CA2388564C - Caspase inhibitor - Google Patents

Info

Publication number

CA2388564C

CA2388564C CA002388564A CA2388564A CA2388564C CA 2388564 C CA2388564 C CA 2388564C CA 002388564 A CA002388564 A CA 002388564A CA 2388564 A CA2388564 A CA 2388564A CA 2388564 C CA2388564 C CA 2388564C

Authority

CA

Canada

Prior art keywords

methyl

carbonylamino

propyl

isoxazole

dihydro

Prior art date

1999-09-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

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• Global Dossier
• CIPO
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• 229940123169 Caspase inhibitor Drugs 0.000 title claims description 22
• 108010076667 Caspases Proteins 0.000 claims abstract description 61
• 102000011727 Caspases Human genes 0.000 claims abstract description 60
• 150000002547 isoxazolines Chemical class 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 201000010099 disease Diseases 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 150000002148 esters Chemical class 0.000 claims abstract description 19
• 208000006454 hepatitis Diseases 0.000 claims abstract description 18
• 231100000283 hepatitis Toxicity 0.000 claims abstract description 17
• 238000004519 manufacturing process Methods 0.000 claims abstract description 14
• 238000002054 transplantation Methods 0.000 claims abstract description 11
• 206010061218 Inflammation Diseases 0.000 claims abstract description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 206010012289 Dementia Diseases 0.000 claims abstract description 7
• 206010040047 Sepsis Diseases 0.000 claims abstract description 7
• 208000007107 Stomach Ulcer Diseases 0.000 claims abstract description 6
• 208000006011 Stroke Diseases 0.000 claims abstract description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 6
• 201000005917 gastric ulcer Diseases 0.000 claims abstract description 6
• 210000000056 organ Anatomy 0.000 claims abstract description 6
• 208000030507 AIDS Diseases 0.000 claims abstract description 5
• 230000004054 inflammatory process Effects 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 239
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 100
• -1 ethanesulfonyl Chemical group 0.000 claims description 82
• 239000000203 mixture Substances 0.000 claims description 78
• 230000006907 apoptotic process Effects 0.000 claims description 65
• 210000004027 cell Anatomy 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 238000006243 chemical reaction Methods 0.000 claims description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 208000007788 Acute Liver Failure Diseases 0.000 claims description 22
• 206010000804 Acute hepatic failure Diseases 0.000 claims description 22
• 150000001413 amino acids Chemical class 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 238000002347 injection Methods 0.000 claims description 16
• 239000007924 injection Substances 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 15
• 230000004913 activation Effects 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
• 208000035196 congenital hypomyelinating 2 neuropathy Diseases 0.000 claims description 7
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 150000001923 cyclic compounds Chemical class 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• AMIBKSPSWDLSAW-JERZPMBSSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound C1([C@@H](NC(=O)C=2C=C3C=CC=CC3=CC=2)C(C)C)=NOC(C(=O)N[C@@H](CC(O)=O)C(C)=O)C1 AMIBKSPSWDLSAW-JERZPMBSSA-N 0.000 claims description 3
• BEYPDRJSGSEUJE-KHLAINANSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-5-naphthalen-2-yloxy-4-oxopentanoic acid Chemical compound C1=CC=CC2=CC(OCC(=O)[C@H](CC(O)=O)NC(=O)C3ON=C(C3)[C@@H](NC(=O)C=3C=C4C=CC=CC4=CC=3)C(C)C)=CC=C21 BEYPDRJSGSEUJE-KHLAINANSA-N 0.000 claims description 3
• XHPWBJPWEBWAKH-UMQIIANQSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1ON=C(C1)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)COC1=CC=CC=C1 XHPWBJPWEBWAKH-UMQIIANQSA-N 0.000 claims description 3
• WTAJUWQGBFCFJD-SXVPRHBSSA-N (3s)-5-(2,6-dichlorobenzoyl)oxy-3-[[3-[(1s)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1ON=C(C1)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)COC(=O)C1=C(Cl)C=CC=C1Cl WTAJUWQGBFCFJD-SXVPRHBSSA-N 0.000 claims description 3
• 230000006735 deficit Effects 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• CAFXLBCDFMSQEF-OZEVUELHSA-N (2s)-2-[[3-[(1s)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]butanedioic acid Chemical compound N([C@@H](C(C)C)C=1CC(COC=2C=CC=CC=2)(ON=1)C(=O)N[C@@H](CC(O)=O)C(O)=O)C(=O)OCC1=CC=CC=C1 CAFXLBCDFMSQEF-OZEVUELHSA-N 0.000 claims description 2
• VJWAKIOTFVYEBR-CJWOSIJFSA-N (3S)-3-[[3-[(1S)-1-(benzylsulfonylamino)-2-methylpropyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]-methylamino]-5-diazo-4-oxopentanoic acid Chemical compound CC(C)[C@H](NS(=O)(=O)Cc1ccccc1)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])c1ccccc1 VJWAKIOTFVYEBR-CJWOSIJFSA-N 0.000 claims description 2
• LYBOETQAQKFHRN-UCWKTWOXSA-N (3S)-3-[[5-benzyl-3-[(1S)-2-methyl-1-(3-phenylprop-2-enoylamino)propyl]-4H-1,2-oxazole-5-carbonyl]amino]-5-diazo-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)C=Cc1ccccc1)C1=NOC(Cc2ccccc2)(C1)C(=O)N[C@@H](CC(O)=O)C(=O)C=[N+]=[N-] LYBOETQAQKFHRN-UCWKTWOXSA-N 0.000 claims description 2
• GQLIIMJKTVIQDZ-WVLLBIQGSA-N (3S)-3-[methyl-[3-[(1S)-2-methyl-1-(naphthalen-2-ylsulfonylamino)propyl]-5-phenoxy-4H-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N[C@@H](C(C)C)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(COC1=CC=CC=C1)=O)C)OC1=CC=CC=C1 GQLIIMJKTVIQDZ-WVLLBIQGSA-N 0.000 claims description 2
• IDSSUOKXTIHRGT-SNXXJJMMSA-N (3S)-3-[methyl-[3-[(1S)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-5-phenoxy-4H-1,2-oxazole-5-carbonyl]amino]-5-naphthalen-1-yloxy-4-oxopentanoic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)N[C@@H](C(C)C)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(COC1=CC=CC2=CC=CC=C12)=O)C)OC1=CC=CC=C1 IDSSUOKXTIHRGT-SNXXJJMMSA-N 0.000 claims description 2
• URCPIFXUJIAFPO-YOGAAICWSA-N (3S)-5-(2,6-dichlorobenzoyl)oxy-3-[[3-[(1S)-1-(isoquinoline-3-carbonylamino)-2-methylpropyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]-methylamino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)c1cc2ccccc2cn1)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)COC(=O)c1c(Cl)cccc1Cl)c1ccccc1 URCPIFXUJIAFPO-YOGAAICWSA-N 0.000 claims description 2
• XOQBEABUTUIXHL-RXKSKBTASA-N (3S)-5-bromo-3-[methyl-[3-[(1S)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-5-phenoxy-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)N[C@@H](C(C)C)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(CBr)=O)C)OC1=CC=CC=C1 XOQBEABUTUIXHL-RXKSKBTASA-N 0.000 claims description 2
• YJNIJSRWVQSXPX-JWFRVCKNSA-N (3S)-5-diazo-3-[[3-[(1S)-1-[3-(1H-indol-3-yl)propanoylamino]-2-methylpropyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]-methylamino]-4-oxopentanoic acid Chemical compound CC([C@H](NC(=O)CCC1=CNC2=CC=CC=C12)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(C=[N+]=[N-])=O)C)C1=CC=CC=C1)C YJNIJSRWVQSXPX-JWFRVCKNSA-N 0.000 claims description 2
• SHSLHDSOCRANTC-MJLQIQFDSA-N (3S)-5-diazo-3-[[3-[(1S)-1-[[2-(1H-indol-3-yl)acetyl]amino]-2-methylpropyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]-methylamino]-4-oxopentanoic acid Chemical compound CC([C@H](NC(=O)CC1=CNC2=CC=CC=C12)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(C=[N+]=[N-])=O)C)C1=CC=CC=C1)C SHSLHDSOCRANTC-MJLQIQFDSA-N 0.000 claims description 2
• IJQDRCQHTQFVRO-OZIHFDBSSA-N (3S)-5-diazo-3-[[3-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)OCc1ccccc1)C1=NOC(C1)C(=O)N[C@@H](CC(O)=O)C(=O)C=[N+]=[N-] IJQDRCQHTQFVRO-OZIHFDBSSA-N 0.000 claims description 2
• BROGERWWRDQCLC-NUOXSBERSA-N (3S)-5-diazo-3-[[3-[(1S)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound C1([C@@H](NC(=O)C=2N=C3C=CC=CC3=CC=2)C(C)C)=NOC(C(=O)N[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])C1 BROGERWWRDQCLC-NUOXSBERSA-N 0.000 claims description 2
• NSEBUYIBQYXRHE-JFCBHCIBSA-N (3S)-5-diazo-3-[methyl-[3-[(1S)-2-methyl-1-(3-phenylpropanoylamino)propyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC([C@H](NC(=O)CCC1=CC=CC=C1)C1=NOC(C1)(C(=O)N([C@@H](CC(=O)O)C(C=[N+]=[N-])=O)C)C1=CC=CC=C1)C NSEBUYIBQYXRHE-JFCBHCIBSA-N 0.000 claims description 2
• OHHNYOJLWDPOSS-RXKSKBTASA-N (3S)-5-diazo-3-[methyl-[3-[(1S)-2-methyl-1-(naphthalene-1-carbonylamino)propyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)c1cccc2ccccc12)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])c1ccccc1 OHHNYOJLWDPOSS-RXKSKBTASA-N 0.000 claims description 2
• OIFGAYYNHNLPDN-SFQDAYOWSA-N (3S)-5-diazo-3-[methyl-[3-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)OCc1ccccc1)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])c1ccccc1 OIFGAYYNHNLPDN-SFQDAYOWSA-N 0.000 claims description 2
• BGIGRGQZRXKGKP-HXVHBBJOSA-N (3S)-5-diazo-3-[methyl-[3-[(1S)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NC(=O)c1ccc2ccccc2n1)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])c1ccccc1 BGIGRGQZRXKGKP-HXVHBBJOSA-N 0.000 claims description 2
• NPYBCRJFMZGCPI-JEVLLQFPSA-N (3s)-3-[[3-[(1s)-1-(benzylsulfonylamino)-2-methylpropyl]-5-phenyl-4h-1,2-oxazole-5-carbonyl]-methylamino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(ON=1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)COC(=O)C=1C(=CC=CC=1Cl)Cl)C=1C=CC=CC=1)S(=O)(=O)CC1=CC=CC=C1 NPYBCRJFMZGCPI-JEVLLQFPSA-N 0.000 claims description 2
• GZQDNGQTIVQLCY-CJWOSIJFSA-N (3s)-3-[[3-[(1s)-1-(benzylsulfonylamino)-2-methylpropyl]-5-phenyl-4h-1,2-oxazole-5-carbonyl]-methylamino]-5-bromo-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(ON=1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)CBr)C=1C=CC=CC=1)S(=O)(=O)CC1=CC=CC=C1 GZQDNGQTIVQLCY-CJWOSIJFSA-N 0.000 claims description 2
• WIEWPGDCGMZZKI-HGAQVFRKSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1ON=C(C1)[C@@H](NC(=O)C=1C=C2C=CC=CC2=CC=1)C(C)C)COC1=CC=CC=C1 WIEWPGDCGMZZKI-HGAQVFRKSA-N 0.000 claims description 2
• QNIUHMFSURKYFW-ZRHIXDKOSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4,5-dihydro-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(ON=1)C(=O)N[C@@H](CC(O)=O)C(C)=O)C(=O)OCC1=CC=CC=C1 QNIUHMFSURKYFW-ZRHIXDKOSA-N 0.000 claims description 2
• JUKMFKWQUZNAMJ-SFQDAYOWSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(COC=2C=CC=CC=2)(ON=1)C(=O)N[C@@H](CC(O)=O)C(C)=O)C(=O)OCC1=CC=CC=C1 JUKMFKWQUZNAMJ-SFQDAYOWSA-N 0.000 claims description 2
• FGUQVUCZQOFWFW-KUVJNVSYSA-N (3s)-3-[[3-[(1s)-3-carboxy-1-(naphthalene-2-carbonylamino)propyl]-5-methyl-4h-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1(ON=C(C1)[C@H](CCC(O)=O)NC(=O)C=1C=C2C=CC=CC2=CC=1)C)COC1=CC=CC=C1 FGUQVUCZQOFWFW-KUVJNVSYSA-N 0.000 claims description 2
• UZQFDHKWLNUAHL-FRAXYZTQSA-N (3s)-3-[[5-(1h-imidazol-2-ylmethyl)-3-[(1s)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2N=C3C=CC=CC3=CC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C=CC=CC=1)CC1=NC=CN1 UZQFDHKWLNUAHL-FRAXYZTQSA-N 0.000 claims description 2
• SGHANKVVISIETA-NUUXIFOFSA-N (3s)-3-[[5-benzyl-3-[(1s)-1-(1h-indole-2-carbonylamino)-2-methylpropyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2NC3=CC=CC=C3C=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC(=O)C=1C(=CC=CC=1Cl)Cl)CC1=CC=CC=C1 SGHANKVVISIETA-NUUXIFOFSA-N 0.000 claims description 2
• JKKFMABMEODGRO-TYNJXUSYSA-N (3s)-3-[[5-benzyl-3-[(1s)-1-(1h-indole-3-carbonylamino)-2-methylpropyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2C3=CC=CC=C3NC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC(=O)C=1C(=CC=CC=1Cl)Cl)CC1=CC=CC=C1 JKKFMABMEODGRO-TYNJXUSYSA-N 0.000 claims description 2
• PIRHZWPTWBUUOY-HVZFRMHZSA-N (3s)-3-[[5-benzyl-3-[(1s)-2-methyl-1-(3-phenylprop-2-enoylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(CC=2C=CC=CC=2)(ON=1)C(=O)N[C@@H](CC(O)=O)C(=O)COC(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C=CC1=CC=CC=C1 PIRHZWPTWBUUOY-HVZFRMHZSA-N 0.000 claims description 2
• PKVQDEXNZLWPRF-UCWKTWOXSA-N (3s)-3-[[5-benzyl-3-[(1s)-2-methyl-1-(3-phenylprop-2-enoylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-bromo-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(CC=2C=CC=CC=2)(ON=1)C(=O)N[C@@H](CC(O)=O)C(=O)CBr)C(=O)C=CC1=CC=CC=C1 PKVQDEXNZLWPRF-UCWKTWOXSA-N 0.000 claims description 2
• UOMFFTQTZBTJLF-UCWKTWOXSA-N (3s)-3-[[5-benzyl-3-[(1s)-2-methyl-1-(3-phenylpropanoylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-bromo-4-oxopentanoic acid Chemical compound N([C@@H](C(C)C)C=1CC(CC=2C=CC=CC=2)(ON=1)C(=O)N[C@@H](CC(O)=O)C(=O)CBr)C(=O)CCC1=CC=CC=C1 UOMFFTQTZBTJLF-UCWKTWOXSA-N 0.000 claims description 2
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