DD148220A5 - Verfahren fuer die herstellung einer neuartigen 6'-n-substituierten-3-n-formylkanamycin-zwischenverbindung - Google Patents

Verfahren fuer die herstellung einer neuartigen 6'-n-substituierten-3-n-formylkanamycin-zwischenverbindung Download PDF

Info

Publication number: DD148220A5
Authority: DD; German Democratic Republic
Prior art keywords: kanamycin; group; compound; acetyl; preparation
Prior art date: 1977-08-18

Application number

DD78216901A

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

1981-05-13

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

1981-05-13 Publication of DD148220A5 publication Critical patent/DD148220A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
238000006170 formylation reaction Methods 0.000 claims description 5
IEXRKQFZXJSHOB-UHFFFAOYSA-N (4-nitrophenyl) formate Chemical compound [O-][N+](=O)C1=CC=C(OC=O)C=C1 IEXRKQFZXJSHOB-UHFFFAOYSA-N 0.000 claims description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 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
230000022244 formylation Effects 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
229960000318 kanamycin Drugs 0.000 abstract description 10
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 abstract description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 6
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 abstract description 5
239000003456 ion exchange resin Substances 0.000 abstract description 5
229920003303 ion-exchange polymer Polymers 0.000 abstract description 5
239000002647 aminoglycoside antibiotic agent Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
HUAYXMGRIABALH-CHOMWAFYSA-N 3'',6'-di-N-acetylkanamycin A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CNC(=O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC(C)=O)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N HUAYXMGRIABALH-CHOMWAFYSA-N 0.000 abstract 1
238000003756 stirring Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
229960001192 bekanamycin Drugs 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
239000000203 mixture Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229920001429 chelating resin Polymers 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229930182823 kanamycin A Natural products 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
-1 1,3-dihydroxyprop-2-yl groups Chemical group 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000001962 electrophoresis Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
239000002585 base Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000004075 acetic anhydrides Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 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
230000000903 blocking effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001514 detection method 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
235000019253 formic acid Nutrition 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229930027917 kanamycin Natural products 0.000 description 1
229930182824 kanamycin B Natural products 0.000 description 1
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 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 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)

DD78216901A 1977-08-18 1978-08-18 Verfahren fuer die herstellung einer neuartigen 6'-n-substituierten-3-n-formylkanamycin-zwischenverbindung DD148220A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD148220A5 true DD148220A5 (de)	1981-05-13

Family

ID=10370176

Family Applications (2)

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

Family Applications After (1)

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

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)	DD148220A5 (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)	PL114954B1 (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
CN101868472B (zh)	2007-11-21	2013-05-29	尔察祯有限公司	抗菌性氨基糖苷类似物
WO2010132760A1 (en)	2009-05-15	2010-11-18	Achaogen, Inc.	Antibacterial derivatives of tobramycin
WO2010132757A2 (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
WO2010132765A2 (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

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 DE DE19782835759 patent/DE2835759A1/de not_active Ceased
- 1978-08-16 GR GR57007A patent/GR70241B/el unknown
- 1978-08-16 SE SE7808702A patent/SE7808702L/xx unknown
- 1978-08-16 FI FI782497A patent/FI782497A7/fi unknown
- 1978-08-16 PT PT68427A patent/PT68427A/pt unknown
- 1978-08-16 BE BE189902A patent/BE869761A/xx unknown
- 1978-08-16 AR AR273328A patent/AR218324A1/es active
- 1978-08-16 PL PL1978209082A patent/PL114954B1/pl unknown
- 1978-08-16 PL PL1978216428A patent/PL114720B1/pl unknown
- 1978-08-16 IE IE1653/78A patent/IE47150B1/en unknown
- 1978-08-17 NO NO782796A patent/NO782796L/no unknown
- 1978-08-17 JP JP10043078A patent/JPS5459256A/ja active Pending
- 1978-08-17 CA CA309,510A patent/CA1106842A/en not_active Expired
- 1978-08-17 CS CS785377A patent/CS201512B2/cs unknown
- 1978-08-17 IT IT26812/78A patent/IT1098281B/it active
- 1978-08-17 LU LU80124A patent/LU80124A1/fr unknown
- 1978-08-17 FR FR7824018A patent/FR2400523A1/fr not_active Withdrawn
- 1978-08-17 ES ES472657A patent/ES472657A1/es not_active Expired
- 1978-08-18 DD DD78216901A patent/DD148220A5/de unknown
- 1978-08-18 NL NL7808566A patent/NL7808566A/xx not_active Application Discontinuation
- 1978-08-18 DD DD78207368A patent/DD139582A5/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
DK308878A (da)	1979-02-19
AR218324A1 (es)	1980-05-30
BE869761A (fr)	1979-02-16
PL209082A1 (cs)	1980-01-02
US4178437A (en)	1979-12-11
IE47150B1 (en)	1983-12-28
GR70241B (cs)	1982-09-01
EG13472A (en)	1981-12-31
DE2835759A1 (de)	1979-03-08
NO782796L (no)	1979-02-20
CA1106842A (en)	1981-08-11
SE7808702L (sv)	1979-02-19
PL114720B1 (en)	1981-02-28
IT1098281B (it)	1985-09-07
NL7808566A (nl)	1979-02-20
AT360154B (de)	1980-12-29
JPS5459256A (en)	1979-05-12
LU80124A1 (fr)	1980-04-21
DD139582A5 (de)	1980-01-09
CS201512B2 (en)	1980-11-28
ES479667A1 (es)	1979-08-01
PT68427A (en)	1978-09-01
FR2400523A1 (fr)	1979-03-16
IT7826812A0 (it)	1978-08-17
IE781653L (en)	1979-02-18
FI782497A7 (fi)	1979-02-19
SU873889A3 (ru)	1981-10-15
ATA590278A (de)	1980-05-15
ES472657A1 (es)	1979-10-16
PL114954B1 (en)	1981-03-31

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DE3049963C2 (de)	1993-11-25	3-ß-Amino-nortropan-Derivate und Verfahren zu ihrer Herstellung
DE2432644C2 (de)	1985-12-19	N-Formyl-aminoglykoside
DE2502935B2 (de)	1977-10-06	Verfahren zur herstellung von 1-n- eckige klammer auf l-(-)-2-hydroxy- 4-aminobutyryl eckige klammer zu-xk-62-2
DE1917874C3 (de)	1980-10-02	14-Halogendaunomycine, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Adriamycin
DE2727805A1 (de)	1979-01-04	Verfahren zur herstellung von oxynormorphon
DE2739624A1 (de)	1978-04-06	Neue rifamyzin-verbindungen (i)
DE2716533A1 (de)	1977-11-03	Neue verbindungen fuer die herstellung von aminoglykosid-antibiotica, verfahren zu ihrer herstellung und ihre verwendung
SU873889A3 (ru)	1981-10-15	Способ получени 6-N-замещенного 3-N-формилканамицина
DE69500481T2 (de)	1998-02-19	Verfahren zur Herstellung von N-Chloracetylglutamin
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