GB1239814A - Process for the preparation of 7-aminocephalosporanic acid and its derivatives - Google Patents
Process for the preparation of 7-aminocephalosporanic acid and its derivativesInfo
- Publication number
- GB1239814A GB1239814A GB35757/68A GB3575768A GB1239814A GB 1239814 A GB1239814 A GB 1239814A GB 35757/68 A GB35757/68 A GB 35757/68A GB 3575768 A GB3575768 A GB 3575768A GB 1239814 A GB1239814 A GB 1239814A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- agent
- group
- prepared
- imino
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 241001137862 IDIR agent Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1,239,814. 7 - Aminocephalosporanic acid derivatives. KONINKLIJKE NEDERLANDSCHE GIST - EN SPIRITUS - FABRIEK N.V. 26 July, 1968 [7 Aug., 1967], No.35757/68. Heading C2C. A 7-aminocephalosporanic acid derivative of Formula I wherein R is H or an esterified OH group, is prepared by treating a 4-silyl ester of Formula II wherein R is as above, R a is an acyl group having any functional groups present blocked, and R b is a silyl group, with an agent (A) to form a 7-imino halide preferably at a temperature below -15 C., treating the 7-imino halide with an agent (B) to form a 7-imino ether, preferably at a temperature below-15 C., and hydrolysing or alcoholysing the product obtained to split the imino ether and form the compound of Formula I. Agent (A) may be phosphorus pentachloride or phosphorus oxychloride and agent (B) is an alcohol e.g. methanol or ethanol. The reaction takes place in the presence of a tertiary amine. The 4-silyl ester of Formula II is prepared by reacting the corresponding free acid or salt thereof with a silylating agent of formula R 1 R 2 R 3 SiX, wherein X is halogen and R 1 , R 2 and R 3 , which may be the same or different, are hydrocarbon radicals or halogen atoms or one of R 1 , R 2 or R 3 may be a hydrogen atom; or where X is amino or HNSiR 1 R 2 R 3 and R 1 , R 2 and R 3 may be the same or different and are hydrocarbon radicals. Cephalosporins of Formula III wherein R c is an acyl group other than the R a group present in the starting material, are produced by acylating in a conventional manner the compounds of Formula I. Pharmaceutical compositions comprise a cephalosporin of Formula III when prepared by the process of the invention, and a pharmaceutical carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL676710835A NL150798B (en) | 1967-08-07 | 1967-08-07 | PROCESS FOR THE PREPARATION OF 7-AMINOCEPHALOSORANIC ACID AND ITS DERIVATIVES. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1239814A true GB1239814A (en) | 1971-07-21 |
Family
ID=19800883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35757/68A Expired GB1239814A (en) | 1967-08-07 | 1968-07-26 | Process for the preparation of 7-aminocephalosporanic acid and its derivatives |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT280475B (en) |
| BE (1) | BE718824A (en) |
| CH (1) | CH513920A (en) |
| DK (1) | DK142912B (en) |
| ES (1) | ES356543A1 (en) |
| FR (1) | FR1583480A (en) |
| GB (1) | GB1239814A (en) |
| IE (1) | IE32230B1 (en) |
| IL (1) | IL30392A (en) |
| IT (1) | IT1035011B (en) |
| NL (1) | NL150798B (en) |
| SE (1) | SE373591B (en) |
| YU (1) | YU34589B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4242509A (en) * | 1979-04-13 | 1980-12-30 | Eli Lilly And Company | Process for producing 7-amino-7-alkoxycephalosporins |
| US4286088A (en) * | 1977-12-12 | 1981-08-25 | Takeda Chemical Industries, Ltd. | Process for preparing 7-aminocephalosporins |
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
| US6642020B2 (en) | 2001-04-19 | 2003-11-04 | Bioferma Murcia S.A. | Process for preparing cephalosporin derivatives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758587A (en) * | 1969-11-17 | 1971-05-06 | Fujisawa Pharmaceutical Co | PROCESS FOR THE PREPARATION OF 7-AMINOCEPHALOSPORANIC ACID DERIVATIVES AND NEW PRODUCTS THUS OBTAINED |
| JPS4948760B1 (en) * | 1970-12-25 | 1974-12-23 | ||
| GB1388267A (en) * | 1971-06-17 | 1975-03-26 | Glaxo Lab Ltd | Preparation of antibiotic compounds |
-
1967
- 1967-08-07 NL NL676710835A patent/NL150798B/en not_active IP Right Cessation
-
1968
- 1968-07-18 IL IL30392A patent/IL30392A/en unknown
- 1968-07-26 GB GB35757/68A patent/GB1239814A/en not_active Expired
- 1968-07-26 ES ES356543A patent/ES356543A1/en not_active Expired
- 1968-07-30 IE IE920/68A patent/IE32230B1/en unknown
- 1968-07-30 CH CH1141768A patent/CH513920A/en not_active IP Right Cessation
- 1968-07-31 BE BE718824D patent/BE718824A/xx not_active IP Right Cessation
- 1968-08-01 DK DK372068AA patent/DK142912B/en not_active IP Right Cessation
- 1968-08-01 YU YU1833/68A patent/YU34589B/en unknown
- 1968-08-05 IT IT38917/68A patent/IT1035011B/en active
- 1968-08-05 SE SE6810565A patent/SE373591B/en unknown
- 1968-08-06 FR FR1583480D patent/FR1583480A/fr not_active Expired
- 1968-08-06 AT AT766168A patent/AT280475B/en not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286088A (en) * | 1977-12-12 | 1981-08-25 | Takeda Chemical Industries, Ltd. | Process for preparing 7-aminocephalosporins |
| US4242509A (en) * | 1979-04-13 | 1980-12-30 | Eli Lilly And Company | Process for producing 7-amino-7-alkoxycephalosporins |
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
| US6642020B2 (en) | 2001-04-19 | 2003-11-04 | Bioferma Murcia S.A. | Process for preparing cephalosporin derivatives |
| US6730497B2 (en) | 2001-04-19 | 2004-05-04 | Bioferma Murcia S.A. | Process for preparing cephalosporanic acid derivatives using β-ketoacid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| DK142912C (en) | 1981-10-05 |
| NL150798B (en) | 1976-09-15 |
| IL30392A0 (en) | 1968-09-26 |
| AT280475B (en) | 1970-04-10 |
| IE32230L (en) | 1969-02-07 |
| IE32230B1 (en) | 1973-05-16 |
| SE373591B (en) | 1975-02-10 |
| DK142912B (en) | 1981-02-23 |
| CH513920A (en) | 1971-10-15 |
| NL6710835A (en) | 1969-02-11 |
| DE1770980B2 (en) | 1977-04-07 |
| IL30392A (en) | 1971-12-29 |
| FR1583480A (en) | 1969-10-31 |
| DE1770980A1 (en) | 1972-03-02 |
| YU34589B (en) | 1979-10-31 |
| YU183368A (en) | 1979-04-30 |
| ES356543A1 (en) | 1970-01-16 |
| IT1035011B (en) | 1979-10-20 |
| BE718824A (en) | 1969-01-31 |
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