IE34074L - Cephalosporin derivatives from penicillins. - Google Patents
Cephalosporin derivatives from penicillins.Info
- Publication number
- IE34074L IE34074L IE700316A IE31670A IE34074L IE 34074 L IE34074 L IE 34074L IE 700316 A IE700316 A IE 700316A IE 31670 A IE31670 A IE 31670A IE 34074 L IE34074 L IE 34074L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- acids
- methyl
- esters
- penicillin
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title abstract 4
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 150000002960 penicillins Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 5
- 150000007513 acids Chemical class 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 3
- 229940049954 penicillin Drugs 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 abstract 2
- 150000003017 phosphorus Chemical class 0.000 abstract 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 abstract 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- GSDOVLJOXOLSHP-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)P(O)(=O)O.BrC1=CC=CC=C1 Chemical class [N+](=O)([O-])C1=C(C=CC=C1)P(O)(=O)O.BrC1=CC=CC=C1 GSDOVLJOXOLSHP-UHFFFAOYSA-N 0.000 abstract 1
- IKFIAYNBJNQVLS-UHFFFAOYSA-N [S].C1CSCN1 Chemical compound [S].C1CSCN1 IKFIAYNBJNQVLS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000002274 desiccant Substances 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- -1 hydrocarbyl sulphonic acid Chemical compound 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 abstract 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 abstract 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003009 phosphonic acids Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/08—Preparation by forming the ring or condensed ring systems
- C07D501/10—Preparation by forming the ring or condensed ring systems from compounds containing the penicillin ring system
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1299734 Preparing 3-Methyl-cephalosporanic acid esters GLAXO LABORATORIES Ltd 10 March 1970 [11 March 1969] 12865/69 Heading C2A 7# -Acylamido-3-methyl-cephalosporanic acid esters are prepared by heating a 6#-acylamidopenicillanic acid 1-oxide ester in a solvent selected from ketones boiling at 75‹ to 120‹ C., esters boiling at 75‹ to 140‹ C., dioxan (the heating being for at least 2 hours at 75‹ to 110‹C. and for at least 45 minutes at higher temperatures in these solvents), and diethylene glycol dimethyl ether, in the presence of a hydrocarbyl sulphonic acid or a phosphorus acid. Suitable ketones and esters are ethyl methyl ketone, isobutyl methyl ketone, methyl n-propyl ketone, n-propyl acetate, n-butyl acetate, iso-butyl acetate, sec-butyl acetate and diethyl carbonate. Hydrocarbyl sulphonic acids may be alkyl, aryl or aralkyl sulphonic acids. Phosphorus acids may be ortho-, poly- or pyrophosphoric acids, phosphonic or phosphorus acids; the phosphonic acids may be aliphatic, araliphatic or aryl and the organic moiety may be substituted e.g. by halogen or nitro. Typical such acids are methane-, ethane-, dichloromethane-, trichloromethane-, iodomethane-, bromobenzene- and nitrobenzenephosphonic acids. The acid is preferably used in a proportion of 0À05 to 0À2 mole and not exceeding 1À0 mole per mole of the penicillin oxide. The reaction is preferably carried out under reflux using a desiccant in the reflux return tube to remove water formed during the reaction. The product is isolated by removing the solvent e.g. by evaporation, and the acid, e.g. by water-washing if the solvent is water-immiscible or else by neutralizing with e.g. CaCO 3 or MgO and filtering, optionally decolorising the charcoal and precipitating the product with water, and crystallising or purifying by chromatography. The penicillin 1-oxide ester is obtained by esterifying the 3-carboxyl group and then oxidising the 1-sulphur group with an oxidising agent in an amount such that at least 1 atom of active oxygen per atom of thiazolidine sulphur is present. Typical oxidising agents are metaperiodic acid, peracetic acid, monoperphthalic acid, m-chloroperbenzoic acid, or t-butylhypochlorite with a weak base, e.g. pyridine. The penicillin 1-oxide ester preferably has protecting groups on any radicles present which are reactive in the various processes.
[GB1299734A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB02865/69A GB1299734A (en) | 1969-03-11 | 1969-03-11 | Improvements in or relating to cephalosporin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34074L true IE34074L (en) | 1970-09-11 |
| IE34074B1 IE34074B1 (en) | 1975-01-22 |
Family
ID=10012562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE316/70A IE34074B1 (en) | 1969-03-11 | 1970-03-10 | Improvements in or relating to cephalosporin compounds |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5417751B1 (en) |
| AT (1) | AT306920B (en) |
| BE (1) | BE747118A (en) |
| BR (1) | BR6915236D0 (en) |
| CH (1) | CH537416A (en) |
| DE (1) | DE2011375A1 (en) |
| ES (1) | ES377329A1 (en) |
| FR (1) | FR2037857A5 (en) |
| GB (1) | GB1299734A (en) |
| HU (1) | HU165811B (en) |
| IE (1) | IE34074B1 (en) |
| NL (1) | NL7003357A (en) |
| SE (1) | SE386901B (en) |
| YU (1) | YU36378B (en) |
| ZA (1) | ZA701626B (en) |
-
1969
- 1969-03-11 GB GB02865/69A patent/GB1299734A/en not_active Expired
- 1969-12-16 BR BR215236/69A patent/BR6915236D0/en unknown
-
1970
- 1970-03-10 SE SE7003188A patent/SE386901B/en unknown
- 1970-03-10 DE DE19702011375 patent/DE2011375A1/en active Pending
- 1970-03-10 CH CH355370A patent/CH537416A/en not_active IP Right Cessation
- 1970-03-10 AT AT225270A patent/AT306920B/en not_active IP Right Cessation
- 1970-03-10 IE IE316/70A patent/IE34074B1/en unknown
- 1970-03-10 FR FR7008449A patent/FR2037857A5/fr not_active Expired
- 1970-03-10 ES ES377329A patent/ES377329A1/en not_active Expired
- 1970-03-10 BE BE747118D patent/BE747118A/en not_active IP Right Cessation
- 1970-03-10 ZA ZA701626A patent/ZA701626B/en unknown
- 1970-03-10 JP JP2002470A patent/JPS5417751B1/ja active Pending
- 1970-03-10 HU HUGA999A patent/HU165811B/hu unknown
- 1970-03-10 NL NL7003357A patent/NL7003357A/xx unknown
- 1970-03-11 YU YU00580/70A patent/YU36378B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1299734A (en) | 1972-12-13 |
| ES377329A1 (en) | 1972-06-16 |
| DE2011375A1 (en) | 1970-09-24 |
| BR6915236D0 (en) | 1973-02-13 |
| YU58070A (en) | 1981-11-13 |
| CH537416A (en) | 1973-05-31 |
| IE34074B1 (en) | 1975-01-22 |
| NL7003357A (en) | 1970-09-15 |
| ZA701626B (en) | 1971-10-27 |
| BE747118A (en) | 1970-09-10 |
| HU165811B (en) | 1974-11-28 |
| SE386901B (en) | 1976-08-23 |
| FR2037857A5 (en) | 1970-12-31 |
| JPS5417751B1 (en) | 1979-07-02 |
| AT306920B (en) | 1973-04-25 |
| YU36378B (en) | 1983-06-30 |
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