JP2009536651A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009536651A5 JP2009536651A5 JP2009509820A JP2009509820A JP2009536651A5 JP 2009536651 A5 JP2009536651 A5 JP 2009536651A5 JP 2009509820 A JP2009509820 A JP 2009509820A JP 2009509820 A JP2009509820 A JP 2009509820A JP 2009536651 A5 JP2009536651 A5 JP 2009536651A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclobutyl
- diazaspiro
- undecane
- undes
- alkyl
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims 59
- 150000003839 salts Chemical class 0.000 claims 59
- 125000000217 alkyl group Chemical group 0.000 claims 55
- 125000001424 substituent group Chemical group 0.000 claims 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 35
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 29
- 150000002367 halogens Chemical class 0.000 claims 29
- -1 amino, cyano, hydroxy, aminocarbonyl Chemical group 0.000 claims 27
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 23
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 21
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 15
- 125000004043 oxo group Chemical group O=* 0.000 claims 15
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- 150000005215 alkyl ethers Chemical class 0.000 claims 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 102000004384 Histamine H3 receptors Human genes 0.000 claims 7
- 108090000981 Histamine H3 receptors Proteins 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 206010016256 fatigue Diseases 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- 229960003966 nicotinamide Drugs 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 2
- QEXPZZLZBPAMMK-UHFFFAOYSA-N 9-cyclobutyl-3-[4-(piperidin-1-ylmethyl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCCCC1 QEXPZZLZBPAMMK-UHFFFAOYSA-N 0.000 claims 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010041349 Somnolence Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 208000002173 dizziness Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 201000003152 motion sickness Diseases 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 201000002859 sleep apnea Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 2
- DLMJEFNQSGXWFE-UHFFFAOYSA-N (9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1(CC1)CCN1C1CCC1 DLMJEFNQSGXWFE-UHFFFAOYSA-N 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- BYEXLPMZDSDQOZ-UHFFFAOYSA-N 1-[4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 BYEXLPMZDSDQOZ-UHFFFAOYSA-N 0.000 claims 1
- MHCJEILYZBIMOR-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)-8-cyclobutyl-2,8-diazaspiro[4.5]decane Chemical compound N1=CC(Br)=CC=C1N1CC2(CCN(CC2)C2CCC2)CC1 MHCJEILYZBIMOR-UHFFFAOYSA-N 0.000 claims 1
- ZSASNKWSKWZNRE-UHFFFAOYSA-N 2-(6-chloropyridazin-3-yl)-8-cyclobutyl-2,8-diazaspiro[4.5]decane Chemical compound N1=NC(Cl)=CC=C1N1CC2(CCN(CC2)C2CCC2)CC1 ZSASNKWSKWZNRE-UHFFFAOYSA-N 0.000 claims 1
- MBXRGGFPRCGEEN-UHFFFAOYSA-N 2-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-1,3-thiazole Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2SC=CN=2)CC1 MBXRGGFPRCGEEN-UHFFFAOYSA-N 0.000 claims 1
- HPJJWQFTTPCSMT-UHFFFAOYSA-N 2-cyclobutyl-8-(4-pyridin-3-ylphenyl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CC2(CCN(CC2)C=2C=CC(=CC=2)C=2C=NC=CC=2)CC1 HPJJWQFTTPCSMT-UHFFFAOYSA-N 0.000 claims 1
- CWXYUJNGEZVIRO-UHFFFAOYSA-N 2-cyclobutyl-8-(6-pyridin-4-ylpyridazin-3-yl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=CN=CC=2)CC1 CWXYUJNGEZVIRO-UHFFFAOYSA-N 0.000 claims 1
- CFJLCRXTEBBGGQ-UHFFFAOYSA-N 2-cyclobutyl-8-[4-(1-methylpyrazol-4-yl)phenyl]-2,8-diazaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CC=C(N2CCC3(CN(CC3)C3CCC3)CC2)C=C1 CFJLCRXTEBBGGQ-UHFFFAOYSA-N 0.000 claims 1
- MJJYENJYHFWQEO-UHFFFAOYSA-N 2-cyclobutyl-8-[6-(6-methoxypyridin-3-yl)pyridazin-3-yl]-2,8-diazaspiro[4.5]decane Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N2CCC3(CN(CC3)C3CCC3)CC2)N=N1 MJJYENJYHFWQEO-UHFFFAOYSA-N 0.000 claims 1
- ZKPNSBJNPXNSDD-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methanone Chemical compound C1CCC2CCCCC2N1C(=O)C(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 ZKPNSBJNPXNSDD-UHFFFAOYSA-N 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- MCIHESAUOBHVKE-UHFFFAOYSA-N 3-(3-bromophenyl)-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound BrC1=CC=CC(N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 MCIHESAUOBHVKE-UHFFFAOYSA-N 0.000 claims 1
- ZKSUKUDYXFGCAE-UHFFFAOYSA-N 3-(6-chloropyridazin-3-yl)-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound N1=NC(Cl)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 ZKSUKUDYXFGCAE-UHFFFAOYSA-N 0.000 claims 1
- SWMWOVXBSUABRR-UHFFFAOYSA-N 3-[4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-ylmethyl)phenyl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC2CCCCC2N1CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 SWMWOVXBSUABRR-UHFFFAOYSA-N 0.000 claims 1
- VDCDQBIYJKKNJC-UHFFFAOYSA-N 3-[4-(azepan-1-ylmethyl)phenyl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCCCCC1 VDCDQBIYJKKNJC-UHFFFAOYSA-N 0.000 claims 1
- HWGDYGVGHVFVCD-CLJLJLNGSA-N 3-[4-[[(4ar,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]methyl]phenyl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C([C@H]1CCCC[C@@H]1CC1)N1CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 HWGDYGVGHVFVCD-CLJLJLNGSA-N 0.000 claims 1
- HWGDYGVGHVFVCD-IZZNHLLZSA-N 3-[4-[[(4as,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]methyl]phenyl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C([C@H]1CCCC[C@H]1CC1)N1CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 HWGDYGVGHVFVCD-IZZNHLLZSA-N 0.000 claims 1
- CUOLVYBQCKSCDI-UHFFFAOYSA-N 3-[5-(4-benzylpiperazin-1-yl)pyridin-2-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=CC=CC=1CN(CC1)CCN1C(C=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 CUOLVYBQCKSCDI-UHFFFAOYSA-N 0.000 claims 1
- ABKBGKLIWLSTGT-UHFFFAOYSA-N 3-[6-(1,3-benzodioxol-5-yl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=C3OCOC3=CC=2)CC1 ABKBGKLIWLSTGT-UHFFFAOYSA-N 0.000 claims 1
- ZWDNFQVJXHZZDB-UHFFFAOYSA-N 3-[6-(2-chlorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound ClC1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 ZWDNFQVJXHZZDB-UHFFFAOYSA-N 0.000 claims 1
- OZQMZZJOGYWXKR-UHFFFAOYSA-N 3-[6-(3-chloro-4-fluorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(Cl)C(F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 OZQMZZJOGYWXKR-UHFFFAOYSA-N 0.000 claims 1
- DYRPPFQKBNGPIB-UHFFFAOYSA-N 3-[6-(3-chlorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound ClC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 DYRPPFQKBNGPIB-UHFFFAOYSA-N 0.000 claims 1
- NVJXQIOWCMBWRE-UHFFFAOYSA-N 3-[6-(4-butylphenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 NVJXQIOWCMBWRE-UHFFFAOYSA-N 0.000 claims 1
- LDNRXDSALSMDMT-UHFFFAOYSA-N 3-[6-(4-chloro-2-fluorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC(Cl)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 LDNRXDSALSMDMT-UHFFFAOYSA-N 0.000 claims 1
- NWJYYIHXPWDNPV-UHFFFAOYSA-N 3-[6-(4-chloro-3-fluorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(Cl)C(F)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 NWJYYIHXPWDNPV-UHFFFAOYSA-N 0.000 claims 1
- VUCLHKUHJVLWBL-UHFFFAOYSA-N 3-[6-(4-chlorophenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 VUCLHKUHJVLWBL-UHFFFAOYSA-N 0.000 claims 1
- AFAHMXMYOQLEKS-UHFFFAOYSA-N 3-[6-(4-tert-butylphenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 AFAHMXMYOQLEKS-UHFFFAOYSA-N 0.000 claims 1
- JFLOZSOXDWCBDV-UHFFFAOYSA-N 3-[6-(5-chloro-2-methoxyphenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=C(Cl)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 JFLOZSOXDWCBDV-UHFFFAOYSA-N 0.000 claims 1
- VLQRSRHUHXSDQN-UHFFFAOYSA-N 3-[6-[2-chloro-5-(trifluoromethyl)phenyl]pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 VLQRSRHUHXSDQN-UHFFFAOYSA-N 0.000 claims 1
- ZTNQTNKOAZZAEG-UHFFFAOYSA-N 3-[6-[3,5-bis(trifluoromethyl)phenyl]pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 ZTNQTNKOAZZAEG-UHFFFAOYSA-N 0.000 claims 1
- ZWPDBOKEUDVMEZ-UHFFFAOYSA-N 3-[6-[4-chloro-3-(trifluoromethyl)phenyl]pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 ZWPDBOKEUDVMEZ-UHFFFAOYSA-N 0.000 claims 1
- QFGKHMXFABGFSP-UHFFFAOYSA-N 4-[1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]piperidin-4-yl]morpholine Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCC(CC2)N2CCOCC2)CC1 QFGKHMXFABGFSP-UHFFFAOYSA-N 0.000 claims 1
- XYHBLFDQOQMZRI-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-2-methoxy-1,3-thiazole Chemical compound S1C(OC)=NC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 XYHBLFDQOQMZRI-UHFFFAOYSA-N 0.000 claims 1
- BJVFQGQEMIQQBX-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]morpholine Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCOCC2)CC1 BJVFQGQEMIQQBX-UHFFFAOYSA-N 0.000 claims 1
- UWWKSKHHCVMJSM-UHFFFAOYSA-N 4-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 UWWKSKHHCVMJSM-UHFFFAOYSA-N 0.000 claims 1
- UUJKKDOTZWISQM-UHFFFAOYSA-N 4-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]morpholine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCOCC1 UUJKKDOTZWISQM-UHFFFAOYSA-N 0.000 claims 1
- FYELDHZQSCJMBR-UHFFFAOYSA-N 4-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]thiomorpholine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCSCC1 FYELDHZQSCJMBR-UHFFFAOYSA-N 0.000 claims 1
- OVUWGWNWUJYWFV-UHFFFAOYSA-N 4-[[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]methyl]morpholine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1CN1CCOCC1 OVUWGWNWUJYWFV-UHFFFAOYSA-N 0.000 claims 1
- XNLFCCRBRSIOCO-UHFFFAOYSA-N 8-(5-bromopyridin-2-yl)-2-cyclobutyl-2,8-diazaspiro[4.5]decane Chemical compound N1=CC(Br)=CC=C1N1CCC2(CN(CC2)C2CCC2)CC1 XNLFCCRBRSIOCO-UHFFFAOYSA-N 0.000 claims 1
- BWVAEOGZBBHJQN-UHFFFAOYSA-N 8-(6-chloropyridazin-3-yl)-2-cyclobutyl-2,8-diazaspiro[4.5]decane Chemical compound N1=NC(Cl)=CC=C1N1CCC2(CN(CC2)C2CCC2)CC1 BWVAEOGZBBHJQN-UHFFFAOYSA-N 0.000 claims 1
- GYIFTMWDYRRGAR-UHFFFAOYSA-N 8-cyclobutyl-2-(4-pyridin-3-ylphenyl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CCC2(CN(CC2)C=2C=CC(=CC=2)C=2C=NC=CC=2)CC1 GYIFTMWDYRRGAR-UHFFFAOYSA-N 0.000 claims 1
- FNOAPJOTTVNLSL-UHFFFAOYSA-N 8-cyclobutyl-2-(6-pyridin-3-ylpyridazin-3-yl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CCC2(CN(CC2)C=2N=NC(=CC=2)C=2C=NC=CC=2)CC1 FNOAPJOTTVNLSL-UHFFFAOYSA-N 0.000 claims 1
- UWFHACILCPYWGW-UHFFFAOYSA-N 8-cyclobutyl-2-(6-pyridin-4-ylpyridazin-3-yl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CCC2(CN(CC2)C=2N=NC(=CC=2)C=2C=CN=CC=2)CC1 UWFHACILCPYWGW-UHFFFAOYSA-N 0.000 claims 1
- IBEYJYAEHDQICE-UHFFFAOYSA-N 8-cyclobutyl-2-[4-(1-methylpyrazol-4-yl)phenyl]-2,8-diazaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CC=C(N2CC3(CC2)CCN(CC3)C2CCC2)C=C1 IBEYJYAEHDQICE-UHFFFAOYSA-N 0.000 claims 1
- STRNGIPUCOZAMG-UHFFFAOYSA-N 9-cyclobutyl-3-(1-methylbenzimidazol-5-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C2N(C)C=NC2=CC=1N(CC1)CCC1(CC1)CCN1C1CCC1 STRNGIPUCOZAMG-UHFFFAOYSA-N 0.000 claims 1
- FSIMJFGVEMWQFK-UHFFFAOYSA-N 9-cyclobutyl-3-(2-pyridin-3-ylpyrimidin-5-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=NC(=NC=2)C=2C=NC=CC=2)CC1 FSIMJFGVEMWQFK-UHFFFAOYSA-N 0.000 claims 1
- BLAACUOBMYDPDC-UHFFFAOYSA-N 9-cyclobutyl-3-(3-pyrimidin-5-ylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=C(C=CC=2)C=2C=NC=NC=2)CC1 BLAACUOBMYDPDC-UHFFFAOYSA-N 0.000 claims 1
- TUJCQMZABNGISZ-UHFFFAOYSA-N 9-cyclobutyl-3-(4-imidazo[1,2-a]pyrimidin-6-ylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C2=CN3C=CN=C3N=C2)CC1 TUJCQMZABNGISZ-UHFFFAOYSA-N 0.000 claims 1
- SNXAVMMUJRFJJM-UHFFFAOYSA-N 9-cyclobutyl-3-(4-methylsulfonylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SNXAVMMUJRFJJM-UHFFFAOYSA-N 0.000 claims 1
- UQAACZLUIVFPNR-UHFFFAOYSA-N 9-cyclobutyl-3-(4-pyridin-3-ylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C=2C=NC=CC=2)CC1 UQAACZLUIVFPNR-UHFFFAOYSA-N 0.000 claims 1
- YVLYOBCWBOFKSU-UHFFFAOYSA-N 9-cyclobutyl-3-(4-pyridin-4-ylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C=2C=CN=CC=2)CC1 YVLYOBCWBOFKSU-UHFFFAOYSA-N 0.000 claims 1
- PARQKIJKXVXULU-UHFFFAOYSA-N 9-cyclobutyl-3-(4-pyrimidin-5-ylphenyl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C=2C=NC=NC=2)CC1 PARQKIJKXVXULU-UHFFFAOYSA-N 0.000 claims 1
- ZLRJWOYCNSUABJ-UHFFFAOYSA-N 9-cyclobutyl-3-(5-imidazo[1,2-a]pyrimidin-6-ylpyridin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)C2=CN3C=CN=C3N=C2)CC1 ZLRJWOYCNSUABJ-UHFFFAOYSA-N 0.000 claims 1
- KDDQBDZNDUOTLK-UHFFFAOYSA-N 9-cyclobutyl-3-(5-piperidin-1-ylpyridin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCCCC2)CC1 KDDQBDZNDUOTLK-UHFFFAOYSA-N 0.000 claims 1
- TVFSRWDEHXIQDN-UHFFFAOYSA-N 9-cyclobutyl-3-(5-pyridin-3-ylpyrazin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=NC=2)C=2C=NC=CC=2)CC1 TVFSRWDEHXIQDN-UHFFFAOYSA-N 0.000 claims 1
- JCRNQHCEHBFGSL-UHFFFAOYSA-N 9-cyclobutyl-3-(5-pyridin-3-ylpyrimidin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CN=2)C=2C=NC=CC=2)CC1 JCRNQHCEHBFGSL-UHFFFAOYSA-N 0.000 claims 1
- WGOBZXCCZGAINC-UHFFFAOYSA-N 9-cyclobutyl-3-(5-pyrimidin-5-ylpyridin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)C=2C=NC=NC=2)CC1 WGOBZXCCZGAINC-UHFFFAOYSA-N 0.000 claims 1
- FOHIDZRAJICPBM-UHFFFAOYSA-N 9-cyclobutyl-3-(5-pyrrolidin-1-ylpyridin-2-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCCC2)CC1 FOHIDZRAJICPBM-UHFFFAOYSA-N 0.000 claims 1
- ILRVRHUHKCBKBW-UHFFFAOYSA-N 9-cyclobutyl-3-(6-dibenzofuran-4-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)CC1 ILRVRHUHKCBKBW-UHFFFAOYSA-N 0.000 claims 1
- KMOLQEBFQWCWRQ-UHFFFAOYSA-N 9-cyclobutyl-3-(6-imidazo[1,2-a]pyridin-6-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C2=CN3C=CN=C3C=C2)CC1 KMOLQEBFQWCWRQ-UHFFFAOYSA-N 0.000 claims 1
- MHANAHOIGTXVMJ-UHFFFAOYSA-N 9-cyclobutyl-3-(6-methoxypyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound N1=NC(OC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 MHANAHOIGTXVMJ-UHFFFAOYSA-N 0.000 claims 1
- SBHKIBKMVMOSFU-UHFFFAOYSA-N 9-cyclobutyl-3-(6-methylsulfonylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound N1=NC(S(=O)(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SBHKIBKMVMOSFU-UHFFFAOYSA-N 0.000 claims 1
- CHIIOKRVGZIADY-UHFFFAOYSA-N 9-cyclobutyl-3-(6-phenylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=CC=CC=2)CC1 CHIIOKRVGZIADY-UHFFFAOYSA-N 0.000 claims 1
- PQYGNJFIEBDJLL-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyrazin-2-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2N=CC=NC=2)CC1 PQYGNJFIEBDJLL-UHFFFAOYSA-N 0.000 claims 1
- FGHWAESTPXFUAC-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyridin-2-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2N=CC=CC=2)CC1 FGHWAESTPXFUAC-UHFFFAOYSA-N 0.000 claims 1
- KWJZNUZIEOEINU-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyridin-3-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=NC=CC=2)CC1 KWJZNUZIEOEINU-UHFFFAOYSA-N 0.000 claims 1
- UDYQPUNAIGXOJH-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyridin-4-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=CN=CC=2)CC1 UDYQPUNAIGXOJH-UHFFFAOYSA-N 0.000 claims 1
- GWGINUBOZNKZLP-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyrimidin-5-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=NC=NC=2)CC1 GWGINUBOZNKZLP-UHFFFAOYSA-N 0.000 claims 1
- IEDRUYATMYUKFS-UHFFFAOYSA-N 9-cyclobutyl-3-(6-pyrimidin-5-ylpyridin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=NC(=CC=2)C=2C=NC=NC=2)CC1 IEDRUYATMYUKFS-UHFFFAOYSA-N 0.000 claims 1
- BPFOUXNXNNNLNN-UHFFFAOYSA-N 9-cyclobutyl-3-[3-(1-methylpyrazol-4-yl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=NN(C)C=C1C1=CC=CC(N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 BPFOUXNXNNNLNN-UHFFFAOYSA-N 0.000 claims 1
- NIAMKGNHKYIPBR-UHFFFAOYSA-N 9-cyclobutyl-3-[4-(1-methylpyrazol-4-yl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=NN(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 NIAMKGNHKYIPBR-UHFFFAOYSA-N 0.000 claims 1
- CZMRGYCDTHUBCS-UHFFFAOYSA-N 9-cyclobutyl-3-[4-(3,6-dihydro-2h-pyridin-1-ylmethyl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCC=CC1 CZMRGYCDTHUBCS-UHFFFAOYSA-N 0.000 claims 1
- VATFECKZJFHYCD-UHFFFAOYSA-N 9-cyclobutyl-3-[4-([1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C2=CN3C=NN=C3C=C2)CC1 VATFECKZJFHYCD-UHFFFAOYSA-N 0.000 claims 1
- GGORUIFSEJOPNJ-UHFFFAOYSA-N 9-cyclobutyl-3-[4-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2C=CC(=CC=2)C2=NN3C=NN=C3C=C2)CC1 GGORUIFSEJOPNJ-UHFFFAOYSA-N 0.000 claims 1
- KIIMWPIOHGIEFN-UHFFFAOYSA-N 9-cyclobutyl-3-[4-(pyrazol-1-ylmethyl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC=NN1CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 KIIMWPIOHGIEFN-UHFFFAOYSA-N 0.000 claims 1
- KFVQMBTUVXYWCJ-UHFFFAOYSA-N 9-cyclobutyl-3-[4-(pyrrolidin-1-ylmethyl)phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CN1CCCC1 KFVQMBTUVXYWCJ-UHFFFAOYSA-N 0.000 claims 1
- MJKIEVRXZHZGTI-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[(2-ethylpiperidin-1-yl)methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound CCC1CCCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 MJKIEVRXZHZGTI-UHFFFAOYSA-N 0.000 claims 1
- YVIFKDFTUXSAIR-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[(2-methylpiperidin-1-yl)methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1CCCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 YVIFKDFTUXSAIR-UHFFFAOYSA-N 0.000 claims 1
- KZKKGCYHAYKDPE-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[(2-methylpyrrolidin-1-yl)methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1CCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 KZKKGCYHAYKDPE-UHFFFAOYSA-N 0.000 claims 1
- UFUDSVITBAEJHW-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[(3,5-dimethylpiperidin-1-yl)methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1C(C)CC(C)CN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 UFUDSVITBAEJHW-UHFFFAOYSA-N 0.000 claims 1
- OVNRJEHQSKLOKW-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[(4-methylpiperidin-1-yl)methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CC(C)CCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 OVNRJEHQSKLOKW-UHFFFAOYSA-N 0.000 claims 1
- AFBRXWSQCBCVPL-RUZDIDTESA-N 9-cyclobutyl-3-[4-[[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound COC[C@H]1CCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 AFBRXWSQCBCVPL-RUZDIDTESA-N 0.000 claims 1
- AFBRXWSQCBCVPL-VWLOTQADSA-N 9-cyclobutyl-3-[4-[[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound COC[C@@H]1CCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 AFBRXWSQCBCVPL-VWLOTQADSA-N 0.000 claims 1
- XOTPJVPYIHAZIA-UHFFFAOYSA-N 9-cyclobutyl-3-[4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]phenyl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=CN=C1C1=NC=CN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 XOTPJVPYIHAZIA-UHFFFAOYSA-N 0.000 claims 1
- NRZXJGLELPPVFN-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(3,5-dimethylpiperidin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1C(C)CC(C)CN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NRZXJGLELPPVFN-UHFFFAOYSA-N 0.000 claims 1
- JNJZTTFUMJTHSE-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-cyclopentylpiperazin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCN(CC2)C2CCCC2)CC1 JNJZTTFUMJTHSE-UHFFFAOYSA-N 0.000 claims 1
- FTDAPICGWSAIRG-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(CC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 FTDAPICGWSAIRG-UHFFFAOYSA-N 0.000 claims 1
- UNVAVZWFGCPSLM-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 UNVAVZWFGCPSLM-UHFFFAOYSA-N 0.000 claims 1
- WDQARBQHANHTSY-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-methylpiperidin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CC(C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 WDQARBQHANHTSY-UHFFFAOYSA-N 0.000 claims 1
- IZRCXBXZXZKBCO-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-methylsulfonylphenyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 IZRCXBXZXZKBCO-UHFFFAOYSA-N 0.000 claims 1
- NVWSMOBMJCNEKX-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-phenylpiperazin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCN(CC2)C=2C=CC=CC=2)CC1 NVWSMOBMJCNEKX-UHFFFAOYSA-N 0.000 claims 1
- FXUUZUQJDMQUGO-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(C(C)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 FXUUZUQJDMQUGO-UHFFFAOYSA-N 0.000 claims 1
- ZCXISCWTBZHIEF-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)N2CCC(CC2)N2CCCC2)CC1 ZCXISCWTBZHIEF-UHFFFAOYSA-N 0.000 claims 1
- JBDGRZJCEBMSLC-UHFFFAOYSA-N 9-cyclobutyl-3-[5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)C2=CN3C=NN=C3C=C2)CC1 JBDGRZJCEBMSLC-UHFFFAOYSA-N 0.000 claims 1
- FCDREZGIAJENIC-UHFFFAOYSA-N 9-cyclobutyl-3-[5-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC(=CC=2)C2=NN3C=NN=C3C=C2)CC1 FCDREZGIAJENIC-UHFFFAOYSA-N 0.000 claims 1
- NXUIFDNOFBGQPK-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(piperidin-1-ylmethyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1CN1CCCCC1 NXUIFDNOFBGQPK-UHFFFAOYSA-N 0.000 claims 1
- UFGRYGIDMIYQNS-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1CN1CCCC1 UFGRYGIDMIYQNS-UHFFFAOYSA-N 0.000 claims 1
- XSVBYXQAYCGFOW-UHFFFAOYSA-N 9-cyclobutyl-3-[5-(trifluoromethyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 XSVBYXQAYCGFOW-UHFFFAOYSA-N 0.000 claims 1
- ALFJRBRBERGVEQ-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[(2-methylpyrrolidin-1-yl)methyl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1CCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 ALFJRBRBERGVEQ-UHFFFAOYSA-N 0.000 claims 1
- NHPBKFFECZMLMX-JOCHJYFZSA-N 9-cyclobutyl-3-[5-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC[C@H]1CCCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NHPBKFFECZMLMX-JOCHJYFZSA-N 0.000 claims 1
- NHPBKFFECZMLMX-QFIPXVFZSA-N 9-cyclobutyl-3-[5-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC[C@@H]1CCCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NHPBKFFECZMLMX-QFIPXVFZSA-N 0.000 claims 1
- ZNDFCIZMDNTJRB-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[(4,4-difluoropiperidin-1-yl)methyl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CC(F)(F)CCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 ZNDFCIZMDNTJRB-UHFFFAOYSA-N 0.000 claims 1
- ZZVRADHWGSILOG-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[(4-fluoropiperidin-1-yl)methyl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CC(F)CCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 ZZVRADHWGSILOG-UHFFFAOYSA-N 0.000 claims 1
- VJQUALRPFAJJRL-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[4-(1-phenylethyl)piperazin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=CC=CC=1C(C)N(CC1)CCN1C(C=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 VJQUALRPFAJJRL-UHFFFAOYSA-N 0.000 claims 1
- JMSWUYNLUAPTRV-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(CCOC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 JMSWUYNLUAPTRV-UHFFFAOYSA-N 0.000 claims 1
- YJJVVTVNHJXQQC-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[4-(2-phenylethyl)piperazin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(C=2C=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)CCN1CCC1=CC=CC=C1 YJJVVTVNHJXQQC-UHFFFAOYSA-N 0.000 claims 1
- DYEYODHBYPCZHA-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[4-(4-fluorophenyl)piperazin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(F)=CC=C1N1CCN(C=2C=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)CC1 DYEYODHBYPCZHA-UHFFFAOYSA-N 0.000 claims 1
- FLENIOJEXWVMRA-UHFFFAOYSA-N 9-cyclobutyl-3-[5-[4-(4-methoxyphenyl)piperazin-1-yl]pyridin-2-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)CC1 FLENIOJEXWVMRA-UHFFFAOYSA-N 0.000 claims 1
- ALANQAKWEMYVMH-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(1-methylbenzimidazol-5-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 ALANQAKWEMYVMH-UHFFFAOYSA-N 0.000 claims 1
- DQUJPUAIQJEDMF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=NN(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 DQUJPUAIQJEDMF-UHFFFAOYSA-N 0.000 claims 1
- ZQJXQEADRXOUAW-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(1h-indazol-5-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=C3C=NNC3=CC=2)CC1 ZQJXQEADRXOUAW-UHFFFAOYSA-N 0.000 claims 1
- KWVRGWYMZIQCKI-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,3-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1F KWVRGWYMZIQCKI-UHFFFAOYSA-N 0.000 claims 1
- BWKZDRDIKXWVBF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=C3OCCOC3=CC=2)CC1 BWKZDRDIKXWVBF-UHFFFAOYSA-N 0.000 claims 1
- IOVKUUPSLKHBCS-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,4,6-trimethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC(C)=CC(C)=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 IOVKUUPSLKHBCS-UHFFFAOYSA-N 0.000 claims 1
- XTZOWFUGUNJVDY-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,4-dichlorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound ClC1=CC(Cl)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 XTZOWFUGUNJVDY-UHFFFAOYSA-N 0.000 claims 1
- OYSOJZPPARGXKI-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,4-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC(F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 OYSOJZPPARGXKI-UHFFFAOYSA-N 0.000 claims 1
- FYMFXIFCLXKKRV-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,4-dimethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 FYMFXIFCLXKKRV-UHFFFAOYSA-N 0.000 claims 1
- OSBFIKOABZHJNX-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,5-dichlorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound ClC1=CC=C(Cl)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 OSBFIKOABZHJNX-UHFFFAOYSA-N 0.000 claims 1
- AEKWXZCXMHGBEW-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,5-difluoro-4-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(F)C(OC)=CC(F)=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 AEKWXZCXMHGBEW-UHFFFAOYSA-N 0.000 claims 1
- AXJHZYBOUSCTQF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=C(F)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 AXJHZYBOUSCTQF-UHFFFAOYSA-N 0.000 claims 1
- LTLKZDXHWIXSGW-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,5-dimethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=C(OC)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 LTLKZDXHWIXSGW-UHFFFAOYSA-N 0.000 claims 1
- DTMGPAZQJGFATQ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,6-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=CC(F)=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 DTMGPAZQJGFATQ-UHFFFAOYSA-N 0.000 claims 1
- LEWWECHMDSDHMF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,6-dimethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=CC(OC)=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 LEWWECHMDSDHMF-UHFFFAOYSA-N 0.000 claims 1
- HPNFLJDIGUANPY-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2,6-dimethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 HPNFLJDIGUANPY-UHFFFAOYSA-N 0.000 claims 1
- WFHLHKPXEOVFLL-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-ethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CCOC1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 WFHLHKPXEOVFLL-UHFFFAOYSA-N 0.000 claims 1
- BGBYGAXXABEOCH-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-fluoro-4-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC(C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 BGBYGAXXABEOCH-UHFFFAOYSA-N 0.000 claims 1
- ZWLOVXVVDQFVRZ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-fluoro-5-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC=C(F)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 ZWLOVXVVDQFVRZ-UHFFFAOYSA-N 0.000 claims 1
- OEDGUEXOVGEOGI-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-fluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 OEDGUEXOVGEOGI-UHFFFAOYSA-N 0.000 claims 1
- NUNBXTQXPDVQRI-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-methoxy-5-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=C(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 NUNBXTQXPDVQRI-UHFFFAOYSA-N 0.000 claims 1
- IAWLVFANGHVQMV-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-methoxy-5-propan-2-ylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=C(C(C)C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 IAWLVFANGHVQMV-UHFFFAOYSA-N 0.000 claims 1
- HJQCMIVPJRMCJX-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-methoxy-6-propan-2-ylpyridin-3-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=NC(C(C)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 HJQCMIVPJRMCJX-UHFFFAOYSA-N 0.000 claims 1
- ORIDIOOHGZWBTQ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 ORIDIOOHGZWBTQ-UHFFFAOYSA-N 0.000 claims 1
- YPULJVJSCIVYFD-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-phenoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C(=CC=CC=2)OC=2C=CC=CC=2)CC1 YPULJVJSCIVYFD-UHFFFAOYSA-N 0.000 claims 1
- ISJGNOOSPCZFRX-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(2-propan-2-ylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC(C)C1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 ISJGNOOSPCZFRX-UHFFFAOYSA-N 0.000 claims 1
- USYUUOQXHWUDIE-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,4-dichlorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 USYUUOQXHWUDIE-UHFFFAOYSA-N 0.000 claims 1
- OXYDVHAWBZQNHR-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,4-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(F)C(F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 OXYDVHAWBZQNHR-UHFFFAOYSA-N 0.000 claims 1
- YDKVESXPCVMELL-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,4-dimethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 YDKVESXPCVMELL-UHFFFAOYSA-N 0.000 claims 1
- GTPGUZWPVPXLBM-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,4-dimethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 GTPGUZWPVPXLBM-UHFFFAOYSA-N 0.000 claims 1
- POSQMLXKALKNDX-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,5-dichlorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound ClC1=CC(Cl)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 POSQMLXKALKNDX-UHFFFAOYSA-N 0.000 claims 1
- HHWSCUBGWKSGRG-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,5-difluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC(F)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 HHWSCUBGWKSGRG-UHFFFAOYSA-N 0.000 claims 1
- YBOZMAXFZIDHBW-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3,5-dimethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC(C)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 YBOZMAXFZIDHBW-UHFFFAOYSA-N 0.000 claims 1
- XJMMEWACADEIHG-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-ethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CCOC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 XJMMEWACADEIHG-UHFFFAOYSA-N 0.000 claims 1
- OLJVUJBOSQOLCC-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-ethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CCC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 OLJVUJBOSQOLCC-UHFFFAOYSA-N 0.000 claims 1
- MUTCSMZNUKSSAP-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-fluoro-4-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 MUTCSMZNUKSSAP-UHFFFAOYSA-N 0.000 claims 1
- AMJRMOUIYYRALH-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-fluoro-4-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(F)C(C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 AMJRMOUIYYRALH-UHFFFAOYSA-N 0.000 claims 1
- HNWLKVPLDIXZBZ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-fluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 HNWLKVPLDIXZBZ-UHFFFAOYSA-N 0.000 claims 1
- QTOTZIHZDXRRNF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 QTOTZIHZDXRRNF-UHFFFAOYSA-N 0.000 claims 1
- KSFMVZZMVXPTJK-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 KSFMVZZMVXPTJK-UHFFFAOYSA-N 0.000 claims 1
- FLRQZTXRXKXXIQ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-methylsulfanylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CSC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 FLRQZTXRXKXXIQ-UHFFFAOYSA-N 0.000 claims 1
- WJIWPAKUHWNYLP-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-methylsulfonylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CS(=O)(=O)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 WJIWPAKUHWNYLP-UHFFFAOYSA-N 0.000 claims 1
- BTPBKEISRPAOJV-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-propan-2-yloxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC(C)OC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 BTPBKEISRPAOJV-UHFFFAOYSA-N 0.000 claims 1
- HUAOYZSNYIECSS-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(3-propan-2-ylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC(C)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 HUAOYZSNYIECSS-UHFFFAOYSA-N 0.000 claims 1
- BCDDMAHHSVYVPP-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-ethoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 BCDDMAHHSVYVPP-UHFFFAOYSA-N 0.000 claims 1
- NWMBCBGUMXUGIA-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-ethylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(CC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 NWMBCBGUMXUGIA-UHFFFAOYSA-N 0.000 claims 1
- CDJYLVOSKVYYTE-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-fluoro-3-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(F)C(C)=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 CDJYLVOSKVYYTE-UHFFFAOYSA-N 0.000 claims 1
- OXADZGMEHAAFTI-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-fluorophenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 OXADZGMEHAAFTI-UHFFFAOYSA-N 0.000 claims 1
- VXUJNCJVNUOURN-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-methoxy-2-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 VXUJNCJVNUOURN-UHFFFAOYSA-N 0.000 claims 1
- CUQLRXNKAUTVEW-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-methoxy-3-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=C(C)C(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 CUQLRXNKAUTVEW-UHFFFAOYSA-N 0.000 claims 1
- FMZVAEKTDIHIGP-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 FMZVAEKTDIHIGP-UHFFFAOYSA-N 0.000 claims 1
- XZRCXGJVSHCCQR-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-methylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 XZRCXGJVSHCCQR-UHFFFAOYSA-N 0.000 claims 1
- FGJWDESWBTUSKB-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-methylsulfonylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 FGJWDESWBTUSKB-UHFFFAOYSA-N 0.000 claims 1
- IDYIHSSZZBCUNZ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-phenoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=NC(=CC=2)C=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 IDYIHSSZZBCUNZ-UHFFFAOYSA-N 0.000 claims 1
- RYBZPOUTGDSWHO-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-propan-2-ylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 RYBZPOUTGDSWHO-UHFFFAOYSA-N 0.000 claims 1
- NHEPRWILUJIZOZ-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-propoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 NHEPRWILUJIZOZ-UHFFFAOYSA-N 0.000 claims 1
- XBLFMWXNAGGRSB-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(4-propylphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 XBLFMWXNAGGRSB-UHFFFAOYSA-N 0.000 claims 1
- KKFXVPFSIGFWRF-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(5-fluoro-2-methoxyphenyl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CC=C(F)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 KKFXVPFSIGFWRF-UHFFFAOYSA-N 0.000 claims 1
- CDEMEAIZSRQTHL-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(5-methoxypyridin-3-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound COC1=CN=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 CDEMEAIZSRQTHL-UHFFFAOYSA-N 0.000 claims 1
- UFUZPOAMIHWAJS-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(6-methoxynaphthalen-2-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(N=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 UFUZPOAMIHWAJS-UHFFFAOYSA-N 0.000 claims 1
- BKNYNZBIMAQFAL-UHFFFAOYSA-N 9-cyclobutyl-3-[6-(6-methoxypyridin-3-yl)pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 BKNYNZBIMAQFAL-UHFFFAOYSA-N 0.000 claims 1
- QXFVYLAWTXFGMK-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[2-(trifluoromethyl)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC(F)(F)C1=CC=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 QXFVYLAWTXFGMK-UHFFFAOYSA-N 0.000 claims 1
- RWOBHBLTVGFICU-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[3-(trifluoromethoxy)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC(F)(F)OC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 RWOBHBLTVGFICU-UHFFFAOYSA-N 0.000 claims 1
- AVJHHGNLPOCYII-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[3-(trifluoromethyl)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound FC(F)(F)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 AVJHHGNLPOCYII-UHFFFAOYSA-N 0.000 claims 1
- RSAFZHDPDBFCLG-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[4-(4-methoxyphenyl)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 RSAFZHDPDBFCLG-UHFFFAOYSA-N 0.000 claims 1
- IHVIMRMIWDHETN-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[4-(trifluoromethoxy)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 IHVIMRMIWDHETN-UHFFFAOYSA-N 0.000 claims 1
- LOQHAHAPBUYJER-UHFFFAOYSA-N 9-cyclobutyl-3-[6-[4-(trifluoromethyl)phenyl]pyridazin-3-yl]-3,9-diazaspiro[5.5]undecane Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 LOQHAHAPBUYJER-UHFFFAOYSA-N 0.000 claims 1
- DPCCTMBQJHVKSV-UHFFFAOYSA-N 9-cyclobutyl-3-pyrazin-2-yl-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=CC=NC=2)CC1 DPCCTMBQJHVKSV-UHFFFAOYSA-N 0.000 claims 1
- XUPUYDPTWMXWKL-UHFFFAOYSA-N 9-cyclobutyl-3-quinolin-2-yl-3,9-diazaspiro[5.5]undecane Chemical compound C1CCC1N1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=CC=2)CC1 XUPUYDPTWMXWKL-UHFFFAOYSA-N 0.000 claims 1
- GGMFVOXUOISYJE-UHFFFAOYSA-N 9-ethyl-3-(6-pyrazin-2-ylpyridazin-3-yl)-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(CC)CCC21CCN(C=1N=NC(=CC=1)C=1N=CC=NC=1)CC2 GGMFVOXUOISYJE-UHFFFAOYSA-N 0.000 claims 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- RHEXJNIQCWQOST-ILBGXUMGSA-N [(4ar,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methanone Chemical compound C([C@H]1CCCC[C@@H]1CC1)N1C(=O)C(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 RHEXJNIQCWQOST-ILBGXUMGSA-N 0.000 claims 1
- KKSQPXMLBDFSAW-ISKFKSNPSA-N [(4ar,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]methanone Chemical compound C([C@H]1CCCC[C@@H]1CC1)N1C(=O)C(C=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 KKSQPXMLBDFSAW-ISKFKSNPSA-N 0.000 claims 1
- RHEXJNIQCWQOST-UKILVPOCSA-N [(4as,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methanone Chemical compound C([C@H]1CCCC[C@H]1CC1)N1C(=O)C(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 RHEXJNIQCWQOST-UKILVPOCSA-N 0.000 claims 1
- KKSQPXMLBDFSAW-LADGPHEKSA-N [(4as,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]methanone Chemical compound C([C@H]1CCCC[C@H]1CC1)N1C(=O)C(C=N1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 KKSQPXMLBDFSAW-LADGPHEKSA-N 0.000 claims 1
- PRMKZSKNWDPKND-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(2,6-dimethylmorpholin-4-yl)methanone Chemical compound C1C(C)OC(C)CN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 PRMKZSKNWDPKND-UHFFFAOYSA-N 0.000 claims 1
- PHFMIWQLVNUEQT-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(2-ethylpiperidin-1-yl)methanone Chemical compound CCC1CCCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 PHFMIWQLVNUEQT-UHFFFAOYSA-N 0.000 claims 1
- OQRXLQCBKRQCRK-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 OQRXLQCBKRQCRK-UHFFFAOYSA-N 0.000 claims 1
- RQKSDLBBIKHZDT-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(3,5-dimethylpiperidin-1-yl)methanone Chemical compound C1C(C)CC(C)CN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 RQKSDLBBIKHZDT-UHFFFAOYSA-N 0.000 claims 1
- VPUJLAUSZSVRNK-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(3,6-dihydro-2h-pyridin-1-yl)methanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCC=CC1 VPUJLAUSZSVRNK-UHFFFAOYSA-N 0.000 claims 1
- XDTOYULHYNZLIS-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 XDTOYULHYNZLIS-UHFFFAOYSA-N 0.000 claims 1
- FUVWFSLUFZJRHT-XMMPIXPASA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@H]1CCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 FUVWFSLUFZJRHT-XMMPIXPASA-N 0.000 claims 1
- FUVWFSLUFZJRHT-DEOSSOPVSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 FUVWFSLUFZJRHT-DEOSSOPVSA-N 0.000 claims 1
- CGQXIGBLJGDVFQ-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCOCC1 CGQXIGBLJGDVFQ-UHFFFAOYSA-N 0.000 claims 1
- DDTHVFVSJYRKBJ-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-piperidin-1-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCCCC1 DDTHVFVSJYRKBJ-UHFFFAOYSA-N 0.000 claims 1
- MAZXNNGKQHJBSV-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCCC1 MAZXNNGKQHJBSV-UHFFFAOYSA-N 0.000 claims 1
- HWINXNUQJXSHPD-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-thiomorpholin-4-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCSCC1 HWINXNUQJXSHPD-UHFFFAOYSA-N 0.000 claims 1
- LBPQBOSGAROWMN-UHFFFAOYSA-N [4-[2-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-5-yl]phenyl]-(2-methylpyrrolidin-1-yl)methanone Chemical compound CC1CCCN1C(=O)C1=CC=C(C=2C=NC(=NC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 LBPQBOSGAROWMN-UHFFFAOYSA-N 0.000 claims 1
- PQESXTGQLZYQNR-UHFFFAOYSA-N [4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]phenyl]-(2-methylpyrrolidin-1-yl)methanone Chemical compound CC1CCCN1C(=O)C1=CC=C(C=2C=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 PQESXTGQLZYQNR-UHFFFAOYSA-N 0.000 claims 1
- OZPIDEMSOVOSPW-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(2,6-dimethylmorpholin-4-yl)methanone Chemical compound C1C(C)OC(C)CN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 OZPIDEMSOVOSPW-UHFFFAOYSA-N 0.000 claims 1
- QTZTXUGIIIJVFT-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(2-ethylpiperidin-1-yl)methanone Chemical compound CCC1CCCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 QTZTXUGIIIJVFT-UHFFFAOYSA-N 0.000 claims 1
- BUSZGNNMWDSYEO-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 BUSZGNNMWDSYEO-UHFFFAOYSA-N 0.000 claims 1
- MDACIZIWKVTGSZ-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(2-methylpyrrolidin-1-yl)methanone Chemical compound CC1CCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 MDACIZIWKVTGSZ-UHFFFAOYSA-N 0.000 claims 1
- YVMMLCFCUVRZON-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(3,5-dimethylpiperidin-1-yl)methanone Chemical compound C1C(C)CC(C)CN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 YVMMLCFCUVRZON-UHFFFAOYSA-N 0.000 claims 1
- DECIRZQOQJQSIA-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(3,6-dihydro-2h-pyridin-1-yl)methanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCC=CC1 DECIRZQOQJQSIA-UHFFFAOYSA-N 0.000 claims 1
- MJRFCHABQBKNTL-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 MJRFCHABQBKNTL-UHFFFAOYSA-N 0.000 claims 1
- GKAPYERRERCAAV-JOCHJYFZSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@H]1CCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 GKAPYERRERCAAV-JOCHJYFZSA-N 0.000 claims 1
- GKAPYERRERCAAV-QFIPXVFZSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 GKAPYERRERCAAV-QFIPXVFZSA-N 0.000 claims 1
- FKUKZWDGMKFIRC-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCOCC1 FKUKZWDGMKFIRC-UHFFFAOYSA-N 0.000 claims 1
- RBBIRNLYYWJEGT-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCCCC1 RBBIRNLYYWJEGT-UHFFFAOYSA-N 0.000 claims 1
- DXXYHJVCNHKTHR-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCCC1 DXXYHJVCNHKTHR-UHFFFAOYSA-N 0.000 claims 1
- UWZWHQRNQMCKQX-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-thiomorpholin-4-ylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCSCC1 UWZWHQRNQMCKQX-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- IKUDVLXQVQHWFV-UHFFFAOYSA-N azepan-1-yl-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N1CCCCCC1 IKUDVLXQVQHWFV-UHFFFAOYSA-N 0.000 claims 1
- JOSBSPPDPOGPPN-UHFFFAOYSA-N azepan-1-yl-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]methanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N1CCCCCC1 JOSBSPPDPOGPPN-UHFFFAOYSA-N 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 claims 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 0 CC*(C)*(CCC(C)(CC*(C*)*C)C1)CC1N*C Chemical compound CC*(C)*(CCC(C)(CC*(C*)*C)C1)CC1N*C 0.000 description 6
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74668006P | 2006-05-08 | 2006-05-08 | |
| US11/745,448 US20080247964A1 (en) | 2006-05-08 | 2007-05-07 | Substituted azaspiro derivatives |
| PCT/US2007/011135 WO2007133561A2 (en) | 2006-05-08 | 2007-05-08 | Substituted azaspiro derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009536651A JP2009536651A (ja) | 2009-10-15 |
| JP2009536651A5 true JP2009536651A5 (https=) | 2010-07-01 |
Family
ID=38694439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009509820A Withdrawn JP2009536651A (ja) | 2006-05-08 | 2007-05-08 | 置換されたアザスピロ誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20080247964A1 (https=) |
| EP (1) | EP2021004A4 (https=) |
| JP (1) | JP2009536651A (https=) |
| KR (1) | KR20090015956A (https=) |
| AU (1) | AU2007249925A1 (https=) |
| CA (1) | CA2651654A1 (https=) |
| IL (1) | IL195132A0 (https=) |
| WO (1) | WO2007133561A2 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR074467A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Tetrahidropiran espiro pirrolidinonas y piperidinonas sustituidas, composiciones farmaceuticas que las contienen y uso de las mismas en el tratamiento y/o prevencion de enfermedades del snc ,tales como alzheimer y parkinson, entre otras. |
| AR074466A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Piperidina espiro pirrolidinona y piperidinona sustituidas y su uso terapeutico en enfermedades mediadas por la modulacion de los receptores h3. |
| TW201206898A (en) * | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-phenyl spirolactam bipyrrolidines, preparation and therapeutic use thereof |
| EP2569297A1 (en) | 2010-05-11 | 2013-03-20 | Sanofi | Substituted n-heterocycloalkyl bipyrrolidinylphenyl amide derivatives, preparation and therapeutic use thereof |
| TW201206889A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-alkyl and N-acyl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| WO2011143162A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| AR083718A1 (es) | 2010-05-11 | 2013-03-20 | Sanofi Aventis | Fenil cicloalquil pirrolidina (piperidina) espirolactamas y amidas sustituidas, preparacion y uso terapeutico de las mismas |
| JP5833105B2 (ja) | 2010-05-11 | 2015-12-16 | サノフイ | 置換ｎ−ヘテロアリールスピロラクタムビピロリジン類、その製造及び治療的使用 |
| WO2011143155A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| JP6215315B2 (ja) * | 2012-06-12 | 2017-10-18 | アッヴィ・インコーポレイテッド | ピリジノンおよびピリダジノン誘導体 |
| US9096528B2 (en) | 2012-07-04 | 2015-08-04 | Agro-Kanesho Co., Ltd. | 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient |
| US8729263B2 (en) * | 2012-08-13 | 2014-05-20 | Novartis Ag | 1,4-disubstituted pyridazine analogs there of and methods for treating SMN-deficiency-related conditions |
| CN103288845B (zh) * | 2013-05-24 | 2015-05-20 | 武汉工程大学 | 螺环化合物2,4,8,10-四羰基-3,9-二氧杂螺环[5,5]十一烷及其合成方法 |
