CA1040563A - Polycyclic ether antibiotic - Google Patents
Polycyclic ether antibioticInfo
- Publication number
- CA1040563A CA1040563A CA232,017A CA232017A CA1040563A CA 1040563 A CA1040563 A CA 1040563A CA 232017 A CA232017 A CA 232017A CA 1040563 A CA1040563 A CA 1040563A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- antibiotic
- sodium
- salt
- process according
- Prior art date
- 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.)
- Expired
Links
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 11
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 21
- 241000187391 Streptomyces hygroscopicus Species 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 55
- 238000000855 fermentation Methods 0.000 claims description 25
- 230000004151 fermentation Effects 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 14
- 159000000000 sodium salts Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 239000003242 anti bacterial agent Substances 0.000 claims description 11
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 229940088710 antibiotic agent Drugs 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 159000000001 potassium salts Chemical class 0.000 claims description 3
- 239000001963 growth medium Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000001902 propagating effect Effects 0.000 claims description 2
- 238000010979 pH adjustment Methods 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 230000001165 anti-coccidial effect Effects 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 235000010633 broth Nutrition 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
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- 239000002609 medium Substances 0.000 description 9
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- 239000002054 inoculum Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 4
- -1 salic raffinosç Chemical compound 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 210000004215 spore Anatomy 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 206010023076 Isosporiasis Diseases 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
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- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
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US49628974A | 1974-08-09 | 1974-08-09 | |
US55878575A | 1975-03-17 | 1975-03-17 |
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CA1040563A true CA1040563A (en) | 1978-10-17 |
Family
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CA232,017A Expired CA1040563A (en) | 1974-08-09 | 1975-07-22 | Polycyclic ether antibiotic |
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JP (1) | JPS51125793A (nl) |
AR (1) | AR206353A1 (nl) |
AU (1) | AU477111B2 (nl) |
CA (1) | CA1040563A (nl) |
CH (1) | CH606424A5 (nl) |
DD (1) | DD122104A5 (nl) |
DE (1) | DE2534342A1 (nl) |
DK (1) | DK139102B (nl) |
ES (1) | ES439841A1 (nl) |
FI (1) | FI752180A (nl) |
FR (1) | FR2281128A1 (nl) |
GB (1) | GB1467919A (nl) |
IE (1) | IE41378B1 (nl) |
IN (1) | IN141744B (nl) |
IT (1) | IT1044145B (nl) |
LU (1) | LU73144A1 (nl) |
NL (1) | NL160612C (nl) |
RO (1) | RO67315A (nl) |
YU (1) | YU36538B (nl) |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2486399B1 (fr) * | 1979-07-11 | 1988-05-06 | Int Minerals & Chem Corp | Complexes zinciques d'antibiotiques de type polyether, leur preparation et leur utilisation comme agents d'amelioration de la croissance et de la fonction cardiovasculaire des animaux |
WO1993012800A1 (en) * | 1987-11-20 | 1993-07-08 | Dirlam John P | An acidic polycyclic ether useful as an anticoccidial agent and as a growth promotant |
JPH0751595B2 (ja) * | 1990-10-04 | 1995-06-05 | ファイザー・インコーポレーテッド | 酸性多環式エーテル抗生物質 |
-
1975
- 1975-01-01 AR AR259887A patent/AR206353A1/es active
- 1975-06-10 IE IE1303/75A patent/IE41378B1/xx unknown
- 1975-07-14 DK DK319175AA patent/DK139102B/da not_active IP Right Cessation
- 1975-07-16 IN IN1393/CAL/75A patent/IN141744B/en unknown
- 1975-07-22 CA CA232,017A patent/CA1040563A/en not_active Expired
- 1975-07-23 GB GB3087775A patent/GB1467919A/en not_active Expired
- 1975-07-25 AU AU83381/75A patent/AU477111B2/en not_active Expired
- 1975-07-29 RO RO7583007A patent/RO67315A/ro unknown
- 1975-07-30 FI FI752180A patent/FI752180A/fi not_active Application Discontinuation
- 1975-07-30 ES ES439841A patent/ES439841A1/es not_active Expired
- 1975-07-31 IT IT50749/75A patent/IT1044145B/it active
- 1975-07-31 CH CH1005675A patent/CH606424A5/xx not_active IP Right Cessation
- 1975-08-01 YU YU01969/75A patent/YU36538B/xx unknown
- 1975-08-01 NL NL7509191.A patent/NL160612C/nl not_active IP Right Cessation
- 1975-08-01 DE DE19752534342 patent/DE2534342A1/de active Pending
- 1975-08-04 JP JP50094946A patent/JPS51125793A/ja active Granted
- 1975-08-04 LU LU73144A patent/LU73144A1/xx unknown
- 1975-08-04 FR FR7524278A patent/FR2281128A1/fr active Granted
- 1975-08-05 DD DD187682A patent/DD122104A5/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK319175A (nl) | 1976-02-10 |
IE41378L (en) | 1976-02-09 |
AU8338175A (en) | 1976-10-14 |
FI752180A (nl) | 1976-02-10 |
FR2281128A1 (fr) | 1976-03-05 |
IE41378B1 (en) | 1979-12-19 |
RO67315A (ro) | 1980-03-15 |
GB1467919A (en) | 1977-03-23 |
YU36538B (en) | 1984-02-29 |
LU73144A1 (nl) | 1976-07-01 |
DE2534342A1 (de) | 1976-02-19 |
DD122104A5 (nl) | 1976-09-12 |
CH606424A5 (nl) | 1978-11-30 |
JPS51125793A (en) | 1976-11-02 |
NL7509191A (nl) | 1976-02-11 |
DK139102C (nl) | 1979-05-14 |
IT1044145B (it) | 1980-03-20 |
JPS5414196B2 (nl) | 1979-06-05 |
ES439841A1 (es) | 1977-03-01 |
AR206353A1 (es) | 1976-07-15 |
DK139102B (da) | 1978-12-18 |
YU196975A (en) | 1982-02-25 |
NL160612B (nl) | 1979-06-15 |
AU477111B2 (en) | 1976-10-14 |
IN141744B (nl) | 1977-04-09 |
NL160612C (nl) | 1979-11-15 |
FR2281128B1 (nl) | 1978-11-03 |
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