CA2558243A1

CA2558243A1 - Inhibitors of histone deacetylase

Inhibitors of histone deacetylase Download PDF

Info

Publication number: CA2558243A1
Authority: CA; Canada
Prior art keywords: thiazole; piperazin; carboxylic acid; acid hydroxyamide; phenyl
Prior art date: 2004-03-08
Legal status : Abandoned

Application number

CA002558243A

Other languages

English (en)

French (fr)

Inventor

Sampath K. Anandan

Xiao-Yi Xiao

Dinesh V. Patel

John S. Ward

Current Assignee

Miikana Therapeutics Inc

Original Assignee

Individual

Priority date

2004-03-08

Filing date

2005-03-08

Publication date

2005-09-22

2005-03-08 Application filed by Individual filed Critical Individual

2005-09-22 Publication of CA2558243A1 publication Critical patent/CA2558243A1/en

Status Abandoned legal-status Critical Current

Links

102000003964 Histone deacetylase Human genes 0.000 title abstract description 31
108090000353 Histone deacetylase Proteins 0.000 title abstract description 31
239000003112 inhibitor Substances 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 171
238000000034 method Methods 0.000 claims abstract description 76
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
230000002062 proliferating effect Effects 0.000 claims abstract description 11
-1 methylimidazolyl Chemical group 0.000 claims description 278
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 246
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 129
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
125000001072 heteroaryl group Chemical group 0.000 claims description 89
229910052739 hydrogen Inorganic materials 0.000 claims description 73
125000002947 alkylene group Chemical group 0.000 claims description 72
125000003118 aryl group Chemical group 0.000 claims description 61
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 56
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 53
125000000623 heterocyclic group Chemical group 0.000 claims description 53
125000000547 substituted alkyl group Chemical group 0.000 claims description 36
125000003107 substituted aryl group Chemical group 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 32
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 27
125000004104 aryloxy group Chemical group 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000002993 cycloalkylene group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
125000004450 alkenylene group Chemical group 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
229940002612 prodrug Drugs 0.000 claims description 19
239000000651 prodrug Substances 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
125000004442 acylamino group Chemical group 0.000 claims description 14
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
125000005415 substituted alkoxy group Chemical group 0.000 claims description 13
125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
125000004001 thioalkyl group Chemical group 0.000 claims description 10
229910052720 vanadium Inorganic materials 0.000 claims description 10
230000000259 anti-tumor effect Effects 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 9
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
239000002246 antineoplastic agent Substances 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
239000003276 histone deacetylase inhibitor Substances 0.000 claims description 6
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
229910052727 yttrium Inorganic materials 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
229910052697 platinum Inorganic materials 0.000 claims description 5
