JP2003530401A5 - - Google Patents

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Publication number

JP2003530401A5

JP2003530401A5 JP2001575586A JP2001575586A JP2003530401A5 JP 2003530401 A5 JP2003530401 A5 JP 2003530401A5 JP 2001575586 A JP2001575586 A JP 2001575586A JP 2001575586 A JP2001575586 A JP 2001575586A JP 2003530401 A5 JP2003530401 A5 JP 2003530401A5

Authority

JP

Japan

Prior art keywords

alkyl

conhch

aryl

compound

conr

Prior art date

2001-04-03

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.)

Granted

Links

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• 150000001875 compounds Chemical class 0.000 description 22
• 125000000217 alkyl group Chemical group 0.000 description 12
• -1 aryl-heteroaryl Chemical group 0.000 description 9
• 239000008194 pharmaceutical composition Substances 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 0 CCCC(C(C(NCC(NC(C(CC(C)C)=O)c1ccccc1)=O)=O)=O)NC(C(CCC1)N1C([C@@](CC=CC(Cc1cccc(OCCC*)c1)=*=C)C(CC1)CCC1C(O)=O)=O)=O Chemical compound CCCC(C(C(NCC(NC(C(CC(C)C)=O)c1ccccc1)=O)=O)=O)NC(C(CCC1)N1C([C@@](CC=CC(Cc1cccc(OCCC*)c1)=*=C)C(CC1)CCC1C(O)=O)=O)=O 0.000 description 5
• 241000711549 Hepacivirus C Species 0.000 description 5
• 125000002877 alkyl aryl group Chemical group 0.000 description 5
• 125000004404 heteroalkyl group Chemical group 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 108091005804 Peptidases Proteins 0.000 description 4
• 239000004365 Protease Substances 0.000 description 4
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 229910052757 nitrogen Inorganic materials 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 125000003710 aryl alkyl group Chemical group 0.000 description 3
• 239000003937 drug carrier Substances 0.000 description 3
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
• 238000000034 method Methods 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 125000004437 phosphorous atom Chemical group 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
• 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 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 102000014150 Interferons Human genes 0.000 description 2
• 108010050904 Interferons Proteins 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
• 150000005215 alkyl ethers Chemical class 0.000 description 2
• 125000005213 alkyl heteroaryl group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 239000003443 antiviral agent Substances 0.000 description 2
• 125000005110 aryl thio group Chemical group 0.000 description 2
• 125000004104 aryloxy group Chemical group 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 235000013877 carbamide Nutrition 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 229940079322 interferon Drugs 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 125000004076 pyridyl group Chemical class 0.000 description 2
• 150000003839 salts Chemical class 0.000 description 2
• 239000012453 solvate Substances 0.000 description 2
• 125000001544 thienyl group Chemical class 0.000 description 2
• 125000006725 C1-C10 alkenyl group Chemical group 0.000 description 1
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
• GGEHEYIXIKBQLC-XTFHHSQUSA-N CCC#C[C@@H](C(C(NCC(N[C@@H](C1Cc2ccccc2C1)C(N(C)C)=O)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O Chemical compound CCC#C[C@@H](C(C(NCC(N[C@@H](C1Cc2ccccc2C1)C(N(C)C)=O)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O GGEHEYIXIKBQLC-XTFHHSQUSA-N 0.000 description 1
• CNDIAFGIFQFOBC-JUBWKJJFSA-N CCCC(C(C(NCC(NC(C(OC(C)(C)C)=O)c1ccccc1)=O)=O)=O)NC(C(C[C@H](C1)OCCCCOc2cc(CC(N[C@H]3C)=O)ccc2)N1C3=O)=O Chemical compound CCCC(C(C(NCC(NC(C(OC(C)(C)C)=O)c1ccccc1)=O)=O)=O)NC(C(C[C@H](C1)OCCCCOc2cc(CC(N[C@H]3C)=O)ccc2)N1C3=O)=O CNDIAFGIFQFOBC-JUBWKJJFSA-N 0.000 description 1
• JQYOUERZBDLNBO-RPSWEREUSA-N CCCC(C(C(NCC(N[C@H](C(O)=O)c1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCCOc2cc(CC(N[C@H]3C4CCCCC4)=O)ccc2)N1C3=O)=O Chemical compound CCCC(C(C(NCC(N[C@H](C(O)=O)c1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCCOc2cc(CC(N[C@H]3C4CCCCC4)=O)ccc2)N1C3=O)=O JQYOUERZBDLNBO-RPSWEREUSA-N 0.000 description 1
• RUQJIWAEEPLRQC-OXHSURQKSA-N CCCC(CC(NCC(N[C@@H](C1Cc2ccccc2C1)C(N(C)C)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O Chemical compound CCCC(CC(NCC(N[C@@H](C1Cc2ccccc2C1)C(N(C)C)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O RUQJIWAEEPLRQC-OXHSURQKSA-N 0.000 description 1
• QKVAUVHKZPMIEL-XJUSNKPOSA-N CCCCCCCC(C(C(NCC(NCc1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OC(C)(C)CCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O Chemical compound CCCCCCCC(C(C(NCC(NCc1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OC(C)(C)CCOc2cccc(CC(N[C@H]3C4CCCCC4)=O)c2)N1C3=O)=O QKVAUVHKZPMIEL-XJUSNKPOSA-N 0.000 description 1
• GVKXBPKXZQLESA-XIARVLQKSA-N CCCC[C@@H](C(C(NCC(NC(C(N(C)C)=O)c1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C(C)(C)C)=O)c2)N1C3=O)=O Chemical compound CCCC[C@@H](C(C(NCC(NC(C(N(C)C)=O)c1ccccc1)=O)=O)=O)NC([C@H](C[C@H](C1)OCCCOc2cccc(CC(N[C@H]3C(C)(C)C)=O)c2)N1C3=O)=O GVKXBPKXZQLESA-XIARVLQKSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 102000006992 Interferon-alpha Human genes 0.000 description 1
• 108010047761 Interferon-alpha Proteins 0.000 description 1
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 description 1
• 101800001838 Serine protease/helicase NS3 Proteins 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000003282 alkyl amino group Chemical group 0.000 description 1
• 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 125000001769 aryl amino group Chemical group 0.000 description 1
• 125000005129 aryl carbonyl group Chemical group 0.000 description 1
• 150000008378 aryl ethers Chemical class 0.000 description 1
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
• UZMZVDOOVXLRID-UHFFFAOYSA-N azanylidyne-(nitrosulfonylamino)methane Chemical class [O-][N+](=O)S(=O)(=O)NC#N UZMZVDOOVXLRID-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000004965 chloroalkyl group Chemical group 0.000 description 1
• 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 150000002678 macrocyclic compounds Chemical class 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• IBGCXOFOCKCBNQ-UHFFFAOYSA-N nitro cyanate Chemical compound [O-][N+](=O)OC#N IBGCXOFOCKCBNQ-UHFFFAOYSA-N 0.000 description 1
• 125000005936 piperidyl group Chemical class 0.000 description 1
• 229960000329 ribavirin Drugs 0.000 description 1
• 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 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1