ZA200600426B - Benzoxazinone-derived sulfonamide compounds, their preparation and use as medicaments - Google Patents

Info

Publication number

ZA200600426B

ZA200600426B ZA200600426A ZA200600426A ZA200600426B ZA 200600426 B ZA200600426 B ZA 200600426B ZA 200600426 A ZA200600426 A ZA 200600426A ZA 200600426 A ZA200600426 A ZA 200600426A ZA 200600426 B ZA200600426 B ZA 200600426B

Authority

ZA

South Africa

Prior art keywords

benzo

dihydro

piperidin

oxazin

phenyl

Prior art date

2003-07-30

Links

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• Global Dossier
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• -1 sulfonamide compounds Chemical class 0.000 title claims description 1863
• 239000003814 drug Substances 0.000 title claims description 50
• HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title claims description 49
• 229940124530 sulfonamide Drugs 0.000 title claims description 28
• 238000002360 preparation method Methods 0.000 title claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 278
• 125000002950 monocyclic group Chemical class 0.000 claims description 159
• 125000005842 heteroatom Chemical group 0.000 claims description 145
• 229910052739 hydrogen Inorganic materials 0.000 claims description 145
• 150000001875 compounds Chemical class 0.000 claims description 142
• 150000003254 radicals Chemical class 0.000 claims description 142
• 125000001424 substituent group Chemical group 0.000 claims description 122
• 125000005605 benzo group Chemical group 0.000 claims description 119
• 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 claims description 109
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
• 238000011282 treatment Methods 0.000 claims description 102
• 238000011321 prophylaxis Methods 0.000 claims description 96
• 239000000460 chlorine Substances 0.000 claims description 95
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 94
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 88
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
• 150000003839 salts Chemical class 0.000 claims description 82
• 229910052731 fluorine Inorganic materials 0.000 claims description 78
• 239000001257 hydrogen Substances 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 72
• 208000035475 disorder Diseases 0.000 claims description 71
• 229910052801 chlorine Inorganic materials 0.000 claims description 70
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 69
• 239000012453 solvate Substances 0.000 claims description 68
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
• 238000002156 mixing Methods 0.000 claims description 58
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 57
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 57
• 229910052794 bromium Inorganic materials 0.000 claims description 49
• 238000000034 method Methods 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical compound C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 41
• 125000005418 aryl aryl group Chemical group 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
• YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 29
• 230000037406 food intake Effects 0.000 claims description 29
• 230000008569 process Effects 0.000 claims description 29
• 125000001544 thienyl group Chemical group 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000003368 amide group Chemical group 0.000 claims description 25
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• 150000003456 sulfonamides Chemical class 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 229920001774 Perfluoroether Polymers 0.000 claims description 20
• 206010012601 diabetes mellitus Diseases 0.000 claims description 20
• 235000012631 food intake Nutrition 0.000 claims description 19
• 229930194542 Keto Chemical group 0.000 claims description 18
• 208000008589 Obesity Diseases 0.000 claims description 18
• 125000000468 ketone group Chemical group 0.000 claims description 18
• 235000020824 obesity Nutrition 0.000 claims description 18
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
• 208000013403 hyperactivity Diseases 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
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• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
• 230000009467 reduction Effects 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 14
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• 208000026139 Memory disease Diseases 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 13
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 13
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 201000000980 schizophrenia Diseases 0.000 claims description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 239000005711 Benzoic acid Substances 0.000 claims description 12
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• 230000037410 cognitive enhancement Effects 0.000 claims description 12
• 230000006735 deficit Effects 0.000 claims description 12
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
• 208000032841 Bulimia Diseases 0.000 claims description 11
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 11
• 206010006895 Cachexia Diseases 0.000 claims description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 208000022531 anorexia Diseases 0.000 claims description 11
• 230000037396 body weight Effects 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 210000003169 central nervous system Anatomy 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 206010061428 decreased appetite Diseases 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 238000012423 maintenance Methods 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 230000003893 regulation of appetite Effects 0.000 claims description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 206010020651 Hyperkinesia Diseases 0.000 claims description 9
• 208000000269 Hyperkinesis Diseases 0.000 claims description 9
• 150000005840 aryl radicals Chemical class 0.000 claims description 9
• 210000000936 intestine Anatomy 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
• 229920002554 vinyl polymer Chemical group 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 208000010877 cognitive disease Diseases 0.000 claims description 8
• 230000001149 cognitive effect Effects 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
• 235000010233 benzoic acid Nutrition 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 150000007522 mineralic acids Chemical class 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 150000007524 organic acids Chemical class 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
• 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 4
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 4
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• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• BKJHJUSDLAXVOO-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)piperidin-4-yl]-6-methyl-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 BKJHJUSDLAXVOO-UHFFFAOYSA-N 0.000 claims 1
• YLPGMLSIWRQZDV-UHFFFAOYSA-N 1-[1-[(2,2,4,6,7-pentamethyl-3h-1-benzofuran-5-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(C)C(C)=C(OC(C)(C)C2)C2=C1C YLPGMLSIWRQZDV-UHFFFAOYSA-N 0.000 claims 1
• XZHKNWMZABGJNS-UHFFFAOYSA-N 1-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]piperidin-4-yl]-8-methoxy-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(OC)=CC=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C=1C(C)=NOC=1C XZHKNWMZABGJNS-UHFFFAOYSA-N 0.000 claims 1
• HFEAIOFRXWTPAC-UHFFFAOYSA-N 1-[1-[(4-chloro-2,1,3-benzoxadiazol-7-yl)sulfonyl]piperidin-4-yl]-8-methyl-4h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C2=NON=C2C(S(=O)(=O)N2CCC(CC2)N2C(=O)OCC=3C=CC=C(C2=3)C)=C1 HFEAIOFRXWTPAC-UHFFFAOYSA-N 0.000 claims 1
• QWGVYZWCRYEONI-UHFFFAOYSA-N 1-[1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]piperidin-4-yl]-6-methyl-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 QWGVYZWCRYEONI-UHFFFAOYSA-N 0.000 claims 1
• HMCBCCCIUDXIGE-UHFFFAOYSA-N 1-[1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]piperidin-4-yl]-8-methyl-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC=CC(C)=C2N1C(CC1)CCN1S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 HMCBCCCIUDXIGE-UHFFFAOYSA-N 0.000 claims 1
• ZVWFHOYKJXNVNS-UHFFFAOYSA-N 1-[1-[4-(4-bromophenoxy)phenyl]sulfonylpiperidin-4-yl]-8-methyl-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(C)=CC=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Br)C=C1 ZVWFHOYKJXNVNS-UHFFFAOYSA-N 0.000 claims 1
• ULANGOPLOFITGE-UHFFFAOYSA-N 1-[1-[4-bromo-2-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl]-6-chloro-4h-3,1-benzoxazin-2-one Chemical compound FC(F)(F)OC1=CC(Br)=CC=C1S(=O)(=O)N1CCC(N2C3=CC=C(Cl)C=C3COC2=O)CC1 ULANGOPLOFITGE-UHFFFAOYSA-N 0.000 claims 1
• SLMNEEYNYGIKJR-UHFFFAOYSA-N 1-[1-[4-bromo-2-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl]-8-methyl-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(C)=CC=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C1=CC=C(Br)C=C1OC(F)(F)F SLMNEEYNYGIKJR-UHFFFAOYSA-N 0.000 claims 1
• JHDVCEFHEMQTSG-UHFFFAOYSA-N 1-[1-[4-bromo-3-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-8-methyl-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(C)=CC=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 JHDVCEFHEMQTSG-UHFFFAOYSA-N 0.000 claims 1
• WGEQHAZBKOBFDU-UHFFFAOYSA-N 1-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-6-methyl-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C2C=CC=C(N(C)C)C2=CC=C1 WGEQHAZBKOBFDU-UHFFFAOYSA-N 0.000 claims 1
• AVDSAKZKHDCARJ-UHFFFAOYSA-N 2-[4-(8-methyl-2-oxo-4h-3,1-benzoxazin-1-yl)piperidin-1-yl]sulfonylbenzonitrile Chemical compound C1=2C(C)=CC=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1C#N AVDSAKZKHDCARJ-UHFFFAOYSA-N 0.000 claims 1
• FMNNPTUXLRICAU-UHFFFAOYSA-N 5-chloro-1-[1-(1,2-dimethylimidazol-4-yl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound CN1C(C)=NC(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC(Cl)=C3COC2=O)=C1 FMNNPTUXLRICAU-UHFFFAOYSA-N 0.000 claims 1
• TYMLELPFFATBSV-UHFFFAOYSA-N 5-chloro-1-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound CC1=NOC(C)=C1S(=O)(=O)N1CCC(N2C3=CC=CC(Cl)=C3COC2=O)CC1 TYMLELPFFATBSV-UHFFFAOYSA-N 0.000 claims 1
• BJIIOXGISLHJLE-UHFFFAOYSA-N 5-chloro-1-[1-[(3-methyl-2-oxo-1,3-benzoxazol-6-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=C(Cl)C=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=C2N(C)C(=O)OC2=C1 BJIIOXGISLHJLE-UHFFFAOYSA-N 0.000 claims 1
• ZTVSKXHSLSXDBS-UHFFFAOYSA-N 5-chloro-1-[1-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=C(Cl)C=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=C2N(C)CCOC2=C1 ZTVSKXHSLSXDBS-UHFFFAOYSA-N 0.000 claims 1
• HOHOAYPEWAQSDC-UHFFFAOYSA-N 5-chloro-1-[1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=C(Cl)C=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2S1 HOHOAYPEWAQSDC-UHFFFAOYSA-N 0.000 claims 1
• OEVNMUWVKNPTMQ-UHFFFAOYSA-N 6,7-difluoro-1-[1-(2-phenylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=2C=C(F)C(F)=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 OEVNMUWVKNPTMQ-UHFFFAOYSA-N 0.000 claims 1
• VPXHOIOJKZNNME-UHFFFAOYSA-N 6,7-difluoro-1-[1-(4-phenylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=2C=C(F)C(F)=CC=2COC(=O)N1C(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 VPXHOIOJKZNNME-UHFFFAOYSA-N 0.000 claims 1
• GJWPPDFHSPOALN-UHFFFAOYSA-N 6-bromo-1-[1-(2,3,5,6-tetramethylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound CC1=CC(C)=C(C)C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Br)C=C3COC2=O)=C1C GJWPPDFHSPOALN-UHFFFAOYSA-N 0.000 claims 1
• CQRJTCOGKFTQDI-UHFFFAOYSA-N 6-bromo-1-[1-(2,4,5-trifluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 CQRJTCOGKFTQDI-UHFFFAOYSA-N 0.000 claims 1
• RNEHIIPIXDSVSZ-UHFFFAOYSA-N 6-bromo-1-[1-(2,6-dichlorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 RNEHIIPIXDSVSZ-UHFFFAOYSA-N 0.000 claims 1
• DCQDUKNFQIUFEK-UHFFFAOYSA-N 6-bromo-1-[1-(2-bromo-4,6-difluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound BrC1=CC(F)=CC(F)=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 DCQDUKNFQIUFEK-UHFFFAOYSA-N 0.000 claims 1
• BXAYXUIVOSCMBD-UHFFFAOYSA-N 6-bromo-1-[1-(2-bromo-4-fluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound BrC1=CC(F)=CC=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 BXAYXUIVOSCMBD-UHFFFAOYSA-N 0.000 claims 1
• OXQDQALKPQDULD-UHFFFAOYSA-N 6-bromo-1-[1-(2-oxochromen-6-yl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O1C(=O)C=CC2=CC(S(=O)(=O)N3CCC(CC3)N3C4=CC=C(C=C4COC3=O)Br)=CC=C21 OXQDQALKPQDULD-UHFFFAOYSA-N 0.000 claims 1
• RFEURJDUCSJKRX-UHFFFAOYSA-N 6-bromo-1-[1-(4-chloro-2,5-difluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C(F)=CC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Br)C=C3COC2=O)=C1F RFEURJDUCSJKRX-UHFFFAOYSA-N 0.000 claims 1
• XFZXAIZACACPIF-UHFFFAOYSA-N 6-bromo-1-[1-(5-bromo-2-methoxyphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound COC1=CC=C(Br)C=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 XFZXAIZACACPIF-UHFFFAOYSA-N 0.000 claims 1
• SMKIJZDNZCDCKY-UHFFFAOYSA-N 6-bromo-1-[1-(5-chloro-2-fluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound FC1=CC=C(Cl)C=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 SMKIJZDNZCDCKY-UHFFFAOYSA-N 0.000 claims 1
• FFLMEUJAUPZAFD-UHFFFAOYSA-N 6-bromo-1-[1-[4-(4-bromophenoxy)phenyl]sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Br)C=C3COC2=O)C=C1 FFLMEUJAUPZAFD-UHFFFAOYSA-N 0.000 claims 1
• NHEXFSLERIXFJM-UHFFFAOYSA-N 6-bromo-1-[1-[4-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1CCC(N2C3=CC=C(Br)C=C3COC2=O)CC1 NHEXFSLERIXFJM-UHFFFAOYSA-N 0.000 claims 1
• DSZDWFRZSMMGIK-UHFFFAOYSA-N 6-chloro-1-(1-isoquinolin-5-ylsulfonylpiperidin-4-yl)-4h-3,1-benzoxazin-2-one;hydrochloride Chemical compound Cl.N1=CC=C2C(S(=O)(=O)N3CCC(CC3)N3C4=CC=C(C=C4COC3=O)Cl)=CC=CC2=C1 DSZDWFRZSMMGIK-UHFFFAOYSA-N 0.000 claims 1
• VXPYOHQVEZTKBU-UHFFFAOYSA-N 6-chloro-1-(1-propan-2-ylsulfonylpiperidin-4-yl)-4h-3,1-benzoxazin-2-one Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1N1C2=CC=C(Cl)C=C2COC1=O VXPYOHQVEZTKBU-UHFFFAOYSA-N 0.000 claims 1
• BDNUTWQWCDGEGX-UHFFFAOYSA-N 6-chloro-1-[1-(1,2-dimethylimidazol-4-yl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound CN1C(C)=NC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 BDNUTWQWCDGEGX-UHFFFAOYSA-N 0.000 claims 1
• ZXQJIHBSOSKMBP-UHFFFAOYSA-N 6-chloro-1-[1-(2,4,6-trichlorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(Cl)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl ZXQJIHBSOSKMBP-UHFFFAOYSA-N 0.000 claims 1
• NFNZTZUODOCTJB-UHFFFAOYSA-N 6-chloro-1-[1-(2,5-difluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound FC1=CC=C(F)C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 NFNZTZUODOCTJB-UHFFFAOYSA-N 0.000 claims 1
• XKGDACAKUFUGFB-UHFFFAOYSA-N 6-chloro-1-[1-(2,5-dimethoxyphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 XKGDACAKUFUGFB-UHFFFAOYSA-N 0.000 claims 1
• OAPMJCCQGAZBPX-UHFFFAOYSA-N 6-chloro-1-[1-(2,6-dichlorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(Cl)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(Cl)C=CC=C1Cl OAPMJCCQGAZBPX-UHFFFAOYSA-N 0.000 claims 1
• LOVUIVSOAFYIBV-UHFFFAOYSA-N 6-chloro-1-[1-(2-methoxy-4-methylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound COC1=CC(C)=CC=C1S(=O)(=O)N1CCC(N2C3=CC=C(Cl)C=C3COC2=O)CC1 LOVUIVSOAFYIBV-UHFFFAOYSA-N 0.000 claims 1
• PLMQUXUZNWPIQG-UHFFFAOYSA-N 6-chloro-1-[1-(3,5-dichloro-4-hydroxyphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1S(=O)(=O)N1CCC(N2C3=CC=C(Cl)C=C3COC2=O)CC1 PLMQUXUZNWPIQG-UHFFFAOYSA-N 0.000 claims 1
• PACGQRWMIOQSAO-UHFFFAOYSA-N 6-chloro-1-[1-(3-chlorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound ClC1=CC=CC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 PACGQRWMIOQSAO-UHFFFAOYSA-N 0.000 claims 1
• AWDUMYSPFGQCMD-UHFFFAOYSA-N 6-chloro-1-[1-(3-methylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound CC1=CC=CC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 AWDUMYSPFGQCMD-UHFFFAOYSA-N 0.000 claims 1
• ANECTLSRDWVUFS-UHFFFAOYSA-N 6-chloro-1-[1-(4-chloro-3-nitrophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 ANECTLSRDWVUFS-UHFFFAOYSA-N 0.000 claims 1
• PJSNUCBSNODKCX-UHFFFAOYSA-N 6-chloro-1-[1-(4-methylsulfonylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)N1CCC(N2C3=CC=C(Cl)C=C3COC2=O)CC1 PJSNUCBSNODKCX-UHFFFAOYSA-N 0.000 claims 1
• XNKMTXOSNYRIGX-UHFFFAOYSA-N 6-chloro-1-[1-(4-phenylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(Cl)=CC=C2N1C(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XNKMTXOSNYRIGX-UHFFFAOYSA-N 0.000 claims 1
• WKRQEZBIQHDSER-UHFFFAOYSA-N 6-chloro-1-[1-(5-chloro-2-fluorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound FC1=CC=C(Cl)C=C1S(=O)(=O)N1CCC(N2C3=CC=C(Cl)C=C3COC2=O)CC1 WKRQEZBIQHDSER-UHFFFAOYSA-N 0.000 claims 1
• NFHZWVTUGHUMNO-UHFFFAOYSA-N 6-chloro-1-[1-[(4-chloro-2,1,3-benzoxadiazol-7-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C2=NON=C2C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(C=C3COC2=O)Cl)=C1 NFHZWVTUGHUMNO-UHFFFAOYSA-N 0.000 claims 1
• MSDUBHQEPAWEEC-UHFFFAOYSA-N 6-chloro-1-[1-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(Cl)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=C2N(C)CCOC2=C1 MSDUBHQEPAWEEC-UHFFFAOYSA-N 0.000 claims 1
• RTWVNLLJJFLFTI-UHFFFAOYSA-N 6-chloro-1-[1-[3-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(Cl)C=C3COC2=O)=C1 RTWVNLLJJFLFTI-UHFFFAOYSA-N 0.000 claims 1
• LHNPLEAFZVRRRJ-UHFFFAOYSA-N 6-methyl-1-[1-(1-methylimidazol-4-yl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CN(C)C=N1 LHNPLEAFZVRRRJ-UHFFFAOYSA-N 0.000 claims 1
• XSNNAPVYEAREMY-UHFFFAOYSA-N 6-methyl-1-[1-(2,3,5,6-tetramethylphenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(C)C(C)=CC(C)=C1C XSNNAPVYEAREMY-UHFFFAOYSA-N 0.000 claims 1
• QFULNFPZZSTMCG-UHFFFAOYSA-N 6-methyl-1-[1-(2,4,6-trichlorophenyl)sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl QFULNFPZZSTMCG-UHFFFAOYSA-N 0.000 claims 1
• IOYOGOVZGWWKJN-UHFFFAOYSA-N 6-methyl-1-[1-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=C2N(C)CCOC2=C1 IOYOGOVZGWWKJN-UHFFFAOYSA-N 0.000 claims 1
• QPAADAIXNMYGFE-UHFFFAOYSA-N 6-methyl-1-[1-[(5-methyl-2,1,3-benzothiadiazol-4-yl)sulfonyl]piperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound C1=CC2=NSN=C2C(S(=O)(=O)N2CCC(CC2)N2C3=CC=C(C=C3COC2=O)C)=C1C QPAADAIXNMYGFE-UHFFFAOYSA-N 0.000 claims 1
• NHUVHXKBMCGKJU-UHFFFAOYSA-N 6-methyl-1-[1-[2-nitro-4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC2=CC(C)=CC=C2N1C(CC1)CCN1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O NHUVHXKBMCGKJU-UHFFFAOYSA-N 0.000 claims 1
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