GB1275473A - Erythromycylamine and process for preparing same - Google Patents
Erythromycylamine and process for preparing sameInfo
- Publication number
- GB1275473A GB1275473A GB43215/69A GB4321569A GB1275473A GB 1275473 A GB1275473 A GB 1275473A GB 43215/69 A GB43215/69 A GB 43215/69A GB 4321569 A GB4321569 A GB 4321569A GB 1275473 A GB1275473 A GB 1275473A
- Authority
- GB
- United Kingdom
- Prior art keywords
- erythromycylamine
- erythromycin
- adduct
- hydrazine
- derivative
- 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
- XCLJRCAJSCMIND-JCTYMORFSA-N (9S)-erythromycyclamine Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)[C@@H](N)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 XCLJRCAJSCMIND-JCTYMORFSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 150000002923 oximes Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 abstract 1
- VIVCRCODGMFTFY-JPRIQSOUSA-N (4s,5s)-3,4-dihydroxy-5-[(1r,2r)-1,2,3-trihydroxypropyl]oxolan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@@H]1OC(=O)C(O)[C@@H]1O VIVCRCODGMFTFY-JPRIQSOUSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 229960003681 gluconolactone Drugs 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75629268A | 1968-08-29 | 1968-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1275473A true GB1275473A (en) | 1972-05-24 |
Family
ID=25042836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43215/69A Expired GB1275473A (en) | 1968-08-29 | 1969-08-29 | 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0955307A1 (en) * | 1998-04-14 | 1999-11-10 | Chemagis Ltd. | Erythromycin a derivatives and methods for the preparation thereof |
| EP0972778A1 (en) * | 1998-07-15 | 2000-01-19 | Chemagis Ltd. | Erythromycin derivatives and methods for the preparation thereof |
Families Citing this family (7)
| 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 |
| 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 IE IE1160/69A patent/IE33572B1/en unknown
- 1969-08-15 CA CA059637A patent/CA918651A/en not_active Expired
- 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 DE DE1943781A patent/DE1943781C3/en not_active Expired
- 1969-08-28 AT AT825169A patent/AT301021B/en not_active IP Right Cessation
- 1969-08-28 DK DK461269AA patent/DK125852B/en not_active IP Right Cessation
- 1969-08-28 BE BE738083D patent/BE738083A/xx unknown
- 1969-08-28 DE DE1966310A patent/DE1966310C3/en not_active Expired
- 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0955307A1 (en) * | 1998-04-14 | 1999-11-10 | Chemagis Ltd. | Erythromycin a derivatives and methods for the preparation thereof |
| EP0972778A1 (en) * | 1998-07-15 | 2000-01-19 | Chemagis Ltd. | Erythromycin derivatives and methods for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1966310B2 (en) | 1980-12-04 |
| FR2016612A1 (en) | 1970-05-08 |
| BE738083A (en) | 1970-03-02 |
| CH520135A (en) | 1972-03-15 |
| DE1943781A1 (en) | 1970-08-20 |
| NL148896B (en) | 1976-03-15 |
| SE363629B (en) | 1974-01-28 |
| DE1943781B2 (en) | 1978-11-23 |
| DE1943781C3 (en) | 1979-07-26 |
| DK125852B (en) | 1973-05-14 |
| DE1966310C3 (en) | 1981-07-16 |
| IE33572B1 (en) | 1974-08-21 |
| ZA695765B (en) | 1971-03-31 |
| IE33572L (en) | 1970-02-28 |
| AT301021B (en) | 1972-08-25 |
| IL32865A (en) | 1973-06-29 |
| NL6913124A (en) | 1970-03-03 |
| CA918651A (en) | 1973-01-09 |
| IL32865A0 (en) | 1969-11-12 |
| DE1966310A1 (en) | 1972-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |