GB1176339A - Hydrocinnamic Acid Compounds and Processes for making them - Google Patents

Hydrocinnamic Acid Compounds and Processes for making them

Info

Publication number
GB1176339A
GB1176339A GB5767766A GB5767766A GB1176339A GB 1176339 A GB1176339 A GB 1176339A GB 5767766 A GB5767766 A GB 5767766A GB 5767766 A GB5767766 A GB 5767766A GB 1176339 A GB1176339 A GB 1176339A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
acid
halogen
ester
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
Application number
GB5767766A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1176339A publication Critical patent/GB1176339A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Abstract

1,176,339. Hydrocinnamic acid derivatives. ELI LILY & CO. 23 Dec., 1966 [27 Dec., 1965], No. 57677/66. Heading C2C. Novel alpha-substituted hydrocinnamic acids of the general formula wherein R<SP>1</SP> is hydrogen, a halogen or a C 1-4 alkyl or alkoxy group; R<SP>2</SP> is hydrogen or a methyl group; R<SP>3</SP> is a halogen, R<SP>4</SP> is hydrogen, a halogen or a C 1-4 alkyl, C 1-4 alkoxy, phenyl or phenoxy group: Z is oxygen or sulphur; and n is 0 or 1; the salts thereof with alkali metals, alkaline earth metals or ammonia, and the C 1-4 alkyl and di-(C 1-4 alkyl) amino C 1-4 alkyl esters thereof, excluding the 2-dimethylaminoethyl ester of α-phenoxyhydrocinnamic acid and excluding the free acid when n is 1 and R<SP>2</SP> and R<SP>4</SP> are hydrogen and the free acid when n is 0, R<SP>2</SP> is hydrogen and R<SP>4</SP> is a halogen, are prepared by hydrolysing an ester of the general formula and, if desired, converting the resulting acid into a salt or ester thereof. The novel esters of the second formula above are prepared by mixing an alkali metal amide and a benzyl halide in an inert organic solvent with a t-butyl- α - (aryloxy)propionate, t - butyl - α - (arylmercapto)propionate, t - butylaryloxy - acetate or t - butylarylmercapto - acetate. The propionates and acetates described above are prepared by reacting an appropriate phenol or thiophenol with a C 1-4 alkyl α-halopropionate, α-halopropionic acid or t-butyl chloroacetate. Pharmaceutical compositions comprising, as active ingredient, an alpha-substituted hydrocinnamic acid of the first general formula above or a salt or ester thereof as defined above, in admixture with a pharmaceutically acceptable carrier, have serum cholesterol and triglyceride reducing and blood sugar lowering properties and may be administered orally. Reference has been directed by the Comptroller to Specification 1,098,111.
GB5767766A 1965-12-27 1966-12-23 Hydrocinnamic Acid Compounds and Processes for making them Expired GB1176339A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US51670865A 1965-12-27 1965-12-27

Publications (1)

Publication Number Publication Date
GB1176339A true GB1176339A (en) 1970-01-01

Family

ID=24056769

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5767766A Expired GB1176339A (en) 1965-12-27 1966-12-23 Hydrocinnamic Acid Compounds and Processes for making them

Country Status (8)

Country Link
BE (1) BE691840A (en)
BR (1) BR6685715D0 (en)
DE (1) DE1543561A1 (en)
ES (1) ES334932A1 (en)
FR (2) FR1602630A (en)
GB (1) GB1176339A (en)
NL (1) NL6618189A (en)
SE (1) SE327192B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004099168A2 (en) * 2003-04-30 2004-11-18 The Institutes For Pharmaceutical Discovery, Llc Substituted carboxylic acids

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004099168A2 (en) * 2003-04-30 2004-11-18 The Institutes For Pharmaceutical Discovery, Llc Substituted carboxylic acids
WO2004099168A3 (en) * 2003-04-30 2005-02-24 Inst For Pharm Discovery Inc Substituted carboxylic acids
US7358364B2 (en) 2003-04-30 2008-04-15 The Institute For Pharmaceutical Discovery Llc Substituted carboxylic acids
AU2004236173B2 (en) * 2003-04-30 2008-07-03 The Institutes For Pharmaceutical Discovery, Llc Substituted carboxylic acids

Also Published As

Publication number Publication date
NL6618189A (en) 1967-06-28
SE327192B (en) 1970-08-17
ES334932A1 (en) 1967-11-16
BR6685715D0 (en) 1973-12-27
FR7023M (en) 1969-06-09
BE691840A (en) 1967-06-27
FR1602630A (en) 1971-01-04
DE1543561A1 (en) 1969-07-31

Similar Documents

Publication Publication Date Title
SE7705637L (en) PROCEDURE FOR THE PREPARATION OF DIBENSOXEPIN DERIVATIVES WITH THERAPEUTIC EFFECT
GB1457022A (en) Esters of oxyalkyltheophyllines the preparation thereof and pharmaceutical compositions containint them
GB1176339A (en) Hydrocinnamic Acid Compounds and Processes for making them
GB1515060A (en) 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters
IE34314L (en) Dibenzodioxocine derivatives
GB1252329A (en)
GB1530074A (en) Rho-acetamidophenol derivatives the preparation thereof and the use of such derivatives as therapeutic agents
GB1288670A (en)
GB1262292A (en) Novel thiazoline derivatives, the preparation thereof and compositions containing the same
GB1065296A (en) Phenthiazine derivatives
ES435604A1 (en) Indolylacetylamino acid derivatives, process for their preparation, and pharmaceutical compositions
GB1529251A (en) 9,10-dihydroergopeptines
GB1139164A (en) New heterocyclic acetic acid compounds and methods for their production
GB1448758A (en) Thiazole derivatives
GB1507723A (en) Acyloxymethyl cephalosporin esters
ES446623A1 (en) Steroid carboxylic acids and derivatives
GB1410275A (en) Phenoxycarboxylic acid derivatives their preparation and compositions containing them
SE7408868L (en)
GB1264197A (en)
GB1437788A (en) Therapeutic compositions
IE33762L (en) Adamantylcarboxamidophenylacetic acid derivatives
GB1237062A (en) ESTERS OF alpha-(1-SUBSTITUTED-3-PYRROLIDINYL)-alpha-PHENYL-ACETIC ACID
GB1223945A (en) Alkyl esters of 1-(disubstituted phenyl or benzyl)-1h-indazol-3-yloxy-acetic acids
GB1504683A (en) Pharmaceutical compositions containing substituted pyrimido-quinoline derivatives
GB1202110A (en) Novel quinoline derivatives and their preparation