GB1312030A - Penicillin compounds and a method of synthesising same - Google Patents
Penicillin compounds and a method of synthesising sameInfo
- Publication number
- GB1312030A GB1312030A GB5861871A GB5861871A GB1312030A GB 1312030 A GB1312030 A GB 1312030A GB 5861871 A GB5861871 A GB 5861871A GB 5861871 A GB5861871 A GB 5861871A GB 1312030 A GB1312030 A GB 1312030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- general formula
- unsubstituted alkyl
- penicillin
- 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
- 150000002960 penicillins Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- -1 dimethylsilyl Chemical group 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-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
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Abstract
1312030 Penicillin compounds INSTYTUT PRZEMYSLU FARMACEUTYZNEGO 17 Dec 1971 [22 Dec 1970] 58618/71 Heading C2A [Also in Division C3] The invention comprises penicillin compounds of the general Formula I wherein R represents a substituted or an unsubstituted alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heterocyclic group or a hydrogen atom; R<SP>1</SP> and R<SP>2</SP>, the same or different, represent a substituted or an unsubstituted alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a hydrogen atom or R<SP>1</SP> and E<SP>2</SP> together form a heterocyclic group; and X represents an hydroxyl group or an OR<SP>3</SP> group wherein R<SP>3</SP> represents a substituted silyl group, a substituted or an unsubstituted alkyl group, an aryl group, an aralkyl group or a cycloalkyl group. The group R<SP>3</SP> may be selected from trimethylsilyl, substituted dimethylsilyl, methyl, ethyl, propyl, butyl, benzyl, #,#,#-trichlorethyl, methoxymethyl, phenacyl, p-bromophenacyl, cyanmethyl, nitrophenyl, acetoxymethyl, propionyloxymethyl and pivaloyloxymethyl. A method of synthesizing a penicillin compound of Formula I comprises chlorinating a 6-acylaminopenicillanic acid compound of general Formula II in the presence of an anhydrous organic solvent immiscible with water and of a tertiary amine to form an imidochloride of general Formula III by means of ammonia or an amine of general Formula IV The pencillin may be isolated as a salt of an acid, e.g. hydrochloric, phosphoric, p-toluenesulphonic, citric, oxalic and tartaric acids. The chlorination reaction may be effected by PCl 5 , PCl 3 , POCl 3 , SOCl 2 , (COCl) 2 or COCl 2 at temperatures within the range - 50‹ to + 20‹ C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14521270A PL79157B1 (en) | 1970-12-22 | 1970-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1312030A true GB1312030A (en) | 1973-04-04 |
Family
ID=19953025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5861871A Expired GB1312030A (en) | 1970-12-22 | 1971-12-17 | Penicillin compounds and a method of synthesising same |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS538718B1 (en) |
| GB (1) | GB1312030A (en) |
| PL (1) | PL79157B1 (en) |
| SU (1) | SU511011A3 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS538718B1 (en) * | 1970-12-22 | 1978-03-31 | ||
| US4508723A (en) * | 1977-05-17 | 1985-04-02 | Ciba Geigy Corporation | 6-Azaoligocycloalkylmethyleneaminopenam compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130546C (en) * | 1966-05-18 | |||
| BE758782A (en) * | 1969-11-11 | 1971-05-10 | Leo Pharm Prod Ltd | NEW DERIVATIVES OF 6-AMIDINO PENICILLANIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS AS ANTIBIOTICS |
| PL79157B1 (en) * | 1970-12-22 | 1975-06-30 |
-
1970
- 1970-12-22 PL PL14521270A patent/PL79157B1/xx unknown
-
1971
- 1971-12-17 GB GB5861871A patent/GB1312030A/en not_active Expired
- 1971-12-21 SU SU1728775A patent/SU511011A3/en active
- 1971-12-22 JP JP10454871A patent/JPS538718B1/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS538718B1 (en) * | 1970-12-22 | 1978-03-31 | ||
| US4508723A (en) * | 1977-05-17 | 1985-04-02 | Ciba Geigy Corporation | 6-Azaoligocycloalkylmethyleneaminopenam compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| SU511011A3 (en) | 1976-04-15 |
| PL79157B1 (en) | 1975-06-30 |
| JPS538718B1 (en) | 1978-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 414F | Notice of opposition given (sect. 14/1949) | ||
| 414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
| 49R | Reference inserted (sect. 9/1949) | ||
| SPA | Amended specification published | ||
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |