IE32839B1 - Urea-antibiotic adducts and process for preparing the same - Google Patents
Urea-antibiotic adducts and process for preparing the sameInfo
- Publication number
- IE32839B1 IE32839B1 IE1448/68A IE144868A IE32839B1 IE 32839 B1 IE32839 B1 IE 32839B1 IE 1448/68 A IE1448/68 A IE 1448/68A IE 144868 A IE144868 A IE 144868A IE 32839 B1 IE32839 B1 IE 32839B1
- Authority
- IE
- Ireland
- Prior art keywords
- urea
- dihydro
- ketone
- reduced
- tylosin
- Prior art date
Links
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Abstract
1,244,019. Macrolide-urea adducts. ELI LILLY & CO. 4 Dec., 1968 [4 Dec., 1967 (2); 15 July, 1968], No. 57629/68. Heading C2A. Novel aldehydic-rnacrolide bis-ureas wherein the aldehyde group of 1 molecule of an appropriate macrolide is combined with 2 molecules of a urea of formula wherein Am is -NH-R, R being phenyl, tolyl, halophenyl or trifluoromethylphenyl; or R<SP>1</SP> and R<SP>11</SP> being independently hydrogen, C 1 to C 4 alkyl or C 3 to C 4 alkenyl and the sum of their carbon atoms not exceeding 4, are prepared by reacting in a neutral solvent, at least 2 moles of the urea with 1 mole of the macrolide. The macrolides may be tylosin, macrosin, desmycosin, lactenocin, carbomycin, carbomycin B, niddamycin, spiramycins A, B, C and D or leucomycins A 1 to A 8 . Ureas may be urea or N-methyl-; N,N-diethyl-; N-n-butyl-; N- allyl-; N-phenyl-; N-(p-chlorophenyl)-; N-(otolyl)-; or N- (p .trifluoromethylphenyl)-urea. The compounds are preferably prepared by adding the macrolide or a salt thereof to a saturated aqueous or alcoholic solution of the urea at room temperature, allowing to stand, diluting with water and bringing to pH 9, and saturating the solution with sodium chloride to precipitate the required product. This is filtered off, dissolved in chloroform, the solution washed with water, and the chloroform evaporated off; the product is finally recrystallized, e.g. from aqueous acetone. Dihydro (ketone reduced) tylosin bis-urea is prepared by reducing tylosin bis-urea in ethanolic solution with sodium borohydride, and is subsequently hydrolysed by treatment with aqueous ethanol at pH 5À0 and 90‹ C. for ¢ hour to give the novel antibiotic dihydro- (ketone reduced) tylosin, this product being extracted from the reaction solution with methyl - ene dichloride at pH 5À0 to 5À5. Alternatively, the dihydro (ketone-reduced) bis-urea is hydrolysed to give the novel antibiotic dihydro/ketone-reduced) desmycosin by aqueous hydrolysis at either pH 2À8 and room temperature for 4 days or pH 3À6 and 100‹ C. for 1¢ hours, the said antibiotic being extracted from the hydrolysate with methylene dichloride at pH 7 to 8. Pharmaceutical compositions comprise one or both of the antibiotics dihydro(ketone-reduced) tylosin and dihydro(ketone-reduced) desmycosin together with a carrier. Veterinary compositions for administering to ruminants comprise an aldehydic-macrolide bis-urea as defined above together with a carrier which may be an animal feedstuff.
[GB1244019A]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68749967A | 1967-12-04 | 1967-12-04 | |
US68749867A | 1967-12-04 | 1967-12-04 | |
US74462768A | 1968-07-15 | 1968-07-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE32839L IE32839L (en) | 1969-06-04 |
IE32839B1 true IE32839B1 (en) | 1973-12-28 |
Family
ID=27418489
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1448/68A IE32839B1 (en) | 1967-12-04 | 1968-11-27 | Urea-antibiotic adducts and process for preparing the same |
Country Status (10)
Country | Link |
---|---|
AT (2) | AT290012B (en) |
BE (1) | BE724757A (en) |
CH (2) | CH494746A (en) |
DE (2) | DE1812471C3 (en) |
DK (2) | DK131785C (en) |
FR (1) | FR1599815A (en) |
GB (1) | GB1244019A (en) |
IE (1) | IE32839B1 (en) |
MY (1) | MY7300492A (en) |
NL (1) | NL146173B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL69666A (en) * | 1982-09-13 | 1987-10-20 | Lilly Co Eli | 20-amino-20-deoxo-5-o-mycaminosyl-23-o-mycinosyltylonolide derivatives,their preparation and veterinary antibiotic use |
-
1968
- 1968-11-27 IE IE1448/68A patent/IE32839B1/en unknown
- 1968-12-02 FR FR1599815D patent/FR1599815A/fr not_active Expired
- 1968-12-02 BE BE724757D patent/BE724757A/xx unknown
- 1968-12-03 DE DE1812471A patent/DE1812471C3/en not_active Expired
- 1968-12-03 AT AT1178668A patent/AT290012B/en not_active IP Right Cessation
- 1968-12-03 DE DE19681817858 patent/DE1817858A1/en active Pending
- 1968-12-03 DK DK589668A patent/DK131785C/en active
- 1968-12-03 AT AT482670A patent/AT293621B/en not_active IP Right Cessation
- 1968-12-04 NL NL686817419A patent/NL146173B/en unknown
- 1968-12-04 CH CH1818568A patent/CH494746A/en not_active IP Right Cessation
- 1968-12-04 GB GB57629/68A patent/GB1244019A/en not_active Expired
- 1968-12-04 CH CH808270A patent/CH496740A/en not_active IP Right Cessation
-
1970
- 1970-03-09 DK DK114770AA patent/DK128456B/en unknown
-
1973
- 1973-12-30 MY MY492/73A patent/MY7300492A/en unknown
Also Published As
Publication number | Publication date |
---|---|
NL146173B (en) | 1975-06-16 |
NL6817419A (en) | 1969-06-06 |
DK128456B (en) | 1974-05-06 |
GB1244019A (en) | 1971-08-25 |
DE1812471A1 (en) | 1969-07-03 |
DE1812471B2 (en) | 1973-12-20 |
DK131785C (en) | 1976-02-02 |
AT290012B (en) | 1971-05-10 |
BE724757A (en) | 1969-06-02 |
CH496740A (en) | 1970-09-30 |
DK131785B (en) | 1975-09-01 |
MY7300492A (en) | 1973-12-31 |
DE1817858A1 (en) | 1972-12-21 |
DE1812471C3 (en) | 1974-07-18 |
IE32839L (en) | 1969-06-04 |
AT293621B (en) | 1971-10-25 |
FR1599815A (en) | 1970-07-20 |
CH494746A (en) | 1970-08-15 |
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