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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2001
- 2001-03-07 HU HU0300068A patent/HUP0300068A2/hu unknown
- 2001-03-07 AP APAP/P/2002/002593A patent/AP1540A/en active
- 2001-03-07 IL IL15096401A patent/IL150964A0/xx unknown
- 2001-03-07 OA OA1200200295A patent/OA12323A/en unknown
- 2001-03-07 WO PCT/US2001/007094 patent/WO2001070232A1/en not_active Ceased
- 2001-03-07 CZ CZ20023168A patent/CZ20023168A3/cs unknown
- 2001-03-07 DZ DZ013318A patent/DZ3318A1/fr active
- 2001-03-07 AU AU2001243441A patent/AU2001243441B2/en not_active Ceased
- 2001-03-07 EA EA200201001A patent/EA005893B1/ru unknown
- 2001-03-07 CA CA002404206A patent/CA2404206A1/en not_active Abandoned
- 2001-03-07 PL PL01357727A patent/PL357727A1/xx not_active Application Discontinuation
- 2001-03-07 CN CN01806446A patent/CN1416346A/zh active Pending
- 2001-03-07 BR BR0109356-8A patent/BR0109356A/pt not_active IP Right Cessation
- 2001-03-07 AU AU4344101A patent/AU4344101A/xx active Pending
- 2001-03-07 MX MXPA02009305A patent/MXPA02009305A/es active IP Right Grant
- 2001-03-07 JP JP2001568430A patent/JP2003527429A/ja active Pending
- 2001-03-07 NZ NZ520588A patent/NZ520588A/en unknown
- 2001-03-07 US US10/239,343 patent/US7071184B2/en not_active Expired - Fee Related
- 2001-03-07 SK SK1363-2002A patent/SK13632002A3/sk unknown
- 2001-03-07 KR KR1020027012366A patent/KR20020082896A/ko not_active Abandoned
- 2001-03-07 EP EP01916412A patent/EP1307203A4/en not_active Withdrawn
- 2001-03-19 UY UY26625A patent/UY26625A1/es not_active Application Discontinuation
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2002
- 2002-07-29 BG BG106962A patent/BG106962A/bg unknown
- 2002-09-20 NO NO20024528A patent/NO20024528L/no not_active Application Discontinuation
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2006
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