NO851066L - Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling derav - Google Patents
Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling deravInfo
- Publication number
- NO851066L NO851066L NO851066A NO851066A NO851066L NO 851066 L NO851066 L NO 851066L NO 851066 A NO851066 A NO 851066A NO 851066 A NO851066 A NO 851066A NO 851066 L NO851066 L NO 851066L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- dimethylamino
- methyl
- pyrimidinamine
- formula
- Prior art date
Links
- 239000000496 cardiotonic agent Substances 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 44
- -1 N-(2- hydroxyethyl) methylamino Chemical group 0.000 claims description 39
- SWSQBOPZIKWTGO-UHFFFAOYSA-N 1,1-dimethylguanidine Chemical compound CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 23
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 14
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- ORTUDDOFSUHQKZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1-methylguanidine Chemical compound NC(=N)N(C)CCO ORTUDDOFSUHQKZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 230000000397 acetylating effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- ACPFLXJEPKOPGF-UHFFFAOYSA-N diaminomethylidene(dimethyl)azanium;hydrogen sulfate Chemical compound [O-]S([O-])(=O)=O.C[NH+](C)C([NH3+])=N ACPFLXJEPKOPGF-UHFFFAOYSA-N 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- FSHIOHCNOLTWBC-UHFFFAOYSA-N 5-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=NC=C1 FSHIOHCNOLTWBC-UHFFFAOYSA-N 0.000 description 7
- 241000700199 Cavia porcellus Species 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000747 cardiac effect Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 210000003540 papillary muscle Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 5
- 230000003177 cardiotonic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- FEYDRISSTYDXTL-UHFFFAOYSA-N n,n,5-trimethyl-4-pyridin-4-ylpyrimidin-2-amine Chemical compound CN(C)C1=NC=C(C)C(C=2C=CN=CC=2)=N1 FEYDRISSTYDXTL-UHFFFAOYSA-N 0.000 description 5
- IBTPGSHNAHARFZ-UHFFFAOYSA-N n,n-dimethyl-4-pyridin-4-ylpyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2C=CN=CC=2)=N1 IBTPGSHNAHARFZ-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BQNIEGASJMSDBW-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1-methylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(=N)N(C)CCO BQNIEGASJMSDBW-UHFFFAOYSA-N 0.000 description 4
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 4
- MZLRFUCMBQWLNV-UHFFFAOYSA-N 3-(dimethylamino)-1-pyridin-3-ylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CN=C1 MZLRFUCMBQWLNV-UHFFFAOYSA-N 0.000 description 4
- PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001746 atrial effect Effects 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002357 guanidines Chemical class 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- YUAFJVLPXRDSCT-UHFFFAOYSA-N n-(5-pyridin-4-ylpyrimidin-2-yl)propanamide Chemical compound C1=NC(NC(=O)CC)=NC=C1C1=CC=NC=C1 YUAFJVLPXRDSCT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- JPABEPAVSTWSCL-UHFFFAOYSA-N 2-[methyl-(4-pyridin-4-ylpyrimidin-2-yl)amino]ethanol Chemical compound OCCN(C)C1=NC=CC(C=2C=CN=CC=2)=N1 JPABEPAVSTWSCL-UHFFFAOYSA-N 0.000 description 2
- JZGHSXBVKSMAKH-UHFFFAOYSA-N 3-(dimethylamino)-1-pyridin-4-ylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=NC=C1 JZGHSXBVKSMAKH-UHFFFAOYSA-N 0.000 description 2
- GUEOXWVKDZNZGR-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-3-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=CN=C1 GUEOXWVKDZNZGR-UHFFFAOYSA-N 0.000 description 2
- RTSJEVLSUJRMPL-UHFFFAOYSA-N 4-methyl-5-pyridin-4-ylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=CC=NC=C1 RTSJEVLSUJRMPL-UHFFFAOYSA-N 0.000 description 2
- FMCZZTJYJOQZHC-UHFFFAOYSA-N 4-pyridin-4-ylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=CN=CC=2)=N1 FMCZZTJYJOQZHC-UHFFFAOYSA-N 0.000 description 2
- USVSSALFFDLXDR-UHFFFAOYSA-N 5-methyl-4-pyridin-4-ylpyrimidin-2-amine Chemical compound CC1=CN=C(N)N=C1C1=CC=NC=C1 USVSSALFFDLXDR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 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
- WVENMCMLSYNNCX-UHFFFAOYSA-N n,n-dimethyl-4-pyridin-3-ylpyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2C=NC=CC=2)=N1 WVENMCMLSYNNCX-UHFFFAOYSA-N 0.000 description 2
- SRDOBKLTYHTYMG-UHFFFAOYSA-N n,n-dimethyl-5-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1=CC=CN=C1 SRDOBKLTYHTYMG-UHFFFAOYSA-N 0.000 description 2
- YPVDONFWADHAPP-UHFFFAOYSA-N n-(5-pyridin-4-ylpyrimidin-2-yl)acetamide Chemical compound C1=NC(NC(=O)C)=NC=C1C1=CC=NC=C1 YPVDONFWADHAPP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- LPNRUMVKXCLEBE-JXVRESAISA-L (3r)-4-[[(e)-2-[5-ethyl-4-(4-fluorophenyl)-6-phenyl-2-propan-2-ylpyridin-3-yl]ethenyl]-oxidophosphoryl]-3-hydroxybutanoate Chemical compound CCC1=C(C=2C=CC=CC=2)N=C(C(C)C)C(\C=C\P([O-])(=O)C[C@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 LPNRUMVKXCLEBE-JXVRESAISA-L 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- QOLHWXNSCZGWHK-BWBORTOCSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecylcarbamoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)NCCCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 QOLHWXNSCZGWHK-BWBORTOCSA-N 0.000 description 1
- MPXSBRUHMJWVIZ-UHFFFAOYSA-N 2-(dimethylamino)-1-pyridin-4-ylbut-2-en-1-one Chemical compound CC=C(N(C)C)C(=O)C1=CC=NC=C1 MPXSBRUHMJWVIZ-UHFFFAOYSA-N 0.000 description 1
- OLMYHOMGARTZPR-UHFFFAOYSA-N 2-[methyl-(4-pyridin-3-ylpyrimidin-2-yl)amino]ethanol Chemical compound OCCN(C)C1=NC=CC(C=2C=NC=CC=2)=N1 OLMYHOMGARTZPR-UHFFFAOYSA-N 0.000 description 1
- XEJZFVHUDVFSIE-UHFFFAOYSA-N 2-[methyl-[4-(2-methylpyridin-3-yl)pyrimidin-2-yl]amino]ethanol Chemical compound OCCN(C)C1=NC=CC(C=2C(=NC=CC=2)C)=N1 XEJZFVHUDVFSIE-UHFFFAOYSA-N 0.000 description 1
- DCIOJVQYSNUSBG-UHFFFAOYSA-N 3-(dimethylamino)-1-(2,6-dimethylpyridin-4-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC(C)=NC(C)=C1 DCIOJVQYSNUSBG-UHFFFAOYSA-N 0.000 description 1
- BBGQIEHILOVAKB-UHFFFAOYSA-N 3-(dimethylamino)-1-(3-ethylpyridin-4-yl)prop-2-en-1-one Chemical compound CCC1=CN=CC=C1C(=O)C=CN(C)C BBGQIEHILOVAKB-UHFFFAOYSA-N 0.000 description 1
- GWBCZEQJRHMMJB-UHFFFAOYSA-N 3-(dimethylamino)-2-(2,6-dimethylpyridin-4-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC(C)=NC(C)=C1 GWBCZEQJRHMMJB-UHFFFAOYSA-N 0.000 description 1
- SUBBRFCUQHQJHO-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-methylpyridin-3-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=CN=C1C SUBBRFCUQHQJHO-UHFFFAOYSA-N 0.000 description 1
- RBZKQLKVNNSDRU-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-methylpyridin-4-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC(C)=C1 RBZKQLKVNNSDRU-UHFFFAOYSA-N 0.000 description 1
- FLHGMYFEEVAZCP-UHFFFAOYSA-N 3-(dimethylamino)-2-(5-methylpyridin-3-yl)but-2-enal Chemical compound CN(C)C(C)=C(C=O)C1=CN=CC(C)=C1 FLHGMYFEEVAZCP-UHFFFAOYSA-N 0.000 description 1
- VWFINOXYULRIHL-UHFFFAOYSA-N 3-(dimethylamino)-2-methyl-1-pyridin-4-ylprop-2-en-1-one Chemical compound CN(C)C=C(C)C(=O)C1=CC=NC=C1 VWFINOXYULRIHL-UHFFFAOYSA-N 0.000 description 1
- CUAAVFXFCLYBBV-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylbut-2-enal Chemical compound CN(C)C(C)=C(C=O)C1=CC=NC=C1 CUAAVFXFCLYBBV-UHFFFAOYSA-N 0.000 description 1
- BBRWZLBJXPHJIH-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-n,n-dimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2C=C(C)N=C(C)C=2)=N1 BBRWZLBJXPHJIH-UHFFFAOYSA-N 0.000 description 1
- LHRFGIOZFUYTRP-UHFFFAOYSA-N 4-(3-ethylpyridin-4-yl)-n,n-dimethylpyrimidin-2-amine Chemical compound CCC1=CN=CC=C1C1=CC=NC(N(C)C)=N1 LHRFGIOZFUYTRP-UHFFFAOYSA-N 0.000 description 1
- VBJFIFFEIMTZNL-UHFFFAOYSA-N 4-methyl-5-(5-methylpyridin-3-yl)pyrimidin-2-amine Chemical compound CC1=CN=CC(C=2C(=NC(N)=NC=2)C)=C1 VBJFIFFEIMTZNL-UHFFFAOYSA-N 0.000 description 1
- LQHQKYWYKPLKCH-UHFFFAOYSA-N 4-pyridin-3-ylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=NC=CC=2)=N1 LQHQKYWYKPLKCH-UHFFFAOYSA-N 0.000 description 1
- PSTFCRFLNNOYJB-UHFFFAOYSA-N 5-(2,6-dimethylpyridin-4-yl)-n,n-dimethylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1=CC(C)=NC(C)=C1 PSTFCRFLNNOYJB-UHFFFAOYSA-N 0.000 description 1
- RVTIDQGTFPZRGE-UHFFFAOYSA-N 5-(2-methylpyridin-3-yl)pyrimidin-2-amine Chemical compound CC1=NC=CC=C1C1=CN=C(N)N=C1 RVTIDQGTFPZRGE-UHFFFAOYSA-N 0.000 description 1
- GQSARKAWVKBQNN-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)pyrimidin-2-amine Chemical compound C1=NC(C)=CC(C=2C=NC(N)=NC=2)=C1 GQSARKAWVKBQNN-UHFFFAOYSA-N 0.000 description 1
- PFUBNHHFFFSNDV-UHFFFAOYSA-N 5-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=CN=C1 PFUBNHHFFFSNDV-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229940126559 Compound 4e Drugs 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 241001465754 Metazoa Species 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 241000282898 Sus scrofa Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229940077388 benzenesulfonate Drugs 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
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- VLGSUBRGDBJMTI-UHFFFAOYSA-N n,n-dimethyl-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1=CC=NC=C1 VLGSUBRGDBJMTI-UHFFFAOYSA-N 0.000 description 1
- ZZLJJAGIUYYIRN-UHFFFAOYSA-N n-(2-pyridin-4-ylpyrimidin-4-yl)acetamide Chemical compound CC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 ZZLJJAGIUYYIRN-UHFFFAOYSA-N 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
- GOERPUSQLHSQHQ-UHFFFAOYSA-N n-methyl-4-pyridin-4-ylpyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2C=CN=CC=2)=N1 GOERPUSQLHSQHQ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007790 scraping Methods 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
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/516,820 US4512993A (en) | 1983-07-25 | 1983-07-25 | 4(Or 5)-(pyridinyl)-2-pyrimidinamines and cardiotonic use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851066L true NO851066L (no) | 1985-03-18 |
Family
ID=24057230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851066A NO851066L (no) | 1983-07-25 | 1985-03-18 | Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling derav |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4512993A (ja) |
| EP (1) | EP0150206A4 (ja) |
| JP (1) | JPS60501952A (ja) |
| KR (1) | KR850001192A (ja) |
| AU (1) | AU561765B2 (ja) |
| DK (1) | DK127385D0 (ja) |
| FI (1) | FI73988C (ja) |
| IL (1) | IL72307A (ja) |
| IT (1) | IT1176419B (ja) |
| NO (1) | NO851066L (ja) |
| NZ (1) | NZ208818A (ja) |
| PH (1) | PH20211A (ja) |
| WO (1) | WO1985000604A1 (ja) |
| ZA (1) | ZA845263B (ja) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4876252A (en) * | 1986-01-13 | 1989-10-24 | American Cyanamid Company | 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines |
| SG47583A1 (en) * | 1986-01-13 | 1998-04-17 | American Cyanamid Co | 4,5,6-Substituted-n- (substituted-phenyl) -2- pyrimidinamines |
| US4788195A (en) * | 1986-01-13 | 1988-11-29 | American Cyanamid Company | 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| US5952331A (en) * | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| US5958934A (en) * | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| USRE43932E1 (en) | 1997-07-18 | 2013-01-15 | Novartis Ag | Crystal modification of a N-phenyl-2-pyrimidineamine derivative, processes for its manufacture and its use |
| WO2009007187A1 (de) * | 2007-07-09 | 2009-01-15 | Basf Se | Substituierte 5-hetarylpyrimidine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US30024A (en) * | 1860-09-11 | Chaeles b | ||
| US4018770A (en) | 1975-03-03 | 1977-04-19 | Sterling Drug Inc. | N-(2-(pyridinyl)-4-pyrimidinyl)-aminomethylenemalonates and analogs |
| US4086233A (en) * | 1976-07-23 | 1978-04-25 | Sterling Drug Inc. | 4-(Substituted-amino)-2-(pyridinyl) pyrimidine derivatives |
-
1983
- 1983-07-25 US US06/516,820 patent/US4512993A/en not_active Expired - Fee Related
-
1984
- 1984-06-29 EP EP19840902865 patent/EP0150206A4/en not_active Ceased
- 1984-06-29 WO PCT/US1984/001051 patent/WO1985000604A1/en not_active Application Discontinuation
- 1984-06-29 AU AU31530/84A patent/AU561765B2/en not_active Ceased
- 1984-06-29 JP JP59502757A patent/JPS60501952A/ja active Pending
- 1984-07-05 IL IL72307A patent/IL72307A/xx unknown
- 1984-07-06 NZ NZ208818A patent/NZ208818A/en unknown
- 1984-07-09 ZA ZA845263A patent/ZA845263B/xx unknown
- 1984-07-18 IT IT21939/84A patent/IT1176419B/it active
- 1984-07-19 KR KR1019840004260A patent/KR850001192A/ko not_active Application Discontinuation
- 1984-07-20 PH PH31007A patent/PH20211A/en unknown
-
1985
- 1985-03-18 NO NO851066A patent/NO851066L/no unknown
- 1985-03-20 FI FI851112A patent/FI73988C/fi not_active IP Right Cessation
- 1985-03-21 DK DK127385A patent/DK127385D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8421939A0 (it) | 1984-07-18 |
| IL72307A0 (en) | 1984-11-30 |
| EP0150206A1 (en) | 1985-08-07 |
| FI851112A0 (fi) | 1985-03-20 |
| NZ208818A (en) | 1988-02-12 |
| DK127385A (da) | 1985-03-21 |
| FI73988C (fi) | 1987-12-10 |
| KR850001192A (ko) | 1985-03-16 |
| FI73988B (fi) | 1987-08-31 |
| EP0150206A4 (en) | 1986-03-18 |
| IT1176419B (it) | 1987-08-18 |
| WO1985000604A1 (en) | 1985-02-14 |
| DK127385D0 (da) | 1985-03-21 |
| PH20211A (en) | 1986-10-20 |
| US4512993A (en) | 1985-04-23 |
| IL72307A (en) | 1987-12-20 |
| IT8421939A1 (it) | 1986-01-18 |
| AU561765B2 (en) | 1987-05-14 |
| FI851112L (fi) | 1985-03-20 |
| AU3153084A (en) | 1985-03-04 |
| JPS60501952A (ja) | 1985-11-14 |
| ZA845263B (en) | 1985-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO811040L (no) | Diaminopyridiner og fremgangsmaate til deres fremstilling | |
| NO802507L (no) | 6-pyridazinoner med kardiotonisk virkning. | |
| NO851066L (no) | Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling derav | |
| US4504482A (en) | [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof | |
| US4298609A (en) | 4,5-Dihydro-6-(4-pyridinyl)-3-pyridazinol and salts, their preparation and use as blood pressure lowering agents | |
| US4391811A (en) | 2-Amino-6-(pyridinyl)-3H-imidazo[4,5-b]pyridines and their cardiotonic use | |
| US4304775A (en) | 3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof | |
| NO803911L (no) | 3-acylamino-5-(pyridinyl)-2(1h)-pyridinoner og fremgangsmaate til fremstilling derav | |
| US4317827A (en) | 4-[4(or 3)-Acylaminophenyl]pyridines and their use as cardiotonics | |
| US4305948A (en) | N-Hydroxy-1,2-dihydro-2-oxo-5-(pyridinyl)-nicotinimidamide and their cardiotonic use | |
| US4346221A (en) | Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from 6-(pyridinyl)-3(2H)-pyridazinones | |
| US4473571A (en) | 8-Substituted-2-(4-pyridinyl)-9H-purin-6-amines and their cardiotonic use | |
| US4590194A (en) | 3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use | |
| US4374141A (en) | 2-Substituted amino-5-(pyridinyl)-nicotinamides and their cardiotonic use | |
| US4362734A (en) | 2-(Substituted-amino)-5-(pyridinyl-nicotinonitriles, and their cardiotonic use | |
| US4337253A (en) | 4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic | |
| US4305943A (en) | 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics | |
| US4304776A (en) | 4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as intermediates and cardiotonics | |
| US4376775A (en) | N-[4-(4-Pyridinyl)phenyl]ureas and their cardiotonic use | |
| US4354026A (en) | 3-Chloro-6-(pyridinyl)-pyridazines | |
| US4338446A (en) | Di-(lower-alkyl)hydroxy-[2-oxo-2-(pyridinyl)ethyl]-propanedioates | |
| US4503228A (en) | 2-(Pyridinyl)-4,5,6-pyrimidinetriamines | |
| US4377585A (en) | Use of 4-[4(or 3)-aminophenyl]pyridines as cardiotonic agents | |
| US4362735A (en) | 3-[(3-Oxo-1-butenyl)amino]-5-(pyridinyl)-2(1H)-pyridinones and their cardiotonic use | |
| US4339584A (en) | Process for preparing 3-amino-5-(pyridinyl)-2(1H)-pyridinones via N-hydroxy-1,2-dihydro-2-oxo-5-(pyridinyl)-nicotinimidamide by reaction with polyphosphoric acid |