CA1151090A - Fortimicin an - Google Patents
Fortimicin anInfo
- Publication number
- CA1151090A CA1151090A CA000346820A CA346820A CA1151090A CA 1151090 A CA1151090 A CA 1151090A CA 000346820 A CA000346820 A CA 000346820A CA 346820 A CA346820 A CA 346820A CA 1151090 A CA1151090 A CA 1151090A
- Authority
- CA
- Canada
- Prior art keywords
- fortimicin
- liters
- seed
- medium
- demethylfortimicin
- 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
- DDVCNPOLKJXLSW-OPMOAULHSA-N CN[C@@H]1[C@@H](O)[C@@H](O)[C@H](NC(=O)CN)[C@@H](O[C@H]2O[C@@H](CC[C@H]2N)[C@H](C)N)[C@@H]1O Chemical compound CN[C@@H]1[C@@H](O)[C@@H](O)[C@H](NC(=O)CN)[C@@H](O[C@H]2O[C@@H](CC[C@H]2N)[C@H](C)N)[C@@H]1O DDVCNPOLKJXLSW-OPMOAULHSA-N 0.000 title claims abstract description 20
- DDVCNPOLKJXLSW-UHFFFAOYSA-N Fortimicin AN Natural products CNC1C(O)C(O)C(NC(=O)CN)C(OC2OC(CCC2N)C(C)N)C1O DDVCNPOLKJXLSW-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 241000187708 Micromonospora Species 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 5
- 238000012258 culturing Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- WFMQYKIRAVMXSU-UHFFFAOYSA-N Fortimicin AE Natural products NC1C(O)C(OC)C(NC)C(O)C1OC1C(N)CCC(C(C)N)O1 WFMQYKIRAVMXSU-UHFFFAOYSA-N 0.000 abstract description 9
- WFMQYKIRAVMXSU-LCVFDZPESA-N Fortimicin B Chemical compound N[C@H]1[C@H](O)[C@H](OC)[C@@H](NC)[C@@H](O)[C@@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 WFMQYKIRAVMXSU-LCVFDZPESA-N 0.000 abstract description 7
- 238000000855 fermentation Methods 0.000 abstract description 7
- 230000004151 fermentation Effects 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 3
- BIDUPMYXGFNAEJ-APGVDKLISA-N astromicin Chemical compound O[C@@H]1[C@H](N(C)C(=O)CN)[C@@H](OC)[C@@H](O)[C@H](N)[C@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 BIDUPMYXGFNAEJ-APGVDKLISA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- 229930195503 Fortimicin Natural products 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- 229940043379 ammonium hydroxide Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- BIDUPMYXGFNAEJ-UHFFFAOYSA-N Fortimicin A Natural products OC1C(N(C)C(=O)CN)C(OC)C(O)C(N)C1OC1C(N)CCC(C(C)N)O1 BIDUPMYXGFNAEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000011218 seed culture Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- KBIFQFMZFNTDKE-KSOXEKJASA-N (1S,2R,3R,4R,5R,6S)-6-amino-5-[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-3-(methylamino)cyclohexane-1,2,4-triol Chemical compound CN[C@@H]1[C@@H](O)[C@@H](O)[C@H](N)[C@@H](O[C@H]2O[C@@H](CC[C@H]2N)C(C)N)[C@@H]1O KBIFQFMZFNTDKE-KSOXEKJASA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WFMQYKIRAVMXSU-QXCYNEMBSA-N Fortimicin KH Chemical compound N[C@H]1[C@H](O)[C@@H](OC)[C@H](NC)[C@@H](O)[C@@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 WFMQYKIRAVMXSU-QXCYNEMBSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000004455 soybean meal Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NVRQSAQBQUUGHN-UHFFFAOYSA-N Fortimicin AS Natural products COC1C(O)C(N)C(OC2OC(CCC2N)C(C)N)C(O)C1N(C)CCO NVRQSAQBQUUGHN-UHFFFAOYSA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 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 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- CEAZRRDELHUEMR-UHFFFAOYSA-N gentamicin Chemical class O1C(C(C)NC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N CEAZRRDELHUEMR-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 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
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940041022 streptomycins Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
- C12P19/48—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being substituted by two or more nitrogen atoms, e.g. destomycin, neamin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/29—Micromonospora
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/025,250 US4219643A (en) | 1979-03-29 | 1979-03-29 | Fortimicin AN |
| US25,250 | 1979-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1151090A true CA1151090A (en) | 1983-08-02 |
Family
ID=21824938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000346820A Expired CA1151090A (en) | 1979-03-29 | 1980-03-03 | Fortimicin an |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4219643A (OSRAM) |
| JP (1) | JPS55130997A (OSRAM) |
| AR (1) | AR224399A1 (OSRAM) |
| AU (1) | AU5628080A (OSRAM) |
| BE (1) | BE882509A (OSRAM) |
| CA (1) | CA1151090A (OSRAM) |
| DE (1) | DE3012208A1 (OSRAM) |
| ES (1) | ES490012A0 (OSRAM) |
| FR (1) | FR2452497A1 (OSRAM) |
| GB (1) | GB2047688B (OSRAM) |
| GR (1) | GR67284B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7794713B2 (en) | 2004-04-07 | 2010-09-14 | Lpath, Inc. | Compositions and methods for the treatment and prevention of hyperproliferative diseases |
| US7862812B2 (en) | 2006-05-31 | 2011-01-04 | Lpath, Inc. | Methods for decreasing immune response and treating immune conditions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5246311B2 (OSRAM) * | 1973-04-17 | 1977-11-24 | ||
| US3931400A (en) * | 1973-04-17 | 1976-01-06 | Abbott Laboratories | Fortimicin B and process for production thereof |
| JPS5145675B2 (OSRAM) * | 1973-07-23 | 1976-12-04 | ||
| US3878193A (en) * | 1973-06-26 | 1975-04-15 | Schering Corp | Process for the preparation of garamine derivatives |
| US3963695A (en) * | 1974-12-19 | 1976-06-15 | Smithkline Corporation | Tetradeoxyneamine and derivatives thereof |
| US4091032A (en) * | 1976-09-23 | 1978-05-23 | Abbott Laboratories | 4-N-acylfortimicin B derivatives and the chemical conversion of fortimicin B to fortimicin A |
| US4124756A (en) * | 1976-12-27 | 1978-11-07 | Abbott Laboratories | 3-DE-O-Methylfortimicins |
-
1979
- 1979-03-29 US US06/025,250 patent/US4219643A/en not_active Expired - Lifetime
-
1980
- 1980-03-03 CA CA000346820A patent/CA1151090A/en not_active Expired
- 1980-03-07 AU AU56280/80A patent/AU5628080A/en not_active Abandoned
- 1980-03-11 GB GB8008093A patent/GB2047688B/en not_active Expired
- 1980-03-26 JP JP3763880A patent/JPS55130997A/ja active Pending
- 1980-03-27 GR GR61539A patent/GR67284B/el unknown
- 1980-03-27 ES ES490012A patent/ES490012A0/es active Granted
- 1980-03-27 FR FR8006888A patent/FR2452497A1/fr active Granted
- 1980-03-28 AR AR280487A patent/AR224399A1/es active
- 1980-03-28 BE BE0/200015A patent/BE882509A/fr not_active IP Right Cessation
- 1980-03-28 DE DE19803012208 patent/DE3012208A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES8104410A1 (es) | 1981-04-01 |
| JPS55130997A (en) | 1980-10-11 |
| US4219643A (en) | 1980-08-26 |
| FR2452497B1 (OSRAM) | 1983-06-03 |
| BE882509A (fr) | 1980-09-29 |
| AR224399A1 (es) | 1981-11-30 |
| FR2452497A1 (fr) | 1980-10-24 |
| ES490012A0 (es) | 1981-04-01 |
| GB2047688A (en) | 1980-12-03 |
| GR67284B (OSRAM) | 1981-06-29 |
| GB2047688B (en) | 1983-03-30 |
| AU5628080A (en) | 1980-10-02 |
| DE3012208A1 (de) | 1980-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |