JP2019502680A5 - - Google Patents

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Publication number: JP2019502680A5
Authority: JP; Japan
Prior art keywords: methyl; alkyl; imidazo; pyrimidin; tetrahydroquinolin
Prior art date: 2016-12-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP2018531058A

Other languages

English (en)

Japanese (ja)

Other versions

JP6856648B2 (ja

JP2019502680A (ja

Filing date

2016-12-14

Publication date

2020-01-23

2016-12-14 Application filed filed Critical

2016-12-14 Priority claimed from PCT/US2016/066575 external-priority patent/WO2017106291A1/en

2019-01-31 Publication of JP2019502680A publication Critical patent/JP2019502680A/ja

2020-01-23 Publication of JP2019502680A5 publication Critical patent/JP2019502680A5/ja

2021-04-07 Application granted granted Critical

2021-04-07 Publication of JP6856648B2 publication Critical patent/JP6856648B2/ja

Status Active legal-status Critical Current

2036-12-14 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 123
-1 tetrahydrocinnolinyl Chemical group 0.000 claims 47
125000000753 cycloalkyl group Chemical group 0.000 claims 38
229910052739 hydrogen Inorganic materials 0.000 claims 31
239000001257 hydrogen Substances 0.000 claims 31
125000001188 haloalkyl group Chemical group 0.000 claims 28
125000005843 halogen group Chemical group 0.000 claims 27
125000003545 alkoxy group Chemical group 0.000 claims 25
125000004438 haloalkoxy group Chemical group 0.000 claims 22
125000001424 substituent group Chemical group 0.000 claims 20
125000004183 alkoxy alkyl group Chemical group 0.000 claims 17
125000002768 hydroxyalkyl group Chemical group 0.000 claims 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
150000002431 hydrogen Chemical class 0.000 claims 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 14
150000001875 compounds Chemical class 0.000 claims 12
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 12
125000004193 piperazinyl group Chemical group 0.000 claims 12
125000002393 azetidinyl group Chemical group 0.000 claims 10
125000002757 morpholinyl group Chemical group 0.000 claims 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
125000003386 piperidinyl group Chemical group 0.000 claims 10
125000004076 pyridyl group Chemical group 0.000 claims 10
125000000719 pyrrolidinyl group Chemical group 0.000 claims 10
125000001544 thienyl group Chemical group 0.000 claims 10
125000004093 cyano group Chemical group *C#N 0.000 claims 9
150000003839 salts Chemical class 0.000 claims 9
125000001475 halogen functional group Chemical group 0.000 claims 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
239000004305 biphenyl Substances 0.000 claims 7
235000010290 biphenyl Nutrition 0.000 claims 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
125000004181 carboxyalkyl group Chemical group 0.000 claims 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 7
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 6
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 5
125000002541 furyl group Chemical group 0.000 claims 5
125000001786 isothiazolyl group Chemical group 0.000 claims 5
125000000842 isoxazolyl group Chemical group 0.000 claims 5
125000001715 oxadiazolyl group Chemical group 0.000 claims 5
125000002971 oxazolyl group Chemical group 0.000 claims 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
125000003373 pyrazinyl group Chemical group 0.000 claims 5
125000003226 pyrazolyl group Chemical group 0.000 claims 5
125000002098 pyridazinyl group Chemical group 0.000 claims 5
125000000168 pyrrolyl group Chemical group 0.000 claims 5
125000003831 tetrazolyl group Chemical group 0.000 claims 5
125000001113 thiadiazolyl group Chemical group 0.000 claims 5
125000000335 thiazolyl group Chemical group 0.000 claims 5
125000001425 triazolyl group Chemical group 0.000 claims 5
239000003814 drug Substances 0.000 claims 4
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 4
125000000714 pyrimidinyl group Chemical group 0.000 claims 4
229940124597 therapeutic agent Drugs 0.000 claims 4
125000004414 alkyl thio group Chemical group 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
IFVOHRLNAVYUBX-UUKMXZOPSA-N (8S)-N-[[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrol-5-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CC3CCNC3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 IFVOHRLNAVYUBX-UUKMXZOPSA-N 0.000 claims 2
CPSBIOBWVCTGGQ-LBAQZLPGSA-N (8S)-N-[[5-(3,4,6,7,9,9a-hexahydro-1H-pyrazino[2,1-c][1,4]oxazin-8-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1OCCN2C1CN(CC2)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C CPSBIOBWVCTGGQ-LBAQZLPGSA-N 0.000 claims 2
QHXULMRXASKLHF-KVZIAJEVSA-N (8S)-N-[[5-(3,6-diazabicyclo[3.2.0]heptan-3-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C12CN(CC2NC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C QHXULMRXASKLHF-KVZIAJEVSA-N 0.000 claims 2
BWASTCHPIZZPOG-CKHPTIKVSA-N (8S)-N-methyl-N-[[5-(1-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-5-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CC3CCN(C)C3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 BWASTCHPIZZPOG-CKHPTIKVSA-N 0.000 claims 2
VEYRVHBWYMJASJ-IRQNMHNUSA-N (8S)-N-methyl-N-[[5-(1-methyl-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b]pyridin-6-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CC3CCCN(C)C3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 VEYRVHBWYMJASJ-IRQNMHNUSA-N 0.000 claims 2
YGVNKXNCNWWXGL-CGAIIQECSA-N (8S)-N-methyl-N-[[5-(3-phenylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CC(NCC2)C2=CC=CC=C2)C=1 YGVNKXNCNWWXGL-CGAIIQECSA-N 0.000 claims 2
RMXJVGZWTJMJKQ-INIZCTEOSA-N (4S)-N-methyl-N-[(5-piperazin-1-ylimidazo[1,2-c]pyrimidin-2-yl)methyl]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCNCC2)=N1)[C@H]1CCOC2=C1N=CC=C2 RMXJVGZWTJMJKQ-INIZCTEOSA-N 0.000 claims 1
FHNOXJUXHNIMEU-KRWDZBQOSA-N (8S)-N-[(7-chloro-5-piperazin-1-ylimidazo[1,2-c]pyrimidin-2-yl)methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound ClC1=CC=2N(C(=N1)N1CCNCC1)C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C FHNOXJUXHNIMEU-KRWDZBQOSA-N 0.000 claims 1
FSBJWIFGTIJMBU-SFHVURJKSA-N (8S)-N-[(7-methoxy-5-piperazin-1-ylimidazo[1,2-c]pyrimidin-2-yl)methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COC1=CC=2N(C(=N1)N1CCNCC1)C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C FSBJWIFGTIJMBU-SFHVURJKSA-N 0.000 claims 1
PXOBFQBPRBONFP-MNLRITNHSA-N (8S)-N-[[5-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N1C2C(CCC1)CN(C2)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C PXOBFQBPRBONFP-MNLRITNHSA-N 0.000 claims 1
SYCJZZJWNRKWAT-KEKNWZKVSA-N (8S)-N-[[5-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN3CCCCC3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 SYCJZZJWNRKWAT-KEKNWZKVSA-N 0.000 claims 1
FIGMUWNNIJLWCI-QLOJAFMTSA-N (8S)-N-[[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CC3CNCC3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 FIGMUWNNIJLWCI-QLOJAFMTSA-N 0.000 claims 1
FEKAPINKCFNKFT-DAFXYXGESA-N (8S)-N-[[5-(3-aminopyrrolidin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound NC1CN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C FEKAPINKCFNKFT-DAFXYXGESA-N 0.000 claims 1
