TW200940083A

TW200940083A - Novel semi-synthetic glycopeptides as antibacterial agents

Novel semi-synthetic glycopeptides as antibacterial agents Download PDF

Info

Publication number: TW200940083A
Authority: TW; Taiwan
Prior art keywords: group; substituted; compound; alkyl; alkoxy
Prior art date: 2007-12-26

Application number

TW097149455A

Other languages

English (en)

Chinese (zh)

Inventor

Daniel Chu

Tao Ye

Original Assignee

Lead Therapeutics Inc

Priority date

2007-12-26

Filing date

2008-12-18

Publication date

2009-10-01

2008-12-18 Application filed by Lead Therapeutics Inc filed Critical Lead Therapeutics Inc

2009-10-01 Publication of TW200940083A publication Critical patent/TW200940083A/zh

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108010015899 Glycopeptides Proteins 0.000 title abstract description 24
102000002068 Glycopeptides Human genes 0.000 title abstract description 24
239000003242 anti bacterial agent Substances 0.000 title description 13
150000001875 compounds Chemical class 0.000 claims abstract description 758
-1 amino acid asparagines Chemical class 0.000 claims abstract description 120
238000000034 method Methods 0.000 claims abstract description 109
230000015572 biosynthetic process Effects 0.000 claims abstract description 99
125000003277 amino group Chemical group 0.000 claims abstract description 79
239000002253 acid Substances 0.000 claims abstract description 35
239000012948 isocyanate Substances 0.000 claims abstract description 34
150000002772 monosaccharides Chemical class 0.000 claims abstract description 34
238000011282 treatment Methods 0.000 claims abstract description 34
238000006243 chemical reaction Methods 0.000 claims abstract description 32
235000000346 sugar Nutrition 0.000 claims abstract description 29
150000002513 isocyanates Chemical class 0.000 claims abstract description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 23
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
230000015556 catabolic process Effects 0.000 claims abstract description 5
238000006731 degradation reaction Methods 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 374
125000003545 alkoxy group Chemical group 0.000 claims description 192
229910052739 hydrogen Inorganic materials 0.000 claims description 154
239000001257 hydrogen Substances 0.000 claims description 154
125000001072 heteroaryl group Chemical group 0.000 claims description 143
125000003118 aryl group Chemical group 0.000 claims description 91
229910052736 halogen Inorganic materials 0.000 claims description 88
150000002367 halogens Chemical class 0.000 claims description 85
125000001424 substituent group Chemical group 0.000 claims description 80
125000003107 substituted aryl group Chemical group 0.000 claims description 70
150000001412 amines Chemical class 0.000 claims description 68
239000000203 mixture Substances 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 67
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 59
150000002431 hydrogen Chemical class 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
125000003282 alkyl amino group Chemical group 0.000 claims description 51
125000004429 atom Chemical group 0.000 claims description 51
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 51
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
125000000753 cycloalkyl group Chemical group 0.000 claims description 47
239000000651 prodrug Substances 0.000 claims description 47
229940002612 prodrug Drugs 0.000 claims description 47
125000003396 thiol group Chemical class [H]S* 0.000 claims description 45
150000001413 amino acids Chemical class 0.000 claims description 44
239000012453 solvate Substances 0.000 claims description 43
150000002148 esters Chemical class 0.000 claims description 38
125000003342 alkenyl group Chemical group 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 36
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
125000004663 dialkyl amino group Chemical group 0.000 claims description 33
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125000000392 cycloalkenyl group Chemical group 0.000 claims description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical class COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000005309 thioalkoxy group Chemical group 0.000 claims description 22
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 21
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QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
125000004104 aryloxy group Chemical group 0.000 claims description 21
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
150000003141 primary amines Chemical class 0.000 claims description 17
238000006467 substitution reaction Methods 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
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239000011593 sulfur Substances 0.000 claims description 16
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
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125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
150000002678 macrocyclic compounds Chemical class 0.000 claims description 10
230000029936 alkylation Effects 0.000 claims description 9
238000005804 alkylation reaction Methods 0.000 claims description 9
125000005418 aryl aryl group Chemical group 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
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239000000052 vinegar Substances 0.000 claims description 9
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241000124008 Mammalia Species 0.000 claims description 8
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XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
239000007789 gas Substances 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
238000012360 testing method Methods 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 6
150000002466 imines Chemical class 0.000 claims description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 6
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
238000006268 reductive amination reaction Methods 0.000 claims description 5
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 4
229960003805 amantadine Drugs 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
150000003512 tertiary amines Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
108010011485 Aspartame Proteins 0.000 claims description 3
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 claims description 3
150000001345 alkine derivatives Chemical class 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
229910052786 argon Inorganic materials 0.000 claims description 3
239000000605 aspartame Substances 0.000 claims description 3
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 3
235000010357 aspartame Nutrition 0.000 claims description 3
229960003438 aspartame Drugs 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
238000006352 cycloaddition reaction Methods 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
MQPWZOCJUCOTTB-UHFFFAOYSA-L [O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.[I+2]C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.[I+2]C1=CC=CC=C1 MQPWZOCJUCOTTB-UHFFFAOYSA-L 0.000 claims description 2
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125000000524 functional group Chemical group 0.000 claims description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 claims 1
125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
235000013877 carbamide Nutrition 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
150000001925 cycloalkenes Chemical class 0.000 claims 1
201000006549 dyspepsia Diseases 0.000 claims 1
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125000004926 indolenyl group Chemical group 0.000 claims 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims 1
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