AU2010294588A1 - Substituted (heteroarylmethyl) thiohydantoins as anticancer drugs - Google Patents

Info

Publication number

AU2010294588A1

AU2010294588A1 AU2010294588A AU2010294588A AU2010294588A1 AU 2010294588 A1 AU2010294588 A1 AU 2010294588A1 AU 2010294588 A AU2010294588 A AU 2010294588A AU 2010294588 A AU2010294588 A AU 2010294588A AU 2010294588 A1 AU2010294588 A1 AU 2010294588A1

Authority

AU

Australia

Prior art keywords

methyl

group

trifluoromethyl

oxo

benzonitrile

Prior art date

2009-09-11

Legal status (The legal status 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 status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 title abstract description 20
• 239000002246 antineoplastic agent Substances 0.000 title description 4
• 229940041181 antineoplastic drug Drugs 0.000 title description 2
• 238000002360 preparation method Methods 0.000 claims abstract description 52
• 238000011282 treatment Methods 0.000 claims abstract description 48
• 206010060862 Prostate cancer Diseases 0.000 claims abstract description 45
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 45
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
• 238000011321 prophylaxis Methods 0.000 claims abstract description 24
• 239000003814 drug Substances 0.000 claims abstract description 20
• 238000000034 method Methods 0.000 claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims description 170
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 163
• -1 tetrahydro-2H-pyranyl)oxy- group Chemical group 0.000 claims description 115
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 54
• 239000012453 solvate Substances 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
• 229910052731 fluorine Inorganic materials 0.000 claims description 30
• 239000000203 mixture Substances 0.000 claims description 30
• 239000011737 fluorine Chemical group 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 239000002904 solvent Substances 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000002883 imidazolyl group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 239000000460 chlorine Chemical group 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims description 10
• 230000003463 hyperproliferative effect Effects 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 108700012941 GNRH1 Proteins 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000000369 oxido group Chemical group [*]=O 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 239000000556 agonist Substances 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000005959 diazepanyl group Chemical group 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• 125000005961 oxazepanyl group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 239000002677 5-alpha reductase inhibitor Substances 0.000 claims description 4
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 claims description 4
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 4
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 239000005557 antagonist Substances 0.000 claims description 4
• 150000007513 acids Chemical class 0.000 claims description 3
• 239000000824 cytostatic agent Substances 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• LQZCLJRKPUSMKK-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(5-methyltetrazol-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NN=NN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S LQZCLJRKPUSMKK-UHFFFAOYSA-N 0.000 claims description 2
• DSMLVMACRTUXNV-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-[4-(trifluoromethyl)imidazol-1-yl]pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(C(F)(F)F)=C1 DSMLVMACRTUXNV-UHFFFAOYSA-N 0.000 claims description 2
• TYPIQCVZXDXIIX-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-3-[[6-[2-(2-oxoimidazolidin-1-yl)ethoxy]pyridin-3-yl]methyl]-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1OCCN1CCNC1=O TYPIQCVZXDXIIX-UHFFFAOYSA-N 0.000 claims description 2
• 229940046836 anti-estrogen Drugs 0.000 claims description 2
• 230000001833 anti-estrogenic effect Effects 0.000 claims description 2
• 239000003418 antiprogestin Substances 0.000 claims description 2
• 229940011871 estrogen Drugs 0.000 claims description 2
• 239000000262 estrogen Substances 0.000 claims description 2
• 239000000328 estrogen antagonist Substances 0.000 claims description 2
• 229940043355 kinase inhibitor Drugs 0.000 claims description 2
• 239000002697 lyase inhibitor Substances 0.000 claims description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• JWOKAJZCYYEKOL-UHFFFAOYSA-N 4-[3-[(2-imidazol-1-ylpyrimidin-5-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CN=C1N1C=CN=C1 JWOKAJZCYYEKOL-UHFFFAOYSA-N 0.000 claims 1
• LGTPUPFZQOFLIO-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-3-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NC(OC)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S LGTPUPFZQOFLIO-UHFFFAOYSA-N 0.000 claims 1
• KLKQEZMEYBOCMI-UHFFFAOYSA-N 4-[3-[[6-(4,5-dichloroimidazol-1-yl)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(Cl)=C1Cl KLKQEZMEYBOCMI-UHFFFAOYSA-N 0.000 claims 1
• BWEITODKSZQYLC-UHFFFAOYSA-N 4-[3-[[6-(4-chloro-2-methylimidazol-1-yl)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NC(Cl)=CN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S BWEITODKSZQYLC-UHFFFAOYSA-N 0.000 claims 1
• PRXMTRSOZRZLCB-UHFFFAOYSA-N 4-[3-[[6-[4-(hydroxymethyl)imidazol-1-yl]pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(CO)=C1 PRXMTRSOZRZLCB-UHFFFAOYSA-N 0.000 claims 1
• WNVXGCCNACRRBU-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(5-methylpyrazol-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=CC=NN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WNVXGCCNACRRBU-UHFFFAOYSA-N 0.000 claims 1
• DRMMKXZBPFROFE-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(C(F)(F)F)=N1 DRMMKXZBPFROFE-UHFFFAOYSA-N 0.000 claims 1
• 229940123407 Androgen receptor antagonist Drugs 0.000 claims 1
• 239000003936 androgen receptor antagonist Substances 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
• 239000000243 solution Substances 0.000 description 70
• 238000005160 1H NMR spectroscopy Methods 0.000 description 69
• 239000000543 intermediate Substances 0.000 description 67
• 108010080146 androgen receptors Proteins 0.000 description 58
• 238000004519 manufacturing process Methods 0.000 description 57
• 102000001307 androgen receptors Human genes 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 43
• 210000004027 cell Anatomy 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• 239000000047 product Substances 0.000 description 38
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 33
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 31
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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• 206010028980 Neoplasm Diseases 0.000 description 29
• 208000035475 disorder Diseases 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 27
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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• 230000000052 comparative effect Effects 0.000 description 23
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• ORIQLMBUPMABDV-UHFFFAOYSA-N 6-chloropyridine-3-carbonitrile Chemical compound ClC1=CC=C(C#N)C=N1 ORIQLMBUPMABDV-UHFFFAOYSA-N 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 19
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• 230000000694 effects Effects 0.000 description 18
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• 125000004432 carbon atom Chemical group C* 0.000 description 17
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 125000000217 alkyl group Chemical group 0.000 description 15
• WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 15
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• SOZGHDCEWOLLHV-UHFFFAOYSA-N 2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#N SOZGHDCEWOLLHV-UHFFFAOYSA-N 0.000 description 10
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