GB1113473A - Water-soluble derivatives of antibiotics containing free amino-groups and method for preparing the same - Google Patents
Water-soluble derivatives of antibiotics containing free amino-groups and method for preparing the sameInfo
- Publication number
- GB1113473A GB1113473A GB2174965A GB2174965A GB1113473A GB 1113473 A GB1113473 A GB 1113473A GB 2174965 A GB2174965 A GB 2174965A GB 2174965 A GB2174965 A GB 2174965A GB 1113473 A GB1113473 A GB 1113473A
- Authority
- GB
- United Kingdom
- Prior art keywords
- colistin
- glycosides
- water
- free amino
- preparing
- 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.)
- Expired
Links
- 125000003277 amino group Chemical group 0.000 title abstract 2
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 abstract 4
- 108010078777 Colistin Proteins 0.000 abstract 3
- 229960003346 colistin Drugs 0.000 abstract 3
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 abstract 3
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 abstract 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 108010040201 Polymyxins Proteins 0.000 abstract 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 abstract 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 abstract 2
- 230000003115 biocidal effect Effects 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 229940041153 polymyxins Drugs 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 abstract 1
- 108010001478 Bacitracin Proteins 0.000 abstract 1
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 abstract 1
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 abstract 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 abstract 1
- 229930182474 N-glycoside Natural products 0.000 abstract 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 abstract 1
- 108010021006 Tyrothricin Proteins 0.000 abstract 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 abstract 1
- 229960003071 bacitracin Drugs 0.000 abstract 1
- 229930184125 bacitracin Natural products 0.000 abstract 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- XDJYMJULXQKGMM-RVYUQJQSSA-N colistin A Chemical compound CC[C@@H](C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O XDJYMJULXQKGMM-RVYUQJQSSA-N 0.000 abstract 1
- 229960003077 cycloserine Drugs 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 abstract 1
- 150000002338 glycosides Chemical class 0.000 abstract 1
- ZESIAEVDVPWEKB-ORCFLVBFSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical class OS(O)(=O)=O.OS(O)(=O)=O.CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O ZESIAEVDVPWEKB-ORCFLVBFSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GSXRBRIWJGAPDU-BBVRJQLQSA-N tyrocidine A Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 GSXRBRIWJGAPDU-BBVRJQLQSA-N 0.000 abstract 1
- 229960003281 tyrothricin Drugs 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/60—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation occurring through the 4-amino group of 2,4-diamino-butanoic acid
- C07K7/62—Polymyxins; Related peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2174965A GB1113473A (en) | 1965-05-21 | 1965-05-21 | Water-soluble derivatives of antibiotics containing free amino-groups and method for preparing the same |
| CH712166A CH449851A (fr) | 1965-05-21 | 1966-05-17 | Procédé pour la préparation d'un dérivé soluble dans l'eau d'une substance antibiotique présentant un ou des groupes amines libres |
| DE19661543545 DE1543545A1 (de) | 1965-05-21 | 1966-05-20 | Methode zur Vorbereitung neuer wasserloeslicher Derivate von Antibiotika enthaltenden Aminogruppen |
| BR17970866A BR6679708D0 (pt) | 1965-05-21 | 1966-05-20 | Derivados soluveis em agua dos grupos aminados livres contendo antibioticos e metodo para os preparar |
| BE681323D BE681323A (cg-RX-API-DMAC7.html) | 1965-05-21 | 1966-05-20 | |
| NL6607007A NL6607007A (cg-RX-API-DMAC7.html) | 1965-05-21 | 1966-05-20 | |
| AT478466A AT275030B (de) | 1965-05-21 | 1966-05-20 | Verfahren zur Herstellung neuer wasserlöslicher Derivate von freie Aminogruppen enthaltenden Antibiotika |
| ES0327030A ES327030A1 (es) | 1965-05-21 | 1966-05-21 | Metodo para preparar los derivados solubles en agua de los grupos amino libres conteniendo antibioticos. |
| LU51165A LU51165A1 (cg-RX-API-DMAC7.html) | 1965-05-21 | 1966-05-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2174965A GB1113473A (en) | 1965-05-21 | 1965-05-21 | Water-soluble derivatives of antibiotics containing free amino-groups and method for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1113473A true GB1113473A (en) | 1968-05-15 |
Family
ID=10168140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2174965A Expired GB1113473A (en) | 1965-05-21 | 1965-05-21 | Water-soluble derivatives of antibiotics containing free amino-groups and method for preparing the same |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT275030B (cg-RX-API-DMAC7.html) |
| BE (1) | BE681323A (cg-RX-API-DMAC7.html) |
| BR (1) | BR6679708D0 (cg-RX-API-DMAC7.html) |
| CH (1) | CH449851A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1543545A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES327030A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1113473A (cg-RX-API-DMAC7.html) |
| LU (1) | LU51165A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL6607007A (cg-RX-API-DMAC7.html) |
-
1965
- 1965-05-21 GB GB2174965A patent/GB1113473A/en not_active Expired
-
1966
- 1966-05-17 CH CH712166A patent/CH449851A/fr unknown
- 1966-05-20 BR BR17970866A patent/BR6679708D0/pt unknown
- 1966-05-20 BE BE681323D patent/BE681323A/xx unknown
- 1966-05-20 DE DE19661543545 patent/DE1543545A1/de active Pending
- 1966-05-20 AT AT478466A patent/AT275030B/de active
- 1966-05-20 NL NL6607007A patent/NL6607007A/xx unknown
- 1966-05-21 ES ES0327030A patent/ES327030A1/es not_active Expired
- 1966-05-23 LU LU51165A patent/LU51165A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES327030A1 (es) | 1967-03-16 |
| BE681323A (cg-RX-API-DMAC7.html) | 1966-10-31 |
| AT275030B (de) | 1969-10-10 |
| CH449851A (fr) | 1968-01-15 |
| BR6679708D0 (pt) | 1973-10-23 |
| LU51165A1 (cg-RX-API-DMAC7.html) | 1966-07-23 |
| DE1543545A1 (de) | 1970-01-02 |
| NL6607007A (cg-RX-API-DMAC7.html) | 1966-11-22 |
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