OA12067A - New oxabispidine compounds useful in the treatmentof cardiac arrhythmias. - Google Patents

Info

Publication number

OA12067A

OA12067A OA1200200113A OA1200200113A OA12067A OA 12067 A OA12067 A OA 12067A OA 1200200113 A OA1200200113 A OA 1200200113A OA 1200200113 A OA1200200113 A OA 1200200113A OA 12067 A OA12067 A OA 12067A

Authority

OA

OAPI

Prior art keywords

oxa

diazabicyclo

benzonitrile

compound

formula

Prior art date

1999-10-18

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 471
• 206010003119 arrhythmia Diseases 0.000 title claims abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 230000006793 arrhythmia Effects 0.000 claims abstract description 15
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 275
• 125000000217 alkyl group Chemical group 0.000 claims description 181
• 238000006243 chemical reaction Methods 0.000 claims description 133
• 125000005843 halogen group Chemical group 0.000 claims description 86
• 125000002947 alkylene group Chemical group 0.000 claims description 77
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 238000000034 method Methods 0.000 claims description 62
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
• 239000002904 solvent Substances 0.000 claims description 57
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
• 125000001424 substituent group Chemical group 0.000 claims description 53
• -1 3- {7-[2-(4-methoxyphenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1 ]-non-3-yl} propyl Chemical group 0.000 claims description 52
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 38
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 230000008569 process Effects 0.000 claims description 29
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 150000001721 carbon Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
• 101100070530 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) het-6 gene Proteins 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000001475 halogen functional group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 8
• 230000003647 oxidation Effects 0.000 claims description 8
• 238000007254 oxidation reaction Methods 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 230000002140 halogenating effect Effects 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000002346 iodo group Chemical group I* 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• 238000010511 deprotection reaction Methods 0.000 claims description 5
• 239000011630 iodine Substances 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
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 5
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 230000001746 atrial effect Effects 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 238000011321 prophylaxis Methods 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• OQHPAEHSQMKXSG-UHFFFAOYSA-N (3-benzoyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N(CC(C1)O2)CC2CN1C(=O)C1=CC=CC=C1 OQHPAEHSQMKXSG-UHFFFAOYSA-N 0.000 claims description 2
• UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 claims description 2
• USHQAANQUPSIEV-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)ethyl 7-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1CN(C(=O)C)CCN1CCOC(=O)N1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 USHQAANQUPSIEV-UHFFFAOYSA-N 0.000 claims description 2
• YKWPCKMVRBLDJR-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)ethyl 7-[3-(4-cyanoanilino)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1CN(C(=O)C)CCN1CCOC(=O)N1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 YKWPCKMVRBLDJR-UHFFFAOYSA-N 0.000 claims description 2
• QUXJOPAIAIISAV-UHFFFAOYSA-N 4-[1-(3,4-dimethoxyphenoxy)-4-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]butyl]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1OC(C=1C=CC(=CC=1)C#N)CCCN1CC(O2)CN(CC(=O)C(C)(C)C)CC2C1 QUXJOPAIAIISAV-UHFFFAOYSA-N 0.000 claims description 2
• SYJFQACWAVOYBU-UHFFFAOYSA-N 4-[2-(3-butylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)ethoxy]benzonitrile Chemical compound C1C(O2)CN(S(=O)(=O)CCCC)CC2CN1CCOC1=CC=C(C#N)C=C1 SYJFQACWAVOYBU-UHFFFAOYSA-N 0.000 claims description 2
• ZFCLEMPZXCRWKC-UHFFFAOYSA-N 4-[2-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzene-1,3-dicarbonitrile Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CCOC1=CC=C(C#N)C=C1C#N ZFCLEMPZXCRWKC-UHFFFAOYSA-N 0.000 claims description 2
• CYXCSOWXRRGAHX-UHFFFAOYSA-N 4-[2-[3-[(2,4-difluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound FC1=CC(F)=CC=C1CN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 CYXCSOWXRRGAHX-UHFFFAOYSA-N 0.000 claims description 2
• TZXOTBUVXNBRLH-UHFFFAOYSA-N 4-[2-[3-[(4-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1CN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 TZXOTBUVXNBRLH-UHFFFAOYSA-N 0.000 claims description 2
• XWAVSDACTDHMOV-UHFFFAOYSA-N 4-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 XWAVSDACTDHMOV-UHFFFAOYSA-N 0.000 claims description 2
• WZSGYCQVVPFHIO-UHFFFAOYSA-N 4-[2-[3-[2-(4-fluorophenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1C(=O)CN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 WZSGYCQVVPFHIO-UHFFFAOYSA-N 0.000 claims description 2
• KIEDYFNJCNMNLR-UHFFFAOYSA-N 4-[2-[7-(2-phenoxyethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CCOC=3C=CC=CC=3)CC2C1 KIEDYFNJCNMNLR-UHFFFAOYSA-N 0.000 claims description 2
• OYCWICGIUMJGOV-UHFFFAOYSA-N 4-[2-[7-(3-ethylsulfonylpropyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound C1C(O2)CN(CCCS(=O)(=O)CC)CC2CN1CCOC1=CC=C(C#N)C=C1 OYCWICGIUMJGOV-UHFFFAOYSA-N 0.000 claims description 2
• DYTDURPBPZILOH-UHFFFAOYSA-N 4-[2-[7-[2-(2-methoxyethoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound C1C(O2)CN(CCOCCOC)CC2CN1CCOC1=CC=C(C#N)C=C1 DYTDURPBPZILOH-UHFFFAOYSA-N 0.000 claims description 2
• PFOCXRBQPDHSAT-UHFFFAOYSA-N 4-[2-[7-[2-(3,4-dimethoxyphenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 PFOCXRBQPDHSAT-UHFFFAOYSA-N 0.000 claims description 2
• JLBAYNLBOJCYHQ-UHFFFAOYSA-N 4-[2-hydroxy-3-[7-[2-(2-methoxyethoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]propoxy]benzonitrile Chemical compound C1C(O2)CN(CCOCCOC)CC2CN1CC(O)COC1=CC=C(C#N)C=C1 JLBAYNLBOJCYHQ-UHFFFAOYSA-N 0.000 claims description 2
• PRAXUAILYHAJER-UHFFFAOYSA-N 4-[3-(3-butylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)-2-hydroxypropoxy]benzonitrile Chemical compound C1C(O2)CN(S(=O)(=O)CCCC)CC2CN1CC(O)COC1=CC=C(C#N)C=C1 PRAXUAILYHAJER-UHFFFAOYSA-N 0.000 claims description 2
• JAHWBGQNAOVQRH-UHFFFAOYSA-N 4-[3-(3-butylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)propylamino]benzonitrile Chemical compound C1C(O2)CN(S(=O)(=O)CCCC)CC2CN1CCCNC1=CC=C(C#N)C=C1 JAHWBGQNAOVQRH-UHFFFAOYSA-N 0.000 claims description 2
• RIOUAQNAYSCREO-UHFFFAOYSA-N 4-[3-[3-(2-phenoxyethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NCCCN1CC(O2)CN(CCOC=3C=CC=CC=3)CC2C1 RIOUAQNAYSCREO-UHFFFAOYSA-N 0.000 claims description 2
• YMONHXMGADKISC-UHFFFAOYSA-N 4-[3-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzamide Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CCCNC1=CC=C(C(N)=O)C=C1 YMONHXMGADKISC-UHFFFAOYSA-N 0.000 claims description 2
• BKWHDRQCLHJLJX-UHFFFAOYSA-N 4-[3-[3-(3-ethylsulfonylpropyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1C(O2)CN(CCCS(=O)(=O)CC)CC2CN1CCCNC1=CC=C(C#N)C=C1 BKWHDRQCLHJLJX-UHFFFAOYSA-N 0.000 claims description 2
• QAGSHMXKZDEBON-UHFFFAOYSA-N 4-[3-[3-(benzenesulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C=1C=CC=CC=1S(=O)(=O)N(CC(C1)O2)CC2CN1CCCNC1=CC=C(C#N)C=C1 QAGSHMXKZDEBON-UHFFFAOYSA-N 0.000 claims description 2
• VPCFUQDOAOYGJG-UHFFFAOYSA-N 4-[3-[3-(cyclopropylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)CCCN(CC(C1)O2)CC2CN1CC1CC1 VPCFUQDOAOYGJG-UHFFFAOYSA-N 0.000 claims description 2
• OLYARRPXIIOBOG-UHFFFAOYSA-N 4-[3-[3-[(2,4-difluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound FC1=CC(F)=CC=C1CN1CC(O2)CN(CCCS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 OLYARRPXIIOBOG-UHFFFAOYSA-N 0.000 claims description 2
• UAMZZHYGFAPMTI-UHFFFAOYSA-N 4-[3-[3-[(4-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=CC(F)=CC=C1CN1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 UAMZZHYGFAPMTI-UHFFFAOYSA-N 0.000 claims description 2
• TUVXEDHSDAEVGN-UHFFFAOYSA-N 4-[3-[3-[(4-fluorophenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound C1=CC(F)=CC=C1CN1CC(O2)CN(CCCS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 TUVXEDHSDAEVGN-UHFFFAOYSA-N 0.000 claims description 2
• HLXZBUMRCSJRKS-UHFFFAOYSA-N 4-[3-[3-[2-(2-methoxyethoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1C(O2)CN(CCOCCOC)CC2CN1CCCNC1=CC=C(C#N)C=C1 HLXZBUMRCSJRKS-UHFFFAOYSA-N 0.000 claims description 2
• NQXLPAJPSZBKEE-UHFFFAOYSA-N 4-[3-[3-[2-(2-methoxyethoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound C1C(O2)CN(CCOCCOC)CC2CN1CCCS(=O)(=O)C1=CC=C(C#N)C=C1 NQXLPAJPSZBKEE-UHFFFAOYSA-N 0.000 claims description 2
• WVYRPQWKUKIKTK-UHFFFAOYSA-N 4-[3-[3-[2-(3,4-dimethoxyphenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 WVYRPQWKUKIKTK-UHFFFAOYSA-N 0.000 claims description 2
• APUNXYIAVLWVDF-UHFFFAOYSA-N 4-[3-[3-[2-(4-fluorophenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1C(=O)CN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 APUNXYIAVLWVDF-UHFFFAOYSA-N 0.000 claims description 2
• KOOYDQAMHRIHEP-UHFFFAOYSA-N 4-[3-[3-[2-(4-hydroxyphenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(O)=CC=C1C(=O)CN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 KOOYDQAMHRIHEP-UHFFFAOYSA-N 0.000 claims description 2
• JVNMOOXYULLGNY-UHFFFAOYSA-N 4-[3-[3-[2-(4-methoxyphenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)CN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 JVNMOOXYULLGNY-UHFFFAOYSA-N 0.000 claims description 2
• CALKXVBMBBBUBX-UHFFFAOYSA-N 4-[3-[3-[2-(4-methoxyphenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)CN1CC(O2)CN(CCCS(=O)(=O)C=3C=CC(=CC=3)C#N)CC2C1 CALKXVBMBBBUBX-UHFFFAOYSA-N 0.000 claims description 2
• XKYGRCMWBWHULR-UHFFFAOYSA-N 4-[3-[3-[2-(4-methylphenyl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(C)=CC=C1C(=O)CN1CC(O2)CN(CCCOC=3C=CC(=CC=3)C#N)CC2C1 XKYGRCMWBWHULR-UHFFFAOYSA-N 0.000 claims description 2
• FREPQAQKUVNPSW-UHFFFAOYSA-N 4-[3-[3-[3-(4-acetylpiperazin-1-yl)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1CN(C(=O)C)CCN1CCCN1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 FREPQAQKUVNPSW-UHFFFAOYSA-N 0.000 claims description 2
• LNXROAAVVLCEKW-UHFFFAOYSA-N 4-[3-[3-[3-(4-bromophenyl)-3-oxopropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=CC(Br)=CC=C1C(=O)CCN1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 LNXROAAVVLCEKW-UHFFFAOYSA-N 0.000 claims description 2
• ZRYZSSPVEBJOIH-UHFFFAOYSA-N 4-[3-[3-[3-(4-cyanoanilino)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NCCCN1CC(O2)CN(CCCNC=3C=CC(=CC=3)C#N)CC2C1 ZRYZSSPVEBJOIH-UHFFFAOYSA-N 0.000 claims description 2
• LOIMFNVIVHPGTM-UHFFFAOYSA-N 4-[3-[7-(3-ethylsulfonylpropyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]propylsulfonyl]benzonitrile Chemical compound C1C(O2)CN(CCCS(=O)(=O)CC)CC2CN1CCCS(=O)(=O)C1=CC=C(C#N)C=C1 LOIMFNVIVHPGTM-UHFFFAOYSA-N 0.000 claims description 2
• PNKUCGCUUPYACP-UHFFFAOYSA-N 4-[3-[7-[3-(4-acetylpiperazin-1-yl)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]-2-hydroxypropoxy]benzonitrile Chemical compound C1CN(C(=O)C)CCN1CCCN1CC(O2)CN(CC(O)COC=3C=CC(=CC=3)C#N)CC2C1 PNKUCGCUUPYACP-UHFFFAOYSA-N 0.000 claims description 2
• NNIHXAQWSNOUEP-UHFFFAOYSA-N 4-[4-(3-butylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)-1-(3,4-dimethoxyphenoxy)butyl]benzonitrile Chemical compound C1C(O2)CN(S(=O)(=O)CCCC)CC2CN1CCCC(C=1C=CC(=CC=1)C#N)OC1=CC=C(OC)C(OC)=C1 NNIHXAQWSNOUEP-UHFFFAOYSA-N 0.000 claims description 2
• DLLQSMSEWJTYEW-UHFFFAOYSA-N 4-[4-[3-(2-phenoxyethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]butyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CCCCN1CC(O2)CN(CCOC=3C=CC=CC=3)CC2C1 DLLQSMSEWJTYEW-UHFFFAOYSA-N 0.000 claims description 2
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