CA2603398A1

CA2603398A1 - Sulfonylpyrroles as histone deacetylase inhibitors

Sulfonylpyrroles as histone deacetylase inhibitors Download PDF

Info

Publication number: CA2603398A1
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; compounds; methyl; cancer
Prior art date: 2005-04-07
Legal status : Abandoned

Application number

CA002603398A

Other languages

English (en)

French (fr)

Inventor

Thomas Maier

Thomas Baer

Thomas Beckers

Frank Dullweber

Volker Gekeler

Astrid Zimmermann

Current Assignee

4SC AG

Original Assignee

Individual

Priority date

2005-04-07

Filing date

2006-04-07

Publication date

2006-10-12

2006-04-07 Application filed by Individual filed Critical Individual

2006-10-12 Publication of CA2603398A1 publication Critical patent/CA2603398A1/en

Status Abandoned legal-status Critical Current

Links

239000003276 histone deacetylase inhibitor Substances 0.000 title claims description 21
229940121372 histone deacetylase inhibitor Drugs 0.000 title claims description 10
JRZBWRPPYOMOJE-UHFFFAOYSA-N 2-sulfonylpyrrole Chemical class O=S(=O)=C1C=CC=N1 JRZBWRPPYOMOJE-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 293
108090000353 Histone deacetylase Proteins 0.000 claims abstract description 88
102000003964 Histone deacetylase Human genes 0.000 claims abstract description 88
-1 1-4C-alkyl Inorganic materials 0.000 claims description 157
229910052739 hydrogen Inorganic materials 0.000 claims description 126
239000001257 hydrogen Substances 0.000 claims description 126
206010028980 Neoplasm Diseases 0.000 claims description 113
150000002431 hydrogen Chemical group 0.000 claims description 97
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 71
201000010099 disease Diseases 0.000 claims description 62
201000011510 cancer Diseases 0.000 claims description 60
229910052757 nitrogen Inorganic materials 0.000 claims description 56
238000000034 method Methods 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 49
125000001072 heteroaryl group Chemical group 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 37
229910052760 oxygen Inorganic materials 0.000 claims description 37
239000001301 oxygen Substances 0.000 claims description 37
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
230000009826 neoplastic cell growth Effects 0.000 claims description 36
239000008194 pharmaceutical composition Substances 0.000 claims description 36
125000005842 heteroatom Chemical group 0.000 claims description 35
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
239000002246 antineoplastic agent Substances 0.000 claims description 33
229910052717 sulfur Inorganic materials 0.000 claims description 32
239000011593 sulfur Substances 0.000 claims description 32
239000003814 drug Substances 0.000 claims description 29
230000000694 effects Effects 0.000 claims description 29
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
230000003211 malignant effect Effects 0.000 claims description 28
125000002950 monocyclic group Chemical group 0.000 claims description 27
239000004480 active ingredient Substances 0.000 claims description 26
125000002619 bicyclic group Chemical group 0.000 claims description 25
125000001624 naphthyl group Chemical group 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
238000011282 treatment Methods 0.000 claims description 24
208000035475 disorder Diseases 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
230000005764 inhibitory process Effects 0.000 claims description 20
101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 18
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
230000006882 induction of apoptosis Effects 0.000 claims description 17
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
238000002560 therapeutic procedure Methods 0.000 claims description 14
230000000973 chemotherapeutic effect Effects 0.000 claims description 11
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
238000009472 formulation Methods 0.000 claims description 9
OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
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 8
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
229960004316 cisplatin Drugs 0.000 claims description 8
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 6
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125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 5
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108010002156 Depsipeptides Proteins 0.000 claims description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
239000005517 L01XE01 - Imatinib Substances 0.000 claims description 5
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 5
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 5
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 5
229960001433 erlotinib Drugs 0.000 claims description 5
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 5
229960002584 gefitinib Drugs 0.000 claims description 5
XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 5
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
229960000435 oblimersen Drugs 0.000 claims description 5
MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 claims description 5
FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
229960003787 sorafenib Drugs 0.000 claims description 5
WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 5
AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims description 5
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims description 5
229960000604 valproic acid Drugs 0.000 claims description 5
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
208000017604 Hodgkin disease Diseases 0.000 claims description 4
208000010747 Hodgkins lymphoma Diseases 0.000 claims description 4
102000014150 Interferons Human genes 0.000 claims description 4
108010050904 Interferons Proteins 0.000 claims description 4
229940124613 TLR 7/8 agonist Drugs 0.000 claims description 4
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 4
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 4
229960000397 bevacizumab Drugs 0.000 claims description 4
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GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 4
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229960004679 doxorubicin Drugs 0.000 claims description 4
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VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 4
229960002949 fluorouracil Drugs 0.000 claims description 4
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IXWNTLSTOZFSCM-YVACAVLKSA-N ombrabulin Chemical compound C1=C(NC(=O)[C@@H](N)CO)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 IXWNTLSTOZFSCM-YVACAVLKSA-N 0.000 claims description 4
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WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 4
229940044655 toll-like receptor 9 agonist Drugs 0.000 claims description 4
239000004066 vascular targeting agent Substances 0.000 claims description 4
FUFGMYHMTZHTRG-DAFODLJHSA-N (e)-3-[1-(1,3-benzothiazol-6-ylsulfonyl)pyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(N=CS2)C2=C1 FUFGMYHMTZHTRG-DAFODLJHSA-N 0.000 claims description 3
UZWJQYHJADXGLH-AATRIKPKSA-N (e)-3-[1-(1-benzothiophen-2-ylsulfonyl)pyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC2=CC=CC=C2S1 UZWJQYHJADXGLH-AATRIKPKSA-N 0.000 claims description 3
BHPNTOIEGASYMJ-ONEGZZNKSA-N (e)-3-[1-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]pyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)N1C=C(\C=C\C(=O)NO)C=C1 BHPNTOIEGASYMJ-ONEGZZNKSA-N 0.000 claims description 3
MRNOJWJLAVFBJS-FMIVXFBMSA-N (e)-n-(2-aminophenyl)-3-(1-naphthalen-2-ylsulfonylpyrrol-3-yl)prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C=C1 MRNOJWJLAVFBJS-FMIVXFBMSA-N 0.000 claims description 3
OTBRMHRCJZDIOC-MDZDMXLPSA-N (e)-n-(2-aminophenyl)-3-[1-(1-benzothiophen-2-ylsulfonyl)pyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2SC3=CC=CC=C3C=2)C=C1 OTBRMHRCJZDIOC-MDZDMXLPSA-N 0.000 claims description 3
PKSVPYNSMZMXKH-ONEGZZNKSA-N (e)-n-hydroxy-3-(1-pyridin-3-ylsulfonylpyrrol-3-yl)prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CN=C1 PKSVPYNSMZMXKH-ONEGZZNKSA-N 0.000 claims description 3
WEGONCAIUXMTKW-NSCUHMNNSA-N (e)-n-hydroxy-3-[1-(1-methylpyrazol-4-yl)sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NN(C)C=C1S(=O)(=O)N1C=C(\C=C\C(=O)NO)C=C1 WEGONCAIUXMTKW-NSCUHMNNSA-N 0.000 claims description 3
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BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 claims description 3
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RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 claims description 3
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