GB1344309A - Method for the production of d - -alpha-aminobenzyl-penicillin - Google Patents
Method for the production of d - -alpha-aminobenzyl-penicillinInfo
- Publication number
- GB1344309A GB1344309A GB5496771A GB5496771A GB1344309A GB 1344309 A GB1344309 A GB 1344309A GB 5496771 A GB5496771 A GB 5496771A GB 5496771 A GB5496771 A GB 5496771A GB 1344309 A GB1344309 A GB 1344309A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- imino
- ampicillin
- ether
- chloroform
- 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
- 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 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
- 229960000723 ampicillin Drugs 0.000 abstract 4
- 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 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 229930182555 Penicillin Natural products 0.000 abstract 3
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract 3
- 229940056360 penicillin g Drugs 0.000 abstract 3
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 239000012320 chlorinating reagent Substances 0.000 abstract 2
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical group ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000855 fermentation Methods 0.000 abstract 2
- 230000004151 fermentation Effects 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 abstract 1
- DVMQNHACVBLYQH-UHFFFAOYSA-N 2-anilinoacetyl chloride;hydrochloride Chemical compound Cl.ClC(=O)CNC1=CC=CC=C1 DVMQNHACVBLYQH-UHFFFAOYSA-N 0.000 abstract 1
- 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
- 229930195708 Penicillin V Natural products 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940056367 penicillin v Drugs 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 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 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- -1 silyl ester Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000004684 trihydrates 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2627971 | 1971-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1344309A true GB1344309A (en) | 1974-01-23 |
Family
ID=11219128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5496771A Expired GB1344309A (en) | 1971-06-25 | 1971-11-26 | Method for the production of d - -alpha-aminobenzyl-penicillin |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3872088A (https=) |
| AR (1) | AR192801A1 (https=) |
| AT (1) | AT320146B (https=) |
| AU (1) | AU461848B2 (https=) |
| BE (1) | BE785376A (https=) |
| CA (1) | CA980764A (https=) |
| CH (1) | CH579573A5 (https=) |
| DE (1) | DE2231072A1 (https=) |
| ES (1) | ES399098A1 (https=) |
| GB (1) | GB1344309A (https=) |
| LU (1) | LU65588A1 (https=) |
| NL (1) | NL7117953A (https=) |
| PH (1) | PH10806A (https=) |
| ZA (1) | ZA72567B (https=) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499909A (en) * | 1966-05-18 | 1970-03-10 | Koninklijke Gist Spiritus | Process for production of 6-aminopenicillanic acid |
| IE33478B1 (en) * | 1968-07-26 | 1974-07-10 | Beecham Group Ltd | Esters of 6-aminopenicillanic acid |
-
1971
- 1971-11-26 GB GB5496771A patent/GB1344309A/en not_active Expired
- 1971-12-28 NL NL7117953A patent/NL7117953A/xx unknown
-
1972
- 1972-01-22 ES ES399098A patent/ES399098A1/es not_active Expired
- 1972-01-28 ZA ZA720567A patent/ZA72567B/xx unknown
- 1972-06-12 US US262123A patent/US3872088A/en not_active Expired - Lifetime
- 1972-06-19 CA CA145,118A patent/CA980764A/en not_active Expired
- 1972-06-22 AT AT538972A patent/AT320146B/de not_active IP Right Cessation
- 1972-06-22 LU LU65588D patent/LU65588A1/xx unknown
- 1972-06-23 BE BE785376A patent/BE785376A/xx unknown
- 1972-06-23 CH CH950772A patent/CH579573A5/xx not_active IP Right Cessation
- 1972-06-23 AU AU43863/72A patent/AU461848B2/en not_active Expired
- 1972-06-23 AR AR242725A patent/AR192801A1/es active
- 1972-06-24 DE DE2231072A patent/DE2231072A1/de active Pending
- 1972-06-26 PH PH13661A patent/PH10806A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH10806A (en) | 1977-09-06 |
| US3872088A (en) | 1975-03-18 |
| BE785376A (fr) | 1972-10-16 |
| AR192801A1 (es) | 1973-03-14 |
| CH579573A5 (https=) | 1976-09-15 |
| LU65588A1 (https=) | 1972-11-28 |
| ZA72567B (en) | 1972-10-25 |
| ES399098A1 (es) | 1974-11-16 |
| CA980764A (en) | 1975-12-30 |
| DE2231072A1 (de) | 1973-01-11 |
| AU461848B2 (en) | 1975-06-05 |
| AU4386372A (en) | 1974-01-03 |
| AT320146B (de) | 1975-01-27 |
| NL7117953A (https=) | 1972-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 433D | Application made for revocation (sect. 33/1949) | ||
| 434A | Offer to surrender (sect. 34/1949) | ||
| 433 | Proceeding terminated by voluntary surrender of the patent (sect. 33/1949) | ||
| 434B | Case decided by the comptroller ** patent revoked (sect. 34/1949) |