SK11082000A3 - Substituované oxoazaheterocyklické inhibítory faktora xa, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Substituované oxoazaheterocyklické inhibítory faktora xa, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK11082000A3
Authority: SK; Slovakia
Prior art keywords: ylmethyl; piperazin; chloro; amino; aminoquinazolin
Prior art date: 1998-01-27

Application number

SK1108-2000A

Other languages

English (en)

Slovak (sk)

Inventor

William R. Ewing

Michael R. Becker

Yong Mi Choi-Sledeski

Heinz W. Pauls

Wei He

Stephen M. Condon

Roderick S. Davis

Barbara A. Hanney

Alfred P. Spada

Christopher J. Burns

John Z. Jiang

Aiwen Li

Michael R. Myers

Wan F. Lau

Gregory B. Poli

Original Assignee

Aventis Pharmaceuticals Products Inc.

Priority date (The priority date 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 date listed.)

1998-01-27

Filing date

1999-01-27

Publication date

2001-01-18

1999-01-27 Application filed by Aventis Pharmaceuticals Products Inc. filed Critical Aventis Pharmaceuticals Products Inc.

2001-01-18 Publication of SK11082000A3 publication Critical patent/SK11082000A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
229940123583 Factor Xa inhibitor Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 270
238000000034 method Methods 0.000 claims abstract description 43
108010074860 Factor Xa Proteins 0.000 claims abstract description 18
230000002401 inhibitory effect Effects 0.000 claims abstract description 6
-1 4-tert-butoxycarbonylaminopyridin-3-yl Chemical group 0.000 claims description 1173
239000000203 mixture Substances 0.000 claims description 87
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 73
125000001072 heteroaryl group Chemical group 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
229910052757 nitrogen Inorganic materials 0.000 claims description 56
229910052717 sulfur Inorganic materials 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 51
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 48
229910052760 oxygen Inorganic materials 0.000 claims description 48
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
125000000623 heterocyclic group Chemical group 0.000 claims description 37
125000000547 substituted alkyl group Chemical group 0.000 claims description 37
150000004702 methyl esters Chemical class 0.000 claims description 36
125000003710 aryl alkyl group Chemical group 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 28
150000001204 N-oxides Chemical class 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 27
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
125000003107 substituted aryl group Chemical group 0.000 claims description 27
150000002431 hydrogen Chemical class 0.000 claims description 26
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 25
239000012453 solvate Substances 0.000 claims description 24
125000004450 alkenylene group Chemical group 0.000 claims description 20
229940002612 prodrug Drugs 0.000 claims description 20
239000000651 prodrug Substances 0.000 claims description 20
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 19
150000001408 amides Chemical class 0.000 claims description 18
125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
230000015572 biosynthetic process Effects 0.000 claims description 17
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
KJCIMSSFGUGTGA-UHFFFAOYSA-N 1-methylpiperazin-2-one Chemical compound CN1CCNCC1=O KJCIMSSFGUGTGA-UHFFFAOYSA-N 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 11
125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 11
125000005156 substituted alkylene group Chemical group 0.000 claims description 11
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 10
APAMKXUATGRDBB-UHFFFAOYSA-N 6-chloro-1-benzothiophene Chemical compound ClC1=CC=C2C=CSC2=C1 APAMKXUATGRDBB-UHFFFAOYSA-N 0.000 claims description 10
125000004419 alkynylene group Chemical group 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
108090000190 Thrombin Proteins 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
229960004072 thrombin Drugs 0.000 claims description 8
GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
125000004494 ethyl ester group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
WDEJJPNCFNYSGS-RUINGEJQSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC=C(Cl)S1 WDEJJPNCFNYSGS-RUINGEJQSA-N 0.000 claims description 6
FSUYPAIFVPOMGN-HNNXBMFYSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=CC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)C)=CC=C21 FSUYPAIFVPOMGN-HNNXBMFYSA-N 0.000 claims description 6
RHESQXOYNCWQQP-FQEVSTJZSA-N (3s)-4-[3-(6-aminopyridin-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=C1 RHESQXOYNCWQQP-FQEVSTJZSA-N 0.000 claims description 6
KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 6
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 description 6
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 description 6
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 6
208000007536 Thrombosis Diseases 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
239000003146 anticoagulant agent Substances 0.000 claims description 6
JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 6
230000001052 transient effect Effects 0.000 claims description 6
XUKLJATTXIDZOK-FQEVSTJZSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 XUKLJATTXIDZOK-FQEVSTJZSA-N 0.000 claims description 5
IULVBFFYXSEISI-OAHLLOKOSA-N (6r)-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-(hydroxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2NC3=CC=NC=C3C=2)CO)N1S(=O)(=O)C=CC1=CC=C(Cl)S1 IULVBFFYXSEISI-OAHLLOKOSA-N 0.000 claims description 5
PLWVUIRWJVKSSD-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C=CS(=O)(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 PLWVUIRWJVKSSD-UHFFFAOYSA-N 0.000 claims description 5
210000004351 coronary vessel Anatomy 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
XFIAZOWJEYRZFE-KRWDZBQOSA-N (3s)-1-[(1-aminoisoquinolin-6-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3C=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(Cl)S1 XFIAZOWJEYRZFE-KRWDZBQOSA-N 0.000 claims description 4
YNNCDVMRFAUEHB-HNNXBMFYSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)C)=CC=C21 YNNCDVMRFAUEHB-HNNXBMFYSA-N 0.000 claims description 4
ZFBLUIGZEYFDJI-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(ethoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COCC)C(=O)COC1=CC=C(Cl)S1 ZFBLUIGZEYFDJI-KRWDZBQOSA-N 0.000 claims description 4
MXYZABNETCECPJ-INIZCTEOSA-N (3s)-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-INIZCTEOSA-N 0.000 claims description 4
GDOHFABQTHNBJK-RUINGEJQSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-ethyl-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)CC)C(=O)COC1=CC=C(Cl)S1 GDOHFABQTHNBJK-RUINGEJQSA-N 0.000 claims description 4
YQOUBCQHPDMPDJ-UWBLVGDVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CSC(Cl)=C1 YQOUBCQHPDMPDJ-UWBLVGDVSA-N 0.000 claims description 4
ULVVVFNFXFHWSH-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-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=CSC(Cl)=C1 ULVVVFNFXFHWSH-KRWDZBQOSA-N 0.000 claims description 4
BYRCHTQDKADKBB-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC(Cl)=CS1 BYRCHTQDKADKBB-ZDUSSCGKSA-N 0.000 claims description 4
YQEMHDLGQQZCKI-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-bromothiophen-2-yl)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=CC1=CC=C(Br)S1 YQEMHDLGQQZCKI-SFHVURJKSA-N 0.000 claims description 4
DPVOUFWSGIVGEM-PKDNWHCCSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC=C(Cl)S1 DPVOUFWSGIVGEM-PKDNWHCCSA-N 0.000 claims description 4
PIRLGEDSPILCDG-FXMQYSIJSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethyl-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)C(C)C1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 PIRLGEDSPILCDG-FXMQYSIJSA-N 0.000 claims description 4
XWVIEMGPBIPVCN-NRFANRHFSA-N (3s)-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-3-(methoxymethyl)-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1SC(Cl)=CC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 XWVIEMGPBIPVCN-NRFANRHFSA-N 0.000 claims description 4
MSFXBEBFVOAJEQ-UHFFFAOYSA-N 1,4-bis(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC=4NC5=CC=NC=C5C=4)CC3=O)=CC2=C1 MSFXBEBFVOAJEQ-UHFFFAOYSA-N 0.000 claims description 4
WJDHFTMQMRRPEF-UHFFFAOYSA-N 1-[(1-aminoisoquinolin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4C=CN=C(C4=CC=3)N)=CC2=C1 WJDHFTMQMRRPEF-UHFFFAOYSA-N 0.000 claims description 4
SEKKRDRUSDOVRH-UHFFFAOYSA-N 1-[(1-aminoisoquinolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=C4C=CN=C(C4=C3)N)=CC2=C1 SEKKRDRUSDOVRH-UHFFFAOYSA-N 0.000 claims description 4
XVVYXVUINZKQRF-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3-chloro-1h-indol-6-yl)methyl]piperazin-2-one Chemical compound C1=C2C(Cl)=CNC2=CC(CN2CCN(C(C2)=O)CC=2C=C3N=CN=C(C3=CC=2)N)=C1 XVVYXVUINZKQRF-UHFFFAOYSA-N 0.000 claims description 4
FEAWZTFWPFWTDN-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 FEAWZTFWPFWTDN-UHFFFAOYSA-N 0.000 claims description 4
UBDHHNYVNUTFEY-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 UBDHHNYVNUTFEY-UHFFFAOYSA-N 0.000 claims description 4
HEVKGOPJZXFCLZ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2C=NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 HEVKGOPJZXFCLZ-UHFFFAOYSA-N 0.000 claims description 4
RTALUUJEFBQNKW-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(C(C3)=O)CC=3C=C4N=CC=C(C4=CC=3)N)=CC2=C1 RTALUUJEFBQNKW-UHFFFAOYSA-N 0.000 claims description 4
VFTFIDJYZGHGCD-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CC=C(C4=CC=3)N)=CC2=C1 VFTFIDJYZGHGCD-UHFFFAOYSA-N 0.000 claims description 4
LITASNRODRZXHG-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]piperazin-2-one Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1)=O)CCN1S(=O)(=O)C=CC1=CC=C(Cl)S1 LITASNRODRZXHG-UHFFFAOYSA-N 0.000 claims description 4
WBHNYUXNVGXADU-KRWDZBQOSA-N 2-[2-[2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-ethyl-3-oxopiperazin-1-yl]-2-oxoethoxy]-5-chlorothiophen-3-yl]acetic acid Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC=1SC(Cl)=CC=1CC(O)=O WBHNYUXNVGXADU-KRWDZBQOSA-N 0.000 claims description 4
TVPJSBRCNWTROP-UHFFFAOYSA-N 3-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-7-chloro-1h-quinolin-2-one Chemical compound C1=C(Cl)C=C2NC(=O)C(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 TVPJSBRCNWTROP-UHFFFAOYSA-N 0.000 claims description 4
BMWPEMIDDMRFQL-UHFFFAOYSA-N 4-(6-chlorothieno[2,3-b]pyridin-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(N=C4S3)Cl)=CC2=C1 BMWPEMIDDMRFQL-UHFFFAOYSA-N 0.000 claims description 4
IKMGUSTUEXADKO-UHFFFAOYSA-N 4-[(6-bromo-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)Br)=CC2=C1 IKMGUSTUEXADKO-UHFFFAOYSA-N 0.000 claims description 4
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YXAPPUAOECRZCR-LJAQVGFWSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-benzyl-4-[(6-chloronaphthalen-2-yl)methyl]piperazin-2-one Chemical compound C([C@@H]1N(CC=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)CC=1C=C2N=CN=C(C2=CC=1)N)C1=CC=CC=C1 YXAPPUAOECRZCR-LJAQVGFWSA-N 0.000 claims description 2
XPCVPCWAXOPYLW-VWLOTQADSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-benzyl-4-[2-(4-chlorophenoxy)acetyl]piperazin-2-one Chemical compound C([C@@H]1N(CCN(C1=O)CC=1C=C2N=CN=C(C2=CC=1)N)C(=O)COC=1C=CC(Cl)=CC=1)C1=CC=CC=C1 XPCVPCWAXOPYLW-VWLOTQADSA-N 0.000 claims description 2
OPOITKPALPAVQE-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-benzyl-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C([C@@H]1N(CCN(C1=O)CC=1C=C2N=CN=C(C2=CC=1)N)C(=O)C=CC=1SC(Cl)=CC=1)C1=CC=CC=C1 OPOITKPALPAVQE-QHCPKHFHSA-N 0.000 claims description 2
BAMWXBZHSKFVFW-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-benzyl-4-[3-(5-chlorothiophen-2-yl)propyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CC=2C=CC=CC=2)=O)CCN1CCCC1=CC=C(Cl)S1 BAMWXBZHSKFVFW-DEOSSOPVSA-N 0.000 claims description 2
QKBOGKQGZZXLPN-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-3-butyl-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)COC1=CSC(Cl)=C1 QKBOGKQGZZXLPN-IBGZPJMESA-N 0.000 claims description 2
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CGRRXTZMFZVYAU-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(2-chloro-1-benzothiophene-6-carbonyl)-3-ethylpiperazin-2-one Chemical compound C1=C2C=C(Cl)SC2=CC(C(=O)N2[C@H](C(N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=O)CC)=C1 CGRRXTZMFZVYAU-IBGZPJMESA-N 0.000 claims description 2
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ONWUZTDBOWSXFS-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3-chloro-1h-indol-6-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4C=C5NC=C(Cl)C5=CC=4)[C@H](C3=O)C)=CC=C21 ONWUZTDBOWSXFS-AWEZNQCLSA-N 0.000 claims description 2
GIMYOOBUEHLNSZ-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)C)=CC=C21 GIMYOOBUEHLNSZ-AWEZNQCLSA-N 0.000 claims description 2
PQRXCNSYCYYVPW-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4SC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)C)=CC=C21 PQRXCNSYCYYVPW-AWEZNQCLSA-N 0.000 claims description 2
FCBCOTPFDAUCKI-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-3-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)C)=CC2=C1 FCBCOTPFDAUCKI-ZDUSSCGKSA-N 0.000 claims description 2
ZLHXWILVUVCHFU-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5N=4)[C@H](C3=O)C)=CC=C21 ZLHXWILVUVCHFU-ZDUSSCGKSA-N 0.000 claims description 2
OCMQMXOWCUTTLQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4C=C5C=CC(Cl)=CC5=CC=4)[C@H](C3=O)C)=CC=C21 OCMQMXOWCUTTLQ-INIZCTEOSA-N 0.000 claims description 2
XPKQDJGCWRNWIX-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chlorothieno[2,3-b]pyridin-2-yl)methyl]-3-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4SC5=NC(Cl)=CC=C5C=4)[C@H](C3=O)C)=CC=C21 XPKQDJGCWRNWIX-ZDUSSCGKSA-N 0.000 claims description 2
BABMVDQHQYVJLN-GYCJOSAFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)[C@@H](C)OC)=CC=C21 BABMVDQHQYVJLN-GYCJOSAFSA-N 0.000 claims description 2
YTZUCGFEWLFGNZ-LGTGAQBVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(2,5-dichlorophenoxy)acetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC(Cl)=CC=C1Cl YTZUCGFEWLFGNZ-LGTGAQBVSA-N 0.000 claims description 2
BATUUIIGKBEHGI-YNNZGITBSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3,5-dichlorophenoxy)acetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC(Cl)=CC(Cl)=C1 BATUUIIGKBEHGI-YNNZGITBSA-N 0.000 claims description 2
MVAKMVXXKKYEKL-YNNZGITBSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chloro-4-fluorophenoxy)acetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC=C(F)C(Cl)=C1 MVAKMVXXKKYEKL-YNNZGITBSA-N 0.000 claims description 2
XRQOAAVQXKNQTP-NRFANRHFSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chloro-5-methoxyphenoxy)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)COC1=CC(Cl)=CC(OC)=C1 XRQOAAVQXKNQTP-NRFANRHFSA-N 0.000 claims description 2
WIXGFFANUNUPPC-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(3-chlorophenoxy)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)COC1=CC=CC(Cl)=C1 WIXGFFANUNUPPC-FQEVSTJZSA-N 0.000 claims description 2
VSWCUNILQIMCDD-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chloro-2-methylphenoxy)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)COC1=CC=C(Cl)C=C1C VSWCUNILQIMCDD-FQEVSTJZSA-N 0.000 claims description 2
DNKBVLUYSVHQIU-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorophenoxy)acetyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)COC1=CC=C(Cl)C=C1 DNKBVLUYSVHQIU-AWEZNQCLSA-N 0.000 claims description 2
OOFKXVRAOJTQHF-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC1=CC(Cl)=CS1 OOFKXVRAOJTQHF-KRWDZBQOSA-N 0.000 claims description 2
BLOMVHIDQQPOQR-LBPRGKRZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)COC1=CC(Cl)=CS1 BLOMVHIDQQPOQR-LBPRGKRZSA-N 0.000 claims description 2
MZSDIUXRVMTHPY-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorothiophen-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)COC1=CC(Cl)=CS1 MZSDIUXRVMTHPY-SFHVURJKSA-N 0.000 claims description 2
RVUOCBNDWAVGSG-MRNPHLECSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chloro-2-methylphenoxy)acetyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)COC1=CC(Cl)=CC=C1C RVUOCBNDWAVGSG-MRNPHLECSA-N 0.000 claims description 2
HDXIXQGVVFWHOU-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chloropyridin-3-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)=C1 HDXIXQGVVFWHOU-IBGZPJMESA-N 0.000 claims description 2
IKHSESRTYOUGAI-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-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)COC1=CC=C(Cl)S1 IKHSESRTYOUGAI-KRWDZBQOSA-N 0.000 claims description 2
NSQHSFPQJAOGFI-XCLFUZPHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)[C@@H](C)OC)C(=O)COC1=CC=C(Cl)S1 NSQHSFPQJAOGFI-XCLFUZPHSA-N 0.000 claims description 2
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PDZBZJIOBNYCCF-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-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)COC1=CC=C(Cl)S1 PDZBZJIOBNYCCF-KRWDZBQOSA-N 0.000 claims description 2
XXKRYBARDAEDSM-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-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)COC1=CSC(Cl)=C1 XXKRYBARDAEDSM-SFHVURJKSA-N 0.000 claims description 2
CBHRYPCDPQMWRT-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)COC1=CSC(Cl)=C1 CBHRYPCDPQMWRT-KRWDZBQOSA-N 0.000 claims description 2
PFSTYVMXTWGWGT-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-fluorothiophen-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(F)S1 PFSTYVMXTWGWGT-INIZCTEOSA-N 0.000 claims description 2
DIJYSOSJXAPYLC-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(6-chloropyridin-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=CC(Cl)=N1 DIJYSOSJXAPYLC-KRWDZBQOSA-N 0.000 claims description 2
LUGUTJIMCGLPIZ-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(6-chloropyridin-3-yl)oxyacetyl]-3-(ethoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COCC)C(=O)COC1=CC=C(Cl)N=C1 LUGUTJIMCGLPIZ-IBGZPJMESA-N 0.000 claims description 2
BFFNMFFIRWERJS-CEISFSOZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(2,5-dichlorophenyl)prop-2-enoyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)C=CC1=CC(Cl)=CC=C1Cl BFFNMFFIRWERJS-CEISFSOZSA-N 0.000 claims description 2
FOTJKXPTWBLCIX-LGTGAQBVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)COC)C(=O)C=CC1=CC(Br)=CS1 FOTJKXPTWBLCIX-LGTGAQBVSA-N 0.000 claims description 2
AGWUXMPCRAFHAO-SZNDQCEHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)[C@@H](C)OC)C(=O)C=CC1=CC(Br)=CS1 AGWUXMPCRAFHAO-SZNDQCEHSA-N 0.000 claims description 2
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VLSKWHGHQDUMMC-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC(Br)=CS1 VLSKWHGHQDUMMC-IBGZPJMESA-N 0.000 claims description 2
BRLIDOSZZOYYBZ-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC(Br)=CS1 BRLIDOSZZOYYBZ-ZDUSSCGKSA-N 0.000 claims description 2
JGPUUXNCEMSQHF-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-bromothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC=C(Br)S1 JGPUUXNCEMSQHF-ZDUSSCGKSA-N 0.000 claims description 2
GRMJYCFPEXLVHM-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)but-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=C(C)C1=CC=C(Cl)S1 GRMJYCFPEXLVHM-AWEZNQCLSA-N 0.000 claims description 2
BVHQPYVSEXRFIJ-HNNXBMFYSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)but-2-enyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)CC=C(C)C1=CC=C(Cl)S1 BVHQPYVSEXRFIJ-HNNXBMFYSA-N 0.000 claims description 2
QQQHNJGTKOJFDI-IBGZPJMESA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(ethoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COCC)C(=O)C=CC1=CC=C(Cl)S1 QQQHNJGTKOJFDI-IBGZPJMESA-N 0.000 claims description 2
DXYCFQASODUPMW-SZNDQCEHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)[C@@H](C)OC)C(=O)C=CC1=CC=C(Cl)S1 DXYCFQASODUPMW-SZNDQCEHSA-N 0.000 claims description 2
HEODAYIDJROIDD-ZDUSSCGKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)C(=O)C=CC1=CC=C(Cl)S1 HEODAYIDJROIDD-ZDUSSCGKSA-N 0.000 claims description 2
HJUMCXQVYCNSMB-MBABXSBOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)propyl]-3-ethyl-6-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C)C1)=O)CC)CCCC1=CC=C(Cl)S1 HJUMCXQVYCNSMB-MBABXSBOSA-N 0.000 claims description 2
BZDOUZIDMFNRHN-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)propyl]-3-methylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)C)CCCC1=CC=C(Cl)S1 BZDOUZIDMFNRHN-AWEZNQCLSA-N 0.000 claims description 2
PPQAUEYZXKIYNI-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-3-yl)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=CC1=CSC(Cl)=C1 PPQAUEYZXKIYNI-SFHVURJKSA-N 0.000 claims description 2
BSSQYTLAFHGVAR-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-3-yl)prop-2-enoyl]-3-ethylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CSC(Cl)=C1 BSSQYTLAFHGVAR-SFHVURJKSA-N 0.000 claims description 2
ROBQZXSQLBIJPA-SANMLTNESA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]-3-ethylpiperazin-2-one Chemical compound NC1=CC=NC2=CC(CN3CCN(CC=4C=C5C=CC(Cl)=CC5=CC=4)[C@H](C3=O)CC)=CC=C21 ROBQZXSQLBIJPA-SANMLTNESA-N 0.000 claims description 2
FPKHGUBTMCBSHO-WUTOIGTNSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)[C@@H](C)OC)C(=O)C=CC1=CC(Br)=CS1 FPKHGUBTMCBSHO-WUTOIGTNSA-N 0.000 claims description 2
FPUMBAUAQAVAQQ-FQEVSTJZSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)COC)C(=O)C=CC1=CC=C(Cl)S1 FPUMBAUAQAVAQQ-FQEVSTJZSA-N 0.000 claims description 2
QUFVGWBUWMPEME-CMJOXMDJSA-N (3s)-1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-[(1r)-1-methoxyethyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(N)C3=CC=2)CC1)=O)[C@@H](C)OC)C(=O)C=CC1=CC=C(Cl)S1 QUFVGWBUWMPEME-CMJOXMDJSA-N 0.000 claims description 2
CRBQZAIDKNSNSG-DTIOYNMSSA-N (3s)-1-[(4-chloroquinolin-7-yl)methyl]-3,5-dimethylpiperazin-2-one Chemical compound O=C1[C@H](C)NC(C)CN1CC1=CC=C(C(Cl)=CC=N2)C2=C1 CRBQZAIDKNSNSG-DTIOYNMSSA-N 0.000 claims description 2
CSNBZVUJZDWSRS-JTQLQIEISA-N (3s)-1-[(4-chloroquinolin-7-yl)methyl]-3-methylpiperazin-2-one Chemical compound O=C1[C@H](C)NCCN1CC1=CC=C(C(Cl)=CC=N2)C2=C1 CSNBZVUJZDWSRS-JTQLQIEISA-N 0.000 claims description 2
AWWPRJSAXAOEDN-CYXJOQHWSA-N (3s)-1-[(7-chloroisoquinolin-3-yl)methyl]-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2N=CC3=CC(Cl)=CC=C3C=2)CC1)=O)COC)C(=O)\C=C\C1=CC=C(Cl)S1 AWWPRJSAXAOEDN-CYXJOQHWSA-N 0.000 claims description 2
QNFASEFJRMIJKK-DEOSSOPVSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-1-[(4-chloroquinolin-7-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound ClC1=CC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)COC)=CC=C21 QNFASEFJRMIJKK-DEOSSOPVSA-N 0.000 claims description 2
BFLDPLPFCJQHRA-QFIPXVFZSA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-3-(methoxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)COC)=CC2=C1 BFLDPLPFCJQHRA-QFIPXVFZSA-N 0.000 claims description 2
QPMDRTXSMAQJQN-XBGMYJNYSA-N (3s)-4-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-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)C(=O)\C=C\C1=CC=C(Cl)C=C1 QPMDRTXSMAQJQN-XBGMYJNYSA-N 0.000 claims description 2
OPPJHIHBJIDVQV-KQPPXVQYSA-N (3s)-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-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(C(=O)\C=C\C=2SC(Cl)=CC=2)CC1 OPPJHIHBJIDVQV-KQPPXVQYSA-N 0.000 claims description 2
XQAOVSSCYCZVOJ-YZTRRJNXSA-N (3s)-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-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)C(=O)\C=C\C1=CC=C(Cl)S1 XQAOVSSCYCZVOJ-YZTRRJNXSA-N 0.000 claims description 2
CTOJTNFXJHUNGS-FQTAANOTSA-N (3s)-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(methoxymethyl)-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1/C=C/C(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 CTOJTNFXJHUNGS-FQTAANOTSA-N 0.000 claims description 2
CSBOZDOLFWPELI-CTMGSCHOSA-N (3s)-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethyl-6-methyl-1-[(4-phenylphenyl)methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1/C=C/C(=O)N([C@H](C1=O)CC)CC(C)N1CC(C=C1)=CC=C1C1=CC=CC=C1 CSBOZDOLFWPELI-CTMGSCHOSA-N 0.000 claims description 2
IQNASPLCFQXXHR-KXKDPZRNSA-N (3s)-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-methyl-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1/C=C/C(=O)N([C@H](C1=O)C)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 IQNASPLCFQXXHR-KXKDPZRNSA-N 0.000 claims description 2
MRJYWARTPLUSST-NRFANRHFSA-N (3s)-4-[2-(4-chlorophenyl)ethenylsulfonyl]-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)S(=O)(=O)C=CC1=CC=C(Cl)C=C1 MRJYWARTPLUSST-NRFANRHFSA-N 0.000 claims description 2
ISAAXJOTMHQBEZ-NRFANRHFSA-N (3s)-4-[2-(4-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C(Cl)=CSC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 ISAAXJOTMHQBEZ-NRFANRHFSA-N 0.000 claims description 2
RGPAZBWNCODDDQ-FQEVSTJZSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 RGPAZBWNCODDDQ-FQEVSTJZSA-N 0.000 claims description 2
UHIVURXWDCNWGB-NRFANRHFSA-N (3s)-4-[3-(4-aminophenyl)prop-2-enoyl]-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)C=CC1=CC=C(N)C=C1 UHIVURXWDCNWGB-NRFANRHFSA-N 0.000 claims description 2
VSPQQTPTCVEGPW-FQEVSTJZSA-N (3s)-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-ethyl-1-[[4-(hydroxyamino)quinolin-7-yl]methyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CC=C(NO)C3=CC=2)CC1)=O)CC)C(=O)C=CC1=CC=C(Cl)S1 VSPQQTPTCVEGPW-FQEVSTJZSA-N 0.000 claims description 2
RHJMEECUWIXNDR-IBGZPJMESA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-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)C=CC1=CC=C(N)N=C1 RHJMEECUWIXNDR-IBGZPJMESA-N 0.000 claims description 2
KBIRRSHMTNLPFD-KBPBESRZSA-N (3s,5s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-3,5-dimethylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3[C@@H](C)C(=O)N(CC=4C=C5N=CN=C(N)C5=CC=4)C[C@@H]3C)=CC2=C1 KBIRRSHMTNLPFD-KBPBESRZSA-N 0.000 claims description 2
GPRVEWOEFMIGDL-GKVSMKOHSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]-3-(methoxymethyl)-6-methylpiperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3[C@@H](C)CN(CC=4C=C5C=CC(Cl)=CC5=CC=4)[C@H](C3=O)COC)=CC=C21 GPRVEWOEFMIGDL-GKVSMKOHSA-N 0.000 claims description 2
OTHALGYTOCLXDJ-UHFFFAOYSA-N (5-chlorothiophen-2-yl)methyl 4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazine-1-carboxylate Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)OCC1=CC=C(Cl)S1 OTHALGYTOCLXDJ-UHFFFAOYSA-N 0.000 claims description 2
XYBHRHQACINKPY-UHFFFAOYSA-N 1,4-bis[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC3=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC=C21 XYBHRHQACINKPY-UHFFFAOYSA-N 0.000 claims description 2
OPXMLUXDXOHAGV-UHFFFAOYSA-N 1,4-bis[(5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(CN3CCN(CC3=O)CC=3NC4=CC=C(C=C4C=3)Cl)=CC2=C1 OPXMLUXDXOHAGV-UHFFFAOYSA-N 0.000 claims description 2
UXHXBUCYFWISAA-UHFFFAOYSA-N 1-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-6-ylmethyl)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1CC2CNCCC2CC1CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 UXHXBUCYFWISAA-UHFFFAOYSA-N 0.000 claims description 2
LBCLWZQZJYVFRN-UHFFFAOYSA-N 1-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-7-ylmethyl)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1CC2CCNCC2CC1CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 LBCLWZQZJYVFRN-UHFFFAOYSA-N 0.000 claims description 2
OTVJALKAUIMVDT-UHFFFAOYSA-N 1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-thieno[2,3-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound C1=CN=C2SC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=C1 OTVJALKAUIMVDT-UHFFFAOYSA-N 0.000 claims description 2
YIQKAPCYLQPOKQ-UHFFFAOYSA-N 1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-thieno[3,2-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound C1=CC=C2SC(S(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=N1 YIQKAPCYLQPOKQ-UHFFFAOYSA-N 0.000 claims description 2
IFGCMKFNHKDDJW-UHFFFAOYSA-N 1-[(1-aminoisoquinolin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3)=O)CC=3C=C4C=CN=C(C4=CC=3)N)=CC2=C1 IFGCMKFNHKDDJW-UHFFFAOYSA-N 0.000 claims description 2
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VAJHDXWBJMGSQJ-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(4-methoxyphenyl)methyl]piperazin-2-one Chemical compound C1=CC(OC)=CC=C1CN1CC(=O)N(CC=2C=C3C=CC(N)=NC3=CC=2)CC1 VAJHDXWBJMGSQJ-UHFFFAOYSA-N 0.000 claims description 2
NNHTYOYEVGEYDN-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC4=CC=C(N=C4C=C3)N)=CC2=C1 NNHTYOYEVGEYDN-UHFFFAOYSA-N 0.000 claims description 2
FRLLINYESBSQQN-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(6-chloronaphthalen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=CC2=CC(CN3CCN(C(C3)=O)CC3=CC4=CC=C(N=C4C=C3)N)=CC=C21 FRLLINYESBSQQN-UHFFFAOYSA-N 0.000 claims description 2
PLHOOQVSQVOUFX-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(6-methoxy-1h-benzimidazol-2-yl)methyl]piperazin-2-one Chemical compound N1=C(N)C=CC2=CC(CN3CCN(CC3=O)CC=3NC4=CC=C(C=C4N=3)OC)=CC=C21 PLHOOQVSQVOUFX-UHFFFAOYSA-N 0.000 claims description 2
NDFNUQOROBVJAA-XBXARRHUSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C1=CC2=NC(N)=CC=C2C=C1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Cl)S1 NDFNUQOROBVJAA-XBXARRHUSA-N 0.000 claims description 2
MSFDOYADHIZDCR-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]-4-[5-(5-chlorothiophen-2-yl)thiophen-2-yl]sulfonylpiperazin-2-one Chemical compound C1=CC2=NC(N)=CC=C2C=C1CN(C(C1)=O)CCN1S(=O)(=O)C(S1)=CC=C1C1=CC=C(Cl)S1 MSFDOYADHIZDCR-UHFFFAOYSA-N 0.000 claims description 2
BWCPGQKVUMWCEZ-UHFFFAOYSA-N 1-[(2-aminoquinolin-6-yl)methyl]piperazin-2-one Chemical compound C1=CC2=NC(N)=CC=C2C=C1CN1CCNCC1=O BWCPGQKVUMWCEZ-UHFFFAOYSA-N 0.000 claims description 2
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JSTUBAABZKIAAC-UHFFFAOYSA-N 1-[(3-amino-1h-indazol-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4NN=C(C4=CC=3)N)=CC2=C1 JSTUBAABZKIAAC-UHFFFAOYSA-N 0.000 claims description 2
LMSGORFMUOAKFM-UHFFFAOYSA-N 1-[(3-amino-4-cyanophenyl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylic acid Chemical compound C1=C(C#N)C(N)=CC(CN2C(CN(CC2C(O)=O)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1 LMSGORFMUOAKFM-UHFFFAOYSA-N 0.000 claims description 2
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NAKLAFVYFZJFGH-UHFFFAOYSA-N 1-[(4-amino-2-methylquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)methyl]piperidin-2-one Chemical compound C1=C(Cl)C=C2NC(CC3CCN(C(C3)=O)CC=3C=CC4=C(N)N=C(N=C4C=3)C)=NC2=C1 NAKLAFVYFZJFGH-UHFFFAOYSA-N 0.000 claims description 2
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RLHZDEXEVGRRTQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(3-chloro-1h-indole-6-carbonyl)piperazin-2-one Chemical compound C1=C2C(Cl)=CNC2=CC(C(=O)N2CCN(C(C2)=O)CC=2C=C3N=CN=C(C3=CC=2)N)=C1 RLHZDEXEVGRRTQ-UHFFFAOYSA-N 0.000 claims description 2
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AUJGNFAMGLGVTO-ZZXKWVIFSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(5-bromothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Br)S1 AUJGNFAMGLGVTO-ZZXKWVIFSA-N 0.000 claims description 2
SZLJRSQDUPBXJX-ZZXKWVIFSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)\C=C\C1=CC=C(Cl)S1 SZLJRSQDUPBXJX-ZZXKWVIFSA-N 0.000 claims description 2
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TVBOGYVJJIRWCA-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chloro-2-methylphenoxy)acetyl]piperazin-2-one Chemical compound CC1=CC(Cl)=CC=C1OCC(=O)N1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 TVBOGYVJJIRWCA-UHFFFAOYSA-N 0.000 claims description 2
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JPXXIJSKCQZARD-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(4-chlorophenyl)sulfanylethyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CCSC1=CC=C(Cl)C=C1 JPXXIJSKCQZARD-UHFFFAOYSA-N 0.000 claims description 2
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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 description 2
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XAWXWRJUYRSRHX-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(2,5-dichlorothiophen-3-yl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC=1C=C(Cl)SC=1Cl XAWXWRJUYRSRHX-UHFFFAOYSA-N 0.000 claims description 2
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OZQAYRYMHQRQSI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-methylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound CC1=CC=CC(C#CCN2CC(=O)N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=C1 OZQAYRYMHQRQSI-UHFFFAOYSA-N 0.000 claims description 2
LUMULQIYXABLTQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(3-phenylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC(C=1)=CC=CC=1C1=CC=CC=C1 LUMULQIYXABLTQ-UHFFFAOYSA-N 0.000 claims description 2
CHBYJJHCWKUQHQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorophenyl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC1=CC=C(Cl)C=C1 CHBYJJHCWKUQHQ-UHFFFAOYSA-N 0.000 claims description 2
JYOHXMSDHLHLGD-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorophenyl)propyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CCCC1=CC=C(Cl)C=C1 JYOHXMSDHLHLGD-UHFFFAOYSA-N 0.000 claims description 2
NEJCXVWBNBCQPO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-methylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound C1=CC(C)=CC=C1C#CCN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 NEJCXVWBNBCQPO-UHFFFAOYSA-N 0.000 claims description 2
IPSHUAIHILKQKU-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-phenylphenyl)prop-2-ynyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC#CC(C=C1)=CC=C1C1=CC=CC=C1 IPSHUAIHILKQKU-UHFFFAOYSA-N 0.000 claims description 2
SMPHVPLIQJYCMS-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3,3-dimethylpiperazin-2-one Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(C)(C)N1C(=O)C=CC1=CC=C(Cl)S1 SMPHVPLIQJYCMS-UHFFFAOYSA-N 0.000 claims description 2
QJKGTSXSFUEUJP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)propanoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)CCC1=CC=C(Cl)S1 QJKGTSXSFUEUJP-UHFFFAOYSA-N 0.000 claims description 2
FOMGIDMGPTYDOQ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonylpiperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1S(=O)(=O)C(S1)=CC=C1C=1C=CON=1 FOMGIDMGPTYDOQ-UHFFFAOYSA-N 0.000 claims description 2
CTECOCZYUFJLEB-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[5-(5-methylthiophen-2-yl)penta-2,4-dienyl]piperazin-2-one Chemical compound S1C(C)=CC=C1C=CC=CCN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 CTECOCZYUFJLEB-UHFFFAOYSA-N 0.000 claims description 2
VABWDILJHVGISM-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 VABWDILJHVGISM-UHFFFAOYSA-N 0.000 claims description 2
ASWKUECSFCYFHI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3,5-bis(trifluoromethyl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ASWKUECSFCYFHI-UHFFFAOYSA-N 0.000 claims description 2
NYZKQGSWOKTZGC-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(1,3-benzoxazol-2-yl)phenyl]methyl]piperazin-2-one Chemical compound C1=CC=C2OC(C=3C=CC=C(C=3)CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 NYZKQGSWOKTZGC-UHFFFAOYSA-N 0.000 claims description 2
VBTAXBQWEZHFSU-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[3-(4-fluorophenoxy)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(C=1)=CC=CC=1OC1=CC=C(F)C=C1 VBTAXBQWEZHFSU-UHFFFAOYSA-N 0.000 claims description 2
PZOLCTVUJSGXHT-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-oxazol-2-yl]methyl]piperazin-2-one Chemical compound O1CCOC2=CC(C3=CN=C(O3)CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC=C21 PZOLCTVUJSGXHT-UHFFFAOYSA-N 0.000 claims description 2
WDFOHEDPLQUVDU-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(3-chlorophenyl)thiophen-2-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(S1)=CC=C1C1=CC=CC(Cl)=C1 WDFOHEDPLQUVDU-UHFFFAOYSA-N 0.000 claims description 2
WGNYAXSXIRVNJE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(3-nitrophenyl)furan-2-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(O1)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 WGNYAXSXIRVNJE-UHFFFAOYSA-N 0.000 claims description 2
BNDUKDAMOVXTDE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(4-chlorophenyl)thiophen-2-yl]methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(S1)=CC=C1C1=CC=C(Cl)C=C1 BNDUKDAMOVXTDE-UHFFFAOYSA-N 0.000 claims description 2
OFGRRWOUXANCCE-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(4-methoxyphenyl)thiophen-2-yl]methyl]piperazin-2-one Chemical compound C1=CC(OC)=CC=C1C(S1)=CC=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 OFGRRWOUXANCCE-UHFFFAOYSA-N 0.000 claims description 2
PNOGJQLRMQXRMT-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophen-2-yl]methyl]piperazin-2-one Chemical compound C1=C(C(F)(F)F)N(C)N=C1C(S1)=CC=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 PNOGJQLRMQXRMT-UHFFFAOYSA-N 0.000 claims description 2
PNRTXGXLSDZDTN-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN1CCNCC1=O PNRTXGXLSDZDTN-UHFFFAOYSA-N 0.000 claims description 2
CIRPVOWZXKBAQV-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(4-bromothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)C=CC1=CC(Br)=CS1 CIRPVOWZXKBAQV-UHFFFAOYSA-N 0.000 claims description 2
HOKVDVWDNLPHCS-UHFFFAOYSA-N 1-[(4-aminoquinolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound C=1C=C2C(N)=CC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)C=CC1=CC=C(Cl)S1 HOKVDVWDNLPHCS-UHFFFAOYSA-N 0.000 claims description 2
KRZZLDPDBPYJCI-UHFFFAOYSA-N 1-[(4-aminothieno[2,3-d]pyrimidin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3)=O)CC=3SC=4N=CN=C(C=4C=3)N)=CC2=C1 KRZZLDPDBPYJCI-UHFFFAOYSA-N 0.000 claims description 2
LXAREMWKFSQBLI-UHFFFAOYSA-N 1-[(4-aminothieno[2,3-d]pyrimidin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4N=CN=C(C=4C=3)N)=CC2=C1 LXAREMWKFSQBLI-UHFFFAOYSA-N 0.000 claims description 2
YQMKOMRTVGHVTH-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-c]pyridin-2-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4C=CN=C(C=4C=3)N)=CC2=C1 YQMKOMRTVGHVTH-UHFFFAOYSA-N 0.000 claims description 2
DQYSLHYVAVEKEN-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-c]pyridin-3-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CSC=4C=CN=C(C3=4)N)=CC2=C1 DQYSLHYVAVEKEN-UHFFFAOYSA-N 0.000 claims description 2
AESJULZFAITDSG-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(CN3CCN(C(C3)=O)CC3=CC=4N=CN=C(C=4S3)N)=CC2=C1 AESJULZFAITDSG-UHFFFAOYSA-N 0.000 claims description 2
PMDVILVEJYXQSD-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=4N=CN=C(C=4S3)N)=CC2=C1 PMDVILVEJYXQSD-UHFFFAOYSA-N 0.000 claims description 2
RAWVFSFXCQMSRQ-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2C=NC(CN3CCN(C(C3)=O)CC3=CC=4N=CN=C(C=4S3)N)=CC2=C1 RAWVFSFXCQMSRQ-UHFFFAOYSA-N 0.000 claims description 2
YCTMZOVIZSALLK-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]piperazin-2-one Chemical compound S1C=2C(N)=NC=NC=2C=C1CN(C(C1)=O)CCN1C(=O)C=CC1=CC=C(Cl)S1 YCTMZOVIZSALLK-UHFFFAOYSA-N 0.000 claims description 2
KVKJYYYQVZHPAU-UHFFFAOYSA-N 1-[(4-aminothieno[3,2-d]pyrimidin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=4N=CN=C(C=4SC=3)N)=CC2=C1 KVKJYYYQVZHPAU-UHFFFAOYSA-N 0.000 claims description 2
WLPDEDJVUXTZSY-UHFFFAOYSA-N 1-[(4-chlorocinnolin-7-yl)methyl]piperazin-2-one Chemical compound C=1C=C2C(Cl)=CN=NC2=CC=1CN1CCNCC1=O WLPDEDJVUXTZSY-UHFFFAOYSA-N 0.000 claims description 2
CMIXLUFBQPQJIC-UHFFFAOYSA-N 1-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-5-oxo-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(=O)N(CC=4NC5=CC=NC=C5C=4)CC3C(=O)O)=CC2=C1 CMIXLUFBQPQJIC-UHFFFAOYSA-N 0.000 claims description 2
CRYKWXSMGAAYGH-UHFFFAOYSA-N 1-[(7-aminothieno[2,3-c]pyridin-2-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=4C=CN=C(C=4S3)N)=CC2=C1 CRYKWXSMGAAYGH-UHFFFAOYSA-N 0.000 claims description 2
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JZJQEMMSTBRCLW-UHFFFAOYSA-N 1-[2-(pyridin-4-ylamino)ethyl]-4-thieno[2,3-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C=2SC3=NC=CC=C3C=2)CCN1CCNC1=CC=NC=C1 JZJQEMMSTBRCLW-UHFFFAOYSA-N 0.000 claims description 2
