DD139582A5 - Verfahren zur herstellung von 1-n-alkyl-substituierten kanamycin-derivaten - Google Patents

Verfahren zur herstellung von 1-n-alkyl-substituierten kanamycin-derivaten Download PDF

Info

Publication number: DD139582A5
Authority: DD; German Democratic Republic
Prior art keywords: group; formula; kanamycin; item; compound
Prior art date: 1977-08-18

Application number

DD78207368A

Other languages

German (de)

English (en)

Inventor

Michael B Thomas

Original Assignee

Pfizer

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.)

1977-08-18

Filing date

1978-08-18

Publication date

1980-01-09

1978-08-18 Application filed by Pfizer filed Critical Pfizer

1980-01-09 Publication of DD139582A5 publication Critical patent/DD139582A5/de

Links

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 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title abstract description 13
229960000318 kanamycin Drugs 0.000 claims abstract description 13
229930182823 kanamycin A Natural products 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 19
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
238000005804 alkylation reaction Methods 0.000 claims description 8
230000029936 alkylation Effects 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
OYELEBBISJGNHJ-UHFFFAOYSA-N 1,3-oxazinan-2-one Chemical compound O=C1NCCCO1 OYELEBBISJGNHJ-UHFFFAOYSA-N 0.000 claims 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 claims 1
239000003242 anti bacterial agent Substances 0.000 abstract description 3
229940088710 antibiotic agent Drugs 0.000 abstract description 3
229930027917 kanamycin Natural products 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
229960001192 bekanamycin Drugs 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
229920001429 chelating resin Polymers 0.000 description 8
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 7
239000000908 ammonium hydroxide Substances 0.000 description 7
239000003456 ion exchange resin Substances 0.000 description 7
229920003303 ion-exchange polymer Polymers 0.000 description 7
239000000203 mixture Substances 0.000 description 7
-1 1,3-dihydroxyprop-2-yl group Chemical group 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000001962 electrophoresis Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229940126575 aminoglycoside Drugs 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910010272 inorganic material Inorganic materials 0.000 description 3
239000011147 inorganic material Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229930182824 kanamycin B Natural products 0.000 description 3
SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical class 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 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WDCDTUKWNICGRZ-UHFFFAOYSA-N 2-aminooxirane-2-carboxylic acid Chemical compound OC(=O)C1(N)CO1 WDCDTUKWNICGRZ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
229910006389 Li—N Inorganic materials 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
YGTPKDKJVZOVCO-KELBJJLKSA-N bekanamycin sulfate Chemical compound OS(O)(=O)=O.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 YGTPKDKJVZOVCO-KELBJJLKSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

DD78207368A 1977-08-18 1978-08-18 Verfahren zur herstellung von 1-n-alkyl-substituierten kanamycin-derivaten DD139582A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3480877		1977-08-18

Publications (1)

Publication Number	Publication Date
DD139582A5 true DD139582A5 (de)	1980-01-09

Family

ID=10370176

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD78207368A DD139582A5 (de)	1977-08-18	1978-08-18	Verfahren zur herstellung von 1-n-alkyl-substituierten kanamycin-derivaten
DD78216901A DD148220A5 (de)	1977-08-18	1978-08-18	Verfahren fuer die herstellung einer neuartigen 6'-n-substituierten-3-n-formylkanamycin-zwischenverbindung

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD78216901A DD148220A5 (de)	1977-08-18	1978-08-18	Verfahren fuer die herstellung einer neuartigen 6'-n-substituierten-3-n-formylkanamycin-zwischenverbindung

Country Status (24)

Country	Link
US (1)	US4178437A (cs)
JP (1)	JPS5459256A (cs)
AR (1)	AR218324A1 (cs)
AT (1)	AT360154B (cs)
BE (1)	BE869761A (cs)
CA (1)	CA1106842A (cs)
CS (1)	CS201512B2 (cs)
DD (2)	DD139582A5 (cs)
DE (1)	DE2835759A1 (cs)
DK (1)	DK308878A (cs)
EG (1)	EG13472A (cs)
ES (2)	ES472657A1 (cs)
FI (1)	FI782497A7 (cs)
FR (1)	FR2400523A1 (cs)
GR (1)	GR70241B (cs)
IE (1)	IE47150B1 (cs)
IT (1)	IT1098281B (cs)
LU (1)	LU80124A1 (cs)
NL (1)	NL7808566A (cs)
NO (1)	NO782796L (cs)
PL (2)	PL114720B1 (cs)
PT (1)	PT68427A (cs)
SE (1)	SE7808702L (cs)
SU (1)	SU873889A3 (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4493831A (en) *	1982-10-25	1985-01-15	Fujisawa Pharmaceutical Co., Ltd.	Aminoglycoside derivatives
US7794713B2 (en)	2004-04-07	2010-09-14	Lpath, Inc.	Compositions and methods for the treatment and prevention of hyperproliferative diseases
US7862812B2 (en)	2006-05-31	2011-01-04	Lpath, Inc.	Methods for decreasing immune response and treating immune conditions
BRPI0819319B8 (pt)	2007-11-21	2021-05-25	Achaogen Inc	análogos de aminoglicosídeo antibacteriano
WO2010132765A2 (en)	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial aminoglycoside analogs
WO2010132768A1 (en)	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial derivatives of sisomicin
WO2010132757A2 (en) *	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial aminoglycoside analogs
WO2010132759A1 (en)	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial derivatives of dibekacin
WO2010132760A1 (en)	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial derivatives of tobramycin

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE630462A (cs) *	1962-04-03
JPS5644076B2 (cs) *	1973-07-12	1981-10-16
US4029882A (en) *	1974-03-19	1977-06-14	Schering Corporation	Selective acylation of the C-1 amino group of aminoglycoside antibiotics
US4044123A (en) *	1975-05-02	1977-08-23	Schering Corporation	6'-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, methods for their use as antibacterial agents and compositions useful therefor
NZ184213A (en) *	1976-06-16	1980-05-27	Pfizer	2-deoxystreptamine aminoglycosides and antibacterial pharmaceutical compositions

1978
- 1978-07-10 DK DK308878A patent/DK308878A/da unknown
- 1978-07-14 US US05/924,515 patent/US4178437A/en not_active Expired - Lifetime
- 1978-07-30 EG EG472/78A patent/EG13472A/xx active
- 1978-08-14 AT AT590278A patent/AT360154B/de not_active IP Right Cessation
- 1978-08-16 SE SE7808702A patent/SE7808702L/xx unknown
- 1978-08-16 FI FI782497A patent/FI782497A7/fi unknown
- 1978-08-16 DE DE19782835759 patent/DE2835759A1/de not_active Ceased
- 1978-08-16 PL PL1978216428A patent/PL114720B1/pl unknown
- 1978-08-16 IE IE1653/78A patent/IE47150B1/en unknown
- 1978-08-16 BE BE189902A patent/BE869761A/xx unknown
- 1978-08-16 GR GR57007A patent/GR70241B/el unknown
- 1978-08-16 PL PL1978209082A patent/PL114954B1/pl unknown
- 1978-08-16 PT PT68427A patent/PT68427A/pt unknown
- 1978-08-16 AR AR273328A patent/AR218324A1/es active
- 1978-08-17 CA CA309,510A patent/CA1106842A/en not_active Expired
- 1978-08-17 LU LU80124A patent/LU80124A1/fr unknown
- 1978-08-17 NO NO782796A patent/NO782796L/no unknown
- 1978-08-17 CS CS785377A patent/CS201512B2/cs unknown
- 1978-08-17 FR FR7824018A patent/FR2400523A1/fr not_active Withdrawn
- 1978-08-17 IT IT26812/78A patent/IT1098281B/it active
- 1978-08-17 JP JP10043078A patent/JPS5459256A/ja active Pending
- 1978-08-17 ES ES472657A patent/ES472657A1/es not_active Expired
- 1978-08-18 NL NL7808566A patent/NL7808566A/xx not_active Application Discontinuation
- 1978-08-18 DD DD78207368A patent/DD139582A5/de unknown
- 1978-08-18 DD DD78216901A patent/DD148220A5/de unknown
1979
- 1979-04-17 ES ES479667A patent/ES479667A1/es not_active Expired
- 1979-09-06 SU SU792807718A patent/SU873889A3/ru active

Also Published As

Publication number	Publication date
FI782497A7 (fi)	1979-02-19
FR2400523A1 (fr)	1979-03-16
IE781653L (en)	1979-02-18
GR70241B (cs)	1982-09-01
PL114954B1 (en)	1981-03-31
PL209082A1 (cs)	1980-01-02
SU873889A3 (ru)	1981-10-15
IT7826812A0 (it)	1978-08-17
CA1106842A (en)	1981-08-11
AT360154B (de)	1980-12-29
US4178437A (en)	1979-12-11
DE2835759A1 (de)	1979-03-08
DK308878A (da)	1979-02-19
BE869761A (fr)	1979-02-16
LU80124A1 (fr)	1980-04-21
NO782796L (no)	1979-02-20
ES472657A1 (es)	1979-10-16
AR218324A1 (es)	1980-05-30
EG13472A (en)	1981-12-31
ES479667A1 (es)	1979-08-01
PL114720B1 (en)	1981-02-28
IT1098281B (it)	1985-09-07
JPS5459256A (en)	1979-05-12
ATA590278A (de)	1980-05-15
SE7808702L (sv)	1979-02-19
PT68427A (en)	1978-09-01
DD148220A5 (de)	1981-05-13
CS201512B2 (en)	1980-11-28
NL7808566A (nl)	1979-02-20
IE47150B1 (en)	1983-12-28

Publication	Publication Date	Title
DE2432644C2 (de)	1985-12-19	N-Formyl-aminoglykoside
US4078138A (en)	1978-03-07	3'-Epi-4'deoxykanamycin B
DE2502935C3 (de)	1978-06-01	Verfahren zur Herstellung von 1-N- [L-(-)-2-Hydroxy- 4-aminobutyryl]-XK-62-2
DD139582A5 (de)	1980-01-09	Verfahren zur herstellung von 1-n-alkyl-substituierten kanamycin-derivaten
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