Oxalylamino-benzofuran- and benzothienyl-derivatives

• US 5,565,488 A
• Filed: 05/23/1995
• Issued: 10/15/1996
• Est. Priority Date: 05/31/1994
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Es-Sayed, Mazen, Fischer, Rudiger, Hanko, Rudolf, Fitzgerald, Mary F., Tudhope, Stephen, Sturton, Graham, Braunlich, Gabriele, McDonald-Gibson, Wendy J., Abram, Trevor
• Primary Examiner(s): DENTZ, BERNARD I
• Application Number:
  US08/448,212
• Time in Patent Office: 511 Days
• Field of Search: 549/51, 549/55, 549/57, 549/466, 549/468, 514/443, 514/469, 514/470
• US Class Current: 514/469
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/08 Bronchodilators
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: C07D 307/80 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 307/83 Oxygen atoms
• CPC Class Codes: C07D 307/84 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 333/56 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

The inventive Oxalylamino-benzofuran- and benzothienyl-derivatives are prepared by reacting the appropriate amino substituted benzofuranes and benzothiophenes with oxalic acid derivatives. The inventive compounds are suitable for the prevention and treatment of acute and chronic inflammatory processes, particularly of the airways.

Claims

1. An oxalylamino-benzofuran- or benzothienyl-derivative formula ##STR346## in which L represents an oxygen or sulfur atom,

R¹ represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms or represents halogen, carboxyl, cyano, nitro, trifluoromethyl or a group of a formula --OR⁵, --SR⁶ or --NR⁷ R⁸, in which

R⁵, R⁶ and R⁸ identical or different and denote hydrogen, cycloalkyl having 3 to 6 carbon atoms, benzyl or a 5 to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms selected from the group consisting of N, S and O and to which a phenyl ring can be fused and which is optionally substituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms, or

denote straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms, or

denote phenyl, which is optionally monosubstituted to disubstituted by identical or different substituents selected from the group consisting of nitro, halogen, carboxy or straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms, or

R⁵ denotes a hydroxyl protecting group, and

R⁷ denotes hydrogen or a straight-chain or branched alkyl having up to 4 carbon atoms

R² represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms,

R³ represents hydroxyl, benzyloxy or straight-chain or branched alkyl or alkoxy each having up to 10 carbon atoms, and each of which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of halogen, carboxyl, trifluoromethyl, phenyl, cyano, or straight-chain or branched alkoxy or oxyacyl each having up to 6 carbon atoms, morpholinyl or by a residue of a formula ##STR347## or represents aryl having 6 to 10 carbon atoms, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms, or represents a group of a formula --NR⁹ R¹⁰, in which

R⁹ and R¹⁰ are identical or different and denote hydrogen, cycloalkyl having 3 to 6 carbon atoms or denote straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms or phenyl, or

denote aryl having 6 to 10 carbon atoms, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms, or

denote a group of a formula --SO₂ R¹¹, in which

R¹¹ denotes straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl, or denotes phenyl, which is optionally substituted by trifluoromethyl, cyano, nitro or straight-chain or branched alkyl having up to 6 carbon atoms, or

R³ represents a residue of a formula ##STR348## T represents an oxygen or sulfur atom, A represents hydrogen, hydroxyl, cycloalkyl having up to 6 carbon atoms, carboxy or straight-chain or branched alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, or represents straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms and each of which is optionally monosubstituted by cyano or by a 5 to 7-membered saturated or unsaturated heterocycle having up to 4 heteroatoms selected from the group consisting of N, S and O, which is optionally substituted by identical or different substituents selected from the group consisting of hydroxy, halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms,

or alkyl and/or alkenyl are optionally substituted by a group of a formula ##STR349## in which denotes a number 1 or 2, and in which both rings are optionally monosubstituted by hydroxy, halogen or by straight-chain or branched alkyl having up to 6 carbon atoms,

or alkyl and/or alkenyl are optionally monosubstituted by a group of a formula --CO--R¹², --CO--NR¹³ R¹⁴, --CONR¹⁵ --SO₂ --R¹⁶ or --PO(OR¹⁷)(OR¹⁸), ##STR350## in which R¹² denotes hydroxyl, cycloalkyloxy having up 3 to 7 carbon atoms or straight-chain or branched alkyl or alkoxy each having up to 8 carbon atoms,

R¹³, R¹⁴ and R¹⁵ are identical or different and represent hydrogen, a straight-chain or branched alkyl having up to 6 carbon atoms, phenyl or benzyl, or

R¹³ denotes hydrogen, and

R¹⁴ denotes a 5- 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, S and O, hydroxyl or a residue of the formula ##STR351## or R¹³ and R¹⁵ together with the nitrogen atom form a 5- or 6-membered saturated heterocycle,

R¹⁶ denotes a straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl or trifluoromethyl, or denotes phenyl, which is optionally substituted by substituents from the series comprising halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms,

R¹⁷, R¹⁸ and R¹⁹ are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms,

R²⁰ denotes hydrogen, an aminoprotecting group or straight-chain or branched alkyl having up to 6 carbon atoms,

R²¹ and R²² are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or

R²¹ has the abovementioned meaning, and

R²² denotes cycloalkyl having 3 to 6 carbon atoms or aryl having up 6 to 10 carbon atoms or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by cyano, methylthio, hydroxy, mercapto, guanidyl or a group of a formula --NR²³ R²⁴ or R²⁵ --CO--, wherein

R²³ and R²⁴ have the meaning shown above for R¹³, R¹⁴ and R¹⁵ and are identical to the latter or different from the latter,

R²⁵ denotes hydroxyl, benzyloxycarbonyl, straight-chain or branched alkoxy having up to 6 carbon atoms or the abovementioned group --NR²³ R²⁴,

or alkyl is optionally substituted by cycloalkyl having 3 to 6 carbon atoms, or by aryl having 6 to 10 carbon atoms, which is optionally substituted by hydroxyl, halogen, nitro, straight-chain or branched alkoxy having up to 8 carbon atoms or by the abovementioned group of the formula --NR²³ R²⁴, or alkyl is optionally substituted by indolyl or by a 5 to 6 membered unsaturated heterocycle having up to 3N-atoms wherein optionally all --NH-functions are protected by straight-chain or branched alkyl having up to 6 carbon atoms or by an amino protecting group, or

A represents a group of the formula --CONR^13'"'"' R^14'"'"', in which

R^13'"'"' and R^14'"'"' are identical or different and have the abovementioned meaning of R¹³ and R¹⁴, and

R⁴ represents phenyl, or represents a 5 to 7 membered, saturated or unsaturated heterocycle, which can contain up to 4 oxygen, sulphur and/or nitrogen atoms as heteroatoms and to which further a benzene ring can be fused and wherein all rings are optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, naphthyl, adamantyl, thiophenyl, cycloalkyl having up to 3 to 6 carbon atoms, halogen, nitro, tetrazolyl, thiazolyl, thienyl, furanyl, pyridyl, trifluoromethyl, phenoxy, difluoromethyl, cyano, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 11 carbon atoms or by a group of formula--NR²⁶ R²⁷, --SR²⁸, SO₂ R²⁹, --O--SO₂ R³⁰, --(CH₂)_b --O--CO--R³¹, ##STR352## in which R²⁶ and R²⁷ have the meaning shown above for R⁹ and R¹⁰ and are identical to the latter or different from the latter, or

R²⁶ denotes hydrogen, and

R²⁷ denotes straight-chain or branched acyl having up to 6 carbon atoms,

R²⁸ denotes straight-chain or branched alkyl having up to 6 carbon atoms,

R²⁹ and R³⁰ are identical or different and represent straight-chain or branched alkyl having up to 6 carbon atoms, benzyl or phenyl, which are optionally substituted by trifluoromethyl, halogen or straight-chain or branched alkyl having up to 6 carbon atoms,

R³¹ denotes straight-chain or branched alkoxycarbonyl or alkyl having up to 6 C-atoms or carboxyl,

b denotes a number 0 or 1, or

phenyl is optionally substituted by phenyl or phenoxy, which are optionally monosubstituted to trisubstituted by halogen, formyl, nitro, straight-chain or branched alkyl, acyl, hydroxyalkyl, alkoxy or alkoxycarbonyl each having up to 6 C-atoms, or

R⁴ represents adamantyl, cycloalkyl or cycloalkenyl each having up to 6 carbon atoms,

or a salt thereof.

2. An oxalylamino-benzofuran- or benzothienyl-derivative according to claim 1, wherein

L represents an oxygen or sulfur atom,

R¹ represents hydrogen, straight-chain or branched fluorine, chlorine, bromine, nitro, trifluoromethyl or a group of a formula --OR⁵, --SR⁶ or --NR⁷ R⁸, in which

R⁷ denotes hydrogen or a straight-chain or branched alkyl having up to 3 carbon atoms,

R⁵, R⁶, R⁸ are identical or different and denote hydrogen, cyclopropyl, cyclopentyl, cyclohexyl, chinolyl, pyridyl, imidazolyl, 1,3-thiazolyl or thienyl, which are optionally substituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro or by a straight-chain or branched alkyl having up to 5 carbon atoms,

denote straight-chain or branched alkyl or alkenyl each having up to 6 carbon atoms, or

denote phenyl, which is optionally monosubstituted to disubstituted by identical or different substituents selected from the consisting of nitro, fluorine, chlorine, bromine, iodine, carboxy or straight-chain or branched alkoxycarbonyl having up to 5 carbon atoms, or

R⁵ denotes benzyl, acetyl or tetrahydropyranyl,

R² represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,

R³ represents hydroxyl, benzyloxy or straight-chain or branched alkyl or alkoxy each having up to 8 carbon atoms, and each of which is optionally monosubstituted to disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, carboxyl, trifluoromethyl, phenyl, cyano, straight-chain or branched oxyacyl or alkoxy each having up to 4 carbon atoms, morpholinyl or by a residue of a formula ##STR353## or represents phenyl, which is optionally monosubstituted by substituents from the series comprising fluorine, chlorine, bromine, iodine, cyano, nitro, carboxyl or by a straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 5 carbon atoms, or

represents a group of a formula --NR⁹ R¹⁰ in which

R⁹ and R¹⁰ are identical or different and denote hydrogen, cyclopropyl, cyclopentyl, cyclohexyl, or denote straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of carboxy, straight-chain or branched alkoxy, alkoxy-carbonyl or acyl each having up to 5 carbon atoms or phenyl, or denote phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, carboxy, cyano, nitro or by a straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 5 carbon atoms, or

denote a group of a formula --SO₂ R¹¹

in which

R¹¹ denotes straight-chain or branched alkyl having up to 4 carbon atoms, which is optionally substituted by phenyl, or denotes phenyl, which is optionally substituted by trifluoromethyl, cyano, nitro or straight-chain or branched alkyl having up to 4 carbon atoms, or

R³ represents a residue of a formula ##STR354## T represents an oxygen or sulfur atom, A represents hydrogen, cyclopropyl, cyclobutyl, cyclopentyl, hydroxyl, carboxy or straight-chain or a branched alkoxy or alkoxycarbonyl each having up to 5 carbon atoms, or straight-chain or branched alkyl or alkenyl each having up to 6 carbon atoms and each of which is optionally monosubstituted by cyano, tetrazolyl, oxazolyl, oxazolinyl, thiazolyl or a group of a formula ##STR355## in which a denotes a number 1 or 2,

and in which all rings are optionally monosubstituted by hydroxy, fluorine, bromine, chlorine or by straight-chain or branched alkyl having up to 4 carbon atoms,

or alkyl or alkenyl are optionally monosubstituted by a group of a formula --CO--R¹², --CO--NR¹³ R¹⁴, --CONR¹⁵ --SO₂ --R¹⁶, --PO(OR¹⁷)(OR¹⁸) or --OR¹⁹, in which

R¹² denotes hydroxyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy or straight-chain or branched alkyl or alkoxy each having up to 6 carbon atoms,

R¹³, R¹⁴ and R¹⁵ are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, phenyl or benzyl, or

R¹³ denotes hydrogen, and

R¹⁴ denotes hydroxyl, thiazolyl, dihydrothiazolyl or a residue of the formula ##STR356## or R¹³ and R¹⁴ together with the nitrogen atom form a pyrrolidinyl, morpholinyl or a piperidinyl ring,

R¹⁶ denotes a straight-chain or branched alkyl having up to 5 carbon atoms, which is optionally substituted by phenyl or trifluoromethyl, or denotes phenyl, which is optionally substituted by substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro or by straight-chain or branched alkyl having up to 4 carbon atoms,

R¹⁷, R¹⁸ and R¹⁹ are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or

A represents a group --CONR^13'"'"' R^14'"'"', in which

R^13'"'"' and R^14'"'"' have the abovementioned meaning of R¹³ and R¹⁴ and are identical or different to the latter, and

R⁴ represents phenyl, or represents pyridyl, imidazolyl, pyrazolyl, thienyl, isothiazolyl, 1,3-thiazolyl or benzo[b]thiophenyl, where in all rings are optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, naphthyl, adamantyl, phenoxy thiophenyl, thienyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine, iodine, nitro, tetrazolyl, thiazolyl, furanyl, pyridyl, trifluoromethyl, difluoromethyl, cyano, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 10 carbon atoms or by a group of formulae --NR²⁶ R²⁷, --SR²⁸, SO₂ R²⁹, --O--SO₂ R³⁰, --(CH₂)_b --O--CO--R³¹, ##STR357## in which R²⁶ and R²⁷ have the meaning shown above for R⁹ and R¹⁰ and are identical to the latter or different from the latter, or

R²⁶ denotes hydrogen, and

R²⁷ denotes straight-chain or branched acyl having up to 6 carbon atoms,

R²⁸ denotes straight-chain or branched alkyl having up to 4 carbon atoms,

R²⁹ and R³⁰ are identical or different and represent straight-chain or branched alkyl having up to 5 carbon atoms or phenyl, which is optionally substituted by trifluoromethyl, fluorine, chlorine, bromine or straight-chain or branched alkyl having up to 3 carbon atoms,

R³¹ denotes straight-chain or branched alkoxycarbonyl or alkyl each having up to 4 carbon atoms or carbonyl,

b denotes a number 0 or 1,

phenyl is optionally substituted by phenyl or phenoxy, which are optionally monosubstituted to trisubstituted by fluorine, chlorine or bromine, formyl, nitro, straight-chain or branched acyl, alkyl, hydroxyalkyl, alkoxy, alkoxycarbonyl each having up to 4 carbon atoms, or

R⁴ represents adamantyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl,

or a salt thereof.

3. An oxalylamino-benzofuran- or benzothienyl-derivative according to claim 1, wherein

L represents an oxygen or sulfur atom,

R¹ represents hydrogen, straight-chain or branched alkyl having up to 3 carbon atoms, fluorine, chlorine, bromine, nitro, trifluoromethyl or a group of a formula --OR⁵, in which

R⁵ denotes hydrogen, benzyl, acetyl or denotes straight-chain or branched alkyl each having up to 3 carbon atoms, or denotes phenyl,

R² represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms,

R³ represents hydroxyl, benzyloxy or straight-chain or branched alkyl or alkoxy each having up to 7 carbon atoms, which is optionally substituted by substituents selected from the group consisting of fluorine, chlorine, bromine, trifluoromethyl, carboxyl, phenyl, cyano, straight-chain or branched alkoxy or oxyacyl each having up to 5 carbon atoms, morpholinyl or by a residue of a formula ##STR358## or represents phenyl, which is optionally monosubstituted by different substituents selected from the group consisting of fluorine, chlorine or bromine, or

represents a group of a formula --NR⁹ R¹⁰, in which

R⁹ and R¹⁰ are identical or different and denote hydrogen, cyclopropyl, cyclopentyl, cyclohexyl or denote straight-chain or branched alkyl having up to 4 carbon atoms or denote phenyl, or

R³ represents a residue of a formula ##STR359## T represents an oxygen atom or sulfur, A represents hydrogen, cyclopropyl, cyclobutyl, cyclopentyl, hydroxyl, carboxy, or straight-chain or a branched alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, or straight-chain or branched alkyl or alkenyl each having up to 5 carbon atoms and each of which is optionally monosubstituted by cyano, tetrazolyl, oxazolyl, oxazolinyl, thiazolyl or a group of the formula ##STR360## in which a denotes a number 1 or 2,

or alkyl or alkenyl are optionally monosubstituted by a group of a formula --CO--R¹², --CO--NR¹³ R¹⁴ or --OR¹⁹, in which

R¹² denotes hydroxyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy or straight-chain or branched alkyl or alkoxy each having up to 5 carbon atoms,

R¹³ and R¹⁴ are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 3 carbon atoms, phenyl or benzyl, or

R¹³ denotes hydrogen, and

R¹⁴ denotes hydroxyl, thiazolyl, dihydrothiazolyl or a residue of the formula ##STR361## or R¹³ and R¹⁴ together with the nitrogen atom form a pyrrolidinyl, morpholinyl or piperidinyl ring,

R¹⁹ denotes hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,

A represents a group of the formula --CONR^13'"'"' R^14'"'"', in which

R^13'"'"' and R^14'"'"' have the abovementioned meaning of R¹³ and R¹⁴ and are identical or different to the latter, and

R⁴ represents phenyl, or represents pyridyl, thienyl, furyl which are optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, naphthyl, adamantyl, thiopenyl, cyclopentyl, cyclohexy, fluorine, chlorine, bromine, nitro, tetrazolyl, thiazolyl, thienyl, furanyl, pyridyl, phenoxy, trifluoromethyl, difluoromethyl, cyano, carboxyl, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 9 carbon atoms or by a group of formulae --NR²⁶ R²⁷, SR²⁸ or --(CH₂)_b --O--CO--R³¹, ##STR362## in which R²⁶ and R²⁷ have the meaning shown above for R⁹ and R¹⁰ and are identical to the latter or different from the latter, or

R²⁶ denotes hydrogen, and

R²⁷ denotes straight-chain or branched acyl having up to 5 carbon atoms,

R²⁸ denotes straight-chain or branched alkyl having up to 4 carbon atoms,

R³¹ denotes straight-chain or branched alkoxycarbonyl or alkyl each having up to 4 carbon atoms or carboxy,

b denotes a number 0 or 1, or

phenyl is optionally substituted by phenyl or phenoxy, which are optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, nitro, formyl or straight-chain or branched acyl, alkoxy, alkyl, hydroxyalkyl or alkoxycarbonyl, each having up to 3 carbon atoms, or

R⁴ represents adamantyl, cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl

or a salt thereof.

4. A compound according to claim 1 wherein such compound is N-[3-methyl-2-(4-methyl-benzoyl)-benzofuran-6-yl]-oxalamic acid ethyl ester of the formula ##STR363## or a salt thereof.

5. A compound according to claim 1 wherein such compound is N-[2-(biphenyl-4-carbonyl)-3-methyl-benzofuran-6-yl]-oxalamic acid of the formula ##STR364## or a salt thereof.

6. A compound according to claim 1 wherein such compound is N-[3-methyl-2-(4-methyl-benzoyl)-benzofuran 6-yl]-oxalamic acid isopropyl ester of the formula ##STR365## or a salt thereof.

7. A compound according to claim 1 wherein such compound is 3-[6-(carboxycarbonylamino)-2-(pyridine-3-carbonyl)-benzofuran-3-yl]-propionic acid of the formula ##STR366## or a salt thereof.

8. A compound according to claim 1 wherein such compound is N-[3-methyl-2-(pyridine-4-carbonyl)-benzofuran-5-yl]-oxalamic acid ethyl ester of the formula ##STR367## or a salt thereof.

9. A compound according to claim 1 wherein such compound is N-[3-ethyl-2-(4-methyl-benzoyl)-benzofuran-5-yl]-oxalamic acid of the formula ##STR368## or a salt thereof.

10. An anti-inflammatory composition comprising an amount effective therefor of a compound or salt according to claim 1 and a pharmacologically acceptable diluent.

11. A method of decreasing inflammation in a patient in need thereof which comprises administering to such patient an amount effective therefor of a compound or salt according to claim 1.

12. The method according to claim 11, wherein such compound is

N-[3-methyl-2-(4-methyl-benzoyl)-benzofuran-6-yl]-oxalamic acid ethyl ester,

N-[2-(biphenyl-4-carbonyl)-3-methyl-benxofuran-6-yl]-oxalamic acid,

N-[3-methyl-2-(4-methyl-benzoyl)-benzofuran 6-yl]-oxalamic acid isopropyl ester,

3-[6-(carboxycarbonylamino)-2-(pyridine-3-carbonyl)-benzofuran-3-yl]-propionic acid,

N-[3-methyl-2-pyridine-4-carbonyl)-benzofuran-5-yl]-oxalamic acid ethyl ester, or

N-[3-ethyl-2-(4-methyl-benzoyl)-benzofuran-5-y]-oxalamic acid

or salt thereof.