CA1147335A - Process for preparing pyrimidones - Google Patents
Process for preparing pyrimidonesInfo
- Publication number
- CA1147335A CA1147335A CA000321100A CA321100A CA1147335A CA 1147335 A CA1147335 A CA 1147335A CA 000321100 A CA000321100 A CA 000321100A CA 321100 A CA321100 A CA 321100A CA 1147335 A CA1147335 A CA 1147335A
- Authority
- CA
- Canada
- Prior art keywords
- pyrimidone
- pyridyl
- methyl
- furylmethylthio
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000008318 pyrimidones Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000019253 formic acid Nutrition 0.000 claims abstract description 5
- 125000006239 protecting group Chemical group 0.000 claims abstract description 5
- 150000003573 thiols Chemical class 0.000 claims abstract description 4
- 150000003141 primary amines Chemical class 0.000 claims abstract description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims abstract 3
- -1 pyridyl N-oxide Chemical class 0.000 claims description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 31
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 11
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- RHHFNUQDIRYPSI-UHFFFAOYSA-N n-[6-oxo-5-(pyridin-3-ylmethyl)-1h-pyrimidin-2-yl]nitramide Chemical compound N1C(N[N+](=O)[O-])=NC(=O)C(CC=2C=NC=CC=2)=C1 RHHFNUQDIRYPSI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- IIQFIDKGTDXLBU-UHFFFAOYSA-N benzyl thiohypochlorite Chemical compound ClSCC1=CC=CC=C1 IIQFIDKGTDXLBU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- CIWFVMDEULCLPN-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-[(5,6-dimethylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CN=C(C)C(C)=C1 CIWFVMDEULCLPN-UHFFFAOYSA-N 0.000 claims description 2
- YMVSCUJJVSENIP-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one;trihydrochloride Chemical compound Cl.Cl.Cl.O1C(CN(C)C)=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CC=C(C)N=C1 YMVSCUJJVSENIP-UHFFFAOYSA-N 0.000 claims description 2
- OAMKHQBKAMPNAB-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-(2-sulfanylethylamino)-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC1=CN=C(NCCS)NC1=O OAMKHQBKAMPNAB-UHFFFAOYSA-N 0.000 claims description 2
- MURUHMTVTKOWBY-UHFFFAOYSA-N donetidine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CC(=O)NC=C1 MURUHMTVTKOWBY-UHFFFAOYSA-N 0.000 claims description 2
- DYSDJZQYNYDJBU-UHFFFAOYSA-N n-[5-[(2-methoxypyridin-4-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(OC)=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 DYSDJZQYNYDJBU-UHFFFAOYSA-N 0.000 claims description 2
- KWBSLRQDOHBJPQ-UHFFFAOYSA-N n-[5-[(6-methylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(C)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O KWBSLRQDOHBJPQ-UHFFFAOYSA-N 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
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- IKEHSFKMCULMKJ-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CC=C(C)N=C1 IKEHSFKMCULMKJ-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- XSRVZSHASIYJMO-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CC=CN=C1 XSRVZSHASIYJMO-UHFFFAOYSA-N 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- VSPDYEHKAMKDNW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CC=CO1 VSPDYEHKAMKDNW-UHFFFAOYSA-N 0.000 claims 1
- ODCDELVLBDIECG-UHFFFAOYSA-N 2-[2-(furan-2-ylmethylsulfanyl)ethylamino]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound N=1C=C(CC=2C=NC=CC=2)C(=O)NC=1NCCSCC1=CC=CO1 ODCDELVLBDIECG-UHFFFAOYSA-N 0.000 claims 1
- ZILHMVNYNCTIEO-UHFFFAOYSA-N 2-[2-[1-[5-(dimethylamino)furan-2-yl]ethylsulfanyl]ethylamino]-5-[(2-oxo-1H-pyridin-4-yl)methyl]-1H-pyrimidin-6-one Chemical compound CN(C1=CC=C(O1)C(SCCNC1=NC=C(C(N1)=O)CC1=CC(=NC=C1)O)C)C ZILHMVNYNCTIEO-UHFFFAOYSA-N 0.000 claims 1
- FEQKZDDVINUMPR-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound N1C(SC)=NC(=O)C(CC=2C=NC(C)=CC=2)=C1 FEQKZDDVINUMPR-UHFFFAOYSA-N 0.000 claims 1
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- WCCXSTMOFAXKAF-UHFFFAOYSA-N n-[5-[(5,6-dimethylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound N1=C(C)C(C)=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 WCCXSTMOFAXKAF-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 10
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 125000000962 organic group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
- 239000000203 mixture Substances 0.000 description 85
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 29
- 238000010992 reflux Methods 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 24
- 229960001340 histamine Drugs 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 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 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 235000011167 hydrochloric acid Nutrition 0.000 description 11
- 229960000443 hydrochloric acid Drugs 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- TYPPUXQQMYIOGM-UHFFFAOYSA-N 5-[2-[(4-methoxyphenyl)methylsulfanyl]ethyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CSCCC1=CN=C(SC)NC1=O TYPPUXQQMYIOGM-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 7
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 5
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- IBEGQUIFACPAGF-UHFFFAOYSA-N ethyl 3-[4-(4-methoxyphenoxy)phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1OC1=CC=C(OC)C=C1 IBEGQUIFACPAGF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- OAZIAOCXVZMCCR-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)prop-2-enoic acid Chemical compound CC1=CC=C(C=CC(O)=O)C=N1 OAZIAOCXVZMCCR-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- HOYGMPDDEVYMNG-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=C(Cl)C=C1 HOYGMPDDEVYMNG-UHFFFAOYSA-N 0.000 description 3
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- OUHPHSYPKKLTKJ-UHFFFAOYSA-N ethyl 3-[3-(trifluoromethyl)phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=CC(C(F)(F)F)=C1 OUHPHSYPKKLTKJ-UHFFFAOYSA-N 0.000 description 3
- QUPOUJMPVNJELS-UHFFFAOYSA-N ethyl 3-[4-(4-chlorophenoxy)phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 QUPOUJMPVNJELS-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 210000003405 ileum Anatomy 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 2
- VOCKNCWQVHJMAE-UHFFFAOYSA-N 2-methoxypyridine-4-carbaldehyde Chemical compound COC1=CC(C=O)=CC=N1 VOCKNCWQVHJMAE-UHFFFAOYSA-N 0.000 description 2
- NZAZWLSRKMDRNS-UHFFFAOYSA-N 2-methoxypyridine-4-carbonitrile Chemical compound COC1=CC(C#N)=CC=N1 NZAZWLSRKMDRNS-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
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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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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GB5740/78 | 1978-02-13 | ||
GB574078 | 1978-02-13 | ||
GB22834/78 | 1978-05-25 | ||
GB2283478 | 1978-05-25 | ||
GB7844259 | 1978-11-13 | ||
GB44259/78 | 1978-11-13 |
Publications (1)
Publication Number | Publication Date |
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CA1147335A true CA1147335A (en) | 1983-05-31 |
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Family Applications (1)
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CA000321100A Expired CA1147335A (en) | 1978-02-13 | 1979-02-08 | Process for preparing pyrimidones |
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US (2) | US4234588A (en, 2012) |
EP (1) | EP0003677B1 (en, 2012) |
JP (1) | JPS54115385A (en, 2012) |
AR (1) | AR223476A1 (en, 2012) |
AT (1) | AT372087B (en, 2012) |
AU (1) | AU531757B2 (en, 2012) |
BG (1) | BG34906A3 (en, 2012) |
CA (1) | CA1147335A (en, 2012) |
DD (1) | DD142052A5 (en, 2012) |
DE (1) | DE2961289D1 (en, 2012) |
DK (1) | DK54879A (en, 2012) |
EG (1) | EG13747A (en, 2012) |
ES (1) | ES477667A1 (en, 2012) |
FI (1) | FI66000C (en, 2012) |
HK (1) | HK15487A (en, 2012) |
HU (1) | HU180945B (en, 2012) |
IE (1) | IE48313B1 (en, 2012) |
IL (1) | IL56611A (en, 2012) |
IN (1) | IN151188B (en, 2012) |
IT (1) | IT1119272B (en, 2012) |
MX (1) | MX5926E (en, 2012) |
MY (1) | MY8500590A (en, 2012) |
NO (1) | NO151546C (en, 2012) |
NZ (1) | NZ189592A (en, 2012) |
PH (2) | PH18073A (en, 2012) |
PL (1) | PL118708B1 (en, 2012) |
PT (1) | PT69203A (en, 2012) |
RO (1) | RO83454A (en, 2012) |
SG (1) | SG61782G (en, 2012) |
SU (1) | SU999971A3 (en, 2012) |
YU (1) | YU29279A (en, 2012) |
Families Citing this family (31)
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US4584384A (en) * | 1978-05-30 | 1986-04-22 | Smith Kline & French Laboratories Limited | Nitro pyrroles |
IL57415A (en) * | 1978-05-30 | 1984-08-31 | Smith Kline French Lab | Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them |
ZA793392B (en) * | 1978-07-15 | 1980-08-27 | Smith Kline French Lab | Isoureas and isothioureas |
ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
YU53681A (en) * | 1980-03-08 | 1983-12-31 | Smith Kline French Lab | Process for obtaining 5-dimethylamino-methyl-2-furane methanol |
CA1155842A (en) * | 1980-03-29 | 1983-10-25 | Thomas H. Brown | Compounds |
ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
US4439609A (en) * | 1980-10-01 | 1984-03-27 | Smith Kline & French Laboratories Limited | Pyridines |
US4352933A (en) * | 1981-02-06 | 1982-10-05 | Smithkline Beckman Corporation | Chemical methods and intermediates for preparing substituted pyrimidinones |
US4439437A (en) * | 1981-04-28 | 1984-03-27 | Smith Kline & French Laboratories Limited | 2-[2-Thiazolyl or 2-guanidino-4-thiazolyl methylthioethyl(or butyl)amino]-3-(hydroxy or carboxy)pyridines, compositions containing same and method of use |
ZA823149B (en) * | 1981-05-27 | 1983-03-30 | Smithkline Beckman Corp | Chemical process |
IE53193B1 (en) * | 1981-07-14 | 1988-08-17 | Smithkline Beckman Corp | Preparation of lower alkyl 2-formyl-3-(6-methyl-3-pyridinyl)-propionates |
WO1983002113A1 (en) * | 1981-12-17 | 1983-06-23 | Yuki, Hiroshi | Propenylamine derivatives and drug containing same |
CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
EP0103366B1 (en) * | 1982-07-20 | 1986-02-19 | Smith Kline & French Laboratories Limited | A process for the preparation of 2-(2-((5-dimethyl-aminomethyl)furan-2-ylmethylthio)ethylamino)-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one |
DE3365869D1 (en) * | 1982-07-30 | 1986-10-09 | Smith Kline French Lab | Amino pyrimidinones and their preparation |
GB8304593D0 (en) * | 1983-02-18 | 1983-03-23 | Beecham Group Plc | Amidines |
GB8311443D0 (en) * | 1983-04-27 | 1983-06-02 | Smith Kline French Lab | Chemical compounds |
GB8318638D0 (en) * | 1983-07-09 | 1983-08-10 | Smith Kline French Lab | Chemical compounds |
GB8319874D0 (en) * | 1983-07-23 | 1983-08-24 | Smith Kline French Lab | Compounds |
GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
GB8328240D0 (en) * | 1983-10-21 | 1983-11-23 | Smith Kline French Lab | Chemical process |
GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
US4785003A (en) * | 1984-10-16 | 1988-11-15 | Biomeasure, Inc. | N-disubstituted glycine and B-amino-propionic acid derivatives having anti-ulcer activity |
US4598067A (en) * | 1984-10-16 | 1986-07-01 | Biomeasure, Inc. | Antiulcer compounds |
CH665838A5 (de) * | 1985-06-20 | 1988-06-15 | Lonza Ag | 3-hydroxy-3-(2-methyl-5-pyridyl)-propionsaeurealkylester, ihre herstellung und verwendung. |
US4912101A (en) * | 1987-03-13 | 1990-03-27 | Fujirebio Kabushiki Kaisha | 4-aminomethyl-pyridyl-2-oxy derivatives having anti-ulcer activity |
NZ541074A (en) * | 2002-12-16 | 2008-04-30 | Mitsubishi Pharma Corp | 3-Substituted-4-pyrimidone derivatives |
US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
GB1223686A (en) * | 1967-02-24 | 1971-03-03 | Ici Ltd | Salts of pyrimidine derivatives and the use thereof as fungicides |
GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
IN146736B (en, 2012) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
US4145546A (en) * | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
MW5076A1 (en) | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
GB1565966A (en) | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
GB1601459A (en) | 1977-05-17 | 1981-10-28 | Allen & Hanburys Ltd | Aminoalkyl thiophene derivatives |
AU527202B2 (en) * | 1978-04-11 | 1983-02-24 | Smith Kline & French Laboratories Limited | 2-aminopyrimidones |
ZA793392B (en) * | 1978-07-15 | 1980-08-27 | Smith Kline French Lab | Isoureas and isothioureas |
ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
PT75074B (en) * | 1981-06-27 | 1986-02-26 | Smith Kline French Lab | Process for preparing certain pyrimidone derivatives and compositions containing them |
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1979
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- 1979-02-07 EP EP79300190A patent/EP0003677B1/en not_active Expired
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- 1979-02-09 BG BG042428A patent/BG34906A3/xx unknown
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- 1979-02-09 IE IE254/79A patent/IE48313B1/en not_active IP Right Cessation
- 1979-02-09 PT PT7969203A patent/PT69203A/pt unknown
- 1979-02-09 DK DK54879A patent/DK54879A/da not_active Application Discontinuation
- 1979-02-09 JP JP1488979A patent/JPS54115385A/ja active Granted
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- 1979-02-12 RO RO79105057A patent/RO83454A/ro unknown
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1982
- 1982-12-07 SG SG617/82A patent/SG61782G/en unknown
-
1985
- 1985-06-21 US US06/747,496 patent/US4649141A/en not_active Expired - Lifetime
- 1985-12-30 MY MY590/85A patent/MY8500590A/xx unknown
-
1987
- 1987-02-19 HK HK154/87A patent/HK15487A/xx unknown
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