IL45283A - N-demethylation of vindoline and vinblastine by s. albogriseolus - Google Patents

N-demethylation of vindoline and vinblastine by s. albogriseolus

Info

Publication number: IL45283A
Authority: IL; Israel
Prior art keywords: vindoline; vinblastine; albogriseolus; des; medium
Prior art date: 1973-09-19

Application number

IL45283A

Other languages

English (en)

Other versions

IL45283A0 (en

Original Assignee

Lilly Co Eli

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.)

1973-09-19

Filing date

1974-07-16

Publication date

1977-05-31

1974-07-16 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1974-10-22 Publication of IL45283A0 publication Critical patent/IL45283A0/xx

1977-05-31 Publication of IL45283A publication Critical patent/IL45283A/en

Links

CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 title claims abstract description 21
WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 title claims abstract description 20
GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 title claims abstract description 20
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 title claims abstract description 17
229960003048 vinblastine Drugs 0.000 title claims abstract description 15
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 title claims abstract description 15
241000187760 Streptomyces albogriseolus Species 0.000 title abstract description 12
238000010520 demethylation reaction Methods 0.000 title 1
238000000855 fermentation Methods 0.000 claims abstract description 18
230000004151 fermentation Effects 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000002609 medium Substances 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229930013930 alkaloid Natural products 0.000 description 6
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 6
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 4
150000002475 indoles Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229960004528 vincristine Drugs 0.000 description 4
150000003797 alkaloid derivatives Chemical class 0.000 description 3
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229930005303 indole alkaloid Natural products 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
241000364057 Peoria Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
JXLYSJRDGCGARV-KSNABSRWSA-N ac1l29ym Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-KSNABSRWSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000036210 malignancy Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
-1 perivinol Chemical class 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
KFWYCGGJKBFGRT-UHFFFAOYSA-N (+)-20R-15,20-dihydro-cleavamine Natural products C1C(CC)CC(CC2)CN1CCC1=C2NC2=CC=CC=C12 KFWYCGGJKBFGRT-UHFFFAOYSA-N 0.000 description 1
GWRGHAJVUZLGHL-OAHLLOKOSA-N (15R)-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,16-pentaene Chemical class C([C@H](CC1)C=C(C2)CC)N2CCC2=C1NC1=CC=CC=C21 GWRGHAJVUZLGHL-OAHLLOKOSA-N 0.000 description 1
240000001829 Catharanthus roseus Species 0.000 description 1
JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-PJXZDTQASA-N 0.000 description 1
LPGWZGMPDKDHEP-HLTPFJCJSA-N Leurosine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC LPGWZGMPDKDHEP-HLTPFJCJSA-N 0.000 description 1
LPGWZGMPDKDHEP-GKWAKPNHSA-N Leurosine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@]6(CC)O[C@@H]6[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C LPGWZGMPDKDHEP-GKWAKPNHSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
230000001335 demethylating effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
HZRZXZZTSRUSLH-WUADLFQHSA-N methyl (1S,12R,14R,15Z,18R)-15-ethylidene-12-hydroxy-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate Chemical compound O=C(OC)[C@H]1[C@H]2N(C)C/C(=C\C)/[C@@H]1C[C@@H](O)c1[nH]c3c(c1C2)cccc3 HZRZXZZTSRUSLH-WUADLFQHSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
URFWOTYPRGLZFU-PEMUAGBOSA-N perivinol Chemical compound C1C(C2=CC=CC=C2N2)=C2[C@@H](O)C[C@H]2\C(=C/C)CN[C@@H]1C2C(=O)OC URFWOTYPRGLZFU-PEMUAGBOSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000004455 soybean meal Substances 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
239000000758 substrate Substances 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
238000004809 thin layer chromatography Methods 0.000 description 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1
CXBGOBGJHGGWIE-ACSXSLCXSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-ACSXSLCXSA-N 0.000 description 1
229950003670 vinrosidine Drugs 0.000 description 1
RUEQYTQFZQYPGF-UHFFFAOYSA-N vobasinol Natural products COC(=O)C1C2CC3C4CCCCC4NC3C(O)CC1C(=CC)CN2C RUEQYTQFZQYPGF-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL45283A 1973-09-19 1974-07-16 N-demethylation of vindoline and vinblastine by s. albogriseolus IL45283A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/398,724 US3989593A (en)	1973-09-19	1973-09-19	N-demethylation of indole alkaloids by S. albogriseolus

Publications (2)

Publication Number	Publication Date
IL45283A0 IL45283A0 (en)	1974-10-22
IL45283A true IL45283A (en)	1977-05-31

Family

ID=23576549

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45283A IL45283A (en)	1973-09-19	1974-07-16	N-demethylation of vindoline and vinblastine by s. albogriseolus

Country Status (10)

Country	Link
US (2)	US3989593A (fr)
BE (1)	BE819078A (fr)
CA (1)	CA1023289A (fr)
DE (1)	DE2440931C2 (fr)
FR (1)	FR2243996B1 (fr)
GB (1)	GB1483292A (fr)
HU (1)	HU167750B (fr)
IE (1)	IE39605B1 (fr)
IL (1)	IL45283A (fr)
ZA (1)	ZA744485B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3989593A (en) *	1973-09-19	1976-11-02	Eli Lilly And Company	N-demethylation of indole alkaloids by S. albogriseolus

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3354163A (en) *	1966-12-15	1967-11-21	Eli Lillty And Company	Nu-desmethylvinblastine
US3422112A (en) *	1968-01-22	1969-01-14	Lilly Co Eli	Indolyl vindolines
ZA728535B (en) *	1972-12-01	1973-09-26	Richter Gedeon Vegyeszet	A semisynthetic process for the preparation of vincristine
US3899493A (en) *	1972-12-29	1975-08-12	Richter Gedeon Vegyeszet	Chromic acid oxidation of vinblastine sulfate to form vincristine
US3989593A (en) *	1973-09-19	1976-11-02	Eli Lilly And Company	N-demethylation of indole alkaloids by S. albogriseolus

1973
- 1973-09-19 US US05/398,724 patent/US3989593A/en not_active Expired - Lifetime
1974
- 1974-07-12 ZA ZA00744485A patent/ZA744485B/xx unknown
- 1974-07-12 IE IE1476/74A patent/IE39605B1/xx unknown
- 1974-07-16 IL IL45283A patent/IL45283A/en unknown
- 1974-07-23 CA CA205,422A patent/CA1023289A/fr not_active Expired
- 1974-08-22 FR FR7428848A patent/FR2243996B1/fr not_active Expired
- 1974-08-22 BE BE1006134A patent/BE819078A/fr not_active IP Right Cessation
- 1974-08-27 DE DE2440931A patent/DE2440931C2/de not_active Expired
- 1974-09-18 GB GB40612/74A patent/GB1483292A/en not_active Expired
- 1974-09-18 HU HUEI565A patent/HU167750B/hu not_active IP Right Cessation
1975
- 1975-12-04 US US05/637,908 patent/US4082754A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2243996B1 (fr)	1980-01-04
HU167750B (fr)	1975-12-25
BE819078A (fr)	1975-02-24
US4082754A (en)	1978-04-04
GB1483292A (en)	1977-08-17
US3989593A (en)	1976-11-02
ZA744485B (en)	1976-02-25
DE2440931A1 (de)	1975-03-20
CA1023289A (fr)	1977-12-27
FR2243996A1 (fr)	1975-04-11
IE39605B1 (en)	1978-11-22
DE2440931C2 (de)	1986-03-13
IL45283A0 (en)	1974-10-22
AU7126274A (en)	1976-01-22

Publication	Publication Date	Title
EP0271581A1 (fr)	1988-06-22	Nouveaux composes dc-88a et dc-89a1, et procede pour leur preparation
CA1113410A (fr)	1981-12-01	Analogues d'alcaloides de l'ergot
CA1054959A (fr)	1979-05-22	Rifamycine produite par le nocardia mediterranea
US4082754A (en)	1978-04-04	Des-n-methylvindoline
US5322854A (en)	1994-06-21	Reveromycin A, method for preparing the same, and antitumor agent and antifungal agent comprising the same
US3060104A (en)	1962-10-23	Process for obtaining new alkaloid derivatives of lysergic acids
Schumann et al.	1982	A new strain of Claviceps purpurea accumulating tetracyclic clavine alkaloids
US3914257A (en)	1975-10-21	Purpuromycin its derivatives and preparation thereof
KIYOTO et al.	1985	NEW ANTITUMOR ANTIBIOTICS, FR-900405 AND FR-900406 II. PRODUCTION, ISOLATION, CHARACTERIZATION AND ANTITUMOR ACTIVITY
US5100921A (en)	1992-03-31	Angucyclinones from streptomycetes, a process for the preparation thereof, and the use thereof
EP0504711B1 (fr)	1995-12-20	Composé UCA1064-B
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WO2000068413A1 (fr)	2000-11-16	Antibiotiques a base de nocathiacine substituee par halogene ou hydroxy
Wang et al.	1994	31-Homorifamycin W, a novel metabolite from Amycolatopsis mediterranei
AU682543B2 (en)	1997-10-09	Antitumor antibiotics
US3564019A (en)	1971-02-16	Tetracyclic lactone antifungal agents
US4086141A (en)	1978-04-25	Process for the fermentation production of ergoline derivatives
US4992570A (en)	1991-02-12	UCN-1028A and UCN-1028C and process for the production thereof
US3162640A (en)	1964-12-22	Alkaloid derivatives of lysergic acids
US3803307A (en)	1974-04-09	Antibiotic sl 21429
CA1285514C (fr)	1991-07-02	Substance fa-4283 physiologiquement active et sa production
EP0408336A2 (fr)	1991-01-16	Antibiotique antitumeur BU-3285T
NZ250302A (en)	1994-12-22	Hispidospermidin, its production and compositions thereof
GB1567871A (en)	1980-05-21	, -diaminoacid and its lactam
GB1567024A (en)	1980-05-08	Antibiotic a-22082 and process for production thereof