DE1493571A1 - Verfahren zur Herstellung von Bacitracin-Metallmethansulfinaten - Google Patents
Verfahren zur Herstellung von Bacitracin-MetallmethansulfinatenInfo
- Publication number
- DE1493571A1 DE1493571A1 DE19651493571 DE1493571A DE1493571A1 DE 1493571 A1 DE1493571 A1 DE 1493571A1 DE 19651493571 DE19651493571 DE 19651493571 DE 1493571 A DE1493571 A DE 1493571A DE 1493571 A1 DE1493571 A1 DE 1493571A1
- Authority
- DE
- Germany
- Prior art keywords
- bacitracin
- metal
- methanesulfinate
- sodium
- formaldehyde sulfoxylate
- 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.)
- Pending
Links
- 108010001478 Bacitracin Proteins 0.000 title claims description 60
- 229960003071 bacitracin Drugs 0.000 title claims description 57
- 229930184125 bacitracin Natural products 0.000 title claims description 57
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 title claims description 57
- 229910052751 metal Inorganic materials 0.000 title claims description 32
- 239000002184 metal Substances 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 9
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical class CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- XNEFVTBPCXGIRX-UHFFFAOYSA-M methanesulfinate Chemical compound CS([O-])=O XNEFVTBPCXGIRX-UHFFFAOYSA-M 0.000 claims description 16
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 7
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 claims description 6
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 claims description 6
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims description 6
- 230000003115 biocidal effect Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 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 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 3
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 3
- 229960005364 bacitracin zinc Drugs 0.000 claims description 3
- 235000002867 manganese chloride Nutrition 0.000 claims description 3
- 239000011565 manganese chloride Substances 0.000 claims description 3
- 229940099607 manganese chloride Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC([O-])=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 0.000 claims description 3
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 1
- 239000010985 leather Substances 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010037867 Rash macular Diseases 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 2
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical class O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- ZCWAUAFXUZOAQO-UHFFFAOYSA-L [Ca+2].O=C.[O-]S[O-] Chemical compound [Ca+2].O=C.[O-]S[O-] ZCWAUAFXUZOAQO-UHFFFAOYSA-L 0.000 description 1
- UFMPHMULHHGPRI-UHFFFAOYSA-L [K+].[K+].O=C.[O-]S[O-] Chemical compound [K+].[K+].O=C.[O-]S[O-] UFMPHMULHHGPRI-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000019730 animal feed additive Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7, Chemical compound [Co+3].N#[C-].C1([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)[N-]\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- LUVYQCQHAJAFEX-UHFFFAOYSA-N formaldehyde;manganese Chemical compound [Mn].O=C LUVYQCQHAJAFEX-UHFFFAOYSA-N 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- JDWCUDYOWWEXAQ-UHFFFAOYSA-M potassium;methanesulfinate Chemical compound [K+].CS([O-])=O JDWCUDYOWWEXAQ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229940045999 vitamin b 12 Drugs 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- 239000011686 zinc sulphate Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42750565A | 1965-01-22 | 1965-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493571A1 true DE1493571A1 (de) | 1969-06-19 |
Family
ID=23695148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651493571 Pending DE1493571A1 (de) | 1965-01-22 | 1965-10-01 | Verfahren zur Herstellung von Bacitracin-Metallmethansulfinaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3441646A (en:Method) |
| BE (1) | BE674314A (en:Method) |
| DE (1) | DE1493571A1 (en:Method) |
| FR (1) | FR1463679A (en:Method) |
| GB (1) | GB1072337A (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1061352B (it) * | 1973-03-27 | 1983-02-28 | Crinos Industria Farmaco | Sali misti di esteri polisolforici di glicopeptidi naturali con metalli e con basi organiche e procedimento per la loro preparazione |
| US3891615A (en) * | 1973-10-25 | 1975-06-24 | Commercial Solvents Corp | Recovery of bacitracin as the calcium or magnesium complex of an alkylbenzenesulfonic acid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774712A (en) * | 1955-11-14 | 1956-12-18 | S B Penick & Company | Bacitracin compound and recovery of bacitracin |
| US3044954A (en) * | 1958-04-11 | 1962-07-17 | Sun Oil Co | Siliceous cracking catalyst with a discontinuous surface glaze |
| US3035919A (en) * | 1959-04-15 | 1962-05-22 | Pabst Brewing Co | Lignin-bacitracin complex as growth stimulant and bacitracin purifier |
| US3061515A (en) * | 1960-05-09 | 1962-10-30 | Bristol Myers Co | Methane sulfonates of telomycins |
| US3205137A (en) * | 1963-03-19 | 1965-09-07 | Warner Lambert Pharmaceutical | Bacitracin derivatives |
-
1965
- 1965-01-22 US US427505A patent/US3441646A/en not_active Expired - Lifetime
- 1965-10-01 DE DE19651493571 patent/DE1493571A1/de active Pending
- 1965-11-19 GB GB49199/65A patent/GB1072337A/en not_active Expired
- 1965-12-24 BE BE674314D patent/BE674314A/xx unknown
-
1966
- 1966-01-17 FR FR46109A patent/FR1463679A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1463679A (fr) | 1966-12-23 |
| GB1072337A (en) | 1967-06-14 |
| BE674314A (en:Method) | 1966-04-15 |
| US3441646A (en) | 1969-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2927056A1 (de) | Platin-diaminkomplexe, verfahren zu deren herstellung und verwendung derselben zur herstellung von arzneimitteln zur krebsbehandlung | |
| DE2329485A1 (de) | Platinkoordinationsverbindungen | |
| CH650003A5 (de) | Platin(iv)-diaminkomplexe, verfahren zu deren herstellung und diese enthaltende krebsmittel. | |
| DE2439282A1 (de) | Neue beta-diketone und ein verfahren zur extraktion von kupfer und nickel unter verwendung derselben als extraktionsmittel | |
| DE2444532A1 (de) | Metforminacetylsalicylat | |
| DE3207472A1 (de) | Platin-diamin-komplexe, ein verfahren zu ihrer herstellung, ein verfahren zur herstellung eines arzneimittels unter einsatz eines derartigen platin-diamin-komplexes fuer die behandlung von krebs sowie das dabei erhaltene arzneimittel | |
| AT390610B (de) | Verfahren zur herstellung von neuen platin-(ii) -diaminkomplexen | |
| DE1795726C3 (de) | 2-Amino-4-methyl-5-alkyl-6-hydroxy- . pyridinderivate | |
| DE2725246C2 (en:Method) | ||
| DE1493571A1 (de) | Verfahren zur Herstellung von Bacitracin-Metallmethansulfinaten | |
| DE4129872C2 (de) | Verfahren zur Herstellung von Huminsäure-Metall-Verbindungen, deren Verwendung als Adsorptions- und/oder Entgiftungsmittel bzw. als Spurenelementquelle | |
| DE69908181T2 (de) | Methode zur herstellung eines antitumormittels und dadurch erhaltenes tumormittel | |
| DE2539179A1 (de) | Aethylendiaminplatin(ii)-2,4-dioxopyrimidin-komplexe | |
| DE2146395C3 (de) | N-p-Toluolsulfonyl-5-methyl- d2 -pyrazolin-1karbonamid und Verfahren zu seiner Herstellung | |
| DE4137930C2 (de) | Platin(II)-Anti-Tumorkomplexe und ein Verfahren zu ihrer Herstellung | |
| DE1567041A1 (de) | Neue Fungizide | |
| DE951567C (de) | Verfahren zur Herstellung von Antibiotikappantothenaten | |
| DE2063027A1 (de) | Salz einer basischen Aminosäure der 5 6,7,8 Tetrahydrofolsaure | |
| DE2235400C3 (de) | ^Chlor-S-sulfamoyl-anthranilsäuren, deren Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Arzneimittel | |
| DE1468954A1 (de) | Verfahren zur Herstellung einer Verbindung mit fungiziden Eigenschaften | |
| DE1237560B (de) | Verfahren zur Herstellung von Cyanameisensaeurethiolestern | |
| DE2136478C3 (de) | Verfahren zur Herstellung von 1 ^-Naphthochinon-Semicarbazon | |
| DE79539C (en:Method) | ||
| DE935667C (de) | Verfahren zur Herstellung von Phenanthridiniumsalzen | |
| DE1545652C (de) | 3-(alpha-Hydroxyäthyl)-6-chlor-7sulfamyl-1,2,4-benzothiadiazin-1,1 dioxyd |