| EP4105208A1 (en) * | 2013-07-31 | 2022-12-21 | Novartis AG | 1,4-disubstituted pyridazine derivatives and their use for treating smn-deficiency-related conditions |
| HUE038764T2 (hu) * | 2014-03-17 | 2018-11-28 | Remynd Nv | 2,7-Diazaspiro[3.5]nonán vegyületek |
| DK3212637T3 (da) | 2014-10-31 | 2021-07-12 | Indivior Uk Ltd | Dopamin-d3-receptorantagonistforbindelser |
| WO2016100940A1 (en) | 2014-12-19 | 2016-06-23 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| US10752588B2 (en) | 2014-12-19 | 2020-08-25 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
| EP3053577A1 (en) * | 2015-02-09 | 2016-08-10 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| EP3256126B1 (en) * | 2015-02-09 | 2024-03-27 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| EA201800367A1 (ru) * | 2015-12-10 | 2019-02-28 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения болезни хантингтона |
| WO2018068296A1 (en) * | 2016-10-14 | 2018-04-19 | Merck Sharp & Dohme Corp. | PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE |
| EP3634953B1 (en) | 2017-06-05 | 2024-01-03 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| EA202092001A1 (ru) | 2018-03-27 | 2021-01-29 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения болезни гентингтона |
| HRP20240935T1 (hr) | 2018-06-27 | 2024-11-22 | Ptc Therapeutics, Inc. | Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| KR20210102887A (ko) * | 2018-11-14 | 2021-08-20 | 알타반트 사이언시스 게엠베하 | 말초 세로토닌과 관련된 질병 또는 장애를 치료하기 위한 트립토판 하이드록실라제 1 (tph1)의 결정질 스피로사이클릭 화합물 억제제 |
| CN109485648A (zh) * | 2018-12-17 | 2019-03-19 | 无锡合全药业有限公司 | 叔丁基-1-甲基-5-氧亚基三氮杂螺[5.5]十一烷-8-甲酸基酯的制备方法 |
| JP7649257B2 (ja) | 2019-05-13 | 2025-03-19 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病を処置するための化合物 |
| CN117177744A (zh) | 2021-01-29 | 2023-12-05 | 塞迪拉治疗股份有限公司 | Cdk2抑制剂及其使用方法 |
| MX2023015436A (es) | 2021-06-26 | 2024-02-21 | Cedilla Therapeutics Inc | Inhibidores de cdk2 y metodos de uso de los mismos. |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH375356A (de) * | 1959-03-25 | 1964-02-29 | Sandoz Ag | Verfahren zur Herstellung von neuen substituierten Succinimiden |
| US3106552A (en) * | 1960-07-19 | 1963-10-08 | Geschickter Fund Med Res | Nu-substituted azaspiranes and azaspirane-diones and processes for their preparation |
| US3282947A (en) * | 1962-05-17 | 1966-11-01 | Geschickter Fund Med Res | Unsymmetrically substituted 3, 9-diazaspiro(5, 5)undecane compounds |
| EP0621267A1 (en) * | 1993-04-07 | 1994-10-26 | Shell Internationale Researchmaatschappij B.V. | Spiropiperidine derivatives and their use as fungicides |
| US5451578A (en) * | 1994-08-12 | 1995-09-19 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE69633245T2 (de) * | 1995-09-29 | 2005-09-08 | Eli Lilly And Co., Indianapolis | Spiroverbindungen als Inhibitoren der Fibrinogen-abhängigen Blutplättchenaggregation |
| GB2309167A (en) * | 1997-05-10 | 1997-07-23 | Anormed Inc | The use of azaspiranes in the treatment of Alzheimer's disease |
| DE69900220T2 (de) * | 1998-06-12 | 2002-05-08 | F. Hoffmann-La Roche Ag, Basel | Diaza-spiro[3,5]nonan-Derivate |
| WO2004005293A2 (en) * | 2002-07-05 | 2004-01-15 | Targacept, Inc. | N-aryl diazaspiracyclic compounds and methods of preparation and use thereof |
| CA2518357A1 (en) * | 2003-03-10 | 2004-09-23 | Callisto Pharmaceuticals, Inc. | Method of treating cancer with azaspirane compositions |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| JPWO2005047286A1 (ja) * | 2003-11-13 | 2007-05-31 | 小野薬品工業株式会社 | スピロ複素環化合物 |
| AU2005277410B2 (en) * | 2004-08-20 | 2010-06-24 | Targacept, Inc. | The use of N-aryl diazaspiracyclic compounds in the treatment of addiction |
| WO2006040329A1 (en) * | 2004-10-12 | 2006-04-20 | Novo Nordisk A/S | 1 ibeta- hydroxysteroid dehydrogenase type 1 active spiro compounds |
| EP1917264B1 (en) * | 2005-06-28 | 2010-11-17 | NeuroSearch A/S | Novel 3,9-diaza-spiro[5.5]undecane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| AR057579A1 (es) * | 2005-11-23 | 2007-12-05 | Merck & Co Inc | Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac) |
-
2007
- 2007-05-07 US US11/745,448 patent/US20080247964A1/en not_active Abandoned
- 2007-05-08 JP JP2009509820A patent/JP2009536651A/ja not_active Withdrawn
- 2007-05-08 AU AU2007249925A patent/AU2007249925A1/en not_active Abandoned
- 2007-05-08 EP EP07756232A patent/EP2021004A4/en not_active Withdrawn
- 2007-05-08 KR KR1020087029820A patent/KR20090015956A/ko not_active Withdrawn
- 2007-05-08 CA CA002651654A patent/CA2651654A1/en not_active Abandoned
- 2007-05-08 WO PCT/US2007/011135 patent/WO2007133561A2/en not_active Ceased
-
2008
- 2008-11-05 IL IL195132A patent/IL195132A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009536651A5 (https=) | ||
| TWI868441B (zh) | 非環氧氮呯化合物及其用途 | |
| US11931363B2 (en) | Triazolopyrimidine compounds and uses thereof | |
| US12030883B2 (en) | Hetero-tricyclic compounds as inhibitors of KRAS | |
| AU2020276802B2 (en) | Inhibitor containing bicyclic derivative, preparation method therefor and use thereof | |
| JP6574859B2 (ja) | Ａｔｒキナーゼ阻害剤として有用な化合物 | |
| JP2014506929A5 (https=) | ||
| ES2398843T3 (es) | Imidazotriazinas e imidazopirimidinas como inhibidores de la quinasa | |
| KR101954044B1 (ko) | 피리돈 및 아자-피리돈 화합물 및 사용 방법 | |
| RU2016124178A (ru) | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет | |
| BR112012010820B1 (pt) | Compostos de octa-hidropirrolo[3,4-c]pirróis dissubstituídos, suas composições farmacêuticas e seu uso | |
| RS63710B1 (sr) | Derivati tetrahidro imidazo[4,5-c] piridina kao induktori internalizacije pd-l1 | |
| EP3472166A1 (en) | Imidazopyrimidine compounds useful for the treatment of cancer | |
| MD3468971T2 (ro) | Noi derivați de piperidinil (hetero)aril-substituiţi, procedeu de obţinere a acestora și compoziții farmaceutice care îi conțin | |
| JP2015522002A5 (https=) | ||
| RU2009125897A (ru) | Ингибиторы фосфоинозитид-3-киназы и способы их применения | |
| JP2016538316A5 (https=) | ||
| JP2010512338A5 (https=) | ||
| KR20150108389A (ko) | 치환된 피롤로피리미딘 화합물, 이의 조성물 및 이에 의한 치료 방법 | |
| JP2021504380A5 (https=) | ||
| US20250002507A1 (en) | 7,8-dihydro-5h-1,6-naphthyridine derivatives as positive allosteric modulators of the muscarinic acetylcholine receptor m4 for treating neurological and psychiatric disorders | |
| JP2013256532A (ja) | キナーゼインヒビターとして有用なアミノピリミジン | |
| US20250230155A1 (en) | 7,8-dihydro-5h-1,6-naphthyridine derivatives as positive allosteric modulators of the muscarinic acetylcholine receptor m4 for treating neurological and psychiatric disorders | |
| ES2278345T3 (es) | Imidazo-pirimidinas y triazolo-pirimidinas: ligandos de receptores de benzodiazepinas. | |
| WO2024220641A1 (en) | 1,6-naphthyridine derivatives as positive allosteric modulators of the muscarinic acetylcholine receptor m4 useful for the treatment of neurological and psychiatric disorders |