EP0209274A2
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Furanone derivatives
Assignee: Eli Lilly and Co
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Filing: 1986-06-25
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Granted: —
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Expires: 2006-06-25
Abstract
Abstract Furanone derivatives of formula (I) wherein R 1 is a C 8 -C 24 straight or branched chain monovalent hydrocarbon radical containing a total of 0-6 double and triple bonds; or a group of the formula where n is 0 or 1 and M is -CHO or -CH 2 0H; or R-alk-where alk is a C 2 -C 12 straight or branched chain monovalent hydrocarbon radical containing 0-2 double and triple bonds and R is naphthalenyloxy or benzylphenoxy, inhibit phosphalipidase A 2 and are useful antiinflammatory and ' antiallergy agents.
Inventors
- 👤 Rosanne Bonjouklian
- 👤 Edward David Mihelich
- 👤 Michael Leroy Phillips
- 👤 Christopher John Montague Meade
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 16:01
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/56; C07D307/60; A; A61; A61P; A61P29/00; A61P37/00; A61P37/08
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
76 words
A compound of the formula (I) wherein R 1 is a C S -C 24 straight or branched chain monovalent hydrocarbon radical containing 0-6 double and triple bonds, or a group of the formula wherein n is 0 or 1 and M is -CHO or -CH 2 OH; or R-alk-where alk is a C 2 -C 12 straight or branched chain monovalent hydrocarbon radical containing 0-2 double and triple bonds and R is naphthalenyloxy or benzylphenoxy.
Claim 2
Dependent Claim
76 words
A compound of the formula (I) wherein R 1 is a C S -C 24 straight or branched chain monovalent hydrocarbon radical containing 0-6 double and triple bonds, or a group of the formula wherein n is 0 or 1 and M is -CHO or -CH 2 OH; or R-alk-where alk is a C 2 -C 12 straight or branched chain monovalent hydrocarbon radical containing 0-2 double and triple bonds and R is naphthalenyloxy or benzylphenoxy.
Claim 3
Dependent Claim
21 words
The compound of claim 1 wherein R 1 is a C 12 -C 16 straight or branched chain monovalent hydrocarbon radical.
Claim 4
Dependent Claim
19 words
The compound of claim 1 wherein R 1 is a C 16 straight or branched chain monovalent hydrocarbon radical.
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is (Z,Z)-4-(7,10-hexadecadienyl)-5-hydroxy-2(5H)-furanone.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is 5-hydroxy-4-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2(5H)-furanone.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 5-hydroxy-4[4-2-naphthalenyloxy)butyl]-2(5H)-furanone.
Claim 8
Dependent Claim
25 words
A pharmaceutical formulation comprising a compound of any one of claims 1 to 6 in association with a pharmaceutically acceptable carrier, excipient, or diluent therefore.
Claim 9
Dependent Claim
127 words
A process for preparing a compound of formula (I) as defined in claim 1 which comprises (a) reacting an aldehyde of formula (IV) where R 1 is as defined above with glycoxylic acid and morpholine hydrochloride, or (b) basic hydrolysis of a compound of formula (XIV') where R 1 is as defined above, or (c) acidic hydrolysis of a compound of formula (XX) wherein Z and Z' are independently methyl or ethyl, or when taken together are di-, or tri-, or tetra-methylene and n is 1 or 2, to provide a compound of formula (I) wherein R 1 is (d) reducing a compound of formula (I) wherein R 1 is where n is 1 or 2, to provide a compound of formula (I) wherein R 1 is
Claim 10
Dependent Claim
33 words
A compound of formula 1 as defined in any one of claims 1 to 6 for use as an antiinflammatory agent, an anti-allergy agent, or as an inhibitor of phospholipidase A 2 .
Claim 11
Dependent Claim
35 words
Use of a compound of formula (I) as defined in any one of claims 1 to 6 for the manufacture of an antiinflammatory agent, an anti-allergy agent, or an inhibitor of phospholipidase A 2 .
Claim 12
Dependent Claim
193 words
A process for preparing a compound of the formula (I) wherein R 1 is a C S -C 24 straight or branched chain monovalent hydrocarbon radical containing 0-6 double or triple bonds, or a group of the formula where n is 0 or 1 and M is -CHO or -CH 2 OH; or R-alk-where alk is a C 2 -C 12 straight or branched chain monovalent hydrocarbon radical containing 0-2 double or triple bonds and R is napthaleneyloxy or benzylphenoxy, which comprises: (a) reacting an aldehyde of formula (IV) where R 1 is as defined above with glycoxylic acid and morpholine hydrochloride, or (b) basic hydrolysis of a compound of formula (XIV') where R 1 is as defined above, or (c) acidic hydrolysis of a compound of formula (XX) wherein Z and Z' are independently methyl or ethyl, or when taken together are di-, or tri-, or tetra-methylene and n is 1 or 2, to provide a compound of formula (I) wherein R 1 is (d) reducing a compound of formula (I) wherein R 1 is where n is 1 or 2, to provide a compound of formula (I) wherein R 1 is
Claim 13
Dependent Claim
193 words
A process for preparing a compound of the formula (I) wherein R 1 is a C S -C 24 straight or branched chain monovalent hydrocarbon radical containing 0-6 double or triple bonds, or a group of the formula where n is 0 or 1 and M is -CHO or -CH 2 OH; or R-alk-where alk is a C 2 -C 12 straight or branched chain monovalent hydrocarbon radical containing 0-2 double or triple bonds and R is napthaleneyloxy or benzylphenoxy, which comprises: (a) reacting an aldehyde of formula (IV) where R 1 is as defined above with glycoxylic acid and morpholine hydrochloride, or (b) basic hydrolysis of a compound of formula (XIV') where R 1 is as defined above, or (c) acidic hydrolysis of a compound of formula (XX) wherein Z and Z' are independently methyl or ethyl, or when taken together are di-, or tri-, or tetra-methylene and n is 1 or 2, to provide a compound of formula (I) wherein R 1 is (d) reducing a compound of formula (I) wherein R 1 is where n is 1 or 2, to provide a compound of formula (I) wherein R 1 is
Claim 14
Dependent Claim
49 words
The process of claim 1 wherein an aldehyde of formula (IVa) wherein R la is a C 12 -C 16 straight or branched chain monovalent hydrocarbon radical, is reacted with glycoxylic acid and morpholine hydrochloride to provide a compound of formula (I) wherein R 1 is R 1a ·
Claim 15
Dependent Claim
47 words
The process of claim 1 wherein an aldehyde of formula (IVb) wherein R 1b is a C 16 straight or branched chain monovalent hydrocarbon radical, is reacted with glycoxylic acid and morpholine hydrochloride to provide a compound of formula (I) wherein R 1 is R 1b ·
Claim 16
Dependent Claim
28 words
The process of claim 1 wherein an aldehyde of the formula (IVc) wherein R lc is (Z,Z)-7,10-hexadecadienyl, is reacted with glycoxylic acid and morpholine hydrochloride to provide (Z,Z)-4-(7.10-hexadecadienyl)-5-hydroxy-2(5H)-furanone.
Claim 17
Dependent Claim
28 words
The process of claim 1 wherein an aldehyde of the formula (IVd) wherein R 1d is 4,8,10-trimethyl-3,7,11-tridecatrienyl, is reacted with glycoxylic acid and morpholine hydrochloride to provide 5-hydroxy-4-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2(5H)-furanone.
Claim 18
Dependent Claim
28 words
The process of claim 1 wherein an aldehyde of the formula (IVe) wherein R 1e is 4-(2-naphthalenyloxy)butyl, is reacted with glycoxylic acid and morpholine hydrochloride to provide 5-hydroxy-4-[4-(2-naphthalenyloxy)butyl]-2(5H)-furanone.
Claim 19
Dependent Claim
16 words
A compound of formula (I) when made by the process of any one of claims 1-6.
References Cited (Backward Citations)
No citation records indexed.
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