JP2003527429A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
- Authority
- 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.)
- Pending
Links
- -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
- 150000003839 salts Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical class [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
- 125000000335 thiazolyl group Chemical class 0.000 description 2
- 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
- TZWRURYXESGTNF-PVSGBFIBSA-N (2r,5s,6s)-5-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-6-hydroxy-2-methyl-n-(oxan-4-yl)azepane-1-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)C(=O)NC1CCOCC1 TZWRURYXESGTNF-PVSGBFIBSA-N 0.000 description 1
- JPZHEVLSVZULPL-PUHATCMVSA-N (2s)-2-(3-cyclohexylpropanoylamino)-4-methyl-n-[(4s,7r)-7-methyl-1-(morpholine-4-carbonyl)-3-oxoazepan-4-yl]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H]1C(CN([C@H](C)CC1)C(=O)N1CCOCC1)=O)C(=O)CCC1CCCCC1 JPZHEVLSVZULPL-PUHATCMVSA-N 0.000 description 1
- JKWNULHYCPCEQM-KAMZKSLDSA-N (2s)-2-(3-cyclohexylpropanoylamino)-n-[(3s,4s,7r)-3-hydroxy-7-methyl-1-(morpholine-4-carbonyl)azepan-4-yl]-4-methylpentanamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H]1[C@H](CN([C@H](C)CC1)C(=O)N1CCOCC1)O)C(=O)CCC1CCCCC1 JKWNULHYCPCEQM-KAMZKSLDSA-N 0.000 description 1
- CUHKGCOOPJFXOX-GBAJDQEWSA-N (2s)-2-[[(2r,5s)-5-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-2-methyl-6-oxoazepane-1-carbonyl]amino]-4-methylpentanoic acid Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(O)=O)CC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 CUHKGCOOPJFXOX-GBAJDQEWSA-N 0.000 description 1
- IPCCAASWTRQQGQ-AKQSQHNNSA-N (2s)-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-AKQSQHNNSA-N 0.000 description 1
- DUAYBRFNHNPANE-DLTYFMDKSA-N (2s)-4-methyl-2-[[(2r,5s)-2-methyl-5-[[(2s)-4-methyl-2-(quinoline-8-carbonylamino)pentanoyl]amino]-6-oxoazepane-1-carbonyl]amino]pentanoic acid Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(O)=O)CC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC=CC2=CC=CN=C12 DUAYBRFNHNPANE-DLTYFMDKSA-N 0.000 description 1
- DTSFMZBNMLHBQM-BWZBUEFSSA-N (3r,4ar,8ar)-2,3,4a,5,6,7,8,8a-octahydrobenzo[b][1,4]dioxine-3-carboxylic acid Chemical compound C1CCC[C@H]2O[C@@H](C(=O)O)CO[C@@H]21 DTSFMZBNMLHBQM-BWZBUEFSSA-N 0.000 description 1
- YGLSNFANPZJKDM-GTNVEZLYSA-N (3r,4ar,8ar)-n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-methylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[b][1,4]dioxine-3-carboxamide Chemical compound O=C([C@@H](NC(=O)[C@@H]1O[C@@H]2CCCC[C@H]2OC1)CC(C)C)N[C@H]1CC[C@@H](C)N(S(C)(=O)=O)C[C@@H]1O YGLSNFANPZJKDM-GTNVEZLYSA-N 0.000 description 1
- QVIKGEPIBIFRCI-GGAORHGYSA-N 1-(3-cyclohexylpropanoylamino)-n-[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]cyclohexane-1-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1(NC(=O)CCC2CCCCC2)CCCCC1 QVIKGEPIBIFRCI-GGAORHGYSA-N 0.000 description 1
- TUUIDAXGGZVJPJ-UHFFFAOYSA-N 1-(3-cyclohexylpropanoylamino)cyclohexane-1-carboxylic acid Chemical compound C1CCCCC1CCC(=O)NC1(C(=O)O)CCCCC1 TUUIDAXGGZVJPJ-UHFFFAOYSA-N 0.000 description 1
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MYDSAMPAYOLUMG-UHFFFAOYSA-N 3-aminothieno[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2C(N)=C(C(O)=O)SC2=C1 MYDSAMPAYOLUMG-UHFFFAOYSA-N 0.000 description 1
- HMLVZLLDKBQVFU-UHFFFAOYSA-N 3-methyl-1-pyridin-2-ylsulfonyl-2,3,4,7-tetrahydroazepine Chemical compound C1C(C)CC=CCN1S(=O)(=O)C1=CC=CC=N1 HMLVZLLDKBQVFU-UHFFFAOYSA-N 0.000 description 1
- OCZVQLJXCRTSQR-UHFFFAOYSA-N 3-methyl-5-pyridin-2-ylsulfonyl-8-oxa-5-azabicyclo[5.1.0]octane Chemical compound C1C(C)CC2OC2CN1S(=O)(=O)C1=CC=CC=N1 OCZVQLJXCRTSQR-UHFFFAOYSA-N 0.000 description 1
- LQUYFDBMLKEUQK-QIJUGHKUSA-N 3-methyl-n-[(2s)-4-methyl-1-[[(4r,6r)-6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@H](C)C[C@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C2=C(C3=CC=CC=C3O2)C)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 LQUYFDBMLKEUQK-QIJUGHKUSA-N 0.000 description 1
- LQUYFDBMLKEUQK-NYVOZVTQSA-N 3-methyl-n-[(2s)-4-methyl-1-[[(4s,6s)-6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C)C[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C2=C(C3=CC=CC=C3O2)C)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 LQUYFDBMLKEUQK-NYVOZVTQSA-N 0.000 description 1
- LOWRYOOFNUMMMS-QUCCMNQESA-N 3-methyl-n-[1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]carbamoyl]cyclohexyl]furo[3,2-b]pyridine-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1(NC(=O)C2=C(C3=NC=CC=C3O2)C)CCCCC1 LOWRYOOFNUMMMS-QUCCMNQESA-N 0.000 description 1
- KIJSABJSBHATSA-UHFFFAOYSA-N 4-amino-6-methyl-1-pyridin-2-ylsulfonylazepan-3-ol Chemical compound C1C(C)CC(N)C(O)CN1S(=O)(=O)C1=CC=CC=N1 KIJSABJSBHATSA-UHFFFAOYSA-N 0.000 description 1
- VIMGDNCXJJETFK-UHFFFAOYSA-N 4-azido-5-methyl-1-pyridin-2-ylsulfonylazepan-3-ol Chemical compound C1C(O)C(N=[N+]=[N-])C(C)CCN1S(=O)(=O)C1=CC=CC=N1 VIMGDNCXJJETFK-UHFFFAOYSA-N 0.000 description 1
- ODXCLJWFBLQBLB-SEPFQZFQSA-N 5-fluoro-n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]sulfonylazepan-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=C(F)C=C2C=1)CC(C)C)S(=O)(=O)C1=CC=C(C(F)(F)F)C=N1 ODXCLJWFBLQBLB-SEPFQZFQSA-N 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- SWLUYNCBZBOISE-NYVOZVTQSA-N 5-methoxy-n-[(2s)-4-methyl-1-[[(4s,6s)-6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C)C[C@@H](C(C1)=O)NC(=O)[C@H](CC(C)C)NC(=O)C=2OC3=CC=C(C=C3C=2)OC)N1S(=O)(=O)C1=CC=CC=N1 SWLUYNCBZBOISE-NYVOZVTQSA-N 0.000 description 1
- 208000000230 African Trypanosomiasis Diseases 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- NLWTVTQPVWREAA-UHFFFAOYSA-N CCc1cc(-c2ncccc2)ccc1 Chemical compound CCc1cc(-c2ncccc2)ccc1 NLWTVTQPVWREAA-UHFFFAOYSA-N 0.000 description 1
- 108090000625 Cathepsin K Proteins 0.000 description 1
- 102000004171 Cathepsin K Human genes 0.000 description 1
- 208000024699 Chagas disease Diseases 0.000 description 1
- 241000223935 Cryptosporidium Species 0.000 description 1
- 241000053763 Cystosoma Species 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 241000223924 Eimeria Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 241000222722 Leishmania <genus> Species 0.000 description 1
- 241000222732 Leishmania major Species 0.000 description 1
- 241000222734 Leishmania mexicana Species 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 241000243985 Onchocerca volvulus Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 241000203992 Spirometra Species 0.000 description 1
- 241000223996 Toxoplasma Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- CNVXGUFWSFAATI-GIVPXCGWSA-N benzyl (2r,5s)-2-methyl-5-[[(2s)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-6-oxoazepane-1-carboxylate Chemical compound C1C(=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 CNVXGUFWSFAATI-GIVPXCGWSA-N 0.000 description 1
- POVDISSTLXBPFJ-JWYYUFOWSA-N benzyl (2r,5s)-6-hydroxy-2-methyl-5-[[(2s)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]azepane-1-carboxylate Chemical compound C1C(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-JWYYUFOWSA-N 0.000 description 1
- POVDISSTLXBPFJ-WSWWRLHASA-N benzyl (2s,5r,6r)-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-WSWWRLHASA-N 0.000 description 1
- DGEXKPJDVGYJKO-UHFFFAOYSA-N benzyl 4-methyl-8-oxa-5-azabicyclo[5.1.0]octane-5-carboxylate Chemical compound CC1CCC2OC2CN1C(=O)OCC1=CC=CC=C1 DGEXKPJDVGYJKO-UHFFFAOYSA-N 0.000 description 1
- CJKVNTNBIZCKJD-UHFFFAOYSA-N benzyl 5-amino-6-hydroxy-2-methylazepane-1-carboxylate Chemical compound CC1CCC(N)C(O)CN1C(=O)OCC1=CC=CC=C1 CJKVNTNBIZCKJD-UHFFFAOYSA-N 0.000 description 1
- BOHJFEPUSOTHGO-UHFFFAOYSA-N benzyl 5-azido-6-hydroxy-2-methylazepane-1-carboxylate Chemical compound CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCC1=CC=CC=C1 BOHJFEPUSOTHGO-UHFFFAOYSA-N 0.000 description 1
- NTUAECGJTISEEG-SECBINFHSA-N benzyl n-[(2r)-1-iodopropan-2-yl]carbamate Chemical compound IC[C@@H](C)NC(=O)OCC1=CC=CC=C1 NTUAECGJTISEEG-SECBINFHSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 108010007459 falcipain Proteins 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000029080 human African trypanosomiasis Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- FJRLTYWBVMHIEK-YGZJECHCSA-N methyl (2r)-2-[[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-hydroxyazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound OC1CN(C(=O)N[C@H](CC(C)C)C(=O)OC)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 FJRLTYWBVMHIEK-YGZJECHCSA-N 0.000 description 1
- HFDMIAOFNFHWBY-JTGIGXABSA-N methyl (2r)-2-[[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-oxoazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound O=C1CN(C(=O)N[C@H](CC(C)C)C(=O)OC)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 HFDMIAOFNFHWBY-JTGIGXABSA-N 0.000 description 1
- UTRSYXQWBXHXAM-SWUCNREESA-N methyl (2s)-2-[[(2r,5s)-5-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-2-methyl-6-oxoazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(=O)OC)CC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 UTRSYXQWBXHXAM-SWUCNREESA-N 0.000 description 1
- XNXVERWDYCAITK-FFYZIMEISA-N methyl (2s)-2-[[(2r,5s,6s)-5-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-6-hydroxy-2-methylazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(=O)OC)C[C@H](O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 XNXVERWDYCAITK-FFYZIMEISA-N 0.000 description 1
- JZQPLGSFZLVQFW-GWCXRDAXSA-N methyl (2s)-2-[[(2r,5s,6s)-6-hydroxy-2-methyl-5-[[(2s)-4-methyl-2-(quinoline-8-carbonylamino)pentanoyl]amino]azepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(=O)OC)C[C@H](O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC=CC2=CC=CN=C12 JZQPLGSFZLVQFW-GWCXRDAXSA-N 0.000 description 1
- FJRLTYWBVMHIEK-NULCOVKLSA-N methyl (2s)-2-[[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-hydroxyazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound OC1CN(C(=O)N[C@@H](CC(C)C)C(=O)OC)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 FJRLTYWBVMHIEK-NULCOVKLSA-N 0.000 description 1
- HFDMIAOFNFHWBY-QIFDKBNDSA-N methyl (2s)-2-[[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-oxoazepane-1-carbonyl]amino]-4-methylpentanoate Chemical compound O=C1CN(C(=O)N[C@@H](CC(C)C)C(=O)OC)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 HFDMIAOFNFHWBY-QIFDKBNDSA-N 0.000 description 1
- DTVMGWFDATVKNB-OCFYOKIWSA-N methyl (2s)-4-methyl-2-[[(2r,5s)-2-methyl-5-[[(2s)-4-methyl-2-(quinoline-8-carbonylamino)pentanoyl]amino]-6-oxoazepane-1-carbonyl]amino]pentanoate Chemical compound C1C[C@@H](C)N(C(=O)N[C@@H](CC(C)C)C(=O)OC)CC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC=CC2=CC=CN=C12 DTVMGWFDATVKNB-OCFYOKIWSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- YOKZGBTWYOITAR-TWHAJKEOSA-N n-[(2s)-1-[[(3r,4r,6r)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound C([C@H](C)C[C@H]([C@@H](C1)O)NC(=O)[C@@H](NC(=O)C2=C(C3=CC=CC=C3O2)C)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 YOKZGBTWYOITAR-TWHAJKEOSA-N 0.000 description 1
- BZXUYHZBHCBSNU-TWHAJKEOSA-N n-[(2s)-1-[[(3r,4r,6r)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound C([C@H](C)C[C@H]([C@@H](C1)O)NC(=O)[C@H](CC(C)C)NC(=O)C=2OC3=CC=C(C=C3C=2)OC)N1S(=O)(=O)C1=CC=CC=N1 BZXUYHZBHCBSNU-TWHAJKEOSA-N 0.000 description 1
- HLBWPWATDURSJJ-PSWRPDDJSA-N n-[(2s)-1-[[(3r,4r,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-PSWRPDDJSA-N 0.000 description 1
- YKQLUBVFTWXVKZ-YRXWBPOGSA-N n-[(2s)-1-[[(3s,4r,6r)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]thieno[3,2-b]thiophene-5-carboxamide Chemical compound C([C@H](C)C[C@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=2SC=3C=CSC=3C=2)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 YKQLUBVFTWXVKZ-YRXWBPOGSA-N 0.000 description 1
- PPUQTCGWPDHECK-QESAQDPVSA-N n-[(2s)-1-[[(3s,4s,6s)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound C([C@@H](C)C[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=2SC3=CC=CC=C3C=2)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 PPUQTCGWPDHECK-QESAQDPVSA-N 0.000 description 1
- YOKZGBTWYOITAR-QGQQZZQASA-N n-[(2s)-1-[[(3s,4s,6s)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C)C[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C2=C(C3=CC=CC=C3O2)C)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 YOKZGBTWYOITAR-QGQQZZQASA-N 0.000 description 1
- YKQLUBVFTWXVKZ-VJANTYMQSA-N n-[(2s)-1-[[(3s,4s,6s)-3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]thieno[3,2-b]thiophene-5-carboxamide Chemical compound C([C@@H](C)C[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=2SC=3C=CSC=3C=2)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 YKQLUBVFTWXVKZ-VJANTYMQSA-N 0.000 description 1
- JIQADHMEGICIFY-GBAJDQEWSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-(morpholine-4-carbonyl)azepan-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)C(=O)N1CCOCC1 JIQADHMEGICIFY-GBAJDQEWSA-N 0.000 description 1
- VYCCAIKPKRJQAS-MNAPGUCWSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]sulfonylazepan-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=C(C(F)(F)F)C=N1 VYCCAIKPKRJQAS-MNAPGUCWSA-N 0.000 description 1
- CSYVZYDNOMNAFB-HZEGPAAWSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-propylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)C[C@H](O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 CSYVZYDNOMNAFB-HZEGPAAWSA-N 0.000 description 1
- OMXVKCTUUWGNLE-PVSGBFIBSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H]([C@H](C1)O)NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)S(=O)(=O)C1=CC=CC=N1 OMXVKCTUUWGNLE-PVSGBFIBSA-N 0.000 description 1
- GGIODQTUMIZFGW-RYCFVGSHSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoline-3-carboxamide Chemical compound N1([C@H](C)CC[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=1C=C2C=CC=CC2=NC=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 GGIODQTUMIZFGW-RYCFVGSHSA-N 0.000 description 1
- HNSQBCJDIUTWJN-VPJOFFEXSA-N n-[(2s)-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H]([C@H](C1)O)NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 HNSQBCJDIUTWJN-VPJOFFEXSA-N 0.000 description 1
- HLBWPWATDURSJJ-QESAQDPVSA-N n-[(2s)-1-[[(3s,4s,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-QESAQDPVSA-N 0.000 description 1
- RIBLUARFWJLRNJ-DLTYFMDKSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)C[C@H](O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC1CCCCC1 RIBLUARFWJLRNJ-DLTYFMDKSA-N 0.000 description 1
- IGEBYMPQDUNVAF-HZEGPAAWSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)C[C@H](O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC=CC=1)CC1CCCCC1 IGEBYMPQDUNVAF-HZEGPAAWSA-N 0.000 description 1
- XBBJFQFWHWGREC-MNAPGUCWSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C1C[C@@H](C)N(CCC)C[C@H](O)[C@H]1NC(=O)[C@@H](NC(=O)C1=CSC=C1)CC1CCCCC1 XBBJFQFWHWGREC-MNAPGUCWSA-N 0.000 description 1
- RUSJOFHLLFKWHU-OCFYOKIWSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(C[C@@H]1O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC2=CC=CC=C2C=1)C1CCCCC1 RUSJOFHLLFKWHU-OCFYOKIWSA-N 0.000 description 1
- USYWWKYLABZBMN-DLTYFMDKSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]-3-methylfuro[3,2-b]pyridine-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(C[C@@H]1O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C1=C(C2=NC=CC=C2O1)C)C1CCCCC1 USYWWKYLABZBMN-DLTYFMDKSA-N 0.000 description 1
- QYHXVJAZBXKHED-GBAJDQEWSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(C[C@@H]1O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC=CC=1)C1CCCCC1 QYHXVJAZBXKHED-GBAJDQEWSA-N 0.000 description 1
- WKYZBYGOWFSHJZ-PVSGBFIBSA-N n-[(2s)-3-cyclohexyl-1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(C[C@@H]1O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C1=CSC=C1)C1CCCCC1 WKYZBYGOWFSHJZ-PVSGBFIBSA-N 0.000 description 1
- STPXQTSZFAJCCI-OIBXWCBGSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC1CCCCC1 STPXQTSZFAJCCI-OIBXWCBGSA-N 0.000 description 1
- JXHNSRQLBAFBHR-HOJAQTOUSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC=CC=1)CC1CCCCC1 JXHNSRQLBAFBHR-HOJAQTOUSA-N 0.000 description 1
- IWXKVAKADOQHIQ-QMMLZNLJSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C1=CSC=C1)CC1CCCCC1 IWXKVAKADOQHIQ-QMMLZNLJSA-N 0.000 description 1
- VPVGADBLERRTAG-QDSKXPNFSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC2=CC=CC=C2C=1)C1CCCCC1 VPVGADBLERRTAG-QDSKXPNFSA-N 0.000 description 1
- OFMCZBXSKSFLHH-OIBXWCBGSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]-3-methylfuro[3,2-b]pyridine-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C1=C(C2=NC=CC=C2O1)C)C1CCCCC1 OFMCZBXSKSFLHH-OIBXWCBGSA-N 0.000 description 1
- KZCODYXMOKIMLT-GIVPXCGWSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC=CC=1)C1CCCCC1 KZCODYXMOKIMLT-GIVPXCGWSA-N 0.000 description 1
- FDRDFLBEJPBZRA-COPCDDAFSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C1=CSC=C1)C1CCCCC1 FDRDFLBEJPBZRA-COPCDDAFSA-N 0.000 description 1
- LBCGIKORTZAZTM-SQNIBIBYSA-N n-[(2s)-4,4-dimethyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)(C)C)C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1=CC=CO1 LBCGIKORTZAZTM-SQNIBIBYSA-N 0.000 description 1
- YRQAJYFCFIUZSE-NEWSRXKRSA-N n-[(2s)-4,4-dimethyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]thiophene-3-carboxamide Chemical compound N([C@@H](CC(C)(C)C)C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C=1C=CSC=1 YRQAJYFCFIUZSE-NEWSRXKRSA-N 0.000 description 1
- SXZXINNPZKFXOV-NRSPTQNISA-N n-[(2s)-4-methyl-1-[[(4r,6r)-6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound C([C@H](C)C[C@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=2SC3=CC=CC=C3C=2)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 SXZXINNPZKFXOV-NRSPTQNISA-N 0.000 description 1
- BWYBBMQLUKXECQ-NRSPTQNISA-N n-[(2s)-4-methyl-1-[[(4r,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-NRSPTQNISA-N 0.000 description 1
- BWYBBMQLUKXECQ-TYPHKJRUSA-N n-[(2s)-4-methyl-1-[[(4r,7s)-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-TYPHKJRUSA-N 0.000 description 1
- SXZXINNPZKFXOV-JBACZVJFSA-N n-[(2s)-4-methyl-1-[[(4s,6s)-6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound C([C@@H](C)C[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=2SC3=CC=CC=C3C=2)CC(C)C)N1S(=O)(=O)C1=CC=CC=N1 SXZXINNPZKFXOV-JBACZVJFSA-N 0.000 description 1
- XAEFPCRSTXMTJA-QMMLZNLJSA-N n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-[5-(trifluoromethyl)pyridin-2-yl]sulfonylazepan-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=C(C(F)(F)F)C=N1 XAEFPCRSTXMTJA-QMMLZNLJSA-N 0.000 description 1
- GEPPKURZODOQJJ-HOJAQTOUSA-N n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 GEPPKURZODOQJJ-HOJAQTOUSA-N 0.000 description 1
- TUCHPHMJJDUWLH-YGOYIFOWSA-N n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]quinoline-3-carboxamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=1C=C2C=CC=CC2=NC=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 TUCHPHMJJDUWLH-YGOYIFOWSA-N 0.000 description 1
- KOHHLWMNTXZYOM-COPCDDAFSA-N n-[(2s)-4-methyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound N1([C@H](C)CC[C@@H](C(C1)=O)NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)S(=O)(=O)C1=CC=CC=N1 KOHHLWMNTXZYOM-COPCDDAFSA-N 0.000 description 1
- BWYBBMQLUKXECQ-JBACZVJFSA-N n-[(2s)-4-methyl-1-[[(4s,7s)-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-JBACZVJFSA-N 0.000 description 1
- YAUUTUXLZAGMCN-XGKIILMVSA-N n-[(3r,4r,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]-4-methyl-2-(3-phenylphenyl)pentanamide Chemical compound N1([C@H](C)CC[C@H]([C@@H](C1)O)NC(=O)C(CC(C)C)C=1C=C(C=CC=1)C=1C=CC=CC=1)S(=O)(=O)C1=CC=CC=N1 YAUUTUXLZAGMCN-XGKIILMVSA-N 0.000 description 1
- LDKSYBHFKPEBEK-NPAAKHOSSA-N n-[(3s,4s,7r)-1-(cyclohexylmethyl)-3-hydroxy-7-methylazepan-4-yl]-1-(3-cyclohexylpropanoylamino)cyclohexane-1-carboxamide Chemical compound N([C@H]1CC[C@H](N(C[C@@H]1O)CC1CCCCC1)C)C(=O)C1(NC(=O)CCC2CCCCC2)CCCCC1 LDKSYBHFKPEBEK-NPAAKHOSSA-N 0.000 description 1
- MEOOYFQGWKAPBI-BVAGGSTKSA-N n-[(4s,7r)-1-(cyclohexylmethyl)-7-methyl-3-oxoazepan-4-yl]-1-(3-cyclohexylpropanoylamino)cyclohexane-1-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1=O)CC1CCCCC1)C)C(=O)C1(NC(=O)CCC2CCCCC2)CCCCC1 MEOOYFQGWKAPBI-BVAGGSTKSA-N 0.000 description 1
- RXNMSPOIOOUCPW-ZODMCCGTSA-N n-[1-[[(3s,4s,7r)-1-(cyclohexylmethyl)-3-hydroxy-7-methylazepan-4-yl]carbamoyl]cyclohexyl]-1-benzofuran-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(C[C@@H]1O)CC1CCCCC1)C)C(=O)C1(NC(=O)C=2OC3=CC=CC=C3C=2)CCCCC1 RXNMSPOIOOUCPW-ZODMCCGTSA-N 0.000 description 1
- SXVFJGGGFFAYPZ-HJNYFJLDSA-N n-[1-[[(3s,4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]carbamoyl]cyclohexyl]-1-benzofuran-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(C[C@@H]1O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1(NC(=O)C=2OC3=CC=CC=C3C=2)CCCCC1 SXVFJGGGFFAYPZ-HJNYFJLDSA-N 0.000 description 1
- JHVBDUGYTWTWBN-QPPBQGQZSA-N n-[1-[[(4s,7r)-1-(cyclohexylmethyl)-7-methyl-3-oxoazepan-4-yl]carbamoyl]cyclohexyl]-1-benzofuran-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1=O)CC1CCCCC1)C)C(=O)C1(NC(=O)C=2OC3=CC=CC=C3C=2)CCCCC1 JHVBDUGYTWTWBN-QPPBQGQZSA-N 0.000 description 1
- HNVGXTNVRQRJDX-LGWYJFNUSA-N n-[1-[[(4s,7r)-3-hydroxy-7-methyl-1-pyridin-2-ylsulfonylazepan-4-yl]carbamoyl]cyclohexyl]-3-methylfuro[3,2-b]pyridine-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1(NC(=O)C2=C(C3=NC=CC=C3O2)C)CCCCC1 HNVGXTNVRQRJDX-LGWYJFNUSA-N 0.000 description 1
- SFBZZCYKACGZCM-CTNGQTDRSA-N n-[1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]carbamoyl]cyclohexyl]-1-benzofuran-2-carboxamide Chemical compound N([C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)C(=O)C1(NC(=O)C=2OC3=CC=CC=C3C=2)CCCCC1 SFBZZCYKACGZCM-CTNGQTDRSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000003177 ocular onchocerciasis Diseases 0.000 description 1
- 208000002042 onchocerciasis Diseases 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DUPBILVWMPJNKH-UHFFFAOYSA-N pyridine;sulfur dioxide Chemical group O=S=O.C1=CC=NC=C1 DUPBILVWMPJNKH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ODHZURYHOKTGAY-VVXOGMOBSA-N tert-butyl n-[(2s)-1-[(3-hydroxy-6-methyl-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound C1C(O)C(NC(=O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)CC(C)CN1S(=O)(=O)C1=CC=CC=N1 ODHZURYHOKTGAY-VVXOGMOBSA-N 0.000 description 1
- PJGONEXTSXVJPE-FYZZASKESA-N tert-butyl n-[(2s)-1-[[(3r,4r,7s)-1-(benzenesulfonyl)-3-hydroxy-7-methylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate 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)N1S(=O)(=O)C1=CC=CC=C1 PJGONEXTSXVJPE-FYZZASKESA-N 0.000 description 1
- JNMCOUZTZNWVRG-LJISPDSOSA-N tert-butyl n-[(2s)-1-[[(3r,4r,7s)-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-LJISPDSOSA-N 0.000 description 1
- PJGONEXTSXVJPE-HZEGPAAWSA-N tert-butyl n-[(2s)-1-[[(3s,4s,7r)-1-(benzenesulfonyl)-3-hydroxy-7-methylazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate 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)N1S(=O)(=O)C1=CC=CC=C1 PJGONEXTSXVJPE-HZEGPAAWSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19100000P | 2000-03-21 | 2000-03-21 | |
| US60/191,000 | 2000-03-21 | ||
| US20634100P | 2000-05-23 | 2000-05-23 | |
| US60/206,341 | 2000-05-23 | ||
| US21175900P | 2000-06-14 | 2000-06-14 | |
| US60/211,759 | 2000-06-14 | ||
| US21744500P | 2000-07-10 | 2000-07-10 | |
| US60/217,445 | 2000-07-10 | ||
| PCT/US2001/007094 WO2001070232A1 (en) | 2000-03-21 | 2001-03-07 | Protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003527429A JP2003527429A (ja) | 2003-09-16 |
| JP2003527429A5 true JP2003527429A5 (OSRAM) | 2008-05-01 |
Family
ID=27497873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001568430A Pending JP2003527429A (ja) | 2000-03-21 | 2001-03-07 | プロテアーゼ阻害物質 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7071184B2 (OSRAM) |
| EP (1) | EP1307203A4 (OSRAM) |
| JP (1) | JP2003527429A (OSRAM) |
| KR (1) | KR20020082896A (OSRAM) |
| CN (1) | CN1416346A (OSRAM) |
| AP (1) | AP1540A (OSRAM) |
| AR (1) | AR032877A1 (OSRAM) |
| AU (2) | AU4344101A (OSRAM) |
| BG (1) | BG106962A (OSRAM) |
| BR (1) | BR0109356A (OSRAM) |
| CA (1) | CA2404206A1 (OSRAM) |
| CZ (1) | CZ20023168A3 (OSRAM) |
| DZ (1) | DZ3318A1 (OSRAM) |
| EA (1) | EA005893B1 (OSRAM) |
| HU (1) | HUP0300068A2 (OSRAM) |
| IL (1) | IL150964A0 (OSRAM) |
| MX (1) | MXPA02009305A (OSRAM) |
| MY (1) | MY141596A (OSRAM) |
| NO (1) | NO20024528L (OSRAM) |
| NZ (1) | NZ520588A (OSRAM) |
| OA (1) | OA12323A (OSRAM) |
| PE (1) | PE20011233A1 (OSRAM) |
| PL (1) | PL357727A1 (OSRAM) |
| SK (1) | SK13632002A3 (OSRAM) |
| UY (1) | UY26625A1 (OSRAM) |
| WO (1) | WO2001070232A1 (OSRAM) |
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 |
| AU1474801A (en) | 1999-11-10 | 2001-06-06 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1232155A4 (en) | 1999-11-10 | 2002-11-20 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| EP1232154A4 (en) | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| BR0109356A (pt) | 2000-03-21 | 2003-06-03 | Smithkline Beecham Corp | Inibidores de protease |
| CO5280093A1 (es) * | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Metodos de tratamiento |
| CO5280088A1 (es) * | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Inhibidores de proteasa |
| WO2002017924A1 (en) * | 2000-09-01 | 2002-03-07 | Smithkline Beecham Corporation | Method of treatment |
| BR0115473A (pt) * | 2000-11-22 | 2004-09-28 | Smithkline Beecham Corp | Inibidores de protease |
| WO2003045909A2 (en) * | 2001-11-21 | 2003-06-05 | Smithkline Beecham Corporation | Methods and intermediates for the synthesis of azepines |
| EP1511745A4 (en) * | 2002-05-22 | 2006-11-15 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| US20060166966A1 (en) * | 2002-10-08 | 2006-07-27 | Cameron Black | 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 |
| JP2007520491A (ja) * | 2004-01-23 | 2007-07-26 | スミスクライン・ビーチャム・コーポレイション | ベンゾフラン−２−カルボン酸｛（ｓ）−３−メチル−１−［（４ｓ，７ｒ）−７−メチル−３−オキソ−１−（ピリジン−２−スルホニル）−アゼパン−４−イルカルバモイル］−ブチル｝−アミドの製造方法 |
| KR100603014B1 (ko) * | 2004-07-21 | 2006-07-24 | 황호연 | 라벨용 포장필름의 제조방법, 상기 제조방법으로 제조된라벨용 포장필름 및 상기 포장필름의 사용방법 |
| WO2006042150A1 (en) * | 2004-10-07 | 2006-04-20 | 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. |
| CN101970007A (zh) | 2007-06-08 | 2011-02-09 | 日本化学医药株式会社 | 脑动脉瘤的治疗或预防药 |
| EP2170815A2 (en) * | 2007-06-20 | 2010-04-07 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
| WO2009096996A1 (en) * | 2007-06-20 | 2009-08-06 | Smithkline Beecham Corporation | Renin inhibitors |
| US20100331545A1 (en) | 2007-10-24 | 2010-12-30 | Nippon Chemiphar Co., Ltd. | Regulator for signaling toll-like receptor, which comprises cathepsin inhibitor as active ingredient |
| EP2719700A1 (en) | 2008-01-09 | 2014-04-16 | Amura Therapeutics Limited | Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases |
| CA2727987A1 (en) * | 2008-06-20 | 2009-12-23 | Vitae Pharmaceuticals, Inc. | Renin inhibitors and method of use thereof |
| 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 |
| 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 |
| EP3009444B1 (en) * | 2013-06-14 | 2017-12-20 | Seikagaku Corporation | Alpha-oxoacyl amino-caprolactam derivative |
| EP4480541A3 (en) | 2016-09-16 | 2025-04-30 | Lighthouse Pharmaceuticals, Inc. | Ketone inhibitors of lysine gingipain |
| CN116194114A (zh) * | 2020-03-26 | 2023-05-30 | 葛兰素史密斯克莱知识产权发展有限公司 | 用于防止或治疗病毒感染的组织蛋白酶抑制剂 |
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 |
| JPS62252779A (ja) | 1986-03-14 | 1987-11-04 | シンテツクス（ユ−・エス・エイ）インコ−ポレイテツド | トランスグルタミナ−ゼ阻害剤 |
| 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 |
| WO1991009844A1 (en) | 1990-01-04 | 1991-07-11 | Pfizer Inc. | Substance p antagonists |
| 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 |
| AU4544993A (en) | 1992-06-24 | 1994-01-24 | Cortex Pharmaceuticals, Inc. | Use of calpain inhibitors in the inhibition and treatment of medical conditions associated with increased calpain activity |
| US5374623A (en) | 1992-08-20 | 1994-12-20 | Prototek, Inc. | Cysteine protease inhibitors effective for in vivo use |
| ATE171171T1 (de) | 1992-12-25 | 1998-10-15 | Mitsubishi Chem Corp | Alpha-aminoketon derivate |
| CA2111930A1 (en) | 1992-12-25 | 1994-06-26 | Ryoichi Ando | Aminoketone derivatives |
| 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 |
| WO1994023033A1 (en) | 1993-04-06 | 1994-10-13 | Forsyth Dental Infirmary For Children | Human osteoclast-specific and -related genes |
| CA2122227A1 (en) | 1993-04-29 | 1994-10-30 | Roland E. Dolle | Peptide analogs as irreversible interleukin-1.beta. protease inhibitors |
| US5866545A (en) | 1993-08-13 | 1999-02-02 | 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 |
| AU2223595A (en) | 1994-04-13 | 1995-11-10 | 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 |
| CA2209109A1 (en) | 1995-10-30 | 1997-05-09 | Thomas Joseph . Carr | Method of inhibiting cathepsin k |
| JP2000500742A (ja) | 1995-10-30 | 2000-01-25 | 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 |
| 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. |
| WO1998008802A1 (en) | 1996-08-28 | 1998-03-05 | Smithkline Beecham Corporation | Inhibitors of cysteine protease |
| 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 |
| NZ334490A (en) | 1996-09-19 | 2000-08-25 | Hoechst Marion Roussel Inc | 3-mercaptoacetylamino-1,5-substituted-2-oxo-azepan derivatives 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. |
| PE68599A1 (es) | 1997-04-25 | 1999-09-26 | Smithkline Beecham Corp | Inhibidores de proteasas |
| 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 |
| HUP0002951A3 (en) | 1997-05-08 | 2002-10-28 | Smithkline Beecham Corp | Bis-aminomethylcarbonyl compounds as protease inhibitors and pharmaceutical compositions containing them |
| AU7288598A (en) | 1997-05-08 | 1998-11-27 | 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 |
| MA26631A1 (fr) | 1998-05-21 | 2004-12-20 | Smithkline Beecham Corp | Composes a fonction bis-aminomethyl-carbonyle nouveaux, procede pour leur preparation et compositions pharmaceutiques les contenant |
| AU9110298A (en) | 1998-05-21 | 1999-12-06 | Smithkline Beecham Corporation | 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 |
| WO2000009653A2 (en) | 1998-08-14 | 2000-02-24 | Smithkline Beecham Corporation | Method of inhibiting cathepsin k |
| CO5150165A1 (es) | 1998-11-13 | 2002-04-29 | Smithkline Beecham Plc | Inhibidores de proteasa: tipo catepsina k |
| 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 |
| CN1253441C (zh) * | 1998-12-23 | 2006-04-26 | 史密丝克莱恩比彻姆公司 | 蛋白酶抑制剂 |
| US20030044399A1 (en) | 1998-12-23 | 2003-03-06 | Smithkline Beecham Corporation | Method of treatment |
| EP1175405A4 (en) | 1999-02-09 | 2002-05-15 | Bristol Myers Squibb Co | LACTAM INHIBITORS OF FACTOR Xa AND ASSOCIATED 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 |
| JP4829449B2 (ja) | 1999-07-28 | 2011-12-07 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 置換オキソアザヘテロシクリル化合物 |
| EP1232155A4 (en) | 1999-11-10 | 2002-11-20 | 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 |
| EP1232154A4 (en) | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| AU1474701A (en) | 1999-11-10 | 2001-06-06 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034154A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034153A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034157A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| JP2003513928A (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 |
| JP2003513956A (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 |
| JP2003513927A (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 |
| AU1474801A (en) * | 1999-11-10 | 2001-06-06 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034155A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| 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 |
| BR0109356A (pt) * | 2000-03-21 | 2003-06-03 | Smithkline Beecham Corp | Inibidores de protease |
| US20030114437A1 (en) | 2002-10-17 | 2003-06-19 | Cummings Maxwell D. | Protease inhibitors |
| WO2002017924A1 (en) | 2000-09-01 | 2002-03-07 | Smithkline Beecham Corporation | Method of treatment |
| BR0115473A (pt) | 2000-11-22 | 2004-09-28 | Smithkline Beecham Corp | Inibidores de protease |
| US20040034013A1 (en) | 2001-04-17 | 2004-02-19 | Cummings Maxwell D | Methods of treatment |
| AU2002342682A1 (en) | 2001-05-17 | 2002-11-25 | Smithkline Beecham Corporation | 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 |
| EP1534292A4 (en) | 2002-05-22 | 2008-04-02 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| AU2003304496A1 (en) | 2002-05-22 | 2005-04-27 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2003103574A2 (en) | 2002-05-22 | 2003-12-18 | Smithkline Beecham Corporation | Protease inhibitors |
| EP1532115A4 (en) | 2002-05-22 | 2006-01-11 | Smithkline Beecham Corp | INHIBITORS OF PROTEASE |
| EP1511745A4 (en) | 2002-05-22 | 2006-11-15 | Smithkline Beecham Corp | 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 BR BR0109356-8A patent/BR0109356A/pt not_active IP Right Cessation
- 2001-03-07 KR KR1020027012366A patent/KR20020082896A/ko not_active Abandoned
- 2001-03-07 WO PCT/US2001/007094 patent/WO2001070232A1/en not_active Ceased
- 2001-03-07 CN CN01806446A patent/CN1416346A/zh active Pending
- 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 PL PL01357727A patent/PL357727A1/xx not_active Application Discontinuation
- 2001-03-07 CA CA002404206A patent/CA2404206A1/en not_active Abandoned
- 2001-03-07 AP APAP/P/2002/002593A patent/AP1540A/en active
- 2001-03-07 NZ NZ520588A patent/NZ520588A/en unknown
- 2001-03-07 EA EA200201001A patent/EA005893B1/ru unknown
- 2001-03-07 IL IL15096401A patent/IL150964A0/xx unknown
- 2001-03-07 US US10/239,343 patent/US7071184B2/en not_active Expired - Fee Related
- 2001-03-07 HU HU0300068A patent/HUP0300068A2/hu unknown
- 2001-03-07 JP JP2001568430A patent/JP2003527429A/ja active Pending
- 2001-03-07 OA OA1200200295A patent/OA12323A/en unknown
- 2001-03-07 CZ CZ20023168A patent/CZ20023168A3/cs unknown
- 2001-03-07 EP EP01916412A patent/EP1307203A4/en not_active Withdrawn
- 2001-03-07 SK SK1363-2002A patent/SK13632002A3/sk unknown
- 2001-03-07 DZ DZ013318A patent/DZ3318A1/fr active
- 2001-03-07 AU AU2001243441A patent/AU2001243441B2/en not_active Ceased
- 2001-03-19 UY UY26625A patent/UY26625A1/es not_active Application Discontinuation
- 2001-03-21 PE PE2001000259A patent/PE20011233A1/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
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003527429A5 (OSRAM) | ||
| US7563784B2 (en) | Protease inhibitors | |
| JP2002533397A5 (OSRAM) | ||
| AU2001243441A1 (en) | Protease inhibitors | |
| US20030225061A1 (en) | Protease inhibitors | |
| JP2004509083A (ja) | 治療方法 | |
| CZ20024086A3 (cs) | Inhibitory proteasy | |
| US7405209B2 (en) | Protease inhibitors | |
| AU2001298052A1 (en) | Protease inhibitors | |
| US20050256100A1 (en) | Protease inhibitors | |
| US20030044399A1 (en) | Method of treatment | |
| WO2003045909A2 (en) | Methods and intermediates for the synthesis of azepines | |
| MXPA01006613A (en) | Protease inhibitors |