NO852869L - Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-derivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-derivater.Info
- Publication number
- NO852869L NO852869L NO852869A NO852869A NO852869L NO 852869 L NO852869 L NO 852869L NO 852869 A NO852869 A NO 852869A NO 852869 A NO852869 A NO 852869A NO 852869 L NO852869 L NO 852869L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- general formula
- spectrum
- salt
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 99
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 5
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 213
- -1 nitro, amino Chemical group 0.000 claims description 178
- 150000003839 salts Chemical class 0.000 claims description 149
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- JMDFZQGHPNKKIW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 JMDFZQGHPNKKIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- DKNNLKOLBQMHAY-UHFFFAOYSA-N [4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 DKNNLKOLBQMHAY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 description 437
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 395
- 238000002844 melting Methods 0.000 description 369
- 230000008018 melting Effects 0.000 description 369
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 270
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 198
- 238000001819 mass spectrum Methods 0.000 description 194
- 238000006243 chemical reaction Methods 0.000 description 130
- 235000002639 sodium chloride Nutrition 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 76
- 239000000203 mixture Substances 0.000 description 72
- 239000002904 solvent Substances 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- 238000001816 cooling Methods 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 230000002411 adverse Effects 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
- 238000000354 decomposition reaction Methods 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical group 0.000 description 10
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- YYYIJTIQGKAAHN-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-[2-(dimethylamino)ethyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 YYYIJTIQGKAAHN-WLHGVMLRSA-N 0.000 description 6
- CINHREJSYYQCLC-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-[2-(dimethylamino)ethyl]-4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 CINHREJSYYQCLC-WLHGVMLRSA-N 0.000 description 6
- PRGSGLJWMPBXME-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-[2-(dimethylamino)ethyl]-4-methyl-6-(5-nitrothiophen-2-yl)-2-phenylpyrimidine-5-carboxamide Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)S1 PRGSGLJWMPBXME-WLHGVMLRSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- NKADGRRWIXIQRY-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-phenylpyrimidin-5-yl]urea Chemical compound CSC1=CC=C([N+]([O-])=O)C=C1C1=NC(C=2C=CC=CC=2)=NC(C)=C1NC(=O)NCCN(C)C NKADGRRWIXIQRY-UHFFFAOYSA-N 0.000 description 6
- DRKBWLVUVSEBRL-UHFFFAOYSA-N 4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CSC1=CC=C([N+]([O-])=O)C=C1C1=NC(C=2C=CC=CC=2)=NC(C)=C1C(O)=O DRKBWLVUVSEBRL-UHFFFAOYSA-N 0.000 description 6
- MLKNSTMLLQZNBD-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 MLKNSTMLLQZNBD-UHFFFAOYSA-N 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 150000007529 inorganic bases Chemical class 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- HAKPZXACCMDCPY-UHFFFAOYSA-N n-(2-chloroethyl)-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound ClCCNC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 HAKPZXACCMDCPY-UHFFFAOYSA-N 0.000 description 6
- AEWXKWFRHISNIQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CSC1=CC=C([N+]([O-])=O)C=C1C1=NC(C=2C=CC=CC=2)=NC(C)=C1C(=O)NCCN(C)C AEWXKWFRHISNIQ-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- HRAJNEVDTMYXHV-UHFFFAOYSA-N 2-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]acetonitrile Chemical compound N#CCC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 HRAJNEVDTMYXHV-UHFFFAOYSA-N 0.000 description 5
- UNWFDIGAYLMMEW-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound NC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 UNWFDIGAYLMMEW-UHFFFAOYSA-N 0.000 description 5
- VKEWVDJEMIZHTI-UHFFFAOYSA-N 5-(bromomethyl)-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine Chemical compound BrCC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 VKEWVDJEMIZHTI-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- YQMBSLJMSDIFSQ-UHFFFAOYSA-N [4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]methanol Chemical compound OCC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 YQMBSLJMSDIFSQ-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 5
- ATZNLLWEWLTDTR-UHFFFAOYSA-N ethyl 4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-pyridin-3-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=NC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1SC ATZNLLWEWLTDTR-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- GNNNPNLLCPPAOV-UHFFFAOYSA-N methyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1Cl GNNNPNLLCPPAOV-UHFFFAOYSA-N 0.000 description 5
- WYNUNFSGJIMNFJ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 WYNUNFSGJIMNFJ-UHFFFAOYSA-N 0.000 description 5
- WXNRZBNVEOZKJJ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 WXNRZBNVEOZKJJ-UHFFFAOYSA-N 0.000 description 5
- FGTGUNRYNDNTQW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-ethyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C=1C(CC)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 FGTGUNRYNDNTQW-UHFFFAOYSA-N 0.000 description 5
- VPMVSLKHIQVWHF-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 VPMVSLKHIQVWHF-UHFFFAOYSA-N 0.000 description 5
- XVKBGNGTUVSEAZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 XVKBGNGTUVSEAZ-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- FAAXBGJBASJZHZ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(4-nitrophenyl)-2-phenylpyrimidin-5-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 FAAXBGJBASJZHZ-UHFFFAOYSA-N 0.000 description 4
- ZPBYSPLMIKJMNK-WLHGVMLRSA-N (e)-but-2-enedioic acid;[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 ZPBYSPLMIKJMNK-WLHGVMLRSA-N 0.000 description 4
- AECMVSTWDLWSFR-UHFFFAOYSA-N 1-(1-ethylpiperidin-3-yl)-3-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]urea Chemical compound C1N(CC)CCCC1NC(=O)NC1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 AECMVSTWDLWSFR-UHFFFAOYSA-N 0.000 description 4
- NJYIRJMRUKKYLA-UHFFFAOYSA-N 1-[4-(4-chloro-3-nitrophenyl)-6-methyl-2-phenylpyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C([N+]([O-])=O)=C1 NJYIRJMRUKKYLA-UHFFFAOYSA-N 0.000 description 4
- NETUKITUSKNVNK-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-phenyl-6-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C1C1=CC=CC=C1 NETUKITUSKNVNK-UHFFFAOYSA-N 0.000 description 4
- OCWLNSBOLUHIIN-UHFFFAOYSA-N 4-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 OCWLNSBOLUHIIN-UHFFFAOYSA-N 0.000 description 4
- FFBAARAAHYRQFT-UHFFFAOYSA-N 4-ethyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(CC)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 FFBAARAAHYRQFT-UHFFFAOYSA-N 0.000 description 4
- SJVMRIOMPMXROC-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carbonitrile Chemical compound N#CC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 SJVMRIOMPMXROC-UHFFFAOYSA-N 0.000 description 4
- QUXVIZZAHHRSNL-UHFFFAOYSA-N 4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=C([N+]([O-])=O)C=C1 QUXVIZZAHHRSNL-UHFFFAOYSA-N 0.000 description 4
- VHPGITAIRGUFKT-UHFFFAOYSA-N 4-methyl-n-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]piperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 VHPGITAIRGUFKT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 235000021342 arachidonic acid Nutrition 0.000 description 4
- 208000026106 cerebrovascular disease Diseases 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- ZPXSTGJEBSKIEB-UHFFFAOYSA-N ethyl 4-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 ZPXSTGJEBSKIEB-UHFFFAOYSA-N 0.000 description 4
- QERWUJOWGVVOIT-UHFFFAOYSA-N ethyl 4-methyl-6-(2-methylsulfonyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1S(C)(=O)=O QERWUJOWGVVOIT-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- QJASEMNWFYUALJ-UHFFFAOYSA-N methyl 4-(3-hydroxyphenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(O)=C1 QJASEMNWFYUALJ-UHFFFAOYSA-N 0.000 description 4
- ZPJUOSCXPHTVTQ-UHFFFAOYSA-N methyl 4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1SC ZPJUOSCXPHTVTQ-UHFFFAOYSA-N 0.000 description 4
- VUWLQIMCHFOAKP-UHFFFAOYSA-N n-(2-acetamidoethyl)-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CC(=O)NCCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 VUWLQIMCHFOAKP-UHFFFAOYSA-N 0.000 description 4
- HJPMJFQBMURZOE-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound OCCNC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 HJPMJFQBMURZOE-UHFFFAOYSA-N 0.000 description 4
- UEPPIYDBTAIZAJ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-nitrophenyl)-2-phenyl-6-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NCCN(C)C)=C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C1C1=CC=CC=C1 UEPPIYDBTAIZAJ-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OOPMAKDNBMIVFC-UHFFFAOYSA-N trimethyl-[2-[[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carbonyl]amino]ethyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCNC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 OOPMAKDNBMIVFC-UHFFFAOYSA-N 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- GRVLDHOXKWXPGD-UHFFFAOYSA-N 1-[4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-phenylpyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(O)C([N+]([O-])=O)=C1 GRVLDHOXKWXPGD-UHFFFAOYSA-N 0.000 description 3
- CTEGZYGHMDAWEG-UHFFFAOYSA-N 1-[4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 CTEGZYGHMDAWEG-UHFFFAOYSA-N 0.000 description 3
- GENREIYGWKFGNQ-UHFFFAOYSA-N 2-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 GENREIYGWKFGNQ-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 3
- DFOWUJFCBFSKTH-UHFFFAOYSA-N 4-methyl-2-phenyl-6-pyridin-4-ylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 DFOWUJFCBFSKTH-UHFFFAOYSA-N 0.000 description 3
- AWQPIDNRBLHAMO-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenyl-n-(2-pyrrolidin-1-ylethyl)pyrimidine-5-carboxamide Chemical compound C1CCCN1CCNC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 AWQPIDNRBLHAMO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- MEGQJYLVHLPQQU-UHFFFAOYSA-N [4-methyl-2-phenyl-6-[3-(trifluoromethyl)phenyl]pyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(C(F)(F)F)=C1 MEGQJYLVHLPQQU-UHFFFAOYSA-N 0.000 description 3
- XJLYYWFLPYJQJZ-UHFFFAOYSA-N [4-methyl-6-(2-nitrophenyl)-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1[N+]([O-])=O XJLYYWFLPYJQJZ-UHFFFAOYSA-N 0.000 description 3
- AQHBHVDVZFWJPV-UHFFFAOYSA-N [4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 AQHBHVDVZFWJPV-UHFFFAOYSA-N 0.000 description 3
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 210000004004 carotid artery internal Anatomy 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- TZJXMKSNTCLVGE-UHFFFAOYSA-N ethyl 2-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]acetate Chemical compound CCOC(=O)CC1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 TZJXMKSNTCLVGE-UHFFFAOYSA-N 0.000 description 3
- FINAQIBOEFEBIR-UHFFFAOYSA-N ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-pyridin-3-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=NC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1Cl FINAQIBOEFEBIR-UHFFFAOYSA-N 0.000 description 3
- NYRXDKGKTJIZMJ-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C(O)=C1 NYRXDKGKTJIZMJ-UHFFFAOYSA-N 0.000 description 3
- VDCCHKNTDNBYLD-UHFFFAOYSA-N ethyl 4-(3-nitrophenyl)-2-phenyl-6-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C1C1=CC=CC=C1 VDCCHKNTDNBYLD-UHFFFAOYSA-N 0.000 description 3
- FUZTYQLGSJVXHX-UHFFFAOYSA-N ethyl 4-(diethoxymethyl)-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C=1C(C(OCC)OCC)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 FUZTYQLGSJVXHX-UHFFFAOYSA-N 0.000 description 3
- HGRDVDRTOUWNNW-UHFFFAOYSA-N ethyl 4-methyl-2-phenyl-6-pyridin-4-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=NC=C1 HGRDVDRTOUWNNW-UHFFFAOYSA-N 0.000 description 3
- VIWTXVPXCWZSSL-UHFFFAOYSA-N ethyl 4-methyl-6-(2-methylsulfanyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1SC VIWTXVPXCWZSSL-UHFFFAOYSA-N 0.000 description 3
- IQEQUTOVOYWVKG-UHFFFAOYSA-N ethyl 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 IQEQUTOVOYWVKG-UHFFFAOYSA-N 0.000 description 3
- FFZLAYLHPDIPRP-UHFFFAOYSA-N ethyl 4-methyl-6-(3-nitrophenyl)-2-pyridin-3-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=NC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 FFZLAYLHPDIPRP-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- RSHAOIXHUHAZPM-UHFFFAOYSA-N magnesium hydride Chemical compound [MgH2] RSHAOIXHUHAZPM-UHFFFAOYSA-N 0.000 description 3
- 229910012375 magnesium hydride Inorganic materials 0.000 description 3
- DMCSXXJVMAKYHP-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-4-methyl-6-(3-nitrophenyl)pyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 DMCSXXJVMAKYHP-UHFFFAOYSA-N 0.000 description 3
- WJEHESGYJCURQT-UHFFFAOYSA-N methyl 4-ethyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C=1C(CC)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 WJEHESGYJCURQT-UHFFFAOYSA-N 0.000 description 3
- WXNZNPDIBDMFTD-UHFFFAOYSA-N methyl 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 WXNZNPDIBDMFTD-UHFFFAOYSA-N 0.000 description 3
- VHYMNCITJMPWSX-UHFFFAOYSA-N methyl 4-methyl-6-[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]-2-phenylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1N1CCN(C)CC1 VHYMNCITJMPWSX-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 210000003470 mitochondria Anatomy 0.000 description 3
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 3
- OKGPGBZBEJDFKL-UHFFFAOYSA-N n-(3-ethylpiperidin-1-yl)-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound C1C(CC)CCCN1NC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 OKGPGBZBEJDFKL-UHFFFAOYSA-N 0.000 description 3
- RTFAAIUPALUWGC-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 RTFAAIUPALUWGC-UHFFFAOYSA-N 0.000 description 3
- ASESJHHKOUUTNL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]acetamide Chemical compound CN(C)CCNC(=O)CC1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 ASESJHHKOUUTNL-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- CBZGTHSGKYVKLD-UHFFFAOYSA-N (4-methyl-2-phenyl-6-pyridin-4-ylpyrimidin-5-yl)methanol Chemical compound OCC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 CBZGTHSGKYVKLD-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HTCLCCLGRBZNMM-UHFFFAOYSA-N 1-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 HTCLCCLGRBZNMM-UHFFFAOYSA-N 0.000 description 2
- LMGMQMSDDXKUPK-UHFFFAOYSA-N 1-[4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidin-5-yl]ethanol Chemical compound CC(O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 LMGMQMSDDXKUPK-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- KIMPXIILIACQOX-UHFFFAOYSA-N 2-hydroxyethyl 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound OCCOC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 KIMPXIILIACQOX-UHFFFAOYSA-N 0.000 description 2
- CZTVBDLVCZBHSA-UHFFFAOYSA-N 4,5-dimethyl-2-phenyl-6-pyridin-4-ylpyrimidine Chemical compound CC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 CZTVBDLVCZBHSA-UHFFFAOYSA-N 0.000 description 2
- QNSQQPUXUVEGIK-UHFFFAOYSA-N 4-[3-(difluoromethoxy)phenyl]-6-methyl-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC(OC(F)F)=C1 QNSQQPUXUVEGIK-UHFFFAOYSA-N 0.000 description 2
- OVJLUBDSTOIKEW-UHFFFAOYSA-N 4-methyl-2-phenyl-6-pyridin-4-ylpyrimidin-5-amine Chemical compound NC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 OVJLUBDSTOIKEW-UHFFFAOYSA-N 0.000 description 2
- HYDGABTVNXMSNZ-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-amine Chemical compound NC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 HYDGABTVNXMSNZ-UHFFFAOYSA-N 0.000 description 2
- PMDQTGOWFJOGSQ-UHFFFAOYSA-N 6-(4-hydroxy-3-nitrophenyl)hex-5-ene-2,4-dione Chemical compound CC(=O)CC(=O)C=CC1=CC=C(O)C([N+]([O-])=O)=C1 PMDQTGOWFJOGSQ-UHFFFAOYSA-N 0.000 description 2
- SAOZLCLVGMUGMC-UHFFFAOYSA-N 6-methyl-4-(3-nitrophenyl)-2-phenyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrimidine-2-carboxamide Chemical compound N1C(C)=CC(C=2C=C(C=CC=2)[N+]([O-])=O)=NC1(C=1C=CC=CC=1)C(=O)NCCN1CCCC1 SAOZLCLVGMUGMC-UHFFFAOYSA-N 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000007953 anoxia Effects 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- DQQUVRFUULNPTJ-UHFFFAOYSA-N ethyl 2-[(3,4-dimethoxyphenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=C(OC)C(OC)=C1 DQQUVRFUULNPTJ-UHFFFAOYSA-N 0.000 description 2
- CMEIMMSCHAUSSE-UHFFFAOYSA-N ethyl 2-[[2-[(4-chlorophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1OCC1=CC=C(Cl)C=C1 CMEIMMSCHAUSSE-UHFFFAOYSA-N 0.000 description 2
- VLMPZGNQKVZMCE-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-(4-nitrobenzoyl)prop-2-enoate Chemical compound CCOC(=O)C(=CN(C)C)C(=O)C1=CC=C([N+]([O-])=O)C=C1 VLMPZGNQKVZMCE-UHFFFAOYSA-N 0.000 description 2
- VKVFQCSTHQVULQ-UHFFFAOYSA-N ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1Cl VKVFQCSTHQVULQ-UHFFFAOYSA-N 0.000 description 2
- RWKLNGHAINWLCK-UHFFFAOYSA-N ethyl 4-(3-methoxyphenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(OC)=C1 RWKLNGHAINWLCK-UHFFFAOYSA-N 0.000 description 2
- CCWYJMFMHOLQBA-UHFFFAOYSA-N ethyl 4-(4-acetyloxy-3-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(OC(C)=O)C([N+]([O-])=O)=C1 CCWYJMFMHOLQBA-UHFFFAOYSA-N 0.000 description 2
- VSJHRUHTYGNRBR-UHFFFAOYSA-N ethyl 4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(O)C([N+]([O-])=O)=C1 VSJHRUHTYGNRBR-UHFFFAOYSA-N 0.000 description 2
- CCJUXYZWBFBSMQ-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]-3-nitrophenyl]-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1OCC1=CC=C(Cl)C=C1 CCJUXYZWBFBSMQ-UHFFFAOYSA-N 0.000 description 2
- CBESPYXFEOBFJG-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]-5-nitrophenyl]-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1OCC1=CC=C(Cl)C=C1 CBESPYXFEOBFJG-UHFFFAOYSA-N 0.000 description 2
- BLGZVRMOUBFSPZ-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]phenyl]-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 BLGZVRMOUBFSPZ-UHFFFAOYSA-N 0.000 description 2
- JRWMXBPKMRUMKD-UHFFFAOYSA-N ethyl 4-acetyloxy-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=CC1=CC=CC([N+]([O-])=O)=C1 JRWMXBPKMRUMKD-UHFFFAOYSA-N 0.000 description 2
- XUBXUOIUJGELSJ-UHFFFAOYSA-N ethyl 4-methyl-6-(2-methylsulfinyl-5-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC([N+]([O-])=O)=CC=C1S(C)=O XUBXUOIUJGELSJ-UHFFFAOYSA-N 0.000 description 2
- ZNUUQIBJSJUSKW-UHFFFAOYSA-N ethyl 4-methyl-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 ZNUUQIBJSJUSKW-UHFFFAOYSA-N 0.000 description 2
- BWJSNKZBQSEBIR-UHFFFAOYSA-N ethyl 4-methyl-6-[2-[(4-nitrophenyl)methoxy]phenyl]-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 BWJSNKZBQSEBIR-UHFFFAOYSA-N 0.000 description 2
- RKJVSWZHANEKLW-UHFFFAOYSA-N ethyl 6-methyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC(C(F)(F)F)=C1 RKJVSWZHANEKLW-UHFFFAOYSA-N 0.000 description 2
- MSQDVCRYLIHBKD-UHFFFAOYSA-N ethyl 6-methyl-2-phenyl-4-pyridin-4-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=NC=C1 MSQDVCRYLIHBKD-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000003447 ipsilateral effect Effects 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229940118019 malondialdehyde Drugs 0.000 description 2
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- HDEQAVSHXBELHJ-UHFFFAOYSA-N propan-2-yl 4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 HDEQAVSHXBELHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- BKPHIIZPHGIYSH-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(4-nitrophenyl)-2-pyridin-4-ylpyrimidin-5-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 BKPHIIZPHGIYSH-UHFFFAOYSA-N 0.000 description 1
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical group C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 1
- VQCUEPAYPNFCNY-UHFFFAOYSA-N 1-$l^{1}-oxidanylpentan-1-one Chemical compound CC[CH]CC([O])=O VQCUEPAYPNFCNY-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- PEHJUONYAQTZIK-UHFFFAOYSA-N 1-(2,4-dipyridin-4-ylpyrimidin-5-yl)ethanone Chemical compound CC(=O)C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=NC=C1 PEHJUONYAQTZIK-UHFFFAOYSA-N 0.000 description 1
- ODTKCFVQVNBOJK-UHFFFAOYSA-N 1-(3h-pyridin-4-ylidene)pentane-2,4-dione Chemical compound CC(=O)CC(=O)C=C1CC=NC=C1 ODTKCFVQVNBOJK-UHFFFAOYSA-N 0.000 description 1
- MLGQPMNRWZEOTG-UHFFFAOYSA-N 1-(4-methyl-2-phenyl-6-pyridin-4-ylpyrimidin-5-yl)ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=NC=C1 MLGQPMNRWZEOTG-UHFFFAOYSA-N 0.000 description 1
- PCYJRNQTBORQRG-UHFFFAOYSA-N 1-(6-methyl-2-phenyl-4-pyridin-4-yl-1,4-dihydropyrimidin-5-yl)ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=NC=C1 PCYJRNQTBORQRG-UHFFFAOYSA-N 0.000 description 1
- MNVQYPJNJWRBEV-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]urea;hydrochloride Chemical compound Cl.CN(C)CCNC(=O)NC1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 MNVQYPJNJWRBEV-UHFFFAOYSA-N 0.000 description 1
- BSEFPBJABNLLED-UHFFFAOYSA-N 1-[4-(4-chloro-3-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C(Cl)C([N+]([O-])=O)=C1 BSEFPBJABNLLED-UHFFFAOYSA-N 0.000 description 1
- MTLROFAFNLVKEL-UHFFFAOYSA-N 1-[4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=C(O)C([N+]([O-])=O)=C1 MTLROFAFNLVKEL-UHFFFAOYSA-N 0.000 description 1
- JSPCYJWGBUHQED-UHFFFAOYSA-N 1-[6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidin-5-yl]ethanone Chemical compound CC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC([N+]([O-])=O)=C1 JSPCYJWGBUHQED-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- HAEOVYIFYGTLSX-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(3-nitrophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 HAEOVYIFYGTLSX-UHFFFAOYSA-N 0.000 description 1
- CVZTYMRWVBZAAO-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-nitrophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 CVZTYMRWVBZAAO-UHFFFAOYSA-N 0.000 description 1
- DVIGLDMXUAOCMC-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-6-(3-nitrophenyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC(Cl)=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 DVIGLDMXUAOCMC-UHFFFAOYSA-N 0.000 description 1
- KHVBMLZFRKVTQI-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-(dimethylamino)ethyl]-4-(4-nitrophenyl)pyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 KHVBMLZFRKVTQI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- OOTKFPUOHJPLPL-UHFFFAOYSA-N 2-methyl-4-(3-nitrophenyl)-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound N1C(C)=NC(COC2=O)=C2C1C1=CC=CC([N+]([O-])=O)=C1 OOTKFPUOHJPLPL-UHFFFAOYSA-N 0.000 description 1
- LUXNUTHBOGRJMY-UHFFFAOYSA-N 2-methyl-4-[2-(trifluoromethyl)phenyl]-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound C1OC(=O)C2=C1NC(C)=NC2C1=CC=CC=C1C(F)(F)F LUXNUTHBOGRJMY-UHFFFAOYSA-N 0.000 description 1
- YUQGUJAMCUWOOY-UHFFFAOYSA-N 2-phenyl-4-pyridin-4-yl-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound O=C1OCC(N=2)=C1C(C=1C=CN=CC=1)NC=2C1=CC=CC=C1 YUQGUJAMCUWOOY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- UXGCGDAMTXPIIJ-UHFFFAOYSA-N 3-[(3-nitrophenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CC([N+]([O-])=O)=C1 UXGCGDAMTXPIIJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HJEGPLGZMFMSIB-UHFFFAOYSA-N 4-(2,3-dimethoxyphenyl)-2-methyl-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound COC1=CC=CC(C2C3=C(COC3=O)N=C(C)N2)=C1OC HJEGPLGZMFMSIB-UHFFFAOYSA-N 0.000 description 1
- SZXOMVLUUKLEJL-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-2-methyl-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C(=O)OC2)=C2N=C(C)N1 SZXOMVLUUKLEJL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BTYGBWDYPPGJFI-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-phenyl-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one Chemical compound [O-][N+](=O)C1=CC=CC(C2C3=C(COC3=O)N=C(N2)C=2C=CC=CC=2)=C1 BTYGBWDYPPGJFI-UHFFFAOYSA-N 0.000 description 1
- FRRFZXNNSISAAN-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 FRRFZXNNSISAAN-UHFFFAOYSA-N 0.000 description 1
- DJJVEDVOERJUBI-UHFFFAOYSA-N 4-(4-nitrophenyl)-2-pyridin-4-ylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 DJJVEDVOERJUBI-UHFFFAOYSA-N 0.000 description 1
- UYMMYFLNPMRZAY-UHFFFAOYSA-N 4-[2-[(4-chlorophenyl)methoxy]phenyl]-2-methyl-4,7-dihydro-1h-furo[3,4-d]pyrimidin-5-one;hydrochloride Chemical compound Cl.C1OC(=O)C2=C1NC(C)=NC2C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 UYMMYFLNPMRZAY-UHFFFAOYSA-N 0.000 description 1
- YTHJCZRFJGXPTL-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1[N+]([O-])=O YTHJCZRFJGXPTL-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- KYFYOFDWCMBLQG-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-phenyl-n-(2-piperidin-1-ylethyl)pyrimidine-5-carboxamide Chemical compound C1CCCCN1CCNC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 KYFYOFDWCMBLQG-UHFFFAOYSA-N 0.000 description 1
- UCKMOHDRMJCMQG-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)-2-pyridin-4-ylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CN=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 UCKMOHDRMJCMQG-UHFFFAOYSA-N 0.000 description 1
- BCOWIQBBZVVQLB-UHFFFAOYSA-N 4-methyl-n-[(4-methylpiperazin-1-yl)methyl]-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound C1CN(C)CCN1CNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 BCOWIQBBZVVQLB-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- PCSMWTIEFMSUFS-UHFFFAOYSA-N 6-(4-nitrophenyl)hex-5-ene-2,4-dione Chemical compound CC(=O)CC(=O)C=CC1=CC=C([N+]([O-])=O)C=C1 PCSMWTIEFMSUFS-UHFFFAOYSA-N 0.000 description 1
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
- XWEGBPZVPUCQBE-UHFFFAOYSA-N 6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxamide Chemical compound N=1C(C)=C(C(N)=O)C(C=2C=C(C=CC=2)[N+]([O-])=O)NC=1C1=CC=CC=C1 XWEGBPZVPUCQBE-UHFFFAOYSA-N 0.000 description 1
- RIFFRJGVOQTXMV-UHFFFAOYSA-N 6-methyl-n-[2-(4-methylpiperazin-1-yl)ethyl]-4-(3-nitrophenyl)-2-phenyl-1h-pyrimidine-2-carboxamide Chemical compound C1CN(C)CCN1CCNC(=O)C1(C=2C=CC=CC=2)N=C(C=2C=C(C=CC=2)[N+]([O-])=O)C=C(C)N1 RIFFRJGVOQTXMV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XSXBTCZMXKJGHW-UHFFFAOYSA-N CCOC(=O)C(C(C)=O)=C1NC=CC=C1 Chemical compound CCOC(=O)C(C(C)=O)=C1NC=CC=C1 XSXBTCZMXKJGHW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 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
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- GDTDQLOBDSTBGX-UHFFFAOYSA-N [2-(4-chlorophenyl)-4-(3-nitrophenyl)pyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 GDTDQLOBDSTBGX-UHFFFAOYSA-N 0.000 description 1
- ANAZRWOIXHHIOM-UHFFFAOYSA-N [2-(4-chlorophenyl)-4-(4-nitrophenyl)pyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 ANAZRWOIXHHIOM-UHFFFAOYSA-N 0.000 description 1
- YPPVASHUGYTLAV-UHFFFAOYSA-N [2-(4-chlorophenyl)-4-methyl-6-(3-nitrophenyl)pyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 YPPVASHUGYTLAV-UHFFFAOYSA-N 0.000 description 1
- UBMKXZKIVLFLHV-UHFFFAOYSA-N [4-(3-amino-4-hydroxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(O)C(N)=C1 UBMKXZKIVLFLHV-UHFFFAOYSA-N 0.000 description 1
- XNOJXZJUXPRDNS-UHFFFAOYSA-N [4-(3-aminophenyl)-6-methyl-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(N)=C1 XNOJXZJUXPRDNS-UHFFFAOYSA-N 0.000 description 1
- YMGQCEUZEUDLQZ-UHFFFAOYSA-N [4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(O)C([N+]([O-])=O)=C1 YMGQCEUZEUDLQZ-UHFFFAOYSA-N 0.000 description 1
- NXDCLURXZOMPFV-UHFFFAOYSA-N [4-[3-(difluoromethoxy)phenyl]-6-methyl-2-phenylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(OC(F)F)=C1 NXDCLURXZOMPFV-UHFFFAOYSA-N 0.000 description 1
- YECVGDCQAMSZRR-UHFFFAOYSA-N [4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]-[4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl]methanone Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C(=O)C=2C(=NC(=NC=2C)C=2C=CC=CC=2)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 YECVGDCQAMSZRR-UHFFFAOYSA-N 0.000 description 1
- IEPXKFCYIIKRDP-UHFFFAOYSA-N [4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidin-5-yl]-piperazin-1-ylmethanone Chemical compound C1CNCCN1C(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC([N+]([O-])=O)=C1 IEPXKFCYIIKRDP-UHFFFAOYSA-N 0.000 description 1
- JNMYXDSSJRWTJM-UHFFFAOYSA-N [4-methyl-6-(3-nitrophenyl)-2-pyridin-4-ylpyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CN=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 JNMYXDSSJRWTJM-UHFFFAOYSA-N 0.000 description 1
- QOXHUJLUBYKSBY-UHFFFAOYSA-N [6-methyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC(C(F)(F)F)=C1 QOXHUJLUBYKSBY-UHFFFAOYSA-N 0.000 description 1
- JHXIREJKJWYZFN-UHFFFAOYSA-N [6-methyl-4-(2-nitrophenyl)-2-phenyl-1,4-dihydropyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC=C1[N+]([O-])=O JHXIREJKJWYZFN-UHFFFAOYSA-N 0.000 description 1
- AKRKYZLCSXNLCE-UHFFFAOYSA-N [6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC([N+]([O-])=O)=C1 AKRKYZLCSXNLCE-UHFFFAOYSA-N 0.000 description 1
- VGHLSLJKSCPQOG-UHFFFAOYSA-N [6-methyl-4-(4-nitrophenyl)-2-phenyl-1,4-dihydropyrimidin-5-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C([N+]([O-])=O)C=C1 VGHLSLJKSCPQOG-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000006383 alkylpyridyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 208000006752 brain edema Diseases 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
- 125000006380 bromopyridyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 210000000269 carotid artery external Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000006378 chloropyridyl group Chemical group 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- OCXGTPDKNBIOTF-UHFFFAOYSA-N dibromo(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 OCXGTPDKNBIOTF-UHFFFAOYSA-N 0.000 description 1
- ASWXNYNXAOQCCD-UHFFFAOYSA-N dichloro(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Cl)(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 ASWXNYNXAOQCCD-UHFFFAOYSA-N 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- KWMUAEYVIFJZEB-UHFFFAOYSA-N diethylalumanylformonitrile Chemical compound CC[Al](CC)C#N KWMUAEYVIFJZEB-UHFFFAOYSA-N 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000678 effect on lipid Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- LHKRRTOSTQRAGV-UHFFFAOYSA-N ethyl 2,4-dimethyl-6-(3-nitrophenyl)pyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)N=C(C)N=C1C1=CC=CC([N+]([O-])=O)=C1 LHKRRTOSTQRAGV-UHFFFAOYSA-N 0.000 description 1
- KBXZPCSQTVFDOH-UHFFFAOYSA-N ethyl 2,4-dimethyl-6-pyridin-3-ylpyrimidine-5-carboxylate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)C1=C(C)N=C(C)N=C1C1=CC=CN=C1 KBXZPCSQTVFDOH-UHFFFAOYSA-N 0.000 description 1
- WQNAMGPKQFPPNL-UHFFFAOYSA-N ethyl 2,4-dimethyl-6-pyridin-4-ylpyrimidine-5-carboxylate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)C1=C(C)N=C(C)N=C1C1=CC=NC=C1 WQNAMGPKQFPPNL-UHFFFAOYSA-N 0.000 description 1
- IHDARUMBHZZDLL-UHFFFAOYSA-N ethyl 2,6-dimethyl-4-[2-[(4-nitrophenyl)methoxy]phenyl]-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(C)=NC1C1=CC=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 IHDARUMBHZZDLL-UHFFFAOYSA-N 0.000 description 1
- MQMUODYRGQEVPD-UHFFFAOYSA-N ethyl 2,6-dimethyl-4-pyridin-3-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)NC1C1=CC=CN=C1 MQMUODYRGQEVPD-UHFFFAOYSA-N 0.000 description 1
- OPFAIKSCSPEZEK-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-4-(3-nitrophenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 OPFAIKSCSPEZEK-UHFFFAOYSA-N 0.000 description 1
- VNIUOZFWUFAZNY-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-4-(4-nitrophenyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 VNIUOZFWUFAZNY-UHFFFAOYSA-N 0.000 description 1
- ACWGFCXASWGLFF-UHFFFAOYSA-N ethyl 2-[(2-chloro-5-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC([N+]([O-])=O)=CC=C1Cl ACWGFCXASWGLFF-UHFFFAOYSA-N 0.000 description 1
- REJMGENXLYEPRA-UHFFFAOYSA-N ethyl 2-[(3-cyanophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC(C#N)=C1 REJMGENXLYEPRA-UHFFFAOYSA-N 0.000 description 1
- WZPCIZKUWHKYHR-UHFFFAOYSA-N ethyl 2-[(3-hydroxy-4-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=C([N+]([O-])=O)C(O)=C1 WZPCIZKUWHKYHR-UHFFFAOYSA-N 0.000 description 1
- DZSCCQUQJNHJIO-UHFFFAOYSA-N ethyl 2-[(3-methoxyphenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC(OC)=C1 DZSCCQUQJNHJIO-UHFFFAOYSA-N 0.000 description 1
- QBLGRAAPADHBOW-UHFFFAOYSA-N ethyl 2-[(4-cyanophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=C(C#N)C=C1 QBLGRAAPADHBOW-UHFFFAOYSA-N 0.000 description 1
- OSHDXNDKYVHBRV-UHFFFAOYSA-N ethyl 2-[(4-hydroxy-3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=C(O)C([N+]([O-])=O)=C1 OSHDXNDKYVHBRV-UHFFFAOYSA-N 0.000 description 1
- IYBMAWHLXMHFPF-UHFFFAOYSA-N ethyl 2-[[2-(4-chlorophenyl)sulfanylphenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1SC1=CC=C(Cl)C=C1 IYBMAWHLXMHFPF-UHFFFAOYSA-N 0.000 description 1
- YQUJWQAIEBIIHC-UHFFFAOYSA-N ethyl 2-[[2-[(2,4-dichlorophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1OCC1=CC=C(Cl)C=C1Cl YQUJWQAIEBIIHC-UHFFFAOYSA-N 0.000 description 1
- RBNYEXBMESSINY-UHFFFAOYSA-N ethyl 2-[[2-[(4-chlorophenyl)methoxy]-3-nitrophenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC([N+]([O-])=O)=C1OCC1=CC=C(Cl)C=C1 RBNYEXBMESSINY-UHFFFAOYSA-N 0.000 description 1
- ONUGANSSQYDINX-UHFFFAOYSA-N ethyl 2-[[2-[(4-methoxyphenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1OCC1=CC=C(OC)C=C1 ONUGANSSQYDINX-UHFFFAOYSA-N 0.000 description 1
- QHVXKJCYHQKZPY-UHFFFAOYSA-N ethyl 2-[[2-[(4-nitrophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 QHVXKJCYHQKZPY-UHFFFAOYSA-N 0.000 description 1
- AMNNOWCRMDNMFH-UHFFFAOYSA-N ethyl 2-[[3-[(4-chlorophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC(OCC=2C=CC(Cl)=CC=2)=C1 AMNNOWCRMDNMFH-UHFFFAOYSA-N 0.000 description 1
- NHKPDXXDHJVWSA-UHFFFAOYSA-N ethyl 2-[[4-[(4-chlorophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound C1=CC(C=C(C(=O)OCC)C(C)=O)=CC=C1OCC1=CC=C(Cl)C=C1 NHKPDXXDHJVWSA-UHFFFAOYSA-N 0.000 description 1
- FQCBXUFUDFABAD-UHFFFAOYSA-N ethyl 2-methyl-4-phenyl-6-pyridin-4-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C=2C=CC=CC=2)N=C(C)N=C1C1=CC=NC=C1 FQCBXUFUDFABAD-UHFFFAOYSA-N 0.000 description 1
- JYVVSXGHZHODLV-UHFFFAOYSA-N ethyl 2-methyl-6-phenyl-4-pyridin-4-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C=2C=CC=CC=2)NC(C)=NC1C1=CC=NC=C1 JYVVSXGHZHODLV-UHFFFAOYSA-N 0.000 description 1
- NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 description 1
- BIFUZMGIVJNRAK-UHFFFAOYSA-N ethyl 3-oxo-2-(2h-pyridin-3-ylidene)butanoate Chemical compound CCOC(=O)C(C(C)=O)=C1CN=CC=C1 BIFUZMGIVJNRAK-UHFFFAOYSA-N 0.000 description 1
- DMHOSINWPLXTDH-UHFFFAOYSA-N ethyl 3-oxo-2-(3h-pyridin-4-ylidene)butanoate Chemical compound CCOC(=O)C(C(C)=O)=C1CC=NC=C1 DMHOSINWPLXTDH-UHFFFAOYSA-N 0.000 description 1
- HRLQOLFOVIQJRG-UHFFFAOYSA-N ethyl 3-oxo-2-[[3-(trifluoromethyl)phenyl]methylidene]butanoate Chemical compound CCOC(=O)C(C(C)=O)=CC1=CC=CC(C(F)(F)F)=C1 HRLQOLFOVIQJRG-UHFFFAOYSA-N 0.000 description 1
- ZTKIGPUVTBIGFP-UHFFFAOYSA-N ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC([N+]([O-])=O)=CC=C1Cl ZTKIGPUVTBIGFP-UHFFFAOYSA-N 0.000 description 1
- KHNLNBSXQJCTRT-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1Cl KHNLNBSXQJCTRT-UHFFFAOYSA-N 0.000 description 1
- OFCVCTHRTKLAAM-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)N=C(C)NC1C1=CC=CC=C1OC OFCVCTHRTKLAAM-UHFFFAOYSA-N 0.000 description 1
- ILCYJBNSLVJUBD-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC=C1OC ILCYJBNSLVJUBD-UHFFFAOYSA-N 0.000 description 1
- NXDBSPXVBGYPLA-UHFFFAOYSA-N ethyl 4-(3,4-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)N=C(C)NC1C1=CC=C(OC)C(OC)=C1 NXDBSPXVBGYPLA-UHFFFAOYSA-N 0.000 description 1
- XKQJUCJHKQOPLY-UHFFFAOYSA-N ethyl 4-(3,4-dimethoxyphenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=C(OC)C(OC)=C1 XKQJUCJHKQOPLY-UHFFFAOYSA-N 0.000 description 1
- BLUVFBKTZXUKML-UHFFFAOYSA-N ethyl 4-(3,4-dimethoxyphenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(OC)C(OC)=C1 BLUVFBKTZXUKML-UHFFFAOYSA-N 0.000 description 1
- PVKKKRAACYLMSR-UHFFFAOYSA-N ethyl 4-(3-chlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(Cl)=C1 PVKKKRAACYLMSR-UHFFFAOYSA-N 0.000 description 1
- GDPARFXHEXVVNF-UHFFFAOYSA-N ethyl 4-(3-cyanophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC(C#N)=C1 GDPARFXHEXVVNF-UHFFFAOYSA-N 0.000 description 1
- YRIBVWTWMFIAAL-UHFFFAOYSA-N ethyl 4-(3-cyanophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(C#N)=C1 YRIBVWTWMFIAAL-UHFFFAOYSA-N 0.000 description 1
- SJJYVKZSBGSEMP-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C([N+]([O-])=O)C(O)=C1 SJJYVKZSBGSEMP-UHFFFAOYSA-N 0.000 description 1
- XELZXPOKTOXPLF-UHFFFAOYSA-N ethyl 4-(3-methoxyphenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC(OC)=C1 XELZXPOKTOXPLF-UHFFFAOYSA-N 0.000 description 1
- LWBZWHNYVIHVGX-UHFFFAOYSA-N ethyl 4-(4,5-dimethoxy-2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=NC1C1=CC(OC)=C(OC)C=C1[N+]([O-])=O LWBZWHNYVIHVGX-UHFFFAOYSA-N 0.000 description 1
- BUMPRWZHKWZENR-UHFFFAOYSA-N ethyl 4-(4-chloro-3-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=C(Cl)C([N+]([O-])=O)=C1 BUMPRWZHKWZENR-UHFFFAOYSA-N 0.000 description 1
- QGCFGSBCBUOHQP-UHFFFAOYSA-N ethyl 4-(4-chloro-3-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C([N+]([O-])=O)=C1 QGCFGSBCBUOHQP-UHFFFAOYSA-N 0.000 description 1
- OKRHDRPOKNFCIG-UHFFFAOYSA-N ethyl 4-(4-cyanophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C(C#N)C=C1 OKRHDRPOKNFCIG-UHFFFAOYSA-N 0.000 description 1
- XEOLTVBEHGLQAJ-UHFFFAOYSA-N ethyl 4-(4-cyanophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(C#N)C=C1 XEOLTVBEHGLQAJ-UHFFFAOYSA-N 0.000 description 1
- KPQFWKMFZWQFEU-UHFFFAOYSA-N ethyl 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC(OC)=C(O)C([N+]([O-])=O)=C1 KPQFWKMFZWQFEU-UHFFFAOYSA-N 0.000 description 1
- XXHMIVHHQXODEI-UHFFFAOYSA-N ethyl 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound COC=1C=C(C=C(C=1O)[N+](=O)[O-])C1=NC(=NC(=C1C(=O)OCC)C)C1=CC=CC=C1 XXHMIVHHQXODEI-UHFFFAOYSA-N 0.000 description 1
- FCKXUHCXEUBJRC-UHFFFAOYSA-N ethyl 4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C(O)C([N+]([O-])=O)=C1 FCKXUHCXEUBJRC-UHFFFAOYSA-N 0.000 description 1
- WQCURZXFZJIDAU-UHFFFAOYSA-N ethyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C(C(=O)OC)C=C1 WQCURZXFZJIDAU-UHFFFAOYSA-N 0.000 description 1
- PKACNXSJFYEGDA-UHFFFAOYSA-N ethyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(C(=O)OC)C=C1 PKACNXSJFYEGDA-UHFFFAOYSA-N 0.000 description 1
- RMGLIKGCUKKUBV-UHFFFAOYSA-N ethyl 4-(4-nitrophenyl)-2-pyridin-4-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 RMGLIKGCUKKUBV-UHFFFAOYSA-N 0.000 description 1
- YSBRMMHWKVCXTB-UHFFFAOYSA-N ethyl 4-[2-(4-chlorophenyl)sulfanylphenyl]-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1SC1=CC=C(Cl)C=C1 YSBRMMHWKVCXTB-UHFFFAOYSA-N 0.000 description 1
- PUYLMIXDLHTGGF-UHFFFAOYSA-N ethyl 4-[2-(4-chlorophenyl)sulfanylphenyl]-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1SC1=CC=C(Cl)C=C1 PUYLMIXDLHTGGF-UHFFFAOYSA-N 0.000 description 1
- QYVIQTLYZPHZCB-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]-3-nitrophenyl]-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC([N+]([O-])=O)=C1OCC1=CC=C(Cl)C=C1 QYVIQTLYZPHZCB-UHFFFAOYSA-N 0.000 description 1
- UXYYYGQFJYOSIU-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]phenyl]-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=NC1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 UXYYYGQFJYOSIU-UHFFFAOYSA-N 0.000 description 1
- BYXYNJFYMSIWJC-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]phenyl]-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(C)=NC1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 BYXYNJFYMSIWJC-UHFFFAOYSA-N 0.000 description 1
- OGSTWRJTFBAZBT-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]phenyl]-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 OGSTWRJTFBAZBT-UHFFFAOYSA-N 0.000 description 1
- LNDWUKPJXMGBKT-UHFFFAOYSA-N ethyl 4-[2-[(4-chlorophenyl)methoxy]phenyl]-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 LNDWUKPJXMGBKT-UHFFFAOYSA-N 0.000 description 1
- WIDFCDLDXBUOSR-UHFFFAOYSA-N ethyl 4-[2-[(4-methoxyphenyl)methoxy]phenyl]-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)N=C(C)NC1C1=CC=CC=C1OCC1=CC=C(OC)C=C1 WIDFCDLDXBUOSR-UHFFFAOYSA-N 0.000 description 1
- MLSRCLAKIWOTIT-UHFFFAOYSA-N ethyl 4-[4-[(4-chlorophenyl)methoxy]phenyl]-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(C)=NC1C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 MLSRCLAKIWOTIT-UHFFFAOYSA-N 0.000 description 1
- WREJJEZFHNTPEW-UHFFFAOYSA-N ethyl 4-acetyloxy-2-[(2-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=CC1=CC=CC=C1[N+]([O-])=O WREJJEZFHNTPEW-UHFFFAOYSA-N 0.000 description 1
- OXHKUEAZKPVTHC-UHFFFAOYSA-N ethyl 4-acetyloxy-2-[(3,4-dimethoxyphenyl)methylidene]-3-oxobutanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=CC1=CC=C(OC)C(OC)=C1 OXHKUEAZKPVTHC-UHFFFAOYSA-N 0.000 description 1
- POAKOSPXKPYCTN-UHFFFAOYSA-N ethyl 4-acetyloxy-2-[[2-[(4-nitrophenyl)methoxy]phenyl]methylidene]-3-oxobutanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=CC1=CC=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 POAKOSPXKPYCTN-UHFFFAOYSA-N 0.000 description 1
- JQXAIKQXDWWSIK-UHFFFAOYSA-N ethyl 4-acetyloxy-3-oxo-2-(3h-pyridin-4-ylidene)butanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=C1CC=NC=C1 JQXAIKQXDWWSIK-UHFFFAOYSA-N 0.000 description 1
- JVZJWNJCCAEGII-UHFFFAOYSA-N ethyl 4-acetyloxy-3-oxo-2-[[2-(trifluoromethyl)phenyl]methylidene]butanoate Chemical compound CC(=O)OCC(=O)C(C(=O)OCC)=CC1=CC=CC=C1C(F)(F)F JVZJWNJCCAEGII-UHFFFAOYSA-N 0.000 description 1
- JGPYHGDGHBSVOQ-UHFFFAOYSA-N ethyl 4-methyl-2-phenyl-6-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC(C(F)(F)F)=C1 JGPYHGDGHBSVOQ-UHFFFAOYSA-N 0.000 description 1
- PKBAMXQMHLTDJT-UHFFFAOYSA-N ethyl 4-methyl-2-phenyl-6-pyridin-2-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=N1 PKBAMXQMHLTDJT-UHFFFAOYSA-N 0.000 description 1
- KRXSXZMNNVFSJJ-UHFFFAOYSA-N ethyl 4-methyl-2-phenyl-6-pyridin-3-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CN=C1 KRXSXZMNNVFSJJ-UHFFFAOYSA-N 0.000 description 1
- XZEFQCXEKWGZDB-UHFFFAOYSA-N ethyl 4-methyl-6-(2-nitrophenyl)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1[N+]([O-])=O XZEFQCXEKWGZDB-UHFFFAOYSA-N 0.000 description 1
- XXONWADFUFSSCT-UHFFFAOYSA-N ethyl 6-(diethoxymethyl)-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1C(C(OCC)OCC)=C(C(=O)OCC)C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C1C1=CC=CC=C1 XXONWADFUFSSCT-UHFFFAOYSA-N 0.000 description 1
- JVQUMLWFYDAZNI-UHFFFAOYSA-N ethyl 6-methyl-2-phenyl-4-pyridin-2-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC=N1 JVQUMLWFYDAZNI-UHFFFAOYSA-N 0.000 description 1
- RQHFQPRCGCJHNM-UHFFFAOYSA-N ethyl 6-methyl-2-phenyl-4-pyridin-3-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CN=C1 RQHFQPRCGCJHNM-UHFFFAOYSA-N 0.000 description 1
- XLAFXIJNPWIPCV-UHFFFAOYSA-N ethyl 6-methyl-4-(3-nitrophenyl)-2-pyridin-3-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=NC=CC=2)=NC1C1=CC=CC([N+]([O-])=O)=C1 XLAFXIJNPWIPCV-UHFFFAOYSA-N 0.000 description 1
- ZLRZRRFQZZSNCC-UHFFFAOYSA-N ethyl 6-methyl-4-[2-[(4-nitrophenyl)methoxy]phenyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 ZLRZRRFQZZSNCC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000006379 fluoropyridyl group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000006377 halopyridyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DNGGJHGMGIPOHK-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC(Cl)=CC=2)NC1C1=CC=CC([N+]([O-])=O)=C1 DNGGJHGMGIPOHK-UHFFFAOYSA-N 0.000 description 1
- BYXFQCREICATSK-UHFFFAOYSA-N methyl 2-methyl-4-(3-nitrophenyl)-6-phenylpyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)C=C1C1=CC=CC([N+]([O-])=O)=C1 BYXFQCREICATSK-UHFFFAOYSA-N 0.000 description 1
- BQNDNSZWSMWLES-UHFFFAOYSA-N methyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(C=2C=CC=CC=2)=NC1C1=CC([N+]([O-])=O)=CC=C1Cl BQNDNSZWSMWLES-UHFFFAOYSA-N 0.000 description 1
- HOFYEOMYELFYHR-UHFFFAOYSA-N methyl 4-(3-hydroxyphenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC(O)=C1 HOFYEOMYELFYHR-UHFFFAOYSA-N 0.000 description 1
- OWFWNAJKVUGPHW-UHFFFAOYSA-N methyl 6-ethyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N=1C(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)NC=1C1=CC=CC=C1 OWFWNAJKVUGPHW-UHFFFAOYSA-N 0.000 description 1
- AYNCUYZTPVTJMT-UHFFFAOYSA-N methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC([N+]([O-])=O)=C1 AYNCUYZTPVTJMT-UHFFFAOYSA-N 0.000 description 1
- PNBYKCWYLFNZDR-UHFFFAOYSA-N methyl 6-methyl-4-(3-nitrophenyl)-2-pyridin-4-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(C=2C=CN=CC=2)=NC1C1=CC=CC([N+]([O-])=O)=C1 PNBYKCWYLFNZDR-UHFFFAOYSA-N 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- XJXVVQHIQXKAEV-UHFFFAOYSA-N n,n-dimethylformamide;methanethiol Chemical compound SC.CN(C)C=O XJXVVQHIQXKAEV-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- JPRBSCIAWCNGNO-UHFFFAOYSA-N n-(2-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxamide Chemical compound N1C(C)=C(C(=O)NCCO)C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C1C1=CC=CC=C1 JPRBSCIAWCNGNO-UHFFFAOYSA-N 0.000 description 1
- GHZZEZFBONZCSC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,4-dimethyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound OCCN(C)C(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 GHZZEZFBONZCSC-UHFFFAOYSA-N 0.000 description 1
- HSEHQMQDVUDHDZ-UHFFFAOYSA-N n-[(dimethylamino)methyl]-4-methyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 HSEHQMQDVUDHDZ-UHFFFAOYSA-N 0.000 description 1
- ROPMRYLYUMBXBZ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[(3-nitrophenyl)methylidene]-3-oxobutanamide Chemical compound CN(C)CCNC(=O)C(C(C)=O)=CC1=CC=CC([N+]([O-])=O)=C1 ROPMRYLYUMBXBZ-UHFFFAOYSA-N 0.000 description 1
- ILQDCYAHKKRXNF-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 ILQDCYAHKKRXNF-UHFFFAOYSA-N 0.000 description 1
- WFXRRFNCXVWDDL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-nitrophenyl)-2-pyridin-4-ylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=C([N+]([O-])=O)C=C1 WFXRRFNCXVWDDL-UHFFFAOYSA-N 0.000 description 1
- XGIJAXFIYUZOSD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-6-(3-nitrophenyl)-2-pyridin-4-ylpyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CN=CC=2)N=C1C1=CC=CC([N+]([O-])=O)=C1 XGIJAXFIYUZOSD-UHFFFAOYSA-N 0.000 description 1
- JYABRVHNMXFFCX-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-6-methyl-4-(3-nitrophenyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=CC([N+]([O-])=O)=C1 JYABRVHNMXFFCX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003463 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LTWZJUPFYLTCCA-UHFFFAOYSA-N tert-butyl n-(4-methyl-2-phenyl-6-pyridin-4-ylpyrimidin-5-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 LTWZJUPFYLTCCA-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 210000002268 wool Anatomy 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
- C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
-
- 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
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848418380A GB8418380D0 (en) | 1984-07-19 | 1984-07-19 | Pyrimidine derivatives |
GB848424711A GB8424711D0 (en) | 1984-10-01 | 1984-10-01 | Pyrimidine derivatives |
GB858509623A GB8509623D0 (en) | 1985-04-15 | 1985-04-15 | Pyrimidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
NO852869L true NO852869L (no) | 1986-01-20 |
Family
ID=27262418
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO852869A NO852869L (no) | 1984-07-19 | 1985-07-18 | Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-derivater. |
Country Status (10)
Country | Link |
---|---|
US (1) | US4698340A (id) |
EP (1) | EP0169712B1 (id) |
JP (1) | JPH0649688B2 (id) |
AU (1) | AU4520285A (id) |
DE (1) | DE3580875D1 (id) |
DK (1) | DK327985A (id) |
ES (1) | ES8700661A1 (id) |
FI (1) | FI852796L (id) |
GR (1) | GR851735B (id) |
NO (1) | NO852869L (id) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3508533A1 (de) * | 1985-03-09 | 1986-09-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von benzylidenverbindungen |
DE3675197D1 (de) * | 1985-12-03 | 1990-11-29 | Sumitomo Chemical Co | Pyridinylpyrimidin-derivate, verfahren zu deren herstellung und diese als wirksamen stoff enthaltende pflanzenkrankheiten-schutzmittel. |
GB8530602D0 (en) * | 1985-12-12 | 1986-01-22 | Fujisawa Pharmaceutical Co | Heterocyclic compounds |
CA1288433C (en) * | 1986-12-03 | 1991-09-03 | Tsuguhiro Katoh | Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient |
FR2649699A1 (fr) * | 1989-07-13 | 1991-01-18 | Rhone Poulenc Agrochimie | 4-phenyl pyrimidine fongicides |
IL91418A (en) * | 1988-09-01 | 1997-11-20 | Rhone Poulenc Agrochimie | (hetero) cyclic amide derivatives, process for their preparation and fungicidal compositions containing them |
HU221855B1 (hu) * | 1994-09-09 | 2003-02-28 | Nippon Shinyaku Co., Ltd. | Szubsztituált piridin-, pirimidin- és triazinszármazékok és ilyen vegyületeket tartalmazó gyógyászati készítmények |
US5594141A (en) * | 1994-11-23 | 1997-01-14 | Neurogen Corporation | Certain aminomethyl biphenyl, aminomethyl phenyl pyridine and aminomethyl phenyl pyrimidine derivatives; novel dopamine receptor subtype selective ligands |
IL137922A0 (en) | 1998-02-17 | 2001-10-31 | Tularik Inc | Anti-viral pyrimidine derivatives |
DE19817264A1 (de) * | 1998-04-18 | 1999-10-21 | Bayer Ag | Neue Dihydropyrimidine |
DE19817265A1 (de) | 1998-04-18 | 1999-10-21 | Bayer Ag | Verwendung von Dihydropyrimidinen als Arzneimittel und neue Stoffe |
US6274588B1 (en) | 1999-05-31 | 2001-08-14 | Hoffmann-La Roche Inc. | 4-phenyl-pyrimidine derivatives |
US6410726B1 (en) | 2000-01-12 | 2002-06-25 | Tularik Inc. | Arylsulfonic acid salts of pyrimidine-based antiviral |
JP4623354B2 (ja) * | 2000-09-14 | 2011-02-02 | 味の素株式会社 | 新規ピリミジン誘導体及び新規ピリジン誘導体 |
DK1578731T3 (da) * | 2002-12-16 | 2010-02-15 | Astrazeneca Uk Ltd | Fremgangsmåde til fremstilling af pyrimidinforbindelser |
HUP0400405A3 (en) * | 2004-02-10 | 2009-03-30 | Sanofi Synthelabo | Pyrimidine derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
RU2572616C2 (ru) | 2008-02-01 | 2016-01-20 | Оркид Рисерч Лабораториз Лимитед | Новые гетероциклы |
GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
BR112013011737A2 (pt) | 2010-11-15 | 2016-08-09 | Univ Leuven Kath | composto, uso de um composto composição farmacêutica, e, método de tratamento ou prevenção de uma infecção por hiv |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3944581A (en) * | 1974-11-01 | 1976-03-16 | Morton-Norwich Products, Inc. | 5-Substituted-2,4-diphenylpyrimidines |
US3969355A (en) * | 1974-11-01 | 1976-07-13 | Morton-Norwich Products, Inc. | 5-Aminoethyl-2,4-diphenylpyrimidine dihydrobromide |
US4382140A (en) * | 1982-01-26 | 1983-05-03 | Norwich Eaton Pharmaceuticals, Inc. | 2,4-Diphenyl-5-pyrimidinecarbonitrile |
DE3234684A1 (de) * | 1982-09-18 | 1984-03-22 | Bayer Ag, 5090 Leverkusen | Neue dihydropyrimidine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
US4727073A (en) * | 1984-10-01 | 1988-02-23 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives and composition of the same |
-
1985
- 1985-07-11 US US06/753,912 patent/US4698340A/en not_active Expired - Fee Related
- 1985-07-12 GR GR851735A patent/GR851735B/el unknown
- 1985-07-17 FI FI852796A patent/FI852796L/fi not_active Application Discontinuation
- 1985-07-18 DE DE8585305143T patent/DE3580875D1/de not_active Expired - Fee Related
- 1985-07-18 DK DK327985A patent/DK327985A/da not_active Application Discontinuation
- 1985-07-18 NO NO852869A patent/NO852869L/no unknown
- 1985-07-18 ES ES545347A patent/ES8700661A1/es not_active Expired
- 1985-07-18 EP EP85305143A patent/EP0169712B1/en not_active Expired - Lifetime
- 1985-07-19 AU AU45202/85A patent/AU4520285A/en not_active Abandoned
- 1985-07-19 JP JP60160784A patent/JPH0649688B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0169712B1 (en) | 1990-12-12 |
FI852796A0 (fi) | 1985-07-17 |
AU4520285A (en) | 1986-01-23 |
DK327985D0 (da) | 1985-07-18 |
GR851735B (id) | 1985-11-26 |
JPH0649688B2 (ja) | 1994-06-29 |
JPS6140272A (ja) | 1986-02-26 |
US4698340A (en) | 1987-10-06 |
ES8700661A1 (es) | 1986-10-16 |
DE3580875D1 (de) | 1991-01-24 |
FI852796L (fi) | 1986-01-20 |
ES545347A0 (es) | 1986-10-16 |
DK327985A (da) | 1986-01-20 |
EP0169712A3 (en) | 1986-12-03 |
EP0169712A2 (en) | 1986-01-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO852869L (no) | Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-derivater. | |
EP1562938B1 (en) | Heteroaryl-pyrimidine derivatives as jak inhibitors | |
AU2002220195B2 (en) | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto | |
JP4734119B2 (ja) | インダゾール化合物及びその医薬用途 | |
KR101666517B1 (ko) | 암의 치료를 위한 wnt 신호전달 경로 억제제로서의 피리딘계 및 피리미딘계 화합물 | |
US8188101B2 (en) | Dihydropyridopyrimidines for the treatment of AB-related pathologies | |
EP3189043B1 (en) | Therapeutic compounds as inhibitors of the orexin-1 receptor | |
KR20040068317A (ko) | 피리미딘 a₂b 선택성 길항 화합물, 그의 합성 방법 및용도 | |
ES2217428T3 (es) | Derivados de vinilpiridina sustituidos y medicamentos que los contienen. | |
WO1999016747A1 (fr) | Derives sulfonyle | |
BRPI0720635A2 (pt) | Compostos orgânicos e seus usos | |
EP3585772B1 (en) | 1, 4, 6-trisubstituted-2-alkyl-1h-benzo[d]imidazole derivatives as dihydroorotate oxygenase inhibitors | |
PT93823B (pt) | Processo para a preparacao de derivados de pirimidina e de composicoes farmaceuticas que os contem | |
KR20010022108A (ko) | 인자 xa를 억제하는 헤테로사이클 유도체 | |
AU2005300733A1 (en) | Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors | |
BR112021010919A2 (pt) | Moduladores de trex1 | |
AU2012335978A1 (en) | Modulators of the G protein-coupled Mas receptor and the treatment of disorders related thereto | |
BRPI0618900A2 (pt) | compostos calcilìticos | |
AU2019214048A1 (en) | Nitrogenated heterocyclic amide compound, and use thereof for medical purposes | |
KR101456316B1 (ko) | 함질소 방향족 6 원자 고리 유도체 그리고 그것들을 포함하는 의약 | |
US4831030A (en) | Diphenylpyridine compounds, processes for the preparation thereof and composition comprising the same | |
BRPI0717374A2 (pt) | Inibidores de mapk/erk quinase | |
ES2770676T3 (es) | Moduladores de quinolina enlazados a metileno de ROR-gamma-T | |
EP0177287B1 (en) | Pyrimidine derivatives, processes for preparation thereof and composition of the same | |
WO2002022588A1 (fr) | Nouveau derive de pyrimidine et nouveau derive de pyridine |