GB1299887A - New penicillin derivatives - Google Patents
New penicillin derivativesInfo
- Publication number
- GB1299887A GB1299887A GB3761669A GB3761669A GB1299887A GB 1299887 A GB1299887 A GB 1299887A GB 3761669 A GB3761669 A GB 3761669A GB 3761669 A GB3761669 A GB 3761669A GB 1299887 A GB1299887 A GB 1299887A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- hydrogen
- july
- hydroxyl
- alkyl
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229930182555 Penicillin Natural products 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 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
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-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
1299887 Penicillins FUVEAU SA 24 July 1970 [25 July 1969] 37616/69 Heading C2A Novel penicillins having the Formula I or a tautomeric form thereof of Formula III wherein R is a hydrogen or halogen atom or a hydroxyl or alkoxy group and R<SP>1</SP> is a hydrogen atom, a C 1-7 alkyl or alkenyl group, or an aryl, aralkyl or cycloalykl radical which radicals may be substituted by C 1-4 alkyl, halogen, hydroxyl, nitro or nitroso, and non-toxic salts thereof, are prepared by reacting an α-aminobenzyl penicillin (having R as defined above as a substituent on the benzene ring) either (1) with an isocyanate of Formula R<SP>1</SP>-N=C=S in which R<SP>1</SP> is as defined above (or with ammonium thiocyanate, when R<SP>1</SP> is hydrogen), or (2) with thiophosgene preferably in the presence of triethylamine, followed by a molecular equivalent of ammonia or an amine of formula R<SP>1</SP>-NH 2 . The reactions are preferably carried out in an organic solvent at a temperature of about 0‹ C. Pharmaceutical compositions having antibacterial activity comprise the novel penicillin of Formulae I or III above together with a compatible pharmaceutical carrier.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3761669A GB1299887A (en) | 1969-07-25 | 1969-07-25 | New penicillin derivatives |
| FR7025868A FR2059556B1 (en) | 1969-07-25 | 1970-07-10 | |
| BE753387A BE753387A (en) | 1969-07-25 | 1970-07-13 | NEW PENICILLINS |
| CH1106670A CH515930A (en) | 1969-07-25 | 1970-07-21 | Process for the preparation of new penicillins |
| DE19702036073 DE2036073A1 (en) | 1969-07-25 | 1970-07-21 | New penicillins, their manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3761669A GB1299887A (en) | 1969-07-25 | 1969-07-25 | New penicillin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1299887A true GB1299887A (en) | 1972-12-13 |
Family
ID=10397761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3761669A Expired GB1299887A (en) | 1969-07-25 | 1969-07-25 | New penicillin derivatives |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE753387A (en) |
| CH (1) | CH515930A (en) |
| DE (1) | DE2036073A1 (en) |
| FR (1) | FR2059556B1 (en) |
| GB (1) | GB1299887A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994875A (en) * | 1974-06-24 | 1976-11-30 | Yeda Research & Development Co. Ltd. | Antibiotics |
| FR2364031A1 (en) * | 1975-07-31 | 1978-04-07 | Bottu | NEW PENICILLINS AND THEIR APPLICATION AS MEDICINAL PRODUCTS |
| PT67170B (en) * | 1976-11-06 | 1979-03-21 | Merck Patent Gmbh | LACTAME METHOD FOR THE PRODUCTION THEREOF AND MEDIUM CONTAINING THESE COMPOUNDS |
-
1969
- 1969-07-25 GB GB3761669A patent/GB1299887A/en not_active Expired
-
1970
- 1970-07-10 FR FR7025868A patent/FR2059556B1/fr not_active Expired
- 1970-07-13 BE BE753387A patent/BE753387A/en unknown
- 1970-07-21 DE DE19702036073 patent/DE2036073A1/en active Pending
- 1970-07-21 CH CH1106670A patent/CH515930A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE753387A (en) | 1970-12-16 |
| DE2036073A1 (en) | 1971-02-04 |
| FR2059556B1 (en) | 1974-06-14 |
| FR2059556A1 (en) | 1971-06-04 |
| CH515930A (en) | 1971-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |