KR20110099028A

KR20110099028A - 항세균제로서의 신규 반-합성 글리코펩티드

항세균제로서의 신규 반-합성 글리코펩티드 Download PDF

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Publication number: KR20110099028A
Authority: KR; South Korea
Prior art keywords: alkyl; alkoxy; substituted; compound; resistant
Prior art date: 2008-12-05
Legal status : Withdrawn

Application number

KR1020117015395A

Other languages

English (en)

Korean (ko)

Inventor

다니엘 추

타오 예

빙 왕

Original Assignee

바이오마린 파머수티컬 인크.

Priority date

2008-12-05

Filing date

2009-09-01

Publication date

2011-09-05

2008-12-05 Priority claimed from PCT/US2008/085716 external-priority patent/WO2009085562A1/en

2009-09-01 Application filed by 바이오마린 파머수티컬 인크. filed Critical 바이오마린 파머수티컬 인크.

2011-09-05 Publication of KR20110099028A publication Critical patent/KR20110099028A/ko

Status Withdrawn legal-status Critical Current

Links

108010015899 Glycopeptides Proteins 0.000 title abstract description 25
102000002068 Glycopeptides Human genes 0.000 title abstract description 25
239000003242 anti bacterial agent Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 691
238000000034 method Methods 0.000 claims abstract description 203
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 93
239000002253 acid Substances 0.000 claims abstract description 19
125000003277 amino group Chemical group 0.000 claims abstract description 19
150000002772 monosaccharides Chemical class 0.000 claims abstract description 18
235000000346 sugar Nutrition 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 16
125000002252 acyl group Chemical group 0.000 claims abstract description 11
150000001408 amides Chemical class 0.000 claims abstract description 10
230000000844 anti-bacterial effect Effects 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims description 229
229910052739 hydrogen Inorganic materials 0.000 claims description 226
239000001257 hydrogen Substances 0.000 claims description 226
150000002148 esters Chemical class 0.000 claims description 224
229940002612 prodrug Drugs 0.000 claims description 222
239000000651 prodrug Substances 0.000 claims description 222
239000012453 solvate Substances 0.000 claims description 222
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 219
125000000217 alkyl group Chemical group 0.000 claims description 200
125000001072 heteroaryl group Chemical group 0.000 claims description 156
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 142
125000003118 aryl group Chemical group 0.000 claims description 112
229910052736 halogen Inorganic materials 0.000 claims description 97
150000002367 halogens Chemical class 0.000 claims description 97
125000001424 substituent group Chemical group 0.000 claims description 86
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 84
150000002431 hydrogen Chemical class 0.000 claims description 78
125000003107 substituted aryl group Chemical group 0.000 claims description 65
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 54
125000003342 alkenyl group Chemical group 0.000 claims description 51
-1 alkyl compound Chemical class 0.000 claims description 50
125000000753 cycloalkyl group Chemical group 0.000 claims description 47
125000004429 atom Chemical group 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 41
125000000304 alkynyl group Chemical group 0.000 claims description 38
125000000392 cycloalkenyl group Chemical group 0.000 claims description 35
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
125000003282 alkyl amino group Chemical group 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 26
125000004104 aryloxy group Chemical group 0.000 claims description 23
150000001413 amino acids Chemical class 0.000 claims description 22
125000004663 dialkyl amino group Chemical group 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 13
150000003138 primary alcohols Chemical class 0.000 claims description 12
125000000547 substituted alkyl group Chemical group 0.000 claims description 12
125000005418 aryl aryl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000005415 substituted alkoxy group Chemical group 0.000 claims description 10
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000000524 functional group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
125000005124 aminocycloalkyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
230000002152 alkylating effect Effects 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 3
150000001345 alkine derivatives Chemical class 0.000 claims description 3
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000010511 deprotection reaction Methods 0.000 claims description 3
150000002466 imines Chemical class 0.000 claims description 3
238000006268 reductive amination reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
238000011282 treatment Methods 0.000 abstract description 151
125000004122 cyclic group Chemical group 0.000 abstract description 13
208000035143 Bacterial infection Diseases 0.000 abstract description 12
208000022362 bacterial infectious disease Diseases 0.000 abstract description 12
229940126062 Compound A Drugs 0.000 abstract description 11
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract description 11
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract description 9
230000010933 acylation Effects 0.000 abstract description 6
238000005917 acylation reaction Methods 0.000 abstract description 6
239000012948 isocyanate Substances 0.000 abstract description 6
238000007385 chemical modification Methods 0.000 abstract description 5
150000002513 isocyanates Chemical class 0.000 abstract description 4
150000002016 disaccharides Chemical group 0.000 abstract description 3
230000006806 disease prevention Effects 0.000 abstract description 3
230000002194 synthesizing effect Effects 0.000 abstract description 3
230000002378 acidificating effect Effects 0.000 abstract description 2
150000002336 glycosamine derivatives Chemical class 0.000 abstract description 2
230000003301 hydrolyzing effect Effects 0.000 abstract 1
108090000765 processed proteins & peptides Proteins 0.000 abstract 1
241000894006 Bacteria Species 0.000 description 992
229930186147 Cephalosporin Natural products 0.000 description 120
229940124587 cephalosporin Drugs 0.000 description 120
150000001780 cephalosporins Chemical class 0.000 description 120
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 91
229960003085 meticillin Drugs 0.000 description 91
239000003782 beta lactam antibiotic agent Substances 0.000 description 49
239000002132 β-lactam antibiotic Substances 0.000 description 49
229940124586 β-lactam antibiotics Drugs 0.000 description 49
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 35
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 24
YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 description 24
229960001585 dicloxacillin Drugs 0.000 description 24
ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 24
229960002182 imipenem Drugs 0.000 description 24
DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 24
229960002260 meropenem Drugs 0.000 description 24
AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 description 22
229960000895 doripenem Drugs 0.000 description 22
229940024606 amino acid Drugs 0.000 description 20
235000001014 amino acid Nutrition 0.000 description 20
238000001990 intravenous administration Methods 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
FMZXNVLFJHCSAF-DNVCBOLYSA-N (6R,7R)-3-[(4-carbamoyl-1-pyridin-1-iumyl)methyl]-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CC=3SC=CC=3)[C@H]2SC1 FMZXNVLFJHCSAF-DNVCBOLYSA-N 0.000 description 12
XSPUSVIQHBDITA-KXDGEKGBSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 XSPUSVIQHBDITA-KXDGEKGBSA-N 0.000 description 12
241000837162 Astragalus aureus Species 0.000 description 12
UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 description 12
241000192125 Firmicutes Species 0.000 description 12
UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
229930182555 Penicillin Natural products 0.000 description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
238000011529 RT qPCR Methods 0.000 description 12
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 12
229950004030 cefaloglycin Drugs 0.000 description 12
229960003866 cefaloridine Drugs 0.000 description 12
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 12
229960000603 cefalotin Drugs 0.000 description 12
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 12
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 12
229960002420 cefatrizine Drugs 0.000 description 12
229960005312 cefazedone Drugs 0.000 description 12
VTLCNEGVSVJLDN-MLGOLLRUSA-N cefazedone Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3C=C(Cl)C(=O)C(Cl)=C3)[C@H]2SC1 VTLCNEGVSVJLDN-MLGOLLRUSA-N 0.000 description 12
229960001139 cefazolin Drugs 0.000 description 12
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 12
HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 description 12
229960002100 cefepime Drugs 0.000 description 12
WYUSVOMTXWRGEK-HBWVYFAYSA-N cefpodoxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/OC)\C1=CSC(N)=N1 WYUSVOMTXWRGEK-HBWVYFAYSA-N 0.000 description 12
229960005090 cefpodoxime Drugs 0.000 description 12
ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 12
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DZMVCVMFETWNIU-LDYMZIIASA-N ceftezole Chemical compound O=C([C@@H](NC(=O)CN1N=NN=C1)[C@H]1SC2)N1C(C(=O)O)=C2CSC1=NN=CS1 DZMVCVMFETWNIU-LDYMZIIASA-N 0.000 description 12
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WJXAHFZIHLTPFR-JLRJEBFFSA-N ceftiolene Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1\C=C\SC1=NNC(=O)C(=O)N1CC=O WJXAHFZIHLTPFR-JLRJEBFFSA-N 0.000 description 12
229950008880 ceftiolene Drugs 0.000 description 12
VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 description 12
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JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 12
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