SG187656A1 - Heterocyclic compound and use thereof - Google Patents

Info

Publication number

SG187656A1

SG187656A1 SG2013007463A SG2013007463A SG187656A1 SG 187656 A1 SG187656 A1 SG 187656A1 SG 2013007463 A SG2013007463 A SG 2013007463A SG 2013007463 A SG2013007463 A SG 2013007463A SG 187656 A1 SG187656 A1 SG 187656A1

Authority

SG

Singapore

Prior art keywords

optionally substituted

halogen atom

alkyl

ring

group

Prior art date

2010-08-10

Links

• Espacenet
• Global Dossier
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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 331
• 150000003839 salts Chemical class 0.000 claims abstract description 130
• 229940126585 therapeutic drug Drugs 0.000 claims abstract description 42
• 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 20
• 230000000069 prophylactic effect Effects 0.000 claims abstract description 12
• 229940043274 prophylactic drug Drugs 0.000 claims abstract description 8
• -1 L is a bond Chemical group 0.000 claims description 518
• 125000005843 halogen group Chemical group 0.000 claims description 303
• 125000001424 substituent group Chemical group 0.000 claims description 224
• 125000000217 alkyl group Chemical group 0.000 claims description 204
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 115
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 99
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 98
• 125000003545 alkoxy group Chemical group 0.000 claims description 92
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 71
• 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 68
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 67
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 57
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 51
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
• 239000003814 drug Substances 0.000 claims description 45
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 42
• 125000004429 atom Chemical group 0.000 claims description 38
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 37
• 125000002947 alkylene group Chemical group 0.000 claims description 35
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 31
• 229910052717 sulfur Inorganic materials 0.000 claims description 31
• 125000004434 sulfur atom Chemical group 0.000 claims description 31
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 30
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 29
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
• JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 27
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 26
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 25
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 24
• 108090000078 AMPA Receptors Proteins 0.000 claims description 23
• 102000003678 AMPA Receptors Human genes 0.000 claims description 23
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 23
• 230000036961 partial effect Effects 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 125000004450 alkenylene group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 21
• IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 21
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 21
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 20
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 18
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 18
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 229930192474 thiophene Natural products 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 17
• 150000001924 cycloalkanes Chemical class 0.000 claims description 17
• 125000004419 alkynylene group Chemical group 0.000 claims description 16
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 16
• 238000011321 prophylaxis Methods 0.000 claims description 16
• 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
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 14
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 14
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 14
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 14
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 13
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 13
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000003566 oxetanyl group Chemical group 0.000 claims description 12
• 125000006850 spacer group Chemical group 0.000 claims description 12
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-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
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 10
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
• 208000020401 Depressive disease Diseases 0.000 claims description 9
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 9
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 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 6
• 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 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims description 3
• 150000001539 azetidines Chemical class 0.000 claims description 3
• 150000001556 benzimidazoles Chemical class 0.000 claims description 3
• 150000005528 benzodioxoles Chemical class 0.000 claims description 3
• 150000002240 furans Chemical class 0.000 claims description 3
• 150000002473 indoazoles Chemical class 0.000 claims description 3
• 150000002475 indoles Chemical class 0.000 claims description 3
• 150000002921 oxetanes Chemical class 0.000 claims description 3
• 150000003053 piperidines Chemical class 0.000 claims description 3
• 150000003222 pyridines Chemical class 0.000 claims description 3
• 150000003248 quinolines Chemical class 0.000 claims description 3
• 229940124597 therapeutic agent Drugs 0.000 claims description 3
• 150000003577 thiophenes Chemical class 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• 230000003389 potentiating effect Effects 0.000 abstract description 9
• 238000006243 chemical reaction Methods 0.000 description 123
• 235000002639 sodium chloride Nutrition 0.000 description 117
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
• 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
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000002904 solvent Substances 0.000 description 61
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 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 37
• 239000002585 base Substances 0.000 description 36
• 125000001153 fluoro group Chemical group F* 0.000 description 33
• 238000010511 deprotection reaction Methods 0.000 description 32
• 230000035484 reaction time Effects 0.000 description 31
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 229940079593 drug Drugs 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 125000003277 amino group Chemical group 0.000 description 23
• 238000006722 reduction reaction Methods 0.000 description 23
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• 150000001721 carbon Chemical group 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 230000007062 hydrolysis Effects 0.000 description 17
• 238000006460 hydrolysis reaction Methods 0.000 description 17
• 229910052751 metal Inorganic materials 0.000 description 17
• 239000002184 metal Substances 0.000 description 17
• 125000004043 oxo group Chemical group O=* 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
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 15
• 125000004414 alkyl thio group Chemical group 0.000 description 15
• 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
• 238000002360 preparation method Methods 0.000 description 15
• 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
• 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
• 239000003446 ligand 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
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 13
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 13
• 125000005129 aryl carbonyl 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
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
• 239000000203 mixture Substances 0.000 description 13
• 125000006239 protecting group Chemical group 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• 230000002378 acidificating effect Effects 0.000 description 12
• 125000001769 aryl amino 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
• 229910052763 palladium Inorganic materials 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 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
• 125000003282 alkyl amino group Chemical group 0.000 description 11
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 11
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
• 239000003960 organic solvent Substances 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• 230000009467 reduction Effects 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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 238000005804 alkylation reaction Methods 0.000 description 10
• 150000001408 amides Chemical class 0.000 description 10
• 125000005116 aryl carbamoyl 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
• 230000032050 esterification Effects 0.000 description 10
• 238000005886 esterification reaction Methods 0.000 description 10
• 150000002170 ethers Chemical class 0.000 description 10
• 150000008282 halocarbons Chemical class 0.000 description 10
• 239000012046 mixed solvent Substances 0.000 description 10
• 150000007524 organic acids Chemical class 0.000 description 10
• 229940001593 sodium carbonate Drugs 0.000 description 10
• 229910000029 sodium carbonate Inorganic materials 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
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
• 229910052802 copper Inorganic materials 0.000 description 9
• 239000010949 copper Substances 0.000 description 9
• 125000004185 ester group Chemical group 0.000 description 9
• 150000007522 mineralic acids Chemical class 0.000 description 9
• 150000002825 nitriles Chemical class 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• 125000000547 substituted alkyl group Chemical group 0.000 description 9
• 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 8
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