CA2944308A1 - Chromene and 1,1 a,2,7b-tetrahydrocyclopropa[c]chromene pyridopyrazinediones as gamma-secretase modulators - Google Patents
Chromene and 1,1 a,2,7b-tetrahydrocyclopropa[c]chromene pyridopyrazinediones as gamma-secretase modulators Download PDFInfo
- Publication number
- CA2944308A1 CA2944308A1 CA2944308A CA2944308A CA2944308A1 CA 2944308 A1 CA2944308 A1 CA 2944308A1 CA 2944308 A CA2944308 A CA 2944308A CA 2944308 A CA2944308 A CA 2944308A CA 2944308 A1 CA2944308 A1 CA 2944308A1
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- Prior art keywords
- alkyl
- alkoxy
- hydroxy
- halo
- cycloalkyl
- Prior art date
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- -1 1,1 a,2,7b-tetrahydrocyclopropa[c]chromene pyridopyrazinediones Chemical class 0.000 title claims description 168
- VHNYOQKVZQVBLC-RTCGXNAVSA-N (4r,7e,9as)-7-[[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]methylidene]-4-(3,4,5-trifluorophenyl)-1,3,4,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazin-6-one Chemical compound C1([C@@H]2COC[C@@H]3CC\C(C(N32)=O)=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC(F)=C(F)C(F)=C1 VHNYOQKVZQVBLC-RTCGXNAVSA-N 0.000 title description 7
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 title description 7
- 229940124648 γ-Secretase Modulator Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 150000003839 salts Chemical class 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 53
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 337
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 190
- 125000005843 halogen group Chemical group 0.000 claims description 180
- 125000001424 substituent group Chemical group 0.000 claims description 133
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 108
- 229910052736 halogen Inorganic materials 0.000 claims description 98
- 229910052799 carbon Inorganic materials 0.000 claims description 80
- 150000002367 halogens Chemical group 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 65
- 150000001721 carbon Chemical group 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
- 125000001153 fluoro group Chemical group F* 0.000 claims description 48
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000002883 imidazolyl group Chemical group 0.000 claims description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 15
- 229910052760 oxygen Chemical group 0.000 claims description 14
- 239000001301 oxygen Chemical group 0.000 claims description 14
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 8
- 125000006005 fluoroethoxy group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 208000020016 psychiatric disease Diseases 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 208000010577 Niemann-Pick disease type C Diseases 0.000 claims description 5
- 208000007930 Type C Niemann-Pick Disease Diseases 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 4
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 10
- SIQJUJBSEDNWPI-UHFFFAOYSA-N CC1(OC2=CC=C(C=C2C(=C1)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)C(F)(F)F)C Chemical compound CC1(OC2=CC=C(C=C2C(=C1)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)C(F)(F)F)C SIQJUJBSEDNWPI-UHFFFAOYSA-N 0.000 claims 1
- NGCLDKLLCXHWGU-UHFFFAOYSA-N CC1(OC2=CC=C(C=C2C(=C1)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)OC(F)(F)F)C Chemical compound CC1(OC2=CC=C(C=C2C(=C1)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)OC(F)(F)F)C NGCLDKLLCXHWGU-UHFFFAOYSA-N 0.000 claims 1
- OXAMLWSJBGIHNL-INIZCTEOSA-N CC1(OC2=CC=C(C=C2C(=C1)[C@H](C)N1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)C(F)(F)F)C Chemical compound CC1(OC2=CC=C(C=C2C(=C1)[C@H](C)N1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O)C(F)(F)F)C OXAMLWSJBGIHNL-INIZCTEOSA-N 0.000 claims 1
- LHTSLMHEFKNOOX-PXDATVDWSA-N CC1(OC=2C=CC(=CC2[C@]2([C@@H]1C2)CN2C(C=1N(CC2)C(C(=CC1)N1C=NC(=C1)C)=O)=O)C(F)(F)F)C Chemical compound CC1(OC=2C=CC(=CC2[C@]2([C@@H]1C2)CN2C(C=1N(CC2)C(C(=CC1)N1C=NC(=C1)C)=O)=O)C(F)(F)F)C LHTSLMHEFKNOOX-PXDATVDWSA-N 0.000 claims 1
- ORLKJYBPSXUASX-PXDATVDWSA-N CC1(OC=2C=CC(=CC2[C@]2([C@@H]1C2)CN2C(C=1N(CC2)C(C(=CC1)N1C=NC(=C1)C)=O)=O)OC(F)(F)F)C Chemical compound CC1(OC=2C=CC(=CC2[C@]2([C@@H]1C2)CN2C(C=1N(CC2)C(C(=CC1)N1C=NC(=C1)C)=O)=O)OC(F)(F)F)C ORLKJYBPSXUASX-PXDATVDWSA-N 0.000 claims 1
- XSHCESWQAGNWDH-CMJOXMDJSA-N CC=1N=CN(C1)C1=CC=C2N(CCN(C2=O)C[C@@]23[C@@H](COC=4C=CC(=CC24)OC(F)(F)F)C3)C1=O Chemical compound CC=1N=CN(C1)C1=CC=C2N(CCN(C2=O)C[C@@]23[C@@H](COC=4C=CC(=CC24)OC(F)(F)F)C3)C1=O XSHCESWQAGNWDH-CMJOXMDJSA-N 0.000 claims 1
- MLZHNNLTXCDNLL-AVRWGWEMSA-N CC=1N=CN(C1)C1=CC=C2N(CCN(C2=O)C[C@]23[C@H](COC=4C=CC(=CC24)C2(CC2)C(F)(F)F)C3)C1=O Chemical compound CC=1N=CN(C1)C1=CC=C2N(CCN(C2=O)C[C@]23[C@H](COC=4C=CC(=CC24)C2(CC2)C(F)(F)F)C3)C1=O MLZHNNLTXCDNLL-AVRWGWEMSA-N 0.000 claims 1
- FRPPYXDKNYDZHE-CMJOXMDJSA-N ClC1=CC(=CC=2[C@]3([C@@H](COC12)C3)CN3C(C=1N(CC3)C(C(=CC1)N1C=NC(=C1)C)=O)=O)C(F)(F)F Chemical compound ClC1=CC(=CC=2[C@]3([C@@H](COC12)C3)CN3C(C=1N(CC3)C(C(=CC1)N1C=NC(=C1)C)=O)=O)C(F)(F)F FRPPYXDKNYDZHE-CMJOXMDJSA-N 0.000 claims 1
- MZPMUGOGQIVILU-UHFFFAOYSA-N ClC=1C=C2C(=CC(OC2=C(C1)F)(C)C)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O Chemical compound ClC=1C=C2C(=CC(OC2=C(C1)F)(C)C)CN1C(C=2N(CC1)C(C(=CC2)N2C=NC(=C2)C)=O)=O MZPMUGOGQIVILU-UHFFFAOYSA-N 0.000 claims 1
- LCNNBFCDMJIFBF-CPJLOUKISA-N FC(C)(OC1=CC=2[C@]3([C@@H](COC2C=C1)C3)CN3C(C=1N(CC3)C(C(=CC1)N1C=NC(=C1)C)=O)=O)F Chemical compound FC(C)(OC1=CC=2[C@]3([C@@H](COC2C=C1)C3)CN3C(C=1N(CC3)C(C(=CC1)N1C=NC(=C1)C)=O)=O)F LCNNBFCDMJIFBF-CPJLOUKISA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 87
- 230000015572 biosynthetic process Effects 0.000 abstract description 83
- 239000000543 intermediate Substances 0.000 abstract description 31
- 208000012902 Nervous system disease Diseases 0.000 abstract description 6
- 208000025966 Neurological disease Diseases 0.000 abstract description 5
- 201000010374 Down Syndrome Diseases 0.000 abstract description 4
- 206010044688 Trisomy 21 Diseases 0.000 abstract description 4
- 230000000626 neurodegenerative effect Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 239000000243 solution Substances 0.000 description 116
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- 239000011541 reaction mixture Substances 0.000 description 79
- 239000000047 product Substances 0.000 description 74
- 238000005160 1H NMR spectroscopy Methods 0.000 description 71
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
- 239000002904 solvent Substances 0.000 description 52
- 125000003545 alkoxy group Chemical group 0.000 description 51
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 50
- 239000012044 organic layer Substances 0.000 description 50
- 239000007787 solid Substances 0.000 description 46
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
- 239000002585 base Substances 0.000 description 45
- 229910052938 sodium sulfate Inorganic materials 0.000 description 45
- 235000011152 sodium sulphate Nutrition 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000012267 brine Substances 0.000 description 34
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 28
- 238000010898 silica gel chromatography Methods 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 25
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 239000003480 eluent Substances 0.000 description 20
- 239000012467 final product Substances 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
- 239000003814 drug Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 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 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 125000006413 ring segment Chemical group 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 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 12
- 238000009472 formulation Methods 0.000 description 12
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- 239000010410 layer Substances 0.000 description 12
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- 229920006395 saturated elastomer Polymers 0.000 description 12
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 11
- 239000010931 gold Substances 0.000 description 11
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- 239000007821 HATU Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
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- 125000006239 protecting group Chemical group 0.000 description 10
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
- 239000005909 Kieselgur Substances 0.000 description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 9
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 8
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000011593 sulfur Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- 241000124008 Mammalia Species 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
- 238000006073 displacement reaction Methods 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 6
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| CN106580997B (zh) * | 2016-12-09 | 2018-01-19 | 张田 | 一种治疗先兆流产的药物组合物 |
| JP6904612B2 (ja) | 2016-12-16 | 2021-07-21 | パイプライン セラピューティクス， インコーポレイテッド | 蝸牛シナプス障害を処置する方法 |
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| WO2007069053A1 (en) | 2005-12-14 | 2007-06-21 | Pfizer Products Inc. | Benzimidazole antagonists of the h-3 receptor |
| WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
| WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| US20090163482A1 (en) | 2006-03-13 | 2009-06-25 | Mchardy Stanton Furst | Tetralines antagonists of the h-3 receptor |
| SI2013208T1 (sl) | 2006-04-21 | 2011-09-30 | Pfizer Prod Inc | Piridin(3,4-b)pirazinoni |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| EP2124933B1 (en) | 2007-01-22 | 2012-10-17 | Pfizer Products Inc. | Tosylate salt of a therapeutic compound and pharmaceutical compositions thereof |
| EP2355659A4 (en) * | 2008-10-23 | 2012-10-10 | Merck Sharp & Dohme | Fused Hetereocyclic M1 Receptor Positive Allosmatic Modulators |
| JP5767393B2 (ja) * | 2011-03-31 | 2015-08-19 | ファイザー・インク | 新規二環式ピリジノン |
| AU2013261023B2 (en) * | 2012-05-16 | 2016-11-24 | Cellzome Limited | Substituted 3, 4 - dihydro - 2H - pyrido [1, 2 -a] pyrazine - 1, 6 - dione derivatives useful for the treatment of (inter alia) Alzheimer's disease |
| UA110688C2 (uk) * | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| CA2891755C (en) * | 2013-01-17 | 2021-10-26 | Janssen Pharmaceutica Nv | Substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| CA2925743C (en) * | 2013-10-04 | 2018-03-06 | Pfizer Inc. | Novel bicyclic pyridinones as gamma-secretase modulators |
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2015
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