IE33572B1 - Erythromycylamine and process for preparing same - Google Patents
Erythromycylamine and process for preparing sameInfo
- Publication number
- IE33572B1 IE33572B1 IE1160/69A IE116069A IE33572B1 IE 33572 B1 IE33572 B1 IE 33572B1 IE 1160/69 A IE1160/69 A IE 1160/69A IE 116069 A IE116069 A IE 116069A IE 33572 B1 IE33572 B1 IE 33572B1
- Authority
- IE
- Ireland
- Prior art keywords
- erythromycylamine
- erythromycin
- adduct
- hydrazine
- derivative
- Prior art date
Links
Classifications
-
- 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)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1275473 Erythromycin derivatives ELI LILLY & CO 29 Aug 1969 [29 Aug 1968] 43215/69 Heading C2A Erythromycylamine which melts at 125 to 127 C. and has the formula is prepared by catalytic hydrogenation of erythromycin oxime (IIa), erythromycin-hydrazine adduct (IIb) or the N<SP>1</SP>-isopropylidene derivative (IIc) of this adduct, which compounds have the general formula wherein R has the meanings The oxime and the hydrazine adduct are prepared by reacting erythromycin with hydroxylamine hydrochloride, and with hydrazine respectively, in a solvent such as methanol. The isopropylidene derivative is prepared by reacting the hydrazine adduct with acetone. These compounds are hydrogenated in an inert solvent such as acetic acid or preferably water containing 1 to 2% #-gluconolactone, glucoheptonolactone or other lactones of a sugar acid, using a noble metal catalyst such as platinum, palladium, ruthenium or rhodium, either as the free metal or the oxide. The oxime or hydrazine adduct are hydrogenated at about 500-2000 p.s.i., while pressures of 50-100 p.s.i. are preferably used in the caes of the isopropylidene derivative. By hydrogenating the isopropylidene derivative in a neutral medium, e.g. ethanol it may be converted to the corresponding N-isopropyl derivative of the erythromycin-hydrazine adduct. This represents an intermediate in the erythromycylamine formation and by further hydrogenation in an acidic medium the isopropyl derivative yields erythromycylamine. Pharmaceutical compositions having antibacterial activity against Gram-positive and Gramnegative micro-organisms comprise the antibiotic erythromycylamine together with a pharmaceutically acceptable diluent or carrier.
[GB1275473A]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US75629268A | 1968-08-29 | 1968-08-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE33572L IE33572L (en) | 1970-02-28 |
IE33572B1 true IE33572B1 (en) | 1974-08-21 |
Family
ID=25042836
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1160/69A IE33572B1 (en) | 1968-08-29 | 1969-08-15 | Erythromycylamine and process for preparing same |
Country Status (13)
Country | Link |
---|---|
AT (1) | AT301021B (en) |
BE (1) | BE738083A (en) |
CA (1) | CA918651A (en) |
CH (1) | CH520135A (en) |
DE (2) | DE1943781C3 (en) |
DK (1) | DK125852B (en) |
FR (1) | FR2016612A1 (en) |
GB (1) | GB1275473A (en) |
IE (1) | IE33572B1 (en) |
IL (1) | IL32865A (en) |
NL (1) | NL148896B (en) |
SE (1) | SE363629B (en) |
ZA (1) | ZA695765B (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE759252A (en) * | 1969-11-21 | 1971-05-21 | Lilly Co Eli | ERYTROMYCYL B AMINE |
ZA71763B (en) * | 1970-04-13 | 1972-03-29 | Lilly Industries Ltd | Erythromycylamines via hydrazones |
US3681326A (en) * | 1971-01-11 | 1972-08-01 | Abbott Lab | 9-substituted erythromycin a and b oximes |
GB8721165D0 (en) * | 1987-09-09 | 1987-10-14 | Beecham Group Plc | Chemical compounds |
DE19518917A1 (en) * | 1995-05-23 | 1996-11-28 | Boehringer Ingelheim Vetmed | Stable, concentrated, locally tolerated erythromycylamine solutions |
IL124084A0 (en) * | 1998-04-14 | 1999-04-11 | Chemagis Ltd | Erythromycin a derivatives and methods for the preparation thereof |
IL125372A0 (en) * | 1998-07-15 | 1999-03-12 | Chemagis Ltd | Erythromycin derivatives and methods for the preparation thereof |
US6437106B1 (en) | 1999-06-24 | 2002-08-20 | Abbott Laboratories | Process for preparing 6-o-substituted erythromycin derivatives |
US6605707B1 (en) | 2000-03-23 | 2003-08-12 | Abbott Laboratories | Process for the preparation of 6-O-propargyl erythromycin derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1100504A (en) * | 1967-08-16 | 1968-01-24 | Pliva Pharm & Chem Works | Erythromycin oxime and 9-amino-3-o-cladinosyl-5-o-desosaminyl-6,11,12-trihydroxy-2,4,6,8,10,12-hexamethylpentadecane-13-olide |
-
1969
- 1969-08-12 ZA ZA695765A patent/ZA695765B/en unknown
- 1969-08-15 CA CA059637A patent/CA918651A/en not_active Expired
- 1969-08-15 IE IE1160/69A patent/IE33572B1/en unknown
- 1969-08-20 IL IL32865A patent/IL32865A/en unknown
- 1969-08-27 SE SE11856/69A patent/SE363629B/xx unknown
- 1969-08-27 NL NL696913124A patent/NL148896B/en not_active IP Right Cessation
- 1969-08-28 BE BE738083D patent/BE738083A/xx unknown
- 1969-08-28 DE DE1943781A patent/DE1943781C3/en not_active Expired
- 1969-08-28 DE DE1966310A patent/DE1966310C3/en not_active Expired
- 1969-08-28 DK DK461269AA patent/DK125852B/en not_active IP Right Cessation
- 1969-08-28 AT AT825169A patent/AT301021B/en not_active IP Right Cessation
- 1969-08-29 GB GB43215/69A patent/GB1275473A/en not_active Expired
- 1969-08-29 CH CH1318469A patent/CH520135A/en not_active IP Right Cessation
- 1969-08-29 FR FR6929701A patent/FR2016612A1/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
DE1943781C3 (en) | 1979-07-26 |
AT301021B (en) | 1972-08-25 |
GB1275473A (en) | 1972-05-24 |
DK125852B (en) | 1973-05-14 |
NL6913124A (en) | 1970-03-03 |
DE1943781B2 (en) | 1978-11-23 |
NL148896B (en) | 1976-03-15 |
DE1943781A1 (en) | 1970-08-20 |
IL32865A (en) | 1973-06-29 |
DE1966310A1 (en) | 1972-04-06 |
DE1966310C3 (en) | 1981-07-16 |
SE363629B (en) | 1974-01-28 |
IL32865A0 (en) | 1969-11-12 |
DE1966310B2 (en) | 1980-12-04 |
BE738083A (en) | 1970-03-02 |
ZA695765B (en) | 1971-03-31 |
CH520135A (en) | 1972-03-15 |
IE33572L (en) | 1970-02-28 |
FR2016612A1 (en) | 1970-05-08 |
CA918651A (en) | 1973-01-09 |
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