MX2012000609A - Compuestos heterociclicos como inhibidores de autotaxina. - Google Patents

Info

Publication number

MX2012000609A

MX2012000609A MX2012000609A MX2012000609A MX2012000609A MX 2012000609 A MX2012000609 A MX 2012000609A MX 2012000609 A MX2012000609 A MX 2012000609A MX 2012000609 A MX2012000609 A MX 2012000609A MX 2012000609 A MX2012000609 A MX 2012000609A

Authority

MX

Mexico

Prior art keywords

phenyl

cyclohepten

dibenzo

triaza

tetrahydro

Prior art date

2009-07-16

Links

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• 239000003112 inhibitor Substances 0.000 title abstract description 39
• 102100021977 Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Human genes 0.000 title abstract description 31
• 108050004000 Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Proteins 0.000 title abstract description 31
• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 157
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 34
• 238000011282 treatment Methods 0.000 claims abstract description 26
• -1 COOA Chemical group 0.000 claims description 473
• KFIFDBHBZHIMNU-UHFFFAOYSA-N 1,6-dihydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C1NC2=CC=CC=C2C(=O)N2CC=NC=C12 KFIFDBHBZHIMNU-UHFFFAOYSA-N 0.000 claims description 109
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 100
• 239000000203 mixture Substances 0.000 claims description 66
• 150000003839 salts Chemical class 0.000 claims description 55
• 239000002253 acid Substances 0.000 claims description 36
• BWQSXFPTCSUKBV-UHFFFAOYSA-N 1,2,3,4,4a,6-hexahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C1NC2=CC=CC=C2C(=O)N2CCNCC12 BWQSXFPTCSUKBV-UHFFFAOYSA-N 0.000 claims description 35
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• MDJKBXHVVRGASB-UHFFFAOYSA-N 1,2,3,4,4a,6,10,10a-octahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C1NC2=CC=CCC2C(=O)N2CCNCC12 MDJKBXHVVRGASB-UHFFFAOYSA-N 0.000 claims description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 12
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
• FNFJZXAWCAEGNI-UHFFFAOYSA-N cycloheptene-1-carboxylic acid Chemical compound OC(=O)C1=CCCCCC1 FNFJZXAWCAEGNI-UHFFFAOYSA-N 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000000565 sulfonamide group Chemical group 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• GTGVFHOLBRCBEC-HSZRJFAPSA-N (4ar)-3-benzylsulfonyl-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)S(=O)(=O)CC=2C=CC=CC=2)C2=O)C2=C1 GTGVFHOLBRCBEC-HSZRJFAPSA-N 0.000 claims description 5
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• LODVRKXUAKFIRB-BPGUCPLFSA-N 9-(4-chlorophenyl)-3-[(2s)-2-hydroxy-3,3-dimethylbutanoyl]-1,2,4,4a,6,11-hexahydropyrazino[2,1-c][1,4]benzodiazepin-5-one Chemical compound C=1C=C2NC(=O)C3CN(C(=O)[C@@H](O)C(C)(C)C)CCN3CC2=CC=1C1=CC=C(Cl)C=C1 LODVRKXUAKFIRB-BPGUCPLFSA-N 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 210000002784 stomach Anatomy 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• BPYXJGYZGGFRJA-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(CCC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F BPYXJGYZGGFRJA-UHFFFAOYSA-N 0.000 claims description 4
• MBAHIMDZHYQSQU-FOIFJWKZSA-N 9-(4-chlorophenyl)-6-ethyl-3-[(2s)-2-hydroxy-3,3-dimethylbutanoyl]-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=C2C(=O)N3CCN(C(=O)[C@@H](O)C(C)(C)C)CC3C(=O)N(CC)C2=CC=C1C1=CC=C(Cl)C=C1 MBAHIMDZHYQSQU-FOIFJWKZSA-N 0.000 claims description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
• 206010033128 Ovarian cancer Diseases 0.000 claims description 4
• 210000004369 blood Anatomy 0.000 claims description 4
• 239000008280 blood Substances 0.000 claims description 4
• 201000008275 breast carcinoma Diseases 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• GVSSIHAGOZKTRS-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F GVSSIHAGOZKTRS-UHFFFAOYSA-N 0.000 claims description 3
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 3
• 210000000867 larynx Anatomy 0.000 claims description 3
• 210000004072 lung Anatomy 0.000 claims description 3
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 3
• KEYURXCDTWLHJE-ZWKOTPCHSA-N (4aR)-9-(1,3-benzodioxol-5-yl)-3-[(4R)-1,3-thiazolidine-4-carbonyl]-2,4,4a,6-tetrahydro-1H-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C([C@H]1N(C(C2=CC(=CC=C2NC1=O)C=1C=C2OCOC2=CC=1)=O)CC1)N1C(=O)[C@@H]1CSCN1 KEYURXCDTWLHJE-ZWKOTPCHSA-N 0.000 claims description 2
• YEZZXICSGSCPNA-OAQYLSRUSA-N (4aR)-9-(4-chlorophenyl)-3-(piperidine-4-carbonyl)-2,4,4a,6-tetrahydro-1H-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)C2CCNCC2)C2=O)C2=C1 YEZZXICSGSCPNA-OAQYLSRUSA-N 0.000 claims description 2
• REKXSERPCPKNDR-VQTJNVASSA-N (4aR)-9-(4-methoxyphenyl)-3-[(4R)-1,3-thiazolidine-4-carbonyl]-2,4,4a,6-tetrahydro-1H-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(OC)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)[C@H]2NCSC2)C2=O)C2=C1 REKXSERPCPKNDR-VQTJNVASSA-N 0.000 claims description 2
• UWHYQQOXWMVTMW-RBUKOAKNSA-N (4aR)-9-phenyl-3-[(4R)-1,3-thiazolidine-4-carbonyl]-2,4,4a,6-tetrahydro-1H-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C([C@H]1N(C(C2=CC(=CC=C2NC1=O)C=1C=CC=CC=1)=O)CC1)N1C(=O)[C@@H]1CSCN1 UWHYQQOXWMVTMW-RBUKOAKNSA-N 0.000 claims description 2
• VTPDAKPVQPICLV-NRFANRHFSA-N (4aS)-3-(cyclopentanecarbonyl)-9-(2-fluorophenyl)-2,4,4a,6-tetrahydro-1H-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC=CC=C1C1=CC=C(NC(=O)[C@H]2N(CCN(C2)C(=O)C2CCCC2)C2=O)C2=C1 VTPDAKPVQPICLV-NRFANRHFSA-N 0.000 claims description 2
• OYYJSHSUNHNJCJ-OAQYLSRUSA-N (4ar)-3-(3,3-dimethylbutanoyl)-9-(4-methoxyphenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(OC)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)CC(C)(C)C)C2=O)C2=C1 OYYJSHSUNHNJCJ-OAQYLSRUSA-N 0.000 claims description 2
• JPNTVVVUKXUSGS-JOCHJYFZSA-N (4ar)-3-(cyclohexanecarbonyl)-9-(2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)C2CCCCC2)C2=O)C2=C1 JPNTVVVUKXUSGS-JOCHJYFZSA-N 0.000 claims description 2
• HGRMXTJFHGWLAA-JOCHJYFZSA-N (4ar)-3-(cyclohexanecarbonyl)-9-phenyl-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C([C@H]1N(C(C2=CC(=CC=C2NC1=O)C=1C=CC=CC=1)=O)CC1)N1C(=O)C1CCCCC1 HGRMXTJFHGWLAA-JOCHJYFZSA-N 0.000 claims description 2
• FHHYKTXDOWJKSS-RPWUZVMVSA-N (4ar)-3-[(2s)-2-hydroxy-2-phenylacetyl]-9-(4-methoxyphenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(OC)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)[C@@H](O)C=2C=CC=CC=2)C2=O)C2=C1 FHHYKTXDOWJKSS-RPWUZVMVSA-N 0.000 claims description 2
• NFIDINZFLQIJSH-JOCHJYFZSA-N (4ar)-3-benzoyl-9-[3-(trifluoromethyl)phenyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC(F)(F)C1=CC=CC(C=2C=C3C(=O)N4CCN(C[C@@H]4C(=O)NC3=CC=2)C(=O)C=2C=CC=CC=2)=C1 NFIDINZFLQIJSH-JOCHJYFZSA-N 0.000 claims description 2
• HKRQHZDDYLKGKA-LJQANCHMSA-N (4ar)-9-(2-fluorophenyl)-3-(thiophene-2-carbonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)C=2SC=CC=2)C2=O)C2=C1 HKRQHZDDYLKGKA-LJQANCHMSA-N 0.000 claims description 2
• VJCNOMOTHBMDGE-QGZVFWFLSA-N (4ar)-9-(2-fluorophenyl)-3-methylsulfonyl-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)S(=O)(=O)C)NC2=CC=C3C1=CC=CC=C1F VJCNOMOTHBMDGE-QGZVFWFLSA-N 0.000 claims description 2
• QUMCVEQKTSCPLE-JWQCQUIFSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-[(2s)-3,3-dimethyl-2-(piperidin-4-ylamino)butanoyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound N([C@@H](C(C)(C)C)C(=O)N1C[C@H]2N(C(C3=CC(=CC=C3NC2=O)C=2C(=CC(Cl)=CC=2)F)=O)CC1)C1CCNCC1 QUMCVEQKTSCPLE-JWQCQUIFSA-N 0.000 claims description 2
• SVZKRAVPADNWAL-QGZVFWFLSA-N (4ar)-9-(4-chlorophenyl)-3-(2-hydroxyacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CO)NC2=CC=C3C1=CC=C(Cl)C=C1 SVZKRAVPADNWAL-QGZVFWFLSA-N 0.000 claims description 2
• LSPZAWBLZHLDKQ-HSZRJFAPSA-N (4ar)-9-(4-chlorophenyl)-3-(2-phenoxyacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)COC=2C=CC=CC=2)C2=O)C2=C1 LSPZAWBLZHLDKQ-HSZRJFAPSA-N 0.000 claims description 2
• HCGZEPGXRZWRGQ-LJQANCHMSA-N (4ar)-9-(4-chlorophenyl)-3-(thiophene-2-carbonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)C=2SC=CC=2)C2=O)C2=C1 HCGZEPGXRZWRGQ-LJQANCHMSA-N 0.000 claims description 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
• RLCCBZNPNCTGJT-UHFFFAOYSA-N 9-(4-chlorophenyl)-3-(3,3-dimethylbutanoyl)-6-methyl-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=C2C(=O)N3CCN(C(=O)CC(C)(C)C)CC3C(=O)N(C)C2=CC=C1C1=CC=C(Cl)C=C1 RLCCBZNPNCTGJT-UHFFFAOYSA-N 0.000 claims description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
• 208000026310 Breast neoplasm Diseases 0.000 claims description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 206010024305 Leukaemia monocytic Diseases 0.000 claims description 2
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 239000004305 biphenyl Substances 0.000 claims description 2
• 235000010290 biphenyl Nutrition 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 210000003679 cervix uteri Anatomy 0.000 claims description 2
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 2
• 210000003238 esophagus Anatomy 0.000 claims description 2
• 210000003128 head Anatomy 0.000 claims description 2
• 210000000987 immune system Anatomy 0.000 claims description 2
• 210000000936 intestine Anatomy 0.000 claims description 2
• 210000003734 kidney Anatomy 0.000 claims description 2
• 210000004185 liver Anatomy 0.000 claims description 2
• 210000004324 lymphatic system Anatomy 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000006894 monocytic leukemia Diseases 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 210000003739 neck Anatomy 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• 210000002307 prostate Anatomy 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• 210000003932 urinary bladder Anatomy 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
• XCEZWRWABJBDAZ-RRPNLBNLSA-N (4aR)-9-(4-chloro-2-fluorophenyl)-6-(2-hydroxyethyl)-3-[(2S)-1-piperidin-4-ylpyrrolidine-2-carbonyl]-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C([C@H]1C(=O)N2CCN3C(=O)C4=CC(=CC=C4N(C([C@H]3C2)=O)CCO)C=2C(=CC(Cl)=CC=2)F)CCN1C1CCNCC1 XCEZWRWABJBDAZ-RRPNLBNLSA-N 0.000 claims 1
• UTPMJXCXUCHTSG-HXUWFJFHSA-N (4ar)-3-(3,3-dimethylbutanoyl)-9-(2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CC(C)(C)C)NC2=CC=C3C1=CC=CC=C1F UTPMJXCXUCHTSG-HXUWFJFHSA-N 0.000 claims 1
• GHEHLCJTQDEZJJ-HSZRJFAPSA-N (4ar)-3-(3-fluorobenzoyl)-9-(4-methoxyphenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(OC)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)C=2C=C(F)C=CC=2)C2=O)C2=C1 GHEHLCJTQDEZJJ-HSZRJFAPSA-N 0.000 claims 1
• RROHQXCLLZSODJ-WOJBJXKFSA-N (4ar)-3-[(2s)-2-amino-3,3-dimethylbutanoyl]-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)[C@@H](N)C(C)(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1F RROHQXCLLZSODJ-WOJBJXKFSA-N 0.000 claims 1
• LICFHJBFTVYNDR-FUHWJXTLSA-N (4ar)-3-[(2s)-2-amino-3-hydroxypropanoyl]-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)[C@H](CO)N)NC2=CC=C3C1=CC=C(Cl)C=C1F LICFHJBFTVYNDR-FUHWJXTLSA-N 0.000 claims 1
• GWKMCKDJWOGORY-CTNGQTDRSA-N (4ar)-3-[(2s)-2-hydroxy-2-phenylacetyl]-9-thiophen-2-yl-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)[C@@H](O)C=1C=CC=CC=1)NC2=CC=C3C1=CC=CS1 GWKMCKDJWOGORY-CTNGQTDRSA-N 0.000 claims 1
• TZDOSKNTPBATBT-GOSISDBHSA-N (4ar)-3-acetyl-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)C)NC2=CC=C3C1=CC=C(Cl)C=C1F TZDOSKNTPBATBT-GOSISDBHSA-N 0.000 claims 1
• UOKUAQTYNCBFHO-HXUWFJFHSA-N (4ar)-9-(1,3-benzodioxol-5-yl)-3-(pyridine-3-carbonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C([C@H]1N(C(C2=CC(=CC=C2NC1=O)C=1C=C2OCOC2=CC=1)=O)CC1)N1C(=O)C1=CC=CN=C1 UOKUAQTYNCBFHO-HXUWFJFHSA-N 0.000 claims 1
• QUOIBVQUHFEIAG-HXUWFJFHSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(2-methylpropylsulfonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)S(=O)(=O)CC(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1F QUOIBVQUHFEIAG-HXUWFJFHSA-N 0.000 claims 1
• GVSSIHAGOZKTRS-HXUWFJFHSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CC(C)(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1F GVSSIHAGOZKTRS-HXUWFJFHSA-N 0.000 claims 1
• YSDSITIHHFSLRG-AREMUKBSSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-6-(2-morpholin-4-ylethyl)-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=CC(=CC=C22)C=3C(=CC(Cl)=CC=3)F)=O)CCN(C1)C(=O)CC(C)(C)C)N2CCN1CCOCC1 YSDSITIHHFSLRG-AREMUKBSSA-N 0.000 claims 1
• SYOFLWJDIVVLRH-HHHXNRCGSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-6-(2-piperidin-4-ylethyl)-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=CC(=CC=C22)C=3C(=CC(Cl)=CC=3)F)=O)CCN(C1)C(=O)CC(C)(C)C)N2CCC1CCNCC1 SYOFLWJDIVVLRH-HHHXNRCGSA-N 0.000 claims 1
• QHMCWQQLKFYWHO-AREMUKBSSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-6-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1CN(C)CCN1C(=O)CN1C(=O)[C@H]2CN(C(=O)CC(C)(C)C)CCN2C(=O)C2=CC(C=3C(=CC(Cl)=CC=3)F)=CC=C21 QHMCWQQLKFYWHO-AREMUKBSSA-N 0.000 claims 1
• YCFRJBKRRKNWSS-HSZRJFAPSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-(cyclohexylmethylsulfonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)S(=O)(=O)CC2CCCCC2)C2=O)C2=C1 YCFRJBKRRKNWSS-HSZRJFAPSA-N 0.000 claims 1
• BOSQPIDUEIUDIU-IZZNHLLZSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-[(2s)-1-(1-methylpiperidin-4-yl)pyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1CN(C)CCC1N1[C@H](C(=O)N2C[C@H]3N(C(C4=CC(=CC=C4NC3=O)C=3C(=CC(Cl)=CC=3)F)=O)CC2)CCC1 BOSQPIDUEIUDIU-IZZNHLLZSA-N 0.000 claims 1
• BHTVGMLQZDXNBK-LOSJGSFVSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-[(2s)-1-(oxan-4-yl)pyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)[C@H]2N(CCC2)C2CCOCC2)C2=O)C2=C1 BHTVGMLQZDXNBK-LOSJGSFVSA-N 0.000 claims 1
• UKQDNEVSVLMMDF-IZZNHLLZSA-N (4ar)-9-(4-chloro-2-fluorophenyl)-3-[(2s)-1-cyclohexylpyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)[C@H]2N(CCC2)C2CCCCC2)C2=O)C2=C1 UKQDNEVSVLMMDF-IZZNHLLZSA-N 0.000 claims 1
• CICVWAHNXVIEQO-RBUKOAKNSA-N (4ar)-9-(4-chlorophenyl)-3-[(4r)-1,3-thiazolidine-4-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@@H]2N(CCN(C2)C(=O)[C@H]2NCSC2)C2=O)C2=C1 CICVWAHNXVIEQO-RBUKOAKNSA-N 0.000 claims 1
• SURKQQVGCDQXQT-CQSZACIVSA-N (4ar)-9-(furan-2-yl)-3-(2-hydroxyacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CO)NC2=CC=C3C1=CC=CO1 SURKQQVGCDQXQT-CQSZACIVSA-N 0.000 claims 1
• RJSJLGLZEUJCDZ-LJQANCHMSA-N (4ar)-9-phenyl-3-(thiophene-2-carbonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@@H]1N(C(C2=C3)=O)CCN(C1)C(=O)C=1SC=CC=1)NC2=CC=C3C1=CC=CC=C1 RJSJLGLZEUJCDZ-LJQANCHMSA-N 0.000 claims 1
• UTPMJXCXUCHTSG-FQEVSTJZSA-N (4as)-3-(3,3-dimethylbutanoyl)-9-(2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CC(C)(C)C)NC2=CC=C3C1=CC=CC=C1F UTPMJXCXUCHTSG-FQEVSTJZSA-N 0.000 claims 1
• RROHQXCLLZSODJ-VQTJNVASSA-N (4as)-3-[(2s)-2-amino-3,3-dimethylbutanoyl]-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@H]1N(C(C2=C3)=O)CCN(C1)C(=O)[C@@H](N)C(C)(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1F RROHQXCLLZSODJ-VQTJNVASSA-N 0.000 claims 1
• PMPVLGMBJBFQPX-VQTJNVASSA-N (4as)-3-[(2s)-2-amino-3,3-dimethylbutanoyl]-9-(4-chlorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@H]1N(C(C2=C3)=O)CCN(C1)C(=O)[C@@H](N)C(C)(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1 PMPVLGMBJBFQPX-VQTJNVASSA-N 0.000 claims 1
• GVSSIHAGOZKTRS-FQEVSTJZSA-N (4as)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@H]1N(C(C2=C3)=O)CCN(C1)C(=O)CC(C)(C)C)NC2=CC=C3C1=CC=C(Cl)C=C1F GVSSIHAGOZKTRS-FQEVSTJZSA-N 0.000 claims 1
• YSDSITIHHFSLRG-SANMLTNESA-N (4as)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-6-(2-morpholin-4-ylethyl)-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O=C([C@H]1N(C(C2=CC(=CC=C22)C=3C(=CC(Cl)=CC=3)F)=O)CCN(C1)C(=O)CC(C)(C)C)N2CCN1CCOCC1 YSDSITIHHFSLRG-SANMLTNESA-N 0.000 claims 1
• QHMCWQQLKFYWHO-SANMLTNESA-N (4as)-9-(4-chloro-2-fluorophenyl)-3-(3,3-dimethylbutanoyl)-6-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,2,4,4a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1CN(C)CCN1C(=O)CN1C(=O)[C@@H]2CN(C(=O)CC(C)(C)C)CCN2C(=O)C2=CC(C=3C(=CC(Cl)=CC=3)F)=CC=C21 QHMCWQQLKFYWHO-SANMLTNESA-N 0.000 claims 1
• PGZGRJCOHFYEGJ-DQEYMECFSA-N (4as)-9-(4-chlorophenyl)-3-[(2s)-1-piperidin-4-ylpyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)[C@H]2N(CCN(C2)C(=O)[C@H]2N(CCC2)C2CCNCC2)C2=O)C2=C1 PGZGRJCOHFYEGJ-DQEYMECFSA-N 0.000 claims 1
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
• QYBKMBQLSZFOGD-UHFFFAOYSA-N 3-(2-amino-1,3-thiazole-4-carbonyl)-9-(4-chlorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound S1C(N)=NC(C(=O)N2CC3N(C(C4=CC(=CC=C4NC3=O)C=3C=CC(Cl)=CC=3)=O)CC2)=C1 QYBKMBQLSZFOGD-UHFFFAOYSA-N 0.000 claims 1
• MBSXQXOMXGUCDJ-UHFFFAOYSA-N 3-(3,3-dimethylbutanoyl)-9-(2,4,5-trifluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC(F)=C(F)C=C1F MBSXQXOMXGUCDJ-UHFFFAOYSA-N 0.000 claims 1
• QNAQRHRBVQZRCR-UHFFFAOYSA-N 3-(3,3-dimethylbutanoyl)-9-(2,4-dimethylphenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound CC1=CC(C)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)CC(C)(C)C)C2=O)C2=C1 QNAQRHRBVQZRCR-UHFFFAOYSA-N 0.000 claims 1
• UTPMJXCXUCHTSG-UHFFFAOYSA-N 3-(3,3-dimethylbutanoyl)-9-(2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=CC=C1F UTPMJXCXUCHTSG-UHFFFAOYSA-N 0.000 claims 1
• XEOPULBQUGVEAF-UHFFFAOYSA-N 3-(5-amino-2-methyl-1,3-thiazole-4-carbonyl)-9-(4-chlorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound S1C(C)=NC(C(=O)N2CC3N(C(C4=CC(=CC=C4NC3=O)C=3C=CC(Cl)=CC=3)=O)CC2)=C1N XEOPULBQUGVEAF-UHFFFAOYSA-N 0.000 claims 1
• PMPVLGMBJBFQPX-ANYOKISRSA-N 3-[(2r)-2-amino-3,3-dimethylbutanoyl]-9-(4-chlorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)[C@H](N)C(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1 PMPVLGMBJBFQPX-ANYOKISRSA-N 0.000 claims 1
• RROHQXCLLZSODJ-GFOWMXPYSA-N 3-[(2s)-2-amino-3,3-dimethylbutanoyl]-9-(4-chloro-2-fluorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)[C@@H](N)C(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F RROHQXCLLZSODJ-GFOWMXPYSA-N 0.000 claims 1
• DEJGISRFLGZMDG-UHFFFAOYSA-N 3-benzoyl-9-(4-chlorophenyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)C=2C=CC=CC=2)C2=O)C2=C1 DEJGISRFLGZMDG-UHFFFAOYSA-N 0.000 claims 1
• CKEYKSSRJOVABH-UHFFFAOYSA-N 4-[3-(3,3-dimethylbutanoyl)-5,11-dioxo-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepin-9-yl]benzonitrile Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(C#N)C=C1 CKEYKSSRJOVABH-UHFFFAOYSA-N 0.000 claims 1
• KGDFUIJCWVYLSR-UHFFFAOYSA-N 9-(2,4-dichlorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1Cl KGDFUIJCWVYLSR-UHFFFAOYSA-N 0.000 claims 1
• COCJDNWRMLCLEV-UHFFFAOYSA-N 9-(2-chlorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=CC=C1Cl COCJDNWRMLCLEV-UHFFFAOYSA-N 0.000 claims 1
• CMRDRCDHNGXVLG-UHFFFAOYSA-N 9-(2-fluorophenyl)-3-(3-pyridin-2-ylpropanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)CCC=2N=CC=CC=2)C2=O)C2=C1 CMRDRCDHNGXVLG-UHFFFAOYSA-N 0.000 claims 1
• OWILZGBBLIJJGM-UHFFFAOYSA-N 9-(3,5-dichlorophenyl)-3-(3,3-dimethylbutanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)CC(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC(Cl)=CC(Cl)=C1 OWILZGBBLIJJGM-UHFFFAOYSA-N 0.000 claims 1
• RNFJILKHFOCSPL-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(2-cyclopropylacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)CC2CC2)C2=O)C2=C1 RNFJILKHFOCSPL-UHFFFAOYSA-N 0.000 claims 1
• JDTQKKACCOWZFF-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(2-methyl-2-phenylpropanoyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C=1C=CC=CC=1C(C)(C)C(=O)N(C1)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F JDTQKKACCOWZFF-UHFFFAOYSA-N 0.000 claims 1
• WENUBMMLGIXPER-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(2-pyridin-2-ylacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)CC=2N=CC=CC=2)C2=O)C2=C1 WENUBMMLGIXPER-UHFFFAOYSA-N 0.000 claims 1
• AHBQFVIWYSGBJX-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(2-thiophen-3-ylacetyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)CC2=CSC=C2)C2=O)C2=C1 AHBQFVIWYSGBJX-UHFFFAOYSA-N 0.000 claims 1
• GVHBIVZIDLWBNU-UHFFFAOYSA-N 9-(4-chloro-2-fluorophenyl)-3-(3-methylimidazole-4-carbonyl)-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound CN1C=NC=C1C(=O)N1CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CC(Cl)=CC=2)F)C2=O)N2CC1 GVHBIVZIDLWBNU-UHFFFAOYSA-N 0.000 claims 1
• WCOXGFCZTHZJEJ-IKOFQBKESA-N 9-(4-chloro-2-fluorophenyl)-3-[(2r)-1-piperidin-4-ylpyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)[C@@H]2N(CCC2)C2CCNCC2)C2=O)C2=C1 WCOXGFCZTHZJEJ-IKOFQBKESA-N 0.000 claims 1
• ZXXPRSLOFJTTCE-GFOWMXPYSA-N 9-(4-chloro-2-fluorophenyl)-3-[(2r)-2-hydroxy-3-methylbutanoyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)[C@H](O)C(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F ZXXPRSLOFJTTCE-GFOWMXPYSA-N 0.000 claims 1
• WCOXGFCZTHZJEJ-SKCDSABHSA-N 9-(4-chloro-2-fluorophenyl)-3-[(2s)-1-piperidin-4-ylpyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(NC(=O)C2N(CCN(C2)C(=O)[C@H]2N(CCC2)C2CCNCC2)C2=O)C2=C1 WCOXGFCZTHZJEJ-SKCDSABHSA-N 0.000 claims 1
• YVMCHOTVPURRKI-GFOWMXPYSA-N 9-(4-chloro-2-fluorophenyl)-3-[(2s)-2-hydroxy-3,3-dimethylbutanoyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1N(C(=O)[C@@H](O)C(C)(C)C)CCN(C(C2=C3)=O)C1C(=O)NC2=CC=C3C1=CC=C(Cl)C=C1F YVMCHOTVPURRKI-GFOWMXPYSA-N 0.000 claims 1
• YFEKQDCGNPFNDG-YPJRHXLCSA-N 9-(4-chloro-2-fluorophenyl)-3-[(2s,3s)-3-hydroxypyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound O[C@H]1CCN[C@@H]1C(=O)N1CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CC(Cl)=CC=2)F)C2=O)N2CC1 YFEKQDCGNPFNDG-YPJRHXLCSA-N 0.000 claims 1
• ATABSLDPARAAMU-CSXXPUDCSA-N 9-(4-chloro-2-fluorophenyl)-3-[(2s,4r)-4-hydroxypyrrolidine-2-carbonyl]-2,4,4a,6-tetrahydro-1h-pyrazino[2,1-c][1,4]benzodiazepine-5,11-dione Chemical compound C1[C@@H](O)CN[C@@H]1C(=O)N1CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CC(Cl)=CC=2)F)C2=O)N2CC1 ATABSLDPARAAMU-CSXXPUDCSA-N 0.000 claims 1
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