EP1613624A2 - Neue verbindungen mit antibakterieller aktivität - Google Patents

Neue verbindungen mit antibakterieller aktivität

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Publication number
EP1613624A2
EP1613624A2 EP04724014A EP04724014A EP1613624A2 EP 1613624 A2 EP1613624 A2 EP 1613624A2 EP 04724014 A EP04724014 A EP 04724014A EP 04724014 A EP04724014 A EP 04724014A EP 1613624 A2 EP1613624 A2 EP 1613624A2
Authority
EP
European Patent Office
Prior art keywords
group
groups
alkyl
compounds according
heteroalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04724014A
Other languages
German (de)
English (en)
French (fr)
Inventor
Christian Hubschwerlen
Jean Phillippe Surivet
Cornelia Zumbrunn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Morphochem AG
Morphochem AG fuer Kombinatorische Chemie
Original Assignee
Morphochem AG
Morphochem AG fuer Kombinatorische Chemie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Morphochem AG, Morphochem AG fuer Kombinatorische Chemie filed Critical Morphochem AG
Priority to EP10013111A priority Critical patent/EP2298762A2/de
Publication of EP1613624A2 publication Critical patent/EP1613624A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present application describes novel compounds with antibacterial activity. These compounds are of interest, inter alia, as inhibitors of topoisomerase IV (topo IV) and of DNA gyrase.
  • the present invention relates to compounds of the general formula (I):
  • A is an oxygen or a sulfur atom, an NH, an alkylene, an alkenylene, an alkynylene or a heteroalkylene group,
  • X 1 , X 2 , X 3 , X 4 and X 5 are independently nitrogen atoms or groups of the formula CH or CR 4 ,
  • Cy is a cycloalkylene, a heterocycloalkylene, an arylene or a heteroarylene group.
  • R 1 represents a hydrogen atom, a halogen atom, a hydroxy, an amino, a thiol, an alkyl, a heteroalkyl, an alkyloxy, a heteroalkyloxy, a cycloalkyl, a heterocycloalkyl, an alkylcycloalkyl, a heteroalkylcycloalkyl -, is a cycloalkyloxy, an alkylcycloalkyloxy, a heterocycloalkyloxy or a heteroalkylcycloalkyloxy group,
  • the radicals R 2 independently of one another are a halogen atom, a hydroxyl, amino, nitro or thiol group, an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, Heterocycloalkyl, aralkyl or a heteroaralkyl radical, or two of the radicals R 2 together form part of an aryl, heteroaryl, cycloalkyl, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, aralkyl or heteroaralkyl ring,
  • R 3 is an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or a heteroaralkyl radical,
  • R 4 is a halogen atom, a hydroxyl, alkyl, alkenyl, alkynyl or a heteroalkyl group,
  • n 0, 1 or 2 and
  • n 0, 1 or 2
  • alkyl refers to a saturated, straight-chain or branched hydrocarbon group which has 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, particularly preferably 1 to 6 carbon atoms, e.g. the methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, 2, 2-dimethylbutyl or n-octyl group.
  • alkenyl and alkynyl refer to at least partially unsaturated, straight-chain or branched hydrocarbon groups which have 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, particularly preferably 2 to 6 carbon atoms, e.g. B. the ethenyl, allyl, acetylenyl, propargyl, isoprenyl or hex-2-enyl group.
  • Alkenyl groups preferably have one or two (particularly preferably one) double bonds or alkynyl groups have one or two (particularly preferably one) triple bonds.
  • alkyl, alkenyl and alkynyl refer to groups in which one or more hydrogen atoms are replaced by a halogen atom (preferably F or Cl), such as, for. B. the 2, 2, 2-trichloroethyl, or the trifluoromethyl group.
  • halogen atom preferably F or Cl
  • heteroalkyl refers to an alkyl, an alkenyl or an alkynyl group in which one or more (preferably 1, 2 or 3) carbon atoms are replaced by an oxygen, nitrogen, phosphorus, boron, selenium, Silicon or sulfur atom are replaced (preferably oxygen, sulfur or nitrogen).
  • heteroalkyl also refers to a carboxylic acid or a group derived from a carboxylic acid, such as. B. acyl, acylalkyl, alkoxycarbonyl, acyloxy, acyloxyalkyl, carboxyalkylamide or alkoxycarbonyloxy.
  • heteroalkyl groups are groups of the formulas R a -0-Y a -, RSY a -, R a -N (R b ) -Y-, R-CO-Y a -, R a -0-CO-Y a - R a -C0-0-Y a -, R a -C0-N (R) -Y a -, R a -N (R b ) -C0-Y a -
  • R a -0-CO-N (R b ) -Y a -, R a -N (R b ) -C0-0-Y a -, R a -N (R b ) -C0-N (R c ) -Y a - R a -0-CO-0-Y a -, R a -N (R b ) -C ( NR d ) -N (R c ) -Y a -, R a -CS-Y- R a -0-CS-Y a -, R a -CS-0-Y a -, R a -CS-N (R b ) -Y a -, R a -N (R b ) -CS-Y a - R a -0-CS-N (R b ) -Y a -, R a -N (R b ) -CS-Y a -
  • heteroalkyl groups are methoxy, trifluoroethoxy, ethoxy, n-propyloxy, iso-propyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, methylamino, ethylamino, dimethylarrtino, diethylamino, iso-propylethylamino, methylaminoethyl, ethylaminomethyl -iso- propylaminoethyl, enol ether, dimethylamino ethyl, dimethylaminoethyl, acetyl, propionyl, butyryloxy, acetyloxy, methoxycarbonyl, ethoxycarbonyl, N-ethyl-N-methylcarbamoyl or N-methylcarbamoyl.
  • heteroalkyl groups are nitrile, isonitrile
  • cycloalkyl refers to a saturated or partially unsaturated (e.g., cycloalkenyl) cyclic group that has one or more rings (preferred 1 or 2) which form a framework which 3 to
  • Cycloalkyl also refers to groups in which one or more hydrogen atoms are replaced by fluorine, chlorine,
  • N0 2 groups are replaced, for.
  • B. cyclic ketones such. B. cyclohexanone, 2-cyclohexenone or cyclopentanone.
  • cycloalkyl groups are the c ⁇ clopro ⁇ yl, cyclobutyl, cyclopentyl, spiro [4,5] decanyl, norborny, cyclohexyl, cyclopentenyl, cyclohexadienyl, decalinyl, bicyclo [4.3.0] nonyl -, tetralin,
  • heterocycloalkyl refers to a cycloalkyl group as defined above in which one or more (preferably 1, 2 or 3) ring carbon atoms are represented by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably oxygen,
  • a heterocycloalkyl group preferably has 1 or 2 rings with 3 to 10 (in particular 3, 4, 5, 6 or 7) ring atoms.
  • alkylcycloalkyl refers to groups which, in accordance with the above definitions, contain both cycloalkyl and also alkyl, alkenyl or alkynyl groups, e.g. B. alkylcycloalkyl, cycloalkylalkyl, alkylcycloalkenyl, alkenylcycloalkyl and alkynylcycloalkyl groups.
  • An alkylcycloalkyl group preferably contains a cycloalkyl group which has one or two ring systems which form a skeleton which contains 3 to 10 (in particular 3, 4, 5, 6 or 7) carbon atoms and one or two alkyl, Alkenyl or alkynyl groups with 1 or 2 to 6 carbon atoms.
  • heteroalkylcycloalkyl refers to alkylcycloalkyl groups, as defined above, in which one or more (preferably 1, 2 or 3) carbon atoms are represented by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably oxygen, sulfur or Nitrogen) are replaced.
  • a heteroakylcycloalkyl group preferably has 1 or 2 ring systems with 3 to 10 (in particular 3, 4, 5, 6 or 7) ring atoms and one or two alkyl, alkenyl, alkynyl or heteroalkyl groups with 1 or 2 to 6 carbon atoms.
  • Examples of such groups are alkyl heterocycloalkyl, alkyl heterocycloalkenyl, alkenyl heterocycloalkyl, alkynyl heterocycloalkyl, heteroalkylcycloalkyl, heteroalkyl heterocycloalkyl and heteroalkyl heterocylcloalkenyl, the cyclic groups being saturated or mono-, di- or trisaturated.
  • aryl or Ar refers to an aromatic group which has one or more rings and is formed by a structure which has 6 to 14 carbon atoms, preferably 6 to 10 (in particular 6) carbon atoms. contains atomic atoms.
  • aryl (or Ar) also refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms or OH, SH, NH 2 or NO 2 groups. Examples are the phenyl, naphthyl, biphenyl, 2-fluorophenyl, anilinyl, 3-nitrophenyl or 4-hydroxyphenyl group.
  • heteroaryl refers to an aromatic group which has one or more rings and is formed by a structure which contains 5 to 14 ring atoms, preferably 5 to 10 (in particular 5 or 6) ring atoms and one or more (preferably 1, 2, 3 or 4) contains oxygen, nitrogen, phosphorus or sulfur ring atoms (preferably 0, S or N).
  • heteroaryl also refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms or OH, SH, NH 2 or NO 2 groups.
  • Examples are 4-pyridyl, 2-imidazolyl, 3-phenylpyrrolyl, thiazolyl, oxazolyl, triazolyl, tetrazolyl, isoxazolyl, indazolyl, indolyl, benzimidazolyl, pyridazinyl, quinolinyl, purinyl -, Carbazolyl, acridinyl, pyrimidyl, 2, 3 '-bifuryl, 3-pyrazolyl and isoquinolinyl groups.
  • aralkyl refers to groups which, according to the above definitions, contain both aryl and also alkyl, alkenyl, alkynyl and / or cycloalkyl groups, such as, for. B. arylalkyl, arylalkenyl, arylalkynyl, arylcycloalkyl, arylcycloalkenyl, alkylarylcycloalkyl and alkylarylcycloalkenyl groups.
