GB1333905A - Method for o-acylating 7-acylaminocephalosporadesic acids and o-acyl-7-acylaminocephalosporadesic acids - Google Patents
Method for o-acylating 7-acylaminocephalosporadesic acids and o-acyl-7-acylaminocephalosporadesic acidsInfo
- Publication number
- GB1333905A GB1333905A GB1634272A GB1634272A GB1333905A GB 1333905 A GB1333905 A GB 1333905A GB 1634272 A GB1634272 A GB 1634272A GB 1634272 A GB1634272 A GB 1634272A GB 1333905 A GB1333905 A GB 1333905A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acyl
- reaction
- acid
- azolide
- hydroxy
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- -1 hydroxy, amino Chemical group 0.000 abstract 4
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical class OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- LJLDRSCHTYPGOW-MRVPVSSYSA-N (2R)-2-hydroxy-2-[2-(2,2,2-trichloroethoxycarbonyl)phenyl]acetic acid Chemical compound ClC(COC(=O)C1=C([C@H](C(=O)O)O)C=CC=C1)(Cl)Cl LJLDRSCHTYPGOW-MRVPVSSYSA-N 0.000 abstract 1
- IFKVSABTHWCIGO-UHFFFAOYSA-N 1,5-dihydropyrazol-5-ide Chemical compound C=1C=NN[C-]=1 IFKVSABTHWCIGO-UHFFFAOYSA-N 0.000 abstract 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
-
- 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)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1333905 O-Acylating 3-hydroxymethylcephalosporins; D-mandelic acid derivatives SMITH KLINE & FRENCH LABORATORIES 10 April 1972 [7 May 1971] 16342/72 Headings C2A and C2C 3 - Acyloxymethyl - 7 - acylaminocephalosporanic acids are prepared by acylating the 3-hydroxymethyl group of a 3-deacetyl-7-acylaminocephalosporanic acid by reaction with an azolide, any hydroxy, amino or thiol groups in the N-acyl group of the azolide being suitably protected during the acylation and the protecting groups being removed thereafter. The azolide is defined as an N-acyl heterocyclic compound wherein the heterocycle is a quasiaromatic 5-membered ring containing at least two nitrogen atoms, e.g. l-acyl-1,2,4-triazole or 1-acyl-1,2,3-triazole. It is prepared in situ by reacting a carboxylic acid with a diazolide of carbonic acid (N,N<SP>1</SP>-carbonyldiimidazole) in a reaction-inert solvent according to the reaction: The 3-deacetylcephalosporin, preferably as an alkali metal salt, is then added to the reaction mixture, when the following reaction takes place. In the formulµ above, is an acyl group found in the 7-acylamino group of a known antibacterial cephalosporin, is the same as except that any hydroxy, amino and carboxy groups have protecting groups, is an acyl group found in the 3-acyloxymethyl group of a known antibacterial cephalosporin except that an easily eliminated #-substituent may not be present, is the same as except that any hydroxy, amino and thiol groups have protecting groups, and -N# is a quasiaromatic five-membered ring. The process is preferably carried out at neutral to mildly basic pH in a reaction-inert solvent (e.g. benzene, tetrahydrofuran, chloroform or dimethyl-formamide) at 0-50‹ C. o - (2,2,2 - Trichloroethoxycarbonyl)- D - mandelic acid is prepared by reacting D-mandelic acid with 2,2,2-trichloroethyl chloroformate in the presence of N,N-dimethylaniline, and is subsequently converted to the acid chloride with thionyl chloride.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US255632A US3905967A (en) | 1971-05-07 | 1972-05-22 | Method for O-acylating 7-acylamino-cephalosporadesic acids |
| US05/577,816 US4007178A (en) | 1972-04-10 | 1975-05-15 | O-acyl-7-acylaminocephalosporadesic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14138071A | 1971-05-07 | 1971-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1333905A true GB1333905A (en) | 1973-10-17 |
Family
ID=22495444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1634272A Expired GB1333905A (en) | 1971-05-07 | 1972-04-10 | Method for o-acylating 7-acylaminocephalosporadesic acids and o-acyl-7-acylaminocephalosporadesic acids |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU458987B2 (en) |
| BE (1) | BE783095A (en) |
| CA (1) | CA999291A (en) |
| DE (1) | DE2222200A1 (en) |
| FR (1) | FR2137569B1 (en) |
| GB (1) | GB1333905A (en) |
| ZA (1) | ZA723060B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987005297A1 (en) * | 1986-03-03 | 1987-09-11 | The University Of Chicago | Cephalosporin derivatives |
-
1972
- 1972-04-10 GB GB1634272A patent/GB1333905A/en not_active Expired
- 1972-05-01 CA CA140,947A patent/CA999291A/en not_active Expired
- 1972-05-04 AU AU41909/72A patent/AU458987B2/en not_active Expired
- 1972-05-05 BE BE783095A patent/BE783095A/en not_active IP Right Cessation
- 1972-05-05 FR FR7216188A patent/FR2137569B1/fr not_active Expired
- 1972-05-05 ZA ZA723060A patent/ZA723060B/en unknown
- 1972-05-05 DE DE19722222200 patent/DE2222200A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987005297A1 (en) * | 1986-03-03 | 1987-09-11 | The University Of Chicago | Cephalosporin derivatives |
| US4783443A (en) * | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA723060B (en) | 1973-02-28 |
| FR2137569A1 (en) | 1972-12-29 |
| FR2137569B1 (en) | 1975-10-31 |
| DE2222200A1 (en) | 1972-11-16 |
| BE783095A (en) | 1972-11-06 |
| CA999291A (en) | 1976-11-02 |
| AU458987B2 (en) | 1975-03-13 |
| AU4190972A (en) | 1973-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |