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
- Authority
- NO
- Norway
- Prior art keywords
- group
- amino
- furyl
- agent
- oxo
- Prior art date
Links
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012156 elution solvent Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920000609 methyl cellulose Polymers 0.000 description 6
- 235000010981 methylcellulose Nutrition 0.000 description 6
- 239000001923 methylcellulose Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 description 4
- RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- 101150051188 Adora2a gene Proteins 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 102000014384 Type C Phospholipases Human genes 0.000 description 4
- 108010079194 Type C Phospholipases Proteins 0.000 description 4
- MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 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
- 230000002152 alkylating effect Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 229910001424 calcium ion Inorganic materials 0.000 description 4
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000003834 intracellular effect Effects 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 230000009870 specific binding Effects 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- XZANRDHLUPXTGP-UHFFFAOYSA-N 2-(3-cyanopyridin-2-yl)oxyacetamide Chemical class NC(=O)COC1=NC=CC=C1C#N XZANRDHLUPXTGP-UHFFFAOYSA-N 0.000 description 3
- XOULJBREWOVDDA-UHFFFAOYSA-N 2-amino-5-bromo-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(C=2OC=CC=2)=C1Br XOULJBREWOVDDA-UHFFFAOYSA-N 0.000 description 3
- 101150007969 ADORA1 gene Proteins 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000007471 Adenosine A2A receptor Human genes 0.000 description 3
- 108010085277 Adenosine A2A receptor Proteins 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 102000030621 adenylate cyclase Human genes 0.000 description 3
- 108060000200 adenylate cyclase Proteins 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 229940014259 gelatin Drugs 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 230000010807 negative regulation of binding Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000003002 pH adjusting agent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- CZMJZCQVFYAVTI-XFFZJAGNSA-N (z)-1-(furan-2-yl)-3-methylsulfanyl-3-propan-2-yloxyprop-2-en-1-one Chemical compound CC(C)OC(/SC)=C/C(=O)C1=CC=CO1 CZMJZCQVFYAVTI-XFFZJAGNSA-N 0.000 description 2
- 125000004733 1,1,2-trimethylpropylthio group Chemical group CC(C(C)C)(S*)C 0.000 description 2
- 125000004727 1,3-dimethylbutylthio group Chemical group CC(CC(C)C)S* 0.000 description 2
- XQSYGQZXBWJMJX-UHFFFAOYSA-N 1-(furan-2-yl)-2-pyridin-4-ylethanone Chemical compound C=1C=COC=1C(=O)CC1=CC=NC=C1 XQSYGQZXBWJMJX-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- YOLYOEXWVQLOKO-UHFFFAOYSA-N 2-[3-cyano-6-(furan-2-yl)pyridin-2-yl]oxyacetamide Chemical compound C1=C(C#N)C(OCC(=O)N)=NC(C=2OC=CC=2)=C1 YOLYOEXWVQLOKO-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- ZHYAIJNGEWGPTH-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxylic acid Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(O)=O)=C(N)N=C1C1=CC=CO1 ZHYAIJNGEWGPTH-UHFFFAOYSA-N 0.000 description 2
- STJOEODJKHJOAS-UHFFFAOYSA-N 2-amino-5-(4-cyanophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(C#N)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 STJOEODJKHJOAS-UHFFFAOYSA-N 0.000 description 2
- OMWKJINXWQGQGH-UHFFFAOYSA-N 2-amino-5-[1-(4-cyanophenyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C=2C=CC(=CC=2)C#N)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 OMWKJINXWQGQGH-UHFFFAOYSA-N 0.000 description 2
- QORPGNXCVBZAKX-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-(4-methoxypyridin-3-yl)-4-propan-2-yloxypyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C1=C(OC(C)C)C(C#N)=C(N)N=C1C1=CC=CC(F)=C1 QORPGNXCVBZAKX-UHFFFAOYSA-N 0.000 description 2
- QDPHEIPZQVVKTB-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-(4-methoxypyridin-3-yl)pyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CC(F)=C1 QDPHEIPZQVVKTB-UHFFFAOYSA-N 0.000 description 2
- KFYDAYYWBVZTAS-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methoxypyridin-3-yl)-4-propan-2-yloxypyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C1=C(OC(C)C)C(C#N)=C(N)N=C1C1=CC=CO1 KFYDAYYWBVZTAS-UHFFFAOYSA-N 0.000 description 2
- TXKRIPUJWAUEKY-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methoxypyridin-3-yl)pyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 TXKRIPUJWAUEKY-UHFFFAOYSA-N 0.000 description 2
- JOMDOOCKRTVVFY-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-propylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound CCCC1=CC=NC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 JOMDOOCKRTVVFY-UHFFFAOYSA-N 0.000 description 2
- NRXHGJLQXAIHAJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(6-oxo-1-propylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 NRXHGJLQXAIHAJ-UHFFFAOYSA-N 0.000 description 2
- KWHKZWCSMWEEPA-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(C=2OC=CC=2)=C1 KWHKZWCSMWEEPA-UHFFFAOYSA-N 0.000 description 2
- DRDZEWZZDSKJCU-UHFFFAOYSA-N 2-chloro-6-(furan-2-yl)-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C=1C=NC=CC=1C=1C=C(C#N)C(Cl)=NC=1C1=CC=CO1 DRDZEWZZDSKJCU-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CITGMZFNHZEDQA-UHFFFAOYSA-N 3-(dimethylamino)-1-(furan-2-yl)-2-pyridin-4-ylprop-2-en-1-one Chemical compound C=1C=NC=CC=1C(=CN(C)C)C(=O)C1=CC=CO1 CITGMZFNHZEDQA-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 2
- PQKKNEIVRPZRNA-UHFFFAOYSA-N 6-(furan-2-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC(C=2OC=CC=2)=C1 PQKKNEIVRPZRNA-UHFFFAOYSA-N 0.000 description 2
- HXNFSHNUOBZIBW-UHFFFAOYSA-N 6-(furan-2-yl)-2-oxo-4-propan-2-yloxy-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=C(OC(C)C)C=C1C1=CC=CO1 HXNFSHNUOBZIBW-UHFFFAOYSA-N 0.000 description 2
- POPNXNJKCHXVHY-UHFFFAOYSA-N 6-(furan-2-yl)-2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound C=1C=NC=CC=1C=1C=C(C#N)C(=O)NC=1C1=CC=CO1 POPNXNJKCHXVHY-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 210000005252 bulbus oculi Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000112 colonic effect Effects 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 230000004941 influx Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- ZFBKVTPTHILOKZ-UHFFFAOYSA-N o-propan-2-yl 3-(furan-2-yl)-3-oxopropanethioate Chemical compound CC(C)OC(=S)CC(=O)C1=CC=CO1 ZFBKVTPTHILOKZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001508 potassium citrate Substances 0.000 description 2
- 229960002635 potassium citrate Drugs 0.000 description 2
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 2
- 235000011082 potassium citrates Nutrition 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005891 transamination reaction Methods 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- CGCFRHMQQKEKKH-BQYQJAHWSA-N (e)-1,3-bis(3-fluorophenyl)prop-2-en-1-one Chemical compound FC1=CC=CC(\C=C\C(=O)C=2C=C(F)C=CC=2)=C1 CGCFRHMQQKEKKH-BQYQJAHWSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- 125000004719 1,1-dimethylpropylthio group Chemical group CC(CC)(S*)C 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000005926 1,2-dimethylbutyloxy group Chemical group 0.000 description 1
- 125000004726 1,2-dimethylbutylthio group Chemical group CC(C(CC)C)S* 0.000 description 1
- 125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
- 125000004720 1,2-dimethylpropylthio group Chemical group CC(C(C)C)S* 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- HCEKGPAHZCYRBZ-UHFFFAOYSA-N 1-(3-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1 HCEKGPAHZCYRBZ-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004728 2,2-dimethylbutylthio group Chemical group CC(CS*)(CC)C 0.000 description 1
- 125000004716 2,2-dimethylpropylthio group Chemical group CC(CS*)(C)C 0.000 description 1
- 125000004729 2,3-dimethylbutylthio group Chemical group CC(CS*)C(C)C 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- QUGPJABAXMLFRJ-UHFFFAOYSA-N 2-amino-4,6-bis(3-fluorophenyl)-5-(4-methoxypyridin-3-yl)pyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C1=C(C=2C=C(F)C=CC=2)N=C(N)C(C#N)=C1C1=CC=CC(F)=C1 QUGPJABAXMLFRJ-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- OAYRZMSWYWURDK-UHFFFAOYSA-N 2-amino-5,6-bis(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=COC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 OAYRZMSWYWURDK-UHFFFAOYSA-N 0.000 description 1
- PGVAUXSAXYXOIH-UHFFFAOYSA-N 2-amino-5-(1,3-benzodioxol-5-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C2OCOC2=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 PGVAUXSAXYXOIH-UHFFFAOYSA-N 0.000 description 1
- LEVXWKWFKQCBSK-UHFFFAOYSA-N 2-amino-5-(1-benzofuran-2-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C2=CC=CC=C2OC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 LEVXWKWFKQCBSK-UHFFFAOYSA-N 0.000 description 1
- IAJSHYDAXSUISN-UHFFFAOYSA-N 2-amino-5-(1-benzothiophen-2-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C2=CC=CC=C2SC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IAJSHYDAXSUISN-UHFFFAOYSA-N 0.000 description 1
- NAZFFONCSIPQQN-UHFFFAOYSA-N 2-amino-5-(1-benzothiophen-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1SC2=CC=CC=C2C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 NAZFFONCSIPQQN-UHFFFAOYSA-N 0.000 description 1
- IDWWEUFEJRJXFJ-UHFFFAOYSA-N 2-amino-5-(1-benzyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC=2C=CC=CC=2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IDWWEUFEJRJXFJ-UHFFFAOYSA-N 0.000 description 1
- MAWHQAOMDKDOJE-UHFFFAOYSA-N 2-amino-5-(1-but-2-ynyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC#CC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 MAWHQAOMDKDOJE-UHFFFAOYSA-N 0.000 description 1
- AORHGFQZPYHCSO-UHFFFAOYSA-N 2-amino-5-(1-but-3-enyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC=C)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 AORHGFQZPYHCSO-UHFFFAOYSA-N 0.000 description 1
- ZRPLHBFKBMXTRO-UHFFFAOYSA-N 2-amino-5-(1-butyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 ZRPLHBFKBMXTRO-UHFFFAOYSA-N 0.000 description 1
- VKGPRTWMBVWGNK-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(2-methylpropyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC(C)C)=C(N)N=C1C1=CC=CO1 VKGPRTWMBVWGNK-UHFFFAOYSA-N 0.000 description 1
- TWRIAVIYZCSNRP-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(2-pyridin-2-ylethyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCC=2N=CC=CC=2)=C(N)N=C1C1=CC=CO1 TWRIAVIYZCSNRP-UHFFFAOYSA-N 0.000 description 1
- AVZLLGRCJWMPTM-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(2-pyridin-4-ylethyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCC=2C=CN=CC=2)=C(N)N=C1C1=CC=CO1 AVZLLGRCJWMPTM-UHFFFAOYSA-N 0.000 description 1
- WRYFRTMAFVQARC-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(3-hydroxypropyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCCO)=C(N)N=C1C1=CC=CO1 WRYFRTMAFVQARC-UHFFFAOYSA-N 0.000 description 1
- FMWFTUXJNOGBBZ-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(pyridin-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC=2N=CC=CC=2)=C(N)N=C1C1=CC=CO1 FMWFTUXJNOGBBZ-UHFFFAOYSA-N 0.000 description 1
- CFYIGJFIIKONEO-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-(pyridin-3-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC=2C=NC=CC=2)=C(N)N=C1C1=CC=CO1 CFYIGJFIIKONEO-UHFFFAOYSA-N 0.000 description 1
- GGKCWQYKCPXJBO-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-[3-(2-oxopyrrolidin-1-yl)propyl]pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCCN2C(CCC2)=O)=C(N)N=C1C1=CC=CO1 GGKCWQYKCPXJBO-UHFFFAOYSA-N 0.000 description 1
- XBFPZVPJVWDFHP-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-methylpyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NC)=C(N)N=C1C1=CC=CO1 XBFPZVPJVWDFHP-UHFFFAOYSA-N 0.000 description 1
- ZRUCWRYDMYENMD-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-phenylpyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NC=2C=CC=CC=2)=C(N)N=C1C1=CC=CO1 ZRUCWRYDMYENMD-UHFFFAOYSA-N 0.000 description 1
- HVHRWPDYJBIJIM-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)-n-prop-2-ynylpyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC#C)=C(N)N=C1C1=CC=CO1 HVHRWPDYJBIJIM-UHFFFAOYSA-N 0.000 description 1
- FEQYPAHUDHEWOW-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(N)=O)=C(N)N=C1C1=CC=CO1 FEQYPAHUDHEWOW-UHFFFAOYSA-N 0.000 description 1
- AOCNGJLCMMFHFQ-UHFFFAOYSA-N 2-amino-5-(1-ethyl-6-oxopyridin-3-yl)-n-(2-fluoroethyl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCF)=C(N)N=C1C1=CC=CO1 AOCNGJLCMMFHFQ-UHFFFAOYSA-N 0.000 description 1
- NNQNLXIHUNCWGO-UHFFFAOYSA-N 2-amino-5-(2,4-dichlorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 NNQNLXIHUNCWGO-UHFFFAOYSA-N 0.000 description 1
- WOXSYHVXFHDTFE-UHFFFAOYSA-N 2-amino-5-(2,4-difluorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WOXSYHVXFHDTFE-UHFFFAOYSA-N 0.000 description 1
- ZIMRBKSDTFGMGB-UHFFFAOYSA-N 2-amino-5-(2,4-dimethoxyphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound COC1=CC(OC)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 ZIMRBKSDTFGMGB-UHFFFAOYSA-N 0.000 description 1
- YJKNXNNVJIBEPH-UHFFFAOYSA-N 2-amino-5-(2,5-dichlorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C(Cl)=CC=C(Cl)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 YJKNXNNVJIBEPH-UHFFFAOYSA-N 0.000 description 1
- ACIZKOXOSXMFQR-UHFFFAOYSA-N 2-amino-5-(2-chlorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC=C(Cl)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ACIZKOXOSXMFQR-UHFFFAOYSA-N 0.000 description 1
- OBBTYKUQMUZVDV-UHFFFAOYSA-N 2-amino-5-(2-fluorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC=C(F)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 OBBTYKUQMUZVDV-UHFFFAOYSA-N 0.000 description 1
- VMQUKACNVZFMAW-UHFFFAOYSA-N 2-amino-5-(2-formylphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC=C(C=O)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 VMQUKACNVZFMAW-UHFFFAOYSA-N 0.000 description 1
- JXCIQSCEEBCNCB-UHFFFAOYSA-N 2-amino-5-(2-formylthiophen-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CSC(C=O)=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 JXCIQSCEEBCNCB-UHFFFAOYSA-N 0.000 description 1
- IMJUKRYYCDNHCC-UHFFFAOYSA-N 2-amino-5-(3,4-dichlorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(Cl)C(Cl)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IMJUKRYYCDNHCC-UHFFFAOYSA-N 0.000 description 1
- AETLIYQPFNECMC-UHFFFAOYSA-N 2-amino-5-(3,4-dimethoxyphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 AETLIYQPFNECMC-UHFFFAOYSA-N 0.000 description 1
- ZNVXZDRGTLGOHF-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC(Cl)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ZNVXZDRGTLGOHF-UHFFFAOYSA-N 0.000 description 1
- RZKMIMLGFQUBMV-UHFFFAOYSA-N 2-amino-5-(3-cyanophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC(C#N)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 RZKMIMLGFQUBMV-UHFFFAOYSA-N 0.000 description 1
- FGDYJNXITWUJTC-UHFFFAOYSA-N 2-amino-5-(3-ethoxyphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound CCOC1=CC=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 FGDYJNXITWUJTC-UHFFFAOYSA-N 0.000 description 1
- QEAWQAVBEKPUBR-UHFFFAOYSA-N 2-amino-5-(3-fluoro-4-phenylphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C(F)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 QEAWQAVBEKPUBR-UHFFFAOYSA-N 0.000 description 1
- IMUZWQMIZWGAFB-UHFFFAOYSA-N 2-amino-5-(3-fluorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC(F)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IMUZWQMIZWGAFB-UHFFFAOYSA-N 0.000 description 1
- MDKMFDHYKCXYJO-UHFFFAOYSA-N 2-amino-5-(3-formylphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC(C=O)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 MDKMFDHYKCXYJO-UHFFFAOYSA-N 0.000 description 1
- IESQIJIFWOCMKI-UHFFFAOYSA-N 2-amino-5-(3-formylthiophen-2-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound S1C=CC(C=O)=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IESQIJIFWOCMKI-UHFFFAOYSA-N 0.000 description 1
- XPNTXFGZXBLEMR-UHFFFAOYSA-N 2-amino-5-(4-ethenylphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(C=C)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 XPNTXFGZXBLEMR-UHFFFAOYSA-N 0.000 description 1
- SXZBTMOGFZOLCS-UHFFFAOYSA-N 2-amino-5-(4-fluorophenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(F)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 SXZBTMOGFZOLCS-UHFFFAOYSA-N 0.000 description 1
- HCLSVVXULMPXII-UHFFFAOYSA-N 2-amino-5-(4-tert-butylphenyl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 HCLSVVXULMPXII-UHFFFAOYSA-N 0.000 description 1
- OVSHPFXYVBGYRU-UHFFFAOYSA-N 2-amino-5-(5-chlorothiophen-2-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(Cl)SC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 OVSHPFXYVBGYRU-UHFFFAOYSA-N 0.000 description 1
- ASNGUXUQUIQKNX-UHFFFAOYSA-N 2-amino-5-(6-but-3-enoxypyridin-3-yl)-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(OCCC=C)N=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ASNGUXUQUIQKNX-UHFFFAOYSA-N 0.000 description 1
- FZIDJILLVWPZFA-UHFFFAOYSA-N 2-amino-5-[1-(2,3-dihydroxypropyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC(O)CO)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 FZIDJILLVWPZFA-UHFFFAOYSA-N 0.000 description 1
- ANQKDAAIWIAZBX-UHFFFAOYSA-N 2-amino-5-[1-(2-cyanoethyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC#N)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ANQKDAAIWIAZBX-UHFFFAOYSA-N 0.000 description 1
- FCYCLLWHLWDRES-UHFFFAOYSA-N 2-amino-5-[1-(2-fluorophenyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C=2C(=CC=CC=2)F)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 FCYCLLWHLWDRES-UHFFFAOYSA-N 0.000 description 1
- NBECXBXKPRJCSJ-UHFFFAOYSA-N 2-amino-5-[1-(3-chloropropyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCCl)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 NBECXBXKPRJCSJ-UHFFFAOYSA-N 0.000 description 1
- RTCFYSWAJRCHPI-UHFFFAOYSA-N 2-amino-5-[1-(3-cyanopropyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCC#N)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 RTCFYSWAJRCHPI-UHFFFAOYSA-N 0.000 description 1
- DIUYDOBOMZAWAI-UHFFFAOYSA-N 2-amino-5-[1-(3-fluorophenyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C=2C=C(F)C=CC=2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 DIUYDOBOMZAWAI-UHFFFAOYSA-N 0.000 description 1
- JSDLZRFCBZARJM-UHFFFAOYSA-N 2-amino-5-[1-(3-fluoropropyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCF)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 JSDLZRFCBZARJM-UHFFFAOYSA-N 0.000 description 1
- CVGXZJQYDCCTHG-UHFFFAOYSA-N 2-amino-5-[1-(4-chlorobutyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCCCl)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 CVGXZJQYDCCTHG-UHFFFAOYSA-N 0.000 description 1
- FBYFZDWFAZUBNM-UHFFFAOYSA-N 2-amino-5-[1-(4-ethenylphenyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C=2C=CC(C=C)=CC=2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 FBYFZDWFAZUBNM-UHFFFAOYSA-N 0.000 description 1
- WTPBYUHPEIINFU-UHFFFAOYSA-N 2-amino-5-[1-(4-fluorophenyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C=2C=CC(F)=CC=2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WTPBYUHPEIINFU-UHFFFAOYSA-N 0.000 description 1
- USUHMDNANVWEHD-UHFFFAOYSA-N 2-amino-5-[1-(6-cyanoheptan-3-yl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(C(CCC(C)C#N)CC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 USUHMDNANVWEHD-UHFFFAOYSA-N 0.000 description 1
- SUVRBRKPWPVWFQ-UHFFFAOYSA-N 2-amino-5-[1-(cyclohexylmethyl)-6-oxopyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC2CCCCC2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 SUVRBRKPWPVWFQ-UHFFFAOYSA-N 0.000 description 1
- FCWJKSJBSHXNIC-UHFFFAOYSA-N 2-amino-5-[3,5-bis(trifluoromethyl)phenyl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 FCWJKSJBSHXNIC-UHFFFAOYSA-N 0.000 description 1
- APFOELZGINSUED-UHFFFAOYSA-N 2-amino-5-[4-(dimethylamino)phenyl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 APFOELZGINSUED-UHFFFAOYSA-N 0.000 description 1
- WGXSTYOUUAQUFU-UHFFFAOYSA-N 2-amino-5-[6-(2,3-dihydroxypropoxy)pyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(OCC(O)CO)N=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WGXSTYOUUAQUFU-UHFFFAOYSA-N 0.000 description 1
- IRTOECRSHKOWHN-UHFFFAOYSA-N 2-amino-5-[6-(5-chloropentoxy)pyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=C(OCCCCCCl)N=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IRTOECRSHKOWHN-UHFFFAOYSA-N 0.000 description 1
- DOJMMYNRVFDLJC-UHFFFAOYSA-N 2-amino-5-[6-[(6,7-dimethoxy-2-oxochromen-4-yl)methoxy]pyridin-3-yl]-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2OC(=O)C=C1COC(N=C1)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 DOJMMYNRVFDLJC-UHFFFAOYSA-N 0.000 description 1
- WOFTWMVJEGODIT-UHFFFAOYSA-N 2-amino-5-dibenzofuran-4-yl-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C=1C=CC(C2=CC=CC=C2O2)=C2C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WOFTWMVJEGODIT-UHFFFAOYSA-N 0.000 description 1
- FWQZFXHABAUERI-UHFFFAOYSA-N 2-amino-6,6-bis(furan-2-yl)-5-(6-oxo-1-phenylpyridin-3-yl)-1h-pyridine-3-carbonitrile Chemical compound C=1C=COC=1C1(C=2OC=CC=2)NC(N)=C(C#N)C=C1C(=C1)C=CC(=O)N1C1=CC=CC=C1 FWQZFXHABAUERI-UHFFFAOYSA-N 0.000 description 1
- VDYPGIUUCHKTIB-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-4-oxo-5-(6-oxo-1h-pyridin-3-yl)-1h-pyridine-3-carbonitrile;hydrobromide Chemical compound Br.C1=CC(=O)NC=C1C=1C(O)=C(C#N)C(N)=NC=1C1=CC=CC(F)=C1 VDYPGIUUCHKTIB-UHFFFAOYSA-N 0.000 description 1
- COLCNOJDPCHNGG-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1N=C(N)C(C(=O)N)=CC=1C1=CC=NC=C1 COLCNOJDPCHNGG-UHFFFAOYSA-N 0.000 description 1
- UKSOTJDMMYKQTJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-4-oxo-5-(6-oxo-1h-pyridin-3-yl)-1h-pyridine-3-carbonitrile;hydrobromide Chemical compound Br.C1=CC(=O)NC=C1C=1C(O)=C(C#N)C(N)=NC=1C1=CC=CO1 UKSOTJDMMYKQTJ-UHFFFAOYSA-N 0.000 description 1
- ZCKOBFRKCVROKL-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(1-heptyl-6-oxopyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCCCCC)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 ZCKOBFRKCVROKL-UHFFFAOYSA-N 0.000 description 1
- RENGEZIWMBNYGK-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(2,3,4,5,6-pentafluorophenyl)pyridine-3-carbonitrile Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 RENGEZIWMBNYGK-UHFFFAOYSA-N 0.000 description 1
- HNIXLNNEKZVYRR-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(2-methylphenyl)pyridine-3-carbonitrile Chemical compound CC1=CC=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 HNIXLNNEKZVYRR-UHFFFAOYSA-N 0.000 description 1
- HKFWNVACHBNSJZ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3,4,5-trimethoxyphenyl)pyridine-3-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 HKFWNVACHBNSJZ-UHFFFAOYSA-N 0.000 description 1
- ZDRCMZLOKYNRLJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3-methoxyphenyl)pyridine-3-carbonitrile Chemical compound COC1=CC=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 ZDRCMZLOKYNRLJ-UHFFFAOYSA-N 0.000 description 1
- CKBZDBYENIROBB-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3-methylphenyl)pyridine-3-carbonitrile Chemical compound CC1=CC=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 CKBZDBYENIROBB-UHFFFAOYSA-N 0.000 description 1
- UAXSSPVSBBZGSA-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3-nitrophenyl)pyridine-3-carbonitrile Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 UAXSSPVSBBZGSA-UHFFFAOYSA-N 0.000 description 1
- BPGQQFCJPDMTHH-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3-phenylmethoxyphenyl)pyridine-3-carbonitrile Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 BPGQQFCJPDMTHH-UHFFFAOYSA-N 0.000 description 1
- MEFZSWIKHCQDPD-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(3-phenylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 MEFZSWIKHCQDPD-UHFFFAOYSA-N 0.000 description 1
- OGHKBPPXFOLZMX-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methyl-3-nitrophenyl)pyridine-3-carbonitrile Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 OGHKBPPXFOLZMX-UHFFFAOYSA-N 0.000 description 1
- JWLCFRHEEAELEO-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 JWLCFRHEEAELEO-UHFFFAOYSA-N 0.000 description 1
- PDUMLTYQHGYVDW-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methylsulfanylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(SC)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 PDUMLTYQHGYVDW-UHFFFAOYSA-N 0.000 description 1
- YXCGKRZYTDZVSC-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methylsulfinylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 YXCGKRZYTDZVSC-UHFFFAOYSA-N 0.000 description 1
- MESCJCHUBHJLAA-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 MESCJCHUBHJLAA-UHFFFAOYSA-N 0.000 description 1
- WGQOUFGWYCJSMJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-methylthiophen-2-yl)pyridine-3-carbonitrile Chemical compound CC1=CSC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 WGQOUFGWYCJSMJ-UHFFFAOYSA-N 0.000 description 1
- VIAZRXWYFHBXBO-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-nitrophenyl)pyridine-3-carbonitrile Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 VIAZRXWYFHBXBO-UHFFFAOYSA-N 0.000 description 1
- GZUUMVJBAUCUMK-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-phenoxyphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 GZUUMVJBAUCUMK-UHFFFAOYSA-N 0.000 description 1
- MJASPERZGWQOLJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-phenylmethoxyphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 MJASPERZGWQOLJ-UHFFFAOYSA-N 0.000 description 1
- CMVKNGQEGYKKDQ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(4-phenylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 CMVKNGQEGYKKDQ-UHFFFAOYSA-N 0.000 description 1
- YEPKMXJRQFMSNX-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(5-methylthiophen-2-yl)pyridine-3-carbonitrile Chemical compound S1C(C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 YEPKMXJRQFMSNX-UHFFFAOYSA-N 0.000 description 1
- OISMLYJKWQQYRP-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(6-heptoxypyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=NC(OCCCCCCC)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 OISMLYJKWQQYRP-UHFFFAOYSA-N 0.000 description 1
- ADDWHMPJWFXWKT-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(6-oxo-1-pent-4-enylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCC=C)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ADDWHMPJWFXWKT-UHFFFAOYSA-N 0.000 description 1
- TVJPMKJHVONPRV-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carboxylic acid Chemical compound C1=CC(=O)NC=C1C=1C=C(C(O)=O)C(N)=NC=1C1=CC=CO1 TVJPMKJHVONPRV-UHFFFAOYSA-N 0.000 description 1
- WNCZOZANHJZKKU-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-(furan-3-yl)pyridine-3-carbonitrile Chemical compound C1=COC=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WNCZOZANHJZKKU-UHFFFAOYSA-N 0.000 description 1
- NXEDWCIOUHSTNO-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(2-methoxyphenyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound COC1=CC=CC=C1N1C(=O)C=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 NXEDWCIOUHSTNO-UHFFFAOYSA-N 0.000 description 1
- NFFAGXXHGMGDQG-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(3-hydroxypropyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCO)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 NFFAGXXHGMGDQG-UHFFFAOYSA-N 0.000 description 1
- SIOIJUHSNQEFCL-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(3-methoxyphenyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(N2C(C=CC(=C2)C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=O)=C1 SIOIJUHSNQEFCL-UHFFFAOYSA-N 0.000 description 1
- OUTIESXHSMQUJY-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(3-methylbutyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC(C)C)C=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 OUTIESXHSMQUJY-UHFFFAOYSA-N 0.000 description 1
- GYZVRZKAVDVXPZ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(4-methoxyphenyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 GYZVRZKAVDVXPZ-UHFFFAOYSA-N 0.000 description 1
- BAKXTULXRJNEPU-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(4-methylphenyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 BAKXTULXRJNEPU-UHFFFAOYSA-N 0.000 description 1
- GFFDUSBECUZKFV-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[1-(oxan-2-ylmethyl)-6-oxopyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CC2OCCCC2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 GFFDUSBECUZKFV-UHFFFAOYSA-N 0.000 description 1
- ZWOCWNVVDAUBTG-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[2-(trifluoromethyl)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=C(C(F)(F)F)C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ZWOCWNVVDAUBTG-UHFFFAOYSA-N 0.000 description 1
- PNFIUEMOCDZDLB-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[3-(trifluoromethyl)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 PNFIUEMOCDZDLB-UHFFFAOYSA-N 0.000 description 1
- GJCKOMNLIDINTJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[4-(trifluoromethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 GJCKOMNLIDINTJ-UHFFFAOYSA-N 0.000 description 1
- WNQFTANCWBTGPB-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[4-(trifluoromethyl)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WNQFTANCWBTGPB-UHFFFAOYSA-N 0.000 description 1
- ZYRSKYMGSDCYDJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-(2-oxopropyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=NC(CC(=O)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 ZYRSKYMGSDCYDJ-UHFFFAOYSA-N 0.000 description 1
- GYKXZTNAFULIDE-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-(3-trimethylsilylprop-2-ynoxy)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=NC(OCC#C[Si](C)(C)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 GYKXZTNAFULIDE-UHFFFAOYSA-N 0.000 description 1
- LVUBAVJGBXGZRM-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-[2-(1h-indol-3-yl)ethoxy]pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C=1C=C(OCCC=2C3=CC=CC=C3NC=2)N=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 LVUBAVJGBXGZRM-UHFFFAOYSA-N 0.000 description 1
- MTYAQQSGRNCPTK-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-oxo-1-(3,3,3-trifluoropropyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC(F)(F)F)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 MTYAQQSGRNCPTK-UHFFFAOYSA-N 0.000 description 1
- LDRCLXRSIDSIPW-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-oxo-1-(3,4,4-trifluorobut-3-enyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCC(F)=C(F)F)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 LDRCLXRSIDSIPW-UHFFFAOYSA-N 0.000 description 1
- ZVQCFQPKWFWUKX-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-[6-oxo-1-(3-phenylpropyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(=O)N(CCCC=2C=CC=CC=2)C=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 ZVQCFQPKWFWUKX-UHFFFAOYSA-N 0.000 description 1
- IDJWLTZPPLYLNW-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-naphthalen-1-ylpyridine-3-carbonitrile Chemical compound C=1C=CC2=CC=CC=C2C=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 IDJWLTZPPLYLNW-UHFFFAOYSA-N 0.000 description 1
- LBIUYQNXMJKTHL-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-naphthalen-2-ylpyridine-3-carbonitrile Chemical compound C=1C=C2C=CC=CC2=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 LBIUYQNXMJKTHL-UHFFFAOYSA-N 0.000 description 1
- DZDXJUWESXMEJQ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-phenylpyridine-3-carbonitrile Chemical compound C=1C=CC=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 DZDXJUWESXMEJQ-UHFFFAOYSA-N 0.000 description 1
- QFCRBYNLDUIYTP-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-pyridin-2-ylpyridine-3-carbonitrile Chemical compound C=1C=CC=NC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 QFCRBYNLDUIYTP-UHFFFAOYSA-N 0.000 description 1
- PCXRAMMEMMZESU-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-pyridin-3-ylpyridine-3-carbonitrile Chemical compound C=1C=CN=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 PCXRAMMEMMZESU-UHFFFAOYSA-N 0.000 description 1
- XJIOXNNTIXXTNR-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C=1C=NC=CC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 XJIOXNNTIXXTNR-UHFFFAOYSA-N 0.000 description 1
- WPHGAWRJEKKTAN-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-thiophen-2-ylpyridine-3-carbonitrile Chemical compound C=1C=CSC=1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 WPHGAWRJEKKTAN-UHFFFAOYSA-N 0.000 description 1
- XGUQZRRZBGELSC-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-5-thiophen-3-ylpyridine-3-carbonitrile Chemical compound C1=CSC=C1C=1C=C(C#N)C(N)=NC=1C1=CC=CO1 XGUQZRRZBGELSC-UHFFFAOYSA-N 0.000 description 1
- ONFKXIROFQJIAJ-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-n,n-dimethyl-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carboxamide Chemical compound C=1C=COC=1C=1N=C(N)C(C(=O)N(C)C)=CC=1C=1C=CC(=O)NC=1 ONFKXIROFQJIAJ-UHFFFAOYSA-N 0.000 description 1
- QOTSJIIEDQVCAN-UHFFFAOYSA-N 2-amino-6-(furan-2-yl)-n-(2-hydroxyethyl)-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)NC=C1C=1C=C(C(=O)NCCO)C(N)=NC=1C1=CC=CO1 QOTSJIIEDQVCAN-UHFFFAOYSA-N 0.000 description 1
- ONZKBYHBZLIRHR-UHFFFAOYSA-N 2-amino-n-(2-amino-2-oxoethyl)-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC(N)=O)=C(N)N=C1C1=CC=CO1 ONZKBYHBZLIRHR-UHFFFAOYSA-N 0.000 description 1
- YKFFCHLIIQWLQT-UHFFFAOYSA-N 2-amino-n-(5-cyanopentyl)-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCCCCCC#N)=C(N)N=C1C1=CC=CO1 YKFFCHLIIQWLQT-UHFFFAOYSA-N 0.000 description 1
- AULQFCAJMBERAU-UHFFFAOYSA-N 2-amino-n-(cyclopropylmethyl)-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NCC2CC2)=C(N)N=C1C1=CC=CO1 AULQFCAJMBERAU-UHFFFAOYSA-N 0.000 description 1
- XOTAMVVDBSARQW-UHFFFAOYSA-N 2-amino-n-cyclopropyl-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C1=CC(C(=O)NC2CC2)=C(N)N=C1C1=CC=CO1 XOTAMVVDBSARQW-UHFFFAOYSA-N 0.000 description 1
- BRRXLINGTRJUAJ-UHFFFAOYSA-N 2-amino-n-cyclopropyl-6-(furan-2-yl)-5-(6-oxo-1h-pyridin-3-yl)pyridine-3-carboxamide Chemical compound C1=CC(=O)NC=C1C=1C=C(C(=O)NC2CC2)C(N)=NC=1C1=CC=CO1 BRRXLINGTRJUAJ-UHFFFAOYSA-N 0.000 description 1
- DKEAJMKKDCUWOC-UHFFFAOYSA-N 2-amino-n-ethyl-5-(1-ethyl-6-oxopyridin-3-yl)-6-(furan-2-yl)pyridine-3-carboxamide Chemical compound C=1C=COC=1C=1N=C(N)C(C(=O)NCC)=CC=1C=1C=CC(=O)N(CC)C=1 DKEAJMKKDCUWOC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- 125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004732 2-ethylbutylthio group Chemical group C(C)C(CS*)CC 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005924 2-methylpentyloxy group Chemical group 0.000 description 1
- 125000004722 2-methylpentylthio group Chemical group CC(CS*)CCC 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- FZMFPCLBMUFJGR-UHFFFAOYSA-N 3-(dimethylamino)-1-(furan-2-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CO1 FZMFPCLBMUFJGR-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
- 125000004723 3-methylpentylthio group Chemical group CC(CCS*)CC 0.000 description 1
- FOHGXUZXQDYQLP-UHFFFAOYSA-N 4,6-bis(3-fluorophenyl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound FC1=CC=CC(C=2NC(=O)C(C#N)=C(C=3C=C(F)C=CC=3)C=2)=C1 FOHGXUZXQDYQLP-UHFFFAOYSA-N 0.000 description 1
- IWALGNIFYOBRKC-UHFFFAOYSA-N 4-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)benzenesulfonic acid Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(S(O)(=O)=O)C=C1 IWALGNIFYOBRKC-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- PYUPGTXIJDVABJ-UHFFFAOYSA-N 5-(2-acetylphenyl)-2-amino-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound CC(=O)C1=CC=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 PYUPGTXIJDVABJ-UHFFFAOYSA-N 0.000 description 1
- CNMKCABUJJTQMU-UHFFFAOYSA-N 5-(3-acetylphenyl)-2-amino-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound CC(=O)C1=CC=CC(C=2C(=NC(N)=C(C#N)C=2)C=2OC=CC=2)=C1 CNMKCABUJJTQMU-UHFFFAOYSA-N 0.000 description 1
- WTXTZLYHYIDGCX-UHFFFAOYSA-N 5-(4-acetylphenyl)-2-amino-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 WTXTZLYHYIDGCX-UHFFFAOYSA-N 0.000 description 1
- YXHMOGFICLBRDI-UHFFFAOYSA-N 5-(5-acetylthiophen-2-yl)-2-amino-6-(furan-2-yl)pyridine-3-carbonitrile Chemical compound S1C(C(=O)C)=CC=C1C1=CC(C#N)=C(N)N=C1C1=CC=CO1 YXHMOGFICLBRDI-UHFFFAOYSA-N 0.000 description 1
- UXPXQSWKWHQUCB-UHFFFAOYSA-N 5-(furan-2-yl)-1h-indole Chemical compound C1=COC(C=2C=C3C=CNC3=CC=2)=C1 UXPXQSWKWHQUCB-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010060263 Adenosine A1 Receptor Proteins 0.000 description 1
- 102000030814 Adenosine A1 receptor Human genes 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101001065501 Escherichia phage MS2 Lysis protein Proteins 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 101000783756 Homo sapiens Adenosine receptor A2b Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010021333 Ileus paralytic Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 229940124532 absorption promoter Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- GLRAHDCHUZLKKC-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid;hydrate Chemical compound O.CC#N.OC(=O)C(F)(F)F GLRAHDCHUZLKKC-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002597 adenosine A2 receptor agonist Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000007131 anti Alzheimer effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 102000055126 human ADORA2B Human genes 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960002050 hydrofluoric acid Drugs 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- FIQGIOAELHTLHM-UHFFFAOYSA-N n-(2-aminoethyl)-2-[4-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)phenoxy]acetamide Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(OCC(=O)NCCN)C=C1 FIQGIOAELHTLHM-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- GNGKJKOKYSKNNW-UHFFFAOYSA-N o-propan-2-yl methylsulfanylmethanethioate Chemical compound CSC(=S)OC(C)C GNGKJKOKYSKNNW-UHFFFAOYSA-N 0.000 description 1
- 229940073665 octyldodecyl myristate Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 201000007620 paralytic ileus Diseases 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 229940067631 phospholipid Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 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
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 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
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 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
- KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
-
- 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
- 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
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
-
- 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
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic 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
- A61P3/04—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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (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)
- Cardiology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (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 |
---|---|
NO20030637D0 NO20030637D0 (no) | 2003-02-07 |
NO20030637L NO20030637L (no) | 2003-04-10 |
NO325873B1 true NO325873B1 (no) | 2008-08-11 |
Family
ID=18735647
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 (ko) |
EP (1) | EP1308441B1 (ko) |
JP (1) | JP4251868B2 (ko) |
KR (1) | KR100804111B1 (ko) |
CN (1) | CN1446202A (ko) |
AT (1) | ATE444752T1 (ko) |
AU (2) | AU2001277741B2 (ko) |
CA (1) | CA2417846A1 (ko) |
DE (1) | DE60140126D1 (ko) |
HU (1) | HUP0700086A2 (ko) |
IL (2) | IL153995A0 (ko) |
MX (1) | MXPA03001136A (ko) |
NO (1) | NO325873B1 (ko) |
NZ (1) | NZ523998A (ko) |
RU (1) | RU2250898C2 (ko) |
TW (1) | TWI298064B (ko) |
WO (1) | WO2002014282A1 (ko) |
ZA (1) | ZA200300482B (ko) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI330183B (ko) * | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
PT2260850T (pt) | 2002-01-28 | 2018-10-24 | 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 |
WO2005040151A1 (en) * | 2003-10-27 | 2005-05-06 | Astellas Pharma Inc. | Pyrazine derivatives and pharmaceutical use thereof |
ES2241496B1 (es) * | 2004-04-15 | 2006-12-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridina. |
WO2006060109A1 (en) * | 2004-10-29 | 2006-06-08 | Merck & Co., Inc. | 2-aminopyridine compounds useful as beta-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 |
MX2007014114A (es) | 2005-05-10 | 2008-03-14 | Intermune Inc | Derivados de piridona para modular el sistema de proteina cinasa activada por estres. |
WO2007011760A2 (en) * | 2005-07-15 | 2007-01-25 | Kalypsys, Inc. | Inhibitors of mitotic kinesin |
ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
ES2274712B1 (es) * | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | 1,4-二取代之3-氰基-吡啶酮衍生物及其作為mGluR2-受體之正向異位性調節劑之用途 |
US20080009623A1 (en) * | 2006-07-06 | 2008-01-10 | Eisai R&D Management Co., Ltd. | Pyrimidine compounds |
ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
PT2203439E (pt) | 2007-09-14 | 2011-02-11 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetra-hidro-2h,1'h-[1,4']bipiridinil-2'- onas 1',3'-dissubstituídas |
EA014100B1 (ru) * | 2008-02-21 | 2010-08-30 | Общество С Ограниченной Ответственностью "Валексфарм" | Производные 2,4-диаминопиридина, фармацевтическая композиция, лекарственное средство на их основе для лечения или предупреждения заболеваний и нарушений, вызванных гиперактивацией nmda-рецепторов и/или в качестве стимуляторов когнитивных функций и способ лечения |
JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン, インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
CN102232074B (zh) | 2008-11-28 | 2014-12-03 | 奥梅-杨森制药有限公司 | 作为代谢性谷氨酸盐受体调节剂的吲哚和苯并噁嗪衍生物 |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CA2760741C (en) | 2009-05-12 | 2018-05-01 | Addex Pharma S.A. | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
JP5852665B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
WO2013185284A1 (en) * | 2012-06-12 | 2013-12-19 | Abbott Laboratories | Pyridinone and pyridazinone derivatives |
AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
CN104837832B (zh) * | 2012-10-05 | 2019-04-26 | 里格尔药品股份有限公司 | Gdf-8抑制剂 |
TWI644899B (zh) | 2013-02-04 | 2018-12-21 | 健生藥品公司 | Flap調節劑 |
WO2014121055A2 (en) | 2013-02-04 | 2014-08-07 | Janssen Pharmaceutica Nv | Flap modulators |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
CA2912747C (en) * | 2013-06-27 | 2021-05-04 | Lg Life Sciences Ltd. | Biaryl derivatives as gpr120 agonists |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
WO2015085925A1 (en) | 2013-12-10 | 2015-06-18 | Abbvie Inc. | Bromodomain inhibitors |
KR20200036063A (ko) | 2014-01-21 | 2020-04-06 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
JP6629740B2 (ja) | 2014-01-21 | 2020-01-15 | ヤンセン ファーマシューティカ エヌ.ベー. | 代謝型グルタミン酸作動性受容体サブタイプ2の正のアロステリック調節因子またはオルトステリックアゴニストを含む組み合わせ、およびそれらの使用 |
CN103804312B (zh) * | 2014-02-17 | 2016-04-20 | 四川百利药业有限责任公司 | 一类氮杂环化合物及其制备方法和用途 |
JP6525437B2 (ja) | 2014-04-02 | 2019-06-05 | インターミューン, インコーポレイテッド | 抗線維性ピリジノン |
ES2580702B1 (es) * | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
JP2017149663A (ja) * | 2016-02-24 | 2017-08-31 | 株式会社Lttバイオファーマ | 過敏性腸症候群治療剤 |
ES2927086T3 (es) | 2017-09-28 | 2022-11-02 | Cstone Pharmaceuticals Suzhou Co Ltd | Derivado de anillo condensado como inhibidor del receptor A2A |
AU2019227607C1 (en) * | 2018-02-27 | 2023-07-20 | Incyte Corporation | Imidazopyrimidines and triazolopyrimidines as A2A / A2B inhibitors |
CN110240593A (zh) * | 2018-03-09 | 2019-09-17 | 四川科伦博泰生物医药股份有限公司 | 取代芳胺化合物及其制备方法和用途 |
CN111018858B (zh) * | 2018-10-10 | 2022-11-18 | 复旦大学 | 杂环类衍生物及其制备方法和用途 |
US20220017483A1 (en) * | 2018-12-28 | 2022-01-20 | Sichuan-Kelun-Biotech Biopharmaceutical Co., Ltd | Aminopyridine compound, preparation method therefor and use thereof |
CN111035638A (zh) * | 2019-06-24 | 2020-04-21 | 南开大学 | 一种具有腺苷a1/a2a受体选择性的腺苷a1受体拮抗剂 |
EP4274551A4 (en) * | 2021-01-06 | 2024-07-03 | Penn State Res Found | METHODS AND MATERIALS FOR TREATING BONE LOSS |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE4117802A1 (de) * | 1991-05-30 | 1992-12-03 | Berlin Chemie Ag | 2-aminopyridin-3-carbonitrile als selektive hemmstoffe des humanen cytomegalievirus |
US5686470A (en) | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
AU9648098A (en) | 1997-10-27 | 1999-05-17 | Takeda Chemical Industries Ltd. | Adenosine a3 receptor antagonists |
JP3990061B2 (ja) | 1998-01-05 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | プリン誘導体および糖尿病の予防・治療剤としてのアデノシンa2受容体拮抗剤 |
US6030969A (en) | 1998-04-09 | 2000-02-29 | Abbott Laboratories | 5,6,7-trisubstituted-4-aminopyrido[2,3-D] pyrimidine compounds |
-
2001
- 2001-08-09 WO PCT/JP2001/006870 patent/WO2002014282A1/ja active IP Right Grant
- 2001-08-09 AU AU2001277741A patent/AU2001277741B2/en not_active Ceased
- 2001-08-09 NZ NZ523998A patent/NZ523998A/en unknown
- 2001-08-09 CN CN01814043A patent/CN1446202A/zh active Pending
- 2001-08-09 JP JP2002519425A patent/JP4251868B2/ja not_active Expired - Fee Related
- 2001-08-09 AU AU7774101A patent/AU7774101A/xx active Pending
- 2001-08-09 HU HU0700086A patent/HUP0700086A2/hu unknown
- 2001-08-09 CA CA002417846A patent/CA2417846A1/en not_active Abandoned
- 2001-08-09 IL IL15399501A patent/IL153995A0/xx active IP Right Grant
- 2001-08-09 MX MXPA03001136A patent/MXPA03001136A/es active IP Right Grant
- 2001-08-09 DE DE60140126T patent/DE60140126D1/de not_active Expired - Lifetime
- 2001-08-09 AT AT01955633T patent/ATE444752T1/de not_active IP Right Cessation
- 2001-08-09 EP EP01955633A patent/EP1308441B1/en not_active Expired - Lifetime
- 2001-08-09 RU RU2003106397/04A patent/RU2250898C2/ru not_active IP Right Cessation
- 2001-08-09 US US10/333,689 patent/US6750232B2/en not_active Expired - Fee Related
- 2001-08-09 KR KR1020037001943A patent/KR100804111B1/ko not_active IP Right Cessation
- 2001-08-10 TW TW090119669A patent/TWI298064B/zh not_active IP Right Cessation
-
2003
- 2003-01-16 IL IL153995A patent/IL153995A/en not_active IP Right Cessation
- 2003-01-17 ZA ZA200300482A patent/ZA200300482B/en unknown
- 2003-02-07 NO NO20030637A patent/NO325873B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE60140126D1 (de) | 2009-11-19 |
CA2417846A1 (en) | 2003-01-30 |
US20040006082A1 (en) | 2004-01-08 |
US6750232B2 (en) | 2004-06-15 |
EP1308441B1 (en) | 2009-10-07 |
MXPA03001136A (es) | 2003-06-24 |
JP4251868B2 (ja) | 2009-04-08 |
IL153995A (en) | 2008-03-20 |
NO20030637L (no) | 2003-04-10 |
IL153995A0 (en) | 2003-07-31 |
TWI298064B (en) | 2008-06-21 |
JPWO2002014282A1 (ja) | 2004-06-10 |
KR20030022382A (ko) | 2003-03-15 |
HUP0700086A2 (en) | 2007-05-29 |
RU2250898C2 (ru) | 2005-04-27 |
EP1308441A4 (en) | 2004-03-03 |
ATE444752T1 (de) | 2009-10-15 |
AU7774101A (en) | 2002-02-25 |
WO2002014282A1 (fr) | 2002-02-21 |
EP1308441A1 (en) | 2003-05-07 |
ZA200300482B (en) | 2004-05-10 |
NZ523998A (en) | 2005-07-29 |
CN1446202A (zh) | 2003-10-01 |
AU2001277741B2 (en) | 2005-12-22 |
KR100804111B1 (ko) | 2008-02-18 |
NO20030637D0 (no) | 2003-02-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO325873B1 (no) | 2-aminopyridinforbindelser, deres anvendelse samt farmasoytisk preparat | |
CN100519549C (zh) | 嘧啶化合物以及含有该化合物的药物组合物 | |
USRE47142E1 (en) | Compounds and methods for treating inflammatory and fibrotic disorders | |
TWI301834B (en) | Pyrimidone compound and pharmaceutical composition including the same | |
CN104870429B (zh) | 苯并呋喃衍生物、其制备方法及其在医药上的应用 | |
KR20020015060A (ko) | 축합 이미다졸 화합물 및 당뇨병 치료약 | |
WO2006016548A1 (ja) | ヘテロ環化合物を含有する新規な抗マラリア剤 | |
CN108602834B (zh) | 一种布鲁顿酪氨酸激酶抑制剂 | |
CN106892898A (zh) | 氮杂糖衍生化的喹唑啉类化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |