EA022078B1 - Гетероциклическое соединение и его применение - Google Patents

Info

Publication number

EA022078B1

EA022078B1 EA201390222A EA201390222A EA022078B1 EA 022078 B1 EA022078 B1 EA 022078B1 EA 201390222 A EA201390222 A EA 201390222A EA 201390222 A EA201390222 A EA 201390222A EA 022078 B1 EA022078 B1 EA 022078B1

Authority

EA

Eurasian Patent Office

Prior art keywords

optionally substituted

halogen atom

group

alkyl

ring

Prior art date

2010-08-10

Links

• Espacenet
• Global Dossier
• Discuss

• 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 325
• 150000003839 salts Chemical class 0.000 claims abstract description 124
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 26
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 23
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 20
• 230000000069 prophylactic effect Effects 0.000 claims abstract description 11
• -1 dihydroinden Chemical compound 0.000 claims description 477
• 125000005843 halogen group Chemical group 0.000 claims description 268
• 125000001424 substituent group Chemical group 0.000 claims description 213
• 125000000217 alkyl group Chemical group 0.000 claims description 142
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 100
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 99
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
• 239000003814 drug Substances 0.000 claims description 82
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 67
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 65
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 58
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 55
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 49
• 229940079593 drug Drugs 0.000 claims description 48
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 33
• 229940124597 therapeutic agent Drugs 0.000 claims description 31
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 27
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 25
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 24
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 24
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 23
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 22
• 108090000078 AMPA Receptors Proteins 0.000 claims description 20
• 102000003678 AMPA Receptors Human genes 0.000 claims description 20
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 19
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 19
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 19
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 19
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
• 229930192474 thiophene Natural products 0.000 claims description 17
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 16
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 16
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 14
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 14
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
• IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 14
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 12
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 12
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
• 125000003566 oxetanyl group Chemical group 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 11
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 10
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 10
• IZPXKCJSCJNGAF-UHFFFAOYSA-N 9-(4-cyclohexyloxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C12=NS(=O)(=O)CCN2C=CC=C1C(C=C1)=CC=C1OC1CCCCC1 IZPXKCJSCJNGAF-UHFFFAOYSA-N 0.000 claims description 10
• VKKLOYOLCCDGLD-UHFFFAOYSA-N 9-(4-phenoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C12=NS(=O)(=O)CCN2C=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 VKKLOYOLCCDGLD-UHFFFAOYSA-N 0.000 claims description 10
• CFZWPHLWYCTJFX-UHFFFAOYSA-N 9-[4-(4-methylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C=2C3=NS(=O)(=O)CCN3C=CC=2)C=C1 CFZWPHLWYCTJFX-UHFFFAOYSA-N 0.000 claims description 10
• 150000001924 cycloalkanes Chemical class 0.000 claims description 10
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 10
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 9
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 8
• LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims description 8
• 206010022437 insomnia Diseases 0.000 claims description 8
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
• 208000020401 Depressive disease Diseases 0.000 claims description 5
• 201000002859 sleep apnea Diseases 0.000 claims description 5
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
• YROIEQHEBPTQKR-UHFFFAOYSA-N 2h-1,2,4-thiadiazine Chemical compound N1SC=CN=C1 YROIEQHEBPTQKR-UHFFFAOYSA-N 0.000 claims 1
• UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 abstract description 7
• 229940043274 prophylactic drug Drugs 0.000 abstract description 2
• 229940126585 therapeutic drug Drugs 0.000 abstract description 2
• 230000003389 potentiating effect Effects 0.000 abstract 1
• 238000006243 chemical reaction Methods 0.000 description 122
• 235000002639 sodium chloride Nutrition 0.000 description 120
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• 125000000623 heterocyclic group Chemical group 0.000 description 77
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000002904 solvent Substances 0.000 description 63
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 229910052757 nitrogen Inorganic materials 0.000 description 54
• 125000004433 nitrogen atom Chemical group N* 0.000 description 51
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 50
• 125000006239 protecting group Chemical group 0.000 description 47
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• 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
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 229910052731 fluorine Inorganic materials 0.000 description 37
• 230000035484 reaction time Effects 0.000 description 37
• 239000002585 base Substances 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 125000001153 fluoro group Chemical group F* 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• 229910052717 sulfur Inorganic materials 0.000 description 29
• 125000004430 oxygen atom Chemical group O* 0.000 description 28
• 125000003277 amino group Chemical group 0.000 description 27
• 125000005842 heteroatom Chemical group 0.000 description 27
• 125000004434 sulfur atom Chemical group 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 23
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
• 239000002253 acid Substances 0.000 description 22
• 229910052799 carbon Inorganic materials 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
• 125000002947 alkylene group Chemical group 0.000 description 21
• 125000004429 atom Chemical group 0.000 description 21
• 150000001721 carbon Chemical group 0.000 description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
• 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 20
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
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• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 19
• 238000002360 preparation method Methods 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 238000006460 hydrolysis reaction Methods 0.000 description 17
• 229910052751 metal Inorganic materials 0.000 description 17
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• 125000004043 oxo group Chemical group O=* 0.000 description 17
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 16
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
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• 230000007062 hydrolysis Effects 0.000 description 16
• 239000003446 ligand Substances 0.000 description 16
• 125000002950 monocyclic group Chemical group 0.000 description 16
• 229910052763 palladium Inorganic materials 0.000 description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
• 229910052801 chlorine Inorganic materials 0.000 description 15
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
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• 229910052783 alkali metal Inorganic materials 0.000 description 14
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 14
• 125000000524 functional group Chemical group 0.000 description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
• 239000000203 mixture Substances 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 208000011580 syndromic disease Diseases 0.000 description 14
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 13
• 239000000651 prodrug Substances 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 125000006413 ring segment Chemical group 0.000 description 13
• 125000001544 thienyl group Chemical group 0.000 description 13
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
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• 230000002378 acidificating effect Effects 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
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
• 239000012046 mixed solvent Substances 0.000 description 11
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• 229910000029 sodium carbonate Inorganic materials 0.000 description 11
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• 239000008096 xylene Substances 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
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• 125000001309 chloro group Chemical group Cl* 0.000 description 10
• 238000005859 coupling reaction Methods 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
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• 230000001225 therapeutic effect Effects 0.000 description 10
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• PXJBHEHFVQVDDS-UHFFFAOYSA-N 9-(4-cyclohexyloxyphenyl)-7-methyl-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound N=1C(C)=CN2CCS(=O)(=O)N=C2C=1C(C=C1)=CC=C1OC1CCCCC1 PXJBHEHFVQVDDS-UHFFFAOYSA-N 0.000 description 9
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
• 206010012289 Dementia Diseases 0.000 description 9
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
• 125000004414 alkyl thio group Chemical group 0.000 description 9
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• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 9
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• 239000010949 copper Substances 0.000 description 9
• 125000004185 ester group Chemical group 0.000 description 9
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• 125000005844 heterocyclyloxy group Chemical group 0.000 description 9
• 150000007522 mineralic acids Chemical class 0.000 description 9
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• 125000006850 spacer group Chemical group 0.000 description 9
• 125000000547 substituted alkyl group Chemical group 0.000 description 9
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
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