 | Fujisawa Pharmaceutical Co., Ltd. | Aminopyrimidine compound and pharmaceutical use thereof |
US20040067955A1 (en) * | 2002-09-06 | 2004-04-08 | Fujisawa Pharmaceutical Co. Ltd. | Pyridazinone compound and pharmaceutical use thereof |
BRPI0415863A (pt) * | 2003-10-27 | 2007-01-09 | Astellas Pharma Inc | derivados pirazina e seus usos farmacêuticos |
ES2241496B1 (es) * | 2004-04-15 | 2006-12-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridina. |
US7932275B2 (en) * | 2004-10-29 | 2011-04-26 | Merck, Sharp & Dohme Corp. | 2-aminopyridine compounds useful as β-secretase inhibitors for the treatment of alzheimer's disease |
DE102004061288A1 (de) | 2004-12-14 | 2006-06-29 | Schering Ag | 3-Amino-Pyrazolo[3,4b]pyridine als Inhibitoren von Proteintyrosinkinasen, deren Herstellung und Verwendung als Arzneimittel |
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DD287260A5 (de) * | 1989-08-29 | 1991-02-21 | Akademie Der Wissenschaften Der Ddr,De | Verfahren zur herstellung von 6-substituierten 2-amino-3-cyan-5-(pyrid-4-yl)-pyridinen |
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US6030969A (en) | 1998-04-09 | 2000-02-29 | Abbott Laboratories | 5,6,7-trisubstituted-4-aminopyrido[2,3-D] pyrimidine compounds |
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2001
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- 2001-08-09 NZ NZ523998A patent/NZ523998A/en unknown
- 2001-08-09 JP JP2002519425A patent/JP4251868B2/ja not_active Expired - Fee Related
- 2001-08-09 CN CN01814043A patent/CN1446202A/zh active Pending
- 2001-08-09 AU AU7774101A patent/AU7774101A/xx active Pending
- 2001-08-09 KR KR1020037001943A patent/KR100804111B1/ko not_active IP Right Cessation
- 2001-08-09 US US10/333,689 patent/US6750232B2/en not_active Expired - Fee Related
- 2001-08-09 DE DE60140126T patent/DE60140126D1/de not_active Expired - Lifetime
- 2001-08-09 MX MXPA03001136A patent/MXPA03001136A/es active IP Right Grant
- 2001-08-09 EP EP01955633A patent/EP1308441B1/fr not_active Expired - Lifetime
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- 2001-08-09 IL IL15399501A patent/IL153995A0/xx active IP Right Grant
- 2001-08-09 WO PCT/JP2001/006870 patent/WO2002014282A1/fr active IP Right Grant
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- 2001-08-09 RU RU2003106397/04A patent/RU2250898C2/ru not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
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NO20030637L (no) | 2003-04-10 |
JP4251868B2 (ja) | 2009-04-08 |
RU2250898C2 (ru) | 2005-04-27 |
EP1308441A1 (fr) | 2003-05-07 |
NO20030637D0 (no) | 2003-02-07 |
TWI298064B (en) | 2008-06-21 |
US6750232B2 (en) | 2004-06-15 |
IL153995A0 (en) | 2003-07-31 |
ZA200300482B (en) | 2004-05-10 |
DE60140126D1 (de) | 2009-11-19 |
AU7774101A (en) | 2002-02-25 |
JPWO2002014282A1 (ja) | 2004-06-10 |
US20040006082A1 (en) | 2004-01-08 |
ATE444752T1 (de) | 2009-10-15 |
KR20030022382A (ko) | 2003-03-15 |
EP1308441B1 (fr) | 2009-10-07 |
CN1446202A (zh) | 2003-10-01 |
NZ523998A (en) | 2005-07-29 |
HUP0700086A2 (en) | 2007-05-29 |
AU2001277741B2 (en) | 2005-12-22 |
KR100804111B1 (ko) | 2008-02-18 |
EP1308441A4 (fr) | 2004-03-03 |
IL153995A (en) | 2008-03-20 |
WO2002014282A1 (fr) | 2002-02-21 |
MXPA03001136A (es) | 2003-06-24 |
CA2417846A1 (fr) | 2003-01-30 |
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