JPS5564598A - Preparation of aminoglycoside antibiotic having selectively protected amino group - Google Patents

Preparation of aminoglycoside antibiotic having selectively protected amino group

Info

Publication number
JPS5564598A
JPS5564598A JP13840278A JP13840278A JPS5564598A JP S5564598 A JPS5564598 A JP S5564598A JP 13840278 A JP13840278 A JP 13840278A JP 13840278 A JP13840278 A JP 13840278A JP S5564598 A JPS5564598 A JP S5564598A
Authority
JP
Japan
Prior art keywords
zinc
complex
amino group
aminoglycoside antibiotic
cations
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
JP13840278A
Other languages
Japanese (ja)
Other versions
JPS631319B2 (en
Inventor
Hamao Umezawa
Sumio Umezawa
Osamu Tsuchiya
Yasushi Takagi
Tomo Naohara
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 JP13840278A priority Critical patent/JPS5564598A/en
Priority to IE2026/79A priority patent/IE48972B1/en
Priority to IE1521/83A priority patent/IE48973B1/en
Priority to ZA00795691A priority patent/ZA795691B/en
Priority to IN1104/CAL/79A priority patent/IN151454B/en
Priority to SE7908850A priority patent/SE446632B/en
Priority to NL7907892A priority patent/NL7907892A/en
Priority to CH184/84A priority patent/CH650005A5/en
Priority to CH9682/79A priority patent/CH650004A5/en
Priority to US06/090,591 priority patent/US4297485A/en
Priority to AT0707979A priority patent/AT367066B/en
Priority to FR7928015A priority patent/FR2441631A1/en
Priority to ES485830A priority patent/ES485830A1/en
Priority to DE2945010A priority patent/DE2945010C2/en
Priority to YU2743/79A priority patent/YU44185B/en
Priority to DE2953878A priority patent/DE2953878C2/en
Priority to MX798478U priority patent/MX6181E/en
Priority to AU52622/79A priority patent/AU529682B2/en
Priority to PH23263A priority patent/PH16263A/en
Priority to BE2/58198A priority patent/BE879925A/en
Priority to CA000339531A priority patent/CA1118416A/en
Priority to DK476679A priority patent/DK476679A/en
Priority to HU79ZA414A priority patent/HU183050B/en
Priority to GB7938894A priority patent/GB2036020B/en
Priority to LU81881A priority patent/LU81881A1/en
Priority to AR79278828A priority patent/AR241915A1/en
Priority to GB8103076A priority patent/GB2065123B/en
Priority to IT09592/79A priority patent/IT1166021B/en
Priority to CS797711A priority patent/CS261853B2/en
Publication of JPS5564598A publication Critical patent/JPS5564598A/en
Priority to ES492479A priority patent/ES492479A0/en
Priority to PH25015A priority patent/PH15906A/en
Priority to FR8110968A priority patent/FR2482109A1/en
Priority to CA386,540A priority patent/CA1131628A/en
Priority to CS829399A priority patent/CS261859B2/en
Priority to SE8406344A priority patent/SE463264B/en
Publication of JPS631319B2 publication Critical patent/JPS631319B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
    • 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
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2

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)

Abstract

PURPOSE: To obtain the title substance useful for preparing antibiotic amikacin, by forming a complex from an aminoglycoside antibiotic, e.g. kanamycin, gentamicin, or sisomicin, with zinc cations, and by acylating the complex.
CONSTITUTION: An aminoglycoside antibiotic consisting of deoxystreptamine having an 3-aminoglycosyl or 3-alkylaminoglycosyl group at the 6-position, e.g. a compound of the formula (R1 is OH or NH2; R2 and R3 are H or OH; R4 is OH, NH2, or 1W4C alkylamino group), is reacted with zinc cations to form a zinc complex. The amino group without forming a complex bond with zinc is acylated and protected to remove the zinc, and the title substance is obtained. The complex bonds are formed at amino and OH groups at positions different from the well-known Ni, Co, Cu, or Cd cations, and various antibiotics can be obtained by introducing the desired acyl group into the amino group at the 1-position after removal of zinc cations.
COPYRIGHT: (C)1980,JPO&Japio
JP13840278A 1978-11-11 1978-11-11 Preparation of aminoglycoside antibiotic having selectively protected amino group Granted JPS5564598A (en)

Priority Applications (35)

Application Number Priority Date Filing Date Title
JP13840278A JPS5564598A (en) 1978-11-11 1978-11-11 Preparation of aminoglycoside antibiotic having selectively protected amino group
IE2026/79A IE48972B1 (en) 1978-11-11 1979-10-23 The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
IE1521/83A IE48973B1 (en) 1978-11-11 1979-10-23 The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
ZA00795691A ZA795691B (en) 1978-11-11 1979-10-24 The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
IN1104/CAL/79A IN151454B (en) 1978-11-11 1979-10-24
SE7908850A SE446632B (en) 1978-11-11 1979-10-25 SET TO MAKE A SELECTIVE PROTECTED N-ACYLATED DERIVATIVE OF AN AMINOGLYCOSIDE ANTIBIOTIC
NL7907892A NL7907892A (en) 1978-11-11 1979-10-26 METHOD FOR PREPARING A SELECTIVE PROTECTED N-ACYLATED DERIVATIVE FROM AN AMINOGLYCOSIDIC ANTIBIOTIC
CH184/84A CH650005A5 (en) 1978-11-11 1979-10-29 METHOD FOR PRODUCING A SELECTIVELY PROTECTED N-ACYLATED AMINOGLYCOSIDE ANTIBIOTIC.
CH9682/79A CH650004A5 (en) 1978-11-11 1979-10-29 METHOD FOR PRODUCING A SELECTIVELY PROTECTED N-ACYLATED AMINOGLYCOSIDE ANTIBIOTIC.
US06/090,591 US4297485A (en) 1978-11-11 1979-11-02 Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic
AT0707979A AT367066B (en) 1978-11-11 1979-11-02 METHOD FOR PRODUCING A SELECTIVELY PROTECTED N-ACYLATED DERIVATIVE OF AN AMINOGLYCOSIDE ANTIBIOTIC
AU52622/79A AU529682B2 (en) 1978-11-11 1979-11-08 N-acylated derivatives of aminoglyosidic antibiotics
ES485830A ES485830A1 (en) 1978-11-11 1979-11-08 Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic
DE2945010A DE2945010C2 (en) 1978-11-11 1979-11-08 Process for the preparation of aminoglycosides N-acylated by protecting groups
YU2743/79A YU44185B (en) 1978-11-11 1979-11-08 Process of a selective acylated n-protected derivatives of an amino-glycoside antibiotic
DE2953878A DE2953878C2 (en) 1978-11-11 1979-11-08 Process for the preparation of aminoglycosides N-acylated by protecting groups
MX798478U MX6181E (en) 1978-11-11 1979-11-08 PROCEDURE FOR THE PREPARATION OF N-PROTECTED DERIVATIVES OF AMINOGLUCOSIDIC ANTIBIOTICS
FR7928015A FR2441631A1 (en) 1978-11-11 1979-11-08 PROCESS FOR THE PREPARATION OF A SELECTIVELY PROTECTED N-ACYL DERIVATIVE OF AN AMINOGLYCOSIDE ANTIBIOTIC
PH23263A PH16263A (en) 1978-11-11 1979-11-08 The production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic
LU81881A LU81881A1 (en) 1978-11-11 1979-11-09 PROCESS FOR THE PREPARATION OF A SELECTIVELY PROTECTED N-ACYL DERIVATIVE OF AN AMINOGLYCOSIDE ANTIBIOTIC
CA000339531A CA1118416A (en) 1978-11-11 1979-11-09 Production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
DK476679A DK476679A (en) 1978-11-11 1979-11-09 METHOD FOR PREPARING A SELECTIVELY PROTECTED N-ACYLATED DERIVATIVE OF AN AMINOGLYCOSID ANTIBIOTIC
HU79ZA414A HU183050B (en) 1978-11-11 1979-11-09 Process for producing n-acyl-derivatives of aminoglycoside antibiotics
GB7938894A GB2036020B (en) 1978-11-11 1979-11-09 Production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic
BE2/58198A BE879925A (en) 1978-11-11 1979-11-09 NEW PROCESS FOR THE PREPARATION OF A SELECTIVELY PROTECTED N-ACYL DERIVATIVE OF AN AMINO-GLYCOSIDE ANTIBIOTIC
AR79278828A AR241915A1 (en) 1978-11-11 1979-11-09 Production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic
GB8103076A GB2065123B (en) 1978-11-11 1979-11-09 Production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
CS797711A CS261853B2 (en) 1978-11-11 1979-11-12 Method of aminoglycoside antibiotic's selectively acylated n-protected derivative production
IT09592/79A IT1166021B (en) 1978-11-11 1979-11-12 PROCEDURE FOR THE PRODUCTION OF A SELECTIVELY PROTECTED N ACYLATED DERIVATIVE OF AN AMINO GLYCASIDIC ANTIBIOTIC
ES492479A ES492479A0 (en) 1978-11-11 1980-06-16 PROCESS FOR THE PRODUCTION OF A SELECTIVELY PROTECTED N-ACYLATED DERIVATIVE OF AN AMINOGLYCOSIDIC ANTIBIOTIC
PH25015A PH15906A (en) 1978-11-11 1980-12-22 The production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic
FR8110968A FR2482109A1 (en) 1978-11-11 1981-06-03 PROCESS FOR THE PREPARATION OF A SELECTIVELY PROTECTED N-ACYL DERIVATIVE OF AN AMINOGLYCOSIDE ANTIBIOTIC
CA386,540A CA1131628A (en) 1978-11-11 1981-09-23 Production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
CS829399A CS261859B2 (en) 1978-11-11 1982-12-20 Method of aminoglycoside antibiotic's selectively protected n-acylated derivative preparation
SE8406344A SE463264B (en) 1978-11-11 1984-12-13 SATISFIED TO MANUFACTURE 1-N-UNPRODUCED BUT IN OTHER N-ACYLATED DERIVATIVE OF AN AMINOGLYCOSID ANTIBIOTIC

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP13840278A JPS5564598A (en) 1978-11-11 1978-11-11 Preparation of aminoglycoside antibiotic having selectively protected amino group

Publications (2)

Publication Number Publication Date
JPS5564598A true JPS5564598A (en) 1980-05-15
JPS631319B2 JPS631319B2 (en) 1988-01-12

Family

ID=15221109

Family Applications (1)

Application Number Title Priority Date Filing Date
JP13840278A Granted JPS5564598A (en) 1978-11-11 1978-11-11 Preparation of aminoglycoside antibiotic having selectively protected amino group

Country Status (5)

Country Link
JP (1) JPS5564598A (en)
BE (1) BE879925A (en)
CS (1) CS261853B2 (en)
HU (1) HU183050B (en)
ZA (1) ZA795691B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6127997A (en) * 1976-06-17 1986-02-07 テクノバイオティック・リミテッド 3,2',6'-tri-n-acyl-3',4'-dideoxykanamycin b
JPH04211696A (en) * 1990-03-08 1992-08-03 Biochimica Opos Spa Preparation of amikacin precursor
KR100450607B1 (en) * 2002-07-11 2004-09-30 경동제약 주식회사 Process for preparing Galamin

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6127997A (en) * 1976-06-17 1986-02-07 テクノバイオティック・リミテッド 3,2',6'-tri-n-acyl-3',4'-dideoxykanamycin b
JPH0132232B2 (en) * 1976-06-17 1989-06-29 Tekunobaioteitsuku Ltd
JPH04211696A (en) * 1990-03-08 1992-08-03 Biochimica Opos Spa Preparation of amikacin precursor
KR100450607B1 (en) * 2002-07-11 2004-09-30 경동제약 주식회사 Process for preparing Galamin

Also Published As

Publication number Publication date
BE879925A (en) 1980-03-03
JPS631319B2 (en) 1988-01-12
CS771179A2 (en) 1988-06-15
CS261853B2 (en) 1989-02-10
ZA795691B (en) 1980-11-26
HU183050B (en) 1984-04-28

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