UA76410C2 - Azaindols, pharmaceutical composition on their basis - Google Patents

Info

Publication number

UA76410C2

UA76410C2 UA2002076056A UA2002076056A UA76410C2 UA 76410 C2 UA76410 C2 UA 76410C2 UA 2002076056 A UA2002076056 A UA 2002076056A UA 2002076056 A UA2002076056 A UA 2002076056A UA 76410 C2 UA76410 C2 UA 76410C2

Authority

UA

Ukraine

Prior art keywords

group

compound according

vya

iia

optionally substituted

Prior art date

1999-12-24

Links

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• Global Dossier
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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 352
• 239000000203 mixture Substances 0.000 claims abstract description 127
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 117
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 85
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 68
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 125000003118 aryl group Chemical group 0.000 claims abstract description 64
• 229940002612 prodrug Drugs 0.000 claims abstract description 49
• 239000000651 prodrug Substances 0.000 claims abstract description 49
• 125000005843 halogen group Chemical group 0.000 claims abstract description 33
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 26
• 239000012453 solvate Substances 0.000 claims abstract description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 24
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 20
• 125000001424 substituent group Chemical group 0.000 claims abstract description 11
• 125000002252 acyl group Chemical group 0.000 claims abstract description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
• 229910014033 C-OH Inorganic materials 0.000 claims abstract description 3
• 229910014570 C—OH Inorganic materials 0.000 claims abstract description 3
• 238000000034 method Methods 0.000 claims description 282
• -1 atom halogen Chemical class 0.000 claims description 207
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 127
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 115
• 239000002253 acid Substances 0.000 claims description 83
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 77
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 72
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 150000004677 hydrates Chemical class 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
• 108091000080 Phosphotransferase Proteins 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
• 102000020233 phosphotransferase Human genes 0.000 claims description 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 125000001041 indolyl group Chemical group 0.000 claims description 14
• TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 13
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical group CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000003367 polycyclic group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 230000003197 catalytic effect Effects 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 239000003112 inhibitor Substances 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
• 201000004681 Psoriasis Diseases 0.000 claims 1
• 206010003246 arthritis Diseases 0.000 claims 1
• 208000006673 asthma Diseases 0.000 claims 1
• 125000000524 functional group Chemical group 0.000 claims 1
• 229940043355 kinase inhibitor Drugs 0.000 claims 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 102000001253 Protein Kinase Human genes 0.000 abstract description 10
• 108060006633 protein kinase Proteins 0.000 abstract description 10
• 239000001257 hydrogen Substances 0.000 abstract description 4
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
• 125000001475 halogen functional group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 366
• 239000007787 solid Substances 0.000 description 296
• 238000001819 mass spectrum Methods 0.000 description 229
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
• 239000000243 solution Substances 0.000 description 158
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 119
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
• 239000011541 reaction mixture Substances 0.000 description 64
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 60
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
• 238000003756 stirring Methods 0.000 description 54
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 50
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 39
• 238000004809 thin layer chromatography Methods 0.000 description 38
• 239000000377 silicon dioxide Substances 0.000 description 37
• 238000003818 flash chromatography Methods 0.000 description 36
• 239000011734 sodium Substances 0.000 description 35
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
• 238000004128 high performance liquid chromatography Methods 0.000 description 34
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 31
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 31
• 235000019341 magnesium sulphate Nutrition 0.000 description 31
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 30
• 235000012239 silicon dioxide Nutrition 0.000 description 30
• 239000000126 substance Substances 0.000 description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
• 239000012299 nitrogen atmosphere Substances 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• 239000012442 inert solvent Substances 0.000 description 26
• 239000012267 brine Substances 0.000 description 25
• 229910052799 carbon Inorganic materials 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
• 150000001721 carbon Chemical group 0.000 description 21
• 239000000284 extract Substances 0.000 description 21
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
• 239000012634 fragment Substances 0.000 description 19
• 239000010410 layer Substances 0.000 description 19
• 229910052938 sodium sulfate Inorganic materials 0.000 description 19
• 235000011152 sodium sulphate Nutrition 0.000 description 19
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 18
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 17
• 229960000583 acetic acid Drugs 0.000 description 17
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 17
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 17
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 235000019260 propionic acid Nutrition 0.000 description 16
• 229940086542 triethylamine Drugs 0.000 description 16
• 235000019441 ethanol Nutrition 0.000 description 15
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
• 239000012312 sodium hydride Substances 0.000 description 12
• 229910000104 sodium hydride Inorganic materials 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 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 12
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
• 239000004146 Propane-1,2-diol Substances 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 229960004063 propylene glycol Drugs 0.000 description 11
• 235000013772 propylene glycol Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
• LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
• 229910052740 iodine Inorganic materials 0.000 description 10
• 239000011572 manganese Substances 0.000 description 10
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 9
• 230000029936 alkylation Effects 0.000 description 9
• 238000005804 alkylation reaction Methods 0.000 description 9
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 9
• 239000012458 free base Substances 0.000 description 9
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
• 235000010469 Glycine max Nutrition 0.000 description 8
• 241000764773 Inna Species 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 238000000354 decomposition reaction Methods 0.000 description 8
• 238000000921 elemental analysis Methods 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
• NFHFRUOZVGFOOS-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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 239000011575 calcium Substances 0.000 description 7
• 239000006071 cream Substances 0.000 description 7
• 235000019253 formic acid Nutrition 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• 102000005962 receptors Human genes 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 238000001228 spectrum Methods 0.000 description 7
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
• CZFFYXFWPCJEGW-UHFFFAOYSA-N 5-methoxy-1h-indole-3-carbonitrile Chemical compound COC1=CC=C2NC=C(C#N)C2=C1 CZFFYXFWPCJEGW-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
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