DD296081A5 - Verfahren zur herstellung antibiotischer verbindungen - Google Patents

Verfahren zur herstellung antibiotischer verbindungen Download PDF

Info

Publication number: DD296081A5
Authority: DD; German Democratic Republic
Prior art keywords: solution; compounds; desxylosyl; give; mixture
Prior art date: 1988-07-19

Application number

DD89338278A

Other languages

German (de)

English (en)

Inventor

Nishio Maki

Kakushima Masatoshi

Konishi Masataka

Oki Toshikazu

Original Assignee

��`��@��k��

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.)

1988-07-19

Filing date

1989-07-18

Publication date

1991-11-21

1989-07-18 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1991-11-21 Publication of DD296081A5 publication Critical patent/DD296081A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 32
230000003115 biocidal effect Effects 0.000 title abstract description 14
238000004519 manufacturing process Methods 0.000 title abstract description 6
238000000034 method Methods 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000988 D-alanyl group Chemical group N[C@@H](C(=O)*)C 0.000 claims description 2
125000001980 alanyl group Chemical group 0.000 claims description 2
229940121375 antifungal agent Drugs 0.000 abstract description 4
239000003429 antifungal agent Substances 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000007787 solid Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
IHIIRQILYAXIOH-NUVDETJMSA-N pradimicin C Chemical compound O([C@H]1[C@@H](N)[C@@H](C)O[C@H]([C@@H]1O)O[C@@H]1[C@@H](O)C=2C=C3C(=O)C4=C(O)C=C(C=C4C(=O)C3=C(O)C=2C2=C(O)C(C(=O)N[C@H](C)C(O)=O)=C(C)C=C21)OC)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O IHIIRQILYAXIOH-NUVDETJMSA-N 0.000 description 12
239000003242 anti bacterial agent Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229940088710 antibiotic agent Drugs 0.000 description 10
125000000214 D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 8
238000000855 fermentation Methods 0.000 description 8
230000004151 fermentation Effects 0.000 description 8
239000002953 phosphate buffered saline Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
241000233866 Fungi Species 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
238000002955 isolation Methods 0.000 description 5
239000002609 medium Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
241000972646 Actinomadura hibisca Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
208000031888 Mycoses Diseases 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
229940041514 candida albicans extract Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000008103 glucose Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000012138 yeast extract Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000222122 Candida albicans Species 0.000 description 3
206010017533 Fungal infection Diseases 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000000843 anti-fungal effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003404 beta-D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000013587 production medium Substances 0.000 description 3
125000001453 quaternary ammonium group Chemical group 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
229920001817 Agar Polymers 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000008272 agar Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
238000003556 assay Methods 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
229940095731 candida albicans Drugs 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
210000005239 tubule Anatomy 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
235000019733 Fish meal Nutrition 0.000 description 1
-1 Lithium aluminum hydride Chemical compound 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005273 aeration Methods 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002021 butanolic extract Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002483 medication Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
239000012449 sabouraud dextrose agar Substances 0.000 description 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 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
- C07H15/24—Condensed ring systems having three or more rings
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- 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
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/244—Anthraquinone radicals, e.g. sennosides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
General Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Public Health (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cephalosporin Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD89338278A 1988-07-19 1989-07-18 Verfahren zur herstellung antibiotischer verbindungen DD296081A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/221,144 US4960755A (en)	1988-07-19	1988-07-19	BU-3608 derivatives

Publications (1)

Publication Number	Publication Date
DD296081A5 true DD296081A5 (de)	1991-11-21

Family

ID=22826542

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD89338278A DD296081A5 (de)	1988-07-19	1989-07-18	Verfahren zur herstellung antibiotischer verbindungen
DD89330937A DD287509A5 (de)	1988-07-19	1989-07-18	Verfahren zur herstellung antibiotischer verbindungen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD89330937A DD287509A5 (de)	1988-07-19	1989-07-18	Verfahren zur herstellung antibiotischer verbindungen

Country Status (23)

Country	Link
US (1)	US4960755A (cs)
EP (1)	EP0351799B1 (cs)
JP (1)	JP2772549B2 (cs)
KR (1)	KR970003127B1 (cs)
AT (1)	ATE100459T1 (cs)
AU (1)	AU622197B2 (cs)
CA (1)	CA1337907C (cs)
CS (1)	CS274700B2 (cs)
DD (2)	DD296081A5 (cs)
DE (1)	DE68912438T2 (cs)
DK (1)	DK170778B1 (cs)
ES (1)	ES2048793T3 (cs)
FI (1)	FI92206C (cs)
HU (2)	HU205131B (cs)
IE (1)	IE62586B1 (cs)
IL (1)	IL91001A (cs)
MY (1)	MY105128A (cs)
NO (1)	NO170544C (cs)
NZ (1)	NZ229964A (cs)
PT (1)	PT91203B (cs)
RU (2)	RU2032693C1 (cs)
YU (1)	YU138289A (cs)
ZA (1)	ZA895455B (cs)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5114857A (en) *	1988-11-10	1992-05-19	Bristol-Myers Company	Actinomadura hibisca microorganism useful for preparing serine analogs of BU-3608 antibiotics
US5183808A (en) *	1988-11-10	1993-02-02	Bristol-Myers Squibb Company	Method for treating fungal infections with serine analogs of BU-3608 antibiotics
JP2643404B2 (ja) *	1989-01-13	1997-08-20	財団法人微生物化学研究会	新抗生物質ｎ―アセチルベナノマイシンｂならびにその製造法
AU634250B2 (en) *	1989-07-10	1993-02-18	Bristol-Myers Squibb Company	Antiviral antibiotic bu-3889v
US5098708A (en) *	1990-06-14	1992-03-24	Bristol-Myers Squibb Company	Antiviral antibiotic BU-3889V
FI92207C (fi) *	1989-11-14	1994-10-10	Squibb Bristol Myers Co	Menetelmä terapeuttisesti käyttökelpoisten pradimisiinijohdannaisten valmistamiseksi
US5227370A (en) *	1989-11-14	1993-07-13	Bristol-Myers Squibb Company	Pradimicin derivatives
CA2030166C (en) *	1989-11-22	1997-10-07	Shimpei Aburaki	Pradimicin derivatives
US5696096A (en) *	1990-09-28	1997-12-09	Bristol-Myers Squibb Company	Pradimicin derivatives
US5843908A (en) *	1990-09-28	1998-12-01	Bristol-Myers Squibb Company	Pradimicins l and fl, and derivatives thereof
US5326867A (en) *	1992-07-16	1994-07-05	Bristol-Myers Squibb Company	Pradimic acids, amides, and pradimicin derivatives
US5338728A (en) *	1992-08-14	1994-08-16	Bristol-Myers Squibb	Pradimicin compounds
RU2220706C2 (ru) *	2001-11-15	2004-01-10	Научный Центр Здоровья детей РАМН	Лекарственное противогрибковое средство

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4591637A (en) *	1985-01-17	1986-05-27	Sri International	Open chain-morpholino adriamycins
US4870165A (en) *	1987-02-02	1989-09-26	Bristol-Myers Company	Antifungal antibiotics
US5055453A (en) *	1987-11-02	1991-10-08	Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai	Benanomicins a and antibiotic compositions
JP2512050B2 (ja) *	1987-12-25	1996-07-03	財団法人微生物化学研究会	新規抗かび性抗生物質デキシロシルベナノマイシンｂならびにその製造法
US5696096A (en) *	1990-09-28	1997-12-09	Bristol-Myers Squibb Company	Pradimicin derivatives

1988
- 1988-07-19 US US07/221,144 patent/US4960755A/en not_active Expired - Lifetime
1989
- 1989-07-07 CA CA000605139A patent/CA1337907C/en not_active Expired - Fee Related
- 1989-07-11 YU YU01382/89A patent/YU138289A/xx unknown
- 1989-07-14 FI FI893426A patent/FI92206C/fi not_active IP Right Cessation
- 1989-07-17 NZ NZ229964A patent/NZ229964A/en unknown
- 1989-07-17 IL IL9100189A patent/IL91001A/en not_active IP Right Cessation
- 1989-07-18 ZA ZA895455A patent/ZA895455B/xx unknown
- 1989-07-18 DK DK354689A patent/DK170778B1/da not_active IP Right Cessation
- 1989-07-18 IE IE232589A patent/IE62586B1/en not_active IP Right Cessation
- 1989-07-18 PT PT91203A patent/PT91203B/pt active IP Right Grant
- 1989-07-18 DD DD89338278A patent/DD296081A5/de unknown
- 1989-07-18 RU SU894614706A patent/RU2032693C1/ru active
- 1989-07-18 DD DD89330937A patent/DD287509A5/de not_active IP Right Cessation
- 1989-07-18 EP EP89113184A patent/EP0351799B1/en not_active Expired - Lifetime
- 1989-07-18 DE DE68912438T patent/DE68912438T2/de not_active Expired - Fee Related
- 1989-07-18 NO NO892939A patent/NO170544C/no not_active IP Right Cessation
- 1989-07-18 KR KR1019890010190A patent/KR970003127B1/ko not_active Expired - Fee Related
- 1989-07-18 AT AT89113184T patent/ATE100459T1/de not_active IP Right Cessation
- 1989-07-18 ES ES89113184T patent/ES2048793T3/es not_active Expired - Lifetime
- 1989-07-19 HU HU908256A patent/HU205131B/hu not_active IP Right Cessation
- 1989-07-19 MY MYPI89000980A patent/MY105128A/en unknown
- 1989-07-19 CS CS440889A patent/CS274700B2/cs unknown
- 1989-07-19 AU AU38274/89A patent/AU622197B2/en not_active Ceased
- 1989-07-19 HU HU893664A patent/HU203112B/hu not_active IP Right Cessation
- 1989-07-19 JP JP1184858A patent/JP2772549B2/ja not_active Expired - Lifetime
1990
- 1990-09-10 RU SU904830946A patent/RU2026302C1/ru active

Also Published As

Publication number	Publication date
MY105128A (en)	1994-08-30
HU908256D0 (en)	1991-06-28
AU622197B2 (en)	1992-04-02
US4960755A (en)	1990-10-02
NZ229964A (en)	1991-07-26
JPH0273095A (ja)	1990-03-13
HUT51283A (en)	1990-04-28
HU203112B (en)	1991-05-28
NO892939D0 (no)	1989-07-18
ZA895455B (en)	1991-12-24
YU138289A (en)	1991-02-28
DE68912438D1 (de)	1994-03-03
RU2032693C1 (ru)	1995-04-10
DD287509A5 (de)	1991-02-28
HU205131B (en)	1992-03-30
EP0351799B1 (en)	1994-01-19
IE892325L (en)	1990-01-19
ES2048793T3 (es)	1994-04-01
CS274700B2 (en)	1991-09-15
DK170778B1 (da)	1996-01-15
FI893426L (fi)	1990-01-20
PT91203A (pt)	1990-02-08
DK354689A (da)	1990-01-20
EP0351799A2 (en)	1990-01-24
RU2026302C1 (ru)	1995-01-09
ATE100459T1 (de)	1994-02-15
KR970003127B1 (ko)	1997-03-14
DK354689D0 (da)	1989-07-18
KR900001715A (ko)	1990-02-27
PT91203B (pt)	1995-03-01
NO170544B (no)	1992-07-20
FI893426A0 (fi)	1989-07-14
DE68912438T2 (de)	1994-06-01
FI92206C (fi)	1994-10-10
JP2772549B2 (ja)	1998-07-02
IL91001A0 (en)	1990-02-09
EP0351799A3 (en)	1991-04-24
IE62586B1 (en)	1995-02-08
NO892939L (no)	1990-01-22
IL91001A (en)	1995-06-29
FI92206B (fi)	1994-06-30
CS440889A2 (en)	1990-11-14
NO170544C (no)	1992-10-28
AU3827489A (en)	1990-01-25
CA1337907C (en)	1996-01-09

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20090719

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DE60132703T2 (de)	2009-02-05	Citrullimycine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel