JP2016535003A5

JP2016535003A5 -

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Publication number: JP2016535003A5
Authority: JP; Japan
Prior art keywords: methyl; quinoline; carbonitrile; cyanoquinolin; carboxamide
Prior art date: 2014-10-14
Legal status : Granted

Application number

JP2016523329A

Other languages

English (en)

Japanese (ja)

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JP6223563B2 (ja

JP2016535003A (ja

Filing date

2014-10-14

Publication date

2017-07-27

2014-10-14 Application filed filed Critical

2014-10-14 Priority claimed from PCT/US2014/060418 external-priority patent/WO2015057659A1/en

2016-11-10 Publication of JP2016535003A publication Critical patent/JP2016535003A/ja

2017-07-27 Publication of JP2016535003A5 publication Critical patent/JP2016535003A5/ja

2017-11-01 Application granted granted Critical

2017-11-01 Publication of JP6223563B2 publication Critical patent/JP6223563B2/ja

Status Active legal-status Critical Current

2034-10-14 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 7
-1 methoxy, ethoxy Chemical group 0.000 claims 80
150000003839 salts Chemical class 0.000 claims 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
LSNOAQQZECGQNS-UHFFFAOYSA-N morpholine-2-carboxamide Chemical compound NC(=O)C1CNCCO1 LSNOAQQZECGQNS-UHFFFAOYSA-N 0.000 claims 15
239000008194 pharmaceutical composition Substances 0.000 claims 15
101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims 8
CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
125000003386 piperidinyl group Chemical group 0.000 claims 7
230000003042 antagnostic effect Effects 0.000 claims 6
206010025135 lupus erythematosus Diseases 0.000 claims 6
UJWGIIHZXUTSNZ-UHFFFAOYSA-N morpholine-2-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1CNCCO1 UJWGIIHZXUTSNZ-UHFFFAOYSA-N 0.000 claims 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
125000004076 pyridyl group Chemical group 0.000 claims 5
229920006395 saturated elastomer Polymers 0.000 claims 5
102100039390 Toll-like receptor 7 Human genes 0.000 claims 4
102000045715 human TLR7 Human genes 0.000 claims 4
NDFGDMVVBHWEPZ-DGCLKSJQSA-N 5-[(2R,6R)-2-formyl-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C=O)c1ccc(C#N)c2ncccc12 NDFGDMVVBHWEPZ-DGCLKSJQSA-N 0.000 claims 3
ROBOGRVDICNRNY-TXEJJXNPSA-N 5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 ROBOGRVDICNRNY-TXEJJXNPSA-N 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 claims 3
206010063663 Neuropsychiatric lupus Diseases 0.000 claims 3
102100033110 Toll-like receptor 8 Human genes 0.000 claims 3
229910052799 carbon Inorganic materials 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
125000000753 cycloalkyl group Chemical group 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
CZWLZIXSFOUABB-UWJPMSJPSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(3S,4R)-4-fluoropyrrolidin-3-yl]-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H]1CNC[C@H]1F)c1ccc(C#N)c2ncccc12 CZWLZIXSFOUABB-UWJPMSJPSA-N 0.000 claims 2
QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical group C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims 2
MGRZCFGYLQCOIY-TZMCWYRMSA-N 5-[(2R,7R)-2-(hydroxymethyl)-7-methyl-1,4-oxazepan-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CCN(C[C@H](CO)O1)c1ccc(C#N)c2ncccc12 MGRZCFGYLQCOIY-TZMCWYRMSA-N 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
125000004193 piperazinyl group Chemical group 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
125000003944 tolyl group Chemical group 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
IVCSMXVHRZGSBM-IAQYHMDHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1,2,4-thiadiazol-5-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)Nc1ncns1)c1ccc(C#N)c2ncccc12 IVCSMXVHRZGSBM-IAQYHMDHSA-N 0.000 claims 1
RCQNCJWXCRHGNB-ZSGSICDHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1-methylazepan-3-yl)morpholine-2-carboxamide hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)NC1CCCCN(C)C1)c1ccc(C#N)c2ncccc12 RCQNCJWXCRHGNB-ZSGSICDHSA-N 0.000 claims 1
BKPTXEHTXHDIIF-JNEOBVTJSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1-methylazepan-4-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1CCCN(C)CC1)c1ccc(C#N)c2ncccc12 BKPTXEHTXHDIIF-JNEOBVTJSA-N 0.000 claims 1
XNYWZLMTRNSWHZ-FOIQADDNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1-methylpiperidin-4-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1CCN(C)CC1)c1ccc(C#N)c2ncccc12 XNYWZLMTRNSWHZ-FOIQADDNSA-N 0.000 claims 1
ZANMOJVKNKAAKY-FZKQIMNGSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1H-pyrazol-4-ylmethyl)morpholine-2-carboxamide Chemical compound N1N=CC(=C1)CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N ZANMOJVKNKAAKY-FZKQIMNGSA-N 0.000 claims 1
QSSPNEXSZOSGID-FZKQIMNGSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(1H-pyrazol-5-ylmethyl)morpholine-2-carboxamide Chemical compound N1N=CC=C1CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N QSSPNEXSZOSGID-FZKQIMNGSA-N 0.000 claims 1
VBLSBIOOIVXEIT-IAQYHMDHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(2,2,2-trifluoroethyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(F)(F)F)c1ccc(C#N)c2ncccc12 VBLSBIOOIVXEIT-IAQYHMDHSA-N 0.000 claims 1
PXJHSYMWFXVUCM-VGOFRKELSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(2-phenoxyethyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCOc1ccccc1)c1ccc(C#N)c2ncccc12 PXJHSYMWFXVUCM-VGOFRKELSA-N 0.000 claims 1
AMQTYCLRMXAEQM-ZAZMHIJSSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(2-phenoxypropyl)morpholine-2-carboxamide Chemical compound CC(CNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12)Oc1ccccc1 AMQTYCLRMXAEQM-ZAZMHIJSSA-N 0.000 claims 1
QMAFGCKVENUQTG-DNVCBOLYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(2-propan-2-yloxyethyl)morpholine-2-carboxamide Chemical compound CC(C)OCCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 QMAFGCKVENUQTG-DNVCBOLYSA-N 0.000 claims 1
DZZVUVGEIVXNGG-DNVCBOLYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(2-propoxyethyl)morpholine-2-carboxamide Chemical compound CCCOCCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 DZZVUVGEIVXNGG-DNVCBOLYSA-N 0.000 claims 1
SMNUDILIPZQSMU-MLGOLLRUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(3,3,3-trifluoropropyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCC(F)(F)F)c1ccc(C#N)c2ncccc12 SMNUDILIPZQSMU-MLGOLLRUSA-N 0.000 claims 1
JXGJTALKZXLZCD-BDJLRTHQSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(3-methyl-1,2,4-thiadiazol-5-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)Nc1nc(C)ns1)c1ccc(C#N)c2ncccc12 JXGJTALKZXLZCD-BDJLRTHQSA-N 0.000 claims 1
AXRZHCWNEVLRJC-DNVCBOLYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(6-methylpyridin-2-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)Nc1cccc(C)n1)c1ccc(C#N)c2ncccc12 AXRZHCWNEVLRJC-DNVCBOLYSA-N 0.000 claims 1
BAFQSXCDDOACSR-JGNDPHQUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(oxetan-2-ylmethyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1CCO1)c1ccc(C#N)c2ncccc12 BAFQSXCDDOACSR-JGNDPHQUSA-N 0.000 claims 1
YPUMSWOBKFRGIU-SJKOYZFVSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(oxetan-3-yl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1COC1)c1ccc(C#N)c2ncccc12 YPUMSWOBKFRGIU-SJKOYZFVSA-N 0.000 claims 1
CMEWJSTZNOCOEP-FZKQIMNGSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(oxetan-3-ylmethyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1COC1)c1ccc(C#N)c2ncccc12 CMEWJSTZNOCOEP-FZKQIMNGSA-N 0.000 claims 1
IFSJSHOQGQHRLY-FOIQADDNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-(pyridin-2-ylmethyl)morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCc1ccccn1)c1ccc(C#N)c2ncccc12 IFSJSHOQGQHRLY-FOIQADDNSA-N 0.000 claims 1
CYQALEQUHFTONN-JNEOBVTJSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[(1-methylpiperidin-2-yl)methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1CCCCN1C)c1ccc(C#N)c2ncccc12 CYQALEQUHFTONN-JNEOBVTJSA-N 0.000 claims 1
JJLPTCFBJVFCKE-RDTXWAMCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[(3-methyloxetan-3-yl)methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1(C)COC1)c1ccc(C#N)c2ncccc12 JJLPTCFBJVFCKE-RDTXWAMCSA-N 0.000 claims 1
IEFINSXGKIVSGA-IIBYNOLFSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[(3-methylpyridin-2-yl)methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCc1ncccc1C)c1ccc(C#N)c2ncccc12 IEFINSXGKIVSGA-IIBYNOLFSA-N 0.000 claims 1
LKMNUDHBTRKEIY-QMBUQHDCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[(4-methylmorpholin-2-yl)methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1CN(C)CCO1)c1ccc(C#N)c2ncccc12 LKMNUDHBTRKEIY-QMBUQHDCSA-N 0.000 claims 1
FSPNWTOJKDWBHV-IIBYNOLFSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[(6-methylpyridin-2-yl)methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCc1cccc(C)n1)c1ccc(C#N)c2ncccc12 FSPNWTOJKDWBHV-IIBYNOLFSA-N 0.000 claims 1
KONRFMWBSLLHQU-CXAGYDPISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[2-(methylamino)ethyl]morpholine-2-carboxamide Chemical compound CNCCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 KONRFMWBSLLHQU-CXAGYDPISA-N 0.000 claims 1
RCNORTFNEGVNDV-MXHNKVEKSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[[(2R,6R)-6-methylmorpholin-2-yl]methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CNC[C@H](CNC(=O)[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)O1 RCNORTFNEGVNDV-MXHNKVEKSA-N 0.000 claims 1
KLGIQPVZIFLVOH-JLTOFOAXSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methyl]morpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCc1ncccc1C(F)(F)F)c1ccc(C#N)c2ncccc12 KLGIQPVZIFLVOH-JLTOFOAXSA-N 0.000 claims 1
VDCTVMISAJVTDO-CXAGYDPISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methyl-N-propan-2-ylmorpholine-2-carboxamide Chemical compound CC(C)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 VDCTVMISAJVTDO-CXAGYDPISA-N 0.000 claims 1
ZFTCTRKCXIWNEJ-SJKOYZFVSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(1,3-dihydroxypropan-2-yl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC(CO)CO)c1ccc(C#N)c2ncccc12 ZFTCTRKCXIWNEJ-SJKOYZFVSA-N 0.000 claims 1
LGELMLJULDBHOP-OXQOHEQNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(1,4-dimethylpiperidin-4-yl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1(C)CCN(C)CC1)c1ccc(C#N)c2ncccc12 LGELMLJULDBHOP-OXQOHEQNSA-N 0.000 claims 1
POUQKOPBKOPIFD-JNEOBVTJSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(1-ethylpiperidin-3-yl)-6-methylmorpholine-2-carboxamide Chemical compound CCN1CCCC(C1)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 POUQKOPBKOPIFD-JNEOBVTJSA-N 0.000 claims 1
IKGVDGXUJOEPBS-IIBYNOLFSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(1-ethylpiperidin-4-yl)-6-methylmorpholine-2-carboxamide Chemical compound CCN1CCC(CC1)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 IKGVDGXUJOEPBS-IIBYNOLFSA-N 0.000 claims 1
PHJRYXNTRUFVON-QMBUQHDCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(1-hydroxyhexan-2-yl)-6-methylmorpholine-2-carboxamide Chemical compound CCCCC(CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 PHJRYXNTRUFVON-QMBUQHDCSA-N 0.000 claims 1
WXXKOTUEKNYQOD-IAQYHMDHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2,2-difluoroethyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(F)F)c1ccc(C#N)c2ncccc12 WXXKOTUEKNYQOD-IAQYHMDHSA-N 0.000 claims 1
AGNSCGDRRRKUMQ-CXAGYDPISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2,2-dimethoxyethyl)-6-methylmorpholine-2-carboxamide Chemical compound COC(CNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12)OC AGNSCGDRRRKUMQ-CXAGYDPISA-N 0.000 claims 1
ZBPOYCVJGWULMA-ZYFOBHMOSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2,3-dihydroxypropyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)CO)c1ccc(C#N)c2ncccc12 ZBPOYCVJGWULMA-ZYFOBHMOSA-N 0.000 claims 1
NOHWDEQAEVEAAE-RDTXWAMCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2,5-dimethylpyrazol-3-yl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)Nc1cc(C)nn1C)c1ccc(C#N)c2ncccc12 NOHWDEQAEVEAAE-RDTXWAMCSA-N 0.000 claims 1
PFIJCZMWPMCDQE-RDTXWAMCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-ethoxyethyl)-6-methylmorpholine-2-carboxamide Chemical compound CCOCCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 PFIJCZMWPMCDQE-RDTXWAMCSA-N 0.000 claims 1
ZMSPCDYNWSWMAH-MLGOLLRUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-fluoroethyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCF)c1ccc(C#N)c2ncccc12 ZMSPCDYNWSWMAH-MLGOLLRUSA-N 0.000 claims 1
STENRCIBAFITNP-QKLBRSPYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxy-3-phenoxypropyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)COc1ccccc1)c1ccc(C#N)c2ncccc12 STENRCIBAFITNP-QKLBRSPYSA-N 0.000 claims 1
YTWGATJHQHIWRI-LRRFZDQKSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxy-3-phenylpropyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)Cc1ccccc1)c1ccc(C#N)c2ncccc12 YTWGATJHQHIWRI-LRRFZDQKSA-N 0.000 claims 1
QOJMXDCFBYCPMN-JNEOBVTJSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxy-3-piperazin-1-ylpropyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)CN1CCNCC1)c1ccc(C#N)c2ncccc12 QOJMXDCFBYCPMN-JNEOBVTJSA-N 0.000 claims 1
ZRLRCQYXPSMFKK-JGNDPHQUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxybutyl)-6-methylmorpholine-2-carboxamide Chemical compound CCC(O)CNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 ZRLRCQYXPSMFKK-JGNDPHQUSA-N 0.000 claims 1
KFADRJNGXYJZMT-NJBLAONRSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxycyclohexyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1CCCCC1O)c1ccc(C#N)c2ncccc12 KFADRJNGXYJZMT-NJBLAONRSA-N 0.000 claims 1
MSERRFNCSWZVLP-MLGOLLRUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-hydroxyethyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCO)c1ccc(C#N)c2ncccc12 MSERRFNCSWZVLP-MLGOLLRUSA-N 0.000 claims 1
XNIUHVCPRMVFGY-CXAGYDPISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(2-methoxyethyl)-6-methylmorpholine-2-carboxamide Chemical compound COCCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 XNIUHVCPRMVFGY-CXAGYDPISA-N 0.000 claims 1
UWZNQDLJHXILAT-DORBDNKASA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(3,4-dihydro-1H-isochromen-1-ylmethyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1OCCc2ccccc12)c1ccc(C#N)c2ncccc12 UWZNQDLJHXILAT-DORBDNKASA-N 0.000 claims 1
OZQZSLWIGYBZRN-CXAGYDPISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-(3-fluoropropyl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCCF)c1ccc(C#N)c2ncccc12 OZQZSLWIGYBZRN-CXAGYDPISA-N 0.000 claims 1
QBXCMPYYIKLVOQ-QGCDCVKKSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(1R)-2-hydroxy-1-phenylethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@@H](CO)c1ccccc1)c1ccc(C#N)c2ncccc12 QBXCMPYYIKLVOQ-QGCDCVKKSA-N 0.000 claims 1
XSDJYFXLCNLARB-FMQLPVHYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(1S)-1,3-dihydroxy-1-phenylpropan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC(CO)[C@@H](O)c1ccccc1)c1ccc(C#N)c2ncccc12 XSDJYFXLCNLARB-FMQLPVHYSA-N 0.000 claims 1
QBXCMPYYIKLVOQ-BSLALVQMSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(1S)-2-hydroxy-1-phenylethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H](CO)c1ccccc1)c1ccc(C#N)c2ncccc12 QBXCMPYYIKLVOQ-BSLALVQMSA-N 0.000 claims 1
NRLZLHMQCMCXEG-IALYEVHXSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H](NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12)[C@@H](O)c1ccc(O)cc1 NRLZLHMQCMCXEG-IALYEVHXSA-N 0.000 claims 1
KFADRJNGXYJZMT-PEFDPPPMSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(1S,2S)-2-hydroxycyclohexyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H]1CCCC[C@@H]1O)c1ccc(C#N)c2ncccc12 KFADRJNGXYJZMT-PEFDPPPMSA-N 0.000 claims 1
YRHCQJYSGHRTHI-DKSSEZFCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-1-hydroxy-3-methylbutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC(C)[C@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 YRHCQJYSGHRTHI-DKSSEZFCSA-N 0.000 claims 1
BZTTWWVUCQFGSE-WRWLIDTKSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-1-hydroxy-4-methylpentan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC(C)C[C@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 BZTTWWVUCQFGSE-WRWLIDTKSA-N 0.000 claims 1
KCCCRZNMWVIJGD-DDUZABMNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-1-hydroxybutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC[C@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 KCCCRZNMWVIJGD-DDUZABMNSA-N 0.000 claims 1
VZNAVEXLEPIYKB-IDHHARJASA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-1-hydroxypentan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CCC[C@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 VZNAVEXLEPIYKB-IDHHARJASA-N 0.000 claims 1
SDWUIMNFSHXAME-PBFPGSCMSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-1-hydroxypropan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 SDWUIMNFSHXAME-PBFPGSCMSA-N 0.000 claims 1
SILVWDKTVXTNMS-PBFPGSCMSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2R)-2-hydroxypropyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H](O)CNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 SILVWDKTVXTNMS-PBFPGSCMSA-N 0.000 claims 1
ROLRUTLYNAOGQH-DHJUGAMNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-cyclohexyl-3-hydroxypropan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H](CO)CC1CCCCC1)c1ccc(C#N)c2ncccc12 ROLRUTLYNAOGQH-DHJUGAMNSA-N 0.000 claims 1
SNXJLUGVKDWCGQ-NIKGAXFTSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H](CO)C(C)(C)C)c1ccc(C#N)c2ncccc12 SNXJLUGVKDWCGQ-NIKGAXFTSA-N 0.000 claims 1
YRHCQJYSGHRTHI-LSBZLQRGSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC(C)[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 YRHCQJYSGHRTHI-LSBZLQRGSA-N 0.000 claims 1
GNPJUEBZOMMKRO-DHJUGAMNSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H](CO)Cc1ccccc1)c1ccc(C#N)c2ncccc12 GNPJUEBZOMMKRO-DHJUGAMNSA-N 0.000 claims 1
BZTTWWVUCQFGSE-OXFYSEKESA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxy-4-methylpentan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC(C)C[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 BZTTWWVUCQFGSE-OXFYSEKESA-N 0.000 claims 1
JZDVLHCVSIRBBH-SIXWZSSISA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxy-4-methylsulfanylbutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CSCC[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 JZDVLHCVSIRBBH-SIXWZSSISA-N 0.000 claims 1
KCCCRZNMWVIJGD-QIIPPGSGSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxybutan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 KCCCRZNMWVIJGD-QIIPPGSGSA-N 0.000 claims 1
PHJRYXNTRUFVON-OXFYSEKESA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxyhexan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CCCC[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 PHJRYXNTRUFVON-OXFYSEKESA-N 0.000 claims 1
SDWUIMNFSHXAME-OGHNNQOOSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S)-1-hydroxypropan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 SDWUIMNFSHXAME-OGHNNQOOSA-N 0.000 claims 1
CHDPFKNRSORUPS-QHDJUILOSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(2S,3S)-1-hydroxy-3-methylpentan-2-yl]-6-methylmorpholine-2-carboxamide Chemical compound CC[C@H](C)[C@@H](CO)NC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 CHDPFKNRSORUPS-QHDJUILOSA-N 0.000 claims 1
FGBGSYYEELCPJT-SPLOXXLWSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(3,4-difluorophenyl)methyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCc1ccc(F)c(F)c1)c1ccc(C#N)c2ncccc12 FGBGSYYEELCPJT-SPLOXXLWSA-N 0.000 claims 1
FZHBWHCAKGBCNC-UEILYKACSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(3S,4R)-4-fluoro-1-methylpyrrolidin-3-yl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H]1CN(C)C[C@H]1F)c1ccc(C#N)c2ncccc12 FZHBWHCAKGBCNC-UEILYKACSA-N 0.000 claims 1
KDRMPEKCDDELBA-VFEPQSPHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(3S,4R)-4-fluoropiperidin-3-yl]-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N[C@H]1CNCC[C@H]1F)c1ccc(C#N)c2ncccc12 KDRMPEKCDDELBA-VFEPQSPHSA-N 0.000 claims 1
LQIOPVGTDYKTPD-UICIEZGTSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(3S,4R)-4-fluoropiperidin-3-yl]-N,6-dimethylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N(C)[C@H]1CNCC[C@H]1F)c1ccc(C#N)c2ncccc12 LQIOPVGTDYKTPD-UICIEZGTSA-N 0.000 claims 1
YUHCMVLYOCHXAC-AEFICSSHSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[(4-fluoropiperidin-4-yl)methyl]-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)NCC1(F)CCNCC1)c1ccc(C#N)c2ncccc12 YUHCMVLYOCHXAC-AEFICSSHSA-N 0.000 claims 1
CAKIQGCJVAUXPK-WWFGYZFLSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(2-fluorophenyl)-2-hydroxyethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)c1ccccc1F)c1ccc(C#N)c2ncccc12 CAKIQGCJVAUXPK-WWFGYZFLSA-N 0.000 claims 1
UNKGICZBNPPIDB-RDTXWAMCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(2-hydroxyethoxy)ethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCOCCO)c1ccc(C#N)c2ncccc12 UNKGICZBNPPIDB-RDTXWAMCSA-N 0.000 claims 1
XKAATRUXXLPODR-WWFGYZFLSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(3-fluorophenyl)-2-hydroxyethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(O)c1cccc(F)c1)c1ccc(C#N)c2ncccc12 XKAATRUXXLPODR-WWFGYZFLSA-N 0.000 claims 1
HYTLCTYUVFKFKG-OPAMFIHVSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(4-fluorophenoxy)ethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCOc1ccc(F)cc1)c1ccc(C#N)c2ncccc12 HYTLCTYUVFKFKG-OPAMFIHVSA-N 0.000 claims 1
QPLQGEXIMLWHIE-DNVCBOLYSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(dimethylamino)-2-methylpropyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCC(C)(C)N(C)C)c1ccc(C#N)c2ncccc12 QPLQGEXIMLWHIE-DNVCBOLYSA-N 0.000 claims 1
SNEKHSBYKQEVIQ-RDTXWAMCSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[2-(dimethylamino)ethyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NCCN(C)C)c1ccc(C#N)c2ncccc12 SNEKHSBYKQEVIQ-RDTXWAMCSA-N 0.000 claims 1
NLWNKBXAXVQVJA-KALAIVBUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-[[(2S,6R)-4,6-dimethylmorpholin-2-yl]methyl]-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C)C[C@H](CNC(=O)[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)O1 NLWNKBXAXVQVJA-KALAIVBUSA-N 0.000 claims 1
QTBUBPHGJUEFTA-SJKOYZFVSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-cyclopropyl-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)NC1CC1)c1ccc(C#N)c2ncccc12 QTBUBPHGJUEFTA-SJKOYZFVSA-N 0.000 claims 1
XKEZRILRHNXXHQ-MLGOLLRUSA-N (2R,6R)-4-(8-cyanoquinolin-5-yl)-N-ethyl-6-methylmorpholine-2-carboxamide Chemical compound CCNC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 XKEZRILRHNXXHQ-MLGOLLRUSA-N 0.000 claims 1
FKPXIFSRYLSSPT-CXAGYDPISA-N (2R,6R)-N-(1-cyanocyclopropyl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(#N)C1(CC1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N FKPXIFSRYLSSPT-CXAGYDPISA-N 0.000 claims 1
QQJWMHQVDXDCGL-CXAGYDPISA-N (2R,6R)-N-(2-amino-2-methylpropyl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound NC(CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N)(C)C QQJWMHQVDXDCGL-CXAGYDPISA-N 0.000 claims 1
MRDDWPWKWXYWAF-NXDRBNLFSA-N (2R,6R)-N-(2-carbamoylpyridin-4-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.C(N)(=O)C1=NC=CC(=C1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N MRDDWPWKWXYWAF-NXDRBNLFSA-N 0.000 claims 1
CCSBNOZESIIXPN-ZJPCWUBNSA-N (2R,6R)-N-(3-amino-4,4,4-trifluorobutyl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound NC(CCNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N)C(F)(F)F CCSBNOZESIIXPN-ZJPCWUBNSA-N 0.000 claims 1
UATDUSPPADMZCN-SJKOYZFVSA-N (2R,6R)-N-(3-carbamoyl-1-methylpyrazol-4-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(N)(=O)C1=NN(C=C1NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N)C UATDUSPPADMZCN-SJKOYZFVSA-N 0.000 claims 1
GSANDVSWJVUMHM-BFUOFWGJSA-N (2R,6R)-N-(3-carbamoylpyridin-4-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(N)(=O)C=1C=NC=CC1NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N GSANDVSWJVUMHM-BFUOFWGJSA-N 0.000 claims 1
RJFNWPNTCJYMCF-SJKOYZFVSA-N (2R,6R)-N-(4-cyano-1H-pyrazol-5-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(#N)C=1C(=NNC1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N RJFNWPNTCJYMCF-SJKOYZFVSA-N 0.000 claims 1
FRBDXELQZOPHDU-DFOOQVQUSA-N (2R,6R)-N-(azepan-3-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.N1CC(CCCC1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N FRBDXELQZOPHDU-DFOOQVQUSA-N 0.000 claims 1
OTYVGODRMHAIOX-DFOOQVQUSA-N (2R,6R)-N-(azepan-4-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.N1CCC(CCC1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N OTYVGODRMHAIOX-DFOOQVQUSA-N 0.000 claims 1
AHELZVUGSRFCSE-SJKOYZFVSA-N (2R,6R)-N-(azetidin-3-yl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound N1CC(C1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N AHELZVUGSRFCSE-SJKOYZFVSA-N 0.000 claims 1
OIRQZYMKVYHPLC-QRGZVCNKSA-N (2R,6R)-N-(azetidin-3-ylmethyl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.N1CC(C1)CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N OIRQZYMKVYHPLC-QRGZVCNKSA-N 0.000 claims 1
JUGQPQOGNUMIHM-MLGOLLRUSA-N (2R,6R)-N-(cyanomethyl)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(#N)CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N JUGQPQOGNUMIHM-MLGOLLRUSA-N 0.000 claims 1
HDBIWAVWVYXGPV-FOIQADDNSA-N (2R,6R)-N-[1-(2-amino-2-oxoethyl)piperidin-4-yl]-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound NC(CN1CCC(CC1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N)=O HDBIWAVWVYXGPV-FOIQADDNSA-N 0.000 claims 1
LMDIJYKQAIRDQO-DXPOFMJKSA-N (2R,6R)-N-[1-(azetidin-3-yl)pyrazol-4-yl]-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide hydrochloride Chemical compound Cl.N1CC(C1)N1N=CC(=C1)NC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N LMDIJYKQAIRDQO-DXPOFMJKSA-N 0.000 claims 1
MACTUHZELBFXGS-WZONZLPQSA-N (2R,6R)-N-[2-(benzylamino)ethyl]-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C(C1=CC=CC=C1)NCCNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N MACTUHZELBFXGS-WZONZLPQSA-N 0.000 claims 1
PIFSVTQUOAWMIJ-RDTXWAMCSA-N (2R,6R)-N-[[3-(aminomethyl)oxetan-3-yl]methyl]-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound NCC1(COC1)CNC(=O)[C@H]1CN(C[C@H](O1)C)C1=C2C=CC=NC2=C(C=C1)C#N PIFSVTQUOAWMIJ-RDTXWAMCSA-N 0.000 claims 1
CWCAKKZSMAHRPR-AOOOYVTPSA-N (2R,6S)-4-(8-chloro-1,7-naphthyridin-5-yl)-2,6-dimethylmorpholine Chemical compound C[C@H]1CN(C[C@@H](C)O1)c1cnc(Cl)c2ncccc12 CWCAKKZSMAHRPR-AOOOYVTPSA-N 0.000 claims 1
HXKFVVSVGBWHHW-TXEJJXNPSA-N (2R,6S)-4-(8-methoxyquinolin-5-yl)-2,6-dimethylmorpholine Chemical compound COc1ccc(N2C[C@H](C)O[C@H](C)C2)c2cccnc12 HXKFVVSVGBWHHW-TXEJJXNPSA-N 0.000 claims 1
TWWBPSSLRHVDDF-IAPIXIRKSA-N (6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxamide Chemical compound C[C@@H]1CN(CC(O1)C(N)=O)c1ccc(C#N)c2ncccc12 TWWBPSSLRHVDDF-IAPIXIRKSA-N 0.000 claims 1
XJMZRAQWRXKVRQ-XLIONFOSSA-N 1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]-N-ethylpiperidine-4-carboxamide Chemical compound CCNC(=O)C1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 XJMZRAQWRXKVRQ-XLIONFOSSA-N 0.000 claims 1
GCHZMBLHCOXKGC-XLCHORMMSA-N 1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]-N-ethylpiperidine-4-carboxamide hydrochloride Chemical compound Cl.CCNC(=O)C1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 GCHZMBLHCOXKGC-XLCHORMMSA-N 0.000 claims 1
VZYQABVHRQWCHL-QAPCUYQASA-N 1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidine-4-carboxamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C(N)=O)O1)c1ccc(C#N)c2ncccc12 VZYQABVHRQWCHL-QAPCUYQASA-N 0.000 claims 1
HUZUKTHEZXDOIM-IWKKHLOMSA-N 2,3-dihydroxybutanedioic acid 5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 HUZUKTHEZXDOIM-IWKKHLOMSA-N 0.000 claims 1
ZXUICRDVIUWNIY-UHFFFAOYSA-N 2-methyl-1-piperidin-4-ylpiperidine Chemical group CC1CCCCN1C1CCNCC1 ZXUICRDVIUWNIY-UHFFFAOYSA-N 0.000 claims 1
BZYWKSUQOSFTCK-QPPBQGQZSA-N 2-methyl-5-[(2R,6S)-2-methyl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCCC2)O1)c1ccc(C#N)c2nc(C)ccc12 BZYWKSUQOSFTCK-QPPBQGQZSA-N 0.000 claims 1
FVDGRWITZVZGTG-WBVHZDCISA-N 4-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperazine-1-carboxamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C(N)=O)O1)c1ccc(C#N)c2ncccc12 FVDGRWITZVZGTG-WBVHZDCISA-N 0.000 claims 1
SYNXGAXPNPLEFM-UHFFFAOYSA-N 5-(3-formyl-5-methylphenyl)quinoline-8-carbonitrile Chemical compound Cc1cc(C=O)cc(c1)-c1ccc(C#N)c2ncccc12 SYNXGAXPNPLEFM-UHFFFAOYSA-N 0.000 claims 1
ADRIIJTVVHBUDT-JUFGAKHDSA-N 5-[(2R,6R)-2-(1,7-diazaspiro[3.4]octane-1-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC11CCNC1)c1ccc(C#N)c2ncccc12 ADRIIJTVVHBUDT-JUFGAKHDSA-N 0.000 claims 1
YJLVFECARCCCNI-MTXUOHNVSA-N 5-[(2R,6R)-2-(1,7-diazaspiro[4.4]nonane-7-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC2(CCCN2)C1)c1ccc(C#N)c2ncccc12 YJLVFECARCCCNI-MTXUOHNVSA-N 0.000 claims 1
ICVOYQUVVKQYGL-SCWIMFDPSA-N 5-[(2R,6R)-2-(1-hydroxypropyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCC(O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 ICVOYQUVVKQYGL-SCWIMFDPSA-N 0.000 claims 1
VNZYHZOROZAAHM-SPTDJYCLSA-N 5-[(2R,6R)-2-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC2CNCC2C1)c1ccc(C#N)c2ncccc12 VNZYHZOROZAAHM-SPTDJYCLSA-N 0.000 claims 1
NQZKGFYMGWOZBI-AEFICSSHSA-N 5-[(2R,6R)-2-(2,7-diazaspiro[3.4]octane-2-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC2(C1)CCNC2)c1ccc(C#N)c2ncccc12 NQZKGFYMGWOZBI-AEFICSSHSA-N 0.000 claims 1
SJYBYUWNHYDSQA-MTXUOHNVSA-N 5-[(2R,6R)-2-(2,7-diazaspiro[4.4]nonane-2-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC2(CCNC2)C1)c1ccc(C#N)c2ncccc12 SJYBYUWNHYDSQA-MTXUOHNVSA-N 0.000 claims 1
UIHKNPHMECWYSF-KYSFMIDTSA-N 5-[(2R,6R)-2-(2,8-diazaspiro[3.5]nonane-2-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC2(C1)CCCNC2)c1ccc(C#N)c2ncccc12 UIHKNPHMECWYSF-KYSFMIDTSA-N 0.000 claims 1
MOCIPFDFRMIGDO-TVNLMDKXSA-N 5-[(2R,6R)-2-(3,9-diazaspiro[5.5]undecane-3-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC2(CCNCC2)CC1)c1ccc(C#N)c2ncccc12 MOCIPFDFRMIGDO-TVNLMDKXSA-N 0.000 claims 1
FNPDIYNOAIVNPY-SJKOYZFVSA-N 5-[(2R,6R)-2-(3-aminoazetidine-1-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC(N)C1)c1ccc(C#N)c2ncccc12 FNPDIYNOAIVNPY-SJKOYZFVSA-N 0.000 claims 1
XAXOATMFUBAWQR-DNVCBOLYSA-N 5-[(2R,6R)-2-(4-amino-4-methylpiperidine-1-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC(C)(N)CC1)c1ccc(C#N)c2ncccc12 XAXOATMFUBAWQR-DNVCBOLYSA-N 0.000 claims 1
WTYAYGCQQSONNL-AUUYWEPGSA-N 5-[(2R,6R)-2-(4-aminopiperidine-1-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC(N)CC1)c1ccc(C#N)c2ncccc12 WTYAYGCQQSONNL-AUUYWEPGSA-N 0.000 claims 1
HDHMKJPPYVBMQY-CXAGYDPISA-N 5-[(2R,6R)-2-(azetidine-1-carbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC1)c1ccc(C#N)c2ncccc12 HDHMKJPPYVBMQY-CXAGYDPISA-N 0.000 claims 1
GKRXTSOLINCJFJ-YPMHNXCESA-N 5-[(2R,6R)-2-(chloromethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CCl)O1)c1ccc(C#N)c2ncccc12 GKRXTSOLINCJFJ-YPMHNXCESA-N 0.000 claims 1
FOLFLNDGCVPUEU-FOIQADDNSA-N 5-[(2R,6R)-2-(cyclohexanecarbonyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)C1CCCCC1)c1ccc(C#N)c2ncccc12 FOLFLNDGCVPUEU-FOIQADDNSA-N 0.000 claims 1
ZDTZTRZLFHWNAW-YLJYHZDGSA-N 5-[(2R,6R)-2-(cyclohexylmethoxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COCC2CCCCC2)O1)c1ccc(C#N)c2ncccc12 ZDTZTRZLFHWNAW-YLJYHZDGSA-N 0.000 claims 1
BYFKWEOLOKUGOW-UKRRQHHQSA-N 5-[(2R,6R)-2-(ethoxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCOC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 BYFKWEOLOKUGOW-UKRRQHHQSA-N 0.000 claims 1
WPTBOUKXAITFTJ-YPMHNXCESA-N 5-[(2R,6R)-2-(fluoromethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CF)O1)c1ccc(C#N)c2ncccc12 WPTBOUKXAITFTJ-YPMHNXCESA-N 0.000 claims 1
MBUCCYMQULHCQH-IEBWSBKVSA-N 5-[(2R,6R)-2-(hexoxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCCCCCOC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MBUCCYMQULHCQH-IEBWSBKVSA-N 0.000 claims 1
ZVVCTRLPKFKYHB-DGCLKSJQSA-N 5-[(2R,6R)-2-(hydroxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CO)O1)c1ccc(C#N)c2ncccc12 ZVVCTRLPKFKYHB-DGCLKSJQSA-N 0.000 claims 1
LGDGBWGGJVGAJO-TZMCWYRMSA-N 5-[(2R,6R)-2-(methoxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound COC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 LGDGBWGGJVGAJO-TZMCWYRMSA-N 0.000 claims 1
QRBIFNLILORNGZ-NPFVIJTESA-N 5-[(2R,6R)-2-[(1R)-1-hydroxy-2-phenylethyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@H](O)Cc1ccccc1)c1ccc(C#N)c2ncccc12 QRBIFNLILORNGZ-NPFVIJTESA-N 0.000 claims 1
XQBPJWGNRMEKMB-NLSFWIRASA-N 5-[(2R,6R)-2-[(1R)-1-hydroxy-3-phenylpropyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@H](O)CCc1ccccc1)c1ccc(C#N)c2ncccc12 XQBPJWGNRMEKMB-NLSFWIRASA-N 0.000 claims 1
ATOYKLASRRVNEY-XHBSWPGZSA-N 5-[(2R,6R)-2-[(1R)-1-hydroxyethyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H](O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 ATOYKLASRRVNEY-XHBSWPGZSA-N 0.000 claims 1
MPFGZIQTDGJBDK-NIKGAXFTSA-N 5-[(2R,6R)-2-[(1R)-1-hydroxypentyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCCC[C@@H](O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MPFGZIQTDGJBDK-NIKGAXFTSA-N 0.000 claims 1
QRBIFNLILORNGZ-URZJWIJPSA-N 5-[(2R,6R)-2-[(1S)-1-hydroxy-2-phenylethyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@@H](O)Cc1ccccc1)c1ccc(C#N)c2ncccc12 QRBIFNLILORNGZ-URZJWIJPSA-N 0.000 claims 1
XQBPJWGNRMEKMB-MQNAVGNWSA-N 5-[(2R,6R)-2-[(1S)-1-hydroxy-3-phenylpropyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@@H](O)CCc1ccccc1)c1ccc(C#N)c2ncccc12 XQBPJWGNRMEKMB-MQNAVGNWSA-N 0.000 claims 1
ATOYKLASRRVNEY-BFQNTYOBSA-N 5-[(2R,6R)-2-[(1S)-1-hydroxyethyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H](O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 ATOYKLASRRVNEY-BFQNTYOBSA-N 0.000 claims 1
MPFGZIQTDGJBDK-MDASCCDHSA-N 5-[(2R,6R)-2-[(1S)-1-hydroxypentyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCCC[C@H](O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MPFGZIQTDGJBDK-MDASCCDHSA-N 0.000 claims 1
ZHNQXNGFJRELIR-AEFFLSMTSA-N 5-[(2R,6R)-2-[(2,2-dimethylpyrrolidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1(N(CCC1)C[C@H]1O[C@@H](CN(C1)C1=C2C=CC=NC2=C(C=C1)C#N)C)C ZHNQXNGFJRELIR-AEFFLSMTSA-N 0.000 claims 1
BWLOULDYMZIDFR-UYAOXDASSA-N 5-[(2R,6R)-2-[(2,6-dimethylphenoxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2c(C)cccc2C)O1)c1ccc(C#N)c2ncccc12 BWLOULDYMZIDFR-UYAOXDASSA-N 0.000 claims 1
AAHRDCUORPTGJB-NVXWUHKLSA-N 5-[(2R,6R)-2-[(2-fluorophenoxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ccccc2F)O1)c1ccc(C#N)c2ncccc12 AAHRDCUORPTGJB-NVXWUHKLSA-N 0.000 claims 1
UABHJIQMQDYPOR-RHSMWYFYSA-N 5-[(2R,6R)-2-[(3,4-difluorophenoxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ccc(F)c(F)c2)O1)c1ccc(C#N)c2ncccc12 UABHJIQMQDYPOR-RHSMWYFYSA-N 0.000 claims 1
FHMWVKNFGVQTNO-DNVCBOLYSA-N 5-[(2R,6R)-2-[(3-fluorophenoxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2cccc(F)c2)O1)c1ccc(C#N)c2ncccc12 FHMWVKNFGVQTNO-DNVCBOLYSA-N 0.000 claims 1
GLLOOQLSYAJRRP-QIIPPGSGSA-N 5-[(2R,6R)-2-[(3S)-3-aminopyrrolidine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC[C@H](N)C1)c1ccc(C#N)c2ncccc12 GLLOOQLSYAJRRP-QIIPPGSGSA-N 0.000 claims 1
QRWGPMYNXDSIFY-OXFYSEKESA-N 5-[(2R,6R)-2-[(3S)-3-ethylpiperazine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@H]1CN(CCN1)C(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 QRWGPMYNXDSIFY-OXFYSEKESA-N 0.000 claims 1
BTGWMZJAOPVTJQ-YLJYHZDGSA-N 5-[(2R,6R)-2-[(4-cyclohexyltriazol-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](Cn2cc(nn2)C2CCCCC2)O1)c1ccc(C#N)c2ncccc12 BTGWMZJAOPVTJQ-YLJYHZDGSA-N 0.000 claims 1
QXPFUQPQIGUOLT-RBQRDFNRSA-N 5-[(2R,6R)-2-[(R)-cyclohexyl(hydroxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@H](O)C1CCCCC1)c1ccc(C#N)c2ncccc12 QXPFUQPQIGUOLT-RBQRDFNRSA-N 0.000 claims 1
QXPFUQPQIGUOLT-QPJICYPMSA-N 5-[(2R,6R)-2-[(S)-cyclohexyl(hydroxy)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@@H](O)C1CCCCC1)c1ccc(C#N)c2ncccc12 QXPFUQPQIGUOLT-QPJICYPMSA-N 0.000 claims 1
GPEMZGOJQHDOBI-FZKQIMNGSA-N 5-[(2R,6R)-2-[3-(aminomethyl)azetidine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC(CN)C1)c1ccc(C#N)c2ncccc12 GPEMZGOJQHDOBI-FZKQIMNGSA-N 0.000 claims 1
MEFCXGDOZAVSBE-FOIQADDNSA-N 5-[(2R,6R)-2-[3-(ethylaminomethyl)azetidine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCNCC1CN(C1)C(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MEFCXGDOZAVSBE-FOIQADDNSA-N 0.000 claims 1
XNJPKNVAIWYDQJ-FOIQADDNSA-N 5-[(2R,6R)-2-[3-[(dimethylamino)methyl]azetidine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC(CN(C)C)C1)c1ccc(C#N)c2ncccc12 XNJPKNVAIWYDQJ-FOIQADDNSA-N 0.000 claims 1
WOKBSHXSCJEGNH-IIBYNOLFSA-N 5-[(2R,6R)-2-[4-(dimethylamino)piperidine-1-carbonyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC(CC1)N(C)C)c1ccc(C#N)c2ncccc12 WOKBSHXSCJEGNH-IIBYNOLFSA-N 0.000 claims 1
ZJARKWSNJDQCHJ-ZIAGYGMSSA-N 5-[(2R,6R)-2-ethyl-6-(hydroxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@@H]1CN(C[C@H](CO)O1)c1ccc(C#N)c2ncccc12 ZJARKWSNJDQCHJ-ZIAGYGMSSA-N 0.000 claims 1
PBICSPYZQQODDR-NHCUHLMSSA-N 5-[(2R,6R)-2-ethyl-6-(phenylmethoxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@@H]1CN(C[C@H](COCc2ccccc2)O1)c1ccc(C#N)c2ncccc12 PBICSPYZQQODDR-NHCUHLMSSA-N 0.000 claims 1
RFDYACRZJKBINE-NVXWUHKLSA-N 5-[(2R,6R)-2-methyl-6-(2-methylpropoxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)COC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 RFDYACRZJKBINE-NVXWUHKLSA-N 0.000 claims 1
ZFZIRSKLYBKNQZ-RDTXWAMCSA-N 5-[(2R,6R)-2-methyl-6-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CC2(COC2)C1)c1ccc(C#N)c2ncccc12 ZFZIRSKLYBKNQZ-RDTXWAMCSA-N 0.000 claims 1
UJHHSSKFNPQIBZ-UZUQRXQVSA-N 5-[(2R,6R)-2-methyl-6-(3-phenylpropanoyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)CCc1ccccc1)c1ccc(C#N)c2ncccc12 UJHHSSKFNPQIBZ-UZUQRXQVSA-N 0.000 claims 1
WGQYPGXGWQNIOL-NTKDMRAZSA-N 5-[(2R,6R)-2-methyl-6-(4-piperidin-1-ylpiperidine-1-carbonyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCC(CC1)N1CCCCC1)c1ccc(C#N)c2ncccc12 WGQYPGXGWQNIOL-NTKDMRAZSA-N 0.000 claims 1
SDBTXBFDXSRKAX-YLJYHZDGSA-N 5-[(2R,6R)-2-methyl-6-(phenylmethoxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COCc2ccccc2)O1)c1ccc(C#N)c2ncccc12 SDBTXBFDXSRKAX-YLJYHZDGSA-N 0.000 claims 1
MAFSBWBENIRRQF-KEZWHQCISA-N 5-[(2R,6R)-2-methyl-6-(piperazine-1-carbonyl)morpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.C[C@@H]1CN(C[C@@H](O1)C(=O)N1CCNCC1)c1ccc(C#N)c2ncccc12 MAFSBWBENIRRQF-KEZWHQCISA-N 0.000 claims 1
GAERNIWOALHHFO-GDBMZVCRSA-N 5-[(2R,6R)-2-methyl-6-(propan-2-yloxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)OC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 GAERNIWOALHHFO-GDBMZVCRSA-N 0.000 claims 1
UOPFPOKSYSUERL-GDBMZVCRSA-N 5-[(2R,6R)-2-methyl-6-(pyrazin-2-yloxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2cnccn2)O1)c1ccc(C#N)c2ncccc12 UOPFPOKSYSUERL-GDBMZVCRSA-N 0.000 claims 1
NNNUBIORVMHCIN-NVXWUHKLSA-N 5-[(2R,6R)-2-methyl-6-(pyridin-2-yloxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ccccn2)O1)c1ccc(C#N)c2ncccc12 NNNUBIORVMHCIN-NVXWUHKLSA-N 0.000 claims 1
FQCPQHGEKHLZOH-GDBMZVCRSA-N 5-[(2R,6R)-2-methyl-6-(pyrimidin-2-yloxymethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ncccn2)O1)c1ccc(C#N)c2ncccc12 FQCPQHGEKHLZOH-GDBMZVCRSA-N 0.000 claims 1
MZRBWWOLPQNYMA-SPYBWZPUSA-N 5-[(2R,6R)-2-methyl-6-[(1R)-1-pyrimidin-2-yloxyethyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H](Oc1ncccn1)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MZRBWWOLPQNYMA-SPYBWZPUSA-N 0.000 claims 1
VTRYBHZCBOFJIE-SACAOSOOSA-N 5-[(2R,6R)-2-methyl-6-[(1R)-3-phenyl-1-pyrrolidin-1-ylpropyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@@H](CCc1ccccc1)N1CCCC1)c1ccc(C#N)c2ncccc12 VTRYBHZCBOFJIE-SACAOSOOSA-N 0.000 claims 1
MZRBWWOLPQNYMA-ZRGWGRIASA-N 5-[(2R,6R)-2-methyl-6-[(1S)-1-pyrimidin-2-yloxyethyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H](Oc1ncccn1)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 MZRBWWOLPQNYMA-ZRGWGRIASA-N 0.000 claims 1
VTRYBHZCBOFJIE-COFKYPDJSA-N 5-[(2R,6R)-2-methyl-6-[(1S)-3-phenyl-1-pyrrolidin-1-ylpropyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@@H](O1)[C@H](CCc1ccccc1)N1CCCC1)c1ccc(C#N)c2ncccc12 VTRYBHZCBOFJIE-COFKYPDJSA-N 0.000 claims 1
YVFYYCSENIJBHS-IEBWSBKVSA-N 5-[(2R,6R)-2-methyl-6-[(2-methylphenoxy)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ccccc2C)O1)c1ccc(C#N)c2ncccc12 YVFYYCSENIJBHS-IEBWSBKVSA-N 0.000 claims 1
WBDZMEDHRBZMQD-YLJYHZDGSA-N 5-[(2R,6R)-2-methyl-6-[(3-methylphenoxy)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2cccc(C)c2)O1)c1ccc(C#N)c2ncccc12 WBDZMEDHRBZMQD-YLJYHZDGSA-N 0.000 claims 1
TTZXNYKKECYKOZ-YLJYHZDGSA-N 5-[(2R,6R)-2-methyl-6-[(4-methylphenoxy)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](COc2ccc(C)cc2)O1)c1ccc(C#N)c2ncccc12 TTZXNYKKECYKOZ-YLJYHZDGSA-N 0.000 claims 1
ZSVXIUYFKWMRIR-YLJYHZDGSA-N 5-[(2R,6R)-2-methyl-6-[(4-phenyltriazol-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](Cn2cc(nn2)-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 ZSVXIUYFKWMRIR-YLJYHZDGSA-N 0.000 claims 1
FKVNELJIICLGSA-HNJSCFAESA-N 5-[(2R,6R)-2-methyl-6-[3-(methylaminomethyl)azetidine-1-carbonyl]morpholin-4-yl]quinoline-8-carbonitrile hydrochloride Chemical compound Cl.CNCC1CN(C1)C(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 FKVNELJIICLGSA-HNJSCFAESA-N 0.000 claims 1
JYGCFFPADDOKDK-SJKOYZFVSA-N 5-[(2R,6R)-2-methyl-6-propanoylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 JYGCFFPADDOKDK-SJKOYZFVSA-N 0.000 claims 1
UEBAKFWDCRVTOV-GASCZTMLSA-N 5-[(2R,6S)-2,6-diethylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@H]1CN(C[C@@H](CC)O1)c1ccc(C#N)c2ncccc12 UEBAKFWDCRVTOV-GASCZTMLSA-N 0.000 claims 1
XKBWHMIKGMPQOI-FYPKGCJUSA-N 5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 XKBWHMIKGMPQOI-FYPKGCJUSA-N 0.000 claims 1
XDNBKNLQWNRHSL-FYPKGCJUSA-N 5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 XDNBKNLQWNRHSL-FYPKGCJUSA-N 0.000 claims 1
KAFGYEYRFIEIBQ-FYPKGCJUSA-N 5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 KAFGYEYRFIEIBQ-FYPKGCJUSA-N 0.000 claims 1
JIYULCKKMREIFC-WBVHZDCISA-N 5-[(2R,6S)-2-methyl-6-(morpholin-4-ylmethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCOCC2)O1)c1ccc(C#N)c2ncccc12 JIYULCKKMREIFC-WBVHZDCISA-N 0.000 claims 1
RWHMNEDYUYDHOS-WBVHZDCISA-N 5-[(2R,6S)-2-methyl-6-(piperazin-1-ylmethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNCC2)O1)c1ccc(C#N)c2ncccc12 RWHMNEDYUYDHOS-WBVHZDCISA-N 0.000 claims 1
PYLHRIOTKDUHLV-AEFFLSMTSA-N 5-[(2R,6S)-2-methyl-6-(piperidin-1-ylmethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCCCC2)O1)c1ccc(C#N)c2ncccc12 PYLHRIOTKDUHLV-AEFFLSMTSA-N 0.000 claims 1
BGUPSVCPXNUXSP-WBVHZDCISA-N 5-[(2R,6S)-2-methyl-6-(pyrrolidin-1-ylmethyl)morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCCC2)O1)c1ccc(C#N)c2ncccc12 BGUPSVCPXNUXSP-WBVHZDCISA-N 0.000 claims 1
KWMUTFCVMLXXMU-APWZRJJASA-N 5-[(2R,6S)-2-methyl-6-[(1,8-naphthyridin-2-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccc3cccnc3n2)O1)c1ccc(C#N)c2ncccc12 KWMUTFCVMLXXMU-APWZRJJASA-N 0.000 claims 1
PEAXLOSJLXJZQK-KMEYYKJISA-N 5-[(2R,6S)-2-methyl-6-[(2,3,4-trimethylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)C(C)C2C)O1)c1ccc(C#N)c2ncccc12 PEAXLOSJLXJZQK-KMEYYKJISA-N 0.000 claims 1
VAUSRCLNVQQYPL-ZZVGESKWSA-N 5-[(2R,6S)-2-methyl-6-[(2,4,5-trimethylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C)N(C)CC2C)O1)c1ccc(C#N)c2ncccc12 VAUSRCLNVQQYPL-ZZVGESKWSA-N 0.000 claims 1
KNLNHSYTJGRCFX-LBVBGPOBSA-N 5-[(2R,6S)-2-methyl-6-[(2-methyl-5-oxopiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(=O)NCC2C)O1)c1ccc(C#N)c2ncccc12 KNLNHSYTJGRCFX-LBVBGPOBSA-N 0.000 claims 1
OBVMTETXZWLANG-MJGOQNOKSA-N 5-[(2R,6S)-2-methyl-6-[(2-methylanilino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccccc2C)O1)c1ccc(C#N)c2ncccc12 OBVMTETXZWLANG-MJGOQNOKSA-N 0.000 claims 1
VGSLZRYLAWNMLR-QIONWKSUSA-N 5-[(2R,6S)-2-methyl-6-[(2-methylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCCCC2C)O1)c1ccc(C#N)c2ncccc12 VGSLZRYLAWNMLR-QIONWKSUSA-N 0.000 claims 1
VRPJMAMKDZSSAE-VCPDFFEISA-N 5-[(2R,6S)-2-methyl-6-[(2-propan-2-ylpyrrolidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)C1CCCN1C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 VRPJMAMKDZSSAE-VCPDFFEISA-N 0.000 claims 1
PYQBDWDMCDTBJZ-QFZUCXBQSA-N 5-[(2R,6S)-2-methyl-6-[(3,3,4-trimethylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CN(C[C@H](CN2CCN(C)C(C)(C)C2)O1)c1ccc(C#N)c2ncccc12 PYQBDWDMCDTBJZ-QFZUCXBQSA-N 0.000 claims 1
LAUNUQQZDCZGDW-XLIONFOSSA-N 5-[(2R,6S)-2-methyl-6-[(3-methylanilino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cccc(C)c2)O1)c1ccc(C#N)c2ncccc12 LAUNUQQZDCZGDW-XLIONFOSSA-N 0.000 claims 1
SURGOJXUFCPOEC-XLIONFOSSA-N 5-[(2R,6S)-2-methyl-6-[(3-morpholin-4-ylazetidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCOCC2)O1)c1ccc(C#N)c2ncccc12 SURGOJXUFCPOEC-XLIONFOSSA-N 0.000 claims 1
JCPKIIJNMJLQGF-QREQTRJTSA-N 5-[(2R,6S)-2-methyl-6-[(3-phenylpyrrolidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(C2)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 JCPKIIJNMJLQGF-QREQTRJTSA-N 0.000 claims 1
XHLYDCVNGWRUBE-XLIONFOSSA-N 5-[(2R,6S)-2-methyl-6-[(3-piperazin-1-ylazetidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCNCC2)O1)c1ccc(C#N)c2ncccc12 XHLYDCVNGWRUBE-XLIONFOSSA-N 0.000 claims 1
LIYLBAGHTABEBE-NQIIRXRSSA-N 5-[(2R,6S)-2-methyl-6-[(3-piperidin-1-ylazetidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 LIYLBAGHTABEBE-NQIIRXRSSA-N 0.000 claims 1
WNYMXQCIRUVBSB-XLIONFOSSA-N 5-[(2R,6S)-2-methyl-6-[(3-pyrrolidin-1-ylazetidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCCC2)O1)c1ccc(C#N)c2ncccc12 WNYMXQCIRUVBSB-XLIONFOSSA-N 0.000 claims 1
IRDMFMYTVZEQSQ-MJGOQNOKSA-N 5-[(2R,6S)-2-methyl-6-[(4-methyl-1,4-diazepan-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 IRDMFMYTVZEQSQ-MJGOQNOKSA-N 0.000 claims 1
PFVAYTNORGIDIO-XLIONFOSSA-N 5-[(2R,6S)-2-methyl-6-[(4-methylanilino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccc(C)cc2)O1)c1ccc(C#N)c2ncccc12 PFVAYTNORGIDIO-XLIONFOSSA-N 0.000 claims 1
BZFWWBBDWOQNPB-AEFFLSMTSA-N 5-[(2R,6S)-2-methyl-6-[(4-methylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 BZFWWBBDWOQNPB-AEFFLSMTSA-N 0.000 claims 1
GUEPFGUDHGCCIT-MJGOQNOKSA-N 5-[(2R,6S)-2-methyl-6-[(4-methylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 GUEPFGUDHGCCIT-MJGOQNOKSA-N 0.000 claims 1
COROWTBTAKIOEO-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[(4-morpholin-4-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCOCC2)O1)c1ccc(C#N)c2ncccc12 COROWTBTAKIOEO-KNQAVFIVSA-N 0.000 claims 1
PIHXTFCYEHJVKI-OFNKIYASSA-N 5-[(2R,6S)-2-methyl-6-[(4-phenylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 PIHXTFCYEHJVKI-OFNKIYASSA-N 0.000 claims 1
LOOMWWFYPUKVEK-YKSBVNFPSA-N 5-[(2R,6S)-2-methyl-6-[(4-phenylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 LOOMWWFYPUKVEK-YKSBVNFPSA-N 0.000 claims 1
NCUNHUBZCTZFCF-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[(4-piperazin-1-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCNCC2)O1)c1ccc(C#N)c2ncccc12 NCUNHUBZCTZFCF-KNQAVFIVSA-N 0.000 claims 1
JGLZIYAZZKWWAG-OFNKIYASSA-N 5-[(2R,6S)-2-methyl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 JGLZIYAZZKWWAG-OFNKIYASSA-N 0.000 claims 1
OTDJQSRILWCSCE-QPBMFBNESA-N 5-[(2R,6S)-2-methyl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 OTDJQSRILWCSCE-QPBMFBNESA-N 0.000 claims 1
FCKFCJYFGYYEQQ-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[(4-piperidin-4-ylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C2CCNCC2)O1)c1ccc(C#N)c2ncccc12 FCKFCJYFGYYEQQ-KNQAVFIVSA-N 0.000 claims 1
FPNCNEBVVYHQRN-XXBNENTESA-N 5-[(2R,6S)-2-methyl-6-[(4-piperidin-4-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C2CCNCC2)O1)c1ccc(C#N)c2ncccc12 FPNCNEBVVYHQRN-XXBNENTESA-N 0.000 claims 1
MUNPMYAXTBJISF-QUCCMNQESA-N 5-[(2R,6S)-2-methyl-6-[(4-propan-2-ylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)N1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 MUNPMYAXTBJISF-QUCCMNQESA-N 0.000 claims 1
QZGRJTMRJUJFIG-QUCCMNQESA-N 5-[(2R,6S)-2-methyl-6-[(4-propylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCCN1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 QZGRJTMRJUJFIG-QUCCMNQESA-N 0.000 claims 1
OVFBZQNGBUJXSC-CTNGQTDRSA-N 5-[(2R,6S)-2-methyl-6-[(4-pyridin-2-ylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)c2ccccn2)O1)c1ccc(C#N)c2ncccc12 OVFBZQNGBUJXSC-CTNGQTDRSA-N 0.000 claims 1
OYIANONYDQUTCF-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[(4-pyridin-4-ylpiperazin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)c2ccncc2)O1)c1ccc(C#N)c2ncccc12 OYIANONYDQUTCF-KNQAVFIVSA-N 0.000 claims 1
MVIRVLSEMZVDHQ-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCC2)O1)c1ccc(C#N)c2ncccc12 MVIRVLSEMZVDHQ-KNQAVFIVSA-N 0.000 claims 1
SXFGPJRVELHKPR-ZBFHGGJFSA-N 5-[(2R,6S)-2-methyl-6-[(pyrazin-2-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cnccn2)O1)c1ccc(C#N)c2ncccc12 SXFGPJRVELHKPR-ZBFHGGJFSA-N 0.000 claims 1
WGAYXQJIUWWRTC-WBVHZDCISA-N 5-[(2R,6S)-2-methyl-6-[(pyridin-2-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccccn2)O1)c1ccc(C#N)c2ncccc12 WGAYXQJIUWWRTC-WBVHZDCISA-N 0.000 claims 1
XKSAQSQWTIDJBN-QAPCUYQASA-N 5-[(2R,6S)-2-methyl-6-[(pyridin-3-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cccnc2)O1)c1ccc(C#N)c2ncccc12 XKSAQSQWTIDJBN-QAPCUYQASA-N 0.000 claims 1
POEVTJMXWMIXSP-QAPCUYQASA-N 5-[(2R,6S)-2-methyl-6-[(pyridin-4-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccncc2)O1)c1ccc(C#N)c2ncccc12 POEVTJMXWMIXSP-QAPCUYQASA-N 0.000 claims 1
OSFSKJDTOLWMNR-ZBFHGGJFSA-N 5-[(2R,6S)-2-methyl-6-[(pyrimidin-2-ylamino)methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ncccn2)O1)c1ccc(C#N)c2ncccc12 OSFSKJDTOLWMNR-ZBFHGGJFSA-N 0.000 claims 1
PRUOZLJETAOXSY-DDUYZKFLSA-N 5-[(2R,6S)-2-methyl-6-[[(2-methylcyclohexyl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCCCC2C)O1)c1ccc(C#N)c2ncccc12 PRUOZLJETAOXSY-DDUYZKFLSA-N 0.000 claims 1
XCLRWHRFBDOYED-NQIIRXRSSA-N 5-[(2R,6S)-2-methyl-6-[[(2-phenylpyrazol-3-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccnn2-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 XCLRWHRFBDOYED-NQIIRXRSSA-N 0.000 claims 1
NAZSXUVVOCRTPN-XXBNENTESA-N 5-[(2R,6S)-2-methyl-6-[[(2-phenylpyridin-4-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccnc(c2)-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 NAZSXUVVOCRTPN-XXBNENTESA-N 0.000 claims 1
KENZMKZRHCGYHW-INMHGKMJSA-N 5-[(2R,6S)-2-methyl-6-[[(2R)-2-methyl-3-oxopiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNC(=O)[C@H]2C)O1)c1ccc(C#N)c2ncccc12 KENZMKZRHCGYHW-INMHGKMJSA-N 0.000 claims 1
KNLNHSYTJGRCFX-INMHGKMJSA-N 5-[(2R,6S)-2-methyl-6-[[(2R)-2-methyl-5-oxopiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(=O)NC[C@H]2C)O1)c1ccc(C#N)c2ncccc12 KNLNHSYTJGRCFX-INMHGKMJSA-N 0.000 claims 1
FBIKGVKAIYSYSF-NUJGCVRESA-N 5-[(2R,6S)-2-methyl-6-[[(2R)-2-methylpiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNC[C@H]2C)O1)c1ccc(C#N)c2ncccc12 FBIKGVKAIYSYSF-NUJGCVRESA-N 0.000 claims 1
BJMDRAUBPWRMCW-NUJGCVRESA-N 5-[(2R,6S)-2-methyl-6-[[(2R)-2-methylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CCCN1C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 BJMDRAUBPWRMCW-NUJGCVRESA-N 0.000 claims 1
NOAPEUYJSQADPL-ALKREAHSSA-N 5-[(2R,6S)-2-methyl-6-[[(2S)-2-(trifluoromethyl)pyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@H]2C(F)(F)F)O1)c1ccc(C#N)c2ncccc12 NOAPEUYJSQADPL-ALKREAHSSA-N 0.000 claims 1
KENZMKZRHCGYHW-VYDXJSESSA-N 5-[(2R,6S)-2-methyl-6-[[(2S)-2-methyl-3-oxopiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNC(=O)[C@@H]2C)O1)c1ccc(C#N)c2ncccc12 KENZMKZRHCGYHW-VYDXJSESSA-N 0.000 claims 1
KNLNHSYTJGRCFX-UXLLHSPISA-N 5-[(2R,6S)-2-methyl-6-[[(2S)-2-methyl-5-oxopiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(=O)NC[C@@H]2C)O1)c1ccc(C#N)c2ncccc12 KNLNHSYTJGRCFX-UXLLHSPISA-N 0.000 claims 1
FBIKGVKAIYSYSF-JZXOWHBKSA-N 5-[(2R,6S)-2-methyl-6-[[(2S)-2-methylpiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNC[C@@H]2C)O1)c1ccc(C#N)c2ncccc12 FBIKGVKAIYSYSF-JZXOWHBKSA-N 0.000 claims 1
BJMDRAUBPWRMCW-JZXOWHBKSA-N 5-[(2R,6S)-2-methyl-6-[[(2S)-2-methylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CCCN1C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 BJMDRAUBPWRMCW-JZXOWHBKSA-N 0.000 claims 1
HALQSSGVOZKPRM-YTQPIUFNSA-N 5-[(2R,6S)-2-methyl-6-[[(3-methylcyclohexyl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1CCCC(C1)NC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 HALQSSGVOZKPRM-YTQPIUFNSA-N 0.000 claims 1
KMRUKLHGNNKICT-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[[(3-phenylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ncccc2-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 KMRUKLHGNNKICT-KNQAVFIVSA-N 0.000 claims 1
UYUBMDDNAVAWLB-NUJGCVRESA-N 5-[(2R,6S)-2-methyl-6-[[(3R)-3-methylpiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CCN1 UYUBMDDNAVAWLB-NUJGCVRESA-N 0.000 claims 1
VGDQGCFQSSWAQL-NUJGCVRESA-N 5-[(2R,6S)-2-methyl-6-[[(3R)-3-methylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C1 VGDQGCFQSSWAQL-NUJGCVRESA-N 0.000 claims 1
GCQRLQWJASDGOH-FCEUIQTBSA-N 5-[(2R,6S)-2-methyl-6-[[(3R)-3-piperidin-1-ylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@H](C2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 GCQRLQWJASDGOH-FCEUIQTBSA-N 0.000 claims 1
HXFXIYICFVYZIE-NRSPTQNISA-N 5-[(2R,6S)-2-methyl-6-[[(3R)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@H](C2)N2CCCC2)O1)c1ccc(C#N)c2ncccc12 HXFXIYICFVYZIE-NRSPTQNISA-N 0.000 claims 1
UYUBMDDNAVAWLB-JZXOWHBKSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-methylpiperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CCN1 UYUBMDDNAVAWLB-JZXOWHBKSA-N 0.000 claims 1
VGDQGCFQSSWAQL-JZXOWHBKSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-methylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C1 VGDQGCFQSSWAQL-JZXOWHBKSA-N 0.000 claims 1
JCPKIIJNMJLQGF-PTUXOGIPSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-phenylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@H](C2)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 JCPKIIJNMJLQGF-PTUXOGIPSA-N 0.000 claims 1
GCQRLQWJASDGOH-HJNYFJLDSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-piperidin-1-ylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@@H](C2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 GCQRLQWJASDGOH-HJNYFJLDSA-N 0.000 claims 1
OLYSFXQKCWDGQI-LOYOPDQSSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-piperidin-1-ylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CN(C[C@H](CN2CC[C@@H](C2)N2CCCCC2)O1)c1ccc(C#N)c2ncccc12 OLYSFXQKCWDGQI-LOYOPDQSSA-N 0.000 claims 1
HXFXIYICFVYZIE-GIVPXCGWSA-N 5-[(2R,6S)-2-methyl-6-[[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@@H](C2)N2CCCC2)O1)c1ccc(C#N)c2ncccc12 HXFXIYICFVYZIE-GIVPXCGWSA-N 0.000 claims 1
YZUSMKYIBWVBOH-YTQPIUFNSA-N 5-[(2R,6S)-2-methyl-6-[[(4-methylcyclohexyl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1CCC(CC1)NC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 YZUSMKYIBWVBOH-YTQPIUFNSA-N 0.000 claims 1
RZJZMKDQHUWUNK-AEFFLSMTSA-N 5-[(2R,6S)-2-methyl-6-[[(4-methylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cc(C)ccn2)O1)c1ccc(C#N)c2ncccc12 RZJZMKDQHUWUNK-AEFFLSMTSA-N 0.000 claims 1
GXWOAILDAKMWQA-XXBNENTESA-N 5-[(2R,6S)-2-methyl-6-[[(4-phenylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cc(ccn2)-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 GXWOAILDAKMWQA-XXBNENTESA-N 0.000 claims 1
FTDJYKKJBKZRFV-AEFFLSMTSA-N 5-[(2R,6S)-2-methyl-6-[[(5-methylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccc(C)cn2)O1)c1ccc(C#N)c2ncccc12 FTDJYKKJBKZRFV-AEFFLSMTSA-N 0.000 claims 1
BNMHOFVUXXKHKH-XXBNENTESA-N 5-[(2R,6S)-2-methyl-6-[[(5-phenylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccc(cn2)-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 BNMHOFVUXXKHKH-XXBNENTESA-N 0.000 claims 1
BQXMRJBDEUVTAQ-AEFFLSMTSA-N 5-[(2R,6S)-2-methyl-6-[[(6-methylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cccc(C)n2)O1)c1ccc(C#N)c2ncccc12 BQXMRJBDEUVTAQ-AEFFLSMTSA-N 0.000 claims 1
XOIDZEAJYFXPER-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[[(6-phenylpyridin-2-yl)amino]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cccc(n2)-c2ccccc2)O1)c1ccc(C#N)c2ncccc12 XOIDZEAJYFXPER-KNQAVFIVSA-N 0.000 claims 1
SYIDHJSNISITBQ-NQIIRXRSSA-N 5-[(2R,6S)-2-methyl-6-[[3-(4-methylpiperazin-1-yl)azetidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 SYIDHJSNISITBQ-NQIIRXRSSA-N 0.000 claims 1
QKALACNMPCIFQQ-NQIIRXRSSA-N 5-[(2R,6S)-2-methyl-6-[[3-(4-methylsulfonylpiperazin-1-yl)azetidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCN(CC2)S(C)(=O)=O)O1)c1ccc(C#N)c2ncccc12 QKALACNMPCIFQQ-NQIIRXRSSA-N 0.000 claims 1
ISZQUJWKNHBOCB-UEXGIBASSA-N 5-[(2R,6S)-2-methyl-6-[[3-[(2S)-2-methylpyrrolidin-1-yl]azetidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CCCN1C1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C1 ISZQUJWKNHBOCB-UEXGIBASSA-N 0.000 claims 1
FNMBNLOEDHIOKZ-OFNKIYASSA-N 5-[(2R,6S)-2-methyl-6-[[3-[4-(2-methylpropanoyl)piperazin-1-yl]azetidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)C(=O)N1CCN(CC1)C1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C1 FNMBNLOEDHIOKZ-OFNKIYASSA-N 0.000 claims 1
UDEXPOOKGJVOAB-OFNKIYASSA-N 5-[(2R,6S)-2-methyl-6-[[4-(1-methylpiperidin-4-yl)piperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 UDEXPOOKGJVOAB-OFNKIYASSA-N 0.000 claims 1
INKVAMPWISWYMY-YKSBVNFPSA-N 5-[(2R,6S)-2-methyl-6-[[4-(1-methylpiperidin-4-yl)piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 INKVAMPWISWYMY-YKSBVNFPSA-N 0.000 claims 1
KKHZQZYURADTQL-KNQAVFIVSA-N 5-[(2R,6S)-2-methyl-6-[[4-(2-oxopiperidin-1-yl)piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCCC2=O)O1)c1ccc(C#N)c2ncccc12 KKHZQZYURADTQL-KNQAVFIVSA-N 0.000 claims 1
MEEMWIAFWUNXTD-OFNKIYASSA-N 5-[(2R,6S)-2-methyl-6-[[4-(4-methylpiperazin-1-yl)piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 MEEMWIAFWUNXTD-OFNKIYASSA-N 0.000 claims 1
DBYFVPCSRPQPTO-YRMHZFCISA-N 5-[(2R,6S)-2-methyl-6-[[4-(4-methylpiperazin-1-yl)piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile trihydrochloride Chemical compound Cl.Cl.Cl.C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCN(C)CC2)O1)c1ccc(C#N)c2ncccc12 DBYFVPCSRPQPTO-YRMHZFCISA-N 0.000 claims 1
XSOJIJUPGJTNMJ-RDGATRHJSA-N 5-[(2R,6S)-2-methyl-6-[[4-[1-(2-methylpropanoyl)piperidin-4-yl]piperazin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)C(=O)N1CCC(CC1)N1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 XSOJIJUPGJTNMJ-RDGATRHJSA-N 0.000 claims 1
DSGYAMAXTAXVCX-GJZUVCINSA-N 5-[(2R,6S)-2-methyl-6-[[4-[1-(2-methylpropanoyl)piperidin-4-yl]piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)C(=O)N1CCC(CC1)C1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 DSGYAMAXTAXVCX-GJZUVCINSA-N 0.000 claims 1
DQPPLXKHVKYCPA-RDGATRHJSA-N 5-[(2R,6S)-2-methyl-6-[[4-[4-(2-methylpropanoyl)piperazin-1-yl]piperidin-1-yl]methyl]morpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC(C)C(=O)N1CCN(CC1)C1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 DQPPLXKHVKYCPA-RDGATRHJSA-N 0.000 claims 1
DVFRPLNFZPIQMU-WBVHZDCISA-N 5-[(2R,6S)-2-methyl-6-pentylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCCCC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 DVFRPLNFZPIQMU-WBVHZDCISA-N 0.000 claims 1
DLYBTVCFXZXEBD-HIFRSBDPSA-N 5-[(2R,6S)-2-methyl-6-propylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 DLYBTVCFXZXEBD-HIFRSBDPSA-N 0.000 claims 1
WWECSDZGJXAKKN-IWKKHLOMSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]quinoline-8-carbonitrile methanesulfonic acid Chemical compound CS(O)(=O)=O.C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 WWECSDZGJXAKKN-IWKKHLOMSA-N 0.000 claims 1
RAZOKVSESISURE-YPMHNXCESA-N 5-[(2S,6R)-2-(aminomethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN)O1)c1ccc(C#N)c2ncccc12 RAZOKVSESISURE-YPMHNXCESA-N 0.000 claims 1
ZKLXMXYOKKSJJT-APWZRJJASA-N 5-[(2S,6R)-2-(anilinomethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccccc2)O1)c1ccc(C#N)c2ncccc12 ZKLXMXYOKKSJJT-APWZRJJASA-N 0.000 claims 1
UZFRKQKIGPOTAF-WBVHZDCISA-N 5-[(2S,6R)-2-(diethylaminomethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCN(CC)C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 UZFRKQKIGPOTAF-WBVHZDCISA-N 0.000 claims 1
ROSRMDCEURJYGL-JIZBTBOESA-N 5-[(2S,6R)-2-[(2,3-dimethylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCNC(C)C2C)O1)c1ccc(C#N)c2ncccc12 ROSRMDCEURJYGL-JIZBTBOESA-N 0.000 claims 1
PCMOELTWSIYMLN-WXVPWVKJSA-N 5-[(2S,6R)-2-[(2,5-dimethylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C(C)CN1 PCMOELTWSIYMLN-WXVPWVKJSA-N 0.000 claims 1
DBTUUWPNMGBKOW-HTPOPCQBSA-N 5-[(2S,6R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC1CCC(C)N1C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 DBTUUWPNMGBKOW-HTPOPCQBSA-N 0.000 claims 1
LCQVVPBJRRTCDV-BPYOIECJSA-N 5-[(2S,6R)-2-[(2-ethylpiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCC1CCCCN1C[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 LCQVVPBJRRTCDV-BPYOIECJSA-N 0.000 claims 1
JYTCZNSLFDTBKQ-UFUZANHXSA-N 5-[(2S,6R)-2-[(3,3-dimethylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CN(C[C@H](CN2CCNC(C)(C)C2)O1)c1ccc(C#N)c2ncccc12 JYTCZNSLFDTBKQ-UFUZANHXSA-N 0.000 claims 1
VTYLWXLSXJWLOE-AEFFLSMTSA-N 5-[(2S,6R)-2-[(3,3-dimethylpyrrolidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(C)(C)C2)O1)c1ccc(C#N)c2ncccc12 VTYLWXLSXJWLOE-AEFFLSMTSA-N 0.000 claims 1
BAAAKMGRGDOUOL-CJNGLKHVSA-N 5-[(2S,6R)-2-[(3-aminoazetidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(N)C2)O1)c1ccc(C#N)c2ncccc12 BAAAKMGRGDOUOL-CJNGLKHVSA-N 0.000 claims 1
CIUMMAAXJMHIKJ-WBVHZDCISA-N 5-[(2S,6R)-2-[(4,4-difluoropiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(F)(F)CC2)O1)c1ccc(C#N)c2ncccc12 CIUMMAAXJMHIKJ-WBVHZDCISA-N 0.000 claims 1
WCMDSNHMGALPQY-APWZRJJASA-N 5-[(2S,6R)-2-[(4-acetylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C(C)=O)O1)c1ccc(C#N)c2ncccc12 WCMDSNHMGALPQY-APWZRJJASA-N 0.000 claims 1
IGFNFZDFXIVOGM-QAPCUYQASA-N 5-[(2S,6R)-2-[(4-aminopiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(N)CC2)O1)c1ccc(C#N)c2ncccc12 IGFNFZDFXIVOGM-QAPCUYQASA-N 0.000 claims 1
GBWIBHSMEKZYHK-OFNKIYASSA-N 5-[(2S,6R)-2-[(4-benzoylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C(=O)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 GBWIBHSMEKZYHK-OFNKIYASSA-N 0.000 claims 1
JEQJOUWCGSNXCU-YKSBVNFPSA-N 5-[(2S,6R)-2-[(4-cyclohexylpiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C2CCCCC2)O1)c1ccc(C#N)c2ncccc12 JEQJOUWCGSNXCU-YKSBVNFPSA-N 0.000 claims 1
MWIQAZAIHPBQMR-MJGOQNOKSA-N 5-[(2S,6R)-2-[(4-ethylpiperazin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCN1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 MWIQAZAIHPBQMR-MJGOQNOKSA-N 0.000 claims 1
XONGMKNLEAVVOA-QAPCUYQASA-N 5-[(2S,6R)-2-[(4-fluoropiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(F)CC2)O1)c1ccc(C#N)c2ncccc12 XONGMKNLEAVVOA-QAPCUYQASA-N 0.000 claims 1
BGSZMYLWUJDQSP-QAPCUYQASA-N 5-[(2S,6R)-2-[(4-hydroxypiperidin-1-yl)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(O)CC2)O1)c1ccc(C#N)c2ncccc12 BGSZMYLWUJDQSP-QAPCUYQASA-N 0.000 claims 1
TVCWTAJCJPABKB-XLIONFOSSA-N 5-[(2S,6R)-2-[(benzylamino)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNCc2ccccc2)O1)c1ccc(C#N)c2ncccc12 TVCWTAJCJPABKB-XLIONFOSSA-N 0.000 claims 1
OERTYVIHMIPGAA-PBHICJAKSA-N 5-[(2S,6R)-2-[(cyclobutylamino)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCC2)O1)c1ccc(C#N)c2ncccc12 OERTYVIHMIPGAA-PBHICJAKSA-N 0.000 claims 1
CPDTYWOJXXKLJI-XLIONFOSSA-N 5-[(2S,6R)-2-[(cycloheptylamino)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCCCCC2)O1)c1ccc(C#N)c2ncccc12 CPDTYWOJXXKLJI-XLIONFOSSA-N 0.000 claims 1
NVJQVEWRTYRIAT-APWZRJJASA-N 5-[(2S,6R)-2-[(cyclohexylamino)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCCCC2)O1)c1ccc(C#N)c2ncccc12 NVJQVEWRTYRIAT-APWZRJJASA-N 0.000 claims 1
VOGBIPLUQHCHDL-QAPCUYQASA-N 5-[(2S,6R)-2-[(cyclopentylamino)methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCCC2)O1)c1ccc(C#N)c2ncccc12 VOGBIPLUQHCHDL-QAPCUYQASA-N 0.000 claims 1
SCOQUWOVVQABKJ-UZLBHIALSA-N 5-[(2S,6R)-2-[[(1,2-dimethylbenzimidazol-5-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ccc3n(C)c(C)nc3c2)O1)c1ccc(C#N)c2ncccc12 SCOQUWOVVQABKJ-UZLBHIALSA-N 0.000 claims 1
REQQCXBFPHVOGD-UTKZUKDTSA-N 5-[(2S,6R)-2-[[(1-ethyl-2-methylbenzimidazol-5-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCn1c(C)nc2cc(NC[C@H]3CN(C[C@@H](C)O3)c3ccc(C#N)c4ncccc34)ccc12 REQQCXBFPHVOGD-UTKZUKDTSA-N 0.000 claims 1
KVVNLGGLFPLKLR-WBVHZDCISA-N 5-[(2S,6R)-2-[[(2,5-dimethylpyrazol-3-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cc(C)nn2C)O1)c1ccc(C#N)c2ncccc12 KVVNLGGLFPLKLR-WBVHZDCISA-N 0.000 claims 1
OZYCWZKLEVRNEP-UBXKQKMASA-N 5-[(2S,6R)-2-[[(2-hydroxycyclopentyl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCCC2O)O1)c1ccc(C#N)c2ncccc12 OZYCWZKLEVRNEP-UBXKQKMASA-N 0.000 claims 1
CTDWZVBFGDEWRG-LMMKCTJWSA-N 5-[(2S,6R)-2-[[(2R)-2,4-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)C[C@H]2C)O1)c1ccc(C#N)c2ncccc12 CTDWZVBFGDEWRG-LMMKCTJWSA-N 0.000 claims 1
WFRSQEXJGXKXPL-NXHRZFHOSA-N 5-[(2S,6R)-2-[[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@@H]2CO)O1)c1ccc(C#N)c2ncccc12 WFRSQEXJGXKXPL-NXHRZFHOSA-N 0.000 claims 1
PCMOELTWSIYMLN-MTNOOBJLSA-N 5-[(2S,6R)-2-[[(2R,5R)-2,5-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)[C@H](C)CN1 PCMOELTWSIYMLN-MTNOOBJLSA-N 0.000 claims 1
PCMOELTWSIYMLN-FAJBIJEISA-N 5-[(2S,6R)-2-[[(2R,5S)-2,5-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)[C@H](C)CN1 PCMOELTWSIYMLN-FAJBIJEISA-N 0.000 claims 1
BJRAKCSSFWLCOK-ZAWLATJESA-N 5-[(2S,6R)-2-[[(2R,6R)-2-(hydroxymethyl)-6-methylmorpholin-4-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C[C@H](CO)O1 BJRAKCSSFWLCOK-ZAWLATJESA-N 0.000 claims 1
WLVNMWGPLVJJSI-AJYBTWMASA-N 5-[(2S,6R)-2-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2[C@@H](C)CCC[C@H]2C)O1)c1ccc(C#N)c2ncccc12 WLVNMWGPLVJJSI-AJYBTWMASA-N 0.000 claims 1
CTDWZVBFGDEWRG-SCTDSRPQSA-N 5-[(2S,6R)-2-[[(2S)-2,4-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)C[C@@H]2C)O1)c1ccc(C#N)c2ncccc12 CTDWZVBFGDEWRG-SCTDSRPQSA-N 0.000 claims 1
WFRSQEXJGXKXPL-NJAFHUGGSA-N 5-[(2S,6R)-2-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@H]2CO)O1)c1ccc(C#N)c2ncccc12 WFRSQEXJGXKXPL-NJAFHUGGSA-N 0.000 claims 1
DVVZHMMLGSTSNM-SPUZQDLCSA-N 5-[(2S,6R)-2-[[(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2C[C@H](O)C[C@H]2CO)O1)c1ccc(C#N)c2ncccc12 DVVZHMMLGSTSNM-SPUZQDLCSA-N 0.000 claims 1
LNYMIWASCDPBPB-NTDBWNAOSA-N 5-[(2S,6R)-2-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)C[C@@H](C)O1 LNYMIWASCDPBPB-NTDBWNAOSA-N 0.000 claims 1
PNHZXADMHGVQNK-AEFFLSMTSA-N 5-[(2S,6R)-2-[[(3-ethoxypyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCOc1cccnc1NC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 PNHZXADMHGVQNK-AEFFLSMTSA-N 0.000 claims 1
PCIYYLZYQWWXFH-WBVHZDCISA-N 5-[(2S,6R)-2-[[(3-methoxypyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound COc1cccnc1NC[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 PCIYYLZYQWWXFH-WBVHZDCISA-N 0.000 claims 1
OVFWPDRJYCMLAM-LMMKCTJWSA-N 5-[(2S,6R)-2-[[(3R)-3,4-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)[C@H](C)C2)O1)c1ccc(C#N)c2ncccc12 OVFWPDRJYCMLAM-LMMKCTJWSA-N 0.000 claims 1
BJAALLOPHYKEJB-QRQLOZEOSA-N 5-[(2S,6R)-2-[[(3R)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@H](C2)N(C)C)O1)c1ccc(C#N)c2ncccc12 BJAALLOPHYKEJB-QRQLOZEOSA-N 0.000 claims 1
BQQZQVFVXQROHE-NXHRZFHOSA-N 5-[(2S,6R)-2-[[(3R)-3-aminopiperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@@H](N)C2)O1)c1ccc(C#N)c2ncccc12 BQQZQVFVXQROHE-NXHRZFHOSA-N 0.000 claims 1
YFUKUALOQXQTGB-NXHRZFHOSA-N 5-[(2S,6R)-2-[[(3R)-3-hydroxypiperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@@H](O)C2)O1)c1ccc(C#N)c2ncccc12 YFUKUALOQXQTGB-NXHRZFHOSA-N 0.000 claims 1
VWEKATHAOZPAIR-OIISXLGYSA-N 5-[(2S,6R)-2-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@@H](O)C2)O1)c1ccc(C#N)c2ncccc12 VWEKATHAOZPAIR-OIISXLGYSA-N 0.000 claims 1
OVFWPDRJYCMLAM-SCTDSRPQSA-N 5-[(2S,6R)-2-[[(3S)-3,4-dimethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(C)[C@@H](C)C2)O1)c1ccc(C#N)c2ncccc12 OVFWPDRJYCMLAM-SCTDSRPQSA-N 0.000 claims 1
BJAALLOPHYKEJB-NEWSRXKRSA-N 5-[(2S,6R)-2-[[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@@H](C2)N(C)C)O1)c1ccc(C#N)c2ncccc12 BJAALLOPHYKEJB-NEWSRXKRSA-N 0.000 claims 1
DCQONGKYWJAQDU-HOJAQTOUSA-N 5-[(2S,6R)-2-[[(3S)-3-ethyl-4-methylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CCN1C DCQONGKYWJAQDU-HOJAQTOUSA-N 0.000 claims 1
MCWZPGJCVGTPGX-NEWSRXKRSA-N 5-[(2S,6R)-2-[[(3S)-3-ethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CC[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CCN1 MCWZPGJCVGTPGX-NEWSRXKRSA-N 0.000 claims 1
