JP2009536651A5 - - Google Patents
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- 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- Withdrawn
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- 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
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- 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
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| PCT/US2007/011135 WO2007133561A2 (en) | 2006-05-08 | 2007-05-08 | Substituted azaspiro derivatives |
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| JP (1) | JP2009536651A (enExample) |
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| CA (1) | CA2651654A1 (enExample) |
| IL (1) | IL195132A0 (enExample) |
| WO (1) | WO2007133561A2 (enExample) |
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 |
| 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. |
| 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. |
| EP2569294B1 (en) | 2010-05-11 | 2015-03-11 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| TW201206939A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted phenyl cycloalkyl pyrrolidine (piperidine) spirolactams and amides, preparation and therapeutic use thereof |
| AR081908A1 (es) | 2010-05-11 | 2012-10-31 | Sanofi Aventis | N-heteroaril-espirolactama-bipirrolidinas sustituidas, preparacion y usos terapeuticos de las mismas |
| JP2013526530A (ja) * | 2010-05-11 | 2013-06-24 | サノフイ | 置換されたｎ−フェニルスピロラクタムビピロリジン、その製造及び治療上の使用 |
| WO2011143161A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heterocycloalkyl bipyrrolidinylphenyl amide derivatives, preparation and therapeutic use thereof |
| AR081034A1 (es) | 2010-05-11 | 2012-05-30 | Sanofi Aventis | Derivados de n-heteroaril tetrahidro-isoquinolina sustituidos, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades del sistema nervioso central |
| JP5766278B2 (ja) | 2010-05-11 | 2015-08-19 | サノフイ | 置換されたｎ−アルキルおよびｎ−アシルテトラヒドロ−イソキノリン誘導体、それらの製造および治療上の使用 |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| HK1208681A1 (en) * | 2012-06-12 | 2016-03-11 | Abbvie Inc. | Pyridinone and pyridazinone derivatives |
| WO2014006945A1 (ja) | 2012-07-04 | 2014-01-09 | アグロカネショウ株式会社 | 2-アミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
| 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 |
| CN105636953B (zh) * | 2013-07-31 | 2018-01-02 | 诺华股份有限公司 | 1,4‑二取代的哒嗪衍生物及其用于治疗与smn缺乏相关的病症的用途 |
| DK3119782T3 (en) * | 2014-03-17 | 2018-03-12 | Remynd Nv Bio Incubator | 2,7-diazaspiro [3.5] NONANFORBINDELSER |
| CA2964103C (en) | 2014-10-31 | 2022-08-30 | Indivior Uk Limited | Dopamine d3 receptor antagonist compounds |
| EP3233077B1 (en) | 2014-12-19 | 2026-05-06 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3233799B1 (en) * | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3256126B1 (en) | 2015-02-09 | 2024-03-27 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| EP3053577A1 (en) * | 2015-02-09 | 2016-08-10 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| CA3119019C (en) * | 2015-12-10 | 2024-06-11 | Ptc Therapeutics, Inc. | Compounds and methods for treating huntington's disease |
| WO2018068296A1 (en) * | 2016-10-14 | 2018-04-19 | Merck Sharp & Dohme Corp. | PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE |
| EP4151627A1 (en) | 2017-06-05 | 2023-03-22 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| 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 |
| CN111163838B (zh) | 2017-06-28 | 2023-03-28 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| BR112020019373A2 (pt) | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
| KR20210038845A (ko) | 2018-06-27 | 2021-04-08 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료를 위한 헤테로아릴 화합물 |
| WO2020005882A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| IL279688B2 (en) | 2018-06-27 | 2025-01-01 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for the treatment of 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 |
| CA3139821A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| KR20230142745A (ko) | 2021-01-29 | 2023-10-11 | 세딜라 테라퓨틱스, 인크. | Cdk2 억제제 및 그의 사용 방법 |
| TW202317560A (zh) | 2021-06-26 | 2023-05-01 | 美商賽迪拉治療股份有限公司 | Ｃｄｋ２抑制劑及其使用方法 |
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| 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 |
| WO1997011940A1 (en) * | 1995-09-29 | 1997-04-03 | Eli Lilly And Company | Spiro compounds as inhibitors of fibrinogen-dependent platelet aggregation |
| GB2309167A (en) * | 1997-05-10 | 1997-07-23 | Anormed Inc | The use of azaspiranes in the treatment of Alzheimer's disease |
| ES2162503T3 (es) * | 1998-06-12 | 2001-12-16 | Hoffmann La Roche | Derivados diaza-espiro(3,5)nonanos. |
| PT1519939E (pt) * | 2002-07-05 | 2010-02-10 | Targacept Inc | Compostos n-arildiazaspirocíclicos e métodos para a sua preparação e utilização |
| MXPA05009708A (es) * | 2003-03-10 | 2006-05-25 | Callisto Pharmaceuticals Inc | Metodo para el tratamiento de cancer con composiciones de azaspirina. |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| WO2005047286A1 (ja) * | 2003-11-13 | 2005-05-26 | Ono Pharmaceutical Co., Ltd. | スピロ複素環化合物 |
| JP2008510711A (ja) * | 2004-08-20 | 2008-04-10 | ターガセプト，インコーポレイテッド | 嗜癖治療におけるｎ−アリールジアザスピラ環状化合物の使用 |
| EP1802623A1 (en) * | 2004-10-12 | 2007-07-04 | Novo Nordisk A/S | 11beta-hydroxysteroid dehydrogenase type 1 active spiro compounds |
| JP2008546826A (ja) * | 2005-06-28 | 2008-12-25 | ノイロサーチ アクティーゼルスカブ | 新規な３，９−ジアザ−スピロ［５．５］ウンデカン誘導体及びモノアミン神経伝達物質再取り込み阻害剤としてのこれらの使用 |
| 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 CA CA002651654A patent/CA2651654A1/en not_active Abandoned
- 2007-05-08 EP EP07756232A patent/EP2021004A4/en not_active Withdrawn
- 2007-05-08 WO PCT/US2007/011135 patent/WO2007133561A2/en not_active Ceased
- 2007-05-08 KR KR1020087029820A patent/KR20090015956A/ko not_active Withdrawn
-
2008
- 2008-11-05 IL IL195132A patent/IL195132A0/en unknown
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