JP2003527429A5 - - Google Patents
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- JP2003527429A5 JP2003527429A5 JP2001568430A JP2001568430A JP2003527429A5 JP 2003527429 A5 JP2003527429 A5 JP 2003527429A5 JP 2001568430 A JP2001568430 A JP 2001568430A JP 2001568430 A JP2001568430 A JP 2001568430A JP 2003527429 A5 JP2003527429 A5 JP 2003527429A5
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- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- azepan
- amide
- butyl
- 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.)
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- -1 2-methanesulfinyl-ethyl Chemical group 0.000 description 160
- 125000000217 alkyl group Chemical group 0.000 description 159
- 150000001875 compounds Chemical class 0.000 description 81
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 125000004076 pyridyl group Chemical class 0.000 description 9
- 125000001544 thienyl group Chemical class 0.000 description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 8
- 125000000499 benzofuranyl group Chemical class O1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 7
- GVZXSZWCZGKLRS-UHFFFAOYSA-N thieno[3,2-b]thiophene-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(=O)O)S2 GVZXSZWCZGKLRS-UHFFFAOYSA-N 0.000 description 7
- 125000005425 toluyl group Chemical group 0.000 description 7
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001972 isopentyl group Chemical class [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
- 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 description 4
- YMZTUCZCQMQFMK-UHFFFAOYSA-N 3-methyl-1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)OC2=C1 YMZTUCZCQMQFMK-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- 108010005843 Cysteine Proteases Proteins 0.000 description 4
- 102000005927 Cysteine Proteases Human genes 0.000 description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 125000004369 butenyl group Chemical class C(=CCC)* 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000002883 imidazolyl group Chemical class 0.000 description 4
- 125000000842 isoxazolyl group Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- CNUBKCREEQZXNE-UHFFFAOYSA-N 3-methylfuro[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2C(C)=C(C(O)=O)OC2=C1 CNUBKCREEQZXNE-UHFFFAOYSA-N 0.000 description 3
- HITUZQPFDWNUHA-UHFFFAOYSA-N 5-fluoro-1-benzofuran-2-carboxylic acid Chemical compound FC1=CC=C2OC(C(=O)O)=CC2=C1 HITUZQPFDWNUHA-UHFFFAOYSA-N 0.000 description 3
- XZELWEMGWISCTP-UHFFFAOYSA-N 5-methoxy-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=C2OC(C(O)=O)=CC2=C1 XZELWEMGWISCTP-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C(*)N*)=O Chemical compound CC(C(*)N*)=O 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- POVDISSTLXBPFJ-GBAJDQEWSA-N benzyl (2r,5s,6s)-6-hydroxy-2-methyl-5-[[(2s)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]azepane-1-carboxylate Chemical compound C1[C@H](O)[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)CC[C@@H](C)N1C(=O)OCC1=CC=CC=C1 POVDISSTLXBPFJ-GBAJDQEWSA-N 0.000 description 3
- VREBIURYOUWZMM-UHFFFAOYSA-N benzyl 2-methyl-2,3,4,7-tetrahydroazepine-1-carboxylate Chemical compound CC1CCC=CCN1C(=O)OCC1=CC=CC=C1 VREBIURYOUWZMM-UHFFFAOYSA-N 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- JNMCOUZTZNWVRG-QPSCCSFWSA-N tert-butyl n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O JNMCOUZTZNWVRG-QPSCCSFWSA-N 0.000 description 3
- XXCUAXLYCFIIJD-ZDUSSCGKSA-N (2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CCC1CCCCC1 XXCUAXLYCFIIJD-ZDUSSCGKSA-N 0.000 description 2
- LTNPMUWQBBVAFH-AWEZNQCLSA-N (2s)-2-(4-cyclohexylbutanoylamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CCCC1CCCCC1 LTNPMUWQBBVAFH-AWEZNQCLSA-N 0.000 description 2
- DYJYPZWDPSSQCC-HNNXBMFYSA-N (2s)-2-(5-cyclohexylpentanoylamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CCCCC1CCCCC1 DYJYPZWDPSSQCC-HNNXBMFYSA-N 0.000 description 2
- BGTMQOCNIPZFBH-LBPRGKRZSA-N (2s)-2-[(2-cyclohexylacetyl)amino]-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CC1CCCCC1 BGTMQOCNIPZFBH-LBPRGKRZSA-N 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- VONNOORMGBWECM-HOJAQTOUSA-N 3-methyl-n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]furo[3,2-b]pyridine-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C1=C(C2=NC=CC=C2O1)C)CC(C)C)S(=O)(=O)C1=CC=CC=N1 VONNOORMGBWECM-HOJAQTOUSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- OWFRWTPPOZSWLL-UHFFFAOYSA-N 5,6-difluoro-1-benzofuran-2-carboxylic acid Chemical compound FC1=C(F)C=C2OC(C(=O)O)=CC2=C1 OWFRWTPPOZSWLL-UHFFFAOYSA-N 0.000 description 2
- GMIDGDXRCTUPNM-UHFFFAOYSA-N 5-fluoro-3-methyl-1-benzofuran-2-carboxylic acid Chemical compound C1=C(F)C=C2C(C)=C(C(O)=O)OC2=C1 GMIDGDXRCTUPNM-UHFFFAOYSA-N 0.000 description 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 241000224466 Giardia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 2
- 241000223109 Trypanosoma cruzi Species 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- DGEXKPJDVGYJKO-BNOWGMLFSA-N benzyl (1r,4r,7s)-4-methyl-8-oxa-5-azabicyclo[5.1.0]octane-5-carboxylate Chemical compound C([C@@H]1O[C@@H]1CC[C@H]1C)N1C(=O)OCC1=CC=CC=C1 DGEXKPJDVGYJKO-BNOWGMLFSA-N 0.000 description 2
- CJKVNTNBIZCKJD-XBFCOCLRSA-N benzyl (2r,5s,6s)-5-amino-6-hydroxy-2-methylazepane-1-carboxylate Chemical compound C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCC1=CC=CC=C1 CJKVNTNBIZCKJD-XBFCOCLRSA-N 0.000 description 2
- BOHJFEPUSOTHGO-XBFCOCLRSA-N benzyl (2r,5s,6s)-5-azido-6-hydroxy-2-methylazepane-1-carboxylate Chemical compound C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCC1=CC=CC=C1 BOHJFEPUSOTHGO-XBFCOCLRSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 2
- 125000001041 indolyl group Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 2
- 201000004792 malaria Diseases 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- HLBWPWATDURSJJ-WSWWRLHASA-N n-[(2s)-1-[[(3r,4r,7s)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound N1([C@@H](C)CC[C@H]([C@@H](C1)O)NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 HLBWPWATDURSJJ-WSWWRLHASA-N 0.000 description 2
- HLBWPWATDURSJJ-GBAJDQEWSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 HLBWPWATDURSJJ-GBAJDQEWSA-N 0.000 description 2
- BWYBBMQLUKXECQ-GIVPXCGWSA-N n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 BWYBBMQLUKXECQ-GIVPXCGWSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 2
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
