NO325365B1 - Fremgangsmate for alkylering av et glykopeptidantibiotikum samt et kompleks av kobber og nevnte alkylerte glykopeptidantibiotikum. - Google Patents
Fremgangsmate for alkylering av et glykopeptidantibiotikum samt et kompleks av kobber og nevnte alkylerte glykopeptidantibiotikum. Download PDFInfo
- Publication number
- NO325365B1 NO325365B1 NO19992415A NO992415A NO325365B1 NO 325365 B1 NO325365 B1 NO 325365B1 NO 19992415 A NO19992415 A NO 19992415A NO 992415 A NO992415 A NO 992415A NO 325365 B1 NO325365 B1 NO 325365B1
- Authority
- NO
- Norway
- Prior art keywords
- glycopeptide antibiotic
- copper
- complex
- mmol
- alkyl
- Prior art date
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- 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 title claims description 38
- 239000003910 polypeptide antibiotic agent Substances 0.000 title claims description 37
- 239000010949 copper Substances 0.000 title claims description 33
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 29
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- 238000000034 method Methods 0.000 title claims description 26
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- -1 4-(4-chlorophenyl)benzyl Chemical group 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000004699 copper complex Chemical class 0.000 claims description 23
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 22
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 15
- 239000003638 chemical reducing agent Substances 0.000 claims description 15
- UXCMNUUPBMYDLJ-UHFFFAOYSA-N 4-(4-chlorophenyl)benzaldehyde Chemical group C1=CC(Cl)=CC=C1C1=CC=C(C=O)C=C1 UXCMNUUPBMYDLJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 13
- 150000001299 aldehydes Chemical class 0.000 claims description 11
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- 239000000047 product Substances 0.000 description 26
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 17
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- 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 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
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- 239000012279 sodium borohydride Substances 0.000 description 8
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- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 7
- UECIPBUIMXSXEI-BNSVOVDNSA-N eremomycin Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 UECIPBUIMXSXEI-BNSVOVDNSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 150000002500 ions Chemical class 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960000808 netilmicin Drugs 0.000 description 1
- ZBGPYVZLYBDXKO-HILBYHGXSA-N netilmycin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@]([C@H](NC)[C@@H](O)CO1)(C)O)NCC)[C@H]1OC(CN)=CC[C@H]1N ZBGPYVZLYBDXKO-HILBYHGXSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 108700036444 orienticin C Proteins 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229960001608 teicoplanin Drugs 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3159696P | 1996-11-21 | 1996-11-21 | |
| PCT/US1997/021238 WO1998022121A1 (en) | 1996-11-21 | 1997-11-20 | Reductive alkylation of glycopeptide antibiotics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992415L NO992415L (no) | 1999-05-20 |
| NO992415D0 NO992415D0 (no) | 1999-05-20 |
| NO325365B1 true NO325365B1 (no) | 2008-04-14 |
Family
ID=21860369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992415A NO325365B1 (no) | 1996-11-21 | 1999-05-20 | Fremgangsmate for alkylering av et glykopeptidantibiotikum samt et kompleks av kobber og nevnte alkylerte glykopeptidantibiotikum. |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP0845478B1 (es) |
| JP (1) | JP4308912B2 (es) |
| KR (1) | KR100514276B1 (es) |
| CN (1) | CN100463917C (es) |
| AR (1) | AR010621A1 (es) |
| AT (1) | ATE286910T1 (es) |
| AU (1) | AU723941B2 (es) |
| BR (1) | BR9713523B1 (es) |
| CA (1) | CA2272240C (es) |
| CO (1) | CO4650045A1 (es) |
| CZ (1) | CZ300528B6 (es) |
| DE (1) | DE69732215T2 (es) |
| EA (1) | EA002925B1 (es) |
| EG (1) | EG23855A (es) |
| HK (1) | HK1011542A1 (es) |
| HU (1) | HU227641B1 (es) |
| ID (1) | ID18900A (es) |
| IL (1) | IL129991A0 (es) |
| MY (1) | MY117383A (es) |
| NO (1) | NO325365B1 (es) |
| NZ (1) | NZ335840A (es) |
| PE (1) | PE17499A1 (es) |
| PL (1) | PL190780B1 (es) |
| TR (1) | TR199901679T2 (es) |
| TW (1) | TW585868B (es) |
| UA (1) | UA58526C2 (es) |
| WO (1) | WO1998022121A1 (es) |
| ZA (1) | ZA9710428B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6831150B2 (en) * | 2000-05-02 | 2004-12-14 | Theravance, Inc. | Reductive alkylation process |
| EP2969004A4 (en) | 2013-03-15 | 2016-09-21 | Melinta Therapeutics Inc | METHOD FOR THE TREATMENT OF INFECTIONS IN OVERWEIGHT AND ADIPOSIVE PATIENTS USING ANTIBIOTICS |
| WO2016011245A1 (en) * | 2014-07-17 | 2016-01-21 | The Medicines Company | High purity oritavancin and method of producing same |
| CN106188243B (zh) * | 2015-05-05 | 2020-06-26 | 博瑞生物医药（苏州）股份有限公司 | 一种奥利万星的制备方法 |
| CN106467570B (zh) * | 2015-08-14 | 2020-04-07 | 正大天晴药业集团股份有限公司 | 糖肽类抗生素的还原烷基化方法 |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051237A (en) * | 1975-08-28 | 1977-09-27 | Bristol-Myers Company | Glycopeptide antibiotics bu-2231 a and b and process for producing same |
| JPS58116497A (ja) * | 1981-12-29 | 1983-07-11 | Microbial Chem Res Found | アミノプロピルアミノブレオマイシン誘導体及びその製造法 |
| US4698327A (en) * | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| NZ236393A (en) * | 1989-12-13 | 1992-05-26 | Lilly Co Eli | N-alkylated glycopeptide derivatives prepared from antibiotics a82846 series and pa-42867-a; pharmaceutical compositions |
| TW457248B (en) * | 1994-01-28 | 2001-10-01 | Lilly Co Eli | Glycopeptide antibiotic derivatives |
-
1997
- 1997-11-13 ID IDP973669A patent/ID18900A/id unknown
- 1997-11-19 AT AT97309305T patent/ATE286910T1/de not_active IP Right Cessation
- 1997-11-19 EP EP97309305A patent/EP0845478B1/en not_active Expired - Lifetime
- 1997-11-19 DE DE69732215T patent/DE69732215T2/de not_active Expired - Lifetime
- 1997-11-19 ZA ZA9710428A patent/ZA9710428B/xx unknown
- 1997-11-19 MY MYPI97005545A patent/MY117383A/en unknown
- 1997-11-19 PE PE1997001054A patent/PE17499A1/es not_active Application Discontinuation
- 1997-11-19 AR ARP970105411A patent/AR010621A1/es active IP Right Grant
- 1997-11-19 CO CO97067572A patent/CO4650045A1/es unknown
- 1997-11-19 EG EG123597A patent/EG23855A/xx active
- 1997-11-20 WO PCT/US1997/021238 patent/WO1998022121A1/en active IP Right Grant
- 1997-11-20 UA UA99052810A patent/UA58526C2/uk unknown
- 1997-11-20 NZ NZ335840A patent/NZ335840A/xx not_active IP Right Cessation
- 1997-11-20 CZ CZ0179499A patent/CZ300528B6/cs not_active IP Right Cessation
- 1997-11-20 PL PL333778A patent/PL190780B1/pl unknown
- 1997-11-20 KR KR10-1999-7004441A patent/KR100514276B1/ko not_active IP Right Cessation
- 1997-11-20 AU AU54497/98A patent/AU723941B2/en not_active Ceased
- 1997-11-20 EA EA199900480A patent/EA002925B1/ru not_active IP Right Cessation
- 1997-11-20 JP JP52387898A patent/JP4308912B2/ja not_active Expired - Fee Related
- 1997-11-20 HU HU0000268A patent/HU227641B1/hu not_active IP Right Cessation
- 1997-11-20 CN CNB971813701A patent/CN100463917C/zh not_active Expired - Fee Related
- 1997-11-20 CA CA2272240A patent/CA2272240C/en not_active Expired - Fee Related
- 1997-11-20 BR BRPI9713523-2A patent/BR9713523B1/pt not_active IP Right Cessation
- 1997-11-20 IL IL12999197A patent/IL129991A0/xx not_active IP Right Cessation
- 1997-11-20 TR TR1999/01679T patent/TR199901679T2/xx unknown
- 1997-11-22 TW TW086117372A patent/TW585868B/zh not_active IP Right Cessation
-
1998
- 1998-12-03 HK HK98112780A patent/HK1011542A1/xx not_active IP Right Cessation
-
1999
- 1999-05-20 NO NO19992415A patent/NO325365B1/no not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |