ZA200400928B - Novel depsipeptides and process for preparing same. - Google Patents

Info

Publication number

ZA200400928B

ZA200400928B ZA200400928A ZA200400928A ZA200400928B ZA 200400928 B ZA200400928 B ZA 200400928B ZA 200400928 A ZA200400928 A ZA 200400928A ZA 200400928 A ZA200400928 A ZA 200400928A ZA 200400928 B ZA200400928 B ZA 200400928B

Authority

ZA

South Africa

Prior art keywords

compound

amino

methyl

formula

hydrido

Prior art date

2001-08-06

Links

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• Global Dossier
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• 238000004519 manufacturing process Methods 0.000 title claims description 9
• 108010002156 Depsipeptides Proteins 0.000 title description 29
• 150000001875 compounds Chemical class 0.000 claims abstract description 306
• 238000000034 method Methods 0.000 claims abstract description 96
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• -1 amino, monosubstituted amino Chemical group 0.000 claims description 234
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 95
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
• 125000006239 protecting group Chemical group 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 62
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 60
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 239000003795 chemical substances by application Substances 0.000 claims description 53
• 239000000203 mixture Substances 0.000 claims description 43
• 125000004442 acylamino group Chemical group 0.000 claims description 39
• 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 230000008569 process Effects 0.000 claims description 25
• 125000003275 alpha amino acid group Chemical group 0.000 claims description 20
• 125000000539 amino acid group Chemical group 0.000 claims description 20
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 11
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
• 208000035143 Bacterial infection Diseases 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 10
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
• 125000001589 carboacyl group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 7
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
• HLHSUNWAPXINQU-GQCTYLIASA-N (E)-3-(3,4-dihydroxyphenyl)-N-prop-2-ynylprop-2-enamide Chemical compound OC=1C=C(C=CC=1O)/C=C/C(=O)NCC#C HLHSUNWAPXINQU-GQCTYLIASA-N 0.000 claims 1
• 208000035823 Non-specific autoimmune cerebellar ataxia without characteristic antibodies Diseases 0.000 claims 1
• 229920000771 poly (alkylcyanoacrylate) Polymers 0.000 claims 1
• OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical class O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 abstract description 20
• 239000000543 intermediate Substances 0.000 abstract description 10
• 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
• AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 100
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• 238000006243 chemical reaction Methods 0.000 description 82
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• 239000000243 solution Substances 0.000 description 55
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 46
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 44
• 239000011541 reaction mixture Substances 0.000 description 41
• 125000000623 heterocyclic group Chemical class 0.000 description 39
• 125000003118 aryl group Chemical group 0.000 description 37
• 125000001072 heteroaryl group Chemical group 0.000 description 36
• 238000011282 treatment Methods 0.000 description 36
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• 230000008878 coupling Effects 0.000 description 19
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• 238000005859 coupling reaction Methods 0.000 description 19
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• 229940024606 amino acid Drugs 0.000 description 18
• 235000001014 amino acid Nutrition 0.000 description 17
• 239000003242 anti bacterial agent Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 125000003342 alkenyl group Chemical group 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 14
• 125000004104 aryloxy group Chemical group 0.000 description 14
• 239000000047 product Substances 0.000 description 14
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• 239000002253 acid Chemical class 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 125000002252 acyl group Chemical group 0.000 description 12
• 125000003545 alkoxy group Chemical group 0.000 description 12
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• 208000015181 infectious disease Diseases 0.000 description 12
• 150000003254 radicals Chemical class 0.000 description 12
• 108010013198 Daptomycin Proteins 0.000 description 11
• 125000000304 alkynyl group Chemical group 0.000 description 11
• 239000002585 base Substances 0.000 description 11
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• 238000002360 preparation method Methods 0.000 description 11
• 125000004423 acyloxy group Chemical group 0.000 description 10
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 10
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• 230000020176 deacylation Effects 0.000 description 10
• 238000005947 deacylation reaction Methods 0.000 description 10
• 125000002795 guanidino group Chemical class C(N)(=N)N* 0.000 description 10
• 238000001990 intravenous administration Methods 0.000 description 10
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• 230000015556 catabolic process Effects 0.000 description 9
• 238000006731 degradation reaction Methods 0.000 description 9
• 125000005843 halogen group Chemical class 0.000 description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 9
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 9
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 9
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