239000012440 retinoic acid metabolism blocking agent Substances 0.000 claims description 5
229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 5
239000000333 selective estrogen receptor modulator Substances 0.000 claims description 5
229910052721 tungsten Inorganic materials 0.000 claims description 5
WPIKKUSJZBLVPY-UHFFFAOYSA-N 2-[4-(4-acetylphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 WPIKKUSJZBLVPY-UHFFFAOYSA-N 0.000 claims description 4
WFYBTESVTKBMEB-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=CC(F)=CC=2)CC1 WFYBTESVTKBMEB-UHFFFAOYSA-N 0.000 claims description 4
SOJXWCHXNJFSHA-UHFFFAOYSA-N 2-[4-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)N(CC1)CCN1C1=NC=C(C(=O)NO)S1 SOJXWCHXNJFSHA-UHFFFAOYSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
229940102550 Estrogen receptor antagonist Drugs 0.000 claims description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 4
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
NDDBGRAAXATVPM-UHFFFAOYSA-N n-hydroxy-2-[4-(4-phenylphenyl)sulfonylpiperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 NDDBGRAAXATVPM-UHFFFAOYSA-N 0.000 claims description 4
PUEIPAZPNFIMBW-UHFFFAOYSA-N n-hydroxy-2-[4-[4-(trifluoromethoxy)phenyl]sulfonylpiperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)CC1 PUEIPAZPNFIMBW-UHFFFAOYSA-N 0.000 claims description 4
KPDDJYNSRQPTKP-UHFFFAOYSA-N n-hydroxy-2-[4-[4-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 KPDDJYNSRQPTKP-UHFFFAOYSA-N 0.000 claims description 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
HEUFSDCAWMYPTG-UHFFFAOYSA-N 2-[4-(2-phenylacetyl)piperazin-1-yl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1N1CCN(C(=O)CC=2C=CC=CC=2)CC1 HEUFSDCAWMYPTG-UHFFFAOYSA-N 0.000 claims description 3
GBYHFKMJQQDMBI-UHFFFAOYSA-N 2-[4-(3,4-dimethoxyphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 GBYHFKMJQQDMBI-UHFFFAOYSA-N 0.000 claims description 3
UFWOOUJZRJGIFE-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=C(C)C(C)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 UFWOOUJZRJGIFE-UHFFFAOYSA-N 0.000 claims description 3
NNKZQUPVEPHEPS-UHFFFAOYSA-N 2-[4-[(3,5-dimethyl-2h-1,2-oxazol-3-yl)sulfonyl]piperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound N1OC(C)=CC1(C)S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 NNKZQUPVEPHEPS-UHFFFAOYSA-N 0.000 claims description 3
YIVMOAUARZOMIP-UHFFFAOYSA-N 2-[4-[2-[3-(dimethylamino)phenyl]phenyl]sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound CN(C)C1=CC=CC(C=2C(=CC=CC=2)S(=O)(=O)N2CCN(CC2)C=2SC(=CN=2)C(=O)NO)=C1 YIVMOAUARZOMIP-UHFFFAOYSA-N 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 3
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 3
229940122803 Vinca alkaloid Drugs 0.000 claims description 3
229930003316 Vitamin D Natural products 0.000 claims description 3
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
239000003968 dna methyltransferase inhibitor Substances 0.000 claims description 3
229940043355 kinase inhibitor Drugs 0.000 claims description 3
ZRJUABKPNNHWEB-UHFFFAOYSA-N n-hydroxy-2-(4-thiophen-2-ylsulfonylpiperazin-1-yl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 ZRJUABKPNNHWEB-UHFFFAOYSA-N 0.000 claims description 3
SINFIJWJVFHMHP-UHFFFAOYSA-N n-hydroxy-2-[4-(4-nitrophenyl)sulfonylpiperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)CC1 SINFIJWJVFHMHP-UHFFFAOYSA-N 0.000 claims description 3
DFQBYXXWJMNWLC-UHFFFAOYSA-N n-hydroxy-2-[4-(4-propan-2-ylphenyl)sulfonylpiperazin-1-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 DFQBYXXWJMNWLC-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
