JPS5982394A - アミノグリコシド誘導体、その製法および用途 - Google Patents

アミノグリコシド誘導体、その製法および用途

Info

Publication number: JPS5982394A
Authority: JP; Japan
Prior art keywords: formula; compound; hydrogen; acid; hydroxy
Prior art date: 1982-09-30
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.): Pending

Application number

JP58182953A

Other languages

English (en)

Japanese (ja)

Inventor

ハンス・ロイプネル

ヴオルフガング・シユトライヒエル

ペ−タ−・シユテユツ

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.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1982-09-30

Filing date

1983-09-29

Publication date

1984-05-12

1983-09-29 Application filed by Sandoz AG filed Critical Sandoz AG

1984-05-12 Publication of JPS5982394A publication Critical patent/JPS5982394A/ja

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 6
229940126575 aminoglycoside Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
-1 amino, methylamino, dimethylamino Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
238000002512 chemotherapy Methods 0.000 claims 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
MNZPFYUUDBYKMD-UHFFFAOYSA-N 2,3,4,5,6-pentachlorophenol;hydrochloride Chemical compound Cl.OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl MNZPFYUUDBYKMD-UHFFFAOYSA-N 0.000 claims 1
241000894006 Bacteria Species 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 claims 1
230000003115 biocidal effect Effects 0.000 claims 1
230000000973 chemotherapeutic effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000000034 method Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
229930182566 Gentamicin Natural products 0.000 description 4
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
229960002518 gentamicin Drugs 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
241000588770 Proteus mirabilis Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
239000007788 liquid Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010029155 Nephropathy toxic Diseases 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000012829 chemotherapy agent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000011254 conventional chemotherapy Methods 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 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
DNYGXMICFMACRA-UHFFFAOYSA-N gentamicin C1A Natural products O1C(CNC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N DNYGXMICFMACRA-UHFFFAOYSA-N 0.000 description 1
VEGXETMJINRLTH-BOZYPMBZSA-N gentamycin C1a Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-BOZYPMBZSA-N 0.000 description 1
125000003563 glycoside group Chemical group 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007694 nephrotoxicity Effects 0.000 description 1
231100000417 nephrotoxicity Toxicity 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 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
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
- 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
- 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)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

JP58182953A 1982-09-30 1983-09-29 アミノグリコシド誘導体、その製法および用途 Pending JPS5982394A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH5763/82		1982-09-30
CH576382		1982-09-30
CH7454/82		1982-12-21
CH7649/82		1982-12-31

Publications (1)

Publication Number	Publication Date
JPS5982394A true JPS5982394A (ja)	1984-05-12

Family

ID=4298941

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58182953A Pending JPS5982394A (ja)	1982-09-30	1983-09-29	アミノグリコシド誘導体、その製法および用途

Country Status (3)

Country	Link
JP (1)	JPS5982394A (fr)
BE (1)	BE897861A (fr)
ZA (1)	ZA837362B (fr)

1983
- 1983-09-29 BE BE1/10878A patent/BE897861A/fr not_active IP Right Cessation
- 1983-09-29 JP JP58182953A patent/JPS5982394A/ja active Pending
- 1983-09-30 ZA ZA837362A patent/ZA837362B/xx unknown

Also Published As

Publication number	Publication date
BE897861A (fr)	1984-03-29
ZA837362B (en)	1985-05-29

Publication	Publication Date	Title
DE69623745T2 (de)	2003-03-06	Derivate von DC 107
DE2742949A1 (de)	1978-03-30	4-n-acylfortimicin b-derivate
JPH03504010A (ja)	1991-09-05	ジベンゾフランカルボキサミド
IE45788B1 (en)	1982-12-01	N-acylated aminoglycosides, methods for their preparation, and compositions containing them
US4169141A (en)	1979-09-25	1-Peptidyl derivatives of di-O-aminoglycosyl-1,3-diaminocyclitol antibacterial agents
GB2030141A (en)	1980-04-02	Novel aminoglycosides, their production and use as anti-microbial agents
US3872079A (en)	1975-03-18	Semisynthetic derivatives of tobramycin
DE69517191T2 (de)	2001-02-15	Wasserlösliche derivate epipodophyllotoxine, verfahren zu ihrer herstellung, ihre verwendung als medikament und ihre verwendung zur herstellung eines antikrebsmittels
DE2355348A1 (de)	1974-05-22	Antibiotische derivate und verfahren zu ihrer herstellung
DE2618009C3 (de)	1979-01-18	1-N-<a-Hydroxy-to-aminoacyl)- derivate des 3'-Deoxykanamycin A und diese enthaltende Arzneimittel
DE2502296A1 (de)	1975-09-25	Diaminocyclitol-derivate und verfahren zu ihrer herstellung
EP0072351B1 (fr)	1985-07-24	Dérivés aminoglycosidiques, leurs procédés de préparation, compositions pharmaceutiques les contenant et de tels dérivés pour l'utilisation comme médicament
JPH07112994A (ja)	1995-05-02	白金錯体（ｉｉおよびｉｖ）、置換フェニルアルキル−エチレン−ジアミン、白金錯体（ｉｉおよびｉｖ）の製造方法、置換フェニルアルキル−エチレン−ジアミンの製造方法、この錯体を含有する抗腫瘍作用を有する医薬ならびにこれを含有する溶液、エマルションおよび懸濁液、および、その製造方法
DE2641388A1 (de)	1977-03-31	Verfahren zur herstellung von derivaten des 3', 4'-dideoxykanamycins b
JPS5982394A (ja)	1984-05-12	アミノグリコシド誘導体、その製法および用途
DE2423591C3 (de)	1980-07-31	1-N-Isoserylkanamycine, Verfahren zu ihrer Herstellung und solche Verbindungen enthaltende Arzneimittel
JPH01502660A (ja)	1989-09-14	Ｎ―１置換スルホニルアミノカルボニル、ｃ―４置換モノバクタム類
DE3044970A1 (de)	1981-09-03	3',4'-dideoxyparomomycin, verfahren zu dessen herstellung und diese verbindung enthaltende arzneimittel
DE2352361A1 (de)	1974-05-16	Antibiotische derivate
JPS58103392A (ja)	1983-06-20	３位においてチオメチルヘテロ環基により置換されたセフアロスポリンの新規な誘導体、これら化合物の製造方法およびこれらを含有する薬学的組成物
DE2458921B2 (de)	1977-08-04	N-(2-hydroxy-4-aminobutyryl)-derivate des antibiotikums xk-62-2, ihre salze, verfahren zu ihrer herstellung und arzneimittel
AU626576B2 (en)	1992-08-06	Crystalline (5r,6s)-2-carbamoyloxymethyl-6-{(1r)- hydroxyethyl}-2-penem-carboxylic acid and its pharmaceutical formulation
DE2741431C3 (de)	1979-10-25	l-N-(L-4-Amino-2-hydroxybutyryl)-3'-desoxykanamycin-C, l-N-(L-4-Amino-2hydroxybutyryl)-3',4'-didesoxykanamycin-C und deren Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Zusammensetzungen
US6080859A (en)	2000-06-27	Pyrroloindole derivatives and intermediates in producing the same
US4487924A (en)	1984-12-11	2'-N-β-Lysyl) aminoglycosides