NO315273B1 - Trisykliske vasopressinagonister, farmasöytiske sammensetninger omfattendedisse, deres anvendelse samt en fremgangsmåte for fremstillingderav - Google Patents

Info

Publication number

NO315273B1

NO315273B1 NO20000242A NO20000242A NO315273B1 NO 315273 B1 NO315273 B1 NO 315273B1 NO 20000242 A NO20000242 A NO 20000242A NO 20000242 A NO20000242 A NO 20000242A NO 315273 B1 NO315273 B1 NO 315273B1

Authority

NO

Norway

Prior art keywords

benzodiazepine

pyrrolo

methanone

phenyl

pyrazol

Prior art date

1997-07-30

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• 238000000034 method Methods 0.000 title claims description 63
• 238000002360 preparation method Methods 0.000 title claims description 20
• 229940083335 Vasopressin agonist Drugs 0.000 title claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
• 230000008569 process Effects 0.000 title claims description 4
• 150000001875 compounds Chemical class 0.000 claims description 279
• 125000004432 carbon atom Chemical group C* 0.000 claims description 74
• -1 [4-(4-Methyl-pyrazol-1-yl)-2-trifluoromethyl-phenyl]-(5H,1H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone Chemical compound 0.000 claims description 73
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• 239000001257 hydrogen Substances 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 46
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 32
• 150000002431 hydrogen Chemical class 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 238000004519 manufacturing process Methods 0.000 claims description 18
• 230000000694 effects Effects 0.000 claims description 17
• FBLUCKXWFZKVCT-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound C1C2=CC=CN2CC2=CC=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=NN1 FBLUCKXWFZKVCT-UHFFFAOYSA-N 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 8
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
• 229910052721 tungsten Inorganic materials 0.000 claims description 8
• 229910052727 yttrium Inorganic materials 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 208000008967 Enuresis Diseases 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 201000010064 diabetes insipidus Diseases 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 230000027939 micturition Effects 0.000 claims description 7
• 208000005346 nocturnal enuresis Diseases 0.000 claims description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 6
• 229910052796 boron Inorganic materials 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 206010046543 Urinary incontinence Diseases 0.000 claims description 5
• 230000000740 bleeding effect Effects 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 206010029446 nocturia Diseases 0.000 claims description 5
• UAKRIFYMKVWWSB-UHFFFAOYSA-N 1-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 UAKRIFYMKVWWSB-UHFFFAOYSA-N 0.000 claims description 4
• IAUVQLCYHAXTKP-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[2-methoxy-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(OC)=CC=1N1C=CC(C)=N1 IAUVQLCYHAXTKP-UHFFFAOYSA-N 0.000 claims description 4
• UQMZWIPRZOTGON-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbaldehyde Chemical compound O=CN1CC2=CC=CN2CC2=CC=CC=C12 UQMZWIPRZOTGON-UHFFFAOYSA-N 0.000 claims description 4
• 206010053567 Coagulopathies Diseases 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 208000031169 hemorrhagic disease Diseases 0.000 claims description 4
• 150000002429 hydrazines Chemical class 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 208000015294 blood coagulation disease Diseases 0.000 claims description 3
• 230000009852 coagulant defect Effects 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• URZRRURVKJYAAW-UHFFFAOYSA-N (2,4-difluorophenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 URZRRURVKJYAAW-UHFFFAOYSA-N 0.000 claims description 2
• PFIHUWCMYUUTJM-UHFFFAOYSA-N (2-chloro-4-pyrrol-1-ylphenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1N1C=CC=C1 PFIHUWCMYUUTJM-UHFFFAOYSA-N 0.000 claims description 2
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
• FLICMWMJGBRJBU-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzamide Chemical compound ClC1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 FLICMWMJGBRJBU-UHFFFAOYSA-N 0.000 claims description 2
• KUIQZKCWIAZFLF-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 KUIQZKCWIAZFLF-UHFFFAOYSA-N 0.000 claims description 2
• DSDRQBPGBZCVCN-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 DSDRQBPGBZCVCN-UHFFFAOYSA-N 0.000 claims description 2
• BPJFXRBPXNGTAI-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-(4-pyrazol-1-ylphenyl)methanone Chemical compound C1C2=CC=CN2CC2=CC=CC=C2N1C(=O)C(C=C1)=CC=C1N1C=CC=N1 BPJFXRBPXNGTAI-UHFFFAOYSA-N 0.000 claims description 2
• MHPFBCSULPHXGZ-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-methylpyrazol-4-yl)phenyl]methanone Chemical compound C1=NN(C)C=C1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 MHPFBCSULPHXGZ-UHFFFAOYSA-N 0.000 claims description 2
• APJKVNDKNAGLPV-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-propylpyrazol-3-yl)phenyl]methanone Chemical compound CCCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 APJKVNDKNAGLPV-UHFFFAOYSA-N 0.000 claims description 2
• FMOQJUMNVLFHBN-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 FMOQJUMNVLFHBN-UHFFFAOYSA-N 0.000 claims description 2
• ZMDLMIADSBRABU-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=CN1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 ZMDLMIADSBRABU-UHFFFAOYSA-N 0.000 claims description 2
• AVPKUAHXGQKTRJ-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(4-methylpyrazol-1-yl)phenyl]methanone Chemical compound C1=C(C)C=NN1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 AVPKUAHXGQKTRJ-UHFFFAOYSA-N 0.000 claims description 2
• QOVQKXLSPAUMBR-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(5-methyl-1h-pyrazol-3-yl)phenyl]methanone Chemical compound N1C(C)=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 QOVQKXLSPAUMBR-UHFFFAOYSA-N 0.000 claims description 2
• FLXNQADSXVDDED-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(2-methylbenzoyl)pyrazol-3-yl]phenyl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 FLXNQADSXVDDED-UHFFFAOYSA-N 0.000 claims description 2
• IRJHPKKQWIRRDH-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(5-fluoro-2-methylbenzoyl)pyrazol-3-yl]phenyl]methanone Chemical compound CC1=CC=C(F)C=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 IRJHPKKQWIRRDH-UHFFFAOYSA-N 0.000 claims description 2
• ZOPZYYBHDGGLSD-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[6-(1-methylpyrazol-4-yl)pyridin-3-yl]methanone Chemical compound C1=NN(C)C=C1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=N1 ZOPZYYBHDGGLSD-UHFFFAOYSA-N 0.000 claims description 2
• KPZHSXCQKPNVKU-UHFFFAOYSA-N [2-chloro-4-(1-methylpyrazol-4-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C1=NN(C)C=C1C(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 KPZHSXCQKPNVKU-UHFFFAOYSA-N 0.000 claims description 2
• SRPPGGPQIGOELK-UHFFFAOYSA-N [2-chloro-4-(2h-tetrazol-5-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1C=1N=NNN=1 SRPPGGPQIGOELK-UHFFFAOYSA-N 0.000 claims description 2
• RTRBDFZJXIBNFC-UHFFFAOYSA-N [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-(9-methyl-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound N1=C(C)C=CN1C(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C(C)=CC=C2C1 RTRBDFZJXIBNFC-UHFFFAOYSA-N 0.000 claims description 2
• JHPDHIYVIDFZBV-UHFFFAOYSA-N [2-chloro-6-(3-methylpyrazol-1-yl)pyridin-3-yl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound N1=C(C)C=CN1C(N=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 JHPDHIYVIDFZBV-UHFFFAOYSA-N 0.000 claims description 2
• VTTSWHYXLTVYDF-UHFFFAOYSA-N [2-chloro-6-(4-methylpyrazol-1-yl)pyridin-3-yl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C1=C(C)C=NN1C(N=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 VTTSWHYXLTVYDF-UHFFFAOYSA-N 0.000 claims description 2
• ABIVFJRWLYBHFL-UHFFFAOYSA-N [4-(3-cyclopropylpyrazol-1-yl)-2-(trifluoromethyl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(C(F)(F)F)=CC=1N(N=1)C=CC=1C1CC1 ABIVFJRWLYBHFL-UHFFFAOYSA-N 0.000 claims description 2
• QOKBTDWACCQPEV-UHFFFAOYSA-N [9-[(dimethylamino)methyl]-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl]-[2-methoxy-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C(CN(C)C)=CC=C3C2)C(OC)=CC=1N1C=CC(C)=N1 QOKBTDWACCQPEV-UHFFFAOYSA-N 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
• 238000012546 transfer Methods 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 4
• WSWLBSBMRCHUEH-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methylpyrazol-1-yl)-2-(trifluoromethyl)phenyl]methanone Chemical compound N1=C(C)C=CN1C(C=C1C(F)(F)F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 WSWLBSBMRCHUEH-UHFFFAOYSA-N 0.000 claims 2
• FBENLRZSVRQZHY-UHFFFAOYSA-N (2-chloro-4-pyrazol-1-ylphenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1N1C=CC=N1 FBENLRZSVRQZHY-UHFFFAOYSA-N 0.000 claims 1
• QVSKPOGUURMZEN-UHFFFAOYSA-N 1-[2-chloro-4-(2-methyl-1,2,4-triazol-3-yl)phenyl]-2-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)ethane-1,2-dione Chemical compound CN1N=CN=C1C(C=C1Cl)=CC=C1C(=O)C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 QVSKPOGUURMZEN-UHFFFAOYSA-N 0.000 claims 1
• JDQPHLSKTFNWKS-UHFFFAOYSA-N 1-[3-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]pyrazol-1-yl]butan-1-one Chemical compound CCCC(=O)N1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 JDQPHLSKTFNWKS-UHFFFAOYSA-N 0.000 claims 1
• XPSWCLNIVATKRD-UHFFFAOYSA-N 1-[3-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]pyrazol-1-yl]propan-1-one Chemical compound CCC(=O)N1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 XPSWCLNIVATKRD-UHFFFAOYSA-N 0.000 claims 1
• GATZRWSXCKUPBW-UHFFFAOYSA-N 1-[3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 GATZRWSXCKUPBW-UHFFFAOYSA-N 0.000 claims 1
• ZACOHTBOHFCQIE-UHFFFAOYSA-N 1-[4-(4,10-dihydropyrazolo[5,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2N=CC=C2C1 ZACOHTBOHFCQIE-UHFFFAOYSA-N 0.000 claims 1
• HZKMKSBSEYMPCW-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[2-fluoro-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=CN1C(C=C1F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 HZKMKSBSEYMPCW-UHFFFAOYSA-N 0.000 claims 1
• ULGQCNKQHORZJF-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-ethylpyrazol-3-yl)phenyl]methanone Chemical compound CCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 ULGQCNKQHORZJF-UHFFFAOYSA-N 0.000 claims 1
• VKBOUDPLTDGHDT-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3,5-dimethylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=C(C)N1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 VKBOUDPLTDGHDT-UHFFFAOYSA-N 0.000 claims 1
• QBUWLGWIBRDKEN-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(methoxymethyl)pyrazol-3-yl]phenyl]methanone Chemical compound COCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 QBUWLGWIBRDKEN-UHFFFAOYSA-N 0.000 claims 1
• CNTDFFHQKBTDDT-UHFFFAOYSA-N [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-[9-[(dimethylamino)methyl]-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl]methanone Chemical compound C12=CC=CC=C2CN2C(CN(C)C)=CC=C2CN1C(=O)C(C(=C1)Cl)=CC=C1N1C=CC(C)=N1 CNTDFFHQKBTDDT-UHFFFAOYSA-N 0.000 claims 1
• HXBSWLVZOHGNHL-UHFFFAOYSA-N [4-[1-(2,4-dichlorobenzoyl)pyrazol-3-yl]phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 HXBSWLVZOHGNHL-UHFFFAOYSA-N 0.000 claims 1
• PSWYTXVNFQEIDD-UHFFFAOYSA-N [4-[1-(2-chloro-4-fluorobenzoyl)pyrazol-3-yl]phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound ClC1=CC(F)=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 PSWYTXVNFQEIDD-UHFFFAOYSA-N 0.000 claims 1
• 230000002152 alkylating effect Effects 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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