CA2419801C

CA2419801C - Steroid derived antibiotics

Steroid derived antibiotics Download PDF

Info

Publication number: CA2419801C
Authority: CA; Canada
Prior art keywords: substituted; unsubstituted; compound; alkylamino; alkyl
Prior art date: 2000-08-15
Legal status : Expired - Lifetime

Application number

CA2419801A

Other languages

English (en)

French (fr)

Other versions

CA2419801A1 (en

Inventor

Paul B. Savage

Chunchong Li

Current Assignee

Brigham Young University

Original Assignee

Brigham Young University

Priority date

2000-08-15

Filing date

2001-08-15

Publication date

2010-08-10

2001-08-15 Application filed by Brigham Young University filed Critical Brigham Young University

2002-02-21 Publication of CA2419801A1 publication Critical patent/CA2419801A1/en

2010-08-10 Application granted granted Critical

2010-08-10 Publication of CA2419801C publication Critical patent/CA2419801C/en

2021-08-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000003431 steroids Chemical class 0.000 title claims abstract description 58
239000003242 anti bacterial agent Substances 0.000 title claims abstract description 42
229940088710 antibiotic agent Drugs 0.000 title claims abstract description 36
241000894006 Bacteria Species 0.000 claims abstract description 60
150000001875 compounds Chemical class 0.000 claims description 385
239000000203 mixture Substances 0.000 claims description 117
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 62
238000000034 method Methods 0.000 claims description 56
-1 C2-alkynyl Chemical group 0.000 claims description 47
239000012528 membrane Substances 0.000 claims description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
125000003282 alkyl amino group Chemical group 0.000 claims description 37
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000002431 aminoalkoxy group Chemical group 0.000 claims description 24
150000001413 amino acids Chemical class 0.000 claims description 21
125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 claims description 20
230000000845 anti-microbial effect Effects 0.000 claims description 20
230000003115 biocidal effect Effects 0.000 claims description 20
125000005416 guanidinoalkyloxy group Chemical group 0.000 claims description 20
125000006239 protecting group Chemical group 0.000 claims description 20
125000005123 aminoalkylcarboxy group Chemical group 0.000 claims description 19
239000004599 antimicrobial Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 18
125000004103 aminoalkyl group Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 17
125000001188 haloalkyl group Chemical group 0.000 claims description 16
125000005647 linker group Chemical group 0.000 claims description 16
230000035699 permeability Effects 0.000 claims description 16
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
239000012039 electrophile Substances 0.000 claims description 13
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
125000004122 cyclic group Chemical group 0.000 claims description 10
239000002243 precursor Substances 0.000 claims description 10
208000035143 Bacterial infection Diseases 0.000 claims description 9
208000022362 bacterial infectious disease Diseases 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
208000015181 infectious disease Diseases 0.000 claims description 9
230000000813 microbial effect Effects 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
230000012010 growth Effects 0.000 claims description 8
GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
230000002708 enhancing effect Effects 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
208000027096 gram-negative bacterial infections Diseases 0.000 claims description 3
125000001165 hydrophobic group Chemical group 0.000 claims description 3
231100000331 toxic Toxicity 0.000 claims description 3
230000002588 toxic effect Effects 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
230000003068 static effect Effects 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
230000001150 spermicidal effect Effects 0.000 claims 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract description 50
229960003276 erythromycin Drugs 0.000 abstract description 25
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229960002950 novobiocin Drugs 0.000 abstract description 17
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 232
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239000011159 matrix material Substances 0.000 description 83
229940035024 thioglycerol Drugs 0.000 description 83
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 68
238000005160 1H NMR spectroscopy Methods 0.000 description 65
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
239000012267 brine Substances 0.000 description 60
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 60
239000000725 suspension Substances 0.000 description 59
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229910001868 water Inorganic materials 0.000 description 52
239000002904 solvent Substances 0.000 description 50
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238000005481 NMR spectroscopy Methods 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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238000003786 synthesis reaction Methods 0.000 description 29
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229910052681 coesite Inorganic materials 0.000 description 23
229910052906 cristobalite Inorganic materials 0.000 description 23
229910052682 stishovite Inorganic materials 0.000 description 23
229910052905 tridymite Inorganic materials 0.000 description 23
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 20
229910010084 LiAlH4 Inorganic materials 0.000 description 19
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 19
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230000002209 hydrophobic effect Effects 0.000 description 17
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
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