ES2396761T3 - Sulfonamidas que inhiben la proteasa de VIH - Google Patents
Sulfonamidas que inhiben la proteasa de VIH Download PDFInfo
- Publication number
- ES2396761T3 ES2396761T3 ES09176641T ES09176641T ES2396761T3 ES 2396761 T3 ES2396761 T3 ES 2396761T3 ES 09176641 T ES09176641 T ES 09176641T ES 09176641 T ES09176641 T ES 09176641T ES 2396761 T3 ES2396761 T3 ES 2396761T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- alkyl
- amino
- benzyl
- sulfonyl
- Prior art date
- 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.)
- Expired - Lifetime
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- 108010010369 HIV Protease Proteins 0.000 title description 7
- 229940124530 sulfonamide Drugs 0.000 title description 2
- 150000003456 sulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 125000000217 alkyl group Chemical group 0.000 claims description 1696
- -1 cycloalkenyl alkyl Chemical group 0.000 claims description 845
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 611
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 474
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 278
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 233
- 229910003827 NRaRb Inorganic materials 0.000 claims description 209
- 125000003342 alkenyl group Chemical group 0.000 claims description 177
- 125000001424 substituent group Chemical group 0.000 claims description 162
- 125000000304 alkynyl group Chemical group 0.000 claims description 156
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 144
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 139
- 125000001072 heteroaryl group Chemical group 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 128
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 126
- 125000001188 haloalkyl group Chemical group 0.000 claims description 116
- 125000000623 heterocyclic group Chemical group 0.000 claims description 114
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 110
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 107
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 104
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 98
- 125000003545 alkoxy group Chemical group 0.000 claims description 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 150000002148 esters Chemical class 0.000 claims description 83
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 80
- 125000004043 oxo group Chemical group O=* 0.000 claims description 77
- 150000003839 salts Chemical group 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 64
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 63
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000004967 formylalkyl group Chemical group 0.000 claims description 58
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 55
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 40
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 229910052705 radium Inorganic materials 0.000 claims description 24
- 229910052701 rubidium Inorganic materials 0.000 claims description 24
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 17
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 14
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 14
- 125000005335 azido alkyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 10
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- RJRULCBXBWECCS-UHFFFAOYSA-N N-[3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]butanamide Chemical compound C(CCC)(=O)NN1C(N(CC1)CC=1N=C(SC=1)C)=O RJRULCBXBWECCS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- XZKFQDCPGMQDKU-LFBNJJMOSA-N (2s)-2-[3-(1-benzofuran-2-ylmethyl)-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2OC3=CC=CC=C3C=2)CC1)=O)CC1=CC=CC=C1 XZKFQDCPGMQDKU-LFBNJJMOSA-N 0.000 claims description 2
- NKYYDSHGWRTBDE-LFBNJJMOSA-N (2s)-2-[3-(1-benzothiophen-3-ylmethyl)-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2C3=CC=CC=C3SC=2)CC1)=O)CC1=CC=CC=C1 NKYYDSHGWRTBDE-LFBNJJMOSA-N 0.000 claims description 2
- DJONSAOXHZCLKL-QAXCHELISA-N (2s)-2-[3-[(2-acetamido-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C(NC(C)=O)SC=2)CC1)=O)CC1=CC=CC=C1 DJONSAOXHZCLKL-QAXCHELISA-N 0.000 claims description 2
- RITHNTVOHMZOON-QAXCHELISA-N (2s)-2-[3-[(2-cyclopropyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-hydroxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(O)=CC=1)NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C(SC=2)C2CC2)CC1)=O)C1=CC=CC=C1 RITHNTVOHMZOON-QAXCHELISA-N 0.000 claims description 2
- CTFHPJSRRCQJOH-PZWMIYICSA-N (2s)-2-[3-[(2-ethyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound S1C(CC)=NC(CN2C(N([C@@H](C(C)C)C(=O)N[C@@H](CC=3C=CC=CC=3)[C@H](O)CN(CC(C)C)S(=O)(=O)C=3C=CC(OC)=CC=3)CC2)=O)=C1 CTFHPJSRRCQJOH-PZWMIYICSA-N 0.000 claims description 2
- SFCNXRUPPMIRFO-UFEXNNADSA-N (2s)-2-[3-[(5-ethyl-2-phenyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@H](C(C)C)N1CCN(C1=O)CC=1N=C(SC=1CC)C=1C=CC=CC=1)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(OC)=CC=1)C1=CC=CC=C1 SFCNXRUPPMIRFO-UFEXNNADSA-N 0.000 claims description 2
- RGBJWHSSCBZNII-BEAALGTASA-N (2s)-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-2-[3-[(4-methoxyquinolin-2-yl)methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C3C=CC=CC3=C(OC)C=2)CC1)=O)CC1=CC=CC=C1 RGBJWHSSCBZNII-BEAALGTASA-N 0.000 claims description 2
- KPBFLJRZLQOIOE-PZWMIYICSA-N (2s)-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-2-[3-[[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound S1C(COC)=NC(CN2C(N([C@@H](C(C)C)C(=O)N[C@@H](CC=3C=CC=CC=3)[C@H](O)CN(CC(C)C)S(=O)(=O)C=3C=CC(OC)=CC=3)CC2)=O)=C1 KPBFLJRZLQOIOE-PZWMIYICSA-N 0.000 claims description 2
- LRRMUUORBQRNTC-DSPMFFIESA-N (2s)-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methyl-2-[2-oxo-3-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]imidazolidin-1-yl]butanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C(SC=2)C(C)C)CC1)=O)CC1=CC=CC=C1 LRRMUUORBQRNTC-DSPMFFIESA-N 0.000 claims description 2
- IYHFPUJUHXLDFR-WTGSTYHVSA-N (2s)-n-[(2s,3r)-4-[(3-amino-4-chlorophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-[(2-ethyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound S1C(CC)=NC(CN2C(N([C@@H](C(C)C)C(=O)N[C@@H](CC=3C=CC=CC=3)[C@H](O)CN(CC(C)C)S(=O)(=O)C=3C=C(N)C(Cl)=CC=3)CC2)=O)=C1 IYHFPUJUHXLDFR-WTGSTYHVSA-N 0.000 claims description 2
- PURCUOBBBWIGFT-GOVYPMRZSA-N (2s)-n-[(2s,3r)-4-[(3-amino-4-hydroxyphenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-[(2-ethyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound S1C(CC)=NC(CN2C(N([C@@H](C(C)C)C(=O)N[C@@H](CC=3C=CC=CC=3)[C@H](O)CN(CC(C)C)S(=O)(=O)C=3C=C(N)C(O)=CC=3)CC2)=O)=C1 PURCUOBBBWIGFT-GOVYPMRZSA-N 0.000 claims description 2
- HDFWEDLDVWHWFC-QAXCHELISA-N (2s)-n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-[(2-cyclopropyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C(SC=2)C2CC2)CC1)=O)C1=CC=CC=C1 HDFWEDLDVWHWFC-QAXCHELISA-N 0.000 claims description 2
- KIKUBSNQYMEVPS-WTGSTYHVSA-N (2s)-n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-[(2-ethyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl]-3-methylbutanamide Chemical compound S1C(CC)=NC(CN2C(N([C@@H](C(C)C)C(=O)N[C@@H](CC=3C=CC=CC=3)[C@H](O)CN(CC(C)C)S(=O)(=O)C=3C=CC(N)=CC=3)CC2)=O)=C1 KIKUBSNQYMEVPS-WTGSTYHVSA-N 0.000 claims description 2
- PEGSWZQYABPRRS-CXRNIHMRSA-N (2s,3s)-2-[3-[[3-[(e)-n'-hydroxycarbamimidoyl]phenyl]methyl]-2-oxoimidazolidin-1-yl]-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-3-methylpentanamide Chemical compound O=C1N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CN(CC(C)C)S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=CC(C(N)=NO)=C1 PEGSWZQYABPRRS-CXRNIHMRSA-N 0.000 claims description 2
- CFKDRWQUQPARHJ-OYPZLXDPSA-N (2s,3s)-n-[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]-2-[3-[[6-(methoxymethyl)pyridin-2-yl]methyl]-2-oxoimidazolidin-1-yl]-3-methylpentanamide Chemical compound O=C1N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CN(CC(C)C)S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=CC(COC)=N1 CFKDRWQUQPARHJ-OYPZLXDPSA-N 0.000 claims description 2
- PRKWIVKWXVTDCG-WJWXAECUSA-N (2s,3s)-n-[(2s,3r)-4-[(3-amino-4-chlorophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-(3h-benzimidazol-5-ylmethyl)-2-oxoimidazolidin-1-yl]-3-methylpentanamide Chemical compound C([C@H](NC(=O)[C@@H](N1C(N(CC=2C=C3N=CNC3=CC=2)CC1)=O)[C@@H](C)CC)[C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C(N)C(Cl)=CC=1)C1=CC=CC=C1 PRKWIVKWXVTDCG-WJWXAECUSA-N 0.000 claims description 2
- SHTKUADDCQFXKM-YKFOITPPSA-N (2s,3s)-n-[(2s,3r)-4-[(4-cyanophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-methyl-2-[2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl]pentanamide Chemical compound O=C1N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CN(CC(C)C)S(=O)(=O)C=2C=CC(=CC=2)C#N)CCN1CC1=CC=CN=C1 SHTKUADDCQFXKM-YKFOITPPSA-N 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- DMRSXVZBZNNZJG-WTGSTYHVSA-N diazonio-[[4-[[3-[(2s)-1-[[(2s,3r)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-2-oxoimidazolidin-1-yl]methyl]-1,3-thiazol-2-yl]methyl]azanide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)[C@H](C(C)C)N1C(N(CC=2N=C(CN=[N+]=[N-])SC=2)CC1)=O)CC1=CC=CC=C1 DMRSXVZBZNNZJG-WTGSTYHVSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 229950010765 pivalate Drugs 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 230000002829 reductive effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940075466 undecylenate Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/175—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine having the group, >N—C(O)—N=N— or, e.g. carbonohydrazides, carbazones, semicarbazides, semicarbazones; Thioanalogues thereof
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/733,915 US20050131042A1 (en) | 2003-12-11 | 2003-12-11 | HIV protease inhibiting compounds |
| US733915 | 2003-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2396761T3 true ES2396761T3 (es) | 2013-02-26 |
Family
ID=34653241
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09176641T Expired - Lifetime ES2396761T3 (es) | 2003-12-11 | 2004-11-10 | Sulfonamidas que inhiben la proteasa de VIH |
| ES10176829T Expired - Lifetime ES2426965T3 (es) | 2003-12-11 | 2004-11-10 | Sulfonamidas inhibidoras de la proteasa de VIH |
| ES04810802T Expired - Lifetime ES2337581T3 (es) | 2003-12-11 | 2004-11-10 | Composicion para inhibir la proteasa del vih. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10176829T Expired - Lifetime ES2426965T3 (es) | 2003-12-11 | 2004-11-10 | Sulfonamidas inhibidoras de la proteasa de VIH |
| ES04810802T Expired - Lifetime ES2337581T3 (es) | 2003-12-11 | 2004-11-10 | Composicion para inhibir la proteasa del vih. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050131042A1 (enExample) |
| EP (3) | EP2264032B1 (enExample) |
| JP (2) | JP2007513944A (enExample) |
| AT (1) | ATE452889T1 (enExample) |
| CA (2) | CA2549389A1 (enExample) |
| DE (1) | DE602004024830D1 (enExample) |
| ES (3) | ES2396761T3 (enExample) |
| MX (1) | MXPA06006610A (enExample) |
| TW (1) | TWI353833B (enExample) |
| WO (1) | WO2005061450A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2224003C (en) | 1995-06-07 | 2010-04-13 | Progenics Pharmaceuticals, Inc. | Fluorescence resonance energy transfer screening assay for the identification of hiv-1 envelope glycoprotein-medicated cell |
| US7118859B2 (en) * | 1996-01-17 | 2006-10-10 | Progenics Pharmaceuticals, Inc. | Methods for inhibiting HIV-1 infection |
| US6344545B1 (en) * | 1996-06-14 | 2002-02-05 | Progenics Pharmaceuticals, Inc. | Method for preventing HIV-1 infection of CD4+ cells |
| US7858298B1 (en) | 1996-04-01 | 2010-12-28 | Progenics Pharmaceuticals Inc. | Methods of inhibiting human immunodeficiency virus type 1 (HIV-1) infection through the administration of CCR5 chemokine receptor antagonists |
| US20080015348A1 (en) * | 1998-12-16 | 2008-01-17 | Progenics Pharmaceuticals, Inc. | Nucleic acids encoding polypeptides of anti-CCR5 antibodies |
| US20040228869A1 (en) * | 1998-12-16 | 2004-11-18 | Progenics Pharmaceuticals, Inc. | Synergistic inhibition of HIV-1 fusion and attachment, compositions and antibodies thereto |
| US7138119B2 (en) * | 2000-09-15 | 2006-11-21 | Progenics Pharmaceuticals, Inc. | Compositions and methods for inhibition of HIV-1 infection |
| US7060273B2 (en) * | 2001-04-06 | 2006-06-13 | Progenics Pharmaceuticals, Inc. | Methods for inhibiting HIV-1 infection |
| US7122185B2 (en) * | 2002-02-22 | 2006-10-17 | Progenics Pharmaceuticals, Inc. | Anti-CCR5 antibody |
| JP4803352B2 (ja) * | 2005-07-13 | 2011-10-26 | Jsr株式会社 | アミノ酸−n−カルボキシ無水物の製造方法 |
| JP2009514790A (ja) * | 2005-07-22 | 2009-04-09 | プロジェニクス・ファーマスーティカルズ・インコーポレイテッド | Hiv−1−感染患者におけるウイルス負荷を減少させる方法 |
| JP2010501583A (ja) * | 2006-08-18 | 2010-01-21 | セコイア、ファーマシューティカルズ、インコーポレイテッド | シトクロムp450を阻害するための組成物および方法 |
| JP5270943B2 (ja) * | 2008-03-28 | 2013-08-21 | 大阪瓦斯株式会社 | フルオレン誘導体およびこのフルオレン誘導体を用いたアミノ基含有フルオレン誘導体の製造方法 |
| BRPI0922366B8 (pt) | 2008-12-03 | 2021-05-25 | Presidio Pharmaceuticals Inc | composto, composição farmacêutica e uso de um composto |
| US8314250B2 (en) | 2009-11-24 | 2012-11-20 | Hoffmann-La Roche Inc. | Sultam derivatives |
| WO2014133059A1 (ja) | 2013-02-28 | 2014-09-04 | 武田薬品工業株式会社 | スルホニルクロライド化合物の製造法 |
| RU2642466C2 (ru) * | 2013-04-02 | 2018-01-25 | Аннцзи Фармасьютикал Ко., Лтд. | Многофункциональные производные хинолина в качестве антинейродегенеративных агентов |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| CN111205206B (zh) * | 2020-02-13 | 2021-10-22 | 中国医学科学院医药生物技术研究所 | 一种包含氨基酸连接链的羰基化合物或其药学上可接受的盐及其制备方法和应用 |
| CN111265499B (zh) * | 2020-02-17 | 2022-11-15 | 江苏艾立康医药科技有限公司 | 一种洛匹那韦吸入气雾剂及其制备方法 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU680635C (en) * | 1992-08-25 | 2007-05-17 | G.D. Searle Llc | Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US5723490A (en) * | 1992-09-08 | 1998-03-03 | Vertex Pharmaceuticals Incorporated | THF-containing sulfonamide inhibitors of aspartyl protease |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| ES2127938T3 (es) * | 1993-08-24 | 1999-05-01 | Searle & Co | Hidroxietilamino sulfonamidas utiles como inhibidores de proteasas retroviricas. |
| UA49803C2 (uk) * | 1994-06-03 | 2002-10-15 | Дж.Д. Сьорль Енд Ко | Спосіб лікування ретровірусних інфекцій |
| US6150556A (en) * | 1995-03-10 | 2000-11-21 | G. D. Dearle & Co. | Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5691372A (en) * | 1995-04-19 | 1997-11-25 | Vertex Pharmaceuticals Incorporated | Oxygenated-Heterocycle containing sulfonamide inhibitors of aspartyl protease |
| EP0861249A1 (en) * | 1995-11-15 | 1998-09-02 | G.D. Searle & Co. | Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5914332A (en) * | 1995-12-13 | 1999-06-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US6436989B1 (en) * | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| AU2010299A (en) * | 1997-12-24 | 1999-07-19 | Vertex Pharmaceuticals Incorporated | Prodrugs os aspartyl protease inhibitors |
| US6251906B1 (en) * | 1998-05-15 | 2001-06-26 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| GB9914821D0 (en) * | 1999-06-24 | 1999-08-25 | Glaxo Group Ltd | Compounds |
| US20020022742A1 (en) * | 2000-07-19 | 2002-02-21 | Harris Gregory D. | Salt forms of an HIV protease inhibitor |
| US6617310B2 (en) * | 2000-07-19 | 2003-09-09 | Bristol-Myers Squibb Pharma Company | Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines |
| DK1387842T3 (da) * | 2001-05-11 | 2009-08-10 | Tibotec Pharm Ltd | Bredspektrede 2-amino-benzoxazolsulfonamid-HIV-protease-inhibitorer |
| US7157489B2 (en) * | 2002-03-12 | 2007-01-02 | The Board Of Trustees Of The University Of Illinois | HIV protease inhibitors |
-
2003
- 2003-12-11 US US10/733,915 patent/US20050131042A1/en not_active Abandoned
-
2004
- 2004-11-10 ES ES09176641T patent/ES2396761T3/es not_active Expired - Lifetime
- 2004-11-10 ES ES10176829T patent/ES2426965T3/es not_active Expired - Lifetime
- 2004-11-10 CA CA002549389A patent/CA2549389A1/en not_active Abandoned
- 2004-11-10 ES ES04810802T patent/ES2337581T3/es not_active Expired - Lifetime
- 2004-11-10 WO PCT/US2004/037745 patent/WO2005061450A2/en not_active Ceased
- 2004-11-10 DE DE602004024830T patent/DE602004024830D1/de not_active Expired - Lifetime
- 2004-11-10 MX MXPA06006610A patent/MXPA06006610A/es active IP Right Grant
- 2004-11-10 EP EP10176829.9A patent/EP2264032B1/en not_active Expired - Lifetime
- 2004-11-10 EP EP09176641A patent/EP2216334B1/en not_active Expired - Lifetime
- 2004-11-10 EP EP04810802A patent/EP1709037B8/en not_active Expired - Lifetime
- 2004-11-10 CA CA2792483A patent/CA2792483A1/en not_active Abandoned
- 2004-11-10 JP JP2006543826A patent/JP2007513944A/ja active Pending
- 2004-11-10 AT AT04810802T patent/ATE452889T1/de not_active IP Right Cessation
- 2004-12-10 TW TW093138495A patent/TWI353833B/zh not_active IP Right Cessation
-
2011
- 2011-08-15 JP JP2011177726A patent/JP2012021006A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1709037A2 (en) | 2006-10-11 |
| ATE452889T1 (de) | 2010-01-15 |
| MXPA06006610A (es) | 2006-08-31 |
| EP1709037B1 (en) | 2009-12-23 |
| EP2264032A3 (en) | 2011-03-23 |
| HK1143579A1 (en) | 2011-01-07 |
| CA2792483A1 (en) | 2005-07-07 |
| TW200529811A (en) | 2005-09-16 |
| JP2012021006A (ja) | 2012-02-02 |
| JP2007513944A (ja) | 2007-05-31 |
| US20050131042A1 (en) | 2005-06-16 |
| EP2264032A2 (en) | 2010-12-22 |
| EP2216334A1 (en) | 2010-08-11 |
| ES2337581T3 (es) | 2010-04-27 |
| WO2005061450A2 (en) | 2005-07-07 |
| EP2264032B1 (en) | 2013-08-07 |
| EP1709037B8 (en) | 2010-02-17 |
| WO2005061450A3 (en) | 2005-10-20 |
| DE602004024830D1 (de) | 2010-02-04 |
| CA2549389A1 (en) | 2005-07-07 |
| TWI353833B (en) | 2011-12-11 |
| EP2216334B1 (en) | 2012-10-31 |
| ES2426965T3 (es) | 2013-10-28 |
| HK1100037A1 (en) | 2007-08-31 |
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