CA2651654A1

CA2651654A1 - Substituted azaspiro derivatives

Substituted azaspiro derivatives Download PDF

Info

Publication number: CA2651654A1
Authority: CA; Canada
Prior art keywords: cyclobutyl; diazaspiro; undecane; undec; pyridazin
Prior art date: 2006-05-08
Legal status : Abandoned

Application number

CA002651654A

Other languages

English (en)

French (fr)

Inventor

Yuelian Xu

Timothy M. Caldwell

Linghong Xie

Bertrand L. Chenard

Current Assignee

Neurogen Corp

Original Assignee

Individual

Priority date

2006-05-08

Filing date

2007-05-08

Publication date

2007-11-22

2007-05-08 Application filed by Individual filed Critical Individual

2007-11-22 Publication of CA2651654A1 publication Critical patent/CA2651654A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 270
102000004384 Histamine H3 receptors Human genes 0.000 claims abstract description 164
108090000981 Histamine H3 receptors Proteins 0.000 claims abstract description 164
238000000034 method Methods 0.000 claims abstract description 88
230000027455 binding Effects 0.000 claims abstract description 48
230000000694 effects Effects 0.000 claims abstract description 44
238000009739 binding Methods 0.000 claims abstract description 33
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
238000011282 treatment Methods 0.000 claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
-1 amino, cyano, hydroxy, aminocarbonyl Chemical group 0.000 claims description 219
239000000203 mixture Substances 0.000 claims description 114
125000001424 substituent group Chemical group 0.000 claims description 87
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 79
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 71
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 60
229910052736 halogen Inorganic materials 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 53
150000002367 halogens Chemical class 0.000 claims description 52
238000003556 assay Methods 0.000 claims description 47
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 35
125000004043 oxo group Chemical group O=* 0.000 claims description 31
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
206010016256 fatigue Diseases 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 27
241000282414 Homo sapiens Species 0.000 claims description 26
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 23
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 21
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 20
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 20
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 20
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 16
229920006395 saturated elastomer Polymers 0.000 claims description 16
208000010877 cognitive disease Diseases 0.000 claims description 15
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 14
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 12
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
208000019695 Migraine disease 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
201000003152 motion sickness Diseases 0.000 claims description 10
201000000980 schizophrenia Diseases 0.000 claims description 10
208000030814 Eating disease Diseases 0.000 claims description 9
208000019454 Feeding and Eating disease Diseases 0.000 claims description 9
208000026139 Memory disease Diseases 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 9
206010039085 Rhinitis allergic Diseases 0.000 claims description 9
208000012886 Vertigo Diseases 0.000 claims description 9
201000010105 allergic rhinitis Diseases 0.000 claims description 9
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
235000020824 obesity Nutrition 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
231100000889 vertigo Toxicity 0.000 claims description 9
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 8
201000003631 narcolepsy Diseases 0.000 claims description 8
208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 7
206010041349 Somnolence Diseases 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
235000005152 nicotinamide Nutrition 0.000 claims description 7
239000011570 nicotinamide Substances 0.000 claims description 7
229960003966 nicotinamide Drugs 0.000 claims description 7
101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 6
208000018737 Parkinson disease Diseases 0.000 claims description 6
101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims description 6
238000001514 detection method Methods 0.000 claims description 6
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 5
MSLLTXUXWWYPRJ-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 MSLLTXUXWWYPRJ-UHFFFAOYSA-N 0.000 claims description 5
BCKBISZSBDATPQ-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BCKBISZSBDATPQ-UHFFFAOYSA-N 0.000 claims description 5
125000001313 C5-C10 heteroaryl 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
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
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
201000002859 sleep apnea Diseases 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
REOOYQCVFHWQKA-UHFFFAOYSA-N 2-cyclobutyl-8-(5-pyridin-4-ylpyridin-2-yl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CC2(CCN(CC2)C=2N=CC(=CC=2)C=2C=CN=CC=2)CC1 REOOYQCVFHWQKA-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
ONFWEUVYHAVCPU-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 ONFWEUVYHAVCPU-UHFFFAOYSA-N 0.000 claims description 4
LRHBKQRIWIOOMI-UHFFFAOYSA-N 6-[(3-cyclobutyl-3-azaspiro[5.5]undecan-9-yl)oxy]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1OC1CCC2(CCN(CC2)C2CCC2)CC1 LRHBKQRIWIOOMI-UHFFFAOYSA-N 0.000 claims description 4
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 4
FWXHWYBNWXKGRM-UHFFFAOYSA-N 8-cyclobutyl-2-(5-pyridin-3-ylpyridin-2-yl)-2,8-diazaspiro[4.5]decane Chemical compound C1CCC1N1CCC2(CN(CC2)C=2N=CC(=CC=2)C=2C=NC=CC=2)CC1 FWXHWYBNWXKGRM-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
239000003395 histamine H3 receptor antagonist Substances 0.000 claims description 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
SYIXFWIVLZMWAV-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SYIXFWIVLZMWAV-UHFFFAOYSA-N 0.000 claims description 3
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 3
BGWKPZBNWRRXQS-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BGWKPZBNWRRXQS-UHFFFAOYSA-N 0.000 claims description 3
NGJRHZOJLBJNGH-UHFFFAOYSA-N 4-(9-cyclopentyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCCC2)CC1 NGJRHZOJLBJNGH-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
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 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
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
CJRRYDFLKYIWAL-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecane-3-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1CCC2(CCN(CC2)C2CCC2)CC1 CJRRYDFLKYIWAL-UHFFFAOYSA-N 0.000 claims description 2
UUUMTNCZXOAGOZ-UHFFFAOYSA-N 1-[4-[(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)sulfonyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CCC2(CCN(CC2)C2CCC2)CC1 UUUMTNCZXOAGOZ-UHFFFAOYSA-N 0.000 claims description 2
NGGUNFUGKKLHJR-UHFFFAOYSA-N 1-[4-[2-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-5-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CN=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NGGUNFUGKKLHJR-UHFFFAOYSA-N 0.000 claims description 2
CPLMREFXTGPMIO-UHFFFAOYSA-N 1-[4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 CPLMREFXTGPMIO-UHFFFAOYSA-N 0.000 claims description 2
XYLQZKAGCOLMOQ-UHFFFAOYSA-N 1-[4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 XYLQZKAGCOLMOQ-UHFFFAOYSA-N 0.000 claims description 2
SOGYFBLNUIYIEL-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]ethanone Chemical compound N1=NC(C(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SOGYFBLNUIYIEL-UHFFFAOYSA-N 0.000 claims description 2
SJKLZKDPQAKXSU-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazine-3-carbonitrile Chemical compound N1=NC(C#N)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SJKLZKDPQAKXSU-UHFFFAOYSA-N 0.000 claims description 2
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
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 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
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 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
JBODUXBIIZRGRJ-UHFFFAOYSA-N ethyl 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JBODUXBIIZRGRJ-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000006187 pill Substances 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 20
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 20
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
HQRVZTKKGWATQJ-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 HQRVZTKKGWATQJ-UHFFFAOYSA-N 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
230000001747 exhibiting effect Effects 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
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
FBLNQSJNVLIABT-UHFFFAOYSA-N 1-[2-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-5-yl]ethanone Chemical compound N1=CC(C(=O)C)=CN=C1N1CCC2(CCN(CC2)C2CCC2)CC1 FBLNQSJNVLIABT-UHFFFAOYSA-N 0.000 claims 1
PSFSNZQSBAHCHN-UHFFFAOYSA-N 1-[3-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 PSFSNZQSBAHCHN-UHFFFAOYSA-N 0.000 claims 1
XFRCBQYJFFRGGC-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-2-methoxyphenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC(N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 XFRCBQYJFFRGGC-UHFFFAOYSA-N 0.000 claims 1
QSGFPBADXAOMIC-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-3,5-difluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC(F)=C1N1CCC2(CCN(CC2)C2CCC2)CC1 QSGFPBADXAOMIC-UHFFFAOYSA-N 0.000 claims 1
IJJOZMVHZTUCIY-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 IJJOZMVHZTUCIY-UHFFFAOYSA-N 0.000 claims 1
VKDYVDWFPLFYNT-UHFFFAOYSA-N 1-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 VKDYVDWFPLFYNT-UHFFFAOYSA-N 0.000 claims 1
UESUTRDLFVJBBS-UHFFFAOYSA-N 1-[4-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 UESUTRDLFVJBBS-UHFFFAOYSA-N 0.000 claims 1
WXCHYLWIUQDYQW-UHFFFAOYSA-N 1-[4-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)piperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(N2CCC3(CCN(CC3)C3CCC3)CC2)CC1 WXCHYLWIUQDYQW-UHFFFAOYSA-N 0.000 claims 1
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OGVMNKTZTLSEBI-UHFFFAOYSA-N 1-[6-(2-cyclobutyl-2,8-diazaspiro[4.5]decan-8-yl)pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1N1CCC2(CN(CC2)C2CCC2)CC1 OGVMNKTZTLSEBI-UHFFFAOYSA-N 0.000 claims 1
RNFWCWPRNRRTNV-UHFFFAOYSA-N 1-[6-(8-cyclobutyl-2,8-diazaspiro[4.5]decan-2-yl)pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1N1CC2(CCN(CC2)C2CCC2)CC1 RNFWCWPRNRRTNV-UHFFFAOYSA-N 0.000 claims 1
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CGZFIYMMKXMZTL-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-diethylpiperidin-4-amine Chemical compound C1CC(N(CC)CC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 CGZFIYMMKXMZTL-UHFFFAOYSA-N 0.000 claims 1
RLWSICKZZPEAHT-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 RLWSICKZZPEAHT-UHFFFAOYSA-N 0.000 claims 1
JFZMJWQZELIYQE-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-diethylpyrrolidin-3-amine Chemical compound C1C(N(CC)CC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 JFZMJWQZELIYQE-UHFFFAOYSA-N 0.000 claims 1
JMNGZHIGOPCNHM-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-dimethylmethanamine Chemical compound N1=CC(CN(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JMNGZHIGOPCNHM-UHFFFAOYSA-N 0.000 claims 1
NABDDTUPOKWYSX-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NABDDTUPOKWYSX-UHFFFAOYSA-N 0.000 claims 1
MCVUBIYJPCATQY-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 MCVUBIYJPCATQY-UHFFFAOYSA-N 0.000 claims 1
ZQTYCQAMBNFLPX-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n-dipropylpiperidin-4-amine Chemical compound C1CC(N(CCC)CCC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 ZQTYCQAMBNFLPX-UHFFFAOYSA-N 0.000 claims 1
JWEQUIZSJMNURG-UHFFFAOYSA-N 1-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JWEQUIZSJMNURG-UHFFFAOYSA-N 0.000 claims 1
PYHXZRMGGLAPPA-UHFFFAOYSA-N 1-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 PYHXZRMGGLAPPA-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
PCZVUZDQNPPYPE-UHFFFAOYSA-N 2-[4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]piperazin-1-yl]-n,n-dimethylethanamine Chemical compound C1CN(CCN(C)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 PCZVUZDQNPPYPE-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
BEGSBHRLLLMRJB-UHFFFAOYSA-N 2-chloro-4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylbenzamide Chemical compound C1=C(Cl)C(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BEGSBHRLLLMRJB-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
WBMZHQTUMFPSRY-UHFFFAOYSA-N 2-cyclobutyl-8-[5-(6-methoxypyridin-3-yl)pyridin-2-yl]-2,8-diazaspiro[4.5]decane Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N2CCC3(CN(CC3)C3CCC3)CC2)N=C1 WBMZHQTUMFPSRY-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
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
RAYBVWRSKHVYEB-UHFFFAOYSA-N 3-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzonitrile Chemical compound N#CC1=CC=CC(N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 RAYBVWRSKHVYEB-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
