HU230190B1 - Glikopeptidszármazékok és ezeket tartalmazó gyógyászati kompozíciók - Google Patents
Glikopeptidszármazékok és ezeket tartalmazó gyógyászati kompozíciók Download PDFInfo
- Publication number
- HU230190B1 HU230190B1 HU0400887A HUP0400887A HU230190B1 HU 230190 B1 HU230190 B1 HU 230190B1 HU 0400887 A HU0400887 A HU 0400887A HU P0400887 A HUP0400887 A HU P0400887A HU 230190 B1 HU230190 B1 HU 230190B1
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- Prior art keywords
- substituted
- alkyl
- hydrogen
- group
- alkenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 title description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 54
- -1 substituted Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004419 alkynylene group Chemical group 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
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- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 235000005911 diet Nutrition 0.000 claims description 2
- 230000000378 dietary effect Effects 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 241001122767 Theaceae Species 0.000 claims 1
- 125000005735 alkanylene group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 1
- 229910000063 azene Inorganic materials 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 53
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
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- 238000000034 method Methods 0.000 description 29
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- 239000000047 product Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- 108010015899 Glycopeptides Proteins 0.000 description 22
- 102000002068 Glycopeptides Human genes 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 20
- 210000002435 tendon Anatomy 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 16
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
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- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
-
- 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
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11372898P | 1998-12-23 | 1998-12-23 | |
| US60/113,728 | 1998-12-23 | ||
| US12931399P | 1999-04-14 | 1999-04-14 | |
| US60/129,313 | 1999-04-14 | ||
| US16402499P | 1999-11-04 | 1999-11-04 | |
| US60/164,024 | 1999-11-04 | ||
| US16997899P | 1999-12-10 | 1999-12-10 | |
| US60/169,978 | 1999-12-10 | ||
| PCT/US1999/030543 WO2000039156A1 (en) | 1998-12-23 | 1999-12-22 | Glycopeptide derivatives and pharmaceutical compositions containing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0400887A2 HUP0400887A2 (hu) | 2004-08-30 |
| HUP0400887A3 HUP0400887A3 (en) | 2012-09-28 |
| HU230190B1 true HU230190B1 (hu) | 2015-09-28 |
Family
ID=27493926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0400887A HU230190B1 (hu) | 1998-12-23 | 1999-12-22 | Glikopeptidszármazékok és ezeket tartalmazó gyógyászati kompozíciók |
Country Status (23)
| Country | Link |
|---|---|
| US (9) | US6392012B1 (enExample) |
| EP (1) | EP1140993B1 (enExample) |
| JP (1) | JP4362017B2 (enExample) |
| KR (1) | KR100665204B1 (enExample) |
| CN (1) | CN1249081C (enExample) |
| AT (1) | ATE242783T1 (enExample) |
| AU (1) | AU768204B2 (enExample) |
| BR (1) | BRPI9914221B8 (enExample) |
| CA (1) | CA2336445C (enExample) |
| CZ (1) | CZ301184B6 (enExample) |
| DE (1) | DE69908819T2 (enExample) |
| DK (1) | DK1140993T3 (enExample) |
| ES (1) | ES2201825T3 (enExample) |
| HK (1) | HK1040721B (enExample) |
| HU (1) | HU230190B1 (enExample) |
| IL (2) | IL140093A0 (enExample) |
| NO (1) | NO326066B1 (enExample) |
| NZ (1) | NZ508594A (enExample) |
| PL (1) | PL198311B1 (enExample) |
| PT (1) | PT1140993E (enExample) |
| SI (1) | SI1140993T1 (enExample) |
| WO (1) | WO2000039156A1 (enExample) |
| ZA (1) | ZA200007222B (enExample) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2201825T3 (es) * | 1998-12-23 | 2004-03-16 | Theravance, Inc. | Derivados del glicopeptidos y composiciones farmaceuticas que los contienen. |
| US6699836B2 (en) | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| WO2000059528A1 (en) * | 1999-04-02 | 2000-10-12 | The Trustees Of Princeton University | Desleucyl glycopeptide antibiotics and methods of making same |
| WO2001057071A2 (en) * | 2000-02-04 | 2001-08-09 | Advanced Medicine, Inc. | Glycopeptide derivatives having antibiotic activity |
| AU2001259298A1 (en) * | 2000-05-02 | 2001-11-12 | Advanced Medicine, Inc. | Polyacid glycopeptide derivatives |
| WO2001083521A2 (en) | 2000-05-02 | 2001-11-08 | Theravance, Inc. | Reductive alkylation process on glycopeptides |
| DE60136926D1 (de) | 2000-05-02 | 2009-01-22 | Theravance Inc | Zusammensetzung die eine zyklodextrin und ein glykopeptid-antibiotikum enthält |
| ATE388960T1 (de) * | 2000-06-22 | 2008-03-15 | Theravance Inc | Glykopeptidderivate mit carboxysacchariden |
| US6872804B2 (en) | 2000-06-22 | 2005-03-29 | Theravance, Inc. | Glycopeptide disulfide and thioester derivatives |
| WO2001098329A1 (en) * | 2000-06-22 | 2001-12-27 | Theravance, Inc. | Polyhydroxy glycopeptide derivatives |
| UA75083C2 (uk) * | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| US6905669B2 (en) * | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| TWI275594B (en) * | 2001-08-24 | 2007-03-11 | Theravance Inc | Process for preparing vancomycin phosphonate derivatives |
| TWI312785B (en) * | 2001-08-24 | 2009-08-01 | Theravance Inc | Process for preparing vancomycin derivatives |
| DE60118737T2 (de) | 2001-09-19 | 2006-10-19 | The Procter & Gamble Company, Cincinnati | Farbbedruckte Mehrschichtstruktur, ein damit hergestellter absorbierender Artikel und Verfahren zu deren Herstellung |
| TWI335332B (en) | 2001-10-12 | 2011-01-01 | Theravance Inc | Cross-linked vancomycin-cephalosporin antibiotics |
| CN101404986B (zh) | 2002-05-17 | 2011-09-28 | 赛奎拉公司 | 用于诊断和治疗感染性疾病的组合物和制药方法 |
| US20040033986A1 (en) | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| WO2003099858A1 (en) | 2002-05-24 | 2003-12-04 | Theravance, Inc. | Cross-linked glycopeptide-cephalosporin antibiotics |
| WO2003106399A2 (en) | 2002-06-17 | 2003-12-24 | Theravance, Inc. | PROCESS FOR PREPARING N-PROTECTED β-AMINO ALDEHYDE COMPOUNDS |
| CN101721412A (zh) * | 2002-07-09 | 2010-06-09 | 法斯根有限责任公司 | 治疗人和动物中微生物感染的方法 |
| US20060074014A1 (en) * | 2002-11-18 | 2006-04-06 | Vicuron Pharmaceuticals Inc. | Dalbavancin compositions for treatment of bacterial infections |
| AU2003298662A1 (en) * | 2002-11-18 | 2004-06-15 | Vicuron Pharmaceuticals Inc. | Dalbavancin compositions for treatment of bacterial infections |
| ATE450540T1 (de) * | 2003-05-23 | 2009-12-15 | Theravance Inc | Quervernetzte glycopeptid-cephalosporin- antibiotika |
| ATE388153T1 (de) * | 2003-07-11 | 2008-03-15 | Theravance Inc | Quervernetzte glycopeptid-cephalosporin- antibiotika |
| DE102004055582A1 (de) * | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-Heterocyclyl-phthalsäurediamide |
| AU2005308160A1 (en) | 2004-11-29 | 2006-06-01 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
| US8304597B2 (en) | 2004-12-15 | 2012-11-06 | The Procter And Gamble Company | Method of using an absorbent article having a functional enhancement indicator |
| US20070185015A1 (en) * | 2005-02-28 | 2007-08-09 | Chiron Corporation and North China Pharmaceutical Corporation | Semi-synthetic desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US7632918B2 (en) * | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
| WO2007038246A2 (en) | 2005-09-22 | 2007-04-05 | Medivas, Llc | Solid polymer delivery compositions and methods for use thereof |
| WO2007035938A2 (en) | 2005-09-22 | 2007-03-29 | Medivas, Llc | BIS-(α-AMINO)-DIOL-DIESTER-CONTAINING POLY(ESTER AMIDE) AND POLY(ESTER URETHANE) COMPOSITIONS AND METHODS OF USE |
| US20070173438A1 (en) * | 2006-01-13 | 2007-07-26 | The Scripps Research Institute | [PSI[CH2NH]PG4] glycopeptide antibiotic analogs |
| TW200808818A (en) * | 2006-05-26 | 2008-02-16 | Shionogi & Co | Glycopeptide antibiotic derivatives |
| WO2009085562A1 (en) * | 2007-12-26 | 2009-07-09 | Lead Therapeutics, Inc. | Novel semi-synthetic glycopeptides as antibacterial agents |
| JP5517153B2 (ja) | 2007-12-26 | 2014-06-11 | 塩野義製薬株式会社 | グリコペプチド抗生物質配糖化誘導体 |
| WO2009123713A1 (en) | 2008-04-01 | 2009-10-08 | Cornell University | Organo-soluble chitosan salts and chitosan-derived biomaterials prepared thereof |
| GB2465863A (en) * | 2008-12-05 | 2010-06-09 | Lead Therapeutics Inc | Semi-synthetic heptapeptidic glycopeptides for the treatment of bacterial infections |
| CN101928330B (zh) * | 2009-06-26 | 2013-10-16 | 上海来益生物药物研究开发中心有限责任公司 | 一种新的化合物及其应用 |
| US20140171357A1 (en) * | 2011-03-24 | 2014-06-19 | Seachaid Pharmaceuticals, Inc. | Vancomycin derivatives |
| WO2014152332A1 (en) | 2013-03-15 | 2014-09-25 | Melinta Therapeutics, Inc. | Methods of treating infections in overweight and obese patients using antibiotics |
| EP3049115A1 (en) * | 2013-09-23 | 2016-08-03 | Jawaharlal Nehru Centre For Advanced Scientific Research | Vancomycin-sugar conjugates and uses thereof |
| EP3240574A1 (en) * | 2014-12-25 | 2017-11-08 | Jawaharlal Nehru Centre For Advanced Scientific Research | Glycopeptides and uses thereof |
| AU2017207875A1 (en) * | 2016-01-15 | 2018-08-09 | Universität Hamburg | Methods for the production of rhamnosylated flavonoids |
| EP3408253A1 (en) * | 2016-01-28 | 2018-12-05 | Acatechol, Inc. | Photo-cleavable primer compositions and methods of use |
| CN107325159A (zh) * | 2016-04-29 | 2017-11-07 | 中国科学院上海药物研究所 | 一类万古霉素衍生物、其制备方法、药物组合物和用途 |
| CA3062570A1 (en) * | 2017-05-22 | 2018-11-29 | Insmed Incorporated | Lipo-glycopeptide cleavable derivatives and uses thereof |
| CN107987131B (zh) * | 2017-11-16 | 2021-03-09 | 上海来益生物药物研究开发中心有限责任公司 | 一组具有抗耐药性细菌活性的化合物、其制备方法和应用 |
| CN108409837B (zh) | 2018-03-06 | 2021-09-24 | 上海来益生物药物研究开发中心有限责任公司 | 一组具有抗耐药性细菌活性的糖肽类化合物、其制备方法和应用 |
| NL2023883B1 (en) * | 2019-09-24 | 2021-04-26 | Univ Leiden | Antibiotic compounds |
| CN111620931B (zh) * | 2020-06-12 | 2021-12-17 | 苏州博源医疗科技有限公司 | 万古霉素衍生物及其制备方法和应用 |
| CN114213284B (zh) * | 2022-01-04 | 2023-08-01 | 丽珠集团福州福兴医药有限公司 | (9h-芴-9-基)-癸基(2-氧代乙基)氨基甲酸甲酯及其合成方法 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4497802A (en) | 1983-10-21 | 1985-02-05 | Eli Lilly And Company | N-Acyl glycopeptide derivatives |
| GB8428619D0 (en) | 1984-11-13 | 1984-12-19 | Lepetit Spa | Derivatives of antibiotic l 17046 |
| US4914187A (en) | 1984-11-13 | 1990-04-03 | Gruppo Lepetit S.P.A | Ester derivatives of antibiotic L 17046 |
| US4698327A (en) | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4643987A (en) | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| US4639433A (en) | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| GB8704847D0 (en) | 1987-03-02 | 1987-04-08 | Lepetit Spa | Substituted alkylamides of teicoplanin compounds |
| FR2632185B1 (fr) * | 1988-06-01 | 1992-05-22 | Rhone Poulenc Chimie | Silice pour compositions dentifrices compatible notamment avec le zinc |
| GB8817397D0 (en) * | 1988-07-21 | 1988-08-24 | Lepetit Spa | N15-alkyl & n15 n15-di-alkyl derivatives of teicoplanin antibiotics carrying functional groups on alkyl side chain |
| US5534420A (en) | 1988-07-28 | 1996-07-09 | Eli Lilly And Company | Biotransformation of glycopeptide antibiotics |
| ATE134646T1 (de) * | 1988-12-27 | 1996-03-15 | Lepetit Spa | C63-amidderivate von 34-de(acetylglucosaminyl)-34-deoxy-teicoplanine |
| IE64155B1 (en) * | 1989-03-29 | 1995-07-12 | Lepetit Spa | New substituted alkylamide derivatives of teicoplanin |
| ZA909847B (en) | 1989-12-13 | 1992-08-26 | Lilly Co Eli | Glycopeptide derivatives |
| AU647122B2 (en) | 1990-05-28 | 1994-03-17 | Gruppo Lepetit S.P.A. | C63-amide derivatives of 34-de(acetylglucosaminyl)-34-deoxy- teicoplanin and their use as medicaments against bacteria resistant to glycopeptide antibiotics |
| WO1992017456A1 (fr) | 1991-03-26 | 1992-10-15 | Fujisawa Pharmaceutical Co., Ltd. | Derive d'acide amine et sel dudit derive |
| US5750509A (en) | 1991-07-29 | 1998-05-12 | Gruppo Lepetit S.P.A. | Amide derivatives of antibiotic A 40926 |
| AU666862B2 (en) | 1991-07-29 | 1996-02-29 | Vicuron Pharmaceuticals Inc. | Amide derivatives of antibiotic A 40926 |
| US5840684A (en) | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| TW457248B (en) | 1994-01-28 | 2001-10-01 | Lilly Co Eli | Glycopeptide antibiotic derivatives |
| IT1282586B1 (it) | 1996-02-08 | 1998-03-31 | Chemical And Biolog Ind | Composizioni farmaceutiche per il trattamento biologico delle infezioni dovute a ceppi di enterococcus faecium resistenti agli |
| JP2000507246A (ja) | 1996-03-21 | 2000-06-13 | トランセル テクノロジーズ インク． | 固体相のリポグリコペプチドライブラリー、組成物及び方法 |
| AU2441697A (en) | 1996-04-12 | 1997-11-07 | Eli Lilly And Company | Covalently-linked glycopeptide dimers |
| JP4159110B2 (ja) | 1996-04-12 | 2008-10-01 | イーライ・リリー・アンド・カンパニー | グリコペプチド化合物 |
| ATE208791T1 (de) | 1996-04-23 | 2001-11-15 | Biosearch Italia Spa | Chemisches verfahren zur herstellung von amidderivaten von a 40926 antibiotikum |
| US5919756A (en) * | 1996-06-28 | 1999-07-06 | Eli Lilly And Company | Amides |
| US5939382A (en) | 1996-11-21 | 1999-08-17 | Eli Lilly And Company | Reducing agent for reductive alkylation of glycopeptide antibiotics |
| US5952466A (en) | 1997-11-12 | 1999-09-14 | Eli Lilly And Company | Reductive alkylation of glycopeptide antibiotics |
| US5916873A (en) | 1997-04-17 | 1999-06-29 | Eli Lilly And Company | Teicoplanin derivatives |
| US5977063A (en) | 1997-05-20 | 1999-11-02 | Eli Lilly And Company | Alkylated hexapeptides |
| US5952310A (en) | 1997-05-20 | 1999-09-14 | Eli Lilly And Company | Glycopeptide hexapeptides |
| US5919771A (en) | 1997-05-20 | 1999-07-06 | Eli Lilly And Company | Urea and thiourea derivatives of glycopeptides |
| US6518242B1 (en) * | 1998-02-20 | 2003-02-11 | Theravance, Inc. | Derivatives of glycopeptide antibacterial agents |
| WO1999042476A1 (en) | 1998-02-20 | 1999-08-26 | Advanced Medicine, Inc. | Novel antibacterial agents |
| EP1073447B1 (en) | 1998-05-01 | 2007-05-09 | Eli Lilly And Company | N1-modified glycopeptides |
| JP2002520422A (ja) | 1998-07-14 | 2002-07-09 | プリンストン ユニバーシティ | グリコペプチド抗生物質、グリコペプチド抗生物質のコンビナトリアルライブラリーおよびその作成方法 |
| ES2201825T3 (es) | 1998-12-23 | 2004-03-16 | Theravance, Inc. | Derivados del glicopeptidos y composiciones farmaceuticas que los contienen. |
| UA75083C2 (uk) * | 2000-06-22 | 2006-03-15 | Тераванс, Інк. | Похідні глікопептидфосфонатів |
| WO2003099858A1 (en) * | 2002-05-24 | 2003-12-04 | Theravance, Inc. | Cross-linked glycopeptide-cephalosporin antibiotics |
| ATE388153T1 (de) * | 2003-07-11 | 2008-03-15 | Theravance Inc | Quervernetzte glycopeptid-cephalosporin- antibiotika |
-
1999
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- 1999-12-22 WO PCT/US1999/030543 patent/WO2000039156A1/en not_active Ceased
- 1999-12-22 KR KR1020017003918A patent/KR100665204B1/ko not_active Expired - Lifetime
- 1999-12-22 AT AT99965331T patent/ATE242783T1/de active
- 1999-12-22 HK HK02102171.5A patent/HK1040721B/en unknown
- 1999-12-22 CZ CZ20010022A patent/CZ301184B6/cs not_active IP Right Cessation
- 1999-12-22 SI SI9930389T patent/SI1140993T1/xx unknown
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- 1999-12-22 IL IL14009399A patent/IL140093A0/xx active IP Right Grant
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- 1999-12-22 PL PL348451A patent/PL198311B1/pl unknown
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- 1999-12-22 CN CNB99809434XA patent/CN1249081C/zh not_active Expired - Lifetime
- 1999-12-22 DK DK99965331T patent/DK1140993T3/da active
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- 2002-03-06 US US10/092,088 patent/US6962970B2/en not_active Expired - Lifetime
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