CA2596202A1

CA2596202A1 - Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer

Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer Download PDF

Info

Publication number: CA2596202A1
Authority: CA; Canada
Prior art keywords: cyano; dihydro; thieno; carboxylic acid; pyridine
Prior art date: 2005-02-09
Legal status : Abandoned

Application number

CA002596202A

Other languages

English (en)

French (fr)

Inventor

Klaus Pekari

Mathias Schmidt

Thomas Bar

Thomas Beckers

Bjoern Bartels

Current Assignee

4SC AG

Original Assignee

Individual

Priority date

2005-02-09

Filing date

2006-02-08

Publication date

2006-08-17

2006-02-08 Application filed by Individual filed Critical Individual

2006-08-17 Publication of CA2596202A1 publication Critical patent/CA2596202A1/en

Status Abandoned legal-status Critical Current

Links

206010028980 Neoplasm Diseases 0.000 title claims abstract description 92
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 72
201000011510 cancer Diseases 0.000 title claims abstract description 48
201000010099 disease Diseases 0.000 title claims abstract description 43
230000002062 proliferating effect Effects 0.000 title claims description 24
238000011282 treatment Methods 0.000 title claims description 22
WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical class N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 478
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 95
125000001424 substituent group Chemical group 0.000 claims abstract description 42
238000002560 therapeutic procedure Methods 0.000 claims abstract description 13
125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 4
-1 1-4C-alkoxycarbonyl Chemical group 0.000 claims description 413
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 172
239000000460 chlorine Substances 0.000 claims description 113
229910052801 chlorine Inorganic materials 0.000 claims description 111
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 110
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 98
239000011737 fluorine Substances 0.000 claims description 80
229910052731 fluorine Inorganic materials 0.000 claims description 80
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 79
125000004076 pyridyl group Chemical group 0.000 claims description 72
150000003839 salts Chemical class 0.000 claims description 69
238000000034 method Methods 0.000 claims description 62
229910052799 carbon Inorganic materials 0.000 claims description 59
229910052757 nitrogen Inorganic materials 0.000 claims description 55
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 52
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 50
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 49
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 48
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 47
125000002541 furyl group Chemical group 0.000 claims description 47
125000001544 thienyl group Chemical group 0.000 claims description 47
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150000003254 radicals Chemical class 0.000 claims description 40
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239000000470 constituent Substances 0.000 claims description 32
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229910052739 hydrogen Inorganic materials 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
239000003814 drug Substances 0.000 claims description 28
125000000623 heterocyclic group Chemical group 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 27
230000003211 malignant effect Effects 0.000 claims description 27
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
230000009826 neoplastic cell growth Effects 0.000 claims description 26
125000005842 heteroatom Chemical group 0.000 claims description 25
230000006882 induction of apoptosis Effects 0.000 claims description 25
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
239000001301 oxygen Chemical group 0.000 claims description 23
125000004122 cyclic group Chemical group 0.000 claims description 20
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
125000002883 imidazolyl group Chemical group 0.000 claims description 19
125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 18
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 17
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229910052717 sulfur Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
239000005864 Sulphur Chemical group 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
125000002971 oxazolyl group Chemical group 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
125000000168 pyrrolyl group Chemical group 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 12
125000000335 thiazolyl group Chemical group 0.000 claims description 12
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125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 10
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230000000973 chemotherapeutic effect Effects 0.000 claims description 10
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 10
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
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229920006395 saturated elastomer Polymers 0.000 claims description 10
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000001425 triazolyl group Chemical group 0.000 claims description 9
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CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 7
229960004316 cisplatin Drugs 0.000 claims description 7
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 7
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
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 6
229930012538 Paclitaxel Natural products 0.000 claims description 6
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 6
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[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
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
229960000435 oblimersen Drugs 0.000 claims description 6
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 6
229960001592 paclitaxel Drugs 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
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
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125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
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 5
239000003795 chemical substances by application Substances 0.000 claims description 5
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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
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
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
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102000014150 Interferons Human genes 0.000 claims description 4
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FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 4
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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
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SJGPTRDNBRAKDG-UHFFFAOYSA-N ethyl 3-cyano-2-[(2-morpholin-4-ylacetyl)amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CN1CCOCC1 SJGPTRDNBRAKDG-UHFFFAOYSA-N 0.000 claims description 4
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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 4
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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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BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 claims description 3
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IDXDMHGZQWHGAV-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 IDXDMHGZQWHGAV-UHFFFAOYSA-N 0.000 claims 2
WSHYFIVKQNBLOX-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 WSHYFIVKQNBLOX-UHFFFAOYSA-N 0.000 claims 2
VLGACCFXZWUYSY-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 VLGACCFXZWUYSY-UHFFFAOYSA-N 0.000 claims 2
IJSBTLYHVZFAQV-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 IJSBTLYHVZFAQV-UHFFFAOYSA-N 0.000 claims 2
BGSQSPCZKPLNDK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=CN=C1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 BGSQSPCZKPLNDK-UHFFFAOYSA-N 0.000 claims 1
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QDDOCCCGTFEHPG-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 QDDOCCCGTFEHPG-UHFFFAOYSA-N 0.000 claims 1
ZUGDTMRHFVDJEN-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 ZUGDTMRHFVDJEN-UHFFFAOYSA-N 0.000 claims 1
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XSYPHRKLEHRGCA-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 XSYPHRKLEHRGCA-UHFFFAOYSA-N 0.000 claims 1
RLUUHGOPGDBVAS-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2C=NC=CC=2)=C2C#N)=C2CC1 RLUUHGOPGDBVAS-UHFFFAOYSA-N 0.000 claims 1
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IIXWTFCZHKOFOG-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 IIXWTFCZHKOFOG-UHFFFAOYSA-N 0.000 claims 1
ZMVCFGQLEXNRBC-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=N1 ZMVCFGQLEXNRBC-UHFFFAOYSA-N 0.000 claims 1
JKJCSLZNLUYLFW-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CN=C1 JKJCSLZNLUYLFW-UHFFFAOYSA-N 0.000 claims 1
SHUYVCSHMBOIAR-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CN=CN1C SHUYVCSHMBOIAR-UHFFFAOYSA-N 0.000 claims 1
QELNEDNOUOZLRT-UHFFFAOYSA-N (3-methylimidazol-4-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=NC=C1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 QELNEDNOUOZLRT-UHFFFAOYSA-N 0.000 claims 1
LFTNBIMSPUTPTK-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC(O)CO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 LFTNBIMSPUTPTK-UHFFFAOYSA-N 0.000 claims 1
JJCSZDOAJMEADZ-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 JJCSZDOAJMEADZ-UHFFFAOYSA-N 0.000 claims 1
LUHNFRINOIKMHI-UHFFFAOYSA-N 2-(2,4-dimethylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCCN1C=C(C)N=C1C LUHNFRINOIKMHI-UHFFFAOYSA-N 0.000 claims 1
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TUFCKEJBYKBYJR-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CC1=NC=CN1CCOC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 TUFCKEJBYKBYJR-UHFFFAOYSA-N 0.000 claims 1
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MDZSCSKZEOGQJF-UHFFFAOYSA-N 2-[3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound S1C=2CN(C(=O)OCC(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 MDZSCSKZEOGQJF-UHFFFAOYSA-N 0.000 claims 1
HUYACICMAUONCQ-UHFFFAOYSA-N 2-[3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound C1N(C(=O)OCC(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 HUYACICMAUONCQ-UHFFFAOYSA-N 0.000 claims 1
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OPWSFZUYWUCXGX-UHFFFAOYSA-N 2-acetyloxyethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCOC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 OPWSFZUYWUCXGX-UHFFFAOYSA-N 0.000 claims 1
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WDOGQTQEKVLZIJ-WAYWQWQTSA-N combretastatin a-4 phosphate Chemical compound C1=C(OP(O)(O)=O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 WDOGQTQEKVLZIJ-WAYWQWQTSA-N 0.000 claims 1
QERKELASDRXTRX-UHFFFAOYSA-N ethyl 2-[3-(1,3-benzodioxol-4-yl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC2=C1OCO2 QERKELASDRXTRX-UHFFFAOYSA-N 0.000 claims 1
LFDUVKNXFWYBKC-UHFFFAOYSA-N ethyl 2-[3-(2-bromophenyl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1Br LFDUVKNXFWYBKC-UHFFFAOYSA-N 0.000 claims 1
UGESIBIPQUWSIR-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenyl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1Cl UGESIBIPQUWSIR-UHFFFAOYSA-N 0.000 claims 1
IBVRGOGPGFVSPF-UHFFFAOYSA-N ethyl 2-[3-(3-chlorophenyl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(Cl)=C1 IBVRGOGPGFVSPF-UHFFFAOYSA-N 0.000 claims 1
LJTHHKCFHVZWQL-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)propanoylamino]-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=C(Cl)C=C1 LJTHHKCFHVZWQL-UHFFFAOYSA-N 0.000 claims 1
LQEYHCYNUJJGOG-UHFFFAOYSA-N ethyl 3-cyano-2-(3-cyclohexylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1CCCCC1 LQEYHCYNUJJGOG-UHFFFAOYSA-N 0.000 claims 1
QPMZVQCJGXEQTE-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 QPMZVQCJGXEQTE-UHFFFAOYSA-N 0.000 claims 1
SPJLEEAKQDTWNM-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CN=C1 SPJLEEAKQDTWNM-UHFFFAOYSA-N 0.000 claims 1
HWMUOKKDTWNHBO-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 HWMUOKKDTWNHBO-UHFFFAOYSA-N 0.000 claims 1
QADDFRXDJAEOBT-UHFFFAOYSA-N ethyl 3-cyano-2-(3-pyrimidin-5-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CN=CN=C1 QADDFRXDJAEOBT-UHFFFAOYSA-N 0.000 claims 1
LKZLMVZBJQVMRP-UHFFFAOYSA-N ethyl 3-cyano-2-[(2-phenylcyclopropanecarbonyl)amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)C1CC1C1=CC=CC=C1 LKZLMVZBJQVMRP-UHFFFAOYSA-N 0.000 claims 1
KFKNSWMQLDEFMI-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2,3-dihydro-1,4-benzodioxin-5-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1CCOC2=C1C=CC=C2CCC(=O)NC(S1)=C(C#N)C2=C1CN(C(=O)OCC)CC2 KFKNSWMQLDEFMI-UHFFFAOYSA-N 0.000 claims 1
MISQHTMFDQFFHU-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-fluorophenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1F MISQHTMFDQFFHU-UHFFFAOYSA-N 0.000 claims 1
KTXNLXRVQDSQHD-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(2-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1C KTXNLXRVQDSQHD-UHFFFAOYSA-N 0.000 claims 1
JHVZMRAARHOQEQ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(3-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC(C)=C1 JHVZMRAARHOQEQ-UHFFFAOYSA-N 0.000 claims 1
CDHRNLISPUMGKK-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-fluorophenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=C(F)C=C1 CDHRNLISPUMGKK-UHFFFAOYSA-N 0.000 claims 1
WMKSYONSCKXRPJ-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(4-methylphenyl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=C(C)C=C1 WMKSYONSCKXRPJ-UHFFFAOYSA-N 0.000 claims 1
VLUFMGNROYTKQS-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(5-methylpyrazol-1-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCN1N=CC=C1C VLUFMGNROYTKQS-UHFFFAOYSA-N 0.000 claims 1
SYRFWYKFRLMPJG-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 SYRFWYKFRLMPJG-UHFFFAOYSA-N 0.000 claims 1
XEQHDALQOYILDN-UHFFFAOYSA-N ethyl 3-cyano-2-[3-(oxolan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1CCCO1 XEQHDALQOYILDN-UHFFFAOYSA-N 0.000 claims 1
QWMCCJNSESILSJ-UHFFFAOYSA-N ethyl 3-cyano-2-[[2-(furan-2-yl)cyclopropanecarbonyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)C1CC1C1=CC=CO1 QWMCCJNSESILSJ-UHFFFAOYSA-N 0.000 claims 1
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PMVUJBIGLXVLLR-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 PMVUJBIGLXVLLR-UHFFFAOYSA-N 0.000 claims 1
WIXIKSKCEZHZLY-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 WIXIKSKCEZHZLY-UHFFFAOYSA-N 0.000 claims 1
PAFSUSZTQWDKQU-UHFFFAOYSA-N pyridin-2-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 PAFSUSZTQWDKQU-UHFFFAOYSA-N 0.000 claims 1
HVRYPCDTMGFNLL-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=CN=C1 HVRYPCDTMGFNLL-UHFFFAOYSA-N 0.000 claims 1
FIUNWHOUCVQLLC-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 FIUNWHOUCVQLLC-UHFFFAOYSA-N 0.000 claims 1
UIXSAJZPFJYUII-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 UIXSAJZPFJYUII-UHFFFAOYSA-N 0.000 claims 1
OLQCBXOJYKFSCG-UHFFFAOYSA-N pyridin-3-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 OLQCBXOJYKFSCG-UHFFFAOYSA-N 0.000 claims 1
OOCHYCXBMDBIBT-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=CC=NC=C1 OOCHYCXBMDBIBT-UHFFFAOYSA-N 0.000 claims 1
PCASJTPNQGJRSA-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 PCASJTPNQGJRSA-UHFFFAOYSA-N 0.000 claims 1
WPTOXDXTEJMNHS-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 WPTOXDXTEJMNHS-UHFFFAOYSA-N 0.000 claims 1
JAVUDBZOJRVZMC-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CN=C1 JAVUDBZOJRVZMC-UHFFFAOYSA-N 0.000 claims 1
RFLLJIRRBAJMGX-UHFFFAOYSA-N pyridin-4-ylmethyl 3-cyano-2-[3-(furan-2-yl)propanoylamino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 RFLLJIRRBAJMGX-UHFFFAOYSA-N 0.000 claims 1
ZLFTTYVNDGLFQL-UHFFFAOYSA-N tert-butyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 ZLFTTYVNDGLFQL-UHFFFAOYSA-N 0.000 claims 1
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