XKGACMSRZDFEED-UHFFFAOYSA-N 3-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 XKGACMSRZDFEED-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
ZXUQJUZHRWGDEC-UHFFFAOYSA-N 3-[4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]piperazin-1-yl]-n,n-dimethylpropan-1-amine Chemical compound C1CN(CCCN(C)C)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 ZXUQJUZHRWGDEC-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
WCWSYSIOUYCNIH-UHFFFAOYSA-N 3-[6-(2-chloro-6-fluoro-3-methylphenyl)pyridazin-3-yl]-9-cyclobutyl-3,9-diazaspiro[5.5]undecane Chemical compound CC1=CC=C(F)C(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1Cl WCWSYSIOUYCNIH-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
SQHKPDGUMSJYQZ-UHFFFAOYSA-N 3-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 SQHKPDGUMSJYQZ-UHFFFAOYSA-N 0.000 claims 1
ZJXQFEVVSLWNGY-UHFFFAOYSA-N 3-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 ZJXQFEVVSLWNGY-UHFFFAOYSA-N 0.000 claims 1
SVHCRDJIOZADSH-UHFFFAOYSA-N 3-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 SVHCRDJIOZADSH-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
AQFCTCBFYPEGNI-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-2-fluoro-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 AQFCTCBFYPEGNI-UHFFFAOYSA-N 0.000 claims 1
NLKCGGUVVKHWBN-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-3-fluoro-n-methylbenzamide Chemical compound FC1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 NLKCGGUVVKHWBN-UHFFFAOYSA-N 0.000 claims 1
INKPTIUJWXNBFY-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 INKPTIUJWXNBFY-UHFFFAOYSA-N 0.000 claims 1
UXZCNJRCLBFJEI-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 UXZCNJRCLBFJEI-UHFFFAOYSA-N 0.000 claims 1
BNUQFBIXWLNJRH-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2,2,2-trifluoroethyl)benzamide Chemical compound C1=CC(C(=O)NCC(F)(F)F)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BNUQFBIXWLNJRH-UHFFFAOYSA-N 0.000 claims 1
FCIBTIPOBFFWFZ-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2,2-dimethylpropyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 FCIBTIPOBFFWFZ-UHFFFAOYSA-N 0.000 claims 1
ZGJHKUMIOQIHRA-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-ethylbutyl)benzamide Chemical compound C1=CC(C(=O)NCC(CC)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 ZGJHKUMIOQIHRA-UHFFFAOYSA-N 0.000 claims 1
WBJZTGXHEUCKPT-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methoxyethyl)-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)N(C(C)C)CCOC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 WBJZTGXHEUCKPT-UHFFFAOYSA-N 0.000 claims 1
NUPZRGMEUUQFED-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 NUPZRGMEUUQFED-UHFFFAOYSA-N 0.000 claims 1
HBOKCRGITLIDPQ-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methylpropyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 HBOKCRGITLIDPQ-UHFFFAOYSA-N 0.000 claims 1
CBGDRQLNCCKXAD-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(3-methylbutyl)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 CBGDRQLNCCKXAD-UHFFFAOYSA-N 0.000 claims 1
PLFAOTXKBYERIP-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(cyclohexylmethyl)benzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NCC1CCCCC1 PLFAOTXKBYERIP-UHFFFAOYSA-N 0.000 claims 1
NCLAWBYMRTZOPA-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(oxan-4-yl)benzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1CCOCC1 NCLAWBYMRTZOPA-UHFFFAOYSA-N 0.000 claims 1
IUZXJODGEVLOCV-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(oxan-4-ylmethyl)benzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NCC1CCOCC1 IUZXJODGEVLOCV-UHFFFAOYSA-N 0.000 claims 1
PDRKQFMINVZQPG-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(pyridin-4-ylmethyl)benzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NCC1=CC=NC=C1 PDRKQFMINVZQPG-UHFFFAOYSA-N 0.000 claims 1
VBOAYSZRDSSLJS-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cycloheptylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1CCCCCC1 VBOAYSZRDSSLJS-UHFFFAOYSA-N 0.000 claims 1
JUEDMGHQHDMODL-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclohexyl-n-ethylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N(CC)C1CCCCC1 JUEDMGHQHDMODL-UHFFFAOYSA-N 0.000 claims 1
ARDNCOLIDVHRIY-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclohexyl-n-methylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)N(C)C1CCCCC1 ARDNCOLIDVHRIY-UHFFFAOYSA-N 0.000 claims 1
PJPPSCMKWBHIHM-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclopentylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1CCCC1 PJPPSCMKWBHIHM-UHFFFAOYSA-N 0.000 claims 1
CAEBJHUIPWGBBI-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclopropylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1CC1 CAEBJHUIPWGBBI-UHFFFAOYSA-N 0.000 claims 1
SLTFDQKZXGOGRG-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-ethyl-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)N(C(C)C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SLTFDQKZXGOGRG-UHFFFAOYSA-N 0.000 claims 1
JPDXCKRQTYVGMD-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JPDXCKRQTYVGMD-UHFFFAOYSA-N 0.000 claims 1
XRKLFGXPFXTXHV-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methyl-2-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 XRKLFGXPFXTXHV-UHFFFAOYSA-N 0.000 claims 1
OSYOHPGYXJQTTJ-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methyl-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)N(C)C(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 OSYOHPGYXJQTTJ-UHFFFAOYSA-N 0.000 claims 1
KDIBMORZHMOQGA-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylnaphthalene-1-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)NC)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 KDIBMORZHMOQGA-UHFFFAOYSA-N 0.000 claims 1
YKKJZHVQNXFFQS-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-pentan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)CCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 YKKJZHVQNXFFQS-UHFFFAOYSA-N 0.000 claims 1
LGNKPWSJTITPMW-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-pentylbenzamide Chemical compound C1=CC(C(=O)NCCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 LGNKPWSJTITPMW-UHFFFAOYSA-N 0.000 claims 1
YKWAJOKGHGVWCS-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 YKWAJOKGHGVWCS-UHFFFAOYSA-N 0.000 claims 1
LLCGTPAJISJCGY-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 LLCGTPAJISJCGY-UHFFFAOYSA-N 0.000 claims 1
IAHFJBZAOSLDLN-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-pyridin-2-ylbenzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1=CC=CC=N1 IAHFJBZAOSLDLN-UHFFFAOYSA-N 0.000 claims 1
SIGBEQRQXWNUNU-UHFFFAOYSA-N 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SIGBEQRQXWNUNU-UHFFFAOYSA-N 0.000 claims 1
NMZAPRVPPZPYLI-UHFFFAOYSA-N 4-(9-ethyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methylbenzamide Chemical compound C1CN(CC)CCC21CCN(C=1C=CC(=CC=1)C(=O)NC)CC2 NMZAPRVPPZPYLI-UHFFFAOYSA-N 0.000 claims 1
WQOBMXGTWBAUGX-UHFFFAOYSA-N 4-[(3-cyclobutyl-3,9-diazaspiro[5.5]undecan-9-yl)methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CN1CCC2(CCN(CC2)C2CCC2)CC1 WQOBMXGTWBAUGX-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
HDPOGMBGOVNXOF-UHFFFAOYSA-N 4-[2-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-5-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 HDPOGMBGOVNXOF-UHFFFAOYSA-N 0.000 claims 1
PDSKCSAQUOXDDA-UHFFFAOYSA-N 4-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-methylpyridin-2-one Chemical compound O=C1N(C)C=CC(C=2C=CC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 PDSKCSAQUOXDDA-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
NOFZWCDDHAYZGJ-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 NOFZWCDDHAYZGJ-UHFFFAOYSA-N 0.000 claims 1
XTGRHOKIKFJXRS-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 XTGRHOKIKFJXRS-UHFFFAOYSA-N 0.000 claims 1
DZOZGSIHKNRXKA-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 DZOZGSIHKNRXKA-UHFFFAOYSA-N 0.000 claims 1
BAHASVGNLBUBKE-UHFFFAOYSA-N 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 BAHASVGNLBUBKE-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
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LAYIEPUIEZFLOL-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-(2,2,2-trifluoroethyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(F)(F)F)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 LAYIEPUIEZFLOL-UHFFFAOYSA-N 0.000 claims 1
LTALCMAXMDIWSH-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-ethylpyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 LTALCMAXMDIWSH-UHFFFAOYSA-N 0.000 claims 1
COSPOKZOFUCCIU-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 COSPOKZOFUCCIU-UHFFFAOYSA-N 0.000 claims 1
ZNFRZIJYMUJGEJ-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-methylpyrimidin-2-one Chemical compound C1=NC(=O)N(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 ZNFRZIJYMUJGEJ-UHFFFAOYSA-N 0.000 claims 1
ZWJPMDBIINRDTQ-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-propan-2-ylpyridin-2-one Chemical compound C1=CC(=O)N(C(C)C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 ZWJPMDBIINRDTQ-UHFFFAOYSA-N 0.000 claims 1
JZIMKYDSWSDADP-UHFFFAOYSA-N 5-[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-1-propylpyridin-2-one Chemical compound C1=CC(=O)N(CCC)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=C1 JZIMKYDSWSDADP-UHFFFAOYSA-N 0.000 claims 1
GEOAYTRYGKVFPT-UHFFFAOYSA-N 5-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 GEOAYTRYGKVFPT-UHFFFAOYSA-N 0.000 claims 1
JRPVEEQNMRUGNH-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2,2,2-trifluoroethyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC(F)(F)F)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JRPVEEQNMRUGNH-UHFFFAOYSA-N 0.000 claims 1
JPFPHQOFGXFNIJ-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2,2-dimethylpropyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC(C)(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JPFPHQOFGXFNIJ-UHFFFAOYSA-N 0.000 claims 1
RNNNVCQBJXNWKD-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-ethylbutyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC(CC)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 RNNNVCQBJXNWKD-UHFFFAOYSA-N 0.000 claims 1
MUHJZVSWMAQKCL-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methoxyethyl)-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)N(C(C)C)CCOC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 MUHJZVSWMAQKCL-UHFFFAOYSA-N 0.000 claims 1
XWNNDSCSEIQBHS-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methylbutyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 XWNNDSCSEIQBHS-UHFFFAOYSA-N 0.000 claims 1
UAIVXUAKPVRYHL-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(2-methylpropyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 UAIVXUAKPVRYHL-UHFFFAOYSA-N 0.000 claims 1
ZSKTWGYLFMCVJU-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(3-methylbutyl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 ZSKTWGYLFMCVJU-UHFFFAOYSA-N 0.000 claims 1
CTLOUDMOHBGHHX-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(cyclohexylmethyl)pyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NCC1CCCCC1 CTLOUDMOHBGHHX-UHFFFAOYSA-N 0.000 claims 1
ITQYBSOIZPNDTE-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-(cyclopropylmethyl)pyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NCC1CC1 ITQYBSOIZPNDTE-UHFFFAOYSA-N 0.000 claims 1
FJTOUJMVYWTTRU-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cycloheptylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NC1CCCCCC1 FJTOUJMVYWTTRU-UHFFFAOYSA-N 0.000 claims 1
BRMLMQOHUCBQGL-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclohexyl-n-ethylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N(CC)C1CCCCC1 BRMLMQOHUCBQGL-UHFFFAOYSA-N 0.000 claims 1
GHQFWFKKABCCFV-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclohexyl-n-methylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)N(C)C1CCCCC1 GHQFWFKKABCCFV-UHFFFAOYSA-N 0.000 claims 1
QYPYOIMUECSUMR-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclopentylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NC1CCCC1 QYPYOIMUECSUMR-UHFFFAOYSA-N 0.000 claims 1
SARKQXNGXTUCLB-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-cyclopropylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NC1CC1 SARKQXNGXTUCLB-UHFFFAOYSA-N 0.000 claims 1
GACJVUVCZUNINE-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-ethyl-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)N(C(C)C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 GACJVUVCZUNINE-UHFFFAOYSA-N 0.000 claims 1
VUQHFJGBMJUJEV-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-ethylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 VUQHFJGBMJUJEV-UHFFFAOYSA-N 0.000 claims 1
FVNIHFGMRPYZME-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methyl-n-(1-methylpiperidin-4-yl)pyridin-3-amine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1N(C)C1CCN(C)CC1 FVNIHFGMRPYZME-UHFFFAOYSA-N 0.000 claims 1
KNVLXLGBVUOXIX-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-methyl-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)N(C)C(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 KNVLXLGBVUOXIX-UHFFFAOYSA-N 0.000 claims 1
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LFLBHTYPBGBTHO-UHFFFAOYSA-N 6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)-n-pentylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 LFLBHTYPBGBTHO-UHFFFAOYSA-N 0.000 claims 1
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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
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
HMUBMYWDBBSOHN-UHFFFAOYSA-N [4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]-phenylmethanone Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)C1=CC=CC=C1 HMUBMYWDBBSOHN-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
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
BUTJXLHUDBAHSO-UHFFFAOYSA-N [6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]methanol Chemical compound N1=CC(CO)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BUTJXLHUDBAHSO-UHFFFAOYSA-N 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
NNCKHQJTFPXYMJ-UHFFFAOYSA-N benzyl 4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzoate Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)OCC1=CC=CC=C1 NNCKHQJTFPXYMJ-UHFFFAOYSA-N 0.000 claims 1
239000006071 cream Substances 0.000 claims 1
IJIFHTKATCHQRZ-UHFFFAOYSA-N ethyl 3-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2N=NC(=CC=2)N2CCC3(CCN(CC3)C3CCC3)CC2)=C1 IJIFHTKATCHQRZ-UHFFFAOYSA-N 0.000 claims 1
IMKRQSKILNKXBH-UHFFFAOYSA-N ethyl 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 IMKRQSKILNKXBH-UHFFFAOYSA-N 0.000 claims 1
CTYXVRXSFMYGOH-UHFFFAOYSA-N ethyl 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 CTYXVRXSFMYGOH-UHFFFAOYSA-N 0.000 claims 1
239000012530 fluid Substances 0.000 claims 1
JPTWNADGMSHTLE-UHFFFAOYSA-N methyl 4-[(3-cyclobutyl-3,9-diazaspiro[5.5]undecan-9-yl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1CCC2(CCN(CC2)C2CCC2)CC1 JPTWNADGMSHTLE-UHFFFAOYSA-N 0.000 claims 1
NXGMCEXGZNAURP-UHFFFAOYSA-N methyl 4-[2-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CN=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 NXGMCEXGZNAURP-UHFFFAOYSA-N 0.000 claims 1
JINQSQDVNNGGRI-UHFFFAOYSA-N methyl 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridazin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=N1 JINQSQDVNNGGRI-UHFFFAOYSA-N 0.000 claims 1
JMPDNBLQSNUOEQ-UHFFFAOYSA-N methyl 4-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=C1 JMPDNBLQSNUOEQ-UHFFFAOYSA-N 0.000 claims 1
NYFNDVJBWNHVCV-UHFFFAOYSA-N n'-[6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridin-3-yl]-n,n,n'-trimethylpropane-1,3-diamine Chemical compound N1=CC(N(C)CCCN(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 NYFNDVJBWNHVCV-UHFFFAOYSA-N 0.000 claims 1
PXHHCKIEZAGVOD-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-1-cyclohexylmethanamine Chemical compound C1CCCCC1CNCC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 PXHHCKIEZAGVOD-UHFFFAOYSA-N 0.000 claims 1
CTSLENWDHKMXES-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-1-cyclopropylmethanamine Chemical compound C1CC1CNCC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 CTSLENWDHKMXES-UHFFFAOYSA-N 0.000 claims 1
HCRRATKWYJIJFA-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-2,2-dimethylpropan-1-amine Chemical compound C1=CC(CNCC(C)(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 HCRRATKWYJIJFA-UHFFFAOYSA-N 0.000 claims 1
QBPHALOQRAWFKN-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-2-ethylbutan-1-amine Chemical compound C1=CC(CNCC(CC)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 QBPHALOQRAWFKN-UHFFFAOYSA-N 0.000 claims 1
UUFGQWCJDDSQSC-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-2-methylbutan-1-amine Chemical compound C1=CC(CNCC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 UUFGQWCJDDSQSC-UHFFFAOYSA-N 0.000 claims 1
MAUHFYJRNOWWLN-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-2-methylpropan-1-amine Chemical compound C1=CC(CNCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 MAUHFYJRNOWWLN-UHFFFAOYSA-N 0.000 claims 1
PBPHIHPBNRPXSN-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-3-methylbutan-1-amine Chemical compound C1=CC(CNCCC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 PBPHIHPBNRPXSN-UHFFFAOYSA-N 0.000 claims 1
LAKFZFUXPKRRIG-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-n-(2-methoxyethyl)propan-2-amine Chemical compound C1=CC(CN(CCOC)C(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 LAKFZFUXPKRRIG-UHFFFAOYSA-N 0.000 claims 1
REZBWVGJOZPTRQ-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 REZBWVGJOZPTRQ-UHFFFAOYSA-N 0.000 claims 1
BPQIDORRLOJZIP-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-n-ethylpropan-2-amine Chemical compound C1=CC(CN(CC)C(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 BPQIDORRLOJZIP-UHFFFAOYSA-N 0.000 claims 1
ZQZPCBXJRSUCCS-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]-n-methylcyclohexanamine Chemical compound C1CCCCC1N(C)CC(C=C1)=CC=C1N(CC1)CCC1(CC1)CCN1C1CCC1 ZQZPCBXJRSUCCS-UHFFFAOYSA-N 0.000 claims 1
JRWIPJQOPQLRFP-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]butan-1-amine Chemical compound C1=CC(CNCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 JRWIPJQOPQLRFP-UHFFFAOYSA-N 0.000 claims 1
HLSSZORENVWXOE-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]butan-2-amine Chemical compound C1=CC(CNC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 HLSSZORENVWXOE-UHFFFAOYSA-N 0.000 claims 1
HTCFNKVNJMBAKB-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]cyclobutanamine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CNC1CCC1 HTCFNKVNJMBAKB-UHFFFAOYSA-N 0.000 claims 1
CECWJVJVBQYZRP-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]cycloheptanamine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CNC1CCCCCC1 CECWJVJVBQYZRP-UHFFFAOYSA-N 0.000 claims 1
OMSSWHSSWFCQRZ-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]cyclohexanamine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CNC1CCCCC1 OMSSWHSSWFCQRZ-UHFFFAOYSA-N 0.000 claims 1
LIASFDAAIMTEHY-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]cyclopentanamine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CNC1CCCC1 LIASFDAAIMTEHY-UHFFFAOYSA-N 0.000 claims 1
IEOGVUCWROAUND-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]cyclopropanamine Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1CNC1CC1 IEOGVUCWROAUND-UHFFFAOYSA-N 0.000 claims 1
MSSBTCJGXOORPF-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]pentan-1-amine Chemical compound C1=CC(CNCCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 MSSBTCJGXOORPF-UHFFFAOYSA-N 0.000 claims 1
KBIABYFFHZCHNJ-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]pentan-2-amine Chemical compound C1=CC(CNC(C)CCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 KBIABYFFHZCHNJ-UHFFFAOYSA-N 0.000 claims 1
QIWCTIAPGCDNHV-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]prop-2-en-1-amine Chemical compound C1=CC(CNCC=C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 QIWCTIAPGCDNHV-UHFFFAOYSA-N 0.000 claims 1
CXONVNHZCHYTMJ-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]propan-1-amine Chemical compound C1=CC(CNCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 CXONVNHZCHYTMJ-UHFFFAOYSA-N 0.000 claims 1
FXNLUPGJMXSHSF-UHFFFAOYSA-N n-[[4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]methyl]propan-2-amine Chemical compound C1=CC(CNC(C)C)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 FXNLUPGJMXSHSF-UHFFFAOYSA-N 0.000 claims 1
ZJEWPODMJRBGHO-UHFFFAOYSA-N n-butan-2-yl-4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzamide Chemical compound C1=CC(C(=O)NC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 ZJEWPODMJRBGHO-UHFFFAOYSA-N 0.000 claims 1
SKQODEMRGAYGIN-UHFFFAOYSA-N n-butan-2-yl-6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC(C)CC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SKQODEMRGAYGIN-UHFFFAOYSA-N 0.000 claims 1
SAQOYCUZZRSAGC-UHFFFAOYSA-N n-butyl-4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzamide Chemical compound C1=CC(C(=O)NCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 SAQOYCUZZRSAGC-UHFFFAOYSA-N 0.000 claims 1
XMJWSZOIZRVCGY-UHFFFAOYSA-N n-butyl-6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCCCC)=CC=C1N1CCC2(CCN(CC2)C2CCC2)CC1 XMJWSZOIZRVCGY-UHFFFAOYSA-N 0.000 claims 1
RNLRWMBQOCEIFG-UHFFFAOYSA-N n-cyclobutyl-4-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)benzamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)C=CC=1C(=O)NC1CCC1 RNLRWMBQOCEIFG-UHFFFAOYSA-N 0.000 claims 1
XJJMKQIBSNWRJX-UHFFFAOYSA-N n-cyclobutyl-6-(9-cyclobutyl-3,9-diazaspiro[5.5]undecan-3-yl)pyridine-3-carboxamide Chemical compound C=1C=C(N2CCC3(CCN(CC3)C3CCC3)CC2)N=CC=1C(=O)NC1CCC1 XJJMKQIBSNWRJX-UHFFFAOYSA-N 0.000 claims 1
YQOQVQLEJMGIBJ-UHFFFAOYSA-N n-methyl-4-(3-propan-2-yl-3,9-diazaspiro[5.5]undecan-9-yl)benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C(C)C)CC1 YQOQVQLEJMGIBJ-UHFFFAOYSA-N 0.000 claims 1
NCRVWNOCHGSBGV-UHFFFAOYSA-N n-methyl-4-[9-(2-methylcyclopentyl)-3,9-diazaspiro[5.5]undecan-3-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2C(CCC2)C)CC1 NCRVWNOCHGSBGV-UHFFFAOYSA-N 0.000 claims 1
MEOKSDSLMJVFOA-UHFFFAOYSA-N n-methyl-4-[9-(oxan-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC2(CCN(CC2)C2CCOCC2)CC1 MEOKSDSLMJVFOA-UHFFFAOYSA-N 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
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