JP2017510595A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017510595A5 JP2017510595A5 JP2016560952A JP2016560952A JP2017510595A5 JP 2017510595 A5 JP2017510595 A5 JP 2017510595A5 JP 2016560952 A JP2016560952 A JP 2016560952A JP 2016560952 A JP2016560952 A JP 2016560952A JP 2017510595 A5 JP2017510595 A5 JP 2017510595A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- anilino
- dihydropyrimido
- indolizine
- methoxy
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 homopiperazinyl Chemical group 0.000 claims description 52
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- VNEZLSKCYNTZLU-UHFFFAOYSA-N C1(CC1)C(=O)N1CCN(CC1)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC Chemical compound C1(CC1)C(=O)N1CCN(CC1)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC VNEZLSKCYNTZLU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 59
- 125000003545 alkoxy group Chemical group 0.000 claims 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 19
- URGAFFAIKGXTJC-UHFFFAOYSA-N indolizine-7-carboxamide Chemical compound C1=C(C(=O)N)C=CN2C=CC=C21 URGAFFAIKGXTJC-UHFFFAOYSA-N 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- UYPNZGVGCJECJV-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC12)C=NC(=N3)NC3=C(C=C(C=C3)N3CCNCC3)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC12)C=NC(=N3)NC3=C(C=C(C=C3)N3CCNCC3)OC UYPNZGVGCJECJV-UHFFFAOYSA-N 0.000 claims 2
- XPORPDHLTHKBQR-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-[2-methoxy-4-[4-(2-methoxyacetyl)piperazin-1-yl]anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(COC)=O)OC XPORPDHLTHKBQR-UHFFFAOYSA-N 0.000 claims 2
- CMSARXIYXRBTSN-UHFFFAOYSA-N N-(3,5-diethyl-1H-pyrazol-4-yl)-2-[2-(difluoromethoxy)-4-(4-methylpiperazin-1-yl)anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC(F)F)CC CMSARXIYXRBTSN-UHFFFAOYSA-N 0.000 claims 2
- PXOSVHWTKXCACO-UHFFFAOYSA-N N-[3,5-diethyl-1-[2-(2-methoxyethoxy)ethyl]pyrazol-4-yl]-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC)CCOCCOC PXOSVHWTKXCACO-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- FEPTTWBIJAOREA-UHFFFAOYSA-N BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C FEPTTWBIJAOREA-UHFFFAOYSA-N 0.000 claims 1
- SCNJHTNENAOJON-UHFFFAOYSA-N BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC Chemical compound BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC SCNJHTNENAOJON-UHFFFAOYSA-N 0.000 claims 1
- LNYQMDKVTIRBIZ-UHFFFAOYSA-N BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C Chemical compound BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C LNYQMDKVTIRBIZ-UHFFFAOYSA-N 0.000 claims 1
- SMTVCUWSXLIKHQ-UHFFFAOYSA-N BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC Chemical compound BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC SMTVCUWSXLIKHQ-UHFFFAOYSA-N 0.000 claims 1
- SKOVQURQPGBBNK-UHFFFAOYSA-N BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C Chemical compound BrC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C SKOVQURQPGBBNK-UHFFFAOYSA-N 0.000 claims 1
- LBDJJKHJZVLVBY-UHFFFAOYSA-N C(#N)C1(CCN(CC1)C(=O)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC)C Chemical compound C(#N)C1(CCN(CC1)C(=O)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC)C LBDJJKHJZVLVBY-UHFFFAOYSA-N 0.000 claims 1
- KKPQZYIFMSQJBT-UHFFFAOYSA-N C(#N)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC Chemical compound C(#N)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC KKPQZYIFMSQJBT-UHFFFAOYSA-N 0.000 claims 1
- QSHOMXOBJBDIRW-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C QSHOMXOBJBDIRW-UHFFFAOYSA-N 0.000 claims 1
- BOBDWLYTHZDBMJ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C Chemical compound C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C BOBDWLYTHZDBMJ-UHFFFAOYSA-N 0.000 claims 1
- MFNREBDYDUKFFP-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC Chemical compound C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC MFNREBDYDUKFFP-UHFFFAOYSA-N 0.000 claims 1
- WHLBQJTZROBCCV-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=CC=C(C=C1)N1CCN(CC1)C Chemical compound C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=CC=C(C=C1)N1CCN(CC1)C WHLBQJTZROBCCV-UHFFFAOYSA-N 0.000 claims 1
- DPRUUGIKMIGILV-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C Chemical compound C(C)C1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C DPRUUGIKMIGILV-UHFFFAOYSA-N 0.000 claims 1
- ZBODMVDQKFDZCC-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CC(NCC1)C)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CC(NCC1)C)OC ZBODMVDQKFDZCC-UHFFFAOYSA-N 0.000 claims 1
- OGGAOOUUURDBQI-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C OGGAOOUUURDBQI-UHFFFAOYSA-N 0.000 claims 1
- HGEIUFJVGHMGRR-GKOSEXJESA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC([2H])([2H])[2H] Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC([2H])([2H])[2H] HGEIUFJVGHMGRR-GKOSEXJESA-N 0.000 claims 1
- VLWWXJPSQIIXON-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C VLWWXJPSQIIXON-UHFFFAOYSA-N 0.000 claims 1
- NBHJPPJQLVRDJM-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC NBHJPPJQLVRDJM-UHFFFAOYSA-N 0.000 claims 1
- SVXSPFBVTLNHQK-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCOCC1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCOCC1)C SVXSPFBVTLNHQK-UHFFFAOYSA-N 0.000 claims 1
- GRNNRSLFMMPOHP-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=NC=1)N1CCN(CC1)C)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=NC=1)N1CCN(CC1)C)OC GRNNRSLFMMPOHP-UHFFFAOYSA-N 0.000 claims 1
- NPYJENQOQDQDTL-VPYROQPTSA-N C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC([2H])([2H])[2H])CC)CCOC Chemical compound C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC([2H])([2H])[2H])CC)CCOC NPYJENQOQDQDTL-VPYROQPTSA-N 0.000 claims 1
- NPYJENQOQDQDTL-UHFFFAOYSA-N C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC)CCOC Chemical compound C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC)CCOC NPYJENQOQDQDTL-UHFFFAOYSA-N 0.000 claims 1
- TWSAJNVVUWAGJA-UHFFFAOYSA-N C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC)CCOC Chemical compound C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC)CCOC TWSAJNVVUWAGJA-UHFFFAOYSA-N 0.000 claims 1
- SLYWKRDDNXNSJS-UHFFFAOYSA-N C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C)CC)CCOC Chemical compound C(C)C1=NN(C(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C)CC)CCOC SLYWKRDDNXNSJS-UHFFFAOYSA-N 0.000 claims 1
- OKAONXZTHIKEGJ-UHFFFAOYSA-N C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C)CC Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C)CC OKAONXZTHIKEGJ-UHFFFAOYSA-N 0.000 claims 1
- NLFIURXIRTXRJC-UHFFFAOYSA-N C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC NLFIURXIRTXRJC-UHFFFAOYSA-N 0.000 claims 1
- ALKFMFBIVZPDBX-UHFFFAOYSA-N C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC ALKFMFBIVZPDBX-UHFFFAOYSA-N 0.000 claims 1
- LDKYLFSTCJOLIB-UHFFFAOYSA-N C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C)CC Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C)CC LDKYLFSTCJOLIB-UHFFFAOYSA-N 0.000 claims 1
- QGLJBTYQTYGABA-UHFFFAOYSA-N C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC Chemical compound C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)CC QGLJBTYQTYGABA-UHFFFAOYSA-N 0.000 claims 1
- QUKFNMJOGZDJEI-UHFFFAOYSA-N C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC Chemical compound C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)CC QUKFNMJOGZDJEI-UHFFFAOYSA-N 0.000 claims 1
- SPCVBNPRJSHJSM-UHFFFAOYSA-N C1(CC1)NC(=O)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC Chemical compound C1(CC1)NC(=O)C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC SPCVBNPRJSHJSM-UHFFFAOYSA-N 0.000 claims 1
- MGPYIJOWGJNBBJ-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCN(CCC1)CC)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCN(CCC1)CC)OC MGPYIJOWGJNBBJ-UHFFFAOYSA-N 0.000 claims 1
- ICVDOGGLOASIIS-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCOCC1)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCOCC1)OC ICVDOGGLOASIIS-UHFFFAOYSA-N 0.000 claims 1
- HUQUKSMBGVAFBL-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCS(CC1)(=O)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(=O)N1CCS(CC1)(=O)=O)OC HUQUKSMBGVAFBL-UHFFFAOYSA-N 0.000 claims 1
- KQBLISXQFLAKSK-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC(C)C)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC(C)C)=O)OC KQBLISXQFLAKSK-UHFFFAOYSA-N 0.000 claims 1
- VTTOYUZFKBLXQH-AELKHGAFSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC1[C@H]2COC[C@@H]12)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC1[C@H]2COC[C@@H]12)=O)OC VTTOYUZFKBLXQH-AELKHGAFSA-N 0.000 claims 1
- KMCOURQJISZVKR-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NCC(C)(C)O)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NCC(C)(C)O)=O)OC KMCOURQJISZVKR-UHFFFAOYSA-N 0.000 claims 1
- YHZIXEPSSAELJP-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NCCOC)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NCCOC)=O)OC YHZIXEPSSAELJP-UHFFFAOYSA-N 0.000 claims 1
- SRCKKJUNSLLPBW-BJKOFHAPSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(N[C@H]1[C@H](CNCC1)F)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(N[C@H]1[C@H](CNCC1)F)=O)OC SRCKKJUNSLLPBW-BJKOFHAPSA-N 0.000 claims 1
- QNNNGVBJQXEDCK-NAKRPHOHSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(N[C@H]1[C@H](CNCC1)OC)=O)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(N[C@H]1[C@H](CNCC1)OC)=O)OC QNNNGVBJQXEDCK-NAKRPHOHSA-N 0.000 claims 1
- HGXWFTJMCPHRRB-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1(CNC1)C)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1(CNC1)C)OC HGXWFTJMCPHRRB-UHFFFAOYSA-N 0.000 claims 1
- MUYCDCOARSMWLA-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1(COC1)C)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1(COC1)C)OC MUYCDCOARSMWLA-UHFFFAOYSA-N 0.000 claims 1
- HHCRSAPTZFIAEK-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1CC(C1)F)OC Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1CC(C1)F)OC HHCRSAPTZFIAEK-UHFFFAOYSA-N 0.000 claims 1
- MKBOGVSXDUWWMC-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C MKBOGVSXDUWWMC-UHFFFAOYSA-N 0.000 claims 1
- WREYRYCBWFQCSO-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCOCC1)C Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCOCC1)C WREYRYCBWFQCSO-UHFFFAOYSA-N 0.000 claims 1
- KAHQNDNXKQWCIM-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C KAHQNDNXKQWCIM-UHFFFAOYSA-N 0.000 claims 1
- SAENSMVHFBWPHD-UHFFFAOYSA-N CN(CCCN(C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC=3C(=NN(C=3C)CCOCCOCCOC)C)N=2)C=C1)OC)C)C Chemical compound CN(CCCN(C1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC=3C(=NN(C=3C)CCOCCOCCOC)C)N=2)C=C1)OC)C)C SAENSMVHFBWPHD-UHFFFAOYSA-N 0.000 claims 1
- HHEZIJFTEXKGOB-UHFFFAOYSA-N CN(CCOC1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC)C Chemical compound CN(CCOC1=CC(=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=C1)OC)C HHEZIJFTEXKGOB-UHFFFAOYSA-N 0.000 claims 1
- JJAOJIXTOMFGPK-UHFFFAOYSA-N COCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C=1C(=NN(C=1C)C)C)OC)C Chemical compound COCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C=1C(=NN(C=1C)C)C)OC)C JJAOJIXTOMFGPK-UHFFFAOYSA-N 0.000 claims 1
- PTKFYFCCZZHLLA-UHFFFAOYSA-N COCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1CN(C1)C)OC)C Chemical compound COCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(=O)C1CN(C1)C)OC)C PTKFYFCCZZHLLA-UHFFFAOYSA-N 0.000 claims 1
- QGKKEKDFRFTNGP-UHFFFAOYSA-N COCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)C Chemical compound COCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)C QGKKEKDFRFTNGP-UHFFFAOYSA-N 0.000 claims 1
- YVLYYEGKAWBIBJ-UHFFFAOYSA-N COCCOCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)C Chemical compound COCCOCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC)C YVLYYEGKAWBIBJ-UHFFFAOYSA-N 0.000 claims 1
- PMRSBOKDCNVKIG-UHFFFAOYSA-N COCCOCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCOC)OC)C Chemical compound COCCOCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCOC)OC)C PMRSBOKDCNVKIG-UHFFFAOYSA-N 0.000 claims 1
- UTRIVKIUQMSOJH-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC1CCN(CC1)C)=O)OC Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC1CCN(CC1)C)=O)OC UTRIVKIUQMSOJH-UHFFFAOYSA-N 0.000 claims 1
- LAAIDRIBFLBTCW-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C LAAIDRIBFLBTCW-UHFFFAOYSA-N 0.000 claims 1
- SCQODQQPSBJUEF-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC(F)F Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC(F)F SCQODQQPSBJUEF-UHFFFAOYSA-N 0.000 claims 1
- MIFCWQHNAMSTAG-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C MIFCWQHNAMSTAG-UHFFFAOYSA-N 0.000 claims 1
- OOESAPRLEIQOOD-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)OC OOESAPRLEIQOOD-UHFFFAOYSA-N 0.000 claims 1
- FTUSRACPOVUNAB-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)C FTUSRACPOVUNAB-UHFFFAOYSA-N 0.000 claims 1
- ZKTJNPRNPUQPIV-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OC1CCN(CC1)C)OC ZKTJNPRNPUQPIV-UHFFFAOYSA-N 0.000 claims 1
- BKCFERJHYSDBIG-UHFFFAOYSA-N ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C Chemical compound ClC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC=1C(=NC(=CC=1)N1CCOCC1)C BKCFERJHYSDBIG-UHFFFAOYSA-N 0.000 claims 1
- WXXHRCLKKWMDIL-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)C WXXHRCLKKWMDIL-UHFFFAOYSA-N 0.000 claims 1
- FPIMPJBOKCFYNW-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC FPIMPJBOKCFYNW-UHFFFAOYSA-N 0.000 claims 1
- ACNSQTJBWTVKKU-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C ACNSQTJBWTVKKU-UHFFFAOYSA-N 0.000 claims 1
- VIHYCKHHIQOMPD-UHFFFAOYSA-N FC(OC1=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=CC(=C1)C(NC1CCN(CC1)C)=O)F Chemical compound FC(OC1=C(NC=2N=CC3=C(N4C=CC(=C4CC3)C(=O)NC3=C(C=CC=C3C)C)N=2)C=CC(=C1)C(NC1CCN(CC1)C)=O)F VIHYCKHHIQOMPD-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AGPXGQNJJJOBLB-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-(2-methyl-4-piperazin-1-ylanilino)-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCNCC1)C AGPXGQNJJJOBLB-UHFFFAOYSA-N 0.000 claims 1
- WRYZBCKSXQMHKO-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-[2-methoxy-4-(oxan-4-ylcarbamoyl)anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound CC1=C(C(=CC=C1)C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)C(NC1CCOCC1)=O)OC WRYZBCKSXQMHKO-UHFFFAOYSA-N 0.000 claims 1
- PNBALSMSDYPXFO-UHFFFAOYSA-N N-[1-[2-(2-ethoxyethoxy)ethyl]-3,5-diethylpyrazol-4-yl]-2-[2-methoxy-4-[4-(2-methoxyacetyl)piperazin-1-yl]anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(COC)=O)OC)CC PNBALSMSDYPXFO-UHFFFAOYSA-N 0.000 claims 1
- NIFYAXNEECFWPW-UHFFFAOYSA-N N-[1-[2-(2-ethoxyethoxy)ethyl]-3,5-diethylpyrazol-4-yl]-2-[4-[4-[2-(ethylamino)acetyl]piperazin-1-yl]-2-methoxyanilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound C(C)OCCOCCN1N=C(C(=C1CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C(CNCC)=O)OC)CC NIFYAXNEECFWPW-UHFFFAOYSA-N 0.000 claims 1
- QVPQDJAVWIJHRM-UHFFFAOYSA-N N-[1-[2-(2-ethoxyethoxy)ethyl]-3,5-dimethylpyrazol-4-yl]-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound C(C)OCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)C QVPQDJAVWIJHRM-UHFFFAOYSA-N 0.000 claims 1
- UFIJTGYZCFZMPA-UHFFFAOYSA-N N-[1-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,5-dimethylpyrazol-4-yl]-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5,6-dihydropyrimido[4,5-e]indolizine-7-carboxamide Chemical compound COCCOCCOCCN1N=C(C(=C1C)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)N1CCN(CC1)C)OC)C UFIJTGYZCFZMPA-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- BBQZWKVMDCAMHS-UHFFFAOYSA-N pyrimido[4,5-e]indolizine-7-carboxamide Chemical compound N1=CN=CC2=C1N1C=CC(=C1C=C2)C(=O)N BBQZWKVMDCAMHS-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- LDUCMSVRKKDATH-UHFFFAOYSA-N 2-bromo-6-methylaniline Chemical compound CC1=CC=CC(Br)=C1N LDUCMSVRKKDATH-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FZIMDRORYRFCMW-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCN(C)C)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCN(C)C)OC FZIMDRORYRFCMW-UHFFFAOYSA-N 0.000 description 1
- YHGJHTMBMIUDIY-UHFFFAOYSA-N C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCN(C)C)OC)CC Chemical compound C(C)C1=NNC(=C1NC(=O)C=1C=CN2C3=C(CCC=12)C=NC(=N3)NC1=C(C=C(C=C1)OCCN(C)C)OC)CC YHGJHTMBMIUDIY-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14163734.8 | 2014-04-07 | ||
| EP14163734 | 2014-04-07 | ||
| EP15153207.4 | 2015-01-30 | ||
| EP15153207 | 2015-01-30 | ||
| PCT/EP2015/056839 WO2015155042A1 (en) | 2014-04-07 | 2015-03-30 | (5,6-dihydro)pyrimido[4,5-e]indolizines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017510595A JP2017510595A (ja) | 2017-04-13 |
| JP2017510595A5 true JP2017510595A5 (cg-RX-API-DMAC7.html) | 2018-05-17 |
| JP6518690B2 JP6518690B2 (ja) | 2019-05-22 |
Family
ID=52774240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016560952A Active JP6518690B2 (ja) | 2014-04-07 | 2015-03-30 | （５，６−ジヒドロ）ピリミド［４，５−ｅ］インドリジン |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | USRE48974E1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3129374B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6518690B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102432420B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN106132963B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2015243694B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112016022342B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2944610C (cg-RX-API-DMAC7.html) |
| DK (1) | DK3129374T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2716165T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE043108T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MX368767B (cg-RX-API-DMAC7.html) |
| PL (1) | PL3129374T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT3129374T (cg-RX-API-DMAC7.html) |
| RU (1) | RU2692479C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015155042A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX368767B (es) * | 2014-04-07 | 2019-10-15 | Netherlands Translational Res Center B V | (5,6-dihidro)pirimido[4,5-e]indolizinas. |
| AU2016247476B2 (en) | 2015-04-17 | 2021-12-16 | SillaJen Inc. | Prognostic biomarkers for TTK inhibitor chemotherapy |
| PL3416964T3 (pl) * | 2016-02-19 | 2021-10-18 | Phoenix Molecular Designs | Pochodne 6-okso-n-(1-(benzylo)-1h-pirazol-4-ilo)-6,7,8,9-tetrahydropirydo[3’,2’:4,5]pirolo[1,2-a]pirazyno-2-karboksyamidu jako inhibitory kinazy rybosomalnej s6 p90 (rsk) do leczenia nowotworu złośliwego |
| KR20230109185A (ko) | 2016-06-07 | 2023-07-19 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| CN106551938B (zh) * | 2016-11-26 | 2017-11-24 | 广东安诺药业股份有限公司 | 一种治疗非酒精性脂肪肝的药物及其应用 |
| PT3601239T (pt) | 2017-03-23 | 2024-10-24 | Jacobio Pharmaceuticals Co Ltd | Novos derivados heterocíclicos úteis como inibidores de shp2 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| AU2020222056A1 (en) | 2019-02-11 | 2021-10-07 | Phoenix Molecular Designs | Crystalline forms of an RSK inhibitor |
| JP2024546977A (ja) * | 2021-12-15 | 2024-12-26 | シルラジェン，インコーポレイテッド | 新生物疾患の処置方法 |
| AU2022415783A1 (en) * | 2021-12-15 | 2024-06-27 | Sillajen, Inc. | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
| MX2024007452A (es) * | 2021-12-15 | 2024-07-09 | Sillajen Inc | Composiciones farmaceuticas que comprenden beta-ciclodextrinas modificadas. |
| KR20240144991A (ko) * | 2022-03-04 | 2024-10-04 | 신라젠(주) | 신생물성 질환 치료에 사용하기 위한 약제학적 병용물 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0212760A (pt) * | 2001-09-19 | 2004-12-07 | Aventis Pharma Sa | Compostos quìmicos |
| JP5043432B2 (ja) | 2003-05-22 | 2012-10-10 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | ピラゾロ−キナゾリン誘導体、その製造方法、およびキナーゼ阻害剤としてのその使用 |
| JP5284973B2 (ja) | 2006-11-28 | 2013-09-11 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | 三環式インドールおよび（４，５−ジヒドロ）インドール |
| EA020703B9 (ru) * | 2008-06-26 | 2015-12-30 | Ле Лаборатуар Сервье | Пиразолохиназолины |
| WO2010111406A2 (en) | 2009-03-24 | 2010-09-30 | Myriad Pharmaceuticals, Inc. | Compounds and therapeutic uses thereof |
| WO2010125004A1 (en) | 2009-04-29 | 2010-11-04 | Nerviano Medical Sciences S.R.L. | Cdk inhibitor salts |
| JP5851990B2 (ja) | 2009-07-29 | 2016-02-03 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | Ｐｌｋ阻害剤の塩 |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| CA2821829A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| EP2668190B1 (en) * | 2011-01-26 | 2016-08-17 | Nerviano Medical Sciences S.r.l. | Tricyclic pyrrolo derivatives, process for their preparation and their use as kinase inhibitors |
| JP6523267B2 (ja) | 2013-06-24 | 2019-05-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｆｓｈｒの調節剤としてのイミダゾール化合物及びその使用 |
| MX368767B (es) * | 2014-04-07 | 2019-10-15 | Netherlands Translational Res Center B V | (5,6-dihidro)pirimido[4,5-e]indolizinas. |
-
2015
- 2015-03-30 MX MX2016012997A patent/MX368767B/es active IP Right Grant
- 2015-03-30 DK DK15712912.3T patent/DK3129374T3/en active
- 2015-03-30 BR BR112016022342-0A patent/BR112016022342B1/pt active IP Right Grant
- 2015-03-30 US US16/728,900 patent/USRE48974E1/en active Active
- 2015-03-30 KR KR1020167031029A patent/KR102432420B1/ko active Active
- 2015-03-30 CA CA2944610A patent/CA2944610C/en active Active
- 2015-03-30 AU AU2015243694A patent/AU2015243694B2/en active Active
- 2015-03-30 WO PCT/EP2015/056839 patent/WO2015155042A1/en not_active Ceased
- 2015-03-30 US US15/128,874 patent/US9856258B2/en not_active Ceased
- 2015-03-30 EP EP15712912.3A patent/EP3129374B1/en active Active
- 2015-03-30 PL PL15712912T patent/PL3129374T3/pl unknown
- 2015-03-30 US US17/579,990 patent/USRE50082E1/en active Active
- 2015-03-30 JP JP2016560952A patent/JP6518690B2/ja active Active
- 2015-03-30 HU HUE15712912A patent/HUE043108T2/hu unknown
- 2015-03-30 RU RU2016141405A patent/RU2692479C2/ru active
- 2015-03-30 CN CN201580017365.8A patent/CN106132963B/zh active Active
- 2015-03-30 PT PT15712912T patent/PT3129374T/pt unknown
- 2015-03-30 ES ES15712912T patent/ES2716165T3/es active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017510595A5 (cg-RX-API-DMAC7.html) | ||
| CA2934137C (en) | Novel carboxamides, method for the production thereof, pharmaceutical preparations comprising them, and use thereof for producing medicaments | |
| CN111989332A (zh) | 作为cdk抑制剂的大环化合物、其制备方法及其在医药上的应用 | |
| JP2015514808A5 (cg-RX-API-DMAC7.html) | ||
| EP3555074B1 (en) | Aminopyrazoles as selective janus kinase inhibitors | |
| IL279800B1 (en) | Selective allosteric inhibitors of epidermal growth factor receptor mutants, pharmaceutical compositions comprising them and use thereof | |
| PH12018500765A1 (en) | N-sulfonylated pyrazolo[3,4-b]pyridin-6-carboxamides and method of use | |
| JP2005539012A5 (cg-RX-API-DMAC7.html) | ||
| JP2017502940A5 (cg-RX-API-DMAC7.html) | ||
| JP2021509113A (ja) | キナーゼ阻害剤としての複素環式アミド | |
| JP2005538099A5 (cg-RX-API-DMAC7.html) | ||
| EA201992126A1 (ru) | Ингибиторы jak, содержащие 4-членный гетероциклический амид | |
| JP2018507877A5 (cg-RX-API-DMAC7.html) | ||
| JP2006524669A5 (cg-RX-API-DMAC7.html) | ||
| JP2019505541A5 (cg-RX-API-DMAC7.html) | ||
| JP2010526129A5 (cg-RX-API-DMAC7.html) | ||
| GEP20084439B (en) | Nitrogen-containing heterocyclic derivatives and pharmaceutical use thereof | |
| CN115443276B (zh) | 吡啶并嘧啶酮衍生物及其作为芳烃受体调节剂的应用 | |
| JP2017525668A5 (cg-RX-API-DMAC7.html) | ||
| JP2017519781A5 (cg-RX-API-DMAC7.html) | ||
| UA113280C2 (xx) | АМІНОСПИРТЗАМІЩЕНІ ПОХІДНІ 2,3-ДИГІДРОІМІДАЗО$1,2-c]ХІНАЗОЛІНУ, ПРИДАТНІ ДЛЯ ЛІКУВАННЯ ГІПЕРПРОЛІФЕРАТИВНИХ ПОРУШЕНЬ І ЗАХВОРЮВАНЬ, ПОВ'ЯЗАНИХ З АНГІОГЕНЕЗОМ | |
| JP2017521407A5 (cg-RX-API-DMAC7.html) | ||
| WO2014031438A3 (en) | SUBSTITUTED PHENYL SPLEEN TYROSINE KINASE (Syk) INHIBITORS | |
| JP2015505301A5 (cg-RX-API-DMAC7.html) | ||
| EA202190681A1 (ru) | Амиды диметиламиноазетидина в качестве jak ингибиторов |