DE2708493C2 - Antibiotikum AM-1042 - Google Patents
Antibiotikum AM-1042Info
- Publication number
- DE2708493C2 DE2708493C2 DE2708493A DE2708493A DE2708493C2 DE 2708493 C2 DE2708493 C2 DE 2708493C2 DE 2708493 A DE2708493 A DE 2708493A DE 2708493 A DE2708493 A DE 2708493A DE 2708493 C2 DE2708493 C2 DE 2708493C2
- Authority
- DE
- Germany
- Prior art keywords
- chloroform
- methanol
- nrrl
- extract
- ethyl acetate
- 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
- SSHVAUUEPNULMP-JHWDTTIQSA-N asukamycin Chemical compound O=C1CCC(O)=C1NC(=O)\C=C\C=C\C=C\[C@@]1(O)[C@@H]2O[C@@H]2C(=O)C(NC(=O)\C=C\C=C\C=C\C2CCCCC2)=C1 SSHVAUUEPNULMP-JHWDTTIQSA-N 0.000 title claims description 62
- 230000003115 biocidal effect Effects 0.000 title claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 21
- 241000122969 Streptomyces nodosus Species 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000862 absorption spectrum Methods 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000009102 absorption Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
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- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 13
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 11
- 239000002609 medium Substances 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000003242 anti bacterial agent Substances 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
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- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 4
- NFOMJDXALJABQF-UHFFFAOYSA-N 4-amino-n-[1-[5-[5-(dimethylamino)-3,4-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]-2-oxopyrimidin-4-yl]benzamide Chemical compound CC1OC(N2C(N=C(NC(=O)C=3C=CC(N)=CC=3)C=C2)=O)CCC1OC1OC(C)C(N(C)C)C(O)C1O NFOMJDXALJABQF-UHFFFAOYSA-N 0.000 description 4
- 244000063299 Bacillus subtilis Species 0.000 description 4
- ZDPIZLCVJAAHHR-UHFFFAOYSA-N Clopidol Chemical compound CC1=NC(C)=C(Cl)C(O)=C1Cl ZDPIZLCVJAAHHR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241000223932 Eimeria tenella Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000001888 Peptone Substances 0.000 description 4
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
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- 208000035473 Communicable disease Diseases 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
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- MOOFYEJFXBSZGE-QJUDHZBZSA-N 1,2-bis[(z)-(4-chlorophenyl)methylideneamino]guanidine Chemical compound C=1C=C(Cl)C=CC=1\C=N/N=C(/N)N\N=C/C1=CC=C(Cl)C=C1 MOOFYEJFXBSZGE-QJUDHZBZSA-N 0.000 description 2
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- 229940095731 candida albicans Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
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- 239000012141 concentrate Substances 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019374 flavomycin Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000012869 germination medium Substances 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229930189958 manumycin Natural products 0.000 description 1
- TWWQHCKLTXDWBD-MVTGTTCWSA-N manumycin A Chemical compound C(/[C@@]1(C=C(C([C@H]2O[C@H]21)=O)NC(=O)C(/C)=C/C(/C)=C/[C@H](C)CCCC)O)=C\C=C\C=C\C(=O)NC1=C(O)CCC1=O TWWQHCKLTXDWBD-MVTGTTCWSA-N 0.000 description 1
- TWWQHCKLTXDWBD-UHFFFAOYSA-N manumycin A Natural products C12OC2C(=O)C(NC(=O)C(C)=CC(C)=CC(C)CCCC)=CC1(O)C=CC=CC=CC(=O)NC1=C(O)CCC1=O TWWQHCKLTXDWBD-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
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- 230000035772 mutation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- KELXKDDAALYTDI-BTVCFUMJSA-N nitric acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound O[N+]([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O KELXKDDAALYTDI-BTVCFUMJSA-N 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 229960001907 nitrofurazone Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51020119A JPS5857160B2 (ja) | 1976-02-27 | 1976-02-27 | 新規抗生物質ａｍ−１０４２物質およびその製造法 |
| JP9242776A JPS5322078A (en) | 1976-08-03 | 1976-08-03 | Formula feed for growth stimulation of poultry |
| JP9242676A JPS5318716A (en) | 1976-08-03 | 1976-08-03 | Prevetive for poultry coccidium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2708493A1 DE2708493A1 (de) | 1977-09-01 |
| DE2708493C2 true DE2708493C2 (de) | 1983-02-17 |
Family
ID=27282907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2708493A Expired DE2708493C2 (de) | 1976-02-27 | 1977-02-26 | Antibiotikum AM-1042 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4226879A (enExample) |
| DE (1) | DE2708493C2 (enExample) |
| FR (1) | FR2342300A1 (enExample) |
| GB (1) | GB1541512A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595770A (en) * | 1982-06-21 | 1986-06-17 | The Upjohn Company | Antibiotic compound and process for recovery thereof from a fermentation broth |
| US4404282A (en) * | 1982-08-19 | 1983-09-13 | Eli Lilly And Company | Process for enzyme inhibitor |
| US4404281A (en) * | 1982-08-19 | 1983-09-13 | Eli Lilly And Company | Process for enzyme inhibitors |
| CA2041237C (en) * | 1990-05-10 | 1996-07-16 | Hirofumi Nakano | Ucf1 compounds derivatives thereof and processes for their preparation |
| US5444087A (en) * | 1993-10-19 | 1995-08-22 | Bristol-Myers Squibb Company | Manumycin compounds |
| JPH08151373A (ja) * | 1994-09-30 | 1996-06-11 | Kyowa Hakko Kogyo Co Ltd | 生理活性物質ｅｉ−１５１１類およびｅｉ−１６２５−２ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927211A (en) * | 1970-08-14 | 1975-12-16 | Gist Brocades Nv | Antibiotic MYC 8003 and process for producing same |
| US3959468A (en) * | 1974-05-06 | 1976-05-25 | The United States Of America As Represented By The Secretary Of Agriculture | Antibiotic equisetin and method of production |
-
1977
- 1977-02-25 FR FR7705544A patent/FR2342300A1/fr active Granted
- 1977-02-25 GB GB8149/77A patent/GB1541512A/en not_active Expired
- 1977-02-26 DE DE2708493A patent/DE2708493C2/de not_active Expired
-
1978
- 1978-09-01 US US05/939,102 patent/US4226879A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US4226879A (en) | 1980-10-07 |
| FR2342300A1 (fr) | 1977-09-23 |
| DE2708493A1 (de) | 1977-09-01 |
| GB1541512A (en) | 1979-03-07 |
| FR2342300B1 (enExample) | 1981-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |