HRP20020076A2 - Substituted oxoazaheterocyclyl compounds - Google Patents
Substituted oxoazaheterocyclyl compounds Download PDFInfo
- Publication number
- HRP20020076A2 HRP20020076A2 HR20020076A HRP20020076A HRP20020076A2 HR P20020076 A2 HRP20020076 A2 HR P20020076A2 HR 20020076 A HR20020076 A HR 20020076A HR P20020076 A HRP20020076 A HR P20020076A HR P20020076 A2 HRP20020076 A2 HR P20020076A2
- Authority
- HR
- Croatia
- Prior art keywords
- ylmethyl
- chloro
- piperazin
- amino
- quinazolin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 409
- 238000000034 method Methods 0.000 claims abstract description 48
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 39
- 108010029144 Factor IIa Proteins 0.000 claims abstract description 25
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- -1 methoxyethylaminomethyl Chemical group 0.000 claims description 357
- 125000001072 heteroaryl group Chemical group 0.000 claims description 150
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- 239000001257 hydrogen Substances 0.000 claims description 127
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000000623 heterocyclic group Chemical group 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 150000002431 hydrogen Chemical class 0.000 claims description 88
- 229910052717 sulfur Inorganic materials 0.000 claims description 70
- 229910052760 oxygen Inorganic materials 0.000 claims description 68
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 125000003107 substituted aryl group Chemical group 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 53
- 150000001721 carbon Chemical group 0.000 claims description 52
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 45
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 45
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 30
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 29
- 150000001204 N-oxides Chemical class 0.000 claims description 28
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 230000009471 action Effects 0.000 claims description 24
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
- 229940002612 prodrug Drugs 0.000 claims description 21
- 125000004442 acylamino group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 claims description 18
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004419 alkynylene group Chemical group 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 8
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- PLLLVRSRXFDRHN-UHFFFAOYSA-N 1h-pyrazole;thiophene Chemical compound C=1C=CSC=1.C=1C=NNC=1 PLLLVRSRXFDRHN-UHFFFAOYSA-N 0.000 claims description 6
- LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical compound C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- GBXYTRIBFXZUBS-UHFFFAOYSA-N oxadiazole;thiophene Chemical compound C=1C=CSC=1.C1=CON=N1 GBXYTRIBFXZUBS-UHFFFAOYSA-N 0.000 claims description 6
- KAVSMINTEBGDTI-UHFFFAOYSA-N pyridine;thiophene Chemical compound C=1C=CSC=1.C1=CC=NC=C1 KAVSMINTEBGDTI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- JEJWGAXKVFYJDN-UHFFFAOYSA-N thiadiazole;thiophene Chemical compound C=1C=CSC=1.C1=CSN=N1 JEJWGAXKVFYJDN-UHFFFAOYSA-N 0.000 claims description 6
- HHNQDLUNMOECFS-UHFFFAOYSA-N thiophene;2h-triazole Chemical compound C=1C=CSC=1.C1=CNN=N1 HHNQDLUNMOECFS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 230000004962 physiological condition Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- REAOXGUQRZZDRL-UHFFFAOYSA-N 1,1-diphenyl-N-(1H-pyrrolo[3,2-b]pyridin-2-yl)methanimine Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=CC2=C(C=CC=N2)N1 REAOXGUQRZZDRL-UHFFFAOYSA-N 0.000 claims description 4
- ULIIZNSKJMOVMX-UHFFFAOYSA-N 1,2-oxazole;thiophene Chemical group C=1C=CSC=1.C=1C=NOC=1 ULIIZNSKJMOVMX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005354 acylalkyl group Chemical group 0.000 claims description 3
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- VPQAQEOATKTJSK-UHFFFAOYSA-N piperidine;pyrimidine Chemical compound C1CCNCC1.C1=CN=CN=C1 VPQAQEOATKTJSK-UHFFFAOYSA-N 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000005569 butenylene group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ZMUADARPXLFDHP-UHFFFAOYSA-N nitrocarbamic acid Chemical compound OC(=O)N[N+]([O-])=O ZMUADARPXLFDHP-UHFFFAOYSA-N 0.000 claims description 2
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- ILWNJPBQNWSXDJ-FQEVSTJZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 ILWNJPBQNWSXDJ-FQEVSTJZSA-N 0.000 claims 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 5
- YRUYPOCCFXKUGQ-FQEVSTJZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=NC2=C1 YRUYPOCCFXKUGQ-FQEVSTJZSA-N 0.000 claims 4
- FLWBPUYNYZDVAW-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 FLWBPUYNYZDVAW-KRWDZBQOSA-N 0.000 claims 4
- SXJRFJQQWDUBFI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(O)=O)=CC2=C1 SXJRFJQQWDUBFI-UHFFFAOYSA-N 0.000 claims 4
- YPRAQQUUXZEJAL-NRFANRHFSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 YPRAQQUUXZEJAL-NRFANRHFSA-N 0.000 claims 3
- WMVJTEVXTPWTIO-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=NC2=C1 WMVJTEVXTPWTIO-QGZVFWFLSA-N 0.000 claims 3
- AFOIEYGNOGPVNW-OAHLLOKOSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=NC2=C1 AFOIEYGNOGPVNW-OAHLLOKOSA-N 0.000 claims 3
- RCXOEPBIGDLMFU-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 RCXOEPBIGDLMFU-LJQANCHMSA-N 0.000 claims 3
- PYKCBKZDYWPYNB-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 PYKCBKZDYWPYNB-QGZVFWFLSA-N 0.000 claims 3
- HMRPAOMZDREQHD-NRFANRHFSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 HMRPAOMZDREQHD-NRFANRHFSA-N 0.000 claims 3
- BVJOOFWNOSOSAN-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 BVJOOFWNOSOSAN-IBGZPJMESA-N 0.000 claims 3
- BNQVIOJIVRWRHU-ZDUSSCGKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 BNQVIOJIVRWRHU-ZDUSSCGKSA-N 0.000 claims 3
- CFDFZWBTINHDGA-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 CFDFZWBTINHDGA-IBGZPJMESA-N 0.000 claims 3
- JDYHHQBKBCKVIJ-ZDUSSCGKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 JDYHHQBKBCKVIJ-ZDUSSCGKSA-N 0.000 claims 3
- WMVJTEVXTPWTIO-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=NC2=C1 WMVJTEVXTPWTIO-KRWDZBQOSA-N 0.000 claims 3
- TWKRFZFCDFYWDU-ZDUSSCGKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 TWKRFZFCDFYWDU-ZDUSSCGKSA-N 0.000 claims 3
- 229930194542 Keto Natural products 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- BVJOOFWNOSOSAN-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 BVJOOFWNOSOSAN-LJQANCHMSA-N 0.000 claims 2
- UTCXKEYSWPZQAZ-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 UTCXKEYSWPZQAZ-QGZVFWFLSA-N 0.000 claims 2
- CFDFZWBTINHDGA-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 CFDFZWBTINHDGA-LJQANCHMSA-N 0.000 claims 2
- YRMPXIRUPGIBLA-GFCCVEGCSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=NC2=C1 YRMPXIRUPGIBLA-GFCCVEGCSA-N 0.000 claims 2
- TWKRFZFCDFYWDU-CYBMUJFWSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 TWKRFZFCDFYWDU-CYBMUJFWSA-N 0.000 claims 2
- UTCXKEYSWPZQAZ-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 UTCXKEYSWPZQAZ-KRWDZBQOSA-N 0.000 claims 2
- YPRAQQUUXZEJAL-OAQYLSRUSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 YPRAQQUUXZEJAL-OAQYLSRUSA-N 0.000 claims 2
- AFOIEYGNOGPVNW-HNNXBMFYSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=NC2=C1 AFOIEYGNOGPVNW-HNNXBMFYSA-N 0.000 claims 2
- YRMPXIRUPGIBLA-LBPRGKRZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=NC2=C1 YRMPXIRUPGIBLA-LBPRGKRZSA-N 0.000 claims 2
- RCXOEPBIGDLMFU-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 RCXOEPBIGDLMFU-IBGZPJMESA-N 0.000 claims 2
- PYKCBKZDYWPYNB-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 PYKCBKZDYWPYNB-KRWDZBQOSA-N 0.000 claims 2
- AIASIFWCSPZBDG-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound ClC1=CC=C2NC(CN3C4CCCCC4N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 AIASIFWCSPZBDG-UHFFFAOYSA-N 0.000 claims 2
- WWBHKWYIBPGIKU-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)CC3COC)=CC=C21 WWBHKWYIBPGIKU-UHFFFAOYSA-N 0.000 claims 2
- UXCDAPQWTIOGBJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 UXCDAPQWTIOGBJ-UHFFFAOYSA-N 0.000 claims 2
- RZKZSZPNNVWFGI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazine-2,3-dione Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3=O)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 RZKZSZPNNVWFGI-UHFFFAOYSA-N 0.000 claims 2
- NPLLUEMGJMFUII-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 NPLLUEMGJMFUII-UHFFFAOYSA-N 0.000 claims 2
- MCUUGAMHPMUIPU-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)C(=O)N)=CC2=C1 MCUUGAMHPMUIPU-UHFFFAOYSA-N 0.000 claims 2
- WATFFCBCBMOTJR-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-6,7-dihydro-5h-1,3-benzothiazol-4-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(S1)=NC2=C1CCCC2=O WATFFCBCBMOTJR-UHFFFAOYSA-N 0.000 claims 2
- CCXQCOZBEONOFB-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound CN(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 CCXQCOZBEONOFB-UHFFFAOYSA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 claims 2
- UGPDGFSYKBGAPB-UHFFFAOYSA-N 4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)S(=O)(=O)C=3NC4=CC=C(C=C4C=3)Cl)=CC2=C1 UGPDGFSYKBGAPB-UHFFFAOYSA-N 0.000 claims 2
- CYZSVYRPFVOTIQ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)piperazin-2-one Chemical compound C1CCCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 CYZSVYRPFVOTIQ-UHFFFAOYSA-N 0.000 claims 2
- ZHFKLZCIFNYJIP-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-hydroxy-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)O)=CC2=C1 ZHFKLZCIFNYJIP-UHFFFAOYSA-N 0.000 claims 2
- XGABEBXUGAILJN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-hydroxyimino-6,7-dihydro-5h-1,3-benzothiazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)=NO)=CC2=C1 XGABEBXUGAILJN-UHFFFAOYSA-N 0.000 claims 2
- RFPWFEJSPIAHBG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[4-(4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl]piperazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 RFPWFEJSPIAHBG-UHFFFAOYSA-N 0.000 claims 2
- FEULSLWGSGKTLE-UHFFFAOYSA-N 4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C(C=C1)=CC=C1CN1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 FEULSLWGSGKTLE-UHFFFAOYSA-N 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- BWLMQHXPIWJDBC-UHFFFAOYSA-N ethyl 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)C(=O)OCC)=CC2=C1 BWLMQHXPIWJDBC-UHFFFAOYSA-N 0.000 claims 2
- NNVWVFCPLVDZEZ-UHFFFAOYSA-N ethyl 3-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-3-methylbutanoate Chemical compound CCOC(=O)CC(C)(C)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 NNVWVFCPLVDZEZ-UHFFFAOYSA-N 0.000 claims 2
- NEGRUALBPOJNNR-UHFFFAOYSA-N methyl 1-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-5-oxo-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylate Chemical compound COC(=O)C1CN(CC=2NC3=CC=NC=C3C=2)C(=O)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 NEGRUALBPOJNNR-UHFFFAOYSA-N 0.000 claims 2
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 2
- PXSNZXGXAWUECB-IBGZPJMESA-N (2S)-4-[(4-aminoquinazolin-7-yl)methyl]-N-(4-chlorophenyl)-2-(methoxymethyl)-3-oxopiperazine-1-sulfonamide Chemical compound ClC1=CC=C(C=C1)NS(=O)(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)COC PXSNZXGXAWUECB-IBGZPJMESA-N 0.000 claims 1
- GNCBTIHINJEKMH-NRFANRHFSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorophenyl)-2-(2-methylpropyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(C)C)C(=O)NC1=CC=C(Cl)C=C1 GNCBTIHINJEKMH-NRFANRHFSA-N 0.000 claims 1
- NPQHGKXCYSHCLB-SFHVURJKSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorophenyl)-2-(hydroxymethyl)-3-oxopiperazine-1-carboxamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)NC1=CC=C(Cl)C=C1 NPQHGKXCYSHCLB-SFHVURJKSA-N 0.000 claims 1
- ZIKSMAACNYWYOY-AWEZNQCLSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-chloro-1,3-thiazol-2-yl)-2-(methoxymethyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)NC1=NC=C(Cl)S1 ZIKSMAACNYWYOY-AWEZNQCLSA-N 0.000 claims 1
- GJIQDXNINSHHBN-HNNXBMFYSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-chloro-1,3-thiazol-2-yl)-3-oxo-2-propylpiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)NC1=NC=C(Cl)S1 GJIQDXNINSHHBN-HNNXBMFYSA-N 0.000 claims 1
- JOXZRCVHHCNRBL-BTYIYWSLSA-N (2s,5s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorophenyl)-5-methyl-3-oxo-2-propylpiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)NC1=CC=C(Cl)C=C1 JOXZRCVHHCNRBL-BTYIYWSLSA-N 0.000 claims 1
- ZAFSRIZLKCJTTR-GUYCJALGSA-N (2s,5s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-chlorothiophen-2-yl)-5-methyl-3-oxo-2-propylpiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)NC1=CC=C(Cl)S1 ZAFSRIZLKCJTTR-GUYCJALGSA-N 0.000 claims 1
- OJSPTVMYYWTQGD-HXOBKFHXSA-N (3S,6R)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(=CC=C12)CN1C([C@@H](N(C[C@H]1C)C(C=CC1=CC=C(C=C1)O)=O)CCC)=O OJSPTVMYYWTQGD-HXOBKFHXSA-N 0.000 claims 1
- ONDMRPOZZIDTRB-QRWLVFNGSA-N (3S,6R)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(=CC=C12)CN1C([C@@H](N(C[C@H]1C)C(C=CC=1SC(=CC1)Cl)=O)CCC)=O ONDMRPOZZIDTRB-QRWLVFNGSA-N 0.000 claims 1
- WITZBTVOTPNBOC-QRWLVFNGSA-N (3S,6R)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-3-yl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(=CC=C12)CN1C([C@@H](N(C[C@H]1C)C(C=CC1=CSC(=C1)Cl)=O)CCC)=O WITZBTVOTPNBOC-QRWLVFNGSA-N 0.000 claims 1
- MXYZABNETCECPJ-MRXNPFEDSA-N (3r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(Cl)S1 MXYZABNETCECPJ-MRXNPFEDSA-N 0.000 claims 1
- YSLYBMBFWXYPCG-SFHVURJKSA-N (3s)-1-[(4-amino-2-methylquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=C(C)N=C(N)C3=CC=2)CC1)=O)CCC)C(=O)COC1=CC=C(Cl)S1 YSLYBMBFWXYPCG-SFHVURJKSA-N 0.000 claims 1
- WROGRTUJEZVSSW-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-(methoxymethyl)-4-[(4-pyrimidin-4-ylphenyl)methyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)CC(C=C1)=CC=C1C1=CC=NC=N1 WROGRTUJEZVSSW-DEOSSOPVSA-N 0.000 claims 1
- UKHYEXSTCVHYKA-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(4-imidazol-1-ylbenzoyl)-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C(C=C1)=CC=C1N1C=CN=C1 UKHYEXSTCVHYKA-QHCPKHFHSA-N 0.000 claims 1
- ZGHRZYDUEORGRH-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(5-chloro-1-benzofuran-2-carbonyl)-3-propylpiperazin-2-one Chemical compound ClC1=CC=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 ZGHRZYDUEORGRH-FQEVSTJZSA-N 0.000 claims 1
- COUFQGIBAIVOAH-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(5-chloro-1-benzothiophene-2-carbonyl)-3-propylpiperazin-2-one Chemical compound ClC1=CC=C2SC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 COUFQGIBAIVOAH-FQEVSTJZSA-N 0.000 claims 1
- XTUVGWUAGYHTME-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzofuran-2-carbonyl)-3-(2-methylsulfanylethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCSC)=CC2=C1 XTUVGWUAGYHTME-FQEVSTJZSA-N 0.000 claims 1
- BVJASOCDBJJIOD-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzothiophene-2-carbonyl)-3-propylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 BVJASOCDBJJIOD-FQEVSTJZSA-N 0.000 claims 1
- DAHDSWRVSTXKNO-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-hydroxynaphthalene-2-carbonyl)-3-propylpiperazin-2-one Chemical compound C1=C(O)C=CC2=CC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC=C21 DAHDSWRVSTXKNO-DEOSSOPVSA-N 0.000 claims 1
- NPEUCYQJPKVJKB-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3,5-dichloro-1h-indol-2-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC4=C(C5=CC(Cl)=CC=C5N4)Cl)[C@H](C3=O)COC)=CC=C21 NPEUCYQJPKVJKB-NRFANRHFSA-N 0.000 claims 1
