CA2041815A1 - Composes a base d'altromycine - Google Patents

Composes a base d'altromycine

Info

Publication number: CA2041815A1
Authority: CA; Canada
Prior art keywords: compounds; altromycin; altromycins; compound; microorganism
Prior art date: 1989-02-07
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.): Abandoned

Application number

CA 2041815

Other languages

English (en)

Inventor

James B. Mcalpine

Marianna Jackson

Gregory M. Brill

James P. Karwowski

Robert J. Theriault

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.)

Abbott Laboratories

Original Assignee

Individual

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.)

1989-02-07

Filing date

1991-05-03

Publication date

1992-11-04

1991-05-03 Application filed by Individual filed Critical Individual

1991-05-03 Priority to CA 2041815 priority Critical patent/CA2041815A1/fr

1992-11-04 Publication of CA2041815A1 publication Critical patent/CA2041815A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 75
229930193638 altromycin Natural products 0.000 title claims abstract description 54
244000005700 microbiome Species 0.000 claims abstract description 19
239000000203 mixture Substances 0.000 claims abstract description 16
230000000844 anti-bacterial effect Effects 0.000 claims abstract description 12
230000001472 cytotoxic effect Effects 0.000 claims abstract description 4
241000203809 Actinomycetales Species 0.000 claims abstract 2
206010028980 Neoplasm Diseases 0.000 claims description 25
241001446247 uncultured actinomycete Species 0.000 claims description 20
238000000855 fermentation Methods 0.000 claims description 18
230000004151 fermentation Effects 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 4
235000015097 nutrients Nutrition 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
238000012258 culturing Methods 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 3
238000002211 ultraviolet spectrum Methods 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000000862 absorption spectrum Methods 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
238000001429 visible spectrum Methods 0.000 claims 2
208000035143 Bacterial infection Diseases 0.000 claims 1
208000022362 bacterial infectious disease Diseases 0.000 claims 1
210000004881 tumor cell Anatomy 0.000 abstract description 3
241000192125 Firmicutes Species 0.000 abstract description 2
FAGGWQMBDCZCOI-UHFFFAOYSA-N methyl 2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-[10-[4-(dimethylamino)-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxyacetate Chemical compound O1C(C)C(O)C(OC)CC1OC1C(N(C)C)(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)(C2C(C(OC)C(O)C(C)O2)O)C(=O)OC)O)OC1C FAGGWQMBDCZCOI-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
RQNWQOXKBDZHHK-UHFFFAOYSA-N methyl 2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-[2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-10-[5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyl-4-(methylamino)oxan-2-yl]-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxyacetate Chemical compound CNC1(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)(C2C(C(OC)C(O)C(C)O2)O)C(=O)OC)O)OC(C)C1OC1CC(OC)C(O)C(C)O1 RQNWQOXKBDZHHK-UHFFFAOYSA-N 0.000 description 26
CSPDCSMLEJFUJJ-UHFFFAOYSA-N methyl 2-[10-[4-(dimethylamino)-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxy-2-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)acetate Chemical compound O1C(C)C(O)C(OC)CC1OC1C(N(C)C)(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)(C2OC(C)C(O)C(OC)C2)C(=O)OC)O)OC1C CSPDCSMLEJFUJJ-UHFFFAOYSA-N 0.000 description 26
239000002609 medium Substances 0.000 description 25
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239000008272 agar Substances 0.000 description 17
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210000004027 cell Anatomy 0.000 description 16
238000012360 testing method Methods 0.000 description 15
239000002054 inoculum Substances 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
231100000331 toxic Toxicity 0.000 description 13
230000002588 toxic effect Effects 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
YRBLXLRNBFXANX-UHFFFAOYSA-N methyl 2-[2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-10-[5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyl-4-(methylamino)oxan-2-yl]-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxy-2-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)acetate Chemical compound CNC1(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)(C2OC(C)C(O)C(OC)C2)C(=O)OC)O)OC(C)C1OC1CC(OC)C(O)C(C)O1 YRBLXLRNBFXANX-UHFFFAOYSA-N 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
230000012010 growth Effects 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
230000005526 G1 to G0 transition Effects 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
GCSUFJBMYLHGSO-UHFFFAOYSA-N methyl 2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-[10-[4-(dimethylamino)-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]acetate Chemical compound O1C(C)C(O)C(OC)CC1OC1C(N(C)C)(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C(C5C(C(OC)C(O)C(C)O5)O)C(=O)OC)C=C4C(=O)C3=CC=2)O)OC1C GCSUFJBMYLHGSO-UHFFFAOYSA-N 0.000 description 8
HUERDIYXSZKKMF-UHFFFAOYSA-N methyl 2-[10-[4-amino-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-hydroxyacetate Chemical compound O1C(C)C(O)C(OC)CC1OC1C(N)(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)(C2C(C(OC)C(O)C(C)O2)O)C(=O)OC)O)OC1C HUERDIYXSZKKMF-UHFFFAOYSA-N 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
229920002472 Starch Polymers 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
BQCHGWYGWQEMTJ-YLGMGCDCSA-N [(2r,3r,4s,6r)-4-(dimethylamino)-6-[8-[(2s,4s,5r,6r)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-11-hydroxy-5-methyl-2-[2-methyl-3-[(z)-prop-1-enyl]oxiran-2-yl]-4,7,12-trioxonaphtho[2,3-h]chromen-10-yl]-2,4-dimethyloxan-3-yl] acetate Chemical compound C\C=C/C1OC1(C)C1=CC(=O)C2=C(C)C=C(C(=O)C=3C(=C(O)C([C@@H]4O[C@H](C)[C@H](OC(C)=O)[C@](C)(C4)N(C)C)=CC=3[C@H]3O[C@H](C)[C@H](O)[C@H](C3)N(C)C)C3=O)C3=C2O1 BQCHGWYGWQEMTJ-YLGMGCDCSA-N 0.000 description 7
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
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238000002955 isolation Methods 0.000 description 7
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229940041514 candida albicans extract Drugs 0.000 description 6
238000011534 incubation Methods 0.000 description 6
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239000012138 yeast extract Substances 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
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102000016943 Muramidase Human genes 0.000 description 4
108010014251 Muramidase Proteins 0.000 description 4
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 4
240000004808 Saccharomyces cerevisiae Species 0.000 description 4
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GIRRNXGFLVLKKQ-UHFFFAOYSA-N altromycin E Natural products CNC1(C)CC(C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C(C5C(C(OC)C(O)C(C)O5)O)C(=O)OC)C=C4C(=O)C3=CC=2)O)OC(C)C1OC1CC(OC)C(O)C(C)O1 GIRRNXGFLVLKKQ-UHFFFAOYSA-N 0.000 description 4
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
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229940088710 antibiotic agent Drugs 0.000 description 4
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
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HUERDIYXSZKKMF-WAAXAXADSA-N methyl 2-[10-[(2r,4s,5s,6s)-4-amino-5-[(2r,4s,5r,6r)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-[(2s,3s,4r,5r,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan- Chemical compound O1[C@H](C)[C@@H](O)[C@@H](OC)C[C@H]1O[C@H]1[C@](N)(C)C[C@H](C=2C(=C3C(=O)C4=C5C(C(C=C(O5)C5(C)C(O5)C)=O)=C(C=C4C(=O)C3=CC=2)C(O)([C@@H]2[C@H]([C@H](OC)[C@H](O)[C@@H](C)O2)O)C(=O)OC)O)O[C@H]1C HUERDIYXSZKKMF-WAAXAXADSA-N 0.000 description 4
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CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
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Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA 2041815 1989-02-07 1991-05-03 Composes a base d'altromycine Abandoned CA2041815A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2041815 CA2041815A1 (fr)	1989-02-07	1991-05-03	Composes a base d'altromycine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US30755589A	1989-02-07	1989-02-07
CA 2041815 CA2041815A1 (fr)	1989-02-07	1991-05-03	Composes a base d'altromycine

Publications (1)

Publication Number	Publication Date
CA2041815A1 true CA2041815A1 (fr)	1992-11-04

Family

ID=25674590

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2041815 Abandoned CA2041815A1 (fr)	1989-02-07	1991-05-03	Composes a base d'altromycine

Country Status (1)

Country	Link
CA (1)	CA2041815A1 (fr)

1991
- 1991-05-03 CA CA 2041815 patent/CA2041815A1/fr not_active Abandoned

Publication	Publication Date	Title
DK172545B1 (da)	1998-12-14	Antibiotiske glycopeptider og fremgangsmåde til deres fremstilling
KR100659680B1 (ko)	2006-12-21	항생 물질 카프라자마이신류 및 그 제조법
JP4538455B2 (ja)	2010-09-08	抗生物質化合物
NL8501708A (nl)	1986-01-16	Antitumor antibioticum.
JP5283927B2 (ja)	2013-09-04	新規化合物アミコラマイシン、その製造方法及びその用途
US4375542A (en)	1983-03-01	Kijanimicin antibiotics and derivatives thereof
WO1990009435A1 (fr)	1990-08-23	Composes d'altromycine
RU2228337C2 (ru)	2004-05-10	Ванкорезмицин (варианты), его использование, штамм amycolatopsis вида hil-006734 для его получения
WO2010122669A1 (fr)	2010-10-28	Nouveau composé amycolamycine, son procédé de production et son utilisation
US4440751A (en)	1984-04-03	Broad spectrum antibiotic complex produced by a novel micromonospora
US4598145A (en)	1986-07-01	Albacarcins V and M
US5994543A (en)	1999-11-30	Antibiotic bravomicins
JPH0229079B2 (fr)	1990-06-27
CA2041815A1 (fr)	1992-11-04	Composes a base d'altromycine
US4137224A (en)	1979-01-30	Process for the preparation of antibiotic W-10 complex and for the isolation of antibiotic 20561 and antibiotic 20562 therefrom
US4461831A (en)	1984-07-24	Antitumor agents albacarcins V and M
Selva et al.	1990	ANTIBIOTIC SB22484: A NOVEL COMPLEX OF THE AURODOX GROUP I. TAXONOMY OF THE PRODUCING ORGANISM, ISOLATION OF THE ANTIBIOTICS AND CHEMICAL AND BIOLOGICAL CHARACTERIZATION
US5171740A (en)	1992-12-15	Coumamidine compounds
JPH0374388A (ja)	1991-03-28	新規なｌ―６８３，５９０の微生物変換生成物
JPH0368583A (ja)	1991-03-25	新規微生物変換物質
EP0094176B1 (fr)	1985-08-21	Antibiotiques macrolides à partir de streptomyces
JPS6317834B2 (fr)	1988-04-15
US20080096856A1 (en)	2008-04-24	Antibiotic Compound
US4732976A (en)	1988-03-22	3,3-neotrehalosadiamine antibiotic and producing it with novel microorganism
US4230799A (en)	1980-10-28	Process for the preparation of antibiotic W-10 complex and for the isolation of Antibiotic 20561 and Antibiotic 20562 therefrom

Legal Events

Date	Code	Title	Description
1994-11-03	FZDE	Dead