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- GURJLSFZKPBFSI-CRBWNDHFSA-N tert-butyl n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-2-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound O[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)CC[C@@H](C)NC1S(=O)(=O)C1=CC=CC=N1 GURJLSFZKPBFSI-CRBWNDHFSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- IPCCAASWTRQQGQ-GJGLBJJNSA-N (2r)-2-[[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-oxoazepane-1-carbonyl]amino]-4-methylpentanoic acid Chemical compound O=C1CN(C(=O)N[C@H](CC(C)C)C(O)=O)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 IPCCAASWTRQQGQ-GJGLBJJNSA-N 0.000 description 1
- CHAYLTJYSWEUAP-XCRWMPKNSA-N (2r)-4-methyl-n-[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]-2-(3-phenylphenyl)pentanamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@H](CC(C)C)C=1C=C(C=CC=1)C=1C=CC=CC=1)S(=O)(=O)C1=CC=CC=N1 CHAYLTJYSWEUAP-XCRWMPKNSA-N 0.000 description 1
- PDDREXKZULOTIF-COPCDDAFSA-N (2r,5s)-5-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-2-methyl-n-(oxan-4-yl)-6-oxoazepane-1-carboxamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)C(=O)NC1CCOCC1 PDDREXKZULOTIF-COPCDDAFSA-N 0.000 description 1
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Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020128476A1 (en) * | 1996-08-08 | 2002-09-12 | Smithkline Beecham Corporation | Inhibitors of cysteine protease |
| US20030144175A1 (en) | 1998-12-23 | 2003-07-31 | Smithkline Beecham Corporation | Protease inhibitors |
| JP2003513971A (ja) | 1999-11-10 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | プロテア−ゼ阻害剤 |
| EP1229914A4 (en) | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| US6583137B1 (en) | 1999-11-10 | 2003-06-24 | Smithkline Beecham Corporation | Protease inhibitors |
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| CO5280088A1 (es) * | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Inhibidores de proteasa |
| CO5280093A1 (es) * | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Metodos de tratamiento |
| JP2004509083A (ja) * | 2000-09-01 | 2004-03-25 | スミスクライン・ビーチャム・コーポレイション | 治療方法 |
| CA2436850A1 (en) * | 2000-11-22 | 2003-07-03 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2003045909A2 (en) * | 2001-11-21 | 2003-06-05 | Smithkline Beecham Corporation | Methods and intermediates for the synthesis of azepines |
| WO2003097593A2 (en) * | 2002-05-22 | 2003-11-27 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1551823A1 (en) * | 2002-10-08 | 2005-07-13 | Merck Frosst Canada Inc. | 4-amino-azepan-3-one compounds as cathepsin k inhibitors useful in the treatment of osteoporosis |
| US20040192674A1 (en) * | 2003-02-14 | 2004-09-30 | Marquis Robert W. | Cathepsin L inhibitors |
| US20080262224A1 (en) * | 2004-01-23 | 2008-10-23 | Smithkline Beecham Corporation | Method of Preparation of Benzofuran-2-Carboxylic Acid -Amide |
| KR100603014B1 (ko) * | 2004-07-21 | 2006-07-24 | 황호연 | 라벨용 포장필름의 제조방법, 상기 제조방법으로 제조된라벨용 포장필름 및 상기 포장필름의 사용방법 |
| AU2005294123C1 (en) * | 2004-10-07 | 2010-01-21 | Vitae Pharmaceuticals, Inc. | Diaminoalkane aspartic protease inhibitors |
