TW201021805A

TW201021805A - Novel semi-synthetic glycopeptides as antibacterial agents

Novel semi-synthetic glycopeptides as antibacterial agents Download PDF

Info

Publication number: TW201021805A
Authority: TW; Taiwan
Prior art keywords: group; compound; alkoxy; alkyl; resistant
Prior art date: 2008-12-05

Application number

TW098129618A

Other languages

English (en)

Chinese (zh)

Inventor

Daniel Chu

Tao Ye

Bing Wang

Original Assignee

Lead Therapeutics Inc

Priority date

2008-12-05

Filing date

2009-09-02

Publication date

2010-06-16

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

2009-09-02 Application filed by Lead Therapeutics Inc filed Critical Lead Therapeutics Inc

2010-06-16 Publication of TW201021805A publication Critical patent/TW201021805A/zh

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 35
150000001875 compounds Chemical class 0.000 claims abstract description 625
238000000034 method Methods 0.000 claims abstract description 280
125000003277 amino group Chemical group 0.000 claims abstract description 84
239000002253 acid Substances 0.000 claims abstract description 29
235000000346 sugar Nutrition 0.000 claims abstract description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
150000002772 monosaccharides Chemical class 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 17
238000011282 treatment Methods 0.000 claims abstract description 16
230000000844 anti-bacterial effect Effects 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
230000015572 biosynthetic process Effects 0.000 claims abstract description 8
239000012948 isocyanate Substances 0.000 claims abstract description 8
238000003786 synthesis reaction Methods 0.000 claims abstract description 8
150000002513 isocyanates Chemical class 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 291
125000001424 substituent group Chemical group 0.000 claims description 219
229910052739 hydrogen Inorganic materials 0.000 claims description 213
239000001257 hydrogen Substances 0.000 claims description 213
150000003839 salts Chemical class 0.000 claims description 199
239000012453 solvate Substances 0.000 claims description 168
150000002148 esters Chemical class 0.000 claims description 154
125000003118 aryl group Chemical group 0.000 claims description 149
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 141
125000001072 heteroaryl group Chemical group 0.000 claims description 115
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 113
-1 C) CrCu-alkyl Chemical group 0.000 claims description 103
239000003814 drug Substances 0.000 claims description 101
229940079593 drug Drugs 0.000 claims description 98
239000000651 prodrug Substances 0.000 claims description 97
229940002612 prodrug Drugs 0.000 claims description 97
125000003545 alkoxy group Chemical group 0.000 claims description 90
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 89
239000002243 precursor Substances 0.000 claims description 77
150000001412 amines Chemical class 0.000 claims description 68
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 67
229910052736 halogen Inorganic materials 0.000 claims description 63
150000002367 halogens Chemical class 0.000 claims description 63
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
125000003342 alkenyl group Chemical group 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 45
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 40
125000004429 atom Chemical group 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 38
125000000304 alkynyl group Chemical group 0.000 claims description 35
229910052799 carbon Inorganic materials 0.000 claims description 33
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
125000000392 cycloalkenyl group Chemical group 0.000 claims description 29
235000001014 amino acid Nutrition 0.000 claims description 28
150000001413 amino acids Chemical class 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000003396 thiol group Chemical group [H]S* 0.000 claims description 25
125000004104 aryloxy group Chemical group 0.000 claims description 23
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
125000003107 substituted aryl group Chemical group 0.000 claims description 23
239000000126 substance Substances 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 20
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 17
125000003282 alkyl amino group Chemical group 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
239000007789 gas Substances 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
230000029936 alkylation Effects 0.000 claims description 11
238000005804 alkylation reaction Methods 0.000 claims description 11
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
125000005418 aryl aryl group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 9
FOLJMFFBEKONJP-UHFFFAOYSA-N adamantane-1,3-diamine Chemical compound C1C(C2)CC3CC1(N)CC2(N)C3 FOLJMFFBEKONJP-UHFFFAOYSA-N 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
150000003138 primary alcohols Chemical class 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
QZWNXXINFABALM-UHFFFAOYSA-N adamantan-2-amine Chemical compound C1C(C2)CC3CC1C(N)C2C3 QZWNXXINFABALM-UHFFFAOYSA-N 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000012360 testing method Methods 0.000 claims description 8
125000005309 thioalkoxy group Chemical group 0.000 claims description 8
229960003805 amantadine Drugs 0.000 claims description 7
150000002923 oximes Chemical class 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 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
150000003973 alkyl amines Chemical class 0.000 claims description 6
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 6
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 6
108090000765 processed proteins & peptides Proteins 0.000 claims description 6
125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
238000006683 Mannich reaction Methods 0.000 claims description 5
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
150000001345 alkine derivatives Chemical class 0.000 claims description 5
125000005124 aminocycloalkyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
150000003141 primary amines Chemical group 0.000 claims description 5
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
238000006352 cycloaddition reaction Methods 0.000 claims description 3
150000002466 imines Chemical class 0.000 claims description 3
125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
238000006268 reductive amination reaction Methods 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
150000003431 steroids Chemical class 0.000 claims description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims 2
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims 1
101000982538 Homo sapiens Inositol polyphosphate 5-phosphatase OCRL Proteins 0.000 claims 1
102100026724 Inositol polyphosphate 5-phosphatase OCRL Human genes 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
235000003704 aspartic acid Nutrition 0.000 claims 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
238000001354 calcination Methods 0.000 claims 1
150000001925 cycloalkenes Chemical class 0.000 claims 1
UHMKISIRZFDJRU-UHFFFAOYSA-L diethyl-methyl-[2-(1,1,6-trimethylpiperidin-1-ium-2-carbonyl)oxyethyl]azanium;diiodide Chemical compound [I-].[I-].CC[N+](C)(CC)CCOC(=O)C1CCCC(C)[N+]1(C)C UHMKISIRZFDJRU-UHFFFAOYSA-L 0.000 claims 1
150000004676 glycans Chemical class 0.000 claims 1
NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims 1
150000002678 macrocyclic compounds Chemical class 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
238000007127 saponification reaction Methods 0.000 claims 1
238000004513 sizing Methods 0.000 claims 1
239000000758 substrate Substances 0.000 claims 1
DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 abstract description 21
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 10
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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 8
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238000003753 real-time PCR Methods 0.000 description 23
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229910052805 deuterium Inorganic materials 0.000 description 21
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 19
238000001990 intravenous administration Methods 0.000 description 19
JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 description 16
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 16
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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 16
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RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 description 9
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WZOZEZRFJCJXNZ-ZBFHGGJFSA-N cefoxitin Chemical compound N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)CC1=CC=CS1 WZOZEZRFJCJXNZ-ZBFHGGJFSA-N 0.000 description 9
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