NO327817B1 - ``Benzodiazepin-derivater, deres fremstilling, medikament inneholdende slike samt anvendelse av disse for fremstilling av medikament for behandling av sykdom`` - Google Patents

Info

Publication number

NO327817B1

NO327817B1 NO20021690A NO20021690A NO327817B1 NO 327817 B1 NO327817 B1 NO 327817B1 NO 20021690 A NO20021690 A NO 20021690A NO 20021690 A NO20021690 A NO 20021690A NO 327817 B1 NO327817 B1 NO 327817B1

Authority

NO

Norway

Prior art keywords

phenyl

mmol

oxo

butyl ester

carbamic acid

Prior art date

1999-10-15

Links

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• Global Dossier
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• 238000002360 preparation method Methods 0.000 title claims description 42
• 239000003814 drug Substances 0.000 title claims description 13
• 229940079593 drug Drugs 0.000 title claims description 8
• 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title 1
• 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
• 238000000034 method Methods 0.000 claims description 545
• 150000001875 compounds Chemical class 0.000 claims description 114
• -1 hydroxyethoxy Chemical group 0.000 claims description 65
• 238000006243 chemical reaction Methods 0.000 claims description 49
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 12
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• FBPIGKDLQMIHLG-UHFFFAOYSA-N 4-(3-iodophenyl)-7-(2-methoxyethoxy)-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound COCCOC1=CC=2N=C(C=3C=C(I)C=CC=3)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 FBPIGKDLQMIHLG-UHFFFAOYSA-N 0.000 claims description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• QDKZHQGXPVFLHU-UHFFFAOYSA-N 1,5-benzodiazepin-2-one Chemical compound O=C1C=CN=C2C=CC=CC2=N1 QDKZHQGXPVFLHU-UHFFFAOYSA-N 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 208000025966 Neurological disease Diseases 0.000 claims description 4
• 208000028017 Psychotic disease Diseases 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• OPTKWCKGENRFQA-UHFFFAOYSA-N methyl 2-[[4-(3-cyanophenyl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-7-yl]sulfanyl]acetate Chemical compound COC(=O)CSC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 OPTKWCKGENRFQA-UHFFFAOYSA-N 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
• UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 3
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical class C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 3
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
• RKIDXLGMZYYSAA-UHFFFAOYSA-N 2-[8-(2-fluorophenyl)-7-hydroxy-2-oxo-1,5-dihydro-1,5-benzodiazepin-4-yl]thiophene-3-carbonitrile Chemical compound OC1=CC=2NC(C3=C(C=CS3)C#N)=CC(=O)NC=2C=C1C1=CC=CC=C1F RKIDXLGMZYYSAA-UHFFFAOYSA-N 0.000 claims description 3
• UVPDZJUTLGSHOW-UHFFFAOYSA-N 3-(7-chloro-2-oxo-8-phenyl-1,3-dihydro-1,5-benzodiazepin-4-yl)benzonitrile Chemical compound ClC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C1=CC=CC=C1 UVPDZJUTLGSHOW-UHFFFAOYSA-N 0.000 claims description 3
• QRRFEMJQTYRNMN-UHFFFAOYSA-N 3-[7-(4-methylpiperazin-1-yl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]benzonitrile Chemical compound C1CN(C)CCN1C(C(=C1)C#CC=2C=CC=CC=2)=CC2=C1NC(=O)CC(C=1C=C(C=CC=1)C#N)=N2 QRRFEMJQTYRNMN-UHFFFAOYSA-N 0.000 claims description 3
• FGIWPVCRHZHHAO-UHFFFAOYSA-N 3-[7-(cyanomethyl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]benzonitrile Chemical compound C1=C2NC(=O)CC(C=3C=C(C=CC=3)C#N)=NC2=CC(CC#N)=C1C#CC1=CC=CC=C1 FGIWPVCRHZHHAO-UHFFFAOYSA-N 0.000 claims description 3
• ZVSMESDSZFNDMJ-UHFFFAOYSA-N 3-[7-methoxy-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]benzonitrile Chemical compound COC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 ZVSMESDSZFNDMJ-UHFFFAOYSA-N 0.000 claims description 3
• JSFNPUJTYTWCLA-UHFFFAOYSA-N 3-[8-(2,5-difluorophenyl)-7-hydroxy-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]benzonitrile Chemical compound OC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C1=CC(F)=CC=C1F JSFNPUJTYTWCLA-UHFFFAOYSA-N 0.000 claims description 3
• MTOSFHOAULLKRN-UHFFFAOYSA-N 4-[8-(2-fluorophenyl)-7-hydroxy-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound OC1=CC=2N=C(C=3C=C(N=CC=3)C#N)CC(=O)NC=2C=C1C1=CC=CC=C1F MTOSFHOAULLKRN-UHFFFAOYSA-N 0.000 claims description 3
• DXDDOWBFRGJDFS-UHFFFAOYSA-N 4-[8-(2-fluorophenyl)-7-methoxy-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound COC1=CC=2N=C(C=3C=C(N=CC=3)C#N)CC(=O)NC=2C=C1C1=CC=CC=C1F DXDDOWBFRGJDFS-UHFFFAOYSA-N 0.000 claims description 3
• IWJJFYANLOIUKW-UHFFFAOYSA-N 4-[8-(4-fluorophenyl)-7-hydroxy-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound OC1=CC=2N=C(C=3C=C(N=CC=3)C#N)CC(=O)NC=2C=C1C1=CC=C(F)C=C1 IWJJFYANLOIUKW-UHFFFAOYSA-N 0.000 claims description 3
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
• DFPPYGYDEAPNML-UHFFFAOYSA-N 5-[8-(2-fluorophenyl)-7-methoxy-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]thiophene-2-carbonitrile Chemical compound COC1=CC=2N=C(C=3SC(=CC=3)C#N)CC(=O)NC=2C=C1C1=CC=CC=C1F DFPPYGYDEAPNML-UHFFFAOYSA-N 0.000 claims description 3
• BAOSWBZMDZMRIY-UHFFFAOYSA-N 8-(2-fluorophenyl)-7-methoxy-4-[3-(2-methylimidazol-1-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound COC1=CC=2N=C(C=3C=C(C=CC=3)N3C(=NC=C3)C)CC(=O)NC=2C=C1C1=CC=CC=C1F BAOSWBZMDZMRIY-UHFFFAOYSA-N 0.000 claims description 3
• FFZSVPXVCARFFX-UHFFFAOYSA-N 8-(4-fluorophenyl)-7-[4-(2-hydroxyethoxy)piperidin-1-yl]-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1CC(OCCO)CCN1C(C(=C1)C=2C=CC(F)=CC=2)=CC2=C1NC(=O)CC(C=1C=C(C=CC=1)N1C=NC=C1)=N2 FFZSVPXVCARFFX-UHFFFAOYSA-N 0.000 claims description 3
• URUMMRWACZFGEQ-UHFFFAOYSA-N 8-[2-(4-fluorophenyl)ethynyl]-7-(hydroxymethyl)-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound OCC1=CC=2N=C(C=3C=C(C=CC=3)N3C=NC=C3)CC(=O)NC=2C=C1C#CC1=CC=C(F)C=C1 URUMMRWACZFGEQ-UHFFFAOYSA-N 0.000 claims description 3
• RFKFAFMEFPSHAN-UHFFFAOYSA-N 8-[2-(4-fluorophenyl)ethynyl]-7-hydroxy-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound OC1=CC=2N=C(C=3C=C(C=CC=3)N3C=NC=C3)CC(=O)NC=2C=C1C#CC1=CC=C(F)C=C1 RFKFAFMEFPSHAN-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• HHKGHOHNMXZGJC-UHFFFAOYSA-N chembl404886 Chemical compound OC1=CC=2N=C(C=3C=C(C=CC=3)N3N=NC=C3)CC(=O)NC=2C=C1C#CC1=CC=C(F)C=C1 HHKGHOHNMXZGJC-UHFFFAOYSA-N 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
• 206010027175 memory impairment Diseases 0.000 claims description 3
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
• OBKSPYGKOAVWPB-UHFFFAOYSA-N 2-[4-(3-cyanophenyl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-7-yl]acetamide Chemical compound NC(=O)CC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 OBKSPYGKOAVWPB-UHFFFAOYSA-N 0.000 claims description 2
• MIKJDYQBHVZYBY-UHFFFAOYSA-N 2-[[4-(3-imidazol-1-ylphenyl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-7-yl]oxy]acetonitrile Chemical compound C1=C2NC(=O)CC(C=3C=C(C=CC=3)N3C=NC=C3)=NC2=CC(OCC#N)=C1C#CC1=CC=CC=C1 MIKJDYQBHVZYBY-UHFFFAOYSA-N 0.000 claims description 2
• RMNNCRGKNMWAII-UHFFFAOYSA-N 4-(3-imidazol-1-ylphenyl)-7-(2-methoxyethoxy)-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound COCCOC1=CC=2N=C(C=3C=C(C=CC=3)N3C=NC=C3)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 RMNNCRGKNMWAII-UHFFFAOYSA-N 0.000 claims description 2
• CHFZTXQHQRTDEM-UHFFFAOYSA-N 8-(2-fluorophenyl)-7-hydroxy-4-[3-(triazol-1-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound OC1=CC=2N=C(C=3C=C(C=CC=3)N3N=NC=C3)CC(=O)NC=2C=C1C1=CC=CC=C1F CHFZTXQHQRTDEM-UHFFFAOYSA-N 0.000 claims description 2
• JGIATRRZRPYCNH-UHFFFAOYSA-N 8-(4-fluorophenyl)-7-hydroxy-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound OC1=CC=2N=C(C=3C=C(C=CC=3)N3C=NC=C3)CC(=O)NC=2C=C1C1=CC=C(F)C=C1 JGIATRRZRPYCNH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 238000010511 deprotection reaction Methods 0.000 claims description 2
• 150000002240 furans Chemical class 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
• RMVBDQZEMLMPAJ-UHFFFAOYSA-N 3-[7-chloro-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]benzonitrile Chemical compound ClC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 RMVBDQZEMLMPAJ-UHFFFAOYSA-N 0.000 claims 1
• OPCXKXGFSLZHAI-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[2-(4-methylimidazol-1-yl)-1,3-thiazol-4-yl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CN1C1=NC(C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=CS1 OPCXKXGFSLZHAI-UHFFFAOYSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 125000003831 tetrazolyl group Chemical class 0.000 claims 1
• 239000007787 solid Substances 0.000 description 294
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 186
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 118
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
• 239000000460 chlorine Substances 0.000 description 89
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 68
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• OABSXOMYUDYCAN-UHFFFAOYSA-N 6-(3-imidazol-1-ylphenyl)-2,2-dimethyl-1,3-dioxin-4-one Chemical compound O1C(C)(C)OC(=O)C=C1C1=CC=CC(N2C=NC=C2)=C1 OABSXOMYUDYCAN-UHFFFAOYSA-N 0.000 description 60
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• 235000019439 ethyl acetate Nutrition 0.000 description 50
• 239000000126 substance Substances 0.000 description 48
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• 230000009467 reduction Effects 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
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• 239000000203 mixture Substances 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
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• PXCREFJJZMYUBE-UHFFFAOYSA-N tert-butyl n-(5-chloro-4-iodo-2-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(I)C=C1[N+]([O-])=O PXCREFJJZMYUBE-UHFFFAOYSA-N 0.000 description 36
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
• 239000011734 sodium Substances 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 31
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• 230000015572 biosynthetic process Effects 0.000 description 28
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• 238000010898 silica gel chromatography Methods 0.000 description 24
• GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 21
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 20
• 239000012267 brine Substances 0.000 description 20
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• HXBXHVQQFVZFNW-UHFFFAOYSA-N 5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-2-nitro-4-(2-phenylethynyl)aniline Chemical compound O1C(C)(C)OCC1COC1=CC(N)=C([N+]([O-])=O)C=C1C#CC1=CC=CC=C1 HXBXHVQQFVZFNW-UHFFFAOYSA-N 0.000 description 4
• LGMFVZGMVCXNBW-UHFFFAOYSA-N 5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-4-iodo-2-nitroaniline Chemical compound O1C(C)(C)OCC1COC1=CC(N)=C([N+]([O-])=O)C=C1I LGMFVZGMVCXNBW-UHFFFAOYSA-N 0.000 description 4
• IXGGSHYJYYQPGR-UHFFFAOYSA-N 6-(3-iodophenyl)-2,2-dimethyl-1,3-dioxin-4-one Chemical compound O1C(C)(C)OC(=O)C=C1C1=CC=CC(I)=C1 IXGGSHYJYYQPGR-UHFFFAOYSA-N 0.000 description 4
• LVKISJSUOVZDAL-UHFFFAOYSA-N 7-(2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-8-(4-fluorophenyl)-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C2OC(C)(C)OC2CN1C1=CC=2N=C(C=3C=C(C=CC=3)N3C=NC=C3)CC(=O)NC=2C=C1C1=CC=C(F)C=C1 LVKISJSUOVZDAL-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• 229910004373 HOAc Inorganic materials 0.000 description 4
• 208000002193 Pain Diseases 0.000 description 4
• 208000027089 Parkinsonian disease Diseases 0.000 description 4
• 206010034010 Parkinsonism Diseases 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 4
• OEQIEDAWGSZELP-UHFFFAOYSA-N [1-[4-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]-3-phenylprop-2-ynyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(OC(=O)C(C)(C)C)C#CC=2C=CC=CC=2)=CC=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 OEQIEDAWGSZELP-UHFFFAOYSA-N 0.000 description 4
• 239000000010 aprotic solvent Substances 0.000 description 4
• 150000001543 aryl boronic acids Chemical class 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• 238000005859 coupling reaction Methods 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• XBGDPLROEPFJDG-UHFFFAOYSA-N methyl 2-[2-iodo-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-nitrophenyl]sulfanylacetate Chemical compound COC(=O)CSC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1I XBGDPLROEPFJDG-UHFFFAOYSA-N 0.000 description 4
• VAZWRTOCBOACHN-UHFFFAOYSA-N methyl 2-[4-(3-cyanophenyl)-2-oxo-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-7-yl]acetate Chemical compound COC(=O)CC1=CC=2N=C(C=3C=C(C=CC=3)C#N)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 VAZWRTOCBOACHN-UHFFFAOYSA-N 0.000 description 4
• RAPFRRQKZXDDEJ-UHFFFAOYSA-N methyl 2-[4-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-phenylethynyl)phenyl]acetate Chemical compound C1=C(C#CC=2C=CC=CC=2)C(CC(=O)OC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 RAPFRRQKZXDDEJ-UHFFFAOYSA-N 0.000 description 4
• NKGYSGGAEUCELQ-UHFFFAOYSA-N methyl 3-(1,2,4-triazol-1-yl)benzoate Chemical compound COC(=O)C1=CC=CC(N2N=CN=C2)=C1 NKGYSGGAEUCELQ-UHFFFAOYSA-N 0.000 description 4
• ZGVYPBINPLNBDH-UHFFFAOYSA-N methyl 3-amino-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C(N)=C1 ZGVYPBINPLNBDH-UHFFFAOYSA-N 0.000 description 4
• NGXJMMQUTLNUSA-UHFFFAOYSA-N methyl 4-amino-2-iodo-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate Chemical compound COC(=O)C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1I NGXJMMQUTLNUSA-UHFFFAOYSA-N 0.000 description 4
• XOHRGNCNWBXUHT-UHFFFAOYSA-N methyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-nitro-2-(2-phenylethynyl)benzoate Chemical compound COC(=O)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C#CC1=CC=CC=C1 XOHRGNCNWBXUHT-UHFFFAOYSA-N 0.000 description 4
• JHSXRBBTSBWXDY-UHFFFAOYSA-N methyl 5-amino-2-iodo-4-nitrobenzoate Chemical compound COC(=O)C1=CC(N)=C([N+]([O-])=O)C=C1I JHSXRBBTSBWXDY-UHFFFAOYSA-N 0.000 description 4
• 150000002828 nitro derivatives Chemical class 0.000 description 4
• 239000000825 pharmaceutical preparation Substances 0.000 description 4
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
• 229920005862 polyol Polymers 0.000 description 4
• 150000003077 polyols Chemical class 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• QVBPZZKELHNMDZ-UHFFFAOYSA-M potassium;3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoate Chemical compound [K+].CC(C)(C)OC(=O)CC([O-])=O QVBPZZKELHNMDZ-UHFFFAOYSA-M 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• DJPLMFDGCAEYNH-UHFFFAOYSA-N tert-butyl 2-[4-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-phenylethynyl)phenoxy]acetate Chemical compound C1=C(C#CC=2C=CC=CC=2)C(OCC(=O)OC(C)(C)C)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 DJPLMFDGCAEYNH-UHFFFAOYSA-N 0.000 description 4
• QGBYZMSEIRCPSS-UHFFFAOYSA-N tert-butyl 2-[4-amino-2-(4-fluorophenyl)-5-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]acetate Chemical compound CC(C)(C)OC(=O)COC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1 QGBYZMSEIRCPSS-UHFFFAOYSA-N 0.000 description 4
• XXTKLKFTERLYLO-UHFFFAOYSA-N tert-butyl 2-[4-amino-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-phenylethynyl)phenoxy]acetate Chemical compound CC(C)(C)OC(=O)COC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=CC=C1 XXTKLKFTERLYLO-UHFFFAOYSA-N 0.000 description 4
• OASOWHFXYOHHTL-UHFFFAOYSA-N tert-butyl 3-(2-imidazol-1-ylpyridin-4-yl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=NC(N2C=NC=C2)=C1 OASOWHFXYOHHTL-UHFFFAOYSA-N 0.000 description 4
• NJGOKCQKYUXLSX-UHFFFAOYSA-N tert-butyl 3-(3-cyanophenyl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C#N)=C1 NJGOKCQKYUXLSX-UHFFFAOYSA-N 0.000 description 4
• FEPASYFSULWDNV-UHFFFAOYSA-N tert-butyl 3-(3-imidazol-1-ylphenyl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(N2C=NC=C2)=C1 FEPASYFSULWDNV-UHFFFAOYSA-N 0.000 description 4
• VTFOIKTXSHSBOV-UHFFFAOYSA-N tert-butyl 3-(5-cyanothiophen-2-yl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=C(C#N)S1 VTFOIKTXSHSBOV-UHFFFAOYSA-N 0.000 description 4
• BSPODPDIDGXFDC-UHFFFAOYSA-N tert-butyl 3-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-3-oxopropanoate Chemical compound O1N=C(C)C=C1C1=CC=CC(C(=O)CC(=O)OC(C)(C)C)=C1 BSPODPDIDGXFDC-UHFFFAOYSA-N 0.000 description 4
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• OKAJZINGJHIPBF-UHFFFAOYSA-N tert-butyl n-[2-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-5-methoxy-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1=C(C#CC=2C=CC=CC=2)C(OC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 OKAJZINGJHIPBF-UHFFFAOYSA-N 0.000 description 4
• KPVIYNHMYGAWKH-UHFFFAOYSA-N tert-butyl n-[2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-(oxan-2-yloxymethyl)-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C(NC(=O)CC(=O)C=2C=C(C=CC=2)N2C=NC=C2)C(NC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 KPVIYNHMYGAWKH-UHFFFAOYSA-N 0.000 description 4
• VODIQALLXVZOCX-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2,5-difluorophenyl)-5-[(2-methylpropan-2-yl)oxy]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(OC(C)(C)C)=C1C1=CC(F)=CC=C1F VODIQALLXVZOCX-UHFFFAOYSA-N 0.000 description 4
• DMXMHIAQOPTQSV-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2-fluorophenyl)-5-(2-methoxyethoxy)phenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=CC=C1F DMXMHIAQOPTQSV-UHFFFAOYSA-N 0.000 description 4
• YRIZVVRDNOYBPF-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2-fluorophenyl)-5-(oxan-2-yloxymethyl)phenyl]carbamate Chemical compound C=1C=CC=C(F)C=1C=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 YRIZVVRDNOYBPF-UHFFFAOYSA-N 0.000 description 4
• QMKMTSBNWHYAON-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(2-fluorophenyl)-5-[(4-methoxyphenyl)methoxy]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1COC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=CC=C1F QMKMTSBNWHYAON-UHFFFAOYSA-N 0.000 description 4
• PDQAAHAJLMSVEV-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluoro-2-methylphenyl)-5-methoxyphenyl]carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1C PDQAAHAJLMSVEV-UHFFFAOYSA-N 0.000 description 4
• AJSSFJHWSDLQIY-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-(2-methoxyethoxy)phenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1 AJSSFJHWSDLQIY-UHFFFAOYSA-N 0.000 description 4
• PPAKDRVPHNVIDV-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-(2-oxo-1,3-oxazolidin-3-yl)phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1N1CCOC1=O PPAKDRVPHNVIDV-UHFFFAOYSA-N 0.000 description 4
• GUSFWQGJUVPZAM-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-(oxan-2-yloxymethyl)phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 GUSFWQGJUVPZAM-UHFFFAOYSA-N 0.000 description 4
• CMYHVFPXSHLTAQ-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-[2-[(2-methylpropan-2-yl)oxy]ethoxy]phenyl]carbamate Chemical compound CC(C)(C)OCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1 CMYHVFPXSHLTAQ-UHFFFAOYSA-N 0.000 description 4
• SUXKZCKJWUGZON-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-[4-[2-(oxan-2-yloxy)ethoxy]piperidin-1-yl]phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1N(CC1)CCC1OCCOC1CCCCO1 SUXKZCKJWUGZON-UHFFFAOYSA-N 0.000 description 4
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• SKEUSPNYZCKXLG-UHFFFAOYSA-N tert-butyl n-[2-amino-4-(4-fluorophenyl)-5-methylphenyl]carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1 SKEUSPNYZCKXLG-UHFFFAOYSA-N 0.000 description 4
• UXBIFDXWPSKRPP-UHFFFAOYSA-N tert-butyl n-[2-amino-4-[2-(4-fluorophenyl)ethynyl]-5-[2-[(2-methylpropan-2-yl)oxy]ethoxy]phenyl]carbamate Chemical compound CC(C)(C)OCCOC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=C(F)C=C1 UXBIFDXWPSKRPP-UHFFFAOYSA-N 0.000 description 4
• ATLRWSZVYYZKBA-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-4-(4-fluorophenyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(N2CC3OC(C)(C)OC3C2)=C1C1=CC=C(F)C=C1 ATLRWSZVYYZKBA-UHFFFAOYSA-N 0.000 description 4
• RKTMIRQEMMSNCD-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(4-methylpiperazin-1-yl)-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=CC=C1 RKTMIRQEMMSNCD-UHFFFAOYSA-N 0.000 description 4
• NRFXUEQJKRANAB-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(cyanomethoxy)-4-(4-fluorophenyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(OCC#N)=C1C1=CC=C(F)C=C1 NRFXUEQJKRANAB-UHFFFAOYSA-N 0.000 description 4
• ILGIMVQKAJRPSN-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(ethoxymethyl)-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CCOCC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=CC=C1 ILGIMVQKAJRPSN-UHFFFAOYSA-N 0.000 description 4
• LNVFWYFPSAUUTJ-UHFFFAOYSA-N tert-butyl n-[2-amino-5-(oxan-2-yloxymethyl)-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 LNVFWYFPSAUUTJ-UHFFFAOYSA-N 0.000 description 4
• IJSWWROTDZSGMC-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1OCC1COC(C)(C)O1 IJSWWROTDZSGMC-UHFFFAOYSA-N 0.000 description 4
• KGIDKLOULPJJLI-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[(dimethylamino)methyl]-4-(4-fluorophenyl)phenyl]carbamate Chemical compound CN(C)CC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C1=CC=C(F)C=C1 KGIDKLOULPJJLI-UHFFFAOYSA-N 0.000 description 4
• NWJSISJEHXIXLL-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[2-(dimethylamino)ethylsulfanyl]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CN(C)CCSC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=CC=C1 NWJSISJEHXIXLL-UHFFFAOYSA-N 0.000 description 4
• ODYPYGUWQIUXHQ-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[2-(oxan-2-yloxy)ethoxy]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1OCCOC1CCCCO1 ODYPYGUWQIUXHQ-UHFFFAOYSA-N 0.000 description 4
• IUQRFBVWYMUBIH-UHFFFAOYSA-N tert-butyl n-[2-amino-5-chloro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(Cl)=C1C#CC1=CC=CC=C1 IUQRFBVWYMUBIH-UHFFFAOYSA-N 0.000 description 4
• BWTGZKRUJNMZQG-UHFFFAOYSA-N tert-butyl n-[2-amino-5-chloro-4-(4-fluorophenyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OC(C)(C)C)=CC(Cl)=C1C1=CC=C(F)C=C1 BWTGZKRUJNMZQG-UHFFFAOYSA-N 0.000 description 4
• BNTRSSCKMCAICO-UHFFFAOYSA-N tert-butyl n-[2-amino-5-methyl-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(N)C=C1C#CC1=CC=CC=C1 BNTRSSCKMCAICO-UHFFFAOYSA-N 0.000 description 4
• RLWLEFJFBNDVLV-UHFFFAOYSA-N tert-butyl n-[2-amino-5-morpholin-4-yl-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C(N)C(NC(=O)OC(C)(C)C)=CC=1N1CCOCC1 RLWLEFJFBNDVLV-UHFFFAOYSA-N 0.000 description 4
• UHNYIRKZORAMQO-UHFFFAOYSA-N tert-butyl n-[2-nitro-5-[2-(oxan-2-yloxy)ethoxy]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1OCCOC1CCCCO1 UHNYIRKZORAMQO-UHFFFAOYSA-N 0.000 description 4
• VYRGIQWROXVXAX-UHFFFAOYSA-N tert-butyl n-[4-(2,5-difluorophenyl)-5-[(2-methylpropan-2-yl)oxy]-2-nitrophenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(OC(C)(C)C)=C1C1=CC(F)=CC=C1F VYRGIQWROXVXAX-UHFFFAOYSA-N 0.000 description 4
• QXJITOYINHAQNV-UHFFFAOYSA-N tert-butyl n-[4-(2,5-difluorophenyl)-5-methoxy-2-nitrophenyl]carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC(F)=CC=C1F QXJITOYINHAQNV-UHFFFAOYSA-N 0.000 description 4
• ZZEDMZIIUFCQTL-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-5-(2-methoxyethoxy)-2-nitrophenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC=CC=C1F ZZEDMZIIUFCQTL-UHFFFAOYSA-N 0.000 description 4
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• GNITZRALWNJULW-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-5-methoxy-2-[[3-oxo-3-[3-(1,2,4-triazol-4-yl)phenyl]propanoyl]amino]phenyl]carbamate Chemical compound C1=C(C=2C(=CC=CC=2)F)C(OC)=CC(NC(=O)OC(C)(C)C)=C1NC(=O)CC(=O)C(C=1)=CC=CC=1N1C=NN=C1 GNITZRALWNJULW-UHFFFAOYSA-N 0.000 description 4
• HMQYDRBAGXYQKR-UHFFFAOYSA-N tert-butyl n-[4-(2-fluorophenyl)-5-methoxy-2-nitrophenyl]carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC=CC=C1F HMQYDRBAGXYQKR-UHFFFAOYSA-N 0.000 description 4
• JWKZCAFVRIPLOY-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-(2-oxo-1,3-oxazolidin-3-yl)phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(NC(=O)CC(=O)C=2C=C(C=CC=2)N2C=NC=C2)C(NC(=O)OC(C)(C)C)=CC=1N1CCOC1=O JWKZCAFVRIPLOY-UHFFFAOYSA-N 0.000 description 4
• PQNLYLHLZBKSFN-NDPHRHSWSA-N tert-butyl n-[4-(4-fluorophenyl)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-[(3r)-3-(oxan-2-yloxy)pyrrolidin-1-yl]phenyl]carbamate Chemical compound O([C@@H]1CCN(C1)C=1C=C(C(=CC=1C=1C=CC(F)=CC=1)NC(=O)CC(=O)C=1C=C(C=CC=1)N1C=NC=C1)NC(=O)OC(C)(C)C)C1CCCCO1 PQNLYLHLZBKSFN-NDPHRHSWSA-N 0.000 description 4
• IOMUFTDYKKYJOW-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-[4-(oxan-2-yloxy)piperidin-1-yl]phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(NC(=O)CC(=O)C=2C=C(C=CC=2)N2C=NC=C2)C(NC(=O)OC(C)(C)C)=CC=1N(CC1)CCC1OC1CCCCO1 IOMUFTDYKKYJOW-UHFFFAOYSA-N 0.000 description 4
• XGDLDXYKJPHFFI-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-[4-[2-(oxan-2-yloxy)ethoxy]piperidin-1-yl]phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C(NC(=O)CC(=O)C=2C=C(C=CC=2)N2C=NC=C2)C(NC(=O)OC(C)(C)C)=CC=1N(CC1)CCC1OCCOC1CCCCO1 XGDLDXYKJPHFFI-UHFFFAOYSA-N 0.000 description 4
• IZPYIDIRZLCWGQ-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-nitro-5-(2-oxo-1,3-oxazolidin-3-yl)phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1N1CCOC1=O IZPYIDIRZLCWGQ-UHFFFAOYSA-N 0.000 description 4
• RPUOVNZKMHYBCW-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-nitro-5-(oxan-2-yloxymethyl)phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1COC1CCCCO1 RPUOVNZKMHYBCW-UHFFFAOYSA-N 0.000 description 4
• TXGWVJWOBBBTQM-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-2-nitro-5-[4-[2-(oxan-2-yloxy)ethoxy]piperidin-1-yl]phenyl]carbamate Chemical compound C=1C=C(F)C=CC=1C=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1N(CC1)CCC1OCCOC1CCCCO1 TXGWVJWOBBBTQM-UHFFFAOYSA-N 0.000 description 4
• YYPIOMYGKGXAEO-UHFFFAOYSA-N tert-butyl n-[4-(4-fluorophenyl)-5-(2-methoxyethoxy)-2-nitrophenyl]carbamate Chemical compound COCCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC=C(F)C=C1 YYPIOMYGKGXAEO-UHFFFAOYSA-N 0.000 description 4
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• JCCAXMAHEKLSMN-UHFFFAOYSA-N tert-butyl n-[4-[2-(4-fluorophenyl)ethynyl]-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-5-[methyl-[2-(oxan-2-yloxy)ethyl]amino]phenyl]carbamate Chemical compound C=1C(NC(=O)OC(C)(C)C)=C(NC(=O)CC(=O)C=2C=C(C=CC=2)N2C=NC=C2)C=C(C#CC=2C=CC(F)=CC=2)C=1N(C)CCOC1CCCCO1 JCCAXMAHEKLSMN-UHFFFAOYSA-N 0.000 description 4
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• RVDLHXADZXWTLR-UHFFFAOYSA-N tert-butyl n-[4-iodo-2-nitro-5-[2-(oxan-2-yloxy)ethoxy]phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(OCCOC2OCCCC2)=C1I RVDLHXADZXWTLR-UHFFFAOYSA-N 0.000 description 4
• UBZUZHIWSFLKQM-UHFFFAOYSA-N tert-butyl n-[4-iodo-5-(4-methoxypiperidin-1-yl)-2-nitrophenyl]carbamate Chemical compound C1CC(OC)CCN1C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1I UBZUZHIWSFLKQM-UHFFFAOYSA-N 0.000 description 4
• WHRQDPYXUJLHIO-UHFFFAOYSA-N tert-butyl n-[4-iodo-5-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]-2-nitrophenyl]carbamate Chemical compound COCCOCCOCCOCCOC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1I WHRQDPYXUJLHIO-UHFFFAOYSA-N 0.000 description 4
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• QGMLHMVRNCFMJC-UHFFFAOYSA-N tert-butyl n-[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1N(CC1)CCC21OCCO2 QGMLHMVRNCFMJC-UHFFFAOYSA-N 0.000 description 4
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• KJAYEARMUQNVTK-UHFFFAOYSA-N tert-butyl n-[5-(2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-4-(4-fluorophenyl)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(N2CC3OC(C)(C)OC3C2)=C(C=2C=CC(F)=CC=2)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1N1C=CN=C1 KJAYEARMUQNVTK-UHFFFAOYSA-N 0.000 description 4
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• MBVCRROMYYYMGZ-UHFFFAOYSA-N tert-butyl n-[5-(4-hydroxypiperidin-1-yl)-4-iodo-2-nitrophenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(N2CCC(O)CC2)=C1I MBVCRROMYYYMGZ-UHFFFAOYSA-N 0.000 description 4
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• NZEYJWOHEOTVJS-UHFFFAOYSA-N tert-butyl n-[5-(4-methylpiperazin-1-yl)-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C#CC1=CC=CC=C1 NZEYJWOHEOTVJS-UHFFFAOYSA-N 0.000 description 4
• JSCUCPPCFXZWEE-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethoxy)-2-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC#N)=C(C#CC=2C=CC=CC=2)C=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 JSCUCPPCFXZWEE-UHFFFAOYSA-N 0.000 description 4
• RKRGBADLKBXODM-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethoxy)-2-[[3-(3-imidazol-1-ylphenyl)-3-oxopropanoyl]amino]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(OCC#N)=C(C#CC=2C=CC=CC=2)C=C1NC(=O)CC(=O)C(C=1)=CC=CC=1N1C=CN=C1 RKRGBADLKBXODM-UHFFFAOYSA-N 0.000 description 4
• JMKSUQDTKXBWCP-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethoxy)-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(OCC#N)=C1C#CC1=CC=CC=C1 JMKSUQDTKXBWCP-UHFFFAOYSA-N 0.000 description 4
• VMMJYRHZUDKFNK-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethoxy)-4-(4-fluorophenyl)-2-nitrophenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(OCC#N)=C1C1=CC=C(F)C=C1 VMMJYRHZUDKFNK-UHFFFAOYSA-N 0.000 description 4
• WSPWSBCKDVPTKD-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethyl)-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(CC#N)=C1C#CC1=CC=CC=C1 WSPWSBCKDVPTKD-UHFFFAOYSA-N 0.000 description 4
• IYWYBJNGEGWVPH-SECBINFHSA-N tert-butyl n-[5-[(3r)-3-hydroxypyrrolidin-1-yl]-4-iodo-2-nitrophenyl]carbamate Chemical compound C1=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC(N2C[C@H](O)CC2)=C1I IYWYBJNGEGWVPH-SECBINFHSA-N 0.000 description 4
• IJZOKEVCYZSSFM-UHFFFAOYSA-N tert-butyl n-[5-[(dimethylamino)methyl]-4-(4-fluorophenyl)-2-nitrophenyl]carbamate Chemical compound CN(C)CC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C1=CC=C(F)C=C1 IJZOKEVCYZSSFM-UHFFFAOYSA-N 0.000 description 4
• DHLSXIHLKCPTQK-UHFFFAOYSA-N tert-butyl n-[5-[2-(dimethylamino)ethylsulfanyl]-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CN(C)CCSC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C#CC1=CC=CC=C1 DHLSXIHLKCPTQK-UHFFFAOYSA-N 0.000 description 4
• JXXRJXOUAAEXPD-UHFFFAOYSA-N tert-butyl n-[5-[2-(dimethylamino)ethylsulfanyl]-4-iodo-2-nitrophenyl]carbamate Chemical compound CN(C)CCSC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1I JXXRJXOUAAEXPD-UHFFFAOYSA-N 0.000 description 4
• DSHHYMTZHRJVHY-UHFFFAOYSA-N tert-butyl n-[5-[2-hydroxyethyl(methyl)amino]-4-iodo-2-nitrophenyl]carbamate Chemical compound OCCN(C)C1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1I DSHHYMTZHRJVHY-UHFFFAOYSA-N 0.000 description 4
• WUJPSFRBMCGSPL-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-4-phenylphenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(C=2C=CC=CC=2)C=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 WUJPSFRBMCGSPL-UHFFFAOYSA-N 0.000 description 4
• YPMXBAYVVVJLCF-UHFFFAOYSA-N tert-butyl n-[5-methyl-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=C1C#CC1=CC=CC=C1 YPMXBAYVVVJLCF-UHFFFAOYSA-N 0.000 description 4
• FRANACVKTYIGSU-UHFFFAOYSA-N tert-butyl n-[5-morpholin-4-yl-2-nitro-4-(2-phenylethynyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1C#CC=1C=C([N+]([O-])=O)C(NC(=O)OC(C)(C)C)=CC=1N1CCOCC1 FRANACVKTYIGSU-UHFFFAOYSA-N 0.000 description 4
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
• LLPVQGDNKWRPQT-UHFFFAOYSA-N (5-chloro-4-iodo-2-nitrophenyl)carbamic acid Chemical compound OC(=O)NC1=CC(Cl)=C(I)C=C1[N+]([O-])=O LLPVQGDNKWRPQT-UHFFFAOYSA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• RBKKYIAGHDZILB-UHFFFAOYSA-N 2,2-dimethyl-6-[3-(2-methylimidazol-1-yl)phenyl]-1,3-dioxin-4-one Chemical compound CC1=NC=CN1C1=CC=CC(C=2OC(C)(C)OC(=O)C=2)=C1 RBKKYIAGHDZILB-UHFFFAOYSA-N 0.000 description 3
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 3
• DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
• GCPHKTQMABHWPY-UHFFFAOYSA-N 3-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C=1SC=CC=1Cl GCPHKTQMABHWPY-UHFFFAOYSA-N 0.000 description 3
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• SRSYAQSQBYDHIR-UHFFFAOYSA-N tert-butyl n-[5-(cyanomethyl)-2-[[3-(3-cyanophenyl)-3-oxopropanoyl]amino]-4-(2-phenylethynyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(CC#N)=C(C#CC=2C=CC=CC=2)C=C1NC(=O)CC(=O)C1=CC=CC(C#N)=C1 SRSYAQSQBYDHIR-UHFFFAOYSA-N 0.000 description 3
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