GB1358114A - One step process for the production of a mono-ester of macrolide antibiotics - Google Patents
One step process for the production of a mono-ester of macrolide antibioticsInfo
- Publication number
- GB1358114A GB1358114A GB3008372A GB3008372A GB1358114A GB 1358114 A GB1358114 A GB 1358114A GB 3008372 A GB3008372 A GB 3008372A GB 3008372 A GB3008372 A GB 3008372A GB 1358114 A GB1358114 A GB 1358114A
- Authority
- GB
- United Kingdom
- Prior art keywords
- leucomycin
- group
- antibiotic
- mono
- ester
- 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
- 239000003120 macrolide antibiotic agent Substances 0.000 title 1
- XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 abstract 5
- 229960004144 josamycin Drugs 0.000 abstract 5
- XJSFLOJWULLJQS-UHFFFAOYSA-N leucomycin A3 Natural products COC1C(OC(C)=O)CC(=O)OC(C)CC=CC=CC(O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 XJSFLOJWULLJQS-UHFFFAOYSA-N 0.000 abstract 5
- DMUAPQTXSSNEDD-QALJCMCCSA-N Midecamycin Chemical compound C1[C@](O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C DMUAPQTXSSNEDD-QALJCMCCSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- -1 SF-837 esters Chemical class 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000000126 substance Substances 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
1358114 Esterifying antibiotic SF-837 and leucomycin A 3 MEIJI SEIKA KAISHA Ltd 27 June 1972 [29 June 1971] 30083/72 Heading C2A Monoesters of the antibiotics SF-837 substance and leucomycin A 3 having the general Formula (II) wherein R and R<SP>1</SP> are both methyl groups (SF-837 esters) or R is hydrogen and R<SP>1</SP> is an isopropyl group (leucomycin A 3 esters), and R<SP>11</SP> is a C 1 -C 4 alkyl group which may be substituted, a C 1 -C 4 alkenyl group, an aromatic group or a heterocyclic group, are prepared by reacting SF-837 or leucomycin A 3 with an acyl halide of formula R<SP>11</SP>COX wherein R<SP>11</SP> has the aforesaid meaning and X is Cl or Br, in solution in a reaction medium selected from benzene, toluene, ethyl acetate and methyl isobutylketone in the presence of pyridine or picoline as an acidbinding agent. Pharmaceutical compositions having antibiotic activity comprise a mono-ester of antibiotic SF-837 or of leucomycin A 3 having the Formula II above together with a pharmaceutically acceptable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4679671A JPS4925271B1 (en) | 1971-06-29 | 1971-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1358114A true GB1358114A (en) | 1974-06-26 |
Family
ID=12757282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3008372A Expired GB1358114A (en) | 1971-06-29 | 1972-06-27 | One step process for the production of a mono-ester of macrolide antibiotics |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4925271B1 (en) |
| CA (1) | CA962263A (en) |
| DE (1) | DE2230729C3 (en) |
| FR (1) | FR2186229B1 (en) |
| GB (1) | GB1358114A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5432493A (en) * | 1977-08-15 | 1979-03-09 | Meiji Seika Kaisha Ltd | Preparation of macrolide antibiotics derivatives |
-
1971
- 1971-06-29 JP JP4679671A patent/JPS4925271B1/ja active Pending
-
1972
- 1972-06-23 DE DE19722230729 patent/DE2230729C3/en not_active Expired
- 1972-06-27 GB GB3008372A patent/GB1358114A/en not_active Expired
- 1972-06-28 CA CA145,918A patent/CA962263A/en not_active Expired
- 1972-06-28 FR FR7223300A patent/FR2186229B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2230729A1 (en) | 1973-01-18 |
| JPS4925271B1 (en) | 1974-06-28 |
| FR2186229A1 (en) | 1974-01-11 |
| FR2186229B1 (en) | 1977-04-15 |
| CA962263A (en) | 1975-02-04 |
| DE2230729C3 (en) | 1975-01-30 |
| DE2230729B2 (en) | 1974-06-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2966269D1 (en) | 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids, process for preparing the same and pharmaceutical compositions containing the same | |
| YU39431B (en) | Process for the manufacture of 13-halo and 13-deoxy derivatives of compounds of the macrolide series, isolated from the fermentation broth of streptomyces avermilitis | |
| GB1392275A (en) | Therapeutic compositions | |
| ES469425A1 (en) | N-Alkyl-N-acyl derivatives of thienamycin | |
| GB1358114A (en) | One step process for the production of a mono-ester of macrolide antibiotics | |
| GB1386036A (en) | Erythromycin derivatives | |
| IE42957L (en) | Rosamicin (antibiotic 67-694) derivatives. | |
| GB1479362A (en) | 3,17,18-trihydroxy-1,3,5(10)-oestratrienes and their derivatives | |
| GB1467296A (en) | Sulphonyl derivatives of erythromycin | |
| ES420213A1 (en) | Antibiotic | |
| IL44445A0 (en) | Process for isolation of antibiotic av290 | |
| IE39770L (en) | Thiazole derivatives | |
| ES8200347A1 (en) | Pyridine derivatives, process for their preparation and medicaments containing them. | |
| ES8200689A1 (en) | Acylated cephalosporin analogs, process for their preparation and pharmaceutical compositions comprising them. | |
| ZA794155B (en) | New aminoglycosides derived from desoxystreptamine,and their salts,their preparation process,their application as medicaments and the pharmaceutical compounds containing them | |
| CA1007240A (en) | (polychlorophenoxy)methyl esters of thiocyanic acid | |
| GB1455396A (en) | 4,-o-sulphonyl-erythromycin-9-o-oxime derivatives | |
| GB1509147A (en) | Midecamycine derivatives | |
| FR2228064A1 (en) | 4-amino-2,6-dihydroxy-(di or tri-alkoxy)-benzyl-pyrimidines - and derivs - intermediates for pharmaceuticals | |
| ES8203417A1 (en) | Macrolide antibiotic | |
| ES8302718A1 (en) | Derivatives of 7-beta-(ketoximinoacylamido)-ceph-3-em-4-carboxylic acids, process for their preparation and their pharmaceutical compositions containing them. | |
| IE38377L (en) | Maleopimarimide derivatives | |
| JPS5444679A (en) | Production of 5-acyluridine derivative | |
| JPS5630999A (en) | Novel macrolide antibiotic derivative and its preparation | |
| GB1452794A (en) | Estriol derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |