GB1358374A - Process for the preparation of cephalosporin derivatives - Google Patents
Process for the preparation of cephalosporin derivativesInfo
- Publication number
- GB1358374A GB1358374A GB1782573A GB1782573A GB1358374A GB 1358374 A GB1358374 A GB 1358374A GB 1782573 A GB1782573 A GB 1782573A GB 1782573 A GB1782573 A GB 1782573A GB 1358374 A GB1358374 A GB 1358374A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- cephalosporin
- solvent
- ester
- methyl
- 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
- 229940124587 cephalosporin Drugs 0.000 title abstract 6
- 229930186147 Cephalosporin Natural products 0.000 title abstract 5
- 150000001780 cephalosporins Chemical class 0.000 title abstract 3
- -1 acyl radical Chemical class 0.000 abstract 17
- 238000006243 chemical reaction Methods 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 abstract 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 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
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000005457 ice water Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000006049 ring expansion reaction Methods 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000008096 xylene Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47040136A JPS5241276B2 (enExample) | 1972-04-20 | 1972-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1358374A true GB1358374A (en) | 1974-07-03 |
Family
ID=12572362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1782573A Expired GB1358374A (en) | 1972-04-20 | 1973-04-13 | Process for the preparation of cephalosporin derivatives |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5241276B2 (enExample) |
| AT (1) | AT331392B (enExample) |
| AU (1) | AU5461773A (enExample) |
| BE (1) | BE798459A (enExample) |
| CA (1) | CA1008067A (enExample) |
| DD (1) | DD106186A5 (enExample) |
| DE (1) | DE2320013A1 (enExample) |
| FR (1) | FR2181013A1 (enExample) |
| GB (1) | GB1358374A (enExample) |
| HU (1) | HU165626B (enExample) |
| NL (1) | NL7305374A (enExample) |
| PL (1) | PL85510B1 (enExample) |
| ZA (1) | ZA732711B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5533981A (en) * | 1979-08-13 | 1980-03-10 | Toto Ltd | Valve |
| JPS58182071U (ja) * | 1982-05-29 | 1983-12-05 | 北村バルブ株式会社 | 給水栓における制水装置 |
| JPS58182072U (ja) * | 1982-05-29 | 1983-12-05 | 北村バルブ株式会社 | 給水栓における制水装置 |
| JP6798557B2 (ja) | 2016-09-28 | 2020-12-09 | 日本製鉄株式会社 | 鋼 |
-
1972
- 1972-04-20 JP JP47040136A patent/JPS5241276B2/ja not_active Expired
-
1973
- 1973-04-13 GB GB1782573A patent/GB1358374A/en not_active Expired
- 1973-04-16 DE DE2320013A patent/DE2320013A1/de active Pending
- 1973-04-17 NL NL7305374A patent/NL7305374A/xx unknown
- 1973-04-18 AU AU54617/73A patent/AU5461773A/en not_active Expired
- 1973-04-18 HU HUTO904A patent/HU165626B/hu unknown
- 1973-04-18 CA CA170,017A patent/CA1008067A/en not_active Expired
- 1973-04-19 DD DD170301A patent/DD106186A5/xx unknown
- 1973-04-19 PL PL1973162029A patent/PL85510B1/xx unknown
- 1973-04-19 BE BE130208A patent/BE798459A/xx unknown
- 1973-04-19 FR FR7314399A patent/FR2181013A1/fr not_active Withdrawn
- 1973-04-19 AT AT349673A patent/AT331392B/de not_active IP Right Cessation
- 1973-04-19 ZA ZA732711A patent/ZA732711B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2320013A1 (de) | 1973-11-15 |
| CA1008067A (en) | 1977-04-05 |
| HU165626B (enExample) | 1974-09-28 |
| JPS5241276B2 (enExample) | 1977-10-17 |
| AU5461773A (en) | 1974-10-24 |
| DD106186A5 (de) | 1974-06-05 |
| ATA349673A (de) | 1975-11-15 |
| FR2181013A1 (enExample) | 1973-11-30 |
| NL7305374A (enExample) | 1973-10-23 |
| ZA732711B (en) | 1974-11-27 |
| JPS49293A (enExample) | 1974-01-05 |
| BE798459A (fr) | 1973-08-16 |
| PL85510B1 (enExample) | 1976-04-30 |
| AT331392B (de) | 1976-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |