CN104926837A - 杂环化合物及其用途 - Google Patents
杂环化合物及其用途 Download PDFInfo
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- CN104926837A CN104926837A CN201510259936.0A CN201510259936A CN104926837A CN 104926837 A CN104926837 A CN 104926837A CN 201510259936 A CN201510259936 A CN 201510259936A CN 104926837 A CN104926837 A CN 104926837A
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- Prior art keywords
- alkyl
- halogen atom
- optionally
- group
- ring
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 150000003839 salts Chemical class 0.000 claims abstract description 128
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 26
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 21
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 19
- -1 2-butoxy-4-octyl phenyl Chemical group 0.000 claims description 455
- 125000005843 halogen group Chemical group 0.000 claims description 302
- 125000000217 alkyl group Chemical group 0.000 claims description 155
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 120
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 99
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 94
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 73
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 70
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 62
- 239000003814 drug Substances 0.000 claims description 60
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 53
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 52
- 229940079593 drug Drugs 0.000 claims description 49
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 39
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 34
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 33
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 27
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 26
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 24
- 108090000078 AMPA Receptors Proteins 0.000 claims description 23
- 102000003678 AMPA Receptors Human genes 0.000 claims description 23
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 22
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 21
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 18
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 18
- 229930192474 thiophene Natural products 0.000 claims description 18
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 17
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 15
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003217 pyrazoles Chemical class 0.000 claims description 12
- 125000006850 spacer group Chemical group 0.000 claims description 12
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 11
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 11
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 11
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 11
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- YROIEQHEBPTQKR-UHFFFAOYSA-N 2h-1,2,4-thiadiazine Chemical compound N1SC=CN=C1 YROIEQHEBPTQKR-UHFFFAOYSA-N 0.000 claims description 6
- 150000002240 furans Chemical class 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- 150000003053 piperidines Chemical class 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 150000003527 tetrahydropyrans Chemical class 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 208000024732 dysthymic disease Diseases 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 6
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 4
- UXMAWJKSGBRJKV-UHFFFAOYSA-N [SiH3][O] Chemical compound [SiH3][O] UXMAWJKSGBRJKV-UHFFFAOYSA-N 0.000 claims 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
- 239000012747 synergistic agent Substances 0.000 claims 1
- 229940126585 therapeutic drug Drugs 0.000 abstract description 7
- 230000003449 preventive effect Effects 0.000 abstract description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 description 188
- 238000006243 chemical reaction Methods 0.000 description 121
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
- 239000002904 solvent Substances 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 44
- 239000002585 base Substances 0.000 description 44
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 39
- 230000035484 reaction time Effects 0.000 description 39
- 125000001153 fluoro group Chemical group F* 0.000 description 33
- 229910052731 fluorine Inorganic materials 0.000 description 31
- 238000010511 deprotection reaction Methods 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 125000000000 cycloalkoxy group Chemical group 0.000 description 24
- 125000004430 oxygen atom Chemical group O* 0.000 description 24
- 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 22
- 238000006722 reduction reaction Methods 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 125000003277 amino group Chemical group 0.000 description 21
- 239000003153 chemical reaction reagent Substances 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 20
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
- 150000001721 carbon Chemical group 0.000 description 19
- 125000004434 sulfur atom Chemical group 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 18
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 125000002947 alkylene group Chemical group 0.000 description 16
- 150000001924 cycloalkanes Chemical class 0.000 description 16
- 125000002950 monocyclic group Chemical group 0.000 description 16
- 230000036961 partial effect Effects 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 15
- 238000006460 hydrolysis reaction Methods 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 15
- 125000005554 pyridyloxy group Chemical group 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 229910052783 alkali metal Inorganic materials 0.000 description 14
- 125000004465 cycloalkenyloxy group Chemical group 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 13
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 13
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 12
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 12
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 12
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 12
- 125000001769 aryl amino group Chemical group 0.000 description 12
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 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 10
- 150000001408 amides Chemical class 0.000 description 10
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 229940093915 gynecological organic acid Drugs 0.000 description 10
- 150000008282 halocarbons Chemical class 0.000 description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 10
- 239000012046 mixed solvent Substances 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 10
- 235000005985 organic acids Nutrition 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 229940001593 sodium carbonate Drugs 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
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Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9150591B2 (en) * | 2010-08-10 | 2015-10-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| EP2694472B1 (en) | 2011-04-05 | 2020-03-11 | Takeda Pharmaceutical Company Limited | Sulfonamide derivative and use thereof |
| WO2013118845A1 (ja) * | 2012-02-08 | 2013-08-15 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US20150011554A1 (en) * | 2013-06-13 | 2015-01-08 | Veroscience Llc | Compositions and Methods for Treating Metabolic Disorders |
| DK3013813T3 (da) | 2013-06-27 | 2019-06-03 | Pfizer | Heteroaromatiske forbindelser og anvendelse deraf som dopamin-d1-ligander |
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| MX2016007259A (es) | 2013-12-03 | 2016-08-04 | Du Pont | Pirrolidinonas como herbicidas. |
| US9944602B2 (en) | 2014-07-02 | 2018-04-17 | E. I. Du Pont De Nemours And Company | Piperidinone herbicides |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| MX373652B (es) * | 2015-04-29 | 2020-04-02 | Janssen Pharmaceutica Nv | Imidazopirazinas y pirazolopirimidinas y su uso como moduladores del receptor de ampa. |
| ES2865330T3 (es) | 2015-04-29 | 2021-10-15 | Janssen Pharmaceutica Nv | Azabenzimidazoles y su uso como moduladores del receptor AMPA |
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| WO2016196019A1 (en) | 2015-05-29 | 2016-12-08 | E I Du Pont De Nemours And Company | Substituted cyclic amides as herbicides |
| CN107709310B (zh) | 2015-06-02 | 2021-09-24 | Fmc公司 | 取代的环酰胺及其作为除草剂的用途 |
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| US20170181292A1 (en) * | 2015-12-16 | 2017-06-22 | Rohm And Haas Electronic Materials Llc | Method for forming organic coating on nickel surface |
| CN105669731B (zh) * | 2016-01-10 | 2017-06-30 | 沧州普瑞东方科技有限公司 | 一种4‑(4‑烷基环己氧基)苯硼酸的合成方法 |
| CA3047724A1 (en) | 2016-12-21 | 2018-06-28 | Fmc Corporation | Nitrone herbicides |
| CN107892697B (zh) | 2016-12-26 | 2020-11-03 | 郑州泰基鸿诺医药股份有限公司 | 一种[1,3]噻嗪-2-胺类化合物及应用，药物组合物 |
| WO2018175231A1 (en) | 2017-03-21 | 2018-09-27 | Fmc Corporation | Herbicidal mixture, composition and method |
| CA3057297A1 (en) | 2017-03-21 | 2018-09-27 | Fmc Corporation | Pyrrolidinones and a process to prepare them |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| US11407748B2 (en) | 2017-10-06 | 2022-08-09 | Takeda Pharmaceutical Company Limited | Substituted pyrido[1,2-a]pyrimidines and pyrazino[1,2-a]pyrimidines for enhancing AMPA receptor function |
| ES2971497T3 (es) | 2017-10-06 | 2024-06-05 | Takeda Pharmaceuticals Co | Compuestos heterocíclicos |
| CR20220160A (es) | 2019-09-16 | 2022-06-16 | Takeda Pharmaceuticals Co | Derivados de piridazin-3(2h)-ona fusionados con azol |
| TW202207944A (zh) * | 2020-05-15 | 2022-03-01 | 日商武田藥品工業股份有限公司 | 抑鬱症之治療 |
| CN113943294A (zh) * | 2020-07-15 | 2022-01-18 | 成都海博为药业有限公司 | 一种作为btk抑制剂的化合物及其制备方法与用途 |
| WO2025224508A1 (en) | 2024-04-22 | 2025-10-30 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition for treating depressive disorders |
| WO2026050231A1 (en) | 2024-08-27 | 2026-03-05 | Neurocrine Biosciences, Inc. | Method of treating a bipolar disorder |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0437742A (ja) * | 1990-06-03 | 1992-02-07 | Konica Corp | 新規な染料を含有するハロゲン化銀写真感光材料 |
| JPH04119890A (ja) * | 1990-09-11 | 1992-04-21 | Konica Corp | ピラゾロチアジアジン系色素 |
| JPH07137462A (ja) * | 1993-11-12 | 1995-05-30 | Konica Corp | 感熱転写材料及び該材料に好適な色素 |
| CN1564817A (zh) * | 2001-10-10 | 2005-01-12 | 神经研究公司 | 新的苯并噻嗪衍生物、其制备和应用 |
| CN1606559A (zh) * | 2001-12-21 | 2005-04-13 | 瑟维尔实验室 | 新的苯并噻嗪和苯并噻二嗪衍生物,其制备方法以及包含所述化合物的药物组合物 |
| US20090163545A1 (en) * | 2007-12-21 | 2009-06-25 | University Of Rochester | Method For Altering The Lifespan Of Eukaryotic Organisms |
| CN101541741A (zh) * | 2006-12-11 | 2009-09-23 | 伊莱利利公司 | Ampa受体增强剂 |
| JP2009248543A (ja) * | 2008-04-11 | 2009-10-29 | Fujifilm Corp | 光情報記録媒体および情報記録方法 |
| WO2009147167A1 (en) * | 2008-06-06 | 2009-12-10 | N.V. Organon | Indane derivatives as ampa receptor modulators |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0437742Y2 (https=) | 1986-10-22 | 1992-09-04 | ||
| JPH0285851A (ja) * | 1988-09-22 | 1990-03-27 | Konica Corp | 新規な写真用カプラー |
| JPH037742A (ja) | 1989-06-05 | 1991-01-14 | Toyo Tire & Rubber Co Ltd | ラバーチエーン用ゴム組成物 |
| DE19704923A1 (de) | 1997-02-10 | 1998-08-13 | Hoechst Schering Agrevo Gmbh | Klebstoffhaltige Schädlingsbekämpfungsmittel |
| JP2003526341A (ja) | 1999-11-04 | 2003-09-09 | コロラド ステート ユニバーシティー リサーチ ファウンデーション | 昆虫を誘引するための装置および方法 |
| FR2801587B1 (fr) | 1999-11-30 | 2002-01-11 | Adir | Nouveaux derives de benzothiadiazines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2854634B1 (fr) | 2003-05-05 | 2005-07-08 | Servier Lab | Nouveaux derives de thiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2865474B1 (fr) | 2004-01-26 | 2008-06-13 | Servier Lab | Nouveaux derives de benzothiazines fluorees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU2007262661A1 (en) | 2006-06-23 | 2007-12-27 | Nufarm Australia Limited | Phenoxy alkanoate herbicidal composition and method of preparation and use |
| US20080167374A1 (en) | 2007-01-09 | 2008-07-10 | Loveland Products, Inc. | Pesticide composition and method of use |
| MX2010005028A (es) | 2007-11-05 | 2010-05-27 | Schering Corp | Moduladores de gamma secretasa. |
| WO2009119088A1 (ja) | 2008-03-25 | 2009-10-01 | 武田薬品工業株式会社 | 複素環化合物 |
| AU2009313527A1 (en) | 2008-11-06 | 2010-05-14 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
| TW201030002A (en) | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| JP2012051806A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | イミダゾリルピラジン誘導体 |
| FR2943342B1 (fr) | 2009-03-20 | 2011-03-04 | Servier Lab | Nouveaux derives de benzothiadiazepines,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| WO2010140339A1 (ja) | 2009-06-01 | 2010-12-09 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2011007756A1 (ja) | 2009-07-13 | 2011-01-20 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| WO2011036889A1 (ja) | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2011036885A1 (ja) | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| US9150591B2 (en) * | 2010-08-10 | 2015-10-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
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Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0437742A (ja) * | 1990-06-03 | 1992-02-07 | Konica Corp | 新規な染料を含有するハロゲン化銀写真感光材料 |
| JPH04119890A (ja) * | 1990-09-11 | 1992-04-21 | Konica Corp | ピラゾロチアジアジン系色素 |
| JPH07137462A (ja) * | 1993-11-12 | 1995-05-30 | Konica Corp | 感熱転写材料及び該材料に好適な色素 |
| CN1564817A (zh) * | 2001-10-10 | 2005-01-12 | 神经研究公司 | 新的苯并噻嗪衍生物、其制备和应用 |
| CN1606559A (zh) * | 2001-12-21 | 2005-04-13 | 瑟维尔实验室 | 新的苯并噻嗪和苯并噻二嗪衍生物,其制备方法以及包含所述化合物的药物组合物 |
| CN101541741A (zh) * | 2006-12-11 | 2009-09-23 | 伊莱利利公司 | Ampa受体增强剂 |
| US20090163545A1 (en) * | 2007-12-21 | 2009-06-25 | University Of Rochester | Method For Altering The Lifespan Of Eukaryotic Organisms |
| JP2009248543A (ja) * | 2008-04-11 | 2009-10-29 | Fujifilm Corp | 光情報記録媒体および情報記録方法 |
| WO2009147167A1 (en) * | 2008-06-06 | 2009-12-10 | N.V. Organon | Indane derivatives as ampa receptor modulators |
Non-Patent Citations (2)
| Title |
|---|
| COLUMBUS, OHIO, US REGISTRY[ONLINE]: ""STN检索报告"", 《STN REGISTRY》 * |
| SIMON E. WARD ET AL.: ""Recent Advances in the Discovery of Selective AMPA Receptor Positive Allosteric Modulators"", 《CURRENT MEDICINAL CHEMISTRY》 * |
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