ANQGHJJBZQPELL-VWLOTQADSA-N (8S)-N-[[5-(4-benzylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C ANQGHJJBZQPELL-VWLOTQADSA-N 0.000 claims 1
NYYSZAFJFOWCRE-QFIPXVFZSA-N (8S)-N-[[5-(4-cyclobutylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1(CCC1)N1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C NYYSZAFJFOWCRE-QFIPXVFZSA-N 0.000 claims 1
XQVBYEARLDIBAE-DEOSSOPVSA-N (8S)-N-[[5-(4-cyclohexylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1(CCCCC1)N1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C XQVBYEARLDIBAE-DEOSSOPVSA-N 0.000 claims 1
NCTFMMKOVGUVQU-FQEVSTJZSA-N (8S)-N-[[5-(4-ethylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN1CCN(CC1)c1nccc2nc(CN(C)[C@H]3CCCc4cccnc34)cn12 NCTFMMKOVGUVQU-FQEVSTJZSA-N 0.000 claims 1
VHPZQGAERZKKAU-SFHVURJKSA-N (8S)-N-[[5-(6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN3C=NN=C3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 VHPZQGAERZKKAU-SFHVURJKSA-N 0.000 claims 1
GNISBZINWLBVRK-IBGZPJMESA-N (8S)-N-[[5-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N=1C=CN2C=1CN(CC2)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C GNISBZINWLBVRK-IBGZPJMESA-N 0.000 claims 1
XLFOKULIOUVDQY-QKLQHJQFSA-N (8S)-N-[[5-[(3R,5S)-3,5-dimethylpiperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C[C@H]1CN(C[C@H](N1)C)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C XLFOKULIOUVDQY-QKLQHJQFSA-N 0.000 claims 1
WLNRVVQWSVGANM-JBACZVJFSA-N (8S)-N-[[5-[(7S,8aS)-7-fluoro-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound F[C@H]1C[C@@H]2N(CCN(C2)C2=NC=CC=3N2C=C(N=3)CN([C@H]2CCCC=3C=CC=NC2=3)C)C1 WLNRVVQWSVGANM-JBACZVJFSA-N 0.000 claims 1
IHXUHJJGTURPBK-SFTDATJTSA-N (8S)-N-[[5-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN3CCC[C@H]3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 IHXUHJJGTURPBK-SFTDATJTSA-N 0.000 claims 1
UGGDWXMDOLJGGU-ANYOKISRSA-N (8S)-N-[[5-[3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(C)C1CCN(C1)C1=NC=CC2=NC(CN(C)[C@H]3CCCC4=C3N=CC=C4)=CN12 UGGDWXMDOLJGGU-ANYOKISRSA-N 0.000 claims 1
QNWZSXRYUMGRHQ-NRFANRHFSA-N (8S)-N-[[5-[4-(1H-imidazol-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=NC=CN3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 QNWZSXRYUMGRHQ-NRFANRHFSA-N 0.000 claims 1
DHTOALAOSQLXGE-FQEVSTJZSA-N (8S)-N-[[5-[4-(2-aminoethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CCN)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 DHTOALAOSQLXGE-FQEVSTJZSA-N 0.000 claims 1
QHMGWUIDNJPKKS-FQEVSTJZSA-N (8S)-N-[[5-[4-(2-fluoroethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CCF)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 QHMGWUIDNJPKKS-FQEVSTJZSA-N 0.000 claims 1
OJGQKLCBXDYYIJ-DEOSSOPVSA-N (8S)-N-[[5-[4-(3-chlorophenyl)sulfonylpiperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound ClC=1C=C(C=CC=1)S(=O)(=O)N1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C OJGQKLCBXDYYIJ-DEOSSOPVSA-N 0.000 claims 1
RRWKZWAJLJOSDO-DEOSSOPVSA-N (8S)-N-[[5-[4-(benzenesulfonyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC2)S(=O)(=O)C2=CC=CC=C2)=N1)[C@H]1CCCC2=C1N=CC=C2 RRWKZWAJLJOSDO-DEOSSOPVSA-N 0.000 claims 1
QRBFPBOGZSHACW-DEOSSOPVSA-N (8S)-N-[[5-[4-(cyclopentylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1(CCCC1)CN1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C QRBFPBOGZSHACW-DEOSSOPVSA-N 0.000 claims 1
QCKVLNRMSRMRNG-QFIPXVFZSA-N (8S)-N-[[5-[4-(cyclopropylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3CC3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 QCKVLNRMSRMRNG-QFIPXVFZSA-N 0.000 claims 1
GELUIMKKZCGLLC-QHCPKHFHSA-N (8S)-N-[[5-[4-(furan-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound O1C(=CC=C1)CN1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C GELUIMKKZCGLLC-QHCPKHFHSA-N 0.000 claims 1
ZPZXKZCIUXHFDU-MHZLTWQESA-N (8S)-N-[[5-[4-[[4-(dimethylamino)phenyl]methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(C1=CC=C(C=C1)CN1CCN(CC1)C1=NC=CC=2N1C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C)C ZPZXKZCIUXHFDU-MHZLTWQESA-N 0.000 claims 1
YVFYATSBHMMITD-IBGZPJMESA-N (8S)-N-[[7-methoxy-5-(4-methylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COc1cc2nc(CN(C)[C@H]3CCCc4cccnc34)cn2c(n1)N1CCN(C)CC1 YVFYATSBHMMITD-IBGZPJMESA-N 0.000 claims 1
YPOGGICGTBXUAW-HNNXBMFYSA-N (8S)-N-methyl-N-[(5-methylsulfanylimidazo[1,2-c]pyrimidin-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)SC)C=1 YPOGGICGTBXUAW-HNNXBMFYSA-N 0.000 claims 1
AHIGYKYVVYUNAV-SFHVURJKSA-N (8S)-N-methyl-N-[(5-morpholin-4-ylimidazo[1,2-c]pyrimidin-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCOCC2)=N1)[C@H]1CCCC2=C1N=CC=C2 AHIGYKYVVYUNAV-SFHVURJKSA-N 0.000 claims 1
OSMYWFFIBKMYSD-GRERDSQWSA-N (8S)-N-methyl-N-[[5-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CC3CN(C)CC3C2)=N1)[C@H]1CCCC2=C1N=CC=C2 OSMYWFFIBKMYSD-GRERDSQWSA-N 0.000 claims 1
RKUCPMGCBOAYKR-IBGZPJMESA-N (8S)-N-methyl-N-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(Cc1cn2c(nccc2n1)N1CCN(C)CC1)[C@H]1CCCc2cccnc12 RKUCPMGCBOAYKR-IBGZPJMESA-N 0.000 claims 1
AANGCPZMXBIIDX-IBGZPJMESA-N (8S)-N-methyl-N-[[5-(4-methylsulfonylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC2)S(C)(=O)=O)=N1)[C@H]1CCCC2=C1N=CC=C2 AANGCPZMXBIIDX-IBGZPJMESA-N 0.000 claims 1
ZJPHXNDCLXBJBW-NRFANRHFSA-N (8S)-N-methyl-N-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)N1CCN(CC1)C1=NC=CC2=NC(CN(C)[C@H]3CCCC4=C3N=CC=C4)=CN12 ZJPHXNDCLXBJBW-NRFANRHFSA-N 0.000 claims 1
NBHTXLQJGFMSDW-NRFANRHFSA-N (8S)-N-methyl-N-[[5-(4-propan-2-ylsulfonylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)S(=O)(=O)N1CCN(CC1)C1=NC=CC2=NC(CN(C)[C@H]3CCCC4=C3N=CC=C4)=CN12 NBHTXLQJGFMSDW-NRFANRHFSA-N 0.000 claims 1
RFDXAXKKTHINBT-QHCPKHFHSA-N (8S)-N-methyl-N-[[5-(4-pyridin-3-ylsulfonylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC2)S(=O)(=O)C2=CC=CN=C2)=N1)[C@H]1CCCC2=C1N=CC=C2 RFDXAXKKTHINBT-QHCPKHFHSA-N 0.000 claims 1
CMHGUYMQOOQIJI-NRFANRHFSA-N (8S)-N-methyl-N-[[5-(4-thiophen-2-ylsulfonylpiperazin-1-yl)imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)S(=O)(=O)C=2SC=CC=2)C=1 CMHGUYMQOOQIJI-NRFANRHFSA-N 0.000 claims 1
NUWLUVUYKVXYLX-UEXGIBASSA-N (8S)-N-methyl-N-[[5-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C[C@H]1CN(C[C@@H](C)N1C)c1nccc2nc(CN(C)[C@H]3CCCc4cccnc34)cn12 NUWLUVUYKVXYLX-UEXGIBASSA-N 0.000 claims 1
KRXQOQBUAKHXPX-NRFANRHFSA-N (8S)-N-methyl-N-[[5-[4-(1,3-thiazol-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=NC=CS3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 KRXQOQBUAKHXPX-NRFANRHFSA-N 0.000 claims 1
ZFBFBBIQHXTWDQ-DEOSSOPVSA-N (8S)-N-methyl-N-[[5-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)C2CCN(CC2)C)C=1 ZFBFBBIQHXTWDQ-DEOSSOPVSA-N 0.000 claims 1
SZGHHZXCNFIIJZ-IBGZPJMESA-N (8S)-N-methyl-N-[[5-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC(F)(F)F)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 SZGHHZXCNFIIJZ-IBGZPJMESA-N 0.000 claims 1
WFUDWZQGVPVMFG-FQEVSTJZSA-N (8S)-N-methyl-N-[[5-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)CCC(F)(F)F)C=1 WFUDWZQGVPVMFG-FQEVSTJZSA-N 0.000 claims 1
YPLVPBAAEABBJC-QHCPKHFHSA-N (8S)-N-methyl-N-[[5-[4-(3-methylbutyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)CCN1CCN(CC1)C1=NC=CC2=NC(CN(C)[C@H]3CCCC4=C3N=CC=C4)=CN12 YPLVPBAAEABBJC-QHCPKHFHSA-N 0.000 claims 1
IUWBEAXSUOGSFS-WCSIJFPASA-N (8S)-N-methyl-N-[[5-[4-(oxolan-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3CCCO3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 IUWBEAXSUOGSFS-WCSIJFPASA-N 0.000 claims 1
SXXFPTBEMTVDDG-AKRCKQFNSA-N (8S)-N-methyl-N-[[5-[4-(oxolan-3-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3CCOC3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 SXXFPTBEMTVDDG-AKRCKQFNSA-N 0.000 claims 1
LPNWQENNSQKLRN-DEOSSOPVSA-N (8S)-N-methyl-N-[[5-[4-(pyridin-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=NC=CC=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 LPNWQENNSQKLRN-DEOSSOPVSA-N 0.000 claims 1
BISMTIZYXADOPJ-DEOSSOPVSA-N (8S)-N-methyl-N-[[5-[4-(pyridin-3-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC=CN=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 BISMTIZYXADOPJ-DEOSSOPVSA-N 0.000 claims 1
GKSSVXGPAZGLKX-DEOSSOPVSA-N (8S)-N-methyl-N-[[5-[4-(pyridin-4-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC=NC=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 GKSSVXGPAZGLKX-DEOSSOPVSA-N 0.000 claims 1
HJUOUQNIOSSDSQ-QHCPKHFHSA-N (8S)-N-methyl-N-[[5-[4-(thiophen-2-ylmethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC=CS3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 HJUOUQNIOSSDSQ-QHCPKHFHSA-N 0.000 claims 1
RKUCPMGCBOAYKR-COJYBMMNSA-N (8S)-N-methyl-N-[[5-[4-(trideuteriomethyl)piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)C([2H])([2H])[2H])C=1 RKUCPMGCBOAYKR-COJYBMMNSA-N 0.000 claims 1
ZOZDIVKOTRPSAJ-QFIPXVFZSA-N (8S)-N-methyl-N-[[5-[4-[(1-methylimidazol-2-yl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=NC=CN3C)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 ZOZDIVKOTRPSAJ-QFIPXVFZSA-N 0.000 claims 1
IAYHNBZPDOKUDP-DEOSSOPVSA-N (8S)-N-methyl-N-[[5-[4-[(1-methylpyrrol-2-yl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)CC=2N(C=CC=2)C)C=1 IAYHNBZPDOKUDP-DEOSSOPVSA-N 0.000 claims 1
LUKQNQYSNAEGAD-QHCPKHFHSA-N (8S)-N-methyl-N-[[5-[4-[(3-methylimidazol-4-yl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CN=CN3C)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 LUKQNQYSNAEGAD-QHCPKHFHSA-N 0.000 claims 1
SGHPJFSCEVQMQM-SANMLTNESA-N (8S)-N-methyl-N-[[5-[4-[(3-methylphenyl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC(C)=CC=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 SGHPJFSCEVQMQM-SANMLTNESA-N 0.000 claims 1
NXFIZMWFMLLHEO-HKBQPEDESA-N (8S)-N-methyl-N-[[5-[4-[(3-phenoxyphenyl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC(OC4=CC=CC=C4)=CC=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 NXFIZMWFMLLHEO-HKBQPEDESA-N 0.000 claims 1
HZQHIFLZKQJVJY-SANMLTNESA-N (8S)-N-methyl-N-[[5-[4-[(4-methylphenyl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC=C(C)C=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 HZQHIFLZKQJVJY-SANMLTNESA-N 0.000 claims 1
SGKJKILHMYYXNS-HKBQPEDESA-N (8S)-N-methyl-N-[[5-[4-[(4-phenylphenyl)methyl]piperazin-1-yl]imidazo[1,2-c]pyrimidin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC3=CC=C(C=C3)C3=CC=CC=C3)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 SGKJKILHMYYXNS-HKBQPEDESA-N 0.000 claims 1
NCPTUBRVAQWRSB-FQEVSTJZSA-N 1-[4-[2-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-c]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CC2)C(C)=O)=N1)[C@H]1CCCC2=C1N=CC=C2 NCPTUBRVAQWRSB-FQEVSTJZSA-N 0.000 claims 1
UENRYYSJOAZKNV-FQEVSTJZSA-N 2-[4-[2-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-c]pyrimidin-5-yl]piperazin-1-yl]ethanol Chemical compound CN(CC1=CN2C(C=CN=C2N2CCN(CCO)CC2)=N1)[C@H]1CCCC2=C1N=CC=C2 UENRYYSJOAZKNV-FQEVSTJZSA-N 0.000 claims 1
FIAKFJOKXMPQTR-KRWDZBQOSA-N 2-[[4-aminobutyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-6H-imidazo[1,2-c]pyrimidin-5-one Chemical compound NCCCCN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)O)C=1 FIAKFJOKXMPQTR-KRWDZBQOSA-N 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
UKOFAXWNKGCWRI-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)imidazo[1,2-c]pyrimidine-2-carbaldehyde Chemical compound CN1CCN(CC1)C1=NC=CC=2N1C=C(N=2)C=O UKOFAXWNKGCWRI-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
206010006187 Breast cancer Diseases 0.000 claims 1
208000026310 Breast neoplasm Diseases 0.000 claims 1
102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims 1
206010009944 Colon cancer Diseases 0.000 claims 1
208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims 1
208000034578 Multiple myelomas Diseases 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 claims 1
206010033128 Ovarian cancer Diseases 0.000 claims 1
206010061535 Ovarian neoplasm Diseases 0.000 claims 1
206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
206010035226 Plasma cell myeloma Diseases 0.000 claims 1
206010060862 Prostate cancer Diseases 0.000 claims 1
208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
206010041067 Small cell lung cancer Diseases 0.000 claims 1
208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 1
201000011176 T-cell adult acute lymphocytic leukemia Diseases 0.000 claims 1
MROQMFAUUWKATN-SFHVURJKSA-N [2-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-piperazin-1-ylimidazo[1,2-c]pyrimidin-3-yl]methanol Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCNCC2)C=1CO MROQMFAUUWKATN-SFHVURJKSA-N 0.000 claims 1
MSDSBOZZEQSSNZ-IBGZPJMESA-N [5-(4-methylpiperazin-1-yl)-2-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-c]pyrimidin-3-yl]methanol Chemical compound CN([C@H]1CCCC=2C=CC=NC1=2)CC=1N=C2N(C(=NC=C2)N2CCN(CC2)C)C=1CO MSDSBOZZEQSSNZ-IBGZPJMESA-N 0.000 claims 1
AUGVJMFIDKSLFX-FQEVSTJZSA-N [7-methoxy-5-(4-methylpiperazin-1-yl)-2-[[methyl-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-c]pyrimidin-8-yl]methanol Chemical compound COC1=C(C=2N(C(=N1)N1CCN(CC1)C)C=C(N=2)CN([C@H]1CCCC=2C=CC=NC1=2)C)CO AUGVJMFIDKSLFX-FQEVSTJZSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical group OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
201000001441 melanoma Diseases 0.000 claims 1
RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
201000002528 pancreatic cancer Diseases 0.000 claims 1
208000008443 pancreatic carcinoma Diseases 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
208000000587 small cell lung carcinoma Diseases 0.000 claims 1
KMQFNRGRKSFZQC-UHFFFAOYSA-N tert-butyl 4-(2-formylimidazo[1,2-c]pyrimidin-5-yl)piperazine-1-carboxylate Chemical compound C(=O)C=1N=C2N(C(=NC=C2)N2CCN(CC2)C(=O)OC(C)(C)C)C=1 KMQFNRGRKSFZQC-UHFFFAOYSA-N 0.000 claims 1
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1

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- 2016-12-14 EP EP16823109.0A patent/EP3390406A1/en not_active Withdrawn
- 2016-12-14 CN CN201680081803.1A patent/CN108602829A/zh active Pending
- 2016-12-14 KR KR1020187019798A patent/KR102738306B1/ko active Active
- 2016-12-14 US US15/776,936 patent/US10450318B2/en active Active
- 2016-12-14 WO PCT/US2016/066575 patent/WO2017106291A1/en not_active Ceased

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