YSUZZDWFUPGXOG-KMARQUQUSA-N 5-[(2S,6R)-2-[[(3S)-3-ethylpiperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile dihydrochloride Chemical compound Cl.Cl.CC[C@H]1CN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CCN1 YSUZZDWFUPGXOG-KMARQUQUSA-N 0.000 claims 1
YFUKUALOQXQTGB-NJAFHUGGSA-N 5-[(2S,6R)-2-[[(3S)-3-hydroxypiperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC[C@H](O)C2)O1)c1ccc(C#N)c2ncccc12 YFUKUALOQXQTGB-NJAFHUGGSA-N 0.000 claims 1
VWEKATHAOZPAIR-PVAVHDDUSA-N 5-[(2S,6R)-2-[[(3S)-3-hydroxypyrrolidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC[C@H](O)C2)O1)c1ccc(C#N)c2ncccc12 VWEKATHAOZPAIR-PVAVHDDUSA-N 0.000 claims 1
YSJCATFPRFTMTA-HJZRJOMTSA-N 5-[(2S,6R)-2-[[(4-hydroxycyclohexyl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNC2CCC(O)CC2)O1)c1ccc(C#N)c2ncccc12 YSJCATFPRFTMTA-HJZRJOMTSA-N 0.000 claims 1
RZCYCBWBFWEILU-QAPCUYQASA-N 5-[(2S,6R)-2-[[(4-methoxypyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound COc1ccnc(NC[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)c1 RZCYCBWBFWEILU-QAPCUYQASA-N 0.000 claims 1
PFSDYOKJHSWERE-QAPCUYQASA-N 5-[(2S,6R)-2-[[(5-ethylpyrimidin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound CCc1cnc(NC[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)nc1 PFSDYOKJHSWERE-QAPCUYQASA-N 0.000 claims 1
DQJSNUPIVYXSOM-CJNGLKHVSA-N 5-[(2S,6R)-2-[[(5-fluoropyrimidin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2ncc(F)cn2)O1)c1ccc(C#N)c2ncccc12 DQJSNUPIVYXSOM-CJNGLKHVSA-N 0.000 claims 1
IGRYKVYFNWOWCO-AEFFLSMTSA-N 5-[(2S,6R)-2-[[(6-amino-3,5-dimethylpyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2nc(N)c(C)cc2C)O1)c1ccc(C#N)c2ncccc12 IGRYKVYFNWOWCO-AEFFLSMTSA-N 0.000 claims 1
OBEVSTHLJXHFBE-ZBFHGGJFSA-N 5-[(2S,6R)-2-[[(6-aminopyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CNc2cccc(N)n2)O1)c1ccc(C#N)c2ncccc12 OBEVSTHLJXHFBE-ZBFHGGJFSA-N 0.000 claims 1
DUOABQUSCJCQFE-WBVHZDCISA-N 5-[(2S,6R)-2-[[(6-methoxypyridin-2-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound COc1cccc(NC[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)n1 DUOABQUSCJCQFE-WBVHZDCISA-N 0.000 claims 1
ANPHNWNBOHJLKL-QAPCUYQASA-N 5-[(2S,6R)-2-[[(6-methoxypyridin-3-yl)amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound COc1ccc(NC[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)cn1 ANPHNWNBOHJLKL-QAPCUYQASA-N 0.000 claims 1
OWPIULAQZYCDKI-WDOSNPKHSA-N 5-[(2S,6R)-2-[[2-(hydroxymethyl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCCCC2CO)O1)c1ccc(C#N)c2ncccc12 OWPIULAQZYCDKI-WDOSNPKHSA-N 0.000 claims 1
QQVJBHZMGSRATI-GCJKJVERSA-N 5-[(2S,6R)-2-[[3-(4-acetylpiperazin-1-yl)azetidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCN(CC2)C(C)=O)O1)c1ccc(C#N)c2ncccc12 QQVJBHZMGSRATI-GCJKJVERSA-N 0.000 claims 1
MLWJYRIJMZYQGK-UTKZUKDTSA-N 5-[(2S,6R)-2-[[3-(4-aminopiperidin-1-yl)azetidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCC(N)CC2)O1)c1ccc(C#N)c2ncccc12 MLWJYRIJMZYQGK-UTKZUKDTSA-N 0.000 claims 1
QXSOVAOLWJPQDU-GJZUVCINSA-N 5-[(2S,6R)-2-[[3-(4-benzoylpiperazin-1-yl)azetidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CCN(CC2)C(=O)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 QXSOVAOLWJPQDU-GJZUVCINSA-N 0.000 claims 1
ZCOUBHXUPQATDZ-UXPWSPDFSA-N 5-[(2S,6R)-2-[[3-[(3S)-3-hydroxypyrrolidin-1-yl]azetidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)N2CC[C@H](O)C2)O1)c1ccc(C#N)c2ncccc12 ZCOUBHXUPQATDZ-UXPWSPDFSA-N 0.000 claims 1
JSCLEKDRYKGKMQ-YKSBVNFPSA-N 5-[(2S,6R)-2-[[4-(1-acetylpiperidin-4-yl)piperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C2CCN(CC2)C(C)=O)O1)c1ccc(C#N)c2ncccc12 JSCLEKDRYKGKMQ-YKSBVNFPSA-N 0.000 claims 1
VDNPUMBRUFNHMO-NLFFAJNJSA-N 5-[(2S,6R)-2-[[4-(1-acetylpiperidin-4-yl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C2CCN(CC2)C(C)=O)O1)c1ccc(C#N)c2ncccc12 VDNPUMBRUFNHMO-NLFFAJNJSA-N 0.000 claims 1
IBMGJVKKZAPFGH-YWEHKCAJSA-N 5-[(2S,6R)-2-[[4-(1-benzoylpiperidin-4-yl)piperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCN(CC2)C2CCN(CC2)C(=O)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 IBMGJVKKZAPFGH-YWEHKCAJSA-N 0.000 claims 1
QMROBLTZYUPCNR-GIGWZHCTSA-N 5-[(2S,6R)-2-[[4-(1-benzoylpiperidin-4-yl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)C2CCN(CC2)C(=O)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 QMROBLTZYUPCNR-GIGWZHCTSA-N 0.000 claims 1
HOZPKKYXFHWGIZ-YKSBVNFPSA-N 5-[(2S,6R)-2-[[4-(4-acetylpiperazin-1-yl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCN(CC2)C(C)=O)O1)c1ccc(C#N)c2ncccc12 HOZPKKYXFHWGIZ-YKSBVNFPSA-N 0.000 claims 1
BOLXYBCPTHLXHX-YWEHKCAJSA-N 5-[(2S,6R)-2-[[4-(4-benzoylpiperazin-1-yl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCN(CC2)C(=O)c2ccccc2)O1)c1ccc(C#N)c2ncccc12 BOLXYBCPTHLXHX-YWEHKCAJSA-N 0.000 claims 1
XFPNMYNRSSLDJP-QPPBQGQZSA-N 5-[(2S,6R)-2-[[4-(azepan-1-yl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCCCCC2)O1)c1ccc(C#N)c2ncccc12 XFPNMYNRSSLDJP-QPPBQGQZSA-N 0.000 claims 1
ZXCITEJNSPRWLM-XLIONFOSSA-N 5-[(2S,6R)-2-[[4-(dimethylamino)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N(C)C)O1)c1ccc(C#N)c2ncccc12 ZXCITEJNSPRWLM-XLIONFOSSA-N 0.000 claims 1
ARXGPCPJZXURKR-APWZRJJASA-N 5-[(2S,6R)-2-[[4-(hydroxymethyl)piperidin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CO)CC2)O1)c1ccc(C#N)c2ncccc12 ARXGPCPJZXURKR-APWZRJJASA-N 0.000 claims 1
WTZNDEGWEAVLTA-SPUZQDLCSA-N 5-[(2S,6R)-2-[[[(1S,3R)-3-hydroxycyclopentyl]amino]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile Chemical compound C[C@@H]1CN(C[C@H](CN[C@H]2CC[C@@H](O)C2)O1)c1ccc(C#N)c2ncccc12 WTZNDEGWEAVLTA-SPUZQDLCSA-N 0.000 claims 1
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ISHTTWSBTOQHJT-UHFFFAOYSA-N 5-[3-(hydroxymethyl)-5-methylphenyl]quinoline-8-carbonitrile Chemical compound Cc1cc(CO)cc(c1)-c1ccc(C#N)c2ncccc12 ISHTTWSBTOQHJT-UHFFFAOYSA-N 0.000 claims 1
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GKGCUEOVFGAHIV-UHFFFAOYSA-N 5-[3-[[4-(dimethylamino)piperidin-1-yl]methyl]-5-methylphenyl]quinoline-8-carbonitrile Chemical compound CN(C)C1CCN(Cc2cc(C)cc(c2)-c2ccc(C#N)c3ncccc23)CC1 GKGCUEOVFGAHIV-UHFFFAOYSA-N 0.000 claims 1
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ZWBUFARCXATSBX-HOJAQTOUSA-N N-[(3S)-1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]pyrrolidin-3-yl]-2-methylpropanamide Chemical compound C(#N)C=1C=CC(=C2C=CC=NC12)N1C[C@@H](O[C@@H](C1)C)CN1C[C@H](CC1)NC(C(C)C)=O ZWBUFARCXATSBX-HOJAQTOUSA-N 0.000 claims 1
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PUOFYMRVHHCDIJ-UZLBHIALSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]azetidin-3-yl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)NS(=O)(=O)c2cn(C)nc2C)O1)c1ccc(C#N)c2ncccc12 PUOFYMRVHHCDIJ-UZLBHIALSA-N 0.000 claims 1
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RECPTVLCYMSIIY-PBHICJAKSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]azetidin-3-yl]methanesulfonamide Chemical compound C[C@@H]1CN(C[C@H](CN2CC(C2)NS(C)(=O)=O)O1)c1ccc(C#N)c2ncccc12 RECPTVLCYMSIIY-PBHICJAKSA-N 0.000 claims 1
VHNMSNTYQWLWMD-GCJKJVERSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)NC(=O)c2cn(C)nc2C)O1)c1ccc(C#N)c2ncccc12 VHNMSNTYQWLWMD-GCJKJVERSA-N 0.000 claims 1
LOFWUSBVWIBNJR-GCJKJVERSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)NS(=O)(=O)c2cn(C)nc2C)O1)c1ccc(C#N)c2ncccc12 LOFWUSBVWIBNJR-GCJKJVERSA-N 0.000 claims 1
BWCOJLAUFGDWPQ-NQIIRXRSSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]-2,2-dimethylpropanamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)NC(=O)C(C)(C)C)O1)c1ccc(C#N)c2ncccc12 BWCOJLAUFGDWPQ-NQIIRXRSSA-N 0.000 claims 1
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GXMUNFPAYYZTAV-WKOQGQMTSA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]-2-methylpropanamide hydrochloride Chemical compound Cl.CC(C)C(=O)NC1CCN(C[C@H]2CN(C[C@@H](C)O2)c2ccc(C#N)c3ncccc23)CC1 GXMUNFPAYYZTAV-WKOQGQMTSA-N 0.000 claims 1
BIUZBAIWKQBUPA-XXBNENTESA-N N-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]-4-fluorobenzenesulfonamide Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)NS(=O)(=O)c2ccc(F)cc2)O1)c1ccc(C#N)c2ncccc12 BIUZBAIWKQBUPA-XXBNENTESA-N 0.000 claims 1
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
239000005837 Spiroxamine Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
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VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 1
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230000001419 dependent effect Effects 0.000 claims 1
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125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
239000012894 fetal calf serum Substances 0.000 claims 1
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238000004020 luminiscence type Methods 0.000 claims 1
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QGHQQWFENKLHMN-IAQYHMDHSA-N methyl (2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholine-2-carboxylate Chemical compound COC(=O)[C@H]1CN(C[C@@H](C)O1)c1ccc(C#N)c2ncccc12 QGHQQWFENKLHMN-IAQYHMDHSA-N 0.000 claims 1
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238000007747 plating Methods 0.000 claims 1
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HPQRQAOVNXWEEQ-UHFFFAOYSA-N quinoline-8-carboxamide Chemical compound C1=CN=C2C(C(=O)N)=CC=CC2=C1 HPQRQAOVNXWEEQ-UHFFFAOYSA-N 0.000 claims 1
PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical group O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
UHUFMTFOWQSXQL-RDGATRHJSA-N tert-butyl 4-[1-[[(2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl]methyl]piperidin-4-yl]piperazine-1-carboxylate Chemical compound C[C@@H]1CN(C[C@H](CN2CCC(CC2)N2CCN(CC2)C(=O)OC(C)(C)C)O1)c1ccc(C#N)c2ncccc12 UHUFMTFOWQSXQL-RDGATRHJSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1

JP2016523329A 2013-10-14 2014-10-14 選択的に置換されたキノリン化合物 Active JP6223563B2 (ja)