CH615685A5 - Process for the preparation of 1-N-(alpha-hydroxy-omega-aminoalkanoyl)-6'-N-methyl-3',4'-dideoxykanam ycin B - Google Patents

Process for the preparation of 1-N-(alpha-hydroxy-omega-aminoalkanoyl)-6'-N-methyl-3',4'-dideoxykanam ycin B Download PDF

Info

Publication number: CH615685A5
Authority: CH; Switzerland
Prior art keywords: amino; methyl; dideoxykanamycin; kanamycin; formula
Prior art date: 1974-10-08

Application number

CH1303375A

Other languages

German (de)

English (en)

Inventor

Hamao Umezawa

Kenji Maeda

Shinichi Kondo

Sumio Umezawa

Original Assignee

Microbial Chem Res Found

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.)

1974-10-08

Filing date

1975-10-07

Publication date

1980-02-15

1975-10-07 Application filed by Microbial Chem Res Found filed Critical Microbial Chem Res Found

1980-02-15 Publication of CH615685A5 publication Critical patent/CH615685A5/de

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 19
230000008569 process Effects 0.000 title claims description 8
-1 L-5-amino-2-hydroxyvaleryl Chemical group 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 49
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
125000006239 protecting group Chemical group 0.000 claims description 39
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 34
229960003807 dibekacin Drugs 0.000 claims description 33
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229960000318 kanamycin Drugs 0.000 claims description 23
230000010933 acylation Effects 0.000 claims description 22
238000005917 acylation reaction Methods 0.000 claims description 22
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239000002253 acid Substances 0.000 claims description 14
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150000003839 salts Chemical class 0.000 claims description 10
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229960001192 bekanamycin Drugs 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 6
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SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 claims description 5
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239000000706 filtrate Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229920003145 methacrylic acid copolymer Polymers 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940007046 shigella dysenteriae Drugs 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Physical Vapour Deposition (AREA)

CH1303375A 1974-10-08 1975-10-07 Process for the preparation of 1-N-(alpha-hydroxy-omega-aminoalkanoyl)-6'-N-methyl-3',4'-dideoxykanam ycin B CH615685A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP49115199A JPS5148634A (en)	1974-10-08	1974-10-08	Taiseikinnyukona 11nn * arufua hidorokishi omega aminoashiru * 6*nn mechiru 3 *hh jideokishikanamaishin b no seizoho

Publications (1)

Publication Number	Publication Date
CH615685A5 true CH615685A5 (en)	1980-02-15

Family

ID=14656799

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1303375A CH615685A5 (en)	1974-10-08	1975-10-07	Process for the preparation of 1-N-(alpha-hydroxy-omega-aminoalkanoyl)-6'-N-methyl-3',4'-dideoxykanam ycin B

Country Status (16)

Country	Link
JP (1)	JPS5148634A (da)
BE (1)	BE834236A (da)
CA (1)	CA1050537A (da)
CH (1)	CH615685A5 (da)
DE (1)	DE2543535C3 (da)
DK (1)	DK148262C (da)
FR (1)	FR2287233A1 (da)
GB (1)	GB1475481A (da)
HU (1)	HU173702B (da)
IE (1)	IE42354B1 (da)
LU (1)	LU73533A1 (da)
NL (1)	NL181503C (da)
SE (1)	SE431216B (da)
SU (1)	SU965359A3 (da)
YU (1)	YU39659B (da)
ZA (1)	ZA756291B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57175198A (en) *	1981-04-20	1982-10-28	Microbial Chem Res Found	1-n-acyl derivative of 5,3,4-trideoxy-6-n-methylkanamycin b and their preparation
JPS60179468U (ja) *	1984-05-11	1985-11-28	大成プラス株式会社	多色スタンプ
DE102006004062A1 (de)	2006-01-28	2007-08-09	Degussa Gmbh	Kautschukmischungen
UA97245C2 (en)	2006-06-02	2012-01-25	Меиджи Сеика Фарма Ко., Лтд.	Aminoglycoside antibiotics

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4001208A (en) *	1972-10-06	1977-01-04	Zaidan Hojin Biseibutsu Kagaku Kenkyo Kai	1-N-[(S)-α-hydroxy-ω-aminoacyl]

1974
- 1974-10-08 JP JP49115199A patent/JPS5148634A/ja active Granted
1975
- 1975-09-16 GB GB3806475A patent/GB1475481A/en not_active Expired
- 1975-09-17 IE IE2043/75A patent/IE42354B1/en unknown
- 1975-09-30 DE DE2543535A patent/DE2543535C3/de not_active Expired
- 1975-10-03 NL NLAANVRAGE7511662,A patent/NL181503C/xx not_active IP Right Cessation
- 1975-10-03 ZA ZA00756291A patent/ZA756291B/xx unknown
- 1975-10-06 BE BE160728A patent/BE834236A/xx not_active IP Right Cessation
- 1975-10-06 LU LU73533A patent/LU73533A1/xx unknown
- 1975-10-07 HU HU75BI525A patent/HU173702B/hu not_active IP Right Cessation
- 1975-10-07 SE SE7511229A patent/SE431216B/xx not_active IP Right Cessation
- 1975-10-07 FR FR7531209A patent/FR2287233A1/fr active Granted
- 1975-10-07 YU YU2530/75A patent/YU39659B/xx unknown
- 1975-10-07 CH CH1303375A patent/CH615685A5/de not_active IP Right Cessation
- 1975-10-07 DK DK451475A patent/DK148262C/da not_active IP Right Cessation
- 1975-10-07 CA CA237,157A patent/CA1050537A/en not_active Expired
- 1975-10-08 SU SU752180255A patent/SU965359A3/ru active

Also Published As

Publication number	Publication date
HU173702B (hu)	1979-07-28
LU73533A1 (da)	1976-08-19
GB1475481A (en)	1977-06-01
SU965359A3 (ru)	1982-10-07
CA1050537A (en)	1979-03-13
JPS5148634A (en)	1976-04-26
ZA756291B (en)	1976-06-30
SE7511229L (sv)	1976-04-09
NL181503C (nl)	1987-09-01
FR2287233A1 (fr)	1976-05-07
DE2543535C3 (de)	1978-06-01
NL181503B (nl)	1987-04-01
AU8518975A (en)	1977-03-31
DE2543535A1 (de)	1976-04-22
JPS5653558B2 (da)	1981-12-19
SE431216B (sv)	1984-01-23
IE42354L (en)	1976-04-08
NL7511662A (nl)	1976-04-12
DK148262B (da)	1985-05-20
FR2287233B1 (da)	1978-11-10
DE2543535B2 (de)	1977-10-13
IE42354B1 (en)	1980-07-30
YU39659B (en)	1985-03-20
DK148262C (da)	1986-02-10
DK451475A (da)	1976-04-09
BE834236A (fr)	1976-04-06
YU253075A (en)	1982-05-31

Legal Events

Date	Code	Title	Description
1993-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2350169C3 (de)	1980-08-21	19.10.72 Japan 103988-72 11.12.72 Japan 123482-72 23.01.73 Japan 9146-73 1-N- [(S)-2-Hydroxy-4-amino-butyryl] -neamin-Derivate, Verfahren zu ihrer Herstellung und solche Derivate enthaltende Arzneimittel
US3940382A (en)	1976-02-24	1,2'-Di-N-substituted kanamycin B compounds
DE2332485C2 (de)	1982-10-21	Gentamicin C1-derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US4107424A (en)	1978-08-15	1-N-[(S)-α-hydroxy-ω-aminoacyl] derivatives of 3',4'-dideoxykanamycin B and 3'-deoxykanamycin B antibiotics
DE2502935A1 (de)	1975-07-31	Verfahren zur herstellung von 1-n- eckige klammer auf l-(-)-alpha-hydroxygamma-aminobutyryl eckige klammer zu -xk-62-2
DE2350203C3 (de)	1981-01-29	Verfahren zur Herstellung von 1 -N- [(S) ^-Hydroxylamino- butyryl] -neamin, -3', 4'-didesoxyneamin,-ribostamycin oder -3\4' -didesoxyribostamycin
US4120955A (en)	1978-10-17	Method for production of kanamycin C and its derivatives
DE2618009C3 (de)	1979-01-18	1-N-<a-Hydroxy-to-aminoacyl)- derivate des 3'-Deoxykanamycin A und diese enthaltende Arzneimittel
CH621558A5 (en)	1981-02-13	Process for the preparation of kanamycin derivatives with antibacterial activity
US3939143A (en)	1976-02-17	1-N-isoserylkanamycins and the production thereof
DE2818992C2 (da)	1988-03-17
CH615685A5 (en)	1980-02-15	Process for the preparation of 1-N-(alpha-hydroxy-omega-aminoalkanoyl)-6'-N-methyl-3',4'-dideoxykanam ycin B
US4147861A (en)	1979-04-03	1N-(α-Hydroxy-ω-aminoalkanoyl)-6'N-methyl-3',4'-dideoxykanamycin B and the production thereof
DE2458921B2 (de)	1977-08-04	N-(2-hydroxy-4-aminobutyryl)-derivate des antibiotikums xk-62-2, ihre salze, verfahren zu ihrer herstellung und arzneimittel
DE3112124A1 (de)	1982-02-11	Neue derivate der istamycin a und b und verfahren zur herstellung derselben
DE2512587C3 (de)	1980-07-24	1 -N-(L-4-Amino-2-hydroxybutyryl)-6' -N-alkylkanamycine A, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
DE3035057C2 (de)	1982-10-14	6"-Desoxy- und 4",6"-Didesoxy-dibekacin sowie deren 1-N(L-4-Amino-2-hydroxybutyryl)-Derivate. Verfahren zu Ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3131731C2 (de)	1984-02-16	An der 6'- oder/und 1-Aminogruppe substituierte 5,3',4'-Tridesoxykanamycine B, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
DE3111859C2 (de)	1983-03-03	Di-N&uarr;6&uarr;&uarr;'&uarr;,O&uarr;3&uarr;-desmethylistamycin A Verfahren zu dessen Herstellung und diese Verbindung enthaltende pharmazeutische Zubereitungen
DE2759475C2 (de)	1982-03-25	Verfahren zur Herstellung von Kanamycin C
DE2234315C3 (de)	1977-11-03	L-Q-Y-Amtno-a-hydroxybutvrylderivate des Kanamycins A und B, deren nicht-toxische Säureadditionssalze und Verfahren zu deren Herstellung
GB1567560A (en)	1980-05-14	Kanamycin c derivatives active against various drug-resistant bacteria
DE2509885A1 (de)	1975-09-11	1-n-(alpha-hydroxy-beta-aminopropionyl)-xk-62-2, verfahren zu seiner herstellung und arzneipraeparate
DE2234315B2 (de)	1977-03-17	L-(-)-gamma-amino-alpha-hydroxybutyrylderivate des kanamycins a und b, deren nicht-toxische saeureadditionssalze und verfahren zu deren herstellung