DE60013147T2 - Caspase-hemmer - Google Patents

Info

Publication number

DE60013147T2

DE60013147T2 DE60013147T DE60013147T DE60013147T2 DE 60013147 T2 DE60013147 T2 DE 60013147T2 DE 60013147 T DE60013147 T DE 60013147T DE 60013147 T DE60013147 T DE 60013147T DE 60013147 T2 DE60013147 T2 DE 60013147T2

Authority

DE

Germany

Prior art keywords

carbonylamino

methyl

propyl

dihydro

isoxazole

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 - Lifetime

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• Global Dossier
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• 108010076667 Caspases Proteins 0.000 title claims abstract description 69
• 102000011727 Caspases Human genes 0.000 title claims abstract description 68
• 239000003112 inhibitor Substances 0.000 title description 26
• 238000006243 chemical reaction Methods 0.000 claims abstract description 38
• 150000002547 isoxazolines Chemical class 0.000 claims abstract description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 208000006454 hepatitis Diseases 0.000 claims abstract description 19
• 150000002148 esters Chemical class 0.000 claims abstract description 18
• 231100000283 hepatitis Toxicity 0.000 claims abstract description 18
• 238000002054 transplantation Methods 0.000 claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 206010012289 Dementia Diseases 0.000 claims abstract description 7
• 206010061218 Inflammation 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
• 206010012601 diabetes mellitus 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
• 201000005917 gastric ulcer Diseases 0.000 claims abstract description 5
• 230000004054 inflammatory process Effects 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 214
• -1 ethanesulfonyl Chemical group 0.000 claims description 179
• 239000000203 mixture Substances 0.000 claims description 96
• 230000006907 apoptotic process Effects 0.000 claims description 66
• 210000004027 cell Anatomy 0.000 claims description 48
• 238000011282 treatment Methods 0.000 claims description 37
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 21
• 150000001413 amino acids Chemical class 0.000 claims description 19
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
• 238000002347 injection Methods 0.000 claims description 17
• 239000007924 injection Substances 0.000 claims description 17
• 229940123169 Caspase inhibitor Drugs 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 230000004913 activation Effects 0.000 claims description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 208000007788 Acute Liver Failure Diseases 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 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 6
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
• 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 5
• QYZMOSOGHHPYDR-MIQQLYACSA-N (3s)-5-(2,6-dichlorobenzoyl)oxy-3-[[5-methyl-3-[(1s)-2-methyl-1-(naphthalene-1-carbonylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1(C)ON=C(C1)[C@@H](NC(=O)C=1C2=CC=CC=C2C=CC=1)C(C)C)COC(=O)C1=C(Cl)C=CC=C1Cl QYZMOSOGHHPYDR-MIQQLYACSA-N 0.000 claims description 5
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 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 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
• 150000001923 cyclic compounds Chemical class 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000006239 protecting group Chemical group 0.000 claims description 4
• 229930192474 thiophene Natural products 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
• 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 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
• 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 3
• VWTNLBJARJITTF-YXBGZAQISA-N (3s)-3-[[5-benzyl-3-[(1s)-2-methyl-1-(quinoline-8-carbonylamino)propyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2C3=NC=CC=C3C=CC=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 VWTNLBJARJITTF-YXBGZAQISA-N 0.000 claims description 3
• ZNBNYEUEHILAPB-ALVJRTDLSA-N (3s)-5-(2,6-dichlorobenzoyl)oxy-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(=O)COC(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)OCC1=CC=CC=C1 ZNBNYEUEHILAPB-ALVJRTDLSA-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
• 206010000804 Acute hepatic failure Diseases 0.000 claims description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• AMIUCRNGFBJBIT-VMZLPSRASA-N (3S)-3-[[5-benzyl-3-[(1S)-1-[[2-(1H-indol-3-yl)acetyl]amino]-2-methylpropyl]-4H-1,2-oxazole-5-carbonyl]amino]-5-diazo-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)CC1=CC=CC=C1)C AMIUCRNGFBJBIT-VMZLPSRASA-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
• 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
• PTQUKSDULXNXDR-MJLQIQFDSA-N (3S)-5-diazo-3-[methyl-[3-[(1S)-2-methyl-1-(naphthalen-1-ylsulfonylamino)propyl]-5-phenyl-4H-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic acid Chemical compound CC(C)[C@H](NS(=O)(=O)c1cccc2ccccc12)C1=NOC(C1)(C(=O)N(C)[C@@H](CC(O)=O)C(=O)C=[N+]=[N-])c1ccccc1 PTQUKSDULXNXDR-MJLQIQFDSA-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
• UDKCKQILALRKRO-XOQPTCEHSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]-4-oxo-5-phenoxypentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2C=C3C=CC=CC3=CC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C=CC=CC=1)COC1=CC=CC=C1 UDKCKQILALRKRO-XOQPTCEHSA-N 0.000 claims description 2
• WECVYUDZYICKDV-NXUCYVCNSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]-5-naphthalen-1-yloxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2C=C3C=CC=CC3=CC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C2=CC=CC=C2C=CC=1)COC1=CC=CC=C1 WECVYUDZYICKDV-NXUCYVCNSA-N 0.000 claims description 2
• BFAKORDSYJJDDO-SNXXJJMMSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(naphthalene-2-carbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]-5-naphthalen-2-yloxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)C=2C=C3C=CC=CC3=CC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C=C2C=CC=CC2=CC=1)COC1=CC=CC=C1 BFAKORDSYJJDDO-SNXXJJMMSA-N 0.000 claims description 2
• XVXKVVGJBYDHLE-HXVHBBJOSA-N (3s)-3-[[3-[(1s)-2-methyl-1-(quinoline-2-carbonylamino)propyl]-5-(phenoxymethyl)-4h-1,2-oxazole-5-carbonyl]amino]-4-oxopentanoic 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(C)=O)COC1=CC=CC=C1 XVXKVVGJBYDHLE-HXVHBBJOSA-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
• KKWSENWDEWIJOL-YXBGZAQISA-N (3s)-3-[[5-benzyl-3-[(1s)-1-(isoquinoline-1-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=C3C=CN=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 KKWSENWDEWIJOL-YXBGZAQISA-N 0.000 claims description 2
• AKXQAZGFKWMLQL-SJVPFVBJSA-N (3s)-3-[[5-benzyl-3-[(1s)-1-[[2-(1h-indol-3-yl)acetyl]amino]-2-methylpropyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-(2,6-dichlorobenzoyl)oxy-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)CC=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 AKXQAZGFKWMLQL-SJVPFVBJSA-N 0.000 claims description 2
• FSCBFBMBTAUVPR-VMZLPSRASA-N (3s)-3-[[5-benzyl-3-[(1s)-1-[[2-(1h-indol-3-yl)acetyl]amino]-2-methylpropyl]-4h-1,2-oxazole-5-carbonyl]amino]-5-bromo-4-oxopentanoic acid Chemical compound C1C([C@@H](NC(=O)CC=2C3=CC=CC=C3NC=2)C(C)C)=NOC1(C(=O)N[C@@H](CC(O)=O)C(=O)CBr)CC1=CC=CC=C1 FSCBFBMBTAUVPR-VMZLPSRASA-N 0.000 claims description 2
• MAXNYXFKLCHDCT-HVZFRMHZSA-N (3s)-3-[[5-benzyl-3-[(1s)-2-methyl-1-(3-phenylpropanoylamino)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)CCC1=CC=CC=C1 MAXNYXFKLCHDCT-HVZFRMHZSA-N 0.000 claims description 2
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