TW201014855A - Compounds for the treatment of hepatitis C - Google Patents

Info

Publication number

TW201014855A

TW201014855A TW098130826A TW98130826A TW201014855A TW 201014855 A TW201014855 A TW 201014855A TW 098130826 A TW098130826 A TW 098130826A TW 98130826 A TW98130826 A TW 98130826A TW 201014855 A TW201014855 A TW 201014855A

Authority

TW

Taiwan

Prior art keywords

group

solvent

phenyl

alkyl

minutes

Prior art date

2008-09-11

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 102
• 238000011282 treatment Methods 0.000 title claims description 11
• 208000005176 Hepatitis C Diseases 0.000 title claims description 3
• 239000000203 mixture Substances 0.000 claims abstract description 108
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 162
• 125000000217 alkyl group Chemical group 0.000 claims description 114
• -1 functional Chemical group 0.000 claims description 109
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 99
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 239000001257 hydrogen Substances 0.000 claims description 89
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 78
• 235000005152 nicotinamide Nutrition 0.000 claims description 50
• 239000011570 nicotinamide Substances 0.000 claims description 50
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 239000007789 gas Substances 0.000 claims description 18
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 8
• 150000003857 carboxamides Chemical class 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000000524 functional group Chemical group 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 3
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• 229910052707 ruthenium Inorganic materials 0.000 claims description 2
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
• XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 claims 1
• 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
• 150000007857 hydrazones Chemical class 0.000 claims 1
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
• 125000005429 oxyalkyl group Chemical group 0.000 claims 1
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• 125000005888 tetrahydroindolyl group Chemical group 0.000 claims 1
• 241000711549 Hepacivirus C Species 0.000 abstract description 68
• 238000000034 method Methods 0.000 abstract description 48
• 230000000694 effects Effects 0.000 abstract description 23
• 239000002904 solvent Substances 0.000 description 820
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 400
• 229910001868 water Inorganic materials 0.000 description 339
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 262
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 260
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 238
• 235000019439 ethyl acetate Nutrition 0.000 description 187
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 187
• 239000000243 solution Substances 0.000 description 182
• 239000007788 liquid Substances 0.000 description 146
• 238000004458 analytical method Methods 0.000 description 141
• 230000014759 maintenance of location Effects 0.000 description 130
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 116
• 238000004090 dissolution Methods 0.000 description 114
• 238000005160 1H NMR spectroscopy Methods 0.000 description 91
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 83
• 239000005695 Ammonium acetate Substances 0.000 description 77
• 235000019257 ammonium acetate Nutrition 0.000 description 77
• 229940043376 ammonium acetate Drugs 0.000 description 77
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 75
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
• 238000002953 preparative HPLC Methods 0.000 description 70
• 239000007787 solid Substances 0.000 description 69
• 229910052796 boron Inorganic materials 0.000 description 64
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
• 239000003643 water by type Substances 0.000 description 55
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 54
• 238000006243 chemical reaction Methods 0.000 description 50
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 49
• 238000005481 NMR spectroscopy Methods 0.000 description 44
• 238000002360 preparation method Methods 0.000 description 43
• 239000012074 organic phase Substances 0.000 description 41
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 38
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
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• 239000007821 HATU Substances 0.000 description 32
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• 239000000047 product Substances 0.000 description 28
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• 235000011152 sodium sulphate Nutrition 0.000 description 27
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 26
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• 238000003756 stirring Methods 0.000 description 13
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