BE569746A - - Google Patents

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Publication number: BE569746A
Authority: BE; Belgium
Prior art keywords: antibiotic; sep; water; acid; components
Prior art date

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English (en)

French (fr)

Publication of BE569746A publication Critical patent/BE569746A/fr

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230000003115 biocidal effect Effects 0.000 claims description 83
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
239000000243 solution Substances 0.000 claims description 51
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 37
YRMCBQLZVBXOSJ-PCFSSPOYSA-N (e)-3-[(6r,6as)-4-hydroxy-6-methoxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide Chemical compound CO[C@H]1NC2=C(O)C(C)=CC=C2C(=O)N2C=C(\C=C\C(N)=O)C[C@@H]12 YRMCBQLZVBXOSJ-PCFSSPOYSA-N 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 16
239000002585 base Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
238000004587 chromatography analysis Methods 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 8
239000002244 precipitate Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 6
239000012736 aqueous medium Substances 0.000 claims description 5
239000001913 cellulose Substances 0.000 claims description 5
229920002678 cellulose Polymers 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 4
239000000047 product Substances 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
229910021653 sulphate ion Inorganic materials 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
235000019161 pantothenic acid Nutrition 0.000 claims description 2
238000000638 solvent extraction Methods 0.000 claims description 2
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 claims 1
239000003957 anion exchange resin Substances 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
229940014662 pantothenate Drugs 0.000 claims 1
239000011713 pantothenic acid Substances 0.000 claims 1
235000021317 phosphate Nutrition 0.000 claims 1
150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
239000000706 filtrate Substances 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
239000000126 substance Substances 0.000 description 17
239000008346 aqueous phase Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
235000015097 nutrients Nutrition 0.000 description 12
239000000284 extract Substances 0.000 description 11
239000012071 phase Substances 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 10
238000001914 filtration Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
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241000187747 Streptomyces Species 0.000 description 8
239000003242 anti bacterial agent Substances 0.000 description 8
238000010828 elution Methods 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000007853 buffer solution Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
239000005695 Ammonium acetate Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229940043376 ammonium acetate Drugs 0.000 description 6
235000019257 ammonium acetate Nutrition 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
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239000008103 glucose Substances 0.000 description 5
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235000019698 starch Nutrition 0.000 description 5
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DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 4
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
229910002651 NO3 Inorganic materials 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000005057 refrigeration Methods 0.000 description 4
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
-1 D-mannite Chemical compound 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
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235000002017 Zea mays subsp mays Nutrition 0.000 description 3
239000002156 adsorbate Substances 0.000 description 3
239000003463 adsorbent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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238000001179 sorption measurement Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
241000186361 Actinobacteria <class> Species 0.000 description 2
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
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WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
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235000020679 tap water Nutrition 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
108010046845 tryptones Proteins 0.000 description 1
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235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
GXFAIFRPOKBQRV-GHXCTMGLSA-N viomycin Chemical compound N1C(=O)\C(=C\NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)C[C@@H](N)CCCN)CNC(=O)[C@@H]1[C@@H]1NC(=N)N[C@@H](O)C1 GXFAIFRPOKBQRV-GHXCTMGLSA-N 0.000 description 1
229950001272 viomycin Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3210246A (en) *	1960-09-22	1965-10-05	Parke Davis & Co	Succinimycin and acid-addition salts thereof

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3210246A (en) *	1960-09-22	1965-10-05	Parke Davis & Co	Succinimycin and acid-addition salts thereof

Publication	Publication Date	Title
CA1113411A (en)	1981-12-01	Physiologically active substance esterastin and production thereof
CH304875A (fr)	1955-01-31	Procédé de préparation d'une nouvelle substance antibiotique.
LU82327A1 (fr)	1981-12-02	Substance antibiotique a/16686 et son procede de preparation
FR2489819A1 (fr)	1982-03-12	Antibiotique bmg162-af2 ayant notamment une activite antitumorale et son procede de preparation a partir d'une souche du genre bacillus
BE569746A (xx)
FR1465395A (fr)	1967-01-13	Composé nouveau, la décoyinine et son procédé de fabrication
DE2652677C2 (de)	1985-05-23	Antibiotica 890A&darr;1&darr; und 890A&darr;3&darr;, Verfahren zu ihrer Herstellung und diese Antibiotika enthaltende antibakterielle Mittel
US3089816A (en)	1963-05-14	Lemacidine and process for its manufacture
CH623566A5 (en)	1981-06-15	Process for producing the new depsipeptide antibiotics neoviridogrisein I, II, III
US3907764A (en)	1975-09-23	Pepsinostrepins, novel protease inhibitors from streptomyces
JPS6020000B2 (ja)	1985-05-18	新抗生物質ｙ−１６４８２物質およびその製造法
US3105794A (en)	1963-10-01	Spiramycin d
FR2460961A1 (fr)	1981-01-30	Derives de tallysomycine, leur procede de production et medicament les contenant
US2914525A (en)	1959-11-24	Nucleocidin and the process of obtaining the same
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FR2459288A1 (fr)	1981-01-09	Procede de preparation de la mildiomycine par un micro-organisme du genre streptoverticillium, dans une culture contenant un compose n-methyle
AT216143B (de)	1961-07-10	Verfahren zur Herstellung eines neuen Antibiotikums
BE860210A (fr)	1978-04-27	Facteurs d et ke de la fortimicine utiles notamment comme antibiotique et leur procede de preparation
AT208509B (de)	1960-04-11	Verfahren zur Herstellung eines neuen Antibiotikums
US3629406A (en)	1971-12-21	Sparsogenin and sparsogenin a and methods of preparation
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