NO841168L - Fremgangsmaate for fremstilling av pyrimidinderivater - Google Patents
Fremgangsmaate for fremstilling av pyrimidinderivaterInfo
- Publication number
- NO841168L NO841168L NO841168A NO841168A NO841168L NO 841168 L NO841168 L NO 841168L NO 841168 A NO841168 A NO 841168A NO 841168 A NO841168 A NO 841168A NO 841168 L NO841168 L NO 841168L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- lower alkyl
- general formula
- dimethoxyphenyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 53
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 hydroxy, amino Chemical group 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000004593 Epoxy Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- IJJUENQVHOKTHU-UHFFFAOYSA-N C1=C(OC)C(OC)=CC=C1C(NC(=O)N1C)=CC1=NC1=C(C)C=C(C)C=C1C Chemical compound C1=C(OC)C(OC)=CC=C1C(NC(=O)N1C)=CC1=NC1=C(C)C=C(C)C=C1C IJJUENQVHOKTHU-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- NFHSJMMFPWGVHO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-dimethyl-6-(2,4,6-trimethoxyphenyl)iminopyrimidin-2-one Chemical compound COC1=CC(OC)=CC(OC)=C1N=C1N(C)C(=O)N(C)C(C=2C=C(OC)C(OC)=CC=2)=C1 NFHSJMMFPWGVHO-UHFFFAOYSA-N 0.000 claims description 2
- YNLQYELKKUHQNR-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-2-ethoxy-3-methyl-n-(2,4,6-trimethylphenyl)pyrimidin-4-imine Chemical compound CN1C(OCC)=NC(C=2C=C(OC)C(OC)=CC=2)=CC1=NC1=C(C)C=C(C)C=C1C YNLQYELKKUHQNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims 1
- WLUQFKLDOJWLIN-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-dimethyl-6-(2,4,6-trimethylphenyl)iminopyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(N(C(=O)N1C)C)=CC1=NC1=C(C)C=C(C)C=C1C WLUQFKLDOJWLIN-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 94
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 88
- 238000002329 infrared spectrum Methods 0.000 description 84
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 39
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 21
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RZYVZALRKACWRX-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-dimethyl-6-sulfanylidenepyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=S)N(C)C(=O)N1C RZYVZALRKACWRX-UHFFFAOYSA-N 0.000 description 11
- JBFXUEXTFAJUSA-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-3-methyl-1h-pyrimidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C)C(=O)N1 JBFXUEXTFAJUSA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000036772 blood pressure Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 150000003230 pyrimidines Chemical class 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- DCEGRFKPBZZMGE-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-3-methyl-4-sulfanylidene-1h-pyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=S)N(C)C(=O)N1 DCEGRFKPBZZMGE-UHFFFAOYSA-N 0.000 description 6
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- BHSYONGONOKNAI-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(OC)C(OC)=C1 BHSYONGONOKNAI-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- HNBBMGXWVDKYSV-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1h-pyrimidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)NC(=O)N1 HNBBMGXWVDKYSV-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000003177 cardiotonic effect Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 230000000304 vasodilatating effect Effects 0.000 description 4
- HDILJLGDCHICLC-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1,3-dimethylpyrimidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C)C(=O)N1C HDILJLGDCHICLC-UHFFFAOYSA-N 0.000 description 3
- OYGHXRNCHYRYRR-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-ethyl-3-methyl-4-(2,4,6-trimethylphenyl)iminopyrimidin-2-one Chemical compound CN1C(=O)N(CC)C(C=2C=C(OC)C(OC)=CC=2)=CC1=NC1=C(C)C=C(C)C=C1C OYGHXRNCHYRYRR-UHFFFAOYSA-N 0.000 description 3