LJZIZLNUGIZUHY-UHFFFAOYSA-N 1-[2-(pyridin-4-ylamino)ethyl]-4-thieno[3,2-b]pyridin-2-ylsulfonylpiperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C=2SC3=CC=CN=C3C=2)CCN1CCNC1=CC=NC=C1 LJZIZLNUGIZUHY-UHFFFAOYSA-N 0.000 claims description 2
VWGALLSZEUGDHF-UHFFFAOYSA-N 1-[2-(pyridin-4-ylamino)ethyl]piperazin-2-one Chemical compound O=C1CNCCN1CCNC1=CC=NC=C1 VWGALLSZEUGDHF-UHFFFAOYSA-N 0.000 claims description 2
WUCQVCASJDWMHL-UHFFFAOYSA-N 1-[2-[(2-amino-3-chloropyridin-4-yl)amino]ethyl]-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]piperazin-2-one Chemical compound NC1=NC=CC(NCCN2C(CN(CC2)S(=O)(=O)C=CC=2SC(Cl)=CC=2)=O)=C1Cl WUCQVCASJDWMHL-UHFFFAOYSA-N 0.000 claims description 2
QOMRBIOVACKYLQ-UHFFFAOYSA-N 1-[2-[(3-methylpyridin-4-yl)amino]ethyl]piperazin-2-one Chemical compound CC1=CN=CC=C1NCCN1C(=O)CNCC1 QOMRBIOVACKYLQ-UHFFFAOYSA-N 0.000 claims description 2
BAYNIUKFHHWSFU-UHFFFAOYSA-N 1-[2-[methyl(pyridin-4-yl)amino]ethyl]piperazin-2-one 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=NC=CC=1N(C)CCN1CCNCC1=O BAYNIUKFHHWSFU-UHFFFAOYSA-N 0.000 claims description 2
SMKHDFNCCGCJSL-UHFFFAOYSA-N 1-[3-(4-aminopyridin-3-yl)prop-1-enyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound NC1=CC=NC=C1CC=CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 SMKHDFNCCGCJSL-UHFFFAOYSA-N 0.000 claims description 2
SUYXAMALHLYLGO-UHFFFAOYSA-N 1-[3-(4-aminopyridin-3-yl)propyl]-4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]piperazin-2-one Chemical compound NC1=CC=NC=C1CCCN1C(=O)CN(S(=O)(=O)C=CC=2SC(Cl)=CC=2)CC1 SUYXAMALHLYLGO-UHFFFAOYSA-N 0.000 claims description 2
PEUXZGBCAOQGRK-UHFFFAOYSA-N 1-benzyl-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC1=CC=CC=C1 PEUXZGBCAOQGRK-UHFFFAOYSA-N 0.000 claims description 2
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NVNOZTZNKBRSDF-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]pyrrolo[3,2-c]pyridin-1-yl]acetic acid Chemical compound N1=CC=C2N(CC(=O)O)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 NVNOZTZNKBRSDF-UHFFFAOYSA-N 0.000 claims description 2
GYZLGQMZRBYZNZ-UHFFFAOYSA-N 2-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazine-1-carbonyl]-6-chloro-4h-1,4-benzothiazin-3-one Chemical compound S1C2=CC=C(Cl)C=C2NC(=O)C1C(=O)N(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 GYZLGQMZRBYZNZ-UHFFFAOYSA-N 0.000 claims description 2
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GFCOASLPAVORJU-UHFFFAOYSA-N 2-[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]-n-pyrimidin-4-ylacetamide Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(=O)NC1=CC=NC=N1 GFCOASLPAVORJU-UHFFFAOYSA-N 0.000 claims description 2
SFBLBGAGMPSGSA-UHFFFAOYSA-N 2-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-3-(4-chlorophenyl)prop-2-enoic acid Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(C(O)=O)=CC1=CC=C(Cl)C=C1 SFBLBGAGMPSGSA-UHFFFAOYSA-N 0.000 claims description 2
PNKLPQGHISAFAX-UHFFFAOYSA-N 2-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-6-chloro-1h-quinazolin-4-one Chemical compound C1=C(Cl)C=C2C(=O)NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=NC2=C1 PNKLPQGHISAFAX-UHFFFAOYSA-N 0.000 claims description 2
BLBHYBAZHKAFNO-UHFFFAOYSA-N 2-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-6-chloro-4h-1,4-benzothiazin-3-one Chemical compound S1C2=CC=C(Cl)C=C2NC(=O)C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 BLBHYBAZHKAFNO-UHFFFAOYSA-N 0.000 claims description 2
ZOBJJZIYTREFDZ-UHFFFAOYSA-N 2-amino-4-[[4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-2-oxopiperidin-1-yl]methyl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC(CN2C(CC(CC=3NC4=CC(Cl)=CC=C4N=3)CC2)=O)=C1 ZOBJJZIYTREFDZ-UHFFFAOYSA-N 0.000 claims description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
PRMSFVUWLBPPLY-UHFFFAOYSA-N 3-({4-[(6-chloro-1-benzothien-2-yl)sulfonyl]-2-oxopiperazin-1-yl}methyl)benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1 PRMSFVUWLBPPLY-UHFFFAOYSA-N 0.000 claims description 2
AVXKXPDUVAYPFZ-UHFFFAOYSA-N 3-[[3-oxo-4-[(3-phenylphenyl)methyl]piperazin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2CC(=O)N(CC=3C=C(C=CC=3)C=3C=CC=CC=3)CC2)=C1 AVXKXPDUVAYPFZ-UHFFFAOYSA-N 0.000 claims description 2
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YOPHZYJZQZFVGX-UHFFFAOYSA-N 3-[[4-(6-methoxynaphthalen-2-yl)sulfonyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC1=CC=CC(C(N)=N)=C1 YOPHZYJZQZFVGX-UHFFFAOYSA-N 0.000 claims description 2
LCARCRIPNVHNNF-UHFFFAOYSA-N 3-[[4-[(2-aminoquinolin-6-yl)methyl]-3-oxopiperazin-1-yl]methyl]-7-fluoro-1h-quinolin-2-one Chemical compound C1=C(F)C=C2NC(=O)C(CN3CCN(C(C3)=O)CC3=CC4=CC=C(N=C4C=C3)N)=CC2=C1 LCARCRIPNVHNNF-UHFFFAOYSA-N 0.000 claims description 2
KTPSLHFCCVXGGJ-UHFFFAOYSA-N 3-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-7-chloro-2h-isoquinolin-1-one Chemical compound C1=C(Cl)C=C2C(O)=NC(CN3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 KTPSLHFCCVXGGJ-UHFFFAOYSA-N 0.000 claims description 2
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AETDBVJJAABBTK-UHFFFAOYSA-N 3-[[4-[(6-chloro-1-benzothiophen-2-yl)methyl]-2,5-dioxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2C(CN(CC=3SC4=CC(Cl)=CC=C4C=3)C(=O)C2)=O)=C1 AETDBVJJAABBTK-UHFFFAOYSA-N 0.000 claims description 2
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YYSHYQCBLKQDPI-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(quinolin-6-ylmethyl)piperazin-2-one Chemical compound N1=CC=CC2=CC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC=C21 YYSHYQCBLKQDPI-UHFFFAOYSA-N 0.000 claims description 2
NVQALUJXUKUUGD-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(thieno[2,3-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=NC=C2SC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 NVQALUJXUKUUGD-UHFFFAOYSA-N 0.000 claims description 2
IOYOXXDRTFYBEV-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(thieno[2,3-c]pyridin-3-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2C(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CSC2=C1 IOYOXXDRTFYBEV-UHFFFAOYSA-N 0.000 claims description 2
ZFEMZURPEYWMCK-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(thieno[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2SC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 ZFEMZURPEYWMCK-UHFFFAOYSA-N 0.000 claims description 2
CBSMNZBRWBTDDH-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-chloroisoquinolin-6-yl)methyl]piperazin-2-one Chemical compound ClC1=NC=CC2=CC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC=C21 CBSMNZBRWBTDDH-UHFFFAOYSA-N 0.000 claims description 2
FFAJTTRYZHEHKY-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-chloroisoquinolin-7-yl)methyl]piperazin-2-one Chemical compound C1=CN=C(Cl)C2=CC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC=C21 FFAJTTRYZHEHKY-UHFFFAOYSA-N 0.000 claims description 2
RYKYSAMFJVJJGW-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-ethylpyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound N1=CC=C2N(CC)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 RYKYSAMFJVJJGW-UHFFFAOYSA-N 0.000 claims description 2
ZTGGRTOLTZKBLG-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-chloro-3-hydroxyphenyl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C(O)=CC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1 ZTGGRTOLTZKBLG-UHFFFAOYSA-N 0.000 claims description 2
GAFDXQLFXQXSRS-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-chlorophenyl)methyl]piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 GAFDXQLFXQXSRS-UHFFFAOYSA-N 0.000 claims description 2
MBROHYWUDGAGES-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[2-(pyridin-4-ylamino)ethyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CCNC1=CC=NC=C1 MBROHYWUDGAGES-UHFFFAOYSA-N 0.000 claims description 2
QENQTDWRYPQVKB-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[2-[(3-methylpyridin-4-yl)amino]ethyl]piperazin-2-one Chemical compound CC1=CN=CC=C1NCCN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 QENQTDWRYPQVKB-UHFFFAOYSA-N 0.000 claims description 2
UGLONZWDIHDYTK-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[2-[methyl(pyridin-4-yl)amino]ethyl]piperazin-2-one Chemical compound C1CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CCN(C)C1=CC=NC=C1 UGLONZWDIHDYTK-UHFFFAOYSA-N 0.000 claims description 2
NZNFLUOJACWZKX-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-(2-hydroxyethyl)pyrrolo[3,2-c]pyridin-2-yl]methyl]piperazin-2-one Chemical compound N1=CC=C2N(CCO)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 NZNFLUOJACWZKX-UHFFFAOYSA-N 0.000 claims description 2
NSFXSTDNAOBFAH-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-(2-methoxyethyl)pyrrolo[3,2-c]pyridin-2-yl]methyl]piperazin-2-one Chemical compound N1=CC=C2N(CCOC)C(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 NSFXSTDNAOBFAH-UHFFFAOYSA-N 0.000 claims description 2
QZZPBHWWPIIQAY-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxo-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3NC4=CC=NC=C4C=3)C(=O)O)=CC2=C1 QZZPBHWWPIIQAY-UHFFFAOYSA-N 0.000 claims description 2
YVRQNQPJAFGRQL-UHFFFAOYSA-N 4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)CC3=NC4=CC=C(C=C4N3)Cl)=CC2=C1 YVRQNQPJAFGRQL-UHFFFAOYSA-N 0.000 claims description 2
RBZUKXXTTQTBIU-UHFFFAOYSA-N 4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-1-[(2,4-diaminoquinazolin-7-yl)methyl]piperidin-2-one Chemical compound C1=C(Cl)C=C2NC(CC3CCN(C(C3)=O)CC=3C=CC4=C(N)N=C(N=C4C=3)N)=NC2=C1 RBZUKXXTTQTBIU-UHFFFAOYSA-N 0.000 claims description 2
HHMWPVNSBJHBDE-UHFFFAOYSA-N 4-[(6-chloro-1h-benzimidazol-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=NC4=CC=C(C=C4N3)Cl)=CC2=C1 HHMWPVNSBJHBDE-UHFFFAOYSA-N 0.000 claims description 2
YMOHXXCSQMLKJX-UHFFFAOYSA-N 4-[(6-chloronaphthalen-2-yl)methyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)CC3=CC4=CC=C(C=C4C=C3)Cl)=CC2=C1 YMOHXXCSQMLKJX-UHFFFAOYSA-N 0.000 claims description 2
VOVOTMDETCHTIU-UHFFFAOYSA-N 4-[(6-fluoro-1-benzothiophen-2-yl)sulfonyl]-1-(furo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2OC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)F)=CC2=C1 VOVOTMDETCHTIU-UHFFFAOYSA-N 0.000 claims description 2
UJWDYGUWYIFRRY-UXBLZVDNSA-N 4-[(E)-2-(4-chlorophenyl)ethenyl]sulfonyl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1\C=C\S(=O)(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 UJWDYGUWYIFRRY-UXBLZVDNSA-N 0.000 claims description 2
DNEWDHXGIQYTBG-DUXPYHPUSA-N 4-[(e)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1\C=C\C(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 DNEWDHXGIQYTBG-DUXPYHPUSA-N 0.000 claims description 2
ALTFPBOGERDBTD-ZZXKWVIFSA-N 4-[(e)-3-(3-amino-4-chlorophenyl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C(N)=CC(\C=C\C(=O)N2CC(=O)N(CC=3C=C4N=CN=C(N)C4=CC=3)CC2)=C1 ALTFPBOGERDBTD-ZZXKWVIFSA-N 0.000 claims description 2
UMEYOPZISKLVDS-ZZXKWVIFSA-N 4-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 UMEYOPZISKLVDS-ZZXKWVIFSA-N 0.000 claims description 2
VADQCXJLTKNVMW-UHFFFAOYSA-N 4-[2-(1-benzothiophen-2-yl)ethenylsulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC=C2SC(C=CS(=O)(=O)N3CC(N(CC3)CC=3NC4=CC=NC=C4C=3)=O)=CC2=C1 VADQCXJLTKNVMW-UHFFFAOYSA-N 0.000 claims description 2
ZBOMVVUHFWBCMQ-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)-2-methylpropanoyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1CN(CC=2NC3=CC=NC=C3C=2)C(=O)CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 ZBOMVVUHFWBCMQ-UHFFFAOYSA-N 0.000 claims description 2
XXDYGNPFEQTQPE-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)acetyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1CC(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 XXDYGNPFEQTQPE-UHFFFAOYSA-N 0.000 claims description 2
SJIYXWACWHVDOA-UHFFFAOYSA-N 4-[2-(5-chloro-3-methyl-1-benzothiophen-2-yl)acetyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1CC(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 SJIYXWACWHVDOA-UHFFFAOYSA-N 0.000 claims description 2
LHLYPNUVSWTKQO-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-1-[2-[(3-methylpyridin-4-yl)amino]ethyl]piperazin-2-one Chemical compound CC1=CN=CC=C1NCCN1C(=O)CN(S(=O)(=O)C=CC=2SC(Cl)=CC=2)CC1 LHLYPNUVSWTKQO-UHFFFAOYSA-N 0.000 claims description 2
ACKUTQKSELGEMB-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-1-[2-[methyl(pyridin-4-yl)amino]ethyl]piperazin-2-one Chemical compound C=1C=NC=CC=1N(C)CCN(C(C1)=O)CCN1S(=O)(=O)C=CC1=CC=C(Cl)S1 ACKUTQKSELGEMB-UHFFFAOYSA-N 0.000 claims description 2
IULVBFFYXSEISI-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-(hydroxymethyl)-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(CO)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 IULVBFFYXSEISI-UHFFFAOYSA-N 0.000 claims description 2
TWYWQKVDFUCHGG-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-6-oxo-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylic acid Chemical compound C1C(=O)N(CC=2NC3=CC=NC=C3C=2)C(C(=O)O)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 TWYWQKVDFUCHGG-UHFFFAOYSA-N 0.000 claims description 2
SDBJDGBRRRGJND-UHFFFAOYSA-N 4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1OCC(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 SDBJDGBRRRGJND-UHFFFAOYSA-N 0.000 claims description 2
BATGWXDNQKGPMZ-UHFFFAOYSA-N 4-[3-(5-chlorothiophen-2-yl)prop-2-ynyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1C#CCN1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 BATGWXDNQKGPMZ-UHFFFAOYSA-N 0.000 claims description 2
KNDKGJXKIRVIMX-UHFFFAOYSA-N 4-[3-(5-chlorothiophen-2-yl)propanoyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound S1C(Cl)=CC=C1CCC(=O)N1CC(=O)N(CC=2NC3=CC=NC=C3C=2)CC1 KNDKGJXKIRVIMX-UHFFFAOYSA-N 0.000 claims description 2
FEKZVVYBNUDVKN-UHFFFAOYSA-N 4-[4-(6-methoxypyridin-3-yl)benzoyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(C(=O)N2CC(=O)N(CC=3NC4=CC=NC=C4C=3)CC2)C=C1 FEKZVVYBNUDVKN-UHFFFAOYSA-N 0.000 claims description 2
QIHAVYPUEXRAOP-LSDHHAIUSA-N 4-[[(3r,5s)-4-[(6-chloro-1-benzothiophen-2-yl)methyl]-3,5-dimethyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C([C@@H](N([C@H](C)C1=O)CC=2SC3=CC(Cl)=CC=C3C=2)C)N1CC1=CC=C(C(N)=N)C=C1 QIHAVYPUEXRAOP-LSDHHAIUSA-N 0.000 claims description 2
DTKIRRUFXIWGOP-UHFFFAOYSA-N 4-[[4-(1-benzothiophen-2-ylsulfonyl)-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC=CC=C3C=2)CC1 DTKIRRUFXIWGOP-UHFFFAOYSA-N 0.000 claims description 2
MFMJJUAODHUZLJ-UHFFFAOYSA-N 4-[[4-(4-chlorothieno[3,2-c]pyridin-2-yl)sulfonyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC=NC(Cl)=C3C=2)CC1 MFMJJUAODHUZLJ-UHFFFAOYSA-N 0.000 claims description 2
DNPBVWONJXADQD-UHFFFAOYSA-N 4-[[4-(4-methoxyphenyl)sulfonyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)N(CC=2C=CC(=CC=2)C(N)=N)CC1 DNPBVWONJXADQD-UHFFFAOYSA-N 0.000 claims description 2
ZSKAHROGRNJTTR-UHFFFAOYSA-N 4-[[4-(7-chlorothieno[2,3-c]pyridin-2-yl)sulfonyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC3=C(Cl)N=CC=C3C=2)CC1 ZSKAHROGRNJTTR-UHFFFAOYSA-N 0.000 claims description 2
FDHDMWOOKCMAGW-UHFFFAOYSA-N 4-[[4-(cyclohexylmethyl)-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(CC2CCCCC2)CC1 FDHDMWOOKCMAGW-UHFFFAOYSA-N 0.000 claims description 2
GXOINXSOXBQARU-UHFFFAOYSA-N 4-[[4-[(6-chloro-1-benzothiophen-2-yl)methyl]-2,5-dioxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(CC=2SC3=CC(Cl)=CC=C3C=2)C(=O)C1 GXOINXSOXBQARU-UHFFFAOYSA-N 0.000 claims description 2
IHUZNHAQGUWFMQ-UHFFFAOYSA-N 4-[[4-[(6-chloro-1-benzothiophen-2-yl)methyl]-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(CC=2SC3=CC(Cl)=CC=C3C=2)CC1 IHUZNHAQGUWFMQ-UHFFFAOYSA-N 0.000 claims description 2
OHGPBYXTOZATGW-UHFFFAOYSA-N 4-[[4-[(6-chloro-1-benzothiophen-2-yl)methyl]-3-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1CC(=O)N(CC=2SC3=CC(Cl)=CC=C3C=2)CC1 OHGPBYXTOZATGW-UHFFFAOYSA-N 0.000 claims description 2
MUARJTKMZRFTOB-UHFFFAOYSA-N 4-[[4-[(6-chloro-1h-benzimidazol-2-yl)methyl]-2-oxopiperidin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CC(CC=2NC3=CC(Cl)=CC=C3N=2)CC1 MUARJTKMZRFTOB-UHFFFAOYSA-N 0.000 claims description 2
KHRQFFNPLVOGCU-SOFGYWHQSA-N 4-[[4-[(e)-3-(5-chlorothiophen-2-yl)prop-2-enoyl]-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(C(=O)\C=C\C=2SC(Cl)=CC=2)CC1 KHRQFFNPLVOGCU-SOFGYWHQSA-N 0.000 claims description 2
YKXQIGTZVBKMFK-UHFFFAOYSA-N 4-[[4-[5-(5-chlorothiophen-2-yl)thiophen-2-yl]sulfonyl-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1CN1C(=O)CN(S(=O)(=O)C=2SC(=CC=2)C=2SC(Cl)=CC=2)CC1 YKXQIGTZVBKMFK-UHFFFAOYSA-N 0.000 claims description 2
TYMPJTQGIPWBAC-UHFFFAOYSA-N 4-[[6-(aminomethyl)-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)CN)=CC2=C1 TYMPJTQGIPWBAC-UHFFFAOYSA-N 0.000 claims description 2
MQEFUFBEWBIBCD-UHFFFAOYSA-N 4-amino-3-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=C(N)C(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=C1 MQEFUFBEWBIBCD-UHFFFAOYSA-N 0.000 claims description 2
HTAXOQIVKCKTJR-UHFFFAOYSA-N 4-bromothiophene Chemical compound BrC1=[C]SC=C1 HTAXOQIVKCKTJR-UHFFFAOYSA-N 0.000 claims description 2
RTELOJSBNKTGFC-UHFFFAOYSA-N 5-[[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxopiperazin-1-yl]methyl]-2-pyridin-2-yl-1h-pyrimidin-6-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1CC(C(=N1)O)=CN=C1C1=CC=CC=N1 RTELOJSBNKTGFC-UHFFFAOYSA-N 0.000 claims description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
KIRXVOCNFBUPAS-UHFFFAOYSA-N 6-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1h-quinazolin-4-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC3=CC=C4N=CN=C(C4=C3)O)=CC2=C1 KIRXVOCNFBUPAS-UHFFFAOYSA-N 0.000 claims description 2
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JMHHQAJYCMWCOZ-UHFFFAOYSA-N 7-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1h-quinazolin-4-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)O)=CC2=C1 JMHHQAJYCMWCOZ-UHFFFAOYSA-N 0.000 claims description 2
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238000010537 deprotonation reaction Methods 0.000 description 1
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239000003574 free electron Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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239000008241 heterogeneous mixture Substances 0.000 description 1
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238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
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238000001727 in vivo Methods 0.000 description 1
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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HRRHKFFXEHQMFI-UHFFFAOYSA-N methyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-6-oxopiperazine-2-carboxylate Chemical compound C1C(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)C(C(=O)OC)CN1C(=O)COC1=CC=C(Cl)S1 HRRHKFFXEHQMFI-UHFFFAOYSA-N 0.000 description 1
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239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910000065 phosphene Inorganic materials 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
QHGWRVOSXCSSPO-UHFFFAOYSA-N piperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1CNCCN1 QHGWRVOSXCSSPO-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000008569 process Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
229940039716 prothrombin Drugs 0.000 description 1
108010014806 prothrombinase complex Proteins 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
MBTRMYMICPKJNH-UHFFFAOYSA-N tert-butyl n-[3-[tert-butyl(dimethyl)silyl]oxy-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)[Si](C)(C)OCC(C(=O)N(C)OC)NC(=O)OC(C)(C)C MBTRMYMICPKJNH-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
ZASCXWTVGGZQIZ-UHFFFAOYSA-N thieno[3,2-d]pyrimidin-2-amine Chemical compound NC1=NC=C2SC=CC2=N1 ZASCXWTVGGZQIZ-UHFFFAOYSA-N 0.000 description 1
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
210000005167 vascular cell Anatomy 0.000 description 1
230000009723 vascular congestion Effects 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Hematology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Psychiatry (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)

SK1108-2000A 1998-01-27 1999-01-27 Substituované oxoazaheterocyklické inhibítory faktora xa, farmaceutický prostriedok s ich obsahom a ich použitie SK11082000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7270798P	1998-01-27	1998-01-27
PCT/US1999/001682 WO1999037304A1 (en)	1998-01-27	1999-01-27	SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS

Publications (1)

Publication Number	Publication Date
SK11082000A3 true SK11082000A3 (sk)	2001-01-18

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SK1108-2000A SK11082000A3 (sk)	1998-01-27	1999-01-27	Substituované oxoazaheterocyklické inhibítory faktora xa, farmaceutický prostriedok s ich obsahom a ich použitie

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US (1)	US7612075B2 (et)
EP (1)	EP1051176B1 (et)
JP (1)	JP4676613B2 (et)
KR (1)	KR20010034442A (et)
CN (1)	CN1291892A (et)
AP (1)	AP2000001889A0 (et)
AT (1)	ATE346050T1 (et)
AU (1)	AU745425B2 (et)
BG (1)	BG104633A (et)
BR (1)	BR9907300A (et)
CA (1)	CA2319198C (et)
DE (1)	DE69934093T2 (et)
EA (1)	EA200000768A1 (et)
EE (1)	EE200000435A (et)
HU (1)	HUP0101810A3 (et)
IL (2)	IL137517A0 (et)
IS (1)	IS5574A (et)
NO (1)	NO20003808L (et)
PL (1)	PL342243A1 (et)
SK (1)	SK11082000A3 (et)
TR (1)	TR200002182T2 (et)
UA (1)	UA59433C2 (et)
WO (1)	WO1999037304A1 (et)
YU (1)	YU47600A (et)
ZA (1)	ZA99607B (et)

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Publication number	Priority date	Publication date	Assignee	Title
ID23991A (id) *	1997-09-30	2000-06-14	Daiichi Seiyaku Co	Turunan-turunan sulfonil
US6403595B1 (en) *	1998-02-05	2002-06-11	Takeda Chemical Industries, Ltd.	Sulfonamide derivatives, processes for producing the same and utilization thereof
US7517884B2 (en)	1998-03-30	2009-04-14	Kalypsys Inc.	Sulfonyl-substituted bicyclic compounds as modulators of PPAR
AU5196399A (en) *	1998-08-11	2000-03-06	Daiichi Pharmaceutical Co., Ltd.	Novel sulfonyl derivatives
JP2003529531A (ja) *	1998-11-25	2003-10-07	アヴェンティスファーマシューティカルズインコーポレイテッド	置換オキソアザへテロシクリルＸａ因子阻害剤
WO2000038683A1 (en) *	1998-12-23	2000-07-06	Du Pont Pharmaceuticals Company	THROMBIN OR FACTOR Xa INHIBITORS
WO2000078747A1 (en)	1999-06-22	2000-12-28	Takeda Chemical Industries, Ltd.	Acylhydrazine derivatives, process for preparing the same and use thereof
PL354998A1 (en) *	1999-07-28	2004-03-22	Aventis Pharmaceuticals Products Inc.	Substituted oxoazaheterocyclyl compounds
SE9902987D0 (sv)	1999-08-24	1999-08-24	Astra Pharma Prod	Novel compounds
DE19962924A1 (de)	1999-12-24	2001-07-05	Bayer Ag	Substituierte Oxazolidinone und ihre Verwendung
JP2001294572A (ja) *	2000-02-09	2001-10-23	Dai Ichi Seiyaku Co Ltd	新規スルホニル誘導体
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GB9715895D0 (en)	1997-07-29	1997-10-01	Zeneca Ltd	Heterocyclic compounds
GB9715892D0 (en) *	1997-07-29	1997-10-01	Zeneca Ltd	Heterocyclic compounds
GB9715894D0 (en)	1997-07-29	1997-10-01	Zeneca Ltd	Heterocyclic derivatives
ID23991A (id) *	1997-09-30	2000-06-14	Daiichi Seiyaku Co	Turunan-turunan sulfonil
EP1048652A4 (en) *	1997-12-26	2001-05-09	Mochida Pharm Co Ltd	AROMATIC COMPOUNDS WITH A CYCLIC AMINO GROUP OR THEIR SALTS
US6403595B1 (en) *	1998-02-05	2002-06-11	Takeda Chemical Industries, Ltd.	Sulfonamide derivatives, processes for producing the same and utilization thereof
JP2000204081A (ja) *	1998-02-05	2000-07-25	Takeda Chem Ind Ltd	スルホンアミド誘導体、その製造法及び用途
WO1999046267A1 (en) *	1998-03-12	1999-09-16	Novo Nordisk A/S	Modulators of protein tyrosine phosphatases (ptpases)
DE19835950A1 (de) *	1998-08-08	2000-02-10	Merck Patent Gmbh	Piperazinonderivate

1999
- 1999-01-27 AU AU26533/99A patent/AU745425B2/en not_active Ceased
- 1999-01-27 UA UA2000085034A patent/UA59433C2/uk unknown
- 1999-01-27 PL PL99342243A patent/PL342243A1/xx not_active Application Discontinuation
- 1999-01-27 JP JP2000528286A patent/JP4676613B2/ja not_active Expired - Fee Related
- 1999-01-27 KR KR1020007008221A patent/KR20010034442A/ko not_active Withdrawn
- 1999-01-27 YU YU47600A patent/YU47600A/sh unknown
- 1999-01-27 SK SK1108-2000A patent/SK11082000A3/sk unknown
- 1999-01-27 ZA ZA9900607A patent/ZA99607B/xx unknown
- 1999-01-27 DE DE69934093T patent/DE69934093T2/de not_active Expired - Lifetime
- 1999-01-27 EP EP99906684A patent/EP1051176B1/en not_active Expired - Lifetime
- 1999-01-27 AT AT99906684T patent/ATE346050T1/de not_active IP Right Cessation
- 1999-01-27 CN CN99803501A patent/CN1291892A/zh active Pending
- 1999-01-27 AP APAP/P/2000/001889A patent/AP2000001889A0/en unknown
- 1999-01-27 CA CA2319198A patent/CA2319198C/en not_active Expired - Fee Related
- 1999-01-27 BR BR9907300-5A patent/BR9907300A/pt not_active IP Right Cessation
- 1999-01-27 WO PCT/US1999/001682 patent/WO1999037304A1/en not_active Ceased
- 1999-01-27 EE EEP200000435A patent/EE200000435A/et unknown
- 1999-01-27 TR TR2000/02182T patent/TR200002182T2/xx unknown
- 1999-01-27 EA EA200000768A patent/EA200000768A1/ru unknown
- 1999-01-27 IL IL13751799A patent/IL137517A0/xx active IP Right Grant
- 1999-01-27 HU HU0101810A patent/HUP0101810A3/hu unknown
2000
- 2000-07-25 NO NO20003808A patent/NO20003808L/no not_active Application Discontinuation
- 2000-07-25 IS IS5574A patent/IS5574A/is unknown
- 2000-07-25 BG BG104633A patent/BG104633A/bg unknown
- 2000-07-25 IL IL137517A patent/IL137517A/en not_active IP Right Cessation
2003
- 2003-07-25 US US10/628,093 patent/US7612075B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP4676613B2 (ja)	2011-04-27
EA200000768A1 (ru)	2001-06-25
CA2319198A1 (en)	1999-07-29
DE69934093T2 (de)	2007-06-21
CN1291892A (zh)	2001-04-18
KR20010034442A (ko)	2001-04-25
WO1999037304A1 (en)	1999-07-29
AP2000001889A0 (en)	2000-09-30
IL137517A (en)	2006-12-10
BR9907300A (pt)	2000-10-24
NO20003808L (no)	2000-09-26
AU2653399A (en)	1999-08-09
NO20003808D0 (no)	2000-07-25
ATE346050T1 (de)	2006-12-15
US20040102450A1 (en)	2004-05-27
AU745425B2 (en)	2002-03-21
TR200002182T2 (tr)	2000-12-21
CA2319198C (en)	2011-02-22
US7612075B2 (en)	2009-11-03
BG104633A (bg)	2001-03-30
EP1051176A1 (en)	2000-11-15
HUP0101810A3 (en)	2002-05-28
EE200000435A (et)	2002-02-15
IS5574A (is)	2000-07-25
HUP0101810A2 (hu)	2002-04-29
JP2002501024A (ja)	2002-01-15
ZA99607B (en)	1999-07-27
EP1051176A4 (en)	2002-06-12
YU47600A (sh)	2002-09-19
UA59433C2 (uk)	2003-09-15
IL137517A0 (en)	2001-07-24
PL342243A1 (en)	2001-06-04
DE69934093D1 (de)	2007-01-04
EP1051176B1 (en)	2006-11-22

Publication	Publication Date	Title
SK11082000A3 (sk)	2001-01-18	Substituované oxoazaheterocyklické inhibítory faktora xa, farmaceutický prostriedok s ich obsahom a ich použitie
AU773227B2 (en)	2004-05-20	Substituted oxoazaheterocyclyl compounds
US6281227B1 (en)	2001-08-28	Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds
JP2003529531A (ja)	2003-10-07	置換オキソアザへテロシクリルＸａ因子阻害剤
EP0944386B1 (en)	2002-09-18	Sulfonic acid or sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds
US6602864B1 (en)	2003-08-05	Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds
SI9720019A (sl)	1999-02-28	Spojine substituirani N-/(aminoiminometil) fenilalkil/-azaheterociklamidi sulfonskih kislin
CZ20002728A3 (cs)	2000-11-15	Substituované oxoazaheterocyklylové inhibitory faktoru Xa, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje
MXPA00007250A (en)	2002-03-05	SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS
CZ20004497A3 (en)	2001-06-13	Sulfonyl- or sulfonylamino-N-(heteroaralkyl)azaheterocyclylamide derivatives and pharmaceutical preparation containing thereof