CA2542226A1 - Novel diazaspiroalkanes and their use for treatment of ccr8 mediated diseases - Google Patents

Info

Publication number

CA2542226A1

CA2542226A1 CA002542226A CA2542226A CA2542226A1 CA 2542226 A1 CA2542226 A1 CA 2542226A1 CA 002542226 A CA002542226 A CA 002542226A CA 2542226 A CA2542226 A CA 2542226A CA 2542226 A1 CA2542226 A1 CA 2542226A1

Authority

CA

Canada

Prior art keywords

diazaspiro

isobutoxybenzyl

undecane

decane

benzyl

Prior art date

2003-10-23

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
• CIPO
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 22
• 201000010099 disease Diseases 0.000 title claims description 19
• 230000001404 mediated effect Effects 0.000 title claims description 8
• 238000011282 treatment Methods 0.000 title description 10
• 238000000034 method Methods 0.000 claims abstract description 308
• 150000001875 compounds Chemical class 0.000 claims abstract description 129
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 230000008569 process Effects 0.000 claims abstract description 7
• -1 1,3-butadienyl Chemical group 0.000 claims description 155
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
• 125000005842 heteroatom Chemical group 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 45
• 150000002367 halogens Chemical class 0.000 claims description 45
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 23
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 20
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 208000006673 asthma Diseases 0.000 claims description 17
• 108010012236 Chemokines Proteins 0.000 claims description 16
• 102000019034 Chemokines Human genes 0.000 claims description 16
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 102000009410 Chemokine receptor Human genes 0.000 claims description 14
• 108050000299 Chemokine receptor Proteins 0.000 claims description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 239000005711 Benzoic acid Substances 0.000 claims description 11
• 235000010233 benzoic acid Nutrition 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 235000010290 biphenyl Nutrition 0.000 claims description 10
• 239000004305 biphenyl Substances 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
• 238000006243 chemical reaction Methods 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• SLBGWOAUEBXQFH-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 SLBGWOAUEBXQFH-UHFFFAOYSA-N 0.000 claims description 7
• 125000006267 biphenyl group Chemical group 0.000 claims description 7
• SQLGFSQGYVLWDP-UHFFFAOYSA-N 1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-2-pyridin-2-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2N=CC=CC=2)CC1 SQLGFSQGYVLWDP-UHFFFAOYSA-N 0.000 claims description 6
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004001 thioalkyl group Chemical group 0.000 claims description 6
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
• 150000001204 N-oxides Chemical class 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• PCJRZWWIGKDMRN-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[7-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(C2)C(=O)CC=2C=CC(Cl)=CC=2)CC1 PCJRZWWIGKDMRN-UHFFFAOYSA-N 0.000 claims description 4
• FSCSFWQSLHTMDZ-UHFFFAOYSA-N [2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-quinolin-2-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C=2N=C3C=CC=CC3=CC=2)CC1 FSCSFWQSLHTMDZ-UHFFFAOYSA-N 0.000 claims description 4
• RUHVEBVCOKMWND-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-quinolin-2-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2N=C3C=CC=CC3=CC=2)CC1 RUHVEBVCOKMWND-UHFFFAOYSA-N 0.000 claims description 4
• PYOMKBWWKXYUSO-UHFFFAOYSA-N [9-[(2-propoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyridin-3-ylmethanone Chemical compound CCCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=NC=CC=2)CC1 PYOMKBWWKXYUSO-UHFFFAOYSA-N 0.000 claims description 4
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
• ZLYJNVAOVLQKJT-UHFFFAOYSA-N furan-3-yl-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C2=COC=C2)CC1 ZLYJNVAOVLQKJT-UHFFFAOYSA-N 0.000 claims description 4
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 4
• JJYUMTIICAOMEF-UHFFFAOYSA-N (2,3-dimethoxyphenyl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2CCC3(CN(CC=4C(=CC=CC=4)OCC(C)C)CC3)CC2)=C1OC JJYUMTIICAOMEF-UHFFFAOYSA-N 0.000 claims description 3
• NKDLCCSVBMTELE-UHFFFAOYSA-N (2,5-dimethylfuran-3-yl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C2=C(OC(C)=C2)C)CC1 NKDLCCSVBMTELE-UHFFFAOYSA-N 0.000 claims description 3
• YQULQZNEONLQEG-UHFFFAOYSA-N (2-chloropyridin-4-yl)-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=C(Cl)N=CC=2)CC1 YQULQZNEONLQEG-UHFFFAOYSA-N 0.000 claims description 3
• ULCNMQIXCYNMTB-UHFFFAOYSA-N (3,4-dimethoxyphenyl)-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=C(OC)C(OC)=CC=2)CC1 ULCNMQIXCYNMTB-UHFFFAOYSA-N 0.000 claims description 3
• NVKPQYKRYJWRDM-UHFFFAOYSA-N (3,4-dimethoxyphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 NVKPQYKRYJWRDM-UHFFFAOYSA-N 0.000 claims description 3
• VABPZOFSXMOXJL-UHFFFAOYSA-N (3-methoxyphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2CCC3(CCN(CC=4C(=CC=CC=4)OCC=4C=CC=CC=4)CC3)CC2)=C1 VABPZOFSXMOXJL-UHFFFAOYSA-N 0.000 claims description 3
• SRFAASSOCWCLLU-UHFFFAOYSA-N (4-chlorophenyl)-[7-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(C2)C(=O)C=2C=CC(Cl)=CC=2)CC1 SRFAASSOCWCLLU-UHFFFAOYSA-N 0.000 claims description 3
• JOAKHURLCLAFIC-UHFFFAOYSA-N (4-chlorophenyl)-[8-[(3-phenylmethoxyphenyl)methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)CC1 JOAKHURLCLAFIC-UHFFFAOYSA-N 0.000 claims description 3
• UWPITOWSOQEZOQ-UHFFFAOYSA-N (4-chlorophenyl)-[8-[[2-(2,4-dichlorophenoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OC=3C(=CC(Cl)=CC=3)Cl)CC2)CC1 UWPITOWSOQEZOQ-UHFFFAOYSA-N 0.000 claims description 3
• JXULUBBOFJCXQM-UHFFFAOYSA-N (4-chlorophenyl)-[8-[[2-[3-(trifluoromethyl)phenoxy]phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CC=2)CN2CCC3(CN(CC3)C(=O)C=3C=CC(Cl)=CC=3)CC2)=C1 JXULUBBOFJCXQM-UHFFFAOYSA-N 0.000 claims description 3
• GXCMLZQVQLFJSZ-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(3-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)CC1 GXCMLZQVQLFJSZ-UHFFFAOYSA-N 0.000 claims description 3
• ARBACXISHQJXDO-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(4-fluoro-3-phenoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CN(CC1)CCC1(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 ARBACXISHQJXDO-UHFFFAOYSA-N 0.000 claims description 3
• MBOIDHAANMPQOU-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(4-phenoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)CC1 MBOIDHAANMPQOU-UHFFFAOYSA-N 0.000 claims description 3
• KPEBIXRQMFUTMJ-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2,4-dichlorophenoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OC=3C(=CC(Cl)=CC=3)Cl)CC2)CC1 KPEBIXRQMFUTMJ-UHFFFAOYSA-N 0.000 claims description 3
• ACKKHACPPWZKLG-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2-methylpropoxy)pyridin-3-yl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=NC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 ACKKHACPPWZKLG-UHFFFAOYSA-N 0.000 claims description 3
• NBHZOOSVENOVAH-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(4-fluorophenoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(F)=CC=C1OC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 NBHZOOSVENOVAH-UHFFFAOYSA-N 0.000 claims description 3
• CRTIODLVLHSSER-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(4-methylphenoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 CRTIODLVLHSSER-UHFFFAOYSA-N 0.000 claims description 3
• YIFAUCXTPJHPQT-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-[3-(trifluoromethyl)phenoxy]phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CC=2)CN2CCC3(CC2)CCN(CC3)C(=O)C=2C=CC(Cl)=CC=2)=C1 YIFAUCXTPJHPQT-UHFFFAOYSA-N 0.000 claims description 3
• WZMHONMKTCMPPF-UHFFFAOYSA-N 1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-2-pyridin-2-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2N=CC=CC=2)CC1 WZMHONMKTCMPPF-UHFFFAOYSA-N 0.000 claims description 3
• TWCHWOJIVRRGOO-UHFFFAOYSA-N 1-[4-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decane-2-carbonyl]phenyl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=CC(=CC=2)C(C)=O)CC1 TWCHWOJIVRRGOO-UHFFFAOYSA-N 0.000 claims description 3
• CPXRORQTVVZAJR-UHFFFAOYSA-N 1-[4-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]phenyl]ethanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(=CC=2)C(C)=O)CC1 CPXRORQTVVZAJR-UHFFFAOYSA-N 0.000 claims description 3
• VAENDSBYFHYBQF-UHFFFAOYSA-N 1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-2-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=C(C=CC=2)C(F)(F)F)CC1 VAENDSBYFHYBQF-UHFFFAOYSA-N 0.000 claims description 3
• PSOZJOZKEVZLKZ-UHFFFAOYSA-N 2,4-dimethyloxazole Chemical group CC1=COC(C)=N1 PSOZJOZKEVZLKZ-UHFFFAOYSA-N 0.000 claims description 3
• CRHQCIKQHKUOCW-UHFFFAOYSA-N 2-(2-fluorophenyl)-1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2C(=CC=CC=2)F)CC1 CRHQCIKQHKUOCW-UHFFFAOYSA-N 0.000 claims description 3
• DAQNUHXQCXYDGV-UHFFFAOYSA-N 2-(4-butoxyphenyl)-1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]ethanone Chemical compound C1=CC(OCCCC)=CC=C1CC(=O)N1CCC2(CN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 DAQNUHXQCXYDGV-UHFFFAOYSA-N 0.000 claims description 3
• KXDXEYRKRLBRMI-UHFFFAOYSA-N 2-(4-methylphenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=CC(C)=CC=2)CC1 KXDXEYRKRLBRMI-UHFFFAOYSA-N 0.000 claims description 3
• FNRZRWBBDDTDHP-UHFFFAOYSA-N 2-[2-[[2-(4-chlorobenzoyl)-2,7-diazaspiro[3.5]nonan-7-yl]methyl]phenoxy]benzonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OC=3C(=CC=CC=3)C#N)CC2)C1 FNRZRWBBDDTDHP-UHFFFAOYSA-N 0.000 claims description 3
• MMTMJNRRGVDDMA-UHFFFAOYSA-N 2-[2-[[2-(4-chlorobenzoyl)-2,8-diazaspiro[4.5]decan-8-yl]methyl]phenoxy]benzonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OC=3C(=CC=CC=3)C#N)CC2)CC1 MMTMJNRRGVDDMA-UHFFFAOYSA-N 0.000 claims description 3
• GZZWLAUGZJGYTD-UHFFFAOYSA-N 3-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C(=O)N(CC1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 GZZWLAUGZJGYTD-UHFFFAOYSA-N 0.000 claims description 3
• NWNSCXYMBGIZNK-UHFFFAOYSA-N 4-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]benzonitrile Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(=CC=2)C#N)CC1 NWNSCXYMBGIZNK-UHFFFAOYSA-N 0.000 claims description 3
• JFDPDCXFTOPMPS-UHFFFAOYSA-N 9-[[2-(2-methylpropoxy)phenyl]methyl]-3-thiophen-2-ylsulfonyl-3,9-diazaspiro[5.5]undecane Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)S(=O)(=O)C=2SC=CC=2)CC1 JFDPDCXFTOPMPS-UHFFFAOYSA-N 0.000 claims description 3
• WOKWCEYISFKDJD-UHFFFAOYSA-N 9-[[2-(2-methylpropoxy)phenyl]methyl]-n-thiophen-3-yl-3,9-diazaspiro[5.5]undecane-3-carboxamide Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)NC2=CSC=C2)CC1 WOKWCEYISFKDJD-UHFFFAOYSA-N 0.000 claims description 3
• 108010017148 CCR8 Receptors Proteins 0.000 claims description 3
• 102000004426 CCR8 Receptors Human genes 0.000 claims description 3
• BJDXLOANZHNDTC-UHFFFAOYSA-N [2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 BJDXLOANZHNDTC-UHFFFAOYSA-N 0.000 claims description 3
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• CCMJSRVNURGYSJ-UHFFFAOYSA-N (4-chlorophenyl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-7-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)C1 CCMJSRVNURGYSJ-UHFFFAOYSA-N 0.000 claims description 2
• RGFVJJRPKXUZTD-UHFFFAOYSA-N (4-chlorophenyl)-[2-[[2-(4-fluorophenoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-7-yl]methanone Chemical compound C1=CC(F)=CC=C1OC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)C1 RGFVJJRPKXUZTD-UHFFFAOYSA-N 0.000 claims description 2
• FUNNUOZFKZTROI-UHFFFAOYSA-N (4-chlorophenyl)-[2-[[2-[3-(trifluoromethyl)phenoxy]phenyl]methyl]-2,7-diazaspiro[3.5]nonan-7-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CC=2)CN2CC3(C2)CCN(CC3)C(=O)C=2C=CC(Cl)=CC=2)=C1 FUNNUOZFKZTROI-UHFFFAOYSA-N 0.000 claims description 2
• NDUXWJLMAYYXCC-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(2-phenoxyphenyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OC=3C=CC=CC=3)CC2)C1 NDUXWJLMAYYXCC-UHFFFAOYSA-N 0.000 claims description 2
• NKBDZFGRQCCUPH-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(2-phenoxyphenyl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CN(CC=3C(=CC=CC=3)OC=3C=CC=CC=3)CC2)CC1 NKBDZFGRQCCUPH-UHFFFAOYSA-N 0.000 claims description 2
• QRSYEGIFRAHIDH-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(2-phenylmethoxyphenyl)methyl]-2,7-diazaspiro[4.4]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 QRSYEGIFRAHIDH-UHFFFAOYSA-N 0.000 claims description 2
• HLPLMCHPJNJQDR-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(2-pyridin-3-yloxyphenyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OC=3C=NC=CC=3)CC2)C1 HLPLMCHPJNJQDR-UHFFFAOYSA-N 0.000 claims description 2
• PSTNRKQEFUMVQG-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(3-phenoxyphenyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)CC2)C1 PSTNRKQEFUMVQG-UHFFFAOYSA-N 0.000 claims description 2
• KTYRHTVPTQJJNB-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(3-phenylmethoxyphenyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)C1 KTYRHTVPTQJJNB-UHFFFAOYSA-N 0.000 claims description 2
• WRRRZUDCUHPTIR-UHFFFAOYSA-N (4-chlorophenyl)-[7-[(4-fluoro-3-phenoxyphenyl)methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CN(CC1)CCC1(C1)CN1C(=O)C1=CC=C(Cl)C=C1 WRRRZUDCUHPTIR-UHFFFAOYSA-N 0.000 claims description 2
• NZLNNNDBXLCGEP-UHFFFAOYSA-N (4-chlorophenyl)-[7-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 NZLNNNDBXLCGEP-UHFFFAOYSA-N 0.000 claims description 2
• MEJZFZDOIBQQQU-UHFFFAOYSA-N (4-chlorophenyl)-[7-[[2-(4-fluorophenoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound C1=CC(F)=CC=C1OC1=CC=CC=C1CN1CCC2(CN(C2)C(=O)C=2C=CC(Cl)=CC=2)CC1 MEJZFZDOIBQQQU-UHFFFAOYSA-N 0.000 claims description 2
• QOQWJTAGQCMGNB-UHFFFAOYSA-N (4-chlorophenyl)-[7-[[2-[3-(trifluoromethyl)phenoxy]phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CC=2)CN2CCC3(CN(C3)C(=O)C=3C=CC(Cl)=CC=3)CC2)=C1 QOQWJTAGQCMGNB-UHFFFAOYSA-N 0.000 claims description 2
• HHKKTCPLAKLKEK-UHFFFAOYSA-N (4-chlorophenyl)-[7-[[3-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[4.4]nonan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC(CN2CC3(CN(CC3)C(=O)C=3C=CC(Cl)=CC=3)CC2)=C1 HHKKTCPLAKLKEK-UHFFFAOYSA-N 0.000 claims description 2
• JYLSDPVKHOMAHG-UHFFFAOYSA-N (4-chlorophenyl)-[8-[(4-phenoxyphenyl)methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)CC1 JYLSDPVKHOMAHG-UHFFFAOYSA-N 0.000 claims description 2
• QAYYCPSHKPIIHS-UHFFFAOYSA-N (4-chlorophenyl)-[8-[[2-(4-fluorophenoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(F)=CC=C1OC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 QAYYCPSHKPIIHS-UHFFFAOYSA-N 0.000 claims description 2
• HREVIXVHGALCMA-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 HREVIXVHGALCMA-UHFFFAOYSA-N 0.000 claims description 2
• RFYUVDOAAJUIDW-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 RFYUVDOAAJUIDW-UHFFFAOYSA-N 0.000 claims description 2
• HYLZAKLWGBKDBY-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(3,5-diethoxypyridin-4-yl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CN=CC(OCC)=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 HYLZAKLWGBKDBY-UHFFFAOYSA-N 0.000 claims description 2
• YHKSOBZFXYKFOV-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(3-phenoxythiophen-2-yl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC3=C(C=CS3)OC=3C=CC=CC=3)CC2)CC1 YHKSOBZFXYKFOV-UHFFFAOYSA-N 0.000 claims description 2
• OFQXWKBMSPQCSI-UHFFFAOYSA-N (4-chlorophenyl)-[9-[(3-pyridin-2-yloxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C=C(OC=4N=CC=CC=4)C=CC=3)CC2)CC1 OFQXWKBMSPQCSI-UHFFFAOYSA-N 0.000 claims description 2
• XWHKMIGQUZFGGZ-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2-fluorophenyl)sulfanylphenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound FC1=CC=CC=C1SC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 XWHKMIGQUZFGGZ-UHFFFAOYSA-N 0.000 claims description 2
• FVIRTVGXWNRAMY-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2-methoxyphenoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound COC1=CC=CC=C1OC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 FVIRTVGXWNRAMY-UHFFFAOYSA-N 0.000 claims description 2
• PNORIZSLKMOCIM-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CCC2)C(=O)C=2C=CC(Cl)=CC=2)CC1 PNORIZSLKMOCIM-UHFFFAOYSA-N 0.000 claims description 2
• AGKGJRFCHDJDTK-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-(pyridin-2-ylmethoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3N=CC=CC=3)CC2)CC1 AGKGJRFCHDJDTK-UHFFFAOYSA-N 0.000 claims description 2
• DFLGBSAJRYIZGO-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[2-[(2,6-dichlorophenyl)methoxy]phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C(=CC=CC=3Cl)Cl)CC2)CC1 DFLGBSAJRYIZGO-UHFFFAOYSA-N 0.000 claims description 2
• QPJDUGWRGZOPGZ-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[3-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC(CN2CCC3(CC2)CCN(CC3)C(=O)C=2C=CC(Cl)=CC=2)=C1 QPJDUGWRGZOPGZ-UHFFFAOYSA-N 0.000 claims description 2
• KHCYJVDMWZFKCD-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[3-(pyridin-2-ylmethoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C=C(OCC=4N=CC=CC=4)C=CC=3)CC2)CC1 KHCYJVDMWZFKCD-UHFFFAOYSA-N 0.000 claims description 2
• UDUUVKFILMVWAO-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[3-(pyridin-3-ylmethoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C=C(OCC=4C=NC=CC=4)C=CC=3)CC2)CC1 UDUUVKFILMVWAO-UHFFFAOYSA-N 0.000 claims description 2
• RBGWZWATTGWGOT-UHFFFAOYSA-N (4-chlorophenyl)-[9-[[6-(2-methylpropoxy)pyridin-2-yl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC(CN2CCC3(CC2)CCN(CC3)C(=O)C=2C=CC(Cl)=CC=2)=N1 RBGWZWATTGWGOT-UHFFFAOYSA-N 0.000 claims description 2
• KYASNWSODINYGC-UHFFFAOYSA-N (4-ethylphenyl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCC2(CN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 KYASNWSODINYGC-UHFFFAOYSA-N 0.000 claims description 2
• HONSGVYPOPVNBD-UHFFFAOYSA-N (4-ethylphenyl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 HONSGVYPOPVNBD-UHFFFAOYSA-N 0.000 claims description 2
• UUCHOWRUVQRXIP-UHFFFAOYSA-N (4-fluorophenyl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(F)=CC=2)CC1 UUCHOWRUVQRXIP-UHFFFAOYSA-N 0.000 claims description 2
• STQOLMSFWBRIHJ-UHFFFAOYSA-N (4-imidazol-1-ylphenyl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(=CC=2)N2C=NC=C2)CC1 STQOLMSFWBRIHJ-UHFFFAOYSA-N 0.000 claims description 2
• WGNKKYRMPQMKAA-UHFFFAOYSA-N (4-methoxyphenyl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC2(CN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 WGNKKYRMPQMKAA-UHFFFAOYSA-N 0.000 claims description 2
• LCCRCFPPCYBQBH-UHFFFAOYSA-N (4-methoxyphenyl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 LCCRCFPPCYBQBH-UHFFFAOYSA-N 0.000 claims description 2
• GPKJBVRVVPHIHD-UHFFFAOYSA-N (4-methoxyphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 GPKJBVRVVPHIHD-UHFFFAOYSA-N 0.000 claims description 2
• QGZGFVBEWICKEP-UHFFFAOYSA-N (4-methoxythiophen-3-yl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound COC1=CSC=C1C(=O)N1CC2(CCN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 QGZGFVBEWICKEP-UHFFFAOYSA-N 0.000 claims description 2
• GIOZKTQYTLMYLM-UHFFFAOYSA-N (4-methylphenyl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=CC(C)=CC=2)CC1 GIOZKTQYTLMYLM-UHFFFAOYSA-N 0.000 claims description 2
• MSNHQFBLJWBGBG-UHFFFAOYSA-N (4-methylphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 MSNHQFBLJWBGBG-UHFFFAOYSA-N 0.000 claims description 2
• LZPSFUFYZVBXOQ-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)N(CC1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 LZPSFUFYZVBXOQ-UHFFFAOYSA-N 0.000 claims description 2
• RGILUVYXGBIFIW-UHFFFAOYSA-N (4-phenoxyphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 RGILUVYXGBIFIW-UHFFFAOYSA-N 0.000 claims description 2
• ASQOWVVTNOKVRU-UHFFFAOYSA-N (4-tert-butylphenyl)-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(=CC=2)C(C)(C)C)CC1 ASQOWVVTNOKVRU-UHFFFAOYSA-N 0.000 claims description 2
• LWCMCHJZIRLPJY-UHFFFAOYSA-N (4-tert-butylphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 LWCMCHJZIRLPJY-UHFFFAOYSA-N 0.000 claims description 2
• VAHNEBNBTSKPQH-UHFFFAOYSA-N (5-chlorothiophen-2-yl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2SC(Cl)=CC=2)CC1 VAHNEBNBTSKPQH-UHFFFAOYSA-N 0.000 claims description 2
• MDORBGCVWZXQJN-UHFFFAOYSA-N (5-methyl-1,2-oxazol-4-yl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C2=C(ON=C2)C)CC1 MDORBGCVWZXQJN-UHFFFAOYSA-N 0.000 claims description 2
• LUPBKYHHQJHCCC-UHFFFAOYSA-N (5-methyl-1,2-oxazol-4-yl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C2=C(ON=C2)C)CC1 LUPBKYHHQJHCCC-UHFFFAOYSA-N 0.000 claims description 2
• OKWMBUHTJRUIHO-UHFFFAOYSA-N (6-chloropyridin-2-yl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2N=C(Cl)C=CC=2)CC1 OKWMBUHTJRUIHO-UHFFFAOYSA-N 0.000 claims description 2
• AJQONPANPQIPGY-UHFFFAOYSA-N (6-chloropyridin-3-yl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C=2C=NC(Cl)=CC=2)CC1 AJQONPANPQIPGY-UHFFFAOYSA-N 0.000 claims description 2
• WSMPDJVQPNLFER-UHFFFAOYSA-N (6-chloropyridin-3-yl)-[9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=NC(Cl)=CC=2)CC1 WSMPDJVQPNLFER-UHFFFAOYSA-N 0.000 claims description 2
• JULCORUJWWZYBP-UHFFFAOYSA-N (6-chloropyridin-3-yl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=NC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 JULCORUJWWZYBP-UHFFFAOYSA-N 0.000 claims description 2
• DQMITIATTVSMGJ-UHFFFAOYSA-N (6-chloropyridin-3-yl)-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=NC(Cl)=CC=2)CC1 DQMITIATTVSMGJ-UHFFFAOYSA-N 0.000 claims description 2
• ATBIGSKBZUKMDC-UHFFFAOYSA-N (6-methoxynaphthalen-2-yl)-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(=O)N(CC1)CCC1(C1)CCN1CC1=CC=CC=C1OCC(C)C ATBIGSKBZUKMDC-UHFFFAOYSA-N 0.000 claims description 2
• IOIHVFIOTCXTOD-UHFFFAOYSA-N (6-methoxynaphthalen-2-yl)-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]methanone Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(=O)N(C1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC(C)C IOIHVFIOTCXTOD-UHFFFAOYSA-N 0.000 claims description 2
• LNXAIMAIZLKSMS-UHFFFAOYSA-N 1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[4.5]decan-7-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CN(CCC2)C(=O)CC=2C=CN=CC=2)CC1 LNXAIMAIZLKSMS-UHFFFAOYSA-N 0.000 claims description 2
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• RULHVRMTPGYCCM-UHFFFAOYSA-N 1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-2-(4-nitrophenyl)ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2C=CC(=CC=2)[N+]([O-])=O)CC1 RULHVRMTPGYCCM-UHFFFAOYSA-N 0.000 claims description 2
• OOHRQHHHLQQFJN-UHFFFAOYSA-N 1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-2-(4-propan-2-ylphenyl)ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2C=CC(=CC=2)C(C)C)CC1 OOHRQHHHLQQFJN-UHFFFAOYSA-N 0.000 claims description 2
• CMQBXKFKKXOHLK-UHFFFAOYSA-N 1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2C=CN=CC=2)CC1 CMQBXKFKKXOHLK-UHFFFAOYSA-N 0.000 claims description 2
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• CLTZYTPUGOPXFJ-UHFFFAOYSA-N 1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-2-[4-(trifluoromethoxy)phenyl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)CC1 CLTZYTPUGOPXFJ-UHFFFAOYSA-N 0.000 claims description 2
• XQRPKJKNVFFUOI-UHFFFAOYSA-N 1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-2-pyridin-3-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=NC=CC=2)CC1 XQRPKJKNVFFUOI-UHFFFAOYSA-N 0.000 claims description 2
• KPURWJGHBAAIOE-UHFFFAOYSA-N 1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=CN=CC=2)CC1 KPURWJGHBAAIOE-UHFFFAOYSA-N 0.000 claims description 2
• IOBWQRZRMWMISJ-UHFFFAOYSA-N 1-[9-[[2-(2-methylpropoxy)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-2-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CCC2)C(=O)CC=2C=CN=CC=2)CC1 IOBWQRZRMWMISJ-UHFFFAOYSA-N 0.000 claims description 2
• WICILWOXXADAAO-UHFFFAOYSA-N 1-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-2-pyridin-2-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)CC=2N=CC=CC=2)CC1 WICILWOXXADAAO-UHFFFAOYSA-N 0.000 claims description 2
• ZMYSAKFIHBDLIB-UHFFFAOYSA-N 1-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-2-pyridin-3-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)CC=2C=NC=CC=2)CC1 ZMYSAKFIHBDLIB-UHFFFAOYSA-N 0.000 claims description 2
• UHAGZAULFKJQKB-UHFFFAOYSA-N 1-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)CC=2C=CN=CC=2)CC1 UHAGZAULFKJQKB-UHFFFAOYSA-N 0.000 claims description 2
• ZOZZIVOEWLWIJP-UHFFFAOYSA-N 2,4-dimethyl-5-[[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]sulfonyl]-1,3-thiazole Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)S(=O)(=O)C2=C(N=C(C)S2)C)CC1 ZOZZIVOEWLWIJP-UHFFFAOYSA-N 0.000 claims description 2
• VMDTUEYHPJLMLD-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=C3OCOC3=CC=2)CC1 VMDTUEYHPJLMLD-UHFFFAOYSA-N 0.000 claims description 2
• PETFYVWPUATJBB-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)CC=2C(=CC(Cl)=CC=2)Cl)CC1 PETFYVWPUATJBB-UHFFFAOYSA-N 0.000 claims description 2
• XGHKIIHJJHZVRC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C(=CC(Cl)=CC=2)Cl)CC1 XGHKIIHJJHZVRC-UHFFFAOYSA-N 0.000 claims description 2
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• OREDVXIKZCFVJU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C(=CC(F)=CC=2)F)CC1 OREDVXIKZCFVJU-UHFFFAOYSA-N 0.000 claims description 2
• YMQSHLLSWNGNOH-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C(=CC=C(F)C=2)F)CC1 YMQSHLLSWNGNOH-UHFFFAOYSA-N 0.000 claims description 2
• DWXDWFCZKNFDDG-UHFFFAOYSA-N 2-(2-fluorophenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C(=CC=CC=2)F)CC1 DWXDWFCZKNFDDG-UHFFFAOYSA-N 0.000 claims description 2
• DPHQOVDDEBDHJF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)N1CCC2(CN(CC=3C(=CC=CC=3)OCC(C)C)CC2)CC1 DPHQOVDDEBDHJF-UHFFFAOYSA-N 0.000 claims description 2
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• BDSVRQWGIQAICL-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=C(F)C=C(F)C=2)CC1 BDSVRQWGIQAICL-UHFFFAOYSA-N 0.000 claims description 2
• LHCXJOCQCRKCPK-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)CC=2C=C(C)C=C(C)C=2)CC1 LHCXJOCQCRKCPK-UHFFFAOYSA-N 0.000 claims description 2
• FFTATLHVUBBLLF-UHFFFAOYSA-N 2-(3-methoxy-4-phenylmethoxyphenyl)-1-[8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]ethanone Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1CC(=O)N(C1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC(C)C FFTATLHVUBBLLF-UHFFFAOYSA-N 0.000 claims description 2
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• IQBJGVGFIOTTGE-UHFFFAOYSA-N [9-[[6-(2-methylpropoxy)pyridin-2-yl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyrimidin-4-ylmethanone Chemical compound CC(C)COC1=CC=CC(CN2CCC3(CC2)CCN(CC3)C(=O)C=2N=CN=CC=2)=N1 IQBJGVGFIOTTGE-UHFFFAOYSA-N 0.000 claims description 2
• KMKFTWPGQMXQGP-UHFFFAOYSA-N furan-3-yl-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[4.5]decan-7-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CN(CCC2)C(=O)C2=COC=C2)CC1 KMKFTWPGQMXQGP-UHFFFAOYSA-N 0.000 claims description 2
• SMLKTYHPZAZXEH-UHFFFAOYSA-N furan-3-yl-[2-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CC2(CCN(CC2)C(=O)C2=COC=C2)CC1 SMLKTYHPZAZXEH-UHFFFAOYSA-N 0.000 claims description 2
• XEZWTZFZEMQSEP-UHFFFAOYSA-N furan-3-yl-[9-[[2-(2-methylpropoxy)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-2-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CCC2)C(=O)C2=COC=C2)CC1 XEZWTZFZEMQSEP-UHFFFAOYSA-N 0.000 claims description 2
• WLLQZCFMJUUOLJ-UHFFFAOYSA-N furan-3-yl-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C2=COC=C2)CC1 WLLQZCFMJUUOLJ-UHFFFAOYSA-N 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• XJQMKTSZVNCLPM-UHFFFAOYSA-N naphthalen-1-yl-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)N(CC1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 XJQMKTSZVNCLPM-UHFFFAOYSA-N 0.000 claims description 2
• 230000003287 optical effect Effects 0.000 claims description 2
• FNJLCLPEIIPUOG-UHFFFAOYSA-N phenyl-[9-[(2-propoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound CCCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC=CC=2)CC1 FNJLCLPEIIPUOG-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
• 125000005843 halogen group Chemical group 0.000 claims 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
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• JMSHGWASLYZJPD-UHFFFAOYSA-N 9-[[2-(2-methylpropoxy)phenyl]methyl]-n-thiophen-2-yl-3,9-diazaspiro[5.5]undecane-3-carboxamide Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)NC=2SC=CC=2)CC1 JMSHGWASLYZJPD-UHFFFAOYSA-N 0.000 claims 1
• WUNGBJBKZCQSIS-UHFFFAOYSA-N [4-(diethylamino)phenyl]-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 WUNGBJBKZCQSIS-UHFFFAOYSA-N 0.000 claims 1
• SKPVSHSMPXHENT-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-(1h-pyrazol-4-yl)methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C2=CNN=C2)CC1 SKPVSHSMPXHENT-UHFFFAOYSA-N 0.000 claims 1
• IRYYKJUTWWQZKQ-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-(2-morpholin-4-ylpyridin-3-yl)methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C(=NC=CC=2)N2CCOCC2)CC1 IRYYKJUTWWQZKQ-UHFFFAOYSA-N 0.000 claims 1
• GVDMZQURFGRXCC-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=CC(OC(C)C)=CC=2)CC1 GVDMZQURFGRXCC-UHFFFAOYSA-N 0.000 claims 1
• WAJKLNCFGJURGG-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 WAJKLNCFGJURGG-UHFFFAOYSA-N 0.000 claims 1
• QKGWWWDIOTVOAF-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-naphthalen-1-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C3=CC=CC=C3C=CC=2)CC1 QKGWWWDIOTVOAF-UHFFFAOYSA-N 0.000 claims 1
• XVVKUAXKWWUJKW-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-naphthalen-2-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C=C3C=CC=CC3=CC=2)CC1 XVVKUAXKWWUJKW-UHFFFAOYSA-N 0.000 claims 1
• FFIWTQYZOIYZMD-UHFFFAOYSA-N [9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-(1-oxidopyridin-1-ium-4-yl)methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=C[N+]([O-])=CC=2)CC1 FFIWTQYZOIYZMD-UHFFFAOYSA-N 0.000 claims 1
• FLGMTJVYOGQTGA-UHFFFAOYSA-N [9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyrimidin-2-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2N=CC=CN=2)CC1 FLGMTJVYOGQTGA-UHFFFAOYSA-N 0.000 claims 1
• XHYHAGAWIQDXFU-UHFFFAOYSA-N [9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyrimidin-4-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2N=CN=CC=2)CC1 XHYHAGAWIQDXFU-UHFFFAOYSA-N 0.000 claims 1
• YFORNXYNZJRFRD-UHFFFAOYSA-N [9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-pyrimidin-5-ylmethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=NC=NC=2)CC1 YFORNXYNZJRFRD-UHFFFAOYSA-N 0.000 claims 1
• KKXLARFJHBJNMN-UHFFFAOYSA-N ethyl 2-[[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]amino]acetate Chemical compound C1CN(C(=O)NCC(=O)OCC)CCC11CCN(CC=2C(=CC=CC=2)OCC(C)C)CC1 KKXLARFJHBJNMN-UHFFFAOYSA-N 0.000 claims 1
• LTTNSPNSWRJGNJ-UHFFFAOYSA-N ethyl 3-[[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC(=O)N2CCC3(CCN(CC=4C(=CC=CC=4)OCC(C)C)CC3)CC2)=C1 LTTNSPNSWRJGNJ-UHFFFAOYSA-N 0.000 claims 1
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