  • aralkyls are toluene, xylene, mesitylene, styrene, benzyl chloride, o-fluorotoluene, 1H-indene, tetralin, Dihydronaphthalenes, indanone, phenylcyclopentyl, cumene, cyclohexylphenyl, fluorene and indane.
  • An aralkyl group preferably contains one or two aromatic ring systems (1 or 2 rings) with 6 to 10 carbon atoms and one or two alkyl, alkenyl and / or alkynyl groups with 1 or 2 to 6 carbon atoms and / or a cycloalkyl group with 5 or 6 ring carbon atoms.
  • heteroaralkyl refers to an aralkyl group as defined above in which one or more (preferably 1, 2, 3 or 4) carbon atoms are represented by an oxygen, nitrogen, silicon, selenium, phosphorus, boron or Sulfur atom (preferably oxygen, sulfur or nitrogen) are replaced, i. H. to groups which, according to the above definitions, contain both aryl or heteroaryl and also alkyl, alkenyl, alkynyl and / or heteroalkyl and / or cycloalkyl and / or heterocycloalkyl groups.
  • a heteroaralkyl group preferably contains one or two aromatic ring systems (1 or 2 rings) with 5 or 6 to 10 carbon atoms and one or two alkyl, alkenyl and / or alkynyl groups with 1 or 2 to 6 carbon atoms and / or a cycloalkyl group with 5 or 6 ring carbon atoms, 1, 2, 3 or 4 of these carbon atoms being replaced by oxygen, sulfur or nitrogen atoms.
  • This expression also refers to groups with unsubstituted Ci-C ⁇ alkyl, C 2 -C6 alkenyl, C 2 -C6 alkynyl, Ci-Ce heteroalkyl, C 3 -C ⁇ o cycloalkyl, C 2 -C 9 heterocycloalkyl -, C ⁇ -Cio aryl, -C-C 9 heteroaryl, C 7 -C ⁇ 2 aralkyl or C-Cn heteroaralkyl groups are substituted.
  • Compounds of formula (I) can contain one or more centers of chirality due to their substitution.
  • the present invention therefore includes both all pure enantiomers and all pure diastereomers, as well as their mixtures in any mixing ratio.
  • the present invention also includes all cis / trans isomers of the compounds of the general formula (I) and mixtures thereof.
  • the present invention encompasses all tautomeric forms of the compounds of the formula (I).
  • Compounds of the formula (I) are further preferred, three, four or five of the groups X 1 , X 2 , X 3 , X 4 and X 5 being CH groups.
  • R 1 is preferably a C ⁇ -C 4 alkyloxy or a C 1 -C 4 heteroalkyloxy group, it being possible for one or more hydrogen atoms of these groups to be replaced by fluorine atoms.
  • R 1 is particularly preferably a methoxy group.
  • R 2 is preferably a hydroxy, a C 1 -C 4 alkyl, C 1 -C 4 heteroalkyl or a Ce-Ci 2 heteroaralkyl group.
  • R 3 is more preferably a heteroalkylcycloalkyl or a heteroaralkyl group.
  • R 3 is particularly preferably a group of the formula -BY, where B is an alkylene (in particular a C 1 -C 4 -alkylene group), alkenylene, alkynylene or a hetero- alkylene group (in particular a C 1 -C 4 heteroalkylene group) and Y is an aryl, heteroaryl, aralkyl, heteroaralkyl, cycloalkyl, heterocycloalkyl, alkylcycloalkyl or a heteroalkylcycloalkyl group (in particular a heterocycloalkyl or an aryl heterocycloalkyl group ) is.
  • B is an alkylene (in particular a C 1 -C 4 -alkylene group), alkenylene, alkynylene or a hetero- alkylene group (in particular a C 1 -C 4 heteroalkylene group)
  • Y is an aryl, heteroaryl, aralkyl, heteroaralkyl,
  • Y preferably has one of the following structures
  • X 6 , X 7 and X 8 are independently nitrogen atoms or groups of the formula CR 9 , X 9 and X 10 are independently oxygen or sulfur atoms or groups of the formula NR 10 , o is 0, 1 or 2, R 5 , R 6 , R 7 , R 8 and R 9 are independently hydrogen atoms, halogen atoms, hydroxyl, alkyl, alkenyl, alkynyl or heteroalkyl groups and R 10 and R u are independently hydrogen atoms, alkyl, alkenyl, alkynyl or heteroalkyl groups.
  • Y particularly preferably has one of the following structures:
  • the linker -A- (CH 2 ) - further preferably has a chain length of 2 or 3 atoms.
  • R 4 is preferably a fluorine or a chlorine atom or a C 1 -C 4 -alkyloxy or a C 3 -C e - dialkylaminomethyl group, it being possible for one or more hydrogen atoms of these groups to be replaced by fluorine atoms.
  • Cy is preferred a cycloalkylene or a heterocycloalkylene group with one or two rings and 4, 5, 6, 7, 8, 9 or 10 ring atoms.
  • Cy is particularly preferably a group of the formulas
  • U is a nitrogen atom or a group of the formula CH or COH and V is a nitrogen atom or a CH group and p is 0 or 1.
  • the substituents can be bound to this group both in an egatory and in an axial manner.
  • compositions according to the present invention contain at least one compound of the formula (I) as active ingredient and optionally excipients and / or adjuvants.
  • pharmacologically acceptable salts of the compounds of formula (I) are salts of physiologically acceptable mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid or salts of organic acids such as methanesulfonic acid, p-toluenesulfonic acid, lactic acid, acetic acid, trifluoroacetic acid, citric acid, succinic acid, fumaric acid, maleic acid and salicylic acid.
  • Further examples of pharmacologically acceptable salts of the compounds of formula (I) are alkali or alkaline earth metal salts such as.
  • the pro-drugs which are also the subject of the present invention, consist of a compound of the formula (I) and at least one pharmacologically acceptable protective group which is split off under physiological conditions, for example an alkoxy, aralkyloxy, acyl or acyloxy group such as an ethoxy, benzyloxy, acetyl or acetyloxy group.
  • the present invention also relates to the use of these active ingredients for the production of medicaments.
  • compounds of formula (I) are administered using known and acceptable modes, either individually or in combination with any other therapeutic agent.
  • Such therapeutically useful agents can be administered in one of the following ways: orally, for example as dragées, coated tablets, pills, semi-solid substances, soft or hard capsules, solutions, emulsions or suspensions; parenterally, eg as an injectable solution; rectally as suppositories; by inhalation, for example as a powder formulation or spray, transdermally or intranasally.
  • the therapeutically usable product can be mixed with pharmacologically inert, inorganic or organic drug carrier substances, for example with lactose, sucrose, glucose, gelatin, malt, silica gel, starch or derivatives the same, talc, stearic acid or its salts, dry skimmed milk and the like.
  • drug carriers such as vegetable oils, petroleum, animal or synthetic oils, wax, fat, polyols can be used.
  • drug carriers such as water, alcohols, aqueous salt solution, aqueous dextrose, polyols, glycerin, vegetable oils, petroleum, animal or synthetic oils can be used.
  • drug carriers such as vegetable oils, petroleum, animal or synthetic oils, wax, fat and polyols can be used.
  • compressed gases that are suitable for this purpose are, such as using oxygen, nitrogen and carbon dioxide.
  • the pharmaceutically usable agents can also contain additives for preservation, stabilization, emulsifiers, sweeteners, flavorings, salts for changing the osmotic pressure, buffers, coating additives and antioxidants.
  • Combinations with other therapeutic agents can include other antimicrobial and antifungal agents.
  • the dose of the biologically active compound according to the invention can vary within wide limits and can be adjusted to individual requirements. Generally a dose of 10 mg to 4000 mg per day is suitable, with a preferred dose being 50 to 3000 mg per day. In suitable cases, the dose can also be below or above the values given above.
  • the daily dose can be administered as a single dose or in multiple doses. A typical single dose contains approximately 50 mg, 100 mg, 250 mg, 500 mg, 1 g or 2 g of the active ingredient.
  • the BOG group was deprotected as in Example 1 using TFA in DCM.
  • Example 7 2- (3- ⁇ [(2,3-dihydrobenzo [1,4] dioxin-6-ylmethyl) amino] methyl ⁇ piperidin-l-yl) -1- (3- methoxy-quinolin-5-yl) ethanol
  • the two phases were separated and the organic phase washed with brine (20mL), dried over MgS0 4 and concentrated.
  • the crude product was quickly filtered through silica (AcOEt / Hex 1: 1).
  • the crude product was taken up in DMF (40 ml) and sodium azide (1.2 g, 18.4 mmol) was added.
  • the reaction mixture was stirred at 80 ° C. for 5 hours, concentrated on a rotary evaporator and mixed with ether and water.
  • the organic phase was dried over MgS0 4 and concentrated.
  • the crude product was purified by chromatography on Si0 2 (hex / EtOAc 4: 1). 2.16 g (9 mmol) could be isolated as an oil.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP04724014A 2003-04-08 2004-03-29 Neue verbindungen mit antibakterieller aktivität Withdrawn EP1613624A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10013111A EP2298762A2 (de) 2003-04-08 2004-03-29 Heterobicyclische Verbindungen mit antibakterieller Aktivität

