KR20070039045A - 신규한 옥사비스피딘 화합물 및 이의 심부정맥의 치료에의용도 - Google Patents

Info

Publication number

KR20070039045A

KR20070039045A KR1020077000930A KR20077000930A KR20070039045A KR 20070039045 A KR20070039045 A KR 20070039045A KR 1020077000930 A KR1020077000930 A KR 1020077000930A KR 20077000930 A KR20077000930 A KR 20077000930A KR 20070039045 A KR20070039045 A KR 20070039045A

Authority

KR

South Korea

Prior art keywords

ethyl

oxa

diazabicyclo

cyano

formula

Prior art date

2004-06-15

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

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 353
• 238000011282 treatment Methods 0.000 title claims abstract description 16
• 210000003462 vein Anatomy 0.000 title description 6
• 206010003119 arrhythmia Diseases 0.000 claims abstract description 20
• 230000006793 arrhythmia Effects 0.000 claims abstract description 19
• 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 5
• 230000001746 atrial effect Effects 0.000 claims abstract description 5
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 226
• -1 substituted aryl compound Chemical class 0.000 claims description 186
• 125000001424 substituent group Chemical group 0.000 claims description 116
• 125000005843 halogen group Chemical group 0.000 claims description 109
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 102
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 92
• 125000003118 aryl group Chemical group 0.000 claims description 77
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 229910052799 carbon Inorganic materials 0.000 claims description 66
• 239000002904 solvent Substances 0.000 claims description 64
• 125000002947 alkylene group Chemical group 0.000 claims description 63
• 239000000203 mixture Substances 0.000 claims description 59
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 44
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 44
• 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 43
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 238000004519 manufacturing process Methods 0.000 claims description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 125000003107 substituted aryl group Chemical group 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 238000006243 chemical reaction Methods 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000004104 aryloxy group Chemical group 0.000 claims description 13
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 12
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• 150000001408 amides Chemical class 0.000 claims description 10
• 125000004122 cyclic group Chemical group 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 10
• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 6
• 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
• 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 5
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
• 125000002015 acyclic group Chemical group 0.000 claims description 4
• XLPZOINVUSQMJC-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XLPZOINVUSQMJC-UHFFFAOYSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• LJNALGCCKPAENZ-UHFFFAOYSA-N 4-cyano-n-[2-[3-[(4-cyano-2-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=C(C#N)C=C1F LJNALGCCKPAENZ-UHFFFAOYSA-N 0.000 claims description 3
• KVCKGSVFJOBICN-UHFFFAOYSA-N 4-cyano-n-[2-[3-[2-(2,6-difluorophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=C(F)C=CC=C1F KVCKGSVFJOBICN-UHFFFAOYSA-N 0.000 claims description 3
• CWQJEYCQFHDOBZ-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(2,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(F)C=C1F CWQJEYCQFHDOBZ-UHFFFAOYSA-N 0.000 claims description 3
• YSEUGKIDEPJNDB-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(2-fluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=CC=C1F YSEUGKIDEPJNDB-UHFFFAOYSA-N 0.000 claims description 3
• JCVUUGGGIYOZFN-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(3,4-difluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(F)C(F)=C1 JCVUUGGGIYOZFN-UHFFFAOYSA-N 0.000 claims description 3
• SVOUIFYZIRHHHY-UHFFFAOYSA-N 4-cyano-n-[2-[7-[2-(4-fluorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(F)C=C1 SVOUIFYZIRHHHY-UHFFFAOYSA-N 0.000 claims description 3
• XXUBZTCWKJTBSM-UHFFFAOYSA-N 4-cyano-n-[2-[7-[3-(2,4-difluorophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCCOC1=CC=C(F)C=C1F XXUBZTCWKJTBSM-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• XETZHZZXWRLZBZ-UHFFFAOYSA-N 5-chloro-n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XETZHZZXWRLZBZ-UHFFFAOYSA-N 0.000 claims description 3
• KWOVTHWLRKOCTM-UHFFFAOYSA-N 5-chloro-n-[2-[7-[3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NCCN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 KWOVTHWLRKOCTM-UHFFFAOYSA-N 0.000 claims description 3
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• IZSJGOHJUONAPF-UHFFFAOYSA-N n-[2-(3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)ethyl]-4-cyano-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CC1=CC=CC=C1 IZSJGOHJUONAPF-UHFFFAOYSA-N 0.000 claims description 3
• WRYJODWAZQEDTO-UHFFFAOYSA-N n-[2-(3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CC=3C=CC=CC=3)CC2C1 WRYJODWAZQEDTO-UHFFFAOYSA-N 0.000 claims description 3
• NBVCPDKXRPINAQ-UHFFFAOYSA-N n-[2-[3-(1,2-benzoxazol-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3C4=CC=CC=C4ON=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 NBVCPDKXRPINAQ-UHFFFAOYSA-N 0.000 claims description 3
• UWJWFBNYVTWXCN-UHFFFAOYSA-N n-[2-[3-(1,3-benzoxazol-2-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3OC4=CC=CC=C4N=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 UWJWFBNYVTWXCN-UHFFFAOYSA-N 0.000 claims description 3
• JKYRVIXUFLUELO-UHFFFAOYSA-N n-[2-[3-(1-benzofuran-3-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1C(O2)CN(CC=3C4=CC=CC=C4OC=3)CC2CN1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 JKYRVIXUFLUELO-UHFFFAOYSA-N 0.000 claims description 3
• VVCAFZDPOWQEGJ-BSSNWTCHSA-N n-[2-[3-[(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C([C@@H](O)CN1CC2CN(CCNS(=O)(=O)CC=3C=CC=CC=3)CC(O2)C1)OC1=CC=C(C#N)C=C1 VVCAFZDPOWQEGJ-BSSNWTCHSA-N 0.000 claims description 3
• SXIUZAIGXHEFLZ-PELRDEGISA-N n-[2-[3-[(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]propane-2-sulfonamide Chemical compound C([C@@H](O)CN1CC2CN(CC(C1)O2)CCNS(=O)(=O)C(C)C)OC1=CC=C(C#N)C=C1 SXIUZAIGXHEFLZ-PELRDEGISA-N 0.000 claims description 3
• OOPOYODXWVTCHK-UHFFFAOYSA-N n-[2-[3-[(4-cyanophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CC=3C=CC(=CC=3)C#N)CC2CN1CCNS(=O)(=O)CC1=CC=CC=C1 OOPOYODXWVTCHK-UHFFFAOYSA-N 0.000 claims description 3
• WJXJSOGBWAHNMS-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCN2CC3CN(CCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 WJXJSOGBWAHNMS-UHFFFAOYSA-N 0.000 claims description 3
• UEQXFWJTIUWOKP-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-1-phenylmethanesulfonamide Chemical compound C1C(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2CN1CCNS(=O)(=O)CC1=CC=CC=C1 UEQXFWJTIUWOKP-UHFFFAOYSA-N 0.000 claims description 3
• QJZIEQUUKOHPKT-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 QJZIEQUUKOHPKT-UHFFFAOYSA-N 0.000 claims description 3
• LJDGRKMMCUOYAA-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 LJDGRKMMCUOYAA-UHFFFAOYSA-N 0.000 claims description 3
• SCGHOSSLGPNTTM-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-2-fluorobenzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 SCGHOSSLGPNTTM-UHFFFAOYSA-N 0.000 claims description 3
• VFNAHQAHRJJPPA-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NCCN2CC3CN(CCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1 VFNAHQAHRJJPPA-UHFFFAOYSA-N 0.000 claims description 3
• SYYICIIXCFHJDS-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 SYYICIIXCFHJDS-UHFFFAOYSA-N 0.000 claims description 3
• HVJJFLMEITXIBQ-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 HVJJFLMEITXIBQ-UHFFFAOYSA-N 0.000 claims description 3
• NJAKHOSWSSLROL-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n,3,5-trimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 NJAKHOSWSSLROL-UHFFFAOYSA-N 0.000 claims description 3
• FBAVHBFHTDLNQC-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]-n-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 FBAVHBFHTDLNQC-UHFFFAOYSA-N 0.000 claims description 3
• BZDRYXYPNHVSJP-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NCCN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 BZDRYXYPNHVSJP-UHFFFAOYSA-N 0.000 claims description 3
• YIRDXIKHDISCGJ-UHFFFAOYSA-N n-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]methanesulfonamide Chemical class C1C(O2)CN(CCNS(=O)(=O)C)CC2CN1CCOC1=CC=C(C#N)C=C1 YIRDXIKHDISCGJ-UHFFFAOYSA-N 0.000 claims description 3
• DISKQMLINWSDKG-UHFFFAOYSA-N n-[2-[7-[2-(4-chlorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyano-n-methylbenzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)CCN(CC(C1)O2)CC2CN1CCC1=CC=C(Cl)C=C1 DISKQMLINWSDKG-UHFFFAOYSA-N 0.000 claims description 3
• DNDXMBRTAVDSHQ-UHFFFAOYSA-N n-[2-[7-[2-(4-chlorophenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]-4-cyanobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1CCN1CC(O2)CN(CCNS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 DNDXMBRTAVDSHQ-UHFFFAOYSA-N 0.000 claims description 3
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