NO831503L - Fremgangsmaate for fremstilling av kondenserte cykloalifatiske derivater av substituerte pyrido (1,2-a) pyrimidiner - Google Patents

Info

Publication number

NO831503L

NO831503L NO831503A NO831503A NO831503L NO 831503 L NO831503 L NO 831503L NO 831503 A NO831503 A NO 831503A NO 831503 A NO831503 A NO 831503A NO 831503 L NO831503 L NO 831503L

Authority

NO

Norway

Prior art keywords

tetrahydro

pyrido

benzylidene

oxo

carboxylic acid

Prior art date

1982-04-29

Links

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• 238000000034 method Methods 0.000 title claims description 10
• 238000002360 preparation method Methods 0.000 title claims description 8
• 150000003230 pyrimidines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 111
• -1 hydroxy, formyloxy Chemical group 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 239000000203 mixture Substances 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 238000005888 cyclopropanation reaction Methods 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 239000002244 precipitate Substances 0.000 description 29
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
• 238000003756 stirring Methods 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 238000001816 cooling Methods 0.000 description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 238000011282 treatment Methods 0.000 description 14
• 230000007935 neutral effect Effects 0.000 description 13
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 11
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 241000700159 Rattus Species 0.000 description 10
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
• 239000005457 ice water Substances 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 238000002425 crystallisation Methods 0.000 description 8
• 230000008025 crystallization Effects 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• QHRQUMBXAYKEMS-UHFFFAOYSA-N 4-benzylidene-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1 QHRQUMBXAYKEMS-UHFFFAOYSA-N 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000011541 reaction mixture Substances 0.000 description 6
• KRNUKLBBDTUZTB-UHFFFAOYSA-N 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1CC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1 KRNUKLBBDTUZTB-UHFFFAOYSA-N 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 238000007796 conventional method Methods 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• UPGZAERNNNZSPM-UHFFFAOYSA-N quinazoline-8-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CC=CC2=C1 UPGZAERNNNZSPM-UHFFFAOYSA-N 0.000 description 5
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 229920002261 Corn starch Polymers 0.000 description 4
• 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 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 239000008120 corn starch Substances 0.000 description 4
• 229940099112 cornstarch Drugs 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 239000000825 pharmaceutical preparation Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
• QWUNOVHGZTXJEZ-UHFFFAOYSA-N 3-(2-methyl-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound CC1=CC=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CC1 QWUNOVHGZTXJEZ-UHFFFAOYSA-N 0.000 description 3
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
• HHYAJVADERPWHO-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 HHYAJVADERPWHO-UHFFFAOYSA-N 0.000 description 3
• ACDGPSFNSGPUJE-UHFFFAOYSA-N 4-[(3-ethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 ACDGPSFNSGPUJE-UHFFFAOYSA-N 0.000 description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 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 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 125000004423 acyloxy group Chemical group 0.000 description 3
• 230000001262 anti-secretory effect Effects 0.000 description 3
• 230000000026 anti-ulcerogenic effect Effects 0.000 description 3
• 239000000427 antigen Substances 0.000 description 3
• 102000036639 antigens Human genes 0.000 description 3
• 108091007433 antigens Proteins 0.000 description 3
• 230000015572 biosynthetic process Effects 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
• 239000003085 diluting agent Substances 0.000 description 3
• 239000003814 drug Substances 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• 150000007529 inorganic bases Chemical class 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 229920000137 polyphosphoric acid Polymers 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000003380 propellant Substances 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 239000000454 talc Substances 0.000 description 3
• 235000012222 talc Nutrition 0.000 description 3
• 229910052623 talc Inorganic materials 0.000 description 3
• 238000005303 weighing Methods 0.000 description 3
• UPRFGIZYNARKEU-UHFFFAOYSA-N 1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid methyl ester Chemical compound O=C1N2C=C(C(=O)OC)C=CC2=NC2=C1CCC2 UPRFGIZYNARKEU-UHFFFAOYSA-N 0.000 description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
• QLKLPUYYQQGZGG-UHFFFAOYSA-N 11-oxo-4-(pyridin-2-ylmethylidene)-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=N1 QLKLPUYYQQGZGG-UHFFFAOYSA-N 0.000 description 2
• BQDHJIPFPPPMPA-UHFFFAOYSA-N 11-oxo-4-(pyridin-3-ylmethylidene)-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CN=C1 BQDHJIPFPPPMPA-UHFFFAOYSA-N 0.000 description 2
• TYIFOIUTIBJJDB-UHFFFAOYSA-N 2-(diethylamino)ethyl quinazoline-8-carboxylate Chemical compound CCN(CC)CCOC(=O)C1=C2N=CN=CC2=CC=C1 TYIFOIUTIBJJDB-UHFFFAOYSA-N 0.000 description 2
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
• OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
• TZSLLMQNITWHRP-UHFFFAOYSA-N 3-(3-ethoxy-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CC2)=C1 TZSLLMQNITWHRP-UHFFFAOYSA-N 0.000 description 2
• SCBJPAJKWKCWHJ-UHFFFAOYSA-N 3-(3-methoxy-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CC2)=C1 SCBJPAJKWKCWHJ-UHFFFAOYSA-N 0.000 description 2
• MFVVEVAMGSGAOU-UHFFFAOYSA-N 3-benzylidene-7-methyl-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one Chemical compound C1CC=2C(=O)N3C=C(C)C=CC3=NC=2C1=CC1=CC=CC=C1 MFVVEVAMGSGAOU-UHFFFAOYSA-N 0.000 description 2
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
• 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 2
• FLESJLOTERFIMR-UHFFFAOYSA-N 4-[(2,3-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1OC FLESJLOTERFIMR-UHFFFAOYSA-N 0.000 description 2
• IFCCSWMUIIBUOV-UHFFFAOYSA-N 4-[(2,5-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=C(OC)C(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 IFCCSWMUIIBUOV-UHFFFAOYSA-N 0.000 description 2
• PQQPWSKHNMAURX-UHFFFAOYSA-N 4-[(2,5-dimethylphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound CC1=CC=C(C)C(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1 PQQPWSKHNMAURX-UHFFFAOYSA-N 0.000 description 2
• ZNHJBGDEZYIZGN-UHFFFAOYSA-N 4-[(2,6-dichlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=C(Cl)C=CC=C1Cl ZNHJBGDEZYIZGN-UHFFFAOYSA-N 0.000 description 2
• MEBGECTZRYZCPD-UHFFFAOYSA-N 4-[(2-chlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1Cl MEBGECTZRYZCPD-UHFFFAOYSA-N 0.000 description 2
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