FR2408579A1 - Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester - Google Patents

Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester

Info

Publication number
FR2408579A1
FR2408579A1 FR7733758A FR7733758A FR2408579A1 FR 2408579 A1 FR2408579 A1 FR 2408579A1 FR 7733758 A FR7733758 A FR 7733758A FR 7733758 A FR7733758 A FR 7733758A FR 2408579 A1 FR2408579 A1 FR 2408579A1
Authority
FR
France
Prior art keywords
ester
protecting
formula
negamycin
acid
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.)
Granted
Application number
FR7733758A
Other languages
French (fr)
Other versions
FR2408579B1 (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.)
AstraZeneca SAS
Original Assignee
ICI Pharma SA
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 ICI Pharma SA filed Critical ICI Pharma SA
Priority to FR7733758A priority Critical patent/FR2408579A1/en
Publication of FR2408579A1 publication Critical patent/FR2408579A1/en
Application granted granted Critical
Publication of FR2408579B1 publication Critical patent/FR2408579B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/34—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a carbon skeleton further substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Prodn. of negamycin of formula (I) in racemic or optically active form with absolute configuration (3R, 5R) comprises first selectively reducing the keto gp. in the cpd. of formula (II). The required isomer, i.e. (3R, 5R/3S, 5S) or (3R, 5R) is sepd.; the OH gp. protected with an acid-labile gps., then the ester function hydrolysed. The resulting acid is condensed with cpds. NH2.N(CH3)CH2COOB (III) to form a peptide bond. The OH-protecting gp. is removed with acid and the prod. of formula (IV) catalytically reduced. In the formulae, A = hydrogenolysable amino-protecting gp. R' = 1-6C alkyl, is not >11C alpha-arylalkyl or is not >10C aryl. B = hydrogenolysable carboxy-protecting gp. The intermediates (II) and (IV) are also claimed as new. (I) is an antibiotic effective against Gram positive and esp. gram-negative species, including Pseudomonas. (I) can be prepd. on the several-gram scale in fewer stages.
FR7733758A 1977-11-09 1977-11-09 Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester Granted FR2408579A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7733758A FR2408579A1 (en) 1977-11-09 1977-11-09 Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7733758A FR2408579A1 (en) 1977-11-09 1977-11-09 Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester

Publications (2)

Publication Number Publication Date
FR2408579A1 true FR2408579A1 (en) 1979-06-08
FR2408579B1 FR2408579B1 (en) 1985-03-29

Family

ID=9197439

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7733758A Granted FR2408579A1 (en) 1977-11-09 1977-11-09 Antibiotic negamycin synthesis - from 6-azido-hexanoate ester and hydrazino-acetate ester

Country Status (1)

Country Link
FR (1) FR2408579A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0050799A1 (en) * 1980-10-21 1982-05-05 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid
EP0271829A2 (en) * 1986-12-10 1988-06-22 Takeda Chemical Industries, Ltd. Delta-hydroxy-beta-lysine derivatives and their production
CN107129440A (en) * 2017-06-20 2017-09-05 上海应用技术大学 A kind of total synthesis method of natural products (+) negamycin

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2331334A1 (en) * 1975-11-11 1977-06-10 Microbial Chem Res Found D-SUBSTITUTES OF NEGAMYCIN AND PROCESS FOR THEIR SYNTHESIS

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2331334A1 (en) * 1975-11-11 1977-06-10 Microbial Chem Res Found D-SUBSTITUTES OF NEGAMYCIN AND PROCESS FOR THEIR SYNTHESIS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0050799A1 (en) * 1980-10-21 1982-05-05 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid
EP0271829A2 (en) * 1986-12-10 1988-06-22 Takeda Chemical Industries, Ltd. Delta-hydroxy-beta-lysine derivatives and their production
EP0271829A3 (en) * 1986-12-10 1989-07-26 Takeda Chemical Industries, Ltd. Delta-hydroxy-beta-lysine derivatives and their production
CN107129440A (en) * 2017-06-20 2017-09-05 上海应用技术大学 A kind of total synthesis method of natural products (+) negamycin

Also Published As

Publication number Publication date
FR2408579B1 (en) 1985-03-29

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