DE3012132A1 - 1-epi-fortimicin a und derivate dieser verbindung - Google Patents
1-epi-fortimicin a und derivate dieser verbindungInfo
- Publication number
- DE3012132A1 DE3012132A1 DE19803012132 DE3012132A DE3012132A1 DE 3012132 A1 DE3012132 A1 DE 3012132A1 DE 19803012132 DE19803012132 DE 19803012132 DE 3012132 A DE3012132 A DE 3012132A DE 3012132 A1 DE3012132 A1 DE 3012132A1
- Authority
- DE
- Germany
- Prior art keywords
- epi
- alkyl
- hydrogen
- fortimicin
- hydroxyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 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 claims 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 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 6
- WFMQYKIRAVMXSU-ZUHZVTTJSA-N 1-epi-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-ZUHZVTTJSA-N 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 claims description 3
- 101100019690 Homo sapiens KAT6B gene Proteins 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003242 anti bacterial agent Substances 0.000 description 14
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- 238000001228 spectrum Methods 0.000 description 13
- TYNZVWXDLOJTIM-QQFWICJTSA-N astromycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.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 TYNZVWXDLOJTIM-QQFWICJTSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- -1 η-butyl Chemical group 0.000 description 12
- 229910052796 boron Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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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 6
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- 239000000706 filtrate Substances 0.000 description 6
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 6
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- 229910052763 palladium Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- 241000588915 Klebsiella aerogenes Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 3
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- 235000019341 magnesium sulphate Nutrition 0.000 description 3
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- 230000001954 sterilising effect Effects 0.000 description 3
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
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- 241000607760 Shigella sonnei Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- CCCCHPPVJTVIDN-UHFFFAOYSA-N 1-hydroxybenzotriazole;1-hydroxypyrrolidine-2,5-dione Chemical compound ON1C(=O)CCC1=O.C1=CC=C2N(O)N=NC2=C1 CCCCHPPVJTVIDN-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002072 seryl group Chemical group 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002114 valyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/025,211 US4218442A (en) | 1979-03-29 | 1979-03-29 | 1-Epi-fortimicin A and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3012132A1 true DE3012132A1 (de) | 1980-10-09 |
Family
ID=21824686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803012132 Withdrawn DE3012132A1 (de) | 1979-03-29 | 1980-03-28 | 1-epi-fortimicin a und derivate dieser verbindung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4218442A (enExample) |
| JP (1) | JPS55130968A (enExample) |
| AR (1) | AR228253A1 (enExample) |
| AU (1) | AU5628280A (enExample) |
| BE (1) | BE882507A (enExample) |
| CA (1) | CA1149813A (enExample) |
| DE (1) | DE3012132A1 (enExample) |
| ES (1) | ES8104318A1 (enExample) |
| FR (1) | FR2452494A1 (enExample) |
| GB (1) | GB2047240B (enExample) |
| GR (1) | GR67745B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340727A (en) * | 1979-09-26 | 1982-07-20 | Abbott Laboratories | 1,2-Modified fortimicins A and B, intermediates therefor and method for their manufacture |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5850235B2 (ja) * | 1974-12-11 | 1983-11-09 | 明治製菓株式会社 | ３′，４′−α−エポキシ−リボスタマイシン又は−カナマイシンＢの製造法 |
| 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 |
| JPS5831603B2 (ja) * | 1977-02-02 | 1983-07-07 | 株式会社東芝 | 分散形ｄｄｃシステムにおける故障バツクアツプ装置 |
| JPS53127401A (en) * | 1977-03-24 | 1978-11-07 | Kowa Co | Novel antibiotics and process for preparing same |
-
1979
- 1979-03-29 US US06/025,211 patent/US4218442A/en not_active Expired - Lifetime
-
1980
- 1980-03-03 CA CA000346821A patent/CA1149813A/en not_active Expired
- 1980-03-07 AU AU56282/80A patent/AU5628280A/en not_active Abandoned
- 1980-03-11 GB GB8008096A patent/GB2047240B/en not_active Expired
- 1980-03-27 ES ES490010A patent/ES8104318A1/es not_active Expired
- 1980-03-27 FR FR8006885A patent/FR2452494A1/fr active Granted
- 1980-03-27 GR GR61538A patent/GR67745B/el unknown
- 1980-03-28 DE DE19803012132 patent/DE3012132A1/de not_active Withdrawn
- 1980-03-28 JP JP3914880A patent/JPS55130968A/ja active Pending
- 1980-03-28 AR AR280484A patent/AR228253A1/es active
- 1980-03-28 BE BE0/200013A patent/BE882507A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR67745B (enExample) | 1981-09-16 |
| GB2047240A (en) | 1980-11-26 |
| FR2452494A1 (fr) | 1980-10-24 |
| JPS55130968A (en) | 1980-10-11 |
| AU5628280A (en) | 1980-10-02 |
| GB2047240B (en) | 1983-07-20 |
| BE882507A (fr) | 1980-09-29 |
| FR2452494B1 (enExample) | 1983-04-22 |
| ES490010A0 (es) | 1981-04-16 |
| CA1149813A (en) | 1983-07-12 |
| US4218442A (en) | 1980-08-19 |
| AR228253A1 (es) | 1983-02-15 |
| ES8104318A1 (es) | 1981-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |