GB1241655A - Improvements in or relating to cephalosporin compounds - Google Patents
Improvements in or relating to cephalosporin compoundsInfo
- Publication number
- GB1241655A GB1241655A GB3849267A GB3849267A GB1241655A GB 1241655 A GB1241655 A GB 1241655A GB 3849267 A GB3849267 A GB 3849267A GB 3849267 A GB3849267 A GB 3849267A GB 1241655 A GB1241655 A GB 1241655A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- halide
- cephalosporin compounds
- blocked
- imide
- 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
- -1 cephalosporin compounds Chemical class 0.000 title abstract 7
- 229940124587 cephalosporin Drugs 0.000 title abstract 5
- 229930186147 Cephalosporin Natural products 0.000 title abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004674 formic acids Chemical class 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only starting from compounds containing carbon-to-metal bonds and followed by conversion of the -O- metal to -OH groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,241,655. N-Deacylating cephalosporin compounds. GLAXO LABORATORIES Ltd. 6 Aug., 1968 [21 Aug., 1967], No. 38492/67. Heading C2A. 7# - Acylamino - 4 - carboxy - cephalosporin compounds (other than those having at position- 7 a #-aminoadipoylamino group which are optionally blocked at the amino and/or carboxy groups) are N-deacylated by reacting with an imide-halide-forming reagent, converting the resulting imide halide into an imino ether and hydrolysing or alcoholysing the latter to give a 7#-amino-cephalosporin compound. The 4- carboxyl group of the starting material is preferably blocked, e.g. by esterification with an easily removable esterifying group such as a diphenylmethyl, t-butyl, #,#,#-trichloroethyl or silyl group. Any other functional groups which may be present are blocked if necessary. Typical 7#-acyl groups which may be removed are thienylacetyl, phenylacetyl, phenoxyacetyl, benzoyl and acetyl. The starting materials may have at the 3-position a methyl, hydroxymethyl, etherified hydroxymethyl, or acyloxymethyl group or a group derived from a nucleophile. Suitable imide-halide-forming agents are acid halides of phosphorus acids, e.g. phosphorus oxychloride or pentachloride. The reaction is preferably effected in an inert organic solvent in the presence of a base such as triethylamine, pyridine, dimethylaniline or calcium carbonate. Conversion to the imino ether is preferably by reacting with an alcohol, e.g. methanol, in the presence of a tertiary amine such as listed above. The imino-ether may be decomposed with water or an alkanol in the presence of an acidic or basic catalyst, e.g. hydrochloric, trifluoroacetic, toluenesulphonic, phosphoric or formic acids, or ammonia or salts of a weak acid with alkali- or alkaline earth-metals. The N-deacylated products are useful as intermediates for re-acylation by a different 7#-acylating group to give antibiotically active cephalosporin compounds.
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3849267A GB1241655A (en) | 1967-08-21 | 1967-08-21 | Improvements in or relating to cephalosporin compounds |
| GB3849268D GB1208515A (en) | 1967-08-21 | 1968-08-12 | Alkylaluminium oxidation process |
| CA027932A CA924302A (en) | 1967-08-21 | 1968-08-20 | Cephalosporin compounds |
| IE102168A IE32915B1 (en) | 1967-08-21 | 1968-08-20 | Improvements in or relating to cephalosporin compounds |
| IL3058168A IL30581A (en) | 1967-08-21 | 1968-08-20 | Preparation of 7-amino cephalosporanic acid |
| BE719712A BE719712A (en) | 1967-08-21 | 1968-08-20 | |
| NL6811828A NL6811828A (en) | 1967-08-21 | 1968-08-20 | |
| DE19681795178 DE1795178A1 (en) | 1967-08-21 | 1968-08-20 | Process for the preparation of compounds of the cephalosporin series |
| AT811568A AT303956B (en) | 1967-08-21 | 1968-08-20 | Process for the preparation of compounds of the cephalosporin series |
| JP5910668A JPS5437157B1 (en) | 1967-08-21 | 1968-08-20 | |
| CH1251268A CH553816A (en) | 1967-08-21 | 1968-08-20 | PROCESS FOR THE PREPARATION OF N-DEACYLATED CEPHALOSPORINE COMPOUNDS. |
| FR1585971D FR1585971A (en) | 1967-08-21 | 1968-08-20 | |
| PH9489*UA PH9433A (en) | 1967-08-21 | 1968-08-21 | Process for the preparation of 7-aminocephalosporins and acid addition salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3849267A GB1241655A (en) | 1967-08-21 | 1967-08-21 | Improvements in or relating to cephalosporin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1241655A true GB1241655A (en) | 1971-08-04 |
Family
ID=10403818
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3849267A Expired GB1241655A (en) | 1967-08-21 | 1967-08-21 | Improvements in or relating to cephalosporin compounds |
| GB3849268D Expired GB1208515A (en) | 1967-08-21 | 1968-08-12 | Alkylaluminium oxidation process |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3849268D Expired GB1208515A (en) | 1967-08-21 | 1968-08-12 | Alkylaluminium oxidation process |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5437157B1 (en) |
| AT (1) | AT303956B (en) |
| BE (1) | BE719712A (en) |
| CA (1) | CA924302A (en) |
| CH (1) | CH553816A (en) |
| DE (1) | DE1795178A1 (en) |
| FR (1) | FR1585971A (en) |
| GB (2) | GB1241655A (en) |
| IL (1) | IL30581A (en) |
| NL (1) | NL6811828A (en) |
| PH (1) | PH9433A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
| US6005101A (en) * | 1994-07-22 | 1999-12-21 | Antibioticos S.P.A. | Glutaryl 7-ACA derivatives and processes for obtaining them |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1385683A (en) * | 1971-03-01 | 1975-02-26 | Glaxo Lab Ltd | Antibiotics |
| GB1385685A (en) * | 1971-04-21 | 1975-02-26 | Glaxo Lab Ltd | Cephalosporin derivatives |
| GB1391271A (en) * | 1971-04-30 | 1975-04-16 | Glaxo Lab Ltd | Preparation of antibiotic compounds |
-
1967
- 1967-08-21 GB GB3849267A patent/GB1241655A/en not_active Expired
-
1968
- 1968-08-12 GB GB3849268D patent/GB1208515A/en not_active Expired
- 1968-08-20 JP JP5910668A patent/JPS5437157B1/ja active Pending
- 1968-08-20 FR FR1585971D patent/FR1585971A/fr not_active Expired
- 1968-08-20 CH CH1251268A patent/CH553816A/en not_active IP Right Cessation
- 1968-08-20 DE DE19681795178 patent/DE1795178A1/en active Pending
- 1968-08-20 IL IL3058168A patent/IL30581A/en unknown
- 1968-08-20 BE BE719712A patent/BE719712A/xx unknown
- 1968-08-20 AT AT811568A patent/AT303956B/en not_active IP Right Cessation
- 1968-08-20 NL NL6811828A patent/NL6811828A/xx unknown
- 1968-08-20 CA CA027932A patent/CA924302A/en not_active Expired
- 1968-08-21 PH PH9489*UA patent/PH9433A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562253A (en) * | 1982-08-06 | 1985-12-31 | Biochemie Gesellschaft M.B.H. | Deacylation of amides |
| US6005101A (en) * | 1994-07-22 | 1999-12-21 | Antibioticos S.P.A. | Glutaryl 7-ACA derivatives and processes for obtaining them |
Also Published As
| Publication number | Publication date |
|---|---|
| PH9433A (en) | 1975-11-26 |
| BE719712A (en) | 1969-02-20 |
| CH553816A (en) | 1974-09-13 |
| DE1795178A1 (en) | 1972-08-10 |
| GB1208515A (en) | 1970-10-14 |
| IL30581A (en) | 1975-05-22 |
| FR1585971A (en) | 1970-02-06 |
| NL6811828A (en) | 1969-02-25 |
| AT303956B (en) | 1972-12-27 |
| JPS5437157B1 (en) | 1979-11-13 |
| CA924302A (en) | 1973-04-10 |
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