ES8405027A1 - Tylosin derivs. - Google Patents

Tylosin derivs.

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Publication number
ES8405027A1
ES8405027A1 ES520908A ES520908A ES8405027A1 ES 8405027 A1 ES8405027 A1 ES 8405027A1 ES 520908 A ES520908 A ES 520908A ES 520908 A ES520908 A ES 520908A ES 8405027 A1 ES8405027 A1 ES 8405027A1
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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
ES520908A
Other languages
Spanish (es)
Other versions
ES520908A0 (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 ES520908A priority Critical patent/ES520908A0/en
Publication of ES8405027A1 publication Critical patent/ES8405027A1/en
Publication of ES520908A0 publication Critical patent/ES520908A0/en
Granted legal-status Critical Current

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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (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.
ES520908A 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE. Granted ES520908A0 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES520908A ES520908A0 (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
ES520908A ES520908A0 (en) 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

Publications (2)

Publication Number Publication Date
ES8405027A1 true ES8405027A1 (en) 1984-05-16
ES520908A0 ES520908A0 (en) 1984-05-16

Family

ID=8485509

Family Applications (1)

Application Number Title Priority Date Filing Date
ES520908A Granted ES520908A0 (en) 1983-03-23 1983-03-23 A METHOD FOR THE PREPARATION OF A THYLOSINE DERIVATIVE.

Country Status (1)

Country Link
ES (1) ES520908A0 (en)

Also Published As

Publication number Publication date
ES520908A0 (en) 1984-05-16

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