GB1239821A - Method for the production of penicillins - Google Patents
Method for the production of penicillinsInfo
- Publication number
- GB1239821A GB1239821A GB3022268A GB3022268A GB1239821A GB 1239821 A GB1239821 A GB 1239821A GB 3022268 A GB3022268 A GB 3022268A GB 3022268 A GB3022268 A GB 3022268A GB 1239821 A GB1239821 A GB 1239821A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- reaction product
- imine reaction
- phenoxymethylpenicillin
- acylated
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 5
- 150000002466 imines Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 3
- 229930195708 Penicillin V Natural products 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 229940056367 penicillin v Drugs 0.000 abstract 2
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 abstract 1
- 229960000723 ampicillin Drugs 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- LQOLIRLGBULYKD-JKIFEVAISA-N cloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl LQOLIRLGBULYKD-JKIFEVAISA-N 0.000 abstract 1
- 229960003326 cloxacillin Drugs 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229960001585 dicloxacillin Drugs 0.000 abstract 1
- YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 229960003085 meticillin Drugs 0.000 abstract 1
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 abstract 1
- 229960001019 oxacillin Drugs 0.000 abstract 1
- VDUVBBMAXXHEQP-SLINCCQESA-M oxacillin sodium Chemical compound [Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 VDUVBBMAXXHEQP-SLINCCQESA-M 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229940083542 sodium Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65469067A | 1967-07-20 | 1967-07-20 | |
| US72953568A | 1968-05-16 | 1968-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1239821A true GB1239821A (en) | 1971-07-21 |
Family
ID=27096794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3022268A Expired GB1239821A (en) | 1967-07-20 | 1968-06-25 | Method for the production of penicillins |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH503760A (enrdf_load_stackoverflow) |
| DE (1) | DE1770838A1 (enrdf_load_stackoverflow) |
| DK (1) | DK120438B (enrdf_load_stackoverflow) |
| FR (1) | FR1596495A (enrdf_load_stackoverflow) |
| GB (1) | GB1239821A (enrdf_load_stackoverflow) |
| SE (1) | SE359839B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1366682A (en) * | 1971-04-30 | 1974-09-11 | Merck & Co Inc | Process to prepare antibiotic intermediates |
| DE2221035C2 (de) * | 1972-04-28 | 1982-03-25 | Merck & Co., Inc., 07065 Rahway, N.J. | Verfahren zur Herstellung von substituierten 6-Iminopenicillinen und 7-Iminocephalosporinen |
-
1968
- 1968-06-25 GB GB3022268A patent/GB1239821A/en not_active Expired
- 1968-06-26 DK DK304368A patent/DK120438B/da unknown
- 1968-07-10 DE DE19681770838 patent/DE1770838A1/de active Pending
- 1968-07-11 FR FR1596495D patent/FR1596495A/fr not_active Expired
- 1968-07-19 CH CH1085868A patent/CH503760A/fr not_active IP Right Cessation
- 1968-07-19 SE SE994168A patent/SE359839B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE359839B (enrdf_load_stackoverflow) | 1973-09-10 |
| DE1770838A1 (de) | 1972-01-13 |
| CH503760A (fr) | 1971-02-28 |
| FR1596495A (enrdf_load_stackoverflow) | 1970-06-22 |
| DK120438B (da) | 1971-06-01 |
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