GB1111214A - Process for preparing semisynthetic penicilins - Google Patents
Process for preparing semisynthetic penicilinsInfo
- Publication number
- GB1111214A GB1111214A GB171366A GB171366A GB1111214A GB 1111214 A GB1111214 A GB 1111214A GB 171366 A GB171366 A GB 171366A GB 171366 A GB171366 A GB 171366A GB 1111214 A GB1111214 A GB 1111214A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cyanomethyl
- amino
- pyridine
- ether
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- -1 cyanomethyl ester Chemical class 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- ORFYDEOVHNVUCK-UHFFFAOYSA-N cyanomethyl 2-(phenylmethoxycarbonylamino)acetate Chemical compound N#CCOC(=O)CNC(=O)OCC1=CC=CC=C1 ORFYDEOVHNVUCK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL107011A PL53617B1 (enrdf_load_stackoverflow) | 1965-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111214A true GB1111214A (en) | 1968-04-24 |
Family
ID=19944472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB171366A Expired GB1111214A (en) | 1965-01-16 | 1966-01-13 | Process for preparing semisynthetic penicilins |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE675128A (enrdf_load_stackoverflow) |
| BR (1) | BR6676457D0 (enrdf_load_stackoverflow) |
| CH (1) | CH468407A (enrdf_load_stackoverflow) |
| DK (1) | DK125596B (enrdf_load_stackoverflow) |
| FR (1) | FR1463536A (enrdf_load_stackoverflow) |
| GB (1) | GB1111214A (enrdf_load_stackoverflow) |
| SE (1) | SE349813B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1062052B (it) * | 1968-11-08 | 1983-06-25 | Lorenzini Sas Inst Biochim | Processo per la produzione dell acido 6 d - alfa aminofenilacetanido penicillanico |
-
1966
- 1966-01-13 FR FR45755A patent/FR1463536A/fr not_active Expired
- 1966-01-13 GB GB171366A patent/GB1111214A/en not_active Expired
- 1966-01-14 BE BE675128D patent/BE675128A/xx unknown
- 1966-01-14 CH CH47666A patent/CH468407A/de unknown
- 1966-01-14 SE SE52166A patent/SE349813B/xx unknown
- 1966-01-17 DK DK25166A patent/DK125596B/da unknown
- 1966-01-17 BR BR17645766A patent/BR6676457D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK125596B (da) | 1973-03-12 |
| CH468407A (de) | 1969-02-15 |
| FR1463536A (fr) | 1966-12-23 |
| SE349813B (enrdf_load_stackoverflow) | 1972-10-09 |
| BE675128A (enrdf_load_stackoverflow) | 1966-05-03 |
| BR6676457D0 (pt) | 1973-09-06 |
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