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US 2011/0034528 A1Published application
Elansolids, Novel Natural Metabolites of Flexibacter and Antibiotically Active Derivatives Thereof
OwnerKlaus Gerth, Heinrich Steinmetz +1inventors
InventorsKlaus Gerth, Heinrich Steinmetz, Gerhard Höfle
Life of this patent
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Abstract
The present invention describes Elansolids, a new class of novel anti-bacterial compounds of formula (I).
Claims17
Compound of general formula (I):
- wherein
- R1 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group,
- R2 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group,
- R3 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group,
- R4 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group,
- R5 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group, and
- R6 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a mercapto, an alkyl, an alkenyl, an alkynyl, a heteroalkyl, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl, an aryl, a heteroaryl, an aralkyl or a heteroaralkyl group, or
- wherein R1 and R6 together are an oxygen atom, a sulfur atom or a NH group,
- or a pharmacologically acceptable salt, solvate, hydrate or a pharmacologically acceptable formulation thereof.
6 more elements
A compound having one of the following formulas:
- R =
- —O—CH2CH3
Compound (Elansolid A1) having the following parameters:
- C37H48O6 MW=588.8 HRMS:
- [El]+ calcd. 588.3451, found 588.3399;
- UV(MeOH):
- λmax (Ig ε)=225 (4,23), 257 sh (4,56), 270 (4,71), 280 (470) nm;
- IR (KBr):
- ν=3419, 2961, 2929, 1693, 1616, 1515, 1249 cm−1;
- TLC (silica gel, UV detection at 254 nm, dichlormethane/methanol 85:15) Rf=0.47;
- Analytical RP-HPLC:
- column 125×2 mm Nucleodur 120 5 μm C18 (Macherey-Nagel), solvent A:
- water/acetonitrile 95/5, 5 mM NH4OAc, pH 5.5, solvent B=water/acetonitrile 5/95, 5 mM NH4OAc, pH 5.5;
- gradient from 10% B to 100% B in 30 min, 10 min 100% B, flow 0.3 ml/min. Rt=20.4 min and 1H- and 13C NMR data as shown in table 1;
- or
- compound (Elansolid A2) having the following parameters:
- C37H48O6 MW=588.8;
- HRMS:
- ESI+ calcd.:
- 589.3529, found 589.3530;
- UV (Ethanol) λmax (Ig ε):
- 229 (4.18), 268 (4.73), 279 sh, 296 sh 319 sh nm;
- IR (KBr) ν=3424, 2962, 2928, 1689, 1627, 1615, 1515, 1235 cm−1;
- Analytical RP-HPLC:
- column 125×2 mm Nucleodur 120 5 μm C18 (Macherey-Nagel), solvent A:
- water/acetonitrile 95/5, 5 mM NH4OAc, pH 5,5—solvent B:
- water/acetonitrile 5/95, 5 mM NH4OAc, pH 5,5;
- solvent gradient from 10% B to 100% B in 10 min;
- flow:
- 0.3 ml/min. Rt=9.4 min, and 1H- and 13C NMR data as shown in table 2.
24 more elements
Compound (Elansolid B1) having the following parameters:
- C37HSOO7, MW=606.8, ESIMS:
- m/z 605.3 [M−H]−;
- UV:
- λ [nm] (Ig=262 (sh 4.61), 272 (4.65), 282 (4.69), 296 (4.51);
- TLC (silica gel 254 nm, dichloromethane/methanol 85:15):
- Rf=0.28;
- HPLC:
- column 125×2 mm Nucleodur 120 5 μm C18 (Macherey-Nagel), solvent A:
- water/acetonitrile 95/5 plus 5 mM NH4OAc, pH 5.5, solvent B:
- water/acetonitrile 5/95 plus 5 mM NH4OAc, pH 5.5) gradient:
- 10% B to 100% B in 30 min, 10 min 100% B, flow 0.3 mL/min. Rt=10.1 min and 1H- and 13C NMR data as shown in table 2.
8 more elements
Compound (Elansolid B2) having the following parameters:
- C38H52O7, MW=620.8;
- ESIMS:
- m/z 619.2 8 M−H]−;
- UV:
- λ [nm] (Ig ε)=229 (4.30), 259 (sh 4.60), 270 (4.66), 281 (4.68), 294 (4.53);
- IR (KBr):
- ν=3390, 3023, 2964, 2926, 2890, 1688, 1615, 1512, 1201 cm−1;
- TLC (silica gel;
- UV 254 nm, dichlormethane/methanol 85:15) :
- Rf=0.40;
- HPLC (column 125×2 mm Nucleodur 120 5 μm C18 (Macherey-Nagel), solvent A:
- water/acetonitrile 95/5, 5 mM NH4OAc, pH 5.5, solvent B:
- water/acetonitrile 5/95, 5 mM NH4OAc, pH 5.5, gradient from 100% A to 100% B in 30 min, 10 min 100% B, flow 0.3 mL/min):
- Rt=15.8 min and 1H- and 13C NMR data as shown in table 3.
11 more elements
Compound (Elansolid C1) having the following parameters:
- C4H55NO8, MW=725.9;
- (+)-HR-ESIMS:
- found 748.3830, calcd. 748.3825 [M+Na]+;
- UV:
- λ [nm] (Ig ε)=220 (4.35), 259 (4.45), 273 (sh), 282 (sh), 346 (3.48);
- IR (KBr):
- ν=3377, 2963, 1686, 1614, 1511, 1237 cm−1;
- TLC (silica gel, UV detection at 254 nm, CH2Cl2/MeOH 85:15):
- Rf=0.48;
- HPLC:
- column 2×125 mm Nucleodur 120 5 μm C18 (Macherey-Nagel), solvent A:
- water/acetonitrile 95/5, 5 mM NH4OAc, pH 5.5, solvent B:
- water/acetonitrile 5/95, 5 mM NH4OAc, pH 5.5, gradient:
- 10% B to 100% B in 10 min, 10 min 100% B, flow 0.3 mL/min. Rt=6.6 min and 1H- and 13C NMR data as shown in table 4.
11 more elements
Compound 067-34, 069-28-7, 070-11, 071-40, 073-47, 074-45, 075-43, 076-21, 077-19, 079-15, 080-18, 081-18, 082-21, 084-11, 085-25, 086-29, 087-30, 088-29, 089-35, 091-14 and 095-33 having the parameters shown in table 7, table 8 or FIGS. 4 to 45.
13-15. (canceled)
A Chitinophaga bacterium deposited as DSM 21134 at the German Collection of Microorganisms and Cell Cultures (DSMZ, Braunschweig, Germany).
Dependencies are inferred from the claim text.