NZ564830A - Pyrrolidine derivatives as antiviral compounds - Google Patents

Info

Publication number

NZ564830A

NZ564830A NZ564830A NZ56483006A NZ564830A NZ 564830 A NZ564830 A NZ 564830A NZ 564830 A NZ564830 A NZ 564830A NZ 56483006 A NZ56483006 A NZ 56483006A NZ 564830 A NZ564830 A NZ 564830A

Authority

NZ

New Zealand

Prior art keywords

alkyl

groups

cycloalkyl

compound

aryl

Prior art date

2005-07-14

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 262
• 230000000840 anti-viral effect Effects 0.000 title description 4
• 150000003235 pyrrolidines Chemical class 0.000 title 1
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 97
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 76
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 66
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 60
• 125000001424 substituent group Chemical group 0.000 claims abstract description 46
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 239000012453 solvate Substances 0.000 claims abstract description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• 208000005176 Hepatitis C Diseases 0.000 claims abstract description 4
• -1 enantiomers thereof Chemical class 0.000 claims description 303
• 125000000217 alkyl group Chemical group 0.000 claims description 198
• 239000000203 mixture Substances 0.000 claims description 91
• 125000000623 heterocyclic group Chemical group 0.000 claims description 80
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000003342 alkenyl group Chemical group 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 125000000304 alkynyl group Chemical group 0.000 claims description 56
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 150000002367 halogens Chemical class 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• 125000004432 carbon atom Chemical group C* 0.000 claims description 37
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 125000005842 heteroatom Chemical group 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 25
• 125000001188 haloalkyl group Chemical group 0.000 claims description 25
• 125000004104 aryloxy group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 229940124530 sulfonamide Drugs 0.000 claims description 24
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 22
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 20
• 241000282414 Homo sapiens Species 0.000 claims description 19
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
• 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 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 11
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
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• 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 10
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• IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims 1
• TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
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