CN101166740B - Imidazo (1,2-a) pyridine derivatives useful as peptide deformylase (PDF) inhibitors - Google Patents
Imidazo (1,2-a) pyridine derivatives useful as peptide deformylase (PDF) inhibitors Download PDFInfo
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- CN101166740B CN101166740B CN2006800140369A CN200680014036A CN101166740B CN 101166740 B CN101166740 B CN 101166740B CN 2006800140369 A CN2006800140369 A CN 2006800140369A CN 200680014036 A CN200680014036 A CN 200680014036A CN 101166740 B CN101166740 B CN 101166740B
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- imidazo
- base
- ethanamide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Abstract
The present invention relates to compounds of formula (I). These compounds are a novel type of peptide deformylase (PDF) inhibitors, and are therefore of great interest especially as new antibiotics.
Description
The present invention relates to new peptide deformylase (PDF) inhibitor.It is as microbiotic that these compounds make us interested especially.
Peptide deformylase is a kind of ferruginous bacterium metalloenzyme.In all bacteriums, can detect this kind of enzyme and it plays an important role in the metabolism of bacterium.Between synthesis phase, the deformylase polypeptide enzyme catalysis removes deformylase from the N-end of bacterioprotein at albumen.When this enzyme not, bacterium can not produce any functional protein.Peptide deformylase is the point of application of a class new antibiotic, and such microbiotic is called as peptide deformylase inhibitor containing 2.
The objective of the invention is to prepare can be with the synthetic new peptide deformylase inhibitor containing 2 that obtains of plain mode.
The present invention relates to compound or its pharmaceutically useful salt, solvate, hydrate or the pharmaceutically useful preparation of formula (I)
Wherein
Radicals R
1, R
2, R
3And R
4Be hydrogen atom, halogen atom, hydroxyl, amino, nitro or mercaptan (thiole) group, alkyl, alkenyl, alkynyl, assorted alkyl, aryl, heteroaryl, cycloalkyl, alkyl-cycloalkyl, assorted alkyl-cycloalkyl, Heterocyclylalkyl, aralkyl or heteroaralkyl independently of one another, wherein these groups can be substituted independently of one another, perhaps radicals R
1, R
2, R
3And R
4In two can be the part of cycloalkyl, Heterocyclylalkyl, aryl or heteroaryl ring together, and these the ring in each the ring can randomly be substituted;
R
5Be hydrogen atom, halogen atom, hydroxyl, amino, nitro or thiol group, alkyl, alkenyl, alkynyl, assorted alkyl, aryl, heteroaryl, cycloalkyl, alkyl-cycloalkyl, assorted alkyl-cycloalkyl, Heterocyclylalkyl, aralkyl or heteroaralkyl, wherein these groups can randomly be substituted separately;
Radicals R
6And R
7Be hydrogen atom or alkyl, alkenyl, alkynyl, assorted alkyl, aryl, heteroaryl, cycloalkyl, alkyl-cycloalkyl, assorted alkyl-cycloalkyl, Heterocyclylalkyl, aralkyl or heteroaralkyl independently of one another, wherein these groups can randomly be substituted independently of one another; And
X be formula-CS-NHOH ,-CH
2-CO-CH
2-OH ,-CO-CH
2-OH ,-CO-NHOH ,-CNH-NHOH ,-CH
2-NOH-CHS ,-NOH-CHS ,-NOH-CHO ,-CH
2-NOH-CHO ,-CH
2-CHOH-CHO ,-CHOH-CHO ,-CHOH-COOH ,-CH (CH
2-OH)-COOH ,-COOH or-CH
2The group of COOH perhaps is selected from following formula:
Wherein U is key, CH
2, NH, O or S, V is O, S, NH or CH
2, W is O, S, NH or CH
2, and Y is OH or NH
2, E is key, CH
2, NH, O or S and group D, G and M be N or CH independently of one another.
The statement of alkyl refers to a kind of saturated straight or branched alkyl, it particularly has 1 to 20 carbon atom, preferably has 1 to 12 carbon atom, most preferably has 1 to 6 carbon atom, for example methyl, ethyl, propyl group, sec.-propyl, just-butyl, isobutyl-, tert-butyl, just-hexyl, 2,2-dimethylbutyl or just-octyl group.
The statement of alkenyl and alkynyl refers to the undersaturated straight or branched alkyl of small part, it particularly has 2 to 20 carbon atoms, preferably have 2 to 12 carbon atoms, most preferably have 2 to 6 carbon atoms, for example vinyl, allyl group, ethynyl, propargyl, isopentene group or own-2-thiazolinyl.Alkenyl preferably has one or two (most preferably having one) two keys and alkynyl has one or two (most preferably having one) triple bond.
In addition, the statement of alkyl, alkenyl and alkynyl also refer to wherein for example one or more hydrogen atoms by halogen atom (preferred F or Cl) ,-COOH ,-OH ,-SH ,-NH
2,-NO
2,=O ,=S ,=the displaced group of NH, as 2,2,2-three chloroethyls or trifluoromethyl.
The statement of assorted alkyl refers to wherein one or more (preferred 1,2 or 3) carbon atoms by the displaced alkyl of oxygen, nitrogen, phosphorus, boron, selenium, silicon or sulphur atom (preferred oxygen, sulphur or nitrogen), alkenyl or alkynyl.The statement of assorted alkyl also refers to carboxylic acid or derives from the group of carboxylic acid, as acyl group, acyl group alkyl, alkoxy carbonyl, acyloxy, acyloxy alkyl, carboxyalkyl acid amides or alkoxyl group carbonyl oxygen base.
The example of assorted alkyl has formula R
a-O-Y
a-, R
a-S-Y
a-, R
a-N (R
b)-Y
a-, R
a-CO-Y
a-, R
a-O-CO-Y
a-, R
a-CO-O-Y
a-, R
a-CO-N (R
b)-Y
a-, R
a-N (R
b)-CO-Y
a-, R
a-O-CO-N (R
b)-Y
a-, R
a-N (R
b)-CO-O-Y
a-, R
a-N (R
b)-CO-N (R
c)-Y
a-, R
a-O-CO-O-Y
a-, R
a-N (R
b)-C (=NR
d)-N (R
c)-Y
a-, R
a-CS-Y
a-, R
a-O-CS-Y
a-, R
a-CS-O-Y
a-, R
a-CS-N (R
b)-Y
a-, R
a-N (R
b)-CS-Y
a-, R
a-O-CS-N (R
b)-Y
a-, R
a-N (R
b)-CS-O-Y
a-, R
a-N (R
b)-CS-N (R
c)-Y
a-, R
a-O-CS-O-Y
a-, R
a-S-CO-Y
a-, R
a-CO-S-Y
a-, R
a-S-CO-N (R
b)-Y
a, R
a-N (R
b)-CO-S-Y
a-, R
a-S-CO-O-Y
a-, R
a-O-CO-S-Y
a-, R
a-S-CO-S-Y
a-, R
a-S-CS-Y
a-, R
a-CS-S-Y
a-, R
a-S-CS-N (R
b)-Y
a-, R
a-N (R
b)-CS-S-Y
a-, R
a-S-CS-O-Y
a-, R
a-O-CS-S-Y
a-group, R wherein
aBe hydrogen atom, C
1-C
6-alkyl-, C
2-C
6-alkenyl-or C
2-C
6-alkynyl; R
bBe hydrogen atom, C
1-C
6-alkyl-, C
2-C
6-alkenyl-or C
2-C
6-alkynyl; R
cBe hydrogen atom, C
1-C
6-alkyl-, C
2-C
6-alkenyl-or C
2-C
6-alkynyl; R
dBe hydrogen atom, C
1-C
6-alkyl-, C
2-C
6-alkenyl-or C
2-C
6-alkynyl and Y
aBe straight key, C
1-C
6-alkylidene group, C
2-C
6-alkylene group or C
2-C
6-alkynylene, wherein each assorted alkyl comprises at least one carbon atom and one or more hydrogen atom can be replaced by the fluorine or chlorine atom.The particular instance of assorted alkyl has methoxyl group; trifluoromethoxy; oxyethyl group; just-propoxy-; isopropoxy; uncle-butoxy; methoxymethyl; ethoxyl methyl; methoxy ethyl; methylamino; ethylamino; dimethylamino; diethylamino; different-the propyl group ethylamino; methyl-amino methyl; the ethylamino methyl; two-different-propyl group amino-ethyl; enol ether; dimethylaminomethyl; dimethyl aminoethyl; ethanoyl; propionyl; butyryl acyloxy; acetoxyl group; methoxycarbonyl; oxyethyl group-carbonyl; N-ethyl-N-methylamino formyl radical or N-methylamino formyl radical.Other examples of assorted alkyl have nitrile, isonitrile, cyanate, thiocyanic ester, isocyanic ester, lsothiocyanates and alkyl nitrile group.
The statement of cycloalkyl refers to saturated or part undersaturated (for example cycloalkenyl group) cyclic group, it comprises one or more (preferred 1 or 2) and has particularly 3 to 14 ring carbon atoms, the ring of preferred 3 to 10 (especially 3,4,5,6 or 7) ring carbon atoms.The statement of cycloalkyl also refer to wherein one or more hydrogen atoms by fluorine, chlorine, bromine or iodine atom or-COOH ,-OH ,=O ,-SH ,=S ,-NH
2,=NH or-NO
2The displaced group of group, that is, for example cyclic ketone such as pimelinketone, 2-cyclonene or cyclopentanone.The concrete example of other of cycloalkyl has cyclopropyl, cyclobutyl, cyclopentyl, volution [4,5] decyl, norborneol alkyl (norbornyl), cyclohexyl, cyclopentenyl, cyclohexadienyl, naphthalane base, cube alkyl (cubanyl), two ring [4.3.0] nonyls, naphthane, cyclopentyl cyclohexyl, fluoro cyclohexyl or hexamethylene-2-thiazolinyl.
The statement of Heterocyclylalkyl refers to wherein one or more (preferred 1,2 or 3) ring carbon atoms by the displaced cycloalkyl as defined above of oxygen, nitrogen, silicon, selenium, phosphorus or sulphur atom (preferred oxygen, sulphur or nitrogen).Heterocyclylalkyl preferably has 1 or 2 ring with 3 to 10 (especially 3,4,5,6 or 7) annular atomses.The statement of Heterocyclylalkyl also refer to wherein one or more hydrogen atoms by fluorine, chlorine, bromine or iodine atom or-COOH ,-OH ,=O ,-SH ,=S ,-NH
2,=NH or-NO
2The displaced group of group.The example has piperidyl, morpholinyl, urotropin, pyrrolidyl, tetrahydro-thienyl, THP trtrahydropyranyl, tetrahydrochysene-furyl, oxa-cyclopropyl, nitrogen heterocyclic propyl group or 2-pyrazolinyl and lactan, lactone, cyclic imide and cyclic acid anhydride.
The statement of alkyl-cycloalkyl refers to the group that comprises cycloalkyl as defined above and alkyl, alkenyl or alkynyl, for example alkyl-cycloalkyl, alkyl cycloalkenyl group, alkenyl cycloalkyl and alkynyl cycloalkyl.Alkyl-cycloalkyl preferably comprises cycloalkyl and one or two alkyl, alkenyl or the alkynyl with 1 or 2 to 6 carbon atoms with one or two ring with 3 to 10 (especially 3,4,5,6 or 7) ring carbon atoms.
The statement of assorted alkyl-cycloalkyl refers to wherein one or more (preferred 1,2 or 3) ring carbon atoms and/or carbon atom by the displaced alkyl-cycloalkyl as defined above of oxygen, nitrogen, silicon, selenium, phosphorus or sulphur atom (preferred oxygen, sulphur or nitrogen).Assorted alkyl-cycloalkyl preferably has 1 or 2 ring with 3 to 10 (especially 3,4,5,6 or 7) annular atomses and has alkyl, alkenyl, alkynyl or the assorted alkyl of 1 or 2 to 6 carbon atoms with one or two.Such examples of groups has alkyl heterocycle alkyl, alkyl heterocycle thiazolinyl, alkenyl Heterocyclylalkyl, alkynyl Heterocyclylalkyl, assorted alkyl-cycloalkyl, assorted alkyl heterocycle alkyl and assorted alkyl heterocycle thiazolinyl, described cyclic group be saturated or single-, two-or three-undersaturated.
The statement of aryl or Ar refers to has one or more particularly 6 to 14 ring carbon atoms that have, the aromatic group of the ring of preferred 6 to 10 (especially 6) ring carbon atoms.The statement of aryl (or Ar) also refer to wherein one or more hydrogen atoms by fluorine, chlorine, bromine or iodine atom or-COOH ,-OH ,-SH ,-NH
2Or-NO
2The displaced group of group.The example has phenyl, naphthyl, xenyl, 2-fluorophenyl, anilino, 3-nitrophenyl or 4-hydroxy phenyl.
The statement of heteroaryl refers to and comprises one or more particularly 5 to 14 annular atomses that have, the aromatic group of preferred 5 to 10 (especially 5 or 6) annular atomses and one or more (preferred 1,2,3 or 4) oxygen, nitrogen, phosphorus or sulphur annular atoms (preferred O, S or N).The statement of heteroaryl also refer to wherein one or more hydrogen atoms by fluorine, chlorine, bromine or iodine atom or-COOH ,-OH ,-SH ,-NH
2Or-NO
2The displaced group of group.The example have 4-pyridyl, 2-imidazolyl, 3-phenylpyrrole base, thiazolyl,
Azoles base, triazolyl, tetrazyl, different
Azoles base, indazolyl, indyl, benzimidazolyl-, pyridazinyl, quinolyl, purine radicals, carbazyl, acridyl, pyrimidyl, 2,3 '-Lian furyl, 3-pyrazolyl and isoquinolyl.
The statement of aralkyl refers to the group that wherein comprises aryl defined above and alkyl, alkenyl, alkynyl and/or cycloalkyl, as arylalkyl, alkylaryl, aromatic yl alkenyl, aromatic yl polysulfide yl, cycloalkyl aryl, aryl rings thiazolinyl, alkylaryl cycloalkyl and alkylaryl cycloalkenyl group.The specific examples of aralkyl has toluene, dimethylbenzene, sym-trimethylbenzene, vinylbenzene, benzyl chloride, neighbour-toluene fluoride, 1H-indenes, naphthane, dihydronaphthalene, indone, benzyl ring amyl group, cumene, cyclohexyl phenyl, fluorenes and indane.Aralkyl preferably comprises one or two aromatic ring with 6 to 10 ring carbon atoms and one or two to have alkyl, alkenyl and/or the alkynyl of 1 or 2 to 6 carbon atoms and/or has the cycloalkyl of 5 or 6 ring carbon atoms.
The statement of heteroaralkyl refers to wherein one or more (preferred 1,2,3 or 4) ring carbon atoms and/or carbon atom by the displaced aralkyl as defined above of oxygen, nitrogen, silicon, selenium, phosphorus, boron or sulphur atom (preferred oxygen, sulphur or nitrogen), and promptly it refers to the group that comprises aryl as defined above or heteroaryl and alkyl, alkenyl, alkynyl and/or assorted alkyl and/or cycloalkyl and/or Heterocyclylalkyl.Heteroaralkyl preferably comprises one or two aromatic ring with 5 or 6 to 10 ring carbon atoms and one or two to have alkyl, alkenyl and/or the alkynyl of 1 or 2 to 6 carbon atoms and/or has the cycloalkyl of 5 or 6 ring carbon atoms, and wherein 1,2,3 or 4 in these carbon atoms is replaced by oxygen, sulphur or nitrogen-atoms.
The example has the aryl alkyl of mixing, the aryl-heterocyclic alkyl, the aryl-heterocyclic thiazolinyl, the arylalkyl Heterocyclylalkyl, the aromatic yl alkenyl Heterocyclylalkyl, the aromatic yl polysulfide yl Heterocyclylalkyl, the arylalkyl heterocycloalkenyl, heteroarylalkyl, the heteroaryl alkenyl, the heteroaryl alkynyl, the heteroaryl alkyl of mixing, the heteroaryl ring alkyl, the heteroaryl ring thiazolinyl, the heteroaryl Heterocyclylalkyl, the heteroaryl heterocycloalkenyl, the heteroarylalkyl cycloalkyl, the heteroarylalkyl heterocycloalkenyl, the heteroaryl alkyl-cycloalkyl of mixing, the assorted alkyl heterocycle alkyl of assorted alkyl cycloalkenyl group of heteroaryl and heteroaryl, described cyclic group be saturated or single-, two-or three-undersaturated.Its specific examples has tetrahydro isoquinolyl, benzoyl, 2-or 3-ethylindole base, 4-picoline-1-base (pyridino), 2-, 3-or 4-p-methoxy-phenyl, 4-ethoxyl phenenyl, 2-, 3-or 4-carboxyl phenyl alkyl.
The statement of cycloalkyl, Heterocyclylalkyl, alkyl-cycloalkyl, assorted alkyl-cycloalkyl, aryl, heteroaryl, aralkyl and heteroaralkyl also refer to wherein one or more hydrogen atoms by fluorine, chlorine, bromine or iodine atom or OH ,=O, SH ,=S, NH
2,=NH or NO
2The displaced group of group.
Statement " randomly substituted " refer to wherein one or more hydrogen atoms by fluorine for example, chlorine, bromine or iodine atom or-COOH ,-OH ,=O ,-SH ,=S ,-NH
2,=NH or-NO
2The displaced group of group.This statement also refers to by unsubstituted C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
1-C
6Assorted alkyl, C
3-C
10Cycloalkyl, C
2-C
9Heterocyclylalkyl, C
6-C
10Aryl, C
1-C
9Heteroaryl, C
7-C
12Aralkyl or C
2-C
11The group that heteroaralkyl replaces.
According to its replacement situation, the compound of formula (I) can comprise one or more chiral centres.Therefore, the present invention includes all pure enantiomers and all pure diastereomers, with and the mixture of any ratio.In addition, the present invention also comprise all cis/trans isomer of general formula (I) compound with and composition thereof.In addition, the present invention also comprises all tautomeric forms of formula (I) compound.
Preferred wherein W is that NH and V are formula (I) compounds of O, S or NH.
One, two or three among also preferred wherein group D, G and the M is formula (I) compound of nitrogen-atoms.
Especially preferably wherein X is formula-CH
2-CO-NHOH ,-CO-NHOH ,-CH
2-NOH-CHS ,-NOH-CHS ,-CH
2-NOH-CHO ,-NOH-CHO ,-CH
2-CO-CH
2OH ,-CO-CH
2OH ,-CH
2-CHOH-CHO ,-group of CHOH-CHO or have formula (I) compound of the group of one of following formula:
X most preferably is the group of formula-CO-NHOH.
In addition, R
1Also preferably hydrogen atom, chlorine atom, bromine atoms, amino, methyl or ethyl; Especially hydrogen atom or amino.
R
2More preferably be hydrogen atom, chlorine atom, bromine atoms, methyl or ethyl; Especially hydrogen atom.
In addition, R
3And R
4Also preferably not hydrogen atom simultaneously.
R
3More preferably be hydrogen atom, chlorine atom, bromine atoms, amino, methyl, ethyl or propyl group, especially chlorine atom, bromine atoms or amino.
R
4Preferably chlorine atom, bromine atoms, methyl, ethyl or propyl group; Especially chlorine atom or bromine atoms.
Especially preferred is R wherein
3Be bromine atoms and R
4Be methyl or R wherein
3Be hydrogen atom and R
4It is formula (I) compound of chlorine atom or bromine atoms.
More preferably be radicals R
1, R
2, R
3And R
4In two be the part of cycloalkyl, Heterocyclylalkyl, aryl or heteroaryl ring together, and these rings can randomly be substituted separately.
R
5Tert-butyl, sec.-propyl, neo-pentyl or just-hexyl preferably; Especially tert-butyl, neo-pentyl or just-hexyl.
Radicals R
6And R
7More preferably be hydrogen atom, hydroxymethyl or methyl independently of one another.
The example of formula (I) compound pharmacologically acceptable salt has the salt of the acceptable mineral acid example hydrochloric acid of physiology, sulfuric acid and phosphoric acid; Organic acid such as methylsulfonic acid, right-toluenesulphonic acids, lactic acid, formic acid, acetate, trifluoroacetic acid, citric acid, succsinic acid, fumaric acid, toxilic acid and salicylic salt.The compound of formula (I) can be by solvation, particularly can be by hydration.Hydration can be for example takes place in preparation process or can be that water absorbability by initial water-free formula (I) compound produces.
Pharmaceutical composition of the present invention comprises at least a formula as activeconstituents (I) compound and randomly comprises carrier and/or auxiliary agent.
The prodrug that is the object of the invention equally (can be referring to for example R.B.Silverman for its definition and example; Medizinische Chemie; VCH Weinheim; 1995; the 8th chapter; the 361ff page or leaf) comprise the compound and the acceptable blocking group of at least a pharmacology cleaved under physiological conditions of formula (I), for example hydroxyl, alkoxyl group, aralkoxy, acyl group or acyloxy are as methoxyl group, oxyethyl group, benzyloxy, ethanoyl or acetoxyl group.
It is purpose of the present invention equally that the treatment of formula (I) compound, the acceptable salt of its pharmacology or solvate and hydrate and preparation and pharmaceutical composition is used.
The compound of formula (I) very interesting especially as the inhibitor of metalloprotease (particularly PDF).These activeconstituentss prevent and/or treat disease in preparation, also are purposes of the present invention by the application in the medicine of the disease of PDF mediation especially.Generally speaking, the compound of formula (I) carries out administration with known acceptable method, and it is by independent administration or with any other therapeutical agent Combined Preparation.For example can finish administration with a kind of in the following mode: oral administration, for example with the form oral administration of dragee, coating tablet, pill, semisolid, soft or hard capsule, solution, emulsion or suspension; Parenteral admin is for example with the form parenteral admin of Injectable solution; Form rectal administration with suppository; Carry out administration by suction, for example with powder formulation or Sprayable, through skin or intranasal administration.For the preparation of such tablet, pill, semisolid, coating tablet, dragee and hard gelatin capsule, can for example lactose, sucrose, glucose, gelatin, maltose, silica gel, starch or derivatives thereof, talcum powder, stearic acid or its salt, dry skimmed milk etc. be admixed together with treating the product of application and the inorganic or organic pharmaceutical carrier of pharmacology inert.For preparation of soft capsule, can use the pharmaceutical carrier such as vegetables oil, oil, animal or synthetic oil, wax, fat, polyvalent alcohol.For liquor and syrupy preparation, can use the pharmaceutical carrier such as water, alcohols, aqueous salt solution, moisture dextrose, polyvalent alcohol, glycerine, vegetables oil, oil, animal or synthetic oil.For suppository, can use the pharmaceutical carrier such as vegetables oil, oil, animal or synthetic oil, wax, fat and polyvalent alcohol.For aerosol, can use the pressurized gas that is applicable to this purpose, as oxygen, nitrogen and carbonic acid gas.Pharmaceutically useful material also can comprise anticorrosion and stabilization additives, emulsifying agent, sweeting agent, perfume compound, the salt that is used to change osmotic pressure, buffer reagent, dressing additive and oxidation inhibitor.
X=-COOCH
3Formula (I) compound can by will be wherein the aforesaid formula of definition (II), (III) and the compound (IV) of each group react and prepare.
By its reaction product and azanol are reacted, can prepare formula (I) compound of X=-CO-NHOH in methyl alcohol.
Embodiment
General operation:
The solution of 50 0.2Ms of μ l amine (II) in methyl alcohol is assigned to (amine that is insoluble to methyl alcohol carries out manual allocation) on the 96-orifice plate.The solution that adds 50 0.2Ms of μ l aldehyde (III) in methyl alcohol.With this plate jolting at room temperature 2 hours.Subsequently, to acetic acid/methanol solution of solution that wherein adds 50 0.2Ms of μ l isocyanide (IV) in methyl alcohol and 50 μ l 0.4M.With one night of this plate jolting at room temperature, solvent evaporated, resistates is dissolved in the NH of 150 μ l 0.5M
2In the OH/ methanol solution.With this plate one night of jolting more at room temperature.
With suitable parent material, prepare following compound and it is identified with mass spectrum according to described general operation.All compounds have all been carried out studying (for this test as the activity of PDF inhibitor, referring to people such as D.Chen, antiseptic-germicide and chemotherapy (Antimicrobial Agents andChemotherapy), in January, 2004,250-261 page or leaf) and these compounds have the IC that scope is 1nmol to 50 μ mol
50Value.
Embodiment | Calculated value [M+H] | Measured value [M+H] |
2-(6-fluoro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 225.09 | 225.08 |
2-(6-bromo-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 299.03 | 299.04 |
2-(6-bromo-3,5-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 313.05 | 313.08 |
N-hydroxyl-2-(6-iodo-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 389.07 | 389.10 |
2-(6-bromo-3,5-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 327.07 | 327.10 |
2-(3-tert-butyl-6-iodo-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 389.07 | 389.11 |
2-(6-bromo-3-ethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 327.07 | 327.10 |
2-(6-chloro-3-cyclopropyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 295.12 | 295.14 |
2-(6-chloro-3-sec.-propyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 297.14 | 297.18 |
2-(6-bromo-3-ethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 341.09 | 341.12 |
2-(6-bromo-3-sec.-propyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.12 |
2-[6-bromo-5-methyl-3-((E)-propenyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 339.07 | 339.11 |
2-(6-chloro-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 297.14 | 297.17 |
2-(3-tert-butyl-6-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 297.14 | 297.16 |
2-(3-tert-butyl-6-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 311.16 | 311.23 |
2-(3-tert-butyl-6-fluoro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 281.17 | 281.15 |
2-(6-fluoro-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 281.17 | 281.19 |
N-hydroxyl-2-(3-isobutyl--5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 277.20 | 277.21 |
2-(6-bromo-5-methyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.12 |
2-(6-bromo-3-isobutyl--5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.14 |
2-(3-tert-butyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.20 |
N-hydroxyl-2-(6-iodo-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-propionic acid amide | 403.09 | 403.12 |
2-(6-bromo-8-methyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 355.11 | 355.08 |
2-(6-bromo-3-tert-butyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.13 |
2-(6-chloro-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 297.14 | 297.16 |
2-(3-tert-butyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 291.22 | 291.22 |
2-(6-chloro-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 311.16 | 311.17 |
2-(6-bromo-5-methyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 355.11 | 355.13 |
2-(6-bromo-3-tert-butyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 369.13 | 369.16 |
2-(6-bromo-3-isobutyl--8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 369.13 | 369.15 |
2-(6-bromo-3-isobutyl--5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 369.13 | 369.15 |
N-hydroxyl-2-(3-hydroxymethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 251.14 | 251.15 |
2-(5-ethyl-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 265.16 | 265.17 |
2-(5-ethyl-3-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 249.16 | 249.17 |
N-hydroxyl-2-[3-(1H-imidazoles-2-yl)-5-methyl-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 287.15 | 287.16 |
2-(3,5-diethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 263.18 | 263.19 |
2-[5-ethyl-3-(1H-imidazoles-2-yl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 301.16 | 301.18 |
2-(5-ethyl-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-propionic acid amide | 279.17 | 279.26 |
2-[5-ethyl-3-((E)-propenyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 275.18 | 0.00 |
2-[7-ethyl-3-(1H-imidazoles-2-yl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 301.16 | 301.18 |
2-(3-furans-2-base-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 287.13 | 287.15 |
N-hydroxyl-2-[8-methyl-3-(1H-pyrazole-3-yl)-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 287.15 | 287.16 |
2-(3-cyclopropyl-5-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 275.18 | 275.18 |
N-hydroxyl-2-(8-hydroxy-3-methyl-imidazo [1,2-a] pyridine-2-base is amino)-3-phenyl-propionic acid amide | 327.17 | 327.10 |
N-hydroxyl-2-(5-methyl-3-phenyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 297.16 | 297.17 |
N-hydroxyl-2-(7-methyl-imidazo [1,2-a] pyridine-2-base is amino)-3-phenyl-propionic acid amide | 311.18 | 311.15 |
2-(3-butyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.22 |
2-(3-ethyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.19 |
N-hydroxyl-2-(3-isobutyl--5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 305.24 | 305.14 |
N-hydroxyl-2-(3-hydroxymethyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 279.17 | 279.17 |
2-(3-benzyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 339.22 | 339.22 |
N-hydroxyl-2-(3-amyl group-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 319.26 | 319.25 |
N-hydroxyl-2-(3-methyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 263.18 | 263.17 |
3-[2-(hydroxyl amino formyl radical methyl-amino)-5-propyl group-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 321.19 | 321.18 |
2-(3,5-dipropyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.21 |
N-hydroxyl-2-[3-(2-methylthio group-ethyl)-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 323.19 | 323.18 |
2-(3-tert-butyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.22 |
2-[3-(2,2-dimethyl-propyl group)-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 319.26 | 319.25 |
2-(3-heptan-1-alkynyl-5-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 343.26 | 343.25 |
N-hydroxyl-2-(3-amyl group-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 345.18 | 345.20 |
2-[3-(2,2-dimethyl-propyl group)-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 345.18 | 345.20 |
2-(3-heptan-1-alkynyl-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.18 | 369.11 |
2-(6-fluoro-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 295.19 | 295.20 |
2-[3-(2,2-dimethyl-propyl group)-6-fluoro-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 295.19 | 295.19 |
2-(3-butyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.19 |
2-(3-benzyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 311.18 | 311.19 |
N-hydroxyl-2-(5-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 291.22 | 291.22 |
N-hydroxyl-2-[5-methyl-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 295.15 | 295.09 |
2-(3-tert-butyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.21 |
2-[3-(2,2-dimethyl-propyl group)-5-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 291.22 | 291.22 |
2-(3-heptan-1-alkynyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 315.22 | 315.23 |
2-(1-butyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 313.20 | 313.21 |
2-(1-benzyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 347.18 | 347.20 |
N-hydroxyl-2-(1-amyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 327.22 | 327.23 |
N-hydroxyl-2-(1-propyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 299.18 | 299.21 |
N-hydroxyl-2-[1-(2-methylthio group-ethyl)-imidazo [1,2-a] quinoline-2-base is amino]-ethanamide | 331.15 | 331.18 |
2-(1-tert-butyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 313.20 | 313.21 |
2-[1-(2,2-dimethyl-propyl group)-imidazo [1,2-a] quinoline-2-base is amino]-N-hydroxyl-ethanamide | 327.22 | 327.23 |
2-(1-heptan-1-alkynyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 351.22 | 351.23 |
2-(6-bromo-3-isobutyl--8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.03 |
2-[6-bromo-3-(2,2-dimethyl-propyl group)-8-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 369.13 | 369.15 |
2-(6-bromo-3-heptan-1-alkynyl-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 393.13 | 393.14 |
2-(6-chloro-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 311.16 | 311.17 |
2-[6-chloro-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 311.16 | 311.17 |
2-(6-chloro-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 335.16 | 335.17 |
2-(3-butyl-6-nitro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 308.16 | 308.15 |
N-hydroxyl-2-(3-isobutyl--6-nitro-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 308.16 | 308.11 |
2-(3-benzyl-6-nitro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 342.14 | 342.17 |
N-hydroxyl-2-(6-nitro-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 322.18 | 322.19 |
2-[3-(2,2-dimethyl-propyl group)-6-nitro-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 322.18 | 322.20 |
2-(3-heptan-1-alkynyl-6-nitro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 346.18 | 346.20 |
2-(3-butyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.18 |
N-hydroxyl-2-(6-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 291.22 | 291.22 |
2-[3-(2,2-dimethyl-propyl group)-6-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 291.22 | 291.22 |
2-(3-heptan-1-alkynyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 315.22 | 315.22 |
2-(3-butyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.23 |
N-hydroxyl-2-(3-isobutyl--5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 291.22 | 291.21 |
N-hydroxyl-2-(3-hydroxymethyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 265.16 | 265.16 |
2-(3-benzyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 325.20 | 325.21 |
2-(5,7-dimethyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.24 |
3-[2-(hydroxyl amino formyl radical methyl-amino)-5,7-dimethyl-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 307.17 | 307.10 |
2-(5,7-dimethyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.26 |
2-[5,7-dimethyl-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 309.17 | 309.18 |
2-(3-tert-butyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.22 |
2-[3-(2,2-dimethyl-propyl group)-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 305.24 | 305.24 |
2-(in 3-heptan-1-alkynyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 329.24 | 329.24 |
2-(6,8-two bromo-3-butyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 419.00 | 419.03 |
2-(6,8-two bromo-3-isobutyl--imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 419.00 | 419.03 |
2-(6,8-two bromo-3-hydroxymethyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 392.93 | 393.00 |
2-(3-benzyl-6,8-two bromo-imidazos [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 452.97 | 453.02 |
2-(6,8-two bromo-3-amyl group-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 433.02 | 433.05 |
2-[6,8-two bromo-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 436.95 | 436.97 |
2-[6,8-two bromo-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 433.02 | 433.02 |
2-(6,8-two bromo-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 457.01 | 457.03 |
2-(3-butyl-8-chloro-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 365.12 | 365.14 |
2-(8-chloro-3-hydroxymethyl-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 339.06 | 339.03 |
2-(3-benzyl-8-chloro-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 399.10 | 399.15 |
2-(8-chloro-3-amyl group-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 379.14 | 379.15 |
2-[8-chloro-3-(2,2-dimethyl-propyl group)-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 379.14 | 379.15 |
2-(8-chloro-3-heptan-1-alkynyl-6-trifluoromethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 403.14 | 403.14 |
2-(6-bromo-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.09 |
2-(6-bromo-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.10 |
2-(6-bromo-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.09 |
2-[6-bromo-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 355.11 | 355.11 |
2-(6-bromo-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 379.11 | 379.12 |
2-(1-butyl-9-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 329.19 | 329.19 |
2-(1-ethyl-9-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 301.15 | 301.16 |
N-hydroxyl-2-(9-hydroxyl-1-isobutyl--imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 329.19 | 329.19 |
2-(1-benzyl-9-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 363.17 | 363.18 |
N-hydroxyl-2-(9-hydroxyl-1-amyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 343.21 | 343.21 |
N-hydroxyl-2-(9-hydroxyl-1-propyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 315.17 | 315.17 |
N-hydroxyl-2-[9-hydroxyl-1-(2-methylthio group-ethyl)-imidazo [1,2-a] quinoline-2-base is amino]-ethanamide | 347.14 | 347.15 |
2-(1-tert-butyl-9-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 329.19 | 329.19 |
2-[1-(2,2-dimethyl-propyl group)-9-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino]-N-hydroxyl-ethanamide | 343.21 | 343.21 |
2-(8-bromo-3-butyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.11 |
2-(8-bromo-6-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.13 | 369.12 |
2-[8-bromo-3-(2,2-dimethyl-propyl group)-6-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 369.13 | 369.12 |
2-(8-bromo-3-heptan-1-alkynyl-6-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 393.13 | 393.13 |
2-(3-butyl-5-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 297.14 | 297.14 |
2-(5-chloro-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 269.10 | 269.14 |
2-(5-chloro-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 297.14 | 297.14 |
2-(5-chloro-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 271.07 | 271.09 |
2-(3-benzyl-5-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 331.12 | 331.13 |
2-(5-chloro-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 311.16 | 311.16 |
2-(5-chloro-3-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 255.08 | 255.09 |
3-[5-chloro-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 313.09 | 313.13 |
2-(5-chloro-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 283.12 | 283.18 |
2-[5-chloro-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 315.09 | 315.10 |
2-(3-tert-butyl-5-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 297.14 | 297.14 |
2-[5-chloro-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 311.16 | 311.16 |
2-(5-chloro-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 335.16 | 335.17 |
N-hydroxyl-2-(5-methyl-6-nitro-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 308.16 | 308.14 |
2-[3-(2,2-dimethyl-propyl group)-5-methyl-6-nitro-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 336.20 | 336.25 |
2-(5-bromo-3-propyl group-imidazo [1,2-b] isoquinoline 99.9-2-base is amino)-N-hydroxyl-ethanamide | 377.09 | 377.13 |
2-[5-bromo-3-(2-methylthio group-ethyl)-imidazo [1,2-b] isoquinoline 99.9-2-base is amino]-N-hydroxyl-ethanamide | 409.06 | 409.08 |
2-(6,8-two bromo-3-butyl-5-methyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 433.02 | 433.05 |
2-(6,8-two bromo-3-ethyl-5-methyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 404.98 | 405.00 |
2-(6,8-two bromo-3-isobutyl--5-methyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 433.02 | 433.03 |
2-(6,8-two bromo-3-hydroxymethyl-5-methyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 406.95 | 406.98 |
2-(3-benzyl-6,8-two bromo-5-methyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 466.99 | 466.96 |
2-(6,8-two bromo-5-methyl-3-amyl group-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 447.03 | 447.04 |
2-(6,8-two bromo-3,5-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 390.96 | 390.98 |
2-(6,8-two bromo-5-methyl-3-propyl group-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 419.00 | 419.01 |
2-[6,8-two bromo-5-methyl-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 450.97 | 451.02 |
2-[6,8-two bromo-3-(2,2-dimethyl-propyl group)-5-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 447.03 | 447.05 |
2-(6,8-two bromo-3-heptan-1-alkynyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 471.03 | 471.08 |
2-(1-butyl-5-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 329.19 | 329.20 |
N-hydroxyl-2-(5-hydroxyl-1-isobutyl--imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 329.19 | 329.20 |
2-(1-benzyl-5-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino)-N-hydroxyl-ethanamide | 363.17 | 363.17 |
N-hydroxyl-2-(5-hydroxyl-1-amyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 343.21 | 343.19 |
N-hydroxyl-2-(5-hydroxyl-1-propyl group-imidazo [1,2-a] quinoline-2-base is amino)-ethanamide | 315.17 | 315.23 |
N-hydroxyl-2-[5-hydroxyl-1-(2-methylthio group-ethyl)-imidazo [1,2-a] quinoline-2-base is amino]-ethanamide | 347.14 | 347.15 |
2-[1-(2,2-dimethyl-propyl group)-5-hydroxyl-imidazo [1,2-a] quinoline-2-base is amino]-N-hydroxyl-ethanamide | 343.21 | 343.21 |
2-(3-butyl-6,8-two fluoro-imidazos [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 299.16 | 299.16 |
2-(6,8-two fluoro-3-isobutyl--imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 299.16 | 299.16 |
2-(6,8-two fluoro-3-amyl group-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 313.18 | 313.18 |
2-[6,8-two fluoro-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 317.11 | 317.12 |
2-[3-(2,2-dimethyl-propyl group)-6,8-two fluoro-imidazos [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 313.18 | 313.18 |
2-(6-bromo-3-isobutyl--7,8-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.13 | 369.13 |
2-(6-bromo-7,8-dimethyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 383.15 | 383.14 |
2-[6-bromo-3-(2,2-dimethyl-propyl group)-7,8-dimethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 383.15 | 383.14 |
2-(in 6-bromo-3-heptan-1-alkynyl-7,8-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 407.15 | 407.15 |
2-[3-(2,2-dimethyl-propyl group)-7-methyl-6-nitro-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 336.20 | 336.21 |
2-(5-bromo-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.09 |
2-(5-bromo-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 313.05 | 313.06 |
2-(5-bromo-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.10 |
2-(5-bromo-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 315.02 | 315.04 |
2-(3-benzyl-5-bromo-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 375.07 | 374.98 |
2-(5-bromo-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.06 |
2-(5-bromo-3-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 299.03 | 299.04 |
3-[5-bromo-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 357.04 | 357.06 |
2-(5-bromo-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 327.07 | 327.07 |
2-[5-bromo-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 359.04 | 359.06 |
2-(5-bromo-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 341.09 | 341.17 |
2-[5-bromo-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 355.11 | 355.11 |
2-(5-bromo-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 379.11 | 379.12 |
2-(3-butyl-8-ethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.23 |
2-(8-ethyl-3-hydroxymethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 279.17 | 279.18 |
2-(3-benzyl-8-ethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 339.22 | 339.22 |
2-(8-ethyl-5-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 319.26 | 319.25 |
2-[3-(2,2-dimethyl-propyl group)-8-ethyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 319.26 | 319.25 |
2-(8-ethyl-3-heptan-1-alkynyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 343.26 | 343.26 |
2-(6,8-two chloro-3-hydroxymethyl-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 305.03 | 305.06 |
2-(6,8-two chloro-3-amyl group-imidazo [1,2-a] pyridines-2-base is amino)-N-hydroxyl-ethanamide | 345.12 | 345.12 |
2-(6-bromo-3-isobutyl--7-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.11 |
2-[6-bromo-3-(2,2-dimethyl-propyl group)-7-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 369.13 | 369.12 |
2-(3-butyl-5-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.22 |
2-(5-ethyl-3-isobutyl--imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.21 |
2-(5-ethyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.23 |
3-[5-ethyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 307.17 | 307.17 |
2-(5-ethyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.19 |
2-[5-ethyl-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 309.17 | 309.18 |
2-(3-tert-butyl-5-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.22 |
2-[3-(2,2-dimethyl-propyl group)-5-ethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 305.24 | 305.24 |
2-(5-ethyl-3-heptan-1-alkynyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 329.24 | 329.24 |
2-(6-bromo-3-butyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.11 | 355.11 |
2-(3-benzyl-6-bromo-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 389.09 | 389.06 |
2-(6-bromo-5-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.13 | 369.13 |
3-[6-bromo-2-(hydroxyl amino formyl radical methyl-amino)-5-methyl-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 371.06 | 371.10 |
2-[6-bromo-5-methyl-3-(2-methylthio group-ethyl)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 373.06 | 373.08 |
2-[6-bromo-3-(2,2-dimethyl-propyl group)-5-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 369.13 | 369.14 |
2-(6-bromo-3-heptan-1-alkynyl-5-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 393.13 | 393.03 |
2-(3,7-two-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 267.13 | 267.13 |
N-hydroxyl-2-(7-hydroxymethyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 279.17 | 279.17 |
2-(3-tert-butyl-7-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 293.19 | 293.18 |
2-(3-cyclohexyl-7-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 319.21 | 319.20 |
3-butyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-6-benzoic acid amides | 306.19 | 306.18 |
2-(hydroxyl amino formyl radical methyl-amino)-3-hydroxymethyl-imidazo [1,2-a] pyridine-6-benzoic acid amides | 280.12 | 280.14 |
3-tert-butyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-6-benzoic acid amides | 306.19 | 306.18 |
2-(hydroxyl amino formyl radical methyl-amino)-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-6-benzoic acid amides | 346.13 | 346.15 |
3-cyclohexyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-6-benzoic acid amides | 332.21 | 332.20 |
2-(6,8-two bromo-3-butyl-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 447.03 | 447.05 |
2-(6,8-two bromo-3-ethyls-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 419.00 | 419.02 |
2-(7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino for 3-benzyl-6,8-two bromo-5)-N-hydroxyl-ethanamide | 481.01 | 481.05 |
2-(6,8-two bromo-5,7-dimethyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 461.05 | 461.08 |
3-[6,8-two bromo-2-(hydroxyl amino formyl radical methyl-amino)-5,7-dimethyl-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 462.98 | 463.01 |
2-[6,8-two bromo-3-(2,2-dimethyl-propyl group)-5,7-dimethyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 461.05 | 461.10 |
2-[6,8-two bromo-5,7-dimethyl-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 486.98 | 487.04 |
2-(8-bromo-6-chloro-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 347.01 | 347.10 |
2-[8-bromo-6-chloro-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 389.07 | 389.07 |
2-(8-bromo-6-chloro-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 401.07 | 401.08 |
2-(8-amino-3-butyl-6-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 312.15 | 312.16 |
2-(8-amino-6-chloro-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 284.11 | 284.12 |
2-(8-amino-6-chloro-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 286.09 | 286.02 |
2-(8-amino-3-benzyl-6-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 346.13 | 346.15 |
2-(8-amino-6-chloro-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 326.17 | 326.18 |
3-[8-amino-6-chloro-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 328.10 | 328.12 |
2-(8-amino-6-chloro-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 298.13 | 298.06 |
2-(8-amino-3-tert-butyl-6-chloro-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 312.15 | 312.16 |
2-[8-amino-6-chloro-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 326.17 | 326.18 |
2-[8-amino-6-chloro-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 352.10 | 352.05 |
2-(8-amino-6-chloro-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 338.17 | 338.18 |
2-(8-amino-6-bromo-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 356.10 | 356.12 |
2-(8-amino-6-bromo-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 328.06 | 328.08 |
2-(8-amino-6-bromo-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 330.04 | 330.06 |
2-(8-amino-3-benzyl-6-bromo-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 390.08 | 390.11 |
2-(8-amino-6-bromo-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 370.12 | 370.13 |
2-(8-amino-6-bromo-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 342.08 | 342.10 |
2-(8-amino-6-bromo-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 356.10 | 356.11 |
2-[8-amino-6-bromo-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 370.12 | 370.13 |
2-[8-amino-6-bromo-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 396.04 | 396.05 |
2-[8-amino-6-bromo-3-(2,2,2-three fluoro-ethyls)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 382.03 | 382.06 |
2-(8-amino-6-bromo-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 382.12 | 382.13 |
2-(6-amino-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.19 |
2-(6-amino-3-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 250.15 | 250.15 |
2-(6-amino-3-benzyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 312.17 | 312.25 |
2-(6-amino-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 292.21 | 292.20 |
3-[6-amino-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridin-3-yl]-propionic acid | 294.14 | 294.15 |
2-(6-amino-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 264.17 | 264.27 |
2-(6-amino-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.18 |
2-[6-amino-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 292.21 | 292.20 |
2-[6-amino-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 318.14 | 318.15 |
2-[6-amino-3-(2,2,2-three fluoro-ethyls)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 304.12 | 304.11 |
2-(6-amino-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 304.21 | 304.20 |
2-(8-amino-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.19 |
2-(8-amino-3-benzyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 312.17 | 312.18 |
2-(8-amino-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 292.21 | 292.20 |
2-(8-amino-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 264.17 | 264.20 |
2-(8-amino-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.19 |
2-[8-amino-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 292.21 | 292.20 |
2-[8-amino-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 318.14 | 318.15 |
2-(5-amino-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.25 |
2-(5-amino-3-benzyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 312.17 | 312.19 |
2-(5-amino-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 292.21 | 292.20 |
2-(5-amino-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 264.17 | 264.17 |
2-(5-amino-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 278.19 | 278.19 |
2-[5-amino-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 318.14 | 318.16 |
2-[5-amino-3-(2,2,2-three fluoro-ethyls)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 304.12 | 304.10 |
2-(5-amino-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 304.21 | 304.21 |
2-(3-butyl-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 277.20 | 277.22 |
N-hydroxyl-2-(3-hydroxymethyl-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 251.14 | 251.13 |
2-(3-benzyl-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 311.18 | 311.11 |
N-hydroxyl-2-(8-methyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 291.22 | 291.21 |
2-[3-(2,2-dimethyl-propyl group)-8-methyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 291.22 | 291.21 |
N-hydroxyl-2-[8-methyl-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 317.14 | 317.15 |
2-(3-cyclohexyl-8-methyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 303.22 | 303.21 |
2-(3-butyl-7-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 291.22 | 291.21 |
2-(7-ethyl-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 265.16 | 265.07 |
2-(3-benzyl-7-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 325.20 | 325.20 |
2-(7-ethyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.24 | 305.23 |
2-(3-cyclohexyl-7-ethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 317.24 | 317.23 |
2-(3-butyl-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 279.17 | 279.20 |
2-(3-ethyl-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 251.14 | 251.14 |
N-hydroxyl-2-(8-hydroxyl-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 253.11 | 253.12 |
2-(3-benzyl-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 313.15 | 313.17 |
N-hydroxyl-2-(8-hydroxyl-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 293.19 | 293.19 |
N-hydroxyl-2-(8-hydroxyl-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-ethanamide | 265.16 | 265.16 |
2-(3-tert-butyl-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 279.17 | 279.17 |
2-[3-(2,2-dimethyl-propyl group)-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 293.19 | 293.19 |
N-hydroxyl-2-[8-hydroxyl-3-(3,3,3-three fluoro-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-ethanamide | 319.12 | 319.13 |
2-(3-cyclohexyl-8-hydroxyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 305.19 | 305.19 |
2-(3-butyl-imidazo [2,1-a] isoquinoline 99.9-2-base is amino)-N-hydroxyl-ethanamide | 313.20 | 313.20 |
2-(3-benzyl-imidazo [2,1-a] isoquinoline 99.9-2-base is amino)-N-hydroxyl-ethanamide | 347.18 | 347.19 |
N-hydroxyl-2-(3-amyl group-imidazo [2,1-a] isoquinoline 99.9-2-base is amino)-ethanamide | 327.22 | 327.22 |
2-[3-(2,2-dimethyl-propyl group)-imidazo [2,1-a] isoquinoline 99.9-2-base is amino]-N-hydroxyl-ethanamide | 327.22 | 327.22 |
2-(3-cyclohexyl-imidazo [2,1-a] isoquinoline 99.9-2-base is amino)-N-hydroxyl-ethanamide | 339.22 | 339.21 |
2-(8-benzyloxy-3-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.23 | 369.23 |
2-(8-benzyloxy-3-hydroxymethyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 343.17 | 343.18 |
2-(8-benzyloxy-3-amyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 383.25 | 383.23 |
2-(8-benzyloxy-3-propyl group-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 355.21 | 355.22 |
2-(8-benzyloxy-3-tert-butyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 369.23 | 369.25 |
2-[8-benzyloxy-3-(2,2-dimethyl-propyl group)-imidazo [1,2-a] pyridine-2-base is amino]-N-hydroxyl-ethanamide | 383.25 | 383.25 |
2-(8-benzyloxy-3-cyclohexyl-imidazo [1,2-a] pyridine-2-base is amino)-N-hydroxyl-ethanamide | 395.25 | 395.25 |
2-(hydroxyl amino formyl radical methyl-amino)-3-amyl group-imidazo [1,2-a] pyridine-6-formic acid | 321.19 | 321.14 |
3-butyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-8-formic acid | 307.17 | 307.20 |
2-(hydroxyl amino formyl radical methyl-amino)-3-amyl group-imidazo [1,2-a] pyridine-8-formic acid | 321.19 | 321.17 |
3-(2,2-dimethyl-propyl group)-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-8-formic acid | 321.19 | 321.19 |
3-cyclohexyl-2-(hydroxyl amino formyl radical methyl-amino)-imidazo [1,2-a] pyridine-8-formic acid | 333.19 | 333.20 |
Claims (13)
1. formula (I) compound or its pharmaceutically useful salt
Wherein
Radicals R
1, R
2, R
3And R
4The C that is hydrogen atom, halogen atom, hydroxyl, amino, nitro independently of one another, is randomly replaced by halogen atom or hydroxyl
1-C
12Alkyl, R wherein
aBe hydrogen atom and Y
aBe the R of straight key
a-O-CO-Y
a-, R wherein
aAnd R
bBe hydrogen atom and Y
aBe the R of straight key
a-N (R
b)-CO-Y
a-or heteroaralkyl, described heteroaralkyl comprise the aromatic ring of 6 ring carbon atoms and one and have 2 to 6 carbon atoms and one of them carbon atom by the displaced alkyl of Sauerstoffatom, perhaps radicals R
1, R
2, R
3And R
4In two can be the part of benzyl ring together;
R
5The C that is hydrogen atom, is randomly replaced by halogen atom or hydroxyl
1-C
12Alkyl, C
2-C
12Alkenyl, C
2-C
12Alkynyl, phenyl, comprise heteroaryl, benzyl, a C with 5 annular atomses and one or two oxygen or azo-cycle atom
3-C
7Cycloalkyl, R wherein
aBe hydrogen atom and Y
aBe C
1-C
6The R of-alkylidene group
a-O-CO-Y
a-or R wherein
aBe C
1-C
6-alkyl-and Y
aBe C
1-C
6The R of-alkylidene group
a-S-Y
a-;
Radicals R
6And R
7Be hydrogen atom or C independently of one another
1-C
6Alkyl; And
X is the group of formula-CO-NHOH.
2. compound as claimed in claim 1, wherein R
1Be hydrogen atom, chlorine atom, bromine atoms, amino, methyl or ethyl.
3. the described compound of claim 1, wherein R
2Be hydrogen atom, chlorine atom, bromine atoms, methyl or ethyl.
4. compound as claimed in claim 1, wherein R
3And R
4Not hydrogen atom simultaneously.
5. compound as claimed in claim 1, wherein R
3Be hydrogen atom, chlorine atom, bromine atoms, amino, methyl, ethyl or propyl group.
6. compound as claimed in claim 1, wherein R
4Be chlorine atom, bromine atoms, methyl, ethyl or propyl group.
7. compound as claimed in claim 1, wherein R
3Be bromine atoms and R
4Be methyl, perhaps R wherein
3Be hydrogen atom and R
4Be chlorine atom or bromine atoms.
8. compound as claimed in claim 1, wherein R
5It is tert-butyl, sec.-propyl, neo-pentyl or just-hexyl.
9. compound as claimed in claim 1, wherein radicals R
6And R
7Be hydrogen atom or methyl independently of one another.
10. comprise the pharmaceutical composition that also randomly comprises carrier as each the described compound in the claim 1 to 9.
11. be used for the application of the medicine of inhibiting peptide deformylase in preparation as each the described compound in the claim 1 to 9.
12. be used for preventing and/or treating application in preparation by the medicine of the disease of deformylase polypeptide enzymic activity mediation as each the described compound in the claim 1 to 9.
13. preparing as the application in the antibiotic medicine as each the described compound in the claim 1 to 9.
Applications Claiming Priority (3)
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DE102005019180.0 | 2005-04-25 | ||
DE102005019180 | 2005-04-25 | ||
PCT/EP2006/003765 WO2006114261A1 (en) | 2005-04-25 | 2006-04-24 | Imidazo(1,2-a)pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
Publications (2)
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CN101166740A CN101166740A (en) | 2008-04-23 |
CN101166740B true CN101166740B (en) | 2010-12-29 |
Family
ID=36686088
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EP (1) | EP1877407A1 (en) |
JP (1) | JP2008538776A (en) |
KR (1) | KR20080002866A (en) |
CN (1) | CN101166740B (en) |
AU (1) | AU2006239546B2 (en) |
BR (1) | BRPI0610842A2 (en) |
CA (1) | CA2606251A1 (en) |
MX (1) | MX2007013237A (en) |
RU (1) | RU2409575C2 (en) |
WO (1) | WO2006114261A1 (en) |
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US7563797B2 (en) | 2006-08-28 | 2009-07-21 | Forest Laboratories Holding Limited | Substituted imidazo(1,2-A)pyrimidines and imidazo(1,2-A) pyridines as cannabinoid receptor ligands |
WO2008045688A1 (en) * | 2006-10-06 | 2008-04-17 | Boehringer Ingelheim International Gmbh | Chymase inhibitors |
KR20190084991A (en) * | 2016-11-28 | 2019-07-17 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | Pyrazole-heteroaryl derivatives, their preparation methods and their medical uses |
CN107245050B (en) * | 2016-12-05 | 2019-10-25 | 徐州医科大学 | Vanillic aldehyde hydroxamic acid derivatives and its application |
EP4214207A1 (en) | 2020-09-15 | 2023-07-26 | 1st Biotherapeutics, Inc. | 2-amino-3-carbonyl imidazopyridine and pyrazolopyridine compounds |
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JPH0717971A (en) * | 1993-07-02 | 1995-01-20 | Takeda Chem Ind Ltd | Imidazole derivative, production and use thereof |
WO1998005635A1 (en) * | 1996-08-07 | 1998-02-12 | Darwin Discovery Limited | Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity |
AR029916A1 (en) * | 2000-05-05 | 2003-07-23 | Smithkline Beecham Corp | N-FORMIL-N-HIDROXI-ARILOXI RENTALS AND METHODS TO TREAT BACTERIAL INFECTIONS |
UY27813A1 (en) * | 2002-05-31 | 2003-12-31 | Smithkline Beecham Corp | PEPTIDE-DISFORMILASE INHIBITORS |
EP1585757B1 (en) * | 2002-12-11 | 2012-08-01 | GlaxoSmithKline LLC | Peptide deformylase inhibitors |
-
2006
- 2006-04-24 BR BRPI0610842-3A patent/BRPI0610842A2/en not_active IP Right Cessation
- 2006-04-24 WO PCT/EP2006/003765 patent/WO2006114261A1/en active Application Filing
- 2006-04-24 CA CA002606251A patent/CA2606251A1/en not_active Abandoned
- 2006-04-24 MX MX2007013237A patent/MX2007013237A/en not_active Application Discontinuation
- 2006-04-24 RU RU2007143501/04A patent/RU2409575C2/en not_active IP Right Cessation
- 2006-04-24 KR KR1020077024436A patent/KR20080002866A/en not_active Application Discontinuation
- 2006-04-24 EP EP06742662A patent/EP1877407A1/en not_active Withdrawn
- 2006-04-24 JP JP2008508132A patent/JP2008538776A/en active Pending
- 2006-04-24 CN CN2006800140369A patent/CN101166740B/en not_active Expired - Fee Related
- 2006-04-24 AU AU2006239546A patent/AU2006239546B2/en not_active Ceased
Non-Patent Citations (4)
Title |
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Chafiq Hamdouchi, et al..A Novel Application of the Ullmann Coupling Reaction for theAlkylsulfenylation of 2-Amino-Imidazo[1,2-a]pyridine.Terahedron55.1999,55541-548. * |
ChafiqHamdouchi et al..A Novel Application of the Ullmann Coupling Reaction for theAlkylsulfenylation of 2-Amino-Imidazo[1 |
Winkelmann, E. et al..Chemotherapeutically effective nitrocompounds.Part3:nitropyridine, nitroimidazopyridine andrelatedcompounds.Arzneim.-Forsch.27 1.1977,27(1),82-89. |
Winkelmann, E. et al..Chemotherapeutically effective nitrocompounds.Part3:nitropyridine, nitroimidazopyridine andrelatedcompounds.Arzneim.-Forsch.27 1.1977,27(1),82-89. * |
Also Published As
Publication number | Publication date |
---|---|
RU2409575C2 (en) | 2011-01-20 |
JP2008538776A (en) | 2008-11-06 |
MX2007013237A (en) | 2008-01-24 |
KR20080002866A (en) | 2008-01-04 |
CA2606251A1 (en) | 2006-11-02 |
BRPI0610842A2 (en) | 2010-07-27 |
AU2006239546B2 (en) | 2010-04-15 |
WO2006114261A1 (en) | 2006-11-02 |
AU2006239546A1 (en) | 2006-11-02 |
CN101166740A (en) | 2008-04-23 |
EP1877407A1 (en) | 2008-01-16 |
RU2007143501A (en) | 2009-06-10 |
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