CA2382755A1 - Substituted oxoazaheterocyclyl compounds - Google Patents

Info

Publication number

CA2382755A1

CA2382755A1 CA002382755A CA2382755A CA2382755A1 CA 2382755 A1 CA2382755 A1 CA 2382755A1 CA 002382755 A CA002382755 A CA 002382755A CA 2382755 A CA2382755 A CA 2382755A CA 2382755 A1 CA2382755 A1 CA 2382755A1

Authority

CA

Canada

Prior art keywords

ylmethyl

chloro

piperazin

amino

quinazolin

Prior art date

1999-07-28

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 443
• 238000000034 method Methods 0.000 claims abstract description 41
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 40
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 108010029144 Factor IIa Proteins 0.000 claims abstract 5
• -1 methoxyethylaminomethyl Chemical group 0.000 claims description 320
• 125000001072 heteroaryl group Chemical group 0.000 claims description 155
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 133
• 239000001257 hydrogen Substances 0.000 claims description 128
• 229910052739 hydrogen Inorganic materials 0.000 claims description 128
• 125000000623 heterocyclic group Chemical group 0.000 claims description 102
• 125000000217 alkyl group Chemical group 0.000 claims description 101
• 125000003118 aryl group Chemical group 0.000 claims description 93
• 150000002431 hydrogen Chemical class 0.000 claims description 87
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 67
• 229910052760 oxygen Inorganic materials 0.000 claims description 65
• 229910052717 sulfur Inorganic materials 0.000 claims description 64
• 125000002947 alkylene group Chemical group 0.000 claims description 63
• 125000004432 carbon atom Chemical group C* 0.000 claims description 62
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
• 125000003107 substituted aryl group Chemical group 0.000 claims description 60
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 56
• 229910052799 carbon Inorganic materials 0.000 claims description 55
• 150000001721 carbon Chemical group 0.000 claims description 51
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 238000002360 preparation method Methods 0.000 claims description 44
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 43
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 32
• 150000001204 N-oxides Chemical class 0.000 claims description 28
• 125000002252 acyl group Chemical group 0.000 claims description 28
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 27
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 26
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 25
• 125000005843 halogen group Chemical group 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 25
• 125000004414 alkyl thio group Chemical group 0.000 claims description 23
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 23
• 125000004442 acylamino group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 229940002612 prodrug Drugs 0.000 claims description 20
• 239000000651 prodrug Substances 0.000 claims description 20
• 125000004450 alkenylene group Chemical group 0.000 claims description 19
• CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
• 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
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 125000004104 aryloxy group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000004419 alkynylene group Chemical group 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 11
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 9
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 8
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 7
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 7
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-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
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
• 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
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
• 125000002795 guanidino group Chemical group C(N)(=N)N* 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
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• VPQAQEOATKTJSK-UHFFFAOYSA-N piperidine;pyrimidine Chemical compound C1CCNCC1.C1=CN=CN=C1 VPQAQEOATKTJSK-UHFFFAOYSA-N 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• 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
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
• 125000005569 butenylene 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
• 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 5
• 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 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
• 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 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
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims 4
• 229930194542 Keto Natural products 0.000 claims 4
• 230000004962 physiological condition Effects 0.000 claims 4
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 4
• 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 3
• 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 3
• 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
• 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 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
• 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
• 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 3
• 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 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
• 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
• 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 2
• GMKLPHFNNRIJIU-QFIPXVFZSA-N (3s)-4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]-3-(methoxymethyl)-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)COC)CC(C=C1)=CC=C1C1=CC=C(Cl)S1 GMKLPHFNNRIJIU-QFIPXVFZSA-N 0.000 claims 2
• LUGWIZQXSYDJDF-BTYIYWSLSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-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(Cl)=CS1 LUGWIZQXSYDJDF-BTYIYWSLSA-N 0.000 claims 2
• JQVUFHKXCOOAGG-OEMAIJDKSA-N (4r)-2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3SC=4CCC[C@H](C=4N=3)C(N)=O)COC)=CC2=C1 JQVUFHKXCOOAGG-OEMAIJDKSA-N 0.000 claims 2
• 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 2
• 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 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
• ZXQOJMMZOHJSTB-GOSISDBHSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)-1-[(4-pyridin-3-yl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(SC=1)=NC=1C1=CC=CN=C1 ZXQOJMMZOHJSTB-GOSISDBHSA-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
• 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
• 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 2
• CVVGDDQYOHBFCF-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)C2CCCCC2N1C(=O)COC1=CC=C(Cl)S1 CVVGDDQYOHBFCF-UHFFFAOYSA-N 0.000 claims 2
• MQUKKRZKNMMSLU-UHFFFAOYSA-N 1-[[4-(1-adamantyl)-1,3-thiazol-2-yl]methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C1=CSC(CN2CCN(CC2=O)S(=O)(=O)C2=CC3=CC=C(C=C3S2)Cl)=N1 MQUKKRZKNMMSLU-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• PIZIWFOGALZFIJ-OAHLLOKOSA-N 2-[[(2r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC1=NC(C(=O)N(C)C)=CS1 PIZIWFOGALZFIJ-OAHLLOKOSA-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
• 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 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
• XCKKFGCBUJHAMH-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyridin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=CC=CC=N1 XCKKFGCBUJHAMH-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
• WQAJCBIDKVJMBV-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(2-hydroxyethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound OCCNC1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 WQAJCBIDKVJMBV-UHFFFAOYSA-N 0.000 claims 2
• WMQMVIRAQZFLQM-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound CN(C)C1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 WMQMVIRAQZFLQM-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
• JOGYDPFHUFGMSS-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(hydroxymethyl)-1-[(1-methylpyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound N1=CC=C2N(C)C(CN3C(CN(CC3CO)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 JOGYDPFHUFGMSS-UHFFFAOYSA-N 0.000 claims 2
