JP2002533397A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002533397A5 JP2002533397A5 JP2000590640A JP2000590640A JP2002533397A5 JP 2002533397 A5 JP2002533397 A5 JP 2002533397A5 JP 2000590640 A JP2000590640 A JP 2000590640A JP 2000590640 A JP2000590640 A JP 2000590640A JP 2002533397 A5 JP2002533397 A5 JP 2002533397A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- azepan
- amide
- ylcarbamoyl
- 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 174
- 150000001875 compounds Chemical class 0.000 description 51
- 125000000217 alkyl group Chemical group 0.000 description 37
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 15
- 239000008194 pharmaceutical composition Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000000499 benzofuranyl group Chemical class O1C(=CC2=C1C=CC=C2)* 0.000 description 8
- MAHAMBLNIDMREX-UHFFFAOYSA-N 1-methylindole-2-carboxylic acid Chemical compound C1=CC=C2N(C)C(C(O)=O)=CC2=C1 MAHAMBLNIDMREX-UHFFFAOYSA-N 0.000 description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000005425 toluyl group Chemical group 0.000 description 7
- AWGCBUDAZSSMQT-UHFFFAOYSA-N 5,6-dimethoxy-1-benzofuran-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1OC(C(O)=O)=C2 AWGCBUDAZSSMQT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000004076 pyridyl group Chemical class 0.000 description 6
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- JJWBLYNHZXZGIQ-UHFFFAOYSA-N 5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)=CC2=CC=1OCCN1CCOCC1 JJWBLYNHZXZGIQ-UHFFFAOYSA-N 0.000 description 5
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 5
- JBVXXGSEMNXAMH-LSLKUGRBSA-N (2s)-2-amino-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound C1C(=O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1S(=O)(=O)C1=CC=CC=N1 JBVXXGSEMNXAMH-LSLKUGRBSA-N 0.000 description 4
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- 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 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000004369 butenyl group Chemical class C(=CCC)* 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical class 0.000 description 4
- 125000000842 isoxazolyl group Chemical class 0.000 description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 4
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 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 3
- ZMAILSBNDKAJFT-UHFFFAOYSA-N 4-amino-1-pyridin-2-ylsulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC=N1 ZMAILSBNDKAJFT-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- ADRFTNFHVKVATK-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 ADRFTNFHVKVATK-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Chemical class 0.000 description 3
- 102000005927 Cysteine Proteases Human genes 0.000 description 3
- 108010005843 Cysteine Proteases Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108091005804 Peptidases Proteins 0.000 description 3
- 239000004365 Protease Substances 0.000 description 3
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-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
- 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
- ZLRXPOZMNSZWTH-UHFFFAOYSA-N 5-(2-piperidin-1-ylethoxy)-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)=CC2=CC=1OCCN1CCCCC1 ZLRXPOZMNSZWTH-UHFFFAOYSA-N 0.000 description 2
- XIPQHWUSDHTXOO-UHFFFAOYSA-N 5-(4-chlorophenyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 XIPQHWUSDHTXOO-UHFFFAOYSA-N 0.000 description 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 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 class 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
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 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
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 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
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-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
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 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
- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 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
- 239000012453 solvate 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
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 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
- 125000004192 tetrahydrofuran-2-yl group Chemical class [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 group 0.000 description 2
- 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 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- AEZJMSICFGBQJC-BHWOMJMDSA-N (2S)-2-amino-N-(1-benzyl-3-oxoazepan-4-yl)-4-methylpentanamide Chemical compound C1C(=O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1CC1=CC=CC=C1 AEZJMSICFGBQJC-BHWOMJMDSA-N 0.000 description 1
- LTLLHZXCLPYHRK-BHWOMJMDSA-N (2S)-2-amino-N-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C1=CC=CC=C1 LTLLHZXCLPYHRK-BHWOMJMDSA-N 0.000 description 1
- MOHLVDJRXGVGOM-SNVBAGLBSA-N (2r)-1-benzyl-5-oxopyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCC(=O)N1CC1=CC=CC=C1 MOHLVDJRXGVGOM-SNVBAGLBSA-N 0.000 description 1
- QPENHNFPZYEKPX-LBAQZLPGSA-N (2s)-2-(benzylcarbamoylamino)-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)NCC1=CC=CC=C1 QPENHNFPZYEKPX-LBAQZLPGSA-N 0.000 description 1
- JMJUONHSNOSQOV-BBMPLOMVSA-N (2s)-2-[5-(4-methoxyphenyl)pentanoylamino]-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound C1=CC(OC)=CC=C1CCCCC(=O)N[C@@H](CC(C)C)C(=O)NC1C(=O)CN(S(=O)(=O)C=2N=CC=CC=2)CCC1 JMJUONHSNOSQOV-BBMPLOMVSA-N 0.000 description 1
- DJORAVRVYPXZCE-LBAQZLPGSA-N (2s)-2-[[2-(4-fluorophenoxy)acetyl]amino]-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)COC1=CC=C(F)C=C1 DJORAVRVYPXZCE-LBAQZLPGSA-N 0.000 description 1
- GKWLXIYCJQUSME-GEVKEYJPSA-N (2s)-2-[[2-(4-methoxy-3-phenylmethoxyphenyl)acetyl]amino]-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound O=C([C@H](CC(C)C)NC(=O)CC1=CC=C(C(=C1)OCC=1C=CC=CC=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GKWLXIYCJQUSME-GEVKEYJPSA-N 0.000 description 1
- IOTALNBOAHNSJU-LYKKTTPLSA-N (2s)-2-acetamido-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound C1C(=O)C(NC(=O)[C@@H](NC(C)=O)CC(C)C)CCCN1S(=O)(=O)C1=CC=CC=N1 IOTALNBOAHNSJU-LYKKTTPLSA-N 0.000 description 1
- FSWZCXHBMVKFCV-GTPINHCMSA-N (2s)-2-amino-n-(1-benzoyl-3-hydroxyazepan-4-yl)-4-methylpentanamide Chemical compound C1C(O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1C(=O)C1=CC=CC=C1 FSWZCXHBMVKFCV-GTPINHCMSA-N 0.000 description 1
- RIQUIYQTTZIVIZ-AOCRQIFASA-N (2s)-2-amino-n-(1-benzyl-3-hydroxyazepan-4-yl)-4-methylpentanamide Chemical compound C1C(O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1CC1=CC=CC=C1 RIQUIYQTTZIVIZ-AOCRQIFASA-N 0.000 description 1
- QNQSYELXGHSKTE-GTPINHCMSA-N (2s)-2-amino-n-[1-(benzenesulfonyl)-3-hydroxyazepan-4-yl]-4-methylpentanamide Chemical compound C1C(O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1S(=O)(=O)C1=CC=CC=C1 QNQSYELXGHSKTE-GTPINHCMSA-N 0.000 description 1
- PQSBQHKJPQBLRS-FHERZECASA-N (2s)-2-amino-n-[3-hydroxy-1-(4-methylpentanoyl)azepan-4-yl]-4-methylpentanamide Chemical compound CC(C)CCC(=O)N1CCCC(NC(=O)[C@@H](N)CC(C)C)C(O)C1 PQSBQHKJPQBLRS-FHERZECASA-N 0.000 description 1
- UGIZNFBYGSACQK-RBKXMNCYSA-N (2s)-2-amino-n-[3-hydroxy-1-[2-(3-pyridin-2-ylphenyl)acetyl]azepan-4-yl]-4-methylpentanamide Chemical compound C1C(O)C(NC(=O)[C@@H](N)CC(C)C)CCCN1C(=O)CC1=CC=CC(C=2N=CC=CC=2)=C1 UGIZNFBYGSACQK-RBKXMNCYSA-N 0.000 description 1
- GMHLVOLYOSEYIQ-GGYWPGCISA-N (2s)-4-methyl-2-(5-oxohexanoylamino)-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound C1C(=O)C(NC(=O)[C@@H](NC(=O)CCCC(C)=O)CC(C)C)CCCN1S(=O)(=O)C1=CC=CC=N1 GMHLVOLYOSEYIQ-GGYWPGCISA-N 0.000 description 1
- XMPFFIJJWCTMLK-JTQLQIEISA-N (2s)-4-methyl-2-[(2-thiophen-2-ylacetyl)amino]pentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CC1=CC=CS1 XMPFFIJJWCTMLK-JTQLQIEISA-N 0.000 description 1
- HCCYLKNNKOGEKR-AMVUTOCUSA-N (2s)-4-methyl-2-[methyl(naphthalen-2-ylmethyl)amino]-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pentanamide Chemical compound O=C([C@@H](N(C)CC=1C=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 HCCYLKNNKOGEKR-AMVUTOCUSA-N 0.000 description 1
- VXTMZNRKXDLOLG-DNKZHYAASA-N (2s)-4-methyl-2-[methyl(naphthalen-2-ylmethyl)amino]-n-[3-oxo-1-[2-(3-pyridin-2-ylphenyl)acetyl]azepan-4-yl]pentanamide Chemical compound O=C([C@@H](N(C)CC=1C=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1C(=O)CC(C=1)=CC=CC=1C1=CC=CC=N1 VXTMZNRKXDLOLG-DNKZHYAASA-N 0.000 description 1
- LEDAAVXWZMNWRH-GGYWPGCISA-N (2s)-4-methyl-n-(1-methylsulfonyl-3-oxoazepan-4-yl)-2-[(2-phenylmethoxyacetyl)amino]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(C)(=O)=O)=O)C(=O)COCC1=CC=CC=C1 LEDAAVXWZMNWRH-GGYWPGCISA-N 0.000 description 1
- RZCNQVJZHKHAJR-ANYOKISRSA-N (2s)-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)-2-(phenylcarbamoylamino)pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)NC1=CC=CC=C1 RZCNQVJZHKHAJR-ANYOKISRSA-N 0.000 description 1
- XCBCKZAJVAZTTL-ZVAWYAOSSA-N (2s)-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)-2-(pyridin-2-ylsulfonylamino)pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)S(=O)(=O)C1=CC=CC=N1 XCBCKZAJVAZTTL-ZVAWYAOSSA-N 0.000 description 1
- WPLYAJIBNJKWAC-LBAQZLPGSA-N (2s)-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)-2-(quinolin-8-ylsulfonylamino)pentanamide Chemical compound O=C([C@@H](NS(=O)(=O)C=1C2=NC=CC=C2C=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 WPLYAJIBNJKWAC-LBAQZLPGSA-N 0.000 description 1
- BULIPGOJFLOUBF-LBAQZLPGSA-N (2s)-4-methyl-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)-2-[(2-phenoxyacetyl)amino]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)COC1=CC=CC=C1 BULIPGOJFLOUBF-LBAQZLPGSA-N 0.000 description 1
- XVSAVHDIMRIOST-CGAIIQECSA-N (2s)-n-[1-(2-cyanophenyl)sulfonyl-3-oxoazepan-4-yl]-4-methyl-2-[(2-phenylmethoxyacetyl)amino]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1C(=CC=CC=1)C#N)=O)C(=O)COCC1=CC=CC=C1 XVSAVHDIMRIOST-CGAIIQECSA-N 0.000 description 1
- DGUQLPSGGQCVMD-CGAIIQECSA-N (2s)-n-[1-(4-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]-4-methyl-2-[(2-phenylmethoxyacetyl)amino]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1C=CC(F)=CC=1)=O)C(=O)COCC1=CC=CC=C1 DGUQLPSGGQCVMD-CGAIIQECSA-N 0.000 description 1
- WHLFDVKBOIGELH-BBMPLOMVSA-N (2s)-n-[1-(4-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]-4-methyl-2-[(2-phenylmethoxyacetyl)amino]pentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)COCC=2C=CC=CC=2)CCC1 WHLFDVKBOIGELH-BBMPLOMVSA-N 0.000 description 1
- NFYHMPLNPXTNHX-UHFFFAOYSA-N 1-(1-benzofuran-2-carbonyl)-n-(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)pyrrolidine-2-carboxamide Chemical compound C1CCN(C(=O)C=2OC3=CC=CC=C3C=2)C1C(=O)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 NFYHMPLNPXTNHX-UHFFFAOYSA-N 0.000 description 1
- DIDKOYZMYJYIFI-ANYOKISRSA-N 1-methyl-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]indole-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N(C2=CC=CC=C2C=1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 DIDKOYZMYJYIFI-ANYOKISRSA-N 0.000 description 1
- UFHXXKMVPZBVTM-UHFFFAOYSA-N 2-(4-amino-3-oxoazepan-1-yl)sulfonylbenzonitrile Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC=C1C#N UFHXXKMVPZBVTM-UHFFFAOYSA-N 0.000 description 1
- BUKCNFAUCKLAPY-LBAQZLPGSA-N 2-[4-[[(2s)-2-(1-benzofuran-2-carbonylamino)-4-methylpentanoyl]amino]-3-oxoazepan-1-yl]sulfonylbenzoic acid Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1C(O)=O BUKCNFAUCKLAPY-LBAQZLPGSA-N 0.000 description 1
- MQSSBVLREFSMDP-UHFFFAOYSA-N 3,4-dihydro-2h-1,5-benzodioxepine-7-carboxylic acid Chemical compound O1CCCOC2=CC(C(=O)O)=CC=C21 MQSSBVLREFSMDP-UHFFFAOYSA-N 0.000 description 1
- UIJGNGQPZZUTHI-WCSIJFPASA-N 3,4-dimethoxy-n-[(2s)-1-[[1-(4-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=2C=C(OC)C(OC)=CC=2)CCC1 UIJGNGQPZZUTHI-WCSIJFPASA-N 0.000 description 1
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 description 1
- AQTVZOSWTCMVKN-KEKNWZKVSA-N 3-methyl-n-[(2s)-4-methyl-1-[[1-(3-methylpyridin-2-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CC=C1C AQTVZOSWTCMVKN-KEKNWZKVSA-N 0.000 description 1
- IATYULMTMJKGFO-KEKNWZKVSA-N 3-methyl-n-[(2s)-4-methyl-1-[[1-(6-methylpyridin-2-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(C)=N1 IATYULMTMJKGFO-KEKNWZKVSA-N 0.000 description 1
- SIMIJQWWNNHOJM-LBAQZLPGSA-N 3-methyl-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 SIMIJQWWNNHOJM-LBAQZLPGSA-N 0.000 description 1
- GHHCFCGJHHZASQ-ANYOKISRSA-N 3-methyl-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 GHHCFCGJHHZASQ-ANYOKISRSA-N 0.000 description 1
- USFXRYVNRUMABJ-UHFFFAOYSA-N 4,5-dibromothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=C(Br)S1 USFXRYVNRUMABJ-UHFFFAOYSA-N 0.000 description 1
- SBJNYOGCJNGBRK-UHFFFAOYSA-N 4-amino-1-(4-fluorophenyl)sulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=C(F)C=C1 SBJNYOGCJNGBRK-UHFFFAOYSA-N 0.000 description 1
- DSBABXDBNWVWCJ-UHFFFAOYSA-N 4-amino-1-(4-methoxyphenyl)sulfonylazepan-3-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)C(N)CCC1 DSBABXDBNWVWCJ-UHFFFAOYSA-N 0.000 description 1
- ZFMDUNSDFISJHE-UHFFFAOYSA-N 4-amino-1-methylsulfonylazepan-3-one Chemical compound CS(=O)(=O)N1CCCC(N)C(=O)C1 ZFMDUNSDFISJHE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KHJNYTUIWBGQQD-ANYOKISRSA-N 5,6-difluoro-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC(F)=C(F)C=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 KHJNYTUIWBGQQD-ANYOKISRSA-N 0.000 description 1
- LHPAENPOUBBFIH-GGYWPGCISA-N 5,6-dimethoxy-n-[(2s)-4-methyl-1-[[1-(1-methylimidazol-4-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=C(C(=CC=2O1)OC)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CN(C)C=N1 LHPAENPOUBBFIH-GGYWPGCISA-N 0.000 description 1
- GHDZJWPAQMDVBA-ANYOKISRSA-N 5,6-dimethoxy-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=C(C(=CC=2S1)OC)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GHDZJWPAQMDVBA-ANYOKISRSA-N 0.000 description 1
- LACXHUNVZROGBY-GGYWPGCISA-N 5,6-dimethoxy-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=C(C(=CC=2O1)OC)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 LACXHUNVZROGBY-GGYWPGCISA-N 0.000 description 1
- UTKAPAFUQBYNLU-UHFFFAOYSA-N 5-(2-pyrrolidin-1-ylethoxy)-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)=CC2=CC=1OCCN1CCCC1 UTKAPAFUQBYNLU-UHFFFAOYSA-N 0.000 description 1
- FDQMAYITLCZAQV-KEKNWZKVSA-N 5-(4-chlorophenyl)-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(O1)=CC=C1C1=CC=C(Cl)C=C1 FDQMAYITLCZAQV-KEKNWZKVSA-N 0.000 description 1
- RPFMNIGUDIOQMV-LYKKTTPLSA-N 5-bromo-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C1=CC=C(Br)O1 RPFMNIGUDIOQMV-LYKKTTPLSA-N 0.000 description 1
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 1
- NSMLFXKMDZNPCH-ANYOKISRSA-N 5-fluoro-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=C(F)C=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 NSMLFXKMDZNPCH-ANYOKISRSA-N 0.000 description 1
- DSDSNIIFNGMUAZ-GGYWPGCISA-N 5-hydroxy-n-[(2s)-4-methyl-1-[[1-(1-methylimidazol-4-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=C(O)C=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CN(C)C=N1 DSDSNIIFNGMUAZ-GGYWPGCISA-N 0.000 description 1
- SQHDKWUFOYINTP-CGAIIQECSA-N 5-methoxy-n-[(2s)-1-[[1-(3-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=3OC4=CC=C(OC)C=C4C=3)CCC2)=C1 SQHDKWUFOYINTP-CGAIIQECSA-N 0.000 description 1
- NPSSHZYEKWSWCB-KEKNWZKVSA-N 5-methoxy-n-[(2s)-4-methyl-1-[[1-(3-methylpyridin-2-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CC=C1C NPSSHZYEKWSWCB-KEKNWZKVSA-N 0.000 description 1
- YVBMVCQQPYLESC-KEKNWZKVSA-N 5-methoxy-n-[(2s)-4-methyl-1-[[1-(6-methylpyridin-2-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(C)=N1 YVBMVCQQPYLESC-KEKNWZKVSA-N 0.000 description 1
- FRJRAYQZMBXNPU-LBAQZLPGSA-N 5-methoxy-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 FRJRAYQZMBXNPU-LBAQZLPGSA-N 0.000 description 1
- NRXSIWOXXMGUAM-ANYOKISRSA-N 5-methoxy-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 NRXSIWOXXMGUAM-ANYOKISRSA-N 0.000 description 1
- YABCPNYCFFUVNM-UHFFFAOYSA-N 5-methyl-2-phenyl-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)OC(C=2C=CC=CC=2)=N1 YABCPNYCFFUVNM-UHFFFAOYSA-N 0.000 description 1
- UOCNTRAAJNWDND-UHFFFAOYSA-N 7-methoxy-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=CC2=C1OC(C(O)=O)=C2 UOCNTRAAJNWDND-UHFFFAOYSA-N 0.000 description 1
- HPXHLORTYPZTDN-GGYWPGCISA-N 7-methoxy-n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 HPXHLORTYPZTDN-GGYWPGCISA-N 0.000 description 1
- NTXRDGAGYCQDBB-ZVAWYAOSSA-N 7-methoxy-n-[(2s)-4-methyl-1-oxo-1-[[3-oxo-1-(1,3-thiazol-2-ylsulfonyl)azepan-4-yl]amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 NTXRDGAGYCQDBB-ZVAWYAOSSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- PEMPXJUBJJOAPX-CGAIIQECSA-N CC(C[C@@H](C(NC1C(CN(CCC1)C(CCC1CCCCC1)=O)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C Chemical compound CC(C[C@@H](C(NC1C(CN(CCC1)C(CCC1CCCCC1)=O)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C PEMPXJUBJJOAPX-CGAIIQECSA-N 0.000 description 1
- ZTNUDRIZSZZYCP-BBMPLOMVSA-N CC(C[C@@H](C(NC1C(CN(CCC1)C(CCC1CCCCC1)=O)=O)=O)NC(=O)C=1OC2=C(C1C)C=CC=C2)C Chemical compound CC(C[C@@H](C(NC1C(CN(CCC1)C(CCC1CCCCC1)=O)=O)=O)NC(=O)C=1OC2=C(C1C)C=CC=C2)C ZTNUDRIZSZZYCP-BBMPLOMVSA-N 0.000 description 1
- AWRFPLLQSFXFAX-HFCFLWKCSA-N CC(C[C@@H](C(NC1C(CN(CCC1)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C1OCCC1)C Chemical compound CC(C[C@@H](C(NC1C(CN(CCC1)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C1OCCC1)C AWRFPLLQSFXFAX-HFCFLWKCSA-N 0.000 description 1
- UJKYNWINJSPUNL-UHFFFAOYSA-N CCC(C1)=CC=CC1c1ncccc1 Chemical compound CCC(C1)=CC=CC1c1ncccc1 UJKYNWINJSPUNL-UHFFFAOYSA-N 0.000 description 1
- 102000004171 Cathepsin K Human genes 0.000 description 1
- 108090000625 Cathepsin K Proteins 0.000 description 1
- UCGKXGFWPKIQJB-WCSIJFPASA-N N([C@@H](CC(C)C)C(=O)NC1C(CN(CC=2C=CC=CC=2)CCC1)=O)C(=O)C1=CC=C(Cl)C(Cl)=C1 Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CC=2C=CC=CC=2)CCC1)=O)C(=O)C1=CC=C(Cl)C(Cl)=C1 UCGKXGFWPKIQJB-WCSIJFPASA-N 0.000 description 1
- VTKHTZRMZFZKCR-KEKNWZKVSA-N N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(O1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(O1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 VTKHTZRMZFZKCR-KEKNWZKVSA-N 0.000 description 1
- KJYLUUVJGMYWOE-CPRJBALCSA-N N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCC1CCCCC1 Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCC1CCCCC1 KJYLUUVJGMYWOE-CPRJBALCSA-N 0.000 description 1
- QWPPTDREYVXKCO-DJNXLDHESA-N N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C1=CC=CO1 Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C1=CC=CO1 QWPPTDREYVXKCO-DJNXLDHESA-N 0.000 description 1
- CSPZCHJIJZBJBZ-RWXFGYRSSA-N N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC=2C=C(C=CC=2)C=2N=CC=CC=2)CCC1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCC1CCCCC1 Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC=2C=C(C=CC=2)C=2N=CC=CC=2)CCC1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCC1CCCCC1 CSPZCHJIJZBJBZ-RWXFGYRSSA-N 0.000 description 1
- QOFMQZUHRZQVRE-ANYOKISRSA-N N-[(2S)-1-[(1-benzoyl-3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-1,3-benzodioxole-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1OC2=CC=CC=C2O1)CC(C)C)NC(C(C1)=O)CCCN1C(=O)C1=CC=CC=C1 QOFMQZUHRZQVRE-ANYOKISRSA-N 0.000 description 1
- FYVYSZZAXIBUJB-KEKNWZKVSA-N N-[(2S)-1-[(1-benzoyl-3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-4-fluorobenzamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)C(=O)C=1C=CC=CC=1)=O)C(=O)C1=CC=C(F)C=C1 FYVYSZZAXIBUJB-KEKNWZKVSA-N 0.000 description 1
- MUGVWVVKZUFFMW-MBMZGMDYSA-N N-[(2S)-1-[benzoyl-(3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)N(C1C(CNCCC1)=O)C(=O)C=1C=CC=CC=1)C(=O)C(OC1=CC=2)=CC1=CC=2OCCN1CCOCC1 MUGVWVVKZUFFMW-MBMZGMDYSA-N 0.000 description 1
- CYUGUEOQYNFNAL-FSRLHOSWSA-N N-[(2S)-1-[methyl-[3-oxo-1-[2-(3-pyridin-2-ylphenyl)acetyl]azepan-4-yl]amino]-1-oxopentan-2-yl]quinoline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)CCC)N(C)C(C(C1)=O)CCCN1C(=O)CC(C=1)=CC=CC=1C1=CC=CC=N1 CYUGUEOQYNFNAL-FSRLHOSWSA-N 0.000 description 1
- QBBVYFZIDVTDCF-FJDUUPPCSA-N N-[(2S)-3-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound CC([C@@H](C(NC1C(CN(CCC1)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)CC QBBVYFZIDVTDCF-FJDUUPPCSA-N 0.000 description 1
- YPPGNLJNGUHTRD-ANYOKISRSA-N N-[(2S)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(=C(O1)C(F)(F)F)N=C1C1=CC=CC=C1 YPPGNLJNGUHTRD-ANYOKISRSA-N 0.000 description 1
- YJWXNSPBAOKASY-HTIIIDOHSA-N N-[(2S)-4-methyl-1-oxo-1-[[3-oxo-1-[2-(3-pyridin-2-ylphenyl)ethyl]azepan-4-yl]amino]pentan-2-yl]-5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC=2C=C(C=CC=2)C=2N=CC=CC=2)CCC1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCN1CCOCC1 YJWXNSPBAOKASY-HTIIIDOHSA-N 0.000 description 1
- YCULWUFYWWSRJZ-IJHRGXPZSA-N N1=C2C(=NO1)C(=CC=C2)S(=O)(=O)N2CC(C(CCC2)NC(=O)[C@H](CC(C)C)NC(=O)C=2OC1=C(C2)C=CC=C1)=O Chemical compound N1=C2C(=NO1)C(=CC=C2)S(=O)(=O)N2CC(C(CCC2)NC(=O)[C@H](CC(C)C)NC(=O)C=2OC1=C(C2)C=CC=C1)=O YCULWUFYWWSRJZ-IJHRGXPZSA-N 0.000 description 1
- LCIUOXMMEGTREE-GGYWPGCISA-N O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 LCIUOXMMEGTREE-GGYWPGCISA-N 0.000 description 1
- LZTGPHQFBCZQAT-ANYOKISRSA-N O=C([C@@H](NC(=O)C1=C(C=2SC(=CC=2S1)C(C)(C)C)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C1=C(C=2SC(=CC=2S1)C(C)(C)C)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 LZTGPHQFBCZQAT-ANYOKISRSA-N 0.000 description 1
- WFAKQRKOMPBMBS-KEKNWZKVSA-N O=C([C@@H](NC(=O)C=1C2=CC=CC=C2C=CN=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1C2=CC=CC=C2C=CN=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 WFAKQRKOMPBMBS-KEKNWZKVSA-N 0.000 description 1
- HAEWQXGKXLGPAL-OBOZPERJSA-N O=C([C@@H](NC(=O)C=1C=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1CCC(C=1)=CC=CC=1C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1C=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1CCC(C=1)=CC=CC=1C1=CC=CC=N1 HAEWQXGKXLGPAL-OBOZPERJSA-N 0.000 description 1
- MPWJDGQRWASNBF-KEKNWZKVSA-N O=C([C@@H](NC(=O)C=1C=C2OCOC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 Chemical compound O=C([C@@H](NC(=O)C=1C=C2OCOC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 MPWJDGQRWASNBF-KEKNWZKVSA-N 0.000 description 1
- XFMHBMUNCAPDJQ-GGYWPGCISA-N O=C([C@@H](NC(=O)C=1N(C2=CC=CC=C2C=1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@@H](NC(=O)C=1N(C2=CC=CC=C2C=1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 XFMHBMUNCAPDJQ-GGYWPGCISA-N 0.000 description 1
- VNQARSLGXJXWIF-ZVAWYAOSSA-N O=C([C@@H](NC(=O)C=1N(C2=CC=CC=C2C=1)C)CC(C)C)NC1CCCN(S(C)(=O)=O)CC1=O Chemical compound O=C([C@@H](NC(=O)C=1N(C2=CC=CC=C2C=1)C)CC(C)C)NC1CCCN(S(C)(=O)=O)CC1=O VNQARSLGXJXWIF-ZVAWYAOSSA-N 0.000 description 1
- CAORPUAEPKVJLQ-IJHRGXPZSA-N O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)CC(C)C)NC1CCCN(S(C)(=O)=O)CC1=O Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)CC(C)C)NC1CCCN(S(C)(=O)=O)CC1=O CAORPUAEPKVJLQ-IJHRGXPZSA-N 0.000 description 1
- VQXFQKSHBSRDJQ-WCSIJFPASA-N O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1C#N Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1C#N VQXFQKSHBSRDJQ-WCSIJFPASA-N 0.000 description 1
- UJZMKJFRAZQOTL-GGYWPGCISA-N O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 UJZMKJFRAZQOTL-GGYWPGCISA-N 0.000 description 1
- XSYZGNALQCHWBJ-ZSXSBBPPSA-N O=C([C@@H](NC(=O)C=1NC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1CCC(C=1)=CC=CC=1C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1NC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1CCC(C=1)=CC=CC=1C1=CC=CC=N1 XSYZGNALQCHWBJ-ZSXSBBPPSA-N 0.000 description 1
- WBLLPEBXKZZSNR-IMMUGOHXSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)C(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)C(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 WBLLPEBXKZZSNR-IMMUGOHXSA-N 0.000 description 1
- YMDJHBQLNMQWCI-MYJWUSKBSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 YMDJHBQLNMQWCI-MYJWUSKBSA-N 0.000 description 1
- NWNRZLFLTABEFY-WCSIJFPASA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 NWNRZLFLTABEFY-WCSIJFPASA-N 0.000 description 1
- ZBICSQFAVPFOLS-ANYOKISRSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=C(C)OCN1C Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=C(C)OCN1C ZBICSQFAVPFOLS-ANYOKISRSA-N 0.000 description 1
- QAZGYBADCWQFJN-KEKNWZKVSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Br)C=C1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Br)C=C1 QAZGYBADCWQFJN-KEKNWZKVSA-N 0.000 description 1
- LHFIKPOLVJQYCY-LBAQZLPGSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(C)=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(C)=N1 LHFIKPOLVJQYCY-LBAQZLPGSA-N 0.000 description 1
- FVYNLUJEBVWJRP-ZVAWYAOSSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 FVYNLUJEBVWJRP-ZVAWYAOSSA-N 0.000 description 1
- XYPUARDMJPZPND-ANYOKISRSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)N1CN(C)C=C1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)N1CN(C)C=C1 XYPUARDMJPZPND-ANYOKISRSA-N 0.000 description 1
- GXGKIJZGCOCBGL-ZENAZSQFSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GXGKIJZGCOCBGL-ZENAZSQFSA-N 0.000 description 1
- QUSUSKZVXILPJR-GGYWPGCISA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 QUSUSKZVXILPJR-GGYWPGCISA-N 0.000 description 1
- JSCUNMJZFQLLKY-ANYOKISRSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCCC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCCC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 JSCUNMJZFQLLKY-ANYOKISRSA-N 0.000 description 1
- APEZKSUFNIIVOZ-HXKVNORTSA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCS(=O)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCS(=O)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 APEZKSUFNIIVOZ-HXKVNORTSA-N 0.000 description 1
- WQVIFQCQTSZCEI-DJNXLDHESA-N O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CO)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CO)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 WQVIFQCQTSZCEI-DJNXLDHESA-N 0.000 description 1
- XZSCJNOIGQNKRA-ZVAWYAOSSA-N O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 XZSCJNOIGQNKRA-ZVAWYAOSSA-N 0.000 description 1
- LHDWIMWCSQGOTJ-ANYOKISRSA-N O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 LHDWIMWCSQGOTJ-ANYOKISRSA-N 0.000 description 1
- OUCRKZNNELTFTD-WCSIJFPASA-N O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1C#N Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1C#N OUCRKZNNELTFTD-WCSIJFPASA-N 0.000 description 1
- SLNRJVHEWRIXQL-GGYWPGCISA-N O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CS1 SLNRJVHEWRIXQL-GGYWPGCISA-N 0.000 description 1
- KUNXUWPXTDZXHQ-ZVAWYAOSSA-N O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC1CCCN(S(C)(=O)=O)CC1=O Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC1CCCN(S(C)(=O)=O)CC1=O KUNXUWPXTDZXHQ-ZVAWYAOSSA-N 0.000 description 1
- GLLREXZHNRBDFY-JKGBFCRXSA-N O=C([C@H](CC=1C=CC=CC=1)NC(=O)C=1N=C2C=CC=CC2=CC=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 Chemical compound O=C([C@H](CC=1C=CC=CC=1)NC(=O)C=1N=C2C=CC=CC2=CC=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GLLREXZHNRBDFY-JKGBFCRXSA-N 0.000 description 1
- VRAKGCJYEQYESY-KEKNWZKVSA-N O=C1CN(C(=O)CCC(C)C)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=C(C)C2=CC=CC=C2O1 Chemical compound O=C1CN(C(=O)CCC(C)C)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=C(C)C2=CC=CC=C2O1 VRAKGCJYEQYESY-KEKNWZKVSA-N 0.000 description 1
- IBGBNFAZGQEGSS-LBAQZLPGSA-N O=C1CN(C(=O)CCC(C)C)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 Chemical compound O=C1CN(C(=O)CCC(C)C)CCCC1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=CC=CC=C2O1 IBGBNFAZGQEGSS-LBAQZLPGSA-N 0.000 description 1
- VGUNUXVONMWDHC-DDRXVLGJSA-N OC([C@@H](C(NC1C(CN(CCC1)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C Chemical compound OC([C@@H](C(NC1C(CN(CCC1)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C VGUNUXVONMWDHC-DDRXVLGJSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ODQMVYJECRSYJM-ANYOKISRSA-N benzyl 4-[[(2s)-2-(2,2-dimethylpropanoylamino)-4-methylpentanoyl]amino]-3-oxoazepane-1-carboxylate Chemical compound C1C(=O)C(NC(=O)[C@@H](NC(=O)C(C)(C)C)CC(C)C)CCCN1C(=O)OCC1=CC=CC=C1 ODQMVYJECRSYJM-ANYOKISRSA-N 0.000 description 1
- ZAIRIKJXUIZRPN-ADKAHSJRSA-N benzyl n-[(2s)-1-[(3-hydroxyazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CNCCC1)O)C(=O)OCC1=CC=CC=C1 ZAIRIKJXUIZRPN-ADKAHSJRSA-N 0.000 description 1
- OBWCUTFNGGQDDT-WOLZVPSQSA-N benzyl n-[(2s)-1-[4-[[(2s)-2-amino-4-methylpentanoyl]amino]-3-hydroxyazepan-1-yl]-4-methylpentan-2-yl]carbamate Chemical compound C([C@H](CC(C)C)NC(=O)OCC=1C=CC=CC=1)N1CCCC(NC(=O)[C@@H](N)CC(C)C)C(O)C1 OBWCUTFNGGQDDT-WOLZVPSQSA-N 0.000 description 1
- OMYYDIWKNKBPIV-LBAQZLPGSA-N benzyl n-[[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]carbamoyl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)NC(=O)OCC1=CC=CC=C1 OMYYDIWKNKBPIV-LBAQZLPGSA-N 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GIJIKNIHYNIDSJ-UHFFFAOYSA-N methyl 1-benzofuran-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=CC2=C1 GIJIKNIHYNIDSJ-UHFFFAOYSA-N 0.000 description 1
- RRFSDGUZULKRGU-UHFFFAOYSA-N methyl 5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxylate Chemical compound C=1C=C2OC(C(=O)OC)=CC2=CC=1OCCN1CCOCC1 RRFSDGUZULKRGU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMKCNDFRBKNJNK-KEKNWZKVSA-N n-[(2s)-1-[(1-benzoyl-3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1C(=O)C1=CC=CC=C1 PMKCNDFRBKNJNK-KEKNWZKVSA-N 0.000 description 1
- VUWJYROJTRQGKP-WCSIJFPASA-N n-[(2s)-1-[(1-benzyl-3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 VUWJYROJTRQGKP-WCSIJFPASA-N 0.000 description 1
- AGBNZOPRZFUHGQ-JKGBFCRXSA-N n-[(2s)-1-[(1-benzyl-3-oxoazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]quinoline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1CC1=CC=CC=C1 AGBNZOPRZFUHGQ-JKGBFCRXSA-N 0.000 description 1
- JCTWFUJBPUAVGX-BGERDNNASA-N n-[(2s)-1-[(6,6-dimethyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CC(C)(C)CN1S(=O)(=O)C1=CC=CC=N1 JCTWFUJBPUAVGX-BGERDNNASA-N 0.000 description 1
- QGXDSBYNGPVUNT-ZVAWYAOSSA-N n-[(2s)-1-[[1-(1h-imidazol-2-ylsulfonyl)-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=NC=CN1 QGXDSBYNGPVUNT-ZVAWYAOSSA-N 0.000 description 1
- ODJPIXBYBJFLCF-LBAQZLPGSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F ODJPIXBYBJFLCF-LBAQZLPGSA-N 0.000 description 1
- PYUSILKKNKVRBZ-LBAQZLPGSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F PYUSILKKNKVRBZ-LBAQZLPGSA-N 0.000 description 1
- BIEMOIDCNHSWJN-KEKNWZKVSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F BIEMOIDCNHSWJN-KEKNWZKVSA-N 0.000 description 1
- IOWPQVLSQNDCMA-KEKNWZKVSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methyl-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=C(C)C=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F IOWPQVLSQNDCMA-KEKNWZKVSA-N 0.000 description 1
- WFFAZODUQODRIA-LBAQZLPGSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-7-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F WFFAZODUQODRIA-LBAQZLPGSA-N 0.000 description 1
- UXEGTEKJBBATFA-KEKNWZKVSA-N n-[(2s)-1-[[1-(2-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1F UXEGTEKJBBATFA-KEKNWZKVSA-N 0.000 description 1
- ASWYDHRNGJTCLS-LBAQZLPGSA-N n-[(2s)-1-[[1-(3,4-dimethoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CCC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(OC)C(OC)=C1 ASWYDHRNGJTCLS-LBAQZLPGSA-N 0.000 description 1
- FJAAZPWTLHCOEZ-KEKNWZKVSA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 FJAAZPWTLHCOEZ-KEKNWZKVSA-N 0.000 description 1
- VOVMFNGJAGIYTB-KEKNWZKVSA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 VOVMFNGJAGIYTB-KEKNWZKVSA-N 0.000 description 1
- AGSZJFBAGFYLQC-WCSIJFPASA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 AGSZJFBAGFYLQC-WCSIJFPASA-N 0.000 description 1
- JNDDSVFREZUXIG-WCSIJFPASA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 JNDDSVFREZUXIG-WCSIJFPASA-N 0.000 description 1
- GYDOWLJAHSRWHB-KEKNWZKVSA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-7-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 GYDOWLJAHSRWHB-KEKNWZKVSA-N 0.000 description 1
- NNLSFRYWZZCQPG-WCSIJFPASA-N n-[(2s)-1-[[1-(3-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC(Cl)=C1 NNLSFRYWZZCQPG-WCSIJFPASA-N 0.000 description 1
- FXCSOFFOVMATCR-WCSIJFPASA-N n-[(2s)-1-[[1-(3-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=3OC4=CC=CC=C4C=3)CCC2)=C1 FXCSOFFOVMATCR-WCSIJFPASA-N 0.000 description 1
- RIFOROAGFJINFW-WCSIJFPASA-N n-[(2s)-1-[[1-(3-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=3SC4=CC=CC=C4C=3)CCC2)=C1 RIFOROAGFJINFW-WCSIJFPASA-N 0.000 description 1
- PRKDXXVRPJRYKC-CGAIIQECSA-N n-[(2s)-1-[[1-(3-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C3=C(C4=CC=CC=C4O3)C)CCC2)=C1 PRKDXXVRPJRYKC-CGAIIQECSA-N 0.000 description 1
- IHTNODSTZAOPQB-CGAIIQECSA-N n-[(2s)-1-[[1-(3-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=3N=C4C=CC=CC4=NC=3)CCC2)=C1 IHTNODSTZAOPQB-CGAIIQECSA-N 0.000 description 1
- YBVQTSMBIKMQFP-KEKNWZKVSA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 YBVQTSMBIKMQFP-KEKNWZKVSA-N 0.000 description 1
- WTEABCZQNQKVAD-KEKNWZKVSA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 WTEABCZQNQKVAD-KEKNWZKVSA-N 0.000 description 1
- FHAONFIZDQILAZ-WCSIJFPASA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C1=C(C2=CC=CC=C2O1)C)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 FHAONFIZDQILAZ-WCSIJFPASA-N 0.000 description 1
- HHHCCOPAVNDQJL-WCSIJFPASA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C=1OC2=CC=C(C=C2C=1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 HHHCCOPAVNDQJL-WCSIJFPASA-N 0.000 description 1
- GTXSIPZGOMXRHI-KEKNWZKVSA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-7-methoxy-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC(C)C)NC(=O)C1=CC=2C=CC=C(C=2O1)OC)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 GTXSIPZGOMXRHI-KEKNWZKVSA-N 0.000 description 1
- NTAPVYANISFHSV-WCSIJFPASA-N n-[(2s)-1-[[1-(4-chlorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 NTAPVYANISFHSV-WCSIJFPASA-N 0.000 description 1
- MPPHZJBKOIOWCW-LBAQZLPGSA-N n-[(2s)-1-[[1-(4-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1,3-benzodioxole-5-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2OCOC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(F)C=C1 MPPHZJBKOIOWCW-LBAQZLPGSA-N 0.000 description 1
- IPVHTBGJYIHNQK-KEKNWZKVSA-N n-[(2s)-1-[[1-(4-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=C(F)C=C1 IPVHTBGJYIHNQK-KEKNWZKVSA-N 0.000 description 1
- CZTZETWBAAXQGO-WCSIJFPASA-N n-[(2s)-1-[[1-(4-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)C=2SC3=CC=CC=C3C=2)CCC1 CZTZETWBAAXQGO-WCSIJFPASA-N 0.000 description 1
- GLLGPTPNNNBTGH-KEKNWZKVSA-N n-[(2s)-1-[[1-(benzenesulfonyl)-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1 GLLGPTPNNNBTGH-KEKNWZKVSA-N 0.000 description 1
- YROCWTBUPGWUAD-WCSIJFPASA-N n-[(2s)-1-[[1-(benzenesulfonyl)-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]-1h-indole-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1NC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=C1 YROCWTBUPGWUAD-WCSIJFPASA-N 0.000 description 1
- RUFODXYCBRKJCI-CGAIIQECSA-N n-[(2s)-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-3-phenylmethoxypropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](COCC=1C=CC=CC=1)NC(=O)C=1OC2=CC=CC=C2C=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 RUFODXYCBRKJCI-CGAIIQECSA-N 0.000 description 1
- VGIWPEJPLFVKSL-WCSIJFPASA-N n-[(2s)-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-3-phenylpropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC=1C=CC=CC=1)NC(=O)C=1OC2=CC=CC=C2C=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 VGIWPEJPLFVKSL-WCSIJFPASA-N 0.000 description 1
- DJZANHMERSTTFE-BBMPLOMVSA-N n-[(2s)-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-3-phenylpropan-2-yl]quinoline-8-carboxamide Chemical compound O=C([C@H](CC=1C=CC=CC=1)NC(=O)C=1C2=NC=CC=C2C=CC=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 DJZANHMERSTTFE-BBMPLOMVSA-N 0.000 description 1
- OAGUTUZNQIDKFF-WCSIJFPASA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C=1OC2=CC=CC=C2C=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 OAGUTUZNQIDKFF-WCSIJFPASA-N 0.000 description 1
- BAZDEYSGPLMATO-ZVAWYAOSSA-N n-[(2s)-4-methyl-1-[(1-methylsulfonyl-3-oxoazepan-4-yl)amino]-1-oxopentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC1CCCN(S(C)(=O)=O)CC1=O BAZDEYSGPLMATO-ZVAWYAOSSA-N 0.000 description 1
- MCKCVIDASJTQSU-MNLRITNHSA-N n-[(2s)-4-methyl-1-[(6-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CC(C)CN1S(=O)(=O)C1=CC=CC=N1 MCKCVIDASJTQSU-MNLRITNHSA-N 0.000 description 1
- QBAUVZVXFGGTNQ-GGYWPGCISA-N n-[(2s)-4-methyl-1-[[1-(1-methylimidazol-4-yl)sulfonyl-3-oxoazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CN(C)C=N1 QBAUVZVXFGGTNQ-GGYWPGCISA-N 0.000 description 1
- OANYTQNMSAUWHY-GGYWPGCISA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1,3-benzodioxole-5-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2OCOC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 OANYTQNMSAUWHY-GGYWPGCISA-N 0.000 description 1
- SHACANFSVRUECR-QWAKEFERSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1,8-naphthyridine-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2N=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 SHACANFSVRUECR-QWAKEFERSA-N 0.000 description 1
- VBPPNJCVXGAZDD-ANYOKISRSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 VBPPNJCVXGAZDD-ANYOKISRSA-N 0.000 description 1
- JJPNYWRFPJDAOT-ANYOKISRSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 JJPNYWRFPJDAOT-ANYOKISRSA-N 0.000 description 1
- FBZBUNUKYICDHW-LBAQZLPGSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1h-indole-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1NC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 FBZBUNUKYICDHW-LBAQZLPGSA-N 0.000 description 1
- PZWBJZVNTRLYSD-IAXKEJLGSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1h-indole-6-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2NC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 PZWBJZVNTRLYSD-IAXKEJLGSA-N 0.000 description 1
- MAKIECPXJZPRFD-KEKNWZKVSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-5-(4-nitrophenyl)furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(O1)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 MAKIECPXJZPRFD-KEKNWZKVSA-N 0.000 description 1
- CNPDOFZBJGECAY-LYKKTTPLSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-5-nitrofuran-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C1=CC=C([N+]([O-])=O)O1 CNPDOFZBJGECAY-LYKKTTPLSA-N 0.000 description 1
- JNSFSCKSTYXIAM-YANBTOMASA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]isoquinoline-3-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=CC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 JNSFSCKSTYXIAM-YANBTOMASA-N 0.000 description 1
- LFKWIZQIKIHFJP-YANBTOMASA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 LFKWIZQIKIHFJP-YANBTOMASA-N 0.000 description 1
- SFBABLMJYIFBRW-WCSIJFPASA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoline-3-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 SFBABLMJYIFBRW-WCSIJFPASA-N 0.000 description 1
- ULISHQZUABJOEO-WCSIJFPASA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoline-6-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2C=CC=NC2=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 ULISHQZUABJOEO-WCSIJFPASA-N 0.000 description 1
- OZNGVEHEJAXJKC-KEKNWZKVSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoline-8-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C2=NC=CC=C2C=CC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 OZNGVEHEJAXJKC-KEKNWZKVSA-N 0.000 description 1
- XERCYXLBBKTDLV-LBAQZLPGSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 XERCYXLBBKTDLV-LBAQZLPGSA-N 0.000 description 1
- YSVHAUZDPDGMGC-GGYWPGCISA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 YSVHAUZDPDGMGC-GGYWPGCISA-N 0.000 description 1
- VOMLQPDVXPWRQU-GGYWPGCISA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]-1-benzothiophene-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1SC2=CC=CC=C2C=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 VOMLQPDVXPWRQU-GGYWPGCISA-N 0.000 description 1
- WDTGYGOTPKZSOT-ANYOKISRSA-N n-[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-thiophen-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]quinoxaline-2-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1N=C2C=CC=CC2=NC=1)CC(C)C)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CS1 WDTGYGOTPKZSOT-ANYOKISRSA-N 0.000 description 1
- KRMYDWCAHQJBOD-DNKZHYAASA-N n-[(2s)-4-methyl-1-oxo-1-[[3-oxo-1-[2-(3-pyridin-2-ylphenyl)acetyl]azepan-4-yl]amino]pentan-2-yl]-5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)C(=O)CC=1C=C(C=CC=1)C=1N=CC=CC=1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCN1CCOCC1 KRMYDWCAHQJBOD-DNKZHYAASA-N 0.000 description 1
- UZOMAHFSRWZWHN-UHFFFAOYSA-N n-[1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]hexan-2-yl]quinoline-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)NC(CCCC)C(=O)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 UZOMAHFSRWZWHN-UHFFFAOYSA-N 0.000 description 1
- IUCXEUAJTJPYPL-ANYOKISRSA-N n-[2-[[(2s)-1-[[1-(2-cyanophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1C(=CC=CC=1)C#N)=O)C(=O)CNC(=O)C1=CC=CO1 IUCXEUAJTJPYPL-ANYOKISRSA-N 0.000 description 1
- NEPBVOOPFIXSGP-ANYOKISRSA-N n-[2-[[(2s)-1-[[1-(4-fluorophenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1C=CC(F)=CC=1)=O)C(=O)CNC(=O)C1=CC=CO1 NEPBVOOPFIXSGP-ANYOKISRSA-N 0.000 description 1
- QCWNNJUXBSSPBJ-LBAQZLPGSA-N n-[2-[[(2s)-1-[[1-(4-methoxyphenyl)sulfonyl-3-oxoazepan-4-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]furan-2-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(=O)C(NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C=2OC=CC=2)CCC1 QCWNNJUXBSSPBJ-LBAQZLPGSA-N 0.000 description 1
- LLVJFBLDVBCPFH-LOACHALJSA-N n-[2-[[(2s)-4-methyl-1-[(1-methylsulfonyl-3-oxoazepan-4-yl)amino]-1-oxopentan-2-yl]amino]-2-oxoethyl]furan-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(C)(=O)=O)=O)C(=O)CNC(=O)C1=CC=CO1 LLVJFBLDVBCPFH-LOACHALJSA-N 0.000 description 1
- DIOXFJPISZXNBO-UHFFFAOYSA-N n-[2-oxo-2-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]ethyl]-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC=CC=C2OC=1C(=O)NCC(=O)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 DIOXFJPISZXNBO-UHFFFAOYSA-N 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 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
- ARIXSJWFRFSRTP-XIJSCUBXSA-N tert-butyl 4-[2-[[2-[[(2s)-4-methyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]pentan-2-yl]carbamoyl]-1-benzofuran-5-yl]oxy]ethyl]piperazine-1-carboxylate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C(=O)C(OC1=CC=2)=CC1=CC=2OCCN1CCN(C(=O)OC(C)(C)C)CC1 ARIXSJWFRFSRTP-XIJSCUBXSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11363698P | 1998-12-23 | 1998-12-23 | |
| US60/113,636 | 1998-12-23 | ||
| US16458199P | 1999-11-10 | 1999-11-10 | |
| US60/164,581 | 1999-11-10 | ||
| PCT/US1999/030730 WO2000038687A1 (en) | 1998-12-23 | 1999-12-21 | Protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002533397A JP2002533397A (ja) | 2002-10-08 |
| JP2002533397A5 true JP2002533397A5 (https=) | 2006-09-07 |
Family
ID=26811293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000590640A Pending JP2002533397A (ja) | 1998-12-23 | 1999-12-21 | プロテアーゼ阻害剤 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US20020147188A1 (https=) |
| EP (1) | EP1158986A4 (https=) |
| JP (1) | JP2002533397A (https=) |
| KR (1) | KR100630986B1 (https=) |
| CN (1) | CN1253441C (https=) |
| AT (1) | ATE411294T1 (https=) |
| AU (1) | AU768565B2 (https=) |
| BR (1) | BR9916488A (https=) |
| CA (1) | CA2356671A1 (https=) |
| CZ (1) | CZ20012277A3 (https=) |
| DE (1) | DE69939752D1 (https=) |
| DZ (1) | DZ2977A1 (https=) |
| ES (1) | ES2315456T3 (https=) |
| GC (1) | GC0000178A (https=) |
| HK (1) | HK1043536A1 (https=) |
| HU (1) | HUP0104768A3 (https=) |
| IL (2) | IL143142A0 (https=) |
| NO (1) | NO318910B1 (https=) |
| NZ (1) | NZ511710A (https=) |
| PE (1) | PE20001340A1 (https=) |
| PL (1) | PL350132A1 (https=) |
| TR (1) | TR200101869T2 (https=) |
| UY (1) | UY25874A1 (https=) |
| WO (1) | WO2000038687A1 (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1231922A4 (en) * | 1999-11-10 | 2004-06-23 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| WO2001034566A2 (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 |
| 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 |
| EP1229914A4 (en) * | 1999-11-10 | 2004-06-23 | 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 |
| 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 |
| WO2001034565A2 (en) * | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | 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 |
| WO2001034154A1 (en) * | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| KR20020082896A (ko) * | 2000-03-21 | 2002-10-31 | 스미스클라인 비참 코포레이션 | 프로테아제 억제제 |
| 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 |
| AU2001268407A1 (en) * | 2000-06-14 | 2001-12-24 | Smithkline Beecham Corporation | 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 |
| US7709510B2 (en) | 2001-02-20 | 2010-05-04 | Chugai Seiyaku Kabushiki Kaisha | Azoles as malonyl-CoA decarboxylase inhibitors useful as metabolic modulators |
| CA2437409C (en) | 2001-02-20 | 2010-10-19 | Chugai Seiyaku Kabushiki Kaisha | Azoles as malonyl-coa decarboxylase inhibitors useful as metabolic modulators |
| EP1401453A4 (en) * | 2001-05-17 | 2005-04-06 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| US6982263B2 (en) | 2001-06-08 | 2006-01-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Nitriles useful as reversible inhibitors of cysteine proteases |
| WO2003097593A2 (en) * | 2002-05-22 | 2003-11-27 | Smithkline Beecham Corporation | Protease inhibitors |
| AU2003233642A1 (en) * | 2002-05-22 | 2003-12-12 | Smithkline Beecham Corporation | Protease inhibitors |
| KR100962972B1 (ko) | 2002-07-26 | 2010-06-09 | 주식회사유한양행 | 1-페닐피페리딘-3-온 유도체 및 그의 제조방법 |
| 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 |
| EP4101846B1 (en) | 2003-04-11 | 2023-08-02 | PTC Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| CA2533747C (en) * | 2003-08-01 | 2012-11-13 | Chugai Seiyaku Kabushiki Kaisha | Heterocyclic compounds useful as malonyl-coa decarboxylase inhibitors |
| CA2533749C (en) | 2003-08-01 | 2012-07-10 | Chugai Seiyaku Kabushiki Kaisha | Piperidine compounds useful as malonyl-coa decarboxylase inhibitors |
| US7786145B2 (en) | 2003-08-01 | 2010-08-31 | Chugai Seiyaku Kabushiki Kaisha | Cyanoguanidine-based azole compounds useful as malonyl-CoA decarboxylase inhibitors |
| JP2007517810A (ja) * | 2004-01-08 | 2007-07-05 | メルク フロスト カナダ リミテツド | カテプシンシステインプロテアーゼ阻害剤 |
| JP2008512461A (ja) * | 2004-09-07 | 2008-04-24 | スミスクライン・ビーチャム・コーポレイション | 新規化合物 |
| WO2007012180A1 (en) * | 2005-07-26 | 2007-02-01 | Merck Frosst Canada Ltd. | Papain family cysteine protease inhibitors for the treatment of parasitic diseases |
| EP2387995A1 (en) | 2006-03-30 | 2011-11-23 | PTC Therapeutics, Inc. | Methods for the production of functional protein from DNA having a nonsense mutation and the treatment of disorders associated therewith |
| 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 |
| TWI695717B (zh) | 2014-03-06 | 2020-06-11 | 美商 Ptc 治療公司 | １,２,４-二唑苯甲酸之鹽及醫藥組合物 |
| CN108348527A (zh) | 2015-10-30 | 2018-07-31 | Ptc医疗公司 | 用于治疗癫痫的方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1195287B (it) * | 1981-11-05 | 1988-10-12 | Ausonia Farma Srl | Derivato tiazolico,procedimento per la sua preparazione e relative composizioni farmaceutiche |
| 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 |
| 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 |
| DE69612962T2 (de) * | 1995-12-12 | 2001-11-15 | Taiho Pharmaceutical Co. Ltd., Tokio/Tokyo | Epoxysuccinamid-derivate oder deren salze und medikamente die diese enthalten |
| US5902882A (en) * | 1996-04-17 | 1999-05-11 | Hoffmann-La Roche Inc. | Assymetric synthesis of azepines |
| DZ2285A1 (fr) * | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
| US6107291A (en) * | 1997-12-19 | 2000-08-22 | Amgen Inc. | Azepine or larger medium ring derivatives and methods of use |
| WO2001034566A2 (en) * | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2001034154A1 (en) * | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| 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 |
| 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 |
| WO2001034565A2 (en) * | 1999-11-10 | 2001-05-17 | 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 |
| 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 |
| WO2001034160A1 (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 |
| NL1013996C2 (nl) * | 1999-12-30 | 2001-07-03 | Innas Free Piston Bv | Vrijezuiger aggregaat voor opwekken van hydraulische energie. |
-
1999
- 1999-12-21 WO PCT/US1999/030730 patent/WO2000038687A1/en not_active Ceased
- 1999-12-21 CZ CZ20012277A patent/CZ20012277A3/cs unknown
- 1999-12-21 KR KR1020017007989A patent/KR100630986B1/ko not_active Expired - Fee Related
- 1999-12-21 IL IL14314299A patent/IL143142A0/xx active IP Right Grant
- 1999-12-21 CN CNB998150932A patent/CN1253441C/zh not_active Expired - Fee Related
- 1999-12-21 AU AU19411/00A patent/AU768565B2/en not_active Ceased
- 1999-12-21 HU HU0104768A patent/HUP0104768A3/hu unknown
- 1999-12-21 NZ NZ511710A patent/NZ511710A/en unknown
- 1999-12-21 AT AT03076211T patent/ATE411294T1/de not_active IP Right Cessation
- 1999-12-21 PL PL99350132A patent/PL350132A1/xx not_active Application Discontinuation
- 1999-12-21 BR BR9916488-4A patent/BR9916488A/pt not_active IP Right Cessation
- 1999-12-21 TR TR2001/01869T patent/TR200101869T2/xx unknown
- 1999-12-21 JP JP2000590640A patent/JP2002533397A/ja active Pending
- 1999-12-21 HK HK02103610.2A patent/HK1043536A1/zh unknown
- 1999-12-21 EP EP99963112A patent/EP1158986A4/en not_active Withdrawn
- 1999-12-21 DE DE69939752T patent/DE69939752D1/de not_active Expired - Lifetime
- 1999-12-21 CA CA002356671A patent/CA2356671A1/en not_active Abandoned
- 1999-12-21 ES ES03076211T patent/ES2315456T3/es not_active Expired - Lifetime
- 1999-12-22 GC GCP1999461 patent/GC0000178A/en active
- 1999-12-22 DZ DZ990277A patent/DZ2977A1/xx active
- 1999-12-22 UY UY25874A patent/UY25874A1/es not_active Application Discontinuation
- 1999-12-23 PE PE1999001312A patent/PE20001340A1/es not_active Application Discontinuation
-
2001
- 2001-05-14 IL IL143142A patent/IL143142A/en not_active IP Right Cessation
- 2001-06-22 NO NO20013124A patent/NO318910B1/no unknown
-
2002
- 2002-02-13 US US10/074,940 patent/US20020147188A1/en not_active Abandoned
-
2003
- 2003-04-01 US US10/404,142 patent/US20030225061A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002533397A5 (https=) | ||
| JP2003527429A5 (https=) | ||
| CA2356671A1 (en) | Protease inhibitors | |
| US8518973B2 (en) | Compounds having 4-pyridylalkylthio group as a substituent | |
| RU2004138079A (ru) | Антагонисты рецептора-1 меланин-концентрирующего гормона (мсн1r) | |
| CN101027295A (zh) | 用于治疗炎性疾病的化合物和含它们的药物组合物 | |
| AU7288598A (en) | Protease inhibitors | |
| NZ518698A (en) | Novel cyclopropanes as CGRP antagonists, medicaments containing said compounds and method for the production thereof | |
| OA12323A (en) | Protease inhibitors. | |
| ZA200206361B (en) | Piperidine and piperazine derivatives which function as 5-HT2A receptor antagonists. | |
| EP1320370A1 (en) | Method of treatment | |
| JP2015520224A5 (https=) | ||
| CA2412353A1 (en) | Protease inhibitors | |
| IE61963B1 (en) | Indan derivatives and process for preparation thereof | |
| US7405209B2 (en) | Protease inhibitors | |
| ZA200104208B (en) | Protease inhibitors. | |
| EP1392657A2 (en) | Protease inhibitors | |
| JP2005232149A (ja) | ４−ピリジルアルキルチオ基を置換基として有する新規化合物 | |
| US20030044399A1 (en) | Method of treatment | |
| EP1289980A1 (en) | Bicyclyl or heterobicyclylmethanesulfonylamino-substituted n-hydroxyformamides | |
| MXPA01006613A (en) | Protease inhibitors | |
| US20040038965A1 (en) | Protease inhibitors |