CA2446963A1 - Agents antibacteriens - Google Patents
Agents antibacteriens Download PDFInfo
- Publication number
- CA2446963A1 CA2446963A1 CA002446963A CA2446963A CA2446963A1 CA 2446963 A1 CA2446963 A1 CA 2446963A1 CA 002446963 A CA002446963 A CA 002446963A CA 2446963 A CA2446963 A CA 2446963A CA 2446963 A1 CA2446963 A1 CA 2446963A1
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- cyclopropyl
- dione
- quinazoline
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 8
- 150000008515 quinazolinediones Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 361
- 238000000034 method Methods 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- -1 wherein n is 0 or 1 Chemical group 0.000 claims description 237
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 190
- 125000001072 heteroaryl group Chemical group 0.000 claims description 153
- 125000003118 aryl group Chemical group 0.000 claims description 119
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 113
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 92
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 86
- 125000003342 alkenyl group Chemical group 0.000 claims description 82
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 75
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 125000003107 substituted aryl group Chemical group 0.000 claims description 65
- 229910052760 oxygen Inorganic materials 0.000 claims description 61
- 229910003204 NH2 Inorganic materials 0.000 claims description 59
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 45
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 44
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 11
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 230000001580 bacterial effect Effects 0.000 claims description 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 108020000946 Bacterial DNA Proteins 0.000 claims description 5
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 5
- GOBMJSWVDWHODH-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(C(F)(F)F)C1 GOBMJSWVDWHODH-UHFFFAOYSA-N 0.000 claims description 4
- OZCXZEMNTYEHQS-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 OZCXZEMNTYEHQS-UHFFFAOYSA-N 0.000 claims description 4
- NDEQZMNLEVGHPO-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 NDEQZMNLEVGHPO-UHFFFAOYSA-N 0.000 claims description 4
- FKDUCTKKVABJGL-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(F)C(C(N)CO)C1 FKDUCTKKVABJGL-UHFFFAOYSA-N 0.000 claims description 4
- HDQLGAWKALFNKZ-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)(F)F)C1 HDQLGAWKALFNKZ-UHFFFAOYSA-N 0.000 claims description 4
- DKFGBIDSBWWHRV-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 DKFGBIDSBWWHRV-UHFFFAOYSA-N 0.000 claims description 4
- ILXSGHZKJVCVPN-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 ILXSGHZKJVCVPN-UHFFFAOYSA-N 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KZDHIRXEXVCFGX-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-hydroxy-3-(hydroxymethyl)piperidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(O)C(CO)C1 KZDHIRXEXVCFGX-UHFFFAOYSA-N 0.000 claims description 3
- VURTUKPTNJVSJW-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 VURTUKPTNJVSJW-UHFFFAOYSA-N 0.000 claims description 3
- XBFKMDLSXNVPFV-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 XBFKMDLSXNVPFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- RDHTVHQGNRTBPU-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 RDHTVHQGNRTBPU-UHFFFAOYSA-N 0.000 claims description 3
- KXFZAYJIMHFIIU-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 KXFZAYJIMHFIIU-UHFFFAOYSA-N 0.000 claims description 3
- VKELWFVUUQKCHN-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(F)C(C(N)CO)C1 VKELWFVUUQKCHN-UHFFFAOYSA-N 0.000 claims description 3
- CKKLSLFTPVNCMT-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)CC(F)(F)F)C1 CKKLSLFTPVNCMT-UHFFFAOYSA-N 0.000 claims description 3
- VNVLOLKUQXREMP-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(CN)C(C(F)(F)F)C1 VNVLOLKUQXREMP-UHFFFAOYSA-N 0.000 claims description 3
- WMLJPALHAZLTRV-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(C(F)(F)F)C1 WMLJPALHAZLTRV-UHFFFAOYSA-N 0.000 claims description 3
- SSHICFUEBLQGAL-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 SSHICFUEBLQGAL-UHFFFAOYSA-N 0.000 claims description 3
- LACIWGIAXKZPDH-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 LACIWGIAXKZPDH-UHFFFAOYSA-N 0.000 claims description 3
- OCADTOFIGLOLMP-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound S1C(C(N)C)=CC(C=2C(=C(O)C=3C(=O)NC(=O)N(C4CC4)C=3C=2C)F)=C1 OCADTOFIGLOLMP-UHFFFAOYSA-N 0.000 claims description 3
- 108010054814 DNA Gyrase Proteins 0.000 claims description 3
- 108010041052 DNA Topoisomerase IV Proteins 0.000 claims description 3
- 101710183280 Topoisomerase Proteins 0.000 claims description 3
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- KIHLTSQPSJWBAS-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(O)C1 KIHLTSQPSJWBAS-UHFFFAOYSA-N 0.000 claims description 2
- ROWWYKDMXBKCNE-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-8-methylquinazoline-2,4-dione Chemical compound C1C(O)C(C)CCN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 ROWWYKDMXBKCNE-UHFFFAOYSA-N 0.000 claims description 2
- SXOYYNVBOLBYNL-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 SXOYYNVBOLBYNL-UHFFFAOYSA-N 0.000 claims description 2
- SZELWYWVDCABFB-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C1(O)CC1 SZELWYWVDCABFB-UHFFFAOYSA-N 0.000 claims description 2
- ZMRUHUMTQXYHTH-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound C1C(CO)C(C)CCN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 ZMRUHUMTQXYHTH-UHFFFAOYSA-N 0.000 claims description 2
- PKGVWUKFUWKIQC-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CO)C1 PKGVWUKFUWKIQC-UHFFFAOYSA-N 0.000 claims description 2
- VIXKLMCCWLQQAA-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CCCC1 VIXKLMCCWLQQAA-UHFFFAOYSA-N 0.000 claims description 2
- ITXXLUOGXFTTGV-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1(O)CCCC1 ITXXLUOGXFTTGV-UHFFFAOYSA-N 0.000 claims description 2
- UWYCDZVHKOVAFG-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CC1 UWYCDZVHKOVAFG-UHFFFAOYSA-N 0.000 claims description 2
- BHPATDJOSQEXJD-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(CO)C1 BHPATDJOSQEXJD-UHFFFAOYSA-N 0.000 claims description 2
- MGOCFBBLXPGVHJ-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 MGOCFBBLXPGVHJ-UHFFFAOYSA-N 0.000 claims description 2
- JVKHVBAEAASXKZ-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 JVKHVBAEAASXKZ-UHFFFAOYSA-N 0.000 claims description 2
- MEJHMJZFSCMEQF-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 MEJHMJZFSCMEQF-UHFFFAOYSA-N 0.000 claims description 2
- CQICSKKBENXJGC-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 CQICSKKBENXJGC-UHFFFAOYSA-N 0.000 claims description 2
- FYIGAMXAZAFQPV-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CC1 FYIGAMXAZAFQPV-UHFFFAOYSA-N 0.000 claims description 2
- HWIKRTCQJQFIHC-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1(O)CC1 HWIKRTCQJQFIHC-UHFFFAOYSA-N 0.000 claims description 2
- KWTKZJDDZZRVDS-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 KWTKZJDDZZRVDS-UHFFFAOYSA-N 0.000 claims description 2
- FBRRDQZVGRRRBP-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[4-hydroxy-3-(hydroxymethyl)piperidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(CO)C1 FBRRDQZVGRRRBP-UHFFFAOYSA-N 0.000 claims description 2
- BCWNMNYIERRKEL-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(F)(F)F)C1 BCWNMNYIERRKEL-UHFFFAOYSA-N 0.000 claims description 2
- YPBPBACAFXLSRA-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCOCC1 YPBPBACAFXLSRA-UHFFFAOYSA-N 0.000 claims description 2
- SXDLGOBBUDMRBB-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 SXDLGOBBUDMRBB-UHFFFAOYSA-N 0.000 claims description 2
- SGBKLKRXUIEGNO-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methyl-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(F)(F)F)C1 SGBKLKRXUIEGNO-UHFFFAOYSA-N 0.000 claims description 2
- OJXSRMIPSLNPEU-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methyl-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 OJXSRMIPSLNPEU-UHFFFAOYSA-N 0.000 claims description 2
- WQNFYQHREYTNLN-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 WQNFYQHREYTNLN-UHFFFAOYSA-N 0.000 claims description 2
- DUGXRDGFJHBSOZ-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 DUGXRDGFJHBSOZ-UHFFFAOYSA-N 0.000 claims description 2
- LVSCBGHQHNEWQD-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 LVSCBGHQHNEWQD-UHFFFAOYSA-N 0.000 claims description 2
- FZPBERIEDGWKRX-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 FZPBERIEDGWKRX-UHFFFAOYSA-N 0.000 claims description 2
- JQBXUOQENNQTFR-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 JQBXUOQENNQTFR-UHFFFAOYSA-N 0.000 claims description 2
- KNPXZOWNNIPKDL-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C1=C(F)C(C(F)F)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC KNPXZOWNNIPKDL-UHFFFAOYSA-N 0.000 claims description 2
- BIUDKRLPQMTCSX-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 BIUDKRLPQMTCSX-UHFFFAOYSA-N 0.000 claims description 2
- ZJFCPAGWFYVXSP-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(C)(C)O)C1 ZJFCPAGWFYVXSP-UHFFFAOYSA-N 0.000 claims description 2
- GZGFLCCAUKRFTF-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)C(C)(C)O)C1 GZGFLCCAUKRFTF-UHFFFAOYSA-N 0.000 claims description 2
- CIHWAISGGZVMCD-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(C)(C)O)C1 CIHWAISGGZVMCD-UHFFFAOYSA-N 0.000 claims description 2
- NHUCUQMZYWAYLH-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CO)C1 NHUCUQMZYWAYLH-UHFFFAOYSA-N 0.000 claims description 2
- VCMHYFVBMYDKBE-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F VCMHYFVBMYDKBE-UHFFFAOYSA-N 0.000 claims description 2
- NMQRGSQFSWNSNN-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C1=C(F)C(C(F)F)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC NMQRGSQFSWNSNN-UHFFFAOYSA-N 0.000 claims description 2
- OJGKCFNJLNXJLN-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 OJGKCFNJLNXJLN-UHFFFAOYSA-N 0.000 claims description 2
- UJXNYNGIBQMKEY-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethyl-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCOCC1 UJXNYNGIBQMKEY-UHFFFAOYSA-N 0.000 claims description 2
- ZYFPGALGBKLBMH-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 ZYFPGALGBKLBMH-UHFFFAOYSA-N 0.000 claims description 2
- ABFOFTRIIREHHM-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 ABFOFTRIIREHHM-UHFFFAOYSA-N 0.000 claims description 2
- KPSLORMWYKPFPX-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-methoxy-8-methyl-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCOCC1 KPSLORMWYKPFPX-UHFFFAOYSA-N 0.000 claims description 2
- SLQUSZDPHMYHBI-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-methoxy-8-methyl-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCNCC1 SLQUSZDPHMYHBI-UHFFFAOYSA-N 0.000 claims description 2
- OFKHGLWYOWNZII-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(O)C(C)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 OFKHGLWYOWNZII-UHFFFAOYSA-N 0.000 claims description 2
- BALAQUVGSQLEEA-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)CCC4C3)=C(C)C=2N1C1CC1 BALAQUVGSQLEEA-UHFFFAOYSA-N 0.000 claims description 2
- SPDHVQZHOLQUTJ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(O)CCCCC4C3)=C(C)C=2N1C1CC1 SPDHVQZHOLQUTJ-UHFFFAOYSA-N 0.000 claims description 2
- OMLHDHZOLSLWSX-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)CCCCC4C3)=C(C)C=2N1C1CC1 OMLHDHZOLSLWSX-UHFFFAOYSA-N 0.000 claims description 2
- IUUZBVXDTNTJQP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C1(O)CC1 IUUZBVXDTNTJQP-UHFFFAOYSA-N 0.000 claims description 2
- OHXLFGRXNJUPDW-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(CO)C(C)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 OHXLFGRXNJUPDW-UHFFFAOYSA-N 0.000 claims description 2
- CYJVLSIOIAWASK-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(CO)C1 CYJVLSIOIAWASK-UHFFFAOYSA-N 0.000 claims description 2
- LFXFRIRABAXQGU-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CC1 LFXFRIRABAXQGU-UHFFFAOYSA-N 0.000 claims description 2
- RVRNNUIZTHZGOB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(CO)C1 RVRNNUIZTHZGOB-UHFFFAOYSA-N 0.000 claims description 2
- OVPGZMWCUKIHPG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-5-hydroxy-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 OVPGZMWCUKIHPG-UHFFFAOYSA-N 0.000 claims description 2
- ZTXZGRGDKLQYOR-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 ZTXZGRGDKLQYOR-UHFFFAOYSA-N 0.000 claims description 2
- LQRLPSWGMOUACK-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 LQRLPSWGMOUACK-UHFFFAOYSA-N 0.000 claims description 2
- XFZKVCCQOUETNJ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CC(F)C1C(O)C1(O)CC1 XFZKVCCQOUETNJ-UHFFFAOYSA-N 0.000 claims description 2
- SUYPBVRFFNLJBS-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CC1 SUYPBVRFFNLJBS-UHFFFAOYSA-N 0.000 claims description 2
- NPRRNOAJPFAMNE-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCCC(CO)C=4C=3)=C(C)C=2N1C1CC1 NPRRNOAJPFAMNE-UHFFFAOYSA-N 0.000 claims description 2
- FZSAGFOZPQPMES-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(CO)C=4C=3)=C(C)C=2N1C1CC1 FZSAGFOZPQPMES-UHFFFAOYSA-N 0.000 claims description 2
- LHQBFIWHJWSYTI-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 LHQBFIWHJWSYTI-UHFFFAOYSA-N 0.000 claims description 2
- HOKKLLRWKWNDAQ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(CO)CC=4C=3)=C(C)C=2N1C1CC1 HOKKLLRWKWNDAQ-UHFFFAOYSA-N 0.000 claims description 2
- GCCVRPWSLAPDQH-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 GCCVRPWSLAPDQH-UHFFFAOYSA-N 0.000 claims description 2
- GPZBZCXORQAPAC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 GPZBZCXORQAPAC-UHFFFAOYSA-N 0.000 claims description 2
- FBUVIWZCXFSLIU-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 FBUVIWZCXFSLIU-UHFFFAOYSA-N 0.000 claims description 2
- YHMIHVAVDKNMBQ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 YHMIHVAVDKNMBQ-UHFFFAOYSA-N 0.000 claims description 2
- KDTSXDFGFMQICG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCOCC1 KDTSXDFGFMQICG-UHFFFAOYSA-N 0.000 claims description 2
- DJFIIQOGDIWSMC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCNCC1 DJFIIQOGDIWSMC-UHFFFAOYSA-N 0.000 claims description 2
- ALOZVQISMHXUJD-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 ALOZVQISMHXUJD-UHFFFAOYSA-N 0.000 claims description 2
- RZCMMVURCJZXGA-WDEREUQCSA-N 1-cyclopropyl-6-fluoro-8-methoxy-7-[(3r)-3-[(1s)-1-(methylamino)ethyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C1[C@H]([C@H](C)NC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1OC RZCMMVURCJZXGA-WDEREUQCSA-N 0.000 claims description 2
- TUZMYXDFIBKDBW-NWDGAFQWSA-N 1-cyclopropyl-6-fluoro-8-methyl-7-[(3r)-3-[(1s)-1-(methylamino)ethyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C1[C@H]([C@H](C)NC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C TUZMYXDFIBKDBW-NWDGAFQWSA-N 0.000 claims description 2
- ZRVYYGQHHUGILT-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 ZRVYYGQHHUGILT-UHFFFAOYSA-N 0.000 claims description 2
- PVRZLAZYTQNDDH-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 PVRZLAZYTQNDDH-UHFFFAOYSA-N 0.000 claims description 2
- UUIJVRCKCWXSJZ-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 UUIJVRCKCWXSJZ-UHFFFAOYSA-N 0.000 claims description 2
- SFJGUXDKLTWVKG-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 SFJGUXDKLTWVKG-UHFFFAOYSA-N 0.000 claims description 2
- SCUWLUABMPTXDA-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 SCUWLUABMPTXDA-UHFFFAOYSA-N 0.000 claims description 2
- RESDFCSUOBXALB-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 RESDFCSUOBXALB-UHFFFAOYSA-N 0.000 claims description 2
- QFEIRHRPGKQAHN-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 QFEIRHRPGKQAHN-UHFFFAOYSA-N 0.000 claims description 2
- IEPGLXCRQYTPAT-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 IEPGLXCRQYTPAT-UHFFFAOYSA-N 0.000 claims description 2
- DNDSEXCNWLDQPK-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 DNDSEXCNWLDQPK-UHFFFAOYSA-N 0.000 claims description 2
- DRLUISCROQDPPA-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 DRLUISCROQDPPA-UHFFFAOYSA-N 0.000 claims description 2
- NYFSALKOCXNGSN-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 NYFSALKOCXNGSN-UHFFFAOYSA-N 0.000 claims description 2
- OVHJWWMTZKONGU-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(F)(F)C(O)C=4C=3)=C(C)C=2N1C1CC1 OVHJWWMTZKONGU-UHFFFAOYSA-N 0.000 claims description 2
- JBDCRWCUBLNYKS-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 JBDCRWCUBLNYKS-UHFFFAOYSA-N 0.000 claims description 2
- FSLDYUBBXRZJCW-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(O)C(F)(F)CCC4C3)=C(C)C=2N1C1CC1 FSLDYUBBXRZJCW-UHFFFAOYSA-N 0.000 claims description 2
- PCMDZPCDUBHKSV-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 PCMDZPCDUBHKSV-UHFFFAOYSA-N 0.000 claims description 2
- AORCQGJTXSUNNZ-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)C(F)(F)CCC4C3)=C(C)C=2N1C1CC1 AORCQGJTXSUNNZ-UHFFFAOYSA-N 0.000 claims description 2
- XCKOCCXWAQHTBY-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 XCKOCCXWAQHTBY-UHFFFAOYSA-N 0.000 claims description 2
- GPLIBQFDIBJIII-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 GPLIBQFDIBJIII-UHFFFAOYSA-N 0.000 claims description 2
- OWUZNFVHCFRNTL-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 OWUZNFVHCFRNTL-UHFFFAOYSA-N 0.000 claims description 2
- WEHHYHOROYHUKG-QWHCGFSZSA-N 1-cyclopropyl-7-[(3r)-3-[(1s)-1-(ethylamino)ethyl]pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](C)NCC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C WEHHYHOROYHUKG-QWHCGFSZSA-N 0.000 claims description 2
- IJVYYAVJDMLZOW-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(CO)C(F)(F)C1 IJVYYAVJDMLZOW-UHFFFAOYSA-N 0.000 claims description 2
- ZMORCLDNGXVZFY-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CO)C(F)(F)C1 ZMORCLDNGXVZFY-UHFFFAOYSA-N 0.000 claims description 2
- GKSFCNUMCOSOJV-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CO)C(F)(F)C1 GKSFCNUMCOSOJV-UHFFFAOYSA-N 0.000 claims description 2
- MNHOYPWNTCXOKW-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CO)C(F)(F)C1 MNHOYPWNTCXOKW-UHFFFAOYSA-N 0.000 claims description 2
- FIFFGFZLMAHFHR-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(C)(C)O)C1 FIFFGFZLMAHFHR-UHFFFAOYSA-N 0.000 claims description 2
- MCFVCCMYLFRMAQ-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(O)C(C)(C)O)C1 MCFVCCMYLFRMAQ-UHFFFAOYSA-N 0.000 claims description 2
- VDECZVVQRUDXLR-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(C)(C)O)C1 VDECZVVQRUDXLR-UHFFFAOYSA-N 0.000 claims description 2
- VKOWIUNNYLFCPE-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CO)C1 VKOWIUNNYLFCPE-UHFFFAOYSA-N 0.000 claims description 2
- MTHBVWIFIHHYGW-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F MTHBVWIFIHHYGW-UHFFFAOYSA-N 0.000 claims description 2
- KQPJTUOQRUPPSU-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-5-hydroxy-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F KQPJTUOQRUPPSU-UHFFFAOYSA-N 0.000 claims description 2
- YMSXQPPQELNXLP-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F YMSXQPPQELNXLP-UHFFFAOYSA-N 0.000 claims description 2
- BISSMNULUZDXIA-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,6-difluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CCC1C(O)C1=C(F)C=CC=C1F BISSMNULUZDXIA-UHFFFAOYSA-N 0.000 claims description 2
- GJOMZEJEPDMLFD-UHFFFAOYSA-N 1-cyclopropyl-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C1=C(F)C(C)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC GJOMZEJEPDMLFD-UHFFFAOYSA-N 0.000 claims description 2
- FIHJOXQAKMBVIV-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCC(F)(F)C(CO)C=4C=3)=C(C)C=2N1C1CC1 FIHJOXQAKMBVIV-UHFFFAOYSA-N 0.000 claims description 2
- CPAIESWXIRZLHF-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(F)(F)C(CO)C=4C=3)=C(C)C=2N1C1CC1 CPAIESWXIRZLHF-UHFFFAOYSA-N 0.000 claims description 2
- PEUSWEYNCDAULX-HNCPQSOCSA-N 1-cyclopropyl-8-(difluoromethoxy)-7-[(1r)-1-methyl-2,3-dihydro-1h-isoindol-5-yl]quinazoline-2,4-dione;hydrochloride Chemical compound Cl.N([C@@H](C1=CC=2)C)CC1=CC=2C(C=1OC(F)F)=CC=C(C(NC2=O)=O)C=1N2C1CC1 PEUSWEYNCDAULX-HNCPQSOCSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- NLGKFMKRTWJMIP-BGFSCIKGSA-N 5-[(3aS,6aR)-4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione hydrochloride Chemical compound Cl.COC1=CC(F)=C(N2C[C@H]3C(N)CC[C@H]3C2)C(C(NC2=O)=O)=C1N2C1CC1 NLGKFMKRTWJMIP-BGFSCIKGSA-N 0.000 claims description 2
- WMGRYWTVASYQDN-QXQDIAAESA-N 5-[(3aS,6aR)-4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=CC(F)=C(N2C[C@H]3C(N)CC[C@H]3C2)C(C(NC2=O)=O)=C1N2C1CC1 WMGRYWTVASYQDN-QXQDIAAESA-N 0.000 claims description 2
- ZVQJWZWBLXONJY-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(O)C1 ZVQJWZWBLXONJY-UHFFFAOYSA-N 0.000 claims description 2
- SVXXJQHHKFXUDI-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 SVXXJQHHKFXUDI-UHFFFAOYSA-N 0.000 claims description 2
- GLKHETRFQFWIDU-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C1(O)CC1 GLKHETRFQFWIDU-UHFFFAOYSA-N 0.000 claims description 2
- FQYKHXUCRHXVKO-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C1(O)CC1 FQYKHXUCRHXVKO-UHFFFAOYSA-N 0.000 claims description 2
- SLEBGMHZJXIHFE-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(CO)C1 SLEBGMHZJXIHFE-UHFFFAOYSA-N 0.000 claims description 2
- OLNUSDGWHBBXOB-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound C1C(CO)C(C)CCN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 OLNUSDGWHBBXOB-UHFFFAOYSA-N 0.000 claims description 2
- BKWBPFCEJUWMCN-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CCCC1 BKWBPFCEJUWMCN-UHFFFAOYSA-N 0.000 claims description 2
- KOQZCBHYTIMPKF-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CC1 KOQZCBHYTIMPKF-UHFFFAOYSA-N 0.000 claims description 2
- CHASXYQUXQVSSS-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(CO)C1 CHASXYQUXQVSSS-UHFFFAOYSA-N 0.000 claims description 2
- NDAYYLCQDXVIAM-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 NDAYYLCQDXVIAM-UHFFFAOYSA-N 0.000 claims description 2
- LKZSCXRGQUFIND-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 LKZSCXRGQUFIND-UHFFFAOYSA-N 0.000 claims description 2
- GECZLKHTSLEFRF-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 GECZLKHTSLEFRF-UHFFFAOYSA-N 0.000 claims description 2
- CAVNZJHTPMODSD-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 CAVNZJHTPMODSD-UHFFFAOYSA-N 0.000 claims description 2
- IYOGCNZLBPGHNL-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CC1 IYOGCNZLBPGHNL-UHFFFAOYSA-N 0.000 claims description 2
- WHMWIVWMAPKFCD-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1(O)CC1 WHMWIVWMAPKFCD-UHFFFAOYSA-N 0.000 claims description 2
- UVYCEHFZRPGIAY-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 UVYCEHFZRPGIAY-UHFFFAOYSA-N 0.000 claims description 2
- JRRRPJYJWDRVOX-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[4-hydroxy-3-(hydroxymethyl)piperidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(CO)C1 JRRRPJYJWDRVOX-UHFFFAOYSA-N 0.000 claims description 2
- JDGOKOHTGIHJHS-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(F)(F)F)C1 JDGOKOHTGIHJHS-UHFFFAOYSA-N 0.000 claims description 2
- NISQQPKZMZWKQT-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 NISQQPKZMZWKQT-UHFFFAOYSA-N 0.000 claims description 2
- HHSDYYIPSICKGN-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCOCC1 HHSDYYIPSICKGN-UHFFFAOYSA-N 0.000 claims description 2
- SPGCQHWIBSPZSR-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCNCC1 SPGCQHWIBSPZSR-UHFFFAOYSA-N 0.000 claims description 2
- HMSQYNZLAUSMIK-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methyl-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(F)(F)F)C1 HMSQYNZLAUSMIK-UHFFFAOYSA-N 0.000 claims description 2
- DSAZJCHNYMPDRK-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(O)C(O)C1 DSAZJCHNYMPDRK-UHFFFAOYSA-N 0.000 claims description 2
- RXRHEUHOQDGULP-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 RXRHEUHOQDGULP-UHFFFAOYSA-N 0.000 claims description 2
- OHZIAXLJUCLWAJ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 OHZIAXLJUCLWAJ-UHFFFAOYSA-N 0.000 claims description 2
- QTIQFYMWGBQONY-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C1=C(F)C(N)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC QTIQFYMWGBQONY-UHFFFAOYSA-N 0.000 claims description 2
- TXMRCPAUJJBPOE-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 TXMRCPAUJJBPOE-UHFFFAOYSA-N 0.000 claims description 2
- MEUDDODGNLNVLU-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 MEUDDODGNLNVLU-UHFFFAOYSA-N 0.000 claims description 2
- VCRYEMXWZKURJQ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 VCRYEMXWZKURJQ-UHFFFAOYSA-N 0.000 claims description 2
- BQZZERMXAUYJOV-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 BQZZERMXAUYJOV-UHFFFAOYSA-N 0.000 claims description 2
- FOSZJQQOBWJPIT-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 FOSZJQQOBWJPIT-UHFFFAOYSA-N 0.000 claims description 2
- KNPATGMKUIGEFT-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 KNPATGMKUIGEFT-UHFFFAOYSA-N 0.000 claims description 2
- WETKGEGQOGKDQS-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CO)C(F)(F)C1 WETKGEGQOGKDQS-UHFFFAOYSA-N 0.000 claims description 2
- IMCCYXFAHLNJQX-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(C)(C)O)C1 IMCCYXFAHLNJQX-UHFFFAOYSA-N 0.000 claims description 2
- KFPPKDGFIAYESF-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)C(C)(C)O)C1 KFPPKDGFIAYESF-UHFFFAOYSA-N 0.000 claims description 2
- QNFDPYMJCZSDGT-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(C)(C)O)C1 QNFDPYMJCZSDGT-UHFFFAOYSA-N 0.000 claims description 2
- WAAJDEVIWQJPQW-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)CO)C1 WAAJDEVIWQJPQW-UHFFFAOYSA-N 0.000 claims description 2
- SGWWRBGXEYIXSL-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F SGWWRBGXEYIXSL-UHFFFAOYSA-N 0.000 claims description 2
- PKBLGEACSBTPIV-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-[(2,6-difluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1=C(F)C=CC=C1F PKBLGEACSBTPIV-UHFFFAOYSA-N 0.000 claims description 2
- YJJQGHSSGIJELN-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C1=C(F)C(N)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC YJJQGHSSGIJELN-UHFFFAOYSA-N 0.000 claims description 2
- USRVKFYPSTVRNJ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 USRVKFYPSTVRNJ-UHFFFAOYSA-N 0.000 claims description 2
- GOLIKUIIWXHCOJ-UHFFFAOYSA-N 5-amino-7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 GOLIKUIIWXHCOJ-UHFFFAOYSA-N 0.000 claims description 2
- HIXWYWVCUIBJJF-UHFFFAOYSA-N 5-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 HIXWYWVCUIBJJF-UHFFFAOYSA-N 0.000 claims description 2
- NNYYIUQBWNRUSU-UHFFFAOYSA-N 5-amino-7-(4-amino-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 NNYYIUQBWNRUSU-UHFFFAOYSA-N 0.000 claims description 2
- JXTBYHAZQCFNFP-UHFFFAOYSA-N 5-amino-7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 JXTBYHAZQCFNFP-UHFFFAOYSA-N 0.000 claims description 2
- FZEQHMKFJSAQJL-UHFFFAOYSA-N 5-amino-7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 FZEQHMKFJSAQJL-UHFFFAOYSA-N 0.000 claims description 2
- FWHKWGKOQZBQEP-UHFFFAOYSA-N 5-amino-7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 FWHKWGKOQZBQEP-UHFFFAOYSA-N 0.000 claims description 2
- UTTNDJKOZAMRQP-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)C(F)(F)F)C1 UTTNDJKOZAMRQP-UHFFFAOYSA-N 0.000 claims description 2
- GDKFASDBFLBPHH-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)C(F)(F)F)C1 GDKFASDBFLBPHH-UHFFFAOYSA-N 0.000 claims description 2
- IHNXCGXTLHWYBA-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)F)C1 IHNXCGXTLHWYBA-UHFFFAOYSA-N 0.000 claims description 2
- QSOQWQFQVSVIKW-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)F)C1 QSOQWQFQVSVIKW-UHFFFAOYSA-N 0.000 claims description 2
- SWLMYMQTHXXHSU-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CF)C1 SWLMYMQTHXXHSU-UHFFFAOYSA-N 0.000 claims description 2
- OEPALGWUJKRTHA-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)CO)C1 OEPALGWUJKRTHA-UHFFFAOYSA-N 0.000 claims description 2
- WINMCXDFLRNYKQ-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CO)C1 WINMCXDFLRNYKQ-UHFFFAOYSA-N 0.000 claims description 2
- OKHAEEPMBJIIEV-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)(F)F)C1 OKHAEEPMBJIIEV-UHFFFAOYSA-N 0.000 claims description 2
- DHLRSYFNNWEQRR-UHFFFAOYSA-N 5-amino-7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 DHLRSYFNNWEQRR-UHFFFAOYSA-N 0.000 claims description 2
- DFNFBCPQPQEHPT-UHFFFAOYSA-N 5-amino-7-[3-(2-amino-1-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CN)C1 DFNFBCPQPQEHPT-UHFFFAOYSA-N 0.000 claims description 2
- UWBUNVCPUWZQQO-UHFFFAOYSA-N 5-amino-7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)N)C1 UWBUNVCPUWZQQO-UHFFFAOYSA-N 0.000 claims description 2
- XPGRAHQRQUANTK-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(F)(F)F)C1 XPGRAHQRQUANTK-UHFFFAOYSA-N 0.000 claims description 2
- DHTSXNCKDIKXLN-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CF)C1 DHTSXNCKDIKXLN-UHFFFAOYSA-N 0.000 claims description 2
- JDLNXCTUMJZRBL-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CF)C1 JDLNXCTUMJZRBL-UHFFFAOYSA-N 0.000 claims description 2
- XDAJBWRMMHHYAP-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)(F)F)C1 XDAJBWRMMHHYAP-UHFFFAOYSA-N 0.000 claims description 2
- IJRAVMOOYJUCFY-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 IJRAVMOOYJUCFY-UHFFFAOYSA-N 0.000 claims description 2
- KPJPTVFZSXWTHZ-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 KPJPTVFZSXWTHZ-UHFFFAOYSA-N 0.000 claims description 2
- MMIGWLUCMKGVOL-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 MMIGWLUCMKGVOL-UHFFFAOYSA-N 0.000 claims description 2
- QJSSTCMUXHZLSI-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(CF)CF)C1 QJSSTCMUXHZLSI-UHFFFAOYSA-N 0.000 claims description 2
- QDBUJFZQKRYWGN-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(CF)CF)C1 QDBUJFZQKRYWGN-UHFFFAOYSA-N 0.000 claims description 2
- XRLLURVGDJAYPG-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 XRLLURVGDJAYPG-UHFFFAOYSA-N 0.000 claims description 2
- OLBXACSBZZTSAX-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 OLBXACSBZZTSAX-UHFFFAOYSA-N 0.000 claims description 2
- VLAOGKOBCHKAJK-UHFFFAOYSA-N 5-amino-7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=COC=N1 VLAOGKOBCHKAJK-UHFFFAOYSA-N 0.000 claims description 2
- DFWNTQDJPGXIFV-UHFFFAOYSA-N 5-amino-7-[3-[amino(cyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1CC1 DFWNTQDJPGXIFV-UHFFFAOYSA-N 0.000 claims description 2
- LDOZFFNCTNTIFL-UHFFFAOYSA-N 5-amino-7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CCCC1 LDOZFFNCTNTIFL-UHFFFAOYSA-N 0.000 claims description 2
- KDZVGJPJZCBMSN-UHFFFAOYSA-N 5-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 KDZVGJPJZCBMSN-UHFFFAOYSA-N 0.000 claims description 2
- AFVIANWHGYCLLQ-UHFFFAOYSA-N 5-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 AFVIANWHGYCLLQ-UHFFFAOYSA-N 0.000 claims description 2
- NGBRBQSERMFBEE-UHFFFAOYSA-N 5-amino-7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 NGBRBQSERMFBEE-UHFFFAOYSA-N 0.000 claims description 2
- ORNDONJWZBODPH-UHFFFAOYSA-N 5-amino-7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 ORNDONJWZBODPH-UHFFFAOYSA-N 0.000 claims description 2
- MXNYWFWPAPTVSW-UHFFFAOYSA-N 5-amino-7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 MXNYWFWPAPTVSW-UHFFFAOYSA-N 0.000 claims description 2
- FJCQJYVSBMGBBI-UHFFFAOYSA-N 5-amino-7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(C(C)N)=C1 FJCQJYVSBMGBBI-UHFFFAOYSA-N 0.000 claims description 2
- CFZBWDLARUWUIE-UHFFFAOYSA-N 5-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 CFZBWDLARUWUIE-UHFFFAOYSA-N 0.000 claims description 2
- JQKRJWHNZCHDDL-UHFFFAOYSA-N 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3NCCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 JQKRJWHNZCHDDL-UHFFFAOYSA-N 0.000 claims description 2
- KXCADVXSWQZLHX-UHFFFAOYSA-N 7-(1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,4-c]pyridin-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3CNCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 KXCADVXSWQZLHX-UHFFFAOYSA-N 0.000 claims description 2
- FFHXACQFYVJKIA-UHFFFAOYSA-N 7-(1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,4-c]pyridin-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3CNCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 FFHXACQFYVJKIA-UHFFFAOYSA-N 0.000 claims description 2
- CVCKARLLTQNASL-UHFFFAOYSA-N 7-(3-amino-2,3,3a,4,6,6a-hexahydrofuro[2,3-c]pyrrol-5-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3C(N)COC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 CVCKARLLTQNASL-UHFFFAOYSA-N 0.000 claims description 2
- RRFVRVDMUWNRHX-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1OC RRFVRVDMUWNRHX-UHFFFAOYSA-N 0.000 claims description 2
- DQNIRZDDPICFCL-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C DQNIRZDDPICFCL-UHFFFAOYSA-N 0.000 claims description 2
- NOIMFWFOFGNGRO-UHFFFAOYSA-N 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(N)C1 NOIMFWFOFGNGRO-UHFFFAOYSA-N 0.000 claims description 2
- XKONWVDQIOYVLH-UHFFFAOYSA-N 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(N)C1 XKONWVDQIOYVLH-UHFFFAOYSA-N 0.000 claims description 2
- VGALXZCUFQYFOF-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 VGALXZCUFQYFOF-UHFFFAOYSA-N 0.000 claims description 2
- HMFLZXKVWPDTPB-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(N)C1 HMFLZXKVWPDTPB-UHFFFAOYSA-N 0.000 claims description 2
- DBNMRSRKVGTVHG-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 DBNMRSRKVGTVHG-UHFFFAOYSA-N 0.000 claims description 2
- IMDRZUAZUIQUAA-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(N)C1 IMDRZUAZUIQUAA-UHFFFAOYSA-N 0.000 claims description 2
- LSFJUAJHQIMAOL-UHFFFAOYSA-N 7-(4-amino-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3C(N)CCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 LSFJUAJHQIMAOL-UHFFFAOYSA-N 0.000 claims description 2
- MDYKPZBMPXRDFP-UHFFFAOYSA-N 7-(4-amino-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 MDYKPZBMPXRDFP-UHFFFAOYSA-N 0.000 claims description 2
- GZCQYOYDQSBRSX-UHFFFAOYSA-N 7-(4-amino-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 GZCQYOYDQSBRSX-UHFFFAOYSA-N 0.000 claims description 2
- GGNKWZLVGPCETK-UHFFFAOYSA-N 7-(4-amino-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 GGNKWZLVGPCETK-UHFFFAOYSA-N 0.000 claims description 2
- ZBHDODJSVIBUBB-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 ZBHDODJSVIBUBB-UHFFFAOYSA-N 0.000 claims description 2
- OYUZVVSXVUMMQE-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(N)C(F)(F)CC4C3)=C(C)C=2N1C1CC1 OYUZVVSXVUMMQE-UHFFFAOYSA-N 0.000 claims description 2
- CUHIKGUKIBZRKX-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 CUHIKGUKIBZRKX-UHFFFAOYSA-N 0.000 claims description 2
- YXVIZMCGXCILTQ-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 YXVIZMCGXCILTQ-UHFFFAOYSA-N 0.000 claims description 2
- GXSKXZHILDWHIG-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 GXSKXZHILDWHIG-UHFFFAOYSA-N 0.000 claims description 2
- SFXNSDOUCYEWJF-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 SFXNSDOUCYEWJF-UHFFFAOYSA-N 0.000 claims description 2
- RKYRUBHIKQSYQL-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 RKYRUBHIKQSYQL-UHFFFAOYSA-N 0.000 claims description 2
- MKOFQMHBFXJFBQ-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(N)C(F)(F)CCCC4C3)=C(C)C=2N1C1CC1 MKOFQMHBFXJFBQ-UHFFFAOYSA-N 0.000 claims description 2
- NZFKIQCBWPWWFT-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 NZFKIQCBWPWWFT-UHFFFAOYSA-N 0.000 claims description 2
- JIDKGHXWYLPZIN-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 JIDKGHXWYLPZIN-UHFFFAOYSA-N 0.000 claims description 2
- OGCXWZQBUWYTBP-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 OGCXWZQBUWYTBP-UHFFFAOYSA-N 0.000 claims description 2
- MHCOUGOOFKZBBG-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 MHCOUGOOFKZBBG-UHFFFAOYSA-N 0.000 claims description 2
- ZASSQHCEIQNBLQ-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 ZASSQHCEIQNBLQ-UHFFFAOYSA-N 0.000 claims description 2
- IYJWFTSXYHIOFV-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 IYJWFTSXYHIOFV-UHFFFAOYSA-N 0.000 claims description 2
- WHPPWMZANIMVPN-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 WHPPWMZANIMVPN-UHFFFAOYSA-N 0.000 claims description 2
- FUBPZVCJWUDQTC-UHFFFAOYSA-N 7-(4-amino-5,6-dihydro-4h-cyclopenta[b]thiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(C=2SC=3CCC(N)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 FUBPZVCJWUDQTC-UHFFFAOYSA-N 0.000 claims description 2
- IJXYLGQADOCEKX-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 IJXYLGQADOCEKX-UHFFFAOYSA-N 0.000 claims description 2
- XMBRSGUYFMTFPK-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(N)C(F)(F)CCC4C3)=C(C)C=2N1C1CC1 XMBRSGUYFMTFPK-UHFFFAOYSA-N 0.000 claims description 2
- VWYICDUCDCCHRD-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 VWYICDUCDCCHRD-UHFFFAOYSA-N 0.000 claims description 2
- RTRBGSCQLKQXPG-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 RTRBGSCQLKQXPG-UHFFFAOYSA-N 0.000 claims description 2
- JAVYYNBEKOQQQW-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 JAVYYNBEKOQQQW-UHFFFAOYSA-N 0.000 claims description 2
- KAKYXFIIWBXVBS-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 KAKYXFIIWBXVBS-UHFFFAOYSA-N 0.000 claims description 2
- BIMDBULUTWINQY-SNVBAGLBSA-N 7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H](C(C)(C)N)C1 BIMDBULUTWINQY-SNVBAGLBSA-N 0.000 claims description 2
- ZZZWCKCIEHGPMO-LLVKDONJSA-N 7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H](C(C)(C)N)C1 ZZZWCKCIEHGPMO-LLVKDONJSA-N 0.000 claims description 2
- WEFFFBUYYAIVFN-BAUSSPIASA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-(fluoromethoxy)quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1OCF WEFFFBUYYAIVFN-BAUSSPIASA-N 0.000 claims description 2
- OUFNPAQEWMMPKY-VZXYPILPSA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H]([C@H](C)N)C1 OUFNPAQEWMMPKY-VZXYPILPSA-N 0.000 claims description 2
- BDYVMYHJPPMPMF-BAUSSPIASA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-8-(difluoromethoxy)quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=CC=C2C(=O)NC(=O)N(C3CC3)C2=C1OC(F)F BDYVMYHJPPMPMF-BAUSSPIASA-N 0.000 claims description 2
- JVXUCBCOBNCLLR-OULXEKPRSA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-8-(difluoromethyl)-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C(F)F JVXUCBCOBNCLLR-OULXEKPRSA-N 0.000 claims description 2
- WGQFMHNHOFCJQD-UFBFGSQYSA-N 7-[(3r,4s)-3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@H](N)[C@@H](CF)C1 WGQFMHNHOFCJQD-UFBFGSQYSA-N 0.000 claims description 2
- UYLOORRMGFXJCQ-ZANVPECISA-N 7-[(3r,4s)-3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1C[C@H](N)[C@@H](CF)C1 UYLOORRMGFXJCQ-ZANVPECISA-N 0.000 claims description 2
- MHUZIZWZKWZAOH-QMMMGPOBSA-N 7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@H](N)C1 MHUZIZWZKWZAOH-QMMMGPOBSA-N 0.000 claims description 2
- PZEXAQCKLCONQN-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)C(F)(F)F)C1 PZEXAQCKLCONQN-UHFFFAOYSA-N 0.000 claims description 2
- WPFOQNACLKXXLJ-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)C(F)(F)F)C1 WPFOQNACLKXXLJ-UHFFFAOYSA-N 0.000 claims description 2
- RRCICTTXIHYVSK-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)C(F)(F)F)C1 RRCICTTXIHYVSK-UHFFFAOYSA-N 0.000 claims description 2
- IFBUJRXNGVIMBJ-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)F)C1 IFBUJRXNGVIMBJ-UHFFFAOYSA-N 0.000 claims description 2
- HOKSNXWEJHVCFY-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C(F)(F)F)C1 HOKSNXWEJHVCFY-UHFFFAOYSA-N 0.000 claims description 2
- QWEOPUFZBWRGSD-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 QWEOPUFZBWRGSD-UHFFFAOYSA-N 0.000 claims description 2
- HLDKCOSFUBUQGV-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 HLDKCOSFUBUQGV-UHFFFAOYSA-N 0.000 claims description 2
- XXKHKAORMUOSSM-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 XXKHKAORMUOSSM-UHFFFAOYSA-N 0.000 claims description 2
- VVXXEWCHTSAJAV-UHFFFAOYSA-N 7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 VVXXEWCHTSAJAV-UHFFFAOYSA-N 0.000 claims description 2
- ARPNQMHANURQAQ-UHFFFAOYSA-N 7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)F)C1 ARPNQMHANURQAQ-UHFFFAOYSA-N 0.000 claims description 2
- QNBGXGKCCIVHSQ-UHFFFAOYSA-N 7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C(F)F)C1 QNBGXGKCCIVHSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZQBGEMUKFNJDKL-UHFFFAOYSA-N 7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)F)C1 ZQBGEMUKFNJDKL-UHFFFAOYSA-N 0.000 claims description 2
- PRPHUSWORIJZBN-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)CF)C1 PRPHUSWORIJZBN-UHFFFAOYSA-N 0.000 claims description 2
- LJKVUVZDWNCYBM-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CF)C1 LJKVUVZDWNCYBM-UHFFFAOYSA-N 0.000 claims description 2
- MOINDRCPBXQFRZ-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C)(C)O)C1 MOINDRCPBXQFRZ-UHFFFAOYSA-N 0.000 claims description 2
- SCIYIMKTLVWDOU-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C)(C)O)C1 SCIYIMKTLVWDOU-UHFFFAOYSA-N 0.000 claims description 2
- DAXJDQNRBNFRIM-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)C(C)(C)O)C1 DAXJDQNRBNFRIM-UHFFFAOYSA-N 0.000 claims description 2
- OMSKDSRHGPJXMX-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C)(C)O)C1 OMSKDSRHGPJXMX-UHFFFAOYSA-N 0.000 claims description 2
- GHIMCHTYJOXZHP-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)CO)C1 GHIMCHTYJOXZHP-UHFFFAOYSA-N 0.000 claims description 2
- YRRPBXZGPMWLOU-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)CO)C1 YRRPBXZGPMWLOU-UHFFFAOYSA-N 0.000 claims description 2
- CUCXHNOXDNNBJV-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)CO)C1 CUCXHNOXDNNBJV-UHFFFAOYSA-N 0.000 claims description 2
- LOJJDMGFMAUUGM-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CO)C1 LOJJDMGFMAUUGM-UHFFFAOYSA-N 0.000 claims description 2
- RCBQVUPRXUYGAB-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)CO)C1 RCBQVUPRXUYGAB-UHFFFAOYSA-N 0.000 claims description 2
- SQXZFTIXNHMKJA-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CO)C1 SQXZFTIXNHMKJA-UHFFFAOYSA-N 0.000 claims description 2
- RZVGYRUSQHUQQF-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)(F)F)C1 RZVGYRUSQHUQQF-UHFFFAOYSA-N 0.000 claims description 2
- WFJLYRAAEFRZSY-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)(F)F)C1 WFJLYRAAEFRZSY-UHFFFAOYSA-N 0.000 claims description 2
- BSYQMTXMMRTBPZ-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)CC(F)F)C1 BSYQMTXMMRTBPZ-UHFFFAOYSA-N 0.000 claims description 2
- JVTLKIMLXWPFAT-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)F)C1 JVTLKIMLXWPFAT-UHFFFAOYSA-N 0.000 claims description 2
- RJEPGVCDJHJVLI-UHFFFAOYSA-N 7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)C(C(N)C)CN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 RJEPGVCDJHJVLI-UHFFFAOYSA-N 0.000 claims description 2
- MDHWJSLMKLYWDE-UHFFFAOYSA-N 7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(F)C(C(C)N)C1 MDHWJSLMKLYWDE-UHFFFAOYSA-N 0.000 claims description 2
- SMNCINVPJLDDGA-UHFFFAOYSA-N 7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(C)N)C1 SMNCINVPJLDDGA-UHFFFAOYSA-N 0.000 claims description 2
- WCZHFVKNCMNYGY-UHFFFAOYSA-N 7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 WCZHFVKNCMNYGY-UHFFFAOYSA-N 0.000 claims description 2
- QEOMFEWNJDLEJB-UHFFFAOYSA-N 7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 QEOMFEWNJDLEJB-UHFFFAOYSA-N 0.000 claims description 2
- PCWQUVGBGKTZFF-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CN)C1 PCWQUVGBGKTZFF-UHFFFAOYSA-N 0.000 claims description 2
- FZYFMKDTQYCAPK-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CN)C1 FZYFMKDTQYCAPK-UHFFFAOYSA-N 0.000 claims description 2
- AVQSSDBWLJZUSC-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)CN)C1 AVQSSDBWLJZUSC-UHFFFAOYSA-N 0.000 claims description 2
- KCBQZTVICMBMDB-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(O)CN)C1 KCBQZTVICMBMDB-UHFFFAOYSA-N 0.000 claims description 2
- ZJVPLHPGOJBHMG-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)CN)C1 ZJVPLHPGOJBHMG-UHFFFAOYSA-N 0.000 claims description 2
- MDIIVAABGWCXOA-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(O)CN)C1 MDIIVAABGWCXOA-UHFFFAOYSA-N 0.000 claims description 2
- BIBRJPGXZOQPRJ-UHFFFAOYSA-N 7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(C)(C)N)C1 BIBRJPGXZOQPRJ-UHFFFAOYSA-N 0.000 claims description 2
- MAMBFHDJUIJQOJ-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-benzylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1(CN)CC1=CC=CC=C1 MAMBFHDJUIJQOJ-UHFFFAOYSA-N 0.000 claims description 2
- QIMJQTALOGYIOQ-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)(CN)C1 QIMJQTALOGYIOQ-UHFFFAOYSA-N 0.000 claims description 2
- GTIUJSGSZPKHQX-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(CN)C(CC(F)(F)F)C1 GTIUJSGSZPKHQX-UHFFFAOYSA-N 0.000 claims description 2
- KQBBKCFFXRIYCU-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(CC(F)(F)F)C1 KQBBKCFFXRIYCU-UHFFFAOYSA-N 0.000 claims description 2
- ZDDNGQBRXWDLBK-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(F)(F)F)C1 ZDDNGQBRXWDLBK-UHFFFAOYSA-N 0.000 claims description 2
- PADPZZSSGBACBL-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(F)(F)F)C1 PADPZZSSGBACBL-UHFFFAOYSA-N 0.000 claims description 2
- RMENUUOIHUPUTR-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)F)C1 RMENUUOIHUPUTR-UHFFFAOYSA-N 0.000 claims description 2
- NEBFIHOWLBIXOO-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)F)C1 NEBFIHOWLBIXOO-UHFFFAOYSA-N 0.000 claims description 2
- NNODQZBCMVGXGN-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)F)C1 NNODQZBCMVGXGN-UHFFFAOYSA-N 0.000 claims description 2
- CZLKLXWYFBONBI-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CF)C1 CZLKLXWYFBONBI-UHFFFAOYSA-N 0.000 claims description 2
- UFFDRALEJIWJRR-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(CF)C1 UFFDRALEJIWJRR-UHFFFAOYSA-N 0.000 claims description 2
- LOKJZVVXLPLSFA-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CF)C1 LOKJZVVXLPLSFA-UHFFFAOYSA-N 0.000 claims description 2
- SLZVZSITBBHAGG-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CF)C1 SLZVZSITBBHAGG-UHFFFAOYSA-N 0.000 claims description 2
- KQHSHMOKKBAMDX-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)(F)F)C1 KQHSHMOKKBAMDX-UHFFFAOYSA-N 0.000 claims description 2
- BHCJIBGACWZTIS-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)(F)F)C1 BHCJIBGACWZTIS-UHFFFAOYSA-N 0.000 claims description 2
- CAELRULHLGFDGH-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(OC(F)(F)F)C1 CAELRULHLGFDGH-UHFFFAOYSA-N 0.000 claims description 2
- FPNKBZUXEQVYCZ-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)(F)F)C1 FPNKBZUXEQVYCZ-UHFFFAOYSA-N 0.000 claims description 2
- IKFQIGDKUHWFFT-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(C(F)(F)F)C1 IKFQIGDKUHWFFT-UHFFFAOYSA-N 0.000 claims description 2
- FRRFZLJZMGUALV-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(C(F)(F)F)C1 FRRFZLJZMGUALV-UHFFFAOYSA-N 0.000 claims description 2
- DEJUJTORWZXDOM-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(C(F)(F)F)C1 DEJUJTORWZXDOM-UHFFFAOYSA-N 0.000 claims description 2
- KNXKPSNPTYWESC-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 KNXKPSNPTYWESC-UHFFFAOYSA-N 0.000 claims description 2
- LCCQXGSDJMNAFC-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 LCCQXGSDJMNAFC-UHFFFAOYSA-N 0.000 claims description 2
- BOELPJOTCFGITB-UHFFFAOYSA-N 7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(CN)C1 BOELPJOTCFGITB-UHFFFAOYSA-N 0.000 claims description 2
- JFQLHTYUISNEPR-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(CN)C1 JFQLHTYUISNEPR-UHFFFAOYSA-N 0.000 claims description 2
- PFTCYAXSIGUYAE-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 PFTCYAXSIGUYAE-UHFFFAOYSA-N 0.000 claims description 2
- JRZBJEMAKDKXDD-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 JRZBJEMAKDKXDD-UHFFFAOYSA-N 0.000 claims description 2
- QDTTXXAXBDAQQA-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 QDTTXXAXBDAQQA-UHFFFAOYSA-N 0.000 claims description 2
- CWGAMWNMMVDOTR-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C(C(F)F)C(F)F)C1 CWGAMWNMMVDOTR-UHFFFAOYSA-N 0.000 claims description 2
- XMZZEUWRBQPJAA-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 XMZZEUWRBQPJAA-UHFFFAOYSA-N 0.000 claims description 2
- CECSOEFFHKMXBO-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)COC(F)(F)F)C1 CECSOEFFHKMXBO-UHFFFAOYSA-N 0.000 claims description 2
- IIFGAHFOZIRIMO-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)COC(F)(F)F)C1 IIFGAHFOZIRIMO-UHFFFAOYSA-N 0.000 claims description 2
- RXADFXGNBCMVMF-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)COC(F)(F)F)C1 RXADFXGNBCMVMF-UHFFFAOYSA-N 0.000 claims description 2
- MVEJJHDSGSLZLY-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)COC(F)(F)F)C1 MVEJJHDSGSLZLY-UHFFFAOYSA-N 0.000 claims description 2
- XPSJOADZKBGRIT-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 XPSJOADZKBGRIT-UHFFFAOYSA-N 0.000 claims description 2
- CDMDZFCWYYBRTM-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 CDMDZFCWYYBRTM-UHFFFAOYSA-N 0.000 claims description 2
- DQQQLSMRMNEMOI-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 DQQQLSMRMNEMOI-UHFFFAOYSA-N 0.000 claims description 2
- WKQLBLCAOMWJQC-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 WKQLBLCAOMWJQC-UHFFFAOYSA-N 0.000 claims description 2
- QFSYRZWMQFGFRX-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 QFSYRZWMQFGFRX-UHFFFAOYSA-N 0.000 claims description 2
- FLKXMZSTIBZTTN-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 FLKXMZSTIBZTTN-UHFFFAOYSA-N 0.000 claims description 2
- RHYFZURZAAPPOS-UHFFFAOYSA-N 7-[3-[1-amino-3,3-difluoro-2,2-bis(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)C(CF)(CF)C(F)F)C1 RHYFZURZAAPPOS-UHFFFAOYSA-N 0.000 claims description 2
- ZTXMDQJBNMIXPS-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(CF)CF)C1 ZTXMDQJBNMIXPS-UHFFFAOYSA-N 0.000 claims description 2
- JEGVLKYIBXABFP-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(CF)CF)C1 JEGVLKYIBXABFP-UHFFFAOYSA-N 0.000 claims description 2
- YMNDMUGYPLNMDR-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C(CF)CF)C1 YMNDMUGYPLNMDR-UHFFFAOYSA-N 0.000 claims description 2
- UGAGYRIOFYPDOV-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(CF)CF)C1 UGAGYRIOFYPDOV-UHFFFAOYSA-N 0.000 claims description 2
- RQMVNHDNAJYASR-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 RQMVNHDNAJYASR-UHFFFAOYSA-N 0.000 claims description 2
- JHJVZYUSXNFMBE-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 JHJVZYUSXNFMBE-UHFFFAOYSA-N 0.000 claims description 2
- PTWONROULOUTKL-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 PTWONROULOUTKL-UHFFFAOYSA-N 0.000 claims description 2
- HJIBHYQLUPBJDB-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 HJIBHYQLUPBJDB-UHFFFAOYSA-N 0.000 claims description 2
- VOPMMCVABYSRCC-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 VOPMMCVABYSRCC-UHFFFAOYSA-N 0.000 claims description 2
- OKSHBSGTMARDJK-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 OKSHBSGTMARDJK-UHFFFAOYSA-N 0.000 claims description 2
- KKAUVUZIKMJBNT-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=COC=N1 KKAUVUZIKMJBNT-UHFFFAOYSA-N 0.000 claims description 2
- XHYNLDYBBYHBQU-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=COC=N1 XHYNLDYBBYHBQU-UHFFFAOYSA-N 0.000 claims description 2
- HLEDOMRFAQEHIJ-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CCC1C(N)C1=COC=N1 HLEDOMRFAQEHIJ-UHFFFAOYSA-N 0.000 claims description 2
- XSSRNIZGOHBRBX-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=COC=N1 XSSRNIZGOHBRBX-UHFFFAOYSA-N 0.000 claims description 2
- LHRWFEPRHHIHDZ-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=COC=N1 LHRWFEPRHHIHDZ-UHFFFAOYSA-N 0.000 claims description 2
- STSRFZMAGXOJSY-UHFFFAOYSA-N 7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=NC=CS1 STSRFZMAGXOJSY-UHFFFAOYSA-N 0.000 claims description 2
- IUCLWDQEZKPKHH-UHFFFAOYSA-N 7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CCC1C(N)C1=NC=CS1 IUCLWDQEZKPKHH-UHFFFAOYSA-N 0.000 claims description 2
- YWIDJYCWGGJLCG-UHFFFAOYSA-N 7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=NC=CS1 YWIDJYCWGGJLCG-UHFFFAOYSA-N 0.000 claims description 2
- HDHMLPNOZWWUAE-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1(O)CCCC1 HDHMLPNOZWWUAE-UHFFFAOYSA-N 0.000 claims description 2
- WPGFBTHBUMFEDO-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CCC1C(N)C1(O)CC1 WPGFBTHBUMFEDO-UHFFFAOYSA-N 0.000 claims description 2
- ZWBGJBYDPFWOEO-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CC1 ZWBGJBYDPFWOEO-UHFFFAOYSA-N 0.000 claims description 2
- ODRXVOUOFNZJSA-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCCC(C=4C=3)C(N)C(F)(F)F)=C(C)C=2N1C1CC1 ODRXVOUOFNZJSA-UHFFFAOYSA-N 0.000 claims description 2
- CDFIATCMTNJBED-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(C=4C=3)C(N)C(F)(F)F)=C(C)C=2N1C1CC1 CDFIATCMTNJBED-UHFFFAOYSA-N 0.000 claims description 2
- HWORMALQYATGMK-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 HWORMALQYATGMK-UHFFFAOYSA-N 0.000 claims description 2
- HLBUTIPGOIBJJQ-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 HLBUTIPGOIBJJQ-UHFFFAOYSA-N 0.000 claims description 2
- LYODAKNDMOJCNG-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 LYODAKNDMOJCNG-UHFFFAOYSA-N 0.000 claims description 2
- MADPQXVVSLPGNU-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(C=4C=3)C(N)CO)=C(C)C=2N1C1CC1 MADPQXVVSLPGNU-UHFFFAOYSA-N 0.000 claims description 2
- RSRADXASFORAJA-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 RSRADXASFORAJA-UHFFFAOYSA-N 0.000 claims description 2
- WFZZKLAWZQMJED-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 WFZZKLAWZQMJED-UHFFFAOYSA-N 0.000 claims description 2
- YYGPGPNWRDJNBP-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 YYGPGPNWRDJNBP-UHFFFAOYSA-N 0.000 claims description 2
- DTEXFNXWVFJLHX-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C(C(=C1O)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 DTEXFNXWVFJLHX-UHFFFAOYSA-N 0.000 claims description 2
- YJAWTJJDCOSYCH-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(C(C)N)C(F)(F)C1 YJAWTJJDCOSYCH-UHFFFAOYSA-N 0.000 claims description 2
- FYUHBXMQSXZRMK-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(C)N)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 FYUHBXMQSXZRMK-UHFFFAOYSA-N 0.000 claims description 2
- JIUCMVZSXQUNDF-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C=1C=2C(C(N)C)CCCC=2SC=1C(C=1C)=C(F)C(C)=C(C(NC2=O)=O)C=1N2C1CC1 JIUCMVZSXQUNDF-UHFFFAOYSA-N 0.000 claims description 2
- GJSIORDBCGPSDS-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(C=4C=3)C(C)N)=C(C)C=2N1C1CC1 GJSIORDBCGPSDS-UHFFFAOYSA-N 0.000 claims description 2
- QPNDKTLHQPCCJU-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(C)N)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 QPNDKTLHQPCCJU-UHFFFAOYSA-N 0.000 claims description 2
- JRPHWTJHDACQET-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(C)N)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 JRPHWTJHDACQET-UHFFFAOYSA-N 0.000 claims description 2
- ZPKZAPVYIBWARB-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C=1C=2C(C(N)C)CCCC=2SC=1C(C=1C)=C(F)C=C(C(NC2=O)=O)C=1N2C1CC1 ZPKZAPVYIBWARB-UHFFFAOYSA-N 0.000 claims description 2
- QFZAYVIVFKDIAE-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 QFZAYVIVFKDIAE-UHFFFAOYSA-N 0.000 claims description 2
- AUGCNTXANXIEQX-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 AUGCNTXANXIEQX-UHFFFAOYSA-N 0.000 claims description 2
- QOEZFJQXWVNSHO-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCCC(C=4C=3)C(O)CN)=C(C)C=2N1C1CC1 QOEZFJQXWVNSHO-UHFFFAOYSA-N 0.000 claims description 2
- HNCIPRAQWPOJCZ-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(C=4C=3)C(O)CN)=C(C)C=2N1C1CC1 HNCIPRAQWPOJCZ-UHFFFAOYSA-N 0.000 claims description 2
- TZLFZLVJODIFPY-UHFFFAOYSA-N 7-[4-(aminomethyl)-3,3-bis(fluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OCF)(OCF)C1 TZLFZLVJODIFPY-UHFFFAOYSA-N 0.000 claims description 2
- DXHGBVKCDJPAPC-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 DXHGBVKCDJPAPC-UHFFFAOYSA-N 0.000 claims description 2
- AGQMFXIIHVCBBT-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCCC(CN)C=4C=3)=C(C)C=2N1C1CC1 AGQMFXIIHVCBBT-UHFFFAOYSA-N 0.000 claims description 2
- RAZDKTFNNYTQSY-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCCC(CN)C=4C=3)=C(C)C=2N1C1CC1 RAZDKTFNNYTQSY-UHFFFAOYSA-N 0.000 claims description 2
- SIXCIWHJDYLNCT-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 SIXCIWHJDYLNCT-UHFFFAOYSA-N 0.000 claims description 2
- IKYAWDHROMFJKZ-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 IKYAWDHROMFJKZ-UHFFFAOYSA-N 0.000 claims description 2
- TZJQEXXVSWMGLK-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 TZJQEXXVSWMGLK-UHFFFAOYSA-N 0.000 claims description 2
- HTULFHLECFUWNX-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCC(F)(F)C(CN)C=4C=3)=C(C)C=2N1C1CC1 HTULFHLECFUWNX-UHFFFAOYSA-N 0.000 claims description 2
- QRIHHCNTEWWARF-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 QRIHHCNTEWWARF-UHFFFAOYSA-N 0.000 claims description 2
- QJVORXGVQKVWCP-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 QJVORXGVQKVWCP-UHFFFAOYSA-N 0.000 claims description 2
- YJALGKVJCNWCRQ-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 YJALGKVJCNWCRQ-UHFFFAOYSA-N 0.000 claims description 2
- ZUABULPFFQTVIY-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 ZUABULPFFQTVIY-UHFFFAOYSA-N 0.000 claims description 2
- GAUXDUKLALPRHK-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(CC=4C=3)C(N)C(F)(F)F)=C(C)C=2N1C1CC1 GAUXDUKLALPRHK-UHFFFAOYSA-N 0.000 claims description 2
- WRJGYQXCEJDRTE-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 WRJGYQXCEJDRTE-UHFFFAOYSA-N 0.000 claims description 2
- SZCSKTOZFPIWTR-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(CC=4C=3)C(N)CO)=C(C)C=2N1C1CC1 SZCSKTOZFPIWTR-UHFFFAOYSA-N 0.000 claims description 2
- APCGGLCIHZXOAV-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)CO)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 APCGGLCIHZXOAV-UHFFFAOYSA-N 0.000 claims description 2
- OKOOLXOFZNZXTI-UHFFFAOYSA-N 7-[5-(1-aminocyclopropyl)thiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C(S1)=CC=C1C1(N)CC1 OKOOLXOFZNZXTI-UHFFFAOYSA-N 0.000 claims description 2
- YVLVXUIFRYVTLC-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(C)N)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 YVLVXUIFRYVTLC-UHFFFAOYSA-N 0.000 claims description 2
- OQPZZSXHJYXZPO-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C=1C=2CC(C(N)C)CCC=2SC=1C(C=1C)=C(F)C(C(F)F)=C(C(NC2=O)=O)C=1N2C1CC1 OQPZZSXHJYXZPO-UHFFFAOYSA-N 0.000 claims description 2
- WGKDAGRMZMWQQV-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(CC=4C=3)C(C)N)=C(C)C=2N1C1CC1 WGKDAGRMZMWQQV-UHFFFAOYSA-N 0.000 claims description 2
- GOHPKFVOBVCJOC-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(C)N)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 GOHPKFVOBVCJOC-UHFFFAOYSA-N 0.000 claims description 2
- DFNQUNBHESQJPK-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C=1C=2CC(C(N)C)CCC=2SC=1C(C=1C)=C(F)C=C(C(NC2=O)=O)C=1N2C1CC1 DFNQUNBHESQJPK-UHFFFAOYSA-N 0.000 claims description 2
- INBMIJPLFXYEBJ-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound S1C(C(N)C)=CC(C=2C(=C(C)C=3C(=O)NC(=O)N(C4CC4)C=3C=2C)F)=C1 INBMIJPLFXYEBJ-UHFFFAOYSA-N 0.000 claims description 2
- YQXUFQLHGWDUII-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 YQXUFQLHGWDUII-UHFFFAOYSA-N 0.000 claims description 2
- QVKJDRUKGFOJLX-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCC(CN)CC=4C=3)=C(C)C=2N1C1CC1 QVKJDRUKGFOJLX-UHFFFAOYSA-N 0.000 claims description 2
- CONCPXIOZPVDPT-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 CONCPXIOZPVDPT-UHFFFAOYSA-N 0.000 claims description 2
- SRXXPLLSPAUVFR-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 SRXXPLLSPAUVFR-UHFFFAOYSA-N 0.000 claims description 2
- CCRWVEABZBIHOY-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 CCRWVEABZBIHOY-UHFFFAOYSA-N 0.000 claims description 2
- QQVALECNWPHYTM-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1C1=CSC(CN)=C1 QQVALECNWPHYTM-UHFFFAOYSA-N 0.000 claims description 2
- VRAQMLLUIVSTIB-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1C1=CSC(CN)=C1 VRAQMLLUIVSTIB-UHFFFAOYSA-N 0.000 claims description 2
- JAULLHFHXDHSAW-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 JAULLHFHXDHSAW-UHFFFAOYSA-N 0.000 claims description 2
- GZNIIQKRJOCZCM-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 GZNIIQKRJOCZCM-UHFFFAOYSA-N 0.000 claims description 2
- KCRGEERZQIUVSD-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 KCRGEERZQIUVSD-UHFFFAOYSA-N 0.000 claims description 2
- URHJZGPEKLJSPP-UHFFFAOYSA-N 7-[7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1h-isoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3(CN)CCCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 URHJZGPEKLJSPP-UHFFFAOYSA-N 0.000 claims description 2
- CRPSKAMOLLIEKS-UHFFFAOYSA-N 7-[7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1h-isoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3(CN)CCCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 CRPSKAMOLLIEKS-UHFFFAOYSA-N 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- YMZXIXVFXVMTJI-UHFFFAOYSA-N FC(F)C1(N)C(F)=C(N2CC(CC2)C(N)C(OCF)(OCF)OCF)C(C)=C2C1C(=O)NC(=O)N2C1CC1 Chemical compound FC(F)C1(N)C(F)=C(N2CC(CC2)C(N)C(OCF)(OCF)OCF)C(C)=C2C1C(=O)NC(=O)N2C1CC1 YMZXIXVFXVMTJI-UHFFFAOYSA-N 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 2
- GJMYBBFREBPCJM-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 GJMYBBFREBPCJM-UHFFFAOYSA-N 0.000 claims 2
- WEZVGBMJABUOFL-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2,3,3,3-pentafluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)C(F)(F)F)C1 WEZVGBMJABUOFL-UHFFFAOYSA-N 0.000 claims 2
- CDKQTPHUFBTGKY-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)(F)F)C1 CDKQTPHUFBTGKY-UHFFFAOYSA-N 0.000 claims 2
- XXRMRLAHAGYDJN-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(C(F)(F)F)C1 XXRMRLAHAGYDJN-UHFFFAOYSA-N 0.000 claims 2
- UVQHUSNJAVIKFG-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)CO)C1 UVQHUSNJAVIKFG-UHFFFAOYSA-N 0.000 claims 2
- IUNQPSBWACKJRX-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CO)C1 IUNQPSBWACKJRX-UHFFFAOYSA-N 0.000 claims 2
- LBKPFVRREBZAAV-UHFFFAOYSA-N 7-[3-[1-amino-3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)(F)F)C(F)(F)F)C1 LBKPFVRREBZAAV-UHFFFAOYSA-N 0.000 claims 2
- MOSUTDLQRQZIOO-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 MOSUTDLQRQZIOO-UHFFFAOYSA-N 0.000 claims 1
- WQZDNPDCEOPVMA-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(CO)C1 WQZDNPDCEOPVMA-UHFFFAOYSA-N 0.000 claims 1
- QQMCFINDWSKBLN-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1(O)CC1 QQMCFINDWSKBLN-UHFFFAOYSA-N 0.000 claims 1
- RIGZQFWWROSHEP-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(CO)C1 RIGZQFWWROSHEP-UHFFFAOYSA-N 0.000 claims 1
- PMLXLFAPDFRJIF-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 PMLXLFAPDFRJIF-UHFFFAOYSA-N 0.000 claims 1
- NAHJXLHYHNUSHG-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[4-hydroxy-3-(hydroxymethyl)piperidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(O)C(CO)C1 NAHJXLHYHNUSHG-UHFFFAOYSA-N 0.000 claims 1
- XMCUXNDAOWHPAQ-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 XMCUXNDAOWHPAQ-UHFFFAOYSA-N 0.000 claims 1
- YLNZYVOZGLJRPV-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 YLNZYVOZGLJRPV-UHFFFAOYSA-N 0.000 claims 1
- VJSYQQQKWUXALI-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 VJSYQQQKWUXALI-UHFFFAOYSA-N 0.000 claims 1
- JZOZOTZIGMDTFI-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCNCC1 JZOZOTZIGMDTFI-UHFFFAOYSA-N 0.000 claims 1
- WRCMPZMDMVLGAW-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(O)C1 WRCMPZMDMVLGAW-UHFFFAOYSA-N 0.000 claims 1
- JNNDYTULZTZRTG-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(O)C(O)C1 JNNDYTULZTZRTG-UHFFFAOYSA-N 0.000 claims 1
- GHQYPPBQGQRAFN-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 GHQYPPBQGQRAFN-UHFFFAOYSA-N 0.000 claims 1
- UGEAIZAJPVHLBK-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 UGEAIZAJPVHLBK-UHFFFAOYSA-N 0.000 claims 1
- BJZVAIDHQRHZQI-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 BJZVAIDHQRHZQI-UHFFFAOYSA-N 0.000 claims 1
- JUBYWDNXMOIHED-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(C)(C)O)C1 JUBYWDNXMOIHED-UHFFFAOYSA-N 0.000 claims 1
- WSZSXGQOAXBMIF-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(O)CO)C1 WSZSXGQOAXBMIF-UHFFFAOYSA-N 0.000 claims 1
- ZLVINVLDCMRPPX-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[3-[(2,6-difluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1=C(F)C=CC=C1F ZLVINVLDCMRPPX-UHFFFAOYSA-N 0.000 claims 1
- UOZVRHONOIXIKQ-UHFFFAOYSA-N 1-cyclopropyl-5-(difluoromethyl)-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(C(O)CO)C21CC2 UOZVRHONOIXIKQ-UHFFFAOYSA-N 0.000 claims 1
- BCAMKWWQMWEVAF-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethyl-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(F)(F)F)C1 BCAMKWWQMWEVAF-UHFFFAOYSA-N 0.000 claims 1
- QVBZRHWVKVGRKK-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethyl-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 QVBZRHWVKVGRKK-UHFFFAOYSA-N 0.000 claims 1
- NCVPWKQSBKFNER-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethyl-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCNCC1 NCVPWKQSBKFNER-UHFFFAOYSA-N 0.000 claims 1
- CNJJGQPSXVSGGB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethyl-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCCC1 CNJJGQPSXVSGGB-UHFFFAOYSA-N 0.000 claims 1
- NVNSEDLKGOWHGM-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CO)C1 NVNSEDLKGOWHGM-UHFFFAOYSA-N 0.000 claims 1
- IAYKWMUFSDDSPS-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 IAYKWMUFSDDSPS-UHFFFAOYSA-N 0.000 claims 1
- OJQSTZXIKKGWRJ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 OJQSTZXIKKGWRJ-UHFFFAOYSA-N 0.000 claims 1
- FKDSOWRAHODZBJ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxy-7-morpholin-4-ylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCOCC1 FKDSOWRAHODZBJ-UHFFFAOYSA-N 0.000 claims 1
- AHHLHVGHXVWVIP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxy-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCNCC1 AHHLHVGHXVWVIP-UHFFFAOYSA-N 0.000 claims 1
- YULXCXMEOCPLTL-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-hydroxy-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 YULXCXMEOCPLTL-UHFFFAOYSA-N 0.000 claims 1
- URNRYSBFCYQACM-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5-methoxy-8-methyl-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCCC1 URNRYSBFCYQACM-UHFFFAOYSA-N 0.000 claims 1
- PHWZLALIBCOOQK-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(O)C1 PHWZLALIBCOOQK-UHFFFAOYSA-N 0.000 claims 1
- KDQLXAVRINZKNV-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 KDQLXAVRINZKNV-UHFFFAOYSA-N 0.000 claims 1
- MFJCFCXRICYGKV-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 MFJCFCXRICYGKV-UHFFFAOYSA-N 0.000 claims 1
- YRHKSLLLSCKZLP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CCC1C1(O)CC1 YRHKSLLLSCKZLP-UHFFFAOYSA-N 0.000 claims 1
- LJQFLSAWVIRDFW-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)-4-methylpiperidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)C(CO)C1 LJQFLSAWVIRDFW-UHFFFAOYSA-N 0.000 claims 1
- VAUSYGOYGFPJCY-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(CO)C1 VAUSYGOYGFPJCY-UHFFFAOYSA-N 0.000 claims 1
- DAFCLPZPTUFWNO-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1(O)CCCC1 DAFCLPZPTUFWNO-UHFFFAOYSA-N 0.000 claims 1
- RIXVGXMTQVENBD-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(O)C1(O)CCCC1 RIXVGXMTQVENBD-UHFFFAOYSA-N 0.000 claims 1
- JPUZDRFXSYHARO-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CCC1C(O)C1(O)CC1 JPUZDRFXSYHARO-UHFFFAOYSA-N 0.000 claims 1
- LSMNZVNCKUKAMG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 LSMNZVNCKUKAMG-UHFFFAOYSA-N 0.000 claims 1
- AIOVLUGENCNGMX-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 AIOVLUGENCNGMX-UHFFFAOYSA-N 0.000 claims 1
- CMXQZWIWHWMSOT-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 CMXQZWIWHWMSOT-UHFFFAOYSA-N 0.000 claims 1
- NVJFZRMAWIORHE-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 NVJFZRMAWIORHE-UHFFFAOYSA-N 0.000 claims 1
- JZVWRYDAXFAJQW-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 JZVWRYDAXFAJQW-UHFFFAOYSA-N 0.000 claims 1
- JYCSXJCUEUUJNF-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 JYCSXJCUEUUJNF-UHFFFAOYSA-N 0.000 claims 1
- BDKNUIDIKRPOOC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-hydroxy-3-(hydroxymethyl)piperidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(CO)C1 BDKNUIDIKRPOOC-UHFFFAOYSA-N 0.000 claims 1
- JMMRKOJRZSFYMP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCC(CO)CC=4C=3)=C(C)C=2N1C1CC1 JMMRKOJRZSFYMP-UHFFFAOYSA-N 0.000 claims 1
- CALAKEKYFFHIQG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-[3-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)C(F)(F)F)C1 CALAKEKYFFHIQG-UHFFFAOYSA-N 0.000 claims 1
- XGBMJVUOMSTRSQ-UHFFFAOYSA-N 1-cyclopropyl-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(O)C(O)C1 XGBMJVUOMSTRSQ-UHFFFAOYSA-N 0.000 claims 1
- XIGYUJIPDNCPPL-UHFFFAOYSA-N 1-cyclopropyl-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(O)C1 XIGYUJIPDNCPPL-UHFFFAOYSA-N 0.000 claims 1
- ROYMHGRVCGCWLX-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(O)C(O)CCC4C3)=C(C)C=2N1C1CC1 ROYMHGRVCGCWLX-UHFFFAOYSA-N 0.000 claims 1
- DAUAGPAUHTVDJS-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 DAUAGPAUHTVDJS-UHFFFAOYSA-N 0.000 claims 1
- CWDXYFROAYRLTA-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 CWDXYFROAYRLTA-UHFFFAOYSA-N 0.000 claims 1
- OYNBKABDZNQAAD-UHFFFAOYSA-N 1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 OYNBKABDZNQAAD-UHFFFAOYSA-N 0.000 claims 1
- ASERFNHUCXLARE-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethyl-3-hydroxypiperidin-1-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound C1C(O)C(CC)CCN1C1=C(F)C(C)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC ASERFNHUCXLARE-UHFFFAOYSA-N 0.000 claims 1
- QYTDMVYKHAMUKZ-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 QYTDMVYKHAMUKZ-UHFFFAOYSA-N 0.000 claims 1
- FYFYVCKHNVTOAG-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)C(F)(F)CC4C3)=C(C)C=2N1C1CC1 FYFYVCKHNVTOAG-UHFFFAOYSA-N 0.000 claims 1
- UOIBILHLMXRROY-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 UOIBILHLMXRROY-UHFFFAOYSA-N 0.000 claims 1
- HQKHRWDAINRFBV-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 HQKHRWDAINRFBV-UHFFFAOYSA-N 0.000 claims 1
- BUICHRYAKSIACO-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)C(F)(F)CCCC4C3)=C(C)C=2N1C1CC1 BUICHRYAKSIACO-UHFFFAOYSA-N 0.000 claims 1
- WEBOYSDVHNZSGI-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 WEBOYSDVHNZSGI-UHFFFAOYSA-N 0.000 claims 1
- SKWYFGAUIZVWFF-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 SKWYFGAUIZVWFF-UHFFFAOYSA-N 0.000 claims 1
- WHXXUUUERVGYKD-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 WHXXUUUERVGYKD-UHFFFAOYSA-N 0.000 claims 1
- ZKJQGJJDCQUHNZ-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 ZKJQGJJDCQUHNZ-UHFFFAOYSA-N 0.000 claims 1
- FLYCZCPLAUTRTE-UHFFFAOYSA-N 1-cyclopropyl-7-(5,5-difluoro-4-hydroxy-6,7-dihydro-4h-1-benzothiophen-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(O)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 FLYCZCPLAUTRTE-UHFFFAOYSA-N 0.000 claims 1
- KKGTURSDFRVXGB-UHFFFAOYSA-N 1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 KKGTURSDFRVXGB-UHFFFAOYSA-N 0.000 claims 1
- OPQSGLRIDRSHPD-PIJUOVFKSA-N 1-cyclopropyl-7-[(3r)-3-[1-(ethylamino)ethyl]pyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C(C)NCC)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1OC OPQSGLRIDRSHPD-PIJUOVFKSA-N 0.000 claims 1
- MGXYYJYRAGEMNX-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CO)C(F)(F)C1 MGXYYJYRAGEMNX-UHFFFAOYSA-N 0.000 claims 1
- NNMSQVAXNRBOGP-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CO)C(F)(F)C1 NNMSQVAXNRBOGP-UHFFFAOYSA-N 0.000 claims 1
- ADSDWWJTAYGKNQ-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CO)C(F)(F)C1 ADSDWWJTAYGKNQ-UHFFFAOYSA-N 0.000 claims 1
- ZALPPDHZUQFMCJ-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(F)C(C(O)C(C)(C)O)C1 ZALPPDHZUQFMCJ-UHFFFAOYSA-N 0.000 claims 1
- GUJKRUHVXQTQPK-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(F)C(C(O)CO)C1 GUJKRUHVXQTQPK-UHFFFAOYSA-N 0.000 claims 1
- HGCQFAIBBZJWAE-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,4-difluorophenyl)-hydroxymethyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1F HGCQFAIBBZJWAE-UHFFFAOYSA-N 0.000 claims 1
- SPTWUQJUSCSJBS-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(2,6-difluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CCC1C(O)C1=C(F)C=CC=C1F SPTWUQJUSCSJBS-UHFFFAOYSA-N 0.000 claims 1
- YJQMVPVSKHFJKR-UHFFFAOYSA-N 1-cyclopropyl-7-[4-ethyl-3-(hydroxymethyl)piperidin-1-yl]-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(CO)C(CC)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 YJQMVPVSKHFJKR-UHFFFAOYSA-N 0.000 claims 1
- DMIRUECJEQDSTE-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 DMIRUECJEQDSTE-UHFFFAOYSA-N 0.000 claims 1
- WAUQKLJKAYOOPI-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 WAUQKLJKAYOOPI-UHFFFAOYSA-N 0.000 claims 1
- ULKCTHCLHWXXQL-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 ULKCTHCLHWXXQL-UHFFFAOYSA-N 0.000 claims 1
- MJONORYGJLNAOS-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 MJONORYGJLNAOS-UHFFFAOYSA-N 0.000 claims 1
- PBCAHUOKQVKJFS-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 PBCAHUOKQVKJFS-UHFFFAOYSA-N 0.000 claims 1
- RWDGITYFEYINJB-UHFFFAOYSA-N 1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 RWDGITYFEYINJB-UHFFFAOYSA-N 0.000 claims 1
- HCWOQGCVDXSCGG-UHFFFAOYSA-N 1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(C(O)CO)C21CC2 HCWOQGCVDXSCGG-UHFFFAOYSA-N 0.000 claims 1
- RCKBKVHDMHXIDA-UHFFFAOYSA-N 1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CC(C(O)CO)C21CC2 RCKBKVHDMHXIDA-UHFFFAOYSA-N 0.000 claims 1
- HLKHEGOCYDIXDR-UHFFFAOYSA-N 1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(C(O)CO)C21CC2 HLKHEGOCYDIXDR-UHFFFAOYSA-N 0.000 claims 1
- QIWUKAVCOIVQGC-UHFFFAOYSA-N 1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(C(O)CO)C21CC2 QIWUKAVCOIVQGC-UHFFFAOYSA-N 0.000 claims 1
- VLBZINODLAQGKJ-UHFFFAOYSA-N 1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(C(O)CO)C21CC2 VLBZINODLAQGKJ-UHFFFAOYSA-N 0.000 claims 1
- ZQDFAKNPBLNTRD-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-(3-hydroxy-4-methylpiperidin-1-yl)-8-methylquinazoline-2,4-dione Chemical compound C1C(O)C(C)CCN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 ZQDFAKNPBLNTRD-UHFFFAOYSA-N 0.000 claims 1
- PIIQTTVTNDFHSC-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CO)C1 PIIQTTVTNDFHSC-UHFFFAOYSA-N 0.000 claims 1
- XORWYGRZKGTYJJ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1(O)CCCC1 XORWYGRZKGTYJJ-UHFFFAOYSA-N 0.000 claims 1
- XXDNBBYKLAYTGA-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-[hydroxy-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(O)C1(O)CC1 XXDNBBYKLAYTGA-UHFFFAOYSA-N 0.000 claims 1
- XCKFLQWOYHXPIO-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(CO)C1 XCKFLQWOYHXPIO-UHFFFAOYSA-N 0.000 claims 1
- LFCSWOSLLDAIGL-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[hydroxy-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1(O)CCCC1 LFCSWOSLLDAIGL-UHFFFAOYSA-N 0.000 claims 1
- UXCHPCLQCBFJFM-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CO)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 UXCHPCLQCBFJFM-UHFFFAOYSA-N 0.000 claims 1
- GSMBQTKMVJPSIJ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 GSMBQTKMVJPSIJ-UHFFFAOYSA-N 0.000 claims 1
- AMPKGRZMQHIPEL-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-[5-(hydroxymethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CO)CC=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 AMPKGRZMQHIPEL-UHFFFAOYSA-N 0.000 claims 1
- ZLXUMGYHMSFMRX-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 ZLXUMGYHMSFMRX-UHFFFAOYSA-N 0.000 claims 1
- CUEVVAJMEBPXRK-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-8-methyl-7-[3-[3,3,3-trifluoro-1,2-dihydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(O)(C(F)(F)F)C(F)(F)F)C1 CUEVVAJMEBPXRK-UHFFFAOYSA-N 0.000 claims 1
- SOKKWRFKVIMUAK-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(3,4-dihydroxypiperidin-1-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)C(O)C1 SOKKWRFKVIMUAK-UHFFFAOYSA-N 0.000 claims 1
- JHZGBZKXHSWBNH-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 JHZGBZKXHSWBNH-UHFFFAOYSA-N 0.000 claims 1
- NTJMQWXCAQSCPU-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 NTJMQWXCAQSCPU-UHFFFAOYSA-N 0.000 claims 1
- FVKSKFZZKPFZEP-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-1,3,3a,4,5,6,7,8,9,9a-decahydrocycloocta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CCCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 FVKSKFZZKPFZEP-UHFFFAOYSA-N 0.000 claims 1
- YZDPVGBNAYRIBB-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 YZDPVGBNAYRIBB-UHFFFAOYSA-N 0.000 claims 1
- OWSIKPGSZYNQFF-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(O)CC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 OWSIKPGSZYNQFF-UHFFFAOYSA-N 0.000 claims 1
- GCQMCABHKFLNKJ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(4,5-dihydroxy-3,3a,4,5,6,7,8,8a-octahydro-1h-cyclohepta[c]pyrrol-2-yl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)C(O)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 GCQMCABHKFLNKJ-UHFFFAOYSA-N 0.000 claims 1
- MKHIYYHNQSKOOS-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-(6,6-difluoro-7-hydroxy-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(O)C(F)(F)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 MKHIYYHNQSKOOS-UHFFFAOYSA-N 0.000 claims 1
- MSYRDNMTHVTMEF-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3,3-difluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CO)C(F)(F)C1 MSYRDNMTHVTMEF-UHFFFAOYSA-N 0.000 claims 1
- SZNKRILSBRXZBQ-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxy-2-methylpropyl)pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)C(C)(C)O)C1 SZNKRILSBRXZBQ-UHFFFAOYSA-N 0.000 claims 1
- GLOMNPYWPKCZLA-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[3-(1,2-dihydroxyethyl)-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(O)CO)C1 GLOMNPYWPKCZLA-UHFFFAOYSA-N 0.000 claims 1
- DQKMPGDGAAGOBU-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 DQKMPGDGAAGOBU-UHFFFAOYSA-N 0.000 claims 1
- GQOMQYKATIVCKH-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[5,5-difluoro-4-(hydroxymethyl)-6,7-dihydro-4h-1-benzothiophen-2-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CO)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 GQOMQYKATIVCKH-UHFFFAOYSA-N 0.000 claims 1
- SOXCNDVYFSXEPP-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(C(O)CO)C21CC2 SOXCNDVYFSXEPP-UHFFFAOYSA-N 0.000 claims 1
- MITQKFMFAFNSRM-UHFFFAOYSA-N 5-amino-1-cyclopropyl-7-[7-(1,2-dihydroxyethyl)-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(C(O)CO)C21CC2 MITQKFMFAFNSRM-UHFFFAOYSA-N 0.000 claims 1
- FSOBASOZYCBWRY-UHFFFAOYSA-N 5-amino-7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C1=C(F)C(N)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC FSOBASOZYCBWRY-UHFFFAOYSA-N 0.000 claims 1
- LIXNFNDJANDRKV-UHFFFAOYSA-N 5-amino-7-(4-amino-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 LIXNFNDJANDRKV-UHFFFAOYSA-N 0.000 claims 1
- LVOANPWDWDUGBB-UHFFFAOYSA-N 5-amino-7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 LVOANPWDWDUGBB-UHFFFAOYSA-N 0.000 claims 1
- DEPNWPXYBPVYKL-UHFFFAOYSA-N 5-amino-7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 DEPNWPXYBPVYKL-UHFFFAOYSA-N 0.000 claims 1
- IJVODFNEZCKHBA-UHFFFAOYSA-N 5-amino-7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 IJVODFNEZCKHBA-UHFFFAOYSA-N 0.000 claims 1
- UQIHZJKYKWBYTN-UHFFFAOYSA-N 5-amino-7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 UQIHZJKYKWBYTN-UHFFFAOYSA-N 0.000 claims 1
- GRYCNPNYQLGXLH-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)F)C1 GRYCNPNYQLGXLH-UHFFFAOYSA-N 0.000 claims 1
- FIBSLQPFJQEODH-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(C)(C)O)C1 FIBSLQPFJQEODH-UHFFFAOYSA-N 0.000 claims 1
- RDGZPPUWDRLKEO-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxy-2-methylpropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C)(C)O)C1 RDGZPPUWDRLKEO-UHFFFAOYSA-N 0.000 claims 1
- IJLSNCYNQGPSDX-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)CO)C1 IJLSNCYNQGPSDX-UHFFFAOYSA-N 0.000 claims 1
- GWALNMJFLVIGHK-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CO)C1 GWALNMJFLVIGHK-UHFFFAOYSA-N 0.000 claims 1
- FJQVQPRJQRAOAU-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)F)C1 FJQVQPRJQRAOAU-UHFFFAOYSA-N 0.000 claims 1
- YGHAPMRPEOWCFB-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)F)C1 YGHAPMRPEOWCFB-UHFFFAOYSA-N 0.000 claims 1
- JVRXUWRJFMSFBT-UHFFFAOYSA-N 5-amino-7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C1(N)CC1 JVRXUWRJFMSFBT-UHFFFAOYSA-N 0.000 claims 1
- YHBVCWKJIOQXRF-UHFFFAOYSA-N 5-amino-7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C1(N)CC1 YHBVCWKJIOQXRF-UHFFFAOYSA-N 0.000 claims 1
- XLDPXYZWHIBBBV-UHFFFAOYSA-N 5-amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(C)N)C1 XLDPXYZWHIBBBV-UHFFFAOYSA-N 0.000 claims 1
- STAVLIZOQILZAB-UHFFFAOYSA-N 5-amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)C(C(N)C)CN1C(C(=C1N)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 STAVLIZOQILZAB-UHFFFAOYSA-N 0.000 claims 1
- KDPUGQQAMLVDFN-UHFFFAOYSA-N 5-amino-7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 KDPUGQQAMLVDFN-UHFFFAOYSA-N 0.000 claims 1
- YJPNNUMHXLACHV-UHFFFAOYSA-N 5-amino-7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)CN)C1 YJPNNUMHXLACHV-UHFFFAOYSA-N 0.000 claims 1
- IXMORRWTKUKBNQ-UHFFFAOYSA-N 5-amino-7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(C)(C)N)C1 IXMORRWTKUKBNQ-UHFFFAOYSA-N 0.000 claims 1
- AUWVZGIWLIUZAT-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(F)(F)F)C1 AUWVZGIWLIUZAT-UHFFFAOYSA-N 0.000 claims 1
- JXWFYPQBBNVKRI-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)F)C1 JXWFYPQBBNVKRI-UHFFFAOYSA-N 0.000 claims 1
- OONUSKWREYJNRT-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)F)C1 OONUSKWREYJNRT-UHFFFAOYSA-N 0.000 claims 1
- BJINXROOKQDDGH-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)(F)F)C1 BJINXROOKQDDGH-UHFFFAOYSA-N 0.000 claims 1
- QVGRDJGBMVYVTC-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 QVGRDJGBMVYVTC-UHFFFAOYSA-N 0.000 claims 1
- NGBCCRHCZJZGRI-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(CN)C1 NGBCCRHCZJZGRI-UHFFFAOYSA-N 0.000 claims 1
- USFSIXQMRILFDI-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-4ah-quinazoline-2,4-dione Chemical compound FC(F)C1(N)C(F)=C(N2CC(CC2)C(N)COC(F)(F)F)C(OC)=C2C1C(=O)NC(=O)N2C1CC1 USFSIXQMRILFDI-UHFFFAOYSA-N 0.000 claims 1
- ITWHDIINCTWOFD-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 ITWHDIINCTWOFD-UHFFFAOYSA-N 0.000 claims 1
- MLPLLEANMLTQFP-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(O)(C(F)(F)F)C(F)(F)F)C1 MLPLLEANMLTQFP-UHFFFAOYSA-N 0.000 claims 1
- VQXLVYXZQWHGIC-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 VQXLVYXZQWHGIC-UHFFFAOYSA-N 0.000 claims 1
- BTSNTMSUAXGFML-UHFFFAOYSA-N 5-amino-7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 BTSNTMSUAXGFML-UHFFFAOYSA-N 0.000 claims 1
- SOGSAMOBJWIEME-UHFFFAOYSA-N 5-amino-7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=NC=CS1 SOGSAMOBJWIEME-UHFFFAOYSA-N 0.000 claims 1
- CXDFZMSBSZXFJR-UHFFFAOYSA-N 5-amino-7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=NC=CS1 CXDFZMSBSZXFJR-UHFFFAOYSA-N 0.000 claims 1
- UPHPMAILCZQPAD-UHFFFAOYSA-N 5-amino-7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1(O)CCCC1 UPHPMAILCZQPAD-UHFFFAOYSA-N 0.000 claims 1
- SWAJYGSGUKZURN-UHFFFAOYSA-N 5-amino-7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CC1 SWAJYGSGUKZURN-UHFFFAOYSA-N 0.000 claims 1
- YIQAEHRJWXJGDN-UHFFFAOYSA-N 5-amino-7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1(O)CC1 YIQAEHRJWXJGDN-UHFFFAOYSA-N 0.000 claims 1
- IFFVTBOZAQIACM-UHFFFAOYSA-N 5-amino-7-[3-[amino-(2,6-difluorophenyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=C(F)C=CC=C1F IFFVTBOZAQIACM-UHFFFAOYSA-N 0.000 claims 1
- UKSVWVSIAIDHLE-UHFFFAOYSA-N 5-amino-7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 UKSVWVSIAIDHLE-UHFFFAOYSA-N 0.000 claims 1
- SXSKXSHDTKBTCU-UHFFFAOYSA-N 5-amino-7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 SXSKXSHDTKBTCU-UHFFFAOYSA-N 0.000 claims 1
- VIOSMSQXQPQZTL-UHFFFAOYSA-N 5-amino-7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 VIOSMSQXQPQZTL-UHFFFAOYSA-N 0.000 claims 1
- KFCICSGXFZJIQD-UHFFFAOYSA-N 5-amino-7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 KFCICSGXFZJIQD-UHFFFAOYSA-N 0.000 claims 1
- MEKLSBWJOUBEQT-UHFFFAOYSA-N 5-amino-7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C=1C=2C(C(N)C)CCCC=2SC=1C(C=1C)=C(F)C(N)=C(C(NC2=O)=O)C=1N2C1CC1 MEKLSBWJOUBEQT-UHFFFAOYSA-N 0.000 claims 1
- PJVLDMCXGUNRDG-UHFFFAOYSA-N 5-amino-7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 PJVLDMCXGUNRDG-UHFFFAOYSA-N 0.000 claims 1
- IQKMLLNFMFJROE-UHFFFAOYSA-N 5-amino-7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 IQKMLLNFMFJROE-UHFFFAOYSA-N 0.000 claims 1
- TYMUOJPIMXLRBZ-UHFFFAOYSA-N 5-amino-7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 TYMUOJPIMXLRBZ-UHFFFAOYSA-N 0.000 claims 1
- XQWMPILPNSRJNG-UHFFFAOYSA-N 5-amino-7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 XQWMPILPNSRJNG-UHFFFAOYSA-N 0.000 claims 1
- AHNNHBMIEGHFFR-UHFFFAOYSA-N 5-amino-7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 AHNNHBMIEGHFFR-UHFFFAOYSA-N 0.000 claims 1
- QMBFLPPWGDIFBM-UHFFFAOYSA-N 5-amino-7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound S1C(C(N)C)=CC(C=2C(=C(N)C=3C(=O)NC(=O)N(C4CC4)C=3C=2C)F)=C1 QMBFLPPWGDIFBM-UHFFFAOYSA-N 0.000 claims 1
- OFDBKMRBZYRXED-UHFFFAOYSA-N 5-amino-7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 OFDBKMRBZYRXED-UHFFFAOYSA-N 0.000 claims 1
- SJVVHIQPGAWHQU-UHFFFAOYSA-N 5-amino-7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 SJVVHIQPGAWHQU-UHFFFAOYSA-N 0.000 claims 1
- PYIVURGCDGRXCJ-UHFFFAOYSA-N 5-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 PYIVURGCDGRXCJ-UHFFFAOYSA-N 0.000 claims 1
- KRMOFQBXNFEOOB-UHFFFAOYSA-N 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3NCCCC3C2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 KRMOFQBXNFEOOB-UHFFFAOYSA-N 0.000 claims 1
- DOFMNULLIXRBGQ-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C1=C(F)C(C(F)F)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC DOFMNULLIXRBGQ-UHFFFAOYSA-N 0.000 claims 1
- SIMHGUSAJNDGDO-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 SIMHGUSAJNDGDO-UHFFFAOYSA-N 0.000 claims 1
- PCFPVFQPRJMERR-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C(C(=C1O)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 PCFPVFQPRJMERR-UHFFFAOYSA-N 0.000 claims 1
- DKNHFHRWNFAKIB-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C(C(=C1OC)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 DKNHFHRWNFAKIB-UHFFFAOYSA-N 0.000 claims 1
- ZMQXSWDFRQZEIQ-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound C1C(N)C(CC)CCN1C1=C(F)C(C)=C2C(=O)NC(=O)N(C3CC3)C2=C1OC ZMQXSWDFRQZEIQ-UHFFFAOYSA-N 0.000 claims 1
- VMEPFMGRQGEMSX-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 VMEPFMGRQGEMSX-UHFFFAOYSA-N 0.000 claims 1
- QQXHNFHXSXXFKS-UHFFFAOYSA-N 7-(4-amino-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 QQXHNFHXSXXFKS-UHFFFAOYSA-N 0.000 claims 1
- IDXNJVGTEYNJOG-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 IDXNJVGTEYNJOG-UHFFFAOYSA-N 0.000 claims 1
- WYBZOISBKUEXQN-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 WYBZOISBKUEXQN-UHFFFAOYSA-N 0.000 claims 1
- CBNKWCAOXOEMBW-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 CBNKWCAOXOEMBW-UHFFFAOYSA-N 0.000 claims 1
- XOZFYNFVLVEIAY-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,7,8,8a-octahydrocyclohepta[c]pyrrol-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCCC3C2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 XOZFYNFVLVEIAY-UHFFFAOYSA-N 0.000 claims 1
- PLFRRLINTLURDB-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 PLFRRLINTLURDB-UHFFFAOYSA-N 0.000 claims 1
- MWWYZCUWWUTEPE-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(F)(F)C(N)C=4C=3)=C(C)C=2N1C1CC1 MWWYZCUWWUTEPE-UHFFFAOYSA-N 0.000 claims 1
- YBYOBSQBQWGMAM-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 YBYOBSQBQWGMAM-UHFFFAOYSA-N 0.000 claims 1
- MYLPHAPGBTZFBK-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(N)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 MYLPHAPGBTZFBK-UHFFFAOYSA-N 0.000 claims 1
- OIZXSFAHIQTNBU-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(N)C(F)(F)CCC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 OIZXSFAHIQTNBU-UHFFFAOYSA-N 0.000 claims 1
- ABGSFJPHEGOKGT-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1h-isoindol-2-yl)-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(N)C(F)(F)CCC4C3)=C(C)C=2N1C1CC1 ABGSFJPHEGOKGT-UHFFFAOYSA-N 0.000 claims 1
- PJBHXZYWCQXGPL-RFVHGSKJSA-N 7-[(3r)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.NC1([C@@H]2CCN(C2)C2=C(C3=C(C(NC(=O)N3C3CC3)=O)C=C2F)C)CC1 PJBHXZYWCQXGPL-RFVHGSKJSA-N 0.000 claims 1
- IEMYEMNYRBXJDD-ZVWHLABXSA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 IEMYEMNYRBXJDD-ZVWHLABXSA-N 0.000 claims 1
- QFXDUSMFLGENNW-OULXEKPRSA-N 7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-8-(difluoromethoxy)-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1OC(F)F QFXDUSMFLGENNW-OULXEKPRSA-N 0.000 claims 1
- PHXRWYOLUZCWNS-VIFPVBQESA-N 7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@H](N)C1 PHXRWYOLUZCWNS-VIFPVBQESA-N 0.000 claims 1
- CZTPKOVZHGBVOZ-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)C(F)(F)F)C1 CZTPKOVZHGBVOZ-UHFFFAOYSA-N 0.000 claims 1
- DSBXXJBZPNXIBF-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(F)C(C(N)C(F)(F)F)C1 DSBXXJBZPNXIBF-UHFFFAOYSA-N 0.000 claims 1
- TWMKTCANNDULQT-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)C(F)(F)F)C1 TWMKTCANNDULQT-UHFFFAOYSA-N 0.000 claims 1
- NJNHQWFYYRWJMK-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)C(F)(F)F)C1 NJNHQWFYYRWJMK-UHFFFAOYSA-N 0.000 claims 1
- UXARQHSCAVDVFV-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)C(F)(F)F)C1 UXARQHSCAVDVFV-UHFFFAOYSA-N 0.000 claims 1
- RIAXZOGNKZZFEF-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)F)C1 RIAXZOGNKZZFEF-UHFFFAOYSA-N 0.000 claims 1
- NNKOTKRCZZRYAO-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(F)(F)F)C1 NNKOTKRCZZRYAO-UHFFFAOYSA-N 0.000 claims 1
- OBTYBGLDODWXBB-UHFFFAOYSA-N 7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)F)C1 OBTYBGLDODWXBB-UHFFFAOYSA-N 0.000 claims 1
- QDBXUWKGUKKQFY-UHFFFAOYSA-N 7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)C(F)F)C1 QDBXUWKGUKKQFY-UHFFFAOYSA-N 0.000 claims 1
- WGGCIPOJWZWRMW-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CF)C1 WGGCIPOJWZWRMW-UHFFFAOYSA-N 0.000 claims 1
- WWVODZOPHAGJMC-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)CF)C1 WWVODZOPHAGJMC-UHFFFAOYSA-N 0.000 claims 1
- PCDNSFMTSSAPEO-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CF)C1 PCDNSFMTSSAPEO-UHFFFAOYSA-N 0.000 claims 1
- KLTYRKQIMLGKED-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(N)CO)C1 KLTYRKQIMLGKED-UHFFFAOYSA-N 0.000 claims 1
- ZJSCVWNEHGVHRY-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(C(N)CO)C1 ZJSCVWNEHGVHRY-UHFFFAOYSA-N 0.000 claims 1
- AQSLDUOIMQECRA-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CO)C1 AQSLDUOIMQECRA-UHFFFAOYSA-N 0.000 claims 1
- ZGCBBBBXLOHRJM-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CO)C1 ZGCBBBBXLOHRJM-UHFFFAOYSA-N 0.000 claims 1
- RPNFHJHPPNAORY-UHFFFAOYSA-N 7-[3-(1-amino-2-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CO)C1 RPNFHJHPPNAORY-UHFFFAOYSA-N 0.000 claims 1
- NXQZTTMGFVHNIW-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)(F)F)C1 NXQZTTMGFVHNIW-UHFFFAOYSA-N 0.000 claims 1
- PCUYEDHKAOIKPW-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)CC(F)(F)F)C1 PCUYEDHKAOIKPW-UHFFFAOYSA-N 0.000 claims 1
- IREMQRMUAHFEIH-UHFFFAOYSA-N 7-[3-(1-amino-3,3,3-trifluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)(F)F)C1 IREMQRMUAHFEIH-UHFFFAOYSA-N 0.000 claims 1
- PDQWTWXMHJDRQC-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)F)C1 PDQWTWXMHJDRQC-UHFFFAOYSA-N 0.000 claims 1
- JEVAVSZSRAQJDB-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)F)C1 JEVAVSZSRAQJDB-UHFFFAOYSA-N 0.000 claims 1
- MCJOQBKHCGBMHE-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)CC(F)F)C1 MCJOQBKHCGBMHE-UHFFFAOYSA-N 0.000 claims 1
- IEBPVJPUCOTCJW-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)F)C1 IEBPVJPUCOTCJW-UHFFFAOYSA-N 0.000 claims 1
- IMODXESPTTZZBB-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(C(F)(F)F)C1C1(N)CC1 IMODXESPTTZZBB-UHFFFAOYSA-N 0.000 claims 1
- JIEPSFBKMLHHBB-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CC(C(F)(F)F)C1C1(N)CC1 JIEPSFBKMLHHBB-UHFFFAOYSA-N 0.000 claims 1
- PDMMCCJNMMGLHR-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C1(N)CC1 PDMMCCJNMMGLHR-UHFFFAOYSA-N 0.000 claims 1
- PREDHOHJOVPLRG-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N(C1)CCC1C1(N)CC1 PREDHOHJOVPLRG-UHFFFAOYSA-N 0.000 claims 1
- CJFGVTDXBPXNEC-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CCC1C1(N)CC1 CJFGVTDXBPXNEC-UHFFFAOYSA-N 0.000 claims 1
- IRNBMRQXNOWXHL-UHFFFAOYSA-N 7-[3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C1(N)CC1 IRNBMRQXNOWXHL-UHFFFAOYSA-N 0.000 claims 1
- JJDCDAZPZWPVRW-UHFFFAOYSA-N 7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 JJDCDAZPZWPVRW-UHFFFAOYSA-N 0.000 claims 1
- UAZDYGABNWHIQY-UHFFFAOYSA-N 7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 UAZDYGABNWHIQY-UHFFFAOYSA-N 0.000 claims 1
- OXGRYRUHBINCHT-UHFFFAOYSA-N 7-[3-(2-amino-1,1,1,3,3,3-hexafluoropropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)(C(F)(F)F)C(F)(F)F)C1 OXGRYRUHBINCHT-UHFFFAOYSA-N 0.000 claims 1
- VZKUCGDCYWNQCY-UHFFFAOYSA-N 7-[3-(2-amino-1-hydroxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)CN)C1 VZKUCGDCYWNQCY-UHFFFAOYSA-N 0.000 claims 1
- PHMMVJXPSYISNF-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(CN)C1 PHMMVJXPSYISNF-UHFFFAOYSA-N 0.000 claims 1
- URQBNJNXPYGXKY-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(F)(F)F)C1 URQBNJNXPYGXKY-UHFFFAOYSA-N 0.000 claims 1
- YFNAJQOJNQMEQT-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(F)(F)F)C1 YFNAJQOJNQMEQT-UHFFFAOYSA-N 0.000 claims 1
- RUIJVLSEBLKUFG-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)F)C1 RUIJVLSEBLKUFG-UHFFFAOYSA-N 0.000 claims 1
- AQJFMKUOJNYPBA-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)F)C1 AQJFMKUOJNYPBA-UHFFFAOYSA-N 0.000 claims 1
- BNMGWQONKLGQKX-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(difluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(OC(F)F)C1 BNMGWQONKLGQKX-UHFFFAOYSA-N 0.000 claims 1
- ZKRYXASUHRMIBD-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(CN)C(CF)C1 ZKRYXASUHRMIBD-UHFFFAOYSA-N 0.000 claims 1
- IPYWKADKSFHCKR-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)(F)F)C1 IPYWKADKSFHCKR-UHFFFAOYSA-N 0.000 claims 1
- WNNCWZCVPGWPCJ-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(OC(F)(F)F)C1 WNNCWZCVPGWPCJ-UHFFFAOYSA-N 0.000 claims 1
- QVVMFDLTTNUIGA-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(OC(F)(F)F)C1 QVVMFDLTTNUIGA-UHFFFAOYSA-N 0.000 claims 1
- GSJCKJBECRXCCO-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(C(F)(F)F)C1 GSJCKJBECRXCCO-UHFFFAOYSA-N 0.000 claims 1
- LIWQYENTRXXHIX-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(C(F)(F)F)C1 LIWQYENTRXXHIX-UHFFFAOYSA-N 0.000 claims 1
- QCKZUNUDZJBTGN-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(C(F)(F)F)C1 QCKZUNUDZJBTGN-UHFFFAOYSA-N 0.000 claims 1
- NSVVDRNQHNJUPB-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 NSVVDRNQHNJUPB-UHFFFAOYSA-N 0.000 claims 1
- MSHHTZGFGNKRMV-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 MSHHTZGFGNKRMV-UHFFFAOYSA-N 0.000 claims 1
- YEDAJFXUWWNDEW-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 YEDAJFXUWWNDEW-UHFFFAOYSA-N 0.000 claims 1
- PXECMRVBAJAZLS-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 PXECMRVBAJAZLS-UHFFFAOYSA-N 0.000 claims 1
- RAYCMBHDXASDKG-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 RAYCMBHDXASDKG-UHFFFAOYSA-N 0.000 claims 1
- IKPSFSGDXNPGMU-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(CN)C1 IKPSFSGDXNPGMU-UHFFFAOYSA-N 0.000 claims 1
- LRKMAOXVMZKMOQ-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(CN)C1 LRKMAOXVMZKMOQ-UHFFFAOYSA-N 0.000 claims 1
- QOCMOYCMCSNRNM-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 QOCMOYCMCSNRNM-UHFFFAOYSA-N 0.000 claims 1
- LFIPCECDOMDDTH-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(C(F)F)C(F)F)C1 LFIPCECDOMDDTH-UHFFFAOYSA-N 0.000 claims 1
- DWPUDNJJSBBOOT-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)COC(F)(F)F)C1 DWPUDNJJSBBOOT-UHFFFAOYSA-N 0.000 claims 1
- MWNMHMUBDMAGCT-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CCC(C(N)COC(F)(F)F)C1 MWNMHMUBDMAGCT-UHFFFAOYSA-N 0.000 claims 1
- DUQXCFBQVWHDIB-UHFFFAOYSA-N 7-[3-[1-amino-2-(trifluoromethoxy)ethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)COC(F)(F)F)C1 DUQXCFBQVWHDIB-UHFFFAOYSA-N 0.000 claims 1
- DRCAHGKHNRMHJP-UHFFFAOYSA-N 7-[3-[1-amino-3,3-difluoro-2,2-bis(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(CF)(CF)C(F)F)C1 DRCAHGKHNRMHJP-UHFFFAOYSA-N 0.000 claims 1
- LFJJHMDKHBBKJL-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(CF)CF)C1 LFJJHMDKHBBKJL-UHFFFAOYSA-N 0.000 claims 1
- KGIZXCBTOLOTOS-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(CF)CF)C1 KGIZXCBTOLOTOS-UHFFFAOYSA-N 0.000 claims 1
- MQSBNCUZDBVYQO-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C(CF)CF)C1 MQSBNCUZDBVYQO-UHFFFAOYSA-N 0.000 claims 1
- DLLRVBLZJLTYSW-UHFFFAOYSA-N 7-[3-[1-amino-3-fluoro-2-(fluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(CF)CF)C1 DLLRVBLZJLTYSW-UHFFFAOYSA-N 0.000 claims 1
- ZUCJTXPFPZHYAW-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 ZUCJTXPFPZHYAW-UHFFFAOYSA-N 0.000 claims 1
- JGMCQGTWEJGNLN-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 JGMCQGTWEJGNLN-UHFFFAOYSA-N 0.000 claims 1
- PEMFQPBQPGGTCU-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)but-2-enyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)C=C(C(F)(F)F)C(F)(F)F)C1 PEMFQPBQPGGTCU-UHFFFAOYSA-N 0.000 claims 1
- UNDBIKPYVOOBHV-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 UNDBIKPYVOOBHV-UHFFFAOYSA-N 0.000 claims 1
- KDBQNPYGYWVFDY-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N1CCC(C(N)CC(C(F)(F)F)C(F)(F)F)C1 KDBQNPYGYWVFDY-UHFFFAOYSA-N 0.000 claims 1
- GNCRAMBEPLWIQI-UHFFFAOYSA-N 7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=COC=N1 GNCRAMBEPLWIQI-UHFFFAOYSA-N 0.000 claims 1
- PFVLRBJFZAWHLK-UHFFFAOYSA-N 7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=NC=CS1 PFVLRBJFZAWHLK-UHFFFAOYSA-N 0.000 claims 1
- YCWGKWOXBVREKM-UHFFFAOYSA-N 7-[3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=NC=CS1 YCWGKWOXBVREKM-UHFFFAOYSA-N 0.000 claims 1
- NIBIKQUXFILIAM-UHFFFAOYSA-N 7-[3-[amino(cyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1CC1 NIBIKQUXFILIAM-UHFFFAOYSA-N 0.000 claims 1
- INDVUDXLRCDLHJ-UHFFFAOYSA-N 7-[3-[amino(cyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1CC1 INDVUDXLRCDLHJ-UHFFFAOYSA-N 0.000 claims 1
- FYDJNXKROOFOGY-UHFFFAOYSA-N 7-[3-[amino(cyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1CC1 FYDJNXKROOFOGY-UHFFFAOYSA-N 0.000 claims 1
- NIWIVIXDHRUDCY-UHFFFAOYSA-N 7-[3-[amino(cyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1CC1 NIWIVIXDHRUDCY-UHFFFAOYSA-N 0.000 claims 1
- RZEVWAHICWCCKO-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CCCC1 RZEVWAHICWCCKO-UHFFFAOYSA-N 0.000 claims 1
- HTULLOXIGKTFHJ-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1(O)CCCC1 HTULLOXIGKTFHJ-UHFFFAOYSA-N 0.000 claims 1
- VIGCXIKFLUUKKS-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopentyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CCCC1 VIGCXIKFLUUKKS-UHFFFAOYSA-N 0.000 claims 1
- FMBPMHXDGAGVPQ-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1(O)CC1 FMBPMHXDGAGVPQ-UHFFFAOYSA-N 0.000 claims 1
- IOGOITGAGDNGLS-UHFFFAOYSA-N 7-[3-[amino-(1-hydroxycyclopropyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1(O)CC1 IOGOITGAGDNGLS-UHFFFAOYSA-N 0.000 claims 1
- XUIIFMBRHDOMNB-UHFFFAOYSA-N 7-[3-[amino-(2,6-difluorophenyl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC1C(N)C1=C(F)C=CC=C1F XUIIFMBRHDOMNB-UHFFFAOYSA-N 0.000 claims 1
- PYVBCXSYYCXIIZ-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 PYVBCXSYYCXIIZ-UHFFFAOYSA-N 0.000 claims 1
- YYYZCZVAADHIHB-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 YYYZCZVAADHIHB-UHFFFAOYSA-N 0.000 claims 1
- CPTCSSHXLKMMQB-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 CPTCSSHXLKMMQB-UHFFFAOYSA-N 0.000 claims 1
- YAPGCZBFRUQVFJ-UHFFFAOYSA-N 7-[4-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(N)C(F)(F)F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 YAPGCZBFRUQVFJ-UHFFFAOYSA-N 0.000 claims 1
- ZYHSBGGPDNQBHA-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(C=3SC=4CCCC(C=4C=3)C(N)CO)=C(C)C=2N1C1CC1 ZYHSBGGPDNQBHA-UHFFFAOYSA-N 0.000 claims 1
- DXIOMLVTGVGDGS-UHFFFAOYSA-N 7-[4-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(N)CO)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 DXIOMLVTGVGDGS-UHFFFAOYSA-N 0.000 claims 1
- XQXPASYNVHPOOE-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 XQXPASYNVHPOOE-UHFFFAOYSA-N 0.000 claims 1
- KVWSPGFFOORPFD-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C(C(=C1C(F)F)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 KVWSPGFFOORPFD-UHFFFAOYSA-N 0.000 claims 1
- XQWCIUAVVUCLTL-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C(C(=C1C)F)=C(C)C2=C1C(=O)NC(=O)N2C1CC1 XQWCIUAVVUCLTL-UHFFFAOYSA-N 0.000 claims 1
- BDGZSKUCSBJWGI-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 BDGZSKUCSBJWGI-UHFFFAOYSA-N 0.000 claims 1
- YUYKPJVDDGEVQN-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 YUYKPJVDDGEVQN-UHFFFAOYSA-N 0.000 claims 1
- UPZNPYXNLIMWTL-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C UPZNPYXNLIMWTL-UHFFFAOYSA-N 0.000 claims 1
- UEKGFPJBTHGVLQ-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C=1C=2C(C(N)C)CCCC=2SC=1C(C=1C)=C(F)C(C(F)F)=C(C(NC2=O)=O)C=1N2C1CC1 UEKGFPJBTHGVLQ-UHFFFAOYSA-N 0.000 claims 1
- RJWDCAWWXXZNAM-UHFFFAOYSA-N 7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound C=1C=2C(C(N)C)CCCC=2SC=1C(C(=C(O)C=1C(=O)NC2=O)F)=C(C)C=1N2C1CC1 RJWDCAWWXXZNAM-UHFFFAOYSA-N 0.000 claims 1
- YLUBVEQSCAFBID-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 YLUBVEQSCAFBID-UHFFFAOYSA-N 0.000 claims 1
- HRILJRZNJXSTNJ-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=C(C)C(C(NC2=O)=O)=C1N2C1CC1 HRILJRZNJXSTNJ-UHFFFAOYSA-N 0.000 claims 1
- IVWQPJIHHCAJAB-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 IVWQPJIHHCAJAB-UHFFFAOYSA-N 0.000 claims 1
- RQEKVLCJSIGHNY-UHFFFAOYSA-N 7-[4-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(C=3C=2)C(O)CN)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 RQEKVLCJSIGHNY-UHFFFAOYSA-N 0.000 claims 1
- QCEISCCDJXRCEA-UHFFFAOYSA-N 7-[4-(aminomethyl)-3,3-bis(fluoromethoxy)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(CN)C(OCF)(OCF)C1 QCEISCCDJXRCEA-UHFFFAOYSA-N 0.000 claims 1
- CUESSKGWTMFUCL-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 CUESSKGWTMFUCL-UHFFFAOYSA-N 0.000 claims 1
- LNCDNJHHFIGGLP-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 LNCDNJHHFIGGLP-UHFFFAOYSA-N 0.000 claims 1
- VIDWAJYQRKBSLD-UHFFFAOYSA-N 7-[4-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(CN)C=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 VIDWAJYQRKBSLD-UHFFFAOYSA-N 0.000 claims 1
- AANUCOSSMQSYBR-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 AANUCOSSMQSYBR-UHFFFAOYSA-N 0.000 claims 1
- AWPCFVRGWSTTDK-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(F)(F)C(CN)C=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 AWPCFVRGWSTTDK-UHFFFAOYSA-N 0.000 claims 1
- GIUQHTSHJKTTTF-UHFFFAOYSA-N 7-[4-(aminomethyl)-5,5-difluoro-6,7-dihydro-4h-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(F)(F)C(CN)C=4C=3)=C(C)C=2N1C1CC1 GIUQHTSHJKTTTF-UHFFFAOYSA-N 0.000 claims 1
- RDJMZHQQXDLTNH-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 RDJMZHQQXDLTNH-UHFFFAOYSA-N 0.000 claims 1
- BYPADLCXGCGPDL-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 BYPADLCXGCGPDL-UHFFFAOYSA-N 0.000 claims 1
- CRQSXETWIHHLTL-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 CRQSXETWIHHLTL-UHFFFAOYSA-N 0.000 claims 1
- WIKNNVSZKPHGHU-UHFFFAOYSA-N 7-[5-(1-amino-2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)C(F)(F)F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 WIKNNVSZKPHGHU-UHFFFAOYSA-N 0.000 claims 1
- SMQSWLOJZRFMQM-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(N)CO)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 SMQSWLOJZRFMQM-UHFFFAOYSA-N 0.000 claims 1
- VSMLKNMOKCBJHE-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)CO)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 VSMLKNMOKCBJHE-UHFFFAOYSA-N 0.000 claims 1
- NWHQSJNQTKOLFP-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)CO)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 NWHQSJNQTKOLFP-UHFFFAOYSA-N 0.000 claims 1
- ZIKZVLZCSIFPNW-UHFFFAOYSA-N 7-[5-(1-amino-2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CC=3C=2)C(N)CO)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 ZIKZVLZCSIFPNW-UHFFFAOYSA-N 0.000 claims 1
- NFYNONHRSOQRPB-UHFFFAOYSA-N 7-[5-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound C=1C=2CC(C(N)C)CCC=2SC=1C(C(=C(O)C=1C(=O)NC2=O)F)=C(C)C=1N2C1CC1 NFYNONHRSOQRPB-UHFFFAOYSA-N 0.000 claims 1
- KQLDRHXTTHAPDR-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=C(C(F)F)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(C(C)N)=C1 KQLDRHXTTHAPDR-UHFFFAOYSA-N 0.000 claims 1
- ZIWOWVKIDWTFLS-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound S1C(C(N)C)=CC(C=2C(=C(C(F)F)C=3C(=O)NC(=O)N(C4CC4)C=3C=2C)F)=C1 ZIWOWVKIDWTFLS-UHFFFAOYSA-N 0.000 claims 1
- KSYKHKFRGCVNAH-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(C(C)N)=C1 KSYKHKFRGCVNAH-UHFFFAOYSA-N 0.000 claims 1
- UCNMOVCFLQIUKI-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(C(C)N)=C1 UCNMOVCFLQIUKI-UHFFFAOYSA-N 0.000 claims 1
- ZKJRFJFKQLBUAB-UHFFFAOYSA-N 7-[5-(1-aminoethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound S1C(C(N)C)=CC(C=2C(=C3C(C(NC(=O)N3C3CC3)=O)=CC=2F)C)=C1 ZKJRFJFKQLBUAB-UHFFFAOYSA-N 0.000 claims 1
- HTSUHRDUYLAXBB-UHFFFAOYSA-N 7-[5-(2-amino-1-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CC=3C=2)C(O)CN)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 HTSUHRDUYLAXBB-UHFFFAOYSA-N 0.000 claims 1
- IHMNAXIODNPWMN-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 IHMNAXIODNPWMN-UHFFFAOYSA-N 0.000 claims 1
- NXSGFOOKNIITMN-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=C(O)C(C(NC2=O)=O)=C1N2C1CC1 NXSGFOOKNIITMN-UHFFFAOYSA-N 0.000 claims 1
- HBCAQTZXNYWPQZ-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(C=3SC=4CCC(CN)CC=4C=3)=C(C)C=2N1C1CC1 HBCAQTZXNYWPQZ-UHFFFAOYSA-N 0.000 claims 1
- KVNXTEIZSBHIBQ-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 KVNXTEIZSBHIBQ-UHFFFAOYSA-N 0.000 claims 1
- KTDWXDBZFIURTR-UHFFFAOYSA-N 7-[5-(aminomethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2SC=3CCC(CN)CC=3C=2)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 KTDWXDBZFIURTR-UHFFFAOYSA-N 0.000 claims 1
- QSUXIUGIUPLXDW-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 QSUXIUGIUPLXDW-UHFFFAOYSA-N 0.000 claims 1
- RTZWDOZGVAOYSF-UHFFFAOYSA-N 7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 RTZWDOZGVAOYSF-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 17
- 230000008569 process Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 136
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 134
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 133
- 125000000217 alkyl group Chemical group 0.000 description 128
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 103
- 239000000243 solution Substances 0.000 description 103
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 68
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 62
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 55
- 239000002585 base Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 43
- 239000002253 acid Substances 0.000 description 41
- 150000001408 amides Chemical class 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 34
- 235000019341 magnesium sulphate Nutrition 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 32
- 238000010992 reflux Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000013459 approach Methods 0.000 description 30
- 239000012267 brine Substances 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 25
- 229910052705 radium Inorganic materials 0.000 description 25
- 239000007858 starting material Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 229910052701 rubidium Inorganic materials 0.000 description 24
- 238000010898 silica gel chromatography Methods 0.000 description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 150000002148 esters Chemical group 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 19
- 125000006239 protecting group Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 229940086542 triethylamine Drugs 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 235000010233 benzoic acid Nutrition 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 230000009467 reduction Effects 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- 238000007363 ring formation reaction Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 239000005711 Benzoic acid Substances 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000010511 deprotection reaction Methods 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 11
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- 229910052703 rhodium Inorganic materials 0.000 description 11
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical group NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
- 229910003827 NRaRb Inorganic materials 0.000 description 9
- 239000007868 Raney catalyst Substances 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 229960003405 ciprofloxacin Drugs 0.000 description 9
- 230000026030 halogenation Effects 0.000 description 9
- 238000005658 halogenation reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 9
- 150000003235 pyrrolidines Chemical class 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- 239000012280 lithium aluminium hydride Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- 229910000085 borane Inorganic materials 0.000 description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000012038 nucleophile Substances 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000010640 amide synthesis reaction Methods 0.000 description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
- 125000003386 piperidinyl group Chemical group 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000080 stannane Inorganic materials 0.000 description 6
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
- ILSRMENRGMPIHQ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=CC(F)=CC(C(NC2=O)=O)=C1N2C1CC1 ILSRMENRGMPIHQ-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 241000282693 Cercopithecidae Species 0.000 description 5
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- NMGODFWGUBLTTA-UHFFFAOYSA-N 3-amino-1h-quinazoline-2,4-dione Chemical group C1=CC=C2C(=O)N(N)C(=O)NC2=C1 NMGODFWGUBLTTA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010958 [3+2] cycloaddition reaction Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000011152 fibreglass Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229960002510 mandelic acid Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- BLIQUJLAJXRXSG-UHFFFAOYSA-N 1-benzyl-3-(trifluoromethyl)pyrrolidin-1-ium-3-carboxylate Chemical compound C1C(C(=O)O)(C(F)(F)F)CCN1CC1=CC=CC=C1 BLIQUJLAJXRXSG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000193996 Streptococcus pyogenes Species 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 150000003936 benzamides Chemical class 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- CLMGCKCDSPUQEE-UHFFFAOYSA-N cyclopropylurea Chemical compound NC(=O)NC1CC1 CLMGCKCDSPUQEE-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000010931 ester hydrolysis Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 229940124307 fluoroquinolone Drugs 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 125000002346 iodo group Chemical group I* 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- YFZGTPLFOVVIHD-UHTWSYAYSA-N (3r,4s)-4-(fluoromethyl)-3-(hydroxymethyl)-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound N1([C@@H](C)C=2C=CC=CC=2)C[C@@H](CF)[C@H](CO)C1=O YFZGTPLFOVVIHD-UHTWSYAYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- DYVNGJKEPLWRHI-UHFFFAOYSA-N 1-(1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)cyclopropane-1-carbonitrile Chemical compound CC1=C(C2(CC2)C#N)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 DYVNGJKEPLWRHI-UHFFFAOYSA-N 0.000 description 2
- BCZJHULRTYMTDK-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 BCZJHULRTYMTDK-UHFFFAOYSA-N 0.000 description 2
- VHLOUICJKIEZJE-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 VHLOUICJKIEZJE-UHFFFAOYSA-N 0.000 description 2
- SSZJFZACPYWCNQ-ZVWHLABXSA-N 1-cyclopropyl-8-methyl-7-[(3r)-3-[(1s)-1-(methylamino)ethyl]pyrrolidin-1-yl]pyrido[4,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@H](C)NC)CCN1C1=NC=C2C(=O)NC(=O)N(C3CC3)C2=C1C SSZJFZACPYWCNQ-ZVWHLABXSA-N 0.000 description 2
- LUQFTTCSOIWEPL-UHFFFAOYSA-N 1h-quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NC(=O)NC2=C1 LUQFTTCSOIWEPL-UHFFFAOYSA-N 0.000 description 2
- NAQKDWDUMWOURZ-UHFFFAOYSA-N 2-fluoro-1-pyrrolidin-3-ylethanamine Chemical compound FCC(N)C1CCNC1 NAQKDWDUMWOURZ-UHFFFAOYSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- MBZWXTFREZMEEU-UHFFFAOYSA-N 4,6-dichloro-5-methylpyridine-3-carboxamide Chemical compound CC1=C(Cl)N=CC(C(N)=O)=C1Cl MBZWXTFREZMEEU-UHFFFAOYSA-N 0.000 description 2
- CQQBZRYFCQUYNU-UHFFFAOYSA-N 4-(1-cyanocyclopropyl)-2,5-difluoro-3-methylbenzoic acid Chemical compound CC1=C(F)C(C(O)=O)=CC(F)=C1C1(C#N)CC1 CQQBZRYFCQUYNU-UHFFFAOYSA-N 0.000 description 2
- OLTZSNKDIHJOSV-CFMCSPIPSA-N 4-(2-fluorobenzoyl)-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound C1C(=O)N([C@@H](C)C=2C=CC=CC=2)CC1C(=O)C1=CC=CC=C1F OLTZSNKDIHJOSV-CFMCSPIPSA-N 0.000 description 2
- REDSEXWGKAYROX-VUWPPUDQSA-N 4-(hydroxymethyl)-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC(CO)CC1=O REDSEXWGKAYROX-VUWPPUDQSA-N 0.000 description 2
- UYRAZWOWJZRADN-CFMCSPIPSA-N 4-[c-(2-fluorophenyl)-n-hydroxycarbonimidoyl]-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound C1C(=O)N([C@@H](C)C=2C=CC=CC=2)CC1C(=NO)C1=CC=CC=C1F UYRAZWOWJZRADN-CFMCSPIPSA-N 0.000 description 2
- QKRJZGHIXGLFDX-UHFFFAOYSA-N 4-bromo-2,5-difluoro-3-methylbenzoic acid Chemical compound CC1=C(F)C(C(O)=O)=CC(F)=C1Br QKRJZGHIXGLFDX-UHFFFAOYSA-N 0.000 description 2
- ZQQSRVPOAHYHEL-UHFFFAOYSA-N 4-bromo-2-fluorobenzoic acid Chemical class OC(=O)C1=CC=C(Br)C=C1F ZQQSRVPOAHYHEL-UHFFFAOYSA-N 0.000 description 2
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical class OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 2
- LHFOJGXXJZHEEP-UHFFFAOYSA-N 6,7-difluoro-3-methoxy-1h-quinazoline-2,4-dione Chemical compound FC1=C(F)C=C2C(=O)N(OC)C(=O)NC2=C1 LHFOJGXXJZHEEP-UHFFFAOYSA-N 0.000 description 2
- GFIWUMNMKJPZBO-FJXQXJEOSA-N 7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)NC(=O)N2C1CC1 GFIWUMNMKJPZBO-FJXQXJEOSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 238000010934 O-alkylation reaction Methods 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- KFTZCNLLRKFMQH-BYPYZUCNSA-N [(3s)-pyrrolidin-3-yl]carbamic acid Chemical compound OC(=O)N[C@H]1CCNC1 KFTZCNLLRKFMQH-BYPYZUCNSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000011482 antibacterial activity assay Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229940054066 benzamide antipsychotics Drugs 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- PJWHQOGDYUZVKD-UHFFFAOYSA-N benzyl 3-(c-cyclopropyl-n-hydroxycarbonimidoyl)pyrrolidine-1-carboxylate Chemical compound C1CN(C(=O)OCC=2C=CC=CC=2)CC1C(=NO)C1CC1 PJWHQOGDYUZVKD-UHFFFAOYSA-N 0.000 description 2
- CFFVWXSTESOUBO-UHFFFAOYSA-N benzyl 3-(cyclopropanecarbonyl)pyrrolidine-1-carboxylate Chemical compound C1CC(C(=O)C2CC2)CN1C(=O)OCC1=CC=CC=C1 CFFVWXSTESOUBO-UHFFFAOYSA-N 0.000 description 2
- UXACEQFWWYDRBH-UHFFFAOYSA-N benzyl 3-(methoxymethylcarbamoyl)pyrrolidine-1-carboxylate Chemical compound C1C(C(=O)NCOC)CCN1C(=O)OCC1=CC=CC=C1 UXACEQFWWYDRBH-UHFFFAOYSA-N 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- VALPXRNQZYGXPS-UHFFFAOYSA-N benzyl pyrrolidine-1-carboxylate Chemical compound C1CCCN1C(=O)OCC1=CC=CC=C1 VALPXRNQZYGXPS-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- SGBOSIHDWPCEJB-IACUBPJLSA-N diazonio-[[(3s,4s)-4-(fluoromethyl)-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]methyl]azanide Chemical compound N1([C@@H](C)C=2C=CC=CC=2)C[C@@H](CF)[C@H](CN=[N+]=[N-])C1 SGBOSIHDWPCEJB-IACUBPJLSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 101150070420 gyrA gene Proteins 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003328 mesylation reaction Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- MXFUZDUNEIGESI-UHFFFAOYSA-N methyl 3-ethylsulfanyl-4,5-difluoro-2-methyl-1h-indole-7-carboxylate Chemical compound C1=C(F)C(F)=C2C(SCC)=C(C)NC2=C1C(=O)OC MXFUZDUNEIGESI-UHFFFAOYSA-N 0.000 description 2
- TYSKEINUAYGBIY-UHFFFAOYSA-N methyl 4,5-difluoro-2-methyl-2,3-dihydro-1h-indole-7-carboxylate Chemical compound COC(=O)C1=CC(F)=C(F)C2=C1NC(C)C2 TYSKEINUAYGBIY-UHFFFAOYSA-N 0.000 description 2
- QWAAJJUJHBTSDP-CFVMTHIKSA-N methyl [(3S,4S)-4-(fluoromethyl)-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]methanesulfonate Chemical compound C1[C@@H](CF)[C@H](CS(=O)(=O)OC)CN1[C@@H](C)C1=CC=CC=C1 QWAAJJUJHBTSDP-CFVMTHIKSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 2
- 238000005497 microtitration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- DWDGPWMXLBVDNG-AMGKYWFPSA-N n-(methoxymethyl)-5-oxo-1-[(1s)-1-phenylethyl]pyrrolidine-3-carboxamide Chemical compound O=C1CC(C(=O)NCOC)CN1[C@@H](C)C1=CC=CC=C1 DWDGPWMXLBVDNG-AMGKYWFPSA-N 0.000 description 2
- PBQZQTQFQFYBNJ-UHFFFAOYSA-N n-methoxybenzamide Chemical class CONC(=O)C1=CC=CC=C1 PBQZQTQFQFYBNJ-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000008512 pyrimidinediones Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- HJUZGKGDCUOVML-BDAKNGLRSA-N tert-butyl n-[(1r)-1-[(3s)-pyrrolidin-3-yl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C)[C@H]1CCNC1 HJUZGKGDCUOVML-BDAKNGLRSA-N 0.000 description 2
- NGSIXWVCERJXKG-UONOGXRCSA-N tert-butyl n-[(1s)-1-[(3r)-1-(1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]carbamate Chemical compound C1[C@H]([C@@H](NC(=O)OC(C)(C)C)C)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1C NGSIXWVCERJXKG-UONOGXRCSA-N 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical group NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GBVBYEVLALCXBL-RQJHMYQMSA-N (1r)-n-methyl-1-[(3s)-pyrrolidin-3-yl]ethanamine Chemical compound CN[C@H](C)[C@H]1CCNC1 GBVBYEVLALCXBL-RQJHMYQMSA-N 0.000 description 1
- PQXKWPLDPFFDJP-ZXZARUISSA-N (2r,3s)-2,3-dimethyloxirane Chemical compound C[C@H]1O[C@H]1C PQXKWPLDPFFDJP-ZXZARUISSA-N 0.000 description 1
- ZNPFXXNHYARXSV-DBVUQKKJSA-N (3r,4s)-4-(fluoromethyl)-1-[(1s)-1-phenylethyl]-3-(phenylmethoxymethyl)pyrrolidin-2-one Chemical compound C([C@H]1[C@H](CF)CN(C1=O)[C@@H](C)C=1C=CC=CC=1)OCC1=CC=CC=C1 ZNPFXXNHYARXSV-DBVUQKKJSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- NHCAOSAVSCXSIT-UHFFFAOYSA-N 1,10-diazatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraene-9,11-dione Chemical compound C1=CC2=CC=CC3=C2N1C(=O)NC3=O NHCAOSAVSCXSIT-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- HKIPCXRNASWFRU-UHFFFAOYSA-N 1,3-difluoropropan-2-one Chemical compound FCC(=O)CF HKIPCXRNASWFRU-UHFFFAOYSA-N 0.000 description 1
- VPKKBWBYGRMALQ-UHFFFAOYSA-N 1-$l^{1}-azanylpyrrolidine Chemical compound [N]N1CCCC1 VPKKBWBYGRMALQ-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
- OXXYSUISWIALQY-UHFFFAOYSA-N 1-benzyl-3-(2-bromoacetyl)pyrrolidin-2-one Chemical compound O=C1C(C(=O)CBr)CCN1CC1=CC=CC=C1 OXXYSUISWIALQY-UHFFFAOYSA-N 0.000 description 1
- PQNZVRYLUYKDEK-UHFFFAOYSA-N 1-benzyl-3-(2-fluoroacetyl)pyrrolidin-2-one Chemical compound O=C1C(C(=O)CF)CCN1CC1=CC=CC=C1 PQNZVRYLUYKDEK-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- KFJCEHHUJXKLDM-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methylquinazoline-2,4-dione 1-cyclopropyl-7-(dimethylamino)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1(CC1)N1C(NC(C2=CC(=C(C(=C12)C)F)F)=O)=O.C1(CC1)N1C(NC(C2=CC(=C(C(=C12)C)N(C)C)F)=O)=O KFJCEHHUJXKLDM-UHFFFAOYSA-N 0.000 description 1
- RYWUCROSFBWYGB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C1(CC1)N1C(NC(C2=C(C(=CC(=C12)C)F)C)=O)=O RYWUCROSFBWYGB-UHFFFAOYSA-N 0.000 description 1
- JKNRKUOBYTXAQU-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(O)CCCC4C3)=C(C)C=2N1C1CC1 JKNRKUOBYTXAQU-UHFFFAOYSA-N 0.000 description 1
- ALLVJEJVIRJOCK-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(OC)=C(F)C(N3CC4C(O)CCCC4C3)=C(C)C=2N1C1CC1 ALLVJEJVIRJOCK-UHFFFAOYSA-N 0.000 description 1
- YHVXUVUISJJHEN-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-5,8-dimethylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(N3CC4C(O)CCC4C3)=C(C)C=2N1C1CC1 YHVXUVUISJJHEN-UHFFFAOYSA-N 0.000 description 1
- JNCIMXWGLWOXHB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(1-hydroxycyclopropyl)pyrrolidin-1-yl]-5-methoxy-8-methylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(OC)=C(F)C=1N(C1)CCC1C1(O)CC1 JNCIMXWGLWOXHB-UHFFFAOYSA-N 0.000 description 1
- DGRYNZUJVRHIPR-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CO)C1 DGRYNZUJVRHIPR-UHFFFAOYSA-N 0.000 description 1
- KIVVICKDWOHNHS-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-(hydroxymethyl)pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound CC=1C=2N(C3CC3)C(=O)NC(=O)C=2C(C)=C(F)C=1N1CC(F)C(CO)C1 KIVVICKDWOHNHS-UHFFFAOYSA-N 0.000 description 1
- NNNUPFXUDBNDAX-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-fluoro-4-[(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]-5,8-dimethylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(O)C1=CC=C(F)C=C1 NNNUPFXUDBNDAX-UHFFFAOYSA-N 0.000 description 1
- DCPYEEYKLICNTD-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=CC(F)=CC(C(NC2=O)=O)=C1N2C1CC1 DCPYEEYKLICNTD-UHFFFAOYSA-N 0.000 description 1
- IYNHFDQCFUAIGU-UHFFFAOYSA-N 1-cyclopropyl-7-(dimethylamino)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC=1C(N(C)C)=C(F)C=C(C(NC2=O)=O)C=1N2C1CC1 IYNHFDQCFUAIGU-UHFFFAOYSA-N 0.000 description 1
- ZGCGNTZEVIIFAM-UHFFFAOYSA-N 1-fluoro-8-methylquinazoline-2,4-dione Chemical compound FN1C(=O)NC(=O)C2=C1C(C)=CC=C2 ZGCGNTZEVIIFAM-UHFFFAOYSA-N 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical class ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- JSASVUTVTRNJHA-UHFFFAOYSA-N 1-phenylmethoxycarbonylpyrrolidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCN1C(=O)OCC1=CC=CC=C1 JSASVUTVTRNJHA-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JQPYINKVAWEQDQ-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=N1 JQPYINKVAWEQDQ-UHFFFAOYSA-N 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- AKAMNXFLKYKFOJ-UHFFFAOYSA-N 2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1F AKAMNXFLKYKFOJ-UHFFFAOYSA-N 0.000 description 1
- KWLIGHXPUYUTBH-UHFFFAOYSA-N 2,4-difluoro-3-methoxybenzoic acid Chemical compound COC1=C(F)C=CC(C(O)=O)=C1F KWLIGHXPUYUTBH-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- JZUPYBRYQINNRE-UHFFFAOYSA-N 2,6-dimethyl-1,4-dioxane Chemical compound CC1COCC(C)O1 JZUPYBRYQINNRE-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- XNGZCSGZQAPBAI-UHFFFAOYSA-N 2-amino-4,5-difluoro-n-methoxybenzamide Chemical compound CONC(=O)C1=CC(F)=C(F)C=C1N XNGZCSGZQAPBAI-UHFFFAOYSA-N 0.000 description 1
- DGOZIZVTANAGCA-UHFFFAOYSA-N 2-amino-4,5-difluorobenzoic acid Chemical compound NC1=CC(F)=C(F)C=C1C(O)=O DGOZIZVTANAGCA-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- HPQCENXKIPSQSA-UHFFFAOYSA-N 2-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CCNC1=O HPQCENXKIPSQSA-UHFFFAOYSA-N 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FPHNWFFKQCPXPI-UHFFFAOYSA-N 3-chlorooxolane Chemical compound ClC1CCOC1 FPHNWFFKQCPXPI-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical class OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 1
- AUHDNNHRDJYDDO-UHFFFAOYSA-N 3-methoxy-1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)N(OC)C(=O)NC2=C1 AUHDNNHRDJYDDO-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- RNEFMHSKWUXTNK-UHFFFAOYSA-N 4,5-difluoro-2-methyl-1h-indole-7-carboxylic acid Chemical compound FC1=CC(C(O)=O)=C2NC(C)=CC2=C1F RNEFMHSKWUXTNK-UHFFFAOYSA-N 0.000 description 1
- CBSZOUNRMFQJOB-UHFFFAOYSA-N 4,6-dichloro-5-methylpyridine-3-carboxylic acid Chemical compound CC1=C(Cl)N=CC(C(O)=O)=C1Cl CBSZOUNRMFQJOB-UHFFFAOYSA-N 0.000 description 1
- ZMQHJILVRARMOP-UHFFFAOYSA-N 4,6-dichloro-n-(cyclopropylcarbamoyl)-5-methylpyridine-3-carboxamide Chemical compound CC1=C(Cl)N=CC(C(=O)NC(=O)NC2CC2)=C1Cl ZMQHJILVRARMOP-UHFFFAOYSA-N 0.000 description 1
- HYKXFMADFPZXHR-UHFFFAOYSA-N 4-(1-cyanocyclopropyl)-n-(cyclopropylcarbamoyl)-2,5-difluoro-3-methylbenzamide Chemical compound CC1=C(F)C(C(=O)NC(=O)NC2CC2)=CC(F)=C1C1(C#N)CC1 HYKXFMADFPZXHR-UHFFFAOYSA-N 0.000 description 1
- LOSHCCKMXMTECP-UHFFFAOYSA-N 4-(fluoromethyl)-1-(1-phenylethyl)pyrrolidin-2-one Chemical compound C=1C=CC=CC=1C(C)N1CC(CF)CC1=O LOSHCCKMXMTECP-UHFFFAOYSA-N 0.000 description 1
- LOSHCCKMXMTECP-VUWPPUDQSA-N 4-(fluoromethyl)-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC(CF)CC1=O LOSHCCKMXMTECP-VUWPPUDQSA-N 0.000 description 1
- CCKZNIFJRKLUTI-XIWWETDGSA-N 4-[amino-(2-fluorophenyl)methyl]-1-[(1s)-1-phenylethyl]pyrrolidin-2-one Chemical compound C1C(=O)N([C@@H](C)C=2C=CC=CC=2)CC1C(N)C1=CC=CC=C1F CCKZNIFJRKLUTI-XIWWETDGSA-N 0.000 description 1
- TVQZQYSBVDCWFT-UHFFFAOYSA-N 4-amino-2,5-difluoro-3-methylbenzoic acid Chemical compound CC1=C(N)C(F)=CC(C(O)=O)=C1F TVQZQYSBVDCWFT-UHFFFAOYSA-N 0.000 description 1
- JRFYDIIVYQRAOP-UHFFFAOYSA-N 4-bromo-2,5-difluoro-3-methylbenzamide Chemical compound CC1=C(F)C(C(N)=O)=CC(F)=C1Br JRFYDIIVYQRAOP-UHFFFAOYSA-N 0.000 description 1
- VJOLCDGRNCRGMJ-UHFFFAOYSA-N 4-methylmorpholine;2-methylpropyl carbonochloridate Chemical compound CN1CCOCC1.CC(C)COC(Cl)=O VJOLCDGRNCRGMJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- MHKXHXIPIFAPCT-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3C(O)CCC3C2)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 MHKXHXIPIFAPCT-UHFFFAOYSA-N 0.000 description 1
- NDFCFTOWEKYFMV-UHFFFAOYSA-N 5-amino-1h-quinazoline-2,4-dione Chemical class N1C(=O)NC(=O)C2=C1C=CC=C2N NDFCFTOWEKYFMV-UHFFFAOYSA-N 0.000 description 1
- NKCBKSSCDAIFKX-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2,2-difluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)F)C1 NKCBKSSCDAIFKX-UHFFFAOYSA-N 0.000 description 1
- IXSRKKQQZGYDER-UHFFFAOYSA-N 5-amino-7-[3-(1-amino-2-hydroxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methyl-6,7-dihydroquinazoline-2,4-dione Chemical compound O=C1NC(=O)C2=C(N)C(F)C(N3CC(C(F)C3)C(N)CO)C(C)=C2N1C1CC1 IXSRKKQQZGYDER-UHFFFAOYSA-N 0.000 description 1
- UOVUUHBQLYJULT-UHFFFAOYSA-N 5-amino-7-[3-(aminomethyl)-4-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(CC(C(F)(F)F)C(F)(F)F)C1 UOVUUHBQLYJULT-UHFFFAOYSA-N 0.000 description 1
- HNNLNDSLURGORN-UHFFFAOYSA-N 5-amino-7-[3-[amino(1,3-oxazol-4-yl)methyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=C(N)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)C1=COC=N1 HNNLNDSLURGORN-UHFFFAOYSA-N 0.000 description 1
- KGJBLCZWIWQBJJ-UHFFFAOYSA-N 5-amino-7-[4-(1-aminoethyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2SC=3CCCC(C=3C=2)C(C)N)C(F)=C(N)C(C(NC2=O)=O)=C1N2C1CC1 KGJBLCZWIWQBJJ-UHFFFAOYSA-N 0.000 description 1
- PMHWMWJIEAQCPA-UHFFFAOYSA-N 5-amino-8,9-difluoro-3-methyl-2,3-dihydro-1-oxa-3a,5-diazaphenalene-4,6-dione Chemical compound O1CC(C)N2C(=O)N(N)C(=O)C3=C2C1=C(F)C(F)=C3 PMHWMWJIEAQCPA-UHFFFAOYSA-N 0.000 description 1
- MRZRYTQAWAFKOC-UHFFFAOYSA-N 5-methoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=CC=C2OC MRZRYTQAWAFKOC-UHFFFAOYSA-N 0.000 description 1
- OVLVVBLYTQYCCS-UHFFFAOYSA-N 5-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=CC=C2C OVLVVBLYTQYCCS-UHFFFAOYSA-N 0.000 description 1
- CFGKWSDAMXTRHE-FTNKSUMCSA-N 5-oxo-1-[(1s)-1-phenylethyl]pyrrolidine-3-carboxylic acid Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC(C(O)=O)CC1=O CFGKWSDAMXTRHE-FTNKSUMCSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- KVXBGKKOZBIJDV-UHFFFAOYSA-N 6,7-difluoro-1-(2-methoxy-1-methylcyclopropyl)quinazoline-2,4-dione Chemical compound COC1CC1(C)N1C(=O)NC(=O)C2=CC(F)=C(F)C=C21 KVXBGKKOZBIJDV-UHFFFAOYSA-N 0.000 description 1
- IDHPZYGPIVKKRC-UHFFFAOYSA-N 6,7-difluoro-3-methoxy-1-(1-methylcyclopropyl)quinazoline-2,4-dione Chemical compound C12=CC(F)=C(F)C=C2C(=O)N(OC)C(=O)N1C1(C)CC1 IDHPZYGPIVKKRC-UHFFFAOYSA-N 0.000 description 1
- FSQFWXNCIOIHJI-UHFFFAOYSA-N 7-(2-amino-5-azaspiro[2.4]heptan-5-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC21CC2N FSQFWXNCIOIHJI-UHFFFAOYSA-N 0.000 description 1
- FQZIICDHFDQSKW-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C(F)(F)CC3C2)C(F)=C(C(F)F)C(C(NC2=O)=O)=C1N2C1CC1 FQZIICDHFDQSKW-UHFFFAOYSA-N 0.000 description 1
- LBFHMYSJZGGIDU-UHFFFAOYSA-N 7-(4-amino-5,5-difluoro-6,7-dihydro-4H-1-benzothiophen-2-yl)-1-cyclopropyl-6-fluoro-5-hydroxy-8-methyl-6,7-dihydroquinazoline-2,4-dione Chemical compound NC1C(CCC=2SC(=CC21)C2C(C(=C1C(NC(N(C1=C2C)C2CC2)=O)=O)O)F)(F)F LBFHMYSJZGGIDU-UHFFFAOYSA-N 0.000 description 1
- LPKNKQKFZJKKDN-UHFFFAOYSA-N 7-(7-amino-6,6-difluoro-3,3a,4,5,7,7a-hexahydro-1H-isoindol-2-yl)-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-6,7-dihydroquinazoline-2,4-dione Chemical compound NC1C2CN(CC2CCC1(F)F)C1C(C(=C2C(NC(N(C2=C1OC)C1CC1)=O)=O)C(F)F)F LPKNKQKFZJKKDN-UHFFFAOYSA-N 0.000 description 1
- ZYKAJZMKNJPESZ-ZETCQYMHSA-N 7-[(3s)-3-aminopyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1Cl ZYKAJZMKNJPESZ-ZETCQYMHSA-N 0.000 description 1
- UOTVQSNCXAVZNT-UHFFFAOYSA-N 7-[3-(1-amino-2,2,2-trifluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)C(F)(F)F)C1 UOTVQSNCXAVZNT-UHFFFAOYSA-N 0.000 description 1
- GPBFHCMFHXCXAK-UHFFFAOYSA-N 7-[3-(1-amino-2-fluoroethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CF)C1 GPBFHCMFHXCXAK-UHFFFAOYSA-N 0.000 description 1
- MCLBYOJRZWPPSS-UHFFFAOYSA-N 7-[3-(1-amino-3,3-difluoropropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-hydroxy-8-methylquinazoline-2,4-dione Chemical compound FC1=C(O)C(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(N)CC(F)F)C1 MCLBYOJRZWPPSS-UHFFFAOYSA-N 0.000 description 1
- KGUVSRPTESZNQJ-UHFFFAOYSA-N 7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(NC(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)N)C1 KGUVSRPTESZNQJ-UHFFFAOYSA-N 0.000 description 1
- RXOQUHRLPJYVFA-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-(difluoromethyl)-6-fluoro-8-methoxy-6,7-dihydroquinazoline-2,4-dione Chemical compound O=C1NC(=O)C2=C(C(F)F)C(F)C(N3CC(C(CN)C3)C(F)(F)F)C(OC)=C2N1C1CC1 RXOQUHRLPJYVFA-UHFFFAOYSA-N 0.000 description 1
- FQZCQYPWXFAAOO-UHFFFAOYSA-N 7-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-6,7-dihydroquinazoline-2,4-dione Chemical compound O=C1NC(=O)C2=CC(F)C(N3CC(C(CN)C3)C(F)(F)F)C(OC)=C2N1C1CC1 FQZCQYPWXFAAOO-UHFFFAOYSA-N 0.000 description 1
- KQNBXHFGEZBOMP-UHFFFAOYSA-N 7-[3-[1-amino-2-(difluoromethyl)-3,3-difluoropropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methyl-6,7-dihydroquinazoline-2,4-dione Chemical compound O=C1NC(=O)C2=CC(F)C(N3CC(CC3)C(N)C(C(F)F)C(F)F)C(C)=C2N1C1CC1 KQNBXHFGEZBOMP-UHFFFAOYSA-N 0.000 description 1
- YNLZJERZORRSQP-UHFFFAOYSA-N 7-[3-[1-amino-4,4,4-trifluoro-3-(trifluoromethyl)butyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methoxy-8-methyl-6,7-dihydroquinazoline-2,4-dione Chemical compound C12=C(C)C(N3CC(CC3)C(N)CC(C(F)(F)F)C(F)(F)F)C(F)C(OC)=C2C(=O)NC(=O)N1C1CC1 YNLZJERZORRSQP-UHFFFAOYSA-N 0.000 description 1
- IMAWIFYMSJHCOO-UHFFFAOYSA-N 7-bromo-3-ethylsulfanyl-4,5-difluoro-2-methyl-1h-indole Chemical compound C1=C(F)C(F)=C2C(SCC)=C(C)NC2=C1Br IMAWIFYMSJHCOO-UHFFFAOYSA-N 0.000 description 1
- QDTWLXJVBYSGPS-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(Cl)N=CC(C(NC2=O)=O)=C1N2C1CC1 QDTWLXJVBYSGPS-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000579120 Coliiformes Species 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 108010067770 Endopeptidase K Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920001917 Ficoll Polymers 0.000 description 1
- 206010016952 Food poisoning Diseases 0.000 description 1
- 208000019331 Foodborne disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241001108452 Neisseria gonorrhoeae MS11 Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GUEGTXPYTZRYQE-UHFFFAOYSA-N O1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3N Chemical compound O1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3N GUEGTXPYTZRYQE-UHFFFAOYSA-N 0.000 description 1
- WXLMNNXUMWCJEG-UHFFFAOYSA-N O1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3[N+]([O-])=O Chemical compound O1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3[N+]([O-])=O WXLMNNXUMWCJEG-UHFFFAOYSA-N 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- RWCOTTLHDJWHRS-YUMQZZPRSA-N Pro-Pro Chemical compound OC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 RWCOTTLHDJWHRS-YUMQZZPRSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- IXEVGHXRXDBAOB-GBIKHYSHSA-N [(1r,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-thiocyanatoacetate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)CSC#N)C[C@@H]1C2(C)C IXEVGHXRXDBAOB-GBIKHYSHSA-N 0.000 description 1
- GLYOPNLBKCBTMI-UHFFFAOYSA-N [2-chloro-2-(1-chloro-2-phenylethoxy)ethyl]benzene Chemical compound C=1C=CC=CC=1CC(Cl)OC(Cl)CC1=CC=CC=C1 GLYOPNLBKCBTMI-UHFFFAOYSA-N 0.000 description 1
- VUJIGDRUEAEHDP-UHFFFAOYSA-N [5-oxo-1-(1-phenylethyl)pyrrolidin-3-yl]methyl methanesulfonate Chemical compound C=1C=CC=CC=1C(C)N1CC(COS(C)(=O)=O)CC1=O VUJIGDRUEAEHDP-UHFFFAOYSA-N 0.000 description 1
- VUJIGDRUEAEHDP-PXYINDEMSA-N [5-oxo-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]methyl methanesulfonate Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC(COS(C)(=O)=O)CC1=O VUJIGDRUEAEHDP-PXYINDEMSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000011543 agarose gel Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 208000037815 bloodstream infection Diseases 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- LKXYJYDRLBPHRS-UHFFFAOYSA-N bromocyclopropane Chemical compound BrC1CC1 LKXYJYDRLBPHRS-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- RUEKPBLTWGFBOD-UHFFFAOYSA-N bromoethyne Chemical group BrC#C RUEKPBLTWGFBOD-UHFFFAOYSA-N 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- ILAJWURWJKXJPW-UHFFFAOYSA-N butanedioic acid;octanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)CCCCCCC(O)=O ILAJWURWJKXJPW-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 150000001916 cyano esters Chemical class 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000005888 cyclopropanation reaction Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-DYCDLGHISA-N deuterium bromide Chemical compound [2H]Br CPELXLSAUQHCOX-DYCDLGHISA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- BQXRRXOXAURMED-CHWSQXEVSA-N diazonio-[[(3s,4s)-4-(fluoromethyl)-1-phenylmethoxycarbonylpyrrolidin-3-yl]methyl]azanide Chemical compound C1[C@@H](CN=[N+]=[N-])[C@H](CF)CN1C(=O)OCC1=CC=CC=C1 BQXRRXOXAURMED-CHWSQXEVSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000006371 dihalo methyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- HPTQKSXAQBHFKL-UHFFFAOYSA-N dipyrrolidin-1-ylmethanone Chemical compound C1CCCN1C(=O)N1CCCC1 HPTQKSXAQBHFKL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- CNLWICAPVKYJDJ-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(C)=C1F CNLWICAPVKYJDJ-UHFFFAOYSA-N 0.000 description 1
- ZUTXKBXBNPVWCO-UHFFFAOYSA-N ethyl 4-(cyanomethyl)-2,5-difluoro-3-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(CC#N)C(C)=C1F ZUTXKBXBNPVWCO-UHFFFAOYSA-N 0.000 description 1
- PHEAEDOAVGIUOY-UHFFFAOYSA-N ethyl 4-[1-cyano-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-2,5-difluoro-3-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(C(C#N)C(=O)OC(C)(C)C)C(C)=C1F PHEAEDOAVGIUOY-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000006419 fluorocyclopropyl group Chemical group 0.000 description 1
- XLPOMDDUVURFBI-UHFFFAOYSA-N fluoromethoxymethylbenzene Chemical compound FCOCC1=CC=CC=C1 XLPOMDDUVURFBI-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- XNABHFLZYMCJHE-UHFFFAOYSA-N furan-3-ylmethanamine Chemical compound NCC=1C=COC=1 XNABHFLZYMCJHE-UHFFFAOYSA-N 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 101150059798 grlA gene Proteins 0.000 description 1
- 101150097244 grxC2 gene Proteins 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000006801 homologous recombination Effects 0.000 description 1
- 238000002744 homologous recombination Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- VLODBNNWEWTQJX-UHFFFAOYSA-N iodocyclopropane Chemical compound IC1CC1 VLODBNNWEWTQJX-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- JJXINDNYLSMEBI-UHFFFAOYSA-N isocyanato thiohypochlorite Chemical compound ClSN=C=O JJXINDNYLSMEBI-UHFFFAOYSA-N 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- YSQFBLFEYNOIBW-UHFFFAOYSA-N lithium;cyclopropane Chemical compound [Li+].C1C[CH-]1 YSQFBLFEYNOIBW-UHFFFAOYSA-N 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 239000012160 loading buffer Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- JFBOGMHOFVEHBH-UHFFFAOYSA-N methyl 4,5-difluoro-2-methyl-1h-indole-7-carboxylate Chemical compound COC(=O)C1=CC(F)=C(F)C2=C1NC(C)=C2 JFBOGMHOFVEHBH-UHFFFAOYSA-N 0.000 description 1
- BENQIPNJLDAXAT-UHFFFAOYSA-N methyl 5-oxo-1-(1-phenylethyl)pyrrolidine-3-carboxylate Chemical compound O=C1CC(C(=O)OC)CN1C(C)C1=CC=CC=C1 BENQIPNJLDAXAT-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 description 1
- MIVGZOMJVVQBAO-UHFFFAOYSA-N n,n-dibenzylprop-2-enamide Chemical compound C=1C=CC=CC=1CN(C(=O)C=C)CC1=CC=CC=C1 MIVGZOMJVVQBAO-UHFFFAOYSA-N 0.000 description 1
- VSPPONOIKZXUBJ-UHFFFAOYSA-N n,n-diethylethanamine;oxolane Chemical compound C1CCOC1.CCN(CC)CC VSPPONOIKZXUBJ-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- VBBUFMFZDHLELS-UHFFFAOYSA-N n-(oxomethylidene)carbamoyl chloride Chemical compound ClC(=O)N=C=O VBBUFMFZDHLELS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 101150110811 parC gene Proteins 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108010077112 prolyl-proline Proteins 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical group C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical group NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 101150079601 recA gene Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 102220040238 rs116211453 Human genes 0.000 description 1
- 102200017867 rs121434558 Human genes 0.000 description 1
- 102200118227 rs34579351 Human genes 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000005797 stannylation reaction Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 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 description 1
- BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 1
- KKJWRIWTSCLEOI-GLXQMMQGSA-N tert-butyl N-[(1S)-1-[(3R)-1-(6-amino-7-fluoro-12-methyl-2,4-dioxo-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-8-yl)pyrrolidin-3-yl]ethyl]carbamate Chemical compound C1[C@H]([C@@H](NC(=O)OC(C)(C)C)C)CCN1C1=C(F)C(N)=C2C(=O)NC(=O)N3C(C)COC1=C32 KKJWRIWTSCLEOI-GLXQMMQGSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- QIYOMZXJQAKHEK-DHBOJHSNSA-N tert-butyl n-[(1r,5s)-3-azabicyclo[3.1.0]hexan-6-yl]carbamate Chemical compound C1NC[C@H]2C(NC(=O)OC(C)(C)C)[C@H]21 QIYOMZXJQAKHEK-DHBOJHSNSA-N 0.000 description 1
- ZDYIGGZEAXUVSM-JTQLQIEISA-N tert-butyl n-[(3s)-1-(8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C2C(=O)NC(=O)N(C3CC3)C2=C1Cl ZDYIGGZEAXUVSM-JTQLQIEISA-N 0.000 description 1
- DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- KYRMVJXDHKIHEH-UHFFFAOYSA-N tert-butyl n-[[1-(1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]-(2-fluorophenyl)methyl]carbamate Chemical compound FC1=CC(C(NC(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(NC(=O)OC(C)(C)C)C1=CC=CC=C1F KYRMVJXDHKIHEH-UHFFFAOYSA-N 0.000 description 1
- UQCWXKSHRQJGPH-UHFFFAOYSA-M tetrabutylazanium;fluoride;hydrate Chemical compound O.[F-].CCCC[N+](CCCC)(CCCC)CCCC UQCWXKSHRQJGPH-UHFFFAOYSA-M 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- MASNJXDMMSOROP-UHFFFAOYSA-N triethylsilane 2,2,2-trifluoroacetic acid Chemical compound CC[SiH](CC)CC.OC(=O)C(F)(F)F MASNJXDMMSOROP-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000006004 trihaloethyl group Chemical group 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
L'invention concerne des composés représentés par la formule (I) dans laquelle R¿1?-R¿6,? J et K ont n'importe lesquelles des valeurs définies dans le descriptif, ainsi que leurs sels pharmaceutiquement acceptables, qui sont utilisés comme agents antibactériens. Par ailleurs, l'invention concerne des compositions pharmaceutiques contenant un ou plusieurs des composés de la formule (I), des procédés de préparation des composés de formule (I), ainsi que des intermédiaires utilisés pour préparer les composés de formule (I).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29924901P | 2001-06-19 | 2001-06-19 | |
US60/299,249 | 2001-06-19 | ||
PCT/IB2002/001768 WO2002102793A2 (fr) | 2001-06-19 | 2002-05-13 | Agents antibacteriens |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2446963A1 true CA2446963A1 (fr) | 2002-12-27 |
Family
ID=23153973
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002446963A Abandoned CA2446963A1 (fr) | 2001-06-19 | 2002-05-13 | Agents antibacteriens |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1401830A2 (fr) |
JP (1) | JP2005501021A (fr) |
AU (1) | AU2002302894A1 (fr) |
BR (1) | BR0210028A (fr) |
CA (1) | CA2446963A1 (fr) |
DO (1) | DOP2002000422A (fr) |
GT (1) | GT200200104A (fr) |
HN (1) | HN2002000150A (fr) |
MX (1) | MXPA03009894A (fr) |
PA (1) | PA8548401A1 (fr) |
PE (1) | PE20030272A1 (fr) |
SV (1) | SV2003001089A (fr) |
WO (1) | WO2002102793A2 (fr) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0414319A (pt) * | 2003-09-12 | 2006-11-07 | Warner Lambert Co | agentes antibacterianos de quinolona |
EP1687296A1 (fr) * | 2003-11-18 | 2006-08-09 | Warner-Lambert Company LLC | Derives antibacteriens d'aminoquinazolidinedione |
WO2012088266A2 (fr) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Imidazopyridazines et benzimidazoles substitués en tant qu'inhibiteurs de fgfr3 |
CN103443085B (zh) | 2011-03-14 | 2016-03-23 | 南京英派药业有限公司 | 喹唑啉二酮及其应用 |
TWI527800B (zh) | 2011-04-01 | 2016-04-01 | 南京英派藥業有限公司 | 作為聚(二磷酸腺苷酸-核醣)聚合酶(parp)之抑制劑之1-(芳基甲基)喹唑啉-2,4(1h,3h)-二酮及其應用 |
CA2876689C (fr) | 2012-06-13 | 2022-04-26 | Incyte Corporation | Composes tricycliques substitues utilises comme inhibiteurs de fgfr |
US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
HUE036571T2 (hu) | 2013-04-19 | 2018-07-30 | Incyte Holdings Corp | Biciklusos heterociklusok mint FGFR inhibitorok |
US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
EP3259269B9 (fr) | 2015-02-20 | 2020-03-04 | Incyte Corporation | Heterocycles bicycliques en tant qu'inhibiteurs de fgfr |
US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
CL2015003780A1 (es) | 2015-12-30 | 2016-09-16 | Univ Chile | Compuestos derivados pirimido-isoquinolin-quinonas, sus sales, isomeros, tautomeros farmacéuticas aceptables; composiciones farmáceuticas; procedimiento de preparación; y su uso en el tratamiento de enfermedades bacterianas y bacterianas multirresistentes. |
AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
US10815249B2 (en) | 2018-02-16 | 2020-10-27 | Sunovion Pharmaceuticals Inc. | Salts, crystal forms, and production methods thereof |
CR20200590A (es) | 2018-05-04 | 2021-04-26 | Incyte Corp | Formas sólidas de un inhibidor de fgfr y procesos para prepararlas |
US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
CN111620866A (zh) * | 2019-02-27 | 2020-09-04 | 南京药石科技股份有限公司 | 一种顺式-7,7-二氟-六氢-1H 吡咯并[3,4-c]吡啶衍生物及其制备方法 |
US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
WO2021007269A1 (fr) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
KR20220100879A (ko) | 2019-10-14 | 2022-07-18 | 인사이트 코포레이션 | Fgfr 저해제로서의 이환식 헤테로사이클 |
WO2021076728A1 (fr) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
CA3162010A1 (fr) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Derives d'un inhibiteur de fgfr |
WO2021113479A1 (fr) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Hétérocycles tricycliques en tant qu'inhibiteurs de fgfr |
WO2021146424A1 (fr) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
MX2022012833A (es) | 2020-04-14 | 2022-11-07 | Sunovion Pharmaceuticals Inc | (s)-(4,5-dihidro-7h-tieno[2,3-c]piran-7-il)-n-metilmetanamina para tratar trastornos neurologicos y psiquiatricos. |
AR126102A1 (es) | 2021-06-09 | 2023-09-13 | Incyte Corp | Heterociclos tricíclicos como inhibidores de fgfr |
WO2023066283A1 (fr) | 2021-10-20 | 2023-04-27 | Insilico Medicine Ip Limited | Inhibiteurs de la méthionine adénosyltransférase 2a (mat2a) et leurs utilisations |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1311573A (en) * | 1970-04-27 | 1973-03-28 | Hisamitsu Pharmaceutical Co | Quinazolinedione derivatives |
DE2334266A1 (de) * | 1972-07-07 | 1974-01-31 | Hisamitsu Pharmaceutical Co | Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidin-2,4 (1h, 3h)-dione |
JPS5758347B2 (fr) * | 1974-04-03 | 1982-12-09 | Hisamitsu Pharmaceutical Co | |
JPS5761743B2 (fr) * | 1974-04-25 | 1982-12-25 | Hisamitsu Pharmaceutical Co | |
DE2446543A1 (de) * | 1974-09-28 | 1976-04-15 | Hoechst Ag | Wasserunloesliche monoazomethinfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
DE2614148A1 (de) * | 1976-04-02 | 1977-10-20 | Henkel & Cie Gmbh | Oxidations-, bleich- und waschmittel mit einem gehalt an bleichaktivatoren |
IT1228293B (it) * | 1989-02-06 | 1991-06-07 | Angeli Inst Spa | Benzoderivati di composti eterociclici contenenti azoto. |
WO1994014809A1 (fr) * | 1992-12-23 | 1994-07-07 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Derives anneles d'uracile |
JPH09208543A (ja) * | 1995-11-29 | 1997-08-12 | Ono Pharmaceut Co Ltd | イソシアナート誘導体およびその関連化合物の製造方 法 |
EP0896961A4 (fr) * | 1995-12-28 | 1999-04-07 | Fuji Chem Ind Co Ltd | Procede de fabrication des derives de la 3-dihalobenzyl-2,4-quinazolinedione |
DE69701647T2 (de) * | 1996-02-01 | 2000-09-07 | Sumitomo Chemical Co | Verfahren zur Herstellung von Dioxochinazolinen |
JPH09295977A (ja) * | 1996-04-30 | 1997-11-18 | Terumo Corp | ピリドピリミジン誘導体及びそれを含有する医薬組成物 |
WO1998018781A2 (fr) * | 1996-10-28 | 1998-05-07 | Versicor, Inc. | Banques combinatoires de 2,4-pyrimidinediones fusionnes et 2,4-pyrimidinediones fusionnes actifs biologiquement |
SI1028950T1 (en) * | 1997-10-28 | 2003-08-31 | Warner-Lambert Company Llc | 7-substituted quinazolin-2,4-diones useful as antibacterial agents |
US7094780B1 (en) * | 2000-01-24 | 2006-08-22 | Warner Lambert Company Llc | 3-aminoquinazolin-2,4-dione antibacterial agents |
EP1288216A1 (fr) * | 2000-04-18 | 2003-03-05 | Sumitomo Pharmaceuticals Company, Limited | Quinazolinediones tricycliques |
JP2002284699A (ja) * | 2001-03-28 | 2002-10-03 | Sumitomo Pharmaceut Co Ltd | 視細胞変性疾患治療剤 |
-
2002
- 2002-05-13 EP EP02730582A patent/EP1401830A2/fr not_active Withdrawn
- 2002-05-13 BR BR0210028-2A patent/BR0210028A/pt not_active IP Right Cessation
- 2002-05-13 MX MXPA03009894A patent/MXPA03009894A/es unknown
- 2002-05-13 WO PCT/IB2002/001768 patent/WO2002102793A2/fr not_active Application Discontinuation
- 2002-05-13 AU AU2002302894A patent/AU2002302894A1/en not_active Abandoned
- 2002-05-13 CA CA002446963A patent/CA2446963A1/fr not_active Abandoned
- 2002-05-13 JP JP2003506266A patent/JP2005501021A/ja not_active Withdrawn
- 2002-05-31 GT GT200200104A patent/GT200200104A/es unknown
- 2002-06-18 HN HN2002000150A patent/HN2002000150A/es unknown
- 2002-06-18 PE PE2002000523A patent/PE20030272A1/es not_active Application Discontinuation
- 2002-06-18 SV SV2002001089A patent/SV2003001089A/es unknown
- 2002-06-19 DO DO2002000422A patent/DOP2002000422A/es unknown
- 2002-06-19 PA PA20028548401A patent/PA8548401A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
PA8548401A1 (es) | 2003-05-14 |
PE20030272A1 (es) | 2003-03-21 |
AU2002302894A1 (en) | 2003-01-02 |
SV2003001089A (es) | 2003-03-18 |
WO2002102793A2 (fr) | 2002-12-27 |
HN2002000150A (es) | 2002-09-13 |
MXPA03009894A (es) | 2004-02-17 |
WO2002102793A3 (fr) | 2003-04-10 |
GT200200104A (es) | 2003-02-11 |
EP1401830A2 (fr) | 2004-03-31 |
JP2005501021A (ja) | 2005-01-13 |
DOP2002000422A (es) | 2002-12-30 |
BR0210028A (pt) | 2004-06-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2446963A1 (fr) | Agents antibacteriens | |
AU780052B2 (en) | Pyrazolopyrimidines as therapeutic agents | |
AU783078B2 (en) | 3-aminoquinazolin-2,4-dione antibacterial agents | |
ES2708998T3 (es) | Carboxamidas primarias como inhibidores de btk | |
AU2020204287A1 (en) | Inhibitors of lysine specific demethylase-1 | |
US7214676B2 (en) | Spirotricyclic derivatives and their use as phosphodiesterase-7 inhibitors | |
CA2646128C (fr) | Pyridopyrazine et derives de celle-ci utilises comme inhibiteurs d'alk et de c-met | |
JP5259587B2 (ja) | イミダゾ[1,2−a]ピリジン−2−カルボキサミド誘導体、その調製方法および治療におけるその使用 | |
TWI531572B (zh) | 作為jak1抑制劑之哌啶-4-基三亞甲亞胺衍生物 | |
US7723347B2 (en) | Substituted phenylamino-pyrimidines | |
AU2011346733C1 (en) | Novel fused pyridine compounds as casein kinase inhibitors | |
KR101421852B1 (ko) | 카세인 키나제 억제제로서의 이미다졸 유도체 | |
WO2014078372A1 (fr) | Composés de n-pyrrolidinyle urée, thio-urée,guanidine et cyanoguanidine en tant qu'inhibiteurs de la kinase trka | |
CA2952692A1 (fr) | Composes imidazo[1,2b]pyridazine substitues | |
TW201020253A (en) | Substituted pyrazolo[1,5-a]pyrimidine compounds as Trk kinase inhibitors | |
CN103641816A (zh) | 作为蛋白激酶抑制剂的化合物和组合物 | |
JP2009523822A (ja) | プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド | |
CA2633563A1 (fr) | Composes chimiques | |
MX2013004003A (es) | Heteroarilos y usos de los mismos. | |
US20220119394A1 (en) | Imidazo[2,1-f][1,2,4]triazin-4-amine derivatives as tlr7 agonist | |
MX2013008629A (es) | Inhibidores de histona desacetilasa y composiciones y metodos para su uso. | |
JP2018527412A (ja) | Perk阻害剤としての1−フェニルピロリジン−2−オン誘導体 | |
KR102008431B1 (ko) | 이소인돌린 또는 이소퀴놀린 화합물, 이들의 제조 방법 및 이들을 함유하는 약학적 조성물 | |
CA3172498A1 (fr) | Degradation de la tyrosine kinase de bruton (btk) par conjugaison d'inhibiteurs de btk avec un ligand de ligase e3 et procedes d'utilisation | |
TW202115078A (zh) | 咪唑並[2,1-f][1,2,4]三嗪-4-胺衍生物作為tlr8促效劑 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Dead |