NO861421L - Pyrimidinon-derivater. - Google Patents
Pyrimidinon-derivater.Info
- Publication number
- NO861421L NO861421L NO861421A NO861421A NO861421L NO 861421 L NO861421 L NO 861421L NO 861421 A NO861421 A NO 861421A NO 861421 A NO861421 A NO 861421A NO 861421 L NO861421 L NO 861421L
- Authority
- NO
- Norway
- Prior art keywords
- group
- alkyl
- formula
- hydrogen atom
- compounds
- Prior art date
Links
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 34
- 230000031864 metaphase Effects 0.000 abstract description 12
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 230000010261 cell growth Effects 0.000 abstract description 6
- 230000002159 abnormal effect Effects 0.000 abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- -1 methoxy, methoxycarbonyl Chemical group 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 159000000000 sodium salts Chemical class 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 150000003230 pyrimidines Chemical class 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 12
- 235000010262 sodium metabisulphite Nutrition 0.000 description 12
- 229940001584 sodium metabisulfite Drugs 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 9
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- OCSYCDVQABSEPJ-UHFFFAOYSA-N 5-chloro-1h-pyrimidin-2-one Chemical compound OC1=NC=C(Cl)C=N1 OCSYCDVQABSEPJ-UHFFFAOYSA-N 0.000 description 4
- XWAYTMNSMIPFPH-UHFFFAOYSA-N 5-chloro-3-[2-(4-methylphenyl)-2-oxoethyl]-2-oxo-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C1=CC(C)=CC=C1C(=O)CN1C(=O)NC(S(O)(=O)=O)C(Cl)=C1 XWAYTMNSMIPFPH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- DNGCBTOMQHYYGA-UHFFFAOYSA-N 5-chloro-1-[2-(4-methylphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 DNGCBTOMQHYYGA-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QCRFGZNXTRZDCM-UHFFFAOYSA-N 3-[2-(4-acetamidophenyl)-2-oxoethyl]-5-chloro-2-oxo-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)CN1C(=O)NC(S(O)(=O)=O)C(Cl)=C1 QCRFGZNXTRZDCM-UHFFFAOYSA-N 0.000 description 2
- MPAYCBXQUMSKOC-UHFFFAOYSA-N 5-chloro-1-(2-oxo-2-thiophen-2-ylethyl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C1=CC=CS1 MPAYCBXQUMSKOC-UHFFFAOYSA-N 0.000 description 2
- OBFQQEXCVFCYQX-UHFFFAOYSA-N 5-chloro-1-(4-oxo-6,7-dihydro-5h-1-benzothiophen-5-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C1C(=O)C(C=CS2)=C2CC1 OBFQQEXCVFCYQX-UHFFFAOYSA-N 0.000 description 2
- LTXLXMLSDCGXCH-UHFFFAOYSA-N 5-chloro-1-[2-(4-methyl-1,3-thiazol-5-yl)-2-oxoethyl]pyrimidin-2-one Chemical compound N1=CSC(C(=O)CN2C(N=CC(Cl)=C2)=O)=C1C LTXLXMLSDCGXCH-UHFFFAOYSA-N 0.000 description 2
- JLJYTUTUQJKATA-UHFFFAOYSA-N 5-chloro-1-[2-[4-(dimethylamino)phenyl]-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(N(C)C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 JLJYTUTUQJKATA-UHFFFAOYSA-N 0.000 description 2
- LLRFTHKBAMMRBU-UHFFFAOYSA-N 5-chloro-2-oxo-3-(3-oxo-1,2-dihydroinden-2-yl)-1,4-dihydropyrimidine-4-sulfonic acid Chemical compound O=C1NC=C(Cl)C(S(=O)(=O)O)N1C1C(=O)C2=CC=CC=C2C1 LLRFTHKBAMMRBU-UHFFFAOYSA-N 0.000 description 2
- DOOTTXXHPBISAM-UHFFFAOYSA-N 5-chloro-2-oxo-3-(3-oxo-1,2-dihydroinden-2-yl)-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C1=C(Cl)C(S(=O)(=O)O)NC(=O)N1C1C(=O)C2=CC=CC=C2C1 DOOTTXXHPBISAM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000017095 negative regulation of cell growth Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- 238000012360 testing method Methods 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- UXVCSPSWUNMPMT-UHFFFAOYSA-N 2-bromo-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(Br)CC2=C1 UXVCSPSWUNMPMT-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- KBLQDFSWVMPYEM-UHFFFAOYSA-N 5-bromo-6,7-dihydro-5h-1-benzothiophen-4-one Chemical compound O=C1C(Br)CCC2=C1C=CS2 KBLQDFSWVMPYEM-UHFFFAOYSA-N 0.000 description 1
- DMMWXAZVWFDMFI-UHFFFAOYSA-N 5-chloro-1-(1-oxo-1-phenylpropan-2-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C(C)C(=O)C1=CC=CC=C1 DMMWXAZVWFDMFI-UHFFFAOYSA-N 0.000 description 1
- PCVDOTNJESCUGU-UHFFFAOYSA-N 5-chloro-1-(1-oxo-1-thiophen-2-ylpropan-2-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C(C)C(=O)C1=CC=CS1 PCVDOTNJESCUGU-UHFFFAOYSA-N 0.000 description 1
- ZJXSNAAUFVMPEL-UHFFFAOYSA-N 5-chloro-1-(2-oxo-1,2-diphenylethyl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 ZJXSNAAUFVMPEL-UHFFFAOYSA-N 0.000 description 1
- FRSHLXMJWGEYGU-UHFFFAOYSA-N 5-chloro-1-(3-oxo-1,2-dihydroinden-2-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C1C(=O)C2=CC=CC=C2C1 FRSHLXMJWGEYGU-UHFFFAOYSA-N 0.000 description 1
- XLISFNGIUCGGKP-UHFFFAOYSA-N 5-chloro-1-phenacylpyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C1=CC=CC=C1 XLISFNGIUCGGKP-UHFFFAOYSA-N 0.000 description 1
- RQVZKORTLYGORT-UHFFFAOYSA-N 5-chloro-2-oxo-3-(1-oxo-1-phenylpropan-2-yl)-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C=1C=CC=CC=1C(=O)C(C)N1C=C(Cl)C(S(O)(=O)=O)NC1=O RQVZKORTLYGORT-UHFFFAOYSA-N 0.000 description 1
- HDGZLFHWMFGZRB-UHFFFAOYSA-N 5-chloro-2-oxo-3-(1-oxo-1-thiophen-2-ylpropan-2-yl)-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C=1C=CSC=1C(=O)C(C)N1C=C(Cl)C(S(O)(=O)=O)NC1=O HDGZLFHWMFGZRB-UHFFFAOYSA-N 0.000 description 1
- VLIZJRULCSYVGN-UHFFFAOYSA-N 5-chloro-2-oxo-3-(2-oxo-2-thiophen-2-ylethyl)-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound C1=C(Cl)C(S(=O)(=O)O)NC(=O)N1CC(=O)C1=CC=CS1 VLIZJRULCSYVGN-UHFFFAOYSA-N 0.000 description 1
- FGXWIUBXZQVCNQ-UHFFFAOYSA-N 5-chloro-2-oxo-3-(4-oxo-6,7-dihydro-5h-1-benzothiophen-5-yl)-1,4-dihydropyrimidine-4-sulfonic acid Chemical compound O=C1NC=C(Cl)C(S(=O)(=O)O)N1C1C(=O)C(C=CS2)=C2CC1 FGXWIUBXZQVCNQ-UHFFFAOYSA-N 0.000 description 1
- UZJVRMWBPVFDSD-UHFFFAOYSA-N 5-chloro-3-[2-(4-methyl-1,3-thiazol-5-yl)-2-oxoethyl]-2-oxo-1,6-dihydropyrimidine-6-sulfonic acid Chemical compound N1=CSC(C(=O)CN2C(NC(C(Cl)=C2)S(O)(=O)=O)=O)=C1C UZJVRMWBPVFDSD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100452236 Caenorhabditis elegans inf-1 gene Proteins 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YNOKTPRQOUTODP-UHFFFAOYSA-N n-[4-[2-(5-chloro-2-oxopyrimidin-1-yl)acetyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 YNOKTPRQOUTODP-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D239/46—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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848420610A GB8420610D0 (en) | 1984-08-14 | 1984-08-14 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO861421L true NO861421L (no) | 1986-04-11 |
Family
ID=10565312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO861421A NO861421L (no) | 1984-08-14 | 1986-04-11 | Pyrimidinon-derivater. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0189472A1 (da) |
| JP (1) | JPS62500028A (da) |
| DK (1) | DK154086D0 (da) |
| GB (1) | GB8420610D0 (da) |
| NO (1) | NO861421L (da) |
| WO (1) | WO1986001205A1 (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4130030B2 (ja) * | 1999-03-09 | 2008-08-06 | 富士フイルム株式会社 | 感光性組成物および１，３−ジヒドロ−１−オキソ−２ｈ−インデン誘導体化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ197715A (en) * | 1980-07-15 | 1984-12-14 | Glaxo Group Ltd | Substituted pyrimin-2-ones and pharmaceutical compositions |
| CA1160226A (en) * | 1980-07-15 | 1984-01-10 | Gordon H. Phillipps | Substituted pyrimidin-2-ones, the salts thereof, processes for their preparation, pharmaceutical compositions containing them and a method therefor |
| GB2135992B (en) * | 1983-01-11 | 1986-09-24 | Nyegaard & Co As | Substituted pyrimidines and processes for their preparation |
-
1984
- 1984-08-14 GB GB848420610A patent/GB8420610D0/en active Pending
-
1985
- 1985-08-13 EP EP19850904010 patent/EP0189472A1/en not_active Withdrawn
- 1985-08-13 WO PCT/GB1985/000360 patent/WO1986001205A1/en not_active Application Discontinuation
- 1985-08-13 JP JP50364385A patent/JPS62500028A/ja active Pending
-
1986
- 1986-04-04 DK DK154086A patent/DK154086D0/da not_active IP Right Cessation
- 1986-04-11 NO NO861421A patent/NO861421L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62500028A (ja) | 1987-01-08 |
| DK154086A (da) | 1986-04-04 |
| DK154086D0 (da) | 1986-04-04 |
| WO1986001205A1 (en) | 1986-02-27 |
| GB8420610D0 (en) | 1984-09-19 |
| EP0189472A1 (en) | 1986-08-06 |
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