- UONHNCBWQSHVBK-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4SC5=C(N)N=CN=C5C=4)[C@H](C3=O)COC)=CC=C21 UONHNCBWQSHVBK-SFHVURJKSA-N 0.000 claims 1
- WSSZRGPFLACFOO-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)CC(C)C)=CC=C21 WSSZRGPFLACFOO-DEOSSOPVSA-N 0.000 claims 1
- NQCZNXOCIOBIHQ-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-(2-methylsulfanylethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)CCSC)=CC=C21 NQCZNXOCIOBIHQ-QHCPKHFHSA-N 0.000 claims 1
- KLDMMXIDDQEBJN-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)CCC)=CC=C21 KLDMMXIDDQEBJN-QHCPKHFHSA-N 0.000 claims 1
- SUWAPORUGXFZIZ-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-3-methyl-1h-indol-2-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC4=C(C5=CC(Cl)=CC=C5N4)C)[C@H](C3=O)COC)=CC=C21 SUWAPORUGXFZIZ-QHCPKHFHSA-N 0.000 claims 1
- HLSPWLSRRNDJDW-QFIPXVFZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzofuran-2-yl)methyl]-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4OC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CCC)=CC=C21 HLSPWLSRRNDJDW-QFIPXVFZSA-N 0.000 claims 1
- WDIUQNRHJJZGNQ-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chlorothieno[2,3-b]pyridin-2-yl)methyl]-3-propylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4SC5=NC(Cl)=CC=C5C=4)[C@H](C3=O)CCC)=CC=C21 WDIUQNRHJJZGNQ-FQEVSTJZSA-N 0.000 claims 1
- PFJNEWFEANJVBC-OWLMGLOSSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(4-hydroxyphenyl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)\C=C\C1=CC=C(O)C=C1 PFJNEWFEANJVBC-OWLMGLOSSA-N 0.000 claims 1
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- SICAEVPEPWTQDS-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-[(dimethylamino)methyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CN(C)C)C(=O)COC1=CC=C(Cl)S1 SICAEVPEPWTQDS-KRWDZBQOSA-N 0.000 claims 1
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- VCCQPBXDRDSSCK-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CSC1=NN=C(N)S1 VCCQPBXDRDSSCK-AWEZNQCLSA-N 0.000 claims 1
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- GEQJMSSNGSOYFP-NRFANRHFSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 GEQJMSSNGSOYFP-NRFANRHFSA-N 0.000 claims 1
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- ZAMDKBNFJHORMO-QHCPKHFHSA-N (3s)-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C=C(Cl)SC=1C=CC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 ZAMDKBNFJHORMO-QHCPKHFHSA-N 0.000 claims 1
- DHZGOKUODGLFHK-NRFANRHFSA-N (3s)-4-[3-(6-amino-2-methylpyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C=CC1=CC=C(N)N=C1C DHZGOKUODGLFHK-NRFANRHFSA-N 0.000 claims 1
- RZGFTDVSSQPDRV-QHCPKHFHSA-N (3s)-4-[[3-(5-chlorothiophen-2-yl)-4-fluorophenyl]methyl]-3-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)CCC)CC(C=1)=CC=C(F)C=1C1=CC=C(Cl)S1 RZGFTDVSSQPDRV-QHCPKHFHSA-N 0.000 claims 1
- IOOMZIUMYRDFQW-QHCPKHFHSA-N (3s)-4-[[4-(2-aminopyrimidin-4-yl)phenyl]methyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)CC(C=C1)=CC=C1C1=CC=NC(N)=N1 IOOMZIUMYRDFQW-QHCPKHFHSA-N 0.000 claims 1
- ULSMRYSLUHIMIZ-QHCPKHFHSA-N (3s)-4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]-3-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)CCC)CC(C=C1)=CC=C1C1=CC=C(Cl)S1 ULSMRYSLUHIMIZ-QHCPKHFHSA-N 0.000 claims 1
- WUFURXUXGHWJAO-NRFANRHFSA-N (3s)-4-[[4-(5-chlorothiophen-2-yl)thiophen-2-yl]methyl]-3-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)CCC)CC(SC=1)=CC=1C1=CC=C(Cl)S1 WUFURXUXGHWJAO-NRFANRHFSA-N 0.000 claims 1
- DVDFFYJYQHEPQR-DEOSSOPVSA-N (3s)-4-[[5-(3-chlorophenyl)furan-2-yl]methyl]-3-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)CCC)CC(O1)=CC=C1C1=CC=CC(Cl)=C1 DVDFFYJYQHEPQR-DEOSSOPVSA-N 0.000 claims 1
- WRUJRZSTPBKCOH-FQEVSTJZSA-N (3s)-4-[[5-(5-chlorothiophen-2-yl)thiophen-2-yl]methyl]-3-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2NC3=CC=NC=C3C=2)CC1)=O)CCC)CC(S1)=CC=C1C1=CC=C(Cl)S1 WRUJRZSTPBKCOH-FQEVSTJZSA-N 0.000 claims 1
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- NFTHTZCCDZZDLC-KSSFIOAISA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)COC1=CC=C(Cl)S1 NFTHTZCCDZZDLC-KSSFIOAISA-N 0.000 claims 1
- LGCCNIXEXADPDD-LIRRHRJNSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)COC1=CSC(Cl)=C1 LGCCNIXEXADPDD-LIRRHRJNSA-N 0.000 claims 1
- ONDMRPOZZIDTRB-YWZLYKJASA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)C=CC1=CC=C(Cl)S1 ONDMRPOZZIDTRB-YWZLYKJASA-N 0.000 claims 1
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- LBFSDQWYKYNZPL-GOSISDBHSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4SC5=CC(Cl)=CC=C5C=4)C[C@@H]3COC)=CC=C21 LBFSDQWYKYNZPL-GOSISDBHSA-N 0.000 claims 1
- FLWBPUYNYZDVAW-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 FLWBPUYNYZDVAW-QGZVFWFLSA-N 0.000 claims 1
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- JDYHHQBKBCKVIJ-CYBMUJFWSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 JDYHHQBKBCKVIJ-CYBMUJFWSA-N 0.000 claims 1
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- URWAZMGKDCTWHY-MRXNPFEDSA-N (6r)-4-(6-chlorothieno[2,3-b]pyridin-2-yl)sulfonyl-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)N=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)COC)=CC2=C1 URWAZMGKDCTWHY-MRXNPFEDSA-N 0.000 claims 1
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- ATAXDZRDMFWGSG-QFIPXVFZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-(morpholin-4-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(CC=2NC3=CC=C(Cl)C=C3C=2)C1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCOCC1 ATAXDZRDMFWGSG-QFIPXVFZSA-N 0.000 claims 1
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- RAAFVQBERCFKKS-OAQYLSRUSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-[[cyclopentyl(methyl)amino]methyl]piperazin-2-one Chemical compound C([C@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)CN(C)C2CCCC2)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RAAFVQBERCFKKS-OAQYLSRUSA-N 0.000 claims 1
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- AGOOXRJLSFZHTE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3,6-bis(methoxymethyl)piperazin-2-one Chemical compound COCC1C(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)C(COC)CN1C(=O)COC1=CC=C(Cl)S1 AGOOXRJLSFZHTE-UHFFFAOYSA-N 0.000 claims 1
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- LASVDNIAVSIVNJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-3-(methoxymethyl)piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(COC)N1CC(ON=1)=CC=1C1=CC=C(Cl)S1 LASVDNIAVSIVNJ-UHFFFAOYSA-N 0.000 claims 1
- UGAMPVZERUGBMO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-3-methylpiperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(C)N1CC(ON=1)=CC=1C1=CC=C(Cl)S1 UGAMPVZERUGBMO-UHFFFAOYSA-N 0.000 claims 1
- CIRUOCWGWWYEOA-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(ON=1)=CC=1C1=CC=C(Cl)S1 CIRUOCWGWWYEOA-UHFFFAOYSA-N 0.000 claims 1
- SSMRLXKJFFIPLJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1h-pyrazol-5-yl]methyl]piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(NN=1)=CC=1C1=CC=C(Cl)S1 SSMRLXKJFFIPLJ-UHFFFAOYSA-N 0.000 claims 1
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- RYKHHWQBGZVZRJ-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)thiophen-2-yl]methyl]piperazine-2,3-dione Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1=O)=O)CCN1CC(S1)=CC=C1C1=CC=C(Cl)S1 RYKHHWQBGZVZRJ-UHFFFAOYSA-N 0.000 claims 1
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- BOQZXGHEWNKPED-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(Cl)=CC=C1C1=CC(CN2C(CN(CC=3NC4=CC=NC=C4C=3)CC2)=O)=NO1 BOQZXGHEWNKPED-UHFFFAOYSA-N 0.000 claims 1
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- HAMYXIGVVLQNKZ-SFHVURJKSA-N 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]acetic acid Chemical compound ClC1=CC=C2NC(CN3C[C@H](CC(O)=O)N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 HAMYXIGVVLQNKZ-SFHVURJKSA-N 0.000 claims 1
- WJZYSVHAHCGIIU-INIZCTEOSA-N 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazin-2-yl]acetic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](CC(O)=O)N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 WJZYSVHAHCGIIU-INIZCTEOSA-N 0.000 claims 1
- UQSJBENEQYVQAZ-QHCPKHFHSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-1-[(7-chloroisoquinolin-3-yl)methyl]-3-oxopiperazin-2-yl]-n-methylacetamide Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC(=O)NC)=CC=C21 UQSJBENEQYVQAZ-QHCPKHFHSA-N 0.000 claims 1
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- FIVQFZAPNBWHCE-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 FIVQFZAPNBWHCE-UHFFFAOYSA-N 0.000 claims 1
- CXSGOTUYEWIDLO-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 CXSGOTUYEWIDLO-UHFFFAOYSA-N 0.000 claims 1
- ROVKSRJAIIXFFP-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 ROVKSRJAIIXFFP-UHFFFAOYSA-N 0.000 claims 1
- UCXVJPXVSGVRMT-UHFFFAOYSA-N 2-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]-n-(5-chlorothiophen-2-yl)-2-oxoacetamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)C(=O)NC1=CC=C(Cl)S1 UCXVJPXVSGVRMT-UHFFFAOYSA-N 0.000 claims 1
- NBEZZGRGQPOHCB-UHFFFAOYSA-N 2-[4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCC1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 NBEZZGRGQPOHCB-UHFFFAOYSA-N 0.000 claims 1
- LWXWAOGUIIMVQX-UHFFFAOYSA-N 2-[4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidin-1-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1N1CCC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)CC1 LWXWAOGUIIMVQX-UHFFFAOYSA-N 0.000 claims 1
- RGAHMMLGOITYPL-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 RGAHMMLGOITYPL-UHFFFAOYSA-N 0.000 claims 1
- LVCGSXRQPUFNGV-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazole-4-carboxylic acid;1,1-dimethylhydrazine Chemical compound CN(C)N.OC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 LVCGSXRQPUFNGV-UHFFFAOYSA-N 0.000 claims 1
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- HXSYAXNITKIPPA-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-5,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-6-one Chemical compound C1C(=O)NCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 HXSYAXNITKIPPA-UHFFFAOYSA-N 0.000 claims 1
- XGTVLQKVDLPYTQ-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC)SC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 XGTVLQKVDLPYTQ-UHFFFAOYSA-N 0.000 claims 1
- YODRMEKVTIZSKI-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n,n,4-trimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)N(C)C)SC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 YODRMEKVTIZSKI-UHFFFAOYSA-N 0.000 claims 1
- UUPVRRCNZZTOFR-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-(2-hydroxyethyl)-n-methyl-1,3-thiazole-4-carboxamide Chemical compound OCCN(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 UUPVRRCNZZTOFR-UHFFFAOYSA-N 0.000 claims 1
- QNYJVKFGTCIWEB-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-methoxy-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CON(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 QNYJVKFGTCIWEB-UHFFFAOYSA-N 0.000 claims 1
- CVLUMURXNKJMGA-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 CVLUMURXNKJMGA-UHFFFAOYSA-N 0.000 claims 1
- PAOGMWFWHFSBRS-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-methyl-n-propan-2-yl-1,3-thiazole-4-carboxamide Chemical compound CC(C)N(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 PAOGMWFWHFSBRS-UHFFFAOYSA-N 0.000 claims 1
- XUSKVXOLHLAJOM-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-propan-2-yl-1,3-thiazole-4-carboxamide Chemical compound CC(C)NC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 XUSKVXOLHLAJOM-UHFFFAOYSA-N 0.000 claims 1
- DTISDDZOXBKBAO-MRXNPFEDSA-N 2-amino-4-[[(2r)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]benzonitrile Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC1=CC=C(C#N)C(N)=C1 DTISDDZOXBKBAO-MRXNPFEDSA-N 0.000 claims 1
- UCKQCJSDSGITBE-UHFFFAOYSA-N 2-imidazol-1-ylethyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylate Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(CN(C1)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)C1C(=O)OCCN1C=CN=C1 UCKQCJSDSGITBE-UHFFFAOYSA-N 0.000 claims 1
- FOUCGQPLTCYURZ-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-3-oxopiperazine-2-carboxylate Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN1CCN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)C(=O)C1C(=O)OCCN1CCCC1 FOUCGQPLTCYURZ-UHFFFAOYSA-N 0.000 claims 1
- YBZNPIRCJDGBSB-UHFFFAOYSA-N 3-[2-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]-2-oxoethyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CC(=O)N2CC(=O)N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=C1 YBZNPIRCJDGBSB-UHFFFAOYSA-N 0.000 claims 1
- WOSKWBOEWXOLMW-QFIPXVFZSA-N 3-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-3-oxoprop-1-enyl]benzonitrile Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=CC(C#N)=C1 WOSKWBOEWXOLMW-QFIPXVFZSA-N 0.000 claims 1
- LPWDETCKVJWGIK-UHFFFAOYSA-N 3-[3-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]-3-oxopropyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CCC(=O)N2CC(=O)N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=C1 LPWDETCKVJWGIK-UHFFFAOYSA-N 0.000 claims 1
- VWEJJKNVTKJDAF-SFHVURJKSA-N 3-amino-5-[[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]methyl]thiophene-2-carbonitrile Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)CC1=CC(N)=C(C#N)S1 VWEJJKNVTKJDAF-SFHVURJKSA-N 0.000 claims 1
- YGFJXYQOBMLQJE-UHFFFAOYSA-N 4-[(3-acetyl-5-chloro-1h-indol-2-yl)methyl]-1-[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(C(=O)C)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 YGFJXYQOBMLQJE-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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HR20020076A HRP20020076A2 (en) | 1999-07-28 | 2002-01-25 | Substituted oxoazaheterocyclyl compounds |
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JP (1) | JP4829449B2 (pt) |
KR (1) | KR20020087041A (pt) |
CN (1) | CN1420882A (pt) |
AT (1) | ATE423113T1 (pt) |
AU (1) | AU773227B2 (pt) |
BG (1) | BG106340A (pt) |
BR (1) | BR0013179A (pt) |
CA (1) | CA2382755A1 (pt) |
CR (1) | CR6563A (pt) |
CZ (1) | CZ2002323A3 (pt) |
DE (1) | DE60041584D1 (pt) |
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HR (1) | HRP20020076A2 (pt) |
HU (1) | HUP0203375A3 (pt) |
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TR (1) | TR200200225T2 (pt) |
WO (1) | WO2001007436A2 (pt) |
ZA (1) | ZA200200543B (pt) |
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HK1054227A1 (zh) | 2003-11-21 |
NO20020214L (no) | 2002-04-02 |
CN1420882A (zh) | 2003-05-28 |
MXPA02000888A (es) | 2002-07-30 |
ATE423113T1 (de) | 2009-03-15 |
EP1208097A2 (en) | 2002-05-29 |
KR20020087041A (ko) | 2002-11-21 |
WO2001007436A2 (en) | 2001-02-01 |
WO2001007436A3 (en) | 2001-08-23 |
ZA200200543B (en) | 2003-08-27 |
HUP0203375A3 (en) | 2005-03-29 |
JP4829449B2 (ja) | 2011-12-07 |
AU6462800A (en) | 2001-02-13 |
BG106340A (en) | 2002-10-31 |
BR0013179A (pt) | 2002-04-02 |
DE60041584D1 (de) | 2009-04-02 |
IL147495A0 (en) | 2002-08-14 |
IL147495A (en) | 2007-07-24 |
EE200200045A (et) | 2003-06-16 |
JP2003508353A (ja) | 2003-03-04 |
EP1208097B1 (en) | 2009-02-18 |
CR6563A (es) | 2008-11-25 |
NO20020214D0 (no) | 2002-01-15 |
HUP0203375A2 (hu) | 2002-12-28 |
AU773227B2 (en) | 2004-05-20 |
SK1182002A3 (en) | 2002-11-06 |
PL354998A1 (en) | 2004-03-22 |
CZ2002323A3 (cs) | 2002-05-15 |
RU2002105011A (ru) | 2004-01-20 |
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