JP2019502680A5 - - Google Patents
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- Publication number
- JP2019502680A5 JP2019502680A5 JP2018531058A JP2018531058A JP2019502680A5 JP 2019502680 A5 JP2019502680 A5 JP 2019502680A5 JP 2018531058 A JP2018531058 A JP 2018531058A JP 2018531058 A JP2018531058 A JP 2018531058A JP 2019502680 A5 JP2019502680 A5 JP 2019502680A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- imidazo
- pyrimidin
- tetrahydroquinolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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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
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| AU2008353145B2 (en) | 2008-01-03 | 2013-09-12 | Universite D' Aix-Marseille | Bitherapy and tritherapy used for treating an HIV-positive patient |
| AR072999A1 (es) | 2008-08-11 | 2010-10-06 | Medarex Inc | Anticuerpos humanos que se unen al gen 3 de activacion linfocitaria (lag-3) y los usos de estos |
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| EP2493862B1 (en) | 2009-10-28 | 2016-10-05 | Newlink Genetics Corporation | Imidazole derivatives as ido inhibitors |
| DK2510010T3 (en) | 2009-12-10 | 2015-12-14 | Hoffmann La Roche | Antibodies that bind to human CSF1R extracellular domain 4 and their use |
| DK2542256T3 (da) | 2010-03-04 | 2019-08-26 | Macrogenics Inc | Antistoffer reagerende med b7-h3, immunologisk aktive fragmenter deraf og anvendelser deraf |
| RU2617971C2 (ru) | 2010-03-05 | 2017-04-28 | Ф.Хоффманн-Ля Рош Аг | Антитела против csf-1r человека и их применение |
| CN102918061B (zh) | 2010-03-05 | 2016-06-08 | 霍夫曼-拉罗奇有限公司 | 针对人csf-1r的抗体及其用途 |
| EP3943154A1 (en) | 2010-05-04 | 2022-01-26 | Five Prime Therapeutics, Inc. | Antibodies that bind csf1r |
| US8080568B1 (en) | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| NZ729044A (en) | 2010-09-09 | 2020-07-31 | Pfizer | 4-1bb binding molecules |
| NO2694640T3 (enExample) | 2011-04-15 | 2018-03-17 | ||
| CA2833636A1 (en) | 2011-04-20 | 2012-10-26 | Amplimmune, Inc. | Antibodies and other molecules that bind b7-h1 and pd-1 |
| BR112014012819B1 (pt) | 2011-11-28 | 2022-08-16 | Merck Patent Gmbh | Anticorpo anti-pd-l1 ou fragmento de ligação ao antígeno do mesmo e composição |
| MX356337B (es) | 2011-12-15 | 2018-05-23 | Hoffmann La Roche | Anticuerpos contra csf-1r humano y sus usos. |
| MX2014008961A (es) | 2012-02-06 | 2014-10-14 | Genentech Inc | Composiciones y metodos para utilizar inhibidores de csf1r. |
| AR090263A1 (es) | 2012-03-08 | 2014-10-29 | Hoffmann La Roche | Terapia combinada de anticuerpos contra el csf-1r humano y las utilizaciones de la misma |
| KR20150018533A (ko) | 2012-05-11 | 2015-02-23 | 파이브 프라임 테라퓨틱스, 인크. | 콜로니 자극 인자 1 수용체(csf1r)에 결속하는 항체들에 의한 질병 상태의 치료 방법 |
| AR091649A1 (es) | 2012-07-02 | 2015-02-18 | Bristol Myers Squibb Co | Optimizacion de anticuerpos que se fijan al gen de activacion de linfocitos 3 (lag-3) y sus usos |
| CN107759690A (zh) | 2012-08-31 | 2018-03-06 | 戊瑞治疗有限公司 | 用结合群落刺激因子1受体(csf1r)的抗体治疗病状的方法 |
-
2016
- 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
- 2016-12-14 EP EP16823109.0A patent/EP3390406A1/en not_active Withdrawn
- 2016-12-14 JP JP2018531058A patent/JP6856648B2/ja active Active
- 2016-12-14 KR KR1020187019798A patent/KR102738306B1/ko active Active
- 2016-12-14 CN CN201680081803.1A patent/CN108602829A/zh active Pending
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