GB1292603A - Improvements relating to penicillins - Google Patents
Improvements relating to penicillinsInfo
- Publication number
- GB1292603A GB1292603A GB92569A GB92569A GB1292603A GB 1292603 A GB1292603 A GB 1292603A GB 92569 A GB92569 A GB 92569A GB 92569 A GB92569 A GB 92569A GB 1292603 A GB1292603 A GB 1292603A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- prepared
- formula
- penicillins
- phenylthiazol
- 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
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
1292603 Penicillins; thiazole and oxazole intermediates therefor JOHN WYETH & BROTHER Ltd 5 Jan 1970 [7 Jan 1969 (2)] 924/69 and 925/69 Headings C2A and C2C Novel penicillins of Formula I and salts thereof, wherein A is C 1 -C 4 alkylene, R<SP>1</SP> is an optionally substituted aryl or heterocyclic radical or a cycloalkyl radical, R<SP>2</SP> is hydrogen, amino, C 1 to C 6 alkyl or an optionally substituted aryl or heterocyclic radical and X is oxygen or sulphur, with the proviso that when A is methylene, R<SP>2</SP> is an aryl or heterocyclic radical are prepared by acylating 6-aminopenicillanic acid or a salt or silyl derivative there. of with an acid of Formula II or an acylating derivative thereof. Substituents of R<SP>1</SP> and R<SP>2</SP> may be halogen, C 1 to C 6 alkyl or alkoxy, CF 3 , or NO 2 . When heterocyclic, R<SP>1</SP> and R<SP>2</SP> may be thienyl, furyl or pyridyl. Acylating derivatives of the acid are preferably the chloride, or an anhydride or mixed anhydride. The reaction is preferably carried out in the presence of a base, e.g. sodium bicarbonate, or triethylamine. The penicillins may be converted to their salts, e.g. of Na, K, ammonium, amines or diamines, or the hydrochloride, sulphate or fumarate. 3 - [2 - Amino - 4 - phenylthiazol - 5 - yl] propionic acid is prepared by cyclizing 4-bromo-4- benzoylbutyric acid and thiourea (see Example 2). 4 - Phenylthiazol - 5 - yl propionic acid is prepared by treating formamide with phosphorus pentasulphide followed by 4-bromobenzoylbutyric acid (Example 4). Ethyl - 6 - bromo - 5 - oxohexanoate and p - chlorothio - benzamide are reacted to give ethyl - 2 - p - chlorophenylthiazol - 4 - yl butyrate which is hydrolysed to the corresponding acid (Example 11). 2 - Ethyl-; 2 - propyl-; and 2 - butyl - 4- phenylthiazol - 5 - yl propionic acids are prepared by reacting respectively, thiopropamide, thiobutyramide and thiovaleramide with 4- benzoyl - 4-bromobutyric acid. These acids and others of Formula II above are converted to the corresponding acid chlorides by treatment with thionyl chloride. Pharmaceutical compositions comprise a penicillin of Formula I above together with a pharmaceutical carrier.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US324915A US3905961A (en) | 1969-01-07 | 1973-01-19 | Thiazole penicillins |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB92469 | 1969-01-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1292603A true GB1292603A (en) | 1972-10-11 |
Family
ID=9712918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB92569A Expired GB1292603A (en) | 1969-01-07 | 1969-01-07 | Improvements relating to penicillins |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1292603A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5239080A (en) * | 1989-02-08 | 1993-08-24 | Takeda Chemical Industries, Ltd. | Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents |
US5371098A (en) * | 1990-02-01 | 1994-12-06 | Takeda Chemical Industries, Ltd. | Use of oxazole compounds to treat osteoporosis |
-
1969
- 1969-01-07 GB GB92569A patent/GB1292603A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5239080A (en) * | 1989-02-08 | 1993-08-24 | Takeda Chemical Industries, Ltd. | Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents |
US5371098A (en) * | 1990-02-01 | 1994-12-06 | Takeda Chemical Industries, Ltd. | Use of oxazole compounds to treat osteoporosis |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
746 | Register noted 'licences of right' (sect. 46/1977) | ||
PCNP | Patent ceased through non-payment of renewal fee |