SE415262B - Sett att framstella sackaridderivat av polyen-makrolidantibiotika - Google Patents
Sett att framstella sackaridderivat av polyen-makrolidantibiotikaInfo
- Publication number
- SE415262B SE415262B SE7210472A SE1047272A SE415262B SE 415262 B SE415262 B SE 415262B SE 7210472 A SE7210472 A SE 7210472A SE 1047272 A SE1047272 A SE 1047272A SE 415262 B SE415262 B SE 415262B
- Authority
- SE
- Sweden
- Prior art keywords
- derivative
- glucose
- derivatives
- salt
- polyfungin
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 23
- 239000003242 anti bacterial agent Substances 0.000 claims description 19
- 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 claims description 16
- 239000008103 glucose Substances 0.000 claims description 16
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 15
- 229960000988 nystatin Drugs 0.000 claims description 13
- 230000003115 biocidal effect Effects 0.000 claims description 12
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- NCXMLFZGDNKEPB-UHFFFAOYSA-N Pimaricin Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCC(C)OC(=O)C=CC2OC2CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 NCXMLFZGDNKEPB-UHFFFAOYSA-N 0.000 claims description 11
- 229960003255 natamycin Drugs 0.000 claims description 11
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 claims description 11
- 150000004291 polyenes Chemical class 0.000 claims description 11
- 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 claims description 10
- 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 claims description 10
- 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 claims description 9
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 8
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 8
- 229960003942 amphotericin b Drugs 0.000 claims description 8
- 229940041033 macrolides Drugs 0.000 claims description 8
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 7
- 229960004348 candicidin Drugs 0.000 claims description 7
- -1 polyfungin Chemical compound 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- YKSVGLFNJPQDJE-YDMQLZBCSA-N (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4R,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid Chemical compound CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(O[C@@H]3O[C@H](C)[C@@H](O)[C@@H](N)[C@@H]3O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1 YKSVGLFNJPQDJE-YDMQLZBCSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229940097043 glucuronic acid Drugs 0.000 claims description 6
- 229930188428 trichomycin Natural products 0.000 claims description 6
- AWGBZRVEGDNLDZ-JCUCCFEFSA-N Rimocidine Chemical compound O([C@H]1/C=C/C=C/C=C/C=C/C[C@H](OC(=O)[C@@H](CC)[C@H](O)CC(=O)CCC[C@H](O)C[C@@]2(O)O[C@H]([C@@H]([C@@H](O)C2)C(O)=O)C1)CCC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O AWGBZRVEGDNLDZ-JCUCCFEFSA-N 0.000 claims description 5
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 4
- 229930091371 Fructose Natural products 0.000 claims description 4
- 239000005715 Fructose Substances 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 4
- AWGBZRVEGDNLDZ-UHFFFAOYSA-N Rimocidin Natural products C1C(C(C(O)C2)C(O)=O)OC2(O)CC(O)CCCC(=O)CC(O)C(CC)C(=O)OC(CCC)CC=CC=CC=CC=CC1OC1OC(C)C(O)C(N)C1O AWGBZRVEGDNLDZ-UHFFFAOYSA-N 0.000 claims description 4
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002772 monosaccharides Chemical class 0.000 claims description 4
- 229920001542 oligosaccharide Polymers 0.000 claims description 4
- 150000002482 oligosaccharides Chemical class 0.000 claims description 4
- 208000007976 Ketosis Diseases 0.000 claims description 3
- 150000001323 aldoses Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002584 ketoses Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 150000001719 carbohydrate derivatives Chemical class 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 229940088710 antibiotic agent Drugs 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
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- 241000222122 Candida albicans Species 0.000 description 10
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- 159000000000 sodium salts Chemical class 0.000 description 9
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- 150000002460 imidazoles Chemical class 0.000 description 8
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- 241000699670 Mus sp. Species 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002303 glucose derivatives Chemical class 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical class O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 description 3
- 208000007163 Dermatomycoses Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- WFBHLGOLOWZMBJ-GVYWOMJSSA-N (4r,5s,6r,7r)-1-bromo-4,5,6,7,8-pentahydroxyoctane-2,3-dione Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)C(=O)CBr WFBHLGOLOWZMBJ-GVYWOMJSSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 241000603729 Geotrichum sp. Species 0.000 description 2
- VQOXZBDYSJBXMA-UHFFFAOYSA-N Nystatin A1 Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CC(O)CCC(O)C(O)CC(O)(CC(O)C2C(O)=O)OC2C1 VQOXZBDYSJBXMA-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012984 antibiotic solution Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
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- 238000001727 in vivo Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- AXVIQHWRLSFEAC-KNYJJKDQSA-N (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxooctanal Chemical compound CC(=O)C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O AXVIQHWRLSFEAC-KNYJJKDQSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 108010023063 Bacto-peptone Proteins 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 208000035484 Cellulite Diseases 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- KBPFKXLJOXNXRQ-UHFFFAOYSA-N N1C=NC=C1.[Na].N1C=NC=C1.[Na] Chemical compound N1C=NC=C1.[Na].N1C=NC=C1.[Na] KBPFKXLJOXNXRQ-UHFFFAOYSA-N 0.000 description 1
- 206010049752 Peau d'orange Diseases 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 229940009444 amphotericin Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 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 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- OPGSFDUODIJJGF-JBUZINEHSA-N candicidin D Chemical compound C=1C=C(N)C=CC=1C(=O)CC(O)C(C)CC(C)C(C(/C=C/C=C/C=C/C=C/C=C/C=C/C=C/1)C)OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC(=O)CC(O)C(C(O)=O)C(O)CC\1OC1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O OPGSFDUODIJJGF-JBUZINEHSA-N 0.000 description 1
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- 231100000517 death Toxicity 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (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)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14999471A PL82224B1 (OSRAM) | 1971-08-13 | 1971-08-13 | |
| PL15516772 | 1972-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE415262B true SE415262B (sv) | 1980-09-22 |
Family
ID=26652844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7210472A SE415262B (sv) | 1971-08-13 | 1972-08-11 | Sett att framstella sackaridderivat av polyen-makrolidantibiotika |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4093796A (OSRAM) |
| JP (2) | JPS528318B2 (OSRAM) |
| BE (1) | BE787531A (OSRAM) |
| BG (1) | BG26812A3 (OSRAM) |
| CH (1) | CH620931A5 (OSRAM) |
| DD (1) | DD100248A5 (OSRAM) |
| DE (1) | DE2239891C2 (OSRAM) |
| ES (1) | ES406311A1 (OSRAM) |
| FI (1) | FI60877C (OSRAM) |
| FR (1) | FR2150776B1 (OSRAM) |
| GB (1) | GB1387187A (OSRAM) |
| HU (1) | HU166615B (OSRAM) |
| NL (1) | NL7211001A (OSRAM) |
| SE (1) | SE415262B (OSRAM) |
| YU (1) | YU206272A (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2417993C2 (de) * | 1974-04-11 | 1982-07-01 | Leningradskij naučno-issledovatel'skij institut antibiotikov, Leningrad | Polyenmacrolidantibiotica-Komplexe, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4195172A (en) * | 1976-04-22 | 1980-03-25 | Politechnika Gdanska | Salts of N-glycosyl derivatives of polyene macrolides, especially N-methylglucamine salts as well as the method of their preparation |
| PL100966B1 (pl) * | 1976-04-22 | 1978-11-30 | Sposob otrzymywania n-glikozylowych pochodnych makrolidow polienowych oraz ich soli,zwlaszcza soli n-metyloglukaminowej | |
| JPS53152764U (OSRAM) * | 1977-05-06 | 1978-12-01 | ||
| JPS53152331U (OSRAM) * | 1977-05-06 | 1978-11-30 | ||
| JPS53152332U (OSRAM) * | 1977-05-06 | 1978-11-30 | ||
| JPS53152333U (OSRAM) * | 1977-05-06 | 1978-11-30 | ||
| PL124284B1 (en) * | 1979-10-17 | 1983-01-31 | Politechnika Gdanska | Process for preparing n-glycosyl derivatives of antibiotics from anthracyclines group |
| ZA807892B (en) * | 1979-12-24 | 1981-12-30 | Dumex Ltd As | Water soluble guanidine derivatives of polyene marcrolides and the esters thereof |
| JPS6378037U (OSRAM) * | 1986-11-07 | 1988-05-24 | ||
| PL180253B1 (pl) * | 1995-05-13 | 2001-01-31 | Politechnika Gdanska | Pochodne N-metylo-N-glikozylowe estrów metylowych antybiotyków z grupy makrolidów polienowych i ich sole oraz sposób ich otrzymywania PL PL PL PL PL PL |
| US5942495A (en) * | 1996-05-10 | 1999-08-24 | Btg International Limited | Antibiotics |
| WO2001051061A1 (en) * | 2000-01-14 | 2001-07-19 | Intrabiotics Pharmaceuticals, Inc. | Derivatives of polyene macrolides and preparation and use thereof |
| US6664241B2 (en) * | 2000-05-31 | 2003-12-16 | Micrologix Biotech Inc. | Water-soluble amide derivatives of polyene macrolides and preparation and uses thereof |
| EP2852601A1 (en) | 2012-03-09 | 2015-04-01 | Blirt S.A. | Semisynthetic derivatives of nystatin a1 |
| AU2013276480B2 (en) | 2012-06-15 | 2018-01-04 | Blirt S.A. | N-substituted second generation derivatives of antifungal antibiotic Amphotericin B and methds of their preparation and application |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE620619A (OSRAM) * | ||||
| US2852429A (en) * | 1953-08-03 | 1958-09-16 | Lilly Co Eli | Antibiotic salts and preparation thereof |
| US2736725A (en) * | 1954-03-11 | 1956-02-28 | American Cyanamid Co | Complexes of tetracycline antibiotics and preparation of same |
| US3244590A (en) * | 1960-12-23 | 1966-04-05 | Rutgers Res And Educational Fo | Polyenic compounds and procedures related thereto |
| GB1061893A (en) * | 1964-02-20 | 1967-03-15 | Leningradsby Nii Antibiotikov | Alkali metal salts of polyene antibiotics |
| DE1670884A1 (de) * | 1967-06-24 | 1971-02-18 | Hoechst Ag | Verfahren zur Herstellung von Nucleosiden |
-
1972
- 1972-08-07 FI FI2187/72A patent/FI60877C/fi active
- 1972-08-10 US US05/279,737 patent/US4093796A/en not_active Expired - Lifetime
- 1972-08-10 YU YU02062/72A patent/YU206272A/xx unknown
- 1972-08-11 CH CH1194472A patent/CH620931A5/de not_active IP Right Cessation
- 1972-08-11 NL NL7211001A patent/NL7211001A/xx unknown
- 1972-08-11 ES ES406311A patent/ES406311A1/es not_active Expired
- 1972-08-11 SE SE7210472A patent/SE415262B/sv unknown
- 1972-08-11 BE BE787531A patent/BE787531A/xx not_active IP Right Cessation
- 1972-08-11 DD DD165009A patent/DD100248A5/xx unknown
- 1972-08-11 FR FR7229188A patent/FR2150776B1/fr not_active Expired
- 1972-08-11 HU HUPO519A patent/HU166615B/hu unknown
- 1972-08-14 GB GB3776672A patent/GB1387187A/en not_active Expired
- 1972-08-14 BG BG021197A patent/BG26812A3/xx unknown
- 1972-08-14 JP JP47081382A patent/JPS528318B2/ja not_active Expired
- 1972-08-14 DE DE2239891A patent/DE2239891C2/de not_active Expired
-
1976
- 1976-07-13 JP JP51083416A patent/JPS527447A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE787531A (fr) | 1972-12-01 |
| FI60877B (fi) | 1981-12-31 |
| US4093796A (en) | 1978-06-06 |
| DD100248A5 (OSRAM) | 1973-09-12 |
| JPS4828487A (OSRAM) | 1973-04-14 |
| JPS527447A (en) | 1977-01-20 |
| FR2150776B1 (OSRAM) | 1975-10-17 |
| BG26812A3 (bg) | 1979-06-12 |
| FI60877C (fi) | 1982-04-13 |
| CH620931A5 (OSRAM) | 1980-12-31 |
| ES406311A1 (es) | 1975-09-16 |
| YU206272A (en) | 1982-02-28 |
| HU166615B (OSRAM) | 1975-04-28 |
| DE2239891C2 (de) | 1983-03-03 |
| GB1387187A (en) | 1975-03-12 |
| JPS565369B2 (OSRAM) | 1981-02-04 |
| NL7211001A (OSRAM) | 1973-02-15 |
| JPS528318B2 (OSRAM) | 1977-03-08 |
| DE2239891A1 (de) | 1973-03-01 |
| FR2150776A1 (OSRAM) | 1973-04-13 |
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