JP4990456B2 - 抗菌剤としてのダプトマイシンアナログ - Google Patents

Info

Publication number

JP4990456B2

JP4990456B2 JP2001544761A JP2001544761A JP4990456B2 JP 4990456 B2 JP4990456 B2 JP 4990456B2 JP 2001544761 A JP2001544761 A JP 2001544761A JP 2001544761 A JP2001544761 A JP 2001544761A JP 4990456 B2 JP4990456 B2 JP 4990456B2

Authority

JP

Japan

Prior art keywords

compound

alkyl

compounds

group

heterocyclyl

Prior art date

1999-12-15

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

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• DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical class C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 title description 43
• 239000003242 anti bacterial agent Substances 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims description 231
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 150000003839 salts Chemical class 0.000 claims description 31
• 238000006467 substitution reaction Methods 0.000 claims description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 98
• -1 Pyridinyl ring Chemical group 0.000 description 81
• 239000011347 resin Substances 0.000 description 73
• 229920005989 resin Polymers 0.000 description 73
• 125000000623 heterocyclic group Chemical group 0.000 description 70
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• 125000001072 heteroaryl group Chemical group 0.000 description 63
• 125000003118 aryl group Chemical group 0.000 description 62
• 125000000753 cycloalkyl group Chemical group 0.000 description 59
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
• 239000000203 mixture Substances 0.000 description 55
• 108010028921 Lipopeptides Proteins 0.000 description 50
• 125000003342 alkenyl group Chemical group 0.000 description 45
• 108010013198 Daptomycin Proteins 0.000 description 42
• 229960005484 daptomycin Drugs 0.000 description 42
• 238000000034 method Methods 0.000 description 41
• 125000000304 alkynyl group Chemical group 0.000 description 39
• 125000003545 alkoxy group Chemical group 0.000 description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 35
• 235000002639 sodium chloride Nutrition 0.000 description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
• 239000007787 solid Substances 0.000 description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
• 125000005843 halogen group Chemical group 0.000 description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 25
• 125000001424 substituent group Chemical group 0.000 description 25
• 238000002360 preparation method Methods 0.000 description 23
• 239000004254 Ammonium phosphate Substances 0.000 description 20
• 229910000148 ammonium phosphate Inorganic materials 0.000 description 20
• 235000019289 ammonium phosphates Nutrition 0.000 description 20
• 125000004104 aryloxy group Chemical group 0.000 description 20
• MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 18
• 150000001413 amino acids Chemical group 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• 239000000872 buffer Substances 0.000 description 16
• 125000006239 protecting group Chemical group 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000002252 acyl group Chemical group 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 239000008194 pharmaceutical composition Substances 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 125000004442 acylamino group Chemical group 0.000 description 14
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
• 125000004093 cyano group Chemical group *C#N 0.000 description 14
• 238000001704 evaporation Methods 0.000 description 14
• 230000008020 evaporation Effects 0.000 description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
• 125000004423 acyloxy group Chemical group 0.000 description 13
• 125000004414 alkyl thio group Chemical group 0.000 description 13
• 150000004678 hydrides Chemical class 0.000 description 13
• 208000015181 infectious disease Diseases 0.000 description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 229940024606 amino acid Drugs 0.000 description 12
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• 229910052799 carbon Inorganic materials 0.000 description 12
• 239000003153 chemical reaction reagent 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
• 230000002829 reductive effect Effects 0.000 description 12
• BVUSBMILHOAJLP-ILWJCMRDSA-N tryptophan daptomycin Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1.C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N BVUSBMILHOAJLP-ILWJCMRDSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 description 11
• 150000003254 radicals Chemical class 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 208000035143 Bacterial infection Diseases 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• 208000022362 bacterial infectious disease Diseases 0.000 description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
• 230000008878 coupling Effects 0.000 description 10
• 238000010168 coupling process Methods 0.000 description 10
• 238000005859 coupling reaction Methods 0.000 description 10
• 239000003814 drug Substances 0.000 description 10
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• 239000000725 suspension Substances 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• 238000011282 treatment Methods 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 230000004048 modification Effects 0.000 description 9
• 238000012986 modification Methods 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• 241000894006 Bacteria Species 0.000 description 8
• 108090000790 Enzymes Proteins 0.000 description 8
• 102000004190 Enzymes Human genes 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• 238000001990 intravenous administration Methods 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• 244000052769 pathogen Species 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 229910052717 sulfur Inorganic materials 0.000 description 8
• 241000192125 Firmicutes Species 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 229940088710 antibiotic agent Drugs 0.000 description 7
• 150000001540 azides Chemical class 0.000 description 7
• 229940125782 compound 2 Drugs 0.000 description 7
• 125000001145 hydrido group Chemical group *[H] 0.000 description 7
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 0 CCC(*)(c1ccccc1*)N Chemical compound CCC(*)(c1ccccc1*)N 0.000 description 6
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 description 6
• 230000000845 anti-microbial effect Effects 0.000 description 6
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• 230000001580 bacterial effect Effects 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• 238000001802 infusion Methods 0.000 description 6
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• 238000012360 testing method Methods 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 5
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 5
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 5
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 5
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 5
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 108010059993 Vancomycin Proteins 0.000 description 5
• 229940121375 antifungal agent Drugs 0.000 description 5
• 238000004113 cell culture Methods 0.000 description 5
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• SGCKSDJIMSBTFY-UHFFFAOYSA-N n-sulfonylformamide Chemical compound O=CN=S(=O)=O SGCKSDJIMSBTFY-UHFFFAOYSA-N 0.000 description 5
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• 125000004043 oxo group Chemical group O=* 0.000 description 5
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• HOAIHZDQHXHYOO-UHFFFAOYSA-N undecylurea Chemical compound CCCCCCCCCCCNC(N)=O HOAIHZDQHXHYOO-UHFFFAOYSA-N 0.000 description 5
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 5
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