• SXNOHZLZDPIQJW-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)COC)=CC2=C1 SXNOHZLZDPIQJW-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
• 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
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-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
• CDNJTKXCEJBXDV-FQEVSTJZSA-N (2S)-4-[(4-aminoquinazolin-7-yl)methyl]-N-(4-chlorophenyl)sulfonyl-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)NS(=O)(=O)C1=CC=C(Cl)C=C1 CDNJTKXCEJBXDV-FQEVSTJZSA-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
• QAIUWZPKZGZREK-FQEVSTJZSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorophenyl)-2-(2-methylsulfanylethyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCSC)C(=O)NC1=CC=C(Cl)C=C1 QAIUWZPKZGZREK-FQEVSTJZSA-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
• LZWKVVOYZSPDLK-AWEZNQCLSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-bromo-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(Br)S1 LZWKVVOYZSPDLK-AWEZNQCLSA-N 0.000 claims 1
• PEDPKCRXTVNVSD-HNNXBMFYSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-bromo-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(Br)S1 PEDPKCRXTVNVSD-HNNXBMFYSA-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
• KXXMYOPBVCFRTO-IERDGZPVSA-N (3S,6R)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-6-methyl-3-propylpiperazin-2-one Chemical compound NC1=CC=C(C=N1)C=CC(=O)N1[C@H](C(N([C@@H](C1)C)CC1=CC=C2C(=NC=NC2=C1)N)=O)CCC KXXMYOPBVCFRTO-IERDGZPVSA-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
• BSHFNWHGGVUZNC-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-(2-methylsulfanylethyl)piperazin-2-one Chemical compound O=C1[C@H](CCSC)NCCN1CC1=CC=C(C(N)=NC=N2)C2=C1 BSHFNWHGGVUZNC-ZDUSSCGKSA-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
• SMIUMFJOKSVRHS-QFIPXVFZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(5-hydroxy-1h-indole-2-carbonyl)-3-propylpiperazin-2-one Chemical compound OC1=CC=C2NC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 SMIUMFJOKSVRHS-QFIPXVFZSA-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
• NJBMALYPNRWOPO-BDQAORGHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzofuran-2-carbonyl)-3-propylpiperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 NJBMALYPNRWOPO-BDQAORGHSA-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
• 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
• UFQAJBVMPZLQEE-VWLOTQADSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC(C)C)=CC=C21 UFQAJBVMPZLQEE-VWLOTQADSA-N 0.000 claims 1
• DCBJAVAQYQVWRJ-PVHVJQTOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(3-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=CC(O)=C1 DCBJAVAQYQVWRJ-PVHVJQTOSA-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
• USJMUPNRINRCNW-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(2-amino-1,3-thiazol-4-yl)acetyl]-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)CC1=CSC(N)=N1 USJMUPNRINRCNW-KRWDZBQOSA-N 0.000 claims 1
• FMEUNAWTMBBNEO-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3,4-dichlorothiophen-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)COC=1SC=C(Cl)C=1Cl FMEUNAWTMBBNEO-INIZCTEOSA-N 0.000 claims 1
• DVGRQJKJCQHZHG-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3,4-dichlorothiophen-2-yl)oxyacetyl]-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)COC=1SC=C(Cl)C=1Cl DVGRQJKJCQHZHG-KRWDZBQOSA-N 0.000 claims 1
• GIZPTEBUSNSQBQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-(hydroxymethyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)COC1=CC(Cl)=CS1 GIZPTEBUSNSQBQ-INIZCTEOSA-N 0.000 claims 1
• PFZSMLHMQHJNJB-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(C)C)C(=O)COC1=CC=C(Cl)S1 PFZSMLHMQHJNJB-SFHVURJKSA-N 0.000 claims 1
• 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
• JBPPHJOLTWFYEQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(6-chloropyrazin-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=CN=CC(Cl)=N1 JBPPHJOLTWFYEQ-INIZCTEOSA-N 0.000 claims 1
• 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
• PWEIMMCYMNAZHU-HNNXBMFYSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl]-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)CSC1=NN=C(N)S1 PWEIMMCYMNAZHU-HNNXBMFYSA-N 0.000 claims 1
• JHQIOJZCXJPJHV-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-(2-methoxyethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCOC)C(=O)C=CC1=CC(Cl)=CS1 JHQIOJZCXJPJHV-FQEVSTJZSA-N 0.000 claims 1
• XDTDNCIISWGSFW-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-(hydroxymethyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)C=CC1=CC(Cl)=CS1 XDTDNCIISWGSFW-SFHVURJKSA-N 0.000 claims 1
• LEHWJMLTKDRSDM-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chloro-6-oxo-1h-pyridin-3-yl)prop-2-enoyl]-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=CNC(=O)C(Cl)=C1 LEHWJMLTKDRSDM-FQEVSTJZSA-N 0.000 claims 1
• VUFALHGSAURHSJ-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(2-methoxyethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCOC)C(=O)C=CC1=CC=C(Cl)S1 VUFALHGSAURHSJ-IBGZPJMESA-N 0.000 claims 1
• QAVKUAXCSGKMJN-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(C)C)C(=O)C=CC1=CC=C(Cl)S1 QAVKUAXCSGKMJN-FQEVSTJZSA-N 0.000 claims 1
• LBIUTUCBLSATKR-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(hydroxymethyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)C=CC1=CC=C(Cl)S1 LBIUTUCBLSATKR-KRWDZBQOSA-N 0.000 claims 1
• AQGIOZUTOKOVPI-TXEPZDRESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1h-pyrazol-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.N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)CC(NN=1)=CC=1C1=CC=C(Cl)S1 AQGIOZUTOKOVPI-TXEPZDRESA-N 0.000 claims 1
• MYYBQVGASMWCLE-GXKRWWSZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)-1h-pyrazol-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.N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)CC(NN=1)=CC=1C1=CC=C(Cl)S1 MYYBQVGASMWCLE-GXKRWWSZSA-N 0.000 claims 1
• KVEVMDOCIXZXFU-SANMLTNESA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CN([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 KVEVMDOCIXZXFU-SANMLTNESA-N 0.000 claims 1
• YVMHXUDIOLWKIW-KRWDZBQOSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-3-methyl-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CN([C@H](C1=O)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 YVMHXUDIOLWKIW-KRWDZBQOSA-N 0.000 claims 1
• AOEYJIWBWFIEDT-IBGZPJMESA-N (3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-methylpiperazin-2-one Chemical compound C1=NC(OC)=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](C)N(CC=2N=CC3=CC(Cl)=CC=C3C=2)CC1 AOEYJIWBWFIEDT-IBGZPJMESA-N 0.000 claims 1
• GYXBYVNSNBXNTQ-MHZLTWQESA-N (3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C2=CC=C(Cl)C=C2C=NC=1CN([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 GYXBYVNSNBXNTQ-MHZLTWQESA-N 0.000 claims 1
• YQGAPIPZBMUTFM-SANMLTNESA-N (3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-3-(methoxymethyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C2=CC=C(Cl)C=C2C=NC=1CN([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 YQGAPIPZBMUTFM-SANMLTNESA-N 0.000 claims 1
• WDYKHICKGGMEAX-SFHVURJKSA-N (3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-3-methyl-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C2=CC=C(Cl)C=C2C=NC=1CN([C@H](C1=O)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 WDYKHICKGGMEAX-SFHVURJKSA-N 0.000 claims 1
• MWJIZTMGTFPLEP-SFHVURJKSA-N (3s)-4-[2-(5-aminopyridin-2-yl)oxyacetyl]-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)C(=O)COC1=CC=C(N)C=N1 MWJIZTMGTFPLEP-SFHVURJKSA-N 0.000 claims 1
• MSJUSNQDWGEVRR-SFHVURJKSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-[(3-imidazol-1-ylphenyl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC(C=1)=CC=CC=1N1C=CN=C1 MSJUSNQDWGEVRR-SFHVURJKSA-N 0.000 claims 1
• GVGWTUVZAWCGGI-INIZCTEOSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-[[2-[2-(dimethylamino)ethylamino]pyrimidin-5-yl]methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC1=CN=C(NCCN(C)C)N=C1 GVGWTUVZAWCGGI-INIZCTEOSA-N 0.000 claims 1
• 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
• XAIVEUFTGGYQSI-FQEVSTJZSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-[[4-(6-oxo-1h-pyridin-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=C1C=1C=CC(=O)NC=1 XAIVEUFTGGYQSI-FQEVSTJZSA-N 0.000 claims 1
• NQVAVXXDOHKLGG-NRFANRHFSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(2-methylpropyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)CC(C)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 NQVAVXXDOHKLGG-NRFANRHFSA-N 0.000 claims 1
• NLSYJBWXPXMVCR-QFIPXVFZSA-N (3s)-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1SC(Cl)=CC=1OCC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 NLSYJBWXPXMVCR-QFIPXVFZSA-N 0.000 claims 1
• JDDVYAGPAZJWEH-NRFANRHFSA-N (3s)-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1SC(Cl)=CC=1OCC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 JDDVYAGPAZJWEH-NRFANRHFSA-N 0.000 claims 1
• CXRLKVOMHFIZQK-INIZCTEOSA-N (3s)-4-[2-(6-aminopyrimidin-4-yl)oxyacetyl]-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)C(=O)COC1=CC(N)=NC=N1 CXRLKVOMHFIZQK-INIZCTEOSA-N 0.000 claims 1
• JYSSDQCSBAUMRK-DEOSSOPVSA-N (3s)-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C(Cl)=CSC=1C=CC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 JYSSDQCSBAUMRK-DEOSSOPVSA-N 0.000 claims 1
• RNTBLIWYQWHUQJ-QHCPKHFHSA-N (3s)-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C(Cl)=CSC=1C=CC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 RNTBLIWYQWHUQJ-QHCPKHFHSA-N 0.000 claims 1
• 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
• LRVKXTVDIBZLLF-QFIPXVFZSA-N (3s)-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-1-[[4-(6-oxo-1h-pyridin-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=C1C=1C=CC(=O)NC=1 LRVKXTVDIBZLLF-QFIPXVFZSA-N 0.000 claims 1
• PDEZSLCUHHYHIO-QHCPKHFHSA-N (3s)-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(2-methylpropyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1C=CC(=O)N([C@H](C1=O)CC(C)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 PDEZSLCUHHYHIO-QHCPKHFHSA-N 0.000 claims 1
• VJCFOSXJHZUYOG-QFIPXVFZSA-N (3s)-4-[3-(6-amino-2-methylpyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-butylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)C=CC1=CC=C(N)N=C1C VJCFOSXJHZUYOG-QFIPXVFZSA-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
• QVOWSXWJCKPWNF-FQEVSTJZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-(2-methoxyethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCOC)C(=O)C=CC1=CC=C(N)N=C1 QVOWSXWJCKPWNF-FQEVSTJZSA-N 0.000 claims 1
• PHGXINZDSDATTO-QHCPKHFHSA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C=C(N)N=CC=1C=CC(=O)N([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 PHGXINZDSDATTO-QHCPKHFHSA-N 0.000 claims 1
• UILDWQZNABTVMZ-DEOSSOPVSA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-3-(2-methylpropyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(N)N=CC=1C=CC(=O)N([C@H](C1=O)CC(C)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 UILDWQZNABTVMZ-DEOSSOPVSA-N 0.000 claims 1
• PLEYYMZQLBJBAY-IBGZPJMESA-N (3s)-4-[3-(6-aminopyridin-3-yl)propanoyl]-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)C(=O)CCC1=CC=C(N)N=C1 PLEYYMZQLBJBAY-IBGZPJMESA-N 0.000 claims 1
• GJNBCDYMKMJBFL-FQEVSTJZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)propanoyl]-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)CCC1=CC=C(N)N=C1 GJNBCDYMKMJBFL-FQEVSTJZSA-N 0.000 claims 1
• PBNALOSNDBJGPY-QFIPXVFZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)propanoyl]-3-(methoxymethyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(N)N=CC=1CCC(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 PBNALOSNDBJGPY-QFIPXVFZSA-N 0.000 claims 1
• IHCRIJWJWPICQA-NDEPHWFRSA-N (3s)-4-[[2-(4-chlorophenyl)-1h-indol-3-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(C1=CC=CC=C1N1)=C1C1=CC=C(Cl)C=C1 IHCRIJWJWPICQA-NDEPHWFRSA-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
• RUOJCTBWKMKIRL-QHCPKHFHSA-N (3s)-4-[[3-(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=1)=CC=CC=1C1=CC=C(Cl)S1 RUOJCTBWKMKIRL-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
• MIZZGMAZUNCQKR-NRFANRHFSA-N (3s)-4-[[5-(5-chlorothiophen-2-yl)pyridin-2-yl]methyl]-3-(methoxymethyl)-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)COC)CC(N=C1)=CC=C1C1=CC=C(Cl)S1 MIZZGMAZUNCQKR-NRFANRHFSA-N 0.000 claims 1
• XVTCAQNWZBWJHW-QFIPXVFZSA-N (3s)-4-[[5-(5-chlorothiophen-2-yl)pyridin-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(N=C1)=CC=C1C1=CC=C(Cl)S1 XVTCAQNWZBWJHW-QFIPXVFZSA-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
• AOKNKSWOMWNPKU-QFIPXVFZSA-N (3s)-4-[[6-(5-chlorothiophen-2-yl)pyridin-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(N=1)=CC=CC=1C1=CC=C(Cl)S1 AOKNKSWOMWNPKU-QFIPXVFZSA-N 0.000 claims 1
• KUQVMQAJGXNEOF-ZHRRBRCNSA-N (3s,6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chlorophenoxy)acetyl]-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=CC(Cl)=C1 KUQVMQAJGXNEOF-ZHRRBRCNSA-N 0.000 claims 1
• XSDMXPUMVWKDEH-KUHUBIRLSA-N (3s,6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-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(Cl)=CS1 XSDMXPUMVWKDEH-KUHUBIRLSA-N 0.000 claims 1
• NFTHTZCCDZZDLC-KDOFPFPSSA-N (3s,6r)-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-KDOFPFPSSA-N 0.000 claims 1
• LGCCNIXEXADPDD-KUHUBIRLSA-N (3s,6r)-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-KUHUBIRLSA-N 0.000 claims 1
• VFZYJAKLLAPZRH-BTYIYWSLSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(5-chloro-1-benzothiophene-2-carbonyl)-6-methyl-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)[C@@H](C)C3)=O)CCC)=CC2=C1 VFZYJAKLLAPZRH-BTYIYWSLSA-N 0.000 claims 1
• FPOUZQOUYUELER-BTYIYWSLSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzofuran-2-carbonyl)-6-methyl-3-propylpiperazin-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)[C@@H](C)C3)=O)CCC)=CC2=C1 FPOUZQOUYUELER-BTYIYWSLSA-N 0.000 claims 1
• VQXNPUMSLCDMKP-BTYIYWSLSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzothiophene-2-carbonyl)-6-methyl-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)[C@@H](C)C3)=O)CCC)=CC2=C1 VQXNPUMSLCDMKP-BTYIYWSLSA-N 0.000 claims 1
• 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
• WRQWWZXJYMQEQB-OAQYLSRUSA-N (5s)-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-propan-2-yl-4-[(1-pyridin-4-ylpiperidin-4-yl)methyl]piperazine-2,3-dione Chemical compound C([C@@H](N(C(=O)C1=O)CC2CCN(CC2)C=2C=CN=CC=2)C(C)C)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 WRQWWZXJYMQEQB-OAQYLSRUSA-N 0.000 claims 1
• FMFJKKAAUZCAFF-LJQANCHMSA-N (6S)-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-propan-2-yl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound CC(C)[C@H]1CN(CC(=O)N1Cc1cc2cnccc2[nH]1)S(=O)(=O)C=Cc1ccc(Cl)s1 FMFJKKAAUZCAFF-LJQANCHMSA-N 0.000 claims 1
• LJAZIGROAHYSIW-KRWDZBQOSA-N (6S)-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-propyl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound CCC[C@H]1CN(CC(=O)N1Cc1cc2cnccc2[nH]1)S(=O)(=O)C=Cc1ccc(Cl)s1 LJAZIGROAHYSIW-KRWDZBQOSA-N 0.000 claims 1
• NURCRLMTZDSNCX-OAQYLSRUSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@H]3CC(C)C)=CC=C21 NURCRLMTZDSNCX-OAQYLSRUSA-N 0.000 claims 1
• BNQVIOJIVRWRHU-CYBMUJFWSA-N (6r)-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-CYBMUJFWSA-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
• QVZKFTXRRXJDLI-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]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)CNC(C)C)=CC2=C1 QVZKFTXRRXJDLI-LJQANCHMSA-N 0.000 claims 1
• TWXOZYVJKKEMRE-CQSZACIVSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)COC)N1C(=O)COC1=CC=C(Cl)S1 TWXOZYVJKKEMRE-CQSZACIVSA-N 0.000 claims 1
• UZZJCFODHGBNAP-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(ethoxymethyl)piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)COCC)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 UZZJCFODHGBNAP-QGZVFWFLSA-N 0.000 claims 1
• KPCCBZMZLJTXIX-MRXNPFEDSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)COC)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 KPCCBZMZLJTXIX-MRXNPFEDSA-N 0.000 claims 1
• ZDACGCXWKCRRPS-JOCHJYFZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(phenylmethoxymethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)OCC1=CC=CC=C1 ZDACGCXWKCRRPS-JOCHJYFZSA-N 0.000 claims 1
• 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
• RVCQJKXSJNFFQP-OAQYLSRUSA-N (6r)-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2NC3=CC=C(Cl)C=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 RVCQJKXSJNFFQP-OAQYLSRUSA-N 0.000 claims 1
• GHQVQVWNSAUJDO-QGZVFWFLSA-N (6r)-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2NC3=CC=C(Cl)C=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 GHQVQVWNSAUJDO-QGZVFWFLSA-N 0.000 claims 1
• IJFRIUWEHKDGFH-OAQYLSRUSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 IJFRIUWEHKDGFH-OAQYLSRUSA-N 0.000 claims 1
• KIVLFZYOQQSSHW-QGZVFWFLSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 KIVLFZYOQQSSHW-QGZVFWFLSA-N 0.000 claims 1
• SXNOHZLZDPIQJW-GOSISDBHSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)COC)=CC2=C1 SXNOHZLZDPIQJW-GOSISDBHSA-N 0.000 claims 1
• FHSBXUVKNRVGGG-MRXNPFEDSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3SC=4CCCCC=4N=3)COC)=CC2=C1 FHSBXUVKNRVGGG-MRXNPFEDSA-N 0.000 claims 1
• SUCXPXLCKUQNSG-LJQANCHMSA-N (6r)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 SUCXPXLCKUQNSG-LJQANCHMSA-N 0.000 claims 1
• UXRAWXVAGJABEX-MRXNPFEDSA-N (6r)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 UXRAWXVAGJABEX-MRXNPFEDSA-N 0.000 claims 1
• SGKFTCOOCKCZTR-OAQYLSRUSA-N (6r)-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 SGKFTCOOCKCZTR-OAQYLSRUSA-N 0.000 claims 1
• KUQPKDBZGAYRFK-QGZVFWFLSA-N (6r)-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 KUQPKDBZGAYRFK-QGZVFWFLSA-N 0.000 claims 1
• YDHXTHMGVOOEPR-INIZCTEOSA-N (6s)-1-[(4-amino-6-chloroquinazolin-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(=CC4=C(N)N=CN=C4C=3)Cl)CC(C)C)=NC2=C1 YDHXTHMGVOOEPR-INIZCTEOSA-N 0.000 claims 1
• 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
• YPWWNMNMNRGREJ-NRFANRHFSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CNC(C)C)=CC=C21 YPWWNMNMNRGREJ-NRFANRHFSA-N 0.000 claims 1
• YVPJSNWYWPVMPW-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]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)CNC(C)C)=CC2=C1 YVPJSNWYWPVMPW-IBGZPJMESA-N 0.000 claims 1
• NLMRMVBWJCEEBL-FQEVSTJZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4SC5=CC(Cl)=CC=C5C=4)C[C@@H]3CC(C)C)=CC=C21 NLMRMVBWJCEEBL-FQEVSTJZSA-N 0.000 claims 1
• ZWBMNNLADQIJPN-FQEVSTJZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(pyrrolidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(C1)S(=O)(=O)C=1SC2=CC(Cl)=CC=C2C=1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCC1 ZWBMNNLADQIJPN-FQEVSTJZSA-N 0.000 claims 1
• VPXKHNAXMIPSQA-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(2-methoxyethylamino)methyl]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)CNCCOC)=CC2=C1 VPXKHNAXMIPSQA-IBGZPJMESA-N 0.000 claims 1
• FOZFNMFFKFHWFK-VWLOTQADSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]piperazin-2-one Chemical compound C([C@@H]1N(C(CN(C1)S(=O)(=O)C=1SC2=CC(Cl)=CC=C2C=1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N(CC1)CCC1N1CCCC1 FOZFNMFFKFHWFK-VWLOTQADSA-N 0.000 claims 1
• QVZKFTXRRXJDLI-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]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)CNC(C)C)=CC2=C1 QVZKFTXRRXJDLI-IBGZPJMESA-N 0.000 claims 1
• ILWNJPBQNWSXDJ-HXUWFJFHSA-N (6s)-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-HXUWFJFHSA-N 0.000 claims 1
• CVPJYLZMAJIUOO-SFHVURJKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(pyrrolidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(C1)S(=O)(=O)C=1NC2=CC(Cl)=CC=C2N=1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCC1 CVPJYLZMAJIUOO-SFHVURJKSA-N 0.000 claims 1
• QDZMGHLCPZAESW-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]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)CNC(C)C)=NC2=C1 QDZMGHLCPZAESW-KRWDZBQOSA-N 0.000 claims 1
• YRUYPOCCFXKUGQ-HXUWFJFHSA-N (6s)-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-HXUWFJFHSA-N 0.000 claims 1
• HZHRIYSVCLZNNH-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]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)CNC(C)C)=CC2=C1 HZHRIYSVCLZNNH-IBGZPJMESA-N 0.000 claims 1
• HMRPAOMZDREQHD-OAQYLSRUSA-N (6s)-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-OAQYLSRUSA-N 0.000 claims 1
• TWXOZYVJKKEMRE-AWEZNQCLSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)COC)N1C(=O)COC1=CC=C(Cl)S1 TWXOZYVJKKEMRE-AWEZNQCLSA-N 0.000 claims 1
• AXFWTRVUGUEQHS-FQEVSTJZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(piperidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCCC1 AXFWTRVUGUEQHS-FQEVSTJZSA-N 0.000 claims 1
• COGJCAUQLJHSBO-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(pyrrolidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCC1 COGJCAUQLJHSBO-IBGZPJMESA-N 0.000 claims 1
• UXMMLTRKZFEPPX-SFHVURJKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)CNC(C)C)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 UXMMLTRKZFEPPX-SFHVURJKSA-N 0.000 claims 1
• 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
• ZXZIDLKPPGQBSV-HXUWFJFHSA-N (6s)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-propan-2-yl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)C(C)C)=CC2=C1 ZXZIDLKPPGQBSV-HXUWFJFHSA-N 0.000 claims 1
• XXQQSSMBNPADTI-IBGZPJMESA-N (6s)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-propyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)CCC)=CC2=C1 XXQQSSMBNPADTI-IBGZPJMESA-N 0.000 claims 1
• KYSCQDJVEQDRIM-FQEVSTJZSA-N (6s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-(methoxymethyl)-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C([C@H]1COC)N(C(=O)COC=2SC(Cl)=CC=2)CC(=O)N1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 KYSCQDJVEQDRIM-FQEVSTJZSA-N 0.000 claims 1
• VJZHTDSMEAFUAW-SFHVURJKSA-N (6s)-6-(aminomethyl)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CN)=CC=C21 VJZHTDSMEAFUAW-SFHVURJKSA-N 0.000 claims 1
• RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims 1
• XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims 1
• PAVDLYMVFNUTSN-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(2-piperidin-3-yloxyacetyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)COC1CCCNC1 PAVDLYMVFNUTSN-UHFFFAOYSA-N 0.000 claims 1
• GXPSLBFHCWQTLO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(2-chloroimidazo[1,2-a]pyridin-7-yl)methyl]piperazin-2-one Chemical compound C1=CN2C=C(Cl)N=C2C=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 GXPSLBFHCWQTLO-UHFFFAOYSA-N 0.000 claims 1
• BCSJWMNINIYXSJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3,5-dichloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(Cl)=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 BCSJWMNINIYXSJ-UHFFFAOYSA-N 0.000 claims 1
• MHSZEDPAOYJKMP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3-bromo-5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(Br)=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 MHSZEDPAOYJKMP-UHFFFAOYSA-N 0.000 claims 1
• BNQVIOJIVRWRHU-UHFFFAOYSA-N 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)N3CC(N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 BNQVIOJIVRWRHU-UHFFFAOYSA-N 0.000 claims 1
• NURCRLMTZDSNCX-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)CC3CC(C)C)=CC=C21 NURCRLMTZDSNCX-UHFFFAOYSA-N 0.000 claims 1
• YEIRMODVXOUDEP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazine-2-carboxylic acid Chemical compound ClC1=CC=C2NC(CN3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(O)=O)=CC2=C1 YEIRMODVXOUDEP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• BQMSIWZKTIVDGW-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]piperazin-2-one;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.ClC1=CC=C2NC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 BQMSIWZKTIVDGW-UHFFFAOYSA-N 0.000 claims 1
• IOWFCFYBWFUKJM-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-3-fluoro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(F)=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 IOWFCFYBWFUKJM-UHFFFAOYSA-N 0.000 claims 1
• CITBBVYURFTNKL-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-3-methyl-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(C)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 CITBBVYURFTNKL-UHFFFAOYSA-N 0.000 claims 1
• DRKAKTXDHWDJKB-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-3-oxo-n-(2-pyrrolidin-1-ylethyl)piperazine-2-carboxamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN1CCN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)C(=O)C1C(=O)NCCN1CCCC1 DRKAKTXDHWDJKB-UHFFFAOYSA-N 0.000 claims 1
• LCEFYSIYMDTACV-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C4CCCCC4N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 LCEFYSIYMDTACV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• QBZNNMLBGQRFHR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound C1=C(Cl)C=C2C=NC(CN3C4CCCCC4N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 QBZNNMLBGQRFHR-UHFFFAOYSA-N 0.000 claims 1
• UMFYOSUBBQFEQX-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chlorophenyl)sulfanylacetyl]piperazin-2-one;1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]-3-(4-chlorophenyl)propane-1,3-dione Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CSC1=CC=CC(Cl)=C1.C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CC(=O)C1=CC=C(Cl)C=C1 UMFYOSUBBQFEQX-UHFFFAOYSA-N 0.000 claims 1
• OUBOAUSHLMWILB-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorophenyl)sulfanylacetyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CSC1=CC=C(Cl)C=C1 OUBOAUSHLMWILB-UHFFFAOYSA-N 0.000 claims 1
• AEHIJBOZNXHLFF-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-oxopiperazine-2-carboxylic acid Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)C(C(O)=O)CN1C(=O)COC1=CC=C(Cl)S1 AEHIJBOZNXHLFF-UHFFFAOYSA-N 0.000 claims 1
• XTUFNNVDMZQLKL-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-chlorophenyl)-3-hydroxyprop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)C=C(O)C1=CC=CC(Cl)=C1 XTUFNNVDMZQLKL-UHFFFAOYSA-N 0.000 claims 1
• GGBGCQDKHYOEGI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)C2CCCCC2N1C(=O)C=CC1=CC=C(Cl)S1 GGBGCQDKHYOEGI-UHFFFAOYSA-N 0.000 claims 1
• 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
• 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
• VWJJWDDLUUVGNL-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(5-chlorothiophen-2-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(C=1)=CC=CC=1C1=CC=C(Cl)S1 VWJJWDDLUUVGNL-UHFFFAOYSA-N 0.000 claims 1
• BAIGVSWNEZQYPE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(C=C1)=CC=C1C1=CC=C(Cl)S1 BAIGVSWNEZQYPE-UHFFFAOYSA-N 0.000 claims 1
• NLKMLCWTICCFIR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]piperazine-2,3-dione Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1=O)=O)CCN1CC(C=C1)=CC=C1C1=CC=C(Cl)S1 NLKMLCWTICCFIR-UHFFFAOYSA-N 0.000 claims 1
• YFUKVRGSOSXBNR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]piperazine-2,3-dione Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1=O)=O)CCN1CC(=NO1)C=C1C1=CC=C(Cl)S1 YFUKVRGSOSXBNR-UHFFFAOYSA-N 0.000 claims 1
• DAOHZQMIUNRYJY-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-chloro-3-(methylaminomethyl)-1h-indol-2-yl]methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(CNC)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 DAOHZQMIUNRYJY-UHFFFAOYSA-N 0.000 claims 1
• YQTOVNOFKMYGKE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-chloro-3-(morpholin-4-ylmethyl)-1h-indol-2-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC=1NC2=CC=C(Cl)C=C2C=1CN1CCOCC1 YQTOVNOFKMYGKE-UHFFFAOYSA-N 0.000 claims 1
• DQAZYAIYJCTXEE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-chloro-3-(pyrrolidin-1-ylmethyl)-1h-indol-2-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC=1NC2=CC=C(Cl)C=C2C=1CN1CCCC1 DQAZYAIYJCTXEE-UHFFFAOYSA-N 0.000 claims 1
• XYPCPKUUOJPTJB-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-chloro-3-[(dimethylamino)methyl]-1h-indol-2-yl]methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(CN(C)C)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 XYPCPKUUOJPTJB-UHFFFAOYSA-N 0.000 claims 1
• ZOUYISFGRYQJMS-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[6-(5-chlorothiophen-2-yl)pyridin-3-yl]methyl]piperazin-2-one 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Nc1ncnc2cc(CN3CCN(Cc4ccc(nc4)-c4ccc(Cl)s4)CC3=O)ccc12 ZOUYISFGRYQJMS-UHFFFAOYSA-N 0.000 claims 1
• NIEWQIUSHZNFEZ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-6-methyl-3-propylpiperazin-2-one Chemical compound O=C1C(CCC)NCC(C)N1CC1=CC=C(C(N)=NC=N2)C2=C1 NIEWQIUSHZNFEZ-UHFFFAOYSA-N 0.000 claims 1
• YYIOZALXURGXFL-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]piperazine-2,3-dione Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1=O)=O)CCN1CC(C=C1)=CC=C1C1=CC=C(Cl)S1 YYIOZALXURGXFL-UHFFFAOYSA-N 0.000 claims 1
• OLYZHWCDBKQORH-UHFFFAOYSA-N 1-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound CC1=C(C(=O)C)SC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 OLYZHWCDBKQORH-UHFFFAOYSA-N 0.000 claims 1
• ROGWVRJJUNEQOV-UHFFFAOYSA-N 1-[(6-chloro-1-benzothiophen-2-yl)methyl]-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2,3-dione Chemical compound N1=CC=C2NC(CN3CCN(C(C3=O)=O)CC3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 ROGWVRJJUNEQOV-UHFFFAOYSA-N 0.000 claims 1
• WSGIXMSIZCPDHM-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(3-chlorophenyl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=CC(Cl)=C1 WSGIXMSIZCPDHM-UHFFFAOYSA-N 0.000 claims 1
• KZMYXJMZEQVWLN-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(4-hydroxyphenyl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=C(O)C=C1 KZMYXJMZEQVWLN-UHFFFAOYSA-N 0.000 claims 1
• ULOLZIWTTFPNIT-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(5-chlorothiophen-2-yl)-2-fluoropropane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)C(F)C(=O)C1=CC=C(Cl)S1 ULOLZIWTTFPNIT-UHFFFAOYSA-N 0.000 claims 1
• QHCJJDVEXUJHGQ-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(5-chlorothiophen-2-yl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=C(Cl)S1 QHCJJDVEXUJHGQ-UHFFFAOYSA-N 0.000 claims 1
• UZWZEXFLFCPVQT-FQEVSTJZSA-N 1-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]-3-ethylurea Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CNC(=O)NCC)=CC=C21 UZWZEXFLFCPVQT-FQEVSTJZSA-N 0.000 claims 1
• NGWXDNUOUCLIAE-DEOSSOPVSA-N 1-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]-3-phenylurea 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)NC(=O)NC1=CC=CC=C1 NGWXDNUOUCLIAE-DEOSSOPVSA-N 0.000 claims 1
• SHQWVCMOTZBCKF-UHFFFAOYSA-N 1-[[4-(3-bromophenyl)-1,3-thiazol-2-yl]methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CC(Br)=C1 SHQWVCMOTZBCKF-UHFFFAOYSA-N 0.000 claims 1
• XTIYEPGZYCNSMA-UHFFFAOYSA-N 1-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2,3-dione Chemical compound S1C(Cl)=CC=C1C(C=C1)=CC=C1CN1C(=O)C(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 XTIYEPGZYCNSMA-UHFFFAOYSA-N 0.000 claims 1
• 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
• GAFJWUZJWIDXOR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-[(4-pyridin-4-ylphenyl)methyl]piperazine-2,3-dione Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C(C(=O)N(CC=3C=CC(=CC=3)C=3C=CN=CC=3)CC2)=O)=NO1 GAFJWUZJWIDXOR-UHFFFAOYSA-N 0.000 claims 1
• 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
• 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
• DQBJCMJYLCEJOO-QFIPXVFZSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-1-[(7-chloroisoquinolin-3-yl)methyl]-3-oxopiperazin-2-yl]acetamide Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC(=O)N)=CC=C21 DQBJCMJYLCEJOO-QFIPXVFZSA-N 0.000 claims 1
• UWBXANVZQKMGSD-HNNXBMFYSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-1-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-oxopiperazin-2-yl]acetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(=O)N)C(=O)COC1=CC=C(Cl)S1 UWBXANVZQKMGSD-HNNXBMFYSA-N 0.000 claims 1
• HSLJRFINDOWMSL-HNNXBMFYSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-n-(5-chlorothiophen-2-yl)-2-oxoacetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C(=O)NC1=CC=C(Cl)S1 HSLJRFINDOWMSL-HNNXBMFYSA-N 0.000 claims 1
• XNDZOHFHBYSJHC-INIZCTEOSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-n-(5-chlorothiophen-2-yl)-2-oxoacetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C(=O)NC1=CC=C(Cl)S1 XNDZOHFHBYSJHC-INIZCTEOSA-N 0.000 claims 1
• JMNXWPRLKZUFQK-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 JMNXWPRLKZUFQK-UHFFFAOYSA-N 0.000 claims 1
• BOQXWPQBBXCQKC-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 BOQXWPQBBXCQKC-UHFFFAOYSA-N 0.000 claims 1
• UZMODBUJHXOIRP-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 UZMODBUJHXOIRP-UHFFFAOYSA-N 0.000 claims 1
• ZFFBLWCLKQADPY-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]acetamide Chemical compound NC(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 ZFFBLWCLKQADPY-UHFFFAOYSA-N 0.000 claims 1
• 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
• FFISDNWFDOYBIC-MRXNPFEDSA-N 2-[[(2r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-n,n,4-trimethyl-1,3-thiazole-5-carboxamide Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC1=NC(C)=C(C(=O)N(C)C)S1 FFISDNWFDOYBIC-MRXNPFEDSA-N 0.000 claims 1
• BZGZPQUEOZHRFI-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-5,6,7,8-tetrahydro-[1,3]thiazolo[4,5-c]azepin-4-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(S1)=NC2=C1CCCNC2=O BZGZPQUEOZHRFI-UHFFFAOYSA-N 0.000 claims 1
• NHUZOIZILDWJKP-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-5,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-6-one Chemical compound C1NC(=O)CC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 NHUZOIZILDWJKP-UHFFFAOYSA-N 0.000 claims 1
• 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
• 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
• 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
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 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
• WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 claims 1
• ZQVYRVKWNGGCLO-FQEVSTJZSA-N 3-[2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-2-oxoethyl]benzenecarboximidamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CC1=CC=CC(C(N)=N)=C1 ZQVYRVKWNGGCLO-FQEVSTJZSA-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
• WAJSOHUQSZOARJ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,3,4-oxadiazol-2-yl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C(O1)=NN=C1CC1C(=O)N(CC=2NC3=CC=NC=C3C=2)CCN1 WAJSOHUQSZOARJ-UHFFFAOYSA-N 0.000 claims 1
• DBMCFCZDENQJRR-UHFFFAOYSA-N 4-(1-benzothiophen-2-ylsulfonyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC=C2SC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=C1 DBMCFCZDENQJRR-UHFFFAOYSA-N 0.000 claims 1
• MJOOKNHBSXXGRD-UHFFFAOYSA-N 4-(7-methoxynaphthalen-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=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1 MJOOKNHBSXXGRD-UHFFFAOYSA-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
• MYKVWZWWOLURHO-UHFFFAOYSA-N 4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)COC)=CC2=C1 MYKVWZWWOLURHO-UHFFFAOYSA-N 0.000 claims 1
• KTOJLHCKDVXMRK-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-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)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 KTOJLHCKDVXMRK-UHFFFAOYSA-N 0.000 claims 1
• VGXFIUFJTPNFJJ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(4,5,6,7-tetrahydro-[1,3]thiazolo[4,5-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1NCCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 VGXFIUFJTPNFJJ-UHFFFAOYSA-N 0.000 claims 1
• UOHKTMNERGZJDS-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1CNCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 UOHKTMNERGZJDS-UHFFFAOYSA-N 0.000 claims 1
• FRKRBNXDBRYDOR-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(piperidin-4-ylmethyl)piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC1CCNCC1 FRKRBNXDBRYDOR-UHFFFAOYSA-N 0.000 claims 1
• GEWADIJSIYYLDE-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyrazin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=CN=CC=N1 GEWADIJSIYYLDE-UHFFFAOYSA-N 0.000 claims 1
• UXJDQBKFDIAYEN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyrimidin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=NC=CC=N1 UXJDQBKFDIAYEN-UHFFFAOYSA-N 0.000 claims 1
• RDJXFURVMDXNFX-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-methyl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 RDJXFURVMDXNFX-UHFFFAOYSA-N 0.000 claims 1
• KULHGWKQZSXESJ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-phenyl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CC=C1 KULHGWKQZSXESJ-UHFFFAOYSA-N 0.000 claims 1
• XLJJJPSJMCFWSM-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-pyridin-2-yl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CC=N1 XLJJJPSJMCFWSM-UHFFFAOYSA-N 0.000 claims 1
• QRYNOSKGUPZZJU-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-pyridin-3-yl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CN=C1 QRYNOSKGUPZZJU-UHFFFAOYSA-N 0.000 claims 1
• PCEDICIDOGFPAY-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-pyridin-4-yl-1,3-thiazol-2-yl)methyl]piperazin-2-one;hydrobromide Chemical compound Br.S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=NC=C1 PCEDICIDOGFPAY-UHFFFAOYSA-N 0.000 claims 1
• VITROVPYFUPPDL-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCN(CC=4N=3)C)=CC2=C1 VITROVPYFUPPDL-UHFFFAOYSA-N 0.000 claims 1
• OOQSLOYEJYAZHO-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=NC=4CCN(CC=4S3)C)=CC2=C1 OOQSLOYEJYAZHO-UHFFFAOYSA-N 0.000 claims 1
• RNDUUDSQVFINDP-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(7-methyl-1h-pyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=4C=NC=C(C=4N3)C)=CC2=C1 RNDUUDSQVFINDP-UHFFFAOYSA-N 0.000 claims 1
• NRWKWQCGTWQPEO-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=CC=NC(Cl)=N1 NRWKWQCGTWQPEO-UHFFFAOYSA-N 0.000 claims 1
• ACAOYSSCQRTQKQ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-(6-methoxypyridin-2-yl)piperidin-4-yl]methyl]piperazin-2-one Chemical compound COC1=CC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 ACAOYSSCQRTQKQ-UHFFFAOYSA-N 0.000 claims 1
• MKTSCPGJYVALCG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-(6-methoxypyridin-3-yl)piperidin-4-yl]methyl]piperazin-2-one Chemical compound C1=NC(OC)=CC=C1N1CCC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)CC1 MKTSCPGJYVALCG-UHFFFAOYSA-N 0.000 claims 1
• WBUXIMNSLSEDKG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(3-imidazol-1-ylpropylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C(N=1)=CC=NC=1NCCCN1C=CN=C1 WBUXIMNSLSEDKG-UHFFFAOYSA-N 0.000 claims 1
• GGDIVQHRVRCCIT-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C(N=1)=CC=NC=1NCCCN1CCOCC1 GGDIVQHRVRCCIT-UHFFFAOYSA-N 0.000 claims 1
• LPWMQHKBHIVWFF-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-[2-(dimethylamino)ethoxy]pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound CN(C)CCOC1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 LPWMQHKBHIVWFF-UHFFFAOYSA-N 0.000 claims 1
• AGUKJCQHGMNERN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-[4-(dimethylamino)butylamino]pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound CN(C)CCCCNC1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 AGUKJCQHGMNERN-UHFFFAOYSA-N 0.000 claims 1
• IKUUZMOAOWNSOZ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[4-(2-hydroxyphenyl)-1,3-thiazol-2-yl]methyl]piperazin-2-one Chemical compound OC1=CC=CC=C1C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 IKUUZMOAOWNSOZ-UHFFFAOYSA-N 0.000 claims 1
• WRCKCDICBAEZRK-JCOPYZAKSA-N 4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one (3S)-4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound ClC1=CC=C2C=C(N=CC2=C1)CN1[C@H](C(N(CC1)CC1=CC=C(C=C1)C=1C=NC(=CC1)OC)=O)CCC.ClC1=CC=C2C=C(N=CC2=C1)CN1CC(N(CC1)CC1=CC=C(C=C1)C=1C=NC(=CC1)OC)=O WRCKCDICBAEZRK-JCOPYZAKSA-N 0.000 claims 1
• BINLCYLOCVHECW-UHFFFAOYSA-N 4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound N1=CC2=CC(Cl)=CC=C2C=C1CN(CC1=O)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 BINLCYLOCVHECW-UHFFFAOYSA-N 0.000 claims 1
• PSWINVZJRGTEEF-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-1-[(7-methyl-1h-pyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound N1C=2C(C)=CN=CC=2C=C1CN(C(C1)=O)CCN1S(=O)(=O)C=CC1=CC=C(Cl)S1 PSWINVZJRGTEEF-UHFFFAOYSA-N 0.000 claims 1
• FOMZRIYDVNSYOD-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-(hydroxymethyl)-1-[(1-methylpyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C=1C2=CN=CC=C2N(C)C=1CN(C(C1)=O)C(CO)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 FOMZRIYDVNSYOD-UHFFFAOYSA-N 0.000 claims 1
• PNJIKIRPUGWUFI-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 PNJIKIRPUGWUFI-UHFFFAOYSA-N 0.000 claims 1
• FPASUXCSBVRIIA-NRFANRHFSA-N 4-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-3-oxoprop-1-enyl]benzenesulfonamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(S(N)(=O)=O)C=C1 FPASUXCSBVRIIA-NRFANRHFSA-N 0.000 claims 1
• AVUFQZZRFHJVRJ-FQEVSTJZSA-N 4-[[(2s)-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-2-(2-methylpropyl)-6-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C([C@@H]1CC(C)C)N(S(=O)(=O)C=2NC3=CC=C(Cl)C=C3C=2)CC(=O)N1CC1=CC=C(C(N)=N)C=C1 AVUFQZZRFHJVRJ-FQEVSTJZSA-N 0.000 claims 1
• BHTZANLPHRFPIT-FQEVSTJZSA-N 4-[[(2s)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(2-methylpropyl)-6-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C([C@@H]1CC(C)C)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC1=CC=C(C(N)=N)C=C1 BHTZANLPHRFPIT-FQEVSTJZSA-N 0.000 claims 1
• RRTRVCANLBOYRA-SFHVURJKSA-N 4-[[(2s)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-2-(2-methylpropyl)-6-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C([C@@H]1CC(C)C)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC1=CC=C(C(N)=N)C=C1 RRTRVCANLBOYRA-SFHVURJKSA-N 0.000 claims 1
• QSRBRJFILWMDSD-UHFFFAOYSA-N 4-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C1=NOC(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=C1 QSRBRJFILWMDSD-UHFFFAOYSA-N 0.000 claims 1
• YQXHQQBEQGRVPC-UHFFFAOYSA-N 4-[[3-(5-chlorothiophen-2-yl)-1h-1,2,4-triazol-5-yl]methyl]-1-(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=NNC(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=N1 YQXHQQBEQGRVPC-UHFFFAOYSA-N 0.000 claims 1
• ZJDZOKBUANAJMW-UHFFFAOYSA-N 4-[[3-(5-chlorothiophen-2-yl)-1h-pyrazol-5-yl]methyl]-1-(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=NNC(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=C1 ZJDZOKBUANAJMW-UHFFFAOYSA-N 0.000 claims 1
• UUEGOZVSGVTBCL-UHFFFAOYSA-N 4-[[3-(5-chlorothiophen-2-yl)phenyl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C1=CC=CC(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=C1 UUEGOZVSGVTBCL-UHFFFAOYSA-N 0.000 claims 1
• AVXIZTSASMZONB-UHFFFAOYSA-N 4-[[4-(5-chlorothiophen-2-yl)phenyl]methyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1CC(C=C1)=CC=C1C1=CC=C(Cl)S1 AVXIZTSASMZONB-UHFFFAOYSA-N 0.000 claims 1
• GOFCHNWBLGFEOC-UHFFFAOYSA-N 4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N)CCC1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 GOFCHNWBLGFEOC-UHFFFAOYSA-N 0.000 claims 1
• XKDHMIDBBNOKNT-UHFFFAOYSA-N 4-[[4-[4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidin-1-yl]pyrimidin-2-yl]-methylamino]butanoic acid Chemical compound OC(=O)CCCN(C)C1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 XKDHMIDBBNOKNT-UHFFFAOYSA-N 0.000 claims 1
• QTOKJSPCFYAAJK-UHFFFAOYSA-N 4-[[5-(3-chlorophenyl)furan-2-yl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound ClC1=CC=CC(C=2OC(CN3CC(=O)N(CC=4NC5=CC=NC=C5C=4)CC3)=CC=2)=C1 QTOKJSPCFYAAJK-UHFFFAOYSA-N 0.000 claims 1
• BKLLPBOJHRLNSI-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-1-(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(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=NO1 BKLLPBOJHRLNSI-UHFFFAOYSA-N 0.000 claims 1
• NUAYNFYFICELME-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]-1-(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=C1C(S1)=NN=C1CN1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 NUAYNFYFICELME-UHFFFAOYSA-N 0.000 claims 1
• HQGAOAVNAVRNBK-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)-1,3-oxazol-2-yl]methyl]-1-(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=C1C(O1)=CN=C1CN1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 HQGAOAVNAVRNBK-UHFFFAOYSA-N 0.000 claims 1
• WAZRUUMAHJTUBT-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)pyridin-2-yl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C(C=N1)=CC=C1CN1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 WAZRUUMAHJTUBT-UHFFFAOYSA-N 0.000 claims 1
• OVNLEOHTDKLZQS-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)pyridin-2-yl]methyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1CC(N=C1)=CC=C1C1=CC=C(Cl)S1 OVNLEOHTDKLZQS-UHFFFAOYSA-N 0.000 claims 1
• WCROBYRVIIKUNR-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)thiophen-2-yl]methyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1CC(S1)=CC=C1C1=CC=C(Cl)S1 WCROBYRVIIKUNR-UHFFFAOYSA-N 0.000 claims 1
• QFJZSUYLFPXCPS-UHFFFAOYSA-N 4-[[6-(5-chlorothiophen-2-yl)pyridin-2-yl]methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C1=CC=CC(CN2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)=N1 QFJZSUYLFPXCPS-UHFFFAOYSA-N 0.000 claims 1
• SXXPCYXZTBJWBT-UHFFFAOYSA-N 4-[[6-(5-chlorothiophen-2-yl)pyridin-2-yl]methyl]-6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1CC(N=1)=CC=CC=1C1=CC=C(Cl)S1 SXXPCYXZTBJWBT-UHFFFAOYSA-N 0.000 claims 1
• PCHBMNCFKJKQPA-UHFFFAOYSA-N 5-chlorothiophen-2-amine Chemical compound NC1=CC=C(Cl)S1 PCHBMNCFKJKQPA-UHFFFAOYSA-N 0.000 claims 1
• VYROBYHYROFIBU-UHFFFAOYSA-N 6-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-[(5-thiophen-2-ylthiophen-2-yl)methyl]piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(COC)CN1CC(S1)=CC=C1C1=CC=CS1 VYROBYHYROFIBU-UHFFFAOYSA-N 0.000 claims 1
• FQGZEESRMSRISX-UHFFFAOYSA-N 6-[4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidin-1-yl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)CC1 FQGZEESRMSRISX-UHFFFAOYSA-N 0.000 claims 1
• GSBLRHZPUXJMIR-INIZCTEOSA-N 6-[[(3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-2-oxopiperazin-1-yl]methyl]-1h-quinazolin-4-one Chemical compound N1([C@H](C(N(CC=2C=C3C(=O)N=CNC3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(Cl)S1 GSBLRHZPUXJMIR-INIZCTEOSA-N 0.000 claims 1
• MVRJRFJKFXWAOE-KRWDZBQOSA-N 6-[[(3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-2-oxopiperazin-1-yl]methyl]-3-methylquinazolin-4-one Chemical compound N1([C@H](C(N(CC=2C=C3C(=O)N(C)C=NC3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(Cl)S1 MVRJRFJKFXWAOE-KRWDZBQOSA-N 0.000 claims 1
• ZPKZBSBPBXZYAJ-UHFFFAOYSA-N 6-propan-2-ylpiperazin-2-one Chemical compound CC(C)C1CNCC(=O)N1 ZPKZBSBPBXZYAJ-UHFFFAOYSA-N 0.000 claims 1
• IKCFXFPVTXLNIA-DEOSSOPVSA-N 7-[[(3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-3-(methoxymethyl)-2-oxopiperazin-1-yl]methyl]-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)COC)=CC=C21 IKCFXFPVTXLNIA-DEOSSOPVSA-N 0.000 claims 1
• RWTSGLHQRCGVOS-KRWDZBQOSA-N 7-[[(3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-2-oxo-3-propylpiperazin-1-yl]methyl]-1h-quinazolin-4-one Chemical compound N1([C@H](C(N(CC=2C=C3C(C(N=CN3)=O)=CC=2)CC1)=O)CCC)C(=O)COC1=CC=C(Cl)S1 RWTSGLHQRCGVOS-KRWDZBQOSA-N 0.000 claims 1
• DDNPAZNSBWHINI-IBGZPJMESA-N 7-[[(3s)-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-2-oxo-3-propylpiperazin-1-yl]methyl]-1h-quinazolin-4-one Chemical compound N1([C@H](C(N(CC=2C=C3C(C(N=CN3)=O)=CC=2)CC1)=O)CCC)C(=O)C=CC1=CC=C(Cl)S1 DDNPAZNSBWHINI-IBGZPJMESA-N 0.000 claims 1
• STLZNZZZHQJODP-UHFFFAOYSA-N 9-[(4-aminoquinazolin-7-yl)methyl]-6,9-diazaspiro[4.5]decan-10-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C1=O)CCNC21CCCC2 STLZNZZZHQJODP-UHFFFAOYSA-N 0.000 claims 1
• XYOFPPSDRNPNPN-UHFFFAOYSA-N C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CS(=O)(=O)C1=CC=CC(Cl)=C1 Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CS(=O)(=O)C1=CC=CC(Cl)=C1 XYOFPPSDRNPNPN-UHFFFAOYSA-N 0.000 claims 1
• JOQVSXLHAPDLTF-NRFANRHFSA-N COC[C@@H]1N(CCN(Cc2ccc3c(N)ncnc3c2)C1=O)C(=O)CCc1cccc(c1)C(N)=N Chemical compound COC[C@@H]1N(CCN(Cc2ccc3c(N)ncnc3c2)C1=O)C(=O)CCc1cccc(c1)C(N)=N JOQVSXLHAPDLTF-NRFANRHFSA-N 0.000 claims 1
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• KLRIITUPJXUDHA-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(=O)N1CC(N(C2CCCCC12)CC1=CC=C2C(=NC=NC2=C1)N)=O Chemical compound ClC1=CC=C(C=C1)NC(=O)N1CC(N(C2CCCCC12)CC1=CC=C2C(=NC=NC2=C1)N)=O KLRIITUPJXUDHA-UHFFFAOYSA-N 0.000 claims 1
• IMLXPLXPDZURHG-IBGZPJMESA-N ClC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)CC(NC)=O Chemical compound ClC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)CC(NC)=O IMLXPLXPDZURHG-IBGZPJMESA-N 0.000 claims 1
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• RJEMWVXETFNMFD-HXUWFJFHSA-N NC1=NC=NC2=CC(=CC=C12)CN1[C@@H](CN(CC1=O)CC=1NC2=CC=C(C=C2C=1)Cl)CNS(=O)(=O)C=1SC(=CC=1)Br Chemical compound NC1=NC=NC2=CC(=CC=C12)CN1[C@@H](CN(CC1=O)CC=1NC2=CC=C(C=C2C=1)Cl)CNS(=O)(=O)C=1SC(=CC=1)Br RJEMWVXETFNMFD-HXUWFJFHSA-N 0.000 claims 1