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2003116081 DE10316081A1 (de) 2003-04-08 2003-04-08 Neue Verbindungen mit antibakterieller Aktivität
PCT/EP2004/003306 WO2004089947A2 (de) 2003-04-08 2004-03-29 Neue verbindungen mit antibakterieller aktivität

Publications (1)

Publication Number Publication Date
EP1613624A2 true EP1613624A2 (de) 2006-01-11

Family

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP10013111A Withdrawn EP2298762A2 (de) 2003-04-08 2004-03-29 Heterobicyclische Verbindungen mit antibakterieller Aktivität
EP04724014A Withdrawn EP1613624A2 (de) 2003-04-08 2004-03-29 Neue verbindungen mit antibakterieller aktivität

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP10013111A Withdrawn EP2298762A2 (de) 2003-04-08 2004-03-29 Heterobicyclische Verbindungen mit antibakterieller Aktivität

Country Status (9)

Country Link
US (1) US20060205719A1 (ru)
EP (2) EP2298762A2 (ru)
AU (1) AU2004228147A1 (ru)
CA (1) CA2534891A1 (ru)
DE (1) DE10316081A1 (ru)
NZ (1) NZ543441A (ru)
RU (1) RU2397982C2 (ru)
WO (1) WO2004089947A2 (ru)
ZA (1) ZA200508981B (ru)

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US20060205719A1 (en) 2006-09-14
RU2005134162A (ru) 2006-09-10
DE10316081A1 (de) 2004-10-21
NZ543441A (en) 2008-12-24
AU2004228147A1 (en) 2004-10-21
CA2534891A1 (en) 2004-10-21
RU2397982C2 (ru) 2010-08-27
EP2298762A2 (de) 2011-03-23
ZA200508981B (en) 2007-03-28
WO2004089947A2 (de) 2004-10-21

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