NO327977B1 - Nye oksabispidinforbindelser som er nyttige i behandlingen av hjertearrytmier, fremgangsmate til fremstilling derav, farmasoytiske sammensetninger som inkluderer nevnte forbindelser, samt mellomprodukter og fremgangsmater til fremstilling av mellomprodukter - Google Patents

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Publication number

NO327977B1

NO327977B1 NO20021811A NO20021811A NO327977B1 NO 327977 B1 NO327977 B1 NO 327977B1 NO 20021811 A NO20021811 A NO 20021811A NO 20021811 A NO20021811 A NO 20021811A NO 327977 B1 NO327977 B1 NO 327977B1

Authority

NO

Norway

Prior art keywords

oxa

diazabicyclo

benzonitrile

formula

compound

Prior art date

1999-10-18

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 467
• 206010003119 arrhythmia Diseases 0.000 title claims abstract description 24
• 238000011282 treatment Methods 0.000 title claims abstract description 19
• 238000000034 method Methods 0.000 title claims description 76
• 238000002360 preparation method Methods 0.000 title claims description 39
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
• 239000000543 intermediate Substances 0.000 title description 23
• 230000006793 arrhythmia Effects 0.000 claims abstract description 15
• 238000011321 prophylaxis Methods 0.000 claims abstract description 7
• 230000001746 atrial effect Effects 0.000 claims abstract description 5
• 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 4
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 207
• 238000006243 chemical reaction Methods 0.000 claims description 84
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 75
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 68
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 239000002904 solvent Substances 0.000 claims description 51
• -1 2-(4-acetyl-1-piperazinyl)ethyl Chemical group 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 32
• 125000002947 alkylene group Chemical group 0.000 claims description 28
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 230000008569 process Effects 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 239000003054 catalyst Substances 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
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
• 239000011630 iodine Substances 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 238000010511 deprotection reaction Methods 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 5
• 230000002140 halogenating effect Effects 0.000 claims description 5
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 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
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 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
• CABBRIUTEWJNNX-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)ethyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1CN(C(=O)C)CCN1CCOC(=O)N1CC(O2)CN(CC(O)COC=3C=CC(=CC=3)C#N)CC2C1 CABBRIUTEWJNNX-UHFFFAOYSA-N 0.000 claims description 2
• WVRPVDXSUTXPJS-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)ethyl 7-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1=C(OC)C(OC)=CC=C1OC(C=1C=CC(=CC=1)C#N)CCCN1CC(O2)CN(C(=O)OCCN3CCN(CC3)C(C)=O)CC2C1 WVRPVDXSUTXPJS-UHFFFAOYSA-N 0.000 claims description 2
• UUMZOQBIWQJDQS-UHFFFAOYSA-N 2-[7-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]-n-propan-2-ylacetamide Chemical compound C1C(O2)CN(CC(=O)NC(C)C)CC2CN1CCOC1=CC=C(C#N)C=C1 UUMZOQBIWQJDQS-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
• BYJIWSCHQPNARL-UHFFFAOYSA-N 4-[1-(3,4-dimethoxyphenoxy)-4-[3-[2-(3,4-dimethoxyphenyl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]butyl]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN1CC(O2)CN(CCCC(OC=3C=C(OC)C(OC)=CC=3)C=3C=CC(=CC=3)C#N)CC2C1 BYJIWSCHQPNARL-UHFFFAOYSA-N 0.000 claims description 2
• RYYDXQOTNIVFHE-UHFFFAOYSA-N 4-[2-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CCOC1=CC=C(C#N)C=C1 RYYDXQOTNIVFHE-UHFFFAOYSA-N 0.000 claims description 2
• DLNQRFVTNDOROI-UHFFFAOYSA-N 4-[2-[3-(imidazo[1,2-a]pyridin-2-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCN1CC(O2)CN(CC=3N=C4C=CC=CN4C=3)CC2C1 DLNQRFVTNDOROI-UHFFFAOYSA-N 0.000 claims description 2
• NVOOJOZGMYNPJV-UHFFFAOYSA-N 4-[2-[3-[1-(2,6-dimethylphenoxy)propan-2-yl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C1C(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2CN1C(C)COC1=C(C)C=CC=C1C NVOOJOZGMYNPJV-UHFFFAOYSA-N 0.000 claims description 2
• CSGHHNHUEHTXHP-UHFFFAOYSA-N 4-[2-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethoxy]benzonitrile Chemical compound C=1C=C2OCCOC2=CC=1C(=O)CN(CC(C1)O2)CC2CN1CCOC1=CC=C(C#N)C=C1 CSGHHNHUEHTXHP-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
• SZDONXTVKAXDLH-UHFFFAOYSA-N 4-[2-[3-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]ethyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 SZDONXTVKAXDLH-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
• 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
• ZZTDZOBVWCNSSA-UHFFFAOYSA-N 4-[2-[7-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound N1=CSC(CCN2CC3CN(CCOC=4C=CC(=CC=4)C#N)CC(O3)C2)=C1C ZZTDZOBVWCNSSA-UHFFFAOYSA-N 0.000 claims description 2
• BXLKDOXGUJOFFK-UHFFFAOYSA-N 4-[2-[7-[3-(4-acetylpiperazin-1-yl)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethoxy]benzonitrile Chemical compound C1CN(C(=O)C)CCN1CCCN1CC(O2)CN(CCOC=3C=CC(=CC=3)C#N)CC2C1 BXLKDOXGUJOFFK-UHFFFAOYSA-N 0.000 claims description 2
• ILMYQYNVENUQBH-UHFFFAOYSA-N 4-[2-hydroxy-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(CC(O)COC=3C=CC(=CC=3)C#N)CC2C1 ILMYQYNVENUQBH-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
• ATVCVFPEZAMBTR-UHFFFAOYSA-N 4-[3-[3-(2-hydroxy-3,3-dimethylbutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1C(O2)CN(CC(O)C(C)(C)C)CC2CN1CCCNC1=CC=C(C#N)C=C1 ATVCVFPEZAMBTR-UHFFFAOYSA-N 0.000 claims description 2
• BOPMSTVIKMTABR-UHFFFAOYSA-N 4-[3-[3-(2-phenoxyethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCCN1CC(O2)CN(CCOC=3C=CC=CC=3)CC2C1 BOPMSTVIKMTABR-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
• WDXMNFWBNDQQHC-UHFFFAOYSA-N 4-[3-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]-2-hydroxypropoxy]benzonitrile Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CC(O)COC1=CC=C(C#N)C=C1 WDXMNFWBNDQQHC-UHFFFAOYSA-N 0.000 claims description 2
• AOEOLHLDYZNZAO-UHFFFAOYSA-N 4-[3-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CCCOC1=CC=C(C#N)C=C1 AOEOLHLDYZNZAO-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
• GXVXNBMDZSSXJO-UHFFFAOYSA-N 4-[3-[3-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylsulfonyl]benzonitrile Chemical compound C1C(O2)CN(CC(=O)C(C)(C)C)CC2CN1CCCS(=O)(=O)C1=CC=C(C#N)C=C1 GXVXNBMDZSSXJO-UHFFFAOYSA-N 0.000 claims description 2
• XQPVCBWJWTYQFE-UHFFFAOYSA-N 4-[3-[3-(3,3-dimethylbutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1C(O2)CN(CCC(C)(C)C)CC2CN1CCCNC1=CC=C(C#N)C=C1 XQPVCBWJWTYQFE-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
• ZRTWXSDCUARRTM-UHFFFAOYSA-N 4-[3-[3-(cyclopropylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propylamino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NCCCN1CC(O2)CN(CC3CC3)CC2C1 ZRTWXSDCUARRTM-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
• CRAXQHFQRVIJRK-UHFFFAOYSA-N 4-[3-[3-(imidazo[1,2-a]pyridin-2-ylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCCN1CC(O2)CN(CC=3N=C4C=CC=CN4C=3)CC2C1 CRAXQHFQRVIJRK-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
• OEYDFULLPBQXOD-UHFFFAOYSA-N 4-[3-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxoethyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl]propoxy]benzonitrile Chemical compound C=1C=C2OCCOC2=CC=1C(=O)CN(CC(C1)O2)CC2CN1CCCOC1=CC=C(C#N)C=C1 OEYDFULLPBQXOD-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
• 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
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