• RPVZYQKVBTZLJW-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Nc1ncnc2cc(CN3CCN(Cc4ccc(cn4)-c4ccc(Cl)s4)CC3=O)ccc12 Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Nc1ncnc2cc(CN3CCN(Cc4ccc(cn4)-c4ccc(Cl)s4)CC3=O)ccc12 RPVZYQKVBTZLJW-UHFFFAOYSA-N 0.000 claims 1
• GDXNCMHLQYCCCC-IBGZPJMESA-N OC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)COC Chemical compound OC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)COC GDXNCMHLQYCCCC-IBGZPJMESA-N 0.000 claims 1
• LMERQYRIZQPDGG-SFHVURJKSA-N [(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methylurea Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CNC(=O)N)=CC=C21 LMERQYRIZQPDGG-SFHVURJKSA-N 0.000 claims 1
• YZEQSIBCEFTLDU-ZDUSSCGKSA-N benzyl (2s)-2-(2-methylsulfanylethyl)-3-oxopiperazine-1-carboxylate Chemical compound C1CNC(=O)[C@H](CCSC)N1C(=O)OCC1=CC=CC=C1 YZEQSIBCEFTLDU-ZDUSSCGKSA-N 0.000 claims 1
• SNXRMIWZSPUNPZ-UHFFFAOYSA-N benzyl 2-cyclopentyl-3-oxopiperazine-1-carboxylate Chemical compound C1CNC(=O)C(C2CCCC2)N1C(=O)OCC1=CC=CC=C1 SNXRMIWZSPUNPZ-UHFFFAOYSA-N 0.000 claims 1
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
• XBCAPAHXPBVJNE-OAHLLOKOSA-N ethyl 2-[[(2r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(CN2C(CN(C[C@@H]2COC)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 XBCAPAHXPBVJNE-OAHLLOKOSA-N 0.000 claims 1
• NROCLZGJIMPDAZ-GOSISDBHSA-N ethyl 3-[2-[[(2r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-3-methylbutanoate Chemical compound CCOC(=O)CC(C)(C)C1=CSC(CN2C(CN(C[C@@H]2COC)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 NROCLZGJIMPDAZ-GOSISDBHSA-N 0.000 claims 1
• UJGNKVLTNDDWET-UHFFFAOYSA-N methyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(=O)OC)=CC2=C1 UJGNKVLTNDDWET-UHFFFAOYSA-N 0.000 claims 1
• VQRXMIGFCMMVRN-UHFFFAOYSA-N methyl 1-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-5-oxo-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(=O)N(CC=4NC5=CC=NC=C5C=4)CC3C(=O)OC)=CC2=C1 VQRXMIGFCMMVRN-UHFFFAOYSA-N 0.000 claims 1
• RVKWHVYFQDHCKM-INIZCTEOSA-N methyl 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-1-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-oxopiperazin-2-yl]acetate Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(=O)OC)C(=O)COC1=CC=C(Cl)S1 RVKWHVYFQDHCKM-INIZCTEOSA-N 0.000 claims 1
• KWZXRUBDWWPWEL-UHFFFAOYSA-N methyl 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]acetate Chemical compound COC(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 KWZXRUBDWWPWEL-UHFFFAOYSA-N 0.000 claims 1
• VGZCRYWFMYLTGA-UHFFFAOYSA-N methyl 4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-oxopiperazine-2-carboxylate Chemical compound COC(=O)C1CN(S(=O)(=O)C=2NC3=CC=C(Cl)C=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 VGZCRYWFMYLTGA-UHFFFAOYSA-N 0.000 claims 1
• PAIANPIJHPNSLO-UHFFFAOYSA-N methyl 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-oxopiperazine-2-carboxylate Chemical compound COC(=O)C1CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 PAIANPIJHPNSLO-UHFFFAOYSA-N 0.000 claims 1
• DAIFKXIICYHYRG-UHFFFAOYSA-N methyl 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxo-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)C(=O)OC)=CC2=C1 DAIFKXIICYHYRG-UHFFFAOYSA-N 0.000 claims 1
• NHJSPUSLYFOJGD-UHFFFAOYSA-N methyl 4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-oxopiperazine-2-carboxylate Chemical compound COC(=O)C1CN(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 NHJSPUSLYFOJGD-UHFFFAOYSA-N 0.000 claims 1
• GUDJJBCDIANKFK-UHFFFAOYSA-N methyl 4-[(6-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-oxopiperazine-2-carboxylate Chemical compound COC(=O)C1CN(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 GUDJJBCDIANKFK-UHFFFAOYSA-N 0.000 claims 1
• BBKNMQLOVMQZRO-UHFFFAOYSA-N methyl 6-chloro-1-benzofuran-2-carboxylate Chemical compound C1=C(Cl)C=C2OC(C(=O)OC)=CC2=C1 BBKNMQLOVMQZRO-UHFFFAOYSA-N 0.000 claims 1
• MOVJEUIWOFBBOR-IBGZPJMESA-N methyl n-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]carbamate Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CNC(=O)OC)=CC=C21 MOVJEUIWOFBBOR-IBGZPJMESA-N 0.000 claims 1
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 claims 1
• VOGSFPXCGJDOFG-NRFANRHFSA-N n-[5-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-3-oxopropyl]pyridin-2-yl]acetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CCC1=CC=C(NC(C)=O)N=C1 VOGSFPXCGJDOFG-NRFANRHFSA-N 0.000 claims 1
• NEGMYNFLPUIGMK-DEOSSOPVSA-N n-[5-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-butyl-3-oxopiperazin-1-yl]-3-oxoprop-1-enyl]-6-methylpyridin-2-yl]acetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)C=CC1=CC=C(NC(C)=O)N=C1C NEGMYNFLPUIGMK-DEOSSOPVSA-N 0.000 claims 1
• GGDKZTYZCFUSEW-QHCPKHFHSA-N n-[5-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-butyl-3-oxopiperazin-1-yl]-3-oxoprop-1-enyl]pyridin-2-yl]acetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)C=CC1=CC=C(NC(C)=O)N=C1 GGDKZTYZCFUSEW-QHCPKHFHSA-N 0.000 claims 1
• WMOZLCPHLIVBMN-QFIPXVFZSA-N n-[5-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-oxoprop-1-enyl]pyridin-2-yl]acetamide 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(NC(C)=O)N=C1 WMOZLCPHLIVBMN-QFIPXVFZSA-N 0.000 claims 1
• PBOOTINXTXIUJQ-NRFANRHFSA-N n-[[(2r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-oxopiperazin-2-yl]methyl]-n-(2-propan-2-yloxyethyl)formamide Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)CN(CCOC(C)C)C=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 PBOOTINXTXIUJQ-NRFANRHFSA-N 0.000 claims 1
• CNXJIWFSMUUYLH-NRFANRHFSA-N n-[[(2r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-oxopiperazin-2-yl]methyl]-n-(2-propan-2-yloxyethyl)methanimidamide Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)CN(CCOC(C)C)C=N)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 CNXJIWFSMUUYLH-NRFANRHFSA-N 0.000 claims 1
• OVABIGPDKNRCDX-IBGZPJMESA-N n-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]formamide Chemical compound ClC1=CC=C2NC(CN3C[C@H](CNC=O)N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 OVABIGPDKNRCDX-IBGZPJMESA-N 0.000 claims 1
• WMGYPXXLVCKHBY-NRFANRHFSA-N n-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]furan-2-carboxamide 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)NC(=O)C1=CC=CO1 WMGYPXXLVCKHBY-NRFANRHFSA-N 0.000 claims 1
• BVIVTOCVZHBRSJ-LJQANCHMSA-N n-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]methanesulfonamide Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@H]3CNS(=O)(=O)C)=CC=C21 BVIVTOCVZHBRSJ-LJQANCHMSA-N 0.000 claims 1
• FHQJVWPLQQELJE-NRFANRHFSA-N propan-2-yl n-[[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]methyl]carbamate Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CNC(=O)OC(C)C)=CC=C21 FHQJVWPLQQELJE-NRFANRHFSA-N 0.000 claims 1
• XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims 1
• JXJFAWJZUYQMJC-IBGZPJMESA-N tert-butyl 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazin-2-yl]acetate 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(=O)OC(C)(C)C)=CC2=C1 JXJFAWJZUYQMJC-IBGZPJMESA-N 0.000 claims 1
• REBNTWUPTFVVKF-UHFFFAOYSA-N tert-butyl 3-(5-chlorothiophen-2-yl)-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=C(Cl)S1 REBNTWUPTFVVKF-UHFFFAOYSA-N 0.000 claims 1
• ILUBQLROFBISHX-UHFFFAOYSA-N tert-butyl 5-chloro-2-chlorosulfonylindole-1-carboxylate Chemical compound ClC1=CC=C2N(C(=O)OC(C)(C)C)C(S(Cl)(=O)=O)=CC2=C1 ILUBQLROFBISHX-UHFFFAOYSA-N 0.000 claims 1
• GBTWJDAEKNGADB-UHFFFAOYSA-N tert-butyl 5-methyl-3-oxo-2-propylpiperazine-1-carboxylate Chemical compound CCCC1N(C(=O)OC(C)(C)C)CC(C)NC1=O GBTWJDAEKNGADB-UHFFFAOYSA-N 0.000 claims 1
• CSWGIYZSJBBEKY-UHFFFAOYSA-N tert-butyl 6-chloro-2-chlorosulfonylindole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OC(C)(C)C)C(S(Cl)(=O)=O)=CC2=C1 CSWGIYZSJBBEKY-UHFFFAOYSA-N 0.000 claims 1
• YVLUPJMJASMZCM-NRFANRHFSA-N tert-butyl n-[6-[2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]-2-oxoethoxy]pyridin-3-yl]carbamate Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(NC(=O)OC(C)(C)C)C=N1 YVLUPJMJASMZCM-NRFANRHFSA-N 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 71
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 53
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