IL32358A - Antibiotic complex axenomycine and method for the preparation thereof - Google Patents
Antibiotic complex axenomycine and method for the preparation thereofInfo
- Publication number
- IL32358A IL32358A IL32358A IL3235869A IL32358A IL 32358 A IL32358 A IL 32358A IL 32358 A IL32358 A IL 32358A IL 3235869 A IL3235869 A IL 3235869A IL 32358 A IL32358 A IL 32358A
- Authority
- IL
- Israel
- Prior art keywords
- axenomycine
- complex
- meoh
- spectrum
- components
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000000741 silica gel Substances 0.000 abstract 3
- 229910002027 silica gel Inorganic materials 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 241000786363 Rhampholeon spectrum Species 0.000 abstract 2
- 241001342522 Vampyrum spectrum Species 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- 238000004458 analytical method Methods 0.000 abstract 2
- 230000008018 melting Effects 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QGPZXNSBZMHHSR-UHFFFAOYSA-N 2-carboxybenzoate;phenylazanium Chemical compound NC1=CC=CC=C1.OC(=O)C1=CC=CC=C1C(O)=O QGPZXNSBZMHHSR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 208000007976 Ketosis Diseases 0.000 abstract 1
- 241000187747 Streptomyces Species 0.000 abstract 1
- 150000001323 aldoses Chemical class 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000499 gel Substances 0.000 abstract 1
- 229910052500 inorganic mineral Chemical class 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 150000002584 ketoses Chemical class 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011707 mineral Chemical class 0.000 abstract 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Chemical class 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HAAYBYDROVFKPU-UHFFFAOYSA-N silver;azane;nitrate Chemical compound N.N.[Ag+].[O-][N+]([O-])=O HAAYBYDROVFKPU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003536 tetrazoles Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
- G21F7/00—Shielded cells or rooms
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21H—OBTAINING ENERGY FROM RADIOACTIVE SOURCES; APPLICATIONS OF RADIATION FROM RADIOACTIVE SOURCES, NOT OTHERWISE PROVIDED FOR; UTILISING COSMIC RADIATION
- G21H5/00—Applications of radiation from radioactive sources or arrangements therefor, not otherwise provided for
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,219,709. The antibiotic axenomycine. SOC. FARMACEUTICI ITALIA. 6 June, 1969 [11 June, 1968], No. 28849/69. Heading C2A. The novel antibiotic axenomycine, also named F.I. 2604, is produced by cultivating Streptomyces lisandri n. sp., I.P.V 1951, I.M.R.U. 3935, I.M.I. 137178, or an axenomycine-producing strain thereof, under aerobic conditions in an aqueous medium containing assimilable sources of carbon and nitrogen and mineral salts, and isolating the axenomycine from the cultivated medium. The cultivation is preferably carried out at 23-37‹ C. and pH 6-9 for 60-160 hours. Axenomycine is a complex of two components, axenomycines A and B. The complex and its components are amorphous yellowish-white substances, soluble in methyl, ethyl and propyl alcohol, sparingly soluble in water, ethyl acetate, acetone and chloroform, and insoluble in benzene and petroleum ether. They reduce Fehling's solution and ammoniacal silver nitrate, give a positive reaction with tetrazole blue and a weakly positive Molisch reaction. They give negative reactions with ferric chloride, the aniline phthalate test for aldoses and the naphthoresorcinol test for ketoses. Axenomycine A has the following characteristics: elementary analysis, 61.74% C, 8.52% H, 28.87% O; molecular weight 1451.3; melting point 127-142‹ C. to give a transparent reddish gel; [α]<SP>23‹</SP> D = + 10À5‹ (C = 0.9 in MeOH); Rf = 0.49 on silica gel at pH 7.0 using n. butanol: acetic acid: water = 4: 0.5: 1; U.V. spectrum in MeOH has absorption peaks at 249, 254 and 330 mÁ and a shoulder at 265-268 mÁ; I.R. spectrum in a KBr disc has peaks at 2.94, 3À44, 5.78, 6.00, 6.16, 6.24, 6.88, 7.25, 7.41, 8.61, 8.85, 9.35, 10.00, 10.40, 10.95, 11.8 and 12À5 Á. Axenomycine B has the characteristics: elementary analysis, 62.8% C., 8.58% H, 27.8% O; molecular weight 1330.2; melting point 122- 140‹ C.; [α]<SP>23‹</SP> D = + 5‹ (C = 0.9 in MeOH); Rf = 0À61 on silica gel at pH 7À0 using n. butanol: acetic acid: water = 4À0 : 0À5: 1; U.V. spectrum in MeOH has absorption peaks at 249, 254 and 330 mÁ and a shoulder at 265- 268 mÁ; I.R. spectrum in a KBr disc has peaks at 2.94, 3À40, 5.82, 6.00, 6.16, 6.24, 6.86, 7.25, 7.41, 8.60, 8.85, 9.35, 10.00, 10.40, 10.98, 11.8, and 12À5 Á. The antibiotic complex may be extracted from the separated mycelium with e.g. methanol, or from the whole broth with a water-immiscible solvent, and purified by precipitation with a non-solvent followed by counter-current distribution. The two components may be separated by chromatography on a silica gel column at pH 7.0, developing with BuOH: HAc: H 2 O, 4: 0À5: 1 by volume. The antibiotics have anthelmintic, antiprotozoal and antifungal activity. Pharmaceutical compositions comprise axenomycine complex or one of its components A or B together with a pharmaceutically acceptable vehicle.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1757068 | 1968-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32358A0 IL32358A0 (en) | 1969-08-27 |
| IL32358A true IL32358A (en) | 1972-11-28 |
Family
ID=11150434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32358A IL32358A (en) | 1968-06-11 | 1969-06-06 | Antibiotic complex axenomycine and method for the preparation thereof |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT285817B (en) |
| BE (1) | BE734341A (en) |
| BR (1) | BR6909580D0 (en) |
| CH (1) | CH506619A (en) |
| CS (1) | CS178807B2 (en) |
| DE (1) | DE1929107C3 (en) |
| DK (1) | DK120716B (en) |
| ES (1) | ES368198A1 (en) |
| FR (1) | FR2010640A1 (en) |
| GB (1) | GB1219709A (en) |
| IE (1) | IE32866B1 (en) |
| IL (1) | IL32358A (en) |
| NL (1) | NL153271B (en) |
| NO (1) | NO127927B (en) |
| SE (1) | SE354483B (en) |
| YU (1) | YU34212B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1044819B (en) * | 1970-05-04 | 1980-04-21 | Farmaceutici Italia | ANTIBIOTIC COMPOUND |
-
1969
- 1969-05-30 NL NL696908269A patent/NL153271B/en unknown
- 1969-06-06 IL IL32358A patent/IL32358A/en unknown
- 1969-06-06 FR FR6918667A patent/FR2010640A1/fr not_active Withdrawn
- 1969-06-06 IE IE769/69A patent/IE32866B1/en unknown
- 1969-06-06 CS CS6900004032A patent/CS178807B2/en unknown
- 1969-06-06 GB GB28849/69A patent/GB1219709A/en not_active Expired
- 1969-06-09 AT AT544069A patent/AT285817B/en not_active IP Right Cessation
- 1969-06-09 BR BR209580/69A patent/BR6909580D0/en unknown
- 1969-06-09 DK DK310069AA patent/DK120716B/en unknown
- 1969-06-09 SE SE08124/69A patent/SE354483B/xx unknown
- 1969-06-09 YU YU1444/69A patent/YU34212B/en unknown
- 1969-06-09 NO NO02366/69A patent/NO127927B/no unknown
- 1969-06-09 DE DE1929107A patent/DE1929107C3/en not_active Expired
- 1969-06-10 CH CH882169A patent/CH506619A/en not_active IP Right Cessation
- 1969-06-10 BE BE734341D patent/BE734341A/xx unknown
- 1969-06-10 ES ES368198A patent/ES368198A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU144469A (en) | 1978-06-30 |
| DK120716B (en) | 1971-07-05 |
| BE734341A (en) | 1969-12-10 |
| DE1929107C3 (en) | 1978-10-12 |
| FR2010640A1 (en) | 1970-02-20 |
| ES368198A1 (en) | 1971-05-01 |
| NL153271B (en) | 1977-05-16 |
| GB1219709A (en) | 1971-01-20 |
| NO127927B (en) | 1973-09-03 |
| DE1929107B2 (en) | 1978-02-09 |
| IE32866B1 (en) | 1973-12-28 |
| BR6909580D0 (en) | 1973-04-19 |
| AT285817B (en) | 1970-11-10 |
| IL32358A0 (en) | 1969-08-27 |
| DE1929107A1 (en) | 1970-02-19 |
| CS178807B2 (en) | 1977-10-31 |
| SE354483B (en) | 1973-03-12 |
| CH506619A (en) | 1971-04-30 |
| IE32866L (en) | 1969-12-11 |
| NL6908269A (en) | 1969-12-15 |
| YU34212B (en) | 1979-02-28 |
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