EA031419B1 - ХРОМЕН И 1,1a,2,7b-ТЕТРАГИДРОЦИКЛОПРОПА[c]ХРОМЕН ПИРИДОПИРАЗИНДИОНЫ В КАЧЕСТВЕ МОДУЛЯТОРА ГАММА-СЕКРЕТАЗЫ - Google Patents

Info

Publication number

EA031419B1

EA031419B1 EA201600619A EA201600619A EA031419B1 EA 031419 B1 EA031419 B1 EA 031419B1 EA 201600619 A EA201600619 A EA 201600619A EA 201600619 A EA201600619 A EA 201600619A EA 031419 B1 EA031419 B1 EA 031419B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

methyl

halogen

mmol

alkoxy

Prior art date

2014-04-01

Links

• Espacenet
• Global Dossier
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• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 title description 8
• 229940124648 γ-Secretase Modulator Drugs 0.000 title description 4
• 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 3
• YIOCEUUNNIKUMJ-UHFFFAOYSA-N 1,1a,2,7b-tetrahydrocyclopropa[c]chromene Chemical compound C1=CC=C2C3CC3COC2=C1 YIOCEUUNNIKUMJ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 157
• 238000000034 method Methods 0.000 claims abstract description 57
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 144
• -1 cyano, hydroxy Chemical group 0.000 claims description 128
• 229910052736 halogen Inorganic materials 0.000 claims description 97
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 92
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 74
• 150000002367 halogens Chemical class 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 25
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
• 239000000460 chlorine Substances 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 125000002883 imidazolyl group Chemical group 0.000 claims description 15
• 208000024827 Alzheimer disease Diseases 0.000 claims description 14
• 150000001721 carbon Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 8
• 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 7
• 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 208000020016 psychiatric disease Diseases 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
• 208000007930 Type C Niemann-Pick Disease Diseases 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000006006 difluoroethoxy group Chemical group 0.000 claims description 5
• 125000006005 fluoroethoxy group Chemical group 0.000 claims description 5
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 125000006013 1,1-difluoroethoxy group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 2
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
• 230000000626 neurodegenerative effect Effects 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• 239000011593 sulfur Chemical group 0.000 claims 2
• 229910052717 sulfur Chemical group 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• 230000003247 decreasing effect Effects 0.000 claims 1
• 238000003786 synthesis reaction Methods 0.000 abstract description 92
• 230000015572 biosynthetic process Effects 0.000 abstract description 91
• 239000000543 intermediate Substances 0.000 abstract description 39
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 225
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 186
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
• 239000000243 solution Substances 0.000 description 99
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
• 238000005481 NMR spectroscopy Methods 0.000 description 90
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
• 239000000047 product Substances 0.000 description 86
• 239000011541 reaction mixture Substances 0.000 description 82
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 54
• 239000012044 organic layer Substances 0.000 description 51
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 49
• 229910052938 sodium sulfate Inorganic materials 0.000 description 49
• 235000011152 sodium sulphate Nutrition 0.000 description 49
• 239000002904 solvent Substances 0.000 description 48
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 47
• 239000007787 solid Substances 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 34
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
• 239000012267 brine Substances 0.000 description 32
• 230000014759 maintenance of location Effects 0.000 description 32
• 238000010898 silica gel chromatography Methods 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000007864 aqueous solution Substances 0.000 description 29
• 238000005516 engineering process Methods 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 239000002585 base Substances 0.000 description 28
• 239000010410 layer Substances 0.000 description 27
• 230000002829 reductive effect Effects 0.000 description 27
• 150000001412 amines Chemical class 0.000 description 26
• 125000006239 protecting group Chemical group 0.000 description 25
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 24
• 239000003480 eluent Substances 0.000 description 22
• 239000012467 final product Substances 0.000 description 21
• 238000003756 stirring Methods 0.000 description 20
• 239000003814 drug Substances 0.000 description 18
• 239000012634 fragment Substances 0.000 description 18
• 239000007788 liquid Substances 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 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 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 17
• 239000001569 carbon dioxide Substances 0.000 description 17
• 229910002092 carbon dioxide Inorganic materials 0.000 description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 16
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
• 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 14
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 description 14
• 238000004587 chromatography analysis Methods 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 229960004484 carbachol Drugs 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
• ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 230000021615 conjugation Effects 0.000 description 11
• 229910052740 iodine Inorganic materials 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
• 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 10
• 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 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 238000004811 liquid chromatography Methods 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 239000002552 dosage form Substances 0.000 description 9
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 8
• 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 8
• 235000019270 ammonium chloride Nutrition 0.000 description 8
• 125000001072 heteroaryl group Chemical group 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 7
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
• 150000001414 amino alcohols Chemical class 0.000 description 7
• 229960002519 amoxapine Drugs 0.000 description 7
• 238000004296 chiral HPLC Methods 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 208000035475 disorder Diseases 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 7
• VJZLQIPZNBPASX-OJJGEMKLSA-L prednisolone sodium phosphate Chemical compound [Na+].[Na+].O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP([O-])([O-])=O)[C@@H]4[C@@H]3CCC2=C1 VJZLQIPZNBPASX-OJJGEMKLSA-L 0.000 description 7
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 6
• BAEOHLZZXNKKJN-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1N1C(=O)C2=CC=CC(=O)N2CC1 BAEOHLZZXNKKJN-UHFFFAOYSA-N 0.000 description 6
• XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 6
• UWLBYMGXNMFPAV-MRXNPFEDSA-N CC1(OC2=CC=C(C=C2C(=C1)CN1C(C=2N(C[C@H]1C)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(C[C@H]1C)C(C(=CC2)N2C=NC(=C2)C)=O)=O)C(F)(F)F)C UWLBYMGXNMFPAV-MRXNPFEDSA-N 0.000 description 6
• 239000007821 HATU Substances 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 239000013543 active substance Substances 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 230000004071 biological effect Effects 0.000 description 6
• 229940097611 cardene Drugs 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 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 6
• 238000010438 heat treatment Methods 0.000 description 6
• 229960001783 nicardipine Drugs 0.000 description 6
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical class BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
• PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 5
• WSTAITCRSVOCTK-UHFFFAOYSA-N 1,4-diazabicyclo[2.2.2]octane;trimethylalumane Chemical compound C[Al](C)C.C[Al](C)C.C1CN2CCN1CC2 WSTAITCRSVOCTK-UHFFFAOYSA-N 0.000 description 5
• VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 description 5
• XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 5
• INJOMKTZOLKMBF-UHFFFAOYSA-N Guanfacine Chemical compound NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl INJOMKTZOLKMBF-UHFFFAOYSA-N 0.000 description 5
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