TWI504604B - 雜環化合物及其用途 - Google Patents

Info

Publication number

TWI504604B

TWI504604B TW100128311A TW100128311A TWI504604B TW I504604 B TWI504604 B TW I504604B TW 100128311 A TW100128311 A TW 100128311A TW 100128311 A TW100128311 A TW 100128311A TW I504604 B TWI504604 B TW I504604B

Authority

TW

Taiwan

Prior art keywords

group

optionally substituted

halogen atom

substituted

compound

Prior art date

2010-08-10

Links

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• Global Dossier
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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
• -1 tetrahydrofuranyloxy Chemical group 0.000 claims description 354
• 150000001875 compounds Chemical class 0.000 claims description 331
• 125000005843 halogen group Chemical group 0.000 claims description 269
• 125000001424 substituent group Chemical group 0.000 claims description 202
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 150
• 150000003839 salts Chemical class 0.000 claims description 126
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 100
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 96
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 78
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 66
• 239000003814 drug Substances 0.000 claims description 62
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 56
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 56
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 54
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 51
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
• 238000011282 treatment Methods 0.000 claims description 36
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 31
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 30
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 30
• 125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 29
• 239000003795 chemical substances by application Substances 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 26
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 25
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
• 201000000980 schizophrenia Diseases 0.000 claims description 24
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 23
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 108090000078 AMPA Receptors Proteins 0.000 claims description 21
• 102000003678 AMPA Receptors Human genes 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
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 19
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 19
• 230000036961 partial effect Effects 0.000 claims description 19
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 17
• IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 17
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 17
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 16
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 16
• 229930192474 thiophene Natural products 0.000 claims description 16
• 208000024827 Alzheimer disease Diseases 0.000 claims description 15
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 14
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
• 150000001924 cycloalkanes Chemical class 0.000 claims description 13
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
• 208000024891 symptom Diseases 0.000 claims description 12
• 125000006612 decyloxy group Chemical group 0.000 claims description 11
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
• XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 10
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 10
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 10
• 229940126585 therapeutic drug Drugs 0.000 claims description 10
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 claims description 8
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 8
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
• UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 7
• YIISYHGSPQJEBJ-UHFFFAOYSA-N C1=CCCC1.N1N=CC=CC2=C1C=CC=C2 Chemical compound C1=CCCC1.N1N=CC=CC2=C1C=CC=C2 YIISYHGSPQJEBJ-UHFFFAOYSA-N 0.000 claims description 7
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
• 239000003623 enhancer Substances 0.000 claims description 7
• 206010022437 insomnia Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 claims description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
• 241000534944 Thia Species 0.000 claims description 4
• 201000002859 sleep apnea Diseases 0.000 claims description 4
• 208000020401 Depressive disease Diseases 0.000 claims description 3
• 239000008177 pharmaceutical agent Substances 0.000 claims description 2
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims 1
• 125000005227 alkyl sulfonate group Chemical group 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 133
• 235000002639 sodium chloride Nutrition 0.000 description 118
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
• 125000000623 heterocyclic group Chemical group 0.000 description 65
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 64
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000002904 solvent Substances 0.000 description 63
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
• 229910052757 nitrogen Inorganic materials 0.000 description 58
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 229940079593 drug Drugs 0.000 description 54
• 238000000034 method Methods 0.000 description 50
• 125000004433 nitrogen atom Chemical group N* 0.000 description 50
• 239000002585 base Substances 0.000 description 49
• 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
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• 229910052731 fluorine Inorganic materials 0.000 description 36
• 125000003277 amino group Chemical class 0.000 description 33
• 125000001153 fluoro group Chemical group F* 0.000 description 33
• 230000035484 reaction time Effects 0.000 description 30
• 229910052717 sulfur Inorganic materials 0.000 description 30
• 150000001335 aliphatic alkanes Chemical class 0.000 description 28
• 125000004429 atom Chemical group 0.000 description 28
• 125000005842 heteroatom Chemical group 0.000 description 28
• 125000004430 oxygen atom Chemical group O* 0.000 description 28
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
• 238000010511 deprotection reaction Methods 0.000 description 27
• 125000004434 sulfur atom Chemical group 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
• 229910052799 carbon Inorganic materials 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• 150000001721 carbon Chemical group 0.000 description 21
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 229910052801 chlorine Inorganic materials 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
• 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
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 16
• 239000000203 mixture Substances 0.000 description 16
• 238000006722 reduction reaction Methods 0.000 description 16
• 239000002253 acid Substances 0.000 description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
• 239000000470 constituent Substances 0.000 description 15
• 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 14
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 14
• 241000124008 Mammalia Species 0.000 description 14
• 230000002378 acidificating effect Effects 0.000 description 14
• 229910052783 alkali metal Inorganic materials 0.000 description 14
• 150000003973 alkyl amines Chemical class 0.000 description 14
• 230000007062 hydrolysis Effects 0.000 description 14
• 238000006460 hydrolysis reaction Methods 0.000 description 14
• 239000003446 ligand Substances 0.000 description 14
• 229910052751 metal Inorganic materials 0.000 description 14
• 239000002184 metal Substances 0.000 description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
• 125000002950 monocyclic group Chemical group 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 229910052763 palladium Inorganic materials 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 14
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• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 13
• 125000003118 aryl group Chemical group 0.000 description 13
• 125000005161 aryl oxy 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
• 238000002360 preparation method Methods 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 12
• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 12
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
• 150000001412 amines Chemical class 0.000 description 12
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 12
• 125000003710 aryl alkyl group Chemical group 0.000 description 12
• 125000001769 aryl amino group Chemical group 0.000 description 12
• 238000005859 coupling reaction Methods 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 125000005914 C6-C14 aryloxy group Chemical group 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
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 239000003960 organic solvent Substances 0.000 description 11
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 11
• 229940001593 sodium carbonate Drugs 0.000 description 11
• 229910000029 sodium carbonate Inorganic materials 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
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 10
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 10
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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• 238000005804 alkylation reaction Methods 0.000 description 10
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
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• 125000001309 chloro group Chemical group Cl* 0.000 description 10
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• 125000004149 thio group Chemical group *S* 0.000 description 10
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
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• 125000002102 aryl alkyloxo group Chemical group 0.000 description 9
• 229910052802 copper Inorganic materials 0.000 description 9
• 239000010949 copper Substances 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 8
• 125000004070 6 membered heterocyclic group Chemical group 0.000 description 8
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
• 229920002472 Starch Polymers 0.000 description 8
• 125000002947 alkylene group Chemical group 0.000 description 8
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 8
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• 150000002576 ketones Chemical class 0.000 description 8
• 235000010355 mannitol Nutrition 0.000 description 8
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 8
• 229940098779 methanesulfonic acid Drugs 0.000 description 8
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
• 230000000069 prophylactic effect Effects 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000008107 starch Substances 0.000 description 8
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