CA2609003A1

CA2609003A1 - Tetrahydropyridothiophenes for use in the treatment of cancer

Tetrahydropyridothiophenes for use in the treatment of cancer Download PDF

Info

Publication number: CA2609003A1
Authority: CA; Canada
Prior art keywords: pyridin; cyano; phenyl; thieno; tetrahydro
Prior art date: 2005-05-25
Legal status : Abandoned

Application number

CA002609003A

Other languages

English (en)

French (fr)

Inventor

Klaus Pekari

Mathias Schmidt

Thomas Baer

Thomas Beckers

Petra Gimmnich

Current Assignee

4SC AG

Original Assignee

Individual

Priority date

2005-05-25

Filing date

2006-05-24

Publication date

2006-11-30

2006-05-24 Application filed by Individual filed Critical Individual

2006-11-30 Publication of CA2609003A1 publication Critical patent/CA2609003A1/en

Status Abandoned legal-status Critical Current

Links

206010028980 Neoplasm Diseases 0.000 title claims description 91
201000011510 cancer Diseases 0.000 title claims description 47
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 9
150000001875 compounds Chemical class 0.000 claims abstract description 495
-1 1-4C-alkoxycarbonyl Chemical group 0.000 claims description 376
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 161
239000000460 chlorine Substances 0.000 claims description 109
229910052801 chlorine Inorganic materials 0.000 claims description 109
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 108
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
150000003839 salts Chemical class 0.000 claims description 77
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 70
239000011737 fluorine Substances 0.000 claims description 69
229910052731 fluorine Inorganic materials 0.000 claims description 69
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 68
125000004076 pyridyl group Chemical group 0.000 claims description 66
238000000034 method Methods 0.000 claims description 60
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 57
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 56
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 46
229910052799 carbon Inorganic materials 0.000 claims description 45
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 41
201000010099 disease Diseases 0.000 claims description 41
125000001424 substituent group Chemical group 0.000 claims description 40
229910052757 nitrogen Inorganic materials 0.000 claims description 39
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239000002246 antineoplastic agent Substances 0.000 claims description 36
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150000003254 radicals Chemical class 0.000 claims description 34
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150000001721 carbon Chemical group 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 28
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 27
230000003211 malignant effect Effects 0.000 claims description 27
239000008194 pharmaceutical composition Substances 0.000 claims description 27
230000009826 neoplastic cell growth Effects 0.000 claims description 26
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230000002062 proliferating effect Effects 0.000 claims description 22
239000000470 constituent Substances 0.000 claims description 20
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125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 15
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000001301 oxygen Chemical group 0.000 claims description 15
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 13
125000003226 pyrazolyl group Chemical group 0.000 claims description 13
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125000004122 cyclic group Chemical group 0.000 claims description 12
238000002560 therapeutic procedure Methods 0.000 claims description 12
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
229910052717 sulfur Chemical group 0.000 claims description 11
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 8
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DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 7
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FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 4
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