HRP980554A2 - 3-substituted tetrahydropyridopyrimidinon derivatives, their preparation and use - Google Patents
3-substituted tetrahydropyridopyrimidinon derivatives, their preparation and useInfo
- Publication number
- HRP980554A2 HRP980554A2 HR19747063.7A HRP980554A HRP980554A2 HR P980554 A2 HRP980554 A2 HR P980554A2 HR P980554 A HRP980554 A HR P980554A HR P980554 A2 HRP980554 A2 HR P980554A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- substituted
- branched
- unbranched
- unsubstituted
- Prior art date
Links
- -1 3-substituted tetrahydropyridopyrimidinon Chemical class 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 24
- 229940076279 serotonin Drugs 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001923 cyclic compounds Chemical class 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 3
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000000697 serotonin reuptake Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 102000007527 Autoreceptors Human genes 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 108010071131 Autoreceptors Proteins 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000003518 presynaptic effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PZFSNQTXBRIQQF-UHFFFAOYSA-N 4-naphthalen-1-yl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C3=CC=CC=C3C=CC=2)=C1 PZFSNQTXBRIQQF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- SSSBLYQLIOQJSB-UHFFFAOYSA-N 4-naphthalen-1-ylpiperidine Chemical compound C1CNCCC1C1=CC=CC2=CC=CC=C12 SSSBLYQLIOQJSB-UHFFFAOYSA-N 0.000 description 2
- 101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 description 2
- 102100027493 5-hydroxytryptamine receptor 1D Human genes 0.000 description 2
- PVNGDFHKRAIVTC-UHFFFAOYSA-N 6-benzyl-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound C1C=2C(=O)N=CNC=2CCN1CC1=CC=CC=C1 PVNGDFHKRAIVTC-UHFFFAOYSA-N 0.000 description 2
- 208000000044 Amnesia Diseases 0.000 description 2
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 101150050738 HTR1B gene Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- 239000004000 serotonin 1B antagonist Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- SWEGVUWSXJEPIF-UHFFFAOYSA-N tert-butyl 4-naphthalen-1-yl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C3=CC=CC=C3C=CC=2)=C1 SWEGVUWSXJEPIF-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 1
- FHLXQXCQSUICIN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrido[3,2-d]pyrimidine Chemical compound C1=CC=C2NCNCC2=N1 FHLXQXCQSUICIN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- VNICFCQJUVFULD-UHFFFAOYSA-N 1-(1-naphthalenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=CC=CC=C12 VNICFCQJUVFULD-UHFFFAOYSA-N 0.000 description 1
- GJOBEWYDAQTKDU-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-4-yl)piperazine Chemical compound C=12CCCC2=CC=CC=1N1CCNCC1 GJOBEWYDAQTKDU-UHFFFAOYSA-N 0.000 description 1
- MUSOMUXTQGJZKD-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCl)CC1 MUSOMUXTQGJZKD-UHFFFAOYSA-N 0.000 description 1
- CZTHNFFYQLEWJT-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(3,4-dimethylphenyl)piperazine Chemical compound C1=C(C)C(C)=CC=C1N1CCN(CCCl)CC1 CZTHNFFYQLEWJT-UHFFFAOYSA-N 0.000 description 1
- MAIPOMCACBNHEI-UHFFFAOYSA-N 1-(2-chloroethyl)piperazine Chemical compound ClCCN1CCNCC1 MAIPOMCACBNHEI-UHFFFAOYSA-N 0.000 description 1
- OIZBMQFOSPOOIS-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCl)CC1 OIZBMQFOSPOOIS-UHFFFAOYSA-N 0.000 description 1
- QYHUWTWTZWQCJT-UHFFFAOYSA-N 1-(3-chloropropyl)-4-naphthalen-1-ylpiperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC2=CC=CC=C12 QYHUWTWTZWQCJT-UHFFFAOYSA-N 0.000 description 1
- FBPPFIPXMJEJCU-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazine Chemical compound C1CCCC2=C1C=CC=C2N1CCNCC1 FBPPFIPXMJEJCU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MLXIGMYNOXFJAH-UHFFFAOYSA-N 1-chloro-4-piperazin-1-ylphthalazine Chemical compound C12=CC=CC=C2C(Cl)=NN=C1N1CCNCC1 MLXIGMYNOXFJAH-UHFFFAOYSA-N 0.000 description 1
- PWMNWKMSCLDPAG-UHFFFAOYSA-N 1-naphthalen-1-ylazepane Chemical compound C1CCCCCN1C1=CC=CC2=CC=CC=C12 PWMNWKMSCLDPAG-UHFFFAOYSA-N 0.000 description 1
- VNOBUFJWMNTPIS-UHFFFAOYSA-N 2-[4-(2-chloroethyl)piperazin-1-yl]pyrimidine Chemical compound C1CN(CCCl)CCN1C1=NC=CC=N1 VNOBUFJWMNTPIS-UHFFFAOYSA-N 0.000 description 1
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 1
- IMAWRJZYXYLGBL-UHFFFAOYSA-N 2-methoxy-1-phenylpiperazine Chemical compound COC1CNCCN1C1=CC=CC=C1 IMAWRJZYXYLGBL-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
- SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 description 1
- NIBZKHUIJGTBOX-UHFFFAOYSA-N 4-piperazin-1-ylisoquinoline Chemical compound C1CNCCN1C1=CN=CC2=CC=CC=C12 NIBZKHUIJGTBOX-UHFFFAOYSA-N 0.000 description 1
- KLTHGJYCURVMAK-UHFFFAOYSA-N 4-piperazin-1-ylquinazoline Chemical compound C1CNCCN1C1=NC=NC2=CC=CC=C12 KLTHGJYCURVMAK-UHFFFAOYSA-N 0.000 description 1
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 1
- SPXJZGXITAWLIO-UHFFFAOYSA-N 6-benzyl-3-(2-chloroethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1C=2C(=O)N(CCCl)C=NC=2CCN1CC1=CC=CC=C1 SPXJZGXITAWLIO-UHFFFAOYSA-N 0.000 description 1
- RYFHYPQWMRYOIM-UHFFFAOYSA-N 6-benzyl-3-[2-(4-isoquinolin-4-ylpiperazin-1-yl)ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1CC=2N=CN(CCN3CCN(CC3)C=3C4=CC=CC=C4C=NC=3)C(=O)C=2CN1CC1=CC=CC=C1 RYFHYPQWMRYOIM-UHFFFAOYSA-N 0.000 description 1
- YXDZFOSTNBHDQZ-UHFFFAOYSA-N 6-benzyl-3-[2-(4-naphthalen-1-ylpiperazin-1-yl)ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1CC=2N=CN(CCN3CCN(CC3)C=3C4=CC=CC=C4C=CC=3)C(=O)C=2CN1CC1=CC=CC=C1 YXDZFOSTNBHDQZ-UHFFFAOYSA-N 0.000 description 1
- LEACNBMPNIFUTQ-UHFFFAOYSA-N 6-benzyl-3-[2-(4-quinazolin-4-ylpiperazin-1-yl)ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1CC=2N=CN(CCN3CCN(CC3)C=3C4=CC=CC=C4N=CN=3)C(=O)C=2CN1CC1=CC=CC=C1 LEACNBMPNIFUTQ-UHFFFAOYSA-N 0.000 description 1
- YGOFUUSDCBDTFQ-UHFFFAOYSA-N 6-benzyl-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C=3CC(CC=4C=CC=CC=4)NCC=3N=C2)=O)CC1 YGOFUUSDCBDTFQ-UHFFFAOYSA-N 0.000 description 1
- KHFDQRBPPUWJCO-UHFFFAOYSA-N 6-benzyl-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C=3CN(CC=4C=CC=CC=4)CCC=3N=C2)=O)CC1 KHFDQRBPPUWJCO-UHFFFAOYSA-N 0.000 description 1
- NDTZNBNFMXWWPK-UHFFFAOYSA-N 6-benzyl-3-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)CN2C(C=3CN(CC=4C=CC=CC=4)CCC=3N=C2)=O)CC1 NDTZNBNFMXWWPK-UHFFFAOYSA-N 0.000 description 1
- WMTKYCXDAWSDBX-UHFFFAOYSA-N 6-benzyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C=3CC(CC=4C=CC=CC=4)NCC=3N=C2)=O)CC1 WMTKYCXDAWSDBX-UHFFFAOYSA-N 0.000 description 1
- JFXLRCFAXQRXCJ-UHFFFAOYSA-N 6-benzyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C=3CN(CC=4C=CC=CC=4)CCC=3N=C2)=O)CC1 JFXLRCFAXQRXCJ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 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
- 208000030814 Eating disease Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 102000017911 HTR1A Human genes 0.000 description 1
- 101150015707 HTR1A gene Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- ULMHMJAEGZPQRY-UHFFFAOYSA-N N-(tert-butoxycarbonyl)piperidin-2-one Chemical compound CC(C)(C)OC(=O)N1CCCCC1=O ULMHMJAEGZPQRY-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010042209 Stress 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
- 206010047163 Vasospasm Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 230000001908 autoinhibitory effect Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- 230000007372 neural signaling Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 230000004963 pathophysiological condition Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 210000000063 presynaptic terminal Anatomy 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Structure And Mechanism Of Cameras (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19747063A DE19747063A1 (de) | 1997-10-24 | 1997-10-24 | 3-substituierte Tetrahydropyridopyrimidinon-Derivate, ihre Herstellung und Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980554A2 true HRP980554A2 (en) | 1999-08-31 |
Family
ID=7846539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19747063.7A HRP980554A2 (en) | 1997-10-24 | 1998-10-21 | 3-substituted tetrahydropyridopyrimidinon derivatives, their preparation and use |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6414157B1 (no) |
| EP (1) | EP1025100B1 (no) |
| JP (1) | JP2001521035A (no) |
| KR (1) | KR20010015787A (no) |
| CN (1) | CN1277611A (no) |
| AR (1) | AR015466A1 (no) |
| AT (1) | ATE212346T1 (no) |
| AU (1) | AU748666B2 (no) |
| BG (1) | BG104291A (no) |
| BR (1) | BR9812970A (no) |
| CA (1) | CA2305258A1 (no) |
| CO (1) | CO4980862A1 (no) |
| DE (2) | DE19747063A1 (no) |
| DK (1) | DK1025100T3 (no) |
| ES (1) | ES2172222T3 (no) |
| HR (1) | HRP980554A2 (no) |
| HU (1) | HUP0004648A3 (no) |
| ID (1) | ID24633A (no) |
| NO (1) | NO20001934L (no) |
| NZ (1) | NZ503486A (no) |
| PL (1) | PL340034A1 (no) |
| PT (1) | PT1025100E (no) |
| SK (1) | SK3872000A3 (no) |
| TR (1) | TR200001102T2 (no) |
| TW (1) | TW432063B (no) |
| WO (1) | WO1999021857A1 (no) |
| ZA (1) | ZA989664B (no) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19900544A1 (de) * | 1999-01-11 | 2000-07-13 | Basf Ag | Verwendung von Verbindungen der Formel I zur Prophylaxe und Therapie der zerebralen Ischämie |
| WO2004014909A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors |
| US20040127501A1 (en) * | 2002-09-24 | 2004-07-01 | Zhengming Chen | Therapeutic agents useful for treating pain |
| JP4654035B2 (ja) | 2002-11-05 | 2011-03-16 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | 抗菌剤 |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| US7160888B2 (en) * | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| DE102004020908A1 (de) | 2004-04-28 | 2005-11-17 | Grünenthal GmbH | Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen |
| MX2007012083A (es) * | 2005-04-01 | 2007-11-20 | Warner Lambert Co | Tetrahidro-piridoazepin-8-onas y compuestos relacionados para el tratamiento de la esquizofrenia. |
| CN101296914B (zh) * | 2005-08-26 | 2012-07-18 | 盐野义制药株式会社 | 具有ppar激动活性的衍生物 |
| CN102952129B (zh) * | 2011-08-16 | 2015-09-23 | 上海师范大学 | 四氢吡啶并二氢嘧啶酮衍生物及其制备方法和应用 |
| WO2022087011A1 (en) | 2020-10-21 | 2022-04-28 | Aligos Therapeutics, Inc. | Bicyclic compounds |
| US11957683B2 (en) | 2021-06-18 | 2024-04-16 | Aligos Therapeutics, Inc. | Bicyclic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0827149A (ja) * | 1994-07-08 | 1996-01-30 | Meiji Seika Kaisha Ltd | ピリミジノン誘導体およびその塩 |
-
1997
- 1997-10-24 DE DE19747063A patent/DE19747063A1/de not_active Withdrawn
-
1998
- 1998-10-05 AT AT98951491T patent/ATE212346T1/de not_active IP Right Cessation
- 1998-10-05 ES ES98951491T patent/ES2172222T3/es not_active Expired - Lifetime
- 1998-10-05 DK DK98951491T patent/DK1025100T3/da active
- 1998-10-05 KR KR1020007004362A patent/KR20010015787A/ko not_active Application Discontinuation
- 1998-10-05 ID IDW20000762D patent/ID24633A/id unknown
- 1998-10-05 SK SK387-2000A patent/SK3872000A3/sk unknown
- 1998-10-05 TR TR2000/01102T patent/TR200001102T2/xx unknown
- 1998-10-05 DE DE59802922T patent/DE59802922D1/de not_active Expired - Fee Related
- 1998-10-05 NZ NZ503486A patent/NZ503486A/en unknown
- 1998-10-05 CN CN98810525A patent/CN1277611A/zh active Pending
- 1998-10-05 BR BR9812970-8A patent/BR9812970A/pt not_active IP Right Cessation
- 1998-10-05 HU HU0004648A patent/HUP0004648A3/hu unknown
- 1998-10-05 JP JP2000517967A patent/JP2001521035A/ja active Pending
- 1998-10-05 AU AU97484/98A patent/AU748666B2/en not_active Ceased
- 1998-10-05 CA CA002305258A patent/CA2305258A1/en not_active Abandoned
- 1998-10-05 WO PCT/EP1998/006305 patent/WO1999021857A1/de not_active Application Discontinuation
- 1998-10-05 PL PL98340034A patent/PL340034A1/xx unknown
- 1998-10-05 EP EP98951491A patent/EP1025100B1/de not_active Expired - Lifetime
- 1998-10-05 PT PT98951491T patent/PT1025100E/pt unknown
- 1998-10-20 TW TW087117332A patent/TW432063B/zh not_active IP Right Cessation
- 1998-10-21 HR HR19747063.7A patent/HRP980554A2/hr not_active Application Discontinuation
- 1998-10-22 CO CO98061508A patent/CO4980862A1/es unknown
- 1998-10-23 AR ARP980105297A patent/AR015466A1/es not_active Application Discontinuation
- 1998-10-23 ZA ZA9809664A patent/ZA989664B/xx unknown
-
2000
- 2000-04-03 BG BG104291A patent/BG104291A/xx unknown
- 2000-04-10 US US09/529,231 patent/US6414157B1/en not_active Expired - Lifetime
- 2000-04-13 NO NO20001934A patent/NO20001934L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0004648A3 (en) | 2001-11-28 |
| SK3872000A3 (en) | 2000-09-12 |
| JP2001521035A (ja) | 2001-11-06 |
| US6414157B1 (en) | 2002-07-02 |
| DK1025100T3 (da) | 2002-05-06 |
| WO1999021857A1 (de) | 1999-05-06 |
| EP1025100A1 (de) | 2000-08-09 |
| BR9812970A (pt) | 2000-08-08 |
| NO20001934D0 (no) | 2000-04-13 |
| CN1277611A (zh) | 2000-12-20 |
| AU748666B2 (en) | 2002-06-06 |
| ATE212346T1 (de) | 2002-02-15 |
| PT1025100E (pt) | 2002-07-31 |
| PL340034A1 (en) | 2001-01-15 |
| NO20001934L (no) | 2000-04-13 |
| DE59802922D1 (de) | 2002-03-14 |
| ID24633A (id) | 2000-07-27 |
| CO4980862A1 (es) | 2000-11-27 |
| TW432063B (en) | 2001-05-01 |
| BG104291A (en) | 2001-05-31 |
| TR200001102T2 (tr) | 2000-08-21 |
| AR015466A1 (es) | 2001-05-02 |
| CA2305258A1 (en) | 1999-05-06 |
| ZA989664B (en) | 2000-04-25 |
| KR20010015787A (ko) | 2001-02-26 |
| HUP0004648A2 (hu) | 2001-05-28 |
| DE19747063A1 (de) | 1999-04-29 |
| ES2172222T3 (es) | 2002-09-16 |
| NZ503486A (en) | 2001-04-27 |
| EP1025100B1 (de) | 2002-01-23 |
| AU9748498A (en) | 1999-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4572195B2 (ja) | ８−置換−６，７，８，９−テトラヒドロピリミド［１，２−ａ］ピリミジン−４−オン誘導体 | |
| HRP980319A2 (en) | 3-substituted 3,4-dihydro-thieno/2,3-d/pyrimidine derivatives, their preparation and use | |
| CZ281676B6 (cs) | 1-piperazin-1,2-dihydroindenové deriváty, farmaceutické prostředky s jejich obsahem a použití uvedených látek pro výrobu farmaceutických prostředků | |
| HRP980554A2 (en) | 3-substituted tetrahydropyridopyrimidinon derivatives, their preparation and use | |
| HRP980555A2 (en) | 2-substituted 1,2-benzoisothiazole derivatives, their preparation and use | |
| KR20010022658A (ko) | 3-치환된 3,4,5,7-테트라히드로-피롤로[3'4':4,5]티에노[2,3-ｄ]피리미딘 유도체, 그의 제법 및 5ｈｔ길항제로서의 용도 | |
| EP1023296A1 (de) | 3-SUBSTITUIERTE PYRIDO 3',4':4,5] THIENO 2,3-d] PYRIMIDIN-DERIVATE, IHRE HERSTELLUNG UND VERWENDUNG | |
| WO2000041697A1 (de) | Verwendung von 2-substituierten 1,2-benzisothiazol-derivaten und von 3-substituierten tetrahydropyridopyrimidinon-derivaten zur prophylaxe und therapie der zerebralen ischämie | |
| MXPA00002601A (en) | 3-substituted tetrahydropyridopyrimidinone derivatives, method for producing the same, and their use | |
| CZ20001454A3 (cs) | Deriváty 3-substituovaného tetrahydropyridopyrimidinonu, způsob jejich přípravy a použití | |
| MXPA00003136A (en) | 2-substituted 1,2-benzisothiazole derivatives and their use as serotonin antagonists (5-ht1a, 5-ht1b and 5-ht1d) | |
| CZ20001436A3 (cs) | Disubstituované deriváty 1,2-benzisotiazolu a jejich použití |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| OBST | Application withdrawn |