239000003528 protein farnesyltransferase inhibitor Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
235000019166 vitamin D Nutrition 0.000 claims description 3
239000011710 vitamin D Substances 0.000 claims description 3
150000003710 vitamin D derivatives Chemical class 0.000 claims description 3
229940046008 vitamin d Drugs 0.000 claims description 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
JYRKKOKBUMZIPS-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1C1=NC=C(C(O)=O)S1 JYRKKOKBUMZIPS-UHFFFAOYSA-N 0.000 claims description 2
GALLLEJEOZLPMY-UHFFFAOYSA-N 2-(4-benzoylpiperazin-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1N1CCN(C(=O)C=2C=CC=CC=2)CC1 GALLLEJEOZLPMY-UHFFFAOYSA-N 0.000 claims description 2
HGKGJEZYUNSVHC-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(CC=2C=CC=CC=2)CC1 HGKGJEZYUNSVHC-UHFFFAOYSA-N 0.000 claims description 2
ZNHRIWFGFHOHDX-UHFFFAOYSA-N 2-(4-benzylsulfonylpiperazin-1-yl)-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 ZNHRIWFGFHOHDX-UHFFFAOYSA-N 0.000 claims description 2
FMNPXFRYSSBHOZ-UHFFFAOYSA-N 2-(4-ethylsulfonylpiperazin-1-yl)-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=NC=C(C(=O)NO)S1 FMNPXFRYSSBHOZ-UHFFFAOYSA-N 0.000 claims description 2
MHBJCMOWAMOGOV-UHFFFAOYSA-N 2-[4-(2,1,3-benzothiadiazol-5-ylsulfonyl)piperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C2=CC3=NSN=C3C=C2)CC1 MHBJCMOWAMOGOV-UHFFFAOYSA-N 0.000 claims description 2
CGTHHJAXHDABPA-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-2-ylsulfonyl)piperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C2OC3=CC=CC=C3C2)CC1 CGTHHJAXHDABPA-UHFFFAOYSA-N 0.000 claims description 2
UKJCXLXVTHZMMK-UHFFFAOYSA-N 2-[4-(2,5-dimethoxyphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)N2CCN(CC2)C=2SC(=CN=2)C(=O)NO)=C1 UKJCXLXVTHZMMK-UHFFFAOYSA-N 0.000 claims description 2
HBBKVCNUVSYCMM-UHFFFAOYSA-N 2-[4-(2,5-dimethylphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2CCN(CC2)C=2SC(=CN=2)C(=O)NO)=C1 HBBKVCNUVSYCMM-UHFFFAOYSA-N 0.000 claims description 2
BEPFYWFQTNUTIV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1CN(CCN)CCN1C1=NC=C(C(=O)NO)S1 BEPFYWFQTNUTIV-UHFFFAOYSA-N 0.000 claims description 2
NBKWNKHXPLQXRE-UHFFFAOYSA-N 2-[4-(2-chloro-5-methoxyphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)N2CCN(CC2)C=2SC(=CN=2)C(=O)NO)=C1 NBKWNKHXPLQXRE-UHFFFAOYSA-N 0.000 claims description 2
OGSULBXSPWXVJZ-UHFFFAOYSA-N 2-[4-(3,4-difluorophenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=C(F)C(F)=CC=2)CC1 OGSULBXSPWXVJZ-UHFFFAOYSA-N 0.000 claims description 2
LUEGKVZPBPBUAA-UHFFFAOYSA-N 2-[4-(3,4-dihydro-1,2-benzodioxin-3-ylsulfonyl)piperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C2OOC3=CC=CC=C3C2)CC1 LUEGKVZPBPBUAA-UHFFFAOYSA-N 0.000 claims description 2
IWKHJIZHKWNSPU-UHFFFAOYSA-N 2-[4-(3,5-difluorophenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=C(F)C=C(F)C=2)CC1 IWKHJIZHKWNSPU-UHFFFAOYSA-N 0.000 claims description 2
YYMQWWSSJUUEAJ-UHFFFAOYSA-N 2-[4-(3-chloro-4-methylphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 YYMQWWSSJUUEAJ-UHFFFAOYSA-N 0.000 claims description 2
HMQYJPLXNUTWEL-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NO)=CN=C1N1CCN(S(=O)(=O)C=2C=C(Cl)C=CC=2)CC1 HMQYJPLXNUTWEL-UHFFFAOYSA-N 0.000 claims description 2
FCUYTJOJEPTJPE-UHFFFAOYSA-N 2-[4-(3-fluoro-4-methylphenyl)sulfonylpiperazin-1-yl]-n-hydroxy-1,3-thiazole-5-carboxamide Chemical compound C1=C(F)C(C)=CC=C1S(=O)(=O)N1CCN(C=2SC(=CN=2)C(=O)NO)CC1 FCUYTJOJEPTJPE-UHFFFAOYSA-N 0.000 claims description 2
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