JP2009536651A - 置換されたアザスピロ誘導体 - Google Patents

Info

Publication number

JP2009536651A

JP2009536651A JP2009509820A JP2009509820A JP2009536651A JP 2009536651 A JP2009536651 A JP 2009536651A JP 2009509820 A JP2009509820 A JP 2009509820A JP 2009509820 A JP2009509820 A JP 2009509820A JP 2009536651 A JP2009536651 A JP 2009536651A

Authority

JP

Japan

Prior art keywords

cyclobutyl

diazaspiro

undecane

undes

alkyl

Prior art date

2006-05-08

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Withdrawn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

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• 150000001875 compounds Chemical class 0.000 claims abstract description 267
• 102000004384 Histamine H3 receptors Human genes 0.000 claims abstract description 162
• 108090000981 Histamine H3 receptors Proteins 0.000 claims abstract description 162
• 238000000034 method Methods 0.000 claims abstract description 101
• 230000027455 binding Effects 0.000 claims abstract description 46
• 230000000694 effects Effects 0.000 claims abstract description 38
• 102000005962 receptors Human genes 0.000 claims abstract description 25
• 108020003175 receptors Proteins 0.000 claims abstract description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 129
• -1 amino, cyano, hydroxy, aminocarbonyl Chemical group 0.000 claims description 117
• 239000000203 mixture Substances 0.000 claims description 107
• 125000001424 substituent group Chemical group 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 79
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 74
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 55
• 229910052736 halogen Inorganic materials 0.000 claims description 53
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 238000003556 assay Methods 0.000 claims description 50
• 239000000243 solution Substances 0.000 claims description 45
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 39
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 239000003814 drug Substances 0.000 claims description 31
• 125000004043 oxo group Chemical group O=* 0.000 claims description 31
• 206010016256 fatigue Diseases 0.000 claims description 30
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 20
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 20
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 20
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 150000005215 alkyl ethers Chemical class 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 208000010877 cognitive disease Diseases 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 16
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 16
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 208000018737 Parkinson disease Diseases 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 12
• 208000028698 Cognitive impairment Diseases 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 208000019695 Migraine disease Diseases 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
• 208000002173 dizziness Diseases 0.000 claims description 10
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 10
• 206010027599 migraine Diseases 0.000 claims description 10
• 201000000980 schizophrenia Diseases 0.000 claims description 10
• 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 description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 208000030814 Eating disease Diseases 0.000 claims description 9
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 9
• 208000008589 Obesity Diseases 0.000 claims description 9
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
• 201000010105 allergic rhinitis Diseases 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• 235000014632 disordered eating Nutrition 0.000 claims description 9
• 206010015037 epilepsy Diseases 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 201000003152 motion sickness Diseases 0.000 claims description 9
• 235000020824 obesity Nutrition 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
• 201000003631 narcolepsy Diseases 0.000 claims description 8
• 208000019116 sleep disease Diseases 0.000 claims description 8
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 8
• 206010041349 Somnolence Diseases 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 5
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
• 206010012289 Dementia Diseases 0.000 claims description 5
• 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 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 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 5
• 206010027175 memory impairment Diseases 0.000 claims description 5
• 201000002859 sleep apnea Diseases 0.000 claims description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 208000026139 Memory disease Diseases 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 239000003395 histamine H3 receptor antagonist Substances 0.000 claims description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 239000000443 aerosol Substances 0.000 claims description 2
• 238000002347 injection Methods 0.000 claims description 2
• 239000007924 injection Substances 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 12
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 9
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
• 125000001589 carboacyl group Chemical group 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
• 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
• 208000020685 sleep-wake disease Diseases 0.000 claims 3
• 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
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 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
• 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
• 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
• 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
• 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
• 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
• 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
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• 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
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• 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
• 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
• 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
• 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
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• 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
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• 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
• 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
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