MXPA06004300A - Nuevos diazaespiroalcanos y su uso para tratamiento de enfermedades mediadas por ccr8. - Google Patents

Info

Publication number

MXPA06004300A

MXPA06004300A MXPA06004300A MXPA06004300A MXPA06004300A MX PA06004300 A MXPA06004300 A MX PA06004300A MX PA06004300 A MXPA06004300 A MX PA06004300A MX PA06004300 A MXPA06004300 A MX PA06004300A MX PA06004300 A MXPA06004300 A MX PA06004300A

Authority

MX

Mexico

Prior art keywords

diazaspiro

isobutoxybenzyl

undecane

decane

chlorobenzoyl

Prior art date

2003-10-23

Links

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• Global Dossier
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 21
• 201000010099 disease Diseases 0.000 title claims description 19
• 238000011282 treatment Methods 0.000 title claims description 11
• 230000001404 mediated effect Effects 0.000 title claims description 8
• 238000000034 method Methods 0.000 claims abstract description 328
• 150000001875 compounds Chemical class 0.000 claims abstract description 136
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 10
• 230000008569 process Effects 0.000 claims abstract description 7
• -1 1,3-butadienyl Chemical group 0.000 claims description 863
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 98
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 95
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 81
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 77
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 66
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 59
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 58
• 125000005842 heteroatom Chemical group 0.000 claims description 58
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 150000002367 halogens Chemical class 0.000 claims description 49
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 46
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 33
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000005336 allyloxy group Chemical group 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 17
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
• 102000009410 Chemokine receptor Human genes 0.000 claims description 15
• 108050000299 Chemokine receptor Proteins 0.000 claims description 15
• 108010012236 Chemokines Proteins 0.000 claims description 15
• 102000019034 Chemokines Human genes 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 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
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
• 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 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
• 239000000460 chlorine Substances 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
• 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
• 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 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
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000004001 thioalkyl group Chemical group 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 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
• 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
• 108010017148 CCR8 Receptors Proteins 0.000 claims description 4
• 102000004426 CCR8 Receptors Human genes 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
• 125000006267 biphenyl group Chemical group 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 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 4
• AIKVZLFNCOSIIX-UHFFFAOYSA-N (2,3-dimethylphenyl)-[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(C)C=CC=2)C)CC1 AIKVZLFNCOSIIX-UHFFFAOYSA-N 0.000 claims description 3
• MOBRKDSATUUXTE-UHFFFAOYSA-N (2-chloropyridin-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)C=2C=C(Cl)N=CC=2)CC1 MOBRKDSATUUXTE-UHFFFAOYSA-N 0.000 claims description 3
• KMHGNIWQUCYDNY-UHFFFAOYSA-N (4-chloro-2-methoxyphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound COC1=CC(Cl)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 KMHGNIWQUCYDNY-UHFFFAOYSA-N 0.000 claims description 3
• JNOFKHJLCGOFGT-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-[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(Cl)=CC=2)S(C)(=O)=O)CC1 JNOFKHJLCGOFGT-UHFFFAOYSA-N 0.000 claims description 3
• TURMTVPAOLGSRH-UHFFFAOYSA-N (4-chlorophenyl)-[2-[(3-phenylmethoxyphenyl)methyl]-2,8-diazaspiro[4.5]decan-8-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CCC2(CN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)CC1 TURMTVPAOLGSRH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• PTNZALIUPQZMPZ-UHFFFAOYSA-N (4-chlorophenyl)-[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=CC(Cl)=CC=2)CC1 PTNZALIUPQZMPZ-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
• 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 3
• MRTLULZPKOHBRQ-UHFFFAOYSA-N (4-chlorophenyl)-[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(Cl)=CC=2)CC1 MRTLULZPKOHBRQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• SFHLTXGPSLHREN-UHFFFAOYSA-N (4-ethylphenyl)-[9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 SFHLTXGPSLHREN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 125000006656 (C2-C4) alkenyl group Chemical group 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
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 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
• ZEPIENLIOYUEJS-UHFFFAOYSA-N 2-[3-[9-[[2-(2-methylpropoxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecane-3-carbonyl]phenyl]acetic acid Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=C(CC(O)=O)C=CC=2)CC1 ZEPIENLIOYUEJS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical group ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 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
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• IMOOTNNUBOUQMM-UHFFFAOYSA-N [4-(diethylamino)phenyl]-[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)N(CC)CC)CC1 IMOOTNNUBOUQMM-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• QELHUYQPGUZUEU-UHFFFAOYSA-N [8-[[2-(2-methylpropoxy)phenyl]methyl]-2,8-diazaspiro[4.5]decan-2-yl]-(4-nitro-1h-pyrazol-5-yl)methanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(CC2)C(=O)C=2C(=CNN=2)[N+]([O-])=O)CC1 QELHUYQPGUZUEU-UHFFFAOYSA-N 0.000 claims description 3
• FIHQZBAPZHAEDQ-UHFFFAOYSA-N [9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-(3-methoxyphenyl)methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=C(OC)C=CC=2)CC1 FIHQZBAPZHAEDQ-UHFFFAOYSA-N 0.000 claims description 3
• SDKRIOSUNQLALH-UHFFFAOYSA-N [9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-(4-methoxyphenyl)methanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C=CC(OC)=CC=2)CC1 SDKRIOSUNQLALH-UHFFFAOYSA-N 0.000 claims description 3
• CEMXWERYZRCODE-UHFFFAOYSA-N [9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-naphthalen-1-ylmethanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2C3=CC=CC=C3C=CC=2)CC1 CEMXWERYZRCODE-UHFFFAOYSA-N 0.000 claims description 3
• WJGCMBDMKFVZTH-UHFFFAOYSA-N [9-[(2-ethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-quinolin-2-ylmethanone Chemical compound CCOC1=CC=CC=C1CN1CCC2(CCN(CC2)C(=O)C=2N=C3C=CC=CC3=CC=2)CC1 WJGCMBDMKFVZTH-UHFFFAOYSA-N 0.000 claims description 3
• RXCVPNWPMJSNRX-UHFFFAOYSA-N [9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2CCC3(CCN(CC=4C(=CC=CC=4)OCC=4C=CC=CC=4)CC3)CC2)=C1 RXCVPNWPMJSNRX-UHFFFAOYSA-N 0.000 claims description 3
• VCRAGBVMECEIHR-UHFFFAOYSA-N [9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1CCC2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)CC1 VCRAGBVMECEIHR-UHFFFAOYSA-N 0.000 claims description 3
• CBCNPHRSABLENZ-UHFFFAOYSA-N [9-[(2-phenylmethoxyphenyl)methyl]-3,9-diazaspiro[5.5]undecan-3-yl]-quinolin-4-ylmethanone Chemical compound C=1C=NC2=CC=CC=C2C=1C(=O)N(CC1)CCC1(CC1)CCN1CC1=CC=CC=C1OCC1=CC=CC=C1 CBCNPHRSABLENZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
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• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
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• 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
• 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 2
• SDHAHASAGDBNTD-UHFFFAOYSA-N 1-[7-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]-2-pyridin-2-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(C2)C(=O)CC=2N=CC=CC=2)CC1 SDHAHASAGDBNTD-UHFFFAOYSA-N 0.000 claims description 2
• BMLKJKPDPGLJRJ-UHFFFAOYSA-N 1-[7-[[2-(2-methylpropoxy)phenyl]methyl]-2,7-diazaspiro[3.5]nonan-2-yl]-2-pyridin-4-ylethanone Chemical compound CC(C)COC1=CC=CC=C1CN1CCC2(CN(C2)C(=O)CC=2C=CN=CC=2)CC1 BMLKJKPDPGLJRJ-UHFFFAOYSA-N 0.000 claims description 2
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• 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
• ITBKTOAUTLJXHO-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-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=C3OCOC3=CC=2)CC1 ITBKTOAUTLJXHO-UHFFFAOYSA-N 0.000 claims description 2
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