ES8405029A1 - A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE. - Google Patents

A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

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Publication number
ES8405029A1
ES8405029A1 ES520910A ES520910A ES8405029A1 ES 8405029 A1 ES8405029 A1 ES 8405029A1 ES 520910 A ES520910 A ES 520910A ES 520910 A ES520910 A ES 520910A ES 8405029 A1 ES8405029 A1 ES 8405029A1
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ES
Spain
Prior art keywords
alkyl
group
opt
substd
bond
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
Application number
ES520910A
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Spanish (es)
Other versions
ES520910A0 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Microbial Chemistry Research Foundation
Original Assignee
Microbial Chemistry Research Foundation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Microbial Chemistry Research Foundation filed Critical Microbial Chemistry Research Foundation
Priority to ES520910A priority Critical patent/ES8405029A1/en
Publication of ES520910A0 publication Critical patent/ES520910A0/en
Publication of ES8405029A1 publication Critical patent/ES8405029A1/en
Expired legal-status Critical Current

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  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

EP--70170 A Tylosin derivs. of formula (I) are new. (R1 is OH, halogen, NR5R6, NX (opt. substd. by an oxo gp., OH, 1-6C alkyl or 1-6C hydroxyalkyl), or imidazolyl, morpholino or piperazino (each opt. substd. by 1-6C alkyl) or O-COCH2R8 R5 is H or 1-6C alkyl opt. substd. by a OH gp. R6 is H, 1-6C alkyl opt. substd. by a OH gp., aryl, aralkyl, 3-10C cycloalkyl, CO(O)mR7 or CH2R13 m is 0 or 1 R7 is 1-6C alkyl, aryl, aralkyl, furaryl or pyridinyl R13 is CH2F, CHF2 or CF3 X is (CH2)n n is 2-15 R8 is NR9R10 or SR11 R9 and R10 are H or 1-6C alkyl or R9 + R10 form 3-7C alkylene R11 is furanyl or pyridinyl R2 is H or 1-6C alkanoyl R3 is Me or CH2CHO R4 is H or OH A is O, (alpha H, beta OH) or (alpha OH, beta H) the wavy line is a single or double bond and the broken line is a single or double bond or an epoxy-bridged single bond. Provided that (1) when R1 is OH, R3 is Me and R4 is H, or the broken line is an epoxy-bridged single bond and (2) when R1 is halogen, R3 is Me or the broken line is an epoxy-bridged bond). - (I) are broad-spectrum antibacterials with greater activity then tylosin. Dose is 0.01-1 g administered 1-4 times daily. EPAB- EP--70170 B Tylosin derivs. of formula (I) are new. (R1 is OH, halogen, NR5R6, NX (opt. substd. by an oxo gp., OH, 1-6C alkyl or 1-6C hydroxyalkyl), or imidazolyl, morpholino or piperazino (each opt. substd. by 1-6C alkyl) or O-COCH2R8 R5 is H or 1-6C alkyl opt. substd. by a OH gp. R6 is H, 1-6C alkyl opt. substd. by a OH gp., aryl, aralkyl, 3-10C cycloalkyl, CO(O)mR7 or CH2R13 m is 0 or 1 R7 is 1-6C alkyl, aryl, aralkyl, furaryl or pyridinyl R13 is CH2F, CHF2 or CF3 X is (CH2)n n is 2-15 R8 is NR9R10 or SR11 R9 and R10 are H or 1-6C alkyl or R9 + R10 form 3-7C alkylene R11 is furanyl or pyridinyl R2 is H or 1-6C alkanoyl R3 is Me or CH2CHO R4 is H or OH A is O, (alpha H, beta OH) or (alpha OH, beta H) the wavy line is a single or double bond and the broken line is a single or double bond or an epoxy-bridged single bond. Provided that (1) when R1 is OH, R3 is Me and R4 is H, or the broken line is an epoxy-bridged single bond and (2) when R1 is halogen, R3 is Me or the broken line is an epoxy-bridged bond). - (I) are broad-spectrum antibacterials with greater activity then tylosin. Dose is 0.01-1 g administered 1-4 times daily. (177pp) - EP--70170 B A tylosin derivative represented by the general formula (I) wherein R1 represents NR5R6 (wherein R5 represents a hydrogen atom or a C1 to C6 alkyl group which may be substituted by a hydroxyl group and R6 represents a hydrogen atom, a C1 to C6 alkyl group which may be substituted by a hydroxyl group, an aryl group, an aralkyl group, a cycloalkyl group having 3-10 carbonatoms, -CO(O)m-R7 (wherein m represents 0 or 1 and R7 represents a C1- to C6 alkyl group, an aryl group, an aralkyl group, a furanyl group or a pyridyl group), or -CH2-R13 (wherein R13 represents a mono-, di-, or trifluoromethyl group)) gp. (a) (wherein n represents an integer of 2-15) and which may be substituted by an oxo, a hydroxyl group, A C1 to C6 alkyl group, or a hydroxy C1 to C6 alkyl group or an imidazolyl, morpholino, or piperazino group which may each be substituted by a C1 to C6 alkyl group R2 represents a hydrogen atom or a C1 to C6 alkanoyl group R3 represents a methyl or -CH2CHO group R4 represents a hydrogen atom or a hydroxyl group A represents O=, (b) or (c) wavy line reprsents a single or double bond and dotted line represents a single, a double bond, or (d) provided that when R1 is a hydroxyl group, R3 is a methyl group and R4 is hydrogen atom or said dotted line is (d), and that when R1 is halogen atom, R3 is methyl group or dotted line is (d). (151pp) USAB- US4477443 A Tylosin cpds. of formula (I) are new. In the formula, R1 or OH, halo, NR5R6, cyclic C(CH2)n which is opt. substd. or OOCCH2R8. R5 is H, alkyl or hydroxyalkyl, R6 is as for R5, aryl, aralkyl, cycloalkyl, etc. n is 2-15. R8 is NR9R10 in which R9 is R10 are H or alkyl or combine to form 3-7C alkylene gp., or is S-R11 in which R11 is furanyl or pyridyl. R2 is H or alkanoyl R3 is CH3 or CH2CHO. R4 is is H or OH. A is O, H and OH is either configuration. The dotted bond is opt. present. X is O, 2H or is absent such that a second CC bond is formed. When R1 is OH, R3 os CH3 and R4 is H or X is O. When R1 is halo, R3 is CH3 or X is O.
ES520910A 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE. Expired ES8405029A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES520910A ES8405029A1 (en) 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES520910A ES8405029A1 (en) 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

Publications (2)

Publication Number Publication Date
ES520910A0 ES520910A0 (en) 1984-05-16
ES8405029A1 true ES8405029A1 (en) 1984-05-16

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ID=8485510

Family Applications (1)

Application Number Title Priority Date Filing Date
ES520910A Expired ES8405029A1 (en) 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

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ES (1) ES8405029A1 (en)

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Publication number Publication date
ES520910A0 (en) 1984-05-16

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