Chemical modification of 2"-amino group in elsamicin A
First Claim
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1. A process for producing the compounds having the formula ##STR16## wherein N(R)(R1) is NHCH(CH3)2, N(CH3)2, NHCH═
- NH, NHCH2 (C6 H6)(OCH3)2, or N(CH3)CH2 (C6 H6)(OCH3)2, which comprises reductive N-alkylation of elsamicin A with aldehydes or ketones, in sodium cyanoborohydride, stirring at room temperature, evaporating, and purification by chromatography.
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Abstract
This invention relates to elsamicin A derivatives wherein the 2"-amino group is selectively modified by acylation or alkylation, a process for producing said elsamicin A derivatives, an antitumor composition containing the same as the active ingredient, and a method for therapy using said compositions.
10 Citations
7 Claims
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1. A process for producing the compounds having the formula ##STR16## wherein N(R)(R1) is NHCH(CH3)2, N(CH3)2, NHCH═
- NH, NHCH2 (C6 H6)(OCH3)2, or N(CH3)CH2 (C6 H6)(OCH3)2, which comprises reductive N-alkylation of elsamicin A with aldehydes or ketones, in sodium cyanoborohydride, stirring at room temperature, evaporating, and purification by chromatography.
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2. A process for producing 2"-N-formimidoylelsamicin A hydrochloride which comprises treating elsamicin A with ethyl formimidate hydrochloride, at 0°
- C., stirring at room temperature, evaporating, followed by purification.
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3. The process for producing 2"-N-methylelsamicin A which comprises debenzylation of 2"-N-(2,4-dimethoxybenzyl)-2"-N-methylelsamicin A, by catalytic hydrogenation, removing the catalyst by filtration and evaporation, followed by purification by column chromatography.
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4. The process for producing 2"-deamino-2"-morpholinoelsamicin A which comprises adding sodium cyanoborohydride to a mixture of elsamicin A with 2,4'"'"'-oxydiacetaldehyde, stirring at room temperature, evaporating, and purification by column chromatography.
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5. The process for producing 2"-N-(3-carboxypropionyl)elsamicin A which comprises N-acylation of elsamicin A with succinic anhydride in dry dioxane, stirring at room temperature, adding methanol at 5°
- C., evaporating, and purification by preparative thin-layer chromatography.
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6. The process for producing 2"-N-(phthalimidoacetyl)elsamicin A which comprises N-acylation of elsamicin A with an active ester of phthaloylglycine, then stirring at room temperature, evaporating, and purification by column chromatography.
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7. The process for producing 2"-glycylelsamicin A which comprises adding hydrazine to a solution of 2"-N-(phthalimidoacetyl)elsamicin A in ethanol, maintaining at room temperature, concentrating, and purification by preparative thin-layer chromatography.
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Current AssigneeBristol-Myers Squibb Company
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Original AssigneeBristol-Myers Squibb Company
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InventorsNishiyama, Yuji, Naito, Takayuki, Yamashita, Haruhiro, Toda, Soichiro
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Primary Examiner(s)NOT, DEFINED
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Application NumberUS07/836,627Time in Patent Office551 DaysField of Search536/16.8, 536/16.1, 536/18.1, 536/18.5, 536/18.6, 536/18.7, 536/55.3, 536/124, 514/27, 514/33, 514/34, 514/202US Class Current536/18.5CPC Class CodesC07H 17/04 Heterocyclic radicals conta...