- OEMVORBXRCANQF-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-methylpyrimidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)NC(=O)N1C OEMVORBXRCANQF-UHFFFAOYSA-N 0.000 description 3
- XIWACCQPMUVSKC-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-3-methyl-1-propylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(CCC)C(C=2C=C(OC)C(OC)=CC=2)=C1 XIWACCQPMUVSKC-UHFFFAOYSA-N 0.000 description 3
- VTGPBXIGZNZSBJ-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-3-methyl-2-propan-2-yloxypyrimidine-4-thione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=S)N(C)C(OC(C)C)=N1 VTGPBXIGZNZSBJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 230000003727 cerebral blood flow Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 210000001105 femoral artery Anatomy 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 150000008512 pyrimidinediones Chemical class 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- IRCRFJUIGMASDZ-UHFFFAOYSA-N 1,3-dimethyl-4-phenyl-6-sulfanylidenepyrimidin-2-one Chemical compound S=C1N(C)C(=O)N(C)C(C=2C=CC=CC=2)=C1 IRCRFJUIGMASDZ-UHFFFAOYSA-N 0.000 description 2
- ZEXLLQDNQFSHJE-UHFFFAOYSA-N 1,3-dimethyl-4-pyridin-3-yl-6-sulfanylidenepyrimidin-2-one Chemical compound S=C1N(C)C(=O)N(C)C(C=2C=NC=CC=2)=C1 ZEXLLQDNQFSHJE-UHFFFAOYSA-N 0.000 description 2
- XPIAHJOLVVSCQH-UHFFFAOYSA-N 1,3-dimethyl-4-sulfanylidene-6-(2,3,4-trimethoxyphenyl)pyrimidin-2-one Chemical compound COC1=C(OC)C(OC)=CC=C1C1=CC(=S)N(C)C(=O)N1C XPIAHJOLVVSCQH-UHFFFAOYSA-N 0.000 description 2
- CHQUSPSYBGOASD-UHFFFAOYSA-N 1,3-dimethyl-4-sulfanylidene-6-(3,4,5-trimethoxyphenyl)pyrimidin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)N(C)C(=S)C=2)C)=C1 CHQUSPSYBGOASD-UHFFFAOYSA-N 0.000 description 2
- PMKLUUOSOUESOS-UHFFFAOYSA-N 1,3-dimethyl-4-sulfanylidenepyrimidin-2-one Chemical compound CN1C=CC(=S)N(C)C1=O PMKLUUOSOUESOS-UHFFFAOYSA-N 0.000 description 2
- WNESBIIIERSULU-UHFFFAOYSA-N 1,3-dimethyl-6-(2,3,4-trimethoxyphenyl)pyrimidine-2,4-dione Chemical compound COC1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C)C(=O)N1C WNESBIIIERSULU-UHFFFAOYSA-N 0.000 description 2
- CBIBVLLVSJJBCF-UHFFFAOYSA-N 1,3-dimethyl-6-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)N(C)C(=O)C=2)C)=C1 CBIBVLLVSJJBCF-UHFFFAOYSA-N 0.000 description 2
- HEXINJDAGJAXRK-UHFFFAOYSA-N 1,3-dimethyl-6-pyridin-3-ylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(C)C(C=2C=NC=CC=2)=C1 HEXINJDAGJAXRK-UHFFFAOYSA-N 0.000 description 2
- CRQONYLOAMLBSG-UHFFFAOYSA-N 1-benzyl-6-(3,4-dimethoxyphenyl)-3-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=S)N(C)C(=O)N1CC1=CC=CC=C1 CRQONYLOAMLBSG-UHFFFAOYSA-N 0.000 description 2
- CQXGREZVBUSLNH-UHFFFAOYSA-N 1-benzyl-6-(3,4-dimethoxyphenyl)-3-methylpyrimidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C)C(=O)N1CC1=CC=CC=C1 CQXGREZVBUSLNH-UHFFFAOYSA-N 0.000 description 2
- FNSAKXLEFPFZOM-UHFFFAOYSA-N 2,4,6-trimethoxyaniline Chemical compound COC1=CC(OC)=C(N)C(OC)=C1 FNSAKXLEFPFZOM-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FXMIXLJKIUMQTP-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1,3-dimethyl-6-sulfanylidenepyrimidin-2-one Chemical compound S=C1N(C)C(=O)N(C)C(C=2C=C(Cl)C(Cl)=CC=2)=C1 FXMIXLJKIUMQTP-UHFFFAOYSA-N 0.000 description 2
- ANAWTBRBLCXKCQ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-diethyl-6-sulfanylidenepyrimidin-2-one Chemical compound S=C1N(CC)C(=O)N(CC)C(C=2C=C(OC)C(OC)=CC=2)=C1 ANAWTBRBLCXKCQ-UHFFFAOYSA-N 0.000 description 2
- ZNVXYGFZHASVGH-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1-methyl-3-propyl-6-sulfanylidenepyrimidin-2-one Chemical compound S=C1N(C)C(=O)N(CCC)C(C=2C=C(OC)C(OC)=CC=2)=C1 ZNVXYGFZHASVGH-UHFFFAOYSA-N 0.000 description 2
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- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838308290A GB8308290D0 (en) | 1983-03-25 | 1983-03-25 | Pyrimidinone derivatives |
| GB838315542A GB8315542D0 (en) | 1983-06-07 | 1983-06-07 | Pyrimidinone derivatives |
| GB838327859A GB8327859D0 (en) | 1983-10-18 | 1983-10-18 | Pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841168L true NO841168L (no) | 1984-09-26 |
Family
ID=27262023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841168A NO841168L (no) | 1983-03-25 | 1984-03-23 | Fremgangsmaate for fremstilling av pyrimidinderivater |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US4612376A (fr) |
| EP (1) | EP0123402B1 (fr) |
| KR (1) | KR840008333A (fr) |
| CA (1) | CA1256107A (fr) |
| DE (1) | DE3473875D1 (fr) |
| DK (1) | DK160492C (fr) |
| ES (2) | ES8505972A1 (fr) |
| FI (1) | FI841128A (fr) |
| GR (1) | GR81758B (fr) |
| HU (1) | HU195195B (fr) |
| NO (1) | NO841168L (fr) |
| PH (1) | PH22022A (fr) |
| SU (2) | SU1349698A3 (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4612376A (en) * | 1983-03-25 | 1986-09-16 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent |
| US4598149A (en) * | 1984-03-02 | 1986-07-01 | Merck & Co., Inc. | 3-amino-2-hydroxypropyl of pyrimidin-4-one useful as antihypertensive, cardioprotective, antiarrythmic, and antianginal agents |
| US4649142A (en) * | 1984-06-25 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | 3,4-dihydro-1,3-disubstituted-6-(substituted phenylimino)-2(1H)-pyrimidinone useful as cardiotonic agent and anti-allergic agent |
| US4708958A (en) * | 1986-09-24 | 1987-11-24 | G. D. Searle & Co. | 6-(imidazolyphenyl)-4-iminopyrimidinones useful as hypotensive agents |
| US5521315A (en) * | 1993-01-12 | 1996-05-28 | Cell Therapeutics, Inc. | Olefin substituted long chain compounds |
| IT1270122B (it) * | 1994-10-04 | 1997-04-28 | Ist Superiore Sanita | 6-benzil-4-ossopirimidine sostituite, processo per la loro preparazione e composizioni farmaceutiche che le contengono |
| US6244121B1 (en) * | 1998-03-06 | 2001-06-12 | Applied Materials, Inc. | Sensor device for non-intrusive diagnosis of a semiconductor processing system |
| US8293751B2 (en) | 2003-01-14 | 2012-10-23 | Arena Pharmaceuticals, Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| WO2005007658A2 (fr) | 2003-07-14 | 2005-01-27 | Arena Pharmaceuticals, Inc. | Derives aryle et heteroaryle condenses utilises comme modulateurs du metabolisme et prophylaxie et traitement des troubles metaboliques |
| DOP2006000009A (es) | 2005-01-13 | 2006-08-15 | Arena Pharm Inc | Procedimiento para preparar eteres de pirazolo [3,4-d] pirimidina |
| US7776870B2 (en) | 2005-08-22 | 2010-08-17 | Melior Pharmaceuticals I, Inc. | Methods for modulating Lyn kinase activity and treating related disorders |
| CA2678813A1 (fr) * | 2007-02-20 | 2008-08-28 | Melior Pharmaceuticals I, Inc. | Procedes d'identification d'activateurs de lyn kinase |
| CA2693809A1 (fr) * | 2007-07-23 | 2009-01-29 | Melior Discovery, Inc. | Procedes d'activation de irs-1 et akt |
| US8552184B2 (en) * | 2008-07-03 | 2013-10-08 | Melior Pharmaceuticals I, Inc. | Compounds and methods for treating disorders related to glucose metabolism |
| TWI393716B (zh) * | 2009-08-04 | 2013-04-21 | Merck Sharp & Dohme | 作為ｉｘａ因子抑制劑之雜環化合物 |
| EP3378854B1 (fr) | 2010-01-27 | 2022-12-21 | Arena Pharmaceuticals, Inc. | Procédés de préparation d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclopenta[b]indol-3-yl) acétique et de ses sels |
| WO2011150300A1 (fr) | 2010-05-28 | 2011-12-01 | Melior Pharmaceuticals I, Inc. | Prévention de la dégénérescence des cellules pancréatiques bêta |
| BR112013008100A2 (pt) | 2010-09-22 | 2016-08-09 | Arena Pharm Inc | "moduladores do receptor de gpr19 e o tratamento de distúrbios relacionados a eles." |
| WO2016031987A1 (fr) * | 2014-08-29 | 2016-03-03 | 国立大学法人東京大学 | Dérivé de pyrimidone ayant une activité inhibitrice de l'autotaxine |
| US10183949B2 (en) | 2014-08-29 | 2019-01-22 | The University Of Tokyo | Pyrimidinone derivative having autotaxin-inhibitory activity |
| CN116850181A (zh) | 2015-01-06 | 2023-10-10 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| MX2017016530A (es) | 2015-06-22 | 2018-03-12 | Arena Pharm Inc | Sal cristalina de l-arginina del acido (r)-2-(7-(4-ciclopentil-3-( trifluorometil)benciloxi)-1,2,3,4-tetrahidrociclopenta[b]indol-3- il)acetico (compuesto1) para ser utilizada en transtornos asociados con el receptor de esfingosina-1-fosfato 1 (s1p1). |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| BR112019021140A2 (pt) | 2017-04-10 | 2020-05-19 | Univ Louisiana State | composição, método para reduzir os níveis de glicose no sangue, ganho de peso ou níveis de depósito de gordura, ou tratamento, método de indução do bege de adipócitos ou prevenção da degeneração das células beta do pâncreas, e, ativador de lyn cinase e agonista de trpm8 para uso na redução dos níveis de glicose no sangue, ganho de peso ou níveis de depósito de gordura, ou tratamento. |
| CN109053589A (zh) * | 2018-09-30 | 2018-12-21 | 浙江师范大学 | 4-亚胺基四氢嘧啶-2-酮类化合物的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296371A (fr) * | 1969-02-26 | 1972-11-15 | ||
| AU1108070A (en) * | 1969-03-06 | 1971-08-12 | Imperial Chemical Industries Limited | Pyrimidine derivatives |
| GB1336138A (en) * | 1969-12-10 | 1973-11-07 | Ici Ltd | Process for the production of pyrimidine derivatives |
| US3923807A (en) * | 1973-09-10 | 1975-12-02 | Takeda Chemical Industries Ltd | 6-Aminouracil derivatives |
| JPS5053381A (fr) * | 1973-09-20 | 1975-05-12 | ||
| US4208366A (en) * | 1978-10-31 | 1980-06-17 | E. I. Du Pont De Nemours And Company | Process for preparing a nonwoven web |
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| US4612376A (en) * | 1983-03-25 | 1986-09-16 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent |
-
1984
- 1984-03-12 US US06/588,902 patent/US4612376A/en not_active Expired - Fee Related
- 1984-03-14 EP EP84301741A patent/EP0123402B1/fr not_active Expired
- 1984-03-14 DE DE8484301741T patent/DE3473875D1/de not_active Expired
- 1984-03-14 GR GR74104A patent/GR81758B/el unknown
- 1984-03-14 PH PH30400A patent/PH22022A/en unknown
- 1984-03-20 KR KR1019840001414A patent/KR840008333A/ko not_active Application Discontinuation
- 1984-03-21 FI FI841128A patent/FI841128A/fi not_active Application Discontinuation
- 1984-03-21 CA CA000450076A patent/CA1256107A/fr not_active Expired
- 1984-03-23 HU HU841170A patent/HU195195B/hu not_active IP Right Cessation
- 1984-03-23 SU SU843718401A patent/SU1349698A3/ru active
- 1984-03-23 DK DK166884A patent/DK160492C/da active IP Right Grant
- 1984-03-23 ES ES530916A patent/ES8505972A1/es not_active Expired
- 1984-03-23 NO NO841168A patent/NO841168L/no unknown
- 1984-11-30 ES ES538190A patent/ES538190A0/es active Granted
-
1985
- 1985-03-28 SU SU853892541A patent/SU1436872A3/ru active
-
1986
- 1986-06-05 US US06/870,826 patent/US4746664A/en not_active Expired - Fee Related
-
1988
- 1988-03-25 US US07/173,584 patent/US4824851A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SU1349698A3 (ru) | 1987-10-30 |
| US4612376A (en) | 1986-09-16 |
| ES8601922A1 (es) | 1985-11-01 |
| DK166884A (da) | 1984-09-26 |
| HU195195B (en) | 1988-04-28 |
| ES530916A0 (es) | 1985-06-16 |
| US4746664A (en) | 1988-05-24 |
| DK160492B (da) | 1991-03-18 |
| CA1256107A (fr) | 1989-06-20 |
| SU1436872A3 (ru) | 1988-11-07 |
| GR81758B (fr) | 1984-12-12 |
| FI841128A0 (fi) | 1984-03-21 |
| FI841128A (fi) | 1984-09-26 |
| ES8505972A1 (es) | 1985-06-16 |
| DK166884D0 (da) | 1984-03-23 |
| US4824851A (en) | 1989-04-25 |
| DK160492C (da) | 1991-08-26 |
| EP0123402B1 (fr) | 1988-09-07 |
| EP0123402A3 (en) | 1985-09-18 |
| DE3473875D1 (en) | 1988-10-13 |
| ES538190A0 (es) | 1985-11-01 |
| PH22022A (en) | 1988-05-13 |
| KR840008333A (ko) | 1984-12-14 |
| EP0123402A2 (fr) | 1984-10-31 |
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