TW201040181A - Macrocyclic serine protease inhibitors - Google Patents

Info

Publication number

TW201040181A

TW201040181A TW099110777A TW99110777A TW201040181A TW 201040181 A TW201040181 A TW 201040181A TW 099110777 A TW099110777 A TW 099110777A TW 99110777 A TW99110777 A TW 99110777A TW 201040181 A TW201040181 A TW 201040181A

Authority

TW

Taiwan

Prior art keywords

group

compound

trifluoromethyl

thiazol

methoxy

Prior art date

2009-04-08

Links

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• Global Dossier
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• 239000003001 serine protease inhibitor Substances 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 293
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 100
• 238000000034 method Methods 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 10
• 208000015181 infectious disease Diseases 0.000 claims abstract description 9
• -1 C: block Chemical group 0.000 claims description 898
• 125000001424 substituent group Chemical group 0.000 claims description 440
• 239000000203 mixture Substances 0.000 claims description 180
• 125000000623 heterocyclic group Chemical group 0.000 claims description 172
• 125000003118 aryl group Chemical group 0.000 claims description 155
• 239000001257 hydrogen Substances 0.000 claims description 137
• 229910052739 hydrogen Inorganic materials 0.000 claims description 137
• 125000001072 heteroaryl group Chemical group 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 127
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 78
• 125000003342 alkenyl group Chemical group 0.000 claims description 75
• 125000000304 alkynyl group Chemical group 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 70
• 239000012453 solvate Substances 0.000 claims description 60
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
• 150000002431 hydrogen Chemical class 0.000 claims description 55
• 239000000651 prodrug Substances 0.000 claims description 54
• 229940002612 prodrug Drugs 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000001153 fluoro group Chemical group F* 0.000 claims description 38
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 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 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 239000007789 gas Substances 0.000 claims description 27
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 24
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 21
• 230000000155 isotopic effect Effects 0.000 claims description 21
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 20
• 229940079322 interferon Drugs 0.000 claims description 20
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 19
• 238000003786 synthesis reaction Methods 0.000 claims description 19
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
• 239000002775 capsule Substances 0.000 claims description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 16
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 14
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 150000002923 oximes Chemical class 0.000 claims description 13
• 239000002904 solvent Substances 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 239000011734 sodium Substances 0.000 claims description 12
• 229910052708 sodium Inorganic materials 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 11
• 125000002950 monocyclic group Chemical group 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000006612 decyloxy group Chemical group 0.000 claims description 10
• 229910052702 rhenium Inorganic materials 0.000 claims description 10
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
• 125000002619 bicyclic group Chemical group 0.000 claims description 9
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• 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 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 208000024891 symptom Diseases 0.000 claims description 8
• 229910052720 vanadium Inorganic materials 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
• 241000219112 Cucumis Species 0.000 claims description 7
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 7
• 241000282414 Homo sapiens Species 0.000 claims description 7
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 7
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 108010022999 Serine Proteases Proteins 0.000 claims description 6
• 102000012479 Serine Proteases Human genes 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
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• 239000002689 soil Substances 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 108010047761 Interferon-alpha Proteins 0.000 claims description 5
• 102000006992 Interferon-alpha Human genes 0.000 claims description 5
• 125000000732 arylene group Chemical group 0.000 claims description 5
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
• 125000005549 heteroarylene group Chemical group 0.000 claims description 5
• 239000003112 inhibitor Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
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• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims description 4
• PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical compound CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
• 108091005804 Peptidases Proteins 0.000 claims description 4
• 206010036790 Productive cough Diseases 0.000 claims description 4
• 239000004365 Protease Substances 0.000 claims description 4
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
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• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 4
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• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
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• YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
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• 229960000329 ribavirin Drugs 0.000 claims description 4
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
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• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
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• 229910052703 rhodium Inorganic materials 0.000 claims description 3
• 210000003802 sputum Anatomy 0.000 claims description 3
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
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• ZGVSLIJCYFJGDQ-UHFFFAOYSA-N 5-propan-2-yl-1,2-oxazole Chemical compound CC(C)C1=CC=NO1 ZGVSLIJCYFJGDQ-UHFFFAOYSA-N 0.000 claims description 2
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• 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 2
• 150000001345 alkine derivatives Chemical class 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
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• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
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• 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
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• BZFIPFGRXRRZSP-UHFFFAOYSA-N 2-propan-2-yl-1,3-thiazole Chemical compound CC(C)C1=NC=CS1 BZFIPFGRXRRZSP-UHFFFAOYSA-N 0.000 claims 3
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• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 2
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• 230000001419 dependent effect Effects 0.000 claims 2
• FIVPIPIDMRVLAY-RBJBARPLSA-N gliotoxin Chemical compound C1C2=CC=C[C@H](O)[C@H]2N2[C@]1(SS1)C(=O)N(C)[C@@]1(CO)C2=O FIVPIPIDMRVLAY-RBJBARPLSA-N 0.000 claims 2
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• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
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