| PE20070171A1 (es) | 2005-06-30 | 2007-03-08 | Boehringer Ingelheim Int | GLICINAMIDAS SUSTITUIDAS CON EFECTO ANTITROMBOTICO E INHIBIDOR DEL FACTOR Xa |
| TWI411607B (zh) * | 2005-11-14 | 2013-10-11 | Vitae Pharmaceuticals Inc | 天門冬胺酸蛋白酶抑制劑 |
| CL2007002689A1 (es) * | 2006-09-18 | 2008-04-18 | Vitae Pharmaceuticals Inc | Compuestos derivados de piperidin-1-carboxamida, inhibidores de la renina; compuestos intermediarios; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como hipertension, insuficiencia cardiaca, fibrosis cardiaca, entre otras. |
| KR20100023948A (ko) | 2007-06-08 | 2010-03-04 | 닛뽕 케미파 가부시키가이샤 | 뇌동맥류의 치료 또는 예방약 |
| EP2167609A1 (en) * | 2007-06-20 | 2010-03-31 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
| WO2008156817A2 (en) * | 2007-06-20 | 2008-12-24 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
| JPWO2009054454A1 (ja) | 2007-10-24 | 2011-03-03 | 国立大学法人 東京医科歯科大学 | カテプシン阻害剤を有効成分として含有するＴｏｌｌ様受容体のシグナル伝達の調整剤 |
| EP2719700A1 (en) | 2008-01-09 | 2014-04-16 | Amura Therapeutics Limited | Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases |
| JP2011525488A (ja) * | 2008-06-20 | 2011-09-22 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | レニン阻害剤およびその使用方法 |
| CN102088850A (zh) * | 2008-06-26 | 2011-06-08 | 生命医药公司 | 甲基2-((r)-(3-氯苯基)((r)-1-((s)-2-(甲氨基)-3((r)-四氢-2h-吡喃-3-基)丙基氨甲酰基)哌啶-3-基)甲氧基)氨基甲酸乙酯的盐 |
| AR077692A1 (es) * | 2009-08-06 | 2011-09-14 | Vitae Pharmaceuticals Inc | Sales de 2-((r)-(3-clorofenil) ((r)-1-((s) -2-(metilamino)-3-((r)-tetrahidro-2h-piran-3-il) propilcarbamoil) piperidin -3-il) metoxi) etilcarbamato de metilo |
| CN103687593B (zh) | 2011-05-16 | 2016-09-28 | 拜耳知识产权有限责任公司 | 组织蛋白酶k抑制用于治疗和/或预防肺动脉高压和/或心力衰竭的用途 |
| CN103275070A (zh) * | 2013-05-10 | 2013-09-04 | 郑彪 | 调节单核细胞增殖的四环化合物及其应用 |
| EP3009444B1 (en) * | 2013-06-14 | 2017-12-20 | Seikagaku Corporation | Alpha-oxoacyl amino-caprolactam derivative |
| JP6226437B2 (ja) * | 2013-06-14 | 2017-11-08 | 生化学工業株式会社 | α−オキソアシルアミノカプロラクタム体 |
| CN109983012B (zh) | 2016-09-16 | 2023-12-01 | 莱特豪斯制药公司 | 赖氨酸牙龈蛋白酶的酮抑制剂 |
| BR112022019245A2 (pt) * | 2020-03-26 | 2022-11-16 | Glaxosmithkline Ip Dev Ltd | Inibidores de catepsina para prevenir ou tratar infecções virais |
Family Cites Families (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038247A (en) * | 1970-05-19 | 1977-07-26 | Ciba-Geigy Corporation | Stabilizing polyolefins with diacyl dihydrazides |
| US5142056A (en) * | 1989-05-23 | 1992-08-25 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US5057525A (en) * | 1981-10-01 | 1991-10-15 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl) benzamide derivatives |
| IT1195287B (it) * | 1981-11-05 | 1988-10-12 | Ausonia Farma Srl | Derivato tiazolico,procedimento per la sua preparazione e relative composizioni farmaceutiche |
| ZA829141B (en) | 1981-12-14 | 1983-09-28 | Merck & Co Inc | Process for reducing lactams |
| ZA839532B (en) | 1982-12-27 | 1985-08-28 | Merck & Co Inc | Lactams and bicyclic lactams as antihypertensive agents |
| US4518528A (en) * | 1983-05-19 | 1985-05-21 | Rasnick David W | α Amino fluoro ketones |
| US4749792A (en) * | 1984-09-26 | 1988-06-07 | E. R. Squibb & Sons, Inc. | Diamino ketones and alcohols as analgesic agents |
| US4638101A (en) | 1985-01-02 | 1987-01-20 | General Electric Company | Compositions |
| US4638010A (en) * | 1985-02-28 | 1987-01-20 | E. R. Squibb & Sons, Inc. | Ester substituted aminoalkanoylureido amino and imino acid and ester compounds |
| JP2570686B2 (ja) | 1985-12-23 | 1997-01-08 | 日産化学工業株式会社 | ピラゾ−ル誘導体 |
| DE3600288A1 (de) | 1986-01-08 | 1987-07-16 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonylharnstoff-derivaten |
| ATE63906T1 (de) | 1986-03-14 | 1991-06-15 | Syntex Inc | 3,5-disubstituierte 4,5-dihydroisoxazole als transglutaminasehemmer. |
| DE3618004A1 (de) | 1986-05-28 | 1987-12-03 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonyliso(thio)-harnstoff-derivaten |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| US4994471A (en) * | 1989-05-12 | 1991-02-19 | Boc, Inc. | N-aryl-N-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
| UA41251C2 (uk) | 1990-01-04 | 2001-09-17 | Пфайзер, Інк. | Гідровані азотвмісні гетероциклічні сполуки, похідні піперидину, фармацевтична композиція та спосіб пригнічення активності речовини р в організмі |
| GB9019558D0 (en) | 1990-09-07 | 1990-10-24 | Szelke Michael | Enzyme inhibitors |
| EP0504938A3 (en) | 1991-03-22 | 1993-04-14 | Suntory Limited | Prophylactic and therapeutic agent for bone diseases comprising di- or tripeptide derivative as active ingredient |
| JP3190431B2 (ja) | 1991-07-01 | 2001-07-23 | 三菱化学株式会社 | ケトン誘導体 |
| JPH05140063A (ja) | 1991-11-19 | 1993-06-08 | Suntory Ltd | ジペプチド誘導体及びそれを有効成分とする骨疾患の予防及び治療剤 |
| US5216168A (en) * | 1992-04-01 | 1993-06-01 | G. D. Searle & Co. | 2- and 3- amino and azido derivatives of 1,5-iminosugars |
| US5206251A (en) * | 1992-04-01 | 1993-04-27 | G. D. Searle & Co. | 2- and 3- amino and azido derivatives of 1,5-iminosugars |
| JPH09500087A (ja) | 1992-06-24 | 1997-01-07 | コーテックス ファーマシューティカルズ インコーポレイテッド | カルパイン活性の増大に関連した健康障害の抑制及び処置におけるカルパイン阻害剤の使用法 |
| US5374623A (en) | 1992-08-20 | 1994-12-20 | Prototek, Inc. | Cysteine protease inhibitors effective for in vivo use |
| CA2111930A1 (en) * | 1992-12-25 | 1994-06-26 | Ryoichi Ando | Aminoketone derivatives |
| DE69321087T2 (de) * | 1992-12-25 | 1999-05-20 | Mitsubishi Chemical Corp., Tokio/Tokyo | Alpha-aminoketon Derivate |
| JPH06199850A (ja) * | 1992-12-28 | 1994-07-19 | Tanabe Seiyaku Co Ltd | インドール含有ペプチド及びその製法 |
| JP2848232B2 (ja) | 1993-02-19 | 1999-01-20 | 武田薬品工業株式会社 | アルデヒド誘導体 |
| CA2159080A1 (en) | 1993-04-06 | 1994-10-13 | Philip Stashenko | Human osteoclast-specific and -related genes |
| TW494094B (en) | 1993-04-29 | 2002-07-11 | Vertex Pharma | Peptide analogs as irreversible interleukin-1β protease inhibitors and pharmaceutical compositions comprising the same |
| WO1995005192A1 (en) | 1993-08-13 | 1995-02-23 | Merck & Co., Inc. | SUBSTITUTED KETONE DERIVATIVES AS INHIBITORS OF INTERLEUKIN-1β CONVERTING ENZYME |
| US5501969A (en) | 1994-03-08 | 1996-03-26 | Human Genome Sciences, Inc. | Human osteoclast-derived cathepsin |
| EP0753003B1 (en) | 1994-04-13 | 1999-06-16 | Takeda Chemical Industries, Ltd. | Aziridine derivatives, their production and use |
| US5585387A (en) | 1994-10-07 | 1996-12-17 | Torcan Chemical Ltd. | Prepration of cisapride |
| US6544767B1 (en) | 1994-10-27 | 2003-04-08 | Axys Pharmaceuticals, Inc. | Cathespin O2 protease |
| US5734977A (en) * | 1994-11-10 | 1998-03-31 | Telefonaktiebolaget Lm Ericsson | Fraud detection in radio communications network |
| TW438591B (en) | 1995-06-07 | 2001-06-07 | Arris Pharm Corp | Reversible cysteine protease inhibitors |
| HUP9802488A3 (en) | 1995-10-30 | 2001-10-29 | Smithkline Beecham Corp | Method of inhibiting cathepsin k |
| SK56798A3 (en) | 1995-10-30 | 1998-12-02 | Smithkline Beecham Corp | Protease inhibitors, pharmaceutical composition containing them and their use |
| US6083947A (en) * | 1996-01-29 | 2000-07-04 | The Regents Of The University Of California | Method for treating sexual dysfunctions |
| US5902882A (en) | 1996-04-17 | 1999-05-11 | Hoffmann-La Roche Inc. | Assymetric synthesis of azepines |
| WO1997049668A1 (en) | 1996-06-13 | 1997-12-31 | Smithkline Beecham Corporation | Inhibitiors of cysteine protease |
| AU6333296A (en) | 1996-06-14 | 1998-01-07 | Human Genome Sciences, Inc. | Cathepsin k gene |
| US5861298A (en) * | 1996-06-17 | 1999-01-19 | Smithkline Beecham Corporation | Cathepsin K gene |
| DZ2285A1 (fr) | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
| US5830850A (en) * | 1996-08-28 | 1998-11-03 | Mount Sinai School Of Medicine Of The City Of New York | Methods for the treatment of bone resorption disorders, including osteoporosis |
| EP0923535A4 (en) | 1996-08-28 | 2001-01-10 | Smithkline Beecham Corp | CYSTEINE PROTEASE INHIBITORS |
| AU718055B2 (en) | 1996-09-19 | 2000-04-06 | Aventisub Ii Inc. | 3-mercaptoacetylamino-1,5-substituted-2-oxo-azepan derivatives useful as inhibitors of matrix metalloproteinase |
| US5948669A (en) | 1997-02-26 | 1999-09-07 | Smithkline Beecham Corporation | Rat cathepsin K polynucleotide and polypeptide sequence |
| AR012374A1 (es) | 1997-04-15 | 2000-10-18 | Smithkline Beecham Corp | Inhibidores de proteasas, composiones farmaceuticas y usos para la preparacion de medicamentos. |
| EP0977743A1 (en) | 1997-04-25 | 2000-02-09 | Smithkline Beecham | Protease inhibitors |
| MA26487A1 (fr) | 1997-04-29 | 2004-12-20 | Smithkline Beecham Corp | Heterocyclecetohydrazides inhibiteurs de proteases, procede pour leur preparation et compositions pharmaceutiques les contenant . |
| US6566373B2 (en) * | 1997-05-06 | 2003-05-20 | Smithkline Beecham Corporation | Protease inhibitors |
| CA2289602A1 (en) | 1997-05-08 | 1998-11-12 | William Edward Bondinell | Protease inhibitors |
| WO1998050534A1 (en) * | 1997-05-08 | 1998-11-12 | Smithkline Beecham Corporation | Protease inhibitors |
| MA26540A1 (fr) | 1997-09-04 | 2004-12-20 | Smithkline Beecham Corp | Composes nouveaux inhibiteurs de proteases et compositions pharmaceutiques les contenant. |
| MA26618A1 (fr) | 1998-04-09 | 2004-12-20 | Smithkline Beecham Corp | Composes et compositions pharmaceutiques pour le traitement du paludisme |
| DZ2796A1 (fr) | 1998-05-21 | 2003-12-01 | Smithkline Beecham Corp | Composés à fonction bis-aminométhyl-carbonyle nouveaux, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| CA2332492A1 (en) | 1998-05-21 | 1999-11-25 | Stacie Marie Halbert | Protease inhibitors |
| DZ2815A1 (fr) | 1998-06-12 | 2003-12-01 | Smithkline Beecham Corp | Inhibiteurs de protéase. |
| AR018915A1 (es) | 1998-06-24 | 2001-12-12 | Smithkline Beecham Corp | Inhibidores de proteasas diacilhidrazinicos, composicion farmaceutica que la comprenden, usos de los mismos para la manufactura de un medicamento, unprocedimiento de fabricacion de dichos compuestos |
| JP2003527819A (ja) | 1998-08-14 | 2003-09-24 | スミスクライン・ビーチャム・コーポレイション | カテプシンｋの阻害方法 |
| CO5150165A1 (es) | 1998-11-13 | 2002-04-29 | Smithkline Beecham Plc | Inhibidores de proteasa: tipo catepsina k |
| WO2000038687A1 (en) * | 1998-12-23 | 2000-07-06 | Smithkline Beecham Corporation | Protease inhibitors |
| US20030044399A1 (en) | 1998-12-23 | 2003-03-06 | Smithkline Beecham Corporation | Method of treatment |
| CO5180541A1 (es) | 1998-12-23 | 2002-07-30 | Smithkline Beechman Corp | Inhibidores de proteasa del tipo de 1,3-diaminocetonas con anillo de 8-14 miembros |
| AU756174B2 (en) | 1999-02-09 | 2003-01-09 | Bristol-Myers Squibb Company | Lactam inhibitors of FXa and method |
| DZ3083A1 (fr) | 1999-02-19 | 2004-06-02 | Smithkline Beecham Corp | Composés nouveaux inhibiteurs de protéases, procédé pour leur préparation et compositions pharmaceutiques les conentant. |
| UY26026A1 (es) | 1999-03-16 | 2000-10-31 | Smithkline Beecham Corportion | Inhibidores de proteasas |
| UY26088A1 (es) | 1999-03-31 | 2000-10-31 | Smithkline Beecham Corp | Inhibidores de proteasas |
| SK1182002A3 (en) | 1999-07-28 | 2002-11-06 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl compounds |
| WO2001034154A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034566A2 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1231922A4 (en) | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| JP2003513971A (ja) | 1999-11-10 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | プロテア−ゼ阻害剤 |
| WO2001034565A2 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1233771A4 (en) | 1999-11-10 | 2003-05-14 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| WO2001034160A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| US6583137B1 (en) * | 1999-11-10 | 2003-06-24 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1229914A4 (en) | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| JP2003513926A (ja) | 1999-11-10 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | プロテアーゼ阻害剤 |
| JP2003513925A (ja) | 1999-11-10 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | プロテア−ゼ阻害剤 |
| JP2003513921A (ja) | 1999-11-10 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | プロテア−ゼ阻害剤 |
| DE10004572A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma | Neue positive allosterische AMPA-Rezeptor Modulatoren (PAARM), Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| KR20020082896A (ko) | 2000-03-21 | 2002-10-31 | 스미스클라인 비참 코포레이션 | 프로테아제 억제제 |
| US20030114437A1 (en) | 2002-10-17 | 2003-06-19 | Cummings Maxwell D. | Protease inhibitors |
| JP2004509083A (ja) | 2000-09-01 | 2004-03-25 | スミスクライン・ビーチャム・コーポレイション | 治療方法 |
| CA2436850A1 (en) | 2000-11-22 | 2003-07-03 | Smithkline Beecham Corporation | Protease inhibitors |
| US20040034013A1 (en) * | 2001-04-17 | 2004-02-19 | Cummings Maxwell D | Methods of treatment |
| EP1401453A4 (en) | 2001-05-17 | 2005-04-06 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| WO2003026770A1 (en) | 2001-09-24 | 2003-04-03 | Smithkline Beecham Corporation | Method for removing metal from the products of olefin metathesis reactions |
| WO2003045909A2 (en) | 2001-11-21 | 2003-06-05 | Smithkline Beecham Corporation | Methods and intermediates for the synthesis of azepines |
| WO2003097593A2 (en) | 2002-05-22 | 2003-11-27 | Smithkline Beecham Corporation | Protease inhibitors |
| US20050203084A1 (en) | 2002-05-22 | 2005-09-15 | Jeong Jae U. | Protease inhibitors |
| WO2003103574A2 (en) | 2002-05-22 | 2003-12-18 | Smithkline Beecham Corporation | Protease inhibitors |
| AU2003233642A1 (en) | 2002-05-22 | 2003-12-12 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2003104257A2 (en) | 2002-05-22 | 2003-12-18 | Smithkline Beecham Corporation | Protease inhibitors |
| US20050030912A1 (en) | 2002-08-22 | 2005-02-10 | Enikia L.L.C. | Use of hybrid (HW/DSP/MCU/SW) architectures for powerline OFDM communication field |
| WO2005013909A2 (en) | 2003-08-07 | 2005-02-17 | Smithkline Beecham Corporation | Novel cathepsin k inhibitors |
| US7366462B2 (en) | 2003-10-24 | 2008-04-29 | Qualcomm Incorporated | Method and apparatus for seamlessly switching reception between multimedia streams in a wireless communication system |
-
2001
- 2001-03-07 KR KR1020027012366A patent/KR20020082896A/ko not_active Abandoned
- 2001-03-07 US US10/239,343 patent/US7071184B2/en not_active Expired - Fee Related
- 2001-03-07 EA EA200201001A patent/EA005893B1/ru unknown
- 2001-03-07 JP JP2001568430A patent/JP2003527429A/ja active Pending
- 2001-03-07 SK SK1363-2002A patent/SK13632002A3/sk unknown
- 2001-03-07 CZ CZ20023168A patent/CZ20023168A3/cs unknown
- 2001-03-07 EP EP01916412A patent/EP1307203A4/en not_active Withdrawn
- 2001-03-07 PL PL01357727A patent/PL357727A1/xx not_active Application Discontinuation
- 2001-03-07 CA CA002404206A patent/CA2404206A1/en not_active Abandoned
- 2001-03-07 AU AU4344101A patent/AU4344101A/xx active Pending
- 2001-03-07 WO PCT/US2001/007094 patent/WO2001070232A1/en not_active Ceased
- 2001-03-07 NZ NZ520588A patent/NZ520588A/en unknown
- 2001-03-07 AP APAP/P/2002/002593A patent/AP1540A/en active
- 2001-03-07 AU AU2001243441A patent/AU2001243441B2/en not_active Ceased
- 2001-03-07 BR BR0109356-8A patent/BR0109356A/pt not_active IP Right Cessation
- 2001-03-07 IL IL15096401A patent/IL150964A0/xx unknown
- 2001-03-07 CN CN01806446A patent/CN1416346A/zh active Pending
- 2001-03-07 HU HU0300068A patent/HUP0300068A2/hu unknown
- 2001-03-07 OA OA1200200295A patent/OA12323A/en unknown
- 2001-03-07 DZ DZ013318A patent/DZ3318A1/fr active
- 2001-03-07 MX MXPA02009305A patent/MXPA02009305A/es active IP Right Grant
- 2001-03-19 UY UY26625A patent/UY26625A1/es not_active Application Discontinuation
- 2001-03-21 AR ARP010101323A patent/AR032877A1/es not_active Application Discontinuation
- 2001-03-21 MY MYPI20011339A patent/MY141596A/en unknown
- 2001-03-21 PE PE2001000259A patent/PE20011233A1/es not_active Application Discontinuation
-
2002
- 2002-07-29 BG BG106962A patent/BG106962A/bg unknown
- 2002-09-20 NO NO20024528A patent/NO20024528L/no not_active Application Discontinuation
-
2006
- 2006-04-25 US US11/410,558 patent/US7563784B2/en not_active Expired - Fee Related
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