DK2271650T3 - QUINUCLIDE COMPOUNDS LIKE ALPHA-7 NICOTINACETYLCHOLINE RECEPTOR LIGANDS - Google Patents

Info

Publication number

DK2271650T3

DK2271650T3 DK09733949.3T DK09733949T DK2271650T3 DK 2271650 T3 DK2271650 T3 DK 2271650T3 DK 09733949 T DK09733949 T DK 09733949T DK 2271650 T3 DK2271650 T3 DK 2271650T3

Authority

DK

Denmark

Prior art keywords

mmol

amine

pyrimidinyl

octan

yield

Prior art date

2008-04-23

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 86
• 239000003446 ligand Substances 0.000 title claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 566
• -1 isoquinolinyl -indolonyl Chemical group 0.000 claims description 528
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 208000024827 Alzheimer disease Diseases 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
• 201000000980 schizophrenia Diseases 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000006396 chloropyrazinyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims description 4
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
• 125000006402 chloropyridazinyl group Chemical group 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 125000006405 methylpyridazinyl group Chemical group 0.000 claims description 3
• 125000006393 methylpyrimidinyl group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000006399 methylpyrazinyl group Chemical group 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• 125000004306 triazinyl group Chemical group 0.000 claims description 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
• 125000004414 alkyl thio group Chemical group 0.000 claims 3
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
• JBOYQZDFEWOILV-UHFFFAOYSA-N 5h-chromene Chemical compound O1C=CC=C2CC=CC=C21 JBOYQZDFEWOILV-UHFFFAOYSA-N 0.000 claims 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000002393 azetidinyl group Chemical group 0.000 claims 1
• 125000001246 bromo group Chemical group Br* 0.000 claims 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
• 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 382
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 293
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 285
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 275
• 238000005160 1H NMR spectroscopy Methods 0.000 description 241
• 239000000203 mixture Substances 0.000 description 228
• 238000006243 chemical reaction Methods 0.000 description 214
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 163
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 157
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 148
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 134
• 235000019439 ethyl acetate Nutrition 0.000 description 133
• 239000007787 solid Substances 0.000 description 129
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 117
• 239000000047 product Substances 0.000 description 115
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 108
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 101
• 239000000843 powder Substances 0.000 description 100
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
• 239000000243 solution Substances 0.000 description 84
• 229910001868 water Inorganic materials 0.000 description 82
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 72
• 238000000034 method Methods 0.000 description 70
• 239000011541 reaction mixture Substances 0.000 description 63
• 238000010898 silica gel chromatography Methods 0.000 description 62
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
• 239000012043 crude product Substances 0.000 description 45
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 44
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
• 239000002244 precipitate Substances 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 34
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
• 235000011114 ammonium hydroxide Nutrition 0.000 description 33
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
• 229910052938 sodium sulfate Inorganic materials 0.000 description 32
• 235000011152 sodium sulphate Nutrition 0.000 description 32
• 239000000725 suspension Substances 0.000 description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• 238000004587 chromatography analysis Methods 0.000 description 30
• OUKVGTYIZUXBIR-JZGIKJSDSA-N [(3s)-3-hydroxy-1-azoniabicyclo[2.2.2]octan-3-yl]methylazanium;dichloride Chemical compound Cl.Cl.C1CC2[C@@](CN)(O)CN1CC2 OUKVGTYIZUXBIR-JZGIKJSDSA-N 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 239000012267 brine Substances 0.000 description 28
• 238000004440 column chromatography Methods 0.000 description 28
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 28
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
• 238000003818 flash chromatography Methods 0.000 description 27
• 239000003921 oil Substances 0.000 description 27
• 235000019198 oils Nutrition 0.000 description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 229910000085 borane Inorganic materials 0.000 description 24
• 239000013058 crude material Substances 0.000 description 24
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• 238000000746 purification Methods 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 21
• 229910002027 silica gel Inorganic materials 0.000 description 21
• KXMMNJQMGILZDB-UHFFFAOYSA-N 1-(2-oxopyridine-1-carbothioyl)pyridin-2-one Chemical compound O=C1C=CC=CN1C(=S)N1C(=O)C=CC=C1 KXMMNJQMGILZDB-UHFFFAOYSA-N 0.000 description 20
• 238000001914 filtration Methods 0.000 description 20
• 239000012071 phase Substances 0.000 description 20
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 18
• 238000004809 thin layer chromatography Methods 0.000 description 18
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 17
• 238000003556 assay Methods 0.000 description 17
• 235000011089 carbon dioxide Nutrition 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 229910000024 caesium carbonate Inorganic materials 0.000 description 16
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 16
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 16
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 15
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 239000000908 ammonium hydroxide Substances 0.000 description 13
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
• 230000003287 optical effect Effects 0.000 description 13
• 102000005962 receptors Human genes 0.000 description 13
• 108020003175 receptors Proteins 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• DUKKRSPKJMHASP-UHFFFAOYSA-N 6-chloropyrimidin-4-amine Chemical compound NC1=CC(Cl)=NC=N1 DUKKRSPKJMHASP-UHFFFAOYSA-N 0.000 description 12
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
• 239000004202 carbamide Substances 0.000 description 10
• 238000012512 characterization method Methods 0.000 description 10
• 230000014759 maintenance of location Effects 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 9
• FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• VPRKGLYZWQCCHU-UHFFFAOYSA-N 6-pyridin-3-ylpyrimidin-4-amine Chemical compound C1=NC(N)=CC(C=2C=NC=CC=2)=N1 VPRKGLYZWQCCHU-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 108091006146 Channels Proteins 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 208000015122 neurodegenerative disease Diseases 0.000 description 7
• QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 7
• 238000002953 preparative HPLC Methods 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 230000002441 reversible effect Effects 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• GTWJGHJRSNOFFG-FQEVSTJZSA-N (3r)-n-(6,8-dimethylisoquinolin-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,5'-4h-1,3-oxazole]-2'-amine Chemical compound C1N(CC2)CCC2[C@]1(O1)CN=C1NC1=CC2=CC(C)=CC(C)=C2C=N1 GTWJGHJRSNOFFG-FQEVSTJZSA-N 0.000 description 6
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 6
• BLGYAIWJMVWVDS-UHFFFAOYSA-N 6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound C1=C(OC)C=CC2=NC(N)=NN21 BLGYAIWJMVWVDS-UHFFFAOYSA-N 0.000 description 6
• 208000019022 Mood disease Diseases 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• 125000005605 benzo group Chemical group 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• YKOUABZEDZDJEY-UHFFFAOYSA-N methyl 2,2-diethoxyethanimidate Chemical compound CCOC(OCC)C(=N)OC YKOUABZEDZDJEY-UHFFFAOYSA-N 0.000 description 6
• PSQGPXUZFGQICZ-UHFFFAOYSA-N n'-[(2,4-dichlorophenyl)methyl]-2,2-diethoxyethanimidamide Chemical compound CCOC(OCC)C(=N)NCC1=CC=C(Cl)C=C1Cl PSQGPXUZFGQICZ-UHFFFAOYSA-N 0.000 description 6
• ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 6
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
• XNKKRHBZOMRNQS-HNNXBMFYSA-N (3r)-n-([1,3]oxazolo[4,5-b]pyridin-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,5'-4h-1,3-oxazole]-2'-amine Chemical compound C1N(CC2)CCC2[C@]21OC(NC=1OC3=CC=CN=C3N=1)=NC2 XNKKRHBZOMRNQS-HNNXBMFYSA-N 0.000 description 5
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
• IKECPQGVQXXBSD-UHFFFAOYSA-N 5,6-dichloro-3-isothiocyanatoisoquinoline Chemical compound C1=NC(N=C=S)=CC2=C(Cl)C(Cl)=CC=C21 IKECPQGVQXXBSD-UHFFFAOYSA-N 0.000 description 5
• KRRTXVSBTPCDOS-UHFFFAOYSA-N 5-bromopyrazin-2-amine Chemical compound NC1=CN=C(Br)C=N1 KRRTXVSBTPCDOS-UHFFFAOYSA-N 0.000 description 5
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 229940045348 brown mixture Drugs 0.000 description 5
• FKGQRXQOODICAT-UHFFFAOYSA-N di(imidazol-1-yl)methanimine Chemical compound C1=CN=CN1C(=N)N1C=CN=C1 FKGQRXQOODICAT-UHFFFAOYSA-N 0.000 description 5
• 201000010099 disease Diseases 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
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