NO760779L - - Google Patents

Info

Publication number: NO760779L
Authority: NO; Norway
Prior art keywords: pyridinyl; pyrimidinyl; formula; pyrimidine; amino
Prior art date: 1975-03-07

Application number

NO760779A

Other languages

English (en)

Norwegian (no)

Inventor

G Y Lesher

B Singh

Original Assignee

Sterling Drug Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-03-07

Filing date

1976-03-05

Publication date

1976-09-08

1976-03-05 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1976-09-08 Publication of NO760779L publication Critical patent/NO760779L/no

Links

-1 2-pyridinyl Chemical group 0.000 claims description 78
150000001875 compounds Chemical class 0.000 claims description 67
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 34
AFNZWLWIUXHAIW-UHFFFAOYSA-N 2-pyridin-4-ylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2C=CN=CC=2)=N1 AFNZWLWIUXHAIW-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
239000004202 carbamide Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 15
MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 claims description 13
239000012458 free base Substances 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000012948 isocyanate Substances 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
150000002513 isocyanates Chemical class 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
239000000203 mixture Substances 0.000 description 53
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
239000007787 solid Substances 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 26
229910000104 sodium hydride Inorganic materials 0.000 description 20
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
239000012312 sodium hydride Substances 0.000 description 19
239000004533 oil dispersion Substances 0.000 description 18
229960001760 dimethyl sulfoxide Drugs 0.000 description 17
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
KNXKVYCVGXFLES-UHFFFAOYSA-N pyridine-2-carboximidamide Chemical compound NC(=N)C1=CC=CC=N1 KNXKVYCVGXFLES-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000003814 drug Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
OBXXCFFJBAUAAE-UHFFFAOYSA-N 1-tert-butyl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CC(C)(C)NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 OBXXCFFJBAUAAE-UHFFFAOYSA-N 0.000 description 5
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 5
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 5
USBDVWRRXXQEOL-UHFFFAOYSA-N 2-pyridin-3-ylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2C=NC=CC=2)=N1 USBDVWRRXXQEOL-UHFFFAOYSA-N 0.000 description 5
239000000463 material Substances 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
UDHZYEWSTDYKCZ-UHFFFAOYSA-N pyridine-4-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=NC=C1 UDHZYEWSTDYKCZ-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
VFMNIYGZWOAILQ-UHFFFAOYSA-N butyl n-(2-pyridin-4-ylpyrimidin-4-yl)carbamate Chemical compound CCCCOC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 VFMNIYGZWOAILQ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
239000000376 reactant Substances 0.000 description 4
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 description 4
238000005406 washing Methods 0.000 description 4
VIHXWWJJHFGFIX-UHFFFAOYSA-N (6-methyl-2-pyridin-4-ylpyrimidin-4-yl)hydrazine Chemical compound CC1=CC(NN)=NC(C=2C=CN=CC=2)=N1 VIHXWWJJHFGFIX-UHFFFAOYSA-N 0.000 description 3
SJJOXQXXTAJQNH-UHFFFAOYSA-N 1-propan-2-yl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CC(C)NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 SJJOXQXXTAJQNH-UHFFFAOYSA-N 0.000 description 3
OPVQYFLTGBIQKG-UHFFFAOYSA-N 2-(piperidin-1-ylmethyl)prop-2-enenitrile Chemical compound N#CC(=C)CN1CCCCC1 OPVQYFLTGBIQKG-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
JMDXPMYETBVHIN-UHFFFAOYSA-N 6-amino-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N1C(N)=CC(=O)N=C1C1=CC=NC=C1 JMDXPMYETBVHIN-UHFFFAOYSA-N 0.000 description 3
UFMQZZRBKSOEKS-UHFFFAOYSA-N 6-methyl-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1C1=CC=NC=C1 UFMQZZRBKSOEKS-UHFFFAOYSA-N 0.000 description 3
KNKKGGMVDGAMLG-UHFFFAOYSA-N 6-methyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C=2C=CN=CC=2)=N1 KNKKGGMVDGAMLG-UHFFFAOYSA-N 0.000 description 3
FDBQKMBNSZRZOG-UHFFFAOYSA-N 6-propyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CCCC1=CC(N)=NC(C=2C=CN=CC=2)=N1 FDBQKMBNSZRZOG-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
239000000043 antiallergic agent Substances 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003610 charcoal Substances 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
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000002768 hydroxyalkyl group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
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 3
GGQNTXJGAGWGFD-UHFFFAOYSA-N n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C1=CN=CN1C(=O)NC(N=1)=CC=NC=1C1=CC=NC=C1 GGQNTXJGAGWGFD-UHFFFAOYSA-N 0.000 description 3
GSBUSAXXQRTXHM-UHFFFAOYSA-N n-ethyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CCNC1=CC=NC(C=2C=CN=CC=2)=N1 GSBUSAXXQRTXHM-UHFFFAOYSA-N 0.000 description 3
XRCXVDGCHVDNNM-UHFFFAOYSA-N n-methyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CNC1=CC=NC(C=2C=CN=CC=2)=N1 XRCXVDGCHVDNNM-UHFFFAOYSA-N 0.000 description 3
DNEXFQYHSNWHMY-UHFFFAOYSA-N n-methyl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(C)C(=O)N1C=CN=C1 DNEXFQYHSNWHMY-UHFFFAOYSA-N 0.000 description 3
GVDHZFJYZKAQNS-UHFFFAOYSA-N n-tert-butyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CC(C)(C)NC1=CC=NC(C=2C=CN=CC=2)=N1 GVDHZFJYZKAQNS-UHFFFAOYSA-N 0.000 description 3
PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 3
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
CNKRRFAEIGKEGM-UHFFFAOYSA-N (2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 CNKRRFAEIGKEGM-UHFFFAOYSA-N 0.000 description 2
HUPVIAINOSTNBJ-HWKANZROSA-N (e)-3-ethoxyprop-2-enenitrile Chemical compound CCO\C=C\C#N HUPVIAINOSTNBJ-HWKANZROSA-N 0.000 description 2
AZEUCUSUIMCPBR-UHFFFAOYSA-N 1-butyl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CCCCNC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 AZEUCUSUIMCPBR-UHFFFAOYSA-N 0.000 description 2
ATGVVYDHVDFRIG-UHFFFAOYSA-N 1-ethyl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CCNC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 ATGVVYDHVDFRIG-UHFFFAOYSA-N 0.000 description 2
RMWJEHRXXITFPZ-UHFFFAOYSA-N 1-phenyl-3-pyrimidin-4-ylurea Chemical compound C=1C=NC=NC=1NC(=O)NC1=CC=CC=C1 RMWJEHRXXITFPZ-UHFFFAOYSA-N 0.000 description 2
NTAKWJMSIAKFNC-UHFFFAOYSA-N 1-propan-2-yl-3-(2-pyridin-3-ylpyrimidin-4-yl)urea Chemical compound CC(C)NC(=O)NC1=CC=NC(C=2C=NC=CC=2)=N1 NTAKWJMSIAKFNC-UHFFFAOYSA-N 0.000 description 2
SLKJVTYGOQRQIM-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)pyrimidin-4-amine Chemical compound CC1=NC(C)=CC(C=2N=C(N)C=CN=2)=C1 SLKJVTYGOQRQIM-UHFFFAOYSA-N 0.000 description 2
AADBRLIAYJLVMH-UHFFFAOYSA-N 2-(2-ethylpyridin-4-yl)pyrimidin-4-amine Chemical compound C1=NC(CC)=CC(C=2N=C(N)C=CN=2)=C1 AADBRLIAYJLVMH-UHFFFAOYSA-N 0.000 description 2
NWPDZYPZSYEIKZ-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)pyrimidin-4-amine Chemical compound C1=NC(C)=CC(C=2N=C(N)C=CN=2)=C1 NWPDZYPZSYEIKZ-UHFFFAOYSA-N 0.000 description 2
CRVQOVRFQOPXPG-UHFFFAOYSA-N 2-(3-methylpyridin-4-yl)pyrimidin-4-amine Chemical compound CC1=CN=CC=C1C1=NC=CC(N)=N1 CRVQOVRFQOPXPG-UHFFFAOYSA-N 0.000 description 2
CRLLPKLYUMUJHY-UHFFFAOYSA-N 2-pyridin-2-ylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2N=CC=CC=2)=N1 CRLLPKLYUMUJHY-UHFFFAOYSA-N 0.000 description 2
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 2
DHNOAUDHLPLXQG-UHFFFAOYSA-N 4-amino-2-pyridin-4-ylpyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(C=2C=CN=CC=2)=N1 DHNOAUDHLPLXQG-UHFFFAOYSA-N 0.000 description 2
ZSRSIZQAKUIMTE-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-4-ylpyrimidine Chemical compound CC1=CC(Cl)=NC(C=2C=CN=CC=2)=N1 ZSRSIZQAKUIMTE-UHFFFAOYSA-N 0.000 description 2
OZQWBFMYEFXYRX-UHFFFAOYSA-N 5-methyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound N1=C(N)C(C)=CN=C1C1=CC=NC=C1 OZQWBFMYEFXYRX-UHFFFAOYSA-N 0.000 description 2
MPYZHDZCEHZQSB-UHFFFAOYSA-N 6-propyl-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound CCCC1=CC(O)=NC(C=2C=CN=CC=2)=N1 MPYZHDZCEHZQSB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NLQDARDXBZWFKE-UHFFFAOYSA-N CC(N(C1=CC=NC(C2=CC=NC=C2)=N1)O)=O Chemical compound CC(N(C1=CC=NC(C2=CC=NC=C2)=N1)O)=O NLQDARDXBZWFKE-UHFFFAOYSA-N 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 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
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
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RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 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
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000037230 mobility Effects 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
QMKKJBRRKIKWFK-UHFFFAOYSA-N n,2,2-trimethylpropanamide Chemical compound CNC(=O)C(C)(C)C QMKKJBRRKIKWFK-UHFFFAOYSA-N 0.000 description 1
HGXADWSUAXJGSP-UHFFFAOYSA-N n,6-dimethyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CNC1=CC(C)=NC(C=2C=CN=CC=2)=N1 HGXADWSUAXJGSP-UHFFFAOYSA-N 0.000 description 1
OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
KMODMELPUBASHE-UHFFFAOYSA-N n-(2-pyridin-4-ylpyrimidin-4-yl)hexanamide Chemical compound CCCCCC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 KMODMELPUBASHE-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
YDFTXRCSHWSELZ-UHFFFAOYSA-N n-ethyl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(CC)C(=O)N1C=CN=C1 YDFTXRCSHWSELZ-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
UJKKNNPWQLWKRY-UHFFFAOYSA-N n-propan-2-yl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(C(C)C)C(=O)N1C=CN=C1 UJKKNNPWQLWKRY-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
GSUAURPIYWEOII-UHFFFAOYSA-N pyridine-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=CN=C1 GSUAURPIYWEOII-UHFFFAOYSA-N 0.000 description 1
RJLCIACWXJHILW-UHFFFAOYSA-N pyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=NC=C1 RJLCIACWXJHILW-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
150000003254 radicals Chemical class 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000007655 standard test method Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc 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
235000012976 tarts Nutrition 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
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO760779A 1975-03-07 1976-03-05 NO760779L (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/556,213 US4008235A (en)	1975-03-07	1975-03-07	N-[2-(pyridinyl)-4-pyrimidinyl]ureas

Publications (1)

Publication Number	Publication Date
NO760779L true NO760779L (de)	1976-09-08

Family

ID=24220364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO760779A NO760779L (de)	1975-03-07	1976-03-05

Country Status (15)

Country	Link
US (1)	US4008235A (de)
JP (1)	JPS51113884A (de)
AU (1)	AU1169176A (de)
BE (1)	BE839163A (de)
CA (1)	CA1051432A (de)
DE (1)	DE2609208A1 (de)
DK (1)	DK97476A (de)
FI (1)	FI760555A (de)
FR (1)	FR2302744A1 (de)
GB (1)	GB1530412A (de)
NL (1)	NL7602379A (de)
NO (1)	NO760779L (de)
PH (1)	PH11387A (de)
SE (1)	SE7603051L (de)
ZA (1)	ZA761300B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4144338A (en) *	1977-02-17	1979-03-13	Merck & Co., Inc.	N-pyrimidinyl-N-dialkylaminoalkyl ureas
US4415575A (en) *	1979-03-13	1983-11-15	Merck & Co., Inc.	Suppression of gastric acid secretion using pyrimidylcarbamates
US4226871A (en) *	1979-03-13	1980-10-07	Merck & Co., Inc.	Heterocyclic carbamates
CA1244028A (en) *	1983-04-14	1988-11-01	Hans Maag	Pyrimidine derivatives
US4504482A (en) *	1983-07-28	1985-03-12	Sterling Drug Inc.	[5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof
EP0234104B1 (de) *	1985-12-03	1990-10-24	Sumitomo Chemical Company, Limited	Pyridinylpyrimidin-Derivate, Verfahren zu deren Herstellung und diese als wirksamen Stoff enthaltende Pflanzenkrankheiten-Schutzmittel
PH23565A (en) *	1986-09-05	1989-08-25	Sumitomo Chemical Co	Novel pyrimidinylpyrimidine derivatives and a plant disease protectant containing them as the active ingredient
NZ219486A (en) *	1987-03-04	1990-05-28	Kenneth Wilfred Feisst	Foldable and rollable building
ATE139117T1 (de) *	1990-07-03	1996-06-15	Mitsui Petrochemical Ind	Pyrimidin-verbindung und ihr pharmazeutisch annehmbares salz
EP2368883A1 (de) *	2010-03-24	2011-09-28	Lonza Ltd.	Verfahren zur Herstellung 2-substituierter 4-Amino-5-cyanpyrimidine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3673184A (en) *	1970-09-02	1972-06-27	Dainippon Pharmaceutical Co	Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives

1975
- 1975-03-07 US US05/556,213 patent/US4008235A/en not_active Expired - Lifetime
1976
- 1976-02-23 GB GB7110/76A patent/GB1530412A/en not_active Expired
- 1976-03-04 FI FI760555A patent/FI760555A/fi not_active Application Discontinuation
- 1976-03-04 ZA ZA761300A patent/ZA761300B/xx unknown
- 1976-03-04 CA CA247,151A patent/CA1051432A/en not_active Expired
- 1976-03-04 AU AU11691/76A patent/AU1169176A/en not_active Expired
- 1976-03-04 BE BE1007228A patent/BE839163A/xx unknown
- 1976-03-05 PH PH18176A patent/PH11387A/en unknown
- 1976-03-05 NO NO760779A patent/NO760779L/no unknown
- 1976-03-05 JP JP51024067A patent/JPS51113884A/ja active Pending
- 1976-03-05 FR FR7606352A patent/FR2302744A1/fr active Granted
- 1976-03-05 SE SE7603051A patent/SE7603051L/xx unknown
- 1976-03-05 NL NL7602379A patent/NL7602379A/xx not_active Application Discontinuation
- 1976-03-05 DE DE19762609208 patent/DE2609208A1/de active Pending
- 1976-03-05 DK DK97476*#A patent/DK97476A/da unknown

Also Published As

Publication number	Publication date
DE2609208A1 (de)	1976-09-16
US4008235A (en)	1977-02-15
AU1169176A (en)	1977-09-08
GB1530412A (en)	1978-11-01
BE839163A (fr)	1976-09-06
CA1051432A (en)	1979-03-27
JPS51113884A (en)	1976-10-07
SE7603051L (sv)	1976-09-08
NL7602379A (nl)	1976-09-09
FR2302744A1 (fr)	1976-10-01
DK97476A (da)	1976-09-08
FR2302744B1 (de)	1979-09-21
ZA761300B (en)	1977-02-23
PH11387A (en)	1977-11-22
FI760555A (de)	1976-09-08

Publication	Publication Date	Title
FI89265C (fi)	1993-09-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade piperazinylpyridiner eller piperazinylimidazoler
DE69826883T2 (de)	2005-02-03	Heteroaryl diazacycloalkane als cholinergische ligande für nikotin-acetylcholin-rezeptoren
NO760779L (de)	1976-09-08
DE2822544A1 (de)	1978-12-07	Neue pharmazeutisch wirksame verbindungen, verfahren zu ihrer herstellung und arzneimittel
US5854232A (en)	1998-12-29	Acyclic anc cyclic amides as neurotransmitter release enhancers
NO834778L (no)	1984-06-25	Fremgangsmaate for fremstilling av pyridinderivater for anvendelse som histamin h1-antagonister
US6951875B2 (en)	2005-10-04	Conjugated aromatic compounds with a pyridine substituent
US5925655A (en)	1999-07-20	αv β3 antagonists
US4118571A (en)	1978-10-03	4-Acylamino-2-(pyridinyl)pyrimidine derivatives
Whitehead et al.	1958	Diuretics. III. 4, 6-Diaminopyrimidines
US5532249A (en)	1996-07-02	Disubstituted polycyclic systems as cognition enhancers
US4053475A (en)	1977-10-11	N-[2-(Pyridinyl)-4-pyrimidinyl]ureas preparation
JPS5995287A (ja)	1984-06-01	２−（ピリジニルまたはヒドロキシフエニル）８−置換ピリド〔２，３−ｄ〕ピリミジン−５（８Ｈ）−オン類、その製造方法およびそれを含む医薬組成物
US4764519A (en)	1988-08-16	3-hydroxypyridines
US4032523A (en)	1977-06-28	4-amino (or halo or hydroxy or hydrazino)-2-(pyridinyl)pyrimidines
JPS60502003A (ja)	1985-11-21	強心剤として有効な〔（ピリジニル）−２−ピリミジニル〕尿素及び同化合物を含む製剤
DE2900288A1 (de)	1979-07-12	Aminoderivate von pyrazol eckige klammer auf 1,5-a eckige klammer zu s-triazin, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
NO851066L (no)	1985-03-18	Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling derav
DE2418498A1 (de)	1974-11-07	Verschmolzene pyrimidine und deren herstellung
US4086233A (en)	1978-04-25	4-(Substituted-amino)-2-(pyridinyl) pyrimidine derivatives
US4077955A (en)	1978-03-07	Amino derivatives of 1,2,3,4-tetrahydro-2-oxopyrido[2,2-b]-pyrazine carboxylic acids and esters
DE3427823A1 (de)	1985-02-07	5-subst.-(1,2,4) triazolo (1,5-c) pyrimidin-2-amine
US4109092A (en)	1978-08-22	Preparation of 2-(pyridinyl)-4-pyrimidinamines
NZ254308A (en)	1997-09-22	Substituted pyridyl- pyrimidylpiperazine derivatives
US4514400A (en)	1985-04-30	Cardiotonic 5-heteroaryl-pyridone