GB1290177A - - Google Patents
Info
- Publication number
- GB1290177A GB1290177A GB1290177DA GB1290177A GB 1290177 A GB1290177 A GB 1290177A GB 1290177D A GB1290177D A GB 1290177DA GB 1290177 A GB1290177 A GB 1290177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkoxy
- carbo
- phenyl
- formula
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1290177 Esters of α-carboxy-penicillins; malonic ester derivatives PFIZER Inc 29 Aug 1969 [4 June 1969 (4)] 43239/69 Headings C2A and C2C Novel penicillins having the general Formula (I): and salts thereof, wherein R 1 is thienyl, furyl, pyridyl, phenyl or substituted phenyl in which the substituent is C 1 to C 6 alkyl, C 1 to C 6 alkoxy, di-(C 1 to C 6 alkyl) amino, chloro, bromo or trifluoromethyl ; and R 2 is a group of formula: in which X 1 is Cl, Br, F, C 1 to C 6 alkyl or C 1 to C 6 alkoxy, X2 is Cl or C 1 to C 6 alkyl, X 3 is hydrogen, phenyl, carboxyvinyl, carbo-(C 1 to C 6 alkoxy)- vinyl, carboxy C 1 to C 6 alkyl or carbo-(C 1 to C 6 alkoxy) C 1 to C 6 alkyl, and X 4 is NO 2 or di-(C 1 to C 6 alkyl) amino; or R 2 is mono-substituted phenyl wherein the substituent is phenyl, carboxyvinyl, carbo-(C 1 to C 6 alkoxy) vinyl, carboxy C 1 to C 6 alkyl or carbo-(C 1 to C 6 alkoxy) C 1 to C 6 alkyl; or R 2 is biphenyl, C 1 to C 6 alkynyl, 3-[1- (R 5 -substituted)-piperidyl], or a group of formula -(CH 2 ) m -NR 5 R 6 , -CH 2 -CH(CH 3 )- NR 5 R 6 , or -CH(CH 3 )-CH 2 -NR 5 R 6 , in which m is 2 or 3, R 5 is H, C 1 to C 6 alkyl or benzyl and R 6 is C 1 to C 6 alkyl, C 1 to C 6 alkanoyl, carbo C 1 to C 6 alkoxy, benzyl or phenyl, provided that when R 5 is H then R 6 is carbo C 1 to C 6 alkoxy and when R 5 is C 1 to C 6 alkyl then R 6 is not C 1 to C 6 alkyl ; or R 2 is γ-phenylallyl, γ- (substituted phenyl) allyl in which the substituent is one or more of Cl, Br, F, C 1 to C 6 alkoxy, C 1 to C 6 alkyl, NO 2 or methylenedioxy; or R 2 is γ-phenylpropargyl or γ-(substituted phenyl)- propargyl in which the substituent is Cl, Br, NO 2 , C 1 to C 6 alkoxy or C 1 to C 6 alkyl ; and also penicillins having the general Formula (I) above wherein R 2 may additionally be (C 1 to C 3 alkylene)-Y 1 in which Y 1 is azetitino, aziridino, pyrrolidino, piperidino, morpholino, thiomorpholino, N - (C 1 to C 6 alkyl) piperazino, pyrrolo, imidazolo, 2-imidazolino, 2,5-dimethylpyrrolidino, 1,4,5,6-tetrahydropyrimidino, 4-methylpiperidino, 2,6-dimethylpiperidino or a radical of formula in which Z is -(CH 2 ) 3 - or -(CH 2 ) 4 -, which radical may be substituted by -CH 3 , Cl or Br; are prepared by reacting a compound of formula wherein M is H, Na, K or tri-(C 1 to C 6 alkyl)- amino, with an acylating agent of formula wherein X is Cl, Br or -OCOR 4 , in which R 4 is benzyl or C 1 to C 6 alkyl and R 1 and R 2 are as previously defined, in a reaction-inert solvent system at pH 5 to 8 and 0‹ to 50‹ C. α-Carbo-(2-biphenyloxy) phenyl acetic acid is prepared by reacting together phenylmalonic acid, thionyl chloride and o-phenylphenol. The product is converted to the corresponding acid chloride by treatment with thionyl chloride. Pharmaceutical compositions having antibiotic activity against gram-positive and -negative bacteria comprise a penicillin of Formula I as defined above or a non-toxic salt thereof, together with a pharmaceutically acceptable diluent or carrier. Reference has been directed by the Comptroller to Specification 1,133,886.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83051669A | 1969-06-04 | 1969-06-04 | |
US83051869A | 1969-06-04 | 1969-06-04 | |
US83051769A | 1969-06-04 | 1969-06-04 | |
US83048169A | 1969-06-04 | 1969-06-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1290177A true GB1290177A (en) | 1972-09-20 |
Family
ID=27505879
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1290177D Expired GB1290177A (en) | 1969-06-04 | 1969-08-29 |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB1290177A (en) |
MY (1) | MY7400195A (en) |
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1969
- 1969-08-29 GB GB1290177D patent/GB1290177A/en not_active Expired
-
1974
- 1974-12-30 MY MY7400195A patent/MY7400195A/en unknown
Also Published As
Publication number | Publication date |
---|---|
MY7400195A